3-{2-[2-(Diphenyl-methyl-ene)hydrazin-yl]thia-zol-4-yl}-2H-chromen-2-one.

In the title compound, C(25)H(17)N(3)O(2)S, the coumarin ring system is essentially planar with a maximum deviation of 0.019 (2) Å. A weak intra-molecular C-H⋯O hydrogen bond stabilizes the mol-ecular structure, so that the coumarin plane is approximately coplanar with the thia-zole ring, making a dihedral angle of 2.5 (10)°. The two phenyl rings are nearly perpendicular to each other, with a dihedral angle of 81.44 (12)°. In the crystal structure, the mol-ecules are linked into an infinite chain along the b axis by inter-molecular C-H⋯O hydrogen bonds. Weak C-H⋯π inter-actions are observed between the chains.

Related literature

For applications of coumarin derivatives, see: Tassies et al. (2002 ▶); Laffitte et al. (2002 ▶); Weber et al. (1998 ▶); Finn et al. (2004 ▶); Kimura et al. (1985 ▶). For applications of amino­thia­zoles derivatives, see: Hiremath et al. (1992 ▶); Karah et al. (1998 ▶); Jayashree et al. (2005 ▶). For related structures, see: Arshad, Osman, Chan et al. (2010a ▶,b ▶); Arshad, Osman, Lam et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). The syntheses of benzophenone thio­semicarbazone and 3-(ω-bromo­acet­yl)coumarin are described by Lobana et al. (2006 ▶) and Siddiqui et al. (2009 ▶), respectively.

Experimental

Crystal data

C25H17N3O2S

M = 423.48

Monoclinic,

a = 13.8705 (18) Å

b = 12.9101 (17) Å

c = 11.8534 (16) Å

β = 107.563 (2)°

V = 2023.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.28 × 0.13 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.993

17920 measured reflections

4181 independent reflections

2909 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.04

4181 reflections

284 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023627/is2564sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023627/is2564Isup2.hkl

