(E)-6-Bromo-3-{2-[2-(2-meth­oxy­benzyl­idene)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/S1600536811024536

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1825

doi:10.1107/S1600536811024536

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(E)-6-Bromo-3-{2-[2-(2-methoxybenzylidene)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 21 June 2011; accepted 22 June 2011; online 25 June 2011)

In the title compound, C₂₀H₁₄BrN₃O₃S, the molecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thiazole ring are approximately planar [maximum deviations = 0.029 (3) and 0.007 (3) Å, respectively]. The chromene ring system is inclined at angles of 7.37 (12) and 13.90 (13)° with respect to the thiazole and benzene rings, respectively, while the thiazole ring makes a dihedral angle of 12.58 (15)° with the benzene ring. In the crystal, molecules are connected by N—H⋯O hydrogen bonds, forming C(8) supramolecular chains along the c axis.

Related literature

For related structures, further synthetic details and background references, see: Arshad et al. (2011a ,b ).

Experimental

Crystal data

C₂₀H₁₄BrN₃O₃S
M_r = 456.31
Monoclinic, P 2₁ /c
a = 7.2802 (12) Å
b = 19.551 (3) Å
c = 14.0638 (18) Å
β = 113.352 (7)°
V = 1837.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 296 K
0.43 × 0.07 × 0.04 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.427, T_max = 0.921
11951 measured reflections
4266 independent reflections
2786 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.089
S = 1.01
4266 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O2ⁱ	0.94	2.10	3.021 (3)	164
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536811024536/hb5923sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024536/hb5923Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024536/hb5923Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of substituted coumarins (Arshad et al., 2011a,b) we now present the crystal structure of the title compound, (I).

In (I), the molecule adopts an E configuration about the central C13═N3 double bond. The chromene (O1/C1–C9) and the thiazole (S1/N1/C10–C12) rings are approximately planar [maximum deviations of 0.029 (3) Å for atom C4 and 0.007 (3) Å for atom C12, respectively]. The chromene (O1/C1–C9) ring system is inclined at angles of 7.37 (12)° and 13.90 (13)° with respect to the thiazole (S1/N1/C10–C12) and benzene (C14–C19) rings, respectively, while the thiazole (S1/N1/C10–C12) ring makes a dihedral angle of 12.58 (15)° with the benzene ((C14–C19) ring.

In the crystal (Fig. 2), the molecules are connected by N2—H1···O2 (Table 1) hydrogen bonds forming supramolecular chains along the c-axis.

Related literature top

For related structures, further synthetic details and background references, see: Arshad et al. (2011a,b).

Experimental top

The title compound was synthesized by the same procedure as mentioned in our previous papers (Arshad et al., 2011a,b). 2-Methoxy benzylidene thiosemicarbazone was reacted with 6-bromo-3- (2-bromoacetyl)-2H-chromen-2-one in chloroform-ethanol (2:1) mixture. The reaction mixture was refluxed for 2–3 hours at 60°C to get dense yellow precipitates. It was cooled in ice bath and basified with ammonia to pH 7–8. The title compound (I) was recrystallized from CHCl₃–EtOH (1:1) as golden yellow needles.

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 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of a one-dimensional supramolecular chain along the c-axis.

(E)-6-Bromo-3-{2-[2-(2-methoxybenzylidene)hydrazinyl]- 1,3-thiazol-4-yl}-2H-chromen-2-one top

Crystal data top

C₂₀H₁₄BrN₃O₃S	F(000) = 920
M_r = 456.31	D_x = 1.649 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2197 reflections
a = 7.2802 (12) Å	θ = 3.0–22.4°
b = 19.551 (3) Å	µ = 2.38 mm⁻¹
c = 14.0638 (18) Å	T = 296 K
β = 113.352 (7)°	Needle, yellow
V = 1837.8 (5) Å³	0.43 × 0.07 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	4266 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.7°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.427, T_max = 0.921	k = −25→24
11951 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.034P)² + 0.488P] where P = (F_o² + 2F_c²)/3
4266 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₄BrN₃O₃S	V = 1837.8 (5) Å³
M_r = 456.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2802 (12) Å	µ = 2.38 mm⁻¹
b = 19.551 (3) Å	T = 296 K
c = 14.0638 (18) Å	0.43 × 0.07 × 0.04 mm
β = 113.352 (7)°

