1-n-Decyl-5-nitro-1H-benzimidazol-2(3H)-one.

The benzimidazolone part of the title mol-ecule, C(17)H(25)N(3)O(3), is almost planar (r.m.s. deviation = 0.016 Å) and its mean plane is aligned at 7.9 (4) ° with respect to the mean plane of the nitro substituent. In the crystal, two mol-ecules are disposed about a center of inversion, generating a N-H⋯O hydrogen-bonded cyclic dimer with a 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 ▶) and for 5-nitro-1-n-octyl-1H-benzimidazol-2(3H)-one, see: Ouzidan et al. (2011 ▶). For graph-set notation, see: Etter (1990 ▶).

Experimental

Crystal data

C17H25N3O3

M = 319.40

Triclinic,

a = 5.4933 (2) Å

b = 10.3063 (4) Å

c = 16.1655 (6) Å

α = 106.504 (2)°

β = 98.545 (2)°

γ = 96.809 (2)°

V = 855.21 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.32 × 0.06 × 0.04 mm

Data collection

Bruker APEXII diffractometer

10701 measured reflections

2971 independent reflections

1600 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.175

S = 0.89

2971 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.31 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/S1600536811004399/zs2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004399/zs2093Isup2.hkl

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

C17H25N3O3	Z = 2
Mr = 319.40	F(000) = 344
Triclinic, P1	Dx = 1.240 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4933 (2) Å	Cell parameters from 1521 reflections
b = 10.3063 (4) Å	θ = 2.7–27.3°
c = 16.1655 (6) Å	µ = 0.09 mm−1
α = 106.504 (2)°	T = 293 K
β = 98.545 (2)°	Prism, colorless
γ = 96.809 (2)°	0.32 × 0.06 × 0.04 mm
V = 855.21 (6) Å3

Bruker APEXII diffractometer	1600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
graphite	θmax = 25.0°, θmin = 3.9°
φ and ω scans	h = −6→6
10701 measured reflections	k = −10→12
2971 independent reflections	l = −19→19

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-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.1056P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
2971 reflections	Δρmax = 0.30 e Å−3
209 parameters	Δρmin = −0.31 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: 0.034 (6)

