4-Hy-droxy-2-methyl-1,1-dioxo-N-phenyl-2H-1λ(6),2-benzothia-zine-3-carboxamide.

In the title mol-ecule, C(16)H(14)N(2)O(4)S, the thia-zine ring adopts a twist chair conformation with the N and adjacent C atom displaced by 0.966 (3) and 0.386 (4) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The dihedral angle between the mean planes of the benzene rings is 37.65 (10)°. The mol-ecular structure features an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For background to the biological activity of benzothia­zine derivatives, and further synthetic details, see: Siddiqui et al. (2007 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2008 ▶; 2009 ▶).

Experimental

Crystal data

C16H14N2O4S

M = 330.35

Monoclinic,

a = 10.502 (2) Å

b = 7.649 (3) Å

c = 19.235 (4) Å

β = 103.395 (15)°

V = 1503.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.10 × 0.08 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.977, T max = 0.984

12580 measured reflections

3450 independent reflections

2901 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.06

3450 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.31 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021708/hb6789sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021708/hb6789Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021708/hb6789Isup3.cml

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

C16H14N2O4S	F(000) = 688
Mr = 330.35	Dx = 1.460 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6808 reflections
a = 10.502 (2) Å	θ = 1.0–27.5°
b = 7.649 (3) Å	µ = 0.24 mm−1
c = 19.235 (4) Å	T = 173 K
β = 103.395 (15)°	Prism, colorless
V = 1503.1 (7) Å3	0.10 × 0.08 × 0.07 mm
Z = 4

Nonius KappaCCD diffractometer	3450 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω and φ scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
Tmin = 0.977, Tmax = 0.984	k = −9→9
12580 measured reflections	l = −24→24

