6-Bromo-1-methyl-4-[2-(4-nitro­benzyl­idene)hydrazin-1-yl­idene]-2,2-dioxo-3,4-dihydro-1H-2λ6,1-benzothia­zine

Shafiq, M.; Harrison, W.T.A.; Khan, I.U.

doi:10.1107/S1600536812035374

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2717

doi:10.1107/S1600536812035374

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6-Bromo-1-methyl-4-[2-(4-nitrobenzylidene)hydrazin-1-ylidene]-2,2-dioxo-3,4-dihydro-1H-2λ⁶,1-benzothiazine

Muhammad Shafiq,^a ^* William T. A. Harrison ^b and Islam Ullah Khan ^c

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^bDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 1 August 2012; accepted 10 August 2012; online 15 August 2012)

In the title compound, C₁₆H₁₃BrN₄O₄S, the dihedral angle between the aromatic rings is 4.1 (2)° and the C=N—N=C torsion angle is 175.5 (3)°. The nitro group is almost coplanar with the benzene ring to which it is attached [dihedral angle = 2.9 (7)°]. The thiazine ring has an S-envelope conformation with the S atom displaced by 0.819 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.017 Å). In the crystal, C—H⋯O interactions link the molecules and weak aromatic π–π stacking [centroid–centroid separation = 3.874 (2) Å] is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011 ). For related structures, see: Shafiq, Khan et al. (2011 ); Shafiq, Harrison et al. (2012 ).

Experimental

Crystal data

C₁₆H₁₃BrN₄O₄S
M_r = 437.27
Triclinic, $[P \overline 1]$
a = 8.2772 (4) Å
b = 9.0572 (4) Å
c = 12.6868 (6) Å
α = 87.132 (4)°
β = 70.976 (3)°
γ = 75.098 (2)°
V = 868.32 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.52 mm⁻¹
T = 296 K
0.36 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.464, T_max = 0.843
17474 measured reflections
4251 independent reflections
2484 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 1.00
4251 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.93	2.56	3.325 (4)	139
C8—H8B⋯O2ⁱⁱ	0.97	2.44	3.310 (4)	150
C13—H13⋯O4ⁱⁱⁱ	0.93	2.53	3.306 (5)	141
C15—H15⋯O2^iv	0.93	2.53	3.426 (4)	162
C16—H16⋯O1^v	0.93	2.45	3.218 (4)	139
Symmetry codes: (i) x, y+1, z+1; (ii) -x+1, -y, -z+1; (iii) -x+1, -y-1, -z; (iv) x, y, z-1; (v) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035374/pv2578sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035374/pv2578Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035374/pv2578Isup3.cml

checkCIF report

Comment top

A number of benzothiazine derivatives have been found to be effective as drugs (Shafiq, Zia-ur-Rehman et al., 2011). As a part of our ongoing studies in this area, we now describe the crystal structure of the title compound in this areticle.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Shafiq, Khan et al., 2011; Shafiq, Harrison et al., 2012). In the title molecule, the dihedral angle between the aromatic rings (C1–C6 and C11–C16) is 4.1 (2)° and the C7═N2—N3═C10 torsion angle is 175.5 (3)°. The nitro group is almost coplanar with benzene ring ((C11–C16) to which it is attached [dihedral angle = 2.9 (7)°]. The thiazine ring adopts an S-envelope conformation with S1 atom displaced by 0.819 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.017 Å).

The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1) linking the molecules to generate a three-dimensional network with all four O atoms acting as acceptors. Weak aromatic π-π stacking [centroid-centroid separation = 3.874 (2) Å] is also observed.

Related literature top

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011). For related structures, see: Shafiq, Khan et al. (2011); Shafiq, Harrison et al. (2012).

Experimental top

The compound was synthesized following the literature procedure (Shafiq, Zia-ur-Rehman et al., 2011) and recrystalized from an ethylacetate solution under slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Fig. 2. A view of the C—-H···O hydrogen bonds (orange double-dashed lines) in the crystal structure of the title compound.

