organic compounds
Ethyl 2-(4-cyanophenyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole-5-carboxylate
aPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India, bDepartment of Chemistry, Mangalore University, Mangaluru 574 199, India, cPG Department of Chemistry, SDM College (Autonomous), Ujire, Karnataka 574 240, India, dDepartment of Material Science, Mangalore University, Mangaluru 574 199, India, and eDepartment of Chemistry, Faculty of Science, An Najah National University, Nablus, West Bank, Palestinian Territories
*Correspondence e-mail: khalil.i@najah.edu
The title benzimidazole derivative, C24H18FN3O2, is T-shaped, with the 4-cyanobenzene and 4-fluorobenzyl rings inclined to the imidazole ring system by 32.89 (10) and 83.63 (10)°, respectively, and by 89.00 (12)° to one another. The terminal methyl group of the ethylcarboxylate group is disordered over three sites and was refined with a fixed occupancy ratio of 1/3:1/3:1/3. In the crystal, molecules are essentially linked by offset π–π interactions, involving inversion-related imidazole rings [inter-centroid distance = 3.763 (1) Å], and stack along the b-axis direction.
Keywords: crystal structure; benzimidazole; offset π–π interactions.
CCDC reference: 1431412
Structure description
Having an interest in the synthesis of benzimidazole derivatives, we present herein the synthesis and . The molecule is T-shaped, with the 4-cyanobenzene ring (C1–C6) and the 4-fluorobenzyl ring (C10–C15) inclined to imidazole ring system (N1/N2/C8/C16–C21) by 32.89 (10) and 83.63 (10)°, respectively, and by 89.00 (12)° to one another.
of the title compound, Fig. 1In the crystal, Fig. 2, molecules are essentially linked by offset π–π interactions, involving inversion-related imidazole ring systems, and stack along the b-axis direction [Cg1⋯Cg4i = 3.763 (1) Å, interplanar distance = 3.556 (1) Å, slippage 1.277 Å, Cg1 and Cg4 are the centroids of rings N1/N2/C8/C16/C17 and C16–C21, respectively; symmetry code (i) −x + 1, −y + 1, −z + 1].
Synthesis and crystallization
Sodium dithionite (3.0 equiv) was added to a stirred solution of ethyl 4-(4-fluorobenzylamino)-3-nitrobenzoate (0.01 mol; 1.0 equiv) and 4-cyanobenzaldehyde (0.01 mol; 1.0 equiv) 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 from N,N-dimethylformamide giving crystals suitable for X-ray diffraction analysis.
Refinement
Crystal data, data collection and structure . The terminal methyl group (C24A, C24B and C24C) of the ethylcarboxylate moiety is disordered over three sites and was refined with a fixed occupancy ratio of 1/3:1/3:1/3.
details are summarized in Table 1Structural data
CCDC reference: 1431412
