Chloromethylhalicyclamine B, a Marine-Derived Protein Kinase CK1δ/ε Inhibitor Germana Esposito, Marie-Lise Bourguet-Kondracki, * Linh H. Mai, Arlette Longeon, Roberta Teta, Laurent Meijer, Rob Van Soest, Alfonso Mangoni, Valeria Costantino * Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS, Muséum National d Histoire Naturelle, 57 rue Cuvier (C.P. 54), 75005 Paris, France The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via D. Montesano 49, 80131 Napoli, Italy ManRos Therapeutics, Perharidy Research Center, 29680 Roscoff, France Naturalis Biodiversity Center, P.O. Box 9517, 2300 RA Leiden, The Netherlands Table of contents Supporting Information Table S1. Activity of compounds 1 and 2 against a panel of 14 kinases.... S2 Figure S1. Inhibition of CK1δ/ε by compound 1... S2 Figure S2. Average interproton distances and NOEs of compound 1... S3 1 H-NMR spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S4 DEPTQ spectrum of chloromethylhalicyclamine B (1) (150 MHz, CD 3 OD)... S5 COSY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S6 NOESY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S7 HSQC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S8 HMBC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)... S9 Table S1. Cartesian coordinates of the 20 lowest-energy conformers of 1 in the CFF91 force field.... S10
S2 Table S1. Activity of compounds 1 and 2 against a panel of 14 kinases. IC 50 (μm) Compound 1 Compound 2 CDK2/cyclin A inactive a not tested CDK5/p25 inactive a inactive a CDK9/cyclin T inactive a inactive a CK1δ/ε 6 μm inactive a LmCK1 inactive a not tested CLK1 inactive a inactive a CLK2 inactive a not tested CLK3 inactive a not tested CLK4 inactive a not tested DYRK1A inactive a inactive a DYRK1B inactive a not tested DYRK2 inactive a not tested DYRK3 inactive a not tested GSK3 inactive a inactive a a Not significantly active at 10 μm Figure S1. Inhibition of CK1δ/ε by compound 1. Data are expressed as SD of mean (n = 2).
S3 Figure S2. Average interproton distances for compound 1 calculated by a molecular dynamics simulation, and NOEs detected from the NOESY spectrum. Because of chemical shift degeneracy, NOESY cross peaks were assigned in an iterative process: only unambiguous NOESY peaks were used at the initial stage to validate the interproton distances generated by MD calculations; after this, average distances themselves were used as a guide to assign the ambiguous NOESY peaks. Only calculated distances < 3.5 Ǻ are shown in the table. The table is color coded. Distances between geminal protons are in blue digits; distances between vicinal protons are in red digits; distances between distal protons are in black digits; distances > 3.5 Ǻ between protons showing NOE are in white digits. A light blue background indicates the presence of NOE. A pink background indicates that the presence (or absence) of NOE was not experimentally accessible, either because the protons involved have very close chemical shifts, or because the correlation would be overlapped with a very strong geminal NOE. A yellow background indicates absence of NOE with a calculated interproton distance < 3.0 Ǻ.
S4 1 H-NMR spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
S5 DEPTQ spectrum of chloromethylhalicyclamine B (1) (150 MHz, CD 3 OD)
S6 COSY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
S7 NOESY spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
S8 HSQC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
S9 HMBC spectrum of chloromethylhalicyclamine B (1) (600 MHz, CD 3 OD)
S10 Table S1. Cartesian coordinates of the 20 lowest-energy conformers of 1 in the CFF91 force field Conformer #1 Energy: -3.2994 kcal/mol N -5.652875423 1.317657113 2.623045206 C -5.025234699-0.107916512 2.738358498 C -4.569676876-0.670670927 1.383069515 C -3.708855867 0.290719956 0.517952979 C -4.217148304 1.752445698 0.522663355 C -4.601612568 2.226665497 1.927202344 C -6.977544785 1.184237480 1.822862625 C -5.843958855 1.886154175 4.021293163 Cl -6.971858501 0.910228193 4.957873821 C -3.645882845-0.200284317-0.939029932 C -4.752438068-0.364142179-1.689709783 H -5.745840073-0.210963354-1.268783450 C -4.708364487-0.592196882-3.188090563 C -3.284011364-0.995753765-3.660797119 N -2.256704092-0.171878576-3.022655249 C -2.275576353-0.361215144-1.569649458 C -0.920038402-0.091562711-3.663098812 C -5.204429626 0.693325460-3.893078089 C -3.281074286 2.789698362-0.167478740 C -6.683212757 1.132819772-3.561608315 C -6.756124496 2.412176132-2.753295183 H -6.173875332 3.237400055-3.176030636 C -7.498100281 2.679896116-1.667236567 H -7.473720551 3.710287571-1.302404165 C -7.741474152 2.474673271 1.482600331 C -0.741794109 1.267295241-4.383331776 C -8.449128151 1.731966257-0.950341105 C -8.871765137 2.210334539 0.451564640 C -0.953132033 2.548987865-3.543450117 C -0.061735880 2.747299194-2.305655718 C -0.467130154 4.015817642-1.581535220 H -0.121925309 4.936977386-2.061237335 C -1.215389371 4.130861282-0.471509635 H -1.435942650 5.142223358-0.117138900 H -5.769261360-0.772985220 3.209986687 H -4.161211967-0.020830430 3.421781778 H -3.982359171-1.583029389 1.596939087 H -5.454272270-1.026901603 0.831284344 H -2.691481829 0.281580180 0.956625581 H -5.139114857 1.795311332-0.085700110 H -5.012009144 3.251559258 1.905955791 H -3.712658644 2.236255646 2.584885120 H -6.720226765 0.671811461 0.883712232 H -7.631933689 0.494899631 2.385543585 H -6.242705345 2.909631491 3.941169977 H -4.869802952 1.896736145 4.536104202 H -5.398119926-1.415292621-3.456308603 H -3.109247208-2.070752859-3.462585688 H -3.224714041-0.882274628-4.757843494 H -1.586838126 0.374095380-1.123820782 H -1.871655345-1.354393601-1.290807486 H -0.115572356-0.212178797-2.919275045 H -0.764173687-0.903795779-4.393575668 H -5.148390770 0.530334830-4.985753059 H -4.495169163 1.517037392-3.694499731 H -3.807508230 3.764081001-0.159182191 H -3.209531784 2.523411036-1.239362717 H -7.211440086 1.323023796-4.514120579 H -7.238192081 0.312779725-3.083944321 H -8.197288513 2.899007082 2.393800735 H -7.074282646 3.250748158 1.074929237 H 0.269493580 1.289231658-4.826533794 H -1.447729826 1.305809021-5.234602928 H -9.360883713 1.635323048-1.567310452 H -8.015739441 0.721950889-0.908665895 H -9.464969635 3.136629581 0.331507683 H -9.576398849 1.469356894 0.874658287 H -2.012016773 2.584501505-3.231231928 H -0.816380501 3.415255308-4.217136860 H -0.122209027 1.876286268-1.641335487 H 1.000231743 2.826394320-2.604902983 C -1.849214792 3.014375687 0.343557209 H -1.830797553 3.305689096 1.409280419 H -1.255340695 2.092936039 0.268144280
