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

In the title compound, C(15)H(22)N(2)O, the octyl group adopts an all-trans conformation. In the crystal, mol-ecules form centrosymmetric dimers with an R(2) (2)(8) graph-set motif, linked by pairs of N-H⋯O hydrogen bonds. In addition, C-H⋯O contacts are observed.

Related literature

For background to benzimidazol-2-one, see: Soderlind et al. (1999 ▶). For similar structures, see: Ouzidan et al. (2011 ▶); Kandri Rodi et al. (2011 ▶).

Experimental

Crystal data

C15H22N2O

M = 246.35

Monoclinic,

a = 14.8888 (18) Å

b = 5.8395 (6) Å

c = 16.6778 (19) Å

β = 91.448 (3)°

V = 1449.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.54 × 0.43 × 0.12 mm

Data collection

Bruker X8 APEX diffractometer

8760 measured reflections

3020 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.03

3020 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013384/bt5862sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013384/bt5862Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013384/bt5862Isup3.cml

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

C15H22N2O	F(000) = 536
Mr = 246.35	Dx = 1.129 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3020 reflections
a = 14.8888 (18) Å	θ = 2.4–26.5°
b = 5.8395 (6) Å	µ = 0.07 mm−1
c = 16.6778 (19) Å	T = 296 K
β = 91.448 (3)°	Needle, colourless
V = 1449.6 (3) Å3	0.54 × 0.43 × 0.12 mm
Z = 4

Bruker X8 APEX diffractometer	1971 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 26.5°, θmin = 2.4°
φ and ω scans	h = −18→18
8760 measured reflections	k = −5→7
3020 independent reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.2949P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3020 reflections	Δρmax = 0.18 e Å−3
164 parameters	Δρmin = −0.14 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: 0.010 (2)

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 > 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	0.94346 (9)	0.1963 (2)	0.56368 (7)	0.0642 (4)
N1	0.94058 (10)	0.1858 (2)	0.42412 (8)	0.0547 (4)
H1	0.9690	0.0598	0.4166	0.066*
N2	0.87525 (9)	0.4734 (2)	0.48345 (8)	0.0517 (4)
C2	0.90690 (11)	0.3264 (3)	0.36345 (10)	0.0486 (4)
C1	0.92224 (11)	0.2755 (3)	0.49722 (10)	0.0509 (4)
C7	0.86541 (11)	0.5096 (3)	0.40093 (10)	0.0499 (4)
C3	0.90920 (12)	0.3128 (3)	0.28082 (10)	0.0596 (5)
H3	0.9368	0.1908	0.2554	0.072*
C6	0.82615 (14)	0.6843 (3)	0.35775 (12)	0.0660 (5)
H6	0.7991	0.8074	0.3830	0.079*
C9	0.74157 (14)	0.6002 (4)	0.55652 (12)	0.0696 (6)
H9A	0.7232	0.7133	0.5954	0.084*
H9B	0.7117	0.6367	0.5058	0.084*
C4	0.86880 (14)	0.4880 (4)	0.23756 (11)	0.0684 (6)
H4	0.8688	0.4832	0.1818	0.082*
C8	0.84181 (13)	0.6198 (3)	0.54643 (11)	0.0613 (5)
H8A	0.8565	0.7776	0.5343	0.074*
H8B	0.8721	0.5802	0.5967	0.074*
C5	0.82845 (15)	0.6697 (4)	0.27511 (12)	0.0721 (6)
H5	0.8022	0.7852	0.2441	0.087*
C10	0.71026 (13)	0.3677 (4)	0.58346 (13)	0.0743 (6)
H10A	0.7399	0.3306	0.6343	0.089*
H10B	0.7282	0.2540	0.5446	0.089*
C11	0.60948 (14)	0.3539 (4)	0.59315 (15)	0.0855 (7)
H11A	0.5922	0.4626	0.6340	0.103*
H11B	0.5800	0.3994	0.5431	0.103*
C12	0.57598 (15)	0.1199 (4)	0.61598 (16)	0.0896 (7)
H12B	0.6050	0.0758	0.6663	0.107*
H12A	0.5944	0.0112	0.5756	0.107*
C13	0.47537 (15)	0.1006 (5)	0.62485 (16)	0.0932 (8)
H13A	0.4568	0.2077	0.6657	0.112*
H13B	0.4460	0.1449	0.5746	0.112*
C14	0.44383 (18)	−0.1364 (6)	0.64722 (19)	0.1112 (9)
H14A	0.4632	−0.2430	0.6065	0.133*
H14B	0.4734	−0.1797	0.6974	0.133*
C15	0.3454 (2)	−0.1625 (6)	0.6560 (2)	0.1342 (12)
H15A	0.3320	−0.3183	0.6697	0.201*
H15B	0.3152	−0.1235	0.6064	0.201*
H15C	0.3255	−0.0627	0.6977	0.201*

