1-(1H-Benzimidazol-2-yl)-4-nitro-benzene dimethyl-formamide solvate.

In the title compound, C(13)H(9)N(3)O(2)·C(3)H(7)NO, the benzimidazole ring system and the benzene ring are essentially coplanar, forming a dihedral angle of 0.86 (5)°. The crystal packing is stabilized by an inter-molecular N-H⋯O hydrogen bond and a π-π stacking inter-action with a centroid-centroid separation of 3.685 (4) Å.

Related literature

For general background to benzimidazole compounds, see: Zarrinmayeh et al. (1998 ▶); Gallagher et al. (2001 ▶); Howarth & Hanlon (2001 ▶).

Experimental

Crystal data

C13H9N3O2·C3H7NO

M = 312.33

Triclinic,

a = 6.6228 (13) Å

b = 10.601 (2) Å

c = 11.886 (2) Å

α = 84.534 (10)°

β = 74.13 (2)°

γ = 81.53 (3)°

V = 792.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.30 × 0.26 × 0.24 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.96, T max = 0.98

7352 measured reflections

3102 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.138

S = 1.01

3102 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005315/rz2294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005315/rz2294Isup2.hkl

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

C13H9N3O2·C3H7NO	Z = 2
Mr = 312.33	F(000) = 328
Triclinic, P1	Dx = 1.309 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6228 (13) Å	Cell parameters from 5280 reflections
b = 10.601 (2) Å	θ = 3.2–27.4°
c = 11.886 (2) Å	µ = 0.09 mm−1
α = 84.534 (10)°	T = 291 K
β = 74.13 (2)°	Block, yellow
γ = 81.53 (3)°	0.30 × 0.26 × 0.24 mm
V = 792.6 (3) Å3

