2-(Pyridin-4-yl)-1H-benzimidazole.

The title compound, C12H9N3, is an unhydrated analogue of the previously reported trihydrate. The mol-ecule is essentially planar, with a 3.62 (11)° angle between the pyridine and benzimidazole planes. In the crystal, N-H⋯N hydrogen bonds result in chains of mol-ecules parallel to [010], which are additionally linked by weak π-π stacking inter-actions [centroid-centroid distance = 3.7469 (17) Å], resulting in extended sheets of molecules parallel to (103).

Related literature

For the structure of the trihydrate of the title compound, see: Huang et al. (2004 ▶)

Experimental

Crystal data

C12H9N3

M = 195.22

Monoclinic,

a = 6.0602 (14) Å

b = 11.610 (3) Å

c = 13.892 (4) Å

β = 101.838 (8)°

V = 956.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.50 × 0.20 × 0.20 mm

Data collection

Bruker SMART X2S CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.53, T max = 0.98

4809 measured reflections

1699 independent reflections

1125 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 0.96

1699 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301252X/im2430sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301252X/im2430Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301252X/im2430Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301252X/im2430Isup4.cml

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

C12H9N3	F(000) = 408
Mr = 195.22	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0602 (14) Å	Cell parameters from 1098 reflections
b = 11.610 (3) Å	θ = 2.3–24.2°
c = 13.892 (4) Å	µ = 0.09 mm−1
β = 101.838 (8)°	T = 200 K
V = 956.6 (4) Å3	Prism, clear yellow
Z = 4	0.50 × 0.20 × 0.20 mm

Bruker SMART X2S CCD diffractometer	1699 independent reflections
Radiation source: XOS X-beam microfocus source	1125 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.058
Detector resolution: 8.3330 pixels mm-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2010)	k = −13→8
Tmin = 0.53, Tmax = 0.98	l = −16→16
4809 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0664P)2] where P = (Fo2 + 2Fc2)/3
1699 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The H atoms bonded to carbon were refined using a riding model with C—H = 0.95 Å and Uiso = 1.2Ueq(C). The coordinates and isotropic thermal parameters of the amine H atom were refined freely.

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	0.4979 (3)	0.67895 (13)	0.38292 (14)	0.0331 (5)
H1	0.618 (4)	0.7118 (19)	0.3528 (19)	0.062 (7)*
N2	0.2493 (3)	0.54899 (13)	0.41681 (13)	0.0303 (5)
N3	0.7075 (3)	0.30522 (13)	0.22238 (14)	0.0357 (5)
C1	0.3669 (3)	0.73593 (15)	0.43732 (16)	0.0294 (5)
C2	0.2130 (3)	0.65460 (15)	0.45835 (16)	0.0286 (5)
C3	0.0506 (3)	0.68515 (17)	0.51158 (17)	0.0338 (6)
H3	−0.0548	0.6305	0.5259	0.041*
C4	0.0490 (3)	0.79775 (16)	0.54271 (18)	0.0389 (6)
H4	−0.0594	0.8211	0.5794	0.047*
C5	0.2039 (3)	0.87851 (17)	0.52133 (19)	0.0412 (6)
H5	0.1968	0.9556	0.5434	0.049*
C6	0.3650 (4)	0.84967 (16)	0.46965 (18)	0.0398 (6)
H6	0.471	0.9046	0.4563	0.048*
C7	0.4191 (3)	0.56767 (15)	0.37324 (16)	0.0284 (5)
C8	0.5194 (3)	0.47905 (15)	0.32041 (16)	0.0295 (5)
C9	0.7077 (4)	0.49937 (16)	0.28180 (18)	0.0368 (6)
H9	0.7769	0.5732	0.2878	0.044*
C10	0.7947 (4)	0.41118 (17)	0.23429 (18)	0.0395 (6)
H10	0.9251	0.4268	0.2084	0.047*
C11	0.5260 (3)	0.28667 (16)	0.26116 (17)	0.0352 (6)
H11	0.4609	0.2119	0.2545	0.042*
C12	0.4278 (3)	0.36867 (15)	0.30996 (17)	0.0336 (6)
H12	0.2992	0.3503	0.3362	0.04*

