Glutaric acid-2-(pyridin-4-yl)-1H-benzimidazole (1/1).

The crystal structure of the title co-crystal, C(12)H(9)N(3)·C(5)H(8)O(4), N-H⋯O and O-H⋯N hydrogen bonds link the components. There are also π-π stacking inter-actions between the imidazole rings, between the imidazole and pyridine rings and between the pyridine and benzene rings [centroid-centroid distances = 3.643 (2), 3.573 (2) and 3.740 (1)Å, respectively].

Related literature

For background to hydrogen bonds, see: Moorthy et al. (2002 ▶); Muthuraman et al. (2000 ▶); Nangia & Desiraju (1999 ▶); Bhattacharjya et al. (2004 ▶). For related structures, see: Bei et al. (2000 ▶); Ozbey et al. (1998 ▶).

Experimental

Crystal data

C12H9N3·C5H8O4

M = 327.34

Triclinic,

a = 7.4384 (15) Å

b = 8.9911 (18) Å

c = 11.868 (2) Å

α = 86.67 (3)°

β = 81.66 (3)°

γ = 85.57 (3)°

V = 782.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.17 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

6041 measured reflections

2664 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.149

S = 1.11

2664 reflections

226 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049695/fj2466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049695/fj2466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049695/fj2466Isup3.cml

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

C12H9N3·C5H8O4	Z = 2
Mr = 327.34	F(000) = 344
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4384 (15) Å	Cell parameters from 25 reflections
b = 8.9911 (18) Å	θ = 4–14°
c = 11.868 (2) Å	µ = 0.10 mm−1
α = 86.67 (3)°	T = 293 K
β = 81.66 (3)°	Block, colorless
γ = 85.57 (3)°	0.20 × 0.17 × 0.15 mm
V = 782.1 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.1°
graphite	h = −7→7
ω scans	k = −10→10
6041 measured reflections	l = −14→13
2664 independent reflections	3 standard reflections every 100 reflections
1657 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.020P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2664 reflections	Δρmax = 0.35 e Å−3
226 parameters	Δρmin = −0.32 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (5)

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	0.2659 (2)	0.5349 (2)	0.58023 (17)	0.0435 (5)
H1A	0.2940	0.6038	0.6206	0.052*
N2	0.2164 (2)	0.4197 (2)	0.42719 (17)	0.0432 (5)
N3	0.4250 (3)	0.9193 (2)	0.24990 (19)	0.0526 (6)
C1	0.1814 (3)	0.3243 (2)	0.5230 (2)	0.0403 (6)
C2	0.1261 (3)	0.1787 (3)	0.5328 (2)	0.0478 (6)
H2B	0.1037	0.1309	0.4693	0.057*
C3	0.1057 (3)	0.1083 (3)	0.6392 (2)	0.0515 (7)
H3B	0.0690	0.0112	0.6477	0.062*
C4	0.1387 (3)	0.1791 (3)	0.7345 (2)	0.0540 (7)
H4A	0.1251	0.1275	0.8051	0.065*
C5	0.1912 (3)	0.3235 (3)	0.7273 (2)	0.0508 (7)
H5A	0.2117	0.3707	0.7915	0.061*
C6	0.2117 (3)	0.3952 (3)	0.6200 (2)	0.0408 (6)
C7	0.2664 (3)	0.5429 (2)	0.4655 (2)	0.0405 (6)
C8	0.3189 (3)	0.6750 (3)	0.3922 (2)	0.0416 (6)
C9	0.3303 (3)	0.6703 (3)	0.2746 (2)	0.0502 (7)
H9A	0.3025	0.5851	0.2416	0.060*
C10	0.3835 (3)	0.7942 (3)	0.2073 (2)	0.0563 (7)
H10A	0.3908	0.7903	0.1286	0.068*
C11	0.4129 (3)	0.9229 (3)	0.3626 (2)	0.0520 (7)
H11A	0.4408	1.0097	0.3934	0.062*
C12	0.3614 (3)	0.8050 (3)	0.4361 (2)	0.0488 (6)
H12A	0.3553	0.8125	0.5144	0.059*
O1	−0.3978 (3)	0.1206 (2)	0.12019 (17)	0.0654 (6)
O2	−0.3751 (2)	0.2383 (2)	0.27704 (16)	0.0599 (5)
O3	0.2390 (4)	0.3965 (3)	0.1101 (2)	0.1041 (9)
O4	0.1264 (3)	0.2629 (2)	0.26029 (18)	0.0776 (7)
C13	−0.3421 (3)	0.2273 (3)	0.1748 (2)	0.0490 (6)
C14	−0.2312 (4)	0.3340 (3)	0.0967 (2)	0.0618 (8)
H14A	−0.1852	0.4040	0.1429	0.074*
H14B	−0.3110	0.3908	0.0497	0.074*
C15	−0.0728 (4)	0.2637 (3)	0.0197 (2)	0.0597 (7)
H15A	−0.0195	0.3404	−0.0327	0.072*
H15B	−0.1176	0.1914	−0.0252	0.072*
C16	0.0758 (4)	0.1854 (3)	0.0833 (2)	0.0619 (8)
H16A	0.0244	0.1063	0.1340	0.074*
H16B	0.1714	0.1405	0.0288	0.074*
C17	0.1557 (4)	0.2930 (3)	0.1513 (3)	0.0601 (8)
H1	0.173 (5)	0.338 (4)	0.308 (3)	0.123 (13)*
H2	−0.456 (4)	0.058 (4)	0.167 (3)	0.133 (15)*

