2-(4-Chloro-phen-yl)-1-phenyl-1H-benz-imidazole.

In the title compound, C(19)H(13)ClN(2), the dihedral angle formed by the imidazole core with the chloro-phenyl and phenyl rings are 24.07 (4) and 67.24 (4)°, respectively.

Related literature

For the applications of benzimidazoles derivatives, see: Velík et al. (2004 ▶); Aljourani et al. (2009 ▶); Tiwari et al. (2007 ▶). For related structures, see: Nor Hashim et al. (2010 ▶); Arumugam et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H13ClN2

M = 304.76

Monoclinic,

a = 8.2981 (1) Å

b = 9.2963 (2) Å

c = 20.7796 (3) Å

β = 112.815 (1)°

V = 1477.56 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.48 × 0.39 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.887, T max = 0.956

33103 measured reflections

5398 independent reflections

4610 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.04

5398 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.28 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006678/bh2413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006678/bh2413Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006678/bh2413Isup3.cml

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

C19H13ClN2	F(000) = 632
Mr = 304.76	Dx = 1.370 Mg m−3
Monoclinic, P21/c	Melting point: 423 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.2981 (1) Å	θ = 2.1–32.7°
b = 9.2963 (2) Å	µ = 0.26 mm−1
c = 20.7796 (3) Å	T = 293 K
β = 112.815 (1)°	Slab, brown
V = 1477.56 (4) Å3	0.48 × 0.39 × 0.18 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	5398 independent reflections
Radiation source: fine-focus sealed tube	4610 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 83.66 pixels mm-1	θmax = 32.7°, θmin = 2.1°
ω scan	h = −9→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→14
Tmin = 0.887, Tmax = 0.956	l = −31→31
33103 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.487P] where P = (Fo2 + 2Fc2)/3
5398 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.28 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cl1	0.72432 (4)	−0.07747 (3)	−0.201084 (13)	0.02762 (8)
N1	0.15677 (11)	0.13941 (9)	−0.51877 (4)	0.01712 (15)
N2	0.19862 (10)	−0.08273 (8)	−0.55312 (4)	0.01549 (15)
C1	0.49136 (12)	−0.11517 (11)	−0.40861 (5)	0.01843 (17)
H1B	0.5057	−0.1695	−0.4436	0.022*
C2	0.60543 (13)	−0.13482 (11)	−0.33949 (5)	0.02010 (18)
H2A	0.6952	−0.2021	−0.3281	0.024*
C3	0.58327 (13)	−0.05256 (11)	−0.28778 (5)	0.01930 (18)
C4	0.45136 (13)	0.05008 (11)	−0.30385 (5)	0.01991 (18)
H4A	0.4393	0.1057	−0.2688	0.024*
C5	0.33807 (13)	0.06833 (10)	−0.37285 (5)	0.01777 (17)
H5A	0.2494	0.1366	−0.3840	0.021*
C6	0.35547 (12)	−0.01485 (10)	−0.42611 (5)	0.01522 (16)
