2-Phenyl-1H-imidazole.

In the title compound, C(9)H(8)N(2), a mirror plane lies perpendicular to the phenyl and imidazole rings and passes through the bridging C-C bond, so that the imidazole ring is disordered over two sites about the mirror plane with the equal site occupancy; the asymmetric unit contains one half-mol-ecule. In the crystal, adjacent mol-ecules are linked via N-H⋯N hydrogen bonds.

Related literature

For structures of 2-phenyl-1H-imidazolium salts, see: Xia et al. (2009 ▶); Xia & Yao (2010 ▶).

Experimental

Crystal data

C9H8N2

M = 144.17

Orthorhombic,

a = 10.0740 (15) Å

b = 18.151 (4) Å

c = 4.1562 (10) Å

V = 760.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.17 × 0.12 × 0.10 mm

Data collection

Stoe IPDS 2T diffractometer

1776 measured reflections

609 independent reflections

304 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.095

S = 0.98

609 reflections

56 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.09 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104699X/xu5367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104699X/xu5367Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104699X/xu5367Isup3.cml

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

C9H8N2	F(000) = 304
Mr = 144.17	Dx = 1.26 Mg m−3
Orthorhombic, Ama2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2a	Cell parameters from 1776 reflections
a = 10.0740 (15) Å	θ = 3.0–29.1°
b = 18.151 (4) Å	µ = 0.08 mm−1
c = 4.1562 (10) Å	T = 298 K
V = 760.0 (3) Å3	Prism, colorless
Z = 4	0.17 × 0.12 × 0.10 mm

Stoe IPDS 2T diffractometer	Rint = 0.082
graphite	θmax = 29.1°, θmin = 3.0°
rotation method scans	h = −13→11
1776 measured reflections	k = −19→24
609 independent reflections	l = −5→4
304 reflections with I > 2σ(I)

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0288P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
609 reflections	Δρmax = 0.14 e Å−3
56 parameters	Δρmin = −0.09 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)

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	Occ. (<1)
C1	0.8165 (3)	0.57694 (18)	0.2820 (10)	0.0683 (10)
H1	0.8705	0.6129	0.1911	0.082*
C2	0.75	0.4784 (3)	0.5302 (10)	0.0489 (13)
C3	0.75	0.4087 (3)	0.7033 (11)	0.0484 (12)
C4	0.6328 (3)	0.3743 (2)	0.7893 (9)	0.0650 (9)
H4	0.5523	0.3965	0.7387	0.078*
C5	0.6329 (4)	0.3080 (2)	0.9474 (10)	0.0778 (12)
H5	0.5528	0.2858	1.0015	0.093*
C6	0.75	0.2743 (3)	1.0264 (15)	0.0799 (17)
H6	0.75	0.2292	1.1323	0.096*
N1	0.8591 (2)	0.51510 (13)	0.4384 (6)	0.0592 (8)
H1B	0.9402	0.5022	0.4716	0.071*	0.5

	U11	U22	U33	U12	U13	U23
C1	0.0563 (17)	0.0625 (19)	0.086 (3)	−0.0063 (15)	0.0075 (18)	0.007 (2)
C2	0.038 (3)	0.054 (3)	0.055 (4)	0	0	−0.010 (3)
C3	0.044 (3)	0.047 (2)	0.054 (3)	0	0	−0.014 (3)
C4	0.0494 (18)	0.069 (2)	0.077 (2)	−0.0027 (18)	−0.001 (2)	0.000 (2)
C5	0.080 (2)	0.071 (2)	0.082 (3)	−0.018 (2)	0.002 (2)	0.003 (3)
C6	0.111 (5)	0.053 (3)	0.076 (4)	0	0	0.001 (3)
N1	0.0398 (15)	0.0607 (16)	0.0771 (18)	−0.0022 (14)	0.0056 (15)	−0.0011 (19)

C1—C1i	1.339 (6)	C4—C5	1.370 (5)
C1—N1	1.367 (4)	C4—H4	0.93
C1—H1	0.93	C5—C6	1.369 (4)
C2—N1i	1.341 (3)	C5—H5	0.93
C2—N1	1.341 (3)	C6—C5i	1.369 (4)
C2—C3	1.456 (6)	C6—H6	0.93
C3—C4i	1.383 (4)	N1—H1B	0.86
C3—C4	1.383 (4)
C1i—C1—N1	108.34 (16)	C3—C4—H4	119.4
C1i—C1—H1	125.8	C6—C5—C4	120.6 (4)
N1—C1—H1	125.8	C6—C5—H5	119.7
N1i—C2—N1	110.2 (4)	C4—C5—H5	119.7
N1i—C2—C3	124.9 (2)	C5—C6—C5i	119.0 (5)
N1—C2—C3	124.9 (2)	C5—C6—H6	120.5
C4i—C3—C4	117.3 (4)	C5i—C6—H6	120.5
C4i—C3—C2	121.4 (2)	C2—N1—C1	106.6 (3)
C4—C3—C2	121.4 (2)	C2—N1—H1B	126.7
C5—C4—C3	121.3 (4)	C1—N1—H1B	126.7
C5—C4—H4	119.4
N1i—C2—C3—C4i	180.0 (4)	C3—C4—C5—C6	0.4 (6)
N1—C2—C3—C4i	0.2 (6)	C4—C5—C6—C5i	0.5 (8)
N1i—C2—C3—C4	−0.2 (6)	N1i—C2—N1—C1	−0.3 (5)
N1—C2—C3—C4	−180.0 (4)	C3—C2—N1—C1	179.5 (4)
C4i—C3—C4—C5	−1.3 (6)	C1i—C1—N1—C2	0.2 (3)
C2—C3—C4—C5	178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N1ii	0.86	2.05	2.891 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯N1i	0.86	2.05	2.891 (3)	165

Symmetry code: (i) .