organic compounds
Ethyl 1-(4-fluorobenzyl)-2-(4-methoxyphenyl)-1H-benzo[d]imidazole-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 benzoimidazole derivative, C24H21FN2O3, is T-shaped, with the methoxyphenyl and fluorobenzyl rings inclined to the benzoimidazole ring system by 40.91 (8) and 86.04 (8)°, respectively, indicating that the fluorobenzyl ring system is nearly orthogonal to the benzoimidazole ring system. The fluorobenzyl and methoxyphenyl rings are inclined to one another by 78.90 (10)°. In the crystal, molecules are linked via two pairs of C—H⋯O hydrogen bonds, forming inversion dimers with R22(28) and R22(22) ring motifs. As a result of these hydrogen bonds, ribbons propagating along [010] are formed.
Keywords: crystal structure; benzoimidazole; methoxyphenyl; fluorobenzyl; C—H⋯O hydrogen bonds.
CCDC reference: 1513685
Structure description
Benzoimidazole-based compounds possess diverse biological activities such as anticancer, antibacterial, antifungal (Venkatesan, 1998), antihelmintic, anti-inflammatory, antihistaminic and proton-pump inhibitor (Veerakumari & Munuswamy, 2000). In our recent work (Madankumar et al., 2016), we have reported on the crystal structures of different benzoimidazoles with varying substitution at positions 1 and 2. Based upon these observations, it was found worth to synthesize some 1,2-disubstituted benzoimidazole-5-carboxylates by using a `one-pot' nitro-reductive method and we report herein on the synthesis and of the title compound.
The molecular structure is shown in Fig. 1. The molecule is T-shaped with the methoxyphenyl (C11–C16) and fluorobenzyl (C19–C24) rings inclined to the benzoimidazole ring system (N1/N2/C1–C7) by 40.91 (8) and 86.04 (8)°, respectively, indicating that the fluorobenzyl ring is almost orthogonal to the benzoimidazole ring system. The fluorobenzyl and methoxyphenyl rings are inclined to one another by 78.9 (1)°. The benzoimidazole ring is, as expected, almost planar, with the maximum deviation being 0.024 (2) Å for atom N1. The methoxy group lies in the plane of the benzene ring and is in a −synclinal conformation as indicated by the value of −17.0 (4)° for torsion angle C15—C14—O3—C17. The mean plane of the ethyl carboxylate group (O1/O2/C8–C10) is inclined to the benzoimidazole ring by 4.53 (12)°.
In the crystal, molecules are linked via two pairs of C—H⋯O hydrogen bonds, forming inversion dimers with (28) and (22) ring motifs. As a result of these hydrogen bonds, ribbons propagating along [010] are formed (Table 1 and Fig. 2). There are no other significant intermolecular interactions present.
