1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one.

In the title compound, C(19)H(30)N(2)O, the fused ring system is essentially planar, the maximum deviation from the mean plane being 0.013 (2) Å for the N atom bearing the dodecyl chain. The 1-dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle of 82.9 (2)°between planes through the fused ring system and the first three C atoms of the chain. The C-C-C-C torsion angles (about ±179°) of the dodecyl group indicate an anti-periplanar conformation. In the crystal, inversion dimers are formed by pairs of N-H⋯O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benzimidazoles and their derivatives, see: Al Muhaimeed (1997 ▶); Scott et al. (2002 ▶); Nakano et al. (2000 ▶); Zhu et al. (2000 ▶); Zarrinmayeh et al. (1998 ▶). For compounds with closely related structures, see: Ouzidan et al. (2011 ▶); Kandri Rodi et al. (2011 ▶); Belaziz et al. (2012 ▶).

Experimental

Crystal data

C19H30N2O

M = 302.45

Monoclinic,

a = 38.3223 (14) Å

b = 4.8318 (2) Å

c = 21.9831 (8) Å

β = 117.843 (2)°

V = 3599.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.47 × 0.31 × 0.14 mm

Data collection

Bruker X8 APEX Diffractometer

29002 measured reflections

4637 independent reflections

3179 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.141

S = 1.01

4637 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812041189/im2402sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041189/im2402Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041189/im2402Isup3.cml

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

C19H30N2O	F(000) = 1328
Mr = 302.45	Dx = 1.116 Mg m−3
Monoclinic, C2/c	Melting point: 346.5 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.3223 (14) Å	Cell parameters from 4637 reflections
b = 4.8318 (2) Å	θ = 2.4–28.7°
c = 21.9831 (8) Å	µ = 0.07 mm−1
β = 117.843 (2)°	T = 296 K
V = 3599.3 (2) Å3	Needle, colourless
Z = 8	0.47 × 0.31 × 0.14 mm

Bruker X8 APEX Diffractometer	3179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 28.7°, θmin = 2.4°
φ and ω scans	h = −51→51
29002 measured reflections	k = −6→6
4637 independent reflections	l = −29→28

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0721P)2 + 1.030P] where P = (Fo2 + 2Fc2)/3
4637 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
N2	0.03233 (3)	0.5579 (2)	0.13178 (5)	0.0394 (2)
N1	−0.01601 (3)	0.7314 (2)	0.03782 (5)	0.0398 (2)
H1	−0.0289	0.8297	0.0014	0.048*
O1	0.04750 (2)	0.91076 (19)	0.07646 (4)	0.0472 (2)
C11	0.13888 (4)	0.6345 (3)	0.37748 (6)	0.0440 (3)
H11A	0.1187	0.6113	0.3920	0.053*
H11B	0.1428	0.8315	0.3747	0.053*
C7	−0.00182 (3)	0.4187 (2)	0.12105 (6)	0.0386 (3)
C9	0.08398 (3)	0.6105 (3)	0.25353 (6)	0.0431 (3)
H9A	0.0644	0.5596	0.2679	0.052*
H9B	0.0844	0.8108	0.2510	0.052*
C15	0.24328 (4)	0.5988 (3)	0.62951 (6)	0.0514 (3)
H15A	0.2457	0.7986	0.6294	0.062*
H15B	0.2233	0.5564	0.6435	0.062*
C12	0.17715 (4)	0.5077 (3)	0.43133 (6)	0.0484 (3)
H12A	0.1737	0.3089	0.4317	0.058*
H12B	0.1977	0.5418	0.4182	0.058*
C1	0.02366 (3)	0.7522 (2)	0.08097 (5)	0.0371 (3)
C13	0.19082 (4)	0.6180 (3)	0.50358 (6)	0.0498 (3)
H13A	0.1705	0.5816	0.5171	0.060*
H13B	0.1940	0.8170	0.5032	0.060*
C8	0.07235 (3)	0.4891 (3)	0.18297 (6)	0.0424 (3)
H8A	0.0906	0.5557	0.1671	0.051*
H8B	0.0749	0.2894	0.1870	0.051*
C2	−0.03246 (3)	0.5297 (2)	0.06114 (6)	0.0383 (3)
C10	0.12435 (4)	0.5075 (3)	0.30657 (6)	0.0463 (3)
H10A	0.1232	0.3081	0.3104	0.056*
H10B	0.1433	0.5476	0.2902	0.056*
C17	0.29647 (4)	0.5852 (3)	0.75462 (6)	0.0513 (3)
H17A	0.2983	0.7854	0.7541	0.062*
H17B	0.2769	0.5392	0.7693	0.062*
C14	0.22938 (4)	0.4922 (3)	0.55680 (6)	0.0517 (3)
H14A	0.2497	0.5298	0.5433	0.062*
H14B	0.2262	0.2930	0.5567	0.062*
C16	0.28233 (4)	0.4785 (3)	0.68205 (6)	0.0522 (3)
H16A	0.2798	0.2788	0.6823	0.063*
H16B	0.3022	0.5199	0.6678	0.063*
C6	−0.00851 (4)	0.2120 (3)	0.15747 (7)	0.0493 (3)
H6	0.0118	0.1406	0.1977	0.059*
C3	−0.07051 (4)	0.4301 (3)	0.03570 (7)	0.0490 (3)
H3	−0.0910	0.5015	−0.0044	0.059*
C5	−0.04689 (4)	0.1145 (3)	0.13174 (7)	0.0553 (4)
H5	−0.0524	−0.0248	0.1552	0.066*
C18	0.33590 (4)	0.4716 (3)	0.80666 (7)	0.0616 (4)
H18A	0.3555	0.5176	0.7921	0.074*
H18B	0.3341	0.2714	0.8072	0.074*
C19	0.34981 (5)	0.5790 (4)	0.87888 (7)	0.0774 (5)
H19A	0.3750	0.4990	0.9090	0.116*
H19B	0.3310	0.5294	0.8944	0.116*
H19C	0.3522	0.7768	0.8791	0.116*
C4	−0.07710 (4)	0.2207 (3)	0.07186 (8)	0.0554 (4)
H4	−0.1024	0.1494	0.0556	0.066*

