Ethyl 1-benzyl-2-(3-chloro­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Kumar, S.M.; Manasa, D.; Kumar, V.; Poojary, B.; Byrappa, K.; Abdoh, M.M.M.

doi:10.1107/S2414314616010683

organic compounds

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ISSN: 2414-3146

Volume 1| Part 7| July 2016| x161068

https://doi.org/10.1107/S2414314616010683

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Ethyl 1-benzyl-2-(3-chlorophenyl)-1H-benzimidazole-5-carboxylate

S. Madan Kumar,^a D. Manasa,^b Vasantha Kumar,^c,^d Boja Poojary,^c K. Byrappa ^e and M. M. M. Abdoh ^f ^*

^aPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India, ^bDepartment of Physics, Bharathi Composite PU College, Bharthi Nagara, Mandya 571 422, India, ^cDepartment of Chemistry, Mangalore University, Mangaluru 574 199, India, ^dPG Department of Chemistry, SDM College (Autonomous), Ujire, India 574 240, India, ^eDepartment of Material Science, Mangalore University, Mangaluru 574 199, India, and ^fDepartment of Physics, Faculty of Science, An Najah National, University, Nabtus, West Bank, Palestinian Territories
^*Correspondence e-mail: muneer@najah.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 June 2016; accepted 1 July 2016; online 12 July 2016)

In the title compound, C₂₃H₁₉ClN₂O₂, the dihedral angles between the imidazole ring system and the chlorobenzene and phenyl rings are 48.05 (14) and 82.53 (15)°, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R₂²(22) loops. Weak C—H⋯π and π–π stacking interactions are also observed.

Keywords: crystal structure; benzimidazole-5-carboxylate.

CCDC reference: 1431411

Structure description

As part of our research on the synthesis and crystal structures of 1,2-disubstituted benzimidazole-5-carboxylates, we report here the crystal and molecular structure of ethyl 1-benzyl-2-(3-chlorophenyl)-1H-benzimidazole-5-carboxylate, (I). The molecular structure of (I) is shown in Fig. 1 and the dihedral angle between the chlorobenzene (C11–C16) and phenyl (C1–C6) rings is 74.06 (18)°.

Figure 1
The molecular structure of (I), showing 50% displacement ellipsods.

In the crystal (Fig. 2), molecules are linked into inversion dimers through pairs of C1—H1⋯O2 hydrogen bonds, forming an $[R_{2}^{2}]$ (22) loop (Table 1) and a weak C—H⋯π bond is observed. Aromatic π–π stacking, with a centroid–centroid distance of 3.866 (2) Å [Cg1⋯Cg2, where Cg1 and Cg2(−x + 2, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ) are the centroids of rings N1/C8/C9/N2/C10 and C1–C6, respectively], also occurs.

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.93	2.54	3.358 (4)	148
C20—H20⋯Cg4ⁱⁱ	0.93	2.87	3.757 (4)	159
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The packing of (I), viewed down [001].

Synthesis and crystallization

Sodium dithionite (3.0 equivalents) was added to a stirred solution of ethyl 4-benzylamino-3-nitrobenzoate (0.01 mol, 1.0 equivalent) and 3-chlorobenzaldehyde (0.01 mol, 1.0 equivalent) in DMSO (20 ml). The reaction mixture was stirred at 363 K for 3 h. After completion of the reaction (monitored by TLC; hexane–ethyl acetate 7:3 v/v), it was poured onto crushed ice. The solid separated was filtered off, washed with water and dried. The product was recrystallized from N,N-dimethyformamide solution to yield colourless blocks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₉ClN₂O₂
M_r	390.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.145 (3), 9.878 (2), 18.355 (4)
β (°)	93.952 (7)
V (Å³)	2015.9 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.26 × 0.21

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku 1999 )
T_min, T_max	0.935, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	14125, 4498, 2287
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.185, 1.04
No. of reflections	4498
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29
Computer programs: CrystalClear SM Expert (Rigaku, 2011 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1431411

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616010683/hb4064sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616010683/hb4064Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616010683/hb4064Isup3.cml

checkCIF report

Computing details top

Data collection: CrystalClear SM Expert (Rigaku, 2011); cell refinement: CrystalClear SM Expert (Rigaku, 2011); data reduction: CrystalClear SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (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).