C7	0.23567 (12)	0.01388 (10)	−0.49847 (5)	0.01518 (16)
C8	0.06201 (12)	0.12524 (10)	−0.59018 (5)	0.01704 (17)
C9	−0.04641 (13)	0.22408 (11)	−0.63856 (5)	0.02113 (19)
H9A	−0.0658	0.3155	−0.6248	0.025*
C10	−0.12370 (13)	0.18085 (12)	−0.70759 (6)	0.0235 (2)
H10A	−0.1965	0.2445	−0.7406	0.028*
C11	−0.09486 (14)	0.04291 (12)	−0.72905 (5)	0.0232 (2)
H11A	−0.1474	0.0183	−0.7760	0.028*
C12	0.00988 (13)	−0.05700 (11)	−0.68185 (5)	0.02010 (18)
H12A	0.0277	−0.1488	−0.6956	0.024*
C13	0.08723 (12)	−0.01221 (10)	−0.61242 (5)	0.01645 (16)
C14	0.23702 (12)	−0.23309 (10)	−0.55279 (5)	0.01539 (16)
C15	0.33740 (12)	−0.28012 (11)	−0.58889 (5)	0.01818 (17)
H15A	0.3838	−0.2146	−0.6109	0.022*
C16	0.36742 (13)	−0.42709 (11)	−0.59159 (5)	0.02123 (19)
H16A	0.4343	−0.4601	−0.6155	0.025*
C17	0.29783 (13)	−0.52407 (11)	−0.55872 (6)	0.0221 (2)
H17A	0.3173	−0.6221	−0.5611	0.027*
C18	0.19916 (14)	−0.47574 (11)	−0.52227 (6)	0.0226 (2)
H18A	0.1546	−0.5413	−0.4996	0.027*
C19	0.16673 (13)	−0.32917 (11)	−0.51960 (5)	0.01932 (18)
H19A	0.0990	−0.2963	−0.4959	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.03461 (15)	0.02418 (13)	0.01779 (12)	−0.00362 (10)	0.00329 (10)	0.00170 (8)
N1	0.0187 (3)	0.0134 (3)	0.0199 (4)	0.0005 (3)	0.0082 (3)	−0.0005 (3)
N2	0.0178 (3)	0.0120 (3)	0.0166 (3)	−0.0001 (3)	0.0067 (3)	−0.0015 (3)
C1	0.0184 (4)	0.0169 (4)	0.0200 (4)	0.0007 (3)	0.0075 (3)	−0.0019 (3)
C2	0.0195 (4)	0.0176 (4)	0.0213 (4)	0.0002 (3)	0.0060 (3)	−0.0005 (3)
C3	0.0219 (4)	0.0177 (4)	0.0170 (4)	−0.0043 (3)	0.0061 (3)	0.0005 (3)
C4	0.0244 (4)	0.0187 (4)	0.0185 (4)	−0.0033 (3)	0.0103 (3)	−0.0031 (3)
C5	0.0190 (4)	0.0155 (4)	0.0204 (4)	−0.0011 (3)	0.0094 (3)	−0.0024 (3)
C6	0.0160 (4)	0.0130 (4)	0.0176 (4)	−0.0020 (3)	0.0076 (3)	−0.0013 (3)
C7	0.0162 (4)	0.0130 (4)	0.0178 (4)	−0.0010 (3)	0.0082 (3)	−0.0018 (3)
C8	0.0174 (4)	0.0149 (4)	0.0195 (4)	−0.0005 (3)	0.0080 (3)	0.0009 (3)
C9	0.0217 (4)	0.0173 (4)	0.0248 (5)	0.0015 (3)	0.0096 (4)	0.0044 (3)
C10	0.0218 (4)	0.0256 (5)	0.0222 (5)	0.0014 (4)	0.0077 (4)	0.0076 (4)
C11	0.0222 (4)	0.0286 (5)	0.0178 (4)	−0.0015 (4)	0.0066 (3)	0.0018 (4)
C12	0.0201 (4)	0.0216 (4)	0.0186 (4)	−0.0015 (3)	0.0074 (3)	−0.0017 (3)
C13	0.0162 (4)	0.0158 (4)	0.0176 (4)	−0.0012 (3)	0.0069 (3)	0.0004 (3)
C14	0.0155 (4)	0.0129 (4)	0.0174 (4)	−0.0008 (3)	0.0060 (3)	−0.0022 (3)
C15	0.0180 (4)	0.0191 (4)	0.0184 (4)	−0.0008 (3)	0.0081 (3)	−0.0032 (3)
C16	0.0185 (4)	0.0220 (5)	0.0213 (4)	0.0025 (3)	0.0057 (3)	−0.0068 (3)
C17	0.0197 (4)	0.0149 (4)	0.0265 (5)	0.0015 (3)	0.0031 (4)	−0.0045 (3)
C18	0.0226 (4)	0.0143 (4)	0.0304 (5)	−0.0018 (3)	0.0098 (4)	0.0005 (4)
C19	0.0199 (4)	0.0159 (4)	0.0249 (5)	−0.0010 (3)	0.0117 (4)	−0.0005 (3)

