4-Hydr­oxy-N-(2,4,6-tribromo­phen­yl)-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide

Arshad, M.N.; Zia-ur-Rehman, M.; Khan, I.U.; Shafiq, M.

doi:10.1107/S1600536809046029

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2998

doi:10.1107/S1600536809046029

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4-Hydroxy-N-(2,4,6-tribromophenyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Muhammad Nadeem Arshad,^a Muhammad Zia-ur-Rehman,^b Islam Ullah Khan ^a ^* and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 30 October 2009; accepted 2 November 2009; online 4 November 2009)

In the title compound, C₁₅H₁₉Br₃N₂O₄S, the thiazine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring. In the crystal, the molecules are linked into a three-dimensional network through intermolecular N—H⋯O, N—H⋯Br and O—H⋯Br hydrogen bonds.

Related literature

For the synthesis of related molecules, see: Kojić-Prodić & Rużić-Toroš (1982 ); Zia-ur-Rehman, Choudary & Ahmad (2005 ). For the applications of 1,2-benzothiazine 1,1-dioxides and their precursor intermediates as non-steroidal anti-inflammatory compounds, see: Turck et al. (1996 ). For bond-length data, see: Weast et al. (1984 ).

Experimental

Crystal data

C₁₅H₉Br₃N₂O₄S
M_r = 553.03
Triclinic, $[P \overline 1]$
a = 7.5082 (4) Å
b = 8.7486 (6) Å
c = 13.0669 (9) Å
α = 83.618 (2)°
β = 86.280 (2)°
γ = 87.684 (2)°
V = 850.72 (9) Å³
Z = 2
Mo Kα radiation
μ = 7.26 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.355, T_max = 0.502
16515 measured reflections
3794 independent reflections
2599 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.01
3794 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 1.16 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.83	2.561 (5)	147
N1—H1⋯O1Aⁱ	0.86	2.29	2.966 (5)	136
N2—H2A⋯Br2ⁱⁱ	0.86	2.79	3.597 (4)	157
O4—H4⋯Br2ⁱⁱⁱ	0.82	2.88	3.403 (3)	124
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1.

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: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046029/bt5126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046029/bt5126Isup2.hkl

checkCIF report

Comment top

Owing to the applications of 1,2-benzothiazine 1,1-dioxides and their precursor intermediates as non-steroidal anti-inflammatory compounds (Turck et al., 1996), considerable attention has been given to their synthesis. As part of a research program synthesizing 1,2-benzothiazines (Zia-ur-Rehman et al., 2005), we herein report the crystal structure of the title compound, (I) (Scheme and figure 1).

The thiazine ring, involving two double bonds, exhibits a sofa conformation; with S1/C1/C6/C7 relatively planar and N1 showing significant departure from plane due to its pyramidal geometry. The enolic hydrogen on O4 is involved in intramolecular hydrogen bonding [O4—H4···O3] with the carbonyl oxygen at C9 giving rise to a six-membered hydrogen bond ring (Table 1). The C1—S1 [1.757 (5) Å] bond is shorter than a normal C—S single bond (1.81–2.55 Å) (Weast et al., 1984) due to partial double bond character and is in agreement with similar molecules (Kojić-Prodić & Rużić-Toroš, 1982). Each molecule is linked to its adjacent one through intermolecular N—H···Br forming a centrosymmetric dimer which is further linked to the next via O—H···Br hydrogen bonds giving rise to a zigzag chain along b (Figure 2). The title molecules are also linked to each other via N—H···O hydrogen bonds forming dimers along b which furthr links to the adjacent dimer through O—H···Br hydrogen bonds giving rise to a zigzag chain along b (Figure 3).

Related literature top

For the synthesis of related molecules, see: Kojić-Prodić & Rużić-Toroš (1982); Zia-ur-Rehman, Choudary & Ahmad (2005). For the applications of 1,2-benzothiazine 1,1-dioxides and their precursor intermediates as non-steroidal anti-inflammatory compounds, see: Turck et al. (1996). For bond-length data, see: Weast et al. (1984).

