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

In the title mol-ecule, C(16)H(23)N(3)O(3), the dihedral angle between the benzimidazole and nitro group planes is 5.34 (9)° and the dihedral angle between the benzimidazole and aliphatic chain mean planes is 73.23 (5)°. The C-C-C-C torsion angles (about 176°) of the nonyl group indicate an all-anti-periplanar conformation. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into inversion dimers. These mol-ecules are further connected through C-H⋯O inter-actions, building tapes parallel to (22).

Related literature

For background to the pharmacological and biochemical properties of benzimidazolo­nes, see: Gbadamassi et al. (1988 ▶); Singh et al. (2000 ▶); Derand et al. (2003 ▶); Badarau et al. (2009 ▶). For similar structures, see: Saber et al. (2010 ▶); Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C16H23N3O3

M = 305.37

Triclinic,

a = 5.483 (1) Å

b = 10.2092 (15) Å

c = 14.746 (3) Å

α = 74.275 (9)°

β = 79.727 (6)°

γ = 83.410 (8)°

V = 779.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.35 × 0.27 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer

21087 measured reflections

6349 independent reflections

5183 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.03

6349 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005654/gk2342sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005654/gk2342Isup2.hkl

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

C16H23N3O3	Z = 2
Mr = 305.37	F(000) = 328
Triclinic, P1	Dx = 1.300 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.483 (1) Å	Cell parameters from 5537 reflections
b = 10.2092 (15) Å	θ = 2.5–34.9°
c = 14.746 (3) Å	µ = 0.09 mm−1
α = 74.275 (9)°	T = 90 K
β = 79.727 (6)°	Needle, colourless
γ = 83.410 (8)°	0.35 × 0.27 × 0.22 mm
V = 779.9 (2) Å3

Nonius KappaCCD diffractometer	5183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 34.9°, θmin = 2.8°
ω and φ scans	h = −8→8
21087 measured reflections	k = −15→16
6349 independent reflections	l = −23→22

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1462P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6349 reflections	Δρmax = 0.45 e Å−3
201 parameters	Δρmin = −0.28 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: 0.023 (5)

