Ethyl 1-benzyl-2-(4-meth­oxy­phen­yl)-1H-benzimid­azole-5-carboxyl­ate

Naveen, S.; Kumar, V.; Poojary, B.; Shivarama Holla, B.; Lokanath, N.K.; Abdoh, M.M.M.

doi:10.1107/S2414314616017594

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161759

https://doi.org/10.1107/S2414314616017594

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Ethyl 1-benzyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate

S. Naveen,^a Vasantha Kumar,^b,^c Boja Poojary,^c B. Shivarama Holla,^b N. K. Lokanath ^d and M. M. M. Abdoh ^e ^*

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 October 2016; accepted 3 November 2016; online 8 November 2016)

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 crystal structure 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)°.

Figure 1
A view of the molecular structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

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).

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 2
A view along the b axis of the title compound, showing layered stacking. The dotted lines represent hydrogen bonds.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂O₃
M_r	386.44
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	10.3178 (11), 10.6067 (11), 10.9071 (12)
α, β, γ (°)	112.306 (3), 104.249 (4), 101.904 (4)
V (Å³)	1008.81 (19)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.68
Crystal size (mm)	0.28 × 0.25 × 0.22

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.832, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	13401, 3314, 2905
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.585

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.204, 1.05
No. of reflections	3314
No. of parameters	264
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.35
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1514744

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616017594/hb4091sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: 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).

Ethyl 1-benzyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₄H₂₂N₂O₃	Z = 2
M_r = 386.44	F(000) = 408
Triclinic, P1	D_x = 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

Data collection top

Bruker X8 Proteum diffractometer	3314 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2905 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.043
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.5°, θ_min = 4.7°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.832, T_max = 0.865	l = −12→12
13401 measured reflections

Refinement top

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(F_o²) + (0.1321P)² + 0.249P] where P = (F_o² + 2F_c²)/3
3314 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

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 U_iso(H) =1.5U_eq(C-methyl) and = 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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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