data reports 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate Structure description Synthesis and crystallization Refinement
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1 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate ISSN Shamantha Kumar, a Chandra, b B. M. Rajesh, c M. Mahendra b and B. H. Doreswamy a * Received 27 December 2016 Accepted 2 February 2017 Edited by M. Bolte, Goethe-Universität Frankfurt, Germany a Department of Physics, SJB Institute of Technology, Kengeri, Bangalore , India, b Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore , India, and c Department of Physics, R V College of Engineering, Bangalore , India. *Correspondence mychandru.10@gmail.com In the title compound, C 18 H 18 O 5, the dihedral angle between the mean planes of the two aromatic rings is (8). The crystal packing features by intermolecular C HO contacts. Keywords: crystal structure; benzoate derivative; hydrogen bonding. CCDC reference: Structural data: full structural data are available from iucrdata.iucr.org Structure description Benzoate and its derivatives are well known heterocyclic compounds, which have a variety of biological activities. As a part of our ongoing research on benzoate derivatives (Kumar et al., 2016), the title compound was prepared and characterized by single-crystal X-ray diffraction. In the molecule (Fig. 1), the dihedral angle between the mean planes of the benzoate (C14 C19) and phenyl groups (C2 C7) is (8). The crystal packing (Fig. 2) features C HO contacts (Table 1). Synthesis and crystallization Potassium carbonate was added to the solution of 3,4-dimethoxybenzoic acid (1) in water and the mixture was stirred for 30 min. Then, a solution of 2-bromo-1-(p-tolyl)ethanone (2) in ethanol was added and the reaction mixture was heated under reflux for 6 h. After completion of the reaction, ethanol was removed under reduced pressure. The obtained crystals were collected by filtration and recrystallized using ethanol. Refinement Crystal data, data collection and structure refinement details are summarized in Table of2
2 Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA C10 H10BO13 i (2) 157 C23 H25BO20 ii (2) 168 C23 H25BO22 ii (2) 131 Symmetry codes: (i) x; y þ 2; z þ 2; (ii) x þ 1; y; z þ 2. Figure 1 The molecular structure of the title compound, showing the atomlabelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles of arbitrary radius. Table 2 Experimental details. Crystal data Chemical formula C 18 H 18 O 5 M r Crystal system, space group Triclinic, P1 Temperature (K) 293 a, b, c (Å) (3), (3), (4),, ( ) (2), (2), (2) V (Å 3 ) (5) Z 2 Radiation type Cu K (mm 1 ) 0.82 Crystal size (mm) Data collection Diffractometer Bruker X8 Proteum No. of measured, independent and 10314, 2522, 2053 observed [I > 2(I)] reflections R int (sin /) max (Å 1 ) Figure 2 The crystal packing. Acknowledgements The authors would like to thank the SJB Institute of Technology, Kengeri, Bangalore, for their support. MM would like to thank UGC, New Delhi, Government of India, for awarding project F /2012(SR). References Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Refinement R[F 2 >2(F 2 )], wr(f 2 ), S 0.046, 0.169, 1.06 No. of reflections 2522 No. of parameters 212 H-atom treatment H-atom parameters constrained max, min (e Å 3 ) 0.30, 0.37 Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 and SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009). Kumar, S., Chandra, Dileep, C. S., Mahendra, M. & Doreswamy, B. H. (2016). IUCrData, 1, x Sheldrick, G. M. (2008). Acta Cryst. A64, Spek, A. L. (2009). Acta Cryst. D65, of2 Kumar et al. C 18 H 18 O 5
3 full crystallographic data [ 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate Shamantha Kumar, Chandra, B. M. Rajesh, M. Mahendra and B. H. Doreswamy 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate Crystal data C 18 H 18 O 5 M r = Triclinic, P1 Hall symbol: -P 1 a = (3) Å b = (3) Å c = (4) Å α = (2) β = (2) γ = (2) V = (5) Å 3 Data collection Bruker X8 Proteum diffractometer Radiation source: Rotating Anode Graphite monochromator Detector resolution: 18.4 pixels mm -1 φ and ω scans measured reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 212 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Z = 2 F(000) = 332 D x = Mg m 3 Cu Kα radiation, λ = Å Cell parameters from 2522 reflections θ = µ = 0.82 mm 1 T = 293 K Block, light yellow mm 2522 independent reflections 2053 reflections with I > 2σ(I) R int = θ max = 64.5, θ min = 5.2 h = 9 9 k = 10 9 l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.121P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.30 e Å 3 Δρ min = 0.37 e Å 3 Extinction correction: shelxl, FC * =KFC[ XFC 2 Λ 3 /SIN(2Θ)] -1/4 Extinction coefficient: (2) Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles data-1
