organic compounds
Ethyl 1-benzyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate
aInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, bPG Department of Chemistry, SDM College (Autonomous), Ujire, 574 240, India, cDepartment of Chemistry, Mangalore University, Mangaluru 574 199, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and eDepartment of Physics, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
*Correspondence e-mail: muneer@najah.edu
The title benzimidazole derivative, C24H22N2O3, is T-shaped with the methoxyphenyl and benzyl rings inclined to the imidazole ring system (r.m.s. deviation = 0.009 Å) by 46.73 (10) and 88.88 (15)°, respectively. The phenyl ring and methoxyphenyl rings are inclined at an angle of 82.14 (16)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into [101] C(14) chains.
Keywords: crystal structure; benzimidazole; hydrogen bonding.
CCDC reference: 1514744
Structure description
Benzimidazole ring systems occur in many marketed drugs such as candesartan and pimobendan. Benzimidazole-5-carboxylates act as anti-HIV agents against hepatitis C virus infections (Zhao et al. 2015). As a part of our ongoing research on benzimidazoles (Saberi et al. 2009), we report herein on the synthesis and of the title compound.
The ORTEP of the molecule is shown in Fig. 1. The molecule is T-shaped with the methoxyphenyl (C8–C13) and the benzyl (C19–C24) rings inclined to the imidazole ring system N1/N2/C1–C7 by 46.73 (10) and 88.88 (15)°, respectively, indicating that the benzyl ring is nearly orthogonal to the imidazole ring system. The phenyl ring and the methoxy phenyl rings are inclined at an angle of 82.14 (16)°.
In the crystal, weak C—H⋯O hydrogen bonds link the molecules into [101] C(14) chains (Table 1). The molecules exhibit layered stacking when viewed along the b axis (Fig. 2).
Synthesis and crystallization
Sodium dithionite (3.0 equiv) was added to a stirred solution of ethyl-4-(4-benzylamino)-3-nitrobenzoate (0.01 mol) and 4-methoxybenzaldehyde (0.01 mol) in DMSO (20 ml). The reaction mixture was stirred at 90°C for 3 h. After the completion of reaction [monitored by TLC; hexane:ethyl acetate (7: 3, v/v)], it was poured onto crushed ice. The solid that separated was filtered off, washed with water and dried. The product was recrystallized from dimethylformamide solution to yield colourless prisms; m.p.: 156–158°C.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1514744