Rigaku Mercury2 diffractometer	3102 independent reflections
Radiation source: fine-focus sealed tube	1567 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.2°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→12
Tmin = 0.96, Tmax = 0.98	l = −14→14
7352 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
3102 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.19 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
C1	−0.0895 (4)	0.3267 (2)	0.7884 (2)	0.0599 (6)
C2	−0.2701 (4)	0.3902 (2)	0.8605 (2)	0.0798 (8)
H2A	−0.2737	0.4732	0.8809	0.096*
C3	−0.4438 (5)	0.3249 (3)	0.9006 (2)	0.0857 (8)
H3A	−0.5668	0.3643	0.9497	0.103*
C4	−0.4385 (4)	0.2011 (2)	0.8689 (2)	0.0798 (8)
H4A	−0.5584	0.1597	0.8973	0.096*
C5	−0.2605 (4)	0.1383 (2)	0.7965 (2)	0.0658 (7)
H5A	−0.2587	0.0557	0.7756	0.079*
C6	−0.0832 (4)	0.20250 (19)	0.75577 (18)	0.0540 (6)
C7	0.2234 (4)	0.26232 (18)	0.67137 (18)	0.0535 (6)
C8	0.4421 (4)	0.26378 (18)	0.60121 (18)	0.0520 (6)
C9	0.5535 (4)	0.36846 (19)	0.5917 (2)	0.0605 (6)
H9A	0.4864	0.4414	0.6308	0.073*
C10	0.7583 (4)	0.3659 (2)	0.5264 (2)	0.0610 (6)
H10A	0.8299	0.4365	0.5202	0.073*
C11	0.8578 (4)	0.2568 (2)	0.46957 (19)	0.0564 (6)
C12	0.7539 (4)	0.1508 (2)	0.4773 (2)	0.0667 (7)
H12A	0.8226	0.0777	0.4389	0.080*
C13	0.5471 (4)	0.1560 (2)	0.5427 (2)	0.0670 (7)
H13A	0.4757	0.0855	0.5480	0.080*
C14	0.7196 (4)	0.3189 (2)	0.2083 (2)	0.0751 (7)
H14A	0.5807	0.3254	0.2545	0.090*
C15	1.0088 (5)	0.1989 (3)	0.0766 (3)	0.1051 (10)
H15A	1.0684	0.2774	0.0694	0.158*
H15B	1.0053	0.1771	0.0006	0.158*
H15C	1.0940	0.1320	0.1093	0.158*
C16	0.6700 (5)	0.1095 (2)	0.1649 (3)	0.1028 (10)
H16A	0.5303	0.1337	0.2136	0.154*
H16B	0.7355	0.0352	0.2002	0.154*
H16C	0.6612	0.0908	0.0891	0.154*
N1	0.1073 (3)	0.36303 (15)	0.73324 (16)	0.0621 (5)
H1A	0.1515	0.4383	0.7376	0.074*
N2	0.1147 (3)	0.16428 (15)	0.68163 (16)	0.0564 (5)
N3	1.0776 (3)	0.2533 (2)	0.39914 (18)	0.0720 (6)
N4	0.7958 (3)	0.21395 (17)	0.15256 (17)	0.0647 (6)
O1	1.1681 (3)	0.34815 (17)	0.39184 (17)	0.0937 (6)
O2	1.1653 (3)	0.15534 (18)	0.35180 (19)	0.1073 (7)
O3	0.8186 (3)	0.40844 (16)	0.20342 (19)	0.1109 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0662 (17)	0.0574 (14)	0.0553 (15)	−0.0032 (13)	−0.0130 (13)	−0.0147 (12)
C2	0.086 (2)	0.0740 (17)	0.0737 (18)	−0.0067 (16)	−0.0048 (16)	−0.0276 (14)
C3	0.071 (2)	0.100 (2)	0.0763 (19)	−0.0065 (17)	0.0020 (15)	−0.0251 (16)
C4	0.076 (2)	0.0857 (19)	0.0749 (19)	−0.0169 (15)	−0.0098 (16)	−0.0081 (15)
C5	0.0683 (18)	0.0643 (15)	0.0641 (16)	−0.0103 (14)	−0.0141 (14)	−0.0081 (13)
C6	0.0637 (16)	0.0493 (12)	0.0487 (14)	−0.0006 (11)	−0.0159 (13)	−0.0085 (10)
C7	0.0644 (17)	0.0431 (12)	0.0561 (15)	0.0000 (11)	−0.0212 (13)	−0.0119 (11)
C8	0.0579 (15)	0.0467 (12)	0.0517 (14)	−0.0007 (11)	−0.0159 (12)	−0.0096 (10)
C9	0.0636 (17)	0.0448 (13)	0.0702 (16)	0.0021 (11)	−0.0139 (14)	−0.0144 (11)
C10	0.0647 (17)	0.0475 (12)	0.0715 (16)	−0.0054 (11)	−0.0179 (14)	−0.0103 (12)
C11	0.0571 (15)	0.0576 (14)	0.0540 (14)	−0.0015 (12)	−0.0149 (12)	−0.0094 (11)
C12	0.0693 (18)	0.0543 (14)	0.0756 (18)	−0.0022 (13)	−0.0139 (15)	−0.0237 (12)
C13	0.0667 (18)	0.0564 (14)	0.0773 (17)	−0.0107 (12)	−0.0098 (15)	−0.0243 (13)
C14	0.0786 (19)	0.0670 (16)	0.0733 (18)	0.0010 (15)	−0.0107 (15)	−0.0157 (14)
C15	0.086 (2)	0.116 (2)	0.097 (2)	0.0080 (18)	−0.0026 (19)	−0.0213 (18)
C16	0.126 (3)	0.0753 (18)	0.118 (3)	−0.0349 (19)	−0.041 (2)	−0.0015 (17)
N1	0.0643 (13)	0.0478 (10)	0.0726 (13)	−0.0072 (9)	−0.0103 (11)	−0.0195 (9)
N2	0.0595 (13)	0.0482 (10)	0.0629 (13)	−0.0041 (9)	−0.0176 (11)	−0.0098 (9)
N3	0.0658 (15)	0.0694 (14)	0.0772 (15)	−0.0028 (12)	−0.0122 (12)	−0.0158 (12)
N4	0.0693 (14)	0.0548 (11)	0.0672 (13)	−0.0039 (10)	−0.0117 (11)	−0.0145 (10)
O1	0.0768 (13)	0.0837 (12)	0.1160 (16)	−0.0240 (11)	−0.0070 (11)	−0.0164 (11)
O2	0.0802 (14)	0.0926 (14)	0.1324 (18)	−0.0057 (11)	0.0111 (12)	−0.0483 (13)
O3	0.1330 (19)	0.0708 (12)	0.1336 (18)	−0.0294 (12)	−0.0241 (14)	−0.0360 (12)