Ethyl 1-benzyl-2-(3-chlorophenyl)-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₃H₁₉ClN₂O₂	F(000) = 816
M_r = 390.85	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 11.145 (3) Å	Cell parameters from 4498 reflections
b = 9.878 (2) Å	θ = 3.0–27.5°
c = 18.355 (4) Å	µ = 0.21 mm⁻¹
β = 93.952 (7)°	T = 296 K
V = 2015.9 (8) Å³	Block, colourless
Z = 4	0.32 × 0.26 × 0.21 mm

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.048
profile data from ω–scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (NUMABS; Rigaku 1999)	h = −14→14
T_min = 0.935, T_max = 0.957	k = −12→12
14125 measured reflections	l = −23→23
4498 independent reflections	4498 standard reflections
2287 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.185	w = 1/[σ²(F_o²) + (0.0581P)² + 1.0114P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4498 reflections	Δρ_max = 0.22 e Å⁻³
254 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.51971 (9)	0.95208 (12)	0.21673 (7)	0.1007 (4)
O1	1.3420 (2)	0.3900 (3)	0.50007 (13)	0.0834 (8)
N1	0.9704 (2)	0.7556 (3)	0.32335 (13)	0.0537 (6)
C6	0.8897 (3)	0.6538 (3)	0.20635 (16)	0.0509 (8)
C9	1.0335 (3)	0.7003 (3)	0.43583 (16)	0.0534 (8)
C8	1.0530 (3)	0.6769 (3)	0.36265 (16)	0.0520 (8)
N2	0.9413 (2)	0.7933 (3)	0.44078 (15)	0.0626 (7)
C17	1.1037 (3)	0.6343 (3)	0.48961 (17)	0.0595 (8)
H17	1.0919	0.6482	0.5387	0.071*
C18	1.1919 (3)	0.5472 (3)	0.46873 (17)	0.0562 (8)
C7	0.9609 (3)	0.7653 (3)	0.24414 (16)	0.0585 (8)
H7A	1.0413	0.7652	0.2270	0.070*
H7B	0.9238	0.8512	0.2303	0.070*
C16	0.7209 (3)	0.8924 (3)	0.30033 (18)	0.0627 (9)
H16	0.7198	0.8098	0.2760	0.075*
C21	1.2678 (3)	0.4790 (4)	0.5267 (2)	0.0688 (10)
C11	0.8119 (3)	0.9214 (3)	0.35294 (18)	0.0582 (8)
C20	1.1417 (3)	0.5909 (3)	0.34119 (17)	0.0586 (8)
H20	1.1541	0.5770	0.2922	0.070*
C5	0.8807 (3)	0.6533 (4)	0.13092 (18)	0.0727 (10)
H5	0.9178	0.7216	0.1058	0.087*
O2	1.2644 (3)	0.5004 (3)	0.59070 (15)	0.1004 (10)
C10	0.9073 (3)	0.8236 (3)	0.37328 (18)	0.0555 (8)
C19	1.2099 (3)	0.5275 (3)	0.39501 (18)	0.0611 (9)
H19	1.2705	0.4691	0.3823	0.073*
C1	0.8341 (3)	0.5539 (3)	0.24296 (18)	0.0608 (9)
H1	0.8386	0.5532	0.2937	0.073*
C12	0.8114 (3)	1.0456 (3)	0.3880 (2)	0.0725 (10)
H12	0.8721	1.0665	0.4236	0.087*
C14	0.6328 (4)	1.1091 (4)	0.3193 (2)	0.0830 (12)
H14	0.5727	1.1725	0.3079	0.100*
C2	0.7709 (3)	0.4538 (4)	0.2039 (2)	0.0799 (11)
H2	0.7324	0.3858	0.2284	0.096*
C15	0.6316 (3)	0.9865 (4)	0.2840 (2)	0.0687 (10)
C3	0.7650 (4)	0.4553 (5)	0.1288 (3)	0.0900 (13)
