(E)-6-Bromo-3-{2-[2-(4-chloro­benzyl­idene)hydrazin­yl]thia­zol-5-yl}-2H-chromen-2-one

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

doi:10.1107/S1600536811011172

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o1007-o1008

doi:10.1107/S1600536811011172

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(E)-6-Bromo-3-{2-[2-(4-chlorobenzylidene)hydrazinyl]thiazol-5-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 19 March 2011; accepted 25 March 2011; online 31 March 2011)

In the title compound, C₁₉H₁₁N₃O₂SClBr, the chromene ring system and the thiazole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The molecule adopts an E configuration about the central C=N double bond. The central thiazole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The molecular structure features a short C—H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains along the b axis. π–π stacking interactions [centroid-centroid distance = 3.4813 (15) Å] are also present.

Related literature

For the biological activity and applications of thiazolyl coumarin derivatives, see: Samsonova et al. (2007 ); Bullock et al. (2009 ); Siddiqui et al. (2009 ); Kalkhambkar et al. (2007 ); Kamal et al. (2009 ); Desai et al. (2008 ). For the synthesis of the title compound, see: Bakkar et al. (2003 ); Vijesh et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₁BrClN₃O₂S
M_r = 460.73
Monoclinic, C 2/c
a = 30.5837 (7) Å
b = 13.6682 (3) Å
c = 9.0454 (1) Å
β = 90.161 (2)°
V = 3781.18 (13) Å³
Z = 8
Mo Kα radiation
μ = 2.45 mm⁻¹
T = 296 K
0.21 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.628, T_max = 0.842
29664 measured reflections
5499 independent reflections
2216 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 0.97
5499 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.81 (4)	2.16 (4)	2.957 (4)	169 (4)
C11—H11A⋯O2	0.93	2.35	2.878 (4)	115
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811011172/sj5122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011172/sj5122Isup2.hkl

checkCIF report

Comment top

Thiazolyl coumarin derivatives are reported to be associated with diverse applications. They have industrial applications as fluorescent probes, laser dyes (Samsonova et al., 2007) and luminescents (Bullock et al., 2009). They also exhibit a variety of biological activities as anticonvulsants (Siddiqui et al., 2009), analgesics, anti-inflammatory (Kalkhambkar et al., 2007) and antimicrobial agents (Kamal et al., 2009; Desai et al., 2008). The title compound is a new derivative of thiazolylcoumarin. We present here its crystal structure.

The molecular structure of the compound, (I), displays a trans configuration with respect to the C13═N3 double bond. The chromene (O1/C1–C9) ring system and thiazole (S1/N1/C10–C12) ring are approximately planar, with the maximum deviation of 0.033 (3) Å for atom C2 and 0.006 (3)Å for atom C12, respectively. The central thiazole (S1/N1/C10–C12) ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl (C14–C19) ring and the chromene (O1/C1–C9) ring, respectively.

In the crystal packing (Fig. 2), the molecular structure is stabilized by an intramolecular C—H···O (Table 1) hydrogen bond which generates an S(6) (Bernstein et al., 1995) ring motif. Furthermore, the crystal structure is stabilized by intermolecular N—H···O hydrogen bonds which link the molecules into chains parallel to the b-axis. π···π [centroid-centroid distance = 3.4813 (15) Å; 1/2-X, 1/2-Y, 2-Z] stacking interactions between the thiazole (S1/N1/C10–C12) and pyran (O1/C3–C7) rings are also observed.

Related literature top

For the biological activity and applications of thiazolyl coumarin derivatives, see: Samsonova et al. (2007); Bullock et al. (2009); Siddiqui et al. (2009); Kalkhambkar et al. (2007); Kamal et al. (2009); Desai et al. (2008). For the synthesis of the title compound, see: Bakkar et al. (2003); Vijesh et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

4-chlorobenzylidene thiosemicarbazone (Bakkar et al., 2003) and 6-bromo-3-(2-bromoacetyl)-2H-chromen-2-one (Vijesh et al., 2010) were synthesized as reported in the literature. The title compound (I) was obtained by the cyclocondensation of 4-chlorobenzylidene thiosemicarbazone with 6-bromo-3-(2-bromoacetyl)- 2H-chromen-2-one. A solution of 6-bromo-3-(2-bromoacetyl)-2H- chromen-2-one (2.5 mmol) and 4-chlorobenzylidene thiosemicarbazone (2.5 mmol) in chloroform-ethanol (2:1) was refluxed for 2 hours at 60°C to yield a dense yellow precipitate. The reaction mixture was cooled in ice bath and basified with ammonia to pH 7–8. The title compound (I) was recrystallized from ethanol-chloroform (1:2) to give yellow block 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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound (I).

