2-(4-Chloro­phenyl)-1H-benzimidazole

The title compound, C₁₃H₉ClN₂, was prepared by reaction of o-phenyl­enediamine with 4-chloro­benzaldehyde under reflux in ethanol. The mol­ecules are linked by N—H...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.073
• wR factor = 0.150
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

Crystal data

C13H9ClN2	F(000) = 944
Mr = 228.67	Dx = 1.408 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.1284 (18) Å	θ = 4–14°
b = 9.783 (2) Å	µ = 0.32 mm^−1
c = 24.156 (5) Å	T = 293 K
V = 2157.2 (8) Å^3	Block, yellow
Z = 8	0.24 × 0.10 × 0.09 mm

Data collection

Bruker P4 diffractometer	Rint = 0.047
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.7°
Graphite monochromator	h = −11→11
ω scans	k = −8→12
9498 measured reflections	l = −29→30
2332 independent reflections	3 standard reflections every 100 reflections
1869 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 1.0854P] where P = (Fo^2 + 2Fc^2)/3
2332 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.34701 (9)	−0.07473 (10)	0.02323 (5)	0.0764 (4)
N1	0.6692 (2)	−0.0889 (2)	0.13941 (10)	0.0378 (5)
N2	0.7172 (2)	0.1341 (2)	0.14534 (9)	0.0374 (5)
H2A	0.7634	0.2102	0.1415	0.045*
C1	0.5544 (3)	−0.0235 (2)	0.16643 (11)	0.0351 (6)
C2	0.4265 (3)	−0.0753 (3)	0.18964 (13)	0.0476 (7)
H2B	0.4043	−0.1679	0.1873	0.057*
C3	0.3334 (3)	0.0140 (3)	0.21623 (13)	0.0517 (8)
H3A	0.2476	−0.0189	0.2321	0.062*
C4	0.3661 (3)	0.1526 (3)	0.21969 (13)	0.0488 (7)
H4A	0.3019	0.2103	0.2383	0.059*
C5	0.4896 (3)	0.2062 (3)	0.19650 (11)	0.0428 (7)
H5A	0.5098	0.2992	0.1983	0.051*
C6	0.5837 (3)	0.1165 (3)	0.17025 (11)	0.0353 (6)
C7	0.7632 (3)	0.0092 (2)	0.12779 (10)	0.0338 (6)
C8	0.9056 (3)	−0.0106 (3)	0.10083 (11)	0.0362 (6)
C9	1.0205 (3)	0.0773 (3)	0.11153 (13)	0.0513 (8)
H9A	1.0058	0.1511	0.1352	0.062*
C10	1.1559 (3)	0.0581 (3)	0.08804 (14)	0.0558 (8)
H10A	1.2323	0.1183	0.0954	0.067*
C11	1.1763 (3)	−0.0510 (3)	0.05364 (13)	0.0468 (7)
C12	1.0652 (3)	−0.1409 (3)	0.04201 (12)	0.0458 (7)
H12A	1.0811	−0.2148	0.0186	0.055*
C13	0.9296 (3)	−0.1199 (3)	0.06552 (11)	0.0409 (7)
H13A	0.8533	−0.1798	0.0576	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0452 (5)	0.0832 (7)	0.1007 (8)	0.0022 (4)	0.0262 (5)	−0.0129 (5)
N1	0.0343 (11)	0.0283 (11)	0.0507 (14)	0.0012 (9)	0.0025 (10)	−0.0002 (9)
N2	0.0394 (12)	0.0241 (11)	0.0486 (13)	−0.0024 (9)	0.0031 (10)	−0.0014 (9)
C1	0.0353 (13)	0.0269 (13)	0.0429 (15)	0.0019 (11)	0.0017 (11)	0.0012 (11)
C2	0.0448 (16)	0.0334 (15)	0.0646 (19)	−0.0031 (13)	0.0090 (14)	0.0026 (13)
C3	0.0413 (16)	0.0502 (18)	0.064 (2)	0.0014 (14)	0.0130 (14)	0.0023 (15)
C4	0.0461 (17)	0.0465 (18)	0.0538 (18)	0.0147 (13)	0.0099 (14)	−0.0009 (13)
C5	0.0485 (16)	0.0309 (14)	0.0491 (17)	0.0075 (12)	0.0009 (13)	−0.0004 (12)
C6	0.0350 (14)	0.0293 (13)	0.0416 (15)	0.0037 (11)	0.0001 (12)	0.0024 (11)
C7	0.0348 (13)	0.0265 (12)	0.0402 (14)	0.0013 (11)	−0.0019 (11)	−0.0005 (10)
C8	0.0344 (13)	0.0289 (13)	0.0453 (15)	0.0003 (11)	0.0015 (11)	0.0032 (11)
C9	0.0460 (16)	0.0424 (16)	0.065 (2)	−0.0050 (13)	0.0072 (15)	−0.0170 (14)
C10	0.0419 (16)	0.0552 (19)	0.070 (2)	−0.0104 (14)	0.0049 (15)	−0.0120 (16)
C11	0.0365 (14)	0.0500 (17)	0.0539 (18)	0.0038 (13)	0.0075 (13)	0.0039 (14)
C12	0.0497 (17)	0.0356 (15)	0.0521 (18)	0.0019 (13)	0.0116 (14)	−0.0066 (13)
C13	0.0423 (15)	0.0328 (14)	0.0478 (17)	−0.0050 (12)	0.0042 (13)	−0.0030 (12)