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: difference Fourier map
wR(F2) = 0.119	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0433P)2 + 1.2798P] where P = (Fo2 + 2Fc2)/3
3450 reflections	(Δ/σ)max = 0.002
210 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.31 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
S1	0.06977 (5)	0.65050 (7)	−0.08374 (3)	0.02930 (15)
O1	0.03451 (13)	0.7324 (2)	−0.02412 (8)	0.0343 (4)
O2	−0.03040 (14)	0.5885 (2)	−0.14150 (8)	0.0397 (4)
O3	0.46114 (13)	0.7361 (2)	0.03008 (8)	0.0336 (3)
H3O	0.4835	0.6611	0.0625	0.050*
O4	0.44020 (13)	0.4617 (2)	0.10046 (7)	0.0327 (3)
N1	0.16698 (15)	0.4874 (2)	−0.05340 (8)	0.0269 (4)
N2	0.25707 (16)	0.2921 (2)	0.06629 (9)	0.0286 (4)
H2N	0.1836	0.2817	0.0335	0.034*
C1	0.1745 (2)	0.7916 (3)	−0.11620 (10)	0.0290 (4)
C2	0.1311 (2)	0.8897 (3)	−0.17712 (11)	0.0344 (5)
H2	0.0429	0.8807	−0.2036	0.041*
C3	0.2174 (2)	1.0016 (3)	−0.19931 (12)	0.0374 (5)
H3	0.1892	1.0690	−0.2415	0.045*
C4	0.3453 (2)	1.0147 (3)	−0.15962 (12)	0.0349 (5)
H4	0.4040	1.0927	−0.1747	0.042*
C5	0.3885 (2)	0.9167 (3)	−0.09875 (11)	0.0312 (4)
H5	0.4762	0.9286	−0.0719	0.037*
C6	0.30455 (19)	0.8003 (3)	−0.07627 (10)	0.0267 (4)
C7	0.34974 (18)	0.6857 (3)	−0.01458 (10)	0.0265 (4)
C8	0.28462 (18)	0.5399 (3)	−0.00344 (10)	0.0258 (4)
C9	0.33296 (18)	0.4289 (3)	0.05864 (10)	0.0275 (4)
C10	0.1852 (2)	0.3560 (3)	−0.10655 (12)	0.0386 (5)
H10A	0.2385	0.2592	−0.0821	0.046*
H10B	0.2296	0.4101	−0.1406	0.046*
H10C	0.0997	0.3115	−0.1322	0.046*
C11	0.28010 (19)	0.1627 (3)	0.12035 (11)	0.0293 (4)
C12	0.3610 (2)	0.1906 (3)	0.18722 (11)	0.0338 (5)
H12	0.4041	0.2997	0.1986	0.041*
C13	0.3782 (2)	0.0577 (3)	0.23736 (13)	0.0426 (6)
H13	0.4344	0.0758	0.2832	0.051*
C14	0.3156 (3)	−0.0998 (4)	0.22204 (15)	0.0486 (6)
H14	0.3279	−0.1898	0.2570	0.058*
C15	0.2342 (3)	−0.1267 (3)	0.15529 (15)	0.0497 (6)
H15	0.1904	−0.2355	0.1445	0.060*
C16	0.2163 (2)	0.0035 (3)	0.10429 (13)	0.0395 (5)
H16	0.1606	−0.0156	0.0584	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0215 (2)	0.0334 (3)	0.0307 (3)	0.0006 (2)	0.00107 (18)	−0.0006 (2)
O1	0.0239 (7)	0.0404 (9)	0.0390 (8)	0.0016 (6)	0.0082 (6)	−0.0030 (7)
O2	0.0295 (8)	0.0462 (10)	0.0373 (8)	−0.0022 (7)	−0.0046 (6)	−0.0019 (7)
O3	0.0269 (7)	0.0359 (8)	0.0334 (8)	−0.0061 (6)	−0.0021 (6)	0.0031 (6)
O4	0.0277 (7)	0.0370 (8)	0.0296 (7)	−0.0034 (6)	−0.0011 (6)	0.0033 (6)
N1	0.0228 (8)	0.0292 (9)	0.0267 (8)	−0.0014 (7)	0.0016 (6)	−0.0016 (7)
N2	0.0238 (8)	0.0316 (9)	0.0288 (8)	0.0000 (7)	0.0027 (6)	0.0034 (7)
C1	0.0293 (10)	0.0288 (11)	0.0283 (10)	0.0018 (8)	0.0052 (8)	0.0002 (8)
C2	0.0357 (11)	0.0340 (12)	0.0301 (10)	0.0059 (9)	0.0010 (8)	0.0011 (9)
C3	0.0528 (14)	0.0295 (11)	0.0295 (10)	0.0065 (10)	0.0088 (9)	0.0033 (9)
C4	0.0445 (12)	0.0261 (11)	0.0376 (11)	0.0015 (9)	0.0166 (9)	0.0016 (9)
C5	0.0310 (10)	0.0286 (10)	0.0349 (11)	0.0022 (8)	0.0093 (8)	−0.0004 (9)
C6	0.0260 (10)	0.0252 (10)	0.0287 (9)	0.0024 (8)	0.0061 (7)	−0.0014 (8)
C7	0.0205 (9)	0.0307 (10)	0.0275 (9)	0.0009 (7)	0.0040 (7)	−0.0032 (8)
C8	0.0219 (9)	0.0280 (10)	0.0260 (9)	0.0002 (7)	0.0025 (7)	−0.0001 (8)
C9	0.0239 (9)	0.0298 (10)	0.0288 (10)	0.0013 (8)	0.0062 (7)	−0.0004 (8)
C10	0.0436 (13)	0.0346 (12)	0.0344 (11)	0.0039 (10)	0.0025 (9)	−0.0071 (9)
C11	0.0256 (10)	0.0294 (10)	0.0353 (11)	0.0050 (8)	0.0117 (8)	0.0044 (9)
C12	0.0358 (11)	0.0349 (12)	0.0317 (10)	0.0027 (9)	0.0099 (8)	0.0020 (9)
C13	0.0440 (13)	0.0511 (15)	0.0342 (11)	0.0086 (11)	0.0118 (10)	0.0098 (11)
C14	0.0510 (15)	0.0430 (14)	0.0551 (15)	0.0076 (12)	0.0188 (12)	0.0207 (12)
C15	0.0505 (15)	0.0320 (13)	0.0688 (17)	−0.0029 (11)	0.0184 (13)	0.0108 (12)
C16	0.0370 (12)	0.0339 (12)	0.0468 (13)	−0.0009 (10)	0.0082 (10)	0.0036 (10)