(E)-6-Bromo-3-{2-[2-(4-chlorobenzylidene)hydrazinyl]thiazol-5-yl}- 2H-chromen-2-one top

Crystal data top

C₁₉H₁₁BrClN₃O₂S	F(000) = 1840
M_r = 460.73	D_x = 1.619 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3684 reflections
a = 30.5837 (7) Å	θ = 2.5–23.1°
b = 13.6682 (3) Å	µ = 2.45 mm⁻¹
c = 9.0454 (1) Å	T = 296 K
β = 90.161 (2)°	Block, yellow
V = 3781.18 (13) Å³	0.21 × 0.16 × 0.07 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5499 independent reflections
Radiation source: fine-focus sealed tube	2216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→42
T_min = 0.628, T_max = 0.842	k = −19→19
29664 measured reflections	l = −12→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0551P)² + 0.960P] where P = (F_o² + 2F_c²)/3
5499 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₁BrClN₃O₂S	V = 3781.18 (13) Å³
M_r = 460.73	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.5837 (7) Å	µ = 2.45 mm⁻¹
b = 13.6682 (3) Å	T = 296 K
c = 9.0454 (1) Å	0.21 × 0.16 × 0.07 mm
β = 90.161 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5499 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2216 reflections with I > 2σ(I)
T_min = 0.628, T_max = 0.842	R_int = 0.058
29664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.31 e Å⁻³
5499 reflections	Δρ_min = −0.34 e Å⁻³
248 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.437955 (16)	0.51731 (4)	1.13651 (6)	0.1287 (3)
Cl1	−0.00680 (3)	0.31602 (10)	−0.05275 (11)	0.1132 (4)
S1	0.19723 (3)	0.13873 (7)	0.60268 (9)	0.0712 (3)
O1	0.33937 (7)	0.13971 (15)	1.0762 (2)	0.0679 (6)
O2	0.29214 (8)	0.04381 (19)	0.9684 (3)	0.0902 (7)
N1	0.23951 (7)	0.28268 (18)	0.7199 (2)	0.0575 (6)
N2	0.18701 (9)	0.3330 (2)	0.5513 (3)	0.0698 (8)
N3	0.15428 (8)	0.3072 (2)	0.4558 (2)	0.0629 (7)
C1	0.41549 (11)	0.3221 (3)	1.2104 (4)	0.0778 (10)
H1A	0.4381	0.3273	1.2790	0.093*
C2	0.39334 (10)	0.2362 (3)	1.1954 (3)	0.0738 (9)
H2A	0.4009	0.1825	1.2533	0.089*
C3	0.35967 (9)	0.2291 (2)	1.0938 (3)	0.0609 (8)
C4	0.30642 (10)	0.1259 (3)	0.9763 (3)	0.0652 (8)
C5	0.29156 (9)	0.2090 (2)	0.8891 (3)	0.0556 (7)
C6	0.31145 (9)	0.2961 (2)	0.9077 (3)	0.0591 (8)
H6A	0.3018	0.3493	0.8524	0.071*
C7	0.34686 (9)	0.3096 (2)	1.0094 (3)	0.0601 (8)
C8	0.36987 (9)	0.3966 (3)	1.0262 (4)	0.0715 (9)
H8A	0.3620	0.4515	0.9716	0.086*
C9	0.40440 (10)	0.4013 (3)	1.1240 (4)	0.0766 (10)
C10	0.25573 (9)	0.1967 (2)	0.7827 (3)	0.0569 (7)
C11	0.23679 (10)	0.1131 (2)	0.7328 (3)	0.0662 (8)
H11A	0.2442	0.0505	0.7645	0.079*
C12	0.20879 (9)	0.2616 (2)	0.6261 (3)	0.0583 (8)
C13	0.13768 (10)	0.3778 (3)	0.3809 (3)	0.0666 (8)
H13A	0.1486	0.4408	0.3935	0.080*
C14	0.10205 (10)	0.3614 (2)	0.2765 (3)	0.0609 (8)
C15	0.08312 (10)	0.2710 (3)	0.2569 (3)	0.0713 (9)
H15A	0.0931	0.2183	0.3128	0.086*
C16	0.04983 (10)	0.2566 (3)	0.1567 (3)	0.0763 (10)
H16A	0.0377	0.1948	0.1440	0.092*
C17	0.03487 (10)	0.3341 (3)	0.0762 (3)	0.0767 (10)
C18	0.05284 (12)	0.4249 (3)	0.0907 (4)	0.0925 (12)