https://doi.org/10.1107/S2414314616017594/hb4091sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017594/hb4091Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616017594/hb4091Isup3.cml
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).C24H22N2O3 | Z = 2 |
Mr = 386.44 | F(000) = 408 |
Triclinic, P1 | Dx = 1.272 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 10.3178 (11) Å | Cell parameters from 2905 reflections |
b = 10.6067 (11) Å | θ = 4.5–64.5° |
c = 10.9071 (12) Å | µ = 0.68 mm−1 |
α = 112.306 (3)° | T = 296 K |
β = 104.249 (4)° | Prism, colourless |
γ = 101.904 (4)° | 0.28 × 0.25 × 0.22 mm |
V = 1008.81 (19) Å3 |
Bruker X8 Proteum diffractometer | 3314 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 2905 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.043 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.5°, θmin = 4.7° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −12→12 |
Tmin = 0.832, Tmax = 0.865 | l = −12→12 |
13401 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1321P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3 |
3314 reflections | (Δ/σ)max < 0.001 |
264 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
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 |
Refinement. Refinement on F2 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 F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. The hydrogen atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
O1 | 1.1345 (2) | 0.4707 (2) | 0.9490 (2) | 0.0819 (7) | |
O2 | 1.2422 (2) | 0.7026 (2) | 1.0151 (2) | 0.1004 (8) | |
O3 | 0.15440 (19) | 0.06462 (19) | −0.0631 (2) | 0.0761 (6) | |
N1 | 0.70029 (18) | 0.34906 (19) | 0.5025 (2) | 0.0541 (6) | |
N2 | 0.75013 (18) | 0.53336 (17) | 0.44821 (18) | 0.0479 (5) | |
C1 | 0.8274 (2) | 0.4539 (2) | 0.6035 (2) | 0.0478 (6) | |
C2 | 0.9192 (2) | 0.4567 (2) | 0.7220 (2) | 0.0523 (7) | |
C3 | 1.0411 (2) | 0.5752 (2) | 0.8052 (2) | 0.0537 (7) | |
C4 | 1.0716 (2) | 0.6898 (2) | 0.7699 (3) | 0.0612 (7) | |
C5 | 0.9822 (2) | 0.6887 (2) | 0.6530 (3) | 0.0593 (7) | |
C6 | 0.8595 (2) | 0.5695 (2) | 0.5706 (2) | 0.0475 (6) | |
C7 | 0.6583 (2) | 0.3990 (2) | 0.4119 (2) | 0.0489 (6) | |
C8 | 0.5275 (2) | 0.3191 (2) | 0.2854 (2) | 0.0515 (7) | |
C9 | 0.4973 (3) | 0.1723 (2) | 0.2028 (3) | 0.0652 (8) | |
C10 | 0.3729 (3) | 0.0916 (3) | 0.0883 (3) | 0.0710 (8) | |
C11 | 0.2729 (2) | 0.1544 (3) | 0.0531 (2) | 0.0589 (7) | |
C12 | 0.3010 (2) | 0.3007 (2) | 0.1350 (2) | 0.0581 (7) | |
