(Z)-2-(4-Chloro-benzyl-idene)benzo[d]thia-zolo[3,2-a]imidazol-3(2H)-one.

The mol-ecule of the title compound, C(16)H(9)ClN(2)OS, is approximately planar, the dihedral angle between the thia-zolo[3,2-a]benzimidazole ring system and the 4-chloro-phenyl ring being 2.10 (5)°. An intra-molecular C-H⋯S inter-action generates an S(6) ring motif. In the crystal, mol-ecules are stacked into columns along the b axis by π-π inter-actions with centroid-centroid distances of 3.6495 (7)-3.9546 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and the biological activity of thia­zolo[3,2-a]benzimidazoles, see: Abdel-Aziz, El-Zahabi & Dawood (2010 ▶); Abdel-Aziz, Hamdy et al. (2007 ▶, 2008 ▶); Abdel-Aziz, Saleh & El-Zahabi (2010 ▶); Al-Rashood & Abdel-Aziz (2010 ▶); Chimirri et al. (1988 ▶); Farag et al. (2011 ▶); Hamdy et al. (2007 ▶); Mavrova et al. (2005 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H9ClN2OS

M = 312.77

Triclinic,

a = 7.0182 (4) Å

b = 7.3443 (4) Å

c = 13.7142 (8) Å

α = 91.742 (1)°

β = 100.836 (1)°

γ = 112.878 (1)°

V = 635.47 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 100 K

0.37 × 0.18 × 0.06 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.848, T max = 0.973

14145 measured reflections

3660 independent reflections

3233 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.05

3660 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015516/is5117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015516/is5117Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015516/is5117Isup3.cml

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

C16H9ClN2OS	Z = 2
Mr = 312.77	F(000) = 320
Triclinic, P1	Dx = 1.635 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0182 (4) Å	Cell parameters from 3660 reflections
b = 7.3443 (4) Å	θ = 1.5–30.0°
c = 13.7142 (8) Å	µ = 0.46 mm−1
α = 91.742 (1)°	T = 100 K
β = 100.836 (1)°	Needle, yellow
γ = 112.878 (1)°	0.37 × 0.18 × 0.06 mm
V = 635.47 (6) Å3

Bruker APEX DUO CCD area-detector diffractometer	3660 independent reflections
Radiation source: sealed tube	3233 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.848, Tmax = 0.973	k = −10→10
14145 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.3855P] where P = (Fo2 + 2Fc2)/3
3660 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.34693 (4)	0.25459 (4)	0.03735 (2)	0.01299 (8)
Cl1	−0.35675 (5)	−0.18707 (5)	−0.43869 (2)	0.02057 (9)
O1	0.88271 (14)	0.27130 (14)	−0.01062 (7)	0.01625 (18)
N1	0.58054 (16)	0.43157 (15)	0.22785 (8)	0.0138 (2)
N2	0.75134 (15)	0.36857 (15)	0.11464 (7)	0.01179 (19)
C1	0.56374 (18)	0.36129 (17)	0.13730 (9)	0.0123 (2)
C2	0.79803 (18)	0.49233 (17)	0.27094 (9)	0.0125 (2)
C3	0.90598 (19)	0.57701 (18)	0.36781 (9)	0.0147 (2)
H3A	0.8365	0.6030	0.4144	0.018*
C4	1.1227 (2)	0.62158 (18)	0.39238 (9)	0.0156 (2)
H4A	1.1988	0.6788	0.4566	0.019*
C5	1.22857 (19)	0.58244 (18)	0.32293 (9)	0.0149 (2)
H5A	1.3731	0.6138	0.3422	0.018*
C6	1.12230 (18)	0.49741 (18)	0.22550 (9)	0.0135 (2)
H6A	1.1918	0.4713	0.1789	0.016*
C7	0.90738 (18)	0.45404 (17)	0.20197 (9)	0.0117 (2)
C8	0.73740 (18)	0.28632 (17)	0.01951 (9)	0.0121 (2)
C9	0.51258 (18)	0.21858 (17)	−0.03702 (9)	0.0120 (2)
C10	0.45896 (18)	0.14096 (17)	−0.13349 (9)	0.0129 (2)
H10A	0.5708	0.1362	−0.1591	0.015*
C11	0.25559 (18)	0.06330 (17)	−0.20435 (9)	0.0125 (2)
C12	0.25076 (19)	−0.00568 (18)	−0.30184 (9)	0.0140 (2)
H12A	0.3757	0.0004	−0.3181	0.017*
C13	0.0643 (2)	−0.08267 (18)	−0.37443 (9)	0.0154 (2)
H13A	0.0636	−0.1272	−0.4388	0.018*
C14	−0.12171 (19)	−0.09177 (18)	−0.34886 (9)	0.0144 (2)
C15	−0.12333 (19)	−0.02595 (18)	−0.25342 (9)	0.0149 (2)
H15A	−0.2493	−0.0337	−0.2377	0.018*
C16	0.06430 (19)	0.05172 (18)	−0.18134 (9)	0.0141 (2)
H16A	0.0635	0.0965	−0.1173	0.017*