	x	y	z	Uiso*/Ueq
O1	0.6868 (3)	0.57512 (19)	0.61197 (12)	0.0413 (6)
O2	0.8896 (4)	−0.0690 (2)	0.29737 (16)	0.0579 (7)
O3	1.2510 (4)	−0.0845 (2)	0.36526 (16)	0.0680 (7)
N1	0.7157 (4)	0.3830 (2)	0.49844 (15)	0.0357 (6)
H1	0.5863	0.3832	0.4592	0.043*
N2	0.9999 (4)	0.4426 (2)	0.61946 (15)	0.0337 (6)
N3	1.0691 (5)	−0.0264 (2)	0.35868 (19)	0.0482 (7)
C1	0.7879 (5)	0.4765 (3)	0.57918 (19)	0.0354 (7)
C2	0.8734 (5)	0.2871 (3)	0.48616 (18)	0.0328 (7)
C3	0.8717 (5)	0.1718 (3)	0.41760 (19)	0.0371 (7)
H3	0.7483	0.1435	0.3671	0.044*
C4	1.0672 (5)	0.1002 (3)	0.4288 (2)	0.0380 (7)
C5	1.2516 (5)	0.1396 (3)	0.5022 (2)	0.0397 (8)
H5	1.3801	0.0890	0.5052	0.048*
C6	1.2493 (5)	0.2538 (3)	0.5717 (2)	0.0385 (7)
H6	1.3723	0.2805	0.6223	0.046*
C7	1.0566 (5)	0.3268 (3)	0.56298 (19)	0.0347 (7)
C8	1.1434 (5)	0.5230 (3)	0.70567 (18)	0.0399 (7)
H8A	1.0786	0.6078	0.7254	0.048*
H8B	1.3157	0.5469	0.7007	0.048*
C9	1.1361 (5)	0.4479 (3)	0.77434 (19)	0.0420 (7)
H9A	1.1954	0.3618	0.7530	0.050*
H9B	1.2519	0.5027	0.8276	0.050*
C10	0.8830 (5)	0.4174 (3)	0.7976 (2)	0.0457 (8)
H10A	0.7678	0.3575	0.7457	0.055*
H10B	0.8185	0.5023	0.8171	0.055*
C11	0.8982 (5)	0.3489 (3)	0.8699 (2)	0.0463 (8)
H11A	0.9593	0.2632	0.8491	0.056*
H11B	1.0202	0.4076	0.9204	0.056*
C12	0.6562 (6)	0.3190 (3)	0.8998 (2)	0.0516 (9)
H12A	0.5896	0.4036	0.9179	0.062*
H12B	0.5366	0.2556	0.8505	0.062*
C13	0.6824 (6)	0.2585 (3)	0.9749 (2)	0.0492 (8)
H13A	0.8060	0.3210	1.0234	0.059*
H13B	0.7457	0.1731	0.9561	0.059*
C14	0.4445 (6)	0.2305 (3)	1.0082 (2)	0.0535 (9)
H14A	0.3754	0.3146	1.0235	0.064*
H14B	0.3244	0.1634	0.9608	0.064*
C15	0.4751 (6)	0.1780 (3)	1.0874 (2)	0.0531 (9)
H15A	0.5400	0.0926	1.0717	0.064*
H15B	0.5981	0.2439	1.1344	0.064*
C16	0.2378 (7)	0.1537 (4)	1.1214 (2)	0.0692 (11)
H16A	0.1189	0.0825	1.0760	0.083*
H16B	0.1659	0.2371	1.1331	0.083*
C17	0.2764 (8)	0.1116 (4)	1.2043 (3)	0.0862 (13)
