6-Chloro-1-(3,5-dimethyl-phenyl-sulfon-yl)-1H-benzimidazol-2(3H)-one.

The title compound, C(15)H(13)ClN(2)O(3)S, is one of a series of N(1)-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethyl-benzene ring and the benzimidazolone ring system, is 88 (1)°, giving a butterfly-like conformation to the mol-ecule. The mol-ecular packing is characterized by a bifurcated N-H⋯(O,O) hydrogen bond and short Cl⋯O contacts of 3.122 (2) Å. In addition, π-π stacking of the benzimidazolone rings is also present, with inter-planar separations of 3.95 (1) Å.

Related literature

For the role of the substituents on the benzene nucleus in anti-HIV-1 compounds, see: Barreca et al. (2007 ▶). For related literature, see: Barreca et al. (2005 ▶); Beddoes et al. (1986 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C15H13ClN2O3S

M = 336.78

Monoclinic,

a = 12.173 (3) Å

b = 14.036 (3) Å

c = 8.949 (2) Å

β = 95.77 (2)°

V = 1521.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 293 (2) K

0.5 × 0.4 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3964 measured reflections

3634 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.133

S = 1.19

3634 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); 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/S1600536808042694/fj2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042694/fj2178Isup2.hkl

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

C15H13ClN2O3S	F(000) = 696
Mr = 336.78	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.173 (3) Å	θ = 9–10°
b = 14.036 (3) Å	µ = 0.40 mm−1
c = 8.949 (2) Å	T = 293 K
β = 95.77 (2)°	Prism, colourless
V = 1521.3 (6) Å3	0.5 × 0.4 × 0.3 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 3.3°
graphite	h = −16→15
Non–profiled ω/2θ scans	k = 0→18
3964 measured reflections	l = 0→11
3634 independent reflections	3 standard reflections every 120 min
3214 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0188P)2 + 1.7615P] where P = (Fo2 + 2Fc2)/3
3634 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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 > 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
S1	0.78957 (6)	0.45343 (4)	0.18441 (6)	0.04124 (17)
Cl1	0.89540 (9)	0.73749 (6)	0.67132 (11)	0.0776 (3)
O3	0.81132 (18)	0.55252 (13)	0.1756 (2)	0.0524 (5)
O1	0.80048 (19)	0.25911 (13)	0.3298 (2)	0.0545 (5)
N2	0.85398 (19)	0.32965 (15)	0.5597 (2)	0.0426 (5)
H2	0.8602	0.2802	0.6166	0.051*
N1	0.83211 (18)	0.42285 (14)	0.3607 (2)	0.0371 (4)
O2	0.83888 (19)	0.38810 (15)	0.0896 (2)	0.0567 (5)
C2	0.8705 (2)	0.42257 (18)	0.6105 (3)	0.0387 (5)
C8	0.6470 (2)	0.4341 (2)	0.1704 (3)	0.0508 (6)
C7	0.85543 (19)	0.48366 (17)	0.4866 (2)	0.0351 (5)
C1	0.8269 (2)	0.32671 (17)	0.4093 (3)	0.0417 (5)
C4	0.9024 (2)	0.5555 (2)	0.7717 (3)	0.0519 (7)
H4	0.9177	0.5817	0.8670	0.062*
C6	0.8637 (2)	0.58080 (18)	0.5011 (3)	0.0425 (5)
H6	0.8547	0.6215	0.4188	0.051*
C3	0.8955 (2)	0.4574 (2)	0.7537 (3)	0.0464 (6)
H3	0.9074	0.4166	0.8356	0.056*
C5	0.8864 (2)	0.61419 (19)	0.6469 (3)	0.0491 (6)
C13	0.6006 (3)	0.3614 (3)	0.0822 (4)	0.0734 (10)
H13	0.6452	0.3204	0.0334	0.088*
C9	0.5842 (3)	0.4951 (3)	0.2471 (4)	0.0671 (9)
H9	0.6174	0.5437	0.3060	0.081*
C11	0.4255 (4)	0.4091 (4)	0.1443 (5)	0.0941 (15)
H11	0.3495	0.3998	0.1362	0.113*
C10	0.4705 (3)	0.4829 (4)	0.2352 (5)	0.0858 (12)
C12	0.4884 (4)	0.3499 (3)	0.0666 (6)	0.0954 (15)
C15	0.4332 (5)	0.2721 (4)	−0.0324 (8)	0.152 (2)
H15A	0.3928	0.2305	0.0274	0.229*
H15B	0.4884	0.2362	−0.0772	0.229*
H15C	0.3835	0.3005	−0.1099	0.229*
C14	0.4004 (4)	0.5506 (5)	0.3165 (7)	0.1339 (17)
H14A	0.4464	0.5843	0.3924	0.201*
H14B	0.3454	0.5152	0.3626	0.201*
H14C	0.3650	0.5953	0.2462	0.201*

