1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one.

The title mol-ecule, C(17)H(25)N(3)O(3), is built up from fused six- and five-membered rings linked to a -C(10)H(21) chain. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is roughly perpendic-ular to this plane, making a dihedral angle of 79.5 (2)°. In the crystal, N-H⋯O hydrogen bonds build infinite chains along [010]. There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155].

Related literature

For the pharmacological and biochemical properties of related compounds, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For related structures, see Ouzidan et al. (2011a ▶,

Experimental

Crystal data

C17H25N3O3

M = 319.40

Monoclinic,

a = 32.9827 (6) Å

b = 4.55881 (9) Å

c = 29.3435 (5) Å

β = 109.481 (2)°

V = 4159.56 (13) Å3

Z = 8

Cu Kα radiation

μ = 0.57 mm−1

T = 206 K

0.15 × 0.11 × 0.05 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) ▶ based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.952, T max = 0.985

20838 measured reflections

4129 independent reflections

3475 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.126

S = 1.09

4129 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011) ▶; cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041389/im2324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041389/im2324Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041389/im2324Isup3.cml

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

C17H25N3O3	F(000) = 1376
Mr = 319.40	Dx = 1.020 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 8979 reflections
a = 32.9827 (6) Å	θ = 2.8–73.1°
b = 4.55881 (9) Å	µ = 0.57 mm−1
c = 29.3435 (5) Å	T = 206 K
β = 109.481 (2)°	Block, colourless
V = 4159.56 (13) Å3	0.15 × 0.11 × 0.05 mm
Z = 8

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer	4129 independent reflections
Radiation source: fine-focus sealed tube	3475 reflections with I > 2σ(I)
mirror	Rint = 0.029
Detector resolution: 0.4051 pixels mm-1	θmax = 73.3°, θmin = 2.8°
ω scans	h = −40→40
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)]	k = −4→5
Tmin = 0.952, Tmax = 0.985	l = −36→36
20838 measured reflections

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.126	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0706P)2 + 0.8537P] where P = (Fo2 + 2Fc2)/3
4129 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. Clark & Reid (1995).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.76316 (3)	0.5176 (2)	0.70158 (3)	0.0389 (3)
H1	0.7727	0.4612	0.7312	0.047*
N2	0.72508 (3)	0.7438 (2)	0.63471 (3)	0.0319 (2)
N3	0.80707 (4)	0.2956 (3)	0.53894 (4)	0.0493 (3)
O1	0.70806 (3)	0.8310 (2)	0.70415 (3)	0.0459 (3)
O2	0.83330 (4)	0.1068 (3)	0.53903 (4)	0.0817 (4)
O3	0.78870 (3)	0.4442 (2)	0.50339 (3)	0.0571 (3)
C1	0.77940 (3)	0.4278 (3)	0.66624 (4)	0.0337 (3)
C2	0.75516 (3)	0.5736 (3)	0.62357 (4)	0.0304 (3)
C3	0.76366 (3)	0.5367 (3)	0.58100 (4)	0.0341 (3)
H3	0.7482	0.6341	0.5527	0.041*
C4	0.79688 (4)	0.3445 (3)	0.58314 (4)	0.0384 (3)
C5	0.82078 (4)	0.1954 (3)	0.62471 (5)	0.0451 (3)
H5	0.8425	0.0676	0.6240	0.054*
C6	0.81208 (4)	0.2379 (3)	0.66730 (4)	0.0433 (3)
H6	0.8278	0.1413	0.6956	0.052*
C7	0.72984 (3)	0.7087 (3)	0.68291 (4)	0.0350 (3)
C11	0.69093 (3)	0.9198 (3)	0.60136 (4)	0.0325 (3)
H11A	0.7026	1.0276	0.5800	0.039*
H11B	0.6806	1.0613	0.6197	0.039*
C12	0.65344 (3)	0.7327 (3)	0.57121 (4)	0.0342 (3)
H12A	0.6418	0.6247	0.5925	0.041*
H12B	0.6637	0.5915	0.5529	0.041*
C13	0.61786 (4)	0.9169 (3)	0.53654 (4)	0.0355 (3)
H13A	0.6063	1.0490	0.5551	0.043*
H13B	0.6300	1.0352	0.5168	0.043*
C14	0.58145 (4)	0.7315 (3)	0.50369 (4)	0.0380 (3)
H14A	0.5691	0.6155	0.5235	0.046*
H14B	0.5931	0.5970	0.4856	0.046*
C15	0.54594 (4)	0.9122 (3)	0.46821 (4)	0.0403 (3)
H15A	0.5584	1.0310	0.4488	0.048*
H15B	0.5339	1.0442	0.4863	0.048*
C16	0.50987 (4)	0.7262 (3)	0.43470 (5)	0.0409 (3)
H16A	0.5220	0.5927	0.4170	0.049*
H16B	0.4973	0.6089	0.4541	0.049*
C17	0.47449 (4)	0.9044 (3)	0.39880 (5)	0.0417 (3)
H17A	0.4611	1.0287	0.4165	0.050*
H17B	0.4873	1.0311	0.3808	0.050*
C18	0.43994 (4)	0.7188 (3)	0.36328 (5)	0.0444 (3)
H18A	0.4535	0.5884	0.3466	0.053*
H18B	0.4263	0.5982	0.3812	0.053*
C19	0.40558 (4)	0.8947 (3)	0.32606 (5)	0.0530 (4)
H19A	0.3908	1.0171	0.3426	0.064*
H19B	0.4193	1.0233	0.3092	0.064*
C20	0.37271 (5)	0.7073 (4)	0.28924 (6)	0.0673 (5)
H20A	0.3528	0.8315	0.2659	0.101*
H20B	0.3575	0.5894	0.3053	0.101*
H20C	0.3871	0.5820	0.2732	0.101*

