1-Nonyl-1H-benzimidazol-2(3H)-one.

The crystal structure of the title compound, C(16)H(24)N(2)O, is built up from two fused six- and five-membered rings linked to C(9)H(19) chains. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is nearly perpendicular to this plane [dihedral angle = 80.27 (17)°]. In the crystal, inter-molecular N-H⋯O hydrogen bonds form dimers with an R(2) (2)(8) graph-set motif. These dimers are further connected through C-H⋯O hydrogen bonds, building sheets parallel to (100).

Related literature

For the pharmacological and biochemical properties of benzimidazol-2-one derivatives, see: El Azzaoui et al. (2006 ▶); Soderlind et al. (1999 ▶); Rémond et al. (1997 ▶); Gribkoff et al. (1994 ▶); Olesen et al. (1994 ▶); McKay et al. (1994 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H24N2O

M = 260.37

Monoclinic,

a = 18.023 (1) Å

b = 5.4585 (2) Å

c = 16.5708 (9) Å

β = 115.543 (7)°

V = 1470.86 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.57 mm−1

T = 123 K

0.54 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.908, T max = 0.955

4966 measured reflections

2656 independent reflections

2073 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.06

2656 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054164/dn2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054164/dn2641Isup2.hkl

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

C16H24N2O	F(000) = 568
Mr = 260.37	Dx = 1.176 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2656 reflections
a = 18.023 (1) Å	θ = 5.3–67.7°
b = 5.4585 (2) Å	µ = 0.57 mm−1
c = 16.5708 (9) Å	T = 123 K
β = 115.543 (7)°	Needle, colorless
V = 1470.86 (15) Å3	0.54 × 0.14 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2656 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2073 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 10.5081 pixels mm-1	θmax = 67.7°, θmin = 5.3°
ω scans	h = −21→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→5
Tmin = 0.908, Tmax = 0.955	l = −15→19
4966 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0758P)2 + 0.0676P] where P = (Fo2 + 2Fc2)/3
2656 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd (2010). Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > 2σ(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	0.04944 (8)	0.7205 (2)	0.58716 (8)	0.0258 (3)
N1	0.11884 (9)	0.9981 (3)	0.53791 (9)	0.0227 (3)
N2	0.05350 (9)	0.6926 (3)	0.44838 (9)	0.0238 (3)
H2N	0.0218 (14)	0.554 (4)	0.4288 (14)	0.040 (6)*
C1	0.07126 (10)	0.7949 (3)	0.53033 (11)	0.0217 (4)
C2	0.08761 (11)	0.8328 (3)	0.40292 (11)	0.0231 (4)
C3	0.08572 (11)	0.8103 (3)	0.31892 (12)	0.0269 (4)
H3A	0.0576	0.6787	0.2803	0.032*
C4	0.12671 (11)	0.9882 (3)	0.29310 (12)	0.0285 (4)