H17A	0.1189	0.0965	1.2220	0.129*
H17B	0.3888	0.1832	1.2503	0.129*
H17C	0.3460	0.0286	1.1932	0.129*

	U11	U22	U33	U12	U13	U23
O1	0.0513 (12)	0.0398 (11)	0.0402 (12)	0.0189 (10)	0.0180 (10)	0.0148 (10)
O2	0.0723 (16)	0.0459 (14)	0.0531 (16)	0.0082 (12)	0.0178 (14)	0.0095 (12)
O3	0.0794 (17)	0.0556 (14)	0.0770 (18)	0.0342 (13)	0.0326 (14)	0.0149 (13)
N1	0.0405 (13)	0.0385 (13)	0.0363 (15)	0.0144 (11)	0.0142 (11)	0.0176 (13)
N2	0.0368 (13)	0.0354 (13)	0.0344 (14)	0.0097 (10)	0.0119 (11)	0.0151 (12)
N3	0.0618 (18)	0.0381 (15)	0.056 (2)	0.0155 (14)	0.0303 (16)	0.0194 (14)
C1	0.0446 (17)	0.0345 (16)	0.0357 (18)	0.0080 (14)	0.0186 (14)	0.0179 (15)
C2	0.0383 (16)	0.0332 (16)	0.0355 (18)	0.0072 (13)	0.0170 (14)	0.0184 (14)
C3	0.0440 (17)	0.0374 (16)	0.0355 (18)	0.0054 (13)	0.0146 (14)	0.0172 (15)
C4	0.0491 (18)	0.0321 (16)	0.0444 (19)	0.0096 (14)	0.0273 (16)	0.0192 (15)
C5	0.0412 (17)	0.0383 (17)	0.051 (2)	0.0139 (14)	0.0212 (16)	0.0215 (16)
C6	0.0371 (16)	0.0431 (17)	0.0436 (19)	0.0086 (13)	0.0137 (14)	0.0226 (16)
C7	0.0415 (16)	0.0346 (16)	0.0376 (18)	0.0073 (13)	0.0212 (14)	0.0191 (14)
C8	0.0435 (16)	0.0414 (17)	0.0352 (18)	0.0068 (13)	0.0102 (14)	0.0114 (15)
C9	0.0466 (17)	0.0414 (17)	0.0382 (18)	0.0102 (14)	0.0075 (14)	0.0119 (14)
C10	0.0541 (19)	0.0456 (18)	0.044 (2)	0.0130 (15)	0.0156 (16)	0.0185 (16)
C11	0.0561 (19)	0.0483 (18)	0.0399 (19)	0.0123 (15)	0.0140 (15)	0.0183 (16)
C12	0.064 (2)	0.0493 (19)	0.050 (2)	0.0120 (16)	0.0166 (17)	0.0237 (17)
C13	0.059 (2)	0.0508 (19)	0.043 (2)	0.0115 (16)	0.0125 (16)	0.0199 (16)
C14	0.060 (2)	0.056 (2)	0.054 (2)	0.0110 (16)	0.0165 (17)	0.0275 (18)
C15	0.070 (2)	0.0456 (18)	0.046 (2)	0.0063 (16)	0.0131 (18)	0.0188 (17)
C16	0.086 (3)	0.071 (2)	0.068 (3)	0.017 (2)	0.036 (2)	0.037 (2)
C17	0.136 (4)	0.076 (3)	0.063 (3)	0.012 (3)	0.041 (3)	0.038 (2)