	U11	U22	U33	U12	U13	U23
N2	0.0357 (5)	0.0440 (5)	0.0272 (4)	0.0014 (4)	0.0053 (4)	0.0030 (4)
N1	0.0355 (5)	0.0458 (6)	0.0282 (4)	0.0032 (4)	0.0065 (4)	0.0038 (4)
O1	0.0404 (4)	0.0546 (5)	0.0378 (4)	−0.0026 (4)	0.0110 (4)	0.0066 (4)
C11	0.0434 (6)	0.0463 (7)	0.0299 (5)	−0.0011 (5)	0.0067 (5)	0.0014 (5)
C7	0.0416 (6)	0.0397 (6)	0.0304 (5)	0.0009 (5)	0.0134 (5)	−0.0038 (4)
C9	0.0410 (6)	0.0450 (7)	0.0305 (6)	0.0040 (5)	0.0061 (5)	0.0011 (5)
C15	0.0462 (7)	0.0619 (8)	0.0314 (6)	−0.0014 (6)	0.0057 (5)	−0.0013 (5)
C12	0.0457 (7)	0.0524 (7)	0.0306 (6)	0.0017 (6)	0.0040 (5)	−0.0013 (5)
C1	0.0373 (6)	0.0405 (6)	0.0267 (5)	0.0026 (5)	0.0092 (4)	−0.0012 (4)
C13	0.0460 (7)	0.0582 (8)	0.0308 (6)	−0.0006 (6)	0.0058 (5)	−0.0010 (5)
C8	0.0366 (6)	0.0470 (7)	0.0302 (6)	0.0069 (5)	0.0044 (5)	0.0026 (5)
C2	0.0396 (6)	0.0404 (6)	0.0309 (5)	0.0014 (5)	0.0131 (5)	−0.0049 (5)
C10	0.0432 (6)	0.0482 (7)	0.0300 (6)	0.0046 (5)	0.0025 (5)	0.0010 (5)
C17	0.0441 (7)	0.0647 (9)	0.0326 (6)	−0.0039 (6)	0.0075 (5)	−0.0003 (6)
C14	0.0478 (7)	0.0579 (8)	0.0314 (6)	−0.0002 (6)	0.0034 (5)	−0.0018 (5)
C16	0.0473 (7)	0.0597 (8)	0.0330 (6)	−0.0001 (6)	0.0048 (5)	−0.0016 (6)
C6	0.0591 (8)	0.0471 (7)	0.0393 (6)	0.0016 (6)	0.0210 (6)	0.0022 (5)
C3	0.0392 (6)	0.0564 (8)	0.0443 (7)	−0.0002 (5)	0.0135 (5)	−0.0078 (6)
C5	0.0690 (9)	0.0500 (8)	0.0572 (8)	−0.0089 (7)	0.0382 (7)	−0.0030 (6)
C18	0.0494 (8)	0.0736 (10)	0.0394 (7)	0.0005 (7)	0.0021 (6)	0.0011 (7)
C19	0.0585 (9)	0.1111 (14)	0.0367 (7)	−0.0096 (9)	0.0006 (7)	0.0009 (8)
C4	0.0502 (8)	0.0569 (8)	0.0632 (9)	−0.0117 (6)	0.0300 (7)	−0.0127 (7)