H18A	0.0426	0.4771	0.0344	0.111*
C19	0.08655 (11)	0.4378 (3)	0.1909 (4)	0.0846 (10)
H19A	0.0991	0.4994	0.2010	0.102*
H1N2	0.1963 (12)	0.388 (3)	0.547 (4)	0.092 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1122 (4)	0.0915 (4)	0.1821 (5)	−0.0164 (3)	−0.0729 (4)	−0.0212 (3)
Cl1	0.0812 (6)	0.1664 (12)	0.0917 (6)	0.0210 (7)	−0.0463 (5)	−0.0255 (7)
S1	0.0712 (5)	0.0676 (6)	0.0748 (5)	−0.0092 (4)	−0.0221 (4)	−0.0101 (4)
O1	0.0663 (13)	0.0633 (15)	0.0739 (13)	0.0083 (11)	−0.0199 (11)	0.0053 (11)
O2	0.0935 (17)	0.0603 (16)	0.1165 (19)	−0.0022 (14)	−0.0368 (14)	0.0108 (15)
N1	0.0574 (14)	0.0579 (16)	0.0572 (13)	0.0024 (12)	−0.0134 (12)	−0.0054 (12)
N2	0.0731 (18)	0.065 (2)	0.0715 (17)	−0.0067 (16)	−0.0335 (14)	−0.0020 (16)
N3	0.0618 (15)	0.0675 (18)	0.0593 (14)	−0.0034 (13)	−0.0222 (12)	−0.0035 (13)
C1	0.062 (2)	0.092 (3)	0.079 (2)	0.012 (2)	−0.0280 (17)	−0.015 (2)
C2	0.071 (2)	0.078 (2)	0.073 (2)	0.0179 (19)	−0.0248 (17)	0.0020 (19)
C3	0.0561 (17)	0.064 (2)	0.0623 (18)	0.0080 (16)	−0.0080 (15)	−0.0052 (16)
C4	0.0615 (19)	0.059 (2)	0.075 (2)	0.0033 (17)	−0.0123 (16)	0.0000 (18)
C5	0.0544 (16)	0.057 (2)	0.0556 (16)	0.0079 (15)	−0.0070 (13)	−0.0087 (15)
C6	0.0574 (17)	0.0558 (19)	0.0639 (17)	0.0043 (15)	−0.0139 (14)	−0.0037 (15)
C7	0.0523 (16)	0.064 (2)	0.0638 (18)	0.0106 (15)	−0.0140 (14)	−0.0096 (16)
C8	0.0622 (19)	0.063 (2)	0.089 (2)	0.0099 (17)	−0.0253 (17)	−0.0119 (19)
C9	0.066 (2)	0.073 (2)	0.091 (2)	0.0052 (18)	−0.0242 (18)	−0.022 (2)
C10	0.0553 (17)	0.058 (2)	0.0577 (17)	0.0031 (15)	−0.0051 (14)	−0.0033 (15)
C11	0.0664 (19)	0.058 (2)	0.074 (2)	0.0010 (16)	−0.0174 (16)	−0.0036 (17)
C12	0.0579 (17)	0.064 (2)	0.0535 (16)	0.0003 (15)	−0.0114 (14)	−0.0064 (15)
C13	0.0686 (19)	0.068 (2)	0.0634 (18)	−0.0012 (17)	−0.0199 (16)	−0.0117 (17)
C14	0.0605 (18)	0.063 (2)	0.0592 (17)	0.0073 (16)	−0.0150 (15)	−0.0078 (16)
C15	0.0673 (19)	0.078 (2)	0.0688 (19)	0.0023 (18)	−0.0228 (16)	−0.0028 (18)
C16	0.066 (2)	0.085 (3)	0.078 (2)	−0.0002 (19)	−0.0202 (17)	−0.011 (2)
C17	0.061 (2)	0.106 (3)	0.0624 (19)	0.017 (2)	−0.0232 (16)	−0.015 (2)
C18	0.095 (3)	0.095 (3)	0.088 (3)	0.025 (2)	−0.037 (2)	0.005 (2)
C19	0.089 (2)	0.074 (2)	0.090 (2)	0.009 (2)	−0.032 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Br1—C9	1.892 (3)	C5—C10	1.466 (4)
Cl1—C17	1.743 (3)	C6—C7	1.431 (4)
S1—C11	1.721 (3)	C6—H6A	0.9300
S1—C12	1.728 (3)	C7—C8	1.390 (4)
O1—C4	1.365 (4)	C8—C9	1.377 (4)
O1—C3	1.379 (4)	C8—H8A	0.9300
O2—C4	1.206 (4)	C10—C11	1.359 (4)
N1—C12	1.297 (3)	C11—H11A	0.9300
N1—C10	1.395 (4)	C13—C14	1.458 (4)
N2—C12	1.361 (4)	C13—H13A	0.9300
N2—N3	1.366 (3)	C14—C15	1.376 (4)
N2—H1N2	0.81 (4)	C14—C19	1.383 (4)
N3—C13	1.283 (4)	C15—C16	1.376 (4)
C1—C2	1.363 (5)	C15—H15A	0.9300
C1—C9	1.377 (5)	C16—C17	1.364 (5)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.382 (4)	C17—C18	1.363 (5)
C2—H2A	0.9300	C18—C19	1.382 (5)
C3—C7	1.395 (4)	C18—H18A	0.9300
C4—C5	1.455 (4)	C19—H19A	0.9300
C5—C6	1.347 (4)