https://doi.org/10.1107/S241431461601124X/su4064sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461601124X/su4064Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461601124X/su4064Isup3.cml
Data collection: CrystalClear (Rigaku, 2011); cell
CrystalClear (Rigaku, 2011); data reduction: CrystalClear (Rigaku, 2011); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C24H18FN3O2 | Dx = 1.321 Mg m−3 |
Mr = 399.41 | Mo Kα radiation, λ = 0.71075 Å |
Orthorhombic, Pbca | Cell parameters from 4608 reflections |
a = 18.4827 (12) Å | θ = 27.5–3.0° |
b = 9.8467 (6) Å | µ = 0.09 mm−1 |
c = 22.0681 (15) Å | T = 293 K |
V = 4016.3 (4) Å3 | Block, colourless |
Z = 8 | 0.43 × 0.28 × 0.13 mm |
F(000) = 1664 |
Rigaku Saturn724+ diffractometer | 2276 reflections with I > 2σ(I) |
profile data from ω–scans | Rint = 0.078 |
Absorption correction: multi-scan (NUMABS; Rigaku, 1999) | θmax = 25.3°, θmin = 3.0° |
Tmin = 0.970, Tmax = 0.988 | h = −22→22 |
37377 measured reflections | k = −11→10 |
3631 independent reflections | l = −26→26 |
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)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0374P)2 + 1.0958P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.004 |
3631 reflections | Δρmax = 0.11 e Å−3 |
281 parameters | Δρmin = −0.15 e Å−3 |
3 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.80220 (9) | 0.00408 (18) | 0.68055 (7) | 0.1111 (6) | |
N1 | 0.57339 (10) | 0.24922 (19) | 0.49515 (8) | 0.0573 (5) | |
N2 | 0.45818 (10) | 0.2120 (2) | 0.46754 (8) | 0.0636 (5) | |
N3 | 0.61148 (16) | −0.2833 (3) | 0.23995 (11) | 0.1117 (9) | |
C1 | 0.60741 (14) | 0.0001 (2) | 0.41557 (11) | 0.0674 (7) | |
H1 | 0.6361 | 0.0050 | 0.4501 | 0.081* | |
C2 | 0.62374 (14) | −0.0929 (3) | 0.37106 (11) | 0.0708 (7) | |
H2 | 0.6636 | −0.1496 | 0.3755 | 0.085* | |
C3 | 0.58132 (14) | −0.1023 (3) | 0.32020 (11) | 0.0655 (7) | |
C4 | 0.52266 (15) | −0.0168 (3) | 0.31341 (11) | 0.0758 (8) | |
H4 | 0.4939 | −0.0227 | 0.2790 | 0.091* | |
C5 | 0.50686 (13) | 0.0770 (3) | 0.35759 (10) | 0.0680 (7) | |
H5 | 0.4676 | 0.1350 | 0.3526 | 0.082* | |
C6 | 0.54866 (12) | 0.0864 (2) | 0.40949 (10) | 0.0556 (6) | |
C7 | 0.59760 (16) | −0.2023 (3) | 0.27484 (13) | 0.0817 (8) | |
C8 | 0.52664 (13) | 0.1830 (2) | 0.45663 (10) | 0.0569 (6) | |
C9 | 0.65188 (11) | 0.2605 (2) | 0.49315 (10) | 0.0608 (6) | |
H9A | 0.6649 | 0.3559 | 0.4939 | 0.073* | |
H9B | 0.6689 | 0.2229 | 0.4551 | 0.073* | |
C10 | 0.69001 (12) | 0.1895 (2) | 0.54441 (9) | 0.0508 (6) | |
C11 | 0.76027 (12) | 0.2258 (2) | 0.55708 (11) | 0.0622 (6) | |
H11 | 0.7824 | 0.2936 | 0.5344 | 0.075* | |
C12 | 0.79824 (14) | 0.1634 (3) | 0.60266 (12) | 0.0758 (8) | |
