Ethyl 2-(4-bromo-phen-yl)-1-phenyl-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(22)H(17)BrN(2)O(2), the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017 (1) Å, and forms dihedral angles of 27.79 (6) and 64.43 (6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, mol-ecules are linked into one-dimensional chains along the a axis by weak C-H⋯O hydrogen bonds. Weak inter-molecular C-H⋯π inter-actions are also present.

Related literature

For background to and the biological activities of benzimidazoles, see: Townsend & Revankar (1970 ▶); Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); Dubey & Sanyal (2010 ▶); Lacey (1990 ▶). For a related structure, see: Arumugam et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H17BrN2O2

M = 421.29

Triclinic,

a = 9.3121 (2) Å

b = 9.8136 (2) Å

c = 11.8458 (2) Å

α = 108.217 (1)°

β = 101.135 (1)°

γ = 109.361 (1)°

V = 915.39 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.27 mm−1

T = 100 K

0.42 × 0.33 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.450, T max = 0.728

21718 measured reflections

5326 independent reflections

4846 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.071

S = 1.06

5326 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019897/lh5466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019897/lh5466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019897/lh5466Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H17BrN2O2	Z = 2
Mr = 421.29	F(000) = 428
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3121 (2) Å	Cell parameters from 9874 reflections
b = 9.8136 (2) Å	θ = 2.4–32.7°
c = 11.8458 (2) Å	µ = 2.27 mm−1
α = 108.217 (1)°	T = 100 K
β = 101.135 (1)°	Block, colourless
γ = 109.361 (1)°	0.42 × 0.33 × 0.15 mm
V = 915.39 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5326 independent reflections
Radiation source: fine-focus sealed tube	4846 reflections with I > I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.450, Tmax = 0.728	k = −13→13
21718 measured reflections	l = −16→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.3723P] where P = (Fo2 + 2Fc2)/3
5326 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
Br1	−0.680059 (17)	−0.321236 (17)	−0.071893 (14)	0.02360 (5)
O1	0.66395 (12)	−0.10601 (12)	0.40079 (10)	0.0201 (2)
O2	0.84619 (13)	0.14498 (13)	0.46778 (10)	0.0230 (2)
N1	0.12223 (14)	−0.10878 (14)	0.20976 (11)	0.0180 (2)
N2	0.16438 (14)	0.14058 (14)	0.23396 (11)	0.0163 (2)
C1	0.31426 (17)	0.14481 (16)	0.28300 (13)	0.0167 (2)
C2	0.46861 (18)	0.26876 (17)	0.34068 (14)	0.0202 (3)
H2A	0.4867	0.3736	0.3505	0.024*
C3	0.59380 (18)	0.23123 (17)	0.38280 (14)	0.0205 (3)
H3A	0.7005	0.3123	0.4226	0.025*
C4	0.56651 (17)	0.07511 (17)	0.36785 (13)	0.0181 (3)
C5	0.41259 (17)	−0.04732 (17)	0.30997 (13)	0.0184 (3)
H5A	0.3946	−0.1522	0.2997	0.022*
C6	0.28543 (17)	−0.01088 (16)	0.26745 (13)	0.0168 (2)
C7	0.05354 (17)	−0.01604 (16)	0.19171 (12)	0.0160 (2)
C8	−0.12145 (16)	−0.07748 (16)	0.13144 (12)	0.0164 (2)
C9	−0.21833 (17)	−0.21394 (17)	0.14191 (13)	0.0182 (3)
H9A	−0.1695	−0.2591	0.1889	0.022*