H3	0.7239	0.3871	0.1026	0.108*
C4	0.8189 (4)	0.5554 (5)	0.0930 (2)	0.0959 (14)
H4	0.8135	0.5570	0.0422	0.115*
C13	0.7226 (4)	1.1370 (4)	0.3709 (2)	0.0867 (12)
H13	0.7235	1.2200	0.3949	0.104*
C22	1.4205 (4)	0.3153 (5)	0.5511 (2)	0.1122 (16)
H22A	1.4797	0.3756	0.5750	0.135*
H22B	1.3745	0.2742	0.5882	0.135*
C23	1.4792 (6)	0.2127 (7)	0.5113 (4)	0.184 (3)
H23A	1.5219	0.2542	0.4735	0.276*
H23B	1.4202	0.1511	0.4899	0.276*
H23C	1.5348	0.1642	0.5439	0.276*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0690 (6)	0.1118 (9)	0.1198 (10)	−0.0021 (6)	−0.0056 (6)	0.0058 (7)
O1	0.0883 (18)	0.0881 (18)	0.0733 (17)	0.0306 (15)	0.0018 (14)	0.0091 (14)
N1	0.0645 (16)	0.0493 (15)	0.0478 (15)	0.0035 (13)	0.0081 (13)	−0.0047 (12)
C6	0.0536 (17)	0.055 (2)	0.0442 (18)	0.0093 (15)	0.0078 (14)	0.0019 (15)
C9	0.0639 (19)	0.0501 (19)	0.0470 (19)	−0.0026 (16)	0.0088 (15)	−0.0090 (15)
C8	0.0611 (19)	0.0429 (18)	0.0520 (19)	0.0000 (15)	0.0041 (15)	−0.0054 (15)
N2	0.0725 (18)	0.0609 (18)	0.0551 (18)	0.0096 (14)	0.0101 (14)	−0.0090 (14)
C17	0.068 (2)	0.066 (2)	0.0446 (18)	−0.0028 (18)	0.0066 (16)	−0.0067 (16)
C18	0.0587 (19)	0.057 (2)	0.053 (2)	−0.0003 (16)	0.0030 (15)	−0.0002 (16)
C7	0.067 (2)	0.059 (2)	0.0499 (19)	0.0057 (17)	0.0119 (16)	0.0058 (16)
C16	0.066 (2)	0.053 (2)	0.071 (2)	−0.0004 (17)	0.0182 (18)	−0.0003 (17)
C21	0.075 (2)	0.070 (2)	0.061 (2)	−0.002 (2)	0.004 (2)	0.0052 (19)
C11	0.065 (2)	0.050 (2)	0.061 (2)	0.0029 (16)	0.0153 (17)	−0.0004 (16)
C20	0.072 (2)	0.057 (2)	0.0472 (19)	0.0066 (17)	0.0067 (16)	−0.0095 (16)
C5	0.082 (2)	0.088 (3)	0.049 (2)	0.003 (2)	0.0085 (18)	0.005 (2)
O2	0.118 (2)	0.128 (3)	0.0543 (17)	0.0326 (19)	−0.0011 (15)	0.0054 (16)
C10	0.066 (2)	0.0480 (19)	0.054 (2)	0.0010 (16)	0.0112 (16)	−0.0060 (16)
C19	0.068 (2)	0.057 (2)	0.059 (2)	0.0052 (17)	0.0108 (17)	−0.0074 (17)
C1	0.068 (2)	0.062 (2)	0.0523 (19)	0.0029 (18)	0.0063 (16)	0.0027 (17)
C12	0.078 (2)	0.059 (2)	0.081 (3)	0.0066 (19)	0.011 (2)	−0.008 (2)
C14	0.079 (3)	0.065 (3)	0.107 (3)	0.022 (2)	0.017 (2)	0.007 (2)
C2	0.069 (2)	0.070 (3)	0.101 (3)	−0.002 (2)	0.011 (2)	−0.001 (2)
C15	0.058 (2)	0.071 (3)	0.079 (2)	−0.0002 (18)	0.0146 (18)	0.009 (2)
C3	0.078 (3)	0.103 (4)	0.086 (3)	0.005 (2)	−0.021 (2)	−0.032 (3)
C4	0.106 (3)	0.123 (4)	0.057 (3)	−0.005 (3)	−0.007 (2)	−0.014 (3)
C13	0.089 (3)	0.064 (3)	0.107 (3)	0.017 (2)	0.003 (3)	−0.017 (2)
C22	0.119 (4)	0.121 (4)	0.095 (3)	0.039 (3)	−0.010 (3)	0.027 (3)
C23	0.165 (6)	0.183 (6)	0.194 (7)	0.103 (5)	−0.066 (5)	−0.041 (5)

