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

In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thia-diazole rings is 6.0 (9)°. In the crystal, mol-ecules are assembled by the formation of centrosymmetric dimers by π-stacking of the thia-diazole and benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.6938 (11) Å] along [010].

Related literature

For related imidazothia­diazole derivatives and their pharmacological potential, see: Palagiano et al. (1995 ▶). For related structures, see: Banu et al. (2011a ▶,b ▶); Fun et al. (2011a ▶,b ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C10H6ClN3S

M = 235.70

Monoclinic,

a = 5.43804 (19) Å

b = 12.4222 (4) Å

c = 14.1684 (4) Å

β = 100.269 (3)°

V = 941.77 (5) Å3

Z = 4

Cu Kα radiation

μ = 5.37 mm−1

T = 173 K

0.26 × 0.12 × 0.06 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.691, T max = 1.000

5495 measured reflections

1846 independent reflections

1650 reflections with I > 2σ(I))

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.06

1846 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049793/im2414sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049793/im2414Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049793/im2414Isup3.cml

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

C10H6ClN3S	F(000) = 480
Mr = 235.70	Dx = 1.676 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 2788 reflections
a = 5.43804 (19) Å	θ = 3.2–72.4°
b = 12.4222 (4) Å	µ = 5.37 mm−1
c = 14.1684 (4) Å	T = 173 K
β = 100.269 (3)°	Chunk, colorless
V = 941.77 (5) Å3	0.26 × 0.12 × 0.06 mm
Z = 4

Agilent Xcalibur (Eos, Gemini) diffractometer	1846 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1650 reflections with I > 2σ(I))
Graphite monochromator	Rint = 0.046
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 4.8°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→15
Tmin = 0.691, Tmax = 1.000	l = −17→13
5495 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2711P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1846 reflections	Δρmax = 0.36 e Å−3
137 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (5)

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 > 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	0.35900 (10)	0.10200 (4)	0.67741 (4)	0.02949 (18)
S1	0.39725 (10)	0.62878 (4)	0.24567 (3)	0.02652 (18)
N1	0.0469 (3)	0.61595 (14)	0.34925 (13)	0.0253 (4)
N2	0.2006 (3)	0.52794 (13)	0.36757 (12)	0.0199 (4)
N3	0.5314 (3)	0.43233 (13)	0.34504 (12)	0.0222 (4)
C1	0.1320 (4)	0.67447 (17)	0.28675 (15)	0.0261 (4)
H1	0.0545	0.7386	0.2645	0.031*
C2	0.3979 (4)	0.51895 (15)	0.32099 (13)	0.0208 (4)
C3	0.2043 (4)	0.44025 (16)	0.42652 (14)	0.0217 (4)
H3	0.0929	0.4235	0.4671	0.026*
C4	0.4101 (4)	0.38271 (15)	0.41207 (13)	0.0190 (4)
C5	0.5067 (3)	0.28278 (15)	0.46084 (13)	0.0192 (4)
C6	0.3963 (3)	0.24196 (15)	0.53512 (14)	0.0205 (4)
H6	0.2605	0.2769	0.5531	0.025*
C7	0.4911 (4)	0.14891 (16)	0.58176 (13)	0.0213 (4)
C8	0.6921 (4)	0.09440 (16)	0.55644 (16)	0.0258 (4)
H8	0.7526	0.0317	0.5881	0.031*
C9	0.8008 (4)	0.13562 (16)	0.48276 (15)	0.0254 (4)
H9	0.9360	0.1001	0.4650	0.030*
C10	0.7107 (4)	0.22930 (15)	0.43499 (14)	0.0219 (4)
H10	0.7861	0.2563	0.3860	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0325 (3)	0.0305 (3)	0.0269 (3)	0.00059 (19)	0.0091 (2)	0.00925 (19)
S1	0.0346 (3)	0.0247 (3)	0.0222 (3)	0.00174 (19)	0.0104 (2)	0.00440 (18)
N1	0.0239 (9)	0.0224 (8)	0.0297 (9)	0.0063 (6)	0.0050 (7)	0.0021 (7)
N2	0.0198 (8)	0.0193 (8)	0.0212 (8)	0.0029 (6)	0.0052 (6)	−0.0002 (6)
N3	0.0228 (8)	0.0234 (8)	0.0221 (8)	0.0031 (7)	0.0087 (7)	0.0004 (6)
C1	0.0292 (11)	0.0235 (10)	0.0246 (10)	0.0033 (8)	0.0019 (8)	0.0003 (8)
C2	0.0243 (10)	0.0224 (9)	0.0167 (9)	−0.0007 (7)	0.0069 (7)	−0.0006 (7)
C3	0.0237 (10)	0.0215 (9)	0.0220 (9)	0.0030 (7)	0.0096 (8)	0.0032 (7)
C4	0.0195 (10)	0.0208 (9)	0.0166 (9)	0.0000 (7)	0.0027 (7)	−0.0023 (7)
C5	0.0190 (9)	0.0200 (9)	0.0181 (9)	−0.0005 (7)	0.0021 (7)	−0.0034 (7)
C6	0.0194 (9)	0.0220 (9)	0.0203 (9)	0.0013 (7)	0.0045 (7)	−0.0021 (7)
C7	0.0212 (10)	0.0228 (9)	0.0197 (9)	−0.0031 (8)	0.0035 (8)	0.0002 (7)
C8	0.0256 (10)	0.0220 (10)	0.0289 (11)	0.0044 (8)	0.0023 (9)	0.0022 (8)
C9	0.0220 (10)	0.0258 (10)	0.0292 (10)	0.0043 (8)	0.0069 (8)	−0.0028 (8)
C10	0.0229 (10)	0.0221 (9)	0.0214 (9)	−0.0003 (8)	0.0063 (8)	−0.0023 (7)

