An ortho-rhom-bic polymorph of 1-benzyl-1H-benzimidazole.

The title compound, C(14)H(12)N(2), in contrast to the previously reported monoclinic polymorph [Lei et al. (2009 ▶). Acta Cryst. E65, o2613], crystallizes in the ortho-rhom-bic crystal system. The dihedral angle between the imidazole ring system and the phenyl ring is 76.78 (16)°. Weak C-H⋯N and C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For the synthesis, see: Lionel et al. (1996 ▶). For the monoclinic polymorph, see: Lei & Zhou (2009 ▶).

Experimental

Crystal data

C14H12N2

M = 208.26

Orthorhombic,

a = 6.124 (3) Å

b = 7.443 (4) Å

c = 23.860 (8) Å

V = 1087.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

3168 measured reflections

1886 independent reflections

892 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.148

S = 0.98

1886 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015114/hb5418sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015114/hb5418Isup2.hkl

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

C14H12N2	Dx = 1.272 Mg m−3
Mr = 208.26	Melting point: 387 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 500 reflections
a = 6.124 (3) Å	θ = 3.2–26.2°
b = 7.443 (4) Å	µ = 0.08 mm−1
c = 23.860 (8) Å	T = 293 K
V = 1087.6 (8) Å3	Block, colorless
Z = 4	0.25 × 0.20 × 0.18 mm
F(000) = 440

Oxford Diffraction Xcalibur Eos Gemini diffractometer	Rint = 0.069
Radiation source: fine-focus sealed tube	θmax = 26.2°, θmin = 3.2°
graphite	h = −7→7
φ and ω scans	k = −9→6
3168 measured reflections	l = −22→29
1886 independent reflections	1886 standard reflections every 0 min
892 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0605P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
1886 reflections	Δρmax = 0.19 e Å−3
154 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (5)

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.

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
N1	0.9512 (6)	0.9532 (5)	0.13981 (13)	0.0379 (9)
C2	0.9503 (7)	1.1255 (6)	0.16196 (16)	0.0376 (11)
C7	0.7567 (8)	0.8802 (8)	0.15157 (18)	0.0515 (13)
H7	0.7190	0.7639	0.1411	0.062*
N2	0.6248 (7)	0.9861 (7)	0.17888 (16)	0.0614 (13)
C3	1.1077 (8)	1.2581 (7)	0.16401 (18)	0.0524 (14)
H3	1.2438	1.2429	0.1474	0.063*
C10	0.9963 (8)	0.9160 (6)	0.01210 (18)	0.0463 (13)
H10	0.8689	0.8567	0.0224	0.056*
C9	1.1566 (7)	0.9393 (6)	0.05047 (16)	0.0379 (11)
C14	1.3448 (8)	1.0270 (7)	0.03496 (18)	0.0478 (13)
H14	1.4553	1.0447	0.0611	0.057*
C8	1.1293 (10)	0.8674 (8)	0.1093 (2)	0.0502 (13)
C13	1.3702 (9)	1.0881 (7)	−0.0187 (2)	0.0567 (15)
H13	1.4984	1.1465	−0.0290	0.068*
C11	1.0182 (9)	0.9782 (7)	−0.04190 (18)	0.0564 (14)
H11	0.9057	0.9624	−0.0676	0.068*
C1	0.7441 (8)	1.1405 (8)	0.18669 (18)	0.0484 (14)
C5	0.8491 (14)	1.4320 (9)	0.2169 (2)	0.0766 (19)
H5	0.8180	1.5377	0.2362	0.092*
C4	1.0542 (12)	1.4117 (8)	0.1914 (2)	0.0692 (17)
H4	1.1550	1.5049	0.1934	0.083*
C12	1.2063 (9)	1.0635 (6)	−0.05752 (19)	0.0570 (15)
H12	1.2236	1.1045	−0.0941	0.068*
C6	0.6953 (10)	1.3013 (9)	0.21424 (19)	0.0647 (17)
H6	0.5588	1.3184	0.2305	0.078*
H8B	1.274 (8)	0.887 (6)	0.1303 (18)	0.058 (15)*
H8A	1.078 (7)	0.746 (6)	0.1111 (16)	0.046 (13)*

	U11	U22	U33	U12	U13	U23
N1	0.037 (2)	0.043 (2)	0.0343 (18)	−0.002 (2)	0.0042 (18)	0.0001 (19)
C2	0.043 (3)	0.047 (3)	0.023 (2)	0.001 (3)	−0.011 (2)	0.000 (2)
C7	0.045 (3)	0.057 (3)	0.052 (3)	−0.010 (3)	0.000 (3)	0.009 (3)
N2	0.051 (3)	0.081 (3)	0.052 (3)	0.001 (3)	0.008 (2)	−0.001 (3)
C3	0.059 (3)	0.051 (3)	0.048 (3)	−0.005 (3)	−0.017 (3)	0.004 (3)
C10	0.051 (3)	0.046 (3)	0.042 (2)	−0.013 (3)	0.005 (3)	−0.007 (2)
C9	0.039 (3)	0.038 (3)	0.037 (2)	0.003 (3)	−0.001 (3)	−0.011 (2)
C14	0.041 (3)	0.054 (3)	0.049 (3)	−0.003 (3)	−0.002 (3)	−0.007 (3)
C8	0.053 (3)	0.052 (3)	0.045 (3)	0.007 (3)	0.004 (3)	0.005 (3)
C13	0.054 (3)	0.053 (4)	0.063 (3)	−0.007 (3)	0.022 (3)	−0.006 (3)
C11	0.064 (3)	0.061 (3)	0.044 (3)	−0.004 (3)	−0.008 (3)	−0.003 (3)
C1	0.048 (3)	0.072 (4)	0.025 (2)	0.021 (3)	0.007 (3)	0.006 (3)
C5	0.119 (6)	0.069 (4)	0.042 (3)	0.032 (5)	−0.038 (4)	−0.026 (3)
C4	0.095 (5)	0.053 (4)	0.060 (3)	0.003 (3)	−0.025 (4)	−0.006 (3)
C12	0.078 (4)	0.048 (3)	0.045 (3)	0.003 (3)	0.016 (3)	−0.003 (3)
C6	0.072 (4)	0.090 (5)	0.032 (3)	0.029 (4)	0.002 (3)	−0.010 (3)