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

C25H17N3O2S	F(000) = 880
Mr = 423.48	Dx = 1.390 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2695 reflections
a = 13.8705 (18) Å	θ = 2.2–25.7°
b = 12.9101 (17) Å	µ = 0.19 mm−1
c = 11.8534 (16) Å	T = 100 K
β = 107.563 (2)°	Plate, brown
V = 2023.6 (5) Å3	0.28 × 0.13 × 0.04 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4181 independent reflections
Radiation source: fine-focus sealed tube	2909 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.949, Tmax = 0.993	k = −16→16
17920 measured reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0488P)2 + 1.1918P] where P = (Fo2 + 2Fc2)/3
4181 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.27268 (5)	0.29137 (5)	0.91250 (6)	0.02688 (18)
O1	0.03690 (14)	0.49303 (13)	1.21227 (16)	0.0322 (5)
O2	0.12420 (15)	0.53063 (13)	1.09019 (17)	0.0375 (5)
N1	0.18366 (15)	0.20621 (15)	1.05262 (17)	0.0216 (4)
N2	0.25985 (16)	0.08768 (16)	0.95524 (19)	0.0257 (5)
N3	0.32315 (15)	0.07961 (15)	0.88597 (17)	0.0230 (5)
C1	0.09314 (19)	0.46244 (19)	1.1393 (2)	0.0267 (6)
C2	−0.00360 (19)	0.42446 (19)	1.2744 (2)	0.0265 (6)
C3	−0.0574 (2)	0.4642 (2)	1.3458 (3)	0.0377 (7)
H3A	−0.0672	0.5352	1.3499	0.045*
C4	−0.0961 (2)	0.3960 (2)	1.4110 (3)	0.0355 (7)
H4A	−0.1313	0.4218	1.4604	0.043*
C5	−0.08363 (19)	0.2904 (2)	1.4042 (2)	0.0274 (6)
H5A	−0.1104	0.2456	1.4485	0.033*
C6	−0.03123 (17)	0.25172 (19)	1.3315 (2)	0.0225 (5)
H6A	−0.0231	0.1805	1.3266	0.027*
C7	0.00990 (17)	0.31838 (18)	1.2649 (2)	0.0209 (5)
C8	0.06701 (18)	0.28439 (18)	1.1895 (2)	0.0213 (5)
H8A	0.0760	0.2137	1.1817	0.026*
C9	0.10832 (17)	0.35054 (18)	1.1294 (2)	0.0212 (5)
C10	0.16787 (18)	0.31334 (18)	1.0546 (2)	0.0209 (5)
C11	0.20939 (19)	0.37041 (19)	0.9838 (2)	0.0268 (6)
H11A	0.2042	0.4420	0.9753	0.032*
C12	0.23598 (18)	0.18608 (18)	0.9809 (2)	0.0225 (5)
C13	0.35407 (18)	−0.01140 (18)	0.8675 (2)	0.0210 (5)
C14	0.42271 (18)	−0.01483 (18)	0.7927 (2)	0.0213 (5)
C15	0.42459 (18)	0.06486 (19)	0.7143 (2)	0.0232 (5)
H15A	0.3784	0.1189	0.7037	0.028*
C16	0.49430 (19)	0.0646 (2)	0.6520 (2)	0.0261 (6)
H16A	0.4949	0.1184	0.6000	0.031*
C17	0.5631 (2)	−0.0155 (2)	0.6670 (2)	0.0288 (6)
H17A	0.6097	−0.0156	0.6247	0.035*
C18	0.56302 (19)	−0.0957 (2)	0.7446 (2)	0.0284 (6)
H18A	0.6098	−0.1492	0.7549	0.034*
C19	0.49287 (18)	−0.09584 (19)	0.8069 (2)	0.0237 (5)
H19A	0.4923	−0.1500	0.8585	0.028*
C20	0.33051 (17)	−0.11039 (18)	0.9191 (2)	0.0210 (5)
C21	0.36721 (19)	−0.12891 (19)	1.0402 (2)	0.0268 (6)
H21A	0.4018	−0.0770	1.0907	0.032*
C22	0.3526 (2)	−0.2240 (2)	1.0859 (2)	0.0288 (6)
H22A	0.3778	−0.2360	1.1669	0.035*
C23	0.30028 (19)	−0.3019 (2)	1.0112 (2)	0.0273 (6)
