2-(1H-1,3-Benzodiazol-2-ylsulfan-yl)-1-(4-chloro-phen-yl)ethanone.

The mol-ecule in the structure of the title compound, C(15)H(11)ClN(2)OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O-C-C-C torsion angle of -173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N-H⋯O and N-H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supra-molecular chain along the c axis via C-H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π-π inter-actions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings.

Related literature

For the biological and pharmacological properties of benzim­idazoles, see: Al-Rashood & Abdel-Aziz (2010 ▶); Abdel-Aziz et al. (2010 ▶). For the synthesis, see: Sarhan et al. (1996 ▶). For a related structure, see: Lynch & McClenaghan (2004 ▶).

Experimental

Crystal data

C15H11ClN2OS

M = 302.77

Monoclinic,

a = 27.3765 (4) Å

b = 9.2784 (2) Å

c = 10.3630 (2) Å

β = 93.087 (1)°

V = 2628.49 (9) Å3

Z = 8

Cu Kα radiation

μ = 4.02 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.710, T max = 1.000

5171 measured reflections

2613 independent reflections

2489 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.07

2613 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103666X/ez2258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103666X/ez2258Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103666X/ez2258Isup3.cml

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

C15H11ClN2OS	F(000) = 1248
Mr = 302.77	Dx = 1.530 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 3792 reflections
a = 27.3765 (4) Å	θ = 3.2–74.1°
b = 9.2784 (2) Å	µ = 4.02 mm−1
c = 10.3630 (2) Å	T = 100 K
β = 93.087 (1)°	Block, light-brown
V = 2628.49 (9) Å3	0.40 × 0.30 × 0.20 mm
Z = 8

Agilent SuperNova Dual diffractometer with Atlas detector	2613 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2489 reflections with I > 2σ(I)
mirror	Rint = 0.016
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 3.2°
ω scan	h = −32→34
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→10
Tmin = 0.710, Tmax = 1.000	l = −9→12
5171 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0442P)2 + 2.8814P] where P = (Fo2 + 2Fc2)/3
2613 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.40 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
Cl1	0.282969 (13)	0.21419 (4)	0.22654 (4)	0.01886 (12)
S1	0.059988 (12)	−0.01719 (4)	0.74205 (3)	0.01091 (11)
O1	0.07341 (4)	0.18383 (12)	0.52818 (10)	0.0138 (2)
N1	0.10732 (4)	0.20841 (14)	0.86384 (12)	0.0121 (3)
N2	0.03011 (4)	0.17240 (14)	0.92176 (12)	0.0118 (3)
H2	−0.0005 (8)	0.142 (2)	0.9163 (19)	0.026 (5)*
C1	0.09605 (5)	0.30740 (16)	0.95916 (13)	0.0111 (3)
C2	0.12521 (5)	0.41479 (17)	1.01856 (14)	0.0147 (3)
H2A	0.1576	0.4315	0.9937	0.018*
C3	0.10522 (6)	0.49602 (17)	1.11487 (15)	0.0156 (3)
H3	0.1244	0.5692	1.1570	0.019*
C4	0.05726 (6)	0.47245 (17)	1.15152 (15)	0.0159 (3)
H4	0.0448	0.5299	1.2181	0.019*
C5	0.02753 (5)	0.36737 (17)	1.09304 (14)	0.0141 (3)
H5	−0.0050	0.3517	1.1173	0.017*
C6	0.04807 (5)	0.28607 (15)	0.99671 (13)	0.0109 (3)
C7	0.06706 (5)	0.13180 (16)	0.84568 (13)	0.0106 (3)
C8	0.11504 (5)	0.00291 (16)	0.65706 (14)	0.0115 (3)
H8A	0.1421	0.0295	0.7196	0.014*
H8B	0.1233	−0.0909	0.6184	0.014*
C9	0.11099 (5)	0.11594 (15)	0.55116 (13)	0.0109 (3)
C10	0.15473 (5)	0.13996 (16)	0.47401 (13)	0.0109 (3)
C11	0.19656 (5)	0.05349 (17)	0.48894 (14)	0.0142 (3)
H11	0.1980	−0.0211	0.5518	0.017*
C12	0.23593 (5)	0.07600 (17)	0.41252 (15)	0.0153 (3)
H12	0.2642	0.0168	0.4222	0.018*
C13	0.23353 (5)	0.18575 (17)	0.32202 (14)	0.0133 (3)
C14	0.19256 (5)	0.27407 (16)	0.30626 (14)	0.0145 (3)
H14	0.1916	0.3498	0.2445	0.017*
C15	0.15315 (5)	0.25001 (17)	0.38202 (14)	0.0129 (3)
H15	0.1248	0.3089	0.3713	0.015*

