(2-Bromo-phen-yl)(4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)methanone.

In the title mol-ecule, C(15)H(10)BrNO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.554 (7) and 0.198 (8) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is consolidated by intra-molecular O-H⋯O inter-actions and the crystal packing features N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the first synthesis of benzothia­zine, see: Braun (1923 ▶). For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ▶). For the biological activity of 1,2-benzothia­zine derivatives, see: Lombardino & Wiseman (1972 ▶); Gupta et al. (1993 ▶, 2002 ▶); Zia-ur-Rehman et al. (2006 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C15H10BrNO4S

M = 380.21

Monoclinic,

a = 12.0433 (4) Å

b = 8.5491 (3) Å

c = 14.7841 (5) Å

β = 106.3950 (19)°

V = 1460.27 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.98 mm−1

T = 173 K

0.14 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.681, T max = 0.797

6205 measured reflections

3339 independent reflections

2528 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.106

S = 1.10

3339 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.61 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013281/aa2054sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013281/aa2054Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013281/aa2054Isup3.cml

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

C15H10BrNO4S	F(000) = 760
Mr = 380.21	Dx = 1.729 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3429 reflections
a = 12.0433 (4) Å	θ = 1.0–27.5°
b = 8.5491 (3) Å	µ = 2.98 mm−1
c = 14.7841 (5) Å	T = 173 K
β = 106.3950 (19)°	Prism, pale yellow
V = 1460.27 (9) Å3	0.14 × 0.12 × 0.08 mm
Z = 4

Nonius KappaCCD diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω and φ scans	θmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −15→15
Tmin = 0.681, Tmax = 0.797	k = −11→10
6205 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0181P)2 + 4.4694P] where P = (Fo2 + 2Fc2)/3
3339 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.61 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	0.27922 (4)	0.40093 (6)	0.66394 (3)	0.03958 (14)
S1	0.81353 (8)	0.40492 (13)	0.89491 (6)	0.0277 (2)
O1	0.8507 (2)	0.2475 (4)	0.9213 (2)	0.0365 (7)
O2	0.8381 (2)	0.5262 (4)	0.9640 (2)	0.0398 (7)
O3	0.6691 (2)	0.2135 (4)	0.62289 (19)	0.0340 (7)
H3O	0.6030	0.1754	0.6166	0.041*
O4	0.4885 (2)	0.1511 (3)	0.67117 (19)	0.0317 (6)
N1	0.6746 (3)	0.4016 (4)	0.8466 (2)	0.0269 (7)
H1N	0.642 (4)	0.484 (5)	0.848 (3)	0.032*
C1	0.8650 (3)	0.4564 (5)	0.7985 (3)	0.0273 (8)
C2	0.9651 (3)	0.5437 (5)	0.8102 (3)	0.0367 (10)
H2	1.0047	0.5867	0.8698	0.044*
C3	1.0058 (4)	0.5666 (6)	0.7323 (3)	0.0415 (11)
H3	1.0734	0.6279	0.7387	0.050*
C4	0.9504 (4)	0.5020 (5)	0.6459 (3)	0.0385 (10)
H4	0.9810	0.5178	0.5940	0.046*
C5	0.8507 (3)	0.4147 (5)	0.6341 (3)	0.0330 (9)
H5	0.8129	0.3709	0.5742	0.040*
C6	0.8057 (3)	0.3911 (5)	0.7107 (3)	0.0264 (8)
C7	0.6983 (3)	0.3029 (5)	0.6993 (3)	0.0241 (8)
C8	0.6335 (3)	0.3124 (5)	0.7626 (3)	0.0249 (8)
C9	0.5241 (3)	0.2322 (5)	0.7435 (3)	0.0262 (8)
C10	0.4524 (3)	0.2456 (5)	0.8110 (3)	0.0262 (8)
C11	0.3407 (3)	0.3076 (5)	0.7837 (3)	0.0267 (8)
C12	0.2732 (4)	0.3111 (5)	0.8461 (3)	0.0374 (10)
H12	0.1979	0.3557	0.8274	0.045*
C13	0.3164 (4)	0.2495 (5)	0.9352 (3)	0.0359 (10)
H13	0.2704	0.2511	0.9779	0.043*
C14	0.4255 (4)	0.1857 (5)	0.9630 (3)	0.0368 (10)
H14	0.4540	0.1419	1.0242	0.044*
C15	0.4942 (4)	0.1852 (5)	0.9020 (3)	0.0328 (9)
H15	0.5703	0.1433	0.9222	0.039*

