(E)-3-(2-{2-[1-(3-Hy­droxy­phen­yl)ethyl­idene]hydrazin­yl}-1,3-thia­zol-4-yl)-2H-chromen-2-one

Arshad, A.; Osman, H.; Lam, C.K.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811012189

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1072-o1073

doi:10.1107/S1600536811012189

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(E)-3-(2-{2-[1-(3-Hydroxyphenyl)ethylidene]hydrazinyl}-1,3-thiazol-4-yl)-2H-chromen-2-one

Afsheen Arshad,^a Hasnah Osman,^a ‡ Chan Kit Lam,^b Madhukar Hemamalini ^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 30 March 2011; accepted 1 April 2011; online 7 April 2011)

In the title compound, C₂₀H₁₅N₃O₃S, the thiazole ring is approximately planar, with a maximum deviation of 0.003 (1) Å, and makes dihedral angles of 7.44 (6) and 1.88 (6)° with the hydroxy-substituted phenyl ring and the pyran ring, respectively. The hydroxyl group is disordered over two sets of sites, with an occupancy ratio of 0.567 (3):0.433 (3). In the crystal, the major disorder component molecules are connected via bifurcated (three-centre) O—H⋯O and C—H⋯O hydrogen bonds, generating R¹₂(6) motifs and resulting in supramolecular chains along the a axis. In the minor occupancy component, however, molecules are connected via C—H⋯O hydrogen bonds, forming supramolecular chains along the b axis. Furthermore, the crystal structure is stabilized by π–π interactions between the thiazole rings [centroid–centroid distance = 3.5476 (7) Å].

Related literature

For details of coumarin derivatives, see: Raghu et al. (2009 ); Gursoy & Karali (2003 ); Chimenti et al. (2010 ); Kamal et al. (2009 ); Kalkhambkar et al. (2007 ). For graph-set notation, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For the synthesis of (E)-2-(1-(3-hydroxyphenyl)ethylidene)hydrazinecarbothioamide, see: Greenbaum et al. (2004 ) and for that of 3-[ω-bromoacetyl coumarin, see: Nadeem et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₅N₃O₃S
M_r = 377.41
Monoclinic, P 2₁ /c
a = 9.1569 (1) Å
b = 9.9070 (2) Å
c = 18.7478 (3) Å
β = 92.040 (1)°
V = 1699.67 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.34 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.929, T_max = 0.979
29914 measured reflections
5400 independent reflections
4641 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.105
S = 1.07
5400 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1OA⋯O2ⁱ	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A⋯O2ⁱ	0.93	2.59	3.3020 (17)	133
Symmetry code: (i) x+1, y-1, z.

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/S1600536811012189/wn2428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012189/wn2428Isup2.hkl

checkCIF report

Comment top

Coumarin derivatives containing the thiazolyl unit exhibit promising antimicrobial activities against different microbial strains (Raghu et al., 2009), including Mycobacterium tuberculosis (Gursoy et al., 2003) and Helicobacter pylori (Chimenti et al., 2010). These types of compounds are also reported to be good anticancer (Kamal et al., 2009), analgesic and anti-inflammatory agents (Kalkhambkar et al., 2007). The title compound is a new derivative of coumarin with the thiazole ring. We present here its crystal structure.

In the molecular structure of the compound, (Fig.1), the thiazole (S1/N1/C10–C12) ring is approximately planar, with a maximum deviation of 0.003 (1) Å for atom C11. The central thiazole (S1/N1/C10–C12) ring makes dihedral angles of 7.44 (6)° and 1.88 (6)° with the hydroxyl- substituted phenyl (C14–C19) ring and the pyran (O1/C1,C2/C7–C9) ring, respectively. The hydroxyl group is disordered over two sites, with an occupancy ratio 0.567 (3):0.433 (3).