	U11	U22	U33	U12	U13	U23
Cl1	0.01085 (18)	0.0243 (2)	0.0221 (2)	0.00010 (14)	0.00726 (14)	0.00128 (14)
S1	0.00850 (18)	0.01265 (19)	0.01167 (18)	−0.00049 (12)	0.00121 (12)	−0.00085 (12)
O1	0.0078 (5)	0.0169 (5)	0.0168 (5)	0.0032 (4)	0.0010 (4)	0.0014 (4)
N1	0.0084 (6)	0.0141 (6)	0.0138 (6)	0.0000 (5)	0.0005 (4)	0.0004 (5)
N2	0.0071 (6)	0.0149 (6)	0.0134 (6)	−0.0017 (5)	0.0011 (4)	−0.0022 (5)
C1	0.0088 (6)	0.0125 (7)	0.0120 (6)	0.0005 (5)	−0.0011 (5)	0.0026 (5)
C2	0.0099 (6)	0.0154 (7)	0.0184 (7)	−0.0025 (6)	−0.0017 (5)	0.0021 (6)
C3	0.0151 (7)	0.0125 (7)	0.0185 (7)	−0.0023 (6)	−0.0054 (6)	0.0001 (6)
C4	0.0176 (7)	0.0147 (7)	0.0152 (7)	0.0019 (6)	−0.0008 (6)	−0.0019 (6)
C5	0.0113 (7)	0.0162 (7)	0.0150 (7)	0.0004 (6)	0.0018 (5)	−0.0008 (6)
C6	0.0096 (6)	0.0110 (7)	0.0118 (6)	−0.0004 (5)	−0.0019 (5)	0.0009 (5)
C7	0.0084 (6)	0.0131 (7)	0.0101 (6)	0.0009 (5)	−0.0004 (5)	0.0018 (5)
C8	0.0080 (6)	0.0146 (7)	0.0120 (6)	0.0016 (5)	0.0017 (5)	−0.0004 (5)
C9	0.0097 (7)	0.0111 (7)	0.0118 (6)	0.0001 (5)	−0.0006 (5)	−0.0038 (5)
C10	0.0076 (6)	0.0130 (7)	0.0122 (6)	−0.0005 (5)	−0.0007 (5)	−0.0032 (5)
C11	0.0112 (7)	0.0156 (7)	0.0158 (7)	0.0026 (6)	0.0007 (5)	0.0016 (6)
C12	0.0090 (7)	0.0173 (8)	0.0195 (7)	0.0037 (6)	0.0004 (5)	−0.0002 (6)
C13	0.0081 (6)	0.0176 (7)	0.0143 (7)	−0.0025 (6)	0.0025 (5)	−0.0037 (6)
C14	0.0123 (7)	0.0143 (7)	0.0168 (7)	−0.0006 (6)	0.0000 (6)	0.0013 (6)
C15	0.0086 (6)	0.0138 (7)	0.0162 (7)	0.0018 (6)	−0.0012 (5)	−0.0008 (6)