Synthesis and crystallization
Sodium dithionite (3.0 equiv) was added to a stirred solution of ethyl-4-(4-fluorobenzylamino)-3-nitrobenzoate (0.01 mol) and 4-methoxybenzaldehyde (0.01 mol) in DMSO (20 ml). The reaction mixture was stirred at 363 K 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 using DMF as the solvent to yield colourless block-like crystals (m.p. 343–345 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1513685
https://doi.org/10.1107/S2414314616017442/su4091sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017442/su4091Isup2.hkl
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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C24H21FN2O3 | F(000) = 848 |
Mr = 404.43 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2yn | Cell parameters from 2930 reflections |
a = 13.5156 (10) Å | θ = 4.8–64.2° |
b = 9.5906 (8) Å | µ = 0.77 mm−1 |
c = 16.1315 (13) Å | T = 296 K |
β = 101.409 (3)° | Block, colourless |
V = 2049.7 (3) Å3 | 0.29 × 0.27 × 0.24 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 3318 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 2930 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.053 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.2°, θmin = 4.8° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −9→10 |
Tmin = 0.808, Tmax = 0.837 | l = −17→18 |
12703 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.1193P)2 + 0.3084P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3318 reflections | Δρmax = 0.21 e Å−3 |
274 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0054 (17) |
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. |
x | y | z | Uiso*/Ueq | ||
F1 | 1.07749 (10) | −0.11559 (17) | 0.77837 (11) | 0.0973 (6) | |
O1 | 0.26807 (12) | −0.0335 (2) | 0.51786 (10) | 0.0797 (6) | |
O2 | 0.31003 (11) | −0.14020 (17) | 0.64310 (10) | 0.0721 (6) | |
O3 | 0.94650 (14) | 0.72073 (18) | 0.50713 (14) | 0.0922 (7) | |
N1 | 0.58231 (12) | 0.29661 (16) | 0.53285 (10) | 0.0538 (5) | |
N2 | 0.68142 (11) | 0.25854 (15) | 0.66019 (9) | 0.0485 (5) | |
C1 | 0.53828 (13) | 0.19655 (19) | 0.57612 (11) | 0.0480 (6) | |
C2 | 0.44881 (14) | 0.1219 (2) | 0.55256 (12) | 0.0527 (6) | |
C3 | 0.42179 (14) | 0.0283 (2) | 0.60977 (12) | 0.0518 (6) | |
C4 | 0.48318 (14) | 0.0107 (2) | 0.69070 (12) | 0.0551 (6) | |
C5 | 0.57209 (14) | 0.0826 (2) | 0.71444 (12) | 0.0535 (6) | |
C6 | 0.59874 (13) | 0.17340 (18) | 0.65591 (11) | 0.0471 (5) | |
C7 | 0.66709 (13) | 0.33072 (18) | 0.58400 (11) | 0.0496 (6) | |
C8 | 0.32629 (15) | −0.0496 (2) | 0.58441 (13) | 0.0593 (7) | |
C9 | 0.2175 (2) | −0.2203 (3) | 0.62499 (19) | 0.0911 (10) | |
C10 | 0.2212 (3) | −0.3276 (4) | 0.6906 (3) | 0.1180 (16) | |
C11 | 0.73916 (14) | 0.43352 (18) | 0.56416 (11) | 0.0510 (6) | |
C12 | 0.84343 (15) | 0.4129 (2) | 0.58535 (12) | 0.0544 (6) | |
C13 | 0.90954 (16) | 0.5105 (2) | 0.56507 (13) | 0.0599 (7) | |
C14 | 0.87388 (18) | 0.6299 (2) | 0.52271 (15) | 0.0660 (8) | |
C15 | 0.77114 (18) | 0.6523 (2) | 0.49977 (16) | 0.0714 (8) | |
C16 | 0.70457 (16) | 0.5549 (2) | 0.52076 (14) | 0.0626 (7) | |
C17 | 0.9192 (3) | 0.8263 (4) | 0.4464 (3) | 0.1321 (18) | |
C18 | 0.76049 (14) | 0.2723 (2) | 0.73505 (11) | 0.0510 (6) | |
C19 | 0.84310 (13) | 0.16391 (18) | 0.74350 (10) | 0.0454 (5) | |
C20 | 0.84912 (14) | 0.06472 (19) | 0.68282 (12) | 0.0510 (6) | |
C21 | 0.92827 (15) | −0.0298 (2) | 0.69431 (14) | 0.0597 (7) | |
C22 | 1.00001 (15) | −0.0228 (2) | 0.76717 (15) | 0.0642 (7) | |
C23 | 0.99693 (16) | 0.0737 (3) | 0.82863 (14) | 0.0683 (8) | |
C24 | 0.91817 (15) | 0.1667 (2) | 0.81640 (12) | 0.0578 (6) | |
H2 | 0.40790 | 0.13460 | 0.49950 | 0.0630* | |
H4 | 0.46300 | −0.05090 | 0.72870 | 0.0660* | |
H5 | 0.61270 | 0.07070 | 0.76760 | 0.0640* | |
H9A | 0.21030 | −0.26400 | 0.56990 | 0.1100* | |
H9B | 0.16000 | −0.15950 | 0.62440 | 0.1100* | |
H10A | 0.27220 | −0.39500 | 0.68560 | 0.1770* | |
H10B | 0.15680 | −0.37310 | 0.68360 | 0.1770* | |
H10C | 0.23690 | −0.28470 | 0.74540 | 0.1770* | |
H12 | 0.86860 | 0.33200 | 0.61360 | 0.0650* | |
H13 | 0.97870 | 0.49520 | 0.58020 | 0.0720* | |
H15 | 0.74670 | 0.73260 | 0.47030 | 0.0860* | |
H16 | 0.63550 | 0.57090 | 0.50550 | 0.0750* | |
H17A | 0.88370 | 0.78580 | 0.39460 | 0.1980* | |
H17B | 0.97890 | 0.87230 | 0.43660 | 0.1980* | |
H17C | 0.87650 | 0.89270 | 0.46670 | 0.1980* | |
H18A | 0.73000 | 0.26730 | 0.78460 | 0.0610* | |
H18B | 0.79080 | 0.36390 | 0.73450 | 0.0610* | |
H20 | 0.79970 | 0.06120 | 0.63380 | 0.0610* | |
H21 | 0.93260 | −0.09660 | 0.65340 | 0.0720* | |
H23 | 1.04670 | 0.07640 | 0.87750 | 0.0820* | |
H24 | 0.91490 | 0.23320 | 0.85780 | 0.0690* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0674 (9) | 0.0911 (10) | 0.1323 (14) | 0.0300 (7) | 0.0171 (8) | 0.0145 (9) |
O1 | 0.0667 (10) | 0.0970 (13) | 0.0703 (10) | −0.0099 (8) | 0.0012 (8) | −0.0012 (9) |
O2 | 0.0679 (9) | 0.0779 (11) | 0.0722 (10) | −0.0165 (7) | 0.0182 (7) | −0.0008 (8) |
O3 | 0.0903 (12) | 0.0650 (10) | 0.1366 (16) | −0.0022 (8) | 0.0599 (12) | 0.0180 (10) |
N1 | 0.0593 (9) | 0.0516 (9) | 0.0509 (9) | 0.0078 (7) | 0.0119 (7) | 0.0079 (7) |
N2 | 0.0508 (8) | 0.0460 (8) | 0.0488 (8) | 0.0047 (6) | 0.0099 (6) | 0.0033 (6) |
