6-(4-Chloro-phen-yl)-3-methyl-imidazo[2,1-b]thia-zole.

In the title compound, C12H9ClN2S, the imidazo[2,1-b]thia-zole fragment is planar (r.m.s. deviation = 0.003 Å), and the benzene ring is twisted slightly [by 5.65 (6)°] relative to this moiety. In the crystal, mol-ecules are linked by π-π stacking inter-actions into columns along [010]. The mol-ecules within the columns are arranged alternatively by their planar rotation of 180°. Thus, in the columns, there are the two types of π-π stacking inter-actions, namely, (i) between two imidazo[2,1-b]thia-zole fragments [inter-planar distance = 3.351 (2) Å] and (ii) between an imidazo[2,1-b]thia-zole fragment and the phenyl ring [inter-planar distance = 3.410 (5) Å]. There are no short contacts between the columns.

Related literature

For the synthesis and properties of related compounds containing an imidazo[2,1-b]thia­zole moiety, see: Raeymaekers et al. (1966 ▶); Metaye et al. (1992 ▶); Carpenter et al. (2003 ▶); Milne et al. (2007 ▶); Scribner et al. (2008 ▶); Chorell et al. (2010 ▶); Guzeldemirci & Kucukbasmaci (2010 ▶); Budriesi et al. (2011 ▶); Yousefi et al. (2011 ▶).

Experimental

Crystal data

C12H9ClN2S

M = 248.73

Triclinic,

a = 7.0624 (5) Å

b = 7.7132 (5) Å

c = 10.3460 (7) Å

α = 93.353 (1)°

β = 90.107 (1)°

γ = 98.832 (1)°

V = 555.92 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.50 mm−1

T = 120 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.864, T max = 0.906

6927 measured reflections

2963 independent reflections

2306 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.05

2963 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813028833/rk2417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028833/rk2417Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028833/rk2417Isup3.cml

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

C12H9ClN2S	Z = 2
Mr = 248.73	F(000) = 256
Triclinic, P1	Dx = 1.486 Mg m−3
Hall symbol: -P 1	Melting point = 397–399 K
a = 7.0624 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7132 (5) Å	Cell parameters from 2226 reflections
c = 10.3460 (7) Å	θ = 2.7–30.6°
α = 93.353 (1)°	µ = 0.50 mm−1
β = 90.107 (1)°	T = 120 K
γ = 98.832 (1)°	Prism, colourless
V = 555.92 (7) Å3	0.30 × 0.20 × 0.20 mm