In the crystal packing (Fig. 2), the major component molecules are connected via bifurcated O3—H1OA···O2 and C19—H19A···O2 hydrogen bonds, generating R¹₂(6) motifs, (Bernstein et al., 1995), resulting in supramolecular chains along the a-axis. In the minor component, however, molecules are connected via C19—H19A···O2 hydrogen bonds, forming one-dimensional supramolecular chains along the b-axis (Fig. 3). Furthermore, the crystal structure is stabilized by π···π interactions between the thiazole (S1/N1/C10–C12) rings [centroid-centroid distance = 3.5476 (7) Å; -x, -y, 1-z].

Related literature top

For details of coumarin derivatives, see: Raghu et al. (2009); Gursoy & Karali (2003); Chimenti et al. (2010); Kamal et al. (2009); Kalkhambkar et al. (2007). For graph-set notation, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For the synthesis of (E)-2-(1-(3-hydroxyphenyl)ethylidene)hydrazinecarbothioamide, see: Greenbaum et al. (2004) and for that of 3-[ω-bromoacetyl coumarin, see: Nadeem et al. (2009).

Experimental top

(E)-2-(1-(3-Hydroxyphenyl)ethylidene)hydrazinecarbothioamide (Greenbaum et al., 2004) and 3-[ω-bromoacetyl coumarin] (Nadeem et al., 2009) were synthesized as reported in the literature. The title compound was prepared by treating (E)-2-(1-(3-hydroxyphenyl)ethylidene)hydrazinecarbothioamide (2.5 mmol) with 3-ω-bromoacetylcoumarin (2.5 mmol) in a chloroform-ethanol (2:1) mixture. The reaction mixture was refluxed for 2–3 hours at 60°C to yield dense yellow precipitates. The precipitates were filtered and boiled with water containing sodium acetate. The title compound was recrystallized as golden crystals from ethanol:chloroform (3:1).

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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. The open bonds represents the minor disordered components.
	Fig. 2. The crystal packing of the title compound, involving the major disorder components of the molecules. Dashed lines indicate hydrogen bonds.
	Fig. 3. The crystal packing of the title compound, involving the minor disorder components of the molecules. Dashed lines indicate hydrogen bonds.

(E)-3-(2-{2-[1-(3-Hydroxyphenyl)ethylidene]hydrazinyl}-1,3- thiazol-4-yl)-2H-chromen-2-one top

