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

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

doi:10.1107/S1600536810021604

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1632-o1633

doi:10.1107/S1600536810021604

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

Afsheen Arshad,^a Hasnah Osman,^a ‡ Chan Kit Lam,^b Ching Kheng Quah ^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 2 June 2010; accepted 7 June 2010; online 16 June 2010)

In the title compound, C₂₀H₁₅N₃O₃S, an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The chromene ring system is inclined at dihedral angles of 14.21 (9) and 9.91 (10)°, respectively, with respect to the thiazole and benzene rings. The thiazole ring makes a dihedral angle of 24.06 (11)° with the benzene ring. In the crystal structure, O—H⋯O hydrogen bonds link the molecules into a zigzag chain along [20 $[\overline{1}]$ ]. Weak N—H⋯O and C—H⋯O interactions connect the chains into a three-dimensional network. π–π stacking interactions with a centroid–centroid distance of 3.4209 (14) Å are also observed between the chains.

Related literature

For a related structure, see: Arshad et al. (2010 ). For the synthesis, see: Siddiqui et al. (2009 ); Liu et al. (2008 ). For general background to and the biological activity of coumarin derivatives, see: Anderson et al. (2002 ); Finn et al. (2004 ); Hofmanova et al. (1998 ). For the biological activity of aminothiazole derivatives, see: Hiremath et al. (1992 ); Gursoy & Karah (2000 ); Jayashree et al. (2005 ); Patt et al. (1992 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₅N₃O₃S
M_r = 377.41
Monoclinic, P 2₁ /c
a = 9.1117 (16) Å
b = 16.225 (3) Å
c = 12.113 (2) Å
β = 104.657 (3)°
V = 1732.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.38 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.922, T_max = 0.990
16535 measured reflections
3957 independent reflections
2932 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.161
S = 1.10
3957 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H12N⋯O3ⁱ	0.88 (2)	2.36 (2)	3.213 (3)	164 (2)
O3—H13O⋯O2ⁱⁱ	0.89 (4)	1.87 (4)	2.743 (3)	169 (3)
C5—H5A⋯O3ⁱⁱⁱ	0.93	2.46	3.386 (3)	173
C11—H11A⋯O2	0.93	2.39	2.915 (3)	115
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) 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/S1600536810021604/is2557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021604/is2557Isup2.hkl

checkCIF report

Comment top

Aminothiazole ring is found to be associated with diverse pharmacological activities such as antifungal (Hiremath et al., 1992), anti-tuberculosis (Gursoy & Karah, 2000), anti-inflammation (Jayashree et al., 2005) and antihypertensive (Patt et al., 1992). In addition, coumarin and its derivatives also exhibit significant enzyme inhibition (Hofmanova et al., 1998), anticoagulant (Anderson et al., 2002) and free radical scavenging (Finn et al., 2004) activities. The title compound is a new derivative of thiazolyl coumarin. We present here its crystal structure.

Bond lengths (Allen et al., 1987) and the angles of the title compound (Fig. 1), are within the normal range and comparable with a related structure (Arshad et al., 2010). The molecular structure is stabilized by intramolecular C11—H11A···O2 hydrogen bond which generates an S(6) ring motif (Bernstein et al., 1995). The chromene (O1/C1–C9) ring system and thiazole (S1/N1/C10–C12) ring are approximately planar, with the maximum deviation of 0.021 (2) Å for atom O1 and 0.008 (2) Å for atom C10. The chromene ring system is inclined at angles of 14.21 (9) and 9.91 (10)° with respect to the thiazole and benzene (C14–C19) rings, respectively. The thiazole ring makes a dihedral angle of 24.06 (11)° with the benzene ring.

In the crystal packing (Fig.2), the N2—H12N···O3 and C5—H5A···O3 interactions form a pair of bifurcated acceptor bonds which together with O3—H13O···O2 interactions link the independent molecules into a three-dimensional network. The short intermolecular distance [3.4209 (14) Å] between symmetry-related S1/N1/C10–C12 (centroid Cg1) and O1/C1/C2/C7–C9 (centroid Cg2) rings [symmetry code: -x, -y, -z] indicates the existence of π–π stacking interaction.