C1 | 0.0512 (9) | 0.0450 (10) | 0.0482 (10) | 0.0096 (7) | 0.0107 (7) | 0.0028 (7) |
C2 | 0.0518 (10) | 0.0554 (11) | 0.0500 (10) | 0.0109 (8) | 0.0080 (8) | 0.0000 (8) |
C3 | 0.0510 (10) | 0.0504 (11) | 0.0549 (10) | 0.0083 (8) | 0.0125 (8) | −0.0029 (8) |
C4 | 0.0581 (11) | 0.0520 (11) | 0.0575 (11) | 0.0054 (8) | 0.0173 (8) | 0.0065 (8) |
C5 | 0.0552 (10) | 0.0539 (11) | 0.0502 (10) | 0.0062 (8) | 0.0077 (8) | 0.0056 (8) |
C6 | 0.0504 (9) | 0.0420 (9) | 0.0494 (9) | 0.0094 (7) | 0.0111 (7) | 0.0025 (7) |
C7 | 0.0552 (10) | 0.0449 (10) | 0.0498 (10) | 0.0103 (8) | 0.0133 (8) | 0.0030 (8) |
C8 | 0.0572 (11) | 0.0607 (12) | 0.0620 (12) | 0.0036 (9) | 0.0168 (9) | −0.0074 (10) |
C9 | 0.0832 (16) | 0.103 (2) | 0.0922 (18) | −0.0344 (15) | 0.0297 (13) | −0.0184 (16) |
C10 | 0.095 (2) | 0.092 (2) | 0.180 (4) | −0.0134 (16) | 0.059 (2) | 0.023 (2) |
C11 | 0.0621 (11) | 0.0441 (10) | 0.0493 (10) | 0.0055 (8) | 0.0168 (8) | 0.0009 (8) |
C12 | 0.0632 (11) | 0.0503 (11) | 0.0527 (10) | 0.0091 (8) | 0.0190 (8) | 0.0049 (8) |
C13 | 0.0608 (11) | 0.0603 (12) | 0.0631 (12) | 0.0049 (9) | 0.0235 (9) | −0.0010 (9) |
C14 | 0.0791 (14) | 0.0505 (11) | 0.0784 (14) | 0.0011 (10) | 0.0397 (11) | 0.0018 (10) |
C15 | 0.0807 (15) | 0.0510 (12) | 0.0899 (16) | 0.0130 (10) | 0.0346 (12) | 0.0197 (11) |
C16 | 0.0649 (12) | 0.0540 (12) | 0.0722 (13) | 0.0103 (9) | 0.0213 (10) | 0.0085 (10) |
C17 | 0.128 (3) | 0.092 (2) | 0.198 (4) | 0.0054 (19) | 0.085 (3) | 0.060 (2) |
C18 | 0.0565 (10) | 0.0497 (10) | 0.0468 (10) | 0.0010 (8) | 0.0101 (8) | −0.0033 (8) |
C19 | 0.0493 (9) | 0.0438 (9) | 0.0436 (9) | −0.0048 (7) | 0.0107 (7) | 0.0038 (7) |
C20 | 0.0546 (10) | 0.0493 (10) | 0.0487 (10) | −0.0017 (8) | 0.0093 (8) | −0.0001 (8) |
C21 | 0.0637 (12) | 0.0488 (11) | 0.0708 (13) | 0.0004 (9) | 0.0236 (10) | −0.0012 (9) |
C22 | 0.0509 (11) | 0.0601 (12) | 0.0816 (14) | 0.0069 (9) | 0.0135 (10) | 0.0170 (11) |
C23 | 0.0578 (11) | 0.0785 (15) | 0.0630 (13) | 0.0005 (10) | −0.0018 (9) | 0.0097 (11) |
C24 | 0.0632 (11) | 0.0603 (12) | 0.0477 (10) | −0.0039 (9) | 0.0059 (8) | −0.0015 (9) |
F1—C22 | 1.359 (3) | C19—C20 | 1.379 (2) |
O1—C8 | 1.209 (3) | C19—C24 | 1.393 (3) |
O2—C8 | 1.335 (3) | C20—C21 | 1.386 (3) |
O2—C9 | 1.447 (3) | C21—C22 | 1.369 (3) |
O3—C14 | 1.372 (3) | C22—C23 | 1.363 (3) |
O3—C17 | 1.406 (5) | C23—C24 | 1.373 (3) |
N1—C1 | 1.388 (2) | C2—H2 | 0.9300 |
N1—C7 | 1.314 (2) | C4—H4 | 0.9300 |
N2—C6 | 1.375 (2) | C5—H5 | 0.9300 |
N2—C7 | 1.390 (2) | C9—H9A | 0.9700 |
N2—C18 | 1.452 (2) | C9—H9B | 0.9700 |
C1—C2 | 1.392 (3) | C10—H10A | 0.9600 |
C1—C6 | 1.399 (2) | C10—H10B | 0.9600 |
