2-(2,4-Dichloro-phen-oxy-meth-yl)-5-(4-methyl-phen-yl)imidazo[2,1-b][1,3,4]thia-diazole.

In the title compound, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thia-diazo-lethia-diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro-benzene and tolyl rings reflects a twist about the O-C(benzene) bond; the Cm-O-Cb-Cb torsion angle = -168.5 (2)° (m = methyl-ene C and b is benzene C). Supra-molecular tapes along the b axis are found in the crystal structure which are mediated by π-π inter-actions occurring between centrosymmetrically related thia-diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].

Related literature

For background to the biological activity of imidazothia­dia­zo­les, see: Abdel-Wahab et al. (2011 ▶); Karki et al. (2011 ▶); Khazi et al. (2011 ▶). For the synthesis, see: Abdel-Wahab et al. (2011 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C18H13Cl2N3OS

M = 390.27

Triclinic,

a = 8.3015 (7) Å

b = 8.3053 (7) Å

c = 14.4374 (13) Å

α = 97.180 (7)°

β = 92.644 (7)°

γ = 118.996 (9)°

V = 857.25 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.856, T max = 1.000

8391 measured reflections

3932 independent reflections

2659 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.172

S = 0.98

3932 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300384X/hg5290sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300384X/hg5290Isup2.hkl

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

C18H13Cl2N3OS	Z = 2
Mr = 390.27	F(000) = 400
Triclinic, P1	Dx = 1.512 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3015 (7) Å	Cell parameters from 1915 reflections
b = 8.3053 (7) Å	θ = 2.8–27.5°
c = 14.4374 (13) Å	µ = 0.51 mm−1
α = 97.180 (7)°	T = 295 K
β = 92.644 (7)°	Prism, colourless
γ = 118.996 (9)°	0.40 × 0.30 × 0.20 mm
V = 857.25 (13) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3932 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2659 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.028
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.8°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
Tmin = 0.856, Tmax = 1.000	l = −18→15
8391 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3932 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 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
Cl1	0.83905 (10)	0.40968 (12)	0.15939 (6)	0.0701 (3)
Cl2	0.16453 (12)	0.30193 (13)	0.04111 (6)	0.0730 (3)
S1	1.00105 (10)	0.30491 (9)	0.41463 (5)	0.0493 (2)
O1	0.6883 (3)	0.3049 (3)	0.32904 (14)	0.0540 (5)
C1	0.5593 (3)	0.3020 (3)	0.26664 (19)	0.0429 (6)
C2	0.6151 (4)	0.3510 (3)	0.1799 (2)	0.0462 (6)
C3	0.4962 (4)	0.3525 (3)	0.1110 (2)	0.0494 (6)
H3	0.5354	0.3847	0.0534	0.059*
C4	0.3174 (4)	0.3053 (3)	0.12837 (19)	0.0476 (6)
C5	0.2607 (4)	0.2588 (4)	0.2137 (2)	0.0522 (7)
H5	0.1408	0.2286	0.2252	0.063*
C6	0.3797 (4)	0.2565 (4)	0.2827 (2)	0.0497 (6)
H6	0.3396	0.2244	0.3402	0.060*
C7	0.6268 (4)	0.2235 (4)	0.40983 (19)	0.0492 (6)
