3-{2-[2-(Diphenyl­methyl­ene)hydrazin­yl]thia­zol-4-yl}-2H-chromen-2-one

Arshad, A.; Osman, H.; Chan, K.L.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810023627

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1788-o1789

doi:10.1107/S1600536810023627

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3-{2-[2-(Diphenylmethylene)hydrazinyl]thiazol-4-yl}-2H-chromen-2-one

Afsheen Arshad,^a Hasnah Osman,^a Kit Lam Chan,^b Chin Sing Yeap ^c ‡ and Hoong-Kun Fun ^c ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 June 2010; accepted 18 June 2010; online 26 June 2010)

In the title compound, C₂₅H₁₇N₃O₂S, the coumarin ring system is essentially planar with a maximum deviation of 0.019 (2) Å. A weak intramolecular C—H⋯O hydrogen bond stabilizes the molecular structure, so that the coumarin plane is approximately coplanar with the thiazole 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 molecules are linked into an infinite chain along the b axis by intermolecular C—H⋯O hydrogen bonds. Weak C—H⋯π interactions 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_r = 423.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.125
S = 1.04
4181 reflections
284 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) $[-x, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) -x+1, -y, -z+2; (iii) -x, -y, -z+2.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Coumarin derivatives having pronounced biological activities are used as anticoagulants (Tassies et al., 2002), antibacterial (Laffitte et al., 2002), cytotoxic (Weber et al., 1998), free radical scavengers (Finn et al., 2004) and enzyme inhibiting (Kimura et al., 1985) agents. Moreover, aminothiazoles derivatives have been reported to exhibit significant antifungal (Hiremath et al., 1992), anti-tuberculosis (Karah et al., 1998) and anti-inflammatory (Jayashree et al., 2005) activities. The title compound is a new coumarinyl thiazolyl hydrazone derivative. We present here its crystal structure.

The geometry parameters of the title compound (Fig. 1) are comparable to those related structures (Arshad, Osman, Chan et al., 2010a,b; Arshad, Osman, Lam et al., 2010). The coumarin group is essentially planar (O1/C1–C9) with a maximum derivation of 0.019 Å at atom C7. The mean plane is approximately coplanar with the thiazole ring (C10–C11–S1–C12–N1) with a dihedral angle being 2.5 (10)°. The other two benzene rings are nearly perpendicular to each other with a dihedral angle being 81.44 (12)°.

In the crystal structure, the molecules are linked into infinite chains along b axis by the intermolecular C6—H6A···O1 hydrogen bonds and stabilized by the weak C—H···π interactions (Fig. 2, Table 1). A weak intramolecular C11—H11A···O2 hydrogen bond stabilizes the molecular structure.

Related literature top

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.

For related literature, see: .

Experimental top

Benzophenone thiosemicarbazone (Lobana et al., 2006) and 3-(ω-bromoacetyl)coumarin (Siddiqui et al., 2009) were synthesized as reported in the literature. A solution of 3-(ω-bromoacetyl)coumarin (2.5 mmol) and benzophenone thiosemicarbazone (2.5 mmol) in chloroform-ethanol (2:1) was refluxed for 1 h. Precipitates formed were filtered and boiled with water containing sodium acetate. The title compound was purified by recrystallization with ethanol-chloroform (1:3) as dark brown feather-like crystals.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, viewed down the b axis, showing the molecules are linked into chains along the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

3-{2-[2-(Diphenylmethylene)hydrazinyl]thiazol-4-yl}-2H-chromen-2-one top

Crystal data top

C₂₅H₁₇N₃O₂S	F(000) = 880
M_r = 423.48	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0488P)² + 1.1918P] where P = (F_o² + 2F_c²)/3
4181 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₅H₁₇N₃O₂S	V = 2023.6 (5) Å³
M_r = 423.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8705 (18) Å	µ = 0.19 mm⁻¹
b = 12.9101 (17) Å	T = 100 K
c = 11.8534 (16) Å	0.28 × 0.13 × 0.04 mm
β = 107.563 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4181 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2909 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.993	R_int = 0.067
17920 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
4181 reflections	Δρ_min = −0.32 e Å⁻³
284 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+5/2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₇N₃O₂S
M_r	423.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.8705 (18), 12.9101 (17), 11.8534 (16)
β (°)	107.563 (2)
V (Å³)	2023.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.13 × 0.04

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.949, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	17920, 4181, 2909
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.04
No. of reflections	4181
No. of parameters	284
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.9300	2.4600	3.377 (3)	168.00
C11—H11A···O2	0.9300	2.3000	2.857 (3)	118.00
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) −x, y−1/2, −z+5/2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

AA, HO and KLC thank the Malaysian Government and Universiti Sains Malaysia (USM) for a grant (RU/1001/PKIMIA/811133) to conduct this work. AA thanks the Pakistan Government and PCSIR for financial scholarship support. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship.

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Volume 66| Part 7| July 2010| Pages o1788-o1789

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