N2—C1	1.3759 (15)	C8—H8A	0.9700
N2—C7	1.3899 (15)	C8—H8B	0.9700
N2—C8	1.4550 (14)	C2—C3	1.3816 (17)
N1—C1	1.3688 (14)	C10—H10A	0.9700
N1—C2	1.3827 (15)	C10—H10B	0.9700
N1—H1	0.8600	C17—C18	1.5095 (18)
O1—C1	1.2314 (14)	C17—C16	1.5156 (18)
C11—C10	1.5184 (16)	C17—H17A	0.9700
C11—C12	1.5187 (16)	C17—H17B	0.9700
C11—H11A	0.9700	C14—H14A	0.9700
C11—H11B	0.9700	C14—H14B	0.9700
C7—C6	1.3771 (18)	C16—H16A	0.9700
C7—C2	1.3986 (16)	C16—H16B	0.9700
C9—C8	1.5177 (16)	C6—C5	1.3885 (19)
C9—C10	1.5218 (16)	C6—H6	0.9300
C9—H9A	0.9700	C3—C4	1.381 (2)
C9—H9B	0.9700	C3—H3	0.9300
C15—C16	1.5157 (18)	C5—C4	1.383 (2)
C15—C14	1.5195 (18)	C5—H5	0.9300
C15—H15A	0.9700	C18—C19	1.511 (2)
C15—H15B	0.9700	C18—H18A	0.9700
C12—C13	1.5180 (17)	C18—H18B	0.9700
C12—H12A	0.9700	C19—H19A	0.9600
C12—H12B	0.9700	C19—H19B	0.9600
C13—C14	1.5186 (17)	C19—H19C	0.9600
C13—H13A	0.9700	C4—H4	0.9300
C13—H13B	0.9700
C1—N2—C7	109.94 (9)	N1—C2—C7	106.97 (10)
C1—N2—C8	123.45 (10)	C11—C10—C9	114.11 (11)
C7—N2—C8	126.15 (10)	C11—C10—H10A	108.7
C1—N1—C2	110.23 (9)	C9—C10—H10A	108.7
C1—N1—H1	124.9	C11—C10—H10B	108.7
C2—N1—H1	124.9	C9—C10—H10B	108.7
C10—C11—C12	113.25 (11)	H10A—C10—H10B	107.6
C10—C11—H11A	108.9	C18—C17—C16	114.41 (12)
C12—C11—H11A	108.9	C18—C17—H17A	108.7
C10—C11—H11B	108.9	C16—C17—H17A	108.7
C12—C11—H11B	108.9	C18—C17—H17B	108.7
H11A—C11—H11B	107.7	C16—C17—H17B	108.7
C6—C7—N2	131.94 (11)	H17A—C17—H17B	107.6
C6—C7—C2	121.55 (11)	C13—C14—C15	114.31 (12)
N2—C7—C2	106.51 (10)	C13—C14—H14A	108.7
C8—C9—C10	111.39 (10)	C15—C14—H14A	108.7
C8—C9—H9A	109.3	C13—C14—H14B	108.7
C10—C9—H9A	109.3	C15—C14—H14B	108.7
C8—C9—H9B	109.3	H14A—C14—H14B	107.6
C10—C9—H9B	109.3	C17—C16—C15	114.33 (12)
H9A—C9—H9B	108.0	C17—C16—H16A	108.7
C16—C15—C14	114.07 (12)	C15—C16—H16A	108.7
C16—C15—H15A	108.7	C17—C16—H16B	108.7
C14—C15—H15A	108.7	C15—C16—H16B	108.7
C16—C15—H15B	108.7	H16A—C16—H16B	107.6
C14—C15—H15B	108.7	C7—C6—C5	117.30 (12)