Related literature top

For a related structure, see: Arshad et al. (2010). For the synthesis, see: Siddiqui et al. (2009); Liu et al. (2008). For general background to and the biological activity of coumarin derivatives, see: Anderson et al. (2002); Finn et al. (2004); Hofmanova et al. (1998). For the biological activity of aminothiazole derivatives, see: Hiremath et al. (1992); Gursoy & Karah (2000); Jayashree et al. (2005); Patt et al. (1992). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

4-Hydroxyacetophenone thiosemicarbazone (Liu et al., 2008) and 3-[ω-bromoacetyl coumarin] (Siddiqui et al., 2009) were synthesized as reported in the literature. The title compound was obtained by the cyclocondensation of 4-hydroxyacetophenone thiosemicarbazone with 3-[ω-bromoacetyl coumarin]. A solution of 3-[ω-bromoacetyl coumarin] (2.5 mmol) and 4-hydroxyacetophenone thiosemicarbazone (2.5 mmol) in chloroform-ethanol (2:1) was refluxed for 45 minutes at 60 °C to get dense yellow precipitates. The reaction mixture was cooled in ice bath and basified with ammonia to pH 7–8. The title compound was recrystallized from ethanol-chloroform (3:2) as yellow needle-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 showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Intramolecular interaction is shown by a dashed line.
	Fig. 2. The crystal structure of the title compound viewed along the c axis. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

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

Crystal data top

C₂₀H₁₅N₃O₃S	F(000) = 784
M_r = 377.41	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2347 reflections
a = 9.1117 (16) Å	θ = 2.8–27.3°
b = 16.225 (3) Å	µ = 0.21 mm⁻¹
c = 12.113 (2) Å	T = 100 K
β = 104.657 (3)°	Needle, yellow
V = 1732.5 (5) Å³	0.38 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	2932 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.922, T_max = 0.990	k = −21→21
16535 measured reflections	l = −15→15