Data collection top

Bruker APEXII DUO CCD diffractometer	4266 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2786 reflections with I > 2σ(I)
T_min = 0.427, T_max = 0.921	R_int = 0.036
11951 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
4266 reflections	Δρ_min = −0.29 e Å⁻³
253 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	0.24394 (5)	1.084300 (17)	0.06129 (3)	0.06481 (13)
S1	0.21746 (11)	0.61887 (3)	0.38892 (5)	0.04655 (18)
O1	0.2719 (3)	0.92795 (9)	0.43367 (12)	0.0453 (4)
O2	0.2679 (3)	0.83501 (10)	0.51902 (14)	0.0567 (5)
O3	0.2197 (3)	0.37198 (9)	0.04438 (13)	0.0518 (5)
N1	0.2186 (3)	0.71059 (10)	0.25691 (15)	0.0403 (5)
N2	0.2131 (3)	0.59752 (10)	0.19923 (16)	0.0459 (6)
H1	0.2264	0.6102	0.1375	0.055*
N3	0.2291 (3)	0.53132 (10)	0.23123 (16)	0.0397 (5)
C1	0.2567 (4)	0.85797 (13)	0.43706 (19)	0.0402 (6)
C2	0.2663 (4)	0.96192 (13)	0.34700 (19)	0.0407 (6)
C3	0.2939 (4)	1.03179 (15)	0.3551 (2)	0.0515 (7)
H3A	0.3160	1.0541	0.4171	0.062*
C4	0.2880 (4)	1.06785 (14)	0.2703 (2)	0.0523 (7)
H4A	0.3068	1.1150	0.2744	0.063*
C5	0.2538 (4)	1.03353 (14)	0.1781 (2)	0.0446 (6)
C6	0.2293 (4)	0.96446 (14)	0.1706 (2)	0.0439 (6)
H6A	0.2081	0.9424	0.1085	0.053*
C7	0.2358 (4)	0.92670 (12)	0.25618 (18)	0.0372 (6)
C8	0.2190 (4)	0.85417 (13)	0.25783 (19)	0.0401 (6)
H8A	0.1991	0.8297	0.1978	0.048*
C9	0.2310 (4)	0.81934 (13)	0.34368 (18)	0.0372 (6)
C10	0.2232 (4)	0.74489 (13)	0.34487 (18)	0.0366 (6)
C11	0.2234 (4)	0.70361 (13)	0.42228 (19)	0.0430 (6)
H11A	0.2264	0.7192	0.4854	0.052*
C12	0.2177 (4)	0.64534 (12)	0.27085 (18)	0.0363 (6)
C13	0.2343 (4)	0.48370 (12)	0.17014 (19)	0.0375 (6)
H13A	0.2209	0.4934	0.1030	0.045*
C14	0.2620 (4)	0.41341 (12)	0.20920 (18)	0.0348 (5)
C15	0.3017 (4)	0.40043 (13)	0.3125 (2)	0.0445 (6)
H15A	0.3043	0.4367	0.3559	0.053*
C16	0.3374 (5)	0.33511 (14)	0.3522 (2)	0.0544 (8)
H16A	0.3618	0.3275	0.4215	0.065*
C17	0.3368 (5)	0.28129 (14)	0.2896 (2)	0.0557 (8)
H17A	0.3650	0.2374	0.3170	0.067*
C18	0.2947 (4)	0.29182 (13)	0.1862 (2)	0.0479 (7)
H18A	0.2917	0.2550	0.1437	0.057*
C19	0.2572 (4)	0.35707 (13)	0.14584 (18)	0.0376 (6)
C20	0.2017 (5)	0.31519 (14)	−0.0228 (2)	0.0530 (7)
H20A	0.1687	0.3315	−0.0920	0.080*
H20B	0.0979	0.2852	−0.0220	0.080*