Bruker APEXII CCD diffractometer	2963 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
Tmin = 0.864, Tmax = 0.906	k = −10→10
6927 measured reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.0291P] where P = (Fo2 + 2Fc2)/3
2963 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.22 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
Cl1	0.38211 (8)	0.73973 (6)	1.00250 (4)	0.04269 (15)
S1	0.13039 (6)	0.04797 (6)	0.19530 (4)	0.02548 (12)
C2	−0.1162 (2)	−0.0288 (2)	0.18876 (16)	0.0239 (3)
H2	−0.1768	−0.1011	0.1184	0.029*
C3	−0.2120 (2)	0.0238 (2)	0.29218 (15)	0.0203 (3)
N4	−0.08638 (17)	0.12958 (16)	0.37993 (12)	0.0180 (3)
C5	−0.0956 (2)	0.21865 (19)	0.49862 (14)	0.0189 (3)
H5	−0.2063	0.2255	0.5495	0.023*
C6	0.0896 (2)	0.29557 (19)	0.52765 (14)	0.0190 (3)
N7	0.21503 (18)	0.25589 (17)	0.42952 (12)	0.0204 (3)
C7A	0.1018 (2)	0.1576 (2)	0.34408 (15)	0.0201 (3)
C8	−0.4178 (2)	−0.0182 (2)	0.32472 (17)	0.0258 (3)
H8A	−0.4875	−0.0863	0.2518	0.039*
H8B	−0.4704	0.0911	0.3422	0.039*
H8C	−0.4314	−0.0873	0.4017	0.039*
C9	0.1606 (2)	0.40574 (19)	0.64315 (14)	0.0188 (3)
C10	0.0334 (2)	0.4576 (2)	0.73671 (15)	0.0230 (3)
H10	−0.1006	0.4220	0.7246	0.028*
C11	0.1012 (3)	0.5600 (2)	0.84631 (16)	0.0272 (4)
H11	0.0142	0.5955	0.9087	0.033*
C12	0.2971 (3)	0.6103 (2)	0.86436 (15)	0.0271 (4)
C13	0.4260 (2)	0.5626 (2)	0.77325 (16)	0.0265 (4)
H13	0.5598	0.5985	0.7860	0.032*
C14	0.3567 (2)	0.4617 (2)	0.66341 (15)	0.0222 (3)
H14	0.4445	0.4298	0.6002	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0636 (3)	0.0379 (3)	0.0254 (2)	0.0095 (2)	−0.0140 (2)	−0.01208 (19)
S1	0.0251 (2)	0.0306 (2)	0.0207 (2)	0.00669 (17)	0.00010 (15)	−0.00563 (16)
C2	0.0266 (8)	0.0227 (8)	0.0224 (8)	0.0048 (7)	−0.0059 (6)	−0.0019 (6)
C3	0.0214 (7)	0.0173 (7)	0.0225 (8)	0.0040 (6)	−0.0064 (6)	0.0014 (6)
N4	0.0190 (6)	0.0166 (6)	0.0190 (6)	0.0045 (5)	−0.0015 (5)	0.0008 (5)
C5	0.0220 (7)	0.0181 (7)	0.0172 (7)	0.0053 (6)	0.0011 (6)	0.0017 (6)
C6	0.0230 (8)	0.0173 (7)	0.0176 (7)	0.0054 (6)	0.0003 (6)	0.0019 (6)
N7	0.0199 (6)	0.0221 (6)	0.0191 (6)	0.0034 (5)	0.0004 (5)	−0.0007 (5)
C7A	0.0211 (7)	0.0215 (7)	0.0187 (7)	0.0064 (6)	0.0011 (6)	0.0007 (6)
C8	0.0212 (8)	0.0263 (8)	0.0292 (9)	0.0027 (7)	−0.0041 (6)	−0.0027 (7)
C9	0.0253 (8)	0.0142 (7)	0.0172 (7)	0.0028 (6)	−0.0018 (6)	0.0031 (6)
C10	0.0275 (8)	0.0190 (7)	0.0230 (8)	0.0049 (6)	0.0014 (6)	0.0027 (6)
C11	0.0417 (10)	0.0228 (8)	0.0192 (8)	0.0107 (7)	0.0030 (7)	0.0021 (6)
C12	0.0438 (10)	0.0193 (7)	0.0178 (7)	0.0047 (7)	−0.0072 (7)	−0.0019 (6)
C13	0.0321 (9)	0.0218 (8)	0.0249 (8)	0.0010 (7)	−0.0067 (7)	0.0027 (7)
C14	0.0262 (8)	0.0199 (7)	0.0200 (7)	0.0019 (6)	0.0000 (6)	0.0022 (6)