H12 | 0.8458 | 0.1879 | 0.6109 | 0.091* | |
C13 | 0.76507 (16) | 0.0659 (3) | 0.63530 (11) | 0.0717 (7) | |
C14 | 0.69539 (15) | 0.0273 (3) | 0.62490 (12) | 0.0724 (7) | |
H14 | 0.6736 | −0.0395 | 0.6484 | 0.087* | |
C15 | 0.65808 (13) | 0.0898 (2) | 0.57864 (11) | 0.0661 (7) | |
H15 | 0.6106 | 0.0641 | 0.5705 | 0.079* | |
C16 | 0.53115 (13) | 0.3252 (2) | 0.53371 (10) | 0.0563 (6) | |
C17 | 0.45998 (13) | 0.3020 (2) | 0.51577 (10) | 0.0576 (6) | |
C18 | 0.40424 (13) | 0.3651 (3) | 0.54635 (11) | 0.0673 (7) | |
H18 | 0.3564 | 0.3507 | 0.5348 | 0.081* | |
C19 | 0.42048 (14) | 0.4497 (3) | 0.59418 (11) | 0.0636 (7) | |
C20 | 0.49223 (15) | 0.4708 (3) | 0.61153 (11) | 0.0696 (7) | |
H20 | 0.5022 | 0.5278 | 0.6441 | 0.084* | |
C21 | 0.54850 (14) | 0.4090 (3) | 0.58150 (11) | 0.0691 (7) | |
H21 | 0.5963 | 0.4233 | 0.5930 | 0.083* | |
O1 | 0.38006 (11) | 0.5953 (2) | 0.67054 (10) | 0.1065 (7) | |
O2 | 0.29671 (13) | 0.4915 (3) | 0.61495 (10) | 0.1189 (9) | |
C22 | 0.3591 (2) | 0.5116 (3) | 0.62677 (13) | 0.0830 (9) | |
C23 | 0.3227 (2) | 0.6538 (5) | 0.7078 (2) | 0.1504 (17) | |
H23A | 0.2788 | 0.6025 | 0.7002 | 0.181* | 0.3333 |
H23B | 0.3356 | 0.6393 | 0.7499 | 0.181* | 0.3333 |
H23C | 0.2914 | 0.7123 | 0.6841 | 0.181* | 0.3333 |
H23D | 0.2938 | 0.5835 | 0.7268 | 0.181* | 0.3333 |
H23E | 0.2863 | 0.6916 | 0.6811 | 0.181* | 0.3333 |
H23F | 0.3000 | 0.5809 | 0.7305 | 0.181* | 0.3333 |
C24A | 0.3082 (7) | 0.7746 (12) | 0.7016 (6) | 0.127 (4) | 0.3333 |
H24A | 0.3516 | 0.8275 | 0.7058 | 0.191* | 0.3333 |
H24B | 0.2739 | 0.8016 | 0.7319 | 0.191* | 0.3333 |
H24C | 0.2879 | 0.7893 | 0.6621 | 0.191* | 0.3333 |
C24B | 0.3638 (13) | 0.733 (2) | 0.7536 (12) | 0.127 (4) | 0.3333 |
H24D | 0.3898 | 0.6715 | 0.7796 | 0.191* | 0.3333 |
H24E | 0.3308 | 0.7859 | 0.7774 | 0.191* | 0.3333 |
H24F | 0.3974 | 0.7918 | 0.7335 | 0.191* | 0.3333 |
C24C | 0.3433 (12) | 0.753 (2) | 0.7480 (13) | 0.127 (4) | 0.3333 |
H24G | 0.3720 | 0.7132 | 0.7796 | 0.191* | 0.3333 |
H24H | 0.3011 | 0.7944 | 0.7652 | 0.191* | 0.3333 |
H24I | 0.3713 | 0.8205 | 0.7271 | 0.191* | 0.3333 |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1119 (13) | 0.1166 (14) | 0.1048 (12) | 0.0200 (11) | −0.0263 (11) | 0.0256 (11) |
N1 | 0.0539 (11) | 0.0617 (12) | 0.0562 (11) | −0.0022 (11) | 0.0002 (10) | −0.0038 (10) |
N2 | 0.0593 (13) | 0.0698 (14) | 0.0617 (13) | −0.0004 (11) | −0.0042 (10) | −0.0023 (11) |
N3 | 0.127 (2) | 0.116 (2) | 0.0915 (19) | −0.0095 (18) | 0.0115 (16) | −0.0401 (17) |
C1 | 0.0764 (18) | 0.0696 (18) | 0.0562 (14) | 0.0054 (15) | −0.0087 (13) | −0.0041 (13) |
C2 | 0.0790 (18) | 0.0679 (18) | 0.0656 (16) | 0.0045 (14) | 0.0008 (14) | −0.0041 (14) |