6-Bromo-1-methyl-4-[2-(4-nitrobenzylidene)hydrazin-1-ylidene]-2,2-dioxo- 3,4-dihydro-1H-2λ⁶,1-benzothiazine top

Crystal data top

C₁₆H₁₃BrN₄O₄S	Z = 2
M_r = 437.27	F(000) = 440
Triclinic, P1	D_x = 1.672 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2772 (4) Å	Cell parameters from 4062 reflections
b = 9.0572 (4) Å	θ = 2.3–22.1°
c = 12.6868 (6) Å	µ = 2.52 mm⁻¹
α = 87.132 (4)°	T = 296 K
β = 70.976 (3)°	Needle, yellow
γ = 75.098 (2)°	0.36 × 0.09 × 0.07 mm
V = 868.32 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	2484 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 28.4°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.464, T_max = 0.843	k = −12→12
17474 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0415P)² + 0.5116P] where P = (F_o² + 2F_c²)/3
4251 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₆H₁₃BrN₄O₄S	γ = 75.098 (2)°
M_r = 437.27	V = 868.32 (7) Å³
Triclinic, P1	Z = 2
a = 8.2772 (4) Å	Mo Kα radiation
b = 9.0572 (4) Å	µ = 2.52 mm⁻¹
c = 12.6868 (6) Å	T = 296 K
α = 87.132 (4)°	0.36 × 0.09 × 0.07 mm
β = 70.976 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4251 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2484 reflections with I > 2σ(I)
T_min = 0.464, T_max = 0.843	R_int = 0.043
17474 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
4251 reflections	Δρ_min = −0.40 e Å⁻³
236 parameters

