2-Methyl-5-nitro-1H-benzimidazole monohydrate.

In the title compound, C(8)H(7)N(3)O(2)·H(2)O, the 2-methyl-5-nitro-1H-benzimidazole mol-ecule, excluding the methyl H atoms, is approximately planar, with a maximum deviation of 0.137 (1) Å. The crystal structure is stabilized by water mol-ecules via N-H⋯O(water), O(water)-H⋯O and O(water)-H⋯N hydrogen bonds, forming sheets parallel to the (100) plane. A short inter-molecular contact between the benzene and imidazole rings, with a centroid-centroid distance of 3.6419 (10) Å, indicates a π-π inter-action.

Related literature

For general background to and the potential biological activity of benzimidazole derivatives, see: Puratchikody et al. (2008 ▶); Tonelli et al. (2010 ▶); Shingalapur et al. (2010 ▶); Refaat (2010 ▶); Lazer et al. (1987 ▶). For the preparation of the title compound, see: Umare et al. (2008 ▶); Singh & Pathak (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Eltayeb et al. (2009 ▶); Arumugam et al. (2010 ▶).

Experimental

Crystal data

C8H7N3O2·H2O

M = 195.18

Triclinic,

a = 6.9051 (10) Å

b = 7.1309 (11) Å

c = 10.0653 (15) Å

α = 79.421 (3)°

β = 73.062 (3)°

γ = 67.517 (3)°

V = 436.61 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.52 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.984

6312 measured reflections

1784 independent reflections

1506 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.06

1784 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.35 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/S1600536811019027/is2711sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019027/is2711Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019027/is2711Isup3.cml

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

C8H7N3O2·H2O	Z = 2
Mr = 195.18	F(000) = 204
Triclinic, P1	Dx = 1.485 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9051 (10) Å	Cell parameters from 2800 reflections
b = 7.1309 (11) Å	θ = 3.1–29.8°
c = 10.0653 (15) Å	µ = 0.12 mm−1
α = 79.421 (3)°	T = 100 K
β = 73.062 (3)°	Needle, brown
γ = 67.517 (3)°	0.52 × 0.19 × 0.14 mm
V = 436.61 (11) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	1784 independent reflections
Radiation source: fine-focus sealed tube	1506 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.942, Tmax = 0.984	k = −8→8
6312 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.1355P] where P = (Fo2 + 2Fc2)/3
1784 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.35 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.23733 (19)	−0.19984 (17)	0.30176 (12)	0.0281 (3)
O2	0.2283 (2)	0.0307 (2)	0.41865 (11)	0.0350 (3)
N1	0.26105 (19)	0.47231 (19)	−0.17804 (12)	0.0176 (3)
N2	0.2160 (2)	0.17912 (19)	−0.18388 (12)	0.0190 (3)
N3	0.2355 (2)	−0.0294 (2)	0.30934 (13)	0.0220 (3)
C1	0.2320 (3)	0.4036 (2)	−0.40419 (15)	0.0248 (4)
H1A	0.1500	0.3383	−0.4285	0.037*
H1B	0.3773	0.3594	−0.4608	0.037*
H1C	0.1669	0.5486	−0.4198	0.037*
C2	0.2349 (2)	0.3487 (2)	−0.25514 (15)	0.0186 (3)
C3	0.2308 (2)	0.1917 (2)	−0.05118 (14)	0.0167 (3)
C4	0.2203 (2)	0.0559 (2)	0.06588 (15)	0.0183 (3)
H4A	0.1994	−0.0652	0.0652	0.022*
C5	0.2426 (2)	0.1109 (2)	0.18391 (15)	0.0185 (3)
C6	0.2731 (2)	0.2924 (2)	0.19023 (15)	0.0189 (3)
H6A	0.2881	0.3206	0.2726	0.023*
C7	0.2808 (2)	0.4286 (2)	0.07407 (15)	0.0187 (3)
H7A	0.2995	0.5504	0.0760	0.022*
C8	0.2594 (2)	0.3764 (2)	−0.04673 (15)	0.0168 (3)
O1W	0.28031 (19)	0.83785 (17)	0.68930 (12)	0.0244 (3)
H1N1	0.265 (3)	0.598 (4)	−0.212 (2)	0.036 (5)*
H1W1	0.269 (3)	0.877 (3)	0.608 (2)	0.036 (5)*
H2W1	0.257 (4)	0.949 (4)	0.734 (2)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0388 (7)	0.0180 (6)	0.0275 (6)	−0.0098 (5)	−0.0114 (5)	0.0032 (5)
O2	0.0605 (8)	0.0352 (7)	0.0160 (6)	−0.0209 (6)	−0.0151 (5)	0.0003 (5)
N1	0.0242 (6)	0.0138 (7)	0.0168 (6)	−0.0068 (5)	−0.0075 (5)	−0.0017 (5)
N2	0.0259 (6)	0.0153 (6)	0.0177 (6)	−0.0062 (5)	−0.0089 (5)	−0.0028 (5)
N3	0.0248 (7)	0.0214 (7)	0.0194 (7)	−0.0065 (5)	−0.0076 (5)	−0.0004 (5)
C1	0.0349 (8)	0.0219 (8)	0.0186 (8)	−0.0083 (7)	−0.0104 (6)	−0.0017 (6)
C2	0.0212 (7)	0.0157 (7)	0.0191 (7)	−0.0040 (6)	−0.0069 (6)	−0.0042 (6)
C3	0.0185 (7)	0.0161 (7)	0.0162 (7)	−0.0041 (6)	−0.0064 (5)	−0.0036 (5)
C4	0.0211 (7)	0.0137 (7)	0.0211 (8)	−0.0056 (6)	−0.0062 (5)	−0.0033 (6)
C5	0.0197 (7)	0.0179 (8)	0.0163 (7)	−0.0043 (6)	−0.0061 (5)	0.0000 (6)
C6	0.0203 (7)	0.0206 (8)	0.0165 (7)	−0.0049 (6)	−0.0066 (5)	−0.0051 (6)
C7	0.0203 (7)	0.0166 (7)	0.0216 (7)	−0.0061 (6)	−0.0066 (6)	−0.0057 (6)
C8	0.0179 (7)	0.0146 (7)	0.0177 (7)	−0.0041 (5)	−0.0053 (5)	−0.0030 (5)
O1W	0.0428 (7)	0.0166 (6)	0.0191 (6)	−0.0125 (5)	−0.0127 (5)	−0.0008 (5)