	U11	U22	U33	U12	U13	U23
N1	0.0502 (11)	0.0392 (11)	0.0437 (13)	−0.0103 (8)	−0.0095 (9)	−0.0083 (9)
N2	0.0464 (11)	0.0400 (12)	0.0465 (13)	−0.0084 (9)	−0.0127 (9)	−0.0063 (10)
N3	0.0573 (12)	0.0472 (13)	0.0568 (15)	−0.0157 (10)	−0.0133 (10)	−0.0024 (11)
C1	0.0380 (12)	0.0384 (13)	0.0466 (15)	−0.0042 (9)	−0.0102 (10)	−0.0064 (11)
C2	0.0524 (14)	0.0402 (14)	0.0547 (17)	−0.0087 (11)	−0.0144 (11)	−0.0120 (12)
C3	0.0589 (15)	0.0391 (14)	0.0592 (18)	−0.0121 (11)	−0.0122 (12)	−0.0039 (13)
C4	0.0646 (16)	0.0458 (15)	0.0515 (17)	−0.0079 (12)	−0.0054 (13)	−0.0029 (13)
C5	0.0653 (16)	0.0461 (15)	0.0427 (16)	−0.0088 (12)	−0.0079 (12)	−0.0089 (12)
C6	0.0403 (12)	0.0364 (13)	0.0472 (15)	−0.0047 (9)	−0.0075 (10)	−0.0084 (11)
C7	0.0375 (12)	0.0408 (13)	0.0454 (15)	−0.0066 (10)	−0.0098 (10)	−0.0061 (11)
C8	0.0387 (12)	0.0406 (13)	0.0475 (15)	−0.0064 (9)	−0.0089 (10)	−0.0071 (11)
C9	0.0582 (15)	0.0474 (15)	0.0499 (16)	−0.0168 (11)	−0.0160 (12)	−0.0054 (12)
C10	0.0678 (17)	0.0572 (17)	0.0500 (17)	−0.0221 (13)	−0.0207 (13)	0.0012 (13)
C11	0.0566 (15)	0.0448 (15)	0.0569 (18)	−0.0151 (11)	−0.0064 (12)	−0.0102 (13)
C12	0.0523 (14)	0.0485 (15)	0.0470 (16)	−0.0128 (11)	−0.0049 (11)	−0.0082 (12)
O1	0.0996 (15)	0.0540 (12)	0.0469 (12)	−0.0322 (11)	−0.0076 (10)	−0.0088 (10)
O2	0.0784 (12)	0.0601 (12)	0.0441 (12)	−0.0230 (9)	−0.0063 (9)	−0.0081 (9)
O3	0.170 (2)	0.0867 (17)	0.0689 (16)	−0.0736 (17)	−0.0346 (15)	0.0149 (13)
O4	0.1193 (18)	0.0732 (15)	0.0487 (14)	−0.0464 (13)	−0.0185 (12)	−0.0038 (11)
C13	0.0623 (15)	0.0415 (14)	0.0453 (17)	−0.0102 (11)	−0.0097 (12)	−0.0044 (12)
C14	0.090 (2)	0.0469 (16)	0.0497 (17)	−0.0231 (14)	−0.0054 (15)	−0.0005 (13)
C15	0.0806 (18)	0.0623 (18)	0.0390 (16)	−0.0253 (14)	−0.0061 (13)	−0.0068 (13)
C16	0.088 (2)	0.0522 (17)	0.0492 (18)	−0.0181 (14)	−0.0124 (14)	−0.0107 (14)
C17	0.0833 (19)	0.0498 (17)	0.0520 (19)	−0.0205 (14)	−0.0195 (14)	0.0043 (14)