H7A	0.5252	0.0964	0.3920	0.059*
H7B	0.5844	0.2946	0.4497	0.059*
C8	0.7883 (4)	0.2255 (3)	0.46024 (18)	0.0431 (6)
C9	1.0864 (4)	0.2605 (3)	0.51522 (18)	0.0444 (6)
C10	1.0183 (4)	0.1610 (4)	0.6497 (2)	0.0506 (6)
H10	0.9573	0.1154	0.7009	0.061*
C11	1.1978 (4)	0.2117 (3)	0.63753 (18)	0.0444 (6)
C12	1.3346 (4)	0.2063 (3)	0.70303 (19)	0.0455 (6)
C13	1.5166 (4)	0.2710 (4)	0.6864 (2)	0.0538 (7)
H13	1.5549	0.3204	0.6319	0.065*
C14	1.6426 (4)	0.2638 (4)	0.7489 (2)	0.0584 (7)
H14	1.7644	0.3099	0.7358	0.070*
C15	1.5936 (4)	0.1901 (4)	0.8307 (2)	0.0541 (7)
C16	1.4112 (5)	0.1263 (4)	0.8480 (2)	0.0650 (8)
H16	1.3732	0.0769	0.9025	0.078*
C17	1.2846 (4)	0.1347 (4)	0.7856 (2)	0.0607 (8)
H17	1.1635	0.0915	0.7993	0.073*
C18	1.7309 (5)	0.1820 (4)	0.8983 (2)	0.0712 (9)
H18A	1.8126	0.1532	0.8640	0.107*
H18B	1.6661	0.0869	0.9355	0.107*
H18C	1.8019	0.3006	0.9389	0.107*
N1	0.7783 (3)	0.1707 (3)	0.54018 (17)	0.0506 (5)
N2	0.9469 (3)	0.1916 (3)	0.57041 (15)	0.0448 (5)
N3	1.2402 (3)	0.2741 (3)	0.55163 (15)	0.0483 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0431 (4)	0.1083 (6)	0.0602 (5)	0.0340 (4)	0.0157 (4)	0.0301 (4)
Cl2	0.0630 (5)	0.1060 (6)	0.0645 (5)	0.0519 (5)	−0.0016 (4)	0.0230 (5)
S1	0.0468 (4)	0.0648 (4)	0.0379 (4)	0.0278 (3)	0.0067 (3)	0.0129 (3)
O1	0.0417 (10)	0.0749 (11)	0.0495 (12)	0.0280 (9)	0.0083 (9)	0.0273 (9)
C1	0.0371 (13)	0.0467 (12)	0.0439 (15)	0.0189 (11)	0.0054 (11)	0.0120 (11)
C2	0.0374 (14)	0.0519 (13)	0.0486 (16)	0.0202 (12)	0.0068 (12)	0.0136 (12)
C3	0.0496 (16)	0.0583 (15)	0.0438 (16)	0.0277 (14)	0.0094 (13)	0.0153 (12)
C4	0.0454 (15)	0.0534 (13)	0.0480 (16)	0.0273 (12)	0.0015 (12)	0.0108 (12)
C5	0.0411 (15)	0.0637 (15)	0.0578 (18)	0.0289 (13)	0.0095 (14)	0.0165 (14)
C6	0.0447 (15)	0.0623 (15)	0.0467 (16)	0.0275 (13)	0.0112 (13)	0.0174 (13)
C7	0.0462 (15)	0.0559 (14)	0.0464 (16)	0.0244 (13)	0.0061 (13)	0.0155 (12)
C8	0.0450 (14)	0.0421 (12)	0.0401 (15)	0.0201 (11)	0.0035 (12)	0.0070 (11)
C9	0.0441 (14)	0.0473 (13)	0.0389 (15)	0.0212 (12)	0.0047 (12)	0.0047 (11)
C10	0.0479 (16)	0.0593 (14)	0.0470 (16)	0.0263 (13)	0.0054 (13)	0.0188 (13)
C11	0.0471 (15)	0.0400 (12)	0.0432 (15)	0.0208 (11)	−0.0017 (12)	0.0039 (11)
C12	0.0445 (15)	0.0424 (12)	0.0434 (15)	0.0193 (12)	−0.0055 (12)	−0.0001 (11)
C13	0.0531 (17)	0.0679 (16)	0.0442 (16)	0.0328 (14)	0.0044 (13)	0.0102 (13)
C14	0.0512 (17)	0.0751 (18)	0.0528 (18)	0.0372 (15)	−0.0016 (14)	0.0013 (15)
C15	0.0609 (19)	0.0463 (14)	0.0535 (18)	0.0282 (14)	−0.0088 (14)	0.0016 (12)
C16	0.066 (2)	0.0637 (17)	0.0558 (19)	0.0232 (16)	−0.0040 (16)	0.0218 (15)
C17	0.0493 (17)	0.0652 (17)	0.0586 (19)	0.0193 (14)	0.0005 (15)	0.0217 (15)
C18	0.072 (2)	0.0674 (17)	0.075 (2)	0.0387 (17)	−0.0184 (18)	0.0059 (17)
N1	0.0425 (13)	0.0618 (12)	0.0509 (14)	0.0255 (11)	0.0078 (11)	0.0217 (11)
N2	0.0397 (12)	0.0514 (11)	0.0443 (13)	0.0218 (10)	0.0059 (10)	0.0141 (10)
N3	0.0427 (12)	0.0599 (12)	0.0424 (13)	0.0252 (11)	0.0050 (10)	0.0107 (10)

