4-Chloro-2-(6-nitro-1H-benzimidazol-2-yl)phenol N,N-dimethyl-form-amide solvate.

In the title compound, C(13)H(8)ClN(3)O(3)·C(3)H(7)NO, the benzimidazole and benzene rings make a dihedral angle of 0.63 (11)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The solvent mol-ecule is hydrogen-bonded to the benzimidazole mol-ecule by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, generating an R(1) (2)(7) ring motif. In the crystal, the mol-ecules are arranged into parallel layers perpendicular to the c axis and stabilized by weak π-π inter-actions [centroid-centroid distances in the range 3.4036 (18)-3.5878 (16) Å].

Related literature

For general background to and the biological activity of benzimidazole derivatives, see: Trivedi et al. (2006 ▶); White et al. (2004 ▶); Garuti et al. (2004 ▶). For related structures, see: Eltayeb et al. (2009 ▶); Yeap et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H8ClN3O3·C3H7NO

M = 362.77

Monoclinic,

a = 15.200 (2) Å

b = 18.355 (2) Å

c = 13.279 (3) Å

β = 119.232 (2)°

V = 3233.1 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.45 × 0.12 × 0.05 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.987

14542 measured reflections

3719 independent reflections

2771 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.201

S = 1.07

3719 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041243/ng5046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041243/ng5046Isup2.hkl

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

C13H8ClN3O3·C3H7NO	F(000) = 1504
Mr = 362.77	Dx = 1.491 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3050 reflections
a = 15.200 (2) Å	θ = 2.8–29.6°
b = 18.355 (2) Å	µ = 0.27 mm−1
c = 13.279 (3) Å	T = 100 K
β = 119.232 (2)°	Plate, orange
V = 3233.1 (9) Å3	0.45 × 0.12 × 0.05 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	3719 independent reflections
Radiation source: fine-focus sealed tube	2771 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.889, Tmax = 0.987	k = −23→23
14542 measured reflections	l = −17→17

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0961P)2 + 7.3038P] where P = (Fo2 + 2Fc2)/3
3719 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	−0.29053 (6)	0.25697 (4)	0.23736 (8)	0.0465 (3)
O1	0.37235 (16)	0.53844 (13)	0.5412 (2)	0.0418 (6)
O2	0.36636 (17)	0.65517 (14)	0.5483 (2)	0.0444 (6)
O3	−0.28130 (16)	0.57579 (11)	0.23880 (19)	0.0362 (5)
H1O3	−0.2293	0.5904	0.2591	0.054*
N1	−0.00189 (16)	0.46895 (13)	0.37354 (18)	0.0242 (5)
H1N1	0.0057	0.4209	0.3772	0.029*
N2	−0.08820 (17)	0.57321 (12)	0.33366 (19)	0.0245 (5)
N3	0.32588 (18)	0.59601 (15)	0.5240 (2)	0.0327 (6)
C1	0.06745 (19)	0.52535 (15)	0.4062 (2)	0.0227 (5)
C2	0.1718 (2)	0.52401 (16)	0.4543 (2)	0.0261 (6)
H2A	0.2085	0.4809	0.4719	0.031*
C3	0.21629 (19)	0.59173 (15)	0.4736 (2)	0.0250 (6)
C4	0.1634 (2)	0.65760 (16)	0.4484 (2)	0.0304 (6)
H4A	0.1978	0.7016	0.4629	0.036*
C5	0.0598 (2)	0.65720 (16)	0.4018 (2)	0.0287 (6)
H5A	0.0233	0.7004	0.3852	0.034*
C6	0.0120 (2)	0.59004 (15)	0.3807 (2)	0.0250 (6)
C7	−0.09359 (19)	0.50080 (15)	0.3299 (2)	0.0228 (5)
C8	−0.18949 (19)	0.46199 (14)	0.2832 (2)	0.0218 (5)
C9	−0.2793 (2)	0.50277 (16)	0.2409 (2)	0.0269 (6)
C10	−0.3707 (2)	0.46580 (18)	0.2000 (3)	0.0342 (7)
H10A	−0.4303	0.4923	0.1719	0.041*
C11	−0.3743 (2)	0.39127 (18)	0.2004 (2)	0.0339 (7)
H11A	−0.4355	0.3674	0.1750	0.041*
C12	−0.2861 (2)	0.35177 (17)	0.2390 (2)	0.0301 (6)
C13	−0.1943 (2)	0.38598 (15)	0.2804 (2)	0.0254 (6)
H13A	−0.1357	0.3586	0.3064	0.030*
O4	0.0524 (2)	0.32533 (15)	0.3936 (3)	0.0728 (9)
N4	0.0760 (2)	0.20375 (15)	0.4053 (2)	0.0374 (6)
C14	0.0997 (3)	0.2715 (2)	0.3954 (4)	0.0526 (9)
H14A	0.1575	0.2787	0.3892	0.063*
C15	−0.0141 (3)	0.1904 (3)	0.4121 (4)	0.0611 (11)
H15A	−0.0317	0.2334	0.4394	0.092*
H15B	−0.0026	0.1509	0.4645	0.092*
H15C	−0.0681	0.1779	0.3370	0.092*
C16	0.1378 (4)	0.1427 (2)	0.4137 (4)	0.0710 (13)
H16A	0.1942	0.1590	0.4061	0.106*
H16B	0.0989	0.1085	0.3534	0.106*
H16C	0.1616	0.1195	0.4873	0.106*