Cl1—C13	1.7392 (15)	C5—C6	1.394 (2)
S1—C7	1.7548 (15)	C5—H5	0.9500
S1—C8	1.7958 (14)	C8—C9	1.518 (2)
O1—C9	1.2187 (17)	C8—H8A	0.9900
N1—C7	1.3165 (19)	C8—H8B	0.9900
N1—C1	1.3955 (19)	C9—C10	1.4920 (19)
N2—C7	1.3685 (18)	C10—C15	1.396 (2)
N2—C6	1.3843 (19)	C10—C11	1.400 (2)
N2—H2	0.88 (2)	C11—C12	1.387 (2)
C1—C2	1.399 (2)	C11—H11	0.9500
C1—C6	1.404 (2)	C12—C13	1.384 (2)
C2—C3	1.386 (2)	C12—H12	0.9500
C2—H2A	0.9500	C13—C14	1.392 (2)
C3—C4	1.403 (2)	C14—C15	1.386 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.388 (2)	C15—H15	0.9500
C4—H4	0.9500
C7—S1—C8	98.65 (7)	C9—C8—H8A	108.9
C7—N1—C1	103.95 (12)	S1—C8—H8A	108.9
C7—N2—C6	106.36 (12)	C9—C8—H8B	108.9
C7—N2—H2	127.0 (14)	S1—C8—H8B	108.9
C6—N2—H2	126.0 (14)	H8A—C8—H8B	107.7
N1—C1—C2	129.61 (13)	O1—C9—C10	120.76 (13)
N1—C1—C6	110.45 (12)	O1—C9—C8	121.77 (13)
C2—C1—C6	119.92 (13)	C10—C9—C8	117.46 (12)
C3—C2—C1	117.78 (14)	C15—C10—C11	119.33 (13)
C3—C2—H2A	121.1	C15—C10—C9	118.61 (13)
C1—C2—H2A	121.1	C11—C10—C9	122.04 (13)
C2—C3—C4	121.42 (14)	C12—C11—C10	120.44 (14)
C2—C3—H3	119.3	C12—C11—H11	119.8
C4—C3—H3	119.3	C10—C11—H11	119.8
C5—C4—C3	121.76 (14)	C11—C12—C13	119.20 (14)
C5—C4—H4	119.1	C11—C12—H12	120.4
C3—C4—H4	119.1	C13—C12—H12	120.4
C4—C5—C6	116.30 (13)	C12—C13—C14	121.44 (14)
C4—C5—H5	121.8	C12—C13—Cl1	119.16 (11)
C6—C5—H5	121.8	C14—C13—Cl1	119.40 (12)
N2—C6—C5	132.02 (14)	C15—C14—C13	119.06 (14)
N2—C6—C1	105.14 (12)	C15—C14—H14	120.5
C5—C6—C1	122.81 (14)	C13—C14—H14	120.5
N1—C7—N2	114.09 (13)	C14—C15—C10	120.53 (13)
N1—C7—S1	125.23 (11)	C14—C15—H15	119.7
N2—C7—S1	120.58 (11)	C10—C15—H15	119.7
C9—C8—S1	113.32 (10)
C7—N1—C1—C2	178.86 (15)	C8—S1—C7—N1	−11.63 (14)
C7—N1—C1—C6	0.28 (15)	C8—S1—C7—N2	172.27 (11)
N1—C1—C2—C3	−177.76 (14)	C7—S1—C8—C9	−79.85 (11)
C6—C1—C2—C3	0.7 (2)	S1—C8—C9—O1	−0.39 (18)
C1—C2—C3—C4	−0.4 (2)	S1—C8—C9—C10	−179.50 (10)
C2—C3—C4—C5	−0.2 (2)	O1—C9—C10—C15	5.2 (2)
C3—C4—C5—C6	0.4 (2)	C8—C9—C10—C15	−175.68 (13)
C7—N2—C6—C5	−178.12 (15)	O1—C9—C10—C11	−173.18 (14)
C7—N2—C6—C1	0.27 (15)	C8—C9—C10—C11	5.9 (2)
C4—C5—C6—N2	178.08 (15)	C15—C10—C11—C12	−0.5 (2)
C4—C5—C6—C1	−0.1 (2)	C9—C10—C11—C12	177.87 (13)
N1—C1—C6—N2	−0.35 (16)	C10—C11—C12—C13	0.5 (2)
C2—C1—C6—N2	−179.09 (13)	C11—C12—C13—C14	0.1 (2)
N1—C1—C6—C5	178.23 (13)	C11—C12—C13—Cl1	179.83 (12)
C2—C1—C6—C5	−0.5 (2)	C12—C13—C14—C15	−0.8 (2)
C1—N1—C7—N2	−0.10 (16)	Cl1—C13—C14—C15	179.50 (11)
C1—N1—C7—S1	−176.42 (10)	C13—C14—C15—C10	0.8 (2)
C6—N2—C7—N1	−0.12 (17)	C11—C10—C15—C14	−0.2 (2)
C6—N2—C7—S1	176.39 (10)	C9—C10—C15—C14	−178.60 (13)

Cg1 and Cg2 are the centroids of the C10–C15 and N1,N2,C1,C6,C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88 (2)	2.14 (2)	2.9104 (16)	144.9 (19)
N2—H2···S1i	0.88 (2)	2.69 (2)	3.4073 (12)	139.1 (16)
C8—H8a···Cg1ii	0.99	2.89	3.5678 (15)	126
C8—H8b···Cg2iii	0.99	2.76	3.4204 (16)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and N1,N2,C1,C6,C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88 (2)	2.14 (2)	2.9104 (16)	144.9 (19)
N2—H2⋯S1i	0.88 (2)	2.69 (2)	3.4073 (12)	139.1 (16)
C8—H8a⋯Cg1ii	0.99	2.89	3.5678 (15)	126
C8—H8b⋯Cg2iii	0.99	2.76	3.4204 (16)	125

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