Special details top

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
C1	0.8000 (4)	0.2966 (4)	0.3910 (3)	0.0429 (8)
C2	0.8376 (5)	0.4239 (4)	0.4267 (3)	0.0591 (10)
H2	0.8240	0.4365	0.5017	0.071*
C3	0.8940 (5)	0.5298 (4)	0.3531 (3)	0.0516 (9)
H3	0.9165	0.6146	0.3784	0.062*
C4	0.9175 (4)	0.5116 (3)	0.2422 (3)	0.0443 (8)
C5	0.8801 (4)	0.3880 (3)	0.2041 (3)	0.0385 (7)
H5	0.8956	0.3769	0.1287	0.046*
C6	0.8192 (4)	0.2795 (3)	0.2783 (2)	0.0371 (7)
C7	0.7760 (4)	0.1511 (3)	0.2351 (2)	0.0336 (7)
C8	0.7034 (4)	0.0381 (4)	0.3145 (2)	0.0438 (8)
H8A	0.7315	−0.0590	0.2750	0.053*
H8B	0.5757	0.0744	0.3446	0.053*
C9	0.6400 (6)	0.2323 (5)	0.5848 (3)	0.0799 (13)
H9A	0.7166	0.2499	0.6229	0.120*
H9B	0.5874	0.1518	0.6195	0.120*
H9C	0.5488	0.3242	0.5886	0.120*
C10	0.7637 (4)	0.0248 (3)	−0.0055 (3)	0.0390 (7)
H10	0.8022	0.1039	−0.0472	0.047*
C11	0.7208 (4)	−0.0903 (3)	−0.0607 (2)	0.0362 (7)
C12	0.6593 (4)	−0.2102 (4)	−0.0032 (2)	0.0413 (7)
H12	0.6451	−0.2187	0.0724	0.050*
C13	0.6194 (4)	−0.3163 (4)	−0.0580 (3)	0.0454 (8)
H13	0.5775	−0.3964	−0.0199	0.054*
C14	0.6428 (4)	−0.3016 (4)	−0.1703 (3)	0.0404 (7)
C15	0.7034 (4)	−0.1855 (4)	−0.2294 (3)	0.0431 (8)
H15	0.7184	−0.1782	−0.3052	0.052*
C16	0.7415 (4)	−0.0794 (4)	−0.1731 (2)	0.0414 (8)
H16	0.7820	0.0010	−0.2116	0.050*
S1	0.79259 (11)	0.01247 (9)	0.42342 (6)	0.0432 (2)
O1	0.9788 (3)	−0.0430 (3)	0.37576 (19)	0.0558 (6)
O2	0.7010 (3)	−0.0721 (3)	0.50933 (18)	0.0569 (6)
O3	0.6135 (4)	−0.3959 (3)	−0.3268 (2)	0.0759 (8)
O4	0.5483 (5)	−0.5195 (3)	−0.1767 (3)	0.0898 (10)
N1	0.7408 (4)	0.1889 (3)	0.4696 (2)	0.0498 (7)
N2	0.7990 (3)	0.1447 (3)	0.1299 (2)	0.0404 (6)
N3	0.7509 (3)	0.0216 (3)	0.0964 (2)	0.0396 (6)
N4	0.5998 (4)	−0.4145 (4)	−0.2289 (3)	0.0559 (8)
Br1	1.00058 (6)	0.65482 (4)	0.13996 (3)	0.06700 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.048 (2)	0.0466 (19)	0.0369 (18)	−0.0160 (15)	−0.0144 (15)	−0.0020 (15)
C2	0.076 (3)	0.063 (2)	0.046 (2)	−0.022 (2)	−0.0239 (19)	−0.0153 (18)
C3	0.069 (2)	0.0375 (18)	0.058 (2)	−0.0180 (17)	−0.0296 (18)	−0.0092 (16)
C4	0.051 (2)	0.0363 (17)	0.052 (2)	−0.0126 (15)	−0.0240 (16)	0.0005 (15)
C5	0.0415 (19)	0.0375 (16)	0.0399 (18)	−0.0096 (14)	−0.0175 (14)	−0.0018 (14)
C6	0.0370 (18)	0.0389 (17)	0.0387 (17)	−0.0117 (14)	−0.0143 (13)	−0.0046 (13)
C7	0.0338 (17)	0.0365 (16)	0.0320 (17)	−0.0101 (13)	−0.0115 (13)	−0.0018 (13)
C8	0.050 (2)	0.0496 (19)	0.0379 (18)	−0.0230 (16)	−0.0139 (15)	0.0011 (15)
C9	0.094 (3)	0.081 (3)	0.046 (2)	−0.023 (2)	0.006 (2)	−0.013 (2)
C10	0.0408 (19)	0.0436 (17)	0.0361 (18)	−0.0185 (14)	−0.0109 (14)	0.0002 (14)
C11	0.0338 (17)	0.0423 (17)	0.0352 (17)	−0.0125 (13)	−0.0121 (13)	−0.0018 (13)
C12	0.049 (2)	0.0495 (19)	0.0304 (17)	−0.0177 (15)	−0.0161 (14)	0.0016 (14)
C13	0.056 (2)	0.0424 (18)	0.046 (2)	−0.0217 (16)	−0.0201 (16)	0.0032 (15)
C14	0.0412 (19)	0.0451 (18)	0.0381 (18)	−0.0107 (15)	−0.0158 (14)	−0.0079 (14)
C15	0.0395 (19)	0.060 (2)	0.0315 (17)	−0.0118 (16)	−0.0128 (14)	−0.0055 (15)
C16	0.0431 (19)	0.0498 (19)	0.0353 (18)	−0.0197 (15)	−0.0123 (14)	0.0032 (14)
S1	0.0471 (5)	0.0504 (5)	0.0333 (4)	−0.0180 (4)	−0.0110 (3)	0.0065 (4)
O1	0.0443 (15)	0.0642 (15)	0.0522 (14)	−0.0085 (11)	−0.0126 (11)	0.0132 (12)
O2	0.0661 (17)	0.0680 (16)	0.0400 (13)	−0.0306 (13)	−0.0132 (11)	0.0155 (11)
O3	0.100 (2)	0.091 (2)	0.0488 (17)	−0.0368 (17)	−0.0284 (15)	−0.0191 (15)
O4	0.143 (3)	0.076 (2)	0.085 (2)	−0.063 (2)	−0.055 (2)	0.0059 (17)
N1	0.064 (2)	0.0584 (18)	0.0280 (14)	−0.0241 (15)	−0.0083 (12)	−0.0028 (12)
N2	0.0479 (17)	0.0391 (14)	0.0405 (16)	−0.0188 (12)	−0.0163 (12)	−0.0023 (12)
N3	0.0482 (16)	0.0375 (14)	0.0382 (16)	−0.0167 (12)	−0.0157 (12)	−0.0036 (11)
N4	0.058 (2)	0.060 (2)	0.057 (2)	−0.0167 (16)	−0.0241 (15)	−0.0144 (16)
Br1	0.0932 (4)	0.0392 (2)	0.0830 (3)	−0.0297 (2)	−0.0394 (2)	0.01409 (18)