Crystal data top

C₂₀H₁₅N₃O₃S	F(000) = 784
M_r = 377.41	D_x = 1.475 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9987 reflections
a = 9.1569 (1) Å	θ = 3.0–30.8°
b = 9.9070 (2) Å	µ = 0.22 mm⁻¹
c = 18.7478 (3) Å	T = 100 K
β = 92.040 (1)°	Plate, yellow
V = 1699.67 (5) Å³	0.34 × 0.32 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5400 independent reflections
Radiation source: fine-focus sealed tube	4641 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 31.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
T_min = 0.929, T_max = 0.979	k = −13→14
29914 measured reflections	l = −27→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0429P)² + 0.8634P] where P = (F_o² + 2F_c²)/3
5400 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₀H₁₅N₃O₃S	V = 1699.67 (5) Å³
M_r = 377.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1569 (1) Å	µ = 0.22 mm⁻¹
b = 9.9070 (2) Å	T = 100 K
c = 18.7478 (3) Å	0.34 × 0.32 × 0.10 mm
β = 92.040 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5400 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4641 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.979	R_int = 0.030
29914 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.39 e Å⁻³
5400 reflections	Δρ_min = −0.30 e Å⁻³
271 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
S1	0.17023 (3)	0.06980 (3)	0.402397 (16)	0.02037 (8)
O1	−0.19100 (10)	0.47170 (9)	0.56457 (5)	0.01965 (18)
O2	−0.14551 (11)	0.40120 (11)	0.45684 (5)	0.0273 (2)
O3	0.75724 (18)	−0.54395 (18)	0.31831 (9)	0.0234 (5)	0.567 (3)
H1OA	0.797 (4)	−0.556 (4)	0.362 (2)	0.040 (10)*	0.567 (3)
O3A	0.4193 (3)	−0.2752 (3)	0.18640 (12)	0.0273 (7)	0.433 (3)
H1OB	0.363 (5)	−0.216 (5)	0.196 (2)	0.028 (11)*	0.433 (3)
N1	0.15618 (11)	0.10211 (11)	0.53942 (6)	0.0183 (2)
N2	0.31472 (13)	−0.07177 (12)	0.50380 (6)	0.0227 (2)
N3	0.36764 (12)	−0.13166 (12)	0.44404 (6)	0.0202 (2)
C1	−0.00034 (13)	0.28351 (13)	0.62488 (7)	0.0184 (2)
H1A	0.0626	0.2198	0.6456	0.022*
C2	−0.07700 (13)	0.37365 (13)	0.67004 (7)	0.0184 (2)
C3	−0.06263 (14)	0.37246 (14)	0.74487 (7)	0.0228 (3)
H3A	−0.0011	0.3101	0.7677	0.027*
C4	−0.13980 (14)	0.46385 (14)	0.78482 (7)	0.0231 (3)
H4A	−0.1304	0.4625	0.8344	0.028*
C5	−0.23196 (14)	0.55839 (14)	0.75060 (7)	0.0214 (2)
H5A	−0.2831	0.6198	0.7778	0.026*
C6	−0.24800 (14)	0.56170 (13)	0.67707 (7)	0.0203 (2)
H6A	−0.3089	0.6248	0.6544	0.024*
C7	−0.17091 (13)	0.46850 (13)	0.63785 (6)	0.0175 (2)
C8	−0.11845 (13)	0.38669 (13)	0.52030 (7)	0.0187 (2)
C9	−0.01694 (13)	0.28851 (12)	0.55271 (6)	0.0167 (2)
C10	0.06365 (13)	0.19757 (12)	0.50645 (6)	0.0169 (2)
C11	0.05871 (14)	0.19493 (13)	0.43358 (7)	0.0194 (2)
C12	0.21703 (13)	0.03050 (13)	0.49064 (7)	0.0183 (2)
C13	0.45893 (13)	−0.23030 (13)	0.45086 (7)	0.0186 (2)
C14	0.50587 (13)	−0.28993 (12)	0.38266 (7)	0.0179 (2)
