1-Isopropyl-4-nitro-6-meth-oxy-1H-benzimidazole.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(11)H(13)N(3)O(3). The inter-planar angles for the two rings of the benzimidazole ring system is 2.21 (12)° in one mol-ecule and 0.72 (12)° in the other. The nitro group is twisted in the same direction relative to the least-squares plane through its attached benzene ring in both mol-ecules, with inter-planar angles of 15.22 (9) and 18.02 (8)°. In the crystal structure, mol-ecules are stacked along the a axis through π-π inter-actions (centroid-centroid distance 4.1954 Å). C-H⋯O hydrogen bonds are also present.

Related literature

For background to the biological applications of benzimidazole cores, see: Townsend & Revankar (1970 ▶); Kamal et al. (2006 ▶); Bentancor et al. (2004 ▶); Somsak et al. (2003 ▶); Scholz et al. (2003 ▶); Sachs et al. (1995 ▶); Shin et al. (1997 ▶); Chackalamannil et al. (2003 ▶); Nicolaou et al. (1998 ▶); Lanusse & Prichard (1993 ▶); Wang (1984 ▶); Banks (1984 ▶); Sharma & Abuzar (1983 ▶); Lopez-Rodriguez et al. (2002 ▶). For other related literature on benzimidazole cores, see: Elderfield et al. (1946 ▶); Grimmett (2002 ▶); Kumar et al. (1982 ▶); Mizzoni & Spoerri (1945 ▶); Reddy & Reddy (1979 ▶). For related literature, see: Flaherty et al. (2008 ▶).

Experimental

Crystal data

C11H13N3O3

M = 235.24

Orthorhombic,

a = 7.63920 (10) Å

b = 16.0029 (3) Å

c = 17.9496 (3) Å

V = 2194.33 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 150 (2) K

0.43 × 0.33 × 0.28 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.959, T max = 0.971

39389 measured reflections

3989 independent reflections

3649 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.09

3989 reflections

313 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 and SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801859X/zl2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801859X/zl2123Isup2.hkl

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

C11H13N3O3	F000 = 992.0
Mr = 235.24	Dx = 1.424 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12882 reflections
a = 7.63920 (10) Å	θ = 2.3–30.9º
b = 16.0029 (3) Å	µ = 0.11 mm−1
c = 17.9496 (3) Å	T = 150 (2) K
V = 2194.33 (6) Å3	Rhomboid, yellow
Z = 8	0.43 × 0.33 × 0.28 mm

Bruker SMART APEXII diffractometer	3989 independent reflections
Radiation source: fine-focus sealed tube	3649 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 296(2) K	θmax = 31.2º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	h = −11→11
Tmin = 0.959, Tmax = 0.971	k = −23→23
39389 measured reflections	l = −25→26

