(2E)-4-(4-Bromo­phen­yl)-2-{(2Z)-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinyl­idene}-3-phenyl-2,3-di­hydro-1,3-thia­zole

Mohamed, S.K.; Akkurt, M.; Mague, J.T.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536813025506

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Pages o1563-o1564

doi:10.1107/S1600536813025506

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(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c Joel T. Mague,^d Alaa A. Hassan ^b and Mustafa R. Albayati ^e ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 11 September 2013; accepted 13 September 2013; online 18 September 2013)

In the title compound, C₂₄H₂₀BrN₃S, the dihydrothiazole ring is approximately planar, with a maximum deviation of 0.008 (2) Å, and is twisted with respect to the 4-bromophenyl ring, the phenyl ring and methylphenyl ring, making dihedral angles of 47.96 (8), 59.52 (9) and 16.96 (9)°, respectively. In the crystal, weak C—H⋯π interactions link inversion-related molecules into supramolecular dimers.

CCDC reference: 960927

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_r = 462.40
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.09
5310 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.52 e Å⁻³

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) -x+3, -y, -z+2.

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 ).

Supporting information

CCDC reference: 960927

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025506/xu5739sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813025506/xu5739Isup3.cml

checkCIF report

Comment top

The syntheses of a variety of thiazolidine-containing compounds have been reported (Masoudi et al., 2010; Darehkordia et al., 2007). Such compounds have been found to possess a wide range of biological properties such as antimicrobial (Pandeya et al., 1999; Shiradkar et al., 2007), antiproliferative (Gududuru et al., 2004), anti-inflammatory, analgesic, anti-ulcer (Taranalli et al., 2009; Kumar et al., 2007), anti-HIV (Rao et al., 2002; Rao et al., 2004; Barreca et al., 2001), antimalarial (Solomon et al., 2007), anticonvulsant (Amin et al., 2008) and antioxidant (Shih & Ying, 2004) activities. With this in mind and to further our ongoing study on the synthesis of various derivatives of thiazolidine compounds, we herein report the crystal structure of the title compound.

In Fig. 1, the thiazole ring (S1/N1/C1–C3) of the title compound is planar with an r.m.s. deviation of 0.002 Å. The 4-bromophenyl ring (C4–C9) makes a dihedral angle of 47.96 (8)° with the thiazole ring while the phenyl group (C10–C15) attached to the ring nitrogen makes a dihedral angle of 59.52 (9)°. The dihedral angle between the 4-methylphenyl ring (C18–C23) and the thiazole ring are 16.96 (9)°.

In the crystal, the packing consists of ribbons approximately parallel to [101] and assisted by C17—H17A···Cg4 (Cg4 is the centroid of the C18–C23 ring at 3 - x, -y, 2 - z; H17A···Cg = 2.77 Å, C17—H17A···Cg = 143°) interactions (Table 1).

Related literature top

For the syntheses of similar thiazolidine compounds, see, for example: Masoudi et al. (2010); Darehkordia et al. (2007) and for the synthesis of the title 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 top

The title compound has been prepared according to our reported method (Mohamed et al., 2013). The crude product has been crystallized from ethanol to afford translucent orange blocks suitable for X-ray diffraction (m.p.: 491 – 493 K).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).

Figures top

	Fig. 1. View of the title compound with 50% probability ellipsoids.
	Fig. 2. Packing of the title compound viewed down the a-axis.

(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole top

Crystal data top

C₂₄H₂₀BrN₃S	Z = 2
M_r = 462.40	F(000) = 472
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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	Δρ_max = 0.97 e Å⁻³
264 parameters	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₄H₂₀BrN₃S	γ = 96.302 (1)°
M_r = 462.40	V = 1027.31 (11) Å³
Triclinic, P1	Z = 2
a = 7.9622 (5) Å	Mo Kα radiation
b = 11.2672 (7) Å	µ = 2.12 mm⁻¹
c = 11.6370 (7) Å	T = 150 K
α = 96.273 (1)°	0.23 × 0.17 × 0.14 mm
β = 94.386 (1)°

Data collection top

Bruker Smart APEX CCD diffractometer	5310 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4582 reflections with i > 2σ(i)
T_min = 0.60, T_max = 0.76	R_int = 0.033
18958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.09	Δρ_max = 0.97 e Å⁻³
5310 reflections	Δρ_min = −0.52 e Å⁻³
264 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Symmetry code: (i) −x+3, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

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) −x+3, −y, −z+2.

Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

References

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Volume 69| Part 10| October 2013| Pages o1563-o1564

doi:10.1107/S1600536813025506

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E)-4-(4-Bromo­phen­yl)-2-{(2Z)-[1-(4-methyl­phen­yl)ethyl­­idene]hydrazinyl­­idene}-3-phenyl-2,3-di­hydro-1,3-thia­zole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole