2-[6-(4-Chloro-phen-yl)imidazo[2,1-b][1,3]thia-zol-2-yl]-N'-[(E)-4-meth-oxy-benzyl-idene]acetohydrazide.

In the imidazo[2,1-b][1,3]thia-zole group of the title compound, C(21)H(17)ClN(4)O(2)S, the dihedral angle between the thia-zole and imidazole rings is 1.9 (2)°. The mean plane of this group makes dihedral angles of 5.5 (2) and 39.9 (2)° with the benzene rings of the chloro-phenyl and meth-oxy-phenyl groups, respectively. The dihedral angle between these two benzene rings is 34.4 (2)°. In the crystal, mol-ecules are connected to each other by inter-molecular N-H⋯O hydrogen bonds along the b axis, generating a C(4) chain. Weak C-H⋯π inter-actions also occur.

Related literature

For the biological activity of imidazo[2,1-b][1,3]thia­zole derivatives, see: Andreani et al. (2005 ▶); Barradas et al. (2008 ▶); Hanson et al. (1991 ▶); Juspin et al. (2010 ▶); Shilcrat et al. (1991 ▶). For details of the synthesis, see: Gürsoy & Ulusoy Güzeldemirci (2007 ▶); Ulusoy Güzeldemirci & Küçükbasmacı (2010 ▶). For related structures, see: Akkurt et al. (2007 ▶, 2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H17ClN4O2S

M = 424.91

Orthorhombic,

a = 13.4591 (6) Å

b = 4.7834 (3) Å

c = 30.4674 (14) Å

V = 1961.50 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.38 × 0.26 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.890, T max = 0.961

10765 measured reflections

3304 independent reflections

2754 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.164

S = 1.01

3304 reflections

265 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1611 Friedel pairs

Flack parameter: 0.15 (11)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052359/vm2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052359/vm2066Isup2.hkl

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

C21H17ClN4O2S	F(000) = 880
Mr = 424.91	Dx = 1.439 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 15357 reflections
a = 13.4591 (6) Å	θ = 1.3–25.1°
b = 4.7834 (3) Å	µ = 0.33 mm−1
c = 30.4674 (14) Å	T = 296 K
V = 1961.50 (18) Å3	Prism, colourless
Z = 4	0.38 × 0.26 × 0.13 mm

Stoe IPDS 2 diffractometer	3304 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2754 reflections with I > 2σ(I)
plane graphite	Rint = 0.092
Detector resolution: 6.67 pixels mm-1	θmax = 24.6°, θmin = 1.3°
ω scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.890, Tmax = 0.961	l = −35→35
10765 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.1136P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.164	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.20 e Å−3
3304 reflections	Δρmin = −0.20 e Å−3
265 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
1 restraint	Extinction coefficient: 0.010 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1611 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.15 (11)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.54087 (14)	1.5430 (3)	0.72891 (5)	0.1113 (6)
S1	1.01901 (8)	0.7353 (3)	0.53219 (5)	0.0824 (4)
O1	0.6911 (2)	0.6101 (5)	0.46534 (10)	0.0706 (10)
O2	0.1795 (3)	0.1793 (9)	0.30456 (13)	0.0947 (12)
N1	0.8812 (3)	0.9668 (8)	0.59159 (12)	0.0709 (11)
N2	0.8350 (2)	0.6242 (7)	0.54579 (11)	0.0612 (10)
N3	0.6651 (3)	0.1742 (7)	0.43926 (12)	0.0689 (11)
N4	0.5793 (3)	0.2476 (7)	0.41650 (13)	0.0676 (11)
C1	0.7215 (3)	1.0549 (9)	0.62971 (14)	0.0647 (12)
C2	0.7662 (4)	1.2522 (10)	0.65723 (15)	0.0770 (14)
C3	0.7105 (4)	1.3995 (11)	0.68731 (17)	0.0863 (19)
C4	0.6104 (4)	1.3556 (10)	0.69031 (16)	0.0800 (19)
C5	0.5640 (4)	1.1665 (12)	0.66394 (17)	0.0823 (17)
C6	0.6196 (4)	1.0159 (11)	0.63367 (15)	0.0767 (17)
C7	0.7810 (3)	0.9024 (9)	0.59711 (15)	0.0653 (12)
C8	0.7513 (3)	0.6957 (8)	0.56975 (14)	0.0630 (12)
C9	0.9110 (3)	0.7939 (9)	0.56040 (15)	0.0680 (12)
C10	0.8635 (3)	0.4461 (8)	0.51164 (14)	0.0620 (12)
C11	0.9596 (3)	0.4809 (10)	0.50111 (17)	0.0720 (17)
C12	0.7937 (3)	0.2362 (8)	0.49197 (16)	0.0655 (14)
C13	0.7124 (3)	0.3618 (8)	0.46392 (14)	0.0596 (11)
C14	0.5417 (4)	0.0495 (10)	0.39367 (16)	0.0723 (16)
C15	0.4478 (4)	0.0818 (9)	0.37059 (15)	0.0700 (14)
C16	0.3780 (4)	0.2839 (9)	0.38208 (16)	0.0730 (16)
C17	0.2884 (4)	0.3090 (11)	0.36042 (17)	0.0790 (17)
C18	0.2698 (4)	0.1353 (10)	0.32490 (17)	0.0750 (16)
C19	0.3377 (4)	−0.0638 (10)	0.31242 (17)	0.0817 (17)
C20	0.4246 (4)	−0.0884 (10)	0.33545 (18)	0.0783 (17)
C21	0.1516 (5)	−0.0120 (16)	0.2706 (2)	0.115 (3)
H2	0.83420	1.28430	0.65520	0.0920*
H3	0.74110	1.52900	0.70560	0.1030*
H3A	0.68770	0.00650	0.43740	0.0830*
H5	0.49580	1.13840	0.66620	0.0980*
H6	0.58800	0.88640	0.61570	0.0920*
H8	0.68810	0.61820	0.56750	0.0760*
H11	0.99130	0.37860	0.47930	0.0860*
H12A	0.76320	0.13000	0.51550	0.0780*
H12B	0.83180	0.10670	0.47420	0.0780*
H14	0.57540	−0.11980	0.39180	0.0870*
H16	0.39220	0.40560	0.40500	0.0880*
H17	0.24140	0.43960	0.36950	0.0950*
H19	0.32490	−0.18020	0.28860	0.0980*
H20	0.46990	−0.22540	0.32710	0.0940*
H21A	0.20130	−0.01150	0.24800	0.1720*
H21B	0.08890	0.04400	0.25840	0.1720*
H21C	0.14580	−0.19670	0.28270	0.1720*

	U11	U22	U33	U12	U13	U23
Cl1	0.1479 (14)	0.0934 (9)	0.0926 (8)	0.0296 (9)	0.0312 (9)	−0.0020 (8)
S1	0.0569 (5)	0.0919 (8)	0.0983 (8)	−0.0039 (5)	0.0019 (6)	−0.0118 (7)
O1	0.0780 (18)	0.0475 (13)	0.0862 (18)	0.0048 (13)	−0.0115 (16)	0.0021 (14)
O2	0.086 (2)	0.102 (2)	0.096 (2)	0.004 (2)	−0.020 (2)	−0.020 (2)
N1	0.0618 (18)	0.076 (2)	0.075 (2)	0.0001 (17)	−0.0067 (18)	−0.005 (2)
N2	0.0554 (17)	0.0586 (16)	0.0697 (19)	−0.0003 (14)	−0.0055 (15)	0.0055 (15)
N3	0.075 (2)	0.0517 (17)	0.080 (2)	0.0084 (15)	−0.0098 (19)	0.0007 (16)
N4	0.069 (2)	0.0569 (17)	0.077 (2)	0.0017 (15)	−0.0060 (17)	−0.0023 (17)
C1	0.068 (2)	0.063 (2)	0.063 (2)	0.0025 (19)	−0.0017 (18)	0.0064 (18)
C2	0.093 (3)	0.068 (2)	0.070 (2)	−0.006 (2)	−0.004 (2)	0.000 (2)
C3	0.108 (4)	0.077 (3)	0.074 (3)	0.001 (3)	−0.007 (3)	−0.010 (3)
C4	0.099 (4)	0.070 (3)	0.071 (3)	0.017 (2)	0.009 (3)	0.002 (2)
C5	0.079 (3)	0.088 (3)	0.080 (3)	0.015 (3)	0.007 (3)	0.003 (3)
C6	0.074 (3)	0.083 (3)	0.073 (3)	0.006 (2)	0.005 (2)	0.003 (2)
C7	0.067 (2)	0.062 (2)	0.067 (2)	0.0017 (18)	−0.004 (2)	0.007 (2)
C8	0.057 (2)	0.062 (2)	0.070 (2)	−0.0038 (18)	0.0016 (18)	0.0042 (19)
C9	0.060 (2)	0.069 (2)	0.075 (2)	0.0014 (19)	−0.003 (2)	0.003 (2)
C10	0.066 (2)	0.055 (2)	0.065 (2)	0.0055 (17)	−0.0037 (19)	0.0025 (18)
C11	0.062 (3)	0.072 (3)	0.082 (3)	0.0067 (19)	−0.002 (2)	0.000 (2)
C12	0.068 (2)	0.0504 (19)	0.078 (3)	0.0026 (17)	−0.006 (2)	0.0034 (18)
C13	0.066 (2)	0.0478 (18)	0.065 (2)	−0.0003 (16)	0.0044 (19)	0.0037 (17)
C14	0.076 (3)	0.064 (2)	0.077 (3)	0.002 (2)	−0.001 (2)	−0.002 (2)
C15	0.078 (3)	0.061 (2)	0.071 (2)	−0.001 (2)	0.000 (2)	0.000 (2)
C16	0.077 (3)	0.068 (2)	0.074 (3)	−0.002 (2)	−0.005 (2)	−0.012 (2)
C17	0.072 (3)	0.076 (3)	0.089 (3)	0.005 (2)	−0.003 (2)	−0.013 (2)
C18	0.071 (3)	0.080 (3)	0.074 (2)	−0.006 (2)	−0.010 (2)	−0.001 (2)
C19	0.080 (3)	0.081 (3)	0.084 (3)	0.000 (2)	−0.009 (2)	−0.018 (2)
C20	0.074 (3)	0.068 (3)	0.093 (3)	0.005 (2)	−0.005 (2)	−0.013 (2)
C21	0.113 (5)	0.123 (5)	0.108 (4)	0.001 (4)	−0.034 (4)	−0.034 (4)

