5-Nitro-1-n-octyl-1H-benzimidazol-2(3H)-one.

The benzimidazolone part of the mol-ecule of the title compound, C(15)H(21)N(3)O(3), is almost planar (r.m.s. deviation = 0.007 Å) with its mean plane aligned at a dihedral angle of 10.4 (3)° with respect to the mean plane of the nitro substituent. In the crystal, two mol-ecules are disposed about a center of inversion, generating an N-H⋯O hydrogen-bonded cyclic dimer with R(2) (2)(8) graph-set motif.

Related literature

For the crystal structure of 1-isopropenyl-1H-benzimidazol-2(3H)-one, see: Saber et al. (2010 ▶). For graph-set notation, see: Etter (1990 ▶).

Experimental

Crystal data

C15H21N3O3

M = 291.35

Triclinic,

a = 4.9997 (3) Å

b = 11.4942 (6) Å

c = 13.8739 (7) Å

α = 74.214 (3)°

β = 79.637 (4)°

γ = 84.108 (4)°

V = 753.50 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.22 × 0.12 × 0.06 mm

Data collection

Bruker APEXII diffractometer

10215 measured reflections

3084 independent reflections

1538 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.144

S = 0.95

3084 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003503/zs2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003503/zs2090Isup2.hkl

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

C15H21N3O3	Z = 2
Mr = 291.35	F(000) = 312
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9997 (3) Å	Cell parameters from 926 reflections
b = 11.4942 (6) Å	θ = 2.1–26.5°
c = 13.8739 (7) Å	µ = 0.09 mm−1
α = 74.214 (3)°	T = 295 K
β = 79.637 (4)°	Block, colorless
γ = 84.108 (4)°	0.22 × 0.12 × 0.06 mm
V = 753.50 (7) Å3

Bruker APEXII diffractometer	1538 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
graphite	θmax = 26.5°, θmin = 2.1°
φ and ω scans	h = −5→6
10215 measured reflections	k = −14→14
3084 independent reflections	l = −17→17

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
3084 reflections	Δρmax = 0.21 e Å−3
195 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (4)

	x	y	z	Uiso*/Ueq
O1	0.6268 (4)	0.47630 (17)	0.37325 (14)	0.0426 (5)
O2	−0.5372 (4)	0.15689 (19)	0.72705 (15)	0.0534 (6)
O3	−0.5678 (4)	0.02018 (19)	0.64945 (15)	0.0534 (6)
N1	0.3626 (4)	0.32787 (19)	0.35991 (16)	0.0325 (6)
N2	0.2757 (5)	0.3907 (2)	0.50001 (18)	0.0351 (6)
N3	−0.4666 (5)	0.1112 (2)	0.65519 (18)	0.0407 (6)
C1	0.1487 (5)	0.2628 (2)	0.42194 (19)	0.0299 (6)
C2	0.0021 (5)	0.1746 (2)	0.4085 (2)	0.0341 (7)
H2	0.0387	0.1491	0.3491	0.041*
C3	−0.2003 (5)	0.1257 (2)	0.48628 (19)	0.0336 (7)
H3	−0.3034	0.0660	0.4800	0.040*
C4	−0.2502 (5)	0.1658 (2)	0.57430 (19)	0.0324 (6)
C5	−0.1062 (5)	0.2549 (2)	0.58994 (19)	0.0339 (7)
H5	−0.1433	0.2802	0.6494	0.041*
C6	0.0937 (5)	0.3025 (2)	0.51182 (19)	0.0316 (7)
C7	0.4414 (6)	0.4067 (3)	0.4080 (2)	0.0364 (7)
C8	0.4867 (6)	0.3212 (3)	0.25805 (19)	0.0399 (7)
H8A	0.5128	0.2370	0.2563	0.048*
H8B	0.6644	0.3549	0.2417	0.048*
C9	0.3124 (6)	0.3898 (2)	0.17815 (19)	0.0381 (7)
H9A	0.4130	0.3908	0.1113	0.046*
H9B	0.1488	0.3469	0.1872	0.046*
C10	0.2313 (6)	0.5199 (2)	0.1835 (2)	0.0407 (7)
H10A	0.1183	0.5181	0.2484	0.049*
H10B	0.3947	0.5602	0.1806	0.049*
C11	0.0788 (6)	0.5937 (3)	0.0999 (2)	0.0429 (8)
H11A	−0.0721	0.5490	0.0964	0.051*
H11B	0.1997	0.6062	0.0354	0.051*
C12	−0.0298 (6)	0.7161 (3)	0.1179 (2)	0.0491 (8)
H12A	0.1215	0.7581	0.1248	0.059*
H12B	−0.1543	0.7024	0.1816	0.059*
C13	−0.1770 (6)	0.7985 (3)	0.0349 (2)	0.0507 (9)
H13A	−0.3121	0.7528	0.0213	0.061*
H13B	−0.2729	0.8647	0.0601	0.061*
C14	0.0045 (6)	0.8505 (3)	−0.0629 (2)	0.0509 (8)
H14A	0.0916	0.7847	−0.0908	0.061*
H14B	0.1463	0.8924	−0.0492	0.061*
C15	−0.1477 (7)	0.9384 (3)	−0.1419 (2)	0.0608 (10)
H15A	−0.0220	0.9683	−0.2027	0.091*
H15B	−0.2301	1.0050	−0.1156	0.091*
H15C	−0.2864	0.8972	−0.1568	0.091*
H1	0.296 (6)	0.428 (3)	0.549 (2)	0.059 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0398 (12)	0.0451 (12)	0.0468 (12)	−0.0145 (11)	−0.0018 (10)	−0.0170 (10)
O2	0.0546 (14)	0.0572 (14)	0.0491 (13)	−0.0085 (12)	0.0087 (11)	−0.0240 (11)
O3	0.0546 (14)	0.0502 (14)	0.0571 (14)	−0.0244 (12)	0.0059 (11)	−0.0184 (11)
N1	0.0301 (13)	0.0333 (13)	0.0366 (13)	−0.0044 (11)	−0.0056 (11)	−0.0123 (10)
N2	0.0323 (13)	0.0398 (14)	0.0369 (14)	−0.0067 (11)	−0.0038 (11)	−0.0153 (11)
N3	0.0350 (14)	0.0398 (15)	0.0446 (15)	−0.0036 (12)	−0.0038 (12)	−0.0074 (12)
C1	0.0253 (15)	0.0291 (15)	0.0350 (15)	−0.0002 (13)	−0.0035 (12)	−0.0089 (12)
C2	0.0343 (16)	0.0342 (16)	0.0353 (15)	0.0021 (13)	−0.0053 (13)	−0.0129 (12)
C3	0.0337 (16)	0.0302 (15)	0.0402 (16)	−0.0038 (13)	−0.0076 (13)	−0.0127 (13)
C4	0.0276 (15)	0.0311 (15)	0.0357 (15)	−0.0002 (13)	−0.0033 (12)	−0.0058 (12)
C5	0.0327 (16)	0.0371 (16)	0.0327 (15)	0.0001 (14)	−0.0044 (13)	−0.0119 (13)
C6	0.0306 (15)	0.0303 (15)	0.0371 (16)	0.0002 (13)	−0.0102 (13)	−0.0115 (12)
C7	0.0348 (17)	0.0355 (16)	0.0426 (17)	−0.0001 (14)	−0.0136 (14)	−0.0123 (14)
C8	0.0335 (16)	0.0457 (18)	0.0409 (17)	−0.0014 (14)	−0.0004 (13)	−0.0159 (14)
C9	0.0344 (16)	0.0467 (18)	0.0353 (16)	−0.0033 (14)	0.0021 (13)	−0.0186 (13)
C10	0.0399 (17)	0.0428 (17)	0.0394 (16)	−0.0041 (14)	−0.0029 (14)	−0.0121 (13)
C11	0.0412 (17)	0.0477 (18)	0.0393 (16)	−0.0004 (15)	−0.0021 (14)	−0.0142 (14)
C12	0.055 (2)	0.0479 (19)	0.0447 (18)	0.0084 (16)	−0.0101 (15)	−0.0150 (15)
C13	0.051 (2)	0.051 (2)	0.0470 (18)	0.0069 (16)	−0.0025 (16)	−0.0134 (15)
C14	0.0452 (19)	0.054 (2)	0.0514 (19)	−0.0034 (16)	−0.0071 (16)	−0.0098 (16)
C15	0.063 (2)	0.061 (2)	0.053 (2)	−0.0012 (19)	−0.0071 (18)	−0.0094 (17)