C3 | 0.0704 (17) | 0.0663 (18) | 0.0598 (16) | −0.0126 (14) | 0.0080 (13) | −0.0070 (13) |
C4 | 0.0740 (18) | 0.094 (2) | 0.0593 (16) | −0.0140 (16) | −0.0077 (14) | −0.0109 (16) |
C5 | 0.0638 (16) | 0.0791 (18) | 0.0611 (15) | 0.0006 (14) | −0.0044 (13) | −0.0043 (15) |
C6 | 0.0590 (14) | 0.0560 (16) | 0.0520 (14) | −0.0051 (13) | 0.0000 (12) | 0.0008 (12) |
C7 | 0.089 (2) | 0.087 (2) | 0.0694 (17) | −0.0167 (17) | 0.0108 (15) | −0.0171 (17) |
C8 | 0.0608 (16) | 0.0571 (16) | 0.0527 (14) | −0.0017 (13) | −0.0045 (12) | 0.0043 (12) |
C9 | 0.0550 (15) | 0.0632 (16) | 0.0642 (15) | −0.0093 (12) | 0.0044 (12) | 0.0008 (13) |
C10 | 0.0501 (14) | 0.0511 (14) | 0.0513 (13) | −0.0018 (11) | 0.0067 (11) | −0.0067 (11) |
C11 | 0.0560 (15) | 0.0618 (16) | 0.0687 (15) | −0.0083 (13) | 0.0041 (13) | −0.0036 (13) |
C12 | 0.0558 (16) | 0.082 (2) | 0.0895 (19) | −0.0015 (15) | −0.0086 (15) | 0.0005 (17) |
C13 | 0.077 (2) | 0.0712 (19) | 0.0669 (16) | 0.0156 (16) | −0.0055 (15) | 0.0065 (15) |
C14 | 0.081 (2) | 0.0649 (18) | 0.0718 (17) | −0.0027 (15) | 0.0073 (15) | 0.0087 (14) |
C15 | 0.0594 (15) | 0.0704 (18) | 0.0684 (16) | −0.0092 (14) | −0.0012 (13) | 0.0031 (14) |
C16 | 0.0609 (16) | 0.0543 (16) | 0.0539 (14) | −0.0019 (13) | 0.0018 (12) | 0.0018 (13) |
C17 | 0.0590 (16) | 0.0574 (16) | 0.0563 (14) | 0.0011 (13) | 0.0019 (12) | 0.0011 (12) |
C18 | 0.0620 (16) | 0.0724 (18) | 0.0674 (16) | 0.0034 (14) | −0.0003 (13) | 0.0047 (14) |
C19 | 0.0699 (17) | 0.0595 (16) | 0.0615 (15) | 0.0059 (14) | 0.0080 (13) | 0.0090 (13) |
C20 | 0.086 (2) | 0.0636 (17) | 0.0593 (15) | −0.0017 (15) | 0.0043 (14) | −0.0079 (13) |
C21 | 0.0655 (16) | 0.0726 (18) | 0.0690 (16) | −0.0041 (14) | 0.0003 (13) | −0.0104 (15) |
O1 | 0.1117 (16) | 0.1008 (16) | 0.1070 (15) | 0.0137 (13) | 0.0386 (13) | −0.0309 (14) |
O2 | 0.0819 (15) | 0.161 (2) | 0.1135 (17) | 0.0187 (15) | 0.0192 (14) | −0.0283 (15) |
C22 | 0.094 (2) | 0.084 (2) | 0.0708 (19) | 0.014 (2) | 0.0188 (18) | 0.0010 (17) |
C23 | 0.135 (3) | 0.159 (4) | 0.157 (3) | 0.020 (3) | 0.054 (3) | −0.062 (3) |
C24A | 0.163 (10) | 0.085 (5) | 0.134 (6) | 0.013 (5) | 0.067 (7) | −0.017 (5) |
C24B | 0.163 (10) | 0.085 (5) | 0.134 (6) | 0.013 (5) | 0.067 (7) | −0.017 (5) |
C24C | 0.163 (10) | 0.085 (5) | 0.134 (6) | 0.013 (5) | 0.067 (7) | −0.017 (5) |
F1—C13 | 1.356 (3) | C16—C21 | 1.377 (3) |
N1—C16 | 1.376 (3) | C16—C17 | 1.393 (3) |
N1—C8 | 1.376 (3) | C17—C18 | 1.379 (3) |
N1—C9 | 1.456 (3) | C18—C19 | 1.378 (3) |
N2—C8 | 1.319 (3) | C18—H18 | 0.9300 |
N2—C17 | 1.385 (3) | C19—C20 | 1.396 (3) |
N3—C7 | 1.138 (3) | C19—C22 | 1.476 (4) |
C1—C2 | 1.376 (3) | C20—C21 | 1.375 (3) |
C1—C6 | 1.386 (3) | C20—H20 | 0.9300 |