C15	0.43761 (13)	−0.25098 (13)	0.31754 (7)	0.0189 (2)
H15A	0.3632	−0.1871	0.3171	0.023*
C16	0.48063 (14)	−0.30725 (13)	0.25395 (7)	0.0210 (2)
H16A	0.4359	−0.2796	0.2111	0.025*	0.567 (3)
C17	0.58993 (15)	−0.40455 (14)	0.25351 (7)	0.0232 (3)
H17A	0.6179	−0.4426	0.2108	0.028*
C18	0.65664 (14)	−0.44400 (14)	0.31770 (8)	0.0232 (3)
H18A	0.7292	−0.5097	0.3178	0.028*	0.433 (3)
C19	0.61671 (14)	−0.38669 (13)	0.38209 (7)	0.0210 (2)
H19A	0.6639	−0.4129	0.4246	0.025*
C20	0.51371 (16)	−0.28472 (15)	0.52150 (7)	0.0262 (3)
H20A	0.5374	−0.2111	0.5531	0.039*
H20B	0.5995	−0.3383	0.5148	0.039*
H20C	0.4394	−0.3396	0.5418	0.039*
H1N2	0.338 (2)	−0.090 (2)	0.5468 (11)	0.038 (5)*
H11	0.0039 (18)	0.2534 (18)	0.4013 (9)	0.029 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02210 (15)	0.02380 (16)	0.01531 (14)	0.00190 (11)	0.00199 (11)	−0.00074 (11)
O1	0.0222 (4)	0.0196 (4)	0.0170 (4)	0.0039 (3)	−0.0006 (3)	0.0017 (3)
O2	0.0337 (5)	0.0307 (5)	0.0174 (4)	0.0105 (4)	−0.0017 (4)	0.0032 (4)
O3	0.0226 (8)	0.0261 (9)	0.0213 (9)	0.0086 (6)	0.0010 (6)	−0.0031 (7)
O3A	0.0396 (14)	0.0249 (13)	0.0179 (11)	0.0025 (10)	0.0077 (9)	−0.0001 (9)
N1	0.0189 (5)	0.0191 (5)	0.0171 (5)	0.0013 (4)	0.0016 (4)	0.0008 (4)
N2	0.0244 (5)	0.0262 (6)	0.0176 (5)	0.0070 (4)	0.0024 (4)	0.0001 (4)
N3	0.0191 (5)	0.0224 (5)	0.0192 (5)	0.0025 (4)	0.0032 (4)	−0.0006 (4)
C1	0.0187 (5)	0.0186 (6)	0.0178 (5)	0.0025 (4)	−0.0005 (4)	0.0002 (4)
C2	0.0178 (5)	0.0197 (6)	0.0176 (5)	0.0012 (4)	−0.0006 (4)	−0.0014 (4)
C3	0.0225 (6)	0.0271 (7)	0.0186 (6)	0.0057 (5)	−0.0026 (5)	−0.0014 (5)
C4	0.0223 (6)	0.0289 (7)	0.0179 (6)	0.0029 (5)	−0.0013 (5)	−0.0045 (5)
C5	0.0193 (6)	0.0213 (6)	0.0236 (6)	0.0009 (5)	0.0018 (5)	−0.0048 (5)
C6	0.0186 (5)	0.0182 (6)	0.0240 (6)	0.0015 (4)	0.0000 (5)	−0.0001 (5)
C7	0.0178 (5)	0.0179 (5)	0.0167 (5)	−0.0012 (4)	−0.0004 (4)	0.0001 (4)
C8	0.0195 (5)	0.0176 (5)	0.0190 (6)	0.0007 (4)	0.0010 (4)	0.0011 (4)
C9	0.0167 (5)	0.0159 (5)	0.0174 (5)	−0.0003 (4)	0.0000 (4)	0.0005 (4)
C10	0.0172 (5)	0.0166 (5)	0.0169 (5)	−0.0009 (4)	0.0011 (4)	0.0010 (4)
C11	0.0219 (6)	0.0200 (6)	0.0164 (5)	0.0011 (4)	0.0003 (4)	0.0002 (4)
C12	0.0177 (5)	0.0199 (6)	0.0174 (5)	−0.0007 (4)	0.0014 (4)	0.0009 (4)
C13	0.0169 (5)	0.0194 (6)	0.0197 (6)	−0.0001 (4)	0.0015 (4)	0.0021 (4)
C14	0.0162 (5)	0.0175 (5)	0.0202 (6)	−0.0017 (4)	0.0019 (4)	0.0018 (4)
C15	0.0188 (5)	0.0167 (5)	0.0213 (6)	0.0005 (4)	0.0021 (4)	0.0028 (4)
C16	0.0240 (6)	0.0191 (6)	0.0201 (6)	−0.0022 (5)	0.0024 (5)	0.0026 (5)
C17	0.0266 (6)	0.0200 (6)	0.0234 (6)	−0.0014 (5)	0.0071 (5)	−0.0015 (5)
C18	0.0208 (6)	0.0192 (6)	0.0297 (7)	0.0026 (5)	0.0037 (5)	−0.0004 (5)
C19	0.0183 (5)	0.0204 (6)	0.0244 (6)	0.0011 (4)	0.0002 (5)	0.0016 (5)
C20	0.0286 (7)	0.0286 (7)	0.0213 (6)	0.0041 (5)	−0.0002 (5)	0.0043 (5)

