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

In the title compound, C(15)H(17)N(3)OS, the dihedral angle between the statistically planar imidazo[2,1-b][1,3,4]thia-dia-zole fused-ring system (r.m.s. deviation = 0.002 Å) and the methyoxbenzene ring is 4.52 (6)°. In the crystal, mol-ecules are arranged into columns and stacked down the a axis. The crystal structure is stabilized by weak C-H⋯π and π-π inter-actions [centroid-centroid separations = 3.6053 (8) and 3.7088 (7) Å].

Related literature

For a related structure and background references to imidazo[2,1-b]-1,3,4-thia­diazole derivatives, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C15H17N3OS

M = 287.38

Triclinic,

a = 5.7139 (1) Å

b = 10.1795 (1) Å

c = 12.9689 (2) Å

α = 85.174 (1)°

β = 85.164 (1)°

γ = 80.690 (1)°

V = 739.84 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.43 × 0.31 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.911, T max = 0.964

23503 measured reflections

6213 independent reflections

3805 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.163

S = 1.03

6213 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 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/S1600536810053225/hb5778sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053225/hb5778Isup2.hkl

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

C15H17N3OS	Z = 2
Mr = 287.38	F(000) = 304
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7139 (1) Å	Cell parameters from 6150 reflections
b = 10.1795 (1) Å	θ = 2.5–30.1°
c = 12.9689 (2) Å	µ = 0.22 mm−1
α = 85.174 (1)°	T = 296 K
β = 85.164 (1)°	Block, colourless
γ = 80.690 (1)°	0.43 × 0.31 × 0.17 mm
V = 739.84 (2) Å3

Bruker SMART APEXII CCD diffractometer	6213 independent reflections
Radiation source: fine-focus sealed tube	3805 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 34.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.911, Tmax = 0.964	k = −16→16
23503 measured reflections	l = −20→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0765P)2 + 0.0748P] where P = (Fo2 + 2Fc2)/3
6213 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
S1	1.14439 (6)	1.02701 (4)	0.26563 (3)	0.05911 (14)
O1	1.1085 (2)	0.33486 (12)	0.78317 (9)	0.0741 (3)
N1	0.7031 (2)	1.05243 (12)	0.33719 (9)	0.0523 (3)
N2	0.82991 (18)	0.94641 (11)	0.39100 (8)	0.0448 (2)
N3	1.16801 (18)	0.81311 (11)	0.42311 (8)	0.0470 (2)
C1	1.2380 (2)	0.58244 (13)	0.57132 (10)	0.0459 (3)
H1A	1.3637	0.6030	0.5258	0.055*
C2	1.2769 (3)	0.47212 (13)	0.64264 (10)	0.0498 (3)
H2A	1.4261	0.4199	0.6442	0.060*
C3	1.0917 (3)	0.44125 (14)	0.71078 (10)	0.0515 (3)
C4	0.8704 (3)	0.52078 (17)	0.70788 (12)	0.0620 (4)
H4A	0.7456	0.5008	0.7542	0.074*
C5	0.8345 (2)	0.62946 (16)	0.63658 (12)	0.0541 (3)
H5A	0.6852	0.6817	0.6354	0.065*
C6	1.0186 (2)	0.66223 (12)	0.56621 (9)	0.0405 (2)
C7	0.9808 (2)	0.77580 (12)	0.48936 (9)	0.0397 (2)
C8	0.7710 (2)	0.85747 (13)	0.47028 (10)	0.0497 (3)
H8A	0.6217	0.8533	0.5038	0.060*
C9	0.8461 (2)	1.10357 (13)	0.26920 (10)	0.0473 (3)
C10	1.0665 (2)	0.91576 (13)	0.36590 (9)	0.0441 (3)
C11	0.7678 (3)	1.22647 (14)	0.20133 (11)	0.0571 (4)
H11A	0.8370	1.2992	0.2240	0.069*
H11B	0.5965	1.2493	0.2123	0.069*
C12	0.8305 (3)	1.21810 (16)	0.08633 (11)	0.0642 (4)
H12A	1.0026	1.1905	0.0754	0.077*
C13	0.7083 (6)	1.1178 (2)	0.04179 (17)	0.1097 (9)
H13A	0.7482	1.0322	0.0783	0.165*
H13B	0.7594	1.1119	−0.0303	0.165*
H13C	0.5393	1.1455	0.0489	0.165*
C14	0.7663 (6)	1.3557 (2)	0.03141 (17)	0.1117 (9)
H14A	0.8461	1.4183	0.0607	0.167*
H14B	0.5975	1.3836	0.0400	0.167*
H14C	0.8148	1.3522	−0.0411	0.167*
C15	1.3354 (4)	0.25718 (19)	0.79377 (16)	0.0840 (6)
H15A	1.3233	0.1863	0.8467	0.126*
H15B	1.4436	0.3125	0.8127	0.126*
H15C	1.3931	0.2200	0.7291	0.126*