Experimental top

A mixture of methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (2.55 g; 10.0 mmoles), 2,3-dimethyl aniline (4.947 g; 15.0 mmoles) and xylene (25.0 ml) was refluxed under nitrogen atmosphere in a Soxhlet apparatus having Linde type 4Å molecular sieves. Three fourth of the xylene was then distilled off and the remaining contents were allowed to stand overnight at room temperature. Settled solids were filtered off, washed with diethyl ether and crystallized from ethanol. Yield: 82%.

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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing N—H···Br and O—H···Br hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. Another perspective view of the three-dimensional crystal packing showing N—H···O and O—H···Br hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

4-Hydroxy-N-(2,4,6-tribromophenyl)-2H-1,2-benzothiazine-3- carboxamide 1,1-dioxide top

Crystal data top

C₁₅H₉Br₃N₂O₄S	Z = 2
M_r = 553.03	F(000) = 532
Triclinic, P1	D_x = 2.159 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5082 (4) Å	Cell parameters from 5092 reflections
b = 8.7486 (6) Å	θ = 2.3–24.2°
c = 13.0669 (9) Å	µ = 7.26 mm⁻¹
α = 83.618 (2)°	T = 296 K
β = 86.280 (2)°	Needle, light yellow
γ = 87.684 (2)°	0.18 × 0.16 × 0.11 mm
V = 850.72 (9) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3794 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→9
T_min = 0.355, T_max = 0.502	k = −11→11
16515 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.049P)² + 2.0189P] where P = (F_o² + 2F_c²)/3
3794 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 1.16 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₅H₉Br₃N₂O₄S	γ = 87.684 (2)°
M_r = 553.03	V = 850.72 (9) Å³
Triclinic, P1	Z = 2
a = 7.5082 (4) Å	Mo Kα radiation
b = 8.7486 (6) Å	µ = 7.26 mm⁻¹
c = 13.0669 (9) Å	T = 296 K
α = 83.618 (2)°	0.18 × 0.16 × 0.11 mm
β = 86.280 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3794 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2599 reflections with I > 2σ(I)
T_min = 0.355, T_max = 0.502	R_int = 0.031
16515 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 1.16 e Å⁻³
3794 reflections	Δρ_min = −0.63 e Å⁻³
227 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
Br1	0.82014 (8)	0.13368 (9)	0.54929 (5)	0.0701 (2)
Br2	0.30934 (9)	0.34516 (6)	0.26785 (4)	0.0603 (2)
Br3	0.17498 (9)	0.43843 (7)	0.68227 (5)	0.0629 (2)
C1	0.8054 (6)	0.2197 (6)	1.0575 (4)	0.0373 (11)
C2	0.8789 (7)	0.2424 (6)	1.1475 (4)	0.0462 (12)
H2	0.9024	0.3412	1.1617	0.055*
C3	0.9184 (8)	0.1144 (8)	1.2182 (5)	0.0591 (15)
H3	0.9641	0.1286	1.2808	0.071*
C4	0.8905 (7)	−0.0287 (8)	1.1956 (5)	0.0625 (17)
H4A	0.9211	−0.1127	1.2419	0.075*
C5	0.8152 (6)	−0.0538 (6)	1.1026 (4)	0.0454 (12)
