1,3-Diallyl-5-chloro-1H-benzimidazol-2(3H)-one.

The benzimidazolone part of the title mol-ecule, C(13)H(13)ClN(2)O, is almost planar (r.m.s. deviation = 0.006 Å) and its mean plane is aligned at dihedral angles of 62.5 (1) and 78.0 (1)° with respect to the mean planes of the allyl substituents.

Related literature

For the synthesis, see: Vernin et al. (1981 ▶).

Experimental

Crystal data

C13H13ClN2O

M = 248.70

Monoclinic,

a = 7.8831 (1) Å

b = 15.2481 (3) Å

c = 10.3593 (2) Å

β = 93.056 (1)°

V = 1243.44 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.35 × 0.20 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.905, T max = 0.944

17723 measured reflections

2858 independent reflections

2230 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.156

S = 1.03

2858 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.34 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003035/jh2259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003035/jh2259Isup2.hkl

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

C13H13ClN2O	F(000) = 520
Mr = 248.70	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4645 reflections
a = 7.8831 (1) Å	θ = 2.4–29.0°
b = 15.2481 (3) Å	µ = 0.29 mm−1
c = 10.3593 (2) Å	T = 295 K
β = 93.056 (1)°	Block, colourless
V = 1243.44 (4) Å3	0.35 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII diffractometer	2858 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→10
Tmin = 0.905, Tmax = 0.944	k = −19→19
17723 measured reflections	l = −12→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0846P)2 + 0.6164P] where P = (Fo2 + 2Fc2)/3
2858 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.25390 (9)	0.66457 (5)	0.19928 (6)	0.0609 (2)
O1	0.6243 (2)	0.62064 (10)	0.86933 (14)	0.0468 (4)
N1	0.5616 (2)	0.66732 (10)	0.65711 (15)	0.0341 (4)
N2	0.4252 (2)	0.55197 (10)	0.72844 (15)	0.0340 (4)
C1	0.4530 (2)	0.63903 (12)	0.55655 (17)	0.0304 (4)
C2	0.4221 (2)	0.67167 (12)	0.43253 (18)	0.0346 (4)
H2	0.4781	0.7208	0.4029	0.042*
C3	0.3021 (3)	0.62631 (14)	0.35525 (19)	0.0388 (5)
C4	0.2168 (3)	0.55288 (14)	0.3964 (2)	0.0407 (5)
H4	0.1391	0.5244	0.3403	0.049*
C5	0.2476 (2)	0.52151 (13)	0.5227 (2)	0.0371 (4)
H5	0.1904	0.4728	0.5526	0.045*
C6	0.3663 (2)	0.56580 (12)	0.60094 (17)	0.0307 (4)
C7	0.5461 (3)	0.61349 (12)	0.76399 (18)	0.0348 (4)
C8	0.6889 (3)	0.73629 (13)	0.6498 (2)	0.0385 (5)
H8A	0.7127	0.7607	0.7353	0.046*
H8B	0.6442	0.7829	0.5941	0.046*
C9	0.8507 (3)	0.70238 (14)	0.5983 (2)	0.0438 (5)
H9	0.9055	0.6560	0.6414	0.053*
C10	0.9186 (3)	0.73440 (16)	0.4965 (3)	0.0548 (6)
H10A	0.8664	0.7808	0.4516	0.066*
H10B	1.0192	0.7109	0.4687	0.066*
C11	0.3710 (3)	0.48204 (13)	0.8125 (2)	0.0410 (5)
H11A	0.4544	0.4757	0.8842	0.049*
H11B	0.3681	0.4274	0.7645	0.049*
C12	0.2008 (3)	0.49716 (17)	0.8649 (2)	0.0561 (7)
H12	0.1536	0.4507	0.9088	0.067*
C13	0.1120 (4)	0.5692 (2)	0.8550 (3)	0.0647 (8)
H13A	0.1540	0.6174	0.8120	0.078*
H13B	0.0066	0.5723	0.8911	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.0596 (4)	0.0792 (5)	0.0427 (3)	−0.0024 (3)	−0.0096 (3)	0.0139 (3)
O1	0.0592 (10)	0.0442 (8)	0.0362 (7)	−0.0043 (7)	−0.0055 (7)	0.0002 (6)
N1	0.0399 (9)	0.0296 (8)	0.0326 (8)	−0.0039 (6)	0.0018 (7)	−0.0010 (6)
N2	0.0393 (9)	0.0291 (8)	0.0339 (8)	−0.0015 (6)	0.0054 (6)	0.0019 (6)
C1	0.0300 (9)	0.0290 (8)	0.0329 (9)	0.0024 (7)	0.0062 (7)	−0.0024 (7)
C2	0.0335 (10)	0.0357 (10)	0.0352 (9)	0.0027 (7)	0.0070 (8)	0.0034 (7)
C3	0.0355 (10)	0.0477 (11)	0.0335 (9)	0.0087 (8)	0.0041 (8)	0.0005 (8)
C4	0.0320 (10)	0.0473 (11)	0.0427 (11)	−0.0002 (8)	0.0013 (8)	−0.0081 (9)
C5	0.0332 (10)	0.0350 (9)	0.0437 (10)	−0.0031 (8)	0.0069 (8)	−0.0039 (8)
C6	0.0303 (9)	0.0288 (8)	0.0336 (9)	0.0028 (7)	0.0071 (7)	−0.0023 (7)
C7	0.0406 (10)	0.0288 (9)	0.0351 (9)	0.0020 (8)	0.0043 (8)	−0.0014 (7)
C8	0.0465 (12)	0.0300 (9)	0.0391 (10)	−0.0081 (8)	0.0024 (8)	−0.0036 (8)
C9	0.0348 (11)	0.0325 (10)	0.0627 (13)	−0.0023 (8)	−0.0097 (9)	0.0045 (9)
C10	0.0429 (13)	0.0474 (12)	0.0750 (17)	−0.0005 (10)	0.0119 (11)	−0.0051 (12)
C11	0.0500 (12)	0.0313 (10)	0.0424 (11)	0.0032 (8)	0.0094 (9)	0.0089 (8)
C12	0.0663 (16)	0.0553 (14)	0.0492 (13)	0.0046 (12)	0.0263 (12)	0.0163 (10)
C13	0.0656 (17)	0.0776 (18)	0.0535 (14)	0.0202 (14)	0.0259 (13)	0.0098 (13)