	U11	U22	U33	U12	U13	U23
Br1	0.0341 (2)	0.0479 (3)	0.0371 (2)	0.0063 (2)	0.01057 (18)	0.0086 (2)
S1	0.0245 (5)	0.0325 (5)	0.0260 (4)	0.0008 (4)	0.0069 (4)	−0.0029 (4)
O1	0.0378 (16)	0.0376 (17)	0.0352 (15)	0.0096 (14)	0.0120 (13)	0.0072 (14)
O2	0.0340 (16)	0.0465 (19)	0.0389 (16)	−0.0021 (14)	0.0102 (13)	−0.0163 (15)
O3	0.0296 (15)	0.0432 (18)	0.0324 (14)	−0.0100 (13)	0.0142 (12)	−0.0119 (14)
O4	0.0300 (14)	0.0371 (17)	0.0300 (14)	−0.0073 (13)	0.0116 (12)	−0.0035 (13)
N1	0.0249 (16)	0.0263 (17)	0.0310 (16)	0.0043 (15)	0.0102 (13)	−0.0028 (15)
C1	0.0242 (18)	0.027 (2)	0.033 (2)	0.0018 (16)	0.0134 (16)	0.0010 (17)
C2	0.029 (2)	0.038 (2)	0.043 (2)	−0.0072 (19)	0.0109 (18)	−0.008 (2)
C3	0.032 (2)	0.042 (3)	0.057 (3)	−0.008 (2)	0.022 (2)	0.000 (2)
C4	0.035 (2)	0.044 (3)	0.042 (2)	−0.005 (2)	0.020 (2)	0.005 (2)
C5	0.032 (2)	0.036 (2)	0.035 (2)	0.0042 (19)	0.0151 (17)	0.0026 (19)
C6	0.0224 (17)	0.025 (2)	0.033 (2)	0.0017 (16)	0.0107 (15)	0.0007 (17)
C7	0.0236 (18)	0.025 (2)	0.0237 (17)	0.0011 (16)	0.0063 (14)	−0.0008 (16)
C8	0.0224 (18)	0.027 (2)	0.0261 (18)	0.0001 (16)	0.0083 (15)	0.0007 (16)
C9	0.0261 (19)	0.026 (2)	0.0285 (18)	0.0013 (16)	0.0102 (15)	0.0036 (17)
C10	0.0230 (18)	0.026 (2)	0.0315 (19)	−0.0055 (16)	0.0100 (15)	−0.0056 (17)
C11	0.0279 (19)	0.025 (2)	0.0281 (19)	−0.0016 (16)	0.0098 (16)	−0.0036 (16)
C12	0.032 (2)	0.036 (2)	0.050 (3)	0.000 (2)	0.021 (2)	−0.005 (2)
C13	0.040 (2)	0.036 (2)	0.038 (2)	−0.004 (2)	0.0227 (19)	−0.005 (2)
C14	0.046 (2)	0.040 (3)	0.026 (2)	−0.002 (2)	0.0127 (18)	0.0008 (19)
C15	0.030 (2)	0.039 (2)	0.030 (2)	0.0002 (19)	0.0095 (17)	−0.0010 (19)