Geometric parameters (Å, º) top

C1—C6	1.398 (4)	C10—N3	1.262 (4)
C1—C2	1.400 (4)	C10—C11	1.459 (4)
C1—N1	1.420 (4)	C10—H10	0.9300
C2—C3	1.367 (5)	C11—C16	1.380 (4)
C2—H2	0.9300	C11—C12	1.391 (4)
C3—C4	1.368 (4)	C12—C13	1.376 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.382 (4)	C13—C14	1.379 (4)
C4—Br1	1.884 (3)	C13—H13	0.9300
C5—C6	1.400 (4)	C14—C15	1.366 (4)
C5—H5	0.9300	C14—N4	1.470 (4)
C6—C7	1.478 (4)	C15—C16	1.381 (4)
C7—N2	1.288 (4)	C15—H15	0.9300
C7—C8	1.497 (4)	C16—H16	0.9300
C8—S1	1.748 (3)	S1—O1	1.420 (2)
C8—H8A	0.9700	S1—O2	1.423 (2)
C8—H8B	0.9700	S1—N1	1.631 (3)
C9—N1	1.443 (4)	O3—N4	1.217 (4)
C9—H9A	0.9600	O4—N4	1.219 (4)
C9—H9B	0.9600	N2—N3	1.402 (3)
C9—H9C	0.9600

C6—C1—C2	119.1 (3)	N3—C10—H10	118.6
C6—C1—N1	121.3 (3)	C11—C10—H10	118.6
C2—C1—N1	119.7 (3)	C16—C11—C12	119.2 (3)
C3—C2—C1	121.0 (3)	C16—C11—C10	119.0 (3)
C3—C2—H2	119.5	C12—C11—C10	121.8 (3)
C1—C2—H2	119.5	C13—C12—C11	120.2 (3)
C2—C3—C4	120.2 (3)	C13—C12—H12	119.9
C2—C3—H3	119.9	C11—C12—H12	119.9
C4—C3—H3	119.9	C12—C13—C14	118.7 (3)
C3—C4—C5	120.3 (3)	C12—C13—H13	120.6
C3—C4—Br1	120.3 (2)	C14—C13—H13	120.6
C5—C4—Br1	119.3 (2)	C15—C14—C13	122.6 (3)
C4—C5—C6	120.4 (3)	C15—C14—N4	118.6 (3)
C4—C5—H5	119.8	C13—C14—N4	118.8 (3)
C6—C5—H5	119.8	C14—C15—C16	117.9 (3)
C1—C6—C5	118.9 (3)	C14—C15—H15	121.0
C1—C6—C7	122.2 (3)	C16—C15—H15	121.0
C5—C6—C7	118.9 (3)	C11—C16—C15	121.3 (3)
N2—C7—C6	117.6 (3)	C11—C16—H16	119.3
N2—C7—C8	123.0 (2)	C15—C16—H16	119.3
C6—C7—C8	119.4 (2)	O1—S1—O2	118.22 (15)
C7—C8—S1	110.5 (2)	O1—S1—N1	110.53 (15)
C7—C8—H8A	109.6	O2—S1—N1	108.09 (14)
S1—C8—H8A	109.6	O1—S1—C8	107.65 (15)
C7—C8—H8B	109.6	O2—S1—C8	110.70 (14)
S1—C8—H8B	109.6	N1—S1—C8	100.17 (15)
H8A—C8—H8B	108.1	C1—N1—C9	122.1 (3)
N1—C9—H9A	109.5	C1—N1—S1	116.7 (2)
N1—C9—H9B	109.5	C9—N1—S1	121.3 (2)
H9A—C9—H9B	109.5	C7—N2—N3	113.8 (2)
N1—C9—H9C	109.5	C10—N3—N2	112.1 (2)
H9A—C9—H9C	109.5	O3—N4—O4	123.4 (3)
H9B—C9—H9C	109.5	O3—N4—C14	117.9 (3)
N3—C10—C11	122.9 (3)	O4—N4—C14	118.7 (3)