N1—C7	1.359 (3)	C9—H9A	0.9300
N1—C6	1.385 (3)	C10—H10A	0.9300
N1—H1A	0.8600	C11—C12	1.375 (3)
N2—C7	1.320 (3)	C11—H11A	0.9300
N2—C1	1.390 (3)	C12—H12A	0.9300
N3—C11	1.330 (3)	O1—C13	1.313 (3)
N3—C10	1.334 (3)	O1—H2	0.866 (10)
C1—C2	1.396 (3)	O2—C13	1.211 (3)
C1—C6	1.402 (3)	O3—C17	1.199 (3)
C2—C3	1.373 (3)	O4—C17	1.296 (3)
C2—H2B	0.9300	O4—H1	1.02 (4)
C3—C4	1.390 (4)	C13—C14	1.503 (3)
C3—H3B	0.9300	C14—C15	1.504 (4)
C4—C5	1.379 (4)	C14—H14A	0.9700
C4—H4A	0.9300	C14—H14B	0.9700
C5—C6	1.387 (4)	C15—C16	1.532 (4)
C5—H5A	0.9300	C15—H15A	0.9700
C7—C8	1.475 (3)	C15—H15B	0.9700
C8—C12	1.383 (3)	C16—C17	1.503 (4)
C8—C9	1.389 (4)	C16—H16A	0.9700
C9—C10	1.381 (3)	C16—H16B	0.9700
C7—N1—C6	107.18 (19)	C9—C10—H10A	118.5
C7—N1—H1A	126.4	N3—C11—C12	123.4 (2)
C6—N1—H1A	126.4	N3—C11—H11A	118.3
C7—N2—C1	105.23 (19)	C12—C11—H11A	118.3
C11—N3—C10	117.5 (2)	C11—C12—C8	119.2 (2)
N2—C1—C2	130.2 (2)	C11—C12—H12A	120.4
N2—C1—C6	109.62 (19)	C8—C12—H12A	120.4
C2—C1—C6	120.2 (2)	C13—O1—H2	111 (3)
C3—C2—C1	117.8 (2)	C17—O4—H1	114 (2)
C3—C2—H2B	121.1	O2—C13—O1	123.9 (2)
C1—C2—H2B	121.1	O2—C13—C14	123.5 (2)
C2—C3—C4	121.4 (2)	O1—C13—C14	112.6 (2)
C2—C3—H3B	119.3	C13—C14—C15	115.5 (2)
C4—C3—H3B	119.3	C13—C14—H14A	108.4
C5—C4—C3	121.9 (2)	C15—C14—H14A	108.4
C5—C4—H4A	119.0	C13—C14—H14B	108.4
C3—C4—H4A	119.0	C15—C14—H14B	108.4
C4—C5—C6	116.9 (2)	H14A—C14—H14B	107.5
C4—C5—H5A	121.6	C14—C15—C16	113.8 (2)
C6—C5—H5A	121.6	C14—C15—H15A	108.8
N1—C6—C5	133.1 (2)	C16—C15—H15A	108.8
N1—C6—C1	105.2 (2)	C14—C15—H15B	108.8
C5—C6—C1	121.7 (2)	C16—C15—H15B	108.8
