(2E)-4-(4-Bromo-phen-yl)-2-{(2Z)-[1-(4-methyl-phen-yl)ethyl-idene]hydrazinyl-idene}-3-phenyl-2,3-di-hydro-1,3-thia-zole.

In the title compound, C24H20BrN3S, the di-hydro-thia-zole ring is approximately planar, with a maximum deviation of 0.008 (2) Å, and is twisted with respect to the 4-bromo-phenyl ring, the phenyl ring and methyl-phenyl ring, making dihedral angles of 47.96 (8), 59.52 (9) and 16.96 (9)°, respectively. In the crystal, weak C-H⋯π inter-actions link inversion-related mol-ecules into supra-molecular dimers.

Related literature

For the syntheses of similar thia­zolidine compounds, see, for example: Masoudi et al. (2010 ▶); Darehkordia et al. (2007 ▶) and for the synthesis of a related compound, see: Mohamed et al. (2013 ▶). For the range of biological activities of thia­zolidine-containing compounds, see: Pandeya et al. (1999 ▶); Shiradkar et al. (2007 ▶); Gududuru et al. (2004 ▶); Taranalli et al. (2009 ▶); Kumar et al. (2007 ▶); Rao et al. (2002 ▶, 2004 ▶); Barreca et al. (2001 ▶); Solomon et al. (2007 ▶); Amin et al. (2008 ▶); Shih & Ying (2004 ▶).

Experimental

Crystal data

C24H20BrN3S

M = 462.40

Triclinic,

a = 7.9622 (5) Å

b = 11.2672 (7) Å

c = 11.6370 (7) Å

α = 96.273 (1)°

β = 94.386 (1)°

γ = 96.302 (1)°

V = 1027.31 (11) Å3

Z = 2

Mo Kα radiation

μ = 2.12 mm−1

T = 150 K

0.23 × 0.17 × 0.14 mm

Data collection

Bruker Smart APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.60, T max = 0.76

18958 measured reflections

5310 independent reflections

4582 reflections with i > 2σ(i)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.09

5310 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025506/xu5739sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025506/xu5739Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025506/xu5739Isup3.cml

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

C24H20BrN3S	Z = 2
Mr = 462.40	F(000) = 472
Triclinic, P1	Dx = 1.495 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9622 (5) Å	Cell parameters from 9928 reflections
b = 11.2672 (7) Å	θ = 2.4–29.1°
c = 11.6370 (7) Å	µ = 2.12 mm−1
α = 96.273 (1)°	T = 150 K
β = 94.386 (1)°	Block, translucent orange
γ = 96.302 (1)°	0.23 × 0.17 × 0.14 mm
V = 1027.31 (11) Å3

Bruker Smart APEX CCD diffractometer	5310 independent reflections
Radiation source: fine-focus sealed tube	4582 reflections with i > 2σ(i)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −14→15
Tmin = 0.60, Tmax = 0.76	l = −15→15
18958 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.097	W = 1/[Σ2(FO2) + (0.0545P)2 + 0.2353P] WHERE P = (FO2 + 2FC2)/3
S = 1.09	(Δ/σ)max = 0.001
5310 reflections	Δρmax = 0.97 e Å−3
264 parameters	Δρmin = −0.52 e Å−3

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame.

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
Br1	0.30655 (3)	0.39026 (2)	0.30405 (2)	0.0337 (1)
S1	0.89651 (6)	−0.07711 (4)	0.65607 (4)	0.0232 (1)
N1	0.91033 (19)	0.15300 (13)	0.65666 (13)	0.0202 (4)
N2	1.0854 (2)	0.09850 (14)	0.80890 (14)	0.0249 (5)
N3	1.1384 (2)	−0.00294 (14)	0.85333 (14)	0.0232 (4)
C1	0.7740 (2)	−0.01832 (17)	0.55032 (17)	0.0236 (5)
C2	0.7931 (2)	0.10264 (17)	0.56284 (15)	0.0201 (5)
C3	0.9789 (2)	0.06878 (16)	0.71838 (16)	0.0209 (5)
C4	0.6892 (2)	0.17839 (16)	0.49902 (16)	0.0206 (5)
C5	0.6570 (2)	0.15626 (18)	0.37854 (17)	0.0235 (5)
C6	0.5459 (2)	0.22100 (18)	0.31982 (17)	0.0249 (5)
C7	0.4664 (2)	0.30698 (17)	0.38211 (17)	0.0231 (5)
C8	0.4987 (2)	0.33198 (17)	0.50162 (17)	0.0253 (5)
C9	0.6109 (2)	0.26850 (17)	0.55927 (16)	0.0227 (5)
C10	0.9755 (2)	0.27811 (16)	0.67949 (16)	0.0201 (5)
C11	1.0510 (2)	0.33501 (17)	0.59380 (17)	0.0235 (5)
C12	1.1144 (3)	0.45611 (18)	0.61650 (19)	0.0284 (6)
C13	1.1018 (3)	0.51860 (18)	0.7235 (2)	0.0306 (6)
C14	1.0260 (3)	0.46116 (19)	0.80881 (19)	0.0300 (6)
C15	0.9628 (2)	0.34014 (18)	0.78762 (17)	0.0248 (5)
C16	1.2045 (2)	0.01738 (17)	0.95964 (16)	0.0212 (5)
C17	1.2183 (3)	0.13675 (18)	1.03341 (17)	0.0272 (6)
C18	1.2755 (2)	−0.08429 (17)	1.00904 (16)	0.0217 (5)
C19	1.3742 (2)	−0.06595 (18)	1.11581 (17)	0.0257 (5)
C20	1.4562 (3)	−0.15780 (19)	1.15694 (18)	0.0287 (6)
C21	1.4419 (3)	−0.27080 (19)	1.09447 (18)	0.0283 (6)
C22	1.3378 (3)	−0.29089 (19)	0.99012 (19)	0.0287 (6)
C23	1.2561 (2)	−0.19953 (18)	0.94795 (17)	0.0258 (5)
C24	1.5419 (3)	−0.3684 (2)	1.1368 (2)	0.0354 (7)
H1	0.70160	−0.06660	0.49030	0.0280*
H5	0.71130	0.09670	0.33630	0.0280*
H6	0.52480	0.20630	0.23770	0.0300*
H8	0.44450	0.39190	0.54330	0.0300*
H9	0.63510	0.28630	0.64090	0.0270*
H11	1.05960	0.29180	0.52010	0.0280*
H12	1.16650	0.49580	0.55810	0.0340*
H13	1.14520	0.60130	0.73870	0.0370*
H14	1.01710	0.50470	0.88230	0.0360*
H15	0.91170	0.30040	0.84640	0.0300*
H17A	1.33760	0.17120	1.04670	0.0410*
H17B	1.17330	0.12550	1.10810	0.0410*
H17C	1.15300	0.19140	0.99360	0.0410*
H19	1.38520	0.01050	1.16090	0.0310*
H20	1.52320	−0.14270	1.22930	0.0340*
H22	1.32270	−0.36860	0.94720	0.0340*
H23	1.18630	−0.21560	0.87680	0.0310*
H24A	1.59110	−0.34280	1.21660	0.0530*
H24B	1.63290	−0.38160	1.08640	0.0530*
H24C	1.46580	−0.44330	1.13440	0.0530*