	U11	U22	U33	U12	U13	U23
Cl1	0.0443 (5)	0.0298 (4)	0.0618 (5)	−0.0138 (3)	0.0230 (4)	−0.0003 (3)
O1	0.0249 (11)	0.0443 (14)	0.0522 (13)	−0.0012 (10)	0.0157 (10)	−0.0013 (10)
O2	0.0298 (12)	0.0452 (14)	0.0561 (14)	−0.0158 (10)	0.0192 (10)	−0.0078 (11)
O3	0.0252 (10)	0.0291 (11)	0.0515 (13)	0.0043 (8)	0.0164 (10)	−0.0016 (9)
N1	0.0197 (11)	0.0250 (12)	0.0278 (11)	0.0006 (9)	0.0116 (9)	0.0019 (9)
N2	0.0230 (11)	0.0238 (12)	0.0279 (11)	−0.0039 (9)	0.0135 (9)	−0.0012 (9)
N3	0.0229 (12)	0.0402 (15)	0.0341 (12)	−0.0047 (11)	0.0133 (10)	−0.0033 (10)
C1	0.0209 (12)	0.0270 (14)	0.0217 (11)	−0.0059 (10)	0.0115 (10)	−0.0023 (10)
C2	0.0226 (13)	0.0301 (15)	0.0271 (12)	0.0008 (11)	0.0134 (10)	−0.0006 (10)
C3	0.0172 (12)	0.0326 (15)	0.0248 (12)	−0.0051 (10)	0.0101 (10)	−0.0024 (10)
C4	0.0292 (15)	0.0276 (15)	0.0334 (14)	−0.0087 (11)	0.0145 (11)	−0.0046 (11)
C5	0.0273 (14)	0.0251 (14)	0.0325 (14)	0.0016 (11)	0.0138 (11)	−0.0001 (11)
C6	0.0235 (13)	0.0276 (14)	0.0235 (12)	−0.0018 (11)	0.0112 (10)	−0.0020 (10)
C7	0.0196 (12)	0.0290 (14)	0.0217 (11)	−0.0008 (10)	0.0114 (10)	0.0009 (10)
C8	0.0187 (12)	0.0248 (14)	0.0219 (11)	−0.0025 (10)	0.0100 (10)	−0.0007 (9)
C9	0.0226 (13)	0.0294 (15)	0.0281 (13)	0.0011 (11)	0.0119 (11)	0.0008 (10)
C10	0.0186 (13)	0.0455 (19)	0.0371 (15)	0.0020 (12)	0.0124 (12)	−0.0009 (13)
C11	0.0227 (14)	0.0443 (18)	0.0328 (14)	−0.0118 (12)	0.0121 (11)	−0.0024 (12)
C12	0.0288 (14)	0.0309 (15)	0.0299 (13)	−0.0094 (12)	0.0138 (11)	−0.0005 (11)
C13	0.0213 (13)	0.0276 (14)	0.0264 (12)	−0.0011 (10)	0.0110 (10)	0.0019 (10)
O4	0.073 (2)	0.0341 (15)	0.099 (2)	0.0211 (14)	0.0322 (18)	0.0026 (14)
N4	0.0405 (15)	0.0347 (15)	0.0394 (14)	−0.0003 (11)	0.0214 (12)	−0.0028 (11)
C14	0.048 (2)	0.041 (2)	0.066 (2)	−0.0015 (17)	0.0258 (18)	0.0046 (17)
C15	0.048 (2)	0.070 (3)	0.064 (2)	−0.001 (2)	0.027 (2)	0.009 (2)
C16	0.092 (4)	0.051 (3)	0.078 (3)	0.023 (2)	0.049 (3)	0.000 (2)