H20C	0.3262	0.2908	0.0005	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0782 (2)	0.0614 (2)	0.0665 (2)	−0.00399 (17)	0.04110 (19)	0.01182 (16)
S1	0.0669 (5)	0.0376 (4)	0.0421 (4)	−0.0001 (3)	0.0291 (3)	0.0017 (3)
O1	0.0660 (12)	0.0354 (10)	0.0349 (10)	0.0021 (9)	0.0203 (9)	−0.0065 (8)
O2	0.0930 (16)	0.0460 (11)	0.0367 (11)	0.0041 (10)	0.0315 (11)	−0.0039 (9)
O3	0.0867 (14)	0.0353 (10)	0.0391 (10)	−0.0008 (10)	0.0310 (10)	−0.0042 (8)
N1	0.0546 (13)	0.0317 (12)	0.0366 (12)	−0.0013 (10)	0.0202 (10)	−0.0057 (9)
N2	0.0760 (16)	0.0297 (12)	0.0394 (12)	−0.0014 (11)	0.0307 (12)	−0.0028 (9)
N3	0.0529 (13)	0.0285 (11)	0.0404 (12)	−0.0002 (10)	0.0213 (10)	−0.0002 (9)
C1	0.0459 (15)	0.0371 (15)	0.0377 (14)	0.0032 (12)	0.0167 (12)	−0.0057 (12)
C2	0.0451 (15)	0.0357 (15)	0.0408 (15)	0.0018 (12)	0.0166 (12)	−0.0033 (12)
C3	0.0630 (19)	0.0439 (17)	0.0441 (16)	−0.0017 (14)	0.0176 (14)	−0.0127 (13)
C4	0.0640 (19)	0.0327 (15)	0.0591 (18)	−0.0057 (14)	0.0234 (16)	−0.0050 (13)
C5	0.0454 (16)	0.0408 (16)	0.0516 (16)	0.0001 (13)	0.0235 (13)	0.0055 (13)
C6	0.0511 (16)	0.0444 (16)	0.0398 (15)	−0.0008 (13)	0.0219 (13)	−0.0045 (12)
C7	0.0410 (14)	0.0340 (14)	0.0366 (14)	0.0012 (11)	0.0155 (12)	−0.0064 (11)
C8	0.0481 (16)	0.0386 (15)	0.0349 (14)	−0.0009 (12)	0.0179 (12)	−0.0093 (11)
C9	0.0400 (14)	0.0367 (14)	0.0359 (14)	0.0016 (11)	0.0159 (12)	−0.0077 (11)
C10	0.0391 (14)	0.0369 (14)	0.0336 (13)	0.0012 (11)	0.0141 (11)	−0.0066 (11)
C11	0.0578 (17)	0.0398 (15)	0.0356 (14)	0.0011 (13)	0.0231 (13)	−0.0046 (11)
C12	0.0444 (15)	0.0334 (14)	0.0324 (13)	−0.0006 (11)	0.0165 (12)	−0.0026 (11)
C13	0.0485 (15)	0.0327 (14)	0.0336 (13)	−0.0012 (12)	0.0187 (12)	−0.0011 (11)
C14	0.0400 (13)	0.0296 (13)	0.0376 (14)	−0.0030 (11)	0.0184 (11)	−0.0013 (11)
C15	0.0605 (18)	0.0359 (15)	0.0404 (15)	−0.0032 (13)	0.0236 (14)	−0.0031 (12)
C16	0.082 (2)	0.0437 (17)	0.0405 (16)	0.0001 (15)	0.0280 (16)	0.0043 (13)
C17	0.079 (2)	0.0344 (15)	0.0556 (18)	0.0057 (15)	0.0293 (17)	0.0109 (13)
C18	0.0691 (19)	0.0311 (15)	0.0502 (16)	−0.0027 (13)	0.0309 (15)	−0.0047 (12)
C19	0.0454 (15)	0.0337 (14)	0.0380 (14)	−0.0032 (11)	0.0211 (12)	−0.0013 (11)
C20	0.073 (2)	0.0473 (17)	0.0419 (16)	−0.0035 (15)	0.0259 (15)	−0.0133 (13)