C10	−0.38444 (17)	−0.28386 (17)	0.08468 (13)	0.0192 (3)
H10A	−0.4497	−0.3741	0.0945	0.023*
C11	−0.45403 (17)	−0.21985 (17)	0.01266 (13)	0.0183 (3)
C12	−0.36095 (17)	−0.08657 (17)	−0.00143 (13)	0.0183 (3)
H12A	−0.4102	−0.0453	−0.0520	0.022*
C13	−0.19447 (17)	−0.01399 (16)	0.05949 (13)	0.0172 (2)
H13A	−0.1303	0.0788	0.0522	0.021*
C14	0.13582 (17)	0.27765 (16)	0.24107 (13)	0.0168 (2)
C15	0.04564 (17)	0.32281 (17)	0.31392 (13)	0.0187 (3)
H15A	0.0000	0.2619	0.3569	0.022*
C16	0.02336 (18)	0.45862 (18)	0.32284 (14)	0.0220 (3)
H16A	−0.0369	0.4914	0.3732	0.026*
C17	0.08845 (19)	0.54698 (18)	0.25870 (15)	0.0236 (3)
H17A	0.0729	0.6397	0.2654	0.028*
C18	0.1760 (2)	0.49909 (18)	0.18500 (15)	0.0250 (3)
H18A	0.2188	0.5582	0.1400	0.030*
C19	0.20176 (19)	0.36444 (17)	0.17651 (14)	0.0208 (3)
H19A	0.2635	0.3326	0.1273	0.025*
C20	0.70792 (17)	0.04581 (17)	0.41792 (13)	0.0183 (3)
C21	0.79333 (17)	−0.14750 (17)	0.44476 (13)	0.0199 (3)
H21A	0.8430	−0.0922	0.5375	0.024*
H21B	0.8778	−0.1179	0.4063	0.024*
C22	0.7174 (2)	−0.32313 (19)	0.40531 (15)	0.0264 (3)
H22A	0.8004	−0.3580	0.4316	0.040*
H22B	0.6670	−0.3758	0.3135	0.040*
H22C	0.6353	−0.3502	0.4451	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.01607 (8)	0.02227 (8)	0.02755 (8)	0.00650 (6)	0.00244 (6)	0.00860 (6)
O1	0.0153 (5)	0.0192 (5)	0.0243 (5)	0.0073 (4)	0.0042 (4)	0.0083 (4)
O2	0.0168 (5)	0.0232 (5)	0.0259 (5)	0.0062 (4)	0.0054 (4)	0.0095 (4)
N1	0.0162 (5)	0.0167 (5)	0.0189 (5)	0.0060 (4)	0.0031 (4)	0.0071 (5)
N2	0.0162 (5)	0.0144 (5)	0.0182 (5)	0.0060 (4)	0.0053 (4)	0.0071 (4)
C1	0.0171 (6)	0.0170 (6)	0.0176 (6)	0.0076 (5)	0.0063 (5)	0.0082 (5)
C2	0.0196 (7)	0.0163 (6)	0.0232 (7)	0.0057 (5)	0.0067 (5)	0.0083 (5)
C3	0.0167 (6)	0.0182 (6)	0.0235 (7)	0.0042 (5)	0.0061 (5)	0.0082 (5)
C4	0.0167 (6)	0.0190 (6)	0.0182 (6)	0.0073 (5)	0.0059 (5)	0.0075 (5)
C5	0.0183 (6)	0.0171 (6)	0.0193 (6)	0.0071 (5)	0.0059 (5)	0.0073 (5)
C6	0.0166 (6)	0.0155 (6)	0.0160 (6)	0.0052 (5)	0.0042 (5)	0.0060 (5)
C7	0.0173 (6)	0.0148 (6)	0.0147 (6)	0.0057 (5)	0.0047 (5)	0.0061 (5)
C8	0.0158 (6)	0.0168 (6)	0.0141 (6)	0.0063 (5)	0.0039 (5)	0.0046 (5)
C9	0.0195 (6)	0.0185 (6)	0.0158 (6)	0.0077 (5)	0.0044 (5)	0.0071 (5)
C10	0.0191 (6)	0.0179 (6)	0.0175 (6)	0.0053 (5)	0.0052 (5)	0.0063 (5)
C11	0.0164 (6)	0.0193 (6)	0.0170 (6)	0.0077 (5)	0.0049 (5)	0.0049 (5)
C12	0.0207 (7)	0.0188 (6)	0.0166 (6)	0.0111 (5)	0.0053 (5)	0.0062 (5)
C13	0.0188 (6)	0.0164 (6)	0.0166 (6)	0.0077 (5)	0.0064 (5)	0.0064 (5)
C14	0.0171 (6)	0.0151 (6)	0.0163 (6)	0.0061 (5)	0.0035 (5)	0.0058 (5)
C15	0.0176 (6)	0.0197 (6)	0.0184 (6)	0.0075 (5)	0.0055 (5)	0.0079 (5)
C16	0.0202 (7)	0.0218 (7)	0.0230 (7)	0.0107 (6)	0.0062 (5)	0.0064 (6)
C17	0.0234 (7)	0.0170 (6)	0.0267 (7)	0.0084 (6)	0.0027 (6)	0.0076 (6)
C18	0.0322 (8)	0.0193 (7)	0.0236 (7)	0.0087 (6)	0.0086 (6)	0.0117 (6)
C19	0.0262 (7)	0.0179 (6)	0.0190 (6)	0.0087 (6)	0.0100 (6)	0.0075 (5)
C20	0.0183 (6)	0.0200 (6)	0.0172 (6)	0.0080 (5)	0.0074 (5)	0.0076 (5)
C21	0.0178 (6)	0.0230 (7)	0.0187 (6)	0.0105 (6)	0.0043 (5)	0.0075 (5)
C22	0.0304 (8)	0.0243 (7)	0.0254 (7)	0.0135 (6)	0.0076 (6)	0.0100 (6)