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.1952P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.006
3989 reflections	Δρmax = 0.47 e Å−3
313 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O6	0.21889 (17)	0.44035 (7)	0.15295 (6)	0.0298 (2)
N4	0.04946 (18)	0.68089 (7)	0.29007 (7)	0.0257 (2)
C14	0.24765 (18)	0.47797 (8)	0.35375 (7)	0.0192 (2)
N6	0.28545 (16)	0.45465 (7)	0.42604 (6)	0.0205 (2)
C16	0.17746 (18)	0.55944 (8)	0.35923 (7)	0.0201 (2)
C18	0.13756 (19)	0.55466 (9)	0.22533 (8)	0.0233 (3)
H5	0.0985	0.5799	0.1817	0.028*
C13	0.26894 (18)	0.43410 (8)	0.28697 (7)	0.0209 (2)
H7	0.3191	0.3812	0.2856	0.025*
O5	−0.0279 (2)	0.70366 (8)	0.23365 (7)	0.0401 (3)
C17	0.12331 (19)	0.59655 (8)	0.29232 (8)	0.0213 (2)
C12	0.2109 (2)	0.47402 (9)	0.22273 (7)	0.0222 (3)
N5	0.17167 (17)	0.58463 (7)	0.43318 (7)	0.0236 (2)
O4	0.0687 (2)	0.72566 (7)	0.34467 (7)	0.0436 (3)
C21	0.2167 (2)	0.30465 (8)	0.43829 (8)	0.0258 (3)
H9A	0.1150	0.3176	0.4675	0.039*
H9B	0.2632	0.2517	0.4537	0.039*
H9C	0.1850	0.3020	0.3866	0.039*
C19	0.2891 (2)	0.35769 (9)	0.14715 (8)	0.0290 (3)
H11A	0.4060	0.3569	0.1668	0.043*
H11B	0.2913	0.3410	0.0958	0.043*
H11C	0.2172	0.3197	0.1750	0.043*
C20	0.35454 (19)	0.37233 (8)	0.44953 (8)	0.0222 (2)
H8	0.4568	0.3588	0.4189	0.027*
C15	0.2357 (2)	0.52027 (8)	0.46970 (8)	0.0235 (3)
H1	0.2463	0.5195	0.5213	0.028*
C22	0.4111 (2)	0.37599 (10)	0.53068 (8)	0.0300 (3)
H10A	0.4943	0.4204	0.5372	0.045*
H10B	0.4640	0.3238	0.5445	0.045*
H10C	0.3108	0.3861	0.5616	0.045*
C5	0.63745 (18)	0.55518 (8)	0.10934 (7)	0.0200 (2)
N1	0.51798 (17)	0.67741 (7)	0.17962 (7)	0.0257 (2)
O3	0.74288 (17)	0.44725 (7)	0.31636 (5)	0.0290 (2)
C6	0.60053 (18)	0.59506 (8)	0.17718 (8)	0.0209 (2)
N3	0.74022 (16)	0.45062 (7)	0.04131 (6)	0.0197 (2)
C3	0.71541 (17)	0.47535 (8)	0.11420 (7)	0.0185 (2)
C1	0.71502 (19)	0.47734 (9)	0.24614 (7)	0.0215 (2)
C2	0.75604 (18)	0.43486 (8)	0.18085 (7)	0.0205 (2)
H18	0.8078	0.3823	0.1816	0.025*
N2	0.61682 (17)	0.57845 (7)	0.03556 (6)	0.0233 (2)
C7	0.63817 (19)	0.55723 (9)	0.24427 (8)	0.0229 (3)
H20	0.6126	0.5847	0.2886	0.027*
O1	0.5265 (2)	0.71814 (9)	0.23746 (8)	0.0493 (4)
O2	0.44371 (17)	0.70267 (7)	0.12361 (7)	0.0342 (3)
C11	0.6778 (2)	0.29985 (8)	0.03307 (8)	0.0252 (3)
H13A	0.6454	0.3014	0.0847	0.038*
H13B	0.7288	0.2465	0.0217	0.038*
H13C	0.5757	0.3082	0.0028	0.038*
C4	0.67924 (19)	0.51421 (8)	−0.00193 (8)	0.0231 (3)
H15	0.6815	0.5125	−0.0537	0.028*
C9	0.80998 (18)	0.36854 (8)	0.01721 (7)	0.0207 (2)
H12	0.9166	0.3568	0.0457	0.025*
C10	0.8569 (2)	0.37134 (10)	−0.06505 (8)	0.0268 (3)
H14A	0.7523	0.3781	−0.0940	0.040*
H14B	0.9138	0.3202	−0.0789	0.040*
H14C	0.9343	0.4175	−0.0742	0.040*
C8	0.8120 (2)	0.36434 (9)	0.32175 (8)	0.0270 (3)
H22A	0.7336	0.3259	0.2978	0.041*
H22B	0.8245	0.3494	0.3733	0.041*
H22C	0.9242	0.3621	0.2978	0.041*