Geometric parameters (Å, º) top

Br1—C5	1.896 (3)	C6—H6A	0.9300
S1—C11	1.718 (3)	C7—C8	1.424 (3)
S1—C12	1.740 (2)	C8—C9	1.359 (3)
O1—C2	1.375 (3)	C8—H8A	0.9300
O1—C1	1.375 (3)	C9—C10	1.457 (3)
O2—C1	1.209 (3)	C10—C11	1.355 (3)
O3—C19	1.374 (3)	C11—H11A	0.9300
O3—C20	1.430 (3)	C13—C14	1.464 (3)
N1—C12	1.291 (3)	C13—H13A	0.9300
N1—C10	1.396 (3)	C14—C15	1.387 (3)
N2—N3	1.360 (3)	C14—C19	1.409 (3)
N2—C12	1.365 (3)	C15—C16	1.377 (4)
N2—H1	0.9449	C15—H15A	0.9300
N3—C13	1.277 (3)	C16—C17	1.371 (4)
C1—C9	1.461 (3)	C16—H16A	0.9300
C2—C3	1.379 (4)	C17—C18	1.377 (4)
C2—C7	1.389 (3)	C17—H17A	0.9300
C3—C4	1.371 (4)	C18—C19	1.379 (3)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.392 (4)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C5—C6	1.361 (4)	C20—H20C	0.9600
C6—C7	1.397 (3)

C11—S1—C12	87.96 (12)	C11—C10—C9	128.1 (2)
C2—O1—C1	122.48 (18)	N1—C10—C9	117.2 (2)
C19—O3—C20	116.75 (19)	C10—C11—S1	111.30 (18)
C12—N1—C10	109.9 (2)	C10—C11—H11A	124.4
N3—N2—C12	115.7 (2)	S1—C11—H11A	124.4
N3—N2—H1	121.9	N1—C12—N2	124.4 (2)
C12—N2—H1	121.1	N1—C12—S1	116.16 (17)
C13—N3—N2	119.5 (2)	N2—C12—S1	119.44 (18)
O2—C1—O1	115.2 (2)	N3—C13—C14	117.9 (2)
O2—C1—C9	126.9 (2)	N3—C13—H13A	121.0
O1—C1—C9	117.8 (2)	C14—C13—H13A	121.0
O1—C2—C3	116.9 (2)	C15—C14—C19	117.5 (2)
O1—C2—C7	120.9 (2)	C15—C14—C13	120.3 (2)
C3—C2—C7	122.1 (2)	C19—C14—C13	122.1 (2)
C4—C3—C2	118.9 (2)	C16—C15—C14	121.5 (2)
C4—C3—H3A	120.5	C16—C15—H15A	119.3
C2—C3—H3A	120.5	C14—C15—H15A	119.3
C3—C4—C5	119.6 (3)	C17—C16—C15	119.9 (3)
C3—C4—H4A	120.2	C17—C16—H16A	120.0
C5—C4—H4A	120.2	C15—C16—H16A	120.0
C6—C5—C4	121.4 (2)	C16—C17—C18	120.4 (3)
C6—C5—Br1	119.5 (2)	C16—C17—H17A	119.8
C4—C5—Br1	119.1 (2)	C18—C17—H17A	119.8
C5—C6—C7	119.9 (2)	C17—C18—C19	119.8 (2)
C5—C6—H6A	120.0	C17—C18—H18A	120.1
C7—C6—H6A	120.0	C19—C18—H18A	120.1
C2—C7—C6	118.0 (2)	O3—C19—C18	123.3 (2)
C2—C7—C8	117.5 (2)	O3—C19—C14	115.9 (2)
C6—C7—C8	124.5 (2)	C18—C19—C14	120.8 (2)
C9—C8—C7	122.5 (2)	O3—C20—H20A	109.5
C9—C8—H8A	118.7	O3—C20—H20B	109.5
C7—C8—H8A	118.7	H20A—C20—H20B	109.5
C8—C9—C10	121.4 (2)	O3—C20—H20C	109.5
C8—C9—C1	118.7 (2)	H20A—C20—H20C	109.5
C10—C9—C1	119.9 (2)	H20B—C20—H20C	109.5
C11—C10—N1	114.7 (2)