	U11	U22	U33	U12	U13	U23
S1	0.0549 (4)	0.0401 (3)	0.0290 (3)	0.0002 (3)	0.0055 (2)	0.0037 (2)
Cl1	0.1068 (7)	0.0451 (4)	0.0801 (6)	−0.0057 (4)	0.0058 (5)	−0.0229 (4)
O3	0.0702 (13)	0.0436 (10)	0.0431 (10)	−0.0050 (9)	0.0043 (9)	0.0112 (8)
O1	0.0876 (15)	0.0359 (9)	0.0394 (10)	−0.0034 (9)	0.0039 (9)	−0.0019 (8)
N2	0.0592 (13)	0.0362 (10)	0.0325 (10)	0.0004 (9)	0.0044 (9)	0.0061 (8)
N1	0.0522 (12)	0.0326 (9)	0.0266 (9)	0.0025 (8)	0.0046 (8)	0.0029 (7)
O2	0.0803 (14)	0.0593 (12)	0.0319 (9)	0.0065 (11)	0.0119 (9)	−0.0046 (8)
C2	0.0415 (12)	0.0424 (13)	0.0326 (11)	−0.0008 (10)	0.0060 (9)	0.0002 (9)
C8	0.0551 (16)	0.0537 (16)	0.0421 (14)	−0.0006 (13)	−0.0025 (12)	0.0088 (12)
C7	0.0357 (11)	0.0383 (12)	0.0316 (11)	0.0015 (9)	0.0055 (8)	−0.0022 (9)
C1	0.0570 (15)	0.0357 (12)	0.0327 (11)	0.0021 (11)	0.0068 (10)	0.0021 (9)
C4	0.0551 (16)	0.0606 (17)	0.0398 (13)	−0.0041 (13)	0.0039 (11)	−0.0130 (12)
C6	0.0491 (14)	0.0375 (12)	0.0410 (13)	0.0005 (11)	0.0051 (10)	−0.0003 (10)
C3	0.0521 (15)	0.0540 (15)	0.0332 (12)	−0.0012 (12)	0.0040 (10)	0.0017 (11)
C5	0.0524 (15)	0.0400 (13)	0.0557 (16)	−0.0051 (11)	0.0096 (12)	−0.0138 (12)
C13	0.076 (2)	0.0580 (19)	0.080 (2)	−0.0021 (17)	−0.0227 (19)	0.0045 (17)
C9	0.0559 (18)	0.089 (3)	0.0559 (18)	−0.0019 (17)	0.0029 (14)	−0.0021 (17)
C11	0.060 (2)	0.121 (4)	0.096 (3)	−0.021 (2)	−0.016 (2)	0.039 (3)
C10	0.063 (2)	0.123 (4)	0.072 (2)	0.008 (2)	0.0080 (19)	0.015 (2)
C12	0.081 (3)	0.079 (3)	0.117 (4)	−0.011 (2)	−0.033 (3)	0.016 (3)
C15	0.138 (5)	0.115 (4)	0.186	−0.035 (4)	−0.075 (4)	−0.004 (4)
C14	0.080 (3)	0.185	0.140 (5)	0.021 (4)	0.027 (3)	−0.019 (5)