	U11	U22	U33	U12	U13	U23
S1	0.04595 (19)	0.0694 (3)	0.0549 (2)	−0.00092 (16)	0.00022 (14)	0.01745 (17)
O1	0.0866 (8)	0.0673 (7)	0.0650 (7)	−0.0162 (6)	−0.0051 (6)	0.0229 (5)
N1	0.0439 (6)	0.0567 (7)	0.0504 (6)	0.0074 (5)	−0.0069 (5)	0.0047 (5)
N2	0.0364 (5)	0.0504 (6)	0.0438 (5)	0.0022 (4)	−0.0044 (4)	0.0022 (4)
N3	0.0361 (5)	0.0551 (6)	0.0462 (6)	−0.0009 (4)	−0.0031 (4)	0.0060 (4)
C1	0.0453 (6)	0.0489 (7)	0.0394 (6)	0.0004 (5)	0.0018 (5)	0.0001 (5)
C2	0.0532 (7)	0.0483 (7)	0.0440 (6)	0.0019 (5)	−0.0021 (5)	−0.0004 (5)
C3	0.0644 (8)	0.0468 (7)	0.0441 (6)	−0.0126 (6)	−0.0077 (6)	0.0034 (5)
C4	0.0531 (8)	0.0731 (10)	0.0584 (8)	−0.0177 (7)	0.0027 (6)	0.0119 (7)
C5	0.0394 (6)	0.0654 (8)	0.0546 (7)	−0.0063 (6)	0.0001 (5)	0.0060 (6)
C6	0.0395 (6)	0.0448 (6)	0.0374 (5)	−0.0054 (5)	−0.0040 (4)	−0.0050 (4)
C7	0.0372 (5)	0.0445 (6)	0.0365 (5)	−0.0023 (4)	−0.0035 (4)	−0.0050 (4)
C8	0.0375 (6)	0.0565 (8)	0.0505 (7)	−0.0008 (5)	0.0019 (5)	0.0051 (6)
C9	0.0514 (7)	0.0489 (7)	0.0394 (6)	0.0027 (5)	−0.0096 (5)	−0.0042 (5)
C10	0.0364 (6)	0.0528 (7)	0.0409 (6)	−0.0022 (5)	−0.0038 (4)	0.0010 (5)
C11	0.0711 (9)	0.0495 (7)	0.0465 (7)	0.0050 (6)	−0.0117 (6)	0.0006 (5)
C12	0.0702 (10)	0.0673 (9)	0.0486 (8)	0.0017 (8)	−0.0023 (7)	0.0078 (7)
C13	0.175 (3)	0.0923 (15)	0.0672 (12)	−0.0145 (17)	−0.0461 (15)	−0.0119 (11)
C14	0.164 (3)	0.0872 (14)	0.0717 (13)	−0.0059 (16)	−0.0039 (14)	0.0319 (11)
C15	0.1056 (16)	0.0615 (10)	0.0816 (12)	−0.0074 (10)	−0.0270 (11)	0.0232 (9)