H4A	0.1271	0.9765	0.2361	0.034*
C5	0.16711 (12)	1.1829 (3)	0.34929 (12)	0.0288 (4)
H5A	0.1941	1.3020	0.3296	0.035*
C6	0.16872 (11)	1.2065 (3)	0.43378 (12)	0.0256 (4)
H6A	0.1960	1.3396	0.4720	0.031*
C7	0.12889 (10)	1.0278 (3)	0.45958 (11)	0.0228 (4)
C8	0.14782 (11)	1.1628 (3)	0.61482 (11)	0.0237 (4)
H8A	0.1212	1.1168	0.6539	0.028*
H8B	0.1306	1.3320	0.5935	0.028*
C9	0.24066 (11)	1.1583 (3)	0.66960 (11)	0.0244 (4)
H9A	0.2555	1.2741	0.7202	0.029*
H9B	0.2670	1.2171	0.6317	0.029*
C10	0.27540 (11)	0.9070 (3)	0.70653 (12)	0.0282 (4)
H10A	0.2660	0.7946	0.6561	0.034*
H10B	0.2457	0.8404	0.7399	0.034*
C11	0.36729 (11)	0.9157 (4)	0.76838 (12)	0.0287 (4)
H11A	0.3963	0.9927	0.7360	0.034*
H11B	0.3761	1.0207	0.8204	0.034*
C12	0.40510 (11)	0.6654 (4)	0.80204 (12)	0.0304 (4)
H12A	0.3996	0.5635	0.7503	0.036*
H12B	0.3741	0.5839	0.8314	0.036*
C13	0.49577 (12)	0.6790 (4)	0.86815 (12)	0.0300 (4)
H13A	0.5267	0.7583	0.8383	0.036*
H13B	0.5012	0.7841	0.9191	0.036*
C14	0.53471 (11)	0.4315 (3)	0.90421 (12)	0.0301 (4)
H14A	0.5305	0.3269	0.8536	0.036*
H14B	0.5035	0.3506	0.9335	0.036*
C15	0.62484 (11)	0.4504 (4)	0.97121 (12)	0.0314 (4)
H15A	0.6556	0.5360	0.9425	0.038*
H15B	0.6288	0.5511	1.0226	0.038*
C16	0.66513 (13)	0.2034 (4)	1.00569 (14)	0.0392 (5)
H16A	0.7224	0.2283	1.0491	0.059*
H16B	0.6637	0.1050	0.9556	0.059*
H16C	0.6353	0.1176	1.0346	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0284 (7)	0.0254 (7)	0.0233 (6)	−0.0011 (5)	0.0109 (5)	0.0012 (5)
N1	0.0246 (8)	0.0227 (8)	0.0190 (7)	0.0001 (6)	0.0077 (6)	0.0002 (6)
N2	0.0242 (8)	0.0228 (8)	0.0225 (8)	−0.0017 (6)	0.0083 (6)	−0.0009 (6)
C1	0.0202 (8)	0.0209 (8)	0.0214 (8)	0.0037 (7)	0.0066 (7)	0.0018 (7)
C2	0.0203 (8)	0.0227 (9)	0.0241 (9)	0.0019 (7)	0.0075 (7)	0.0012 (7)
C3	0.0265 (9)	0.0269 (10)	0.0231 (9)	0.0010 (7)	0.0065 (7)	−0.0024 (7)
C4	0.0306 (10)	0.0331 (10)	0.0216 (8)	0.0037 (8)	0.0112 (8)	0.0025 (8)
C5	0.0301 (10)	0.0290 (10)	0.0283 (10)	0.0003 (8)	0.0135 (8)	0.0044 (7)
C6	0.0254 (9)	0.0227 (9)	0.0258 (9)	−0.0010 (7)	0.0082 (7)	−0.0005 (7)
C7	0.0211 (9)	0.0246 (9)	0.0202 (8)	0.0048 (7)	0.0065 (7)	0.0026 (7)
C8	0.0266 (9)	0.0224 (9)	0.0203 (8)	0.0009 (7)	0.0083 (7)	−0.0006 (7)
C9	0.0257 (9)	0.0246 (9)	0.0218 (9)	−0.0014 (7)	0.0093 (7)	−0.0015 (7)
C10	0.0258 (10)	0.0274 (10)	0.0272 (9)	−0.0001 (8)	0.0076 (8)	0.0010 (7)
C11	0.0253 (10)	0.0310 (10)	0.0254 (9)	−0.0003 (8)	0.0066 (8)	0.0017 (7)
C12	0.0274 (10)	0.0312 (10)	0.0281 (9)	−0.0006 (8)	0.0077 (8)	0.0008 (8)
C13	0.0267 (10)	0.0304 (10)	0.0279 (10)	0.0013 (8)	0.0071 (8)	0.0026 (8)
C14	0.0272 (10)	0.0307 (10)	0.0293 (9)	0.0007 (8)	0.0092 (8)	0.0022 (8)
C15	0.0278 (10)	0.0320 (10)	0.0299 (10)	0.0015 (8)	0.0080 (8)	0.0030 (8)
C16	0.0313 (11)	0.0384 (12)	0.0405 (12)	0.0061 (9)	0.0084 (9)	0.0048 (9)