Geometric parameters (Å, º) top

S1—C11	1.7216 (13)	C5—C6	1.3815 (18)
S1—C12	1.7382 (13)	C5—H5A	0.9300
O1—C8	1.3706 (15)	C6—C7	1.3887 (17)
O1—C7	1.3799 (15)	C6—H6A	0.9300
O2—C8	1.2151 (15)	C8—C9	1.4626 (17)
O3—C18	1.352 (2)	C9—C10	1.4678 (17)
O3—H1OA	0.89 (4)	C10—C11	1.3655 (17)
O3A—C16	1.403 (3)	C11—H11	0.965 (17)
O3A—H1OB	0.80 (5)	C13—C14	1.4858 (17)
N1—C12	1.2987 (16)	C13—C20	1.4996 (18)
N1—C10	1.3990 (16)	C14—C19	1.3964 (17)
N2—C12	1.3682 (16)	C14—C15	1.4057 (17)
N2—N3	1.3713 (15)	C15—C16	1.3858 (18)
N2—H1N2	0.85 (2)	C15—H15A	0.9300
N3—C13	1.2894 (16)	C16—C17	1.3898 (18)
C1—C9	1.3570 (17)	C16—H16A	0.9300
C1—C2	1.4316 (17)	C17—C18	1.386 (2)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C7	1.3964 (17)	C18—C19	1.3946 (19)
C2—C3	1.4044 (17)	C18—H18A	0.9300
C3—C4	1.3849 (18)	C19—H19A	0.9300
C3—H3A	0.9300	C20—H20A	0.9600
C4—C5	1.4009 (19)	C20—H20B	0.9600
C4—H4A	0.9300	C20—H20C	0.9600

C11—S1—C12	88.13 (6)	C10—C11—S1	110.77 (10)
C8—O1—C7	122.58 (10)	C10—C11—H11	127.8 (10)
C18—O3—H1OA	111 (2)	S1—C11—H11	121.4 (10)
C16—O3A—H1OB	102 (3)	N1—C12—N2	124.87 (12)
C12—N1—C10	109.05 (10)	N1—C12—S1	116.77 (10)
C12—N2—N3	114.89 (11)	N2—C12—S1	118.36 (9)
C12—N2—H1N2	118.2 (13)	N3—C13—C14	114.99 (11)
N3—N2—H1N2	126.9 (13)	N3—C13—C20	123.73 (12)
C13—N3—N2	119.58 (11)	C14—C13—C20	121.27 (11)
C9—C1—C2	121.80 (11)	C19—C14—C15	118.86 (12)
C9—C1—H1A	119.1	C19—C14—C13	120.81 (11)
C2—C1—H1A	119.1	C15—C14—C13	120.33 (11)
C7—C2—C3	118.15 (11)	C16—C15—C14	120.36 (12)
C7—C2—C1	118.13 (11)	C16—C15—H15A	119.8
C3—C2—C1	123.71 (12)	C14—C15—H15A	119.8
C4—C3—C2	120.22 (12)	C15—C16—C17	120.73 (12)
C4—C3—H3A	119.9	C15—C16—O3A	124.63 (15)
C2—C3—H3A	119.9	C17—C16—O3A	114.63 (15)
C3—C4—C5	120.00 (12)	C15—C16—H16A	119.6
C3—C4—H4A	120.0	C17—C16—H16A	119.6
C5—C4—H4A	120.0	O3A—C16—H16A	5.1
C6—C5—C4	120.91 (12)	C18—C17—C16	119.04 (12)
C6—C5—H5A	119.5	C18—C17—H17A	120.5
C4—C5—H5A	119.5	C16—C17—H17A	120.5
C5—C6—C7	118.34 (12)	O3—C18—C17	119.52 (14)
C5—C6—H6A	120.8	O3—C18—C19	119.37 (14)
C7—C6—H6A	120.8	C17—C18—C19	121.04 (12)
O1—C7—C6	117.37 (11)	O3—C18—H18A	2.7
O1—C7—C2	120.27 (11)	C17—C18—H18A	119.5
C6—C7—C2	122.37 (12)	C19—C18—H18A	119.5
O2—C8—O1	115.71 (11)	C18—C19—C14	119.94 (12)
O2—C8—C9	126.15 (12)	C18—C19—H19A	120.0
O1—C8—C9	118.14 (11)	C14—C19—H19A	120.0
C1—C9—C8	119.05 (11)	C13—C20—H20A	109.5
C1—C9—C10	121.73 (11)	C13—C20—H20B	109.5
C8—C9—C10	119.22 (11)	H20A—C20—H20B	109.5
C11—C10—N1	115.28 (11)	C13—C20—H20C	109.5
C11—C10—C9	127.12 (11)	H20A—C20—H20C	109.5
N1—C10—C9	117.59 (10)	H20B—C20—H20C	109.5