O1—C1	1.240 (3)	C10—C11	1.525 (4)
O2—N3	1.228 (3)	C10—H10A	0.9700
O3—N3	1.231 (3)	C10—H10B	0.9700
N1—C1	1.353 (3)	C11—C12	1.508 (4)
N1—C2	1.382 (3)	C11—H11A	0.9700
N1—H1	0.8800	C11—H11B	0.9700
N2—C1	1.379 (3)	C12—C13	1.511 (4)
N2—C7	1.382 (3)	C12—H12A	0.9700
N2—C8	1.454 (4)	C12—H12B	0.9700
N3—C4	1.468 (4)	C13—C14	1.513 (4)
C2—C3	1.374 (4)	C13—H13A	0.9700
C2—C7	1.402 (4)	C13—H13B	0.9700
C3—C4	1.391 (4)	C14—C15	1.520 (4)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.367 (4)	C14—H14B	0.9700
C5—C6	1.380 (4)	C15—C16	1.509 (4)
C5—H5	0.9300	C15—H15A	0.9700
C6—C7	1.382 (3)	C15—H15B	0.9700
C6—H6	0.9300	C16—C17	1.517 (5)
C8—C9	1.526 (4)	C16—H16A	0.9700
C8—H8A	0.9700	C16—H16B	0.9700
C8—H8B	0.9700	C17—H17A	0.9600
C9—C10	1.514 (4)	C17—H17B	0.9600
C9—H9A	0.9700	C17—H17C	0.9600
C9—H9B	0.9700
C1—N1—C2	110.5 (2)	C9—C10—H10B	109.3
C1—N1—H1	124.7	C11—C10—H10B	109.3
C2—N1—H1	124.7	H10A—C10—H10B	108.0
C1—N2—C7	109.0 (2)	C12—C11—C10	115.4 (2)
C1—N2—C8	124.0 (2)	C12—C11—H11A	108.4
C7—N2—C8	126.9 (2)	C10—C11—H11A	108.4
O2—N3—O3	123.7 (3)	C12—C11—H11B	108.4
O2—N3—C4	118.5 (2)	C10—C11—H11B	108.4
O3—N3—C4	117.8 (3)	H11A—C11—H11B	107.5
O1—C1—N1	127.5 (3)	C13—C12—C11	113.7 (2)
O1—C1—N2	125.5 (3)	C13—C12—H12A	108.8
N1—C1—N2	107.0 (2)	C11—C12—H12A	108.8
C3—C2—N1	132.1 (3)	C13—C12—H12B	108.8
C3—C2—C7	121.8 (2)	C11—C12—H12B	108.8
N1—C2—C7	106.1 (2)	H12A—C12—H12B	107.7
C2—C3—C4	115.5 (3)	C12—C13—C14	115.2 (2)
C2—C3—H3	122.3	C12—C13—H13A	108.5
C4—C3—H3	122.3	C14—C13—H13A	108.5
C5—C4—C3	123.6 (3)	C12—C13—H13B	108.5
C5—C4—N3	118.8 (3)	C14—C13—H13B	108.5
C3—C4—N3	117.6 (3)	H13A—C13—H13B	107.5
C4—C5—C6	120.7 (2)	C15—C14—C13	115.0 (3)
C4—C5—H5	119.6	C15—C14—H14A	108.5
C6—C5—H5	119.6	C13—C14—H14A	108.5
C7—C6—C5	117.2 (3)	C15—C14—H14B	108.5
C7—C6—H6	121.4	C13—C14—H14B	108.5
C5—C6—H6	121.4	H14A—C14—H14B	107.5
N2—C7—C6	131.5 (3)	C16—C15—C14	114.5 (3)
N2—C7—C2	107.3 (2)	C16—C15—H15A	108.6
C6—C7—C2	121.2 (3)	C14—C15—H15A	108.6
N2—C8—C9	113.2 (2)	C16—C15—H15B	108.6
N2—C8—H8A	108.9	C14—C15—H15B	108.6
C9—C8—H8A	108.9	H15A—C15—H15B	107.6
N2—C8—H8B	108.9	C15—C16—C17	113.5 (3)
C9—C8—H8B	108.9	C15—C16—H16A	108.9
H8A—C8—H8B	107.8	C17—C16—H16A	108.9
C10—C9—C8	115.7 (2)	C15—C16—H16B	108.9
C10—C9—H9A	108.4	C17—C16—H16B	108.9
C8—C9—H9A	108.4	H16A—C16—H16B	107.7
C10—C9—H9B	108.4	C16—C17—H17A	109.5
C8—C9—H9B	108.4	C16—C17—H17B	109.5
H9A—C9—H9B	107.4	H17A—C17—H17B	109.5
C9—C10—C11	111.6 (2)	C16—C17—H17C	109.5
C9—C10—H10A	109.3	H17A—C17—H17C	109.5
C11—C10—H10A	109.3	H17B—C17—H17C	109.5
C2—N1—C1—O1	−179.0 (2)	C8—N2—C7—C6	2.5 (4)
C2—N1—C1—N2	1.4 (3)	C1—N2—C7—C2	−0.7 (3)
C7—N2—C1—O1	180.0 (2)	C8—N2—C7—C2	−177.4 (2)
C8—N2—C1—O1	−3.2 (4)	C5—C6—C7—N2	179.3 (3)
C7—N2—C1—N1	−0.4 (3)	C5—C6—C7—C2	−0.8 (4)
C8—N2—C1—N1	176.4 (2)	C3—C2—C7—N2	−177.8 (2)
C1—N1—C2—C3	177.4 (3)	N1—C2—C7—N2	1.4 (3)
C1—N1—C2—C7	−1.7 (3)	C3—C2—C7—C6	2.3 (4)
N1—C2—C3—C4	179.3 (2)	N1—C2—C7—C6	−178.4 (2)
C7—C2—C3—C4	−1.7 (4)	C1—N2—C8—C9	114.0 (3)
C2—C3—C4—C5	−0.3 (4)	C7—N2—C8—C9	−69.7 (3)
C2—C3—C4—N3	178.0 (2)	N2—C8—C9—C10	−65.3 (3)
O2—N3—C4—C5	172.5 (2)	C8—C9—C10—C11	−177.1 (2)
O3—N3—C4—C5	−7.0 (4)	C9—C10—C11—C12	177.9 (3)
O2—N3—C4—C3	−5.8 (4)	C10—C11—C12—C13	−176.8 (3)
O3—N3—C4—C3	174.7 (2)	C11—C12—C13—C14	178.5 (3)
C3—C4—C5—C6	1.8 (4)	C12—C13—C14—C15	−176.4 (3)
N3—C4—C5—C6	−176.5 (2)	C13—C14—C15—C16	178.6 (3)
C4—C5—C6—C7	−1.2 (4)	C14—C15—C16—C17	−175.7 (3)
C1—N2—C7—C6	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.92	2.784 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.92	2.784 (3)	168

Symmetry code: (i) .