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) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0927P)²] where P = (F_o² + 2F_c²)/3
3957 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₀H₁₅N₃O₃S	V = 1732.5 (5) Å³
M_r = 377.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1117 (16) Å	µ = 0.21 mm⁻¹
b = 16.225 (3) Å	T = 100 K
c = 12.113 (2) Å	0.38 × 0.06 × 0.05 mm
β = 104.657 (3)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3957 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2932 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.990	R_int = 0.060
16535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.40 e Å⁻³
3957 reflections	Δρ_min = −0.41 e Å⁻³
253 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	0.38934 (7)	0.12646 (3)	0.08727 (5)	0.01862 (18)
O1	−0.03963 (18)	−0.12925 (9)	0.20648 (14)	0.0161 (4)
O2	0.05580 (19)	−0.00659 (10)	0.25771 (15)	0.0200 (4)
O3	0.8063 (2)	0.48865 (10)	−0.15666 (16)	0.0223 (4)
N1	0.2563 (2)	−0.00002 (11)	−0.02742 (17)	0.0157 (4)
N2	0.4034 (2)	0.07847 (12)	−0.12284 (19)	0.0180 (4)
N3	0.4819 (2)	0.15129 (11)	−0.11761 (17)	0.0153 (4)
C1	0.0479 (3)	−0.06337 (13)	0.1917 (2)	0.0155 (5)
C2	−0.0638 (2)	−0.19722 (13)	0.1346 (2)	0.0148 (5)
C3	−0.1574 (3)	−0.25933 (14)	0.1574 (2)	0.0181 (5)
H3A	−0.2042	−0.2544	0.2170	0.022*
C4	−0.1785 (3)	−0.32860 (14)	0.0888 (2)	0.0198 (5)
H4A	−0.2406	−0.3708	0.1025	0.024*
C5	−0.1085 (3)	−0.33653 (14)	−0.0009 (2)	0.0212 (5)
H5A	−0.1237	−0.3838	−0.0458	0.025*
C6	−0.0166 (3)	−0.27378 (14)	−0.0225 (2)	0.0190 (5)
H6A	0.0295	−0.2789	−0.0825	0.023*
C7	0.0075 (2)	−0.20265 (13)	0.0454 (2)	0.0152 (5)
C8	0.1015 (3)	−0.13536 (13)	0.0300 (2)	0.0147 (5)
H8A	0.1499	−0.1381	−0.0289	0.018*
C9	0.1230 (2)	−0.06783 (13)	0.0976 (2)	0.0146 (5)
C10	0.2180 (2)	0.00109 (13)	0.07732 (19)	0.0138 (5)
C11	0.2764 (3)	0.06418 (14)	0.1475 (2)	0.0194 (5)
H11A	0.2582	0.0730	0.2188	0.023*
C12	0.3457 (2)	0.06236 (13)	−0.0311 (2)	0.0151 (5)
C13	0.5341 (3)	0.17206 (13)	−0.2030 (2)	0.0160 (5)
C14	0.6101 (2)	0.25398 (13)	−0.1918 (2)	0.0150 (5)
C15	0.5766 (3)	0.31265 (14)	−0.1168 (2)	0.0184 (5)
H15A	0.5077	0.2996	−0.0745	0.022*
C16	0.6444 (3)	0.38995 (14)	−0.1045 (2)	0.0207 (5)
H16A	0.6213	0.4280	−0.0541	0.025*
C17	0.7469 (3)	0.41031 (13)	−0.1679 (2)	0.0177 (5)
C18	0.7836 (3)	0.35256 (13)	−0.2415 (2)	0.0159 (5)
H18A	0.8541	0.3655	−0.2826	0.019*
C19	0.7150 (3)	0.27562 (13)	−0.2536 (2)	0.0166 (5)
H19A	0.7392	0.2377	−0.3038	0.020*
C20	0.5172 (3)	0.12174 (14)	−0.3094 (2)	0.0208 (5)
H20A	0.4122	0.1084	−0.3403	0.031*
H20B	0.5749	0.0718	−0.2914	0.031*
H20C	0.5537	0.1528	−0.3644	0.031*
H12N	0.364 (3)	0.0512 (15)	−0.186 (2)	0.016 (7)*
H13O	0.894 (4)	0.491 (2)	−0.176 (3)	0.060 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0201 (3)	0.0173 (3)	0.0188 (3)	−0.0056 (2)	0.0057 (3)	−0.0023 (2)
O1	0.0168 (8)	0.0155 (8)	0.0185 (9)	−0.0017 (6)	0.0093 (7)	−0.0006 (6)
O2	0.0204 (9)	0.0213 (8)	0.0198 (9)	−0.0021 (6)	0.0081 (8)	−0.0047 (7)
O3	0.0233 (10)	0.0163 (8)	0.0321 (11)	−0.0043 (7)	0.0162 (9)	−0.0022 (7)
N1	0.0157 (10)	0.0157 (9)	0.0173 (11)	−0.0020 (7)	0.0070 (9)	0.0005 (7)
N2	0.0210 (11)	0.0158 (9)	0.0193 (12)	−0.0052 (8)	0.0089 (9)	−0.0005 (8)
N3	0.0126 (9)	0.0149 (9)	0.0176 (11)	−0.0022 (7)	0.0023 (8)	0.0020 (7)
C1	0.0134 (11)	0.0169 (10)	0.0156 (12)	0.0005 (8)	0.0024 (9)	0.0012 (9)
C2	0.0131 (11)	0.0149 (10)	0.0152 (12)	0.0017 (8)	0.0016 (9)	0.0007 (8)
C3	0.0165 (11)	0.0222 (11)	0.0162 (12)	0.0000 (9)	0.0053 (10)	0.0032 (9)
C4	0.0169 (12)	0.0190 (11)	0.0236 (14)	−0.0052 (9)	0.0050 (10)	0.0024 (9)
C5	0.0224 (13)	0.0186 (11)	0.0213 (14)	−0.0040 (9)	0.0033 (11)	−0.0030 (10)
C6	0.0200 (12)	0.0212 (11)	0.0162 (13)	−0.0018 (9)	0.0055 (10)	−0.0020 (9)
C7	0.0141 (11)	0.0162 (10)	0.0143 (12)	0.0013 (8)	0.0017 (9)	0.0010 (8)
C8	0.0144 (11)	0.0188 (11)	0.0114 (12)	0.0017 (8)	0.0041 (9)	0.0018 (8)
C9	0.0122 (11)	0.0164 (10)	0.0161 (12)	0.0010 (8)	0.0054 (9)	0.0020 (9)
C10	0.0109 (11)	0.0170 (10)	0.0127 (12)	0.0016 (8)	0.0018 (9)	0.0028 (8)
C11	0.0227 (12)	0.0187 (11)	0.0194 (13)	−0.0024 (9)	0.0100 (11)	0.0000 (9)
C12	0.0129 (11)	0.0161 (10)	0.0159 (12)	0.0014 (8)	0.0029 (9)	0.0017 (9)
C13	0.0129 (11)	0.0174 (11)	0.0178 (13)	0.0009 (8)	0.0041 (10)	0.0027 (9)
C14	0.0127 (11)	0.0179 (11)	0.0140 (12)	0.0011 (8)	0.0027 (9)	0.0037 (9)
C15	0.0174 (12)	0.0202 (11)	0.0207 (13)	−0.0025 (9)	0.0106 (10)	0.0015 (9)
C16	0.0243 (13)	0.0168 (11)	0.0246 (14)	−0.0010 (9)	0.0127 (12)	−0.0037 (9)
C17	0.0183 (12)	0.0125 (10)	0.0233 (14)	−0.0009 (8)	0.0073 (10)	0.0027 (9)
C18	0.0139 (11)	0.0193 (11)	0.0162 (12)	0.0004 (8)	0.0067 (10)	0.0028 (9)
C19	0.0166 (11)	0.0188 (11)	0.0149 (12)	0.0033 (8)	0.0049 (10)	0.0015 (9)
C20	0.0208 (12)	0.0223 (12)	0.0198 (13)	−0.0039 (9)	0.0061 (11)	−0.0015 (10)

