Ferromagnetic Coupling in Copper Benzimidazole Chloride: Structural, Mass Spectrometry, Magnetism, and DFT Studies
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Ferromagnetic Coupling in Copper Benzimidazole Chloride: Structural, Mass Spectrometry, Magnetism, and DFT Studies Xing-Xing Shi, +,a Yuexing Zhang, +,b Qiu-Jie Chen, +,b Zheng Yin, c Xue-Li Chen, b Zhenxing Wang, d Zhong-Wen Ouyang, d Mohamedally Kurmoo, e Ming-Hua Zeng *,a,b a Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, , P. R. China. b Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University, Wuhan , P. R. China. c College of Chemistry and Chemical Engineering Shaanxi University of Science and Technology, Xi an, , P. R. China. d Wuhan National High Magnetic Field Center & School of Physics, Huazhong University of Science and Technology, Wuhan, , P. R. China. e Institut de Chimie de Strasbourg, CNRS-UMR 7177, Université de Strasbourg, Strasbourg, France.
2 Figure S1. The synthesis procedure and photograph of CBC crystals. Figure S2. (Left) TGA of CBC. There is no weight loss until a turning point at nearly 175 C, suggesting no solvent in the structure of CBC. The first weight loss of 50.9% from 175 C to 370 C corresponds to the departure decomposition of the Hmbm ligand (Calc. 54.6%). The residue may be CuO with residuals of 28.7% (Calc %). (Right) Experimental and simulated PXRD patterns for CBC. S1
3 Table S1. Crystal and structure refinement data for CBC at 296 and 90 K. CBC (296 K) CBC (90 K) Formula C 9 H 10 Cl 2 CuN 2 O C 9 H 10 Cl 2 CuN 2 O Weight Crystal System monoclinic monoclinic Space Group P 2 1 /n P 2 1 /n a (Å) 9.752(3) 9.723(3) b (Å) 7.817(2) 7.711(3) c (Å) (4) (5) β ( ) (3) (4) V (Å 3 ) (5) (6) Z 4 4 D c (g cm 3 ) F (000) μ (mm 1 ) Reflection collected Unique Reflection R int R 1a, wr 2 b [I > 2σ(I)] / / R 1, wr 2 (all data) / / GOF H-atom treatment refall refall Δρ max, Δρ min, (e Å 3 ) 0.311, , a R 1 =Σ F o - F c /Σ F o, b wr 2 =[Σw(F o2 -F c2 ) 2 /Σw(F o2 ) 2 ] 1/2. S2
4 Table S2. Cell parameters, selected bond lengths (Å) and angles ( ) for CBC at 296 and 90 K. CBC(296 K) CBC(90 K) Max. deviation a a / Å 9.752(3) 9.723(3) 0.30% b / Å 7.817(2) 7.711(3) 1.36% c / Å (4) (5) 0.82% β ( ) (3) (4) -0.23% V / Å (5) (6) 2.53% Cu(1)-N(1) 1.970(12) 1.969(18) 0.05% Cu(1)-Cl(1) 2.251(6) 2.253(6) -0.09% Cu(1)-O(1) 2.071(12) 2.062(16) 0.43% Cu(1)-Cl(2) 2.225(6) 2.228(6) -0.13% Cu Cl 2.998(8) 2.948(6) 1.67% Cu Cu 4.581(9) 4.543(4) 0.83% N(1)-Cu(1)-O(1) 80.58(5) 80.86(7) -0.35% O(1)-Cu(1)-Cl(1) (4) (5) 0.28% O(1)-Cu(1)-Cl(2) 86.95(4) 86.88(5) 0.08% C(8)-O(1)-Cu(1) (9) (13) 0.06% C(2)-N(1)-Cu(1) (10) (15) 0.15% N(1)-Cu(1)-Cl(1) (4) 99.81(5) 0.27% N(1)-Cu(1)-Cl(2) (4) (6) -0.31% Cl(2)-Cu(1)-Cl(1) 94.45(2) 94.33(2) 0.13% Cu(1)-O(1)-H(1) 110.7(16) 109.0(2) 1.5% C(3)-N(1)-Cu(1) (10) (15) -0.11% Cu(1)-Cl(1) Cu (8) (6) -0.24% a Max. deviation = [CBC(296 K)-CBC(90 K)]/Max.{CBC(296 K), CBC(90 K)} S3
5 Table S3. The CShM values calculated by SHAPE 2.0 for CBC. 4_Coordination a A regular polyhedron with one or two vertices removed. CBC_90 K CBC_296 K Ideal structures Square Tetrahedron Seesaw or sawhorse a (cisdivacant octahedron) S4