	U11	U22	U33	U12	U13	U23
O6	0.0465 (6)	0.0262 (5)	0.0168 (4)	0.0047 (5)	0.0021 (4)	−0.0026 (4)
N4	0.0284 (6)	0.0188 (5)	0.0301 (6)	−0.0002 (5)	−0.0001 (5)	0.0018 (4)
C14	0.0220 (6)	0.0178 (5)	0.0179 (5)	−0.0014 (5)	0.0023 (4)	−0.0004 (4)
N6	0.0256 (5)	0.0189 (5)	0.0169 (5)	0.0000 (4)	0.0010 (4)	−0.0004 (4)
C16	0.0227 (5)	0.0177 (5)	0.0201 (5)	−0.0023 (5)	0.0020 (5)	−0.0006 (4)
C18	0.0282 (6)	0.0230 (6)	0.0187 (6)	−0.0020 (5)	0.0006 (5)	0.0012 (5)
C13	0.0250 (6)	0.0192 (5)	0.0185 (5)	−0.0004 (5)	0.0031 (5)	−0.0010 (4)
O5	0.0549 (8)	0.0277 (6)	0.0377 (7)	0.0083 (6)	−0.0124 (6)	0.0042 (5)
C17	0.0233 (6)	0.0171 (5)	0.0236 (6)	−0.0016 (5)	0.0014 (5)	0.0007 (5)
C12	0.0277 (6)	0.0225 (6)	0.0165 (5)	−0.0024 (5)	0.0026 (5)	−0.0004 (5)
N5	0.0296 (6)	0.0204 (5)	0.0207 (5)	−0.0006 (4)	0.0031 (4)	−0.0032 (4)
O4	0.0650 (9)	0.0257 (5)	0.0402 (7)	0.0130 (6)	−0.0125 (7)	−0.0092 (5)
C21	0.0304 (7)	0.0203 (6)	0.0266 (6)	−0.0002 (5)	0.0000 (5)	−0.0001 (5)
C19	0.0358 (8)	0.0259 (7)	0.0252 (6)	−0.0001 (6)	0.0027 (6)	−0.0064 (5)
C20	0.0237 (6)	0.0210 (6)	0.0218 (6)	0.0029 (5)	0.0009 (5)	0.0013 (5)
C15	0.0294 (7)	0.0218 (6)	0.0194 (6)	−0.0021 (5)	0.0019 (5)	−0.0031 (5)
C22	0.0319 (7)	0.0327 (7)	0.0254 (7)	0.0010 (6)	−0.0068 (6)	0.0043 (6)
C5	0.0221 (5)	0.0175 (5)	0.0204 (6)	−0.0012 (5)	−0.0016 (5)	−0.0002 (4)
N1	0.0285 (6)	0.0191 (5)	0.0296 (6)	0.0024 (4)	−0.0017 (5)	−0.0039 (5)
O3	0.0439 (6)	0.0263 (5)	0.0167 (4)	0.0065 (5)	−0.0040 (4)	0.0010 (4)
C6	0.0228 (6)	0.0167 (5)	0.0230 (6)	0.0002 (5)	−0.0020 (5)	−0.0028 (5)
N3	0.0256 (5)	0.0179 (5)	0.0157 (4)	0.0001 (4)	−0.0005 (4)	−0.0007 (4)
C3	0.0215 (5)	0.0170 (5)	0.0170 (5)	−0.0018 (5)	−0.0001 (4)	−0.0016 (4)
C1	0.0257 (6)	0.0225 (6)	0.0162 (5)	−0.0012 (5)	−0.0023 (5)	−0.0003 (5)
C2	0.0247 (6)	0.0187 (5)	0.0181 (5)	0.0000 (5)	−0.0021 (5)	0.0001 (4)
N2	0.0291 (6)	0.0197 (5)	0.0210 (5)	0.0005 (4)	−0.0031 (4)	0.0008 (4)
C7	0.0275 (6)	0.0226 (6)	0.0185 (5)	0.0001 (5)	−0.0022 (5)	−0.0032 (5)
O1	0.0723 (10)	0.0350 (7)	0.0405 (8)	0.0216 (7)	−0.0183 (7)	−0.0192 (6)
O2	0.0425 (7)	0.0281 (5)	0.0320 (6)	0.0112 (5)	−0.0047 (5)	0.0008 (4)
C11	0.0312 (7)	0.0197 (6)	0.0247 (6)	−0.0003 (5)	0.0022 (5)	−0.0016 (5)
C4	0.0292 (6)	0.0214 (6)	0.0187 (6)	−0.0005 (5)	−0.0022 (5)	0.0017 (5)
C9	0.0237 (6)	0.0195 (5)	0.0189 (5)	0.0024 (5)	0.0000 (5)	−0.0020 (4)
C10	0.0306 (7)	0.0297 (7)	0.0201 (6)	0.0021 (6)	0.0036 (5)	−0.0017 (5)
C8	0.0335 (7)	0.0232 (6)	0.0243 (6)	−0.0003 (6)	−0.0019 (6)	0.0051 (5)