C1—N1	1.381 (3)	C10—H10A	0.9300
C1—C2	1.389 (3)	C11—C12	1.385 (3)
C1—C6	1.400 (3)	C11—N3	1.464 (3)
C2—C3	1.379 (3)	C12—C13	1.374 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.393 (3)	C13—H13A	0.9300
C3—H3A	0.9300	C14—O3	1.219 (3)
C4—C5	1.377 (3)	C14—N4	1.313 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.392 (3)	C15—N4	1.448 (3)
C5—H5A	0.9300	C15—H15A	0.9600
C6—N2	1.392 (3)	C15—H15B	0.9600
C7—N2	1.327 (2)	C15—H15C	0.9600
C7—N1	1.368 (2)	C16—N4	1.454 (3)
C7—C8	1.462 (3)	C16—H16A	0.9600
C8—C13	1.387 (3)	C16—H16B	0.9600
C8—C9	1.400 (3)	C16—H16C	0.9600
C9—C10	1.364 (3)	N1—H1A	0.8998
C9—H9A	0.9300	N3—O2	1.220 (2)
C10—C11	1.381 (3)	N3—O1	1.229 (2)
N1—C1—C2	132.3 (2)	C12—C11—N3	119.2 (2)
N1—C1—C6	105.77 (19)	C13—C12—C11	118.5 (2)
C2—C1—C6	121.9 (2)	C13—C12—H12A	120.7
C3—C2—C1	117.2 (2)	C11—C12—H12A	120.7
C3—C2—H2A	121.4	C12—C13—C8	121.7 (2)
C1—C2—H2A	121.4	C12—C13—H13A	119.2
C2—C3—C4	121.3 (2)	C8—C13—H13A	119.2
C2—C3—H3A	119.4	O3—C14—N4	124.4 (3)
C4—C3—H3A	119.4	O3—C14—H14A	117.8
C5—C4—C3	121.8 (3)	N4—C14—H14A	117.8
C5—C4—H4A	119.1	N4—C15—H15A	109.5
C3—C4—H4A	119.1	N4—C15—H15B	109.5
C4—C5—C6	117.8 (2)	H15A—C15—H15B	109.5
C4—C5—H5A	121.1	N4—C15—H15C	109.5
C6—C5—H5A	121.1	H15A—C15—H15C	109.5
C5—C6—N2	130.4 (2)	H15B—C15—H15C	109.5
C5—C6—C1	120.1 (2)	N4—C16—H16A	109.5
N2—C6—C1	109.5 (2)	N4—C16—H16B	109.5
N2—C7—N1	112.44 (19)	H16A—C16—H16B	109.5
N2—C7—C8	124.12 (18)	N4—C16—H16C	109.5
N1—C7—C8	123.44 (19)	H16A—C16—H16C	109.5
C13—C8—C9	117.9 (2)	H16B—C16—H16C	109.5
C13—C8—C7	119.0 (2)	C7—N1—C1	107.00 (17)
C9—C8—C7	123.09 (19)	C7—N1—H1A	126.3
C10—C9—C8	121.5 (2)	C1—N1—H1A	126.7
C10—C9—H9A	119.3	C7—N2—C6	105.30 (17)
C8—C9—H9A	119.3	O2—N3—O1	122.4 (2)
C9—C10—C11	119.0 (2)	O2—N3—C11	118.7 (2)
C9—C10—H10A	120.5	O1—N3—C11	118.9 (2)
C11—C10—H10A	120.5	C14—N4—C15	120.7 (2)
C10—C11—C12	121.5 (2)	C14—N4—C16	121.4 (2)
C10—C11—N3	119.3 (2)	C15—N4—C16	117.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.90	1.89	2.753 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.90	1.89	2.753 (2)	161

Symmetry code: (i) .