H23A	0.2916	−0.3664	1.0417	0.033*
C24	0.26132 (19)	−0.28293 (19)	0.8913 (2)	0.0282 (6)
H24A	0.2250	−0.3342	0.8411	0.034*
C25	0.27632 (18)	−0.18767 (19)	0.8457 (2)	0.0238 (5)
H25A	0.2498	−0.1753	0.7649	0.029*
H1N2	0.2549 (19)	0.034 (2)	1.003 (2)	0.027 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0327 (4)	0.0239 (3)	0.0311 (4)	−0.0054 (3)	0.0203 (3)	−0.0020 (3)
O1	0.0445 (11)	0.0185 (9)	0.0433 (11)	0.0005 (8)	0.0277 (10)	−0.0013 (8)
O2	0.0531 (13)	0.0196 (9)	0.0524 (12)	−0.0013 (9)	0.0350 (11)	0.0020 (9)
N1	0.0227 (10)	0.0206 (10)	0.0244 (11)	0.0010 (9)	0.0116 (9)	−0.0006 (9)
N2	0.0305 (12)	0.0211 (11)	0.0344 (12)	0.0012 (9)	0.0230 (11)	0.0009 (10)
N3	0.0245 (11)	0.0237 (11)	0.0260 (11)	−0.0008 (9)	0.0153 (10)	−0.0015 (9)
C1	0.0319 (14)	0.0208 (13)	0.0312 (14)	0.0010 (11)	0.0153 (13)	−0.0020 (11)
C2	0.0302 (14)	0.0219 (13)	0.0313 (14)	−0.0006 (11)	0.0153 (12)	0.0014 (11)
C3	0.0533 (19)	0.0200 (13)	0.0517 (18)	0.0034 (13)	0.0336 (16)	−0.0029 (13)
C4	0.0405 (16)	0.0312 (15)	0.0456 (17)	0.0047 (12)	0.0292 (15)	−0.0048 (13)
C5	0.0262 (13)	0.0299 (14)	0.0304 (14)	−0.0022 (11)	0.0150 (12)	0.0003 (11)
C6	0.0223 (12)	0.0202 (12)	0.0254 (13)	−0.0009 (10)	0.0077 (11)	−0.0005 (10)
C7	0.0182 (12)	0.0224 (13)	0.0211 (12)	−0.0005 (10)	0.0046 (10)	−0.0008 (10)
C8	0.0208 (12)	0.0188 (12)	0.0227 (12)	0.0003 (10)	0.0044 (11)	−0.0027 (10)
C9	0.0184 (12)	0.0222 (13)	0.0220 (12)	−0.0015 (10)	0.0048 (11)	−0.0036 (10)
C10	0.0217 (12)	0.0184 (12)	0.0241 (12)	−0.0017 (10)	0.0091 (11)	−0.0020 (10)
C11	0.0329 (14)	0.0202 (13)	0.0321 (14)	−0.0029 (11)	0.0172 (13)	−0.0030 (11)
C12	0.0224 (13)	0.0215 (13)	0.0262 (13)	−0.0012 (10)	0.0113 (11)	−0.0002 (10)
C13	0.0209 (12)	0.0231 (13)	0.0210 (12)	−0.0017 (10)	0.0094 (11)	−0.0010 (10)
C14	0.0237 (13)	0.0222 (13)	0.0205 (12)	−0.0039 (10)	0.0106 (11)	−0.0051 (10)
C15	0.0230 (13)	0.0269 (13)	0.0182 (12)	0.0006 (11)	0.0040 (11)	−0.0019 (10)
C16	0.0301 (14)	0.0316 (14)	0.0182 (13)	−0.0013 (11)	0.0096 (12)	0.0012 (11)
C17	0.0310 (14)	0.0332 (15)	0.0287 (14)	−0.0007 (12)	0.0189 (13)	−0.0057 (12)
C18	0.0296 (14)	0.0305 (14)	0.0298 (14)	0.0035 (11)	0.0161 (13)	−0.0047 (11)
C19	0.0263 (13)	0.0237 (13)	0.0240 (13)	−0.0030 (10)	0.0119 (12)	−0.0039 (10)
C20	0.0196 (12)	0.0209 (12)	0.0269 (13)	0.0007 (10)	0.0137 (11)	−0.0015 (10)
C21	0.0285 (14)	0.0250 (13)	0.0283 (14)	−0.0027 (11)	0.0106 (12)	−0.0017 (11)
C22	0.0309 (14)	0.0321 (15)	0.0223 (13)	0.0011 (11)	0.0062 (12)	0.0043 (11)
C23	0.0279 (14)	0.0249 (13)	0.0311 (14)	−0.0021 (11)	0.0120 (12)	0.0040 (11)
C24	0.0296 (14)	0.0256 (14)	0.0312 (15)	−0.0059 (11)	0.0119 (12)	−0.0043 (11)
C25	0.0227 (13)	0.0306 (14)	0.0174 (12)	−0.0039 (11)	0.0052 (11)	−0.0025 (10)