C13 | 0.4272 (2) | 0.3818 (2) | 0.2499 (2) | 0.0559 (7) | |
C14 | 0.0398 (3) | 0.1163 (3) | −0.0935 (3) | 0.0814 (10) | |
C15 | 1.1414 (3) | 0.5745 (3) | 0.9281 (3) | 0.0622 (8) | |
C16 | 1.3552 (4) | 0.7102 (5) | 1.1320 (4) | 0.1037 (14) | |
C17 | 1.4595 (5) | 0.6764 (9) | 1.0836 (6) | 0.181 (3) | |
C18 | 0.7560 (2) | 0.6083 (2) | 0.3608 (2) | 0.0549 (7) | |
C19 | 0.7436 (2) | 0.7562 (2) | 0.4225 (2) | 0.0496 (6) | |
C20 | 0.6656 (3) | 0.7919 (3) | 0.5065 (3) | 0.0737 (10) | |
C21 | 0.6474 (5) | 0.9258 (3) | 0.5525 (4) | 0.1012 (15) | |
C22 | 0.7078 (4) | 1.0245 (3) | 0.5153 (5) | 0.1011 (15) | |
C23 | 0.7836 (4) | 0.9912 (4) | 0.4318 (6) | 0.121 (2) | |
C24 | 0.8041 (4) | 0.8571 (4) | 0.3853 (4) | 0.0938 (14) | |
H2 | 0.89910 | 0.38060 | 0.74480 | 0.0630* | |
H4 | 1.15460 | 0.76830 | 0.82740 | 0.0730* | |
H5 | 1.00300 | 0.76460 | 0.63000 | 0.0710* | |
H9 | 0.56230 | 0.12810 | 0.22530 | 0.0780* | |
H10 | 0.35520 | −0.00630 | 0.03370 | 0.0850* | |
H12 | 0.23530 | 0.34430 | 0.11290 | 0.0700* | |
H13 | 0.44520 | 0.47980 | 0.30430 | 0.0670* | |
H14A | 0.00560 | 0.14070 | −0.01620 | 0.1220* | |
H14B | −0.03540 | 0.04250 | −0.17890 | 0.1220* | |
H14C | 0.07180 | 0.20060 | −0.10620 | 0.1220* | |
H16A | 1.39300 | 0.80690 | 1.21060 | 0.1240* | |
H16B | 1.31810 | 0.64270 | 1.16510 | 0.1240* | |
H17A | 1.42420 | 0.57690 | 1.01350 | 0.2710* | |
H17B | 1.53920 | 0.69110 | 1.16130 | 0.2710* | |
H17C | 1.48860 | 0.73720 | 1.04200 | 0.2710* | |
H18A | 0.68000 | 0.54940 | 0.26930 | 0.0660* | |
H18B | 0.84510 | 0.61700 | 0.34470 | 0.0660* | |
H20 | 0.62380 | 0.72530 | 0.53340 | 0.0880* | |
H21 | 0.59330 | 0.94790 | 0.60940 | 0.1210* | |
H22 | 0.69670 | 1.11490 | 0.54750 | 0.1220* | |
H23 | 0.82320 | 1.05820 | 0.40430 | 0.1450* | |
H24 | 0.85890 | 0.83630 | 0.32900 | 0.1120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0830 (12) | 0.0793 (13) | 0.0802 (12) | 0.0231 (10) | 0.0081 (10) | 0.0481 (11) |
O2 | 0.0881 (14) | 0.0772 (13) | 0.0923 (14) | 0.0109 (11) | −0.0177 (11) | 0.0349 (12) |
O3 | 0.0630 (10) | 0.0582 (10) | 0.0732 (11) | 0.0116 (8) | 0.0016 (8) | 0.0147 (9) |
N1 | 0.0513 (10) | 0.0429 (9) | 0.0650 (11) | 0.0133 (8) | 0.0130 (8) | 0.0274 (8) |
N2 | 0.0523 (9) | 0.0384 (9) | 0.0529 (10) | 0.0154 (7) | 0.0155 (8) | 0.0226 (7) |
C1 | 0.0482 (10) | 0.0389 (10) | 0.0580 (12) | 0.0179 (8) | 0.0192 (9) | 0.0218 (9) |
C2 | 0.0554 (11) | 0.0470 (11) | 0.0629 (12) | 0.0224 (9) | 0.0225 (10) | 0.0298 (10) |
