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

In the title compound, C(14)H(14)ClN(3)S, the imidazo[2,1-b][1,3,4]thia-diazole system is essentially planar, with a maximum deviation of 0.006 (2) Å. The dihedral angle between the imidazo[2,1-b][1,3,4]thia-diazole and chloro-phenyl rings is 5.07 (8)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak π-π [centroid-centroid distance = 3.5697 (11) Å] and C-H⋯π inter-actions.

Related literature

For applications of imidazo [2,1-b]-1,3,4-thia­diazole derivatives, see: Terzioglu & Gursoy (2003 ▶); Kolavi et al. (2006 ▶); Gadad et al. (2000 ▶); Andotra et al. (1997 ▶); Khazi et al. (1996 ▶); Andreani et al. (1982 ▶,1987 ▶,1991 ▶); Eberle & Robert (1977 ▶).

Experimental

Crystal data

C14H14ClN3S

M = 291.79

Monoclinic,

a = 5.7552 (1) Å

b = 26.4052 (5) Å

c = 9.7662 (2) Å

β = 101.388 (1)°

V = 1454.92 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 296 K

0.47 × 0.31 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.835, T max = 0.897

12320 measured reflections

3353 independent reflections

2646 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.135

S = 1.05

3353 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.32 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 datablocks global, I. DOI: 10.1107/S1600536810052621/ng5089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052621/ng5089Isup2.hkl

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

C14H14ClN3S	F(000) = 608
Mr = 291.79	Dx = 1.332 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5357 reflections
a = 5.7552 (1) Å	θ = 2.3–28.5°
b = 26.4052 (5) Å	µ = 0.40 mm−1
c = 9.7662 (2) Å	T = 296 K
β = 101.388 (1)°	Block, colourless
V = 1454.92 (5) Å3	0.47 × 0.31 × 0.28 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3353 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→7
Tmin = 0.835, Tmax = 0.897	k = −23→34
12320 measured reflections	l = −12→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.4615P] where P = (Fo2 + 2Fc2)/3
3353 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
Cl1	0.79047 (16)	−0.15309 (3)	0.31411 (7)	0.0936 (3)
S1	0.87829 (9)	0.11339 (2)	0.99277 (7)	0.0661 (2)
N1	0.8370 (3)	0.03334 (6)	0.79472 (18)	0.0536 (4)
N2	1.1813 (3)	0.05331 (6)	0.93125 (17)	0.0517 (4)
N3	1.3144 (3)	0.08204 (7)	1.03504 (19)	0.0609 (5)
C1	0.7404 (4)	−0.04026 (8)	0.5763 (2)	0.0544 (5)
H1A	0.6230	−0.0182	0.5931	0.065*
C2	0.6859 (4)	−0.07545 (8)	0.4702 (2)	0.0610 (5)
H2A	0.5347	−0.0767	0.4147	0.073*
C3	0.8587 (4)	−0.10854 (8)	0.4479 (2)	0.0617 (5)
C4	1.0837 (4)	−0.10677 (9)	0.5281 (3)	0.0686 (6)
H4A	1.1991	−0.1294	0.5116	0.082*
C5	1.1370 (4)	−0.07123 (8)	0.6331 (2)	0.0613 (5)
H5A	1.2889	−0.0701	0.6877	0.074*
C6	0.9657 (3)	−0.03694 (7)	0.65853 (19)	0.0471 (4)
C7	1.0177 (3)	0.00199 (7)	0.76767 (19)	0.0468 (4)
C8	0.9462 (3)	0.06335 (7)	0.8937 (2)	0.0507 (4)
C9	1.1782 (4)	0.11490 (8)	1.0758 (2)	0.0578 (5)
C10	1.2301 (3)	0.01388 (8)	0.8507 (2)	0.0544 (5)
H10A	1.3760	−0.0015	0.8522	0.065*
C11	1.2613 (5)	0.15173 (9)	1.1910 (2)	0.0731 (6)
H11A	1.4291	0.1461	1.2261	0.088*
H11B	1.1795	0.1445	1.2666	0.088*
C12	1.2254 (5)	0.20690 (10)	1.1527 (3)	0.0813 (7)
H12A	1.0588	0.2118	1.1082	0.098*
C13	1.2777 (9)	0.23946 (14)	1.2842 (4)	0.1384 (16)
H13A	1.1748	0.2297	1.3459	0.208*
H13B	1.2516	0.2745	1.2591	0.208*
H13C	1.4397	0.2347	1.3303	0.208*
C14	1.3764 (8)	0.22228 (13)	1.0505 (4)	0.1297 (15)
H14A	1.3400	0.2011	0.9691	0.195*
H14B	1.5407	0.2185	1.0930	0.195*
H14C	1.3448	0.2570	1.0240	0.195*

	U11	U22	U33	U12	U13	U23
Cl1	0.1320 (7)	0.0746 (4)	0.0756 (4)	0.0014 (4)	0.0239 (4)	−0.0144 (3)
S1	0.0529 (3)	0.0606 (3)	0.0842 (4)	0.0008 (2)	0.0124 (3)	−0.0096 (3)
N1	0.0371 (8)	0.0555 (10)	0.0668 (10)	0.0018 (7)	0.0068 (7)	0.0014 (8)
N2	0.0405 (8)	0.0511 (9)	0.0604 (9)	−0.0010 (7)	0.0024 (7)	0.0085 (7)
N3	0.0512 (9)	0.0583 (10)	0.0671 (11)	−0.0053 (8)	−0.0031 (8)	0.0042 (8)
C1	0.0496 (10)	0.0545 (11)	0.0571 (11)	0.0090 (8)	0.0055 (8)	0.0064 (9)
C2	0.0614 (12)	0.0627 (13)	0.0556 (11)	0.0045 (10)	0.0034 (9)	0.0072 (10)
C3	0.0819 (15)	0.0540 (12)	0.0523 (11)	0.0005 (10)	0.0207 (10)	0.0066 (9)
C4	0.0682 (14)	0.0641 (14)	0.0796 (15)	0.0138 (11)	0.0292 (12)	0.0028 (11)
C5	0.0460 (10)	0.0638 (13)	0.0753 (14)	0.0076 (9)	0.0149 (10)	0.0042 (11)
C6	0.0441 (9)	0.0481 (10)	0.0503 (10)	0.0030 (7)	0.0122 (7)	0.0138 (8)
C7	0.0386 (9)	0.0475 (10)	0.0541 (10)	0.0027 (7)	0.0088 (7)	0.0129 (8)
C8	0.0392 (9)	0.0492 (10)	0.0637 (11)	−0.0002 (8)	0.0103 (8)	0.0074 (9)
C9	0.0599 (11)	0.0516 (11)	0.0594 (12)	−0.0095 (9)	0.0055 (9)	0.0108 (9)
C10	0.0398 (9)	0.0570 (11)	0.0650 (12)	0.0078 (8)	0.0069 (8)	0.0076 (9)
C11	0.0872 (17)	0.0662 (14)	0.0625 (13)	−0.0168 (12)	0.0068 (12)	0.0047 (11)
C12	0.0844 (17)	0.0661 (15)	0.0928 (18)	−0.0077 (13)	0.0157 (14)	−0.0147 (13)
C13	0.193 (4)	0.103 (3)	0.133 (3)	−0.032 (3)	0.066 (3)	−0.052 (2)
C14	0.208 (4)	0.088 (2)	0.104 (2)	−0.059 (2)	0.055 (3)	−0.0064 (18)

Cl1—C3	1.744 (2)	C5—H5A	0.9300
S1—C8	1.727 (2)	C6—C7	1.468 (3)
S1—C9	1.757 (2)	C7—C10	1.363 (3)
N1—C8	1.311 (3)	C9—C11	1.492 (3)
N1—C7	1.395 (2)	C10—H10A	0.9300
N2—C8	1.356 (2)	C11—C12	1.508 (3)
N2—C10	1.367 (3)	C11—H11A	0.9700
N2—N3	1.372 (2)	C11—H11B	0.9700
N3—C9	1.284 (3)	C12—C14	1.503 (4)
C1—C2	1.381 (3)	C12—C13	1.525 (4)
C1—C6	1.387 (3)	C12—H12A	0.9800
C1—H1A	0.9300	C13—H13A	0.9600
C2—C3	1.373 (3)	C13—H13B	0.9600
C2—H2A	0.9300	C13—H13C	0.9600
C3—C4	1.376 (3)	C14—H14A	0.9600
C4—C5	1.379 (3)	C14—H14B	0.9600
C4—H4A	0.9300	C14—H14C	0.9600
C5—C6	1.397 (3)
C8—S1—C9	88.02 (10)	N3—C9—C11	123.3 (2)
C8—N1—C7	103.40 (15)	N3—C9—S1	116.48 (16)
C8—N2—C10	107.48 (16)	C11—C9—S1	120.14 (18)
C8—N2—N3	118.26 (17)	C7—C10—N2	104.82 (16)
C10—N2—N3	134.26 (16)	C7—C10—H10A	127.6
C9—N3—N2	108.46 (16)	N2—C10—H10A	127.6
C2—C1—C6	121.66 (19)	C9—C11—C12	115.8 (2)
C2—C1—H1A	119.2	C9—C11—H11A	108.3
C6—C1—H1A	119.2	C12—C11—H11A	108.3
C3—C2—C1	118.9 (2)	C9—C11—H11B	108.3
C3—C2—H2A	120.6	C12—C11—H11B	108.3
C1—C2—H2A	120.6	H11A—C11—H11B	107.4
C2—C3—C4	121.2 (2)	C14—C12—C11	110.9 (3)
C2—C3—Cl1	118.99 (18)	C14—C12—C13	111.3 (3)
C4—C3—Cl1	119.80 (18)	C11—C12—C13	110.0 (3)
C3—C4—C5	119.5 (2)	C14—C12—H12A	108.2
C3—C4—H4A	120.2	C11—C12—H12A	108.2
C5—C4—H4A	120.2	C13—C12—H12A	108.2
C4—C5—C6	120.8 (2)	C12—C13—H13A	109.5
C4—C5—H5A	119.6	C12—C13—H13B	109.5
C6—C5—H5A	119.6	H13A—C13—H13B	109.5
C1—C6—C5	117.93 (19)	C12—C13—H13C	109.5
C1—C6—C7	119.84 (17)	H13A—C13—H13C	109.5
C5—C6—C7	122.23 (17)	H13B—C13—H13C	109.5
C10—C7—N1	111.42 (17)	C12—C14—H14A	109.5
C10—C7—C6	128.53 (17)	C12—C14—H14B	109.5
N1—C7—C6	120.03 (15)	H14A—C14—H14B	109.5
N1—C8—N2	112.88 (17)	C12—C14—H14C	109.5
N1—C8—S1	138.34 (15)	H14A—C14—H14C	109.5
N2—C8—S1	108.78 (14)	H14B—C14—H14C	109.5
C8—N2—N3—C9	−0.8 (2)	C7—N1—C8—S1	179.56 (18)
C10—N2—N3—C9	179.7 (2)	C10—N2—C8—N1	0.2 (2)
C6—C1—C2—C3	1.3 (3)	N3—N2—C8—N1	−179.44 (16)
C1—C2—C3—C4	−0.7 (3)	C10—N2—C8—S1	−179.60 (13)
C1—C2—C3—Cl1	179.91 (16)	N3—N2—C8—S1	0.8 (2)
C2—C3—C4—C5	0.2 (3)	C9—S1—C8—N1	179.9 (2)
Cl1—C3—C4—C5	179.57 (17)	C9—S1—C8—N2	−0.42 (14)
C3—C4—C5—C6	−0.3 (3)	N2—N3—C9—C11	178.09 (18)
C2—C1—C6—C5	−1.4 (3)	N2—N3—C9—S1	0.4 (2)
C2—C1—C6—C7	178.29 (18)	C8—S1—C9—N3	−0.01 (17)
C4—C5—C6—C1	0.9 (3)	C8—S1—C9—C11	−177.76 (18)
C4—C5—C6—C7	−178.82 (19)	N1—C7—C10—N2	0.1 (2)
C8—N1—C7—C10	0.0 (2)	C6—C7—C10—N2	178.64 (17)
C8—N1—C7—C6	−178.69 (16)	C8—N2—C10—C7	−0.1 (2)
C1—C6—C7—C10	−174.21 (19)	N3—N2—C10—C7	179.36 (19)
C5—C6—C7—C10	5.5 (3)	N3—C9—C11—C12	122.0 (3)
C1—C6—C7—N1	4.2 (3)	S1—C9—C11—C12	−60.4 (3)
C5—C6—C7—N1	−176.07 (17)	C9—C11—C12—C14	−66.3 (3)
C7—N1—C8—N2	−0.1 (2)	C9—C11—C12—C13	170.2 (3)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg3i	0.97	2.70	3.544 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg3i	0.97	2.70	3.544 (2)	145

Symmetry code: (i) .