2-Isobutyl-6-phenyl-imidazo[2,1-b][1,3,4]thia-diazole.

In the title compound, C(14)H(15)N(3)S, the imidazo[2,1-b][1,3,4]thia-diazole fused-ring system is close to planar, with a maximum deviation of 0.042 (1) Å, and the dihedral angle between it and the phenyl ring is 24.21 (6)°. The isobutyl group is disordered over two sets of sites in a 0.899 (9):0.101 (9) ratio. In the crystal, weak aromatic π-π stacking inter-actions involving the imidazole and thia-diazole rings with a centroid-centroid distance of 3.8067 (7) Å occur.

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

C14H15N3S

M = 257.35

Monoclinic,

a = 5.6921 (1) Å

b = 19.6453 (4) Å

c = 12.3610 (2) Å

β = 96.127 (1)°

V = 1374.35 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.65 × 0.48 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.870, T max = 0.947

36499 measured reflections

4038 independent reflections

3378 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.03

4038 reflections

191 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 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/S1600536810053201/hb5776sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053201/hb5776Isup2.hkl

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

C14H15N3S	F(000) = 544
Mr = 257.35	Dx = 1.244 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9875 reflections
a = 5.6921 (1) Å	θ = 2.7–30.3°
b = 19.6453 (4) Å	µ = 0.22 mm−1
c = 12.3610 (2) Å	T = 296 K
β = 96.127 (1)°	Block, yellow
V = 1374.35 (4) Å3	0.65 × 0.48 × 0.25 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4038 independent reflections
Radiation source: fine-focus sealed tube	3378 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.870, Tmax = 0.947	k = −27→27
36499 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.2698P] where P = (Fo2 + 2Fc2)/3
4038 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.31 e Å−3
3 restraints	Δρmin = −0.30 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	Occ. (<1)
S1	−0.10652 (5)	0.001167 (15)	0.83286 (3)	0.04296 (11)
N1	−0.09710 (16)	0.12234 (5)	0.96090 (8)	0.0375 (2)
N2	0.23227 (16)	0.07221 (5)	0.91884 (8)	0.0369 (2)
N3	0.34801 (18)	0.02027 (5)	0.87202 (9)	0.0412 (2)
C1	−0.1245 (2)	0.25685 (7)	1.06391 (14)	0.0544 (3)
H1A	−0.2492	0.2450	1.0125	0.065*
C2	−0.1425 (3)	0.31387 (9)	1.12942 (17)	0.0724 (5)
H2A	−0.2792	0.3401	1.1213	0.087*
C3	0.0404 (3)	0.33173 (9)	1.20606 (16)	0.0731 (5)
H3A	0.0269	0.3697	1.2498	0.088*
C4	0.2424 (3)	0.29331 (9)	1.21764 (14)	0.0688 (4)
H4A	0.3664	0.3055	1.2691	0.083*
C5	0.2629 (3)	0.23646 (8)	1.15317 (12)	0.0540 (3)
H5A	0.4005	0.2106	1.1620	0.065*
C6	0.0797 (2)	0.21756 (6)	1.07525 (10)	0.0395 (2)
C7	0.10261 (19)	0.15721 (6)	1.00717 (9)	0.0361 (2)
C8	−0.00847 (18)	0.07150 (6)	0.90932 (9)	0.0346 (2)
C9	0.1913 (2)	−0.02035 (6)	0.82471 (10)	0.0387 (2)
C10	0.3078 (2)	0.12707 (6)	0.98180 (10)	0.0406 (3)
H10A	0.4625	0.1408	1.0026	0.049*
C11	0.2544 (2)	−0.08474 (6)	0.77025 (11)	0.0456 (3)
H11A	0.1916	−0.1229	0.8079	0.055*	0.899 (9)
H11B	0.4251	−0.0891	0.7778	0.055*	0.899 (9)
H11C	0.1818	−0.1211	0.8065	0.055*	0.101 (9)
H11D	0.4220	−0.0903	0.7866	0.055*	0.101 (9)
C12	0.1633 (7)	−0.08944 (18)	0.6491 (3)	0.0618 (9)	0.899 (9)
H12A	−0.0066	−0.0798	0.6399	0.074*	0.899 (9)
C13	0.2898 (12)	−0.03784 (19)	0.5858 (3)	0.1205 (16)	0.899 (9)
H13A	0.2567	0.0071	0.6105	0.181*	0.899 (9)
H13B	0.2362	−0.0418	0.5098	0.181*	0.899 (9)
H13C	0.4569	−0.0460	0.5970	0.181*	0.899 (9)
C14	0.2053 (8)	−0.16347 (16)	0.6126 (3)	0.0948 (11)	0.899 (9)
H14A	0.1100	−0.1940	0.6500	0.142*	0.899 (9)
H14B	0.3690	−0.1750	0.6295	0.142*	0.899 (9)
H14C	0.1629	−0.1673	0.5355	0.142*	0.899 (9)
C12A	0.205 (7)	−0.0960 (19)	0.666 (2)	0.081 (12)	0.101 (9)
H12B	0.0650	−0.1245	0.6708	0.097*	0.101 (9)
C13A	0.096 (9)	−0.0463 (17)	0.583 (3)	0.122 (14)	0.101 (9)
H13D	0.0313	−0.0705	0.5196	0.182*	0.101 (9)
H13E	0.2154	−0.0152	0.5641	0.182*	0.101 (9)
H13F	−0.0266	−0.0214	0.6131	0.182*	0.101 (9)
C14A	0.347 (8)	−0.147 (2)	0.601 (2)	0.119 (13)	0.101 (9)
H14D	0.2895	−0.1445	0.5251	0.179*	0.101 (9)
H14E	0.3267	−0.1923	0.6271	0.179*	0.101 (9)
H14F	0.5114	−0.1350	0.6105	0.179*	0.101 (9)