O1—N3	1.2271 (18)	C3—C4	1.384 (2)
O2—N3	1.2334 (17)	C3—C8	1.414 (2)
N1—C2	1.3660 (18)	C4—C5	1.383 (2)
N1—C8	1.3710 (19)	C4—H4A	0.9300
N1—H1N1	0.91 (2)	C5—C6	1.404 (2)
N2—C2	1.320 (2)	C6—C7	1.378 (2)
N2—C3	1.3905 (18)	C6—H6A	0.9300
N3—C5	1.4609 (19)	C7—C8	1.3973 (19)
C1—C2	1.483 (2)	C7—H7A	0.9300
C1—H1A	0.9600	O1W—H1W1	0.83 (2)
C1—H1B	0.9600	O1W—H2W1	0.92 (3)
C1—H1C	0.9600
C2—N1—C8	107.18 (12)	N2—C3—C8	109.57 (13)
C2—N1—H1N1	122.1 (13)	C5—C4—C3	116.11 (13)
C8—N1—H1N1	130.4 (13)	C5—C4—H4A	121.9
C2—N2—C3	104.83 (12)	C3—C4—H4A	121.9
O1—N3—O2	123.11 (13)	C4—C5—C6	124.00 (14)
O1—N3—C5	119.20 (13)	C4—C5—N3	117.95 (13)
O2—N3—C5	117.69 (13)	C6—C5—N3	118.05 (13)
C2—C1—H1A	109.5	C7—C6—C5	119.80 (13)
C2—C1—H1B	109.5	C7—C6—H6A	120.1
H1A—C1—H1B	109.5	C5—C6—H6A	120.1
C2—C1—H1C	109.5	C6—C7—C8	117.33 (14)
H1A—C1—H1C	109.5	C6—C7—H7A	121.3
H1B—C1—H1C	109.5	C8—C7—H7A	121.3
N2—C2—N1	113.13 (13)	N1—C8—C7	132.77 (14)
N2—C2—C1	124.88 (13)	N1—C8—C3	105.30 (12)
N1—C2—C1	121.98 (13)	C7—C8—C3	121.93 (14)
C4—C3—N2	129.61 (13)	H1W1—O1W—H2W1	109 (2)
C4—C3—C8	120.82 (13)
C3—N2—C2—N1	−0.04 (16)	O2—N3—C5—C6	9.3 (2)
C3—N2—C2—C1	179.09 (13)	C4—C5—C6—C7	0.4 (2)
C8—N1—C2—N2	0.05 (16)	N3—C5—C6—C7	179.98 (12)
C8—N1—C2—C1	−179.10 (13)	C5—C6—C7—C8	−0.6 (2)
C2—N2—C3—C4	179.60 (14)	C2—N1—C8—C7	179.43 (15)
C2—N2—C3—C8	0.01 (15)	C2—N1—C8—C3	−0.04 (15)
N2—C3—C4—C5	179.45 (13)	C6—C7—C8—N1	−179.40 (14)
C8—C3—C4—C5	−1.0 (2)	C6—C7—C8—C3	0.0 (2)
C3—C4—C5—C6	0.4 (2)	C4—C3—C8—N1	−179.62 (12)
C3—C4—C5—N3	−179.17 (12)	N2—C3—C8—N1	0.02 (15)
O1—N3—C5—C4	9.0 (2)	C4—C3—C8—C7	0.8 (2)
O2—N3—C5—C4	−171.14 (13)	N2—C3—C8—C7	−179.52 (12)
O1—N3—C5—C6	−170.60 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1Wi	0.91 (3)	1.84 (2)	2.7347 (18)	170 (2)
O1W—H1W1···O2ii	0.831 (19)	2.06 (2)	2.8737 (17)	168.5 (19)
O1W—H2W1···N2iii	0.92 (3)	1.86 (3)	2.7808 (18)	177.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1Wi	0.91 (3)	1.84 (2)	2.7347 (18)	170 (2)
O1W—H1W1⋯O2ii	0.831 (19)	2.06 (2)	2.8737 (17)	168.5 (19)
O1W—H2W1⋯N2iii	0.92 (3)	1.86 (3)	2.7808 (18)	177.2 (17)

Symmetry codes: (i) ; (ii) ; (iii) .