Cl1—C12	1.741 (3)	C8—C13	1.397 (4)
O1—N3	1.229 (3)	C8—C9	1.411 (4)
O2—N3	1.212 (3)	C9—C10	1.396 (4)
O3—C9	1.341 (3)	C10—C11	1.369 (5)
O3—H1O3	0.7498	C10—H10A	0.9300
N1—C7	1.354 (3)	C11—C12	1.384 (4)
N1—C1	1.387 (3)	C11—H11A	0.9300
N1—H1N1	0.8875	C12—C13	1.376 (4)
N2—C7	1.331 (4)	C13—H13A	0.9300
N2—C6	1.370 (3)	O4—C14	1.216 (5)
N3—C3	1.463 (3)	N4—C14	1.319 (5)
C1—C2	1.391 (4)	N4—C16	1.431 (5)
C1—C6	1.399 (4)	N4—C15	1.437 (5)
C2—C3	1.378 (4)	C14—H14A	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.399 (4)	C15—H15B	0.9600
C4—C5	1.383 (4)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.388 (4)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C7—C8	1.461 (4)
C9—O3—H1O3	110.0	O3—C9—C8	123.1 (2)
C7—N1—C1	106.1 (2)	C10—C9—C8	118.9 (3)
C7—N1—H1N1	122.1	C11—C10—C9	121.2 (3)
C1—N1—H1N1	131.8	C11—C10—H10A	119.4
C7—N2—C6	106.1 (2)	C9—C10—H10A	119.4
O2—N3—O1	123.4 (3)	C10—C11—C12	119.5 (3)
O2—N3—C3	119.1 (3)	C10—C11—H11A	120.3
O1—N3—C3	117.5 (2)	C12—C11—H11A	120.3
N1—C1—C2	130.7 (3)	C13—C12—C11	121.3 (3)
N1—C1—C6	106.4 (2)	C13—C12—Cl1	119.1 (2)
C2—C1—C6	122.9 (3)	C11—C12—Cl1	119.6 (2)
C3—C2—C1	114.6 (3)	C12—C13—C8	119.7 (3)
C3—C2—H2A	122.7	C12—C13—H13A	120.1
C1—C2—H2A	122.7	C8—C13—H13A	120.1
C2—C3—C4	124.2 (3)	C14—N4—C16	123.0 (4)
C2—C3—N3	118.6 (3)	C14—N4—C15	118.9 (3)
C4—C3—N3	117.1 (2)	C16—N4—C15	118.0 (4)
C5—C4—C3	119.9 (3)	O4—C14—N4	125.4 (4)
C5—C4—H4A	120.0	O4—C14—H14A	117.3
C3—C4—H4A	120.0	N4—C14—H14A	117.3
C4—C5—C6	117.6 (3)	N4—C15—H15A	109.5
C4—C5—H5A	121.2	N4—C15—H15B	109.5
C6—C5—H5A	121.2	H15A—C15—H15B	109.5
N2—C6—C5	130.4 (3)	N4—C15—H15C	109.5
N2—C6—C1	108.9 (2)	H15A—C15—H15C	109.5
C5—C6—C1	120.8 (2)	H15B—C15—H15C	109.5
N2—C7—N1	112.6 (2)	N4—C16—H16A	109.5
N2—C7—C8	122.2 (2)	N4—C16—H16B	109.5
N1—C7—C8	125.2 (2)	H16A—C16—H16B	109.5
C13—C8—C9	119.4 (2)	N4—C16—H16C	109.5
C13—C8—C7	121.8 (2)	H16A—C16—H16C	109.5
C9—C8—C7	118.8 (2)	H16B—C16—H16C	109.5
O3—C9—C10	118.0 (3)
C7—N1—C1—C2	−179.0 (3)	C6—N2—C7—C8	−179.2 (2)
C7—N1—C1—C6	0.6 (3)	C1—N1—C7—N2	−0.9 (3)
N1—C1—C2—C3	178.8 (2)	C1—N1—C7—C8	179.1 (2)
C6—C1—C2—C3	−0.8 (4)	N2—C7—C8—C13	−179.5 (2)
C1—C2—C3—C4	0.2 (4)	N1—C7—C8—C13	0.4 (4)
C1—C2—C3—N3	−180.0 (2)	N2—C7—C8—C9	−0.2 (4)
O2—N3—C3—C2	−175.2 (3)	N1—C7—C8—C9	179.8 (2)
O1—N3—C3—C2	3.6 (4)	C13—C8—C9—O3	−178.9 (2)
O2—N3—C3—C4	4.6 (4)	C7—C8—C9—O3	1.7 (4)
O1—N3—C3—C4	−176.6 (2)	C13—C8—C9—C10	1.7 (4)
C2—C3—C4—C5	0.5 (4)	C7—C8—C9—C10	−177.7 (2)
N3—C3—C4—C5	−179.3 (2)	O3—C9—C10—C11	−179.4 (3)
C3—C4—C5—C6	−0.7 (4)	C8—C9—C10—C11	0.0 (4)
C7—N2—C6—C5	178.3 (3)	C9—C10—C11—C12	−1.9 (4)
C7—N2—C6—C1	−0.4 (3)	C10—C11—C12—C13	2.1 (4)
C4—C5—C6—N2	−178.5 (3)	C10—C11—C12—Cl1	−178.9 (2)
C4—C5—C6—C1	0.1 (4)	C11—C12—C13—C8	−0.4 (4)
N1—C1—C6—N2	−0.1 (3)	Cl1—C12—C13—C8	−179.4 (2)
C2—C1—C6—N2	179.5 (2)	C9—C8—C13—C12	−1.5 (4)
N1—C1—C6—C5	−179.0 (2)	C7—C8—C13—C12	177.9 (2)
C2—C1—C6—C5	0.6 (4)	C16—N4—C14—O4	−176.2 (4)
C6—N2—C7—N1	0.8 (3)	C15—N4—C14—O4	1.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.75	1.90	2.568 (4)	149
N1—H1N1···O4	0.89	1.86	2.736 (4)	167
C13—H13A···O4	0.93	2.58	3.472 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2	0.75	1.90	2.568 (4)	149
N1—H1N1⋯O4	0.89	1.86	2.736 (4)	167
C13—H13A⋯O4	0.93	2.58	3.472 (5)	161