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
O1	0.92795 (11)	1.07035 (6)	0.37556 (4)	0.01618 (12)
O2	0.40529 (12)	0.45052 (6)	0.71989 (4)	0.02109 (13)
O3	0.12666 (12)	0.41865 (6)	0.64166 (5)	0.02143 (13)
N1	0.78463 (12)	0.88673 (7)	0.50035 (5)	0.01369 (12)
H1	0.8751	0.8904	0.5431	0.016*
N2	0.61923 (12)	0.93607 (7)	0.36748 (4)	0.01292 (12)
N3	0.29292 (13)	0.48382 (7)	0.65097 (5)	0.01591 (13)
C1	0.79248 (13)	0.97452 (8)	0.41127 (5)	0.01294 (13)
C2	0.50448 (13)	0.82444 (7)	0.42883 (5)	0.01255 (13)
C3	0.61268 (13)	0.79137 (8)	0.51286 (5)	0.01240 (13)
C4	0.54726 (13)	0.68061 (8)	0.58770 (5)	0.01379 (13)
H4	0.6229	0.6565	0.6437	0.017*
C5	0.36219 (13)	0.60623 (7)	0.57568 (5)	0.01384 (13)
C6	0.24677 (14)	0.63920 (8)	0.49481 (6)	0.01500 (13)
H6	0.1193	0.5860	0.4912	0.018*
C7	0.31799 (14)	0.75013 (8)	0.41917 (5)	0.01431 (13)
H7	0.2421	0.7740	0.3632	0.017*
C8	0.56136 (14)	1.00911 (8)	0.27295 (5)	0.01453 (13)
H8A	0.6475	1.0948	0.2508	0.017*
H8B	0.3804	1.0338	0.2778	0.017*
C9	0.63787 (14)	0.92606 (8)	0.19926 (5)	0.01496 (13)
H9A	0.5714	0.9758	0.1402	0.018*
H9B	0.5589	0.8382	0.2237	0.018*
C10	0.91760 (14)	0.89612 (8)	0.17380 (5)	0.01536 (14)
H10A	0.9848	0.8397	0.2311	0.018*
H10B	1.0005	0.9829	0.1522	0.018*
C11	0.97314 (15)	0.82089 (8)	0.09493 (6)	0.01648 (14)
H11A	0.8959	0.7325	0.1186	0.020*
H11B	0.8936	0.8751	0.0400	0.020*
C12	1.24889 (15)	0.79376 (8)	0.06003 (6)	0.01714 (14)
H12A	1.3281	0.7349	0.1137	0.021*
H12B	1.3293	0.8813	0.0386	0.021*
C13	1.29159 (14)	0.72462 (8)	−0.02204 (6)	0.01650 (14)
H13A	1.2188	0.6349	0.0010	0.020*
H13B	1.2018	0.7809	−0.0735	0.020*
C14	1.56428 (15)	0.70296 (8)	−0.06374 (6)	0.01707 (14)
H14A	1.6346	0.7928	−0.0918	0.020*
H14B	1.6575	0.6522	−0.0118	0.020*
C15	1.59873 (15)	0.62433 (9)	−0.14015 (6)	0.01812 (15)
H15A	1.5350	0.5330	−0.1111	0.022*
H15B	1.4981	0.6728	−0.1903	0.022*
C16	1.86819 (17)	0.60708 (10)	−0.18635 (7)	0.02506 (18)
H16A	1.9271	0.6967	−0.2215	0.038*
H16B	1.8795	0.5492	−0.2304	0.038*
H16C	1.9712	0.5643	−0.1368	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0171 (2)	0.0163 (3)	0.0153 (2)	−0.00631 (19)	−0.00140 (19)	−0.0029 (2)
O2	0.0265 (3)	0.0195 (3)	0.0162 (3)	−0.0041 (2)	−0.0049 (2)	−0.0008 (2)
O3	0.0224 (3)	0.0188 (3)	0.0235 (3)	−0.0096 (2)	−0.0006 (2)	−0.0048 (2)
N1	0.0147 (3)	0.0147 (3)	0.0125 (3)	−0.0040 (2)	−0.0026 (2)	−0.0035 (2)
N2	0.0138 (3)	0.0137 (3)	0.0117 (3)	−0.0029 (2)	−0.0018 (2)	−0.0032 (2)
N3	0.0177 (3)	0.0143 (3)	0.0153 (3)	−0.0031 (2)	0.0006 (2)	−0.0044 (2)
C1	0.0130 (3)	0.0138 (3)	0.0126 (3)	−0.0014 (2)	−0.0010 (2)	−0.0048 (2)
C2	0.0120 (3)	0.0132 (3)	0.0126 (3)	−0.0014 (2)	−0.0005 (2)	−0.0043 (2)
C3	0.0119 (3)	0.0133 (3)	0.0130 (3)	−0.0020 (2)	−0.0009 (2)	−0.0052 (2)
C4	0.0143 (3)	0.0145 (3)	0.0128 (3)	−0.0020 (2)	−0.0011 (2)	−0.0041 (2)
C5	0.0147 (3)	0.0123 (3)	0.0141 (3)	−0.0024 (2)	0.0000 (2)	−0.0034 (2)
C6	0.0140 (3)	0.0150 (3)	0.0168 (3)	−0.0028 (2)	−0.0017 (2)	−0.0051 (3)
C7	0.0132 (3)	0.0159 (3)	0.0148 (3)	−0.0020 (2)	−0.0030 (2)	−0.0046 (2)
C8	0.0158 (3)	0.0147 (3)	0.0125 (3)	0.0003 (2)	−0.0026 (2)	−0.0028 (2)
C9	0.0157 (3)	0.0172 (3)	0.0125 (3)	−0.0017 (2)	−0.0026 (2)	−0.0043 (2)
C10	0.0163 (3)	0.0171 (3)	0.0135 (3)	−0.0011 (2)	−0.0024 (2)	−0.0053 (3)
C11	0.0173 (3)	0.0189 (3)	0.0142 (3)	−0.0006 (3)	−0.0017 (2)	−0.0065 (3)
C12	0.0179 (3)	0.0196 (4)	0.0153 (3)	−0.0003 (3)	−0.0029 (3)	−0.0071 (3)
C13	0.0168 (3)	0.0184 (3)	0.0150 (3)	−0.0001 (3)	−0.0020 (2)	−0.0063 (3)
C14	0.0173 (3)	0.0181 (3)	0.0157 (3)	−0.0004 (3)	−0.0015 (3)	−0.0053 (3)
C15	0.0200 (3)	0.0183 (4)	0.0157 (3)	0.0012 (3)	−0.0015 (3)	−0.0056 (3)
C16	0.0217 (4)	0.0302 (5)	0.0221 (4)	0.0022 (3)	0.0013 (3)	−0.0094 (3)