O6—C12	1.3649 (16)	C5—N2	1.3846 (17)
O6—C19	1.4312 (18)	C5—C6	1.4035 (18)
N4—O4	1.2229 (17)	C5—C3	1.4122 (18)
N4—O5	1.2279 (18)	N1—O2	1.2231 (17)
N4—C17	1.4635 (17)	N1—O1	1.2277 (17)
C14—N6	1.3807 (16)	N1—C6	1.4615 (17)
C14—C13	1.3986 (17)	O3—C1	1.3659 (16)
C14—C16	1.4131 (18)	O3—C8	1.4314 (17)
N6—C15	1.3643 (17)	C6—C7	1.3781 (19)
N6—C20	1.4805 (16)	N3—C4	1.3620 (17)
C16—N5	1.3879 (17)	N3—C3	1.3800 (16)
C16—C17	1.4022 (18)	N3—C9	1.4820 (16)
C18—C17	1.3810 (19)	C3—C2	1.3955 (17)
C18—C12	1.408 (2)	C1—C2	1.3907 (18)
C18—H5	0.9300	C1—C7	1.4073 (19)
C13—C12	1.3908 (18)	C2—H18	0.9300
C13—H7	0.9300	N2—C4	1.3179 (18)
N5—C15	1.3153 (18)	C7—H20	0.9300
C21—C20	1.524 (2)	C11—C9	1.5195 (19)
C21—H9A	0.9600	C11—H13A	0.9600
C21—H9B	0.9600	C11—H13B	0.9600
C21—H9C	0.9600	C11—H13C	0.9600
C19—H11A	0.9600	C4—H15	0.9300
C19—H11B	0.9600	C9—C10	1.5202 (19)
C19—H11C	0.9600	C9—H12	0.9800
C20—C22	1.520 (2)	C10—H14A	0.9600
C20—H8	0.9800	C10—H14B	0.9600
C15—H1	0.9300	C10—H14C	0.9600
C22—H10A	0.9600	C8—H22A	0.9600
C22—H10B	0.9600	C8—H22B	0.9600
C22—H10C	0.9600	C8—H22C	0.9600
C12—O6—C19	116.63 (11)	N2—C5—C6	133.21 (12)
O4—N4—O5	123.03 (13)	N2—C5—C3	110.51 (11)
O4—N4—C17	118.16 (12)	C6—C5—C3	116.26 (11)
O5—N4—C17	118.82 (13)	O2—N1—O1	122.99 (13)
N6—C14—C13	130.20 (12)	O2—N1—C6	118.27 (12)
N6—C14—C16	105.27 (11)	O1—N1—C6	118.75 (13)
C13—C14—C16	124.53 (12)	C1—O3—C8	116.52 (11)
C15—N6—C14	105.88 (11)	C7—C6—C5	121.09 (12)
C15—N6—C20	128.35 (11)	C7—C6—N1	117.39 (12)
C14—N6—C20	125.65 (11)	C5—C6—N1	121.51 (12)
N5—C16—C17	133.37 (12)	C4—N3—C3	106.19 (11)
N5—C16—C14	110.28 (11)	C4—N3—C9	128.25 (11)
C17—C16—C14	116.30 (11)	C3—N3—C9	125.47 (11)
C17—C18—C12	120.35 (12)	N3—C3—C2	130.47 (12)
C17—C18—H5	119.8	N3—C3—C5	105.00 (11)