Br1—C11	1.8967 (14)	C10—C11	1.391 (2)
O1—C20	1.3428 (17)	C10—H10A	0.9500
O1—C21	1.4506 (17)	C11—C12	1.390 (2)
O2—C20	1.2124 (18)	C12—C13	1.3949 (19)
N1—C7	1.3182 (17)	C12—H12A	0.9500
N1—C6	1.3856 (18)	C13—H13A	0.9500
N2—C1	1.3858 (17)	C14—C19	1.3889 (19)
N2—C7	1.3950 (17)	C14—C15	1.3906 (19)
N2—C14	1.4360 (17)	C15—C16	1.391 (2)
C1—C2	1.398 (2)	C15—H15A	0.9500
C1—C6	1.4047 (19)	C16—C17	1.392 (2)
C2—C3	1.385 (2)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.386 (2)
C3—C4	1.414 (2)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.396 (2)
C4—C5	1.3898 (19)	C18—H18A	0.9500
C4—C20	1.4915 (19)	C19—H19A	0.9500
C5—C6	1.3953 (19)	C21—C22	1.500 (2)
C5—H5A	0.9500	C21—H21A	0.9900
C7—C8	1.4692 (19)	C21—H21B	0.9900
C8—C13	1.4022 (19)	C22—H22A	0.9800
C8—C9	1.4031 (19)	C22—H22B	0.9800
C9—C10	1.387 (2)	C22—H22C	0.9800
C9—H9A	0.9500
C20—O1—C21	115.96 (11)	C11—C12—H12A	120.3
C7—N1—C6	105.29 (11)	C13—C12—H12A	120.3
C1—N2—C7	106.01 (11)	C12—C13—C8	120.27 (13)
C1—N2—C14	124.37 (11)	C12—C13—H13A	119.9
C7—N2—C14	129.28 (12)	C8—C13—H13A	119.9
N2—C1—C2	131.97 (13)	C19—C14—C15	121.23 (13)
N2—C1—C6	105.65 (12)	C19—C14—N2	119.07 (12)
C2—C1—C6	122.36 (13)	C15—C14—N2	119.69 (12)
C3—C2—C1	116.72 (13)	C14—C15—C16	118.92 (13)
C3—C2—H2A	121.6	C14—C15—H15A	120.5
C1—C2—H2A	121.6	C16—C15—H15A	120.5
C2—C3—C4	121.52 (13)	C15—C16—C17	120.63 (14)
C2—C3—H3A	119.2	C15—C16—H16A	119.7
C4—C3—H3A	119.2	C17—C16—H16A	119.7
C5—C4—C3	121.27 (13)	C18—C17—C16	119.74 (14)
C5—C4—C20	120.79 (13)	C18—C17—H17A	120.1
C3—C4—C20	117.94 (13)	C16—C17—H17A	120.1
C4—C5—C6	117.74 (13)	C17—C18—C19	120.41 (14)
C4—C5—H5A	121.1	C17—C18—H18A	119.8
C6—C5—H5A	121.1	C19—C18—H18A	119.8
N1—C6—C5	129.29 (13)	C14—C19—C18	119.06 (13)
N1—C6—C1	110.30 (12)	C14—C19—H19A	120.5
C5—C6—C1	120.40 (13)	C18—C19—H19A	120.5
N1—C7—N2	112.74 (12)	O2—C20—O1	123.35 (13)
N1—C7—C8	121.69 (12)	O2—C20—C4	125.07 (13)
N2—C7—C8	125.56 (12)	O1—C20—C4	111.58 (12)
C13—C8—C9	119.05 (13)	O1—C21—C22	106.03 (12)
C13—C8—C7	124.21 (12)	O1—C21—H21A	110.5
C9—C8—C7	116.64 (12)	C22—C21—H21A	110.5
C10—C9—C8	120.93 (13)	O1—C21—H21B	110.5
C10—C9—H9A	119.5	C22—C21—H21B	110.5
