(1Z,2E)-1-(3,4-Diphenyl-2,3-di-hydro-1,3-thia-zol-2-yl-idene)-2-(1-p-tolyl-ethyl-idene)hydrazine.

In the title compound, C24H21N3S, the thia-zole ring makes dihedral angles of 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively, with the two phenyl rings and the benzene ring. In the crystal, weak C-H⋯π inter-actions occur between inversion-related mol-ecules.

Related literature

For the syntheses and bioactivity of thia­zole-containing compounds, see: Siddiqui et al. (2009 ▶); Ramla et al. (2006 ▶); Popsavin et al. (2007 ▶); Kumar et al. (2007 ▶); Pandeya et al. (1999 ▶); Narayana et al. (2004 ▶); Shiradkar et al. (2007 ▶); Amin et al. (2008 ▶); Shih & Ying (2004 ▶); Andreani et al. (1987 ▶).

Experimental

Crystal data

C24H21N3S

M = 383.51

Triclinic,

a = 7.9370 (8) Å

b = 10.7587 (11) Å

c = 11.9325 (13) Å

α = 94.922 (2)°

β = 97.436 (2)°

γ = 95.383 (2)°

V = 1000.95 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 150 K

0.30 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.83, T max = 0.98

17908 measured reflections

4870 independent reflections

4287 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.06

4870 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 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 ▶) and DIAMOND (Brandenburg & Putz, 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/S1600536813020254/xu5722sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020254/xu5722Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020254/xu5722Isup3.cml

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

C24H21N3S	Z = 2
Mr = 383.51	F(000) = 404
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9370 (8) Å	Cell parameters from 9946 reflections
b = 10.7587 (11) Å	θ = 2.5–29.1°
c = 11.9325 (13) Å	µ = 0.18 mm−1
α = 94.922 (2)°	T = 150 K
β = 97.436 (2)°	Block, translucent yellow
γ = 95.383 (2)°	0.30 × 0.15 × 0.12 mm
V = 1000.95 (18) Å3

Bruker SMART APEX CCD diffractometer	4870 independent reflections
Radiation source: fine-focus sealed tube	4287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 28.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −10→10
Tmin = 0.83, Tmax = 0.98	k = −14→13
17908 measured reflections	l = −15→15

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.119	W = 1/[Σ2(FO2) + (0.0663P)2 + 0.2395P] WHERE P = (FO2 + 2FC2)/3
S = 1.06	(Δ/σ)max < 0.001
4870 reflections	Δρmax = 0.33 e Å−3
255 parameters	Δρmin = −0.30 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 20 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
S1	0.39566 (4)	0.41513 (3)	0.16060 (3)	0.0296 (1)
N1	0.40562 (13)	0.65478 (10)	0.15561 (9)	0.0266 (3)
N2	0.58080 (15)	0.59963 (11)	0.31261 (10)	0.0320 (3)
N3	0.63650 (14)	0.49413 (11)	0.36084 (9)	0.0304 (3)
C1	0.27238 (16)	0.47641 (12)	0.05087 (11)	0.0294 (3)
C2	0.28971 (15)	0.60194 (12)	0.06040 (10)	0.0250 (3)
C3	0.47515 (15)	0.56729 (12)	0.22097 (10)	0.0269 (3)
C4	0.18436 (15)	0.68175 (12)	−0.00790 (10)	0.0250 (3)
C5	0.16266 (16)	0.66568 (13)	−0.12623 (11)	0.0299 (4)
C6	0.05372 (18)	0.73637 (14)	−0.18849 (12)	0.0353 (4)
C7	−0.03595 (18)	0.82156 (13)	−0.13387 (13)	0.0371 (4)
C8	−0.01560 (18)	0.83778 (13)	−0.01614 (13)	0.0354 (4)
C9	0.09520 (17)	0.76964 (12)	0.04655 (11)	0.0298 (3)
C10	0.46544 (15)	0.78546 (12)	0.17887 (11)	0.0268 (3)
C11	0.54876 (16)	0.84599 (12)	0.10073 (11)	0.0296 (4)
C12	0.60307 (18)	0.97346 (14)	0.12303 (12)	0.0357 (4)
C13	0.5727 (2)	1.03903 (14)	0.22148 (14)	0.0417 (5)
C14	0.4910 (2)	0.97690 (16)	0.30020 (14)	0.0445 (5)
C15	0.43855 (18)	0.84986 (14)	0.27966 (12)	0.0361 (4)
C16	0.72732 (18)	0.64349 (13)	0.53188 (11)	0.0338 (4)
C17	0.70933 (16)	0.51734 (13)	0.46504 (11)	0.0281 (3)
C18	0.78315 (15)	0.41138 (13)	0.51776 (10)	0.0283 (4)
C19	0.89132 (17)	0.43040 (14)	0.62146 (11)	0.0323 (4)
C20	0.97073 (17)	0.33273 (15)	0.66605 (11)	0.0347 (4)
C21	0.94400 (18)	0.21266 (15)	0.61090 (12)	0.0357 (4)
C22	0.83119 (19)	0.19244 (15)	0.50894 (12)	0.0371 (4)
C23	0.75304 (17)	0.28937 (14)	0.46339 (11)	0.0328 (4)
C24	1.0340 (3)	0.10791 (18)	0.65903 (15)	0.0536 (6)
H1	0.20060	0.42600	−0.00920	0.0350*
H5	0.22240	0.60630	−0.16440	0.0360*
H6	0.04080	0.72610	−0.26910	0.0420*
H7	−0.11130	0.86890	−0.17690	0.0440*
H8	−0.07780	0.89580	0.02150	0.0430*
H9	0.11080	0.78260	0.12710	0.0360*
H11	0.56870	0.80090	0.03250	0.0360*
H12	0.66140	1.01550	0.07020	0.0430*
H13	0.60740	1.12650	0.23550	0.0500*
H14	0.47120	1.02200	0.36840	0.0530*
H15	0.38460	0.80710	0.33410	0.0430*
H16A	0.84650	0.68030	0.54040	0.0510*
H16B	0.69340	0.63410	0.60710	0.0510*
H16C	0.65380	0.69850	0.49190	0.0510*
H19	0.91060	0.51160	0.66190	0.0390*
H20	1.04510	0.34850	0.73600	0.0420*
H22	0.80820	0.11030	0.47050	0.0440*
H23	0.67750	0.27310	0.39400	0.0390*
H24A	1.14520	0.10640	0.63190	0.0800*
H24B	0.96450	0.02770	0.63440	0.0800*
H24C	1.05080	0.12150	0.74220	0.0800*