C6—C1—C2—C3	−0.6 (5)	C13—C14—C15—C16	−0.2 (5)
N1—C1—C2—C3	−179.7 (3)	N4—C14—C15—C16	179.3 (3)
C1—C2—C3—C4	−1.1 (6)	C12—C11—C16—C15	−0.3 (5)
C2—C3—C4—C5	1.7 (5)	C10—C11—C16—C15	179.8 (3)
C2—C3—C4—Br1	−178.5 (3)	C14—C15—C16—C11	0.5 (5)
C3—C4—C5—C6	−0.5 (5)	C7—C8—S1—O1	−60.1 (3)
Br1—C4—C5—C6	179.6 (2)	C7—C8—S1—O2	169.3 (2)
C2—C1—C6—C5	1.7 (5)	C7—C8—S1—N1	55.4 (2)
N1—C1—C6—C5	−179.2 (3)	C6—C1—N1—C9	−149.0 (4)
C2—C1—C6—C7	−177.8 (3)	C2—C1—N1—C9	30.0 (5)
N1—C1—C6—C7	1.2 (5)	C6—C1—N1—S1	31.0 (4)
C4—C5—C6—C1	−1.2 (5)	C2—C1—N1—S1	−149.9 (3)
C4—C5—C6—C7	178.4 (3)	O1—S1—N1—C1	57.5 (3)
C1—C6—C7—N2	−179.6 (3)	O2—S1—N1—C1	−171.7 (2)
C5—C6—C7—N2	0.8 (4)	C8—S1—N1—C1	−55.9 (3)
C1—C6—C7—C8	2.2 (4)	O1—S1—N1—C9	−122.5 (3)
C5—C6—C7—C8	−177.4 (3)	O2—S1—N1—C9	8.3 (4)
N2—C7—C8—S1	148.6 (3)	C8—S1—N1—C9	124.2 (3)
C6—C7—C8—S1	−33.3 (4)	C6—C7—N2—N3	−178.5 (3)
N3—C10—C11—C16	−178.9 (3)	C8—C7—N2—N3	−0.4 (4)
N3—C10—C11—C12	1.2 (5)	C11—C10—N3—N2	−179.8 (3)
C16—C11—C12—C13	−0.1 (5)	C7—N2—N3—C10	175.5 (3)
C10—C11—C12—C13	179.7 (3)	C15—C14—N4—O3	−2.8 (5)
C11—C12—C13—C14	0.4 (5)	C13—C14—N4—O3	176.7 (3)
C12—C13—C14—C15	−0.3 (5)	C15—C14—N4—O4	178.9 (3)
C12—C13—C14—N4	−179.8 (3)	C13—C14—N4—O4	−1.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.56	3.325 (4)	139
C8—H8B···O2ⁱⁱ	0.97	2.44	3.310 (4)	150
C13—H13···O4ⁱⁱⁱ	0.93	2.53	3.306 (5)	141
C15—H15···O2^iv	0.93	2.53	3.426 (4)	162
C16—H16···O1^v	0.93	2.45	3.218 (4)	139

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrN₄O₄S
M_r	437.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2772 (4), 9.0572 (4), 12.6868 (6)
α, β, γ (°)	87.132 (4), 70.976 (3), 75.098 (2)
V (Å³)	868.32 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.52
Crystal size (mm)	0.36 × 0.09 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.464, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	17474, 4251, 2484
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.00
No. of reflections	4251
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.56	3.325 (4)	139
C8—H8B···O2ⁱⁱ	0.97	2.44	3.310 (4)	150
C13—H13···O4ⁱⁱⁱ	0.93	2.53	3.306 (5)	141
C15—H15···O2^iv	0.93	2.53	3.426 (4)	162
C16—H16···O1^v	0.93	2.45	3.218 (4)	139

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

Acknowledgements

MS acknowledges the Higher Education Commission of Pakistan for financial support and GC University Lahore, Pakistan for provision of facilities during his PhD studies.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Shafiq, M., Harrison, W. T. A., Khan, I. U., Bukhari, I. H. & Bokhari, T. H. (2012). Acta Cryst. E68, o2643. CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011). Acta Cryst. E67, o2092. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Zia-ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011). J. Chilean Chem. Soc. 56, 527–531. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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