Cl1—C12	1.7450 (17)	C8—H8A	0.9800
S1—C7A	1.7399 (16)	C8—H8B	0.9800
S1—C2	1.7512 (17)	C8—H8C	0.9800
C2—C3	1.343 (2)	C9—C14	1.397 (2)
C2—H2	0.9500	C9—C10	1.404 (2)
C3—N4	1.4018 (19)	C10—C11	1.384 (2)
C3—C8	1.483 (2)	C10—H10	0.9500
N4—C7A	1.3685 (19)	C11—C12	1.388 (2)
N4—C5	1.3782 (19)	C11—H11	0.9500
C5—C6	1.376 (2)	C12—C13	1.385 (2)
C5—H5	0.9500	C13—C14	1.383 (2)
C6—N7	1.3996 (18)	C13—H13	0.9500
C6—C9	1.466 (2)	C14—H14	0.9500
N7—C7A	1.315 (2)
C7A—S1—C2	89.68 (7)	H8A—C8—H8B	109.5
C3—C2—S1	113.96 (12)	C3—C8—H8C	109.5
C3—C2—H2	123.0	H8A—C8—H8C	109.5
S1—C2—H2	123.0	H8B—C8—H8C	109.5
C2—C3—N4	110.46 (14)	C14—C9—C10	118.13 (14)
C2—C3—C8	130.15 (15)	C14—C9—C6	120.96 (14)
N4—C3—C8	119.35 (13)	C10—C9—C6	120.91 (14)
C7A—N4—C5	106.48 (12)	C11—C10—C9	120.71 (16)
C7A—N4—C3	115.56 (13)	C11—C10—H10	119.6
C5—N4—C3	137.96 (13)	C9—C10—H10	119.6
C6—C5—N4	105.33 (12)	C10—C11—C12	119.54 (15)
C6—C5—H5	127.3	C10—C11—H11	120.2
N4—C5—H5	127.3	C12—C11—H11	120.2
C5—C6—N7	111.17 (13)	C13—C12—C11	121.06 (15)
C5—C6—C9	128.03 (14)	C13—C12—Cl1	119.50 (14)
N7—C6—C9	120.79 (14)	C11—C12—Cl1	119.43 (13)
C7A—N7—C6	103.37 (12)	C14—C13—C12	118.94 (16)
N7—C7A—N4	113.65 (13)	C14—C13—H13	120.5
N7—C7A—S1	136.01 (12)	C12—C13—H13	120.5
N4—C7A—S1	110.33 (11)	C13—C14—C9	121.60 (15)
C3—C8—H8A	109.5	C13—C14—H14	119.2
C3—C8—H8B	109.5	C9—C14—H14	119.2
C7A—S1—C2—C3	−0.51 (13)	C3—N4—C7A—S1	−0.54 (16)
S1—C2—C3—N4	0.30 (17)	C2—S1—C7A—N7	179.01 (17)
S1—C2—C3—C8	−177.40 (14)	C2—S1—C7A—N4	0.57 (12)
C2—C3—N4—C7A	0.17 (19)	C5—C6—C9—C14	174.39 (15)
C8—C3—N4—C7A	178.15 (13)	N7—C6—C9—C14	−5.4 (2)
C2—C3—N4—C5	−179.57 (16)	C5—C6—C9—C10	−5.4 (2)
C8—C3—N4—C5	−1.6 (3)	N7—C6—C9—C10	174.78 (14)
C7A—N4—C5—C6	−0.14 (16)	C14—C9—C10—C11	−0.6 (2)
C3—N4—C5—C6	179.61 (16)	C6—C9—C10—C11	179.28 (14)
N4—C5—C6—N7	−0.20 (17)	C9—C10—C11—C12	−0.7 (2)
N4—C5—C6—C9	−179.99 (14)	C10—C11—C12—C13	1.2 (2)
C5—C6—N7—C7A	0.46 (16)	C10—C11—C12—Cl1	179.89 (12)
C9—C6—N7—C7A	−179.73 (13)	C11—C12—C13—C14	−0.6 (2)
C6—N7—C7A—N4	−0.56 (17)	Cl1—C12—C13—C14	−179.23 (12)
C6—N7—C7A—S1	−178.95 (14)	C12—C13—C14—C9	−0.7 (2)
C5—N4—C7A—N7	0.46 (17)	C10—C9—C14—C13	1.2 (2)
C3—N4—C7A—N7	−179.35 (12)	C6—C9—C14—C13	−178.60 (14)
C5—N4—C7A—S1	179.27 (10)