	U11	U22	U33	U12	U13	U23
O1	0.0772 (8)	0.0636 (8)	0.0520 (8)	0.0168 (6)	0.0057 (6)	0.0123 (6)
N1	0.0628 (9)	0.0464 (8)	0.0552 (9)	0.0099 (7)	0.0081 (7)	−0.0002 (7)
N2	0.0616 (9)	0.0464 (8)	0.0471 (8)	0.0075 (7)	0.0023 (6)	0.0000 (6)
C2	0.0494 (9)	0.0448 (9)	0.0518 (9)	−0.0031 (7)	0.0033 (7)	0.0014 (8)
C1	0.0515 (9)	0.0476 (10)	0.0538 (10)	0.0006 (8)	0.0054 (7)	0.0034 (8)
C7	0.0569 (10)	0.0452 (9)	0.0474 (9)	−0.0018 (8)	0.0001 (7)	0.0005 (7)
C3	0.0656 (11)	0.0592 (11)	0.0543 (11)	−0.0016 (9)	0.0079 (8)	−0.0064 (9)
C6	0.0856 (14)	0.0506 (11)	0.0615 (12)	0.0135 (10)	−0.0020 (9)	0.0009 (9)
C9	0.0782 (13)	0.0693 (13)	0.0614 (12)	0.0253 (11)	0.0050 (9)	−0.0062 (10)
C4	0.0807 (13)	0.0761 (14)	0.0483 (10)	−0.0052 (11)	0.0001 (9)	0.0033 (10)
C8	0.0783 (13)	0.0520 (11)	0.0536 (10)	0.0100 (9)	0.0000 (9)	−0.0082 (9)
C5	0.0938 (15)	0.0654 (13)	0.0569 (12)	0.0094 (11)	−0.0057 (10)	0.0111 (10)
C10	0.0684 (13)	0.0785 (14)	0.0764 (14)	0.0186 (11)	0.0086 (10)	0.0031 (11)
C11	0.0713 (14)	0.0938 (17)	0.0919 (16)	0.0211 (12)	0.0106 (11)	0.0036 (14)
C12	0.0739 (14)	0.0947 (18)	0.1004 (18)	0.0153 (13)	0.0087 (12)	−0.0010 (15)
C13	0.0711 (14)	0.107 (2)	0.1020 (18)	0.0144 (14)	0.0064 (12)	−0.0025 (16)
C14	0.0817 (17)	0.112 (2)	0.140 (3)	0.0135 (16)	0.0050 (16)	0.0126 (19)
C15	0.088 (2)	0.141 (3)	0.174 (3)	0.0011 (19)	0.0011 (19)	0.013 (2)