Cl1—C3	1.741 (2)	C5—H5	0.9300
O1—C7	1.229 (2)	C8—C9	1.501 (3)
N1—C1	1.382 (2)	C8—H8A	0.9700
N1—C7	1.389 (2)	C8—H8B	0.9700
N1—C8	1.459 (2)	C9—C10	1.303 (3)
N2—C7	1.373 (3)	C9—H9	0.9300
N2—C6	1.393 (2)	C10—H10A	0.9300
N2—C11	1.455 (2)	C10—H10B	0.9300
C1—C2	1.387 (3)	C11—C12	1.492 (3)
C1—C6	1.400 (3)	C11—H11A	0.9700
C2—C3	1.390 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—C13	1.303 (4)
C3—C4	1.385 (3)	C12—H12	0.9300
C4—C5	1.402 (3)	C13—H13A	0.9300
C4—H4	0.9300	C13—H13B	0.9300
C5—C6	1.381 (3)
C1—N1—C7	109.83 (16)	N2—C7—N1	106.21 (16)
C1—N1—C8	125.89 (16)	N1—C8—C9	111.75 (16)
C7—N1—C8	123.90 (17)	N1—C8—H8A	109.3
C7—N2—C6	110.02 (15)	C9—C8—H8A	109.3
C7—N2—C11	124.17 (17)	N1—C8—H8B	109.3
C6—N2—C11	125.80 (17)	C9—C8—H8B	109.3
N1—C1—C2	131.12 (17)	H8A—C8—H8B	107.9
N1—C1—C6	107.17 (16)	C10—C9—C8	123.5 (2)
C2—C1—C6	121.71 (18)	C10—C9—H9	118.2
C3—C2—C1	115.81 (18)	C8—C9—H9	118.2
C3—C2—H2	122.1	C9—C10—H10A	120.0
C1—C2—H2	122.1	C9—C10—H10B	120.0
C4—C3—C2	123.46 (19)	H10A—C10—H10B	120.0
C4—C3—Cl1	118.11 (17)	N2—C11—C12	113.75 (17)
C2—C3—Cl1	118.43 (16)	N2—C11—H11A	108.8
C3—C4—C5	120.04 (19)	C12—C11—H11A	108.8
C3—C4—H4	120.0	N2—C11—H11B	108.8
C5—C4—H4	120.0	C12—C11—H11B	108.8
C6—C5—C4	117.31 (18)	H11A—C11—H11B	107.7
C6—C5—H5	121.3	C13—C12—C11	126.3 (2)
C4—C5—H5	121.3	C13—C12—H12	116.9
C5—C6—N2	131.58 (17)	C11—C12—H12	116.9
C5—C6—C1	121.65 (18)	C12—C13—H13A	120.0
N2—C6—C1	106.76 (16)	C12—C13—H13B	120.0
O1—C7—N2	127.35 (18)	H13A—C13—H13B	120.0
O1—C7—N1	126.44 (18)
C7—N1—C1—C2	179.23 (19)	C2—C1—C6—C5	1.1 (3)
C8—N1—C1—C2	−7.7 (3)	N1—C1—C6—N2	0.17 (19)
C7—N1—C1—C6	0.2 (2)	C2—C1—C6—N2	−178.95 (16)
C8—N1—C1—C6	173.33 (17)	C6—N2—C7—O1	179.96 (19)
N1—C1—C2—C3	−179.86 (18)	C11—N2—C7—O1	−1.2 (3)
C6—C1—C2—C3	−1.0 (3)	C6—N2—C7—N1	0.6 (2)
C1—C2—C3—C4	−0.1 (3)	C11—N2—C7—N1	179.50 (16)
C1—C2—C3—Cl1	178.90 (14)	C1—N1—C7—O1	−179.86 (19)
C2—C3—C4—C5	1.1 (3)	C8—N1—C7—O1	6.9 (3)
Cl1—C3—C4—C5	−177.91 (15)	C1—N1—C7—N2	−0.5 (2)
C3—C4—C5—C6	−1.0 (3)	C8—N1—C7—N2	−173.81 (16)
C4—C5—C6—N2	179.97 (18)	C1—N1—C8—C9	−83.2 (2)
C4—C5—C6—C1	−0.1 (3)	C7—N1—C8—C9	88.9 (2)
C7—N2—C6—C5	179.44 (19)	N1—C8—C9—C10	122.9 (2)
C11—N2—C6—C5	0.6 (3)	C7—N2—C11—C12	104.9 (2)
C7—N2—C6—C1	−0.5 (2)	C6—N2—C11—C12	−76.4 (3)
C11—N2—C6—C1	−179.34 (17)	N2—C11—C12—C13	−9.0 (4)
N1—C1—C6—C5	−179.79 (17)