N1—C7	1.339 (6)	C14—C13	1.367 (6)
N1—C2	1.387 (5)	C14—H14	0.9300
N1—C8	1.459 (6)	C8—H8B	1.03 (5)
C2—C3	1.380 (6)	C8—H8A	0.96 (5)
C2—C1	1.398 (6)	C13—C12	1.379 (6)
C7—N2	1.303 (6)	C13—H13	0.9300
C7—H7	0.9300	C11—C12	1.367 (6)
N2—C1	1.374 (6)	C11—H11	0.9300
C3—C4	1.358 (7)	C1—C6	1.398 (7)
C3—H3	0.9300	C5—C6	1.356 (8)
C10—C9	1.354 (5)	C5—C4	1.404 (8)
C10—C11	1.376 (6)	C5—H5	0.9300
C10—H10	0.9300	C4—H4	0.9300
C9—C14	1.375 (6)	C12—H12	0.9300
C9—C8	1.511 (6)	C6—H6	0.9300
C7—N1—C2	107.0 (4)	N1—C8—H8A	98 (3)
C7—N1—C8	126.3 (4)	C9—C8—H8A	114 (2)
C2—N1—C8	126.7 (4)	H8B—C8—H8A	113 (4)
C3—C2—N1	132.2 (4)	C14—C13—C12	120.1 (5)
C3—C2—C1	124.0 (5)	C14—C13—H13	119.9
N1—C2—C1	103.8 (4)	C12—C13—H13	119.9
N2—C7—N1	114.3 (5)	C12—C11—C10	119.6 (5)
N2—C7—H7	122.9	C12—C11—H11	120.2
N1—C7—H7	122.9	C10—C11—H11	120.2
C7—N2—C1	104.1 (4)	N2—C1—C6	131.7 (5)
C4—C3—C2	116.8 (5)	N2—C1—C2	110.9 (4)
C4—C3—H3	121.6	C6—C1—C2	117.4 (6)
C2—C3—H3	121.6	C6—C5—C4	121.6 (5)
C9—C10—C11	121.3 (5)	C6—C5—H5	119.2
C9—C10—H10	119.4	C4—C5—H5	119.2
C11—C10—H10	119.4	C3—C4—C5	121.1 (6)
C10—C9—C14	119.1 (4)	C3—C4—H4	119.5
C10—C9—C8	120.2 (5)	C5—C4—H4	119.5
C14—C9—C8	120.7 (4)	C11—C12—C13	119.5 (4)
C13—C14—C9	120.4 (5)	C11—C12—H12	120.3
C13—C14—H14	119.8	C13—C12—H12	120.3
C9—C14—H14	119.8	C5—C6—C1	119.2 (6)
N1—C8—C9	113.0 (4)	C5—C6—H6	120.4
N1—C8—H8B	110 (2)	C1—C6—H6	120.4
C9—C8—H8B	108 (2)
C7—N1—C2—C3	177.5 (5)	C14—C9—C8—N1	116.5 (6)
C8—N1—C2—C3	−2.7 (7)	C9—C14—C13—C12	0.5 (8)
C7—N1—C2—C1	0.4 (4)	C9—C10—C11—C12	0.8 (7)
C8—N1—C2—C1	−179.8 (4)	C7—N2—C1—C6	−178.1 (4)
C2—N1—C7—N2	0.5 (5)	C7—N2—C1—C2	1.5 (5)
C8—N1—C7—N2	−179.2 (4)	C3—C2—C1—N2	−178.6 (4)
N1—C7—N2—C1	−1.2 (5)	N1—C2—C1—N2	−1.2 (5)
N1—C2—C3—C4	−177.3 (4)	C3—C2—C1—C6	1.1 (6)
C1—C2—C3—C4	−0.7 (7)	N1—C2—C1—C6	178.5 (4)
C11—C10—C9—C14	0.0 (7)	C2—C3—C4—C5	0.8 (7)
C11—C10—C9—C8	−179.2 (5)	C6—C5—C4—C3	−1.4 (8)
C10—C9—C14—C13	−0.6 (7)	C10—C11—C12—C13	−0.9 (7)
C8—C9—C14—C13	178.5 (5)	C14—C13—C12—C11	0.3 (7)
C7—N1—C8—C9	106.1 (5)	C4—C5—C6—C1	1.8 (8)
C2—N1—C8—C9	−73.7 (6)	N2—C1—C6—C5	178.0 (5)
C10—C9—C8—N1	−64.3 (6)	C2—C1—C6—C5	−1.6 (7)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N2i	1.03 (5)	2.55 (5)	3.570 (8)	171 (4)
C12—H12···Cg2ii	0.93	2.66	3.559 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯N2i	1.03 (5)	2.55 (5)	3.570 (8)	171 (4)
C12—H12⋯Cg2ii	0.93	2.66	3.559 (5)	162

Symmetry codes: (i) ; (ii) .