4-[4-(1H-Imidazol-4-yl)phen-yl]-1H-imidazole.

In the mol-ecule of the title compound, C(12)H(10)N(4), the two imidazole substituents are related by inversion symmetry and each forms a dihedral angle of 25.02 (8)° with the benzene ring. In the crystal, mol-ecules are linked through N-H⋯N hydrogen bonds, forming cyclic units [graph-set R(4) (4)(28)], which generate a layered structure extending across (011).

Related literature

For the synthesis of the title compound, see: Petersen (1950 ▶); Huisman (1997 ▶); Have (1997 ▶). For a similar structure, see: Gao & Duan (2012 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C12H10N4

M = 210.24

Orthorhombic,

a = 6.8604 (2) Å

b = 9.4534 (3) Å

c = 16.4789 (6) Å

V = 1068.72 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.975

11170 measured reflections

932 independent reflections

746 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.07

932 reflections

77 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032485/zs2214sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032485/zs2214Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032485/zs2214Isup3.cml

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

C12H10N4	F(000) = 440
Mr = 210.24	Dx = 1.307 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2852 reflections
a = 6.8604 (2) Å	θ = 2.5–23.0°
b = 9.4534 (3) Å	µ = 0.08 mm−1
c = 16.4789 (6) Å	T = 296 K
V = 1068.72 (6) Å3	Block, colorless
Z = 4	0.40 × 0.35 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	932 independent reflections
Radiation source: fine-focus sealed tube	746 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.967, Tmax = 0.975	k = −11→11
11170 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1236P] where P = (Fo2 + 2Fc2)/3
932 reflections	(Δ/σ)max < 0.001
77 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.13 e Å−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
N1	−0.04339 (18)	0.62662 (12)	0.21679 (8)	0.0486 (4)
N2	0.03252 (17)	0.85297 (11)	0.21277 (7)	0.0465 (3)
C1	0.0142 (2)	0.74017 (14)	0.25866 (10)	0.0505 (4)
H1A	0.0387	0.7394	0.3142	0.061*
C2	−0.0646 (2)	0.66854 (14)	0.13827 (9)	0.0459 (4)
H2A	−0.1035	0.6125	0.0948	0.055*
C3	−0.01772 (19)	0.80895 (14)	0.13570 (8)	0.0402 (3)
C4	−0.01031 (18)	0.90577 (13)	0.06630 (8)	0.0398 (4)
C5	−0.1213 (2)	0.88440 (13)	−0.00307 (8)	0.0465 (4)
H5A	−0.2038	0.8065	−0.0059	0.056*
C6	0.1116 (2)	1.02373 (13)	0.06775 (8)	0.0461 (4)
H6A	0.1879	1.0407	0.1134	0.055*
H1B	−0.054 (3)	0.5309 (18)	0.2395 (11)	0.081 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0551 (7)	0.0350 (6)	0.0558 (8)	0.0034 (5)	0.0020 (6)	0.0067 (6)
N2	0.0532 (7)	0.0382 (6)	0.0483 (7)	−0.0007 (5)	−0.0064 (5)	0.0016 (5)
C1	0.0568 (9)	0.0458 (8)	0.0490 (9)	0.0034 (7)	−0.0077 (6)	0.0040 (7)
C2	0.0524 (8)	0.0376 (7)	0.0477 (9)	−0.0004 (6)	0.0043 (6)	−0.0035 (6)
C3	0.0402 (7)	0.0346 (7)	0.0458 (8)	0.0014 (5)	0.0024 (6)	−0.0020 (6)
C4	0.0423 (7)	0.0327 (7)	0.0442 (8)	0.0004 (5)	0.0044 (6)	−0.0033 (5)
C5	0.0523 (8)	0.0383 (7)	0.0488 (8)	−0.0125 (6)	0.0001 (6)	−0.0032 (6)
C6	0.0504 (8)	0.0440 (7)	0.0441 (8)	−0.0093 (6)	−0.0029 (6)	−0.0017 (6)

N1—C1	1.3359 (17)	C2—H2A	0.9300
N1—C2	1.3611 (19)	C3—C4	1.4657 (18)
N1—H1B	0.981 (17)	C4—C5	1.3883 (19)
N2—C1	1.3133 (17)	C4—C6	1.3940 (18)
N2—C3	1.3801 (18)	C5—C6i	1.3766 (17)
C1—H1A	0.9300	C5—H5A	0.9300
C2—C3	1.3665 (19)	C6—H6A	0.9300
C1—N1—C2	106.79 (12)	C2—C3—C4	129.71 (12)
C1—N1—H1B	124.5 (11)	N2—C3—C4	121.40 (11)
C2—N1—H1B	128.5 (11)	C5—C4—C6	117.36 (12)
C1—N2—C3	105.14 (11)	C5—C4—C3	122.18 (12)
N2—C1—N1	112.54 (14)	C6—C4—C3	120.46 (12)
N2—C1—H1A	123.7	C6i—C5—C4	121.28 (12)
N1—C1—H1A	123.7	C6i—C5—H5A	119.4
N1—C2—C3	106.67 (12)	C4—C5—H5A	119.4
N1—C2—H2A	126.7	C5i—C6—C4	121.36 (12)
C3—C2—H2A	126.7	C5i—C6—H6A	119.3
C2—C3—N2	108.86 (12)	C4—C6—H6A	119.3
C3—N2—C1—N1	0.22 (16)	N2—C3—C4—C5	−156.22 (12)
C2—N1—C1—N2	−0.19 (16)	C2—C3—C4—C6	−153.60 (14)
C1—N1—C2—C3	0.07 (15)	N2—C3—C4—C6	24.22 (18)
N1—C2—C3—N2	0.06 (15)	C6—C4—C5—C6i	−0.1 (2)
N1—C2—C3—C4	178.10 (13)	C3—C4—C5—C6i	−179.71 (13)
C1—N2—C3—C2	−0.17 (15)	C5—C4—C6—C5i	0.1 (2)
C1—N2—C3—C4	−178.40 (12)	C3—C4—C6—C5i	179.72 (12)
C2—C3—C4—C5	26.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N2ii	0.981 (17)	1.863 (18)	2.8364 (17)	170.8 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯N2i	0.981 (17)	1.863 (18)	2.8364 (17)	170.8 (17)

Symmetry code: (i) .