C11—S1—C12	88.34 (15)	C1—C9—Br1	119.5 (2)
C4—O1—C3	122.0 (2)	C8—C9—Br1	119.5 (3)
C12—N1—C10	109.6 (2)	C11—C10—N1	115.0 (2)
C12—N2—N3	119.1 (3)	C11—C10—C5	129.2 (3)
C12—N2—H1N2	122 (3)	N1—C10—C5	115.8 (3)
N3—N2—H1N2	118 (3)	C10—C11—S1	110.7 (2)
C13—N3—N2	115.4 (3)	C10—C11—H11A	124.6
C2—C1—C9	120.0 (3)	S1—C11—H11A	124.6
C2—C1—H1A	120.0	N1—C12—N2	121.2 (3)
C9—C1—H1A	120.0	N1—C12—S1	116.4 (2)
C1—C2—C3	119.7 (3)	N2—C12—S1	122.4 (2)
C1—C2—H2A	120.1	N3—C13—C14	121.3 (3)
C3—C2—H2A	120.1	N3—C13—H13A	119.3
O1—C3—C2	118.3 (3)	C14—C13—H13A	119.3
O1—C3—C7	120.6 (2)	C15—C14—C19	117.6 (3)
C2—C3—C7	121.1 (3)	C15—C14—C13	122.4 (3)
O2—C4—O1	115.7 (3)	C19—C14—C13	120.0 (3)
O2—C4—C5	125.6 (3)	C16—C15—C14	121.6 (3)
O1—C4—C5	118.7 (3)	C16—C15—H15A	119.2
C6—C5—C4	118.8 (3)	C14—C15—H15A	119.2
C6—C5—C10	121.3 (3)	C17—C16—C15	119.2 (3)
C4—C5—C10	119.9 (3)	C17—C16—H16A	120.4
C5—C6—C7	122.3 (3)	C15—C16—H16A	120.4
C5—C6—H6A	118.8	C18—C17—C16	121.4 (3)
C7—C6—H6A	118.8	C18—C17—Cl1	119.2 (3)
C8—C7—C3	118.3 (3)	C16—C17—Cl1	119.4 (3)
C8—C7—C6	124.2 (3)	C17—C18—C19	118.6 (4)
C3—C7—C6	117.5 (3)	C17—C18—H18A	120.7
C9—C8—C7	119.8 (3)	C19—C18—H18A	120.7
C9—C8—H8A	120.1	C18—C19—C14	121.6 (4)
C7—C8—H8A	120.1	C18—C19—H19A	119.2
C1—C9—C8	121.0 (3)	C14—C19—H19A	119.2