	U11	U22	U33	U12	U13	U23
Br1	0.0380 (1)	0.0275 (1)	0.0349 (1)	0.0071 (1)	−0.0114 (1)	0.0072 (1)
S1	0.0258 (2)	0.0195 (2)	0.0240 (2)	0.0029 (2)	0.0006 (2)	0.0024 (2)
N1	0.0203 (7)	0.0190 (7)	0.0203 (8)	0.0009 (6)	−0.0019 (6)	0.0022 (6)
N2	0.0260 (8)	0.0240 (8)	0.0239 (8)	0.0026 (6)	−0.0043 (6)	0.0046 (6)
N3	0.0222 (7)	0.0247 (8)	0.0229 (8)	0.0025 (6)	−0.0008 (6)	0.0054 (6)
C1	0.0238 (9)	0.0248 (9)	0.0209 (9)	0.0015 (7)	−0.0013 (7)	0.0008 (7)
C2	0.0186 (8)	0.0252 (9)	0.0157 (8)	0.0015 (7)	0.0008 (6)	0.0009 (6)
C3	0.0212 (8)	0.0213 (8)	0.0202 (9)	0.0020 (7)	0.0017 (7)	0.0033 (7)
C4	0.0173 (8)	0.0223 (9)	0.0210 (9)	−0.0001 (7)	−0.0010 (7)	0.0018 (7)
C5	0.0213 (8)	0.0277 (9)	0.0204 (9)	0.0025 (7)	0.0011 (7)	−0.0013 (7)
C6	0.0253 (9)	0.0310 (10)	0.0167 (9)	−0.0004 (8)	−0.0020 (7)	0.0019 (7)
C7	0.0215 (8)	0.0222 (9)	0.0247 (9)	0.0003 (7)	−0.0051 (7)	0.0057 (7)
C8	0.0255 (9)	0.0243 (9)	0.0255 (10)	0.0042 (7)	0.0005 (7)	0.0009 (7)
C9	0.0241 (9)	0.0245 (9)	0.0185 (9)	0.0025 (7)	−0.0001 (7)	0.0003 (7)
C10	0.0165 (8)	0.0200 (8)	0.0230 (9)	0.0024 (6)	−0.0017 (6)	0.0017 (7)
C11	0.0231 (9)	0.0254 (9)	0.0220 (9)	0.0044 (7)	0.0013 (7)	0.0021 (7)
C12	0.0256 (9)	0.0276 (10)	0.0330 (11)	0.0027 (8)	0.0007 (8)	0.0096 (8)
C13	0.0284 (10)	0.0216 (9)	0.0397 (12)	0.0020 (8)	−0.0064 (9)	0.0014 (8)
C14	0.0297 (10)	0.0301 (10)	0.0274 (11)	0.0055 (8)	−0.0030 (8)	−0.0067 (8)
C15	0.0224 (9)	0.0293 (10)	0.0225 (9)	0.0045 (7)	0.0004 (7)	0.0022 (7)
C16	0.0187 (8)	0.0244 (9)	0.0203 (9)	0.0004 (7)	0.0018 (7)	0.0036 (7)
C17	0.0327 (10)	0.0271 (10)	0.0213 (10)	0.0022 (8)	−0.0002 (8)	0.0033 (7)
C18	0.0184 (8)	0.0283 (9)	0.0192 (9)	0.0021 (7)	0.0030 (7)	0.0058 (7)
C19	0.0257 (9)	0.0293 (10)	0.0211 (9)	−0.0001 (7)	0.0000 (7)	0.0040 (7)
C20	0.0258 (9)	0.0373 (11)	0.0231 (10)	0.0008 (8)	−0.0007 (7)	0.0092 (8)
C21	0.0254 (9)	0.0347 (11)	0.0278 (11)	0.0058 (8)	0.0056 (8)	0.0126 (8)
C22	0.0305 (10)	0.0272 (10)	0.0292 (11)	0.0059 (8)	0.0032 (8)	0.0041 (8)
C23	0.0254 (9)	0.0298 (10)	0.0220 (9)	0.0027 (8)	0.0004 (7)	0.0035 (7)
C24	0.0367 (11)	0.0373 (12)	0.0357 (12)	0.0131 (9)	0.0028 (9)	0.0114 (9)

Br1—C7	1.8966 (18)	C18—C23	1.397 (3)
S1—C1	1.7439 (19)	C19—C20	1.391 (3)
S1—C3	1.7573 (19)	C20—C21	1.384 (3)
N1—C2	1.406 (2)	C21—C22	1.399 (3)
N1—C3	1.385 (2)	C21—C24	1.529 (3)
N1—C10	1.437 (2)	C22—C23	1.390 (3)
N2—N3	1.398 (2)	C1—H1	0.9500
N2—C3	1.290 (2)	C5—H5	0.9500
N3—C16	1.293 (2)	C6—H6	0.9500
C1—C2	1.345 (3)	C8—H8	0.9500
C2—C4	1.471 (2)	C9—H9	0.9500
C4—C5	1.396 (3)	C11—H11	0.9500
C4—C9	1.401 (3)	C12—H12	0.9500
C5—C6	1.393 (3)	C13—H13	0.9500
C6—C7	1.384 (3)	C14—H14	0.9500
C7—C8	1.387 (3)	C15—H15	0.9500
C8—C9	1.383 (3)	C17—H17A	0.9800
C10—C11	1.383 (3)	C17—H17B	0.9800
C10—C15	1.387 (3)	C17—H17C	0.9800
C11—C12	1.391 (3)	C19—H19	0.9500
C12—C13	1.378 (3)	C20—H20	0.9500
C13—C14	1.384 (3)	C22—H22	0.9500
C14—C15	1.389 (3)	C23—H23	0.9500
C16—C17	1.503 (3)	C24—H24A	0.9800
C16—C18	1.483 (3)	C24—H24B	0.9800
C18—C19	1.401 (3)	C24—H24C	0.9800
C1—S1—C3	90.57 (9)	C21—C22—C23	121.4 (2)
C2—N1—C3	113.95 (15)	C18—C23—C22	120.76 (18)
C2—N1—C10	124.72 (15)	S1—C1—H1	124.00
C3—N1—C10	120.74 (15)	C2—C1—H1	124.00
N3—N2—C3	111.32 (15)	C4—C5—H5	120.00
N2—N3—C16	114.04 (16)	C6—C5—H5	120.00
S1—C1—C2	112.77 (14)	C5—C6—H6	120.00
N1—C2—C1	112.72 (16)	C7—C6—H6	120.00
N1—C2—C4	121.09 (16)	C7—C8—H8	120.00
C1—C2—C4	125.66 (16)	C9—C8—H8	120.00
S1—C3—N1	109.97 (12)	C4—C9—H9	120.00
S1—C3—N2	127.42 (14)	C8—C9—H9	119.00
N1—C3—N2	122.60 (16)	C10—C11—H11	120.00
C2—C4—C5	120.73 (16)	C12—C11—H11	120.00
C2—C4—C9	120.26 (16)	C11—C12—H12	120.00
C5—C4—C9	118.85 (16)	C13—C12—H12	120.00
C4—C5—C6	120.42 (17)	C12—C13—H13	120.00
C5—C6—C7	119.41 (18)	C14—C13—H13	120.00
Br1—C7—C6	119.81 (14)	C13—C14—H14	120.00
Br1—C7—C8	118.99 (13)	C15—C14—H14	120.00
C6—C7—C8	121.18 (17)	C10—C15—H15	120.00
C7—C8—C9	119.13 (17)	C14—C15—H15	120.00
C4—C9—C8	120.97 (17)	C16—C17—H17A	109.00
N1—C10—C11	119.67 (16)	C16—C17—H17B	109.00
N1—C10—C15	119.49 (16)	C16—C17—H17C	109.00
C11—C10—C15	120.85 (17)	H17A—C17—H17B	109.00
C10—C11—C12	119.43 (18)	H17A—C17—H17C	109.00
C11—C12—C13	120.2 (2)	H17B—C17—H17C	109.00
C12—C13—C14	120.13 (19)	C18—C19—H19	119.00
C13—C14—C15	120.4 (2)	C20—C19—H19	119.00
C10—C15—C14	119.06 (18)	C19—C20—H20	119.00