Geometric parameters (Å, º) top

S1—C11	1.730 (2)	C6—H6A	0.9300
S1—C12	1.735 (2)	C7—C8	1.429 (3)
O1—C1	1.372 (3)	C8—C9	1.352 (3)
O1—C2	1.388 (3)	C8—H8A	0.9300
O2—C1	1.210 (3)	C9—C10	1.472 (3)
O3—C17	1.375 (3)	C10—C11	1.351 (3)
O3—H13O	0.89 (4)	C11—H11A	0.9300
N1—C12	1.307 (3)	C13—C14	1.489 (3)
N1—C10	1.399 (3)	C13—C20	1.500 (3)
N2—C12	1.369 (3)	C14—C19	1.400 (3)
N2—N3	1.374 (3)	C14—C15	1.401 (3)
N2—H12N	0.88 (3)	C15—C16	1.389 (3)
N3—C13	1.288 (3)	C15—H15A	0.9300
C1—C9	1.471 (3)	C16—C17	1.391 (3)
C2—C3	1.393 (3)	C16—H16A	0.9300
C2—C7	1.397 (3)	C17—C18	1.391 (3)
C3—C4	1.382 (3)	C18—C19	1.387 (3)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.397 (3)	C19—H19A	0.9300
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.385 (3)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—C7	1.402 (3)

C11—S1—C12	87.85 (11)	C11—C10—C9	128.6 (2)
C1—O1—C2	122.81 (18)	N1—C10—C9	115.73 (19)
C17—O3—H13O	112 (2)	C10—C11—S1	110.99 (18)
C12—N1—C10	108.79 (19)	C10—C11—H11A	124.5
C12—N2—N3	115.41 (19)	S1—C11—H11A	124.5
C12—N2—H12N	117.1 (17)	N1—C12—N2	123.1 (2)
N3—N2—H12N	124.5 (17)	N1—C12—S1	116.75 (18)
C13—N3—N2	118.8 (2)	N2—C12—S1	120.13 (17)
O2—C1—O1	116.5 (2)	N3—C13—C14	114.7 (2)
O2—C1—C9	126.0 (2)	N3—C13—C20	124.7 (2)
O1—C1—C9	117.55 (19)	C14—C13—C20	120.6 (2)
O1—C2—C3	117.3 (2)	C19—C14—C15	117.8 (2)
O1—C2—C7	120.29 (19)	C19—C14—C13	122.7 (2)
C3—C2—C7	122.4 (2)	C15—C14—C13	119.5 (2)
C4—C3—C2	117.9 (2)	C16—C15—C14	121.3 (2)
C4—C3—H3A	121.1	C16—C15—H15A	119.4
C2—C3—H3A	121.1	C14—C15—H15A	119.4
C3—C4—C5	121.4 (2)	C15—C16—C17	119.8 (2)
C3—C4—H4A	119.3	C15—C16—H16A	120.1
C5—C4—H4A	119.3	C17—C16—H16A	120.1
C6—C5—C4	119.7 (2)	O3—C17—C16	117.8 (2)
C6—C5—H5A	120.1	O3—C17—C18	122.3 (2)
C4—C5—H5A	120.1	C16—C17—C18	119.8 (2)
C5—C6—C7	120.5 (2)	C19—C18—C17	120.0 (2)
C5—C6—H6A	119.8	C19—C18—H18A	120.0
C7—C6—H6A	119.8	C17—C18—H18A	120.0
C2—C7—C6	118.1 (2)	C18—C19—C14	121.3 (2)
C2—C7—C8	117.6 (2)	C18—C19—H19A	119.4
C6—C7—C8	124.3 (2)	C14—C19—H19A	119.4
C9—C8—C7	122.7 (2)	C13—C20—H20A	109.5
C9—C8—H8A	118.7	C13—C20—H20B	109.5
C7—C8—H8A	118.7	H20A—C20—H20B	109.5
C8—C9—C1	119.0 (2)	C13—C20—H20C	109.5
C8—C9—C10	121.0 (2)	H20A—C20—H20C	109.5
C1—C9—C10	120.02 (19)	H20B—C20—H20C	109.5
C11—C10—N1	115.6 (2)