O1—C1	1.2387 (9)	C9—H9A	0.9900
O2—N3	1.2313 (9)	C9—H9B	0.9900
O3—N3	1.2352 (9)	C10—C11	1.5297 (11)
N1—C1	1.3715 (10)	C10—H10A	0.9900
N1—C3	1.3864 (9)	C10—H10B	0.9900
N1—H1	0.8800	C11—C12	1.5268 (11)
N2—C1	1.3838 (10)	C11—H11A	0.9900
N2—C2	1.3842 (10)	C11—H11B	0.9900
N2—C8	1.4628 (10)	C12—C13	1.5303 (11)
N3—C5	1.4646 (10)	C12—H12A	0.9900
C2—C7	1.3893 (10)	C12—H12B	0.9900
C2—C3	1.4109 (10)	C13—C14	1.5272 (11)
C3—C4	1.3787 (11)	C13—H13A	0.9900
C4—C5	1.3970 (11)	C13—H13B	0.9900
C4—H4	0.9500	C14—C15	1.5263 (11)
C5—C6	1.3924 (11)	C14—H14A	0.9900
C6—C7	1.3930 (11)	C14—H14B	0.9900
C6—H6	0.9500	C15—C16	1.5246 (12)
C7—H7	0.9500	C15—H15A	0.9900
C8—C9	1.5266 (11)	C15—H15B	0.9900
C8—H8A	0.9900	C16—H16A	0.9800
C8—H8B	0.9900	C16—H16B	0.9800
C9—C10	1.5284 (11)	C16—H16C	0.9800
C1—N1—C3	109.78 (6)	C9—C10—C11	110.76 (6)
C1—N1—H1	125.1	C9—C10—H10A	109.5
C3—N1—H1	125.1	C11—C10—H10A	109.5
C1—N2—C2	109.39 (6)	C9—C10—H10B	109.5
C1—N2—C8	124.01 (6)	C11—C10—H10B	109.5
C2—N2—C8	126.52 (6)	H10A—C10—H10B	108.1
O2—N3—O3	123.41 (7)	C12—C11—C10	114.85 (6)
O2—N3—C5	118.20 (7)	C12—C11—H11A	108.6
O3—N3—C5	118.39 (7)	C10—C11—H11A	108.6
O1—C1—N1	127.21 (7)	C12—C11—H11B	108.6
O1—C1—N2	125.74 (7)	C10—C11—H11B	108.6
N1—C1—N2	107.04 (6)	H11A—C11—H11B	107.5
N2—C2—C7	131.59 (7)	C11—C12—C13	112.22 (6)
N2—C2—C3	106.99 (6)	C11—C12—H12A	109.2
C7—C2—C3	121.42 (7)	C13—C12—H12A	109.2
C4—C3—N1	131.24 (7)	C11—C12—H12B	109.2
C4—C3—C2	121.98 (7)	C13—C12—H12B	109.2
N1—C3—C2	106.77 (6)	H12A—C12—H12B	107.9
C3—C4—C5	115.49 (7)	C14—C13—C12	114.38 (7)
C3—C4—H4	122.3	C14—C13—H13A	108.7
C5—C4—H4	122.3	C12—C13—H13A	108.7
C6—C5—C4	123.69 (7)	C14—C13—H13B	108.7
C6—C5—N3	118.32 (7)	C12—C13—H13B	108.7
C4—C5—N3	117.95 (7)	H13A—C13—H13B	107.6
C5—C6—C7	120.08 (7)	C15—C14—C13	112.45 (7)