Br1—C11	1.892 (4)	C4—H4	0.9500
S1—O2	1.427 (3)	C5—C6	1.401 (5)
S1—O1	1.437 (3)	C5—H5	0.9500
S1—N1	1.623 (3)	C6—C7	1.466 (5)
S1—C1	1.763 (4)	C7—C8	1.378 (5)
O3—C7	1.327 (4)	C8—C9	1.441 (5)
O3—H3O	0.8400	C9—C10	1.498 (5)
O4—C9	1.245 (5)	C10—C11	1.395 (5)
N1—C8	1.423 (5)	C10—C15	1.395 (5)
N1—H1N	0.81 (5)	C11—C12	1.392 (5)
C1—C2	1.387 (5)	C12—C13	1.378 (6)
C1—C6	1.409 (5)	C12—H12	0.9500
C2—C3	1.386 (6)	C13—C14	1.374 (6)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.379 (6)	C14—C15	1.385 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.382 (6)	C15—H15	0.9500
O2—S1—O1	120.01 (19)	O3—C7—C8	123.1 (3)
O2—S1—N1	107.91 (18)	O3—C7—C6	114.0 (3)
O1—S1—N1	107.86 (19)	C8—C7—C6	122.8 (3)
O2—S1—C1	110.4 (2)	C7—C8—N1	120.0 (3)
O1—S1—C1	107.41 (18)	C7—C8—C9	120.0 (3)
N1—S1—C1	101.73 (18)	N1—C8—C9	119.9 (3)
C7—O3—H3O	109.5	O4—C9—C8	120.5 (3)
C8—N1—S1	117.0 (3)	O4—C9—C10	119.4 (3)
C8—N1—H1N	116 (3)	C8—C9—C10	120.0 (3)
S1—N1—H1N	114 (3)	C11—C10—C15	118.4 (3)
C2—C1—C6	121.6 (4)	C11—C10—C9	121.8 (3)
C2—C1—S1	121.7 (3)	C15—C10—C9	119.7 (3)
C6—C1—S1	116.4 (3)	C12—C11—C10	120.8 (4)
C3—C2—C1	118.1 (4)	C12—C11—Br1	117.6 (3)
C3—C2—H2	120.9	C10—C11—Br1	121.5 (3)
C1—C2—H2	120.9	C13—C12—C11	119.5 (4)
C4—C3—C2	121.4 (4)	C13—C12—H12	120.3
C4—C3—H3	119.3	C11—C12—H12	120.3
C2—C3—H3	119.3	C14—C13—C12	120.6 (4)
C3—C4—C5	120.7 (4)	C14—C13—H13	119.7
C3—C4—H4	119.7	C12—C13—H13	119.7
C5—C4—H4	119.7	C13—C14—C15	120.2 (4)
C4—C5—C6	119.7 (4)	C13—C14—H14	119.9
C4—C5—H5	120.2	C15—C14—H14	119.9
C6—C5—H5	120.2	C14—C15—C10	120.5 (4)
C5—C6—C1	118.5 (4)	C14—C15—H15	119.8
C5—C6—C7	120.8 (4)	C10—C15—H15	119.8
C1—C6—C7	120.7 (3)
O2—S1—N1—C8	167.0 (3)	C6—C7—C8—N1	−4.8 (6)
O1—S1—N1—C8	−61.9 (3)	O3—C7—C8—C9	−4.8 (6)
C1—S1—N1—C8	50.9 (3)	C6—C7—C8—C9	175.2 (4)
O2—S1—C1—C2	34.0 (4)	S1—N1—C8—C7	−34.1 (5)
O1—S1—C1—C2	−98.5 (4)	S1—N1—C8—C9	145.9 (3)
N1—S1—C1—C2	148.3 (4)	C7—C8—C9—O4	1.6 (6)
O2—S1—C1—C6	−152.1 (3)	N1—C8—C9—O4	−178.4 (4)
O1—S1—C1—C6	75.4 (3)	C7—C8—C9—C10	−178.5 (4)
N1—S1—C1—C6	−37.7 (3)	N1—C8—C9—C10	1.4 (6)
C6—C1—C2—C3	0.3 (6)	O4—C9—C10—C11	−60.3 (5)
S1—C1—C2—C3	173.9 (3)	C8—C9—C10—C11	119.8 (4)
C1—C2—C3—C4	−1.3 (7)	O4—C9—C10—C15	115.1 (4)
C2—C3—C4—C5	1.2 (7)	C8—C9—C10—C15	−64.7 (5)
C3—C4—C5—C6	−0.2 (7)	C15—C10—C11—C12	0.9 (6)
C4—C5—C6—C1	−0.7 (6)	C9—C10—C11—C12	176.4 (4)
C4—C5—C6—C7	178.2 (4)	C15—C10—C11—Br1	177.0 (3)
C2—C1—C6—C5	0.7 (6)	C9—C10—C11—Br1	−7.5 (5)
S1—C1—C6—C5	−173.3 (3)	C10—C11—C12—C13	−1.4 (6)
C2—C1—C6—C7	−178.2 (4)	Br1—C11—C12—C13	−177.7 (3)
S1—C1—C6—C7	7.8 (5)	C11—C12—C13—C14	0.4 (7)
C5—C6—C7—O3	18.6 (5)	C12—C13—C14—C15	1.1 (7)
C1—C6—C7—O3	−162.5 (4)	C13—C14—C15—C10	−1.6 (7)
C5—C6—C7—C8	−161.3 (4)	C11—C10—C15—C14	0.6 (6)
C1—C6—C7—C8	17.5 (6)	C9—C10—C15—C14	−175.0 (4)
O3—C7—C8—N1	175.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.81 (5)	2.08 (5)	2.861 (4)	160 (4)
C13—H13···O2ii	0.95	2.59	3.305 (5)	132
O3—H3O···O4	0.84	1.80	2.530 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.81 (5)	2.08 (5)	2.861 (4)	160 (4)
C13—H13⋯O2ii	0.95	2.59	3.305 (5)	132
O3—H3O⋯O4	0.84	1.80	2.530 (4)	145

Symmetry codes: (i) ; (ii) .