S11 Conformer #2 Energy: -2.6913 kcal/mol N -4.662939548 1.055608153 2.776572227 C -4.929003716-0.452352077 2.470746517 C -5.242904663-0.713575065 0.990104675 C -4.262825489-0.066035934-0.028644476 C -3.828276157 1.373606682 0.348921090 C -3.511345148 1.515559554 1.841591239 C -5.990900993 1.825701952 2.542592049 C -4.130818367 1.181661367 4.196633339 Cl -5.320271492 0.633347273 5.374059677 C -4.892313004-0.039182790-1.434369206 C -6.059679508 0.585529029-1.683437109 H -6.630342960 1.053043485-0.881472647 C -6.583573341 0.833999455-3.083560944 C -5.838116646-0.039639745-4.128545761 N -4.394653320-0.055329155-3.893634319 C -4.084045887-0.627141535-2.578004360 C -3.584082365-0.511835873-5.034541607 C -6.454602242 2.343986273-3.396577597 C -2.664670229 1.966540456-0.503346205 C -7.273542881 3.311414003-2.457645178 C -6.393894196 4.148456573-1.551851869 H -5.593317509 4.679156780-2.077270985 C -6.528547764 4.388310432-0.238160446 H -5.835124969 5.111730576 0.199130222 C -5.966561794 3.355104208 2.696390867 C -2.059402466-0.566349089-4.760798454 C -7.606809139 3.842100382 0.686702192 C -7.283775806 3.997581005 2.184411526 C -1.419682384 0.747586608-4.253325939 C -0.180936158 0.541966975-3.362224817 C 0.132486254 1.797843099-2.571020603 H 0.773030400 2.521036386-3.084282398 C -0.332296520 2.113885641-1.350203037 H -0.030171335 3.078409433-0.931542933 H -5.759675026-0.791571259 3.113594770 H -4.018267155-1.002979159 2.768307924 H -5.230461121-1.810446978 0.849211216 H -6.285245895-0.415814281 0.793567419 H -3.357728958-0.704659283-0.039315838 H -4.677248001 2.051075697 0.142514423 H -3.271789312 2.562088251 2.100111008 H -2.633352518 0.896898389 2.104781389 H -6.311815262 1.582260609 1.518516779 H -6.745993137 1.389440179 3.220515251 H -3.893147945 2.237886190 4.398637295 H -3.223953724 0.563071609 4.292008400 H -7.657064438 0.567665577-3.128789902 H -6.250663757-1.067224741-4.120426655 H -6.046041965 0.356770515-5.138672352 H -3.016579628-0.454711825-2.361781359 H -4.219198227-1.726541996-2.575368643 H -3.907774448-1.513004661-5.379968166 H -3.770824432 0.180913046-5.875357151 H -6.810969830 2.512629986-4.430162430 H -5.386085987 2.625011444-3.417290449 H -2.548421621 3.027267456-0.207230732 H -2.993359089 2.007536411-1.559640050 H -7.842071533 4.014779091-3.093731642 H -8.034913063 2.755531073-1.891932964 H -5.838384628 3.630573750 3.757389545 H -5.123218536 3.806833029 2.150058508 H -1.868155956-1.376263022-4.033229828 H -1.552662134-0.887537539-5.687607288 H -8.542511940 4.392533302 0.479870528 H -7.823129654 2.792937040 0.437201142 H -7.264933586 5.078686237 2.419296265 H -8.131306648 3.590251207 2.767791271 H -2.169005156 1.318033576-3.677482367 H -1.166836381 1.394905567-5.110970020 H -0.355754077-0.299026042-2.674383640 H 0.696516514 0.255331129-3.970837355 C -1.274713874 1.305209637-0.474853098 H -0.856971025 1.269763231 0.547170222 H -1.339726925 0.263031244-0.817333698
S12 Conformer #3 Energy: -2.2555 kcal/mol N -3.817542246 0.979785047 2.854480177 C -4.673840211-0.321509382 2.731809405 C -5.505566320-0.362803645 1.440436232 C -4.716591528-0.032377047 0.142438186 C -3.735383337 1.156593303 0.289203756 C -2.924321616 1.076224149 1.587808090 C -4.813592916 2.167211877 2.994885192 C -2.931661331 0.892206321 4.091539143 Cl -1.841434690-0.492468243 4.044472131 C -5.683852893 0.266542540-1.016290341 C -6.586715132 1.264527167-0.959070192 H -6.702387046 1.867090487-0.058798729 C -7.375370344 1.736182430-2.165236612 C -7.305575747 0.708073892-3.328498309 N -5.946573100 0.195370045-3.505541135 C -5.505178350-0.516565011-2.303122933 C -5.587888691-0.417884229-4.808779451 C -6.837218127 3.122988093-2.592087247 C -2.794221335 1.399489850-0.929127463 C -6.955923089 4.267917604-1.513466281 C -5.615315231 4.698941666-0.955193246 H -4.875833258 4.949556959-1.722802186 C -5.259958275 4.894171714 0.324273145 H -4.261890018 5.306918778 0.494419648 C -4.230621875 3.590934295 3.018432973 C -4.711217404 0.548618538-5.642034088 C -6.130717963 4.697746554 1.557383418 C -5.342972547 4.665347913 2.880322683 C -3.415489351 1.077624719-4.983225581 C -2.370835754 0.043457331-4.530398513 C -1.214752516 0.748776628-3.849330641 H -0.522211887 1.244228894-4.536791691 C -0.976665797 0.862264877-2.531892797 H -0.103520786 1.447034979-2.227351522 H -5.307019195-0.391053045 3.633563939 H -3.978476301-1.178313172 2.735173782 H -5.913629868-1.387433696 1.356952070 H -6.389523415 0.284327890 1.553687634 H -4.120181487-0.935069297-0.097534551 H -4.330184747 2.086344622 0.342512894 H -2.264256044 1.952122927 1.711545743 H -2.286772868 0.175318309 1.568245808 H -5.520225713 2.092515074 2.155461617 H -5.392395616 1.982576410 3.918689508 H -3.576542921 0.801446830 4.980289994 H -2.327173453 1.810296655 4.159498301 H -8.439557931 1.856142960-1.885411982 H -8.020148467-0.117913702-3.148139321 H -7.644348999 1.196275557-4.259493647 H -4.438576843-0.762578577-2.428054993 H -6.024899309-1.489594266-2.201194497 H -5.042190407-1.364755686-4.665085359 H -6.481812822-0.684396495-5.398192455 H -7.403988257 3.452205545-3.483193809 H -5.794620202 3.020166504-2.943408861 H -2.216904489 2.320952567-0.718970543 H -3.423905198 1.659779565-1.801204104 H -7.404027598 5.155968458-1.996344994 H -7.661251625 3.985590547-0.718814437 H -3.695080469 3.771240945 3.966226213 H -3.497153171 3.745840943 2.210745034 H -4.453873669 0.045301098-6.590735570 H -5.326484828 1.425329969-5.920012485 H -6.845346848 5.539320642 1.605482275 H -6.748642342 3.795178656 1.442946107 H -4.890025498 5.663751495 3.030677386 H -6.062889684 4.546968981 3.712204966 H -3.699919964 1.701325875-4.117116800 H -2.936059033 1.770545016-5.699426233 H -2.825936596-0.701374941-3.865698204 H -1.986602660-0.521867763-5.400063384 C -1.808381805 0.311630591-1.384241580 H -1.124109324 0.007837061-0.571295134 H -2.340747199-0.599191033-1.691135040
S13 Conformer #4 Energy: -2.0040 kcal/mol N -4.582811939 0.754472616 2.884021274 C -5.919123048-0.017878341 2.613633371 C -6.509194667 0.247141934 1.221532795 C -5.502200557 0.094465204 0.051267144 C -4.123150847 0.727686298 0.346557411 C -3.599698485 0.375312225 1.744292056 C -4.941254649 2.264324132 2.936178000 C -4.047884401 0.201702466 4.199428435 Cl -2.455929384 0.848042841 4.582422561 C -6.067213338 0.716467051-1.237874399 C -6.415693027 2.015187735-1.316112021 H -6.359289146 2.665585587-0.443909292 C -6.742001812 2.706823812-2.625388471 C -7.001231789 1.679495584-3.762146698 N -6.013602947 0.600004532-3.738225179 C -6.100620065-0.150323454-2.482509287 C -5.803276083-0.193079961-4.974709022 C -5.583482499 3.670478345-2.978040107 C -3.022436164 0.464691917-0.725052325 C -5.291528163 4.809361747-1.927536824 C -4.001563090 4.595464391-1.162657734 H -3.130038605 4.422382175-1.802312699 C -3.785396060 4.676140547 0.159460297 H -2.748256601 4.577802522 0.490919215 C -3.811850170 3.308437836 3.024399266 C -4.491052714 0.233266192-5.677051742 C -4.818406235 4.981696000 1.235693295 C -4.323933794 4.732738107 2.672100269 C -3.191517317 0.185265336-4.839378486 C -2.780385192-1.168209051-4.235287053 C -1.531477539-0.992988369-3.394394171 H -0.609049386-0.891421735-3.974540135 C -1.441193463-0.909510461-2.056495349 H -0.447909890-0.741817752-1.629257000 H -6.627435190 0.255580978 3.416020075 H -5.689467686-1.094817960 2.713648162 H -7.333092330-0.477623872 1.082915379 H -6.996558556 1.234845648 1.210797359 H -5.353614472-0.993385623-0.098157500 H -4.244441948 1.826239199 0.330066331 H -2.641323672 0.887430013 1.934562658 H -3.423735943-0.712383592 1.831750111 H -5.519327162 2.470915525 2.023249276 H -5.633210404 2.393264454 3.788374881 H -3.963096703-0.893433566 4.111179648 H -4.746987413 0.464309331 5.009207923 H -7.660567304 3.311999042-2.501989184 H -8.029579573 1.277469049-3.683657453 H -6.959690107 2.202085872-4.734254882 H -5.255182262-0.856189120-2.450981784 H -7.013395329-0.777397343-2.454072785 H -5.756877175-1.271327380-4.750826480 H -6.640467102-0.079173065-5.684456257 H -5.829300131 4.164386563-3.936901708 H -4.668906465 3.086985425-3.187660832 H -2.129721131 1.049681488-0.429026022 H -3.351390448 0.924548789-1.676503981 H -5.187500824 5.766513571-2.471422538 H -6.150328897 4.950664833-1.255653518 H -3.406498179 3.349535903 4.049543364 H -2.964348955 3.067057404 2.363182167 H -4.364194386-0.394820489-6.576474253 H -4.613109677 1.269809726-6.044684916 H -5.092145705 6.048811404 1.150579879 H -5.745218745 4.425353330 1.034078132 H -3.513136945 5.456438675 2.881021528 H -5.137576519 5.002305971 3.371874840 H -3.279031399 0.927446452-4.025873641 H -2.367235216 0.548512760-5.480904094 H -3.600241348-1.592196449-3.642185354 H -2.575816270-1.901866794-5.037389919 C -2.571003069-0.970175845-1.041040187 H -2.202873883-1.494745676-0.140783055 H -3.407624276-1.570488682-1.424122033
S14 Conformer #5 Energy: -1.6326 kcal/mol N -4.683303356 0.836402357 2.866806269 C -5.237982273-0.580038905 2.508544922 C -5.628036499-0.722059965 1.028562427 C -4.543234825-0.269419312 0.013712587 C -3.890622139 1.075061202 0.413924962 C -3.510518789 1.128308177 1.898464084 C -5.850104809 1.858291626 2.741431236 C -4.075126648 0.769926548 4.262490749 Cl -5.295722485 0.393732935 5.475187778 C -5.125929832-0.118487000-1.403720140 C -6.202776432 0.650555134-1.660181999 H -6.753887177 1.127756834-0.850682616 C -6.580515862 1.103999853-3.060825348 C -5.881999016 0.239118516-4.143981457 N -4.473468304 0.003480329-3.829799891 C -4.338509083-0.714271367-2.558425665 C -3.598974705-0.457095981-4.937694550 C -6.204620838 2.608160019-3.157527447 C -2.677287102 1.543458462-0.444714069 C -7.110916138 3.562479019-2.316215754 C -6.351838589 4.760052681-1.787280202 H -5.974490166 5.433737278-2.563259125 C -6.125758171 5.103312016-0.507345498 H -5.594362259 6.044931412-0.336059868 C -5.516261101 3.357669830 2.971162796 C -2.715198278 0.701744437-5.458355427 C -6.540555000 4.368940830 0.753748775 C -5.337708950 4.243060589 1.710516334 C -1.822014332 1.422722697-4.422475338 C -0.811012030 0.564627051-3.642927885 C -0.101937361 1.417517662-2.610825539 H 0.669485033 2.076205969-3.021414518 C -0.342805266 1.479804397-1.290736079 H 0.247244179 2.190712214-0.704694152 H -6.102985382-0.782976449 3.163681746 H -4.442190170-1.305642128 2.757018805 H -5.854483128-1.791929603 0.863405466 H -6.583657265-0.200864613 0.863450706 H -3.761025429-1.054122686 0.009703992 H -4.648489475 1.861648440 0.246000096 H -3.100456715 2.117765665 2.168711901 H -2.732546806 0.372421741 2.113203287 H -6.295370579 1.718128681 1.745322943 H -6.619659901 1.538364768 3.465853214 H -3.618248701 1.740658998 4.508033752 H -3.306942940-0.020200100 4.275733948 H -7.672582626 1.006251574-3.210896730 H -6.426241398-0.717590451-4.264894485 H -5.962100029 0.752927065-5.118655205 H -3.268678427-0.732598662-2.296232462 H -4.633704185-1.776415825-2.669291735 H -2.947026491-1.283942819-4.611540318 H -4.182865620-0.865914166-5.780430317 H -6.247409344 2.944579840-4.209310055 H -5.143682003 2.717752695-2.865998030 H -2.412483215 2.561956406-0.098487757 H -3.021037579 1.689357162-1.485838532 H -7.943100929 3.922893524-2.949415922 H -7.597986698 3.021738529-1.494825482 H -6.361098766 3.774372339 3.551921844 H -4.636512756 3.503637314 3.619484901 H -2.078987122 0.307343304-6.270319939 H -3.370389223 1.460923076-5.925786495 H -7.354392529 4.932383537 1.245707750 H -6.955630779 3.382879257 0.509491563 H -4.457383633 3.894565105 1.142869711 H -5.072234631 5.261370659 2.054217100 H -2.480793953 1.943347216-3.704941750 H -1.272032022 2.223470926-4.950685978 H -1.313187838-0.288370758-3.169235945 H -0.062147662 0.131136402-4.331914902 C -1.387770176 0.708370924-0.498691231 H -0.979077220 0.509053051 0.508289039 H -1.573931456-0.275305599-0.951758683