	U11	U22	U33	U12	U13	U23
S1	0.01026 (13)	0.01520 (14)	0.01318 (14)	0.00536 (10)	0.00154 (10)	−0.00024 (10)
Cl1	0.01474 (14)	0.02600 (17)	0.01591 (15)	0.00557 (12)	−0.00226 (11)	−0.00026 (11)
O1	0.0137 (4)	0.0197 (4)	0.0166 (4)	0.0080 (3)	0.0038 (3)	−0.0002 (3)
N1	0.0123 (4)	0.0143 (5)	0.0146 (5)	0.0056 (4)	0.0021 (4)	0.0006 (4)
N2	0.0103 (4)	0.0130 (4)	0.0123 (4)	0.0052 (3)	0.0018 (3)	0.0012 (4)
C1	0.0108 (5)	0.0127 (5)	0.0145 (5)	0.0056 (4)	0.0029 (4)	0.0021 (4)
C2	0.0126 (5)	0.0113 (5)	0.0140 (5)	0.0056 (4)	0.0024 (4)	0.0015 (4)
C3	0.0163 (5)	0.0142 (5)	0.0136 (5)	0.0065 (4)	0.0029 (4)	0.0007 (4)
C4	0.0176 (5)	0.0135 (5)	0.0134 (5)	0.0057 (4)	−0.0007 (4)	0.0004 (4)
C5	0.0129 (5)	0.0139 (5)	0.0163 (6)	0.0050 (4)	0.0001 (4)	0.0021 (4)
C6	0.0124 (5)	0.0131 (5)	0.0153 (5)	0.0056 (4)	0.0028 (4)	0.0021 (4)
C7	0.0131 (5)	0.0108 (5)	0.0108 (5)	0.0050 (4)	0.0013 (4)	0.0013 (4)
C8	0.0125 (5)	0.0104 (5)	0.0126 (5)	0.0044 (4)	0.0016 (4)	0.0013 (4)
C9	0.0096 (5)	0.0112 (5)	0.0155 (5)	0.0047 (4)	0.0023 (4)	0.0023 (4)
C10	0.0125 (5)	0.0121 (5)	0.0149 (5)	0.0059 (4)	0.0029 (4)	0.0024 (4)
C11	0.0130 (5)	0.0106 (5)	0.0135 (5)	0.0047 (4)	0.0017 (4)	0.0017 (4)
C12	0.0141 (5)	0.0141 (5)	0.0143 (5)	0.0062 (4)	0.0030 (4)	0.0013 (4)
C13	0.0176 (5)	0.0152 (5)	0.0125 (5)	0.0064 (4)	0.0020 (4)	0.0008 (4)
C14	0.0136 (5)	0.0125 (5)	0.0142 (5)	0.0042 (4)	−0.0009 (4)	0.0016 (4)
C15	0.0129 (5)	0.0158 (5)	0.0161 (6)	0.0059 (4)	0.0033 (4)	0.0027 (4)
C16	0.0148 (5)	0.0144 (5)	0.0131 (5)	0.0061 (4)	0.0028 (4)	0.0010 (4)