S1—C11	1.724 (2)	C10—C11	1.368 (3)
S1—C12	1.736 (2)	C11—H11A	0.9300
O1—C2	1.375 (3)	C13—C14	1.485 (3)
O1—C1	1.386 (3)	C13—C20	1.495 (3)
O2—C1	1.205 (3)	C14—C15	1.392 (3)
N1—C12	1.300 (3)	C14—C19	1.404 (3)
N1—C10	1.402 (3)	C15—C16	1.382 (3)
N2—C12	1.370 (3)	C15—H15A	0.9300
N2—N3	1.375 (2)	C16—C17	1.382 (3)
N2—H1N2	0.91 (3)	C16—H16A	0.9300
N3—C13	1.292 (3)	C17—C18	1.385 (3)
C1—C9	1.470 (3)	C17—H17A	0.9300
C2—C3	1.385 (3)	C18—C19	1.388 (3)
C2—C7	1.391 (3)	C18—H18A	0.9300
C3—C4	1.382 (4)	C19—H19A	0.9300
C3—H3A	0.9300	C20—C25	1.387 (3)
C4—C5	1.380 (4)	C20—C21	1.391 (3)
C4—H4A	0.9300	C21—C22	1.382 (3)
C5—C6	1.378 (3)	C21—H21A	0.9300
C5—H5A	0.9300	C22—C23	1.391 (4)
C6—C7	1.400 (3)	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.382 (4)
C7—C8	1.430 (3)	C23—H23A	0.9300
C8—C9	1.346 (3)	C24—C25	1.384 (3)
C8—H8A	0.9300	C24—H24A	0.9300
C9—C10	1.464 (3)	C25—H25A	0.9300
C11—S1—C12	88.29 (11)	N1—C12—S1	116.69 (18)
C2—O1—C1	123.27 (19)	N2—C12—S1	119.88 (16)
C12—N1—C10	109.20 (19)	N3—C13—C14	115.7 (2)
C12—N2—N3	116.31 (19)	N3—C13—C20	125.68 (19)
C12—N2—H1N2	119.7 (16)	C14—C13—C20	118.54 (19)
N3—N2—H1N2	119.8 (16)	C15—C14—C19	118.6 (2)
C13—N3—N2	118.33 (19)	C15—C14—C13	121.4 (2)
O2—C1—O1	116.4 (2)	C19—C14—C13	119.8 (2)
O2—C1—C9	126.8 (2)	C16—C15—C14	120.8 (2)
O1—C1—C9	116.8 (2)	C16—C15—H15A	119.6
O1—C2—C3	118.1 (2)	C14—C15—H15A	119.6
O1—C2—C7	120.3 (2)	C17—C16—C15	120.0 (2)
C3—C2—C7	121.6 (2)	C17—C16—H16A	120.0
C4—C3—C2	118.5 (2)	C15—C16—H16A	120.0
C4—C3—H3A	120.7	C16—C17—C18	120.4 (2)
C2—C3—H3A	120.7	C16—C17—H17A	119.8
C5—C4—C3	121.3 (2)	C18—C17—H17A	119.8
C5—C4—H4A	119.3	C17—C18—C19	119.7 (2)
C3—C4—H4A	119.3	C17—C18—H18A	120.1
C6—C5—C4	119.6 (2)	C19—C18—H18A	120.1
C6—C5—H5A	120.2	C18—C19—C14	120.5 (2)
C4—C5—H5A	120.2	C18—C19—H19A	119.8
C5—C6—C7	120.8 (2)	C14—C19—H19A	119.8
C5—C6—H6A	119.6	C25—C20—C21	119.0 (2)
C7—C6—H6A	119.6	C25—C20—C13	120.1 (2)
C2—C7—C6	118.2 (2)	C21—C20—C13	120.8 (2)
C2—C7—C8	117.8 (2)	C22—C21—C20	120.4 (2)
C6—C7—C8	124.1 (2)	C22—C21—H21A	119.8
C9—C8—C7	122.7 (2)	C20—C21—H21A	119.8
C9—C8—H8A	118.6	C21—C22—C23	120.2 (2)
C7—C8—H8A	118.6	C21—C22—H22A	119.9
C8—C9—C10	121.4 (2)	C23—C22—H22A	119.9
C8—C9—C1	119.2 (2)	C24—C23—C22	119.6 (2)
C10—C9—C1	119.4 (2)	C24—C23—H23A	120.2
C11—C10—N1	115.1 (2)	C22—C23—H23A	120.2
C11—C10—C9	127.9 (2)	C23—C24—C25	120.1 (2)