C2—C3 | 1.387 (3) | C10—H10C | 0.9600 |
C3—C4 | 1.412 (3) | C12—H12 | 0.9300 |
C3—C8 | 1.477 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.373 (3) | C15—H15 | 0.9300 |
C5—C6 | 1.384 (3) | C16—H16 | 0.9300 |
C7—C11 | 1.465 (3) | C17—H17A | 0.9600 |
C9—C10 | 1.470 (5) | C17—H17B | 0.9600 |
C11—C12 | 1.397 (3) | C17—H17C | 0.9600 |
C11—C16 | 1.391 (3) | C18—H18A | 0.9700 |
C12—C13 | 1.377 (3) | C18—H18B | 0.9700 |
C13—C14 | 1.371 (3) | C20—H20 | 0.9300 |
C14—C15 | 1.381 (3) | C21—H21 | 0.9300 |
C15—C16 | 1.385 (3) | C23—H23 | 0.9300 |
C18—C19 | 1.512 (3) | C24—H24 | 0.9300 |
C8—O2—C9 | 117.34 (18) | C19—C24—C23 | 121.56 (18) |
C14—O3—C17 | 119.1 (2) | C1—C2—H2 | 121.00 |
C1—N1—C7 | 105.29 (15) | C3—C2—H2 | 121.00 |
C6—N2—C7 | 106.36 (14) | C3—C4—H4 | 119.00 |
C6—N2—C18 | 123.58 (15) | C5—C4—H4 | 119.00 |
C7—N2—C18 | 129.87 (15) | C4—C5—H5 | 121.00 |
N1—C1—C2 | 130.85 (17) | C6—C5—H5 | 121.00 |
N1—C1—C6 | 109.99 (16) | O2—C9—H9A | 110.00 |
C2—C1—C6 | 119.16 (17) | O2—C9—H9B | 110.00 |
C1—C2—C3 | 118.69 (17) | C10—C9—H9A | 110.00 |
C2—C3—C4 | 120.58 (18) | C10—C9—H9B | 110.00 |
C2—C3—C8 | 118.27 (17) | H9A—C9—H9B | 108.00 |
C4—C3—C8 | 121.14 (17) | C9—C10—H10A | 109.00 |
C3—C4—C5 | 121.33 (18) | C9—C10—H10B | 109.00 |
C4—C5—C6 | 117.23 (17) | C9—C10—H10C | 109.00 |
N2—C6—C1 | 105.84 (15) | H10A—C10—H10B | 109.00 |
N2—C6—C5 | 131.18 (17) | H10A—C10—H10C | 110.00 |
C1—C6—C5 | 122.97 (17) | H10B—C10—H10C | 109.00 |
N1—C7—N2 | 112.51 (15) | C11—C12—H12 | 119.00 |
N1—C7—C11 | 124.42 (16) | C13—C12—H12 | 119.00 |
N2—C7—C11 | 123.08 (16) | C12—C13—H13 | 120.00 |
O1—C8—O2 | 122.92 (19) | C14—C13—H13 | 120.00 |
O1—C8—C3 | 124.12 (19) | C14—C15—H15 | 120.00 |
O2—C8—C3 | 112.97 (17) | C16—C15—H15 | 120.00 |
O2—C9—C10 | 108.7 (3) | C11—C16—H16 | 119.00 |
C7—C11—C12 | 122.24 (16) | C15—C16—H16 | 119.00 |
C7—C11—C16 | 120.09 (17) | O3—C17—H17A | 109.00 |
C12—C11—C16 | 117.65 (18) | O3—C17—H17B | 109.00 |
C11—C12—C13 | 121.07 (18) | O3—C17—H17C | 109.00 |
C12—C13—C14 | 120.4 (2) | H17A—C17—H17B | 110.00 |
O3—C14—C13 | 115.3 (2) | H17A—C17—H17C | 110.00 |
O3—C14—C15 | 124.73 (19) | H17B—C17—H17C | 109.00 |
C13—C14—C15 | 119.9 (2) | N2—C18—H18A | 109.00 |
C14—C15—C16 | 119.8 (2) | N2—C18—H18B | 109.00 |
C11—C16—C15 | 121.2 (2) | C19—C18—H18A | 109.00 |
N2—C18—C19 | 114.93 (15) | C19—C18—H18B | 109.00 |
C18—C19—C20 | 123.82 (16) | H18A—C18—H18B | 108.00 |
C18—C19—C24 | 117.67 (15) | C19—C20—H20 | 120.00 |
C20—C19—C24 | 118.50 (17) | C21—C20—H20 | 120.00 |
C19—C20—C21 | 120.57 (18) | C20—C21—H21 | 121.00 |
C20—C21—C22 | 118.64 (19) | C22—C21—H21 | 121.00 |