H5	0.7971	−0.1533	1.0878	0.055*
C6	0.7687 (6)	0.0711 (5)	1.0339 (4)	0.0360 (10)
C7	0.6899 (6)	0.0507 (5)	0.9372 (4)	0.0364 (10)
C8	0.6194 (6)	0.1678 (5)	0.8750 (4)	0.0354 (10)
C9	0.5696 (6)	0.1459 (6)	0.7707 (4)	0.0382 (11)
C10	0.4863 (6)	0.2808 (5)	0.6055 (4)	0.0361 (10)
C11	0.5909 (6)	0.2214 (5)	0.5271 (4)	0.0392 (11)
C12	0.5352 (7)	0.2323 (6)	0.4267 (4)	0.0430 (12)
H12	0.6034	0.1874	0.3753	0.052*
C13	0.3776 (7)	0.3105 (5)	0.4054 (4)	0.0383 (11)
C14	0.2718 (7)	0.3729 (5)	0.4799 (4)	0.0421 (12)
H14	0.1655	0.4259	0.4638	0.050*
C15	0.3259 (6)	0.3557 (5)	0.5797 (4)	0.0401 (11)
N1	0.6041 (5)	0.3207 (4)	0.9051 (3)	0.0383 (9)
H1	0.5118	0.3798	0.8931	0.046*
N2	0.5404 (6)	0.2763 (5)	0.7070 (3)	0.0430 (10)
H2A	0.5560	0.3627	0.7303	0.052*
O2	0.9238 (5)	0.3836 (4)	0.8929 (3)	0.0500 (9)
O3	0.5570 (5)	0.0166 (4)	0.7438 (3)	0.0492 (9)
O4	0.6955 (5)	−0.0922 (4)	0.9118 (3)	0.0470 (9)
H4	0.6471	−0.0940	0.8575	0.070*
O1A	0.7151 (5)	0.5147 (4)	1.0094 (3)	0.0481 (9)
S1	0.77172 (16)	0.37606 (13)	0.96331 (10)	0.0381 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0467 (3)	0.1064 (6)	0.0550 (4)	0.0271 (3)	−0.0078 (3)	−0.0070 (3)
Br2	0.0949 (5)	0.0455 (3)	0.0440 (3)	0.0073 (3)	−0.0311 (3)	−0.0082 (2)
Br3	0.0685 (4)	0.0635 (4)	0.0548 (4)	0.0185 (3)	0.0116 (3)	−0.0145 (3)
C1	0.032 (2)	0.046 (3)	0.034 (3)	0.0044 (19)	−0.0033 (19)	−0.005 (2)
C2	0.048 (3)	0.052 (3)	0.041 (3)	−0.002 (2)	−0.008 (2)	−0.011 (2)
C3	0.051 (3)	0.085 (5)	0.044 (3)	−0.008 (3)	−0.007 (3)	−0.018 (3)
C4	0.043 (3)	0.067 (4)	0.070 (4)	−0.005 (3)	−0.004 (3)	0.024 (3)
C5	0.038 (3)	0.050 (3)	0.047 (3)	−0.003 (2)	−0.003 (2)	0.005 (2)
C6	0.029 (2)	0.042 (3)	0.037 (3)	0.0009 (19)	0.0021 (19)	−0.006 (2)
C7	0.035 (2)	0.037 (3)	0.038 (3)	0.0014 (19)	0.002 (2)	−0.007 (2)
C8	0.036 (2)	0.037 (3)	0.035 (3)	0.0008 (19)	−0.0050 (19)	−0.013 (2)
C9	0.039 (3)	0.041 (3)	0.035 (3)	0.003 (2)	−0.004 (2)	−0.009 (2)
C10	0.043 (3)	0.034 (2)	0.033 (3)	−0.002 (2)	−0.007 (2)	−0.006 (2)
C11	0.043 (3)	0.038 (3)	0.037 (3)	0.004 (2)	−0.007 (2)	−0.005 (2)
C12	0.050 (3)	0.042 (3)	0.038 (3)	0.003 (2)	0.002 (2)	−0.010 (2)
C13	0.047 (3)	0.030 (2)	0.039 (3)	−0.001 (2)	−0.011 (2)	−0.006 (2)
C14	0.044 (3)	0.037 (3)	0.046 (3)	0.005 (2)	−0.010 (2)	−0.004 (2)
C15	0.043 (3)	0.035 (3)	0.042 (3)	0.000 (2)	0.005 (2)	−0.009 (2)
N1	0.040 (2)	0.037 (2)	0.041 (2)	0.0094 (17)	−0.0127 (17)	−0.0113 (18)
N2	0.062 (3)	0.036 (2)	0.033 (2)	0.0022 (19)	−0.0145 (19)	−0.0089 (18)
O2	0.048 (2)	0.050 (2)	0.050 (2)	0.0003 (16)	0.0008 (17)	0.0019 (17)
O3	0.067 (2)	0.041 (2)	0.042 (2)	−0.0016 (17)	−0.0091 (17)	−0.0152 (17)
O4	0.056 (2)	0.041 (2)	0.047 (2)	−0.0037 (16)	0.0011 (17)	−0.0202 (16)
O1A	0.053 (2)	0.045 (2)	0.052 (2)	0.0170 (16)	−0.0234 (17)	−0.0265 (17)
S1	0.0404 (6)	0.0357 (6)	0.0399 (7)	0.0042 (5)	−0.0088 (5)	−0.0094 (5)