	U11	U22	U33	U12	U13	U23
S1	0.03290 (16)	0.04292 (18)	0.0523 (2)	0.00072 (10)	0.00121 (12)	−0.00946 (12)
N1	0.0321 (4)	0.0376 (5)	0.0430 (5)	0.0029 (4)	0.0052 (4)	−0.0013 (4)
N2	0.0301 (4)	0.0383 (5)	0.0433 (5)	0.0006 (3)	0.0085 (3)	−0.0043 (4)
N3	0.0344 (5)	0.0421 (5)	0.0484 (6)	0.0028 (4)	0.0112 (4)	−0.0066 (4)
C1	0.0432 (7)	0.0453 (7)	0.0753 (9)	0.0023 (5)	0.0096 (6)	−0.0114 (6)
C2	0.0595 (9)	0.0530 (8)	0.1081 (14)	0.0077 (7)	0.0254 (9)	−0.0217 (9)
C3	0.0771 (11)	0.0602 (9)	0.0865 (12)	−0.0070 (8)	0.0290 (9)	−0.0330 (9)
C4	0.0735 (11)	0.0698 (10)	0.0628 (9)	−0.0057 (8)	0.0062 (8)	−0.0265 (8)
C5	0.0543 (8)	0.0548 (8)	0.0522 (7)	0.0028 (6)	0.0029 (6)	−0.0118 (6)
C6	0.0416 (6)	0.0358 (5)	0.0426 (6)	−0.0016 (4)	0.0116 (5)	−0.0015 (4)
C7	0.0354 (5)	0.0351 (5)	0.0383 (5)	−0.0004 (4)	0.0068 (4)	0.0000 (4)
C8	0.0297 (5)	0.0364 (5)	0.0378 (5)	0.0012 (4)	0.0038 (4)	0.0004 (4)
C9	0.0371 (5)	0.0393 (5)	0.0403 (6)	0.0034 (4)	0.0077 (4)	−0.0009 (4)
C10	0.0328 (5)	0.0413 (6)	0.0482 (6)	−0.0040 (4)	0.0071 (4)	−0.0070 (5)
C11	0.0472 (6)	0.0403 (6)	0.0503 (7)	0.0036 (5)	0.0107 (5)	−0.0065 (5)
C12	0.0621 (18)	0.0715 (19)	0.0501 (12)	0.0138 (12)	−0.0009 (11)	−0.0205 (13)
C13	0.182 (5)	0.123 (3)	0.0616 (15)	−0.005 (3)	0.037 (2)	0.0168 (16)
C14	0.104 (2)	0.0893 (19)	0.0898 (18)	0.0083 (16)	0.0063 (16)	−0.0506 (15)
C12A	0.049 (13)	0.082 (17)	0.11 (3)	0.033 (11)	−0.001 (12)	0.044 (17)
C13A	0.15 (4)	0.12 (3)	0.088 (19)	−0.01 (2)	0.00 (2)	−0.037 (19)
C14A	0.15 (3)	0.14 (3)	0.070 (14)	−0.02 (2)	0.020 (18)	−0.055 (16)

S1—C8	1.7324 (11)	C11—C12	1.534 (3)
S1—C9	1.7605 (12)	C11—H11A	0.9700
N1—C8	1.3142 (14)	C11—H11B	0.9700
N1—C7	1.3963 (15)	C11—H11C	0.9600
N2—C8	1.3629 (14)	C11—H11D	0.9600
N2—C10	1.3714 (15)	C12—C13	1.509 (5)
N2—N3	1.3753 (13)	C12—C14	1.549 (4)
N3—C9	1.2895 (16)	C12—H12A	0.9800
C1—C6	1.3894 (18)	C13—H13A	0.9600
C1—C2	1.392 (2)	C13—H13B	0.9600
C1—H1A	0.9300	C13—H13C	0.9600
C2—C3	1.376 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.370 (3)	C14—H14C	0.9600
C3—H3A	0.9300	C12A—C13A	1.501 (18)
C4—C5	1.384 (2)	C12A—C14A	1.563 (18)
C4—H4A	0.9300	C12A—H12B	0.9800
C5—C6	1.3925 (19)	C13A—H13D	0.9600
C5—H5A	0.9300	C13A—H13E	0.9600
C6—C7	1.4678 (16)	C13A—H13F	0.9600
C7—C10	1.3753 (15)	C14A—H14D	0.9600
C9—C11	1.4946 (16)	C14A—H14E	0.9600
C10—H10A	0.9300	C14A—H14F	0.9600
C11—C12A	1.30 (3)
C8—S1—C9	88.09 (5)	C12A—C11—H11C	106.0
C8—N1—C7	103.51 (9)	C9—C11—H11C	106.5
C8—N2—C10	107.97 (9)	C12—C11—H11C	107.0
C8—N2—N3	118.59 (9)	H11B—C11—H11C	111.4
C10—N2—N3	133.36 (10)	C12A—C11—H11D	107.0
C9—N3—N2	108.10 (9)	C9—C11—H11D	106.5
C6—C1—C2	120.06 (15)	C12—C11—H11D	115.0
C6—C1—H1A	120.0	H11A—C11—H11D	102.7
C2—C1—H1A	120.0	H11C—C11—H11D	106.5
C3—C2—C1	120.55 (16)	C13—C12—C11	109.6 (3)
C3—C2—H2A	119.7	C13—C12—C14	112.5 (3)
C1—C2—H2A	119.7	C11—C12—C14	107.1 (3)
C4—C3—C2	119.75 (15)	C13—C12—H12A	109.2
C4—C3—H3A	120.1	C11—C12—H12A	109.2
C2—C3—H3A	120.1	C14—C12—H12A	109.2
C3—C4—C5	120.38 (16)	C12—C13—H13A	109.5
C3—C4—H4A	119.8	C12—C13—H13B	109.5
C5—C4—H4A	119.8	H13A—C13—H13B	109.5
C4—C5—C6	120.69 (14)	C12—C13—H13C	109.5
C4—C5—H5A	119.7	H13A—C13—H13C	109.5
C6—C5—H5A	119.7	H13B—C13—H13C	109.5
C1—C6—C5	118.57 (12)	C12—C14—H14A	109.5
C1—C6—C7	121.03 (12)	C12—C14—H14B	109.5
C5—C6—C7	120.40 (11)	H14A—C14—H14B	109.5
C10—C7—N1	111.69 (10)	C12—C14—H14C	109.5
C10—C7—C6	127.46 (11)	H14A—C14—H14C	109.5