C12—N2—N3—C13	−174.7 (3)	C12—N1—C10—C5	178.7 (2)
C9—C1—C2—C3	−0.3 (5)	C6—C5—C10—C11	168.5 (3)
C4—O1—C3—C2	−178.7 (3)	C4—C5—C10—C11	−11.1 (5)
C4—O1—C3—C7	0.3 (4)	C6—C5—C10—N1	−9.3 (4)
C1—C2—C3—O1	176.8 (3)	C4—C5—C10—N1	171.1 (3)
C1—C2—C3—C7	−2.2 (5)	N1—C10—C11—S1	0.1 (3)
C3—O1—C4—O2	178.1 (3)	C5—C10—C11—S1	−177.7 (2)
C3—O1—C4—C5	−1.8 (4)	C12—S1—C11—C10	−0.5 (2)
O2—C4—C5—C6	−178.4 (3)	C10—N1—C12—N2	178.9 (3)
O1—C4—C5—C6	1.4 (4)	C10—N1—C12—S1	−1.0 (3)
O2—C4—C5—C10	1.2 (5)	N3—N2—C12—N1	−178.7 (3)
O1—C4—C5—C10	−179.0 (3)	N3—N2—C12—S1	1.2 (4)
C4—C5—C6—C7	0.4 (4)	C11—S1—C12—N1	0.9 (2)
C10—C5—C6—C7	−179.2 (3)	C11—S1—C12—N2	−179.0 (3)
O1—C3—C7—C8	−176.8 (3)	N2—N3—C13—C14	−179.1 (3)
C2—C3—C7—C8	2.2 (4)	N3—C13—C14—C15	2.8 (5)
O1—C3—C7—C6	1.5 (4)	N3—C13—C14—C19	−176.2 (3)
C2—C3—C7—C6	−179.5 (3)	C19—C14—C15—C16	−0.3 (5)
C5—C6—C7—C8	176.3 (3)	C13—C14—C15—C16	−179.3 (3)
C5—C6—C7—C3	−1.9 (4)	C14—C15—C16—C17	−0.8 (5)
C3—C7—C8—C9	0.3 (5)	C15—C16—C17—C18	1.4 (5)
C6—C7—C8—C9	−177.9 (3)	C15—C16—C17—Cl1	179.1 (2)
C2—C1—C9—C8	2.8 (5)	C16—C17—C18—C19	−0.8 (6)
C2—C1—C9—Br1	−175.8 (3)	Cl1—C17—C18—C19	−178.5 (3)
C7—C8—C9—C1	−2.8 (5)	C17—C18—C19—C14	−0.4 (6)
C7—C8—C9—Br1	175.8 (2)	C15—C14—C19—C18	1.0 (5)
C12—N1—C10—C11	0.6 (4)	C13—C14—C19—C18	180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.81 (4)	2.16 (4)	2.957 (4)	169 (4)
C11—H11A···O2	0.93	2.35	2.878 (4)	115

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₁BrClN₃O₂S
M_r	460.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	30.5837 (7), 13.6682 (3), 9.0454 (1)
β (°)	90.161 (2)
V (Å³)	3781.18 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.21 × 0.16 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.628, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	29664, 5499, 2216
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 0.97
No. of reflections	5499
No. of parameters	248
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

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
N2—H1N2···O2ⁱ	0.81 (4)	2.16 (4)	2.957 (4)	169 (4)
C11—H11A···O2	0.93	2.35	2.878 (4)	115

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

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 Universiti Sains Malaysia for a fellowship. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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