O1—C7	1.230 (3)	C9—C10	1.526 (4)
O2—N3	1.231 (3)	C9—H9A	0.9700
O3—N3	1.235 (3)	C9—H9B	0.9700
N1—C7	1.385 (3)	C10—C11	1.515 (4)
N1—C1	1.388 (3)	C10—H10A	0.9700
N1—C8	1.457 (3)	C10—H10B	0.9700
N2—C7	1.368 (3)	C11—C12	1.524 (4)
N2—C6	1.389 (3)	C11—H11A	0.9700
N2—H1	0.93 (3)	C11—H11B	0.9700
N3—C4	1.464 (3)	C12—C13	1.527 (4)
C1—C2	1.380 (4)	C12—H12A	0.9700
C1—C6	1.414 (3)	C12—H12B	0.9700
C2—C3	1.378 (4)	C13—C14	1.500 (4)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.392 (4)	C13—H13B	0.9700
C3—H3	0.9300	C14—C15	1.529 (4)
C4—C5	1.394 (4)	C14—H14A	0.9700
C5—C6	1.369 (4)	C14—H14B	0.9700
C5—H5	0.9300	C15—H15A	0.9600
C8—C9	1.530 (3)	C15—H15B	0.9600
C8—H8A	0.9700	C15—H15C	0.9600
C8—H8B	0.9700
C7—N1—C1	109.6 (2)	C10—C9—H9B	108.9
C7—N1—C8	123.1 (2)	C8—C9—H9B	108.9
C1—N1—C8	127.3 (2)	H9A—C9—H9B	107.8
C7—N2—C6	110.3 (2)	C11—C10—C9	114.5 (2)
C7—N2—H1	123.8 (19)	C11—C10—H10A	108.6
C6—N2—H1	125.6 (19)	C9—C10—H10A	108.6
O2—N3—O3	122.7 (2)	C11—C10—H10B	108.6
O2—N3—C4	118.5 (3)	C9—C10—H10B	108.6
O3—N3—C4	118.8 (2)	H10A—C10—H10B	107.6
C2—C1—N1	131.6 (2)	C10—C11—C12	111.7 (2)
C2—C1—C6	121.5 (2)	C10—C11—H11A	109.3
N1—C1—C6	106.8 (2)	C12—C11—H11A	109.3
C3—C2—C1	117.6 (3)	C10—C11—H11B	109.3
C3—C2—H2	121.2	C12—C11—H11B	109.3
C1—C2—H2	121.2	H11A—C11—H11B	107.9
C2—C3—C4	119.8 (3)	C11—C12—C13	115.1 (2)
C2—C3—H3	120.1	C11—C12—H12A	108.5
C4—C3—H3	120.1	C13—C12—H12A	108.5
C3—C4—C5	123.8 (3)	C11—C12—H12B	108.5
C3—C4—N3	118.1 (3)	C13—C12—H12B	108.5
C5—C4—N3	118.0 (2)	H12A—C12—H12B	107.5
C6—C5—C4	115.4 (2)	C14—C13—C12	114.8 (2)
C6—C5—H5	122.3	C14—C13—H13A	108.6
C4—C5—H5	122.3	C12—C13—H13A	108.6
C5—C6—N2	131.8 (3)	C14—C13—H13B	108.6
C5—C6—C1	121.7 (3)	C12—C13—H13B	108.6
N2—C6—C1	106.5 (2)	H13A—C13—H13B	107.6
O1—C7—N2	127.7 (3)	C13—C14—C15	113.2 (2)
O1—C7—N1	125.5 (3)	C13—C14—H14A	108.9
N2—C7—N1	106.8 (3)	C15—C14—H14A	108.9
N1—C8—C9	112.1 (2)	C13—C14—H14B	108.9
N1—C8—H8A	109.2	C15—C14—H14B	108.9
C9—C8—H8A	109.2	H14A—C14—H14B	107.8
N1—C8—H8B	109.2	C14—C15—H15A	109.5
C9—C8—H8B	109.2	C14—C15—H15B	109.5
H8A—C8—H8B	107.9	H15A—C15—H15B	109.5
C10—C9—C8	113.2 (2)	C14—C15—H15C	109.5
C10—C9—H9A	108.9	H15A—C15—H15C	109.5
C8—C9—H9A	108.9	H15B—C15—H15C	109.5
C7—N1—C1—C2	−179.8 (3)	C2—C1—C6—C5	0.4 (4)
C8—N1—C1—C2	2.2 (4)	N1—C1—C6—C5	−179.3 (2)
C7—N1—C1—C6	−0.2 (3)	C2—C1—C6—N2	−179.9 (2)
C8—N1—C1—C6	−178.2 (2)	N1—C1—C6—N2	0.5 (3)
N1—C1—C2—C3	179.3 (2)	C6—N2—C7—O1	−179.2 (3)
C6—C1—C2—C3	−0.3 (3)	C6—N2—C7—N1	0.4 (3)
C1—C2—C3—C4	0.0 (4)	C1—N1—C7—O1	179.5 (2)
C2—C3—C4—C5	0.1 (4)	C8—N1—C7—O1	−2.4 (4)
C2—C3—C4—N3	−179.8 (2)	C1—N1—C7—N2	−0.1 (3)
O2—N3—C4—C3	−170.3 (2)	C8—N1—C7—N2	177.9 (2)
O3—N3—C4—C3	10.9 (3)	C7—N1—C8—C9	−100.3 (3)
O2—N3—C4—C5	9.7 (3)	C1—N1—C8—C9	77.4 (3)
O3—N3—C4—C5	−169.1 (2)	N1—C8—C9—C10	52.0 (3)
C3—C4—C5—C6	0.0 (4)	C8—C9—C10—C11	175.1 (2)
N3—C4—C5—C6	179.9 (2)	C9—C10—C11—C12	172.1 (3)
C4—C5—C6—N2	−179.9 (2)	C10—C11—C12—C13	177.7 (3)
C4—C5—C6—C1	−0.2 (3)	C11—C12—C13—C14	−71.2 (4)
C7—N2—C6—C5	179.2 (3)	C12—C13—C14—C15	−176.5 (3)
C7—N2—C6—C1	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.93 (3)	1.84 (3)	2.755 (3)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.93 (3)	1.84 (3)	2.755 (3)	169 (3)

Symmetry code: (i) .