C3 | 0.0544 (12) | 0.0482 (12) | 0.0581 (12) | 0.0224 (10) | 0.0182 (10) | 0.0223 (10) |
C4 | 0.0538 (12) | 0.0457 (12) | 0.0701 (14) | 0.0097 (9) | 0.0103 (10) | 0.0232 (11) |
C5 | 0.0604 (12) | 0.0443 (12) | 0.0683 (14) | 0.0110 (10) | 0.0162 (11) | 0.0283 (11) |
C6 | 0.0505 (11) | 0.0395 (10) | 0.0539 (11) | 0.0176 (8) | 0.0182 (9) | 0.0215 (9) |
C7 | 0.0516 (11) | 0.0397 (10) | 0.0569 (12) | 0.0188 (9) | 0.0189 (9) | 0.0220 (9) |
C8 | 0.0533 (11) | 0.0433 (11) | 0.0578 (12) | 0.0169 (9) | 0.0183 (9) | 0.0236 (10) |
C9 | 0.0602 (13) | 0.0473 (13) | 0.0771 (15) | 0.0215 (10) | 0.0130 (12) | 0.0228 (12) |
C10 | 0.0675 (14) | 0.0408 (12) | 0.0777 (16) | 0.0147 (11) | 0.0082 (12) | 0.0129 (11) |
C11 | 0.0571 (12) | 0.0510 (12) | 0.0569 (12) | 0.0114 (10) | 0.0144 (10) | 0.0200 (10) |
C12 | 0.0576 (12) | 0.0534 (13) | 0.0616 (13) | 0.0227 (10) | 0.0166 (10) | 0.0251 (11) |
C13 | 0.0592 (12) | 0.0434 (11) | 0.0572 (12) | 0.0185 (10) | 0.0148 (10) | 0.0180 (10) |
C14 | 0.0644 (15) | 0.0829 (19) | 0.0781 (17) | 0.0157 (13) | 0.0071 (13) | 0.0339 (15) |
C15 | 0.0599 (13) | 0.0604 (14) | 0.0596 (13) | 0.0218 (11) | 0.0144 (11) | 0.0242 (12) |
C16 | 0.085 (2) | 0.110 (3) | 0.092 (2) | 0.0154 (19) | −0.0024 (18) | 0.052 (2) |
C17 | 0.101 (3) | 0.354 (9) | 0.128 (4) | 0.081 (4) | 0.035 (3) | 0.151 (5) |
C18 | 0.0626 (12) | 0.0553 (13) | 0.0558 (12) | 0.0217 (10) | 0.0252 (10) | 0.0307 (10) |
C19 | 0.0471 (10) | 0.0444 (11) | 0.0572 (12) | 0.0109 (8) | 0.0123 (9) | 0.0293 (10) |
C20 | 0.103 (2) | 0.0551 (14) | 0.0897 (18) | 0.0356 (14) | 0.0527 (16) | 0.0433 (13) |
C21 | 0.149 (3) | 0.0676 (18) | 0.122 (3) | 0.061 (2) | 0.073 (2) | 0.0500 (19) |
C22 | 0.112 (3) | 0.0550 (17) | 0.140 (3) | 0.0331 (17) | 0.038 (2) | 0.0497 (19) |
C23 | 0.118 (3) | 0.079 (2) | 0.205 (5) | 0.026 (2) | 0.066 (3) | 0.103 (3) |
C24 | 0.096 (2) | 0.083 (2) | 0.143 (3) | 0.0294 (16) | 0.067 (2) | 0.077 (2) |
O1—C15 | 1.198 (4) | C19—C24 | 1.371 (5) |
O2—C15 | 1.334 (4) | C20—C21 | 1.386 (5) |
O2—C16 | 1.464 (5) | C21—C22 | 1.352 (6) |
O3—C11 | 1.360 (3) | C22—C23 | 1.337 (7) |
O3—C14 | 1.422 (4) | C23—C24 | 1.398 (7) |
N1—C1 | 1.388 (3) | C2—H2 | 0.9300 |
N1—C7 | 1.314 (3) | C4—H4 | 0.9300 |
N2—C6 | 1.376 (3) | C5—H5 | 0.9300 |
N2—C7 | 1.384 (3) | C9—H9 | 0.9300 |
N2—C18 | 1.459 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.388 (3) | C12—H12 | 0.9300 |
C1—C6 | 1.402 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.380 (3) | C14—H14A | 0.9600 |
C3—C4 | 1.408 (3) | C14—H14B | 0.9600 |