C12—N2—N3—C13	−177.2 (2)	C8—C9—C10—N1	12.9 (3)
C2—O1—C1—O2	177.4 (2)	C1—C9—C10—N1	−166.16 (19)
C2—O1—C1—C9	−2.4 (3)	N1—C10—C11—S1	−1.4 (3)
C1—O1—C2—C3	−178.8 (2)	C9—C10—C11—S1	176.69 (18)
C1—O1—C2—C7	2.9 (3)	C12—S1—C11—C10	0.95 (18)
O1—C2—C3—C4	−177.9 (2)	C10—N1—C12—N2	180.0 (2)
C7—C2—C3—C4	0.3 (4)	C10—N1—C12—S1	−0.4 (2)
C2—C3—C4—C5	0.0 (4)	N3—N2—C12—N1	173.3 (2)
C3—C4—C5—C6	−0.4 (4)	N3—N2—C12—S1	−6.3 (3)
C4—C5—C6—C7	0.4 (4)	C11—S1—C12—N1	−0.31 (19)
O1—C2—C7—C6	177.9 (2)	C11—S1—C12—N2	179.3 (2)
C3—C2—C7—C6	−0.3 (3)	N2—N3—C13—C14	176.85 (19)
O1—C2—C7—C8	−1.6 (3)	N2—N3—C13—C20	−0.7 (3)
C3—C2—C7—C8	−179.8 (2)	N3—C13—C14—C19	158.3 (2)
C5—C6—C7—C2	−0.1 (3)	C20—C13—C14—C19	−24.1 (3)
C5—C6—C7—C8	179.4 (2)	N3—C13—C14—C15	−21.8 (3)
C2—C7—C8—C9	−0.1 (3)	C20—C13—C14—C15	155.9 (2)
C6—C7—C8—C9	−179.6 (2)	C19—C14—C15—C16	0.4 (4)
C7—C8—C9—C1	0.5 (3)	C13—C14—C15—C16	−179.6 (2)
C7—C8—C9—C10	−178.6 (2)	C14—C15—C16—C17	0.4 (4)
O2—C1—C9—C8	−179.2 (2)	C15—C16—C17—O3	177.3 (2)
O1—C1—C9—C8	0.7 (3)	C15—C16—C17—C18	−1.4 (4)
O2—C1—C9—C10	−0.1 (4)	O3—C17—C18—C19	−177.0 (2)
O1—C1—C9—C10	179.81 (19)	C16—C17—C18—C19	1.6 (4)
C12—N1—C10—C11	1.2 (3)	C17—C18—C19—C14	−0.9 (4)
C12—N1—C10—C9	−177.19 (19)	C15—C14—C19—C18	−0.1 (3)
C8—C9—C10—C11	−165.2 (2)	C13—C14—C19—C18	179.8 (2)
C1—C9—C10—C11	15.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H12N···O3ⁱ	0.88 (2)	2.36 (2)	3.213 (3)	164 (2)
O3—H13O···O2ⁱⁱ	0.89 (4)	1.87 (4)	2.743 (3)	169 (3)
C5—H5A···O3ⁱⁱⁱ	0.93	2.46	3.386 (3)	173
C11—H11A···O2	0.93	2.39	2.915 (3)	115

Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x+1, −y+1/2, z−1/2; (iii) 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)	9.1117 (16), 16.225 (3), 12.113 (2)
β (°)	104.657 (3)
V (Å³)	1732.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.38 × 0.06 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.922, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	16535, 3957, 2932
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.161, 1.10
No. of reflections	3957
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.41

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N2—H12N···O3ⁱ	0.88 (2)	2.36 (2)	3.213 (3)	164 (2)
O3—H13O···O2ⁱⁱ	0.89 (4)	1.87 (4)	2.743 (3)	169 (3)
C5—H5A···O3ⁱⁱⁱ	0.9300	2.4600	3.386 (3)	173.00
C11—H11A···O2	0.9300	2.3900	2.915 (3)	115.00

Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x+1, −y+1/2, z−1/2; (iii) x−1, y−1, z.

Footnotes

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

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

We thank the Malaysian Government and Universiti Sains Malaysia (USM) for a Short Term grant (304/PKIMIA/639004) and an RU Grant (1001/PKIMIA/811133) to conduct this work. HKF and CKQ thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). AA thanks the Pakistan Government and PCSIR for financial scholarship support. CKQ also thanks USM for the award of USM Fellowship.

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