S15 Conformer #6 Energy: -1.5979 kcal/mol N -4.466070570 0.906994478 2.852432656 C -5.591740563-0.137525592 2.565556106 C -6.215827476 0.034105139 1.172625730 C -5.197108633 0.158995660 0.003450811 C -3.967347499 1.047626499 0.326727344 C -3.405180127 0.773854735 1.727777679 C -5.143148688 2.306971978 2.894488015 C -3.817517613 0.599316800 4.197295618 Cl -3.116570425-1.017329214 4.255787205 C -5.894176653 0.711445726-1.254213089 C -6.519828289 1.904404715-1.260024728 H -6.595463913 2.504203376-0.353738526 C -7.016422885 2.573088531-2.526114044 C -7.068755997 1.570635872-3.710709663 N -5.873969806 0.728922320-3.762940009 C -5.747832455-0.078060137-2.543377468 C -5.647870692 0.047596352-5.048043766 C -6.104916379 3.784457944-2.835631239 C -2.819038124 1.005890649-0.728022872 C -6.072121241 4.915478033-1.737293998 C -4.752328324 4.988640497-0.997768942 H -3.878526553 5.048470142-1.654788064 C -4.533314341 5.080201708 0.323136792 H -3.495830051 5.226240703 0.635764536 C -4.233230254 3.535556347 3.064245726 C -4.401128583-0.872827301-5.078003872 C -5.582539109 5.103801187 1.425572931 C -5.013004738 4.858275940 2.834813412 C -3.063114598-0.206124439-4.680185285 C -2.039453112-1.172281142-4.056145154 C -0.957594424-0.411169487-3.313251524 H -0.104267983-0.102941038-3.924327958 C -0.975516704-0.051624016-2.018396843 H -0.122375937 0.521456035-1.643512407 H -6.344042168-0.047558796 3.368597747 H -5.138524516-1.141403164 2.632104629 H -6.849920843-0.854744015 0.995759665 H -6.918651054 0.881786501 1.191736981 H -4.829795392-0.866899331-0.197449780 H -4.296215467 2.102692731 0.315798941 H -2.573053445 1.456900031 1.971409062 H -3.016107483-0.258203226 1.770544522 H -5.706994579 2.417039531 1.956581801 H -5.884325019 2.271681867 3.714177911 H -4.585124897 0.677791246 4.983830275 H -3.017151391 1.333289013 4.380449956 H -8.043217580 2.953472390-2.363749908 H -7.984491140 0.952286935-3.638481361 H -7.165809644 2.137464931-4.654097612 H -4.753520789-0.554805980-2.537018935 H -6.481011577-0.908288539-2.532805940 H -6.528772273-0.556074048-5.341276226 H -5.534408642 0.826737433-5.823786478 H -6.459882176 4.250189558-3.774178764 H -5.084415863 3.428344078-3.065672884 H -2.076071811 1.772453243-0.433677300 H -3.220484647 1.364024589-1.695414661 H -6.214692324 5.891062910-2.237884449 H -6.924452143 4.817132386-1.049821786 H -3.806561452 3.561832795 4.081494647 H -3.379972284 3.509551271 2.367304185 H -4.594463580-1.737338484-4.416802904 H -4.311063166-1.301109917-6.091591896 H -6.060396740 6.100222969 1.418228380 H -6.387927068 4.390999032 1.195540550 H -4.349462809 5.707440924 3.086215862 H -5.844579129 4.916616070 3.562409383 H -3.261186606 0.602672382-3.955490872 H -2.622475281 0.299023794-5.557176907 H -2.552237134-1.859606177-3.366418856 H -1.580260222-1.812138951-4.832127424 C -2.067513608-0.311286179-0.994620690 H -1.597295553-0.708574352-0.077140067 H -2.764451072-1.086145384-1.343032141
S16 Conformer #7 Energy: -1.5900 kcal/mol N -5.960827351 1.254243731 2.664726496 C -5.646790028-0.272916377 2.630169630 C -5.104932785-0.735548615 1.271086693 C -3.974704266 0.133136630 0.640109122 C -4.134761333 1.669253826 0.861526132 C -4.657277584 1.994315743 2.268364429 C -7.138128757 1.519169331 1.687051535 C -6.259581566 1.661257386 4.100357533 Cl -7.694521427 0.841421843 4.709000111 C -3.887932777-0.192551002-0.863532722 C -4.917086601 0.032898773-1.702896357 H -5.859381199 0.439453632-1.338558555 C -4.823953152-0.138533622-3.205713987 C -3.533874512-0.901679099-3.615026236 N -2.374437094-0.471293271-2.833700895 C -2.577740669-0.737153292-1.404587388 C -1.034368992-0.757678747-3.387244225 C -4.920509815 1.254708767-3.872637510 C -2.831321716 2.495398045 0.626445711 C -6.267095089 2.032996655-3.621124029 C -6.127848148 3.173286676-2.634347677 H -5.323812008 3.874524117-2.879935980 C -6.903024197 3.472960234-1.580252171 H -6.677487850 4.407396793-1.059620023 C -7.576531410 2.977304220 1.476095676 C -0.515774846 0.418402433-4.256141663 C -8.123765945 2.703581572-1.094750166 C -8.599612236 3.101719379 0.314601392 C -0.539070308 1.829740763-3.617894411 C 0.136409327 1.976092458-2.246700048 C -0.142712653 3.331082106-1.611062050 H 0.670336962 4.058545113-1.686144233 C -1.272684813 3.689999580-0.977568805 H -1.324742556 4.699432373-0.561271727 H -6.569130898-0.820820332 2.889850616 H -4.900619030-0.462507039 3.422794819 H -4.724167347-1.764591813 1.409684420 H -5.956617832-0.841630101 0.579308391 H -3.033682108-0.171468213 1.139883041 H -4.885403633 2.060820580 0.152440697 H -4.848688602 3.076950312 2.376361132 H -3.897739172 1.712734818 3.022204399 H -6.829872131 1.104745746 0.715382874 H -7.993548393 0.911946714 2.032795906 H -6.430297852 2.748603582 4.137679100 H -5.398953438 1.389744520 4.732632160 H -5.687531948-0.734721601-3.558718681 H -3.695969343-1.991745234-3.509386063 H -3.342640162-0.734164417-4.689753532 H -1.741088867-0.278473645-0.847452998 H -2.524193048-1.821710467-1.186728954 H -0.312606633-0.928343832-2.571473598 H -1.021461964-1.686288595-3.985524654 H -4.823913097 1.116767406-4.966084480 H -4.049021721 1.869502187-3.586866379 H -1.965681195 1.964780569 1.062954187 H -2.904353619 3.449012280 1.182312727 H -6.595104694 2.478333235-4.578862667 H -7.068762779 1.336127758-3.336399078 H -8.048276901 3.372806072 2.392058372 H -6.717422962 3.631212711 1.256313086 H 0.517067254 0.177315667-4.563850880 H -1.106846929 0.462348402-5.190095425 H -8.950788498 2.898243189-1.801378012 H -7.936587811 1.621407986-1.155331254 H -8.958826065 4.147388458 0.271073520 H -9.494626045 2.499355793 0.561126590 H -1.593646526 2.148130894-3.544331789 H -0.070754491 2.537489891-4.326050758 H -0.206387773 1.189877748-1.559586763 H 1.229470015 1.836816549-2.341896534 C -2.531075001 2.857649326-0.836406410 H -2.453065872 1.952338457-1.448077440 H -3.373546362 3.433966875-1.261322856
S17 Conformer #8 Energy: -1.4874 kcal/mol N -5.863700895 1.135313089 2.557333077 C -5.575877262-0.400068095 2.552115819 C -5.068810639-0.909412911 1.195268545 C -3.897865541-0.098225335 0.570933411 C -4.020786006 1.441830096 0.754656724 C -4.557988435 1.853257115 2.130719266 C -7.049483780 1.399411270 1.591781054 C -6.139429608 1.571994288 3.989457704 Cl -7.589797559 0.799587104 4.623371975 C -3.780206051-0.385180543-0.941625650 C -4.818643741-0.196486259-1.781895745 H -5.792975065 0.120515224-1.411321597 C -4.697018576-0.262027416-3.292065158 C -3.339187602-0.874262529-3.726599489 N -2.233718791-0.371234729-2.911069283 C -2.420095614-0.765667944-1.508981187 C -0.869011075-0.511130552-3.471514528 C -4.890019831 1.155944053-3.881005924 C -2.680804590 2.186142935 0.491203800 C -6.287692970 1.834810843-3.616967748 C -6.194167094 3.038049851-2.702016159 H -5.424950344 3.760911095-2.992848557 C -6.979725916 3.362635726-1.664018157 H -6.799568481 4.336170846-1.199816985 C -7.501200703 2.855556587 1.401922652 C -0.328864061 0.834328235-4.011649877 C -8.164032197 2.571065219-1.131337447 C -8.582429490 2.969013594 0.295061530 C -0.089594416 1.958982787-2.973172010 C -1.258782390 2.921245526-2.690222787 C -0.853087197 3.910532209-1.614334534 H 0.086007707 4.436094803-1.812677519 C -1.499653426 4.199726959-0.472863871 H -1.045426275 4.927694572 0.205365485 H -6.502932715-0.923074083 2.844433763 H -4.817351074-0.584073565 3.334395910 H -4.736946205-1.953111202 1.348647363 H -5.926166047-0.984135420 0.507806703 H -2.975156081-0.427361874 1.088783675 H -4.743430734 1.812352520 0.004793359 H -4.745710717 2.940281319 2.174831991 H -3.807556982 1.612204932 2.907240848 H -6.745070737 0.997378801 0.613267236 H -7.897447921 0.783339601 1.940617388 H -6.281094783 2.663913731 4.011730771 H -5.280541041 1.288334445 4.618769170 H -5.501511336-0.906355219-3.695801604 H -3.391045664-1.979333380-3.682205312 H -3.159815498-0.629823843-4.788907100 H -1.615391927-0.298322133-0.914736672 H -2.278976161-1.857234982-1.381786389 H -0.163498893-0.890170449-2.713278613 H -0.839026239-1.254856842-4.286972155 H -4.762978813 1.089421728-4.978030624 H -4.066952603 1.809107592-3.543418374 H -2.095404530 1.639910239-0.265008774 H -2.046469105 2.170128372 1.395789670 H -6.688891579 2.192789226-4.582947585 H -7.020080771 1.099033504-3.255944293 H -7.927714131 3.253442129 2.338595859 H -6.654521532 3.508841584 1.136031244 H 0.640768335 0.612737076-4.493132869 H -0.987891111 1.199759547-4.820193710 H -9.022677134 2.749415767-1.803917211 H -7.960358438 1.491993939-1.194268573 H -8.953099701 4.011108505 0.265557404 H -9.458508322 2.358916954 0.586189354 H 0.759012725 2.568601730-3.335037297 H 0.257053089 1.507276792-2.026149609 H -1.518418143 3.472893772-3.611972571 H -2.157863400 2.360222183-2.404760892 C -2.834840526 3.621089767-0.026514516 H -3.525164862 3.628478446-0.886252187 H -3.279772106 4.287337099 0.734241731
S18 Conformer #9 Energy: -1.4184 kcal/mol N -5.816638947 0.940245152 2.709200621 C -5.631164074-0.587442696 2.450974226 C -5.191511631-0.896903217 1.012976527 C -4.013268471-0.039463084 0.457915604 C -4.024842262 1.453037381 0.901972353 C -4.470769405 1.627116799 2.359855652 C -7.001121044 1.425814390 1.830854774 C -6.032414436 1.163575649 4.198987961 Cl -7.510132790 0.381912917 4.753116131 C -3.978240252-0.116680928-1.078320384 C -5.056265831 0.170262098-1.833136320 H -6.000119209 0.472255975-1.381112695 C -5.024476051 0.192832038-3.345426559 C -3.771660805-0.552554488-3.877398252 N -2.555765867-0.155679643-3.168596029 C -2.651391983-0.465650797-1.736654401 C -1.309996009-0.595804691-3.801955462 C -5.105372429 1.651630044-3.849539518 C -2.645303965 2.152878761 0.706936300 C -6.371741772 2.467787504-3.393883228 C -6.070267200 3.463253021-2.292191982 H -5.211317062 4.109151363-2.501623154 C -6.761076927 3.708352327-1.168101549 H -6.417539597 4.548107147-0.558334827 C -7.333492279 2.925870895 1.840975761 C -0.043319523 0.195756987-3.397853851 C -8.030551910 3.007322550-0.706004024 C -8.397929192 3.274470568 0.765221417 C 0.080423251 1.630361676-3.964200974 C -0.813014686 2.730930567-3.351752758 C -0.330422103 3.182174921-1.990921617 H 0.712397575 3.513536692-1.973957419 C -1.026178479 3.284200430-0.848029017 H -0.498979151 3.697183132 0.016548419 H -6.583033085-1.094509721 2.685831547 H -4.868523121-0.941071987 3.168125391 H -4.892373085-1.961448193 0.990597963 H -6.079621315-0.842518508 0.364021331 H -3.091273546-0.498913229 0.867815495 H -4.758471489 2.002897024 0.285829961 H -4.569413185 2.697318792 2.615299463 H -3.713725805 1.189178705 3.037615538 H -6.757342339 1.133589506 0.798275352 H -7.888952732 0.838562250 2.125726700 H -6.109835625 2.244948864 4.392690182 H -5.177076340 0.739187241 4.748926163 H -5.913218498-0.342946678-3.732013226 H -3.932359219-1.646113634-3.808736324 H -3.659460068-0.332564354-4.954521179 H -1.841789365 0.078765497-1.218857527 H -2.458460569-1.541467071-1.552519560 H -1.129459977-1.672927260-3.616360426 H -1.412619710-0.502925515-4.898669720 H -5.111783504 1.625111103-4.955626011 H -4.180686474 2.193438053-3.586454630 H -1.834536672 1.408860087 0.810755432 H -2.467148542 2.879078865 1.521397233 H -6.738021851 3.050328493-4.259527206 H -7.196568012 1.790971875-3.128430367 H -7.729050159 3.228152037 2.825818062 H -6.436688900 3.539526463 1.658533812 H 0.088610254 0.202164605-2.302543402 H 0.814587533-0.375341058-3.799133539 H -8.864878654 3.364010572-1.336701512 H -7.956483841 1.927459121-0.902647853 H -8.662659645 4.344330311 0.863095820 H -9.330278397 2.724173546 0.994425893 H -0.123904988 1.585484624-5.050499916 H 1.136973977 1.946181417-3.884907246 H -0.780560017 3.610955000-4.022091866 H -1.861937404 2.410934925-3.340513468 C -2.478928566 2.928652525-0.614989996 H -2.874505520 2.349560499-1.459372640 H -3.077290535 3.856431961-0.578137934
S19 Conformer #10 Energy: -1.3300 kcal/mol N -3.954247387 0.540007366 2.774810121 C -4.896426053-0.677939781 2.486281659 C -5.715807033-0.525968588 1.197933087 C -4.893394241-0.121487483-0.055321559 C -3.834416827 0.972133334 0.229102738 C -3.052748415 0.721741413 1.525794829 C -4.871552201 1.755040607 3.077330774 C -3.084404656 0.114370115 3.951999259 Cl -1.835854168 1.303060516 4.308543610 C -5.828938134 0.368145293-1.176982112 C -6.667903469 1.408084012-1.006509558 H -6.746931916 1.914778952-0.045315199 C -7.433998365 2.049785083-2.145758751 C -7.438972272 1.140750725-3.404535879 N -6.119391165 0.564838725-3.661042888 C -5.690262601-0.282801833-2.542259239 C -5.919895474 0.038956546-5.021026986 C -6.817363631 3.437825615-2.441179591 C -2.842084840 1.261673224-0.938901754 C -6.851318851 4.471008885-1.251574022 C -5.489163765 4.714866727-0.635690531 H -4.715297794 4.984790320-1.361538308 C -5.145094187 4.727080764 0.661393663 H -4.118104690 5.023091958 0.891229101 C -4.244786290 3.149881382 3.259603106 C -4.525034041-0.590317881-5.267868986 C -6.060230208 4.462811625 1.849208272 C -5.319007091 4.270121400 3.184153067 C -3.313585295 0.317252332-4.949011955 C -2.043803390-0.448005986-4.533348579 C -1.061088622 0.473029159-3.834962695 H -0.371266210 1.003876129-4.497544262 C -0.996339285 0.724476648-2.516327399 H -0.242108335 1.440845913-2.177214434 H -5.546663724-0.810105398 3.369491434 H -4.247483224-1.569343523 2.403804337 H -6.195685511-1.504559451 1.009646879 H -6.551734876 0.168414442 1.377199761 H -4.361302911-1.033960323-0.389579449 H -4.367335846 1.930482200 0.369546182 H -2.361856374 1.559485737 1.720658030 H -2.449377077-0.200590633 1.442491809 H -5.582768588 1.813552076 2.239923198 H -5.456045027 1.490580846 3.977372792 H -2.590547965-0.837204563 3.697183900 H -3.722450755-0.015182886 4.840578933 H -8.486502377 2.204698713-1.839773912 H -8.201747166 0.346163504-3.291317340 H -7.759577207 1.739477995-4.275966324 H -4.628825304-0.545197622-2.685430857 H -6.240761813-1.243907225-2.531887194 H -6.689506845-0.715510001-5.275598576 H -6.062211804 0.877005805-5.727543003 H -7.377730605 3.888595523-3.281824923 H -5.788067550 3.311951124-2.822993364 H -2.239666475 2.143600910-0.646003060 H -3.423649171 1.601548904-1.817290261 H -7.204557080 5.442598662-1.644130947 H -7.596660458 4.174852625-0.499380147 H -3.759245008 3.227863490 4.246989761 H -3.465021503 3.359026018 2.509899127 H -4.456040487-1.521041554-4.675566654 H -4.473079588-0.915861228-6.321535802 H -6.736109160 5.330226585 1.957379343 H -6.715831001 3.606576204 1.633970335 H -4.838748771 5.232008628 3.446647686 H -6.070467072 4.097569485 3.977810659 H -3.582719630 1.008679672-4.131569251 H -3.097807302 0.968969454-5.813436169 H -2.314773613-1.279667306-3.865598103 H -1.560413442-0.913004286-5.412271406 C -1.878141521 0.159755573-1.415851305 H -1.227145280-0.197594568-0.597951853 H -2.441637881-0.716034381-1.766412034
S20 Conformer #11 Energy: -1.0352 kcal/mol N -5.570820332 1.078799486 2.585088730 C -5.619997025-0.480367929 2.557875395 C -5.298989296-1.076636672 1.179178834 C -4.039965153-0.506749690 0.439770192 C -3.735951424 1.007131100 0.731676221 C -4.149529457 1.487783670 2.131490231 C -6.689269066 1.620693445 1.656405807 C -5.710894108 1.541912317 4.028487682 Cl -7.283287525 1.099544048 4.687088490 C -4.151031971-0.690253794-1.090609312 C -5.281524181-0.399131149-1.771517873 H -6.178788185-0.075884886-1.249707818 C -5.391356945-0.357374877-3.289292097 C -4.096667767-0.891546309-3.951076269 N -2.848090410-0.581608891-3.256933928 C -2.915623665-1.119131327-1.882539511 C -2.363627195 0.800492167-3.383168936 C -5.753637314 1.094137669-3.714129210 C -2.237036705 1.354638219 0.521173239 C -7.190171719 1.533264518-3.346493721 C -7.364275455 3.043658733-3.347219467 H -7.758404255 3.472782373-4.272965431 C -7.095265388 3.867210865-2.318983555 H -7.293416023 4.934921741-2.450267315 C -6.864359379 3.154941082 1.548149109 C -0.830015361 0.924765468-3.252122641 C -6.476209164 3.472643375-0.993616641 C -7.463049412 3.578325748 0.182212159 C -0.298631847 2.355757713-3.494872570 C -0.674900532 3.410974026-2.429758787 C 0.085737012 3.207967997-1.137828708 H 1.173543692 3.263827324-1.245810032 C -0.402896047 2.972697973 0.090326883 H 0.317621738 2.828674316 0.901024461 H -6.623475552-0.799480736 2.889136076 H -4.886367321-0.831823707 3.305923462 H -5.150961399-2.162255526 1.329895377 H -6.214003086-1.005256414 0.573238313 H -3.180989504-1.097349644 0.815752208 H -4.306360245 1.613200068 0.006168829 H -4.083189011 2.587217331 2.200631380 H -3.456651688 1.064114332 2.883166075 H -6.478426933 1.205866694 0.659131527 H -7.638924599 1.162000537 1.984640121 H -5.608126640 2.637885809 4.065672398 H -4.923024178 1.065528274 4.633785248 H -6.218874931-1.014460206-3.619924784 H -4.165718079-1.994184494-4.011210442 H -4.033253670-0.555833697-5.001824856 H -1.977189541-0.892179608-1.353519559 H -2.932109833-2.222052336-1.961158156 H -2.633032799 1.180222511-4.385286808 H -2.860007763 1.475138903-2.663275957 H -5.636985779 1.203887105-4.807809353 H -5.020153046 1.790768981-3.273184776 H -1.907741427 0.945727468-0.446332246 H -1.625979781 0.832683146 1.280702472 H -7.911184311 1.085234165-4.056280613 H -7.485564709 1.154398322-2.358042717 H -7.533280849 3.497291088 2.357089996 H -5.920960903 3.708684921 1.684669614 H -0.489348441 0.563430607-2.266820431 H -0.367653310 0.249070272-3.996227980 H -6.074420929 2.454399109-1.068746924 H -5.603919983 4.129045963-0.811553776 H -7.809729576 4.626224995 0.252063215 H -8.367868423 2.978804111-0.027687270 H -0.670034587 2.698893785-4.478600025 H 0.801530480 2.321678877-3.595963955 H -0.419111997 4.415593624-2.817385674 H -1.762661219 3.419640303-2.276329756 C -1.860188127 2.844097853 0.490783960 H -2.507176638 3.377278805-0.222464606 H -2.003180981 3.335625172 1.469531417
S21 Conformer #12 Energy: -0.9011 kcal/mol N -4.661044161 0.711867715 2.766943063 C -5.068446187-0.733831992 2.336976630 C -5.459470261-0.837385457 0.854751141 C -4.446690671-0.216601832-0.148229410 C -3.906015742 1.157187038 0.324906742 C -3.531830650 1.170825314 1.813093941 C -5.925507342 1.614545896 2.695801500 C -4.039838297 0.635556892 4.156544727 Cl -5.210103919 0.081223866 5.350330247 C -5.084214709-0.035829694-1.540340121 C -6.245015814 0.626493274-1.715898840 H -6.812558344 0.995720372-0.862545406 C -6.731647494 1.103136606-3.073505655 C -5.993641142 0.370934679-4.224145740 N -4.555443500 0.264851985-3.985824921 C -4.275930828-0.478733469-2.750484098 C -3.778698453-0.111702950-5.179239789 C -6.530586724 2.642972713-3.104799914 C -2.724016647 1.759178098-0.495707168 C -7.513191581 3.442715900-2.191274996 C -6.881371895 4.692228819-1.617633086 H -6.606149087 5.443200211-2.365067162 C -6.658482764 4.993965479-0.326790056 H -6.231822468 5.980050644-0.117050439 C -5.745460852 3.124465952 3.015874065 C -2.260345018-0.297173941-4.935871863 C -6.949951719 4.153731925 0.901928567 C -5.704046872 4.096141680 1.808515360 C -1.530700501 0.915967646-4.315859838 C -0.291835901 0.548033279-3.478619857 C 0.087441370 1.686110065-2.550071101 H 0.770530213 2.426797113-2.975857094 C -0.373470617 1.885604983-1.303720465 H -0.025464738 2.778063165-0.775318632 H -5.900101689-1.061044287 2.984979152 H -4.198267106-1.383728874 2.541717750 H -5.571069101-1.915040318 0.632334856 H -6.469160772-0.416872072 0.730041340 H -3.597129465-0.924011557-0.219628148 H -4.724405785 1.887729259 0.191278808 H -3.222195596 2.181954043 2.132709522 H -2.681037088 0.487129915 1.990009151 H -6.351488798 1.489978973 1.689133327 H -6.659470244 1.174596834 3.393578507 H -3.678732197 1.632833483 4.450392871 H -3.197732741-0.074850683 4.128661146 H -7.811871440 0.890448180-3.186817588 H -6.444061214-0.630397306-4.370221980 H -6.171500285 0.919013049-5.167095501 H -3.206004020-0.363702708-2.510327804 H -4.436226363-1.565448912-2.893646497 H -4.169013830-1.045053698-5.630165952 H -3.923722259 0.680940089-5.935994791 H -6.646794705 3.022007551-4.136317391 H -5.479912056 2.860205210-2.837312346 H -2.556586103 2.785506708-0.114137835 H -3.054474214 1.905593481-1.541319410 H -8.400726192 3.735070700-2.783056718 H -7.908743309 2.807315456-1.388625808 H -6.607431663 3.413130061 3.646773439 H -4.862909109 3.325739701 3.645232146 H -2.118379464-1.184549744-4.292383540 H -1.785658641-0.559291254-5.897588674 H -7.795094634 4.605335868 1.453104966 H -7.276136805 3.145833743 0.615645777 H -4.816182293 3.870933185 1.192146278 H -5.527584507 5.114567923 2.204876879 H -2.234750674 1.468597901-3.670060308 H -1.252770339 1.630702079-5.109884716 H -0.497113173-0.359109890-2.890365322 H 0.563294569 0.295658864-4.132305598 C -1.366117865 1.033341667-0.531151169 H -0.959895198 0.867224557 0.482471431 H -1.477082273 0.038112929-0.983927705