C12—N2—N3—C13	−177.2 (2)	C1—C9—C10—C11	4.9 (4)
C2—O1—C1—O2	178.6 (2)	C8—C9—C10—N1	4.9 (4)
C2—O1—C1—C9	−0.9 (3)	C1—C9—C10—N1	−173.7 (2)
C1—O1—C2—C3	−176.6 (2)	N1—C10—C11—S1	−0.1 (3)
C1—O1—C2—C7	2.9 (4)	C9—C10—C11—S1	−178.8 (2)
O1—C2—C3—C4	−179.5 (3)	C12—S1—C11—C10	0.6 (2)
C7—C2—C3—C4	1.0 (4)	C10—N1—C12—N2	179.9 (2)
C2—C3—C4—C5	0.3 (4)	C10—N1—C12—S1	1.2 (3)
C3—C4—C5—C6	−1.1 (4)	N3—N2—C12—N1	174.9 (2)
C3—C4—C5—Br1	179.5 (2)	N3—N2—C12—S1	−6.4 (3)
C4—C5—C6—C7	0.8 (4)	C11—S1—C12—N1	−1.1 (2)
Br1—C5—C6—C7	−179.84 (19)	C11—S1—C12—N2	−179.8 (2)
O1—C2—C7—C6	179.2 (2)	N2—N3—C13—C14	176.9 (2)
C3—C2—C7—C6	−1.3 (4)	N3—C13—C14—C15	−6.5 (4)
O1—C2—C7—C8	−2.6 (4)	N3—C13—C14—C19	176.0 (2)
C3—C2—C7—C8	176.9 (2)	C19—C14—C15—C16	0.7 (4)
C5—C6—C7—C2	0.4 (4)	C13—C14—C15—C16	−177.0 (3)
C5—C6—C7—C8	−177.7 (2)	C14—C15—C16—C17	0.9 (5)
C2—C7—C8—C9	0.3 (4)	C15—C16—C17—C18	−2.0 (5)
C6—C7—C8—C9	178.4 (3)	C16—C17—C18—C19	1.4 (5)
C7—C8—C9—C10	−176.9 (2)	C20—O3—C19—C18	5.8 (4)
C7—C8—C9—C1	1.7 (4)	C20—O3—C19—C14	−176.2 (2)
O2—C1—C9—C8	179.2 (3)	C17—C18—C19—O3	178.1 (3)
O1—C1—C9—C8	−1.4 (4)	C17—C18—C19—C14	0.2 (4)
O2—C1—C9—C10	−2.1 (4)	C15—C14—C19—O3	−179.3 (2)
O1—C1—C9—C10	177.3 (2)	C13—C14—C19—O3	−1.7 (4)
C12—N1—C10—C11	−0.7 (3)	C15—C14—C19—C18	−1.3 (4)
C12—N1—C10—C9	178.2 (2)	C13—C14—C19—C18	176.4 (2)
C8—C9—C10—C11	−176.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O2ⁱ	0.94	2.10	3.021 (3)	164

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄BrN₃O₃S
M_r	456.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.2802 (12), 19.551 (3), 14.0638 (18)
β (°)	113.352 (7)
V (Å³)	1837.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.43 × 0.07 × 0.04

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.427, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	11951, 4266, 2786
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.089, 1.01
No. of reflections	4266
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

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—H1···O2ⁱ	0.94	2.10	3.021 (3)	164

Symmetry code: (i) x, −y+3/2, z−1/2.

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.

References

Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011a). Acta Cryst. E67, o1072–o1073. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011b). Acta Cryst. E67, o1007–o1008. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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