Geometric parameters (Å, º)

Cl1—C11	1.738 (3)	C5—C6	1.382 (4)
N1—C7	1.317 (3)	C5—H5A	0.9300
N1—C1	1.390 (3)	C7—C8	1.467 (4)
N2—C7	1.360 (3)	C8—C9	1.380 (4)
N2—C6	1.370 (3)	C8—C13	1.386 (4)
N2—H2A	0.8600	C9—C10	1.373 (4)
C1—C2	1.391 (4)	C9—H9A	0.9300
C1—C6	1.398 (3)	C10—C11	1.366 (4)
C2—C3	1.377 (4)	C10—H10A	0.9300
C2—H2B	0.9300	C11—C12	1.371 (4)
C3—C4	1.391 (4)	C12—C13	1.377 (4)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.364 (4)	C13—H13A	0.9300
C4—H4A	0.9300
Cl1···Cl1^i	3.3465 (15)
C7—N1—C1	104.9 (2)	N1—C7—N2	112.8 (2)
C7—N2—C6	107.3 (2)	N1—C7—C8	125.2 (2)
C7—N2—H2A	126.3	N2—C7—C8	122.0 (2)
C6—N2—H2A	126.3	C9—C8—C13	118.4 (2)
N1—C1—C2	130.9 (2)	C9—C8—C7	120.5 (2)
N1—C1—C6	109.7 (2)	C13—C8—C7	121.0 (2)
C2—C1—C6	119.4 (2)	C10—C9—C8	121.4 (3)
C3—C2—C1	118.4 (3)	C10—C9—H9A	119.3
C3—C2—H2B	120.8	C8—C9—H9A	119.3
C1—C2—H2B	120.8	C11—C10—C9	118.8 (3)
C2—C3—C4	120.9 (3)	C11—C10—H10A	120.6
C2—C3—H3A	119.5	C9—C10—H10A	120.6
C4—C3—H3A	119.5	C10—C11—C12	121.7 (3)
C5—C4—C3	121.8 (3)	C10—C11—Cl1	118.9 (2)
C5—C4—H4A	119.1	C12—C11—Cl1	119.4 (2)
C3—C4—H4A	119.1	C11—C12—C13	119.0 (3)
C4—C5—C6	117.3 (3)	C11—C12—H12A	120.5
C4—C5—H5A	121.4	C13—C12—H12A	120.5
C6—C5—H5A	121.4	C12—C13—C8	120.7 (2)
N2—C6—C5	132.4 (2)	C12—C13—H13A	119.6
N2—C6—C1	105.3 (2)	C8—C13—H13A	119.6
C5—C6—C1	122.2 (2)

Symmetry code: (i) −x+3, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^ii	0.86	2.06	2.905 (2)	167

Symmetry code: (ii) −x+3/2, y+1/2, z.