F1—C22—C21 | 118.57 (19) | C22—C23—H23 | 121.00 |
F1—C22—C23 | 118.8 (2) | C24—C23—H23 | 121.00 |
C21—C22—C23 | 122.6 (2) | C19—C24—H24 | 119.00 |
C22—C23—C24 | 118.1 (2) | C23—C24—H24 | 119.00 |
C9—O2—C8—O1 | −0.7 (3) | C4—C3—C8—O1 | 175.9 (2) |
C9—O2—C8—C3 | 179.00 (19) | C4—C3—C8—O2 | −3.8 (3) |
C8—O2—C9—C10 | 171.5 (2) | C3—C4—C5—C6 | 0.3 (3) |
C17—O3—C14—C13 | 163.7 (3) | C4—C5—C6—N2 | −179.81 (18) |
C17—O3—C14—C15 | −17.0 (4) | C4—C5—C6—C1 | 1.7 (3) |
C7—N1—C1—C2 | −179.0 (2) | N1—C7—C11—C12 | −139.31 (19) |
C7—N1—C1—C6 | 1.1 (2) | N1—C7—C11—C16 | 38.9 (3) |
C1—N1—C7—N2 | −0.5 (2) | N2—C7—C11—C12 | 41.0 (3) |
C1—N1—C7—C11 | 179.72 (17) | N2—C7—C11—C16 | −140.85 (19) |
C7—N2—C6—C1 | 0.87 (19) | C7—C11—C12—C13 | 179.22 (18) |
C7—N2—C6—C5 | −177.82 (19) | C16—C11—C12—C13 | 1.0 (3) |
C18—N2—C6—C1 | 176.28 (16) | C7—C11—C16—C15 | −178.68 (19) |
C18—N2—C6—C5 | −2.4 (3) | C12—C11—C16—C15 | −0.4 (3) |
C6—N2—C7—N1 | −0.2 (2) | C11—C12—C13—C14 | −0.6 (3) |
C6—N2—C7—C11 | 179.54 (16) | C12—C13—C14—O3 | 178.9 (2) |
C18—N2—C7—N1 | −175.24 (17) | C12—C13—C14—C15 | −0.4 (3) |
C18—N2—C7—C11 | 4.5 (3) | O3—C14—C15—C16 | −178.3 (2) |
C6—N2—C18—C19 | 85.6 (2) | C13—C14—C15—C16 | 0.9 (3) |
C7—N2—C18—C19 | −100.2 (2) | C14—C15—C16—C11 | −0.5 (3) |
N1—C1—C2—C3 | −178.97 (19) | N2—C18—C19—C20 | 4.7 (3) |
C6—C1—C2—C3 | 1.0 (3) | N2—C18—C19—C24 | −176.44 (16) |
N1—C1—C6—N2 | −1.2 (2) | C18—C19—C20—C21 | 178.77 (18) |
N1—C1—C6—C5 | 177.60 (17) | C24—C19—C20—C21 | −0.1 (3) |
C2—C1—C6—N2 | 178.81 (16) | C18—C19—C24—C23 | −178.88 (19) |
C2—C1—C6—C5 | −2.4 (3) | C20—C19—C24—C23 | 0.0 (3) |
C1—C2—C3—C4 | 0.9 (3) | C19—C20—C21—C22 | 0.2 (3) |
C1—C2—C3—C8 | 179.53 (17) | C20—C21—C22—F1 | 179.9 (2) |
C2—C3—C4—C5 | −1.6 (3) | C20—C21—C22—C23 | −0.3 (3) |
C8—C3—C4—C5 | 179.83 (18) | F1—C22—C23—C24 | −179.98 (19) |
C2—C3—C8—O1 | −2.7 (3) | C21—C22—C23—C24 | 0.3 (3) |
C2—C3—C8—O2 | 177.62 (17) | C22—C23—C24—C19 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17C···O1i | 0.96 | 2.43 | 3.356 (4) | 163 |
C20—H20···O1ii | 0.93 | 2.45 | 3.324 (2) | 156 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −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
Madankumar, S., Vasantha, K., Boja, P., Byrappa, K. & Warad, I. (2016). IUCr Data 1, x161124. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Veerakumari, L. & Munuswamy, N. (2000). Vet. Parasitol. 91, 129–140. Web of Science CrossRef PubMed CAS Google Scholar
Venkatesan, P. (1998). J. Antimic. Chemoth. 41, 145–147. Web of Science CrossRef CAS Google Scholar
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