Geometric parameters (Å, º) top

Br1—C11	1.882 (5)	C8—C9	1.471 (6)
Br2—C13	1.890 (5)	C9—O3	1.230 (6)
Br3—C15	1.886 (5)	C9—N2	1.355 (6)
C1—C2	1.368 (7)	C10—C11	1.385 (7)
C1—C6	1.411 (7)	C10—C15	1.391 (7)
C1—S1	1.757 (5)	C10—N2	1.408 (6)
C2—C3	1.405 (8)	C11—C12	1.395 (7)
C2—H2	0.9300	C12—C13	1.371 (7)
C3—C4	1.345 (9)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.363 (7)
C4—C5	1.415 (8)	C14—C15	1.381 (7)
C4—H4A	0.9300	C14—H14	0.9300
C5—C6	1.383 (7)	N1—S1	1.628 (4)
C5—H5	0.9300	N1—H1	0.8600
C6—C7	1.461 (7)	N2—H2A	0.8600
C7—O4	1.328 (5)	O2—S1	1.418 (4)
C7—C8	1.348 (7)	O4—H4	0.8200
C8—N1	1.435 (6)	O1A—S1	1.450 (3)

C2—C1—C6	121.6 (5)	C15—C10—N2	119.5 (4)
C2—C1—S1	119.9 (4)	C10—C11—C12	121.3 (4)
C6—C1—S1	118.2 (4)	C10—C11—Br1	121.5 (4)
C1—C2—C3	119.1 (5)	C12—C11—Br1	117.1 (4)
C1—C2—H2	120.4	C13—C12—C11	118.6 (4)
C3—C2—H2	120.4	C13—C12—H12	120.7
C4—C3—C2	120.2 (6)	C11—C12—H12	120.7
C4—C3—H3	119.9	C14—C13—C12	122.0 (5)
C2—C3—H3	119.9	C14—C13—Br2	118.1 (4)
C3—C4—C5	121.2 (6)	C12—C13—Br2	119.8 (4)
C3—C4—H4A	119.4	C13—C14—C15	118.5 (4)
C5—C4—H4A	119.4	C13—C14—H14	120.7
C6—C5—C4	119.4 (5)	C15—C14—H14	120.7
C6—C5—H5	120.3	C14—C15—C10	122.1 (4)
C4—C5—H5	120.3	C14—C15—Br3	117.9 (4)
C5—C6—C1	118.3 (5)	C10—C15—Br3	120.0 (4)
C5—C6—C7	121.3 (5)	C8—N1—S1	116.2 (3)
C1—C6—C7	120.4 (4)	C8—N1—H1	121.9
O4—C7—C8	120.9 (4)	S1—N1—H1	121.9
O4—C7—C6	115.6 (4)	C9—N2—C10	124.8 (4)
C8—C7—C6	123.4 (4)	C9—N2—H2A	117.6
C7—C8—N1	120.9 (4)	C10—N2—H2A	117.6
C7—C8—C9	121.2 (4)	C7—O4—H4	109.5
N1—C8—C9	117.7 (4)	O2—S1—O1A	117.6 (2)
O3—C9—N2	122.8 (4)	O2—S1—N1	108.5 (2)
O3—C9—C8	121.5 (4)	O1A—S1—N1	107.9 (2)
N2—C9—C8	115.8 (4)	O2—S1—C1	108.0 (2)
C11—C10—C15	117.4 (4)	O1A—S1—C1	111.6 (2)
C11—C10—N2	123.0 (4)	N1—S1—C1	101.9 (2)