C12—C18—H5	119.8	C2—C3—C5	124.53 (12)
C12—C13—C14	116.29 (12)	O3—C1—C2	124.77 (12)
C12—C13—H7	121.9	O3—C1—C7	114.03 (11)
C14—C13—H7	121.9	C2—C1—C7	121.20 (12)
C18—C17—C16	121.13 (12)	C1—C2—C3	116.45 (12)
C18—C17—N4	117.00 (12)	C1—C2—H18	121.8
C16—C17—N4	121.87 (12)	C3—C2—H18	121.8
O6—C12—C13	124.43 (13)	C4—N2—C5	103.73 (11)
O6—C12—C18	114.21 (12)	C6—C7—C1	120.47 (12)
C13—C12—C18	121.36 (12)	C6—C7—H20	119.8
C15—N5—C16	103.74 (11)	C1—C7—H20	119.8
C20—C21—H9A	109.5	C9—C11—H13A	109.5
C20—C21—H9B	109.5	C9—C11—H13B	109.5
H9A—C21—H9B	109.5	H13A—C11—H13B	109.5
C20—C21—H9C	109.5	C9—C11—H13C	109.5
H9A—C21—H9C	109.5	H13A—C11—H13C	109.5
H9B—C21—H9C	109.5	H13B—C11—H13C	109.5
O6—C19—H11A	109.5	N2—C4—N3	114.57 (12)
O6—C19—H11B	109.5	N2—C4—H15	122.7
H11A—C19—H11B	109.5	N3—C4—H15	122.7
O6—C19—H11C	109.5	N3—C9—C10	110.01 (11)
H11A—C19—H11C	109.5	N3—C9—C11	110.34 (11)
H11B—C19—H11C	109.5	C10—C9—C11	111.10 (12)
N6—C20—C22	109.87 (11)	N3—C9—H12	108.4
N6—C20—C21	110.38 (11)	C10—C9—H12	108.4
C22—C20—C21	110.53 (12)	C11—C9—H12	108.4
N6—C20—H8	108.7	C9—C10—H14A	109.5
C22—C20—H8	108.7	C9—C10—H14B	109.5
C21—C20—H8	108.7	H14A—C10—H14B	109.5
N5—C15—N6	114.83 (12)	C9—C10—H14C	109.5
N5—C15—H1	122.6	H14A—C10—H14C	109.5
N6—C15—H1	122.6	H14B—C10—H14C	109.5
C20—C22—H10A	109.5	O3—C8—H22A	109.5
C20—C22—H10B	109.5	O3—C8—H22B	109.5
H10A—C22—H10B	109.5	H22A—C8—H22B	109.5
C20—C22—H10C	109.5	O3—C8—H22C	109.5
H10A—C22—H10C	109.5	H22A—C8—H22C	109.5
H10B—C22—H10C	109.5	H22B—C8—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C15—H1···O6i	0.93	2.46	3.3670 (8)	164
C4—H15···O3ii	0.93	2.49	3.3723 (8)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H1⋯O6i	0.93	2.46	3.3670 (8)	164
C4—H15⋯O3ii	0.93	2.49	3.3723 (8)	159

Symmetry codes: (i) ; (ii) .