C3—C15 | 1.482 (4) | C14—H14C | 0.9600 |
C4—C5 | 1.372 (4) | C16—H16A | 0.9700 |
C5—C6 | 1.388 (3) | C16—H16B | 0.9700 |
C7—C8 | 1.472 (3) | C17—H17A | 0.9600 |
C8—C9 | 1.389 (3) | C17—H17B | 0.9600 |
C8—C13 | 1.395 (3) | C17—H17C | 0.9600 |
C9—C10 | 1.373 (4) | C18—H18A | 0.9700 |
C10—C11 | 1.392 (4) | C18—H18B | 0.9700 |
C11—C12 | 1.387 (4) | C20—H20 | 0.9300 |
C12—C13 | 1.387 (3) | C21—H21 | 0.9300 |
C16—C17 | 1.364 (7) | C22—H22 | 0.9300 |
C18—C19 | 1.501 (3) | C23—H23 | 0.9300 |
C19—C20 | 1.362 (4) | C24—H24 | 0.9300 |
C15—O2—C16 | 117.5 (3) | C3—C2—H2 | 121.00 |
C11—O3—C14 | 118.6 (2) | C3—C4—H4 | 119.00 |
C1—N1—C7 | 105.3 (2) | C5—C4—H4 | 119.00 |
C6—N2—C7 | 106.36 (18) | C4—C5—H5 | 121.00 |
C6—N2—C18 | 123.52 (19) | C6—C5—H5 | 121.00 |
C7—N2—C18 | 128.33 (17) | C8—C9—H9 | 120.00 |
N1—C1—C2 | 130.1 (2) | C10—C9—H9 | 120.00 |
N1—C1—C6 | 109.81 (18) | C9—C10—H10 | 120.00 |
C2—C1—C6 | 120.1 (2) | C11—C10—H10 | 120.00 |
C1—C2—C3 | 118.4 (2) | C11—C12—H12 | 120.00 |
C2—C3—C4 | 120.7 (2) | C13—C12—H12 | 120.00 |
C2—C3—C15 | 118.0 (2) | C8—C13—H13 | 119.00 |
C4—C3—C15 | 121.3 (2) | C12—C13—H13 | 119.00 |
C3—C4—C5 | 121.8 (2) | O3—C14—H14A | 110.00 |
C4—C5—C6 | 117.1 (2) | O3—C14—H14B | 109.00 |
N2—C6—C1 | 105.79 (18) | O3—C14—H14C | 109.00 |
N2—C6—C5 | 132.2 (2) | H14A—C14—H14B | 109.00 |
C1—C6—C5 | 122.1 (2) | H14A—C14—H14C | 109.00 |
N1—C7—N2 | 112.80 (18) | H14B—C14—H14C | 109.00 |
N1—C7—C8 | 123.1 (2) | O2—C16—H16A | 110.00 |
N2—C7—C8 | 124.14 (19) | O2—C16—H16B | 110.00 |
C7—C8—C9 | 118.8 (2) | C17—C16—H16A | 110.00 |
C7—C8—C13 | 122.90 (19) | C17—C16—H16B | 110.00 |
C9—C8—C13 | 118.2 (2) | H16A—C16—H16B | 108.00 |
C8—C9—C10 | 120.9 (3) | C16—C17—H17A | 109.00 |
C9—C10—C11 | 120.9 (3) | C16—C17—H17B | 109.00 |
O3—C11—C10 | 115.8 (3) | C16—C17—H17C | 110.00 |
O3—C11—C12 | 125.2 (2) | H17A—C17—H17B | 109.00 |
C10—C11—C12 | 119.0 (2) | H17A—C17—H17C | 110.00 |
C11—C12—C13 | 119.9 (2) | H17B—C17—H17C | 109.00 |
C8—C13—C12 | 121.2 (2) | N2—C18—H18A | 109.00 |
O1—C15—O2 | 122.6 (3) | N2—C18—H18B | 109.00 |
O1—C15—C3 | 124.3 (3) | C19—C18—H18A | 108.00 |
O2—C15—C3 | 113.1 (3) | C19—C18—H18B | 109.00 |
O2—C16—C17 | 108.2 (4) | H18A—C18—H18B | 108.00 |
N2—C18—C19 | 114.94 (17) | C19—C20—H20 | 119.00 |
C18—C19—C20 | 122.7 (2) | C21—C20—H20 | 119.00 |
C18—C19—C24 | 119.2 (2) | C20—C21—H21 | 120.00 |
C20—C19—C24 | 118.0 (3) | C22—C21—H21 | 120.00 |
C19—C20—C21 | 121.1 (3) | C21—C22—H22 | 120.00 |
C20—C21—C22 | 120.4 (4) | C23—C22—H22 | 120.00 |