C1—H1 | 0.9300 | C21—H21 | 0.9300 |
C2—C3 | 1.372 (3) | O1—C22 | 1.328 (3) |
C2—H2 | 0.9300 | O1—C23 | 1.460 (4) |
C3—C4 | 1.381 (3) | O2—C22 | 1.198 (3) |
C3—C7 | 1.436 (4) | C23—C24A | 1.227 (10) |
C4—C5 | 1.375 (3) | C23—C24C | 1.37 (2) |
C4—H4 | 0.9300 | C23—C24B | 1.48 (2) |
C5—C6 | 1.385 (3) | C23—H23A | 0.9700 |
C5—H5 | 0.9300 | C23—H23B | 0.9700 |
C6—C8 | 1.467 (3) | C23—H23C | 0.9700 |
C9—C10 | 1.505 (3) | C23—H23D | 0.9700 |
C9—H9A | 0.9700 | C23—H23E | 0.9700 |
C9—H9B | 0.9700 | C23—H23F | 0.9700 |
C10—C15 | 1.372 (3) | C24A—H24A | 0.9600 |
C10—C11 | 1.375 (3) | C24A—H24B | 0.9600 |
C11—C12 | 1.371 (3) | C24A—H24C | 0.9600 |
C11—H11 | 0.9300 | C24B—H24D | 0.9600 |
C12—C13 | 1.348 (3) | C24B—H24E | 0.9600 |
C12—H12 | 0.9300 | C24B—H24F | 0.9600 |
C13—C14 | 1.362 (3) | C24C—H24G | 0.9600 |
C14—C15 | 1.377 (3) | C24C—H24H | 0.9600 |
C14—H14 | 0.9300 | C24C—H24I | 0.9600 |
C15—H15 | 0.9300 | ||
C16—N1—C8 | 106.45 (18) | C18—C17—C16 | 119.5 (2) |
C16—N1—C9 | 122.88 (19) | N2—C17—C16 | 110.2 (2) |
C8—N1—C9 | 130.0 (2) | C19—C18—C17 | 119.0 (2) |
C8—N2—C17 | 104.81 (19) | C19—C18—H18 | 120.5 |
C2—C1—C6 | 120.7 (2) | C17—C18—H18 | 120.5 |
C2—C1—H1 | 119.6 | C18—C19—C20 | 120.5 (2) |
C6—C1—H1 | 119.6 | C18—C19—C22 | 117.1 (3) |
C3—C2—C1 | 120.2 (2) | C20—C19—C22 | 122.4 (3) |
C3—C2—H2 | 119.9 | C21—C20—C19 | 121.4 (2) |
C1—C2—H2 | 119.9 | C21—C20—H20 | 119.3 |
C2—C3—C4 | 119.8 (2) | C19—C20—H20 | 119.3 |
C2—C3—C7 | 119.8 (3) | C20—C21—C16 | 117.3 (2) |
C4—C3—C7 | 120.5 (2) | C20—C21—H21 | 121.4 |
C5—C4—C3 | 120.0 (2) | C16—C21—H21 | 121.4 |
C5—C4—H4 | 120.0 | C22—O1—C23 | 116.3 (3) |
C3—C4—H4 | 120.0 | O2—C22—O1 | 122.8 (3) |
C4—C5—C6 | 120.9 (2) | O2—C22—C19 | 124.5 (3) |
C4—C5—H5 | 119.6 | O1—C22—C19 | 112.7 (3) |
C6—C5—H5 | 119.6 | C24A—C23—O1 | 118.5 (7) |
C5—C6—C1 | 118.5 (2) | C24C—C23—O1 | 116.3 (10) |
C5—C6—C8 | 118.4 (2) | C24B—C23—O1 | 102.6 (10) |
C1—C6—C8 | 123.1 (2) | C24A—C23—H23A | 107.7 |
N3—C7—C3 | 178.3 (4) | O1—C23—H23A | 107.7 |
N2—C8—N1 | 112.8 (2) | C24A—C23—H23B | 107.7 |
N2—C8—C6 | 122.4 (2) | O1—C23—H23B | 107.7 |
N1—C8—C6 | 124.8 (2) | H23A—C23—H23B | 107.1 |
N1—C9—C10 | 114.12 (18) | C24B—C23—H23C | 111.2 |
N1—C9—H9A | 108.7 | O1—C23—H23C | 111.2 |
C10—C9—H9A | 108.7 | C24B—C23—H23D | 111.2 |
N1—C9—H9B | 108.7 | O1—C23—H23D | 111.2 |
C10—C9—H9B | 108.7 | H23C—C23—H23D | 109.2 |
H9A—C9—H9B | 107.6 | C24C—C23—H23E | 108.2 |
C15—C10—C11 | 118.7 (2) | O1—C23—H23E | 108.2 |
C15—C10—C9 | 123.0 (2) | C24C—C23—H23F | 108.2 |
C11—C10—C9 | 118.3 (2) | O1—C23—H23F | 108.2 |
C12—C11—C10 | 121.1 (2) | H23E—C23—H23F | 107.4 |
C12—C11—H11 | 119.5 | C23—C24A—H24A | 109.5 |
C10—C11—H11 | 119.5 | C23—C24A—H24B | 109.5 |