	U11	U22	U33	U12	U13	U23
S1	0.0294 (2)	0.0278 (2)	0.0296 (2)	−0.0005 (1)	−0.0006 (1)	0.0023 (1)
N1	0.0260 (5)	0.0270 (5)	0.0233 (5)	−0.0051 (4)	−0.0028 (4)	0.0006 (4)
N2	0.0311 (5)	0.0341 (6)	0.0279 (5)	−0.0028 (4)	−0.0036 (4)	0.0043 (4)
N3	0.0277 (5)	0.0358 (6)	0.0255 (5)	−0.0031 (4)	−0.0008 (4)	0.0040 (4)
C1	0.0282 (6)	0.0294 (6)	0.0273 (6)	−0.0009 (5)	−0.0031 (5)	−0.0007 (5)
C2	0.0221 (5)	0.0291 (6)	0.0213 (5)	−0.0028 (4)	0.0002 (4)	−0.0010 (4)
C3	0.0238 (5)	0.0312 (6)	0.0243 (6)	−0.0028 (5)	0.0020 (4)	0.0027 (5)
C4	0.0213 (5)	0.0258 (6)	0.0253 (6)	−0.0045 (4)	−0.0002 (4)	0.0004 (4)
C5	0.0262 (6)	0.0337 (7)	0.0265 (6)	−0.0027 (5)	−0.0002 (5)	−0.0026 (5)
C6	0.0334 (7)	0.0401 (8)	0.0277 (6)	−0.0067 (6)	−0.0064 (5)	0.0051 (5)
C7	0.0299 (6)	0.0306 (7)	0.0480 (8)	−0.0027 (5)	−0.0052 (6)	0.0112 (6)
C8	0.0319 (6)	0.0249 (6)	0.0491 (8)	0.0002 (5)	0.0068 (6)	0.0031 (6)
C9	0.0300 (6)	0.0275 (6)	0.0300 (6)	−0.0030 (5)	0.0043 (5)	−0.0008 (5)
C10	0.0234 (5)	0.0276 (6)	0.0260 (6)	−0.0037 (4)	−0.0022 (4)	−0.0004 (5)
C11	0.0292 (6)	0.0315 (7)	0.0258 (6)	−0.0018 (5)	0.0006 (5)	0.0007 (5)
C12	0.0333 (7)	0.0338 (7)	0.0369 (7)	−0.0064 (5)	−0.0017 (6)	0.0071 (6)
C13	0.0401 (8)	0.0297 (7)	0.0491 (9)	−0.0065 (6)	−0.0044 (6)	−0.0044 (6)
C14	0.0436 (8)	0.0439 (9)	0.0404 (8)	−0.0039 (7)	0.0045 (6)	−0.0158 (6)
C15	0.0331 (7)	0.0413 (8)	0.0306 (7)	−0.0064 (6)	0.0059 (5)	−0.0057 (6)
C16	0.0362 (7)	0.0374 (7)	0.0252 (6)	−0.0020 (6)	0.0002 (5)	0.0017 (5)
C17	0.0236 (5)	0.0349 (7)	0.0240 (6)	−0.0047 (5)	0.0021 (4)	0.0024 (5)
C18	0.0235 (6)	0.0380 (7)	0.0225 (6)	−0.0024 (5)	0.0041 (5)	0.0035 (5)
C19	0.0313 (6)	0.0379 (7)	0.0248 (6)	−0.0064 (5)	0.0009 (5)	0.0030 (5)
C20	0.0291 (6)	0.0480 (8)	0.0256 (6)	−0.0024 (6)	0.0001 (5)	0.0085 (6)
C21	0.0317 (7)	0.0482 (8)	0.0301 (7)	0.0097 (6)	0.0088 (5)	0.0077 (6)
C22	0.0386 (7)	0.0406 (8)	0.0321 (7)	0.0076 (6)	0.0068 (6)	−0.0027 (6)
C23	0.0317 (6)	0.0414 (8)	0.0235 (6)	0.0031 (5)	0.0009 (5)	−0.0024 (5)
C24	0.0609 (11)	0.0606 (11)	0.0427 (9)	0.0267 (9)	0.0043 (8)	0.0063 (8)