S22 Conformer #13 Energy: -0.6431 kcal/mol N -4.227087975 0.531259179 2.735129833 C -5.205648422-0.671129107 2.547137737 C -5.886264801-0.675343692 1.170488358 C -4.919807911-0.503564358-0.031546999 C -3.824945450 0.577454269 0.186298296 C -3.190992117 0.482519269 1.577763200 C -5.075440884 1.832244158 2.740516186 C -3.434313059 0.319117010 4.017184734 Cl -4.490306854 0.305317014 5.426724911 C -5.672304153-0.156762972-1.324715376 C -6.513108253 0.895554662-1.398569822 H -6.777351856 1.464629769-0.507569134 C -6.935355663 1.528689265-2.713973045 C -6.613949299 0.607627571-3.923734188 N -5.290182590-0.001515309-3.784590244 C -5.248476028-0.867244899-2.602068901 C -4.617389679-0.492275506-5.002134800 C -6.188141823 2.882971525-2.821769953 C -2.751615047 0.559966266-0.948054194 C -6.575263977 3.979214191-1.759491563 C -5.352736950 4.587347031-1.102626681 H -4.590422630 4.929767132-1.810140133 C -5.127089024 4.820479870 0.200053096 H -4.205083847 5.354384422 0.448366761 C -4.331988811 3.174348593 2.829332352 C -3.772431374 0.620802999-5.669265747 C -6.057146549 4.532822132 1.366568089 C -5.321877480 4.362898350 2.710819721 C -2.733429432 1.355889916-4.787299156 C -1.681249022 0.509910226-4.051077843 C -0.736837566 1.421471357-3.293070793 H 0.048590790 1.834099770-3.937175512 C -0.712018430 1.820100784-2.008423805 H 0.098622963 2.511347771-1.742271185 H -5.954454899-0.632365882 3.357115984 H -4.607847691-1.591499090 2.676583052 H -6.408795834-1.645302653 1.074549675 H -6.687446117 0.079719447 1.168157578 H -4.405445099-1.478148937-0.156312719 H -4.299412251 1.573965549 0.118088491 H -2.470865726 1.299432516 1.756606936 H -2.646666527-0.474572957 1.681902885 H -5.664571762 1.823705554 1.810589194 H -5.796521664 1.745312452 3.572910547 H -2.705447435 1.137100339 4.128796101 H -2.911503792-0.648844302 3.954351425 H -8.024176598 1.724279284-2.709382296 H -7.397400379-0.166910112-4.031781197 H -6.659103394 1.205086589-4.851226807 H -4.219068527-1.251328349-2.490434647 H -5.881848812-1.765204787-2.739659309 H -3.945224762-1.330111146-4.752718925 H -5.333684444-0.899139822-5.738586903 H -6.358486176 3.317662954-3.823853493 H -5.103068352 2.677298546-2.785140038 H -3.280543089 0.794296026-1.886220574 H -2.338088989-0.457573473-1.062144756 H -7.128296852 4.788513660-2.269714832 H -7.275936604 3.584434271-1.011692643 H -3.804434776 3.262875080 3.794248343 H -3.570259094 3.267916441 2.038191080 H -3.254653215 0.174226478-6.536684036 H -4.454013824 1.386126757-6.085993290 H -6.747534752 5.391199112 1.463105440 H -6.696224689 3.664487839 1.152151227 H -4.781867981 5.303843498 2.928178787 H -6.078629017 4.275238991 3.513664484 H -3.277747869 1.962828279-4.042516232 H -2.211146593 2.085254908-5.434338093 H -2.161933184-0.231763870-3.402215958 H -1.084171295-0.074849397-4.776902199 C -1.599087358 1.567042589-0.806207955 H -2.010265589 2.555444241-0.523746669 H -0.923655212 1.259390473 0.013976694
S23 Conformer #14 Energy: -0.5885 kcal/mol N -5.790727615 1.068593621 2.401007652 C -5.711664200-0.489737481 2.356803179 C -5.275097370-1.031669497 0.988971472 C -4.000541687-0.374753028 0.374747902 C -3.871203899 1.166056395 0.641337991 C -4.398318291 1.613559604 2.011551380 C -6.918179512 1.523360729 1.436665773 C -6.020535469 1.493312597 3.846534014 Cl -7.576972485 0.921483994 4.440534115 C -3.931746721-0.596951067-1.149218917 C -4.985145092-0.335181981-1.954471707 H -5.949895859-0.040393975-1.544642925 C -4.879321098-0.193166956-3.466596603 C -3.509917021-0.689168096-4.001338005 N -2.436896563-0.258083344-3.104278088 C -2.588080645-0.921291530-1.798412919 C -1.082732797-0.033979610-3.630327225 C -5.096245766 1.309906125-3.789181948 C -2.399592638 1.647216797 0.513562381 C -6.548716068 1.856291771-3.563150644 C -6.538228512 3.219649792-2.904998302 H -5.884561062 3.950031519-3.392827988 C -7.266897202 3.648110628-1.862323880 H -7.164345741 4.703622818-1.592518687 C -7.171411991 3.033285141 1.297786593 C -0.382364362 1.157034755-2.923040152 C -8.307963371 2.873361588-1.076339006 C -8.403391838 3.310240984 0.398343205 C -1.191161633 2.476340532-2.941297770 C -0.499918163 3.700299263-2.329098940 C 0.050120365 3.539969206-0.917916894 H 1.141097426 3.616834402-0.863212824 C -0.621868551 3.328438044 0.224911630 H -0.032271288 3.227972031 1.141152501 H -6.701624870-0.890821874 2.635466099 H -4.987960815-0.793232679 3.134863853 H -5.084413052-2.113081694 1.120700479 H -6.141920090-0.981301486 0.313304186 H -3.138213873-0.872438490 0.861548066 H -4.464925766 1.699202180-0.124511339 H -4.445910454 2.715095043 2.072476149 H -3.703703165 1.264218807 2.798969507 H -6.661983013 1.122932553 0.442727685 H -7.842228889 1.013118386 1.762781501 H -5.999765873 2.592542410 3.908006191 H -5.221388817 1.065641880 4.473313808 H -5.677995682-0.779407918-3.958629131 H -3.513226032-1.789431334-4.119135380 H -3.354647398-0.285947353-5.016871452 H -1.748501182-0.647482395-1.141276121 H -2.503220320-2.020605326-1.903422236 H -0.455548137-0.941808701-3.562156439 H -1.147775888 0.207630306-4.705248356 H -4.830576897 1.507335544-4.843963146 H -4.364903927 1.893739343-3.201208115 H -1.960208297 1.215220094-0.397024691 H -1.809282899 1.221407056 1.346724510 H -7.054753304 1.942970276-4.541711807 H -7.157423973 1.144743443-2.990013838 H -7.366789341 3.496649265 2.279361010 H -6.289841175 3.541133165 0.872302234 H -0.149232283 0.882517695-1.879287720 H 0.592786193 1.321248651-3.415062428 H -9.289652824 3.059036970-1.551184893 H -8.143529892 1.789496422-1.153247237 H -8.635499001 4.391678810 0.426289469 H -9.285313606 2.817301989 0.850441635 H -2.157872200 2.318055153-2.435893536 H -1.443750501 2.722013235-3.989769220 H 0.348457336 3.997122049-2.976283550 H -1.199181437 4.552723885-2.347006083 C -2.118196249 3.154322624 0.405592263 H -2.668691874 3.578459501-0.448474675 H -2.439309835 3.716018200 1.300302029