4 Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wr and all goodnesses of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The observed criterion of F 2 > 2sigma(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (18) (14) (13) (5) O (17) (14) (13) (5) O (17) (14) (13) (5) O (16) (13) (12) (4) O (16) (14) (12) (4) C (3) (3) (2) (7) C (2) (2) (18) (6) C (2) (2) (18) (6) C (2) (2) (18) (6) C (2) (2) (17) (6) C (2) (2) (19) (6) C (2) (2) (19) (6) C (2) (2) (17) (6) C (2) (2) (19) (6) C (2) (2) (18) (6) C (2) (2) (18) (6) C (2) (2) (19) (6) C (2) (2) (18) (6) C (2) (19) (18) (6) C (2) (19) (18) (6) C (2) (2) (18) (6) C (3) (2) (18) (6) C (3) (2) (19) (6) H * H * H * H * H10A * H10B * H * H * H * H25A * H25B * H25C * H28A * H28B * H28C * H99A * data-2
5 H99B * H99C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (9) (7) (9) (5) (7) (6) O (8) (7) (9) (5) (6) (6) O (8) (7) (9) (6) (7) (6) O (8) (7) (8) (5) (6) (5) O (8) (6) (8) (5) (6) (5) C (14) (11) (13) (9) (11) (9) C (11) (10) (12) (8) (9) (8) C (11) (9) (12) (7) (9) (8) C (10) (9) (11) (7) (8) (8) C (10) (10) (11) (7) (8) (7) C (10) (10) (12) (7) (9) (8) C (11) (10) (11) (8) (8) (8) C (10) (9) (11) (7) (9) (8) C (11) (9) (12) (7) (9) (8) C (10) (9) (12) (7) (9) (8) C (10) (9) (12) (7) (8) (8) C (10) (9) (12) (7) (9) (8) C (10) (9) (11) (7) (8) (8) C (9) (9) (12) (7) (8) (8) C (9) (9) (11) (7) (8) (7) C (9) (9) (11) (7) (8) (8) C (11) (9) (11) (8) (9) (8) C (11) (9) (12) (8) (9) (8) Geometric parameters (Å, º) O9 C (2) C16 C (3) O11 C (2) C17 C (3) O11 C (2) C18 C (2) O13 C (2) C1 H99A O20 C (2) C1 H99B O20 C (2) C1 H99C O22 C (2) C3 H O22 C (2) C4 H C1 C (3) C6 H C2 C (3) C7 H C2 C (3) C10 H10A C3 C (3) C10 H10B C4 C (2) C15 H C5 C (3) C16 H C5 C (3) C19 H C6 C (3) C21 H28A data-3
6 C8 C (3) C21 H28B C12 C (2) C21 H28C C14 C (3) C23 H25A C14 C (3) C23 H25B C15 C (2) C23 H25C C10 O11 C (14) H99A C1 H99B C18 O20 C (14) H99A C1 H99C C17 O22 C (15) H99B C1 H99C C1 C2 C (17) C2 C3 H C1 C2 C (18) C4 C3 H C3 C2 C (17) C3 C4 H C2 C3 C (17) C5 C4 H C3 C4 C (17) C5 C6 H C4 C5 C (16) C7 C6 H C4 C5 C (16) C2 C7 H C6 C5 C (16) C6 C7 H C5 C6 C (17) O11 C10 H10A C2 C7 C (18) O11 C10 H10B O9 C8 C (16) C8 C10 H10A O9 C8 C (16) C8 C10 H10B C5 C8 C (15) H10A C10 H10B O11 C10 C (15) C14 C15 H O11 C12 O (16) C16 C15 H O11 C12 C (15) C15 C16 H O13 C12 C (18) C17 C16 H C12 C14 C (16) C14 C19 H C12 C14 C (17) C18 C19 H C15 C14 C (16) O20 C21 H28A C14 C15 C (17) O20 C21 H28B C15 C16 C (18) O20 C21 H28C O22 C17 C (17) H28A C21 H28B O22 C17 C (16) H28A C21 H28C C16 C17 C (16) H28B C21 H28C O20 C18 C (15) O22 C23 H25A O20 C18 C (17) O22 C23 H25B C17 C18 C (17) O22 C23 H25C C14 C19 C (18) H25A C23 H25B C2 C1 H99A H25A C23 H25C C2 C1 H99B H25B C23 H25C C2 C1 H99C C12 O11 C10 C (18) C5 C6 C7 C2 0.3 (3) C10 O11 C12 O (3) O9 C8 C10 O (2) C10 O11 C12 C (14) C5 C8 C10 O (15) C21 O20 C18 C (16) O11 C12 C14 C (16) C21 O20 C18 C (2) O11 C12 C14 C (2) C23 O22 C17 C (3) O13 C12 C14 C (3) data-4
7 C23 O22 C17 C (16) O13 C12 C14 C (17) C1 C2 C3 C (18) C12 C14 C15 C (16) C7 C2 C3 C4 0.7 (3) C19 C14 C15 C (3) C1 C2 C7 C (18) C12 C14 C19 C (16) C3 C2 C7 C6 0.8 (3) C15 C14 C19 C (3) C2 C3 C4 C5 0.5 (3) C14 C15 C16 C (3) C3 C4 C5 C6 1.6 (3) C15 C16 C17 O (16) C3 C4 C5 C (16) C15 C16 C17 C (3) C4 C5 C6 C7 1.5 (3) O22 C17 C18 O (2) C8 C5 C6 C (16) O22 C17 C18 C (15) C4 C5 C8 O (17) C16 C17 C18 O (15) C4 C5 C8 C (2) C16 C17 C18 C (3) C6 C5 C8 O9 6.5 (3) O20 C18 C19 C (16) C6 C5 C8 C (16) C17 C18 C19 C (3) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C10 H10B O (2) 106 C10 H10B O13 i (2) 157 C19 H19 O (2) 100 C23 H25B O20 ii (2) 168 C23 H25B O22 ii (2) 131 Symmetry codes: (i) x, y+2, z+2; (ii) x+1, y, z+2. data-5
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