	U11	U22	U33	U12	U13	U23
N1	0.0368 (5)	0.0594 (7)	0.0176 (4)	−0.0018 (5)	0.0051 (3)	0.0043 (4)
N2	0.0304 (4)	0.0432 (6)	0.0192 (4)	−0.0013 (4)	0.0046 (3)	−0.0007 (4)
N3	0.0505 (6)	0.0633 (8)	0.0392 (6)	0.0032 (6)	0.0218 (5)	−0.0011 (5)
O1	0.0411 (4)	0.0714 (7)	0.0241 (4)	−0.0004 (4)	0.0095 (3)	−0.0087 (4)
O2	0.0945 (9)	0.1005 (10)	0.0648 (7)	0.0446 (8)	0.0461 (7)	0.0090 (7)
O3	0.0644 (6)	0.0789 (8)	0.0333 (5)	0.0066 (5)	0.0236 (4)	0.0067 (5)
C1	0.0310 (5)	0.0458 (7)	0.0217 (5)	−0.0058 (5)	0.0051 (4)	0.0020 (4)
C2	0.0287 (5)	0.0372 (6)	0.0228 (5)	−0.0059 (4)	0.0054 (4)	−0.0003 (4)
C3	0.0357 (5)	0.0422 (7)	0.0227 (5)	−0.0028 (5)	0.0075 (4)	0.0027 (4)
C4	0.0390 (6)	0.0479 (7)	0.0299 (6)	−0.0012 (5)	0.0137 (5)	−0.0006 (5)
C5	0.0398 (6)	0.0542 (8)	0.0399 (6)	0.0078 (6)	0.0115 (5)	0.0037 (6)
C6	0.0393 (6)	0.0544 (8)	0.0312 (6)	0.0046 (6)	0.0050 (5)	0.0098 (5)
C7	0.0316 (5)	0.0510 (7)	0.0199 (5)	−0.0082 (5)	0.0052 (4)	−0.0048 (5)
C11	0.0329 (5)	0.0361 (6)	0.0251 (5)	−0.0005 (5)	0.0050 (4)	−0.0008 (4)
C12	0.0330 (6)	0.0345 (6)	0.0299 (5)	−0.0011 (5)	0.0037 (4)	−0.0006 (5)
C13	0.0330 (5)	0.0337 (7)	0.0341 (6)	0.0002 (5)	0.0037 (4)	−0.0001 (5)
C14	0.0349 (6)	0.0345 (7)	0.0366 (6)	0.0005 (5)	0.0013 (5)	−0.0007 (5)
C15	0.0350 (6)	0.0365 (7)	0.0403 (6)	0.0008 (5)	0.0003 (5)	−0.0010 (5)
C16	0.0367 (6)	0.0362 (7)	0.0403 (6)	0.0005 (5)	0.0000 (5)	−0.0011 (5)
C17	0.0366 (6)	0.0381 (7)	0.0413 (6)	0.0013 (5)	0.0006 (5)	−0.0014 (5)
C18	0.0372 (6)	0.0414 (7)	0.0436 (7)	0.0011 (5)	−0.0011 (5)	−0.0024 (5)
C19	0.0447 (7)	0.0489 (9)	0.0499 (7)	0.0060 (6)	−0.0050 (6)	−0.0026 (6)
C20	0.0483 (8)	0.0687 (11)	0.0608 (9)	0.0079 (7)	−0.0140 (7)	−0.0078 (8)