C5—C6—H6	120.0	C15—C14—H14A	109.1
C7—C6—H6	120.0	C13—C14—H14A	109.1
C2—C7—C6	117.29 (7)	C15—C14—H14B	109.1
C2—C7—H7	121.4	C13—C14—H14B	109.1
C6—C7—H7	121.4	H14A—C14—H14B	107.8
N2—C8—C9	113.04 (6)	C16—C15—C14	113.56 (7)
N2—C8—H8A	109.0	C16—C15—H15A	108.9
C9—C8—H8A	109.0	C14—C15—H15A	108.9
N2—C8—H8B	109.0	C16—C15—H15B	108.9
C9—C8—H8B	109.0	C14—C15—H15B	108.9
H8A—C8—H8B	107.8	H15A—C15—H15B	107.7
C8—C9—C10	115.31 (6)	C15—C16—H16A	109.5
C8—C9—H9A	108.4	C15—C16—H16B	109.5
C10—C9—H9A	108.4	H16A—C16—H16B	109.5
C8—C9—H9B	108.4	C15—C16—H16C	109.5
C10—C9—H9B	108.4	H16A—C16—H16C	109.5
H9A—C9—H9B	107.5	H16B—C16—H16C	109.5
C3—N1—C1—O1	−178.59 (7)	C3—C4—C5—N3	177.28 (6)
C3—N1—C1—N2	1.29 (8)	O2—N3—C5—C6	175.91 (7)
C2—N2—C1—O1	179.64 (7)	O3—N3—C5—C6	−3.41 (11)
C8—N2—C1—O1	−3.45 (12)	O2—N3—C5—C4	−1.82 (10)
C2—N2—C1—N1	−0.24 (8)	O3—N3—C5—C4	178.86 (7)
C8—N2—C1—N1	176.67 (6)	C4—C5—C6—C7	1.40 (12)
C1—N2—C2—C7	178.96 (8)	N3—C5—C6—C7	−176.19 (7)
C8—N2—C2—C7	2.15 (13)	N2—C2—C7—C6	178.47 (7)
C1—N2—C2—C3	−0.87 (8)	C3—C2—C7—C6	−1.72 (11)
C8—N2—C2—C3	−177.68 (6)	C5—C6—C7—C2	−0.33 (11)
C1—N1—C3—C4	176.91 (8)	C1—N2—C8—C9	113.65 (8)
C1—N1—C3—C2	−1.82 (8)	C2—N2—C8—C9	−69.97 (9)
N2—C2—C3—C4	−177.25 (7)	N2—C8—C9—C10	−66.44 (9)
C7—C2—C3—C4	2.90 (11)	C8—C9—C10—C11	−176.26 (6)
N2—C2—C3—N1	1.62 (8)	C9—C10—C11—C12	176.47 (7)
C7—C2—C3—N1	−178.23 (7)	C10—C11—C12—C13	−177.19 (7)
N1—C3—C4—C5	179.65 (7)	C11—C12—C13—C14	176.46 (7)
C2—C3—C4—C5	−1.79 (11)	C12—C13—C14—C15	175.71 (7)
C3—C4—C5—C6	−0.32 (11)	C13—C14—C15—C16	177.26 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.89	2.7651 (9)	170
C6—H6···O3ii	0.95	2.58	3.3139 (11)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.89	2.7651 (9)	170
C6—H6⋯O3ii	0.95	2.58	3.3139 (11)	134

Symmetry codes: (i) ; (ii) .