Cl1—C4	1.750 (5)	C12—C13	1.513 (6)
S1—C9	1.712 (4)	C14—C15	1.455 (7)
S1—C11	1.737 (5)	C15—C20	1.381 (7)
O1—C13	1.223 (5)	C15—C16	1.393 (7)
O2—C18	1.380 (7)	C16—C17	1.380 (7)
O2—C21	1.431 (8)	C17—C18	1.387 (7)
N1—C7	1.394 (6)	C18—C19	1.374 (7)
N1—C9	1.322 (6)	C19—C20	1.369 (8)
N2—C8	1.385 (5)	C2—H2	0.9300
N2—C9	1.380 (5)	C3—H3	0.9300
N2—C10	1.398 (5)	C5—H5	0.9300
N3—N4	1.392 (6)	C6—H6	0.9300
N3—C13	1.332 (5)	C8—H8	0.9300
N4—C14	1.280 (6)	C11—H11	0.9300
N3—H3A	0.8600	C12—H12A	0.9700
C1—C6	1.389 (7)	C12—H12B	0.9700
C1—C7	1.470 (6)	C14—H14	0.9300
C1—C2	1.399 (6)	C16—H16	0.9300
C2—C3	1.378 (7)	C17—H17	0.9300
C3—C4	1.367 (8)	C19—H19	0.9300
C4—C5	1.362 (7)	C20—H20	0.9300
C5—C6	1.389 (7)	C21—H21A	0.9600
C7—C8	1.354 (6)	C21—H21B	0.9600
C10—C12	1.500 (6)	C21—H21C	0.9600
C10—C11	1.343 (6)
C9—S1—C11	89.9 (2)	C16—C17—C18	118.6 (5)
C18—O2—C21	117.3 (5)	O2—C18—C19	124.6 (5)
C7—N1—C9	104.0 (4)	O2—C18—C17	114.7 (5)
C8—N2—C9	106.7 (3)	C17—C18—C19	120.7 (5)
C8—N2—C10	140.0 (3)	C18—C19—C20	119.1 (5)
C9—N2—C10	113.3 (3)	C15—C20—C19	122.7 (5)
N4—N3—C13	120.5 (3)	C1—C2—H2	120.00
N3—N4—C14	114.3 (4)	C3—C2—H2	120.00
C13—N3—H3A	120.00	C2—C3—H3	120.00
N4—N3—H3A	120.00	C4—C3—H3	120.00
C2—C1—C7	120.4 (4)	C4—C5—H5	120.00
C2—C1—C6	117.6 (4)	C6—C5—H5	120.00
C6—C1—C7	122.0 (4)	C1—C6—H6	119.00
C1—C2—C3	120.7 (5)	C5—C6—H6	119.00
C2—C3—C4	120.2 (5)	N2—C8—H8	127.00
C3—C4—C5	121.0 (5)	C7—C8—H8	127.00
Cl1—C4—C5	119.5 (4)	S1—C11—H11	123.00
Cl1—C4—C3	119.6 (4)	C10—C11—H11	123.00
C4—C5—C6	119.3 (5)	C10—C12—H12A	109.00
C1—C6—C5	121.3 (5)	C10—C12—H12B	109.00
N1—C7—C1	120.0 (4)	C13—C12—H12A	109.00
N1—C7—C8	111.9 (4)	C13—C12—H12B	109.00
C1—C7—C8	128.2 (4)	H12A—C12—H12B	108.00
N2—C8—C7	105.4 (3)	N4—C14—H14	119.00
N1—C9—N2	112.0 (4)	C15—C14—H14	119.00
S1—C9—N1	136.1 (3)	C15—C16—H16	119.00
S1—C9—N2	111.8 (3)	C17—C16—H16	119.00
N2—C10—C11	111.5 (4)	C16—C17—H17	121.00
N2—C10—C12	122.2 (3)	C18—C17—H17	121.00
C11—C10—C12	126.2 (4)	C18—C19—H19	120.00
S1—C11—C10	113.6 (4)	C20—C19—H19	120.00
