2-(1H-Benzimidazol-2-yl)-4-nitro-phenol.

The title compound, C(13)H(9)N(3)O(3), was prepared by the reaction of 5-nitro-salicyl-aldehyde with 1,2-diamino-benzene in methanol. The whole mol-ecule is approximately planar, with a mean deviation from the plane defined by the non-H atoms of 0.0311 (4) Å, and with a dihedral angle between the benzene ring and the benzimidazole ring system of 1.1 (3)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, adjacent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For Schiff base compounds, see: Miura et al. (2009 ▶); Zhao et al. (2010 ▶); Karadağ et al. (2011) ▶; Bingöl Alpaslan et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H9N3O3

M = 255.23

Monoclinic,

a = 8.117 (3) Å

b = 6.769 (2) Å

c = 20.842 (3) Å

β = 99.235 (2)°

V = 1130.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.978, T max = 0.980

8933 measured reflections

2469 independent reflections

1283 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.153

S = 1.04

2469 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001644/hg2791sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001644/hg2791Isup2.hkl

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

C13H9N3O3	F(000) = 528
Mr = 255.23	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1124 reflections
a = 8.117 (3) Å	θ = 2.5–24.5°
b = 6.769 (2) Å	µ = 0.11 mm−1
c = 20.842 (3) Å	T = 298 K
β = 99.235 (2)°	Block, yellow
V = 1130.2 (5) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	1283 reflections with I > 2σ(I)
graphite	Rint = 0.061
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.978, Tmax = 0.980	k = −8→8
8933 measured reflections	l = −26→24

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1494P] where P = (Fo2 + 2Fc2)/3
2469 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.14 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
O1	0.7974 (3)	0.7492 (3)	0.12518 (10)	0.0680 (7)
H1	0.8172	0.7776	0.0889	0.102*
O2	0.4484 (3)	−0.0641 (3)	0.07368 (10)	0.0687 (7)
O3	0.4555 (3)	−0.0423 (3)	0.17662 (11)	0.0764 (8)
N1	0.8286 (3)	0.7006 (4)	0.00445 (12)	0.0547 (7)
N2	0.7411 (3)	0.4267 (3)	−0.04913 (12)	0.0495 (7)
N3	0.4870 (3)	0.0226 (4)	0.12571 (12)	0.0520 (7)
C1	0.6985 (3)	0.4551 (4)	0.06634 (13)	0.0425 (7)
C2	0.7228 (4)	0.5722 (4)	0.12303 (15)	0.0477 (8)
C3	0.6712 (4)	0.5046 (5)	0.17926 (14)	0.0562 (9)
H3	0.6878	0.5828	0.2164	0.067*
C4	0.5966 (4)	0.3252 (4)	0.18085 (14)	0.0492 (8)
H4	0.5632	0.2799	0.2189	0.059*
C5	0.5710 (3)	0.2113 (4)	0.12517 (14)	0.0425 (7)
C6	0.6205 (3)	0.2741 (4)	0.06832 (13)	0.0423 (7)
H6	0.6016	0.1950	0.0314	0.051*
C7	0.7560 (3)	0.5267 (4)	0.00778 (14)	0.0461 (7)
C8	0.8628 (4)	0.7151 (4)	−0.05876 (14)	0.0484 (8)
C9	0.8092 (3)	0.5440 (4)	−0.09285 (15)	0.0475 (7)
C10	0.8259 (4)	0.5165 (5)	−0.15689 (15)	0.0594 (9)
H10	0.7902	0.4011	−0.1791	0.071*
C11	0.8983 (4)	0.6692 (5)	−0.18671 (16)	0.0645 (10)
H11	0.9114	0.6565	−0.2300	0.077*
C12	0.9518 (4)	0.8413 (5)	−0.15324 (18)	0.0694 (10)
H12	0.9996	0.9414	−0.1747	0.083*
C13	0.9354 (4)	0.8666 (5)	−0.08904 (17)	0.0645 (9)
H13	0.9719	0.9816	−0.0668	0.077*
H2	0.698 (4)	0.307 (2)	−0.0610 (15)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0862 (18)	0.0561 (14)	0.0638 (17)	−0.0234 (12)	0.0183 (14)	−0.0113 (11)
O2	0.1090 (19)	0.0552 (13)	0.0445 (14)	−0.0268 (12)	0.0203 (13)	−0.0100 (11)
O3	0.122 (2)	0.0662 (15)	0.0487 (14)	−0.0165 (14)	0.0369 (14)	0.0101 (12)
N1	0.0620 (18)	0.0552 (15)	0.0460 (17)	−0.0161 (13)	0.0055 (13)	0.0067 (13)
N2	0.0588 (17)	0.0435 (14)	0.0465 (16)	−0.0102 (12)	0.0096 (13)	0.0012 (13)
N3	0.0713 (18)	0.0478 (15)	0.0403 (16)	−0.0029 (13)	0.0192 (13)	0.0019 (13)
C1	0.0475 (18)	0.0399 (16)	0.0387 (17)	−0.0038 (14)	0.0033 (14)	0.0005 (13)
C2	0.0458 (18)	0.0434 (17)	0.052 (2)	−0.0057 (14)	0.0037 (15)	−0.0061 (15)
C3	0.070 (2)	0.058 (2)	0.0413 (19)	−0.0124 (17)	0.0117 (16)	−0.0126 (16)
C4	0.061 (2)	0.0553 (19)	0.0328 (17)	−0.0008 (16)	0.0108 (15)	−0.0021 (15)
C5	0.0489 (18)	0.0390 (15)	0.0393 (18)	−0.0027 (14)	0.0058 (14)	0.0026 (13)
C6	0.0547 (18)	0.0418 (16)	0.0302 (16)	−0.0045 (14)	0.0061 (13)	−0.0025 (13)
C7	0.0497 (18)	0.0412 (16)	0.0462 (19)	−0.0073 (14)	0.0038 (14)	0.0028 (15)
C8	0.0494 (19)	0.0516 (18)	0.0422 (19)	−0.0055 (15)	0.0014 (15)	0.0085 (15)
C9	0.0442 (18)	0.0535 (18)	0.0447 (19)	−0.0026 (15)	0.0070 (14)	0.0107 (15)
C10	0.063 (2)	0.065 (2)	0.050 (2)	0.0030 (17)	0.0071 (16)	0.0009 (17)
C11	0.069 (2)	0.082 (3)	0.045 (2)	0.003 (2)	0.0157 (18)	0.0130 (19)
C12	0.070 (2)	0.075 (2)	0.064 (3)	−0.009 (2)	0.0121 (19)	0.028 (2)
C13	0.070 (2)	0.061 (2)	0.062 (2)	−0.0165 (18)	0.0115 (18)	0.0127 (18)

O1—C2	1.340 (3)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.381 (4)
O2—N3	1.228 (3)	C4—H4	0.9300
O3—N3	1.213 (3)	C5—C6	1.378 (4)
N1—C7	1.323 (3)	C6—H6	0.9300
N1—C8	1.393 (4)	C8—C13	1.384 (4)
N2—C7	1.354 (3)	C8—C9	1.392 (4)
N2—C9	1.388 (3)	C9—C10	1.376 (4)
N2—H2	0.902 (10)	C10—C11	1.385 (4)
N3—C5	1.449 (3)	C10—H10	0.9300
C1—C6	1.383 (4)	C11—C12	1.391 (5)
C1—C2	1.410 (4)	C11—H11	0.9300
C1—C7	1.458 (4)	C12—C13	1.376 (5)
C2—C3	1.384 (4)	C12—H12	0.9300
C3—C4	1.360 (4)	C13—H13	0.9300
C2—O1—H1	109.5	C5—C6—H6	120.1
C7—N1—C8	105.7 (2)	C1—C6—H6	120.1
C7—N2—C9	107.5 (2)	N1—C7—N2	112.1 (2)
C7—N2—H2	132 (2)	N1—C7—C1	123.0 (3)
C9—N2—H2	121 (2)	N2—C7—C1	124.9 (2)
O3—N3—O2	122.7 (3)	C13—C8—C9	120.3 (3)
O3—N3—C5	119.4 (3)	C13—C8—N1	130.4 (3)
O2—N3—C5	117.9 (2)	C9—C8—N1	109.3 (2)
C6—C1—C2	118.4 (3)	C10—C9—N2	132.1 (3)
C6—C1—C7	121.9 (2)	C10—C9—C8	122.5 (3)
C2—C1—C7	119.6 (2)	N2—C9—C8	105.4 (3)
O1—C2—C3	117.6 (3)	C9—C10—C11	116.7 (3)
O1—C2—C1	122.2 (3)	C9—C10—H10	121.7
C3—C2—C1	120.2 (3)	C11—C10—H10	121.7
C4—C3—C2	120.8 (3)	C10—C11—C12	121.4 (3)
C4—C3—H3	119.6	C10—C11—H11	119.3
C2—C3—H3	119.6	C12—C11—H11	119.3
C3—C4—C5	119.1 (3)	C13—C12—C11	121.4 (3)
C3—C4—H4	120.5	C13—C12—H12	119.3
C5—C4—H4	120.5	C11—C12—H12	119.3
C6—C5—C4	121.7 (3)	C12—C13—C8	117.7 (3)
C6—C5—N3	118.8 (2)	C12—C13—H13	121.1
C4—C5—N3	119.6 (3)	C8—C13—H13	121.1
C5—C6—C1	119.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.02 (1)	2.898 (3)	164 (3)
O1—H1···N1	0.82	1.85	2.590 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.02 (1)	2.898 (3)	164 (3)
O1—H1⋯N1	0.82	1.85	2.590 (3)	149

Symmetry code: (i) .