S24 Conformer #15 Energy: -0.5411 kcal/mol N -4.026428699 0.158735111 2.221339464 C -5.284429073-0.738104641 2.263434887 C -5.895478725-1.173352718 0.902648866 C -5.181733608-0.803472877-0.469176650 C -3.638155222-0.372067720-0.309966266 C -3.084625244-0.392407775 1.126469016 C -4.481655598 1.615456581 1.963349462 C -3.280101061 0.004391208 3.541750193 Cl -4.279232025 0.521666586 4.897331238 C -5.906094074 0.230862632-1.327608943 C -6.871363163 1.084857464-0.920541942 H -7.240420818 1.092207313 0.104618393 C -7.459482670 2.168460846-1.821604848 C -7.092325211 1.939562082-3.311963797 N -5.684426308 1.580283284-3.444663048 C -5.449056149 0.293105751-2.785344839 C -5.101245880 1.764837503-4.779628277 C -6.967668533 3.564872265-1.362989902 C -2.673798323-1.186696529-1.214126945 C -7.435775280 4.055233955 0.019900899 C -6.818759918 5.409193993 0.311709106 H -7.209680557 6.232022285-0.294665843 C -5.839481831 5.681809902 1.190031767 H -5.469728470 6.709328651 1.253254890 C -3.403461456 2.716446161 1.966576338 C -3.596832752 1.394344568-4.897486210 C -5.151568890 4.672130585 2.091913462 C -3.966637611 4.020219803 1.356825709 C -2.647753000 2.056263924-3.871271849 C -1.173092365 1.647820234-3.987668991 C -0.897807777 0.149347678-4.014268875 H -0.621628106-0.230692700-5.003370762 C -0.942871571-0.726878285-2.997187138 H -0.698795497-1.769432902-3.222526550 H -6.041963577-0.224547014 2.880398273 H -5.001557827-1.655625463 2.811293125 H -5.904661179-2.279773474 0.928494215 H -6.965251923-0.906858325 0.889091611 H -5.218330860-1.741329908-1.060213447 H -3.565808773 0.679947257-0.645761549 H -2.140809774 0.178957626 1.177336931 H -2.859923601-1.434300423 1.423526168 H -4.990853786 1.611894488 0.986104786 H -5.249040604 1.847784162 2.722290993 H -2.368014574 0.621136725 3.515164137 H -3.013706684-1.056015134 3.679612160 H -8.563163757 2.147878885-1.739867687 H -7.746472359 1.164563775-3.756575108 H -7.304263592 2.863507986-3.879334211 H -4.371836185 0.089040786-2.830249548 H -5.930522442-0.536346018-3.340646267 H -5.658404350 1.191627145-5.546311855 H -5.218050957 2.831019878-5.047629833 H -7.298935890 4.311900616-2.109142065 H -5.863693237 3.581685066-1.404695988 H -3.184377909-1.451012015-2.158096313 H -2.449559689-2.166118622-0.754197001 H -8.537808418 4.147790909 0.039493464 H -7.176102161 3.322225571 0.794481456 H -3.048362255 2.912757874 2.992062092 H -2.522669792 2.424736023 1.370684862 H -3.492021561 0.295810819-4.838582993 H -3.269284487 1.665923119-5.917331219 H -4.805113316 5.177094936 3.013146639 H -5.888262749 3.926803589 2.421863794 H -4.256386757 3.800369740 0.312013686 H -3.158587456 4.771397591 1.278023958 H -2.996757984 1.845323443-2.847270966 H -2.712301493 3.154554844-3.982437611 H -0.747122288 2.074392080-4.916712284 H -0.605106771 2.109145164-3.163486958 C -1.338919163-0.452753901-1.562690020 H -1.443281889 0.632140696-1.411249876 H -0.522885263-0.774957061-0.891968131
S25 Conformer #16 Energy: -0.5287 kcal/mol N -3.789376734 0.392560654 2.276277751 C -5.089394389-0.428208285 2.442482238 C -5.769120587-0.932894239 1.140016771 C -5.146489899-0.596280938-0.280897275 C -3.570096087-0.275792412-0.234524348 C -2.938201562-0.276840079 1.168098674 C -4.197125888 1.850834963 1.951223888 C -2.976000172 0.284368912 3.560224761 Cl -3.874936456 0.921734468 4.934677458 C -5.876222012 0.456890676-1.107450796 C -6.867711201 1.270035343-0.686362895 H -7.228758508 1.262688480 0.341841013 C -7.527601509 2.295180297-1.601634347 C -7.333513184 1.903569949-3.090546101 N -5.924191040 1.650958102-3.371044120 C -5.417706821 0.539309404-2.565820726 C -5.538402212 1.662357649-4.787712327 C -6.966163462 3.708906207-1.317763565 C -2.771161051-1.211436831-1.180931444 C -7.255836905 4.305420694 0.072977520 C -6.539590070 5.634266266 0.212581349 H -6.937911327 6.437603195-0.414803603 C -5.469604199 5.904638944 0.978952788 H -5.040815849 6.909980865 0.933172364 C -3.082850437 2.901501505 1.786086027 C -4.014532458 1.742741439-5.046015226 C -4.757305589 4.923225703 1.892945025 C -3.654679250 4.175885952 1.121246112 C -3.209875736 0.414143053-4.982970793 C -1.774308292 0.583953607-4.449210761 C -1.135924196-0.755517971-4.135960990 H -0.820391824-1.327823255-5.013582231 C -0.955963154-1.308826174-2.923265049 H -0.509905545-2.306632891-2.878428078 H -5.792682341 0.178017857 3.039196116 H -4.837070126-1.312171472 3.056154318 H -5.736263982-2.037654109 1.201596842 H -6.846201325-0.700955349 1.183406793 H -5.282156313-1.534886221-0.857576901 H -3.426306293 0.752520716-0.615908080 H -1.958474355 0.232426753 1.145141430 H -2.767708590-1.315840662 1.507297682 H -4.788102233 1.807195185 1.022456796 H -4.887515489 2.171821845 2.750848646 H -2.043797313 0.859601535 3.445791996 H -2.744720328-0.776712863 3.747285544 H -8.616927164 2.306090123-1.403833944 H -7.959250398 1.025797931-3.343457030 H -7.701228406 2.728425234-3.726876674 H -4.320502527 0.633399721-2.570637612 H -5.659753602-0.430802312-3.044376089 H -5.970229597 0.804312869-5.338417538 H -5.987843965 2.565158201-5.241567842 H -7.370747635 4.405643509-2.075917847 H -5.873931348 3.696699273-1.485855787 H -3.357856242-1.347963536-2.109137489 H -2.697713346-2.225181976-0.747362252 H -8.342815069 4.461728143 0.203781560 H -6.950414186 3.602418531 0.858868653 H -2.640465268 3.159939112 2.762662644 H -2.262944115 2.531356248 1.148363771 H -3.860040130 2.172059255-6.052063707 H -3.590432965 2.484293846-4.344958328 H -4.325749912 5.469728883 2.752540420 H -5.495616223 4.231970637 2.321825116 H -4.036179646 3.888501161 0.122894604 H -2.834017814 4.889750069 0.920589670 H -3.177603737-0.030405604-5.993668851 H -3.734061619-0.336479958-4.371040657 H -1.152289685 1.122592072-5.188276179 H -1.797563530 1.223208412-3.554842626 C -1.364285512-0.712636266-1.586405035 H -1.358150101 0.385470800-1.654035831 H -0.608084756-0.971104426-0.823361476