C21—C22—C23 | 119.5 (4) | C22—C23—H23 | 119.00 |
C22—C23—C24 | 120.9 (4) | C24—C23—H23 | 120.00 |
C19—C24—C23 | 120.1 (4) | C19—C24—H24 | 120.00 |
C1—C2—H2 | 121.00 | C23—C24—H24 | 120.00 |
C16—O2—C15—O1 | 6.0 (4) | C2—C3—C15—O2 | −169.0 (2) |
C16—O2—C15—C3 | −173.9 (3) | C4—C3—C15—O1 | −166.1 (3) |
C15—O2—C16—C17 | 87.3 (6) | C4—C3—C15—O2 | 13.8 (4) |
C14—O3—C11—C10 | 171.4 (3) | C3—C4—C5—C6 | 0.2 (4) |
C14—O3—C11—C12 | −9.7 (4) | C4—C5—C6—N2 | −179.1 (2) |
C7—N1—C1—C2 | −178.7 (2) | C4—C5—C6—C1 | −0.5 (3) |
C7—N1—C1—C6 | 0.5 (2) | N1—C7—C8—C9 | −44.3 (3) |
C1—N1—C7—N2 | −0.8 (2) | N1—C7—C8—C13 | 131.1 (2) |
C1—N1—C7—C8 | 178.96 (19) | N2—C7—C8—C9 | 135.4 (2) |
C7—N2—C6—C1 | −0.5 (2) | N2—C7—C8—C13 | −49.2 (3) |
C7—N2—C6—C5 | 178.4 (2) | C7—C8—C9—C10 | 176.4 (2) |
C18—N2—C6—C1 | −166.32 (19) | C13—C8—C9—C10 | 0.8 (4) |
C18—N2—C6—C5 | 12.5 (4) | C7—C8—C13—C12 | −175.8 (2) |
C6—N2—C7—N1 | 0.8 (2) | C9—C8—C13—C12 | −0.4 (3) |
C6—N2—C7—C8 | −179.0 (2) | C8—C9—C10—C11 | −0.9 (4) |
C18—N2—C7—N1 | 165.8 (2) | C9—C10—C11—O3 | 179.4 (3) |
C18—N2—C7—C8 | −14.0 (3) | C9—C10—C11—C12 | 0.5 (4) |
C6—N2—C18—C19 | −73.5 (3) | O3—C11—C12—C13 | −178.8 (2) |
C7—N2—C18—C19 | 123.9 (2) | C10—C11—C12—C13 | 0.0 (4) |
N1—C1—C2—C3 | 179.3 (2) | C11—C12—C13—C8 | 0.0 (3) |
C6—C1—C2—C3 | 0.1 (3) | N2—C18—C19—C20 | −31.9 (3) |
N1—C1—C6—N2 | 0.0 (2) | N2—C18—C19—C24 | 153.0 (3) |
N1—C1—C6—C5 | −179.0 (2) | C18—C19—C20—C21 | −174.9 (3) |
C2—C1—C6—N2 | 179.32 (19) | C24—C19—C20—C21 | 0.3 (4) |
C2—C1—C6—C5 | 0.3 (3) | C18—C19—C24—C23 | 174.5 (3) |
C1—C2—C3—C4 | −0.4 (3) | C20—C19—C24—C23 | −0.8 (5) |
C1—C2—C3—C15 | −177.5 (2) | C19—C20—C21—C22 | −0.4 (6) |
C2—C3—C4—C5 | 0.2 (4) | C20—C21—C22—C23 | 1.0 (7) |
C15—C3—C4—C5 | 177.3 (2) | C21—C22—C23—C24 | −1.6 (7) |
C2—C3—C15—O1 | 11.0 (4) | C22—C23—C24—C19 | 1.5 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14C···O1i | 0.96 | 2.59 | 3.498 (4) | 157 |
Symmetry code: (i) x−1, y, z−1. |
Acknowledgements
The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.
References
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Saberi, A., Manjunath, H. R., Naveen, S., Prasad, T. N. M., Rangappa, K. S., Sridhar, M. A. & Prasad, J. S. (2009). Mol. Cryst. Liq. Cryst. 515, 199–206. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, C., Wang, Y. & Ma, S. (2015). Eur. J. Med. Chem. 102, 188–214. Web of Science CrossRef CAS Google Scholar
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