C6—C1—C2—C3	−0.1 (7)	C10—C11—C12—C13	3.3 (7)
S1—C1—C2—C3	−174.8 (4)	Br1—C11—C12—C13	−172.9 (4)
C1—C2—C3—C4	2.5 (8)	C11—C12—C13—C14	−2.3 (8)
C2—C3—C4—C5	−2.3 (9)	C11—C12—C13—Br2	173.8 (4)
C3—C4—C5—C6	−0.3 (8)	C12—C13—C14—C15	−0.2 (8)
C4—C5—C6—C1	2.6 (7)	Br2—C13—C14—C15	−176.4 (4)
C4—C5—C6—C7	−179.7 (5)	C13—C14—C15—C10	1.8 (7)
C2—C1—C6—C5	−2.4 (7)	C13—C14—C15—Br3	−178.5 (4)
S1—C1—C6—C5	172.3 (3)	C11—C10—C15—C14	−0.8 (7)
C2—C1—C6—C7	179.9 (4)	N2—C10—C15—C14	175.5 (4)
S1—C1—C6—C7	−5.3 (6)	C11—C10—C15—Br3	179.5 (4)
C5—C6—C7—O4	−11.4 (6)	N2—C10—C15—Br3	−4.2 (6)
C1—C6—C7—O4	166.2 (4)	C7—C8—N1—S1	40.0 (6)
C5—C6—C7—C8	170.3 (5)	C9—C8—N1—S1	−135.0 (4)
C1—C6—C7—C8	−12.1 (7)	O3—C9—N2—C10	2.5 (7)
O4—C7—C8—N1	176.5 (4)	C8—C9—N2—C10	−178.0 (4)
C6—C7—C8—N1	−5.3 (7)	C11—C10—N2—C9	−64.1 (7)
O4—C7—C8—C9	−8.7 (7)	C15—C10—N2—C9	119.8 (5)
C6—C7—C8—C9	169.5 (4)	C8—N1—S1—O2	65.2 (4)
C7—C8—C9—O3	14.5 (7)	C8—N1—S1—O1A	−166.3 (3)
N1—C8—C9—O3	−170.5 (4)	C8—N1—S1—C1	−48.6 (4)
C7—C8—C9—N2	−165.0 (4)	C2—C1—S1—O2	93.0 (4)
N1—C8—C9—N2	10.0 (6)	C6—C1—S1—O2	−81.8 (4)
C15—C10—C11—C12	−1.8 (7)	C2—C1—S1—O1A	−37.8 (5)
N2—C10—C11—C12	−178.0 (5)	C6—C1—S1—O1A	147.4 (4)
C15—C10—C11—Br1	174.3 (4)	C2—C1—S1—N1	−152.7 (4)
N2—C10—C11—Br1	−1.9 (7)	C6—C1—S1—N1	32.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.83	2.561 (5)	147
N1—H1···O1Aⁱ	0.86	2.29	2.966 (5)	136
N2—H2A···Br2ⁱⁱ	0.86	2.79	3.597 (4)	157
O4—H4···Br2ⁱⁱⁱ	0.82	2.88	3.403 (3)	124

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

Experimental details

Crystal data
Chemical formula	C₁₅H₉Br₃N₂O₄S
M_r	553.03
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5082 (4), 8.7486 (6), 13.0669 (9)
α, β, γ (°)	83.618 (2), 86.280 (2), 87.684 (2)
V (Å³)	850.72 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.26
Crystal size (mm)	0.18 × 0.16 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.355, 0.502
No. of measured, independent and observed [I > 2σ(I)] reflections	16515, 3794, 2599
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.01
No. of reflections	3794
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.16, −0.63

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.8200	1.8300	2.561 (5)	147.00
N1—H1···O1Aⁱ	0.86	2.29	2.966 (5)	136.0
N2—H2A···Br2ⁱⁱ	0.86	2.79	3.597 (4)	157.0
O4—H4···Br2ⁱⁱⁱ	0.82	2.88	3.403 (3)	123.6

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

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for a grant.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kojić-Prodić, B. & Rużić-Toroš, Ž. (1982). Acta Cryst. B38, 2948–2951. CSD CrossRef Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2007). 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
Turck, D., Busch, U., Heinzel, G., Narjes, H. & Nehmiz, G. (1996). J. Clin. Pharmacol. 36, 79–84. PubMed Web of Science Google Scholar
Weast, R. C., Astle, M. J. & Beyer, W. H. (1984). Handbook of Chemistry and Physics, 65th ed. Boca Raton, Florida: CRC Press. Google Scholar
Zia-ur-Rehman, M., Choudary, J. A. & Ahmad, S. (2005). Bull. Korean Chem. Soc. 26, 1771–1175. CAS Google Scholar

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Volume 65| Part 12| December 2009| Page o2998

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4-Hydr­­oxy-N-(2,4,6-tri­bromo­phen­yl)-2H-1,2-benzo­thia­zine-3-carboxamide 1,1-dioxide

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