O1—C1	1.235 (2)	C8—H8B	0.9700
N1—C1	1.361 (2)	C5—H5	0.9300
N1—C2	1.387 (2)	C10—C11	1.515 (3)
N1—H1	0.8600	C10—H10A	0.9700
N2—C1	1.367 (2)	C10—H10B	0.9700
N2—C7	1.396 (2)	C11—C12	1.507 (4)
N2—C8	1.452 (2)	C11—H11A	0.9700
C2—C3	1.382 (2)	C11—H11B	0.9700
C2—C7	1.391 (2)	C12—C13	1.513 (3)
C7—C6	1.371 (2)	C12—H12B	0.9700
C3—C4	1.381 (3)	C12—H12A	0.9700
C3—H3	0.9300	C13—C14	1.511 (4)
C6—C5	1.382 (3)	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C9—C10	1.507 (3)	C14—C15	1.484 (4)
C9—C8	1.511 (3)	C14—H14A	0.9700
C9—H9A	0.9700	C14—H14B	0.9700
C9—H9B	0.9700	C15—H15A	0.9600
C4—C5	1.378 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C8—H8A	0.9700
C1—N1—C2	110.42 (14)	C6—C5—H5	119.2
C1—N1—H1	124.8	C9—C10—C11	113.20 (18)
C2—N1—H1	124.8	C9—C10—H10A	108.9
C1—N2—C7	109.50 (14)	C11—C10—H10A	108.9
C1—N2—C8	124.01 (14)	C9—C10—H10B	108.9
C7—N2—C8	126.49 (14)	C11—C10—H10B	108.9
C3—C2—N1	132.54 (16)	H10A—C10—H10B	107.8
C3—C2—C7	120.98 (16)	C12—C11—C10	114.20 (18)
N1—C2—C7	106.48 (14)	C12—C11—H11A	108.7
O1—C1—N1	127.41 (16)	C10—C11—H11A	108.7
O1—C1—N2	125.84 (16)	C12—C11—H11B	108.7
N1—C1—N2	106.75 (14)	C10—C11—H11B	108.7
C6—C7—C2	121.62 (16)	H11A—C11—H11B	107.6
C6—C7—N2	131.52 (16)	C11—C12—C13	115.3 (2)
C2—C7—N2	106.85 (14)	C11—C12—H12B	108.5
C4—C3—C2	117.20 (17)	C13—C12—H12B	108.5
C4—C3—H3	121.4	C11—C12—H12A	108.5
C2—C3—H3	121.4	C13—C12—H12A	108.5
C7—C6—C5	117.19 (18)	H12B—C12—H12A	107.5
C7—C6—H6	121.4	C14—C13—C12	114.0 (2)
C5—C6—H6	121.4	C14—C13—H13A	108.7
C10—C9—C8	114.54 (16)	C12—C13—H13A	108.7
C10—C9—H9A	108.6	C14—C13—H13B	108.7
C8—C9—H9A	108.6	C12—C13—H13B	108.7
C10—C9—H9B	108.6	H13A—C13—H13B	107.6
C8—C9—H9B	108.6	C15—C14—C13	115.6 (2)
H9A—C9—H9B	107.6	C15—C14—H14A	108.4
C5—C4—C3	121.48 (18)	C13—C14—H14A	108.4
C5—C4—H4	119.3	C15—C14—H14B	108.4
C3—C4—H4	119.3	C13—C14—H14B	108.4
N2—C8—C9	113.18 (15)	H14A—C14—H14B	107.4
N2—C8—H8A	108.9	C14—C15—H15A	109.5
C9—C8—H8A	108.9	C14—C15—H15B	109.5
N2—C8—H8B	108.9	H15A—C15—H15B	109.5
C9—C8—H8B	108.9	C14—C15—H15C	109.5
H8A—C8—H8B	107.8	H15A—C15—H15C	109.5
C4—C5—C6	121.53 (19)	H15B—C15—H15C	109.5
C4—C5—H5	119.2
C1—N1—C2—C3	178.89 (18)	N1—C2—C3—C4	−179.26 (18)
C1—N1—C2—C7	−0.48 (18)	C7—C2—C3—C4	0.0 (3)
C2—N1—C1—O1	−178.99 (16)	C2—C7—C6—C5	0.8 (3)
C2—N1—C1—N2	0.88 (18)	N2—C7—C6—C5	179.37 (18)
C7—N2—C1—O1	178.93 (16)	C2—C3—C4—C5	0.5 (3)
C8—N2—C1—O1	−1.0 (3)	C1—N2—C8—C9	−105.19 (19)
C7—N2—C1—N1	−0.95 (18)	C7—N2—C8—C9	74.9 (2)
C8—N2—C1—N1	179.15 (15)	C10—C9—C8—N2	64.2 (2)
C3—C2—C7—C6	−0.7 (3)	C3—C4—C5—C6	−0.3 (3)
N1—C2—C7—C6	178.77 (17)	C7—C6—C5—C4	−0.3 (3)
C3—C2—C7—N2	−179.57 (15)	C8—C9—C10—C11	179.88 (17)
N1—C2—C7—N2	−0.11 (17)	C9—C10—C11—C12	177.1 (2)
C1—N2—C7—C6	−178.07 (19)	C10—C11—C12—C13	−179.1 (2)
C8—N2—C7—C6	1.8 (3)	C11—C12—C13—C14	179.6 (2)
C1—N2—C7—C2	0.66 (18)	C12—C13—C14—C15	−179.7 (3)
C8—N2—C7—C2	−179.44 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.01	2.8257 (19)	159
C4—H4···O1ii	0.93	2.52	3.312 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.01	2.8257 (19)	159
C4—H4⋯O1ii	0.93	2.52	3.312 (2)	144

Symmetry codes: (i) ; (ii) .