	U11	U22	U33	U12	U13	U23
N1	0.0314 (10)	0.0239 (9)	0.0474 (13)	−0.0038 (7)	0.0161 (9)	−0.0026 (8)
N2	0.0291 (10)	0.0267 (9)	0.0376 (12)	−0.0014 (7)	0.0130 (9)	0.0002 (7)
N3	0.0372 (11)	0.0305 (9)	0.0406 (13)	0.0062 (8)	0.0110 (9)	−0.0012 (8)
C1	0.0284 (11)	0.0270 (10)	0.0342 (14)	0.0005 (8)	0.0098 (10)	−0.0002 (9)
C2	0.0270 (11)	0.0259 (10)	0.0334 (13)	−0.0006 (8)	0.0075 (10)	0.0002 (9)
C3	0.0296 (12)	0.0350 (11)	0.0381 (15)	−0.0014 (9)	0.0104 (11)	0.0019 (9)
C4	0.0375 (13)	0.0379 (12)	0.0454 (16)	0.0028 (10)	0.0182 (12)	−0.0031 (10)
C5	0.0478 (14)	0.0292 (11)	0.0501 (16)	−0.0011 (9)	0.0185 (12)	−0.0083 (10)
C6	0.0426 (14)	0.0274 (11)	0.0519 (17)	−0.0073 (9)	0.0158 (12)	−0.0059 (10)
C7	0.0261 (11)	0.0242 (10)	0.0353 (14)	−0.0011 (8)	0.0074 (10)	0.0010 (9)
C8	0.0279 (12)	0.0241 (9)	0.0362 (14)	0.0036 (8)	0.0056 (10)	0.0019 (9)
C9	0.0380 (13)	0.0252 (10)	0.0511 (17)	−0.0010 (9)	0.0183 (12)	0.0008 (9)
C10	0.0374 (13)	0.0362 (11)	0.0496 (16)	0.0028 (9)	0.0201 (12)	0.0032 (10)
C11	0.0339 (13)	0.0276 (10)	0.0450 (16)	0.0005 (9)	0.0105 (11)	−0.0047 (9)
C12	0.0297 (12)	0.0293 (11)	0.0437 (15)	−0.0021 (9)	0.0119 (11)	−0.0013 (9)

N1—C1	1.373 (3)	C4—H4	0.95
N1—C7	1.374 (2)	C5—C6	1.367 (3)
N1—H1	0.99 (2)	C5—H5	0.95
N2—C7	1.315 (3)	C6—H6	0.95
N2—C2	1.392 (2)	C7—C8	1.466 (3)
N3—C10	1.336 (2)	C8—C9	1.377 (3)
N3—C11	1.338 (3)	C8—C12	1.392 (3)
C1—C6	1.396 (3)	C9—C10	1.380 (3)
C1—C2	1.399 (3)	C9—H9	0.95
C2—C3	1.393 (3)	C10—H10	0.95
C3—C4	1.378 (3)	C11—C12	1.373 (3)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.401 (3)	C12—H12	0.95
C1—N1—C7	106.18 (16)	C5—C6—H6	121.5
C1—N1—H1	127.4 (13)	C1—C6—H6	121.5
C7—N1—H1	126.4 (14)	N2—C7—N1	113.51 (17)
C7—N2—C2	104.53 (15)	N2—C7—C8	123.97 (16)
C10—N3—C11	115.83 (18)	N1—C7—C8	122.52 (18)
N1—C1—C6	132.60 (19)	C9—C8—C12	117.48 (19)
N1—C1—C2	105.96 (16)	C9—C8—C7	122.43 (17)
C6—C1—C2	121.44 (19)	C12—C8—C7	120.06 (19)
N2—C2—C3	129.31 (18)	C8—C9—C10	119.18 (18)
N2—C2—C1	109.83 (18)	C8—C9—H9	120.4
C3—C2—C1	120.84 (18)	C10—C9—H9	120.4
C4—C3—C2	117.37 (19)	N3—C10—C9	124.2 (2)
C4—C3—H3	121.3	N3—C10—H10	117.9
C2—C3—H3	121.3	C9—C10—H10	117.9
C3—C4—C5	121.4 (2)	N3—C11—C12	124.24 (18)
C3—C4—H4	119.3	N3—C11—H11	117.9
C5—C4—H4	119.3	C12—C11—H11	117.9
C6—C5—C4	121.96 (19)	C11—C12—C8	119.1 (2)
C6—C5—H5	119.0	C11—C12—H12	120.5
C4—C5—H5	119.0	C8—C12—H12	120.5
C5—C6—C1	117.04 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.99 (2)	1.96 (2)	2.924 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.99 (2)	1.96 (2)	2.924 (2)	165 (2)

Symmetry code: (i) .