C8—C9—H9A	119.5	H21A—C21—H21B	108.7
C9—C10—C11	119.00 (13)	C21—C22—H22A	109.5
C9—C10—H10A	120.5	C21—C22—H22B	109.5
C11—C10—H10A	120.5	H22A—C22—H22B	109.5
C12—C11—C10	121.39 (13)	C21—C22—H22C	109.5
C12—C11—Br1	119.62 (11)	H22A—C22—H22C	109.5
C10—C11—Br1	118.97 (11)	H22B—C22—H22C	109.5
C11—C12—C13	119.32 (13)
C7—N2—C1—C2	−178.43 (15)	C13—C8—C9—C10	−1.5 (2)
C14—N2—C1—C2	−4.5 (2)	C7—C8—C9—C10	−177.86 (12)
C7—N2—C1—C6	0.05 (14)	C8—C9—C10—C11	2.2 (2)
C14—N2—C1—C6	173.96 (12)	C9—C10—C11—C12	−0.9 (2)
N2—C1—C2—C3	178.10 (14)	C9—C10—C11—Br1	177.12 (10)
C6—C1—C2—C3	−0.2 (2)	C10—C11—C12—C13	−1.0 (2)
C1—C2—C3—C4	0.1 (2)	Br1—C11—C12—C13	−179.04 (10)
C2—C3—C4—C5	0.1 (2)	C11—C12—C13—C8	1.7 (2)
C2—C3—C4—C20	−179.00 (13)	C9—C8—C13—C12	−0.5 (2)
C3—C4—C5—C6	−0.3 (2)	C7—C8—C13—C12	175.61 (13)
C20—C4—C5—C6	178.81 (12)	C1—N2—C14—C19	65.95 (18)
C7—N1—C6—C5	178.30 (14)	C7—N2—C14—C19	−121.62 (16)
C7—N1—C6—C1	−0.54 (15)	C1—N2—C14—C15	−112.87 (15)
C4—C5—C6—N1	−178.52 (13)	C7—N2—C14—C15	59.56 (19)
C4—C5—C6—C1	0.2 (2)	C19—C14—C15—C16	−0.8 (2)
N2—C1—C6—N1	0.30 (15)	N2—C14—C15—C16	178.04 (13)
C2—C1—C6—N1	178.95 (13)	C14—C15—C16—C17	0.8 (2)
N2—C1—C6—C5	−178.66 (12)	C15—C16—C17—C18	0.1 (2)
C2—C1—C6—C5	0.0 (2)	C16—C17—C18—C19	−1.1 (2)
C6—N1—C7—N2	0.58 (15)	C15—C14—C19—C18	−0.2 (2)
C6—N1—C7—C8	179.77 (12)	N2—C14—C19—C18	−179.03 (13)
C1—N2—C7—N1	−0.40 (15)	C17—C18—C19—C14	1.2 (2)
C14—N2—C7—N1	−173.91 (13)	C21—O1—C20—O2	−0.62 (19)
C1—N2—C7—C8	−179.56 (12)	C21—O1—C20—C4	179.17 (11)
C14—N2—C7—C8	6.9 (2)	C5—C4—C20—O2	178.78 (14)
N1—C7—C8—C13	−149.98 (14)	C3—C4—C20—O2	−2.1 (2)
N2—C7—C8—C13	29.1 (2)	C5—C4—C20—O1	−1.01 (18)
N1—C7—C8—C9	26.20 (19)	C3—C4—C20—O1	178.09 (12)
N2—C7—C8—C9	−154.71 (13)	C20—O1—C21—C22	−175.08 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2i	0.95	2.38	3.311 (2)	166
C19—H19A···Cg2ii	0.95	2.59	3.4534 (18)	152
C21—H21A···Cg1iii	0.99	2.64	3.5288 (15)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N1/C1/C6/C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2i	0.95	2.38	3.311 (2)	166
C19—H19A⋯Cg2ii	0.95	2.59	3.4534 (18)	152
C21—H21A⋯Cg1iii	0.99	2.64	3.5288 (15)	149

Symmetry codes: (i) ; (ii) ; (iii) .