H15A—C15—H15B	107.6	C7—C6—H6	121.3
C13—C12—C11	114.18 (11)	C5—C6—H6	121.3
C13—C12—H12A	108.7	C4—C3—C2	117.68 (12)
C11—C12—H12A	108.7	C4—C3—H3	121.2
C13—C12—H12B	108.7	C2—C3—H3	121.2
C11—C12—H12B	108.7	C4—C5—C6	121.22 (13)
H12A—C12—H12B	107.6	C4—C5—H5	119.4
O1—C1—N1	127.98 (10)	C6—C5—H5	119.4
O1—C1—N2	125.67 (10)	C17—C18—C19	114.10 (14)
N1—C1—N2	106.35 (10)	C17—C18—H18A	108.7
C12—C13—C14	113.68 (12)	C19—C18—H18A	108.7
C12—C13—H13A	108.8	C17—C18—H18B	108.7
C14—C13—H13A	108.8	C19—C18—H18B	108.7
C12—C13—H13B	108.8	H18A—C18—H18B	107.6
C14—C13—H13B	108.8	C18—C19—H19A	109.5
H13A—C13—H13B	107.7	C18—C19—H19B	109.5
N2—C8—C9	113.73 (10)	H19A—C19—H19B	109.5
N2—C8—H8A	108.8	C18—C19—H19C	109.5
C9—C8—H8A	108.8	H19A—C19—H19C	109.5
N2—C8—H8B	108.8	H19B—C19—H19C	109.5
C9—C8—H8B	108.8	C3—C4—C5	121.52 (13)
H8A—C8—H8B	107.7	C3—C4—H4	119.2
C3—C2—N1	132.32 (11)	C5—C4—H4	119.2
C3—C2—C7	120.71 (12)
C1—N2—C7—C6	−179.18 (12)	N2—C7—C2—C3	178.75 (10)
C8—N2—C7—C6	8.5 (2)	C6—C7—C2—N1	179.65 (10)
C1—N2—C7—C2	0.61 (13)	N2—C7—C2—N1	−0.17 (12)
C8—N2—C7—C2	−171.76 (10)	C12—C11—C10—C9	174.05 (11)
C10—C11—C12—C13	−176.14 (11)	C8—C9—C10—C11	176.53 (11)
C2—N1—C1—O1	−179.33 (11)	C12—C13—C14—C15	−179.52 (12)
C2—N1—C1—N2	0.70 (12)	C16—C15—C14—C13	−178.39 (12)
C7—N2—C1—O1	179.22 (11)	C18—C17—C16—C15	−178.41 (13)
C8—N2—C1—O1	−8.16 (18)	C14—C15—C16—C17	179.67 (12)
C7—N2—C1—N1	−0.81 (12)	N2—C7—C6—C5	−179.26 (12)
C8—N2—C1—N1	171.81 (10)	C2—C7—C6—C5	0.99 (18)
C11—C12—C13—C14	−179.29 (11)	N1—C2—C3—C4	179.30 (12)
C1—N2—C8—C9	104.30 (13)	C7—C2—C3—C4	0.70 (18)
C7—N2—C8—C9	−84.31 (15)	C7—C6—C5—C4	0.1 (2)
C10—C9—C8—N2	174.01 (10)	C16—C17—C18—C19	179.99 (13)
C1—N1—C2—C3	−179.08 (12)	C2—C3—C4—C5	0.4 (2)
C1—N1—C2—C7	−0.33 (13)	C6—C5—C4—C3	−0.9 (2)
C6—C7—C2—C3	−1.43 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.97	2.815 (1)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.97	2.815 (1)	168

Symmetry code: (i) .