4-Hydr-oxy-N-(2,4,6-tribromo-phen-yl)-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

In the title compound, C(15)H(19)Br(3)N(2)O(4)S, the thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. In the crystal, the mol-ecules are linked into a three-dimensional network through inter-molecular 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 = 553.03

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.01

3794 reflections

227 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −0.63 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H9Br3N2O4S	Z = 2
Mr = 553.03	F(000) = 532
Triclinic, P1	Dx = 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

Bruker APEXII CCD area-detector diffractometer	3794 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→9
Tmin = 0.355, Tmax = 0.502	k = −11→11
16515 measured reflections	l = −16→16

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(Fo2) + (0.049P)2 + 2.0189P] where P = (Fo2 + 2Fc2)/3
3794 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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⋯O1A i	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) ; (ii) ; (iii) .