2-Phenyl-1H-imidazole

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 m a 2

• 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[F² > 2σ(F²)] = 0.056

• wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯N1^i	0.86	2.05	2.891 (3)	165
Symmetry code: (i) -x+2, -y+1, z.

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).

Supporting information

S1. 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).

Related literature

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

S2. 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%).

S3. 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.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures

	Fig. 1. The molecular structure with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. Packing diagram.

2-Phenyl-1H-imidazole

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) Å^3	Prism, colorless
Z = 4	0.17 × 0.12 × 0.10 mm

Data collection

Stoe IPDS 2T diffractometer	Rint = 0.082
Graphite monochromator	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 F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0288P)^2] where P = (Fo^2 + 2Fc^2)/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)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

C1—C1^i	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—N1^i	1.341 (3)	C5—H5	0.93
C2—N1	1.341 (3)	C6—C5^i	1.369 (4)
C2—C3	1.456 (6)	C6—H6	0.93
C3—C4^i	1.383 (4)	N1—H1B	0.86
C3—C4	1.383 (4)
C1^i—C1—N1	108.34 (16)	C3—C4—H4	119.4
C1^i—C1—H1	125.8	C6—C5—C4	120.6 (4)
N1—C1—H1	125.8	C6—C5—H5	119.7
N1^i—C2—N1	110.2 (4)	C4—C5—H5	119.7
N1^i—C2—C3	124.9 (2)	C5—C6—C5^i	119.0 (5)
N1—C2—C3	124.9 (2)	C5—C6—H6	120.5
C4^i—C3—C4	117.3 (4)	C5^i—C6—H6	120.5
C4^i—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
N1^i—C2—C3—C4^i	180.0 (4)	C3—C4—C5—C6	0.4 (6)
N1—C2—C3—C4^i	0.2 (6)	C4—C5—C6—C5^i	0.5 (8)
N1^i—C2—C3—C4	−0.2 (6)	N1^i—C2—N1—C1	−0.3 (5)
N1—C2—C3—C4	−180.0 (4)	C3—C2—N1—C1	179.5 (4)
C4^i—C3—C4—C5	−1.3 (6)	C1^i—C1—N1—C2	0.2 (3)
C2—C3—C4—C5	178.9 (4)

Symmetry code: (i) −x+3/2, y, z.

Hydrogen-bond geometry (Å, º)

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

Symmetry code: (ii) −x+2, −y+1, z.