Cl1—C7	1.7432 (19)	C4—C5	1.471 (3)
S1—C2	1.7318 (19)	C5—C6	1.397 (3)
S1—C1	1.744 (2)	C5—C10	1.397 (3)
N1—C1	1.293 (3)	C6—C7	1.385 (3)
N1—N2	1.373 (2)	C6—H6	0.9300
N2—C2	1.361 (3)	C7—C8	1.386 (3)
N2—C3	1.371 (2)	C8—C9	1.386 (3)
N3—C2	1.309 (2)	C8—H8	0.9300
N3—C4	1.393 (2)	C9—C10	1.391 (3)
C1—H1	0.9300	C9—H9	0.9300
C3—C4	1.373 (3)	C10—H10	0.9300
C3—H3	0.9300
C2—S1—C1	87.81 (9)	C6—C5—C10	119.54 (18)
C1—N1—N2	107.27 (17)	C6—C5—C4	119.66 (17)
C2—N2—C3	107.63 (16)	C10—C5—C4	120.79 (18)
C2—N2—N1	118.68 (16)	C7—C6—C5	119.29 (17)
C3—N2—N1	133.69 (17)	C7—C6—H6	120.4
C2—N3—C4	103.49 (15)	C5—C6—H6	120.4
N1—C1—S1	117.63 (16)	C6—C7—C8	121.87 (18)
N1—C1—H1	121.2	C6—C7—Cl1	118.69 (15)
S1—C1—H1	121.2	C8—C7—Cl1	119.41 (16)
N3—C2—N2	112.95 (17)	C9—C8—C7	118.44 (19)
N3—C2—S1	138.46 (15)	C9—C8—H8	120.8
N2—C2—S1	108.59 (14)	C7—C8—H8	120.8
N2—C3—C4	104.29 (16)	C8—C9—C10	121.00 (19)
N2—C3—H3	127.9	C8—C9—H9	119.5
C4—C3—H3	127.9	C10—C9—H9	119.5
C3—C4—N3	111.64 (16)	C9—C10—C5	119.86 (18)
C3—C4—C5	126.96 (18)	C9—C10—H10	120.1
N3—C4—C5	121.37 (17)	C5—C10—H10	120.1
C1—N1—N2—C2	0.2 (2)	C2—N3—C4—C3	0.4 (2)
C1—N1—N2—C3	179.7 (2)	C2—N3—C4—C5	−177.68 (17)
N2—N1—C1—S1	0.3 (2)	C3—C4—C5—C6	−4.9 (3)
C2—S1—C1—N1	−0.45 (17)	N3—C4—C5—C6	172.90 (17)
C4—N3—C2—N2	−0.1 (2)	C3—C4—C5—C10	176.33 (19)
C4—N3—C2—S1	179.75 (18)	N3—C4—C5—C10	−5.9 (3)
C3—N2—C2—N3	−0.2 (2)	C10—C5—C6—C7	−0.1 (3)
N1—N2—C2—N3	179.44 (17)	C4—C5—C6—C7	−178.88 (17)
C3—N2—C2—S1	179.87 (13)	C5—C6—C7—C8	−0.4 (3)
N1—N2—C2—S1	−0.5 (2)	C5—C6—C7—Cl1	177.50 (14)
C1—S1—C2—N3	−179.4 (2)	C6—C7—C8—C9	0.5 (3)
C1—S1—C2—N2	0.47 (14)	Cl1—C7—C8—C9	−177.37 (15)
C2—N2—C3—C4	0.5 (2)	C7—C8—C9—C10	−0.1 (3)
N1—N2—C3—C4	−179.12 (19)	C8—C9—C10—C5	−0.4 (3)
N2—C3—C4—N3	−0.6 (2)	C6—C5—C10—C9	0.5 (3)
N2—C3—C4—C5	177.43 (17)	C4—C5—C10—C9	179.27 (18)