C10—C12—C13	114.4 (3)	C15—C20—H20	119.00
N3—C13—C12	113.4 (3)	C19—C20—H20	119.00
O1—C13—C12	122.4 (4)	O2—C21—H21A	110.00
O1—C13—N3	124.2 (4)	O2—C21—H21B	109.00
N4—C14—C15	121.9 (4)	O2—C21—H21C	109.00
C16—C15—C20	116.9 (5)	H21A—C21—H21B	110.00
C14—C15—C16	122.6 (4)	H21A—C21—H21C	110.00
C14—C15—C20	120.6 (4)	H21B—C21—H21C	109.00
C15—C16—C17	122.0 (4)
C11—S1—C9—N2	−0.2 (3)	C6—C1—C7—C8	−5.7 (7)
C11—S1—C9—N1	−177.4 (5)	C2—C1—C7—C8	176.1 (4)
C9—S1—C11—C10	0.4 (4)	C1—C2—C3—C4	−0.5 (7)
C21—O2—C18—C17	−173.8 (5)	C2—C3—C4—Cl1	179.6 (4)
C21—O2—C18—C19	5.6 (8)	C2—C3—C4—C5	0.2 (8)
C7—N1—C9—N2	0.2 (5)	Cl1—C4—C5—C6	−179.3 (4)
C7—N1—C9—S1	177.4 (4)	C3—C4—C5—C6	0.2 (8)
C9—N1—C7—C1	−180.0 (4)	C4—C5—C6—C1	−0.2 (8)
C9—N1—C7—C8	−0.1 (5)	C1—C7—C8—N2	179.9 (4)
C9—N2—C8—C7	0.1 (4)	N1—C7—C8—N2	0.0 (5)
C10—N2—C9—N1	177.8 (4)	C11—C10—C12—C13	−111.4 (5)
C10—N2—C8—C7	−177.0 (5)	N2—C10—C11—S1	−0.6 (5)
C8—N2—C9—S1	−178.1 (3)	C12—C10—C11—S1	−177.6 (3)
C9—N2—C10—C12	177.6 (4)	N2—C10—C12—C13	71.8 (5)
C10—N2—C9—S1	−0.1 (4)	C10—C12—C13—O1	−16.2 (6)
C8—N2—C9—N1	−0.2 (5)	C10—C12—C13—N3	166.1 (4)
C8—N2—C10—C12	−5.4 (7)	N4—C14—C15—C20	158.2 (5)
C9—N2—C10—C11	0.4 (5)	N4—C14—C15—C16	−21.1 (7)
C8—N2—C10—C11	177.4 (5)	C14—C15—C20—C19	−179.3 (5)
N4—N3—C13—O1	−7.0 (7)	C16—C15—C20—C19	0.1 (7)
C13—N3—N4—C14	179.3 (4)	C14—C15—C16—C17	−178.8 (5)
N4—N3—C13—C12	170.6 (4)	C20—C15—C16—C17	1.9 (7)
N3—N4—C14—C15	175.0 (4)	C15—C16—C17—C18	−3.0 (8)
C2—C1—C7—N1	−4.1 (6)	C16—C17—C18—C19	2.1 (8)
C2—C1—C6—C5	−0.2 (7)	C16—C17—C18—O2	−178.5 (4)
C6—C1—C2—C3	0.5 (7)	O2—C18—C19—C20	−179.6 (5)
C7—C1—C6—C5	−178.4 (5)	C17—C18—C19—C20	−0.2 (8)
C7—C1—C2—C3	178.8 (4)	C18—C19—C20—C15	−0.9 (8)
C6—C1—C7—N1	174.1 (4)

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.86	2.08	2.835 (4)	146
C2—H2···N1	0.93	2.54	2.874 (6)	101
C12—H12A···Cg1i	0.97	2.54	3.282 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1i	0.86	2.08	2.835 (4)	146
C12—H12A⋯Cg1i	0.97	2.54	3.282 (5)	133

Symmetry code: (i) .