C12—N2—N3—C13	−179.10 (12)	C8—C9—C10—N1	−177.98 (11)
C9—C1—C2—C7	0.02 (19)	N1—C10—C11—S1	0.55 (14)
C9—C1—C2—C3	−179.70 (13)	C9—C10—C11—S1	−179.34 (10)
C7—C2—C3—C4	−0.2 (2)	C12—S1—C11—C10	−0.43 (10)
C1—C2—C3—C4	179.48 (13)	C10—N1—C12—N2	179.60 (12)
C2—C3—C4—C5	−0.4 (2)	C10—N1—C12—S1	0.00 (14)
C3—C4—C5—C6	0.3 (2)	N3—N2—C12—N1	−178.57 (12)
C4—C5—C6—C7	0.28 (19)	N3—N2—C12—S1	1.03 (15)
C8—O1—C7—C6	178.55 (11)	C11—S1—C12—N1	0.26 (11)
C8—O1—C7—C2	−1.91 (17)	C11—S1—C12—N2	−179.37 (11)
C5—C6—C7—O1	178.62 (11)	N2—N3—C13—C14	178.40 (11)
C5—C6—C7—C2	−0.91 (19)	N2—N3—C13—C20	−0.57 (19)
C3—C2—C7—O1	−178.63 (11)	N3—C13—C14—C19	172.60 (12)
C1—C2—C7—O1	1.64 (18)	C20—C13—C14—C19	−8.40 (18)
C3—C2—C7—C6	0.89 (19)	N3—C13—C14—C15	−8.30 (17)
C1—C2—C7—C6	−178.84 (12)	C20—C13—C14—C15	170.69 (12)
C7—O1—C8—O2	−179.37 (11)	C19—C14—C15—C16	−0.43 (18)
C7—O1—C8—C9	0.49 (17)	C13—C14—C15—C16	−179.54 (11)
C2—C1—C9—C8	−1.41 (18)	C14—C15—C16—C17	1.10 (19)
C2—C1—C9—C10	178.93 (11)	C14—C15—C16—O3A	179.92 (16)
O2—C8—C9—C1	−178.99 (13)	C15—C16—C17—C18	−0.56 (19)
O1—C8—C9—C1	1.17 (17)	O3A—C16—C17—C18	−179.49 (15)
O2—C8—C9—C10	0.7 (2)	C16—C17—C18—O3	176.29 (14)
O1—C8—C9—C10	−179.16 (11)	C16—C17—C18—C19	−0.7 (2)
C12—N1—C10—C11	−0.35 (15)	O3—C18—C19—C14	−175.63 (14)
C12—N1—C10—C9	179.55 (11)	C17—C18—C19—C14	1.3 (2)
C1—C9—C10—C11	−178.43 (13)	C15—C14—C19—C18	−0.76 (18)
C8—C9—C10—C11	1.90 (19)	C13—C14—C19—C18	178.35 (12)
C1—C9—C10—N1	1.68 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1OA···O2ⁱ	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A···O2ⁱ	0.93	2.59	3.3020 (17)	133

Symmetry code: (i) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₃O₃S
M_r	377.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.1569 (1), 9.9070 (2), 18.7478 (3)
β (°)	92.040 (1)
V (Å³)	1699.67 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.32 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.929, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	29914, 5400, 4641
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.07
No. of reflections	5400
No. of parameters	271
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1OA···O2ⁱ	0.89 (4)	1.89 (4)	2.7693 (19)	171 (4)
C19—H19A···O2ⁱ	0.93	2.59	3.3020 (17)	133

Symmetry code: (i) x+1, y−1, z.

Footnotes

‡Additional correspondence author, e-mail: ohasnah@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

AA, HO, CKL thank the Malaysian Government and Universiti Sains Malaysia (USM) for a grant [1001/PKimia/811133] to conduct this work. AA also thanks USM for a fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks USM for a post-doctoral research fellowship.

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