N1—C7—C6	120.84 (10)	H14B—C14—H14C	109.5
N1—C8—N2	112.63 (10)	C11—C12A—C13A	126 (2)
N1—C8—S1	138.83 (9)	C11—C12A—C14A	123 (2)
N2—C8—S1	108.52 (8)	C13A—C12A—C14A	105 (2)
N3—C9—C11	122.70 (11)	C11—C12A—H12B	97.6
N3—C9—S1	116.69 (9)	C13A—C12A—H12B	97.6
C11—C9—S1	120.53 (9)	C14A—C12A—H12B	97.6
N2—C10—C7	104.19 (10)	C12A—C13A—H13D	109.5
N2—C10—H10A	127.9	C12A—C13A—H13E	109.5
C7—C10—H10A	127.9	H13D—C13A—H13E	109.5
C12A—C11—C9	123.4 (13)	C12A—C13A—H13F	109.5
C9—C11—C12	114.71 (15)	H13D—C13A—H13F	109.5
C12A—C11—H11A	106.9	H13E—C13A—H13F	109.5
C9—C11—H11A	108.6	C12A—C14A—H14D	109.5
C12—C11—H11A	108.6	C12A—C14A—H14E	109.5
C12A—C11—H11B	100.8	H14D—C14A—H14E	109.5
C9—C11—H11B	108.6	C12A—C14A—H14F	109.5
C12—C11—H11B	108.6	H14D—C14A—H14F	109.5
H11A—C11—H11B	107.6	H14E—C14A—H14F	109.5
C8—N2—N3—C9	0.80 (15)	C9—S1—C8—N1	−177.43 (13)
C10—N2—N3—C9	177.01 (12)	C9—S1—C8—N2	1.10 (9)
C6—C1—C2—C3	−0.3 (3)	N2—N3—C9—C11	−176.63 (11)
C1—C2—C3—C4	0.3 (3)	N2—N3—C9—S1	0.17 (13)
C2—C3—C4—C5	−0.4 (3)	C8—S1—C9—N3	−0.77 (10)
C3—C4—C5—C6	0.3 (3)	C8—S1—C9—C11	176.10 (10)
C2—C1—C6—C5	0.2 (2)	C8—N2—C10—C7	−0.12 (13)
C2—C1—C6—C7	179.96 (14)	N3—N2—C10—C7	−176.62 (12)
C4—C5—C6—C1	−0.2 (2)	N1—C7—C10—N2	−0.26 (13)
C4—C5—C6—C7	−179.99 (13)	C6—C7—C10—N2	178.61 (11)
C8—N1—C7—C10	0.54 (13)	N3—C9—C11—C12A	−117 (2)
C8—N1—C7—C6	−178.42 (10)	S1—C9—C11—C12A	66 (2)
C1—C6—C7—C10	156.55 (13)	N3—C9—C11—C12	−121.5 (2)
C5—C6—C7—C10	−23.69 (19)	S1—C9—C11—C12	61.8 (2)
C1—C6—C7—N1	−24.67 (17)	C12A—C11—C12—C13	−89 (14)
C5—C6—C7—N1	155.09 (12)	C9—C11—C12—C13	67.7 (4)
C7—N1—C8—N2	−0.62 (13)	C12A—C11—C12—C14	33 (13)
C7—N1—C8—S1	177.88 (11)	C9—C11—C12—C14	−170.0 (2)
C10—N2—C8—N1	0.49 (13)	C9—C11—C12A—C13A	5(6)
N3—N2—C8—N1	177.59 (10)	C12—C11—C12A—C13A	30 (10)
C10—N2—C8—S1	−178.47 (8)	C9—C11—C12A—C14A	155 (3)
N3—N2—C8—S1	−1.36 (13)