C13—C12—C11 | 118.6 (2) | H24A—C24A—H24B | 109.5 |
C13—C12—H12 | 120.7 | C23—C24A—H24C | 109.5 |
C11—C12—H12 | 120.7 | H24A—C24A—H24C | 109.5 |
C12—C13—F1 | 118.9 (3) | H24B—C24A—H24C | 109.5 |
C12—C13—C14 | 122.6 (2) | C23—C24B—H24D | 109.5 |
F1—C13—C14 | 118.5 (3) | C23—C24B—H24E | 109.5 |
C13—C14—C15 | 118.3 (2) | H24D—C24B—H24E | 109.5 |
C13—C14—H14 | 120.9 | C23—C24B—H24F | 109.5 |
C15—C14—H14 | 120.9 | H24D—C24B—H24F | 109.5 |
C10—C15—C14 | 120.8 (2) | H24E—C24B—H24F | 109.5 |
C10—C15—H15 | 119.6 | C23—C24C—H24G | 109.5 |
C14—C15—H15 | 119.6 | C23—C24C—H24H | 109.5 |
N1—C16—C21 | 131.9 (2) | H24G—C24C—H24H | 109.5 |
N1—C16—C17 | 105.7 (2) | C23—C24C—H24I | 109.5 |
C21—C16—C17 | 122.4 (2) | H24G—C24C—H24I | 109.5 |
C18—C17—N2 | 130.3 (2) | H24H—C24C—H24I | 109.5 |
C6—C1—C2—C3 | −0.7 (4) | C11—C10—C15—C14 | 0.2 (3) |
C1—C2—C3—C4 | 0.8 (4) | C9—C10—C15—C14 | 179.6 (2) |
C1—C2—C3—C7 | −178.2 (2) | C13—C14—C15—C10 | −0.8 (4) |
C2—C3—C4—C5 | −0.1 (4) | C8—N1—C16—C21 | 178.9 (2) |
C7—C3—C4—C5 | 178.9 (2) | C9—N1—C16—C21 | −9.5 (4) |
C3—C4—C5—C6 | −0.7 (4) | C8—N1—C16—C17 | −0.7 (2) |
C4—C5—C6—C1 | 0.8 (4) | C9—N1—C16—C17 | 170.88 (19) |
C4—C5—C6—C8 | −176.5 (2) | C8—N2—C17—C18 | −179.6 (2) |
C2—C1—C6—C5 | −0.1 (3) | C8—N2—C17—C16 | −0.5 (2) |
C2—C1—C6—C8 | 177.0 (2) | N1—C16—C17—C18 | 180.0 (2) |
C17—N2—C8—N1 | 0.0 (2) | C21—C16—C17—C18 | 0.3 (3) |
C17—N2—C8—C6 | 178.0 (2) | N1—C16—C17—N2 | 0.8 (3) |
C16—N1—C8—N2 | 0.5 (3) | C21—C16—C17—N2 | −178.9 (2) |
C9—N1—C8—N2 | −170.3 (2) | N2—C17—C18—C19 | 178.9 (2) |
C16—N1—C8—C6 | −177.5 (2) | C16—C17—C18—C19 | −0.1 (3) |
C9—N1—C8—C6 | 11.7 (4) | C17—C18—C19—C20 | −0.2 (4) |
C5—C6—C8—N2 | 32.9 (3) | C17—C18—C19—C22 | −178.1 (2) |
C1—C6—C8—N2 | −144.3 (2) | C18—C19—C20—C21 | 0.4 (4) |
C5—C6—C8—N1 | −149.4 (2) | C22—C19—C20—C21 | 178.2 (2) |
C1—C6—C8—N1 | 33.5 (3) | C19—C20—C21—C16 | −0.2 (4) |
C16—N1—C9—C10 | 77.3 (3) | N1—C16—C21—C20 | −179.7 (2) |
C8—N1—C9—C10 | −113.2 (3) | C17—C16—C21—C20 | −0.2 (4) |
N1—C9—C10—C15 | 19.3 (3) | C23—O1—C22—O2 | 5.3 (5) |
N1—C9—C10—C11 | −161.2 (2) | C23—O1—C22—C19 | −175.9 (3) |
C15—C10—C11—C12 | 0.4 (3) | C18—C19—C22—O2 | 1.2 (4) |
C9—C10—C11—C12 | −179.1 (2) | C20—C19—C22—O2 | −176.7 (3) |
C10—C11—C12—C13 | −0.4 (4) | C18—C19—C22—O1 | −177.6 (2) |
C11—C12—C13—F1 | −179.8 (2) | C20—C19—C22—O1 | 4.5 (4) |
C11—C12—C13—C14 | −0.2 (4) | C22—O1—C23—C24A | −108.1 (10) |
C12—C13—C14—C15 | 0.8 (4) | C22—O1—C23—C24C | −172.1 (14) |
F1—C13—C14—C15 | −179.6 (2) | C22—O1—C23—C24B | 176.4 (12) |
Acknowledgements
The authors thank DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility.
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