N3—C16—C17	124.44 (17)	C21—C20—H20	119.00
N3—C16—C18	116.73 (17)	C21—C22—H22	119.00
C17—C16—C18	118.80 (16)	C23—C22—H22	119.00
C16—C18—C19	120.75 (17)	C18—C23—H23	120.00
C16—C18—C23	121.50 (16)	C22—C23—H23	120.00
C19—C18—C23	117.62 (17)	C21—C24—H24A	109.00
C18—C19—C20	121.12 (18)	C21—C24—H24B	109.00
C19—C20—C21	121.2 (2)	C21—C24—H24C	109.00
C20—C21—C22	117.8 (2)	H24A—C24—H24B	109.00
C20—C21—C24	120.7 (2)	H24A—C24—H24C	110.00
C22—C21—C24	121.52 (19)	H24B—C24—H24C	109.00
C1—S1—C3—N2	178.97 (17)	C5—C4—C9—C8	2.3 (3)
C3—S1—C1—C2	−0.78 (14)	C4—C5—C6—C7	−0.5 (3)
C1—S1—C3—N1	−0.03 (14)	C5—C6—C7—Br1	−176.96 (14)
C3—N1—C10—C11	116.25 (19)	C5—C6—C7—C8	1.7 (3)
C3—N1—C2—C1	−1.4 (2)	C6—C7—C8—C9	−0.8 (3)
C3—N1—C10—C15	−63.3 (2)	Br1—C7—C8—C9	177.83 (13)
C10—N1—C3—N2	10.2 (3)	C7—C8—C9—C4	−1.2 (3)
C10—N1—C2—C4	−18.1 (2)	N1—C10—C11—C12	−179.80 (17)
C10—N1—C3—S1	−170.78 (13)	C11—C10—C15—C14	0.5 (3)
C2—N1—C3—N2	−178.25 (16)	C15—C10—C11—C12	−0.2 (3)
C3—N1—C2—C4	170.66 (15)	N1—C10—C15—C14	−179.91 (18)
C2—N1—C10—C15	126.02 (18)	C10—C11—C12—C13	0.0 (3)
C10—N1—C2—C1	169.77 (16)	C11—C12—C13—C14	0.0 (4)
C2—N1—C10—C11	−54.4 (2)	C12—C13—C14—C15	0.3 (4)
C2—N1—C3—S1	0.81 (18)	C13—C14—C15—C10	−0.6 (3)
N3—N2—C3—S1	2.6 (2)	N3—C16—C18—C19	169.30 (16)
C3—N2—N3—C16	−161.26 (16)	N3—C16—C18—C23	−6.5 (2)
N3—N2—C3—N1	−178.52 (15)	C17—C16—C18—C19	−8.8 (2)
N2—N3—C16—C17	2.6 (3)	C17—C16—C18—C23	175.40 (17)
N2—N3—C16—C18	−175.39 (14)	C16—C18—C19—C20	−173.07 (18)
S1—C1—C2—N1	1.38 (19)	C23—C18—C19—C20	2.9 (3)
S1—C1—C2—C4	−170.28 (14)	C16—C18—C23—C22	173.41 (18)
N1—C2—C4—C5	140.44 (17)	C19—C18—C23—C22	−2.5 (3)
C1—C2—C4—C9	126.8 (2)	C18—C19—C20—C21	−0.6 (3)
C1—C2—C4—C5	−48.6 (3)	C19—C20—C21—C22	−2.0 (3)
N1—C2—C4—C9	−44.2 (2)	C19—C20—C21—C24	176.0 (2)
C2—C4—C9—C8	−173.15 (16)	C20—C21—C22—C23	2.3 (3)
C2—C4—C5—C6	174.01 (17)	C24—C21—C22—C23	−175.6 (2)
C9—C4—C5—C6	−1.4 (3)	C21—C22—C23—C18	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···N2	0.98	2.28	2.713 (3)	105
C17—H17A···Cg4i	0.98	2.77	3.595 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg4i	0.98	2.77	3.595 (3)	143

Symmetry code: (i) .