N2—C7—N1	112.81 (19)	H15A—C15—H15B	107.7
N2—C7—C8	124.0 (2)	C17—C16—C15	111.4 (2)
N1—C7—C8	123.2 (2)	C17—C16—H16A	109.3
C12—C8—C9	117.8 (2)	C15—C16—H16A	109.3
C12—C8—C7	122.3 (2)	C17—C16—H16B	109.3
C9—C8—C7	119.9 (2)	C15—C16—H16B	109.3
C10—C9—C8	118.9 (2)	H16A—C16—H16B	108.0
C10—C9—H9A	120.5	O3—C17—O4	122.6 (3)
C8—C9—H9A	120.5	O3—C17—C16	124.1 (3)
N3—C10—C9	123.1 (3)	O4—C17—C16	113.3 (2)
N3—C10—H10A	118.5
C7—N2—C1—C2	−179.2 (2)	N2—C7—C8—C12	176.6 (2)
C7—N2—C1—C6	0.2 (2)	N1—C7—C8—C12	−4.0 (3)
N2—C1—C2—C3	178.4 (2)	N2—C7—C8—C9	−4.7 (3)
C6—C1—C2—C3	−1.0 (3)	N1—C7—C8—C9	174.8 (2)
C1—C2—C3—C4	0.0 (4)	C12—C8—C9—C10	0.2 (4)
C2—C3—C4—C5	0.8 (4)	C7—C8—C9—C10	−178.6 (2)
C3—C4—C5—C6	−0.7 (4)	C11—N3—C10—C9	−0.3 (4)
C7—N1—C6—C5	178.0 (2)	C8—C9—C10—N3	0.0 (4)
C7—N1—C6—C1	0.0 (2)	C10—N3—C11—C12	0.4 (4)
C4—C5—C6—N1	−178.0 (2)	N3—C11—C12—C8	−0.2 (4)
C4—C5—C6—C1	−0.2 (3)	C9—C8—C12—C11	−0.1 (3)
N2—C1—C6—N1	−0.1 (2)	C7—C8—C12—C11	178.7 (2)
C2—C1—C6—N1	179.4 (2)	O2—C13—C14—C15	126.6 (3)
N2—C1—C6—C5	−178.4 (2)	O1—C13—C14—C15	−52.9 (3)
C2—C1—C6—C5	1.1 (3)	C13—C14—C15—C16	−64.9 (3)
C1—N2—C7—N1	−0.2 (2)	C14—C15—C16—C17	−60.6 (3)
C1—N2—C7—C8	179.28 (19)	C15—C16—C17—O3	−64.2 (4)
C6—N1—C7—N2	0.2 (2)	C15—C16—C17—O4	116.1 (3)
C6—N1—C7—C8	−179.33 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.10	2.957 (3)	176.
O1—H2···N3ii	0.87 (1)	1.75 (1)	2.615 (3)	173 (4)
O4—H1···N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.10	2.957 (3)	176
O1—H2⋯N3ii	0.87 (1)	1.75 (1)	2.615 (3)	173 (4)
O4—H1⋯N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)

Symmetry codes: (i) ; (ii) .