Cl1—C2	1.729 (3)	C10—C11	1.365 (4)
Cl2—C4	1.734 (3)	C10—N2	1.373 (3)
S1—C9	1.743 (3)	C10—H10	0.9300
S1—C8	1.753 (3)	C11—N3	1.398 (3)
O1—C1	1.356 (3)	C11—C12	1.465 (4)
O1—C7	1.413 (3)	C12—C13	1.381 (4)
C1—C6	1.388 (4)	C12—C17	1.390 (4)
C1—C2	1.395 (4)	C13—C14	1.379 (4)
C2—C3	1.374 (4)	C13—H13	0.9300
C3—C4	1.384 (4)	C14—C15	1.384 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—C16	1.388 (4)
C5—C6	1.378 (4)	C15—C18	1.499 (4)
C5—H5	0.9300	C16—C17	1.386 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.487 (4)	C17—H17	0.9300
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—N1	1.284 (3)	C18—H18C	0.9600
C9—N3	1.305 (3)	N1—N2	1.367 (3)
C9—N2	1.364 (3)
C9—S1—C8	88.01 (12)	N2—C10—H10	127.3
C1—O1—C7	117.4 (2)	C10—C11—N3	110.8 (2)
O1—C1—C6	125.4 (2)	C10—C11—C12	126.9 (3)
O1—C1—C2	116.3 (2)	N3—C11—C12	122.2 (2)
C6—C1—C2	118.3 (3)	C13—C12—C17	117.1 (3)
C3—C2—C1	121.5 (2)	C13—C12—C11	122.4 (3)
C3—C2—Cl1	119.7 (2)	C17—C12—C11	120.5 (2)
C1—C2—Cl1	118.7 (2)	C14—C13—C12	121.3 (3)
C2—C3—C4	119.2 (3)	C14—C13—H13	119.3
C2—C3—H3	120.4	C12—C13—H13	119.3
C4—C3—H3	120.4	C13—C14—C15	122.0 (3)
C5—C4—C3	120.1 (3)	C13—C14—H14	119.0
C5—C4—Cl2	120.3 (2)	C15—C14—H14	119.0
C3—C4—Cl2	119.6 (2)	C14—C15—C16	116.8 (3)
C4—C5—C6	120.7 (2)	C14—C15—C18	121.9 (3)
C4—C5—H5	119.6	C16—C15—C18	121.3 (3)
C6—C5—H5	119.6	C17—C16—C15	121.2 (3)
C5—C6—C1	120.2 (3)	C17—C16—H16	119.4
C5—C6—H6	119.9	C15—C16—H16	119.4
C1—C6—H6	119.9	C16—C17—C12	121.5 (3)
O1—C7—C8	106.6 (2)	C16—C17—H17	119.3
O1—C7—H7A	110.4	C12—C17—H17	119.3
C8—C7—H7A	110.4	C15—C18—H18A	109.5
O1—C7—H7B	110.4	C15—C18—H18B	109.5
C8—C7—H7B	110.4	H18A—C18—H18B	109.5
H7A—C7—H7B	108.6	C15—C18—H18C	109.5
N1—C8—C7	121.1 (2)	H18A—C18—H18C	109.5
N1—C8—S1	116.9 (2)	H18B—C18—H18C	109.5
C7—C8—S1	121.93 (19)	C8—N1—N2	108.3 (2)
N3—C9—N2	113.1 (2)	C9—N2—N1	118.9 (2)
N3—C9—S1	139.0 (2)	C9—N2—C10	106.8 (2)
N2—C9—S1	107.86 (19)	N1—N2—C10	134.3 (2)
C11—C10—N2	105.4 (2)	C9—N3—C11	103.8 (2)
C11—C10—H10	127.3
C7—O1—C1—C6	12.1 (4)	C10—C11—C12—C17	3.8 (4)
C7—O1—C1—C2	−168.5 (2)	N3—C11—C12—C17	−176.8 (2)
O1—C1—C2—C3	179.8 (2)	C17—C12—C13—C14	0.3 (4)
C6—C1—C2—C3	−0.8 (4)	C11—C12—C13—C14	−179.7 (2)
O1—C1—C2—Cl1	0.1 (3)	C12—C13—C14—C15	0.7 (4)
C6—C1—C2—Cl1	179.52 (18)	C13—C14—C15—C16	−1.2 (4)
C1—C2—C3—C4	0.4 (4)	C13—C14—C15—C18	179.8 (3)
Cl1—C2—C3—C4	−179.96 (18)	C14—C15—C16—C17	0.6 (4)
C2—C3—C4—C5	0.4 (4)	C18—C15—C16—C17	179.7 (3)
C2—C3—C4—Cl2	−178.67 (19)	C15—C16—C17—C12	0.4 (4)
C3—C4—C5—C6	−0.7 (4)	C13—C12—C17—C16	−0.8 (4)
Cl2—C4—C5—C6	178.4 (2)	C11—C12—C17—C16	179.2 (3)
C4—C5—C6—C1	0.2 (4)	C7—C8—N1—N2	−178.7 (2)
O1—C1—C6—C5	179.9 (2)	S1—C8—N1—N2	0.5 (3)
C2—C1—C6—C5	0.5 (4)	N3—C9—N2—N1	179.9 (2)
C1—O1—C7—C8	173.7 (2)	S1—C9—N2—N1	0.0 (3)
O1—C7—C8—N1	175.6 (2)	N3—C9—N2—C10	0.9 (3)
O1—C7—C8—S1	−3.6 (3)	S1—C9—N2—C10	−178.94 (16)
C9—S1—C8—N1	−0.4 (2)	C8—N1—N2—C9	−0.3 (3)
C9—S1—C8—C7	178.8 (2)	C8—N1—N2—C10	178.3 (3)
C8—S1—C9—N3	−179.7 (3)	C11—C10—N2—C9	−0.6 (3)
C8—S1—C9—N2	0.19 (17)	C11—C10—N2—N1	−179.3 (2)
N2—C10—C11—N3	0.1 (3)	N2—C9—N3—C11	−0.8 (3)
N2—C10—C11—C12	179.6 (2)	S1—C9—N3—C11	179.0 (2)
C10—C11—C12—C13	−176.2 (2)	C10—C11—N3—C9	0.4 (3)
N3—C11—C12—C13	3.2 (3)	C12—C11—N3—C9	−179.1 (2)