N1—C10—C9	116.96 (19)	C23—C24—H24A	120.0
C10—C11—S1	110.66 (18)	C25—C24—H24A	120.0
C10—C11—H11A	124.7	C24—C25—C20	120.7 (2)
S1—C11—H11A	124.7	C24—C25—H25A	119.6
N1—C12—N2	123.4 (2)	C20—C25—H25A	119.6
C12—N2—N3—C13	174.6 (2)	C10—N1—C12—N2	−176.8 (2)
C2—O1—C1—O2	−179.9 (2)	C10—N1—C12—S1	1.2 (3)
C2—O1—C1—C9	0.3 (4)	N3—N2—C12—N1	−174.4 (2)
C1—O1—C2—C3	179.2 (3)	N3—N2—C12—S1	7.6 (3)
C1—O1—C2—C7	−0.7 (4)	C11—S1—C12—N1	−1.5 (2)
O1—C2—C3—C4	−178.3 (3)	C11—S1—C12—N2	176.6 (2)
C7—C2—C3—C4	1.6 (4)	N2—N3—C13—C14	−179.6 (2)
C2—C3—C4—C5	−1.1 (5)	N2—N3—C13—C20	−2.6 (4)
C3—C4—C5—C6	0.2 (4)	N3—C13—C14—C15	−22.3 (3)
C4—C5—C6—C7	0.3 (4)	C20—C13—C14—C15	160.5 (2)
O1—C2—C7—C6	178.9 (2)	N3—C13—C14—C19	152.8 (2)
C3—C2—C7—C6	−1.0 (4)	C20—C13—C14—C19	−24.5 (3)
O1—C2—C7—C8	0.2 (4)	C19—C14—C15—C16	−0.2 (4)
C3—C2—C7—C8	−179.6 (3)	C13—C14—C15—C16	174.9 (2)
C5—C6—C7—C2	0.0 (4)	C14—C15—C16—C17	0.1 (4)
C5—C6—C7—C8	178.6 (2)	C15—C16—C17—C18	−0.3 (4)
C2—C7—C8—C9	0.7 (4)	C16—C17—C18—C19	0.5 (4)
C6—C7—C8—C9	−177.9 (2)	C17—C18—C19—C14	−0.6 (4)
C7—C8—C9—C10	178.9 (2)	C15—C14—C19—C18	0.5 (4)
C7—C8—C9—C1	−1.1 (4)	C13—C14—C19—C18	−174.7 (2)
O2—C1—C9—C8	−179.1 (3)	N3—C13—C20—C25	117.4 (3)
O1—C1—C9—C8	0.6 (4)	C14—C13—C20—C25	−65.7 (3)
O2—C1—C9—C10	0.9 (4)	N3—C13—C20—C21	−66.3 (3)
O1—C1—C9—C10	−179.4 (2)	C14—C13—C20—C21	110.6 (3)
C12—N1—C10—C11	−0.1 (3)	C25—C20—C21—C22	2.0 (3)
C12—N1—C10—C9	178.9 (2)	C13—C20—C21—C22	−174.3 (2)
C8—C9—C10—C11	176.1 (3)	C20—C21—C22—C23	−0.5 (4)
C1—C9—C10—C11	−3.9 (4)	C21—C22—C23—C24	−1.3 (4)
C8—C9—C10—N1	−2.8 (3)	C22—C23—C24—C25	1.4 (4)
C1—C9—C10—N1	177.2 (2)	C23—C24—C25—C20	0.1 (4)
N1—C10—C11—S1	−1.0 (3)	C21—C20—C25—C24	−1.9 (3)
C9—C10—C11—S1	−179.9 (2)	C13—C20—C25—C24	174.5 (2)
C12—S1—C11—C10	1.3 (2)

Cg1 and Cg2 are the centroids of the C14–C19 and C2–C7 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1i	0.93	2.46	3.377 (3)	168
C11—H11A···O2	0.93	2.30	2.857 (3)	118
C21—H21A···Cg1ii	0.93	2.49	3.387 (3)	162
C24—H24A···Cg2iii	0.93	2.78	3.536 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C19 and C2–C7 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1i	0.93	2.46	3.377 (3)	168
C11—H11A⋯O2	0.93	2.30	2.857 (3)	118
C21—H21A⋯Cg1ii	0.93	2.49	3.387 (3)	162
C24—H24A⋯Cg2iii	0.93	2.78	3.536 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .