2-Phenyl-1H-imidazole

Abstract

In the title compound, C₉H₈N₂, 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-mol­ecule. In the crystal, adjacent mol­ecules 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 _r = 144.17

• Orthorhombic,

• a = 10.0740 (15) Å

• b = 18.151 (4) Å

• c = 4.1562 (10) Å

• V = 760.0 (3) ų

• 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

• Δρ_max = 0.14 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

2-Phenylimidazole, as an important compound with potential N donor atom that may contribute in classical hydrogen bonding in generation of supramolecular assemblies. There are some crystal structure reports that show 2-phenylimidazole can be protonated (Xia et al., 2009; Xia & Yao, 2010).

The asymmetric unit of the title compound contains one half-molecule, a mirror plane passes through the C—C connecting two rings (Fig. 1). In this molecule the bond lengths and angles are within normal ranges. The imidazole and phenyl rings are nearly co-planar. The intermolecular N—H···N hydrogen bonds (Table 1) occurs in the crystal structure (Table 1).

Experimental

The title compound has been obtained during the stirring of 2-phenyl-1H-imidazole and aniline in 1:1 molar ration in methanol for synthesis of co-crystal of reagents. The suitable crystals for X-ray analysis were obtained by slow evaporation from methanol solution after one week (yield; 86.5%).

Refinement

All of the H atoms were positioned geometrically with C—H = 0.93 and N—H = 0.86 Å, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C,N). The molecule is disordered over two sites in the crystal structure and H1B atom is in 50% occupancy. Friedel pairs were merged as no significant anomalous scatterings.

Figures

Fig. 1.

The molecular structure with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.

Fig. 2.

Packing diagram.

Crystal data

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

Data collection

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

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)

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	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

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

Symmetry codes: (i) −x+3/2, y, z.

Hydrogen-bond geometry (Å, °)

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

Symmetry codes: (ii) −x+2, −y+1, z.