S1—O3	1.419 (2)	C6—C5	1.388 (4)
S1—O2	1.423 (2)	C6—H6	0.9300
S1—N1	1.6667 (19)	C3—H3	0.9300
S1—C8	1.749 (3)	C13—C12	1.368 (6)
Cl1—C5	1.746 (3)	C13—H13	0.9300
O1—C1	1.210 (3)	C9—C10	1.388 (5)
N2—C1	1.354 (3)	C9—H9	0.9300
N2—C2	1.389 (3)	C11—C12	1.367 (7)
N2—H2	0.8600	C11—C10	1.395 (7)
N1—C7	1.419 (3)	C11—H11	0.9300
N1—C1	1.421 (3)	C10—C14	1.512 (7)
C2—C3	1.376 (3)	C12—C15	1.520 (7)
C2—C7	1.399 (3)	C15—H15A	0.9600
C8—C13	1.375 (4)	C15—H15B	0.9600
C8—C9	1.376 (5)	C15—H15C	0.9600
C7—C6	1.372 (3)	C14—H14A	0.9600
C4—C5	1.385 (4)	C14—H14B	0.9600
C4—C3	1.389 (4)	C14—H14C	0.9600
C4—H4	0.9300
O3—S1—O2	120.41 (13)	C4—C3—H3	121.1
O3—S1—N1	105.25 (11)	C4—C5—C6	123.8 (3)
O2—S1—N1	106.81 (11)	C4—C5—Cl1	119.1 (2)
O3—S1—C8	109.74 (14)	C6—C5—Cl1	117.1 (2)
O2—S1—C8	109.40 (14)	C12—C13—C8	119.6 (4)
N1—S1—C8	103.86 (12)	C12—C13—H13	120.2
C1—N2—C2	111.5 (2)	C8—C13—H13	120.2
C1—N2—H2	124.2	C8—C9—C10	119.0 (4)
C2—N2—H2	124.2	C8—C9—H9	120.5
C7—N1—C1	109.87 (18)	C10—C9—H9	120.5
C7—N1—S1	127.94 (16)	C12—C11—C10	122.8 (4)
C1—N1—S1	120.99 (16)	C12—C11—H11	118.6
C3—C2—N2	130.5 (2)	C10—C11—H11	118.6
C3—C2—C7	121.3 (2)	C9—C10—C11	117.8 (4)
N2—C2—C7	108.2 (2)	C9—C10—C14	119.5 (5)
C13—C8—C9	122.0 (3)	C11—C10—C14	122.7 (4)
C13—C8—S1	120.2 (3)	C11—C12—C13	118.7 (4)
C9—C8—S1	117.7 (2)	C11—C12—C15	119.7 (5)
C6—C7—C2	122.1 (2)	C13—C12—C15	121.5 (5)
C6—C7—N1	132.8 (2)	C12—C15—H15A	109.5
C2—C7—N1	105.1 (2)	C12—C15—H15B	109.5
O1—C1—N2	129.2 (2)	H15A—C15—H15B	109.5
O1—C1—N1	125.6 (2)	C12—C15—H15C	109.5
N2—C1—N1	105.1 (2)	H15A—C15—H15C	109.5
C5—C4—C3	119.6 (2)	H15B—C15—H15C	109.5
C5—C4—H4	120.2	C10—C14—H14A	109.5
C3—C4—H4	120.2	C10—C14—H14B	109.5
C7—C6—C5	115.5 (2)	H14A—C14—H14B	109.5
C7—C6—H6	122.3	C10—C14—H14C	109.5
C5—C6—H6	122.3	H14A—C14—H14C	109.5
C2—C3—C4	117.7 (2)	H14B—C14—H14C	109.5
C2—C3—H3	121.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.18	2.852 (3)	135 (1)
N2—H2···O2i	0.86	2.39	3.075 (3)	138 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.18	2.852 (3)	135
N2—H2⋯O2i	0.86	2.39	3.075 (3)	138

Symmetry code: (i) .