O1—C1	1.235 (2)	C9—H9B	0.9900
N1—C1	1.375 (2)	C10—C11	1.527 (2)
N1—C7	1.395 (2)	C10—H10A	0.9900
N1—C8	1.460 (2)	C10—H10B	0.9900
N2—C1	1.372 (2)	C11—C12	1.522 (3)
N2—C2	1.389 (2)	C11—H11A	0.9900
N2—H2N	0.92 (2)	C11—H11B	0.9900
C2—C3	1.383 (2)	C12—C13	1.527 (3)
C2—C7	1.402 (2)	C12—H12A	0.9900
C3—C4	1.395 (3)	C12—H12B	0.9900
C3—H3A	0.9500	C13—C14	1.521 (3)
C4—C5	1.393 (3)	C13—H13A	0.9900
C4—H4A	0.9500	C13—H13B	0.9900
C5—C6	1.394 (2)	C14—C15	1.525 (2)
C5—H5A	0.9500	C14—H14A	0.9900
C6—C7	1.384 (2)	C14—H14B	0.9900
C6—H6A	0.9500	C15—C16	1.521 (3)
C8—C9	1.521 (2)	C15—H15A	0.9900
C8—H8A	0.9900	C15—H15B	0.9900
C8—H8B	0.9900	C16—H16A	0.9800
C9—C10	1.523 (2)	C16—H16B	0.9800
C9—H9A	0.9900	C16—H16C	0.9800
C1—N1—C7	109.57 (14)	C11—C10—H10A	109.1
C1—N1—C8	123.43 (14)	C9—C10—H10B	109.1
C7—N1—C8	126.84 (15)	C11—C10—H10B	109.1
C1—N2—C2	110.10 (15)	H10A—C10—H10B	107.9
C1—N2—H2N	121.8 (13)	C12—C11—C10	113.73 (16)
C2—N2—H2N	128.0 (13)	C12—C11—H11A	108.8
O1—C1—N2	127.30 (17)	C10—C11—H11A	108.8
O1—C1—N1	125.93 (16)	C12—C11—H11B	108.8
N2—C1—N1	106.77 (14)	C10—C11—H11B	108.8
C3—C2—N2	132.22 (17)	H11A—C11—H11B	107.7
C3—C2—C7	121.15 (16)	C11—C12—C13	113.00 (16)
N2—C2—C7	106.63 (15)	C11—C12—H12A	109.0
C2—C3—C4	117.41 (17)	C13—C12—H12A	109.0
C2—C3—H3A	121.3	C11—C12—H12B	109.0
C4—C3—H3A	121.3	C13—C12—H12B	109.0
C5—C4—C3	121.29 (16)	H12A—C12—H12B	107.8
C5—C4—H4A	119.4	C14—C13—C12	114.10 (16)
C3—C4—H4A	119.4	C14—C13—H13A	108.7
C4—C5—C6	121.35 (17)	C12—C13—H13A	108.7
C4—C5—H5A	119.3	C14—C13—H13B	108.7
C6—C5—H5A	119.3	C12—C13—H13B	108.7
C7—C6—C5	117.15 (17)	H13A—C13—H13B	107.6
C7—C6—H6A	121.4	C13—C14—C15	113.07 (16)
C5—C6—H6A	121.4	C13—C14—H14A	109.0
C6—C7—N1	131.46 (16)	C15—C14—H14A	109.0
C6—C7—C2	121.64 (16)	C13—C14—H14B	109.0
N1—C7—C2	106.89 (15)	C15—C14—H14B	109.0
N1—C8—C9	113.48 (14)	H14A—C14—H14B	107.8
N1—C8—H8A	108.9	C16—C15—C14	113.53 (17)
C9—C8—H8A	108.9	C16—C15—H15A	108.9
N1—C8—H8B	108.9	C14—C15—H15A	108.9
C9—C8—H8B	108.9	C16—C15—H15B	108.9
H8A—C8—H8B	107.7	C14—C15—H15B	108.9
C8—C9—C10	114.21 (15)	H15A—C15—H15B	107.7
C8—C9—H9A	108.7	C15—C16—H16A	109.5
C10—C9—H9A	108.7	C15—C16—H16B	109.5
C8—C9—H9B	108.7	H16A—C16—H16B	109.5
C10—C9—H9B	108.7	C15—C16—H16C	109.5
H9A—C9—H9B	107.6	H16A—C16—H16C	109.5
C9—C10—C11	112.36 (16)	H16B—C16—H16C	109.5
C9—C10—H10A	109.1
C2—N2—C1—O1	178.67 (16)	C8—N1—C7—C6	2.0 (3)
C2—N2—C1—N1	−1.54 (18)	C1—N1—C7—C2	−1.36 (18)
C7—N1—C1—O1	−178.42 (16)	C8—N1—C7—C2	−176.97 (15)
C8—N1—C1—O1	−2.6 (3)	C3—C2—C7—C6	0.6 (3)
C7—N1—C1—N2	1.78 (18)	N2—C2—C7—C6	−178.71 (16)
C8—N1—C1—N2	177.57 (14)	C3—C2—C7—N1	179.70 (15)
C1—N2—C2—C3	−178.49 (18)	N2—C2—C7—N1	0.39 (18)
C1—N2—C2—C7	0.71 (19)	C1—N1—C8—C9	113.44 (17)
N2—C2—C3—C4	179.37 (18)	C7—N1—C8—C9	−71.5 (2)
C7—C2—C3—C4	0.3 (2)	N1—C8—C9—C10	−58.51 (19)
C2—C3—C4—C5	−0.8 (3)	C8—C9—C10—C11	−174.43 (14)
C3—C4—C5—C6	0.5 (3)	C9—C10—C11—C12	−176.51 (15)
C4—C5—C6—C7	0.3 (3)	C10—C11—C12—C13	−176.55 (14)
C5—C6—C7—N1	−179.73 (17)	C11—C12—C13—C14	178.92 (15)
C5—C6—C7—C2	−0.9 (3)	C12—C13—C14—C15	−179.06 (15)
C1—N1—C7—C6	177.62 (18)	C13—C14—C15—C16	−178.32 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.92 (2)	1.92 (2)	2.817 (2)	166.1 (19)
C4—H4A···O1ii	0.95	2.50	3.284 (2)	140
C8—H8B···O1iii	0.99	2.55	3.453 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.92 (2)	1.92 (2)	2.817 (2)	166.1 (19)
C4—H4A⋯O1ii	0.95	2.50	3.284 (2)	140
C8—H8B⋯O1iii	0.99	2.55	3.453 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) .