S1—C1	1.7411 (12)	C6—C7	1.3849 (16)
S1—C9	1.7692 (12)	C6—H6A	0.9300
Cl1—C14	1.7363 (12)	C8—C9	1.4981 (16)
O1—C8	1.2108 (14)	C9—C10	1.3480 (16)
N1—C1	1.2967 (15)	C10—C11	1.4556 (16)
N1—C2	1.4119 (15)	C10—H10A	0.9300
N2—C1	1.3903 (14)	C11—C12	1.4049 (16)
N2—C8	1.3909 (15)	C11—C16	1.4076 (16)
N2—C7	1.3980 (15)	C12—C13	1.3871 (17)
C2—C3	1.3895 (16)	C12—H12A	0.9300
C2—C7	1.4097 (16)	C13—C14	1.3917 (17)
C3—C4	1.3955 (17)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.3850 (17)
C4—C5	1.3990 (17)	C15—C16	1.3888 (17)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.3942 (17)	C16—H16A	0.9300
C5—H5A	0.9300
C1—S1—C9	90.12 (5)	O1—C8—C9	126.82 (11)
C1—N1—C2	103.32 (10)	N2—C8—C9	107.93 (10)
C1—N2—C8	116.71 (10)	C10—C9—C8	119.68 (10)
C1—N2—C7	105.85 (9)	C10—C9—S1	128.06 (9)
C8—N2—C7	137.35 (10)	C8—C9—S1	112.26 (8)
N1—C1—N2	115.19 (10)	C9—C10—C11	130.90 (11)
N1—C1—S1	131.92 (9)	C9—C10—H10A	114.5
N2—C1—S1	112.88 (9)	C11—C10—H10A	114.5
C3—C2—C7	120.04 (11)	C12—C11—C16	118.15 (11)
C3—C2—N1	128.60 (11)	C12—C11—C10	117.52 (10)
C7—C2—N1	111.36 (10)	C16—C11—C10	124.33 (11)
C2—C3—C4	117.38 (11)	C13—C12—C11	121.66 (11)
C2—C3—H3A	121.3	C13—C12—H12A	119.2
C4—C3—H3A	121.3	C11—C12—H12A	119.2
C3—C4—C5	121.78 (11)	C12—C13—C14	118.53 (11)
C3—C4—H4A	119.1	C12—C13—H13A	120.7
C5—C4—H4A	119.1	C14—C13—H13A	120.7
C6—C5—C4	121.47 (11)	C15—C14—C13	121.46 (11)
C6—C5—H5A	119.3	C15—C14—Cl1	119.27 (9)
C4—C5—H5A	119.3	C13—C14—Cl1	119.26 (9)
C7—C6—C5	116.23 (11)	C14—C15—C16	119.61 (11)
C7—C6—H6A	121.9	C14—C15—H15A	120.2
C5—C6—H6A	121.9	C16—C15—H15A	120.2
C6—C7—N2	132.61 (11)	C15—C16—C11	120.58 (11)
C6—C7—C2	123.10 (11)	C15—C16—H16A	119.7
N2—C7—C2	104.28 (10)	C11—C16—H16A	119.7
O1—C8—N2	125.24 (11)
C2—N1—C1—N2	0.05 (14)	C1—N2—C8—O1	−176.11 (12)
C2—N1—C1—S1	179.02 (10)	C7—N2—C8—O1	−0.2 (2)
C8—N2—C1—N1	177.22 (10)	C1—N2—C8—C9	3.12 (14)
C7—N2—C1—N1	0.13 (14)	C7—N2—C8—C9	178.99 (13)
C8—N2—C1—S1	−1.95 (13)	O1—C8—C9—C10	−3.77 (19)
C7—N2—C1—S1	−179.04 (8)	N2—C8—C9—C10	177.02 (11)
C9—S1—C1—N1	−178.97 (13)	O1—C8—C9—S1	176.23 (11)
C9—S1—C1—N2	0.01 (9)	N2—C8—C9—S1	−2.99 (12)
C1—N1—C2—C3	−179.20 (12)	C1—S1—C9—C10	−178.28 (12)
C1—N1—C2—C7	−0.20 (13)	C1—S1—C9—C8	1.72 (9)
C7—C2—C3—C4	0.23 (18)	C8—C9—C10—C11	179.37 (11)
N1—C2—C3—C4	179.15 (12)	S1—C9—C10—C11	−0.6 (2)
C2—C3—C4—C5	−0.26 (18)	C9—C10—C11—C12	178.99 (12)
C3—C4—C5—C6	0.22 (19)	C9—C10—C11—C16	−1.5 (2)
C4—C5—C6—C7	−0.14 (18)	C16—C11—C12—C13	0.28 (18)
C5—C6—C7—N2	−179.28 (12)	C10—C11—C12—C13	179.85 (11)
C5—C6—C7—C2	0.12 (18)	C11—C12—C13—C14	−0.30 (19)
C1—N2—C7—C6	179.25 (13)	C12—C13—C14—C15	0.04 (19)
C8—N2—C7—C6	3.1 (2)	C12—C13—C14—Cl1	179.84 (9)
C1—N2—C7—C2	−0.24 (12)	C13—C14—C15—C16	0.24 (19)
C8—N2—C7—C2	−176.40 (13)	Cl1—C14—C15—C16	−179.57 (9)
C3—C2—C7—C6	−0.17 (18)	C14—C15—C16—C11	−0.26 (19)
N1—C2—C7—C6	−179.26 (11)	C12—C11—C16—C15	0.01 (18)
C3—C2—C7—N2	179.38 (11)	C10—C11—C16—C15	−179.53 (11)
N1—C2—C7—N2	0.28 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···S1	0.93	2.50	3.2161 (13)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯S1	0.93	2.50	3.2161 (13)	133