6 Table S4 Calculated complexation energies without and after basis set superposition errors correction (BSSE) (CE and CE-BSSE, in kcal/mol) between CBC monomer and its all possible neighbors in CBC crystals, the magnetic interaction J between Cu atoms in some dimers are also given. Interaction schemes of negative complexation energy smaller than -4 kcal/mol and positive complexation energy are not given. Method CE CE-BSSE J /cm -1 Interaction Types and Scheme dimer67_14 dimer38_14 dimer64_14 B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP LC-BLYP/(6-311G*,SDD) LC-BLYP/TZVP B97XD/(6-311G*,SDD) B97XD/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP PhC 3 N 2 PhC 3 N 2 (3.525, 3.339) Cl1a H-O1 (3.094), Cl2a Cu1 (2.998) 2 PhC 3 N 2 CH 3 (3.516) S5
7 B97D-D3/(6-311G*,SDD) dimer58_14 dimer95_14 dimer47_14 dimer94_14 B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP LC-BLYP/(6-311G*,SDD) LC-BLYP/TZVP Cl2a CH 2 (4.799) Cl1a C(Me) H(3.774) Cl1a CH 2 (3.843) S6
8 B97XD/(6-311G*,SDD) B97XD/TZVP B3LYP-D3/(6-311G*,SDD) dimer50_14 Cl1a_Cu B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP Cl2a_Cu CuCl2_L B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP B3LYP-D3/(6-311G*,SDD) B3LYP-D3/TZVP B97D-D3/(6-311G*,SDD) B97D-D3/TZVP CuCl2_CuCl2L B3LYP-D3/(6-311G*,SDD) S7
9 CuCl2movingCl_Cu Cl2L B3LYP-D3/(6-311G*,SDD) CuCl_CuCl2L B3LYP-D3/(6-311G*,SDD) CuCl2LmovingCl_C ucl2lmovingcl B3LYP-D3/(6-311G*,SDD) CuClL_CuClL B3LYP-D3/(6-311G*,SDD) L_CuCl2LmovingCl B3LYP-D3/(6-311G*,SDD) L_L B3LYP-D3/(6-311G*,SDD) S8
10 Table S5. Bond order analysis of CBC. Atomic labels are shown below the table. Bond length Mayer bond order analysis Wiberg bond order analysis in Lowdin orthogonalized basis Fuzzy bond order analysis Laplacian bond order Cu1-Cl Cu1-Cl Cu1-N Cu1-O Cu26-Cl Cu26-Cl Cu26-N Cu26-O Cl3 Cu Cl2 H S9
11 Table S6. List of H-bonds, C H π and π π interactions for CBC. H-bond Distance a, Å Distance b, Å Angle e, Complexation energy f, kcal/mol Cu1 Cl2a Cu 2.998(8) 2.998(8) (19) O1 H Cl1a i 3.094(14) 2.304(23) (21) C-H Cl2a ii 4.799(17) 3.865(18) (17) /2 π π g Distance c, Å Distance d, Å PhC 3 N 2 PhC 3 N (7) 3.339(6) C(Me)-H π Distance c, Å Distance b, Å Angle e, C(Me)-H π(phc 3 N 2 ) 3.516(24) 3.018(25) (16) /2 Symmetric code: i) 1-x, -y, -z; ii) 1-x, -y, 1-z. a Distance between acceptor and donor; b Distance between acceptor and H; c Centroid-to- centroid distance; d Interplanar distance; e Angle of acceptor-hydrogen-donor; f Complexation energies were calculated using B3LYP functional with BSSE correction; g the interaction between two CBC molecules infact including other types of interaction involving Cu π and Cl CH(Ph). Figure S3. View of the 3D packing structure of CBC along the b axis. S10
12 Figure S4. Intermolecular interactions in the structure of CBC. (a) π(phc 3 N 2 ) π(phc 3 N 2 ) (dark dotted line); (b) Cu1 Cl2a (light orange dotted line); H1 Cl1a (indigo red dotted line); (c) C H π(phc 3 N 2 ) (pink dotted line) ; (d) H1B Cl2a (bright green dotted line), E is calculated complexation energy between different CBC. Figure S5. The positive mode (left) and negative mode (right) ESI-MS of CBC for different insource energies of 0, 20, 40 and 100 ev. The crystals were dissolved in DMSO and diluted by CH 3 CN for ESI-MS measurements. S11
13 Table S7. Peak assignments, relative intensity and R deviation of the ESI-MS spectrum of CBC under different in-source energy. m/z of the peak Fragment Positive Mode 0eV (R) Relative Intensity / R a (%) 20eV 40eV 100eV [(Hmbc)+H] + (161.07) (0.2) [Hmbm+H] + (163.09) 100 (0.63) [Cu I (DMSO)(CH 3 CN)] + (181.97) (4.27) [Cu II (OH)(DMSO) 2 ] + (236.00) (10.33) [Cu I (mbm)(ch 3 CN)+H] + (266.04) (0.89) [Cu II (mbm)(dmso)] + (302.02) 22.7 (3.28) [Cu I (mbm)(dmso)+h] + (303.02) (4.73) [Cu II (mbm)cl(dmso)+h] + (337.99) 10.1 (1.39) [Cu I (mbm)(dmso)(ch 3 CN) 2 +H] + (385.08) (3.28) [Cu II (mbm)(hmbm)] + (386.08) (2.21) [Cu II 2(mbm) 2 Cl] + (484.97) (5.58) [Cu II 2(mbm) 3 ] + (609.07) (1.40) [Cu II 3(mbm) 3 Cl 2 ] + (743.94) (7.52) [Cu II 4(mbm) 3 Cl 4 ] + (878.80) (10.54) [Cu II 4(mbm) 4 Cl 3 ] + ( ) (7.27) [Cu II 5(mbm) 4 Cl 5 ] + ( ) (35.10) Negative Mode [Cu II Cl 3 ] - (169.83) 100 (1.69) (1.13) [Cu I 2Cl 3 ] - (232.76) (3.62) [Cu I Cu II Cl 4 ] - (267.73) (3.28) [Cu II 2Cl 5 ] - (304.69) (4.53) [Cu I Cu II 2Cl 6 ] - (402.60) (9.92) [Cu II 3Cl 7 ] - (437.56) (14.79) [Cu I Cu II 2Cl 6 (CH 3 CN) 2 (H 2 O) 2 ] - (520.67) (21.36) [Cu II 4Cl 9 ] - (572.43) (12.36) [Cu I Cu II 3Cl 8 (CH 3 CN) 2 (H 2 O) 2 ] - (655.56) (24.52) a R is a convenient index of the match between the observed and calculated MS data. R factor was defined as R = (Σ{ Iobs Ical / Ical})/100. Iobs and Ical are the observed and calculated intensity of each single peak at m/z, respectively. 1 [1] S. A. R. Knox, J. W. Koepke, M. A. Andrews, H. D. Kaesz, J. Am. Chem. Soc. 1975, 97, (R) S12
14 S13
15 Figure S6. The experimental and calculated MS spectra of different fragments. S14
16 Table S8. Hirshfeld surfaces mapped with d norm (left) showing Shape-index (middle) and Curvedness (right) for the CBC. Hirshfeld surface analysis were performed using CrystalExplorer (Version 3.1), S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, University of Western Australia, d norm Shape Index Curvedness 90K or 296K 296K S15
17 Table S9. Fingerprint plot for different interactions for CBC showing the percentage of contacts created to the total Hirshfeld surface area of the CBC molecules. d i is the closest internal distance from a given point on the Hirshfeld surface; d e is the closest external contact. Inside + outside 90K 296K All All H H 90K: 35.6% 296K: 32.4% Cl H 90K: 36.6% 296K: 33.6% O H 90K: 3.9% 296K: 3.5% N H 90K: 2.2% 296K: 2.1% S16
18 Cu H 90K: 2.1% 296K: 2.1% C H 90K: 12.1% 296K: 10.9% Cu All 90K: 2.9% 296K: 2.6% Cu Cl 90K: 1.6% 296K: 2.9% S17
19 Table S10. Calculated orbitals energy for MS fragments CuL 2 (7), Cu 2 L 2 Cl (8), Cu 2 L 3 (9), and Cu 4 L 4 Cl 3 (10). Compound HOMO / a.u. LUMO / a.u. Picture Energe / a.u. Alpha Alpha CuL 2 (7) Beta Beta Cu 2 L 2 Cl(8) Alpha Beta Alpha Beta Cu 2 L 3 (9) Alpha Beta Alpha Beta Cu 4 L 4 Cl 3 (10) Alpha Beta Alpha Beta Table S11. Selected bond lengths (Å) and angles ( ) for the optimized MS fragments MS fragments CuL 2 (7), Cu 2 L 2 Cl (8), Cu 2 L 3 (9), and Cu 4 L 4 Cl 3 (10). CuL 2 (7) Cu23-O Cu23-O Cu23-N Cu23-N O40-Cu23-N O40-Cu23-N O17-Cu23-N O17-Cu23-N S18
20 Cu 2 L 2 Cl (8) Cu22-O Cu22-O Cu22-N Cu44-O Cu44-O Cu44-N Cu44-Cl O17-Cu22-N O89-Cu22-O Cl45-Cu44-O Cl45-Cu44-N O17-Cu44-O O89-Cu44-N Cu 2 L 3 (9) Cu22-O Cu22-O Cu22-N Cu22-N Cu44-O Cu44-O Cu44-N Cu44-O N60-Cu22-N N60-Cu22-O O61-Cu22-O N16-Cu22-O O61-Cu44-O O61-Cu44-N N38-Cu44-O O17-Cu44-O Cu 4 L 4 Cl 3 (10) Cu22-N Cu22-Cl Cu22-O Cu22-O Cu44-O Cu44-Cl Cu44-O Cu44-O Cu44-N S19
21 Cu67-N Cu67-O Cu67-O Cu67-Cl Cu67-O Cu89-O Cu89-Cl Cu89-N Cu89-O Cu89-Cl N16-Cu22-Cl Cl91-Cu22-O N16-Cu22-O O17-Cu22-O O17-Cu44-O N38-Cu44-O O17-Cu44-Cl N38-Cu44-Cl O39-Cu44-O O84-Cu44-Cl N61-Cu67-O O62-Cu67-O N61-Cu67-Cl O84-Cu67-Cl Cl91-Cu67-O O17-Cu67-O O62-Cu89-O N83-Cu89-O O62-Cu89-Cl N83-Cu89-Cl Cl45-Cu89-Cl Cl45-Cu89-O T (cm 3 K / mol) Temperature (K) Figure S7. Temperature dependence of χ m T for CBC in a static field of 1 koe. Figure S8. (Left) The FC-ZFC magnetic susceptibility of CBC. (Right) The temperature dependence of ac magnetic susceptibility of CBC. S20
22 Figure S9. The isothermal magnetization of CBC at 2 K. The red line corresponds to the simulation employing the Brillouin function for S = 1/2 with the g-values from HF-EPR (g x = 2.24, g y = 2.16, and g z = 2.09). Figure S10. View of J value vs Cl2a Cu1 distance. The J value increases with decreased Cl2a Cu1 distance. S21
23 Table S12. Examine part of the literatures about magnetic exchange via weak interaction. (F = Ferromagnetic, AF = Antiferromagnetic, BS = broken-symmetry). No. Compound M M distance / Å Magnetic Exchange Pathway Magnetism Theoretica l Reference [1] Cu 2 C 20 H 28 N 4 Na 4 O (2) Cu-N-Ph-N- Cu F DFT-BS Angew. Chem. Int. Ed. 2001, 40, [2] 9.017(1) π π Stacking F DFT-BS Sci. Rep. 2015, 5, Co(bzi) 2 (NSC) 2 [3] Cu 2 (SCN) 2 (PhenOH) (OCH 3 ) 2 (HOCH 3 ) (2) π π Stacking F DFT-BS Dalton Trans. 2011, 40, [4] MnC 18 H 20 N 4 O (3) Hydrogen Bonding (N H-O) F No Dalton Trans. 2013, 42, [5] CuF 2 (H 2 O) 2 (pyz) 5.331(3) 5.351(3) 6.869(1) Hydrogen Bonding (F H-O) AF DFT-BS Chem. Commun. 2013, 49, 499. S22
24 [6] N 5.903(2) Hydrogen Bonding (N-H Cl) AF DFT-BS Inorg. Chem. 2012, 51, ic 12 H 16 C l2 N 4 [7] 7.441(5) Hydrogen Bonding (F H-O) F No CrystEng Comm 2013, 15, [Cu(TPT)(H 2 O) 2 (BF 4 )] + [8] 6.202(1) Hydrogen Bonding (O H-O) F DFT-BS Inorg. Chem. 2002, 41, Cu 3 C 21 H 48 F 12 N 6 O 9 P 2 [9] nc 45 H 30 N 4 Br M 9.558(2) Hydrogen Bonding (C-H Br) F No Inorg. Chem. 2008, 47, [10] Cu 2 C 12 H 10 Cl 4 N 4 OS 4.283(5) Chloride Neighbor Cu-Cl Cu AF DFT-BS Inorg. Chem. 2004, 43, [11] Cu 2 C 24 H 32 N 12 O (2) Hydrogen Bonding AF DFT-BS Inorg. Chem. 2011, 50, S23
25 [12] 4.581(9) Cu-Cl Cu Cu-O- H Cl-Cu F DFT-BS This work Cu(C 9 H 10 N 2 O)Cl 2 S24
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