S1—C10	1.7290 (13)	C6—C7	1.4622 (16)
S1—C9	1.7545 (14)	C7—C8	1.3722 (17)
O1—C3	1.3690 (16)	C8—H8A	0.9300
O1—C15	1.416 (2)	C9—C11	1.4966 (18)
N1—C9	1.2864 (19)	C11—C12	1.510 (2)
N1—N2	1.3721 (14)	C11—H11A	0.9700
N2—C10	1.3554 (16)	C11—H11B	0.9700
N2—C8	1.3689 (16)	C12—C13	1.503 (3)
N3—C10	1.3133 (15)	C12—C14	1.521 (2)
N3—C7	1.3957 (16)	C12—H12A	0.9800
C1—C6	1.3825 (17)	C13—H13A	0.9600
C1—C2	1.3947 (17)	C13—H13B	0.9600
C1—H1A	0.9300	C13—H13C	0.9600
C2—C3	1.379 (2)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.388 (2)	C14—H14C	0.9600
C4—C5	1.381 (2)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.3967 (18)	C15—H15C	0.9600
C5—H5A	0.9300
C10—S1—C9	88.40 (6)	N3—C10—N2	112.76 (11)
C3—O1—C15	117.66 (14)	N3—C10—S1	138.85 (10)
C9—N1—N2	108.55 (11)	N2—C10—S1	108.39 (9)
C10—N2—C8	107.69 (10)	C9—C11—C12	116.36 (12)
C10—N2—N1	118.51 (11)	C9—C11—H11A	108.2
C8—N2—N1	133.79 (11)	C12—C11—H11A	108.2
C10—N3—C7	103.73 (10)	C9—C11—H11B	108.2
C6—C1—C2	122.09 (12)	C12—C11—H11B	108.2
C6—C1—H1A	119.0	H11A—C11—H11B	107.4
C2—C1—H1A	119.0	C13—C12—C11	112.03 (16)
C3—C2—C1	119.33 (13)	C13—C12—C14	110.67 (17)
C3—C2—H2A	120.3	C11—C12—C14	109.10 (15)
C1—C2—H2A	120.3	C13—C12—H12A	108.3
O1—C3—C2	124.39 (14)	C11—C12—H12A	108.3
O1—C3—C4	115.99 (14)	C14—C12—H12A	108.3
C2—C3—C4	119.62 (13)	C12—C13—H13A	109.5
C5—C4—C3	120.36 (14)	C12—C13—H13B	109.5
C5—C4—H4A	119.8	H13A—C13—H13B	109.5
C3—C4—H4A	119.8	C12—C13—H13C	109.5
C4—C5—C6	121.14 (14)	H13A—C13—H13C	109.5
C4—C5—H5A	119.4	H13B—C13—H13C	109.5
C6—C5—H5A	119.4	C12—C14—H14A	109.5
C1—C6—C5	117.46 (12)	C12—C14—H14B	109.5
C1—C6—C7	121.12 (11)	H14A—C14—H14B	109.5
C5—C6—C7	121.42 (11)	C12—C14—H14C	109.5
C8—C7—N3	111.03 (11)	H14A—C14—H14C	109.5
C8—C7—C6	127.62 (11)	H14B—C14—H14C	109.5
N3—C7—C6	121.35 (10)	O1—C15—H15A	109.5
N2—C8—C7	104.79 (11)	O1—C15—H15B	109.5
N2—C8—H8A	127.6	H15A—C15—H15B	109.5
C7—C8—H8A	127.6	O1—C15—H15C	109.5
N1—C9—C11	122.38 (13)	H15A—C15—H15C	109.5
N1—C9—S1	116.15 (10)	H15B—C15—H15C	109.5
C11—C9—S1	121.36 (11)
C9—N1—N2—C10	0.23 (17)	C10—N2—C8—C7	0.06 (15)
C9—N1—N2—C8	179.94 (14)	N1—N2—C8—C7	−179.67 (13)
C6—C1—C2—C3	−0.3 (2)	N3—C7—C8—N2	0.03 (15)
C15—O1—C3—C2	4.8 (2)	C6—C7—C8—N2	−179.34 (11)
C15—O1—C3—C4	−175.43 (15)	N2—N1—C9—C11	−176.23 (11)
C1—C2—C3—O1	179.30 (13)	N2—N1—C9—S1	−0.04 (15)
C1—C2—C3—C4	−0.4 (2)	C10—S1—C9—N1	−0.10 (12)
O1—C3—C4—C5	−179.11 (14)	C10—S1—C9—C11	176.13 (11)
C2—C3—C4—C5	0.7 (2)	C7—N3—C10—N2	0.14 (15)
C3—C4—C5—C6	−0.2 (2)	C7—N3—C10—S1	−179.92 (13)
C2—C1—C6—C5	0.7 (2)	C8—N2—C10—N3	−0.13 (16)
C2—C1—C6—C7	−178.73 (12)	N1—N2—C10—N3	179.65 (11)
C4—C5—C6—C1	−0.5 (2)	C8—N2—C10—S1	179.92 (9)
C4—C5—C6—C7	178.95 (13)	N1—N2—C10—S1	−0.31 (15)
C10—N3—C7—C8	−0.10 (14)	C9—S1—C10—N3	−179.73 (16)
C10—N3—C7—C6	179.31 (11)	C9—S1—C10—N2	0.21 (10)
C1—C6—C7—C8	175.00 (13)	N1—C9—C11—C12	−129.32 (16)
C5—C6—C7—C8	−4.5 (2)	S1—C9—C11—C12	54.69 (18)
C1—C6—C7—N3	−4.31 (18)	C9—C11—C12—C13	64.3 (2)
C5—C6—C7—N3	176.24 (12)	C9—C11—C12—C14	−172.81 (17)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cg3i	0.97	2.60	3.5063 (16)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg3i	0.97	2.60	3.5063 (16)	155

Symmetry code: (i) .