S1—C1	1.7447 (13)	C19—C20	1.385 (2)
S1—C3	1.7559 (13)	C20—C21	1.383 (2)
N1—C2	1.4074 (16)	C21—C22	1.402 (2)
N1—C3	1.3823 (16)	C21—C24	1.505 (3)
N1—C10	1.4328 (17)	C22—C23	1.378 (2)
N2—N3	1.3983 (17)	C1—H1	0.9500
N2—C3	1.2894 (17)	C5—H5	0.9500
N3—C17	1.2946 (17)	C6—H6	0.9500
C1—C2	1.3381 (18)	C7—H7	0.9500
C2—C4	1.4762 (18)	C8—H8	0.9500
C4—C5	1.3938 (18)	C9—H9	0.9500
C4—C9	1.3986 (18)	C11—H11	0.9500
C5—C6	1.390 (2)	C12—H12	0.9500
C6—C7	1.383 (2)	C13—H13	0.9500
C7—C8	1.387 (2)	C14—H14	0.9500
C8—C9	1.384 (2)	C15—H15	0.9500
C10—C11	1.3834 (18)	C16—H16A	0.9800
C10—C15	1.3868 (19)	C16—H16B	0.9800
C11—C12	1.391 (2)	C16—H16C	0.9800
C12—C13	1.378 (2)	C19—H19	0.9500
C13—C14	1.391 (2)	C20—H20	0.9500
C14—C15	1.382 (2)	C22—H22	0.9500
C16—C17	1.4990 (19)	C23—H23	0.9500
C17—C18	1.4804 (19)	C24—H24A	0.9800
C18—C19	1.3996 (18)	C24—H24B	0.9800
C18—C23	1.399 (2)	C24—H24C	0.9800
C1—S1—C3	90.54 (6)	S1—C1—H1	124.00
C2—N1—C3	113.96 (10)	C2—C1—H1	124.00
C2—N1—C10	124.82 (11)	C4—C5—H5	120.00
C3—N1—C10	120.84 (10)	C6—C5—H5	120.00
N3—N2—C3	110.94 (11)	C5—C6—H6	120.00
N2—N3—C17	113.90 (11)	C7—C6—H6	120.00
S1—C1—C2	112.82 (10)	C6—C7—H7	120.00
N1—C2—C1	112.76 (11)	C8—C7—H7	120.00
N1—C2—C4	120.69 (11)	C7—C8—H8	120.00
C1—C2—C4	125.95 (11)	C9—C8—H8	120.00
S1—C3—N1	109.91 (9)	C4—C9—H9	120.00
S1—C3—N2	128.02 (10)	C8—C9—H9	120.00
N1—C3—N2	122.07 (12)	C10—C11—H11	120.00
C2—C4—C5	121.26 (11)	C12—C11—H11	120.00
C2—C4—C9	119.58 (11)	C11—C12—H12	120.00
C5—C4—C9	119.02 (12)	C13—C12—H12	120.00
C4—C5—C6	120.09 (12)	C12—C13—H13	120.00
C5—C6—C7	120.45 (13)	C14—C13—H13	120.00
C6—C7—C8	119.83 (13)	C13—C14—H14	120.00
C7—C8—C9	120.12 (13)	C15—C14—H14	120.00
C4—C9—C8	120.47 (12)	C10—C15—H15	120.00
N1—C10—C11	119.80 (11)	C14—C15—H15	120.00
N1—C10—C15	119.42 (12)	C17—C16—H16A	109.00
C11—C10—C15	120.78 (12)	C17—C16—H16B	109.00
C10—C11—C12	119.34 (12)	C17—C16—H16C	109.00
C11—C12—C13	120.31 (13)	H16A—C16—H16B	109.00
C12—C13—C14	119.87 (14)	H16A—C16—H16C	109.00
C13—C14—C15	120.31 (15)	H16B—C16—H16C	109.00
C10—C15—C14	119.35 (13)	C18—C19—H19	119.00
N3—C17—C16	124.23 (12)	C20—C19—H19	119.00
N3—C17—C18	116.36 (12)	C19—C20—H20	119.00
C16—C17—C18	119.37 (11)	C21—C20—H20	119.00
C17—C18—C19	121.26 (12)	C21—C22—H22	119.00
C17—C18—C23	121.15 (11)	C23—C22—H22	119.00
C19—C18—C23	117.54 (12)	C18—C23—H23	119.00
C18—C19—C20	121.03 (13)	C22—C23—H23	120.00
C19—C20—C21	121.36 (13)	C21—C24—H24A	109.00
C20—C21—C22	117.72 (14)	C21—C24—H24B	109.00
C20—C21—C24	120.83 (13)	C21—C24—H24C	109.00
C22—C21—C24	121.45 (15)	H24A—C24—H24B	110.00
C21—C22—C23	121.27 (14)	H24A—C24—H24C	109.00
C18—C23—C22	121.02 (12)	H24B—C24—H24C	109.00
C3—S1—C1—C2	−0.49 (11)	C2—C4—C9—C8	−174.46 (12)
C1—S1—C3—N1	−0.21 (9)	C5—C4—C9—C8	1.3 (2)
C1—S1—C3—N2	179.04 (13)	C4—C5—C6—C7	−1.0 (2)
C3—N1—C2—C1	−1.24 (15)	C5—C6—C7—C8	0.8 (2)
C3—N1—C2—C4	170.45 (11)	C6—C7—C8—C9	0.5 (2)
C10—N1—C2—C1	171.65 (11)	C7—C8—C9—C4	−1.6 (2)
C10—N1—C2—C4	−16.66 (18)	N1—C10—C11—C12	178.63 (12)
C2—N1—C3—S1	0.84 (13)	C15—C10—C11—C12	−1.2 (2)
C2—N1—C3—N2	−178.47 (12)	N1—C10—C15—C14	−177.75 (13)
C10—N1—C3—S1	−172.37 (9)	C11—C10—C15—C14	2.1 (2)
C10—N1—C3—N2	8.33 (18)	C10—C11—C12—C13	−0.6 (2)
C2—N1—C10—C11	−58.30 (17)	C11—C12—C13—C14	1.5 (2)
C2—N1—C10—C15	121.54 (14)	C12—C13—C14—C15	−0.6 (2)
C3—N1—C10—C11	114.13 (14)	C13—C14—C15—C10	−1.2 (2)
C3—N1—C10—C15	−66.03 (16)	N3—C17—C18—C19	168.14 (12)
C3—N2—N3—C17	−164.53 (12)	N3—C17—C18—C23	−9.15 (18)
N3—N2—C3—S1	2.76 (17)	C16—C17—C18—C19	−9.91 (18)
N3—N2—C3—N1	−178.07 (11)	C16—C17—C18—C23	172.80 (12)
N2—N3—C17—C16	2.60 (18)	C17—C18—C19—C20	−174.87 (12)
N2—N3—C17—C18	−175.34 (11)	C23—C18—C19—C20	2.51 (19)
S1—C1—C2—N1	1.06 (14)	C17—C18—C23—C22	175.55 (13)
S1—C1—C2—C4	−170.11 (10)	C19—C18—C23—C22	−1.8 (2)
N1—C2—C4—C5	136.04 (13)	C18—C19—C20—C21	−1.1 (2)
N1—C2—C4—C9	−48.28 (17)	C19—C20—C21—C22	−1.1 (2)
C1—C2—C4—C5	−53.44 (19)	C19—C20—C21—C24	178.69 (15)
C1—C2—C4—C9	122.24 (15)	C20—C21—C22—C23	1.8 (2)
C2—C4—C5—C6	175.69 (12)	C24—C21—C22—C23	−178.01 (15)
C9—C4—C5—C6	0.0 (2)	C21—C22—C23—C18	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···S1i	0.98	3.03	4.0031 (14)	175
C16—H16C···N2	0.98	2.28	2.7053 (18)	105
C15—H15···Cg4i	0.95	2.71	3.6170 (16)	160
C16—H16A···Cg4ii	0.98	2.77	3.5984 (16)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg4i	0.95	2.71	3.6170 (16)	160
C16—H16A⋯Cg4ii	0.98	2.77	3.5984 (16)	143

Symmetry codes: (i) ; (ii) .