Geometric parameters (Å, º) top

Cl1—C15	1.728 (4)	C11—C12	1.386 (4)
O1—C21	1.324 (4)	C20—H20	0.9300
O1—C22	1.440 (4)	C20—C19	1.357 (4)
N1—C8	1.372 (4)	C5—H5	0.9300
N1—C7	1.454 (4)	C5—C4	1.352 (5)
N1—C10	1.369 (4)	C19—H19	0.9300
C6—C7	1.499 (4)	C1—H1	0.9300
C6—C5	1.381 (4)	C1—C2	1.385 (5)
C6—C1	1.367 (4)	C12—H12	0.9300
C9—C8	1.395 (4)	C12—C13	1.360 (5)
C9—N2	1.387 (4)	C14—H14	0.9300
C9—C17	1.380 (4)	C14—C15	1.373 (5)
C8—C20	1.381 (4)	C14—C13	1.359 (5)
N2—C10	1.305 (4)	C2—H2	0.9300
C17—H17	0.9300	C2—C3	1.375 (5)
C17—C18	1.380 (4)	C3—H3	0.9300
C18—C21	1.475 (5)	C3—C4	1.351 (6)
C18—C19	1.395 (4)	C4—H4	0.9300
C7—H7A	0.9700	C13—H13	0.9300
C7—H7B	0.9700	C22—H22A	0.9700
C16—H16	0.9300	C22—H22B	0.9700
C16—C11	1.381 (4)	C22—C23	1.433 (7)
C16—C15	1.379 (5)	C23—H23A	0.9600
C21—O2	1.197 (4)	C23—H23B	0.9600
C11—C10	1.465 (4)	C23—H23C	0.9600

C21—O1—C22	117.9 (3)	N2—C10—N1	113.2 (3)
C8—N1—C7	124.3 (3)	N2—C10—C11	123.4 (3)
C10—N1—C8	106.5 (3)	C18—C19—H19	119.0
C10—N1—C7	129.2 (3)	C20—C19—C18	122.1 (3)
C5—C6—C7	117.8 (3)	C20—C19—H19	119.0
C1—C6—C7	123.1 (3)	C6—C1—H1	120.2
C1—C6—C5	119.1 (3)	C6—C1—C2	119.5 (3)
N2—C9—C8	109.8 (3)	C2—C1—H1	120.2
C17—C9—C8	119.5 (3)	C11—C12—H12	119.8
C17—C9—N2	130.7 (3)	C13—C12—C11	120.5 (4)
N1—C8—C9	105.6 (3)	C13—C12—H12	119.8
N1—C8—C20	131.8 (3)	C15—C14—H14	120.3
C20—C8—C9	122.6 (3)	C13—C14—H14	120.3
C10—N2—C9	104.9 (2)	C13—C14—C15	119.4 (4)
C9—C17—H17	120.8	C1—C2—H2	120.0
C9—C17—C18	118.4 (3)	C3—C2—C1	119.9 (4)
C18—C17—H17	120.8	C3—C2—H2	120.0
C17—C18—C21	117.9 (3)	C16—C15—Cl1	119.8 (3)
C17—C18—C19	120.6 (3)	C14—C15—Cl1	119.6 (3)
C19—C18—C21	121.5 (3)	C14—C15—C16	120.6 (4)
N1—C7—C6	114.5 (3)	C2—C3—H3	119.9
N1—C7—H7A	108.6	C4—C3—C2	120.2 (4)
N1—C7—H7B	108.6	C4—C3—H3	119.9
C6—C7—H7A	108.6	C5—C4—H4	120.0
C6—C7—H7B	108.6	C3—C4—C5	120.1 (4)
H7A—C7—H7B	107.6	C3—C4—H4	120.0
C11—C16—H16	120.1	C12—C13—H13	119.5
C15—C16—H16	120.1	C14—C13—C12	121.0 (4)
C15—C16—C11	119.8 (3)	C14—C13—H13	119.5
O1—C21—C18	112.3 (3)	O1—C22—H22A	110.1
O2—C21—O1	122.8 (3)	O1—C22—H22B	110.1
O2—C21—C18	124.9 (4)	H22A—C22—H22B	108.4
C16—C11—C10	121.8 (3)	C23—C22—O1	108.0 (4)
C16—C11—C12	118.8 (3)	C23—C22—H22A	110.1
C12—C11—C10	119.4 (3)	C23—C22—H22B	110.1
C8—C20—H20	121.6	C22—C23—H23A	109.5
C19—C20—C8	116.9 (3)	C22—C23—H23B	109.5
C19—C20—H20	121.6	C22—C23—H23C	109.5
C6—C5—H5	119.4	H23A—C23—H23B	109.5
C4—C5—C6	121.2 (4)	H23A—C23—H23C	109.5
C4—C5—H5	119.4	H23B—C23—H23C	109.5
N1—C10—C11	123.4 (3)

N1—C8—C20—C19	179.6 (3)	C16—C11—C10—N1	48.3 (5)
C6—C5—C4—C3	−0.3 (6)	C16—C11—C10—N2	−132.2 (3)
C6—C1—C2—C3	0.3 (5)	C16—C11—C12—C13	0.0 (5)
C9—C8—C20—C19	0.7 (5)	C21—O1—C22—C23	171.8 (5)
C9—N2—C10—N1	0.6 (4)	C21—C18—C19—C20	−179.2 (3)
C9—N2—C10—C11	−178.9 (3)	C11—C16—C15—Cl1	178.5 (2)
C9—C17—C18—C21	179.0 (3)	C11—C16—C15—C14	0.4 (5)
C9—C17—C18—C19	0.5 (5)	C11—C12—C13—C14	0.0 (6)
C8—N1—C7—C6	83.0 (4)	C5—C6—C7—N1	−177.5 (3)
C8—N1—C10—N2	−1.1 (4)	C5—C6—C1—C2	0.6 (5)
C8—N1—C10—C11	178.5 (3)	C10—N1—C8—C9	1.0 (3)
C8—C9—N2—C10	0.1 (3)	C10—N1—C8—C20	−178.0 (3)
C8—C9—C17—C18	0.3 (5)	C10—N1—C7—C6	−100.5 (4)
C8—C20—C19—C18	0.2 (5)	C10—C11—C12—C13	−178.9 (3)
N2—C9—C8—N1	−0.7 (3)	C19—C18—C21—O1	−6.7 (5)
N2—C9—C8—C20	178.4 (3)	C19—C18—C21—O2	173.0 (4)
N2—C9—C17—C18	−178.9 (3)	C1—C6—C7—N1	2.5 (4)
C17—C9—C8—N1	179.9 (3)	C1—C6—C5—C4	−0.6 (5)
C17—C9—C8—C20	−0.9 (5)	C1—C2—C3—C4	−1.2 (6)
C17—C9—N2—C10	179.4 (3)	C12—C11—C10—N1	−132.8 (3)
C17—C18—C21—O1	174.8 (3)	C12—C11—C10—N2	46.6 (5)
C17—C18—C21—O2	−5.5 (5)	C2—C3—C4—C5	1.2 (7)
C17—C18—C19—C20	−0.7 (5)	C15—C16—C11—C10	178.6 (3)
C7—N1—C8—C9	178.2 (3)	C15—C16—C11—C12	−0.3 (5)
C7—N1—C8—C20	−0.9 (5)	C15—C14—C13—C12	0.2 (6)
C7—N1—C10—N2	−178.0 (3)	C13—C14—C15—Cl1	−178.4 (3)
C7—N1—C10—C11	1.5 (5)	C13—C14—C15—C16	−0.4 (6)
C7—C6—C5—C4	179.4 (3)	C22—O1—C21—C18	−179.5 (3)
C7—C6—C1—C2	−179.5 (3)	C22—O1—C21—O2	0.8 (6)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.54	3.358 (4)	148
C20—H20···Cg4ⁱⁱ	0.93	2.87	3.757 (4)	159

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+1/2.

Acknowledgements

The Authors thank DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals 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
Rigaku. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2011). CrystalClear SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 1| Part 7| July 2016| x161068

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-benzyl-2-(3-chloro­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Ethyl 1-benzyl-2-(3-chlorophenyl)-1H-benzimidazole-5-carboxylate