N1—C7	1.3659 (16)	C13—C14	1.5208 (15)
N1—C1	1.3785 (15)	C13—H13A	0.9700
N1—H1	0.8600	C13—H13B	0.9700
N2—C7	1.3793 (13)	C14—C15	1.5235 (15)
N2—C2	1.3819 (15)	C14—H14A	0.9700
N2—C11	1.4612 (14)	C14—H14B	0.9700
N3—O2	1.2198 (16)	C15—C16	1.5235 (16)
N3—O3	1.2218 (15)	C15—H15A	0.9700
N3—C4	1.4612 (15)	C15—H15B	0.9700
O1—C7	1.2304 (14)	C16—C17	1.5201 (16)
C1—C6	1.3745 (18)	C16—H16A	0.9700
C1—C2	1.4077 (15)	C16—H16B	0.9700
C2—C3	1.3789 (14)	C17—C18	1.5194 (16)
C3—C4	1.3879 (17)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.3890 (17)	C18—C19	1.5148 (17)
C5—C6	1.3862 (18)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—H6	0.9300	C19—C20	1.5138 (19)
C11—C12	1.5197 (15)	C19—H19A	0.9700
C11—H11A	0.9700	C19—H19B	0.9700
C11—H11B	0.9700	C20—H20A	0.9600
C12—C13	1.5234 (15)	C20—H20B	0.9600
C12—H12A	0.9700	C20—H20C	0.9600
C12—H12B	0.9700
C7—N1—C1	110.52 (9)	C14—C13—H13B	109.0
C7—N1—H1	124.7	C12—C13—H13B	109.0
C1—N1—H1	124.7	H13A—C13—H13B	107.8
C7—N2—C2	109.41 (9)	C13—C14—C15	113.41 (10)
C7—N2—C11	123.32 (9)	C13—C14—H14A	108.9
C2—N2—C11	127.13 (8)	C15—C14—H14A	108.9
O2—N3—O3	122.85 (11)	C13—C14—H14B	108.9
O2—N3—C4	118.60 (11)	C15—C14—H14B	108.9
O3—N3—C4	118.55 (11)	H14A—C14—H14B	107.7
C6—C1—N1	131.94 (10)	C14—C15—C16	113.39 (10)
C6—C1—C2	121.76 (10)	C14—C15—H15A	108.9
N1—C1—C2	106.31 (10)	C16—C15—H15A	108.9
C3—C2—N2	131.46 (10)	C14—C15—H15B	108.9
C3—C2—C1	121.41 (10)	C16—C15—H15B	108.9
N2—C2—C1	107.12 (9)	H15A—C15—H15B	107.7
C2—C3—C4	115.61 (10)	C17—C16—C15	113.80 (10)
C2—C3—H3	122.2	C17—C16—H16A	108.8
C4—C3—H3	122.2	C15—C16—H16A	108.8
C3—C4—C5	123.84 (11)	C17—C16—H16B	108.8
C3—C4—N3	117.89 (10)	C15—C16—H16B	108.8
C5—C4—N3	118.28 (12)	H16A—C16—H16B	107.7
C6—C5—C4	119.74 (12)	C18—C17—C16	113.88 (10)
C6—C5—H5	120.1	C18—C17—H17A	108.8
C4—C5—H5	120.1	C16—C17—H17A	108.8
C1—C6—C5	117.64 (11)	C18—C17—H17B	108.8
C1—C6—H6	121.2	C16—C17—H17B	108.8
C5—C6—H6	121.2	H17A—C17—H17B	107.7
O1—C7—N1	127.86 (10)	C19—C18—C17	114.19 (11)
O1—C7—N2	125.50 (11)	C19—C18—H18A	108.7
N1—C7—N2	106.64 (9)	C17—C18—H18A	108.7
N2—C11—C12	112.17 (10)	C19—C18—H18B	108.7
N2—C11—H11A	109.2	C17—C18—H18B	108.7
C12—C11—H11A	109.2	H18A—C18—H18B	107.6
N2—C11—H11B	109.2	C20—C19—C18	113.67 (12)
C12—C11—H11B	109.2	C20—C19—H19A	108.8
H11A—C11—H11B	107.9	C18—C19—H19A	108.8
C11—C12—C13	112.06 (10)	C20—C19—H19B	108.8
C11—C12—H12A	109.2	C18—C19—H19B	108.8
C13—C12—H12A	109.2	H19A—C19—H19B	107.7
C11—C12—H12B	109.2	C19—C20—H20A	109.5
C13—C12—H12B	109.2	C19—C20—H20B	109.5
H12A—C12—H12B	107.9	H20A—C20—H20B	109.5
C14—C13—C12	112.76 (10)	C19—C20—H20C	109.5
C14—C13—H13A	109.0	H20A—C20—H20C	109.5
C12—C13—H13A	109.0	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.88	2.743 (1)	178.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.88	2.743 (1)	178

Symmetry code: (i) .