2-(4-Chloro­phen­yl)-1-phenyl-1H-benz­imidazole

Kassim, K.; Hashim, N.Z.N.; Fadzil, A.H.; Yusof, M.S.M.

doi:10.1107/S1600536812006678

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o799

doi:10.1107/S1600536812006678

Open

access

2-(4-Chlorophenyl)-1-phenyl-1H-benzimidazole

Karimah Kassim,^a N. Zakiah N. Hashim,^a Adibatul Husna Fadzil ^a and M. Sukeri M. Yusof ^b ^*

^aDepartment of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and ^bDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia
^*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 8 February 2012; accepted 14 February 2012; online 24 February 2012)

In the title compound, C₁₉H₁₃ClN₂, the dihedral angle formed by the imidazole core with the chlorophenyl 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_r = 304.76
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.04
5398 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006678/bh2413sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812006678/bh2413Isup3.cml

checkCIF report

Comment top

Benzimidazoles derivatives exhibit wide interest, especially in fields as biological compounds (Velík et al., 2004), corrosion inhibitors (Aljourani et al., 2009) and medicinal related chemistry (Tiwari et al., 2007). A number of synthesis routes for substituted benzimidazole-containing structures have been developed, affording molecules that posses significant activity.

The title compound (Fig. 1) contains three six- and a one five-membered rings. The bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable to those found in N-[(E)-4-chlorobenzylidene]-N'-phenylbenzene-1,4-diamine (Nor Hashim et al., 2010) and ethyl 1-sec-butyl-2-(2-hydroxyphenyl)-1H-benzimidazole-5-carboxylate (Arumugam et al., 2010). The dihedral angle between benzene (C1···C6) and benzimidazole (N1/N2/C7···C13) rings is 24.07 (4)°. In the crystal structure (Fig. 2), there are no intra- and inter-molecule interactions.

Related literature top

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 top

4-Chlorobenzaldehyde (0.50 g, 3.6 mmol) in 10 ml of ethanol and N-phenyl-o-phenylenediamine (0.66 g, 3.6 mmol) in 10 ml of ethanol, were mixed in a round bottom flask. The mixture was refluxed for 5 h. The reaction mixture was then cooled to room temperature and left to stand in an open air vessel for about 48 h. Brown crystals were collected after evaporation of the solvent. Yield: 65%; m.p. 150.0–150.5°C.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the b axis.

2-(4-Chlorophenyl)-1-phenyl-1H-benzimidazole top

Crystal data top

C₁₉H₁₃ClN₂	F(000) = 632
M_r = 304.76	D_x = 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

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	5398 independent reflections
Radiation source: fine-focus sealed tube	4610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 83.66 pixels mm^-1	θ_max = 32.7°, θ_min = 2.1°
ω scan	h = −9→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→14
T_min = 0.887, T_max = 0.956	l = −31→31
33103 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0532P)² + 0.487P] where P = (F_o² + 2F_c²)/3
5398 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³
0 constraints

Crystal data top

C₁₉H₁₃ClN₂	V = 1477.56 (4) Å³
M_r = 304.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2981 (1) Å	µ = 0.26 mm⁻¹
b = 9.2963 (2) Å	T = 293 K
c = 20.7796 (3) Å	0.48 × 0.39 × 0.18 mm
β = 112.815 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	5398 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4610 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.956	R_int = 0.027
33103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	Δρ_max = 0.49 e Å⁻³
5398 reflections	Δρ_min = −0.28 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃ClN₂
M_r	304.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.2981 (1), 9.2963 (2), 20.7796 (3)
β (°)	112.815 (1)
V (Å³)	1477.56 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.48 × 0.39 × 0.18

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.887, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	33103, 5398, 4610
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.04
No. of reflections	5398
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia, Universiti Teknologi MARA, for the Young Lecture Scheme and the research grants Nos. 600-RMI/ST/FRGS and 5/3/Fst(47/2010).

References

Aljourani, J., Raeissi, K. & Golozar, M. A. (2009). Corros. Sci. 51, 1836–1843. Web of Science CrossRef CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arumugam, N., Abdul Rahim, A. S., Osman, H., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o1285–o1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Nor Hashim, N. Z., Kassim, K. & Yamin, B. M. (2010). Acta Cryst. E66, o2039. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiwari, A. K., Mishra, A. K., Bajpai, A., Mishra, P., Singh, S., Sinha, D. & Singh, V. K. (2007). Bioorg. Med. Chem. Lett. 17, 2749–2755. Web of Science CrossRef PubMed CAS Google Scholar
Velík, J., Baliharová, V., Fink-Gremmels, J., Bull, S., Lamka, J. & Skálová, L. (2004). Res. Vet. Sci. 76, 95–108. Web of Science PubMed Google Scholar