Cl1—C3	1.7418 (10)	C9—C10	1.3845 (15)
N1—C7	1.3245 (12)	C9—H9A	0.9300
N1—C8	1.3902 (12)	C10—C11	1.4083 (16)
N2—C13	1.3853 (12)	C10—H10A	0.9300
N2—C7	1.3856 (12)	C11—C12	1.3853 (15)
N2—C14	1.4331 (12)	C11—H11A	0.9300
C1—C2	1.3921 (14)	C12—C13	1.3960 (14)
C1—C6	1.3985 (13)	C12—H12A	0.9300
C1—H1B	0.9300	C14—C19	1.3876 (13)
C2—C3	1.3880 (14)	C14—C15	1.3900 (13)
C2—H2A	0.9300	C15—C16	1.3938 (14)
C3—C4	1.3917 (15)	C15—H15A	0.9300
C4—C5	1.3867 (14)	C16—C17	1.3852 (16)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.4026 (13)	C17—C18	1.3880 (15)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.4701 (13)	C18—C19	1.3942 (14)
C8—C9	1.4011 (13)	C18—H18A	0.9300
C8—C13	1.4019 (13)	C19—H19A	0.9300
C7—N1—C8	105.16 (8)	C9—C10—C11	121.67 (10)
C13—N2—C7	106.36 (8)	C9—C10—H10A	119.2
C13—N2—C14	122.43 (8)	C11—C10—H10A	119.2
C7—N2—C14	130.55 (8)	C12—C11—C10	121.55 (10)
C2—C1—C6	120.86 (9)	C12—C11—H11A	119.2
C2—C1—H1B	119.6	C10—C11—H11A	119.2
C6—C1—H1B	119.6	C11—C12—C13	116.27 (10)
C3—C2—C1	119.03 (9)	C11—C12—H12A	121.9
C3—C2—H2A	120.5	C13—C12—H12A	121.9
C1—C2—H2A	120.5	N2—C13—C12	131.22 (9)
C2—C3—C4	121.33 (9)	N2—C13—C8	105.76 (8)
C2—C3—Cl1	119.33 (8)	C12—C13—C8	123.03 (9)
C4—C3—Cl1	119.34 (8)	C19—C14—C15	121.41 (9)
C5—C4—C3	119.13 (9)	C19—C14—N2	119.64 (8)
C5—C4—H4A	120.4	C15—C14—N2	118.87 (8)
C3—C4—H4A	120.4	C14—C15—C16	118.94 (9)
C4—C5—C6	120.83 (9)	C14—C15—H15A	120.5
C4—C5—H5A	119.6	C16—C15—H15A	120.5
C6—C5—H5A	119.6	C17—C16—C15	120.19 (9)
C1—C6—C5	118.80 (9)	C17—C16—H16A	119.9
C1—C6—C7	122.98 (8)	C15—C16—H16A	119.9
C5—C6—C7	118.11 (8)	C16—C17—C18	120.35 (9)
N1—C7—N2	112.64 (8)	C16—C17—H17A	119.8
N1—C7—C6	122.71 (8)	C18—C17—H17A	119.8
N2—C7—C6	124.59 (8)	C17—C18—C19	120.12 (10)
N1—C8—C9	130.08 (9)	C17—C18—H18A	119.9
N1—C8—C13	110.08 (8)	C19—C18—H18A	119.9
C9—C8—C13	119.84 (9)	C14—C19—C18	118.98 (9)
C10—C9—C8	117.62 (10)	C14—C19—H19A	120.5
C10—C9—H9A	121.2	C18—C19—H19A	120.5
C8—C9—H9A	121.2
C6—C1—C2—C3	−0.36 (15)	C9—C10—C11—C12	1.15 (16)
C1—C2—C3—C4	−0.95 (15)	C10—C11—C12—C13	−1.15 (15)
C1—C2—C3—Cl1	179.49 (8)	C7—N2—C13—C12	179.43 (10)
C2—C3—C4—C5	1.21 (15)	C14—N2—C13—C12	−9.02 (16)
Cl1—C3—C4—C5	−179.23 (7)	C7—N2—C13—C8	−0.15 (10)
C3—C4—C5—C6	−0.16 (15)	C14—N2—C13—C8	171.41 (8)
C2—C1—C6—C5	1.37 (14)	C11—C12—C13—N2	−179.23 (10)
C2—C1—C6—C7	177.63 (9)	C11—C12—C13—C8	0.28 (15)
C4—C5—C6—C1	−1.11 (14)	N1—C8—C13—N2	0.38 (10)
C4—C5—C6—C7	−177.54 (9)	C9—C8—C13—N2	−179.76 (8)
C8—N1—C7—N2	0.37 (10)	N1—C8—C13—C12	−179.24 (9)
C8—N1—C7—C6	177.69 (8)	C9—C8—C13—C12	0.62 (15)
C13—N2—C7—N1	−0.14 (10)	C13—N2—C14—C19	−107.24 (11)
C14—N2—C7—N1	−170.76 (9)	C7—N2—C14—C19	62.08 (13)
C13—N2—C7—C6	−177.40 (8)	C13—N2—C14—C15	69.63 (12)
C14—N2—C7—C6	11.99 (15)	C7—N2—C14—C15	−121.05 (11)
C1—C6—C7—N1	−152.39 (9)	C19—C14—C15—C16	0.04 (14)
C5—C6—C7—N1	23.89 (13)	N2—C14—C15—C16	−176.77 (8)
C1—C6—C7—N2	24.60 (14)	C14—C15—C16—C17	0.01 (15)
C5—C6—C7—N2	−159.12 (9)	C15—C16—C17—C18	−0.62 (15)
C7—N1—C8—C9	179.70 (10)	C16—C17—C18—C19	1.17 (15)
C7—N1—C8—C13	−0.46 (10)	C15—C14—C19—C18	0.50 (14)
N1—C8—C9—C10	179.19 (10)	N2—C14—C19—C18	177.29 (9)
C13—C8—C9—C10	−0.64 (14)	C17—C18—C19—C14	−1.10 (15)
C8—C9—C10—C11	−0.21 (15)