S1—O2	1.4228 (15)	C5—C6	1.390 (3)
S1—O1	1.4288 (15)	C5—H5	0.9500
S1—N1	1.6316 (18)	C6—C7	1.463 (3)
S1—C1	1.756 (2)	C7—C8	1.351 (3)
O3—C7	1.338 (2)	C8—C9	1.458 (3)
O3—H3O	0.8400	C10—H10A	0.9800
O4—C9	1.249 (2)	C10—H10B	0.9800
N1—C8	1.436 (2)	C10—H10C	0.9800
N1—C10	1.478 (3)	C11—C12	1.384 (3)
N2—C9	1.344 (3)	C11—C16	1.389 (3)
N2—C11	1.415 (3)	C12—C13	1.384 (3)
N2—H2N	0.8800	C12—H12	0.9500
C1—C2	1.377 (3)	C13—C14	1.372 (4)
C1—C6	1.405 (3)	C13—H13	0.9500
C2—C3	1.385 (3)	C14—C15	1.383 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.386 (3)	C15—C16	1.380 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.376 (3)	C16—H16	0.9500
C4—H4	0.9500
O2—S1—O1	119.39 (9)	O3—C7—C6	114.78 (17)
O2—S1—N1	108.21 (10)	C8—C7—C6	122.84 (18)
O1—S1—N1	107.76 (9)	C7—C8—N1	120.90 (17)
O2—S1—C1	109.76 (10)	C7—C8—C9	121.19 (18)
O1—S1—C1	108.43 (10)	N1—C8—C9	117.89 (17)
N1—S1—C1	101.85 (9)	O4—C9—N2	123.74 (19)
C7—O3—H3O	109.5	O4—C9—C8	120.11 (18)
C8—N1—C10	115.09 (16)	N2—C9—C8	116.15 (17)
C8—N1—S1	113.31 (14)	N1—C10—H10A	109.5
C10—N1—S1	116.32 (13)	N1—C10—H10B	109.5
C9—N2—C11	128.34 (17)	H10A—C10—H10B	109.5
C9—N2—H2N	115.8	N1—C10—H10C	109.5
C11—N2—H2N	115.8	H10A—C10—H10C	109.5
C2—C1—C6	121.9 (2)	H10B—C10—H10C	109.5
C2—C1—S1	121.73 (16)	C12—C11—C16	120.2 (2)
C6—C1—S1	116.40 (15)	C12—C11—N2	122.6 (2)
C1—C2—C3	119.2 (2)	C16—C11—N2	117.26 (19)
C1—C2—H2	120.4	C11—C12—C13	119.1 (2)
C3—C2—H2	120.4	C11—C12—H12	120.4
C4—C3—C2	119.7 (2)	C13—C12—H12	120.4
C4—C3—H3	120.2	C14—C13—C12	121.1 (2)
C2—C3—H3	120.2	C14—C13—H13	119.4
C5—C4—C3	121.1 (2)	C12—C13—H13	119.4
C5—C4—H4	119.5	C13—C14—C15	119.5 (2)
C3—C4—H4	119.5	C13—C14—H14	120.2
C4—C5—C6	120.4 (2)	C15—C14—H14	120.2
C4—C5—H5	119.8	C16—C15—C14	120.4 (2)
C6—C5—H5	119.8	C16—C15—H15	119.8
C5—C6—C1	117.81 (18)	C14—C15—H15	119.8
C5—C6—C7	121.73 (18)	C15—C16—C11	119.7 (2)
C1—C6—C7	120.43 (18)	C15—C16—H16	120.2
O3—C7—C8	122.38 (18)	C11—C16—H16	120.2
O2—S1—N1—C8	169.66 (13)	C1—C6—C7—C8	17.5 (3)
O1—S1—N1—C8	−59.96 (15)	O3—C7—C8—N1	−178.49 (17)
C1—S1—N1—C8	54.02 (15)	C6—C7—C8—N1	1.4 (3)
O2—S1—N1—C10	32.92 (18)	O3—C7—C8—C9	0.1 (3)
O1—S1—N1—C10	163.30 (15)	C6—C7—C8—C9	179.90 (18)
C1—S1—N1—C10	−82.72 (16)	C10—N1—C8—C7	96.1 (2)
O2—S1—C1—C2	29.0 (2)	S1—N1—C8—C7	−41.2 (2)
O1—S1—C1—C2	−103.00 (19)	C10—N1—C8—C9	−82.5 (2)
N1—S1—C1—C2	143.52 (18)	S1—N1—C8—C9	140.21 (16)
O2—S1—C1—C6	−151.62 (16)	C11—N2—C9—O4	0.2 (3)
O1—S1—C1—C6	76.36 (17)	C11—N2—C9—C8	179.09 (18)
N1—S1—C1—C6	−37.12 (18)	C7—C8—C9—O4	−4.3 (3)
C6—C1—C2—C3	−0.7 (3)	N1—C8—C9—O4	174.32 (18)
S1—C1—C2—C3	178.60 (17)	C7—C8—C9—N2	176.80 (18)
C1—C2—C3—C4	−0.8 (3)	N1—C8—C9—N2	−4.6 (3)
C2—C3—C4—C5	0.8 (3)	C9—N2—C11—C12	23.9 (3)
C3—C4—C5—C6	0.8 (3)	C9—N2—C11—C16	−156.9 (2)
C4—C5—C6—C1	−2.2 (3)	C16—C11—C12—C13	0.6 (3)
C4—C5—C6—C7	175.80 (19)	N2—C11—C12—C13	179.77 (19)
C2—C1—C6—C5	2.2 (3)	C11—C12—C13—C14	−0.7 (3)
S1—C1—C6—C5	−177.17 (15)	C12—C13—C14—C15	0.3 (4)
C2—C1—C6—C7	−175.82 (19)	C13—C14—C15—C16	0.2 (4)
S1—C1—C6—C7	4.8 (3)	C14—C15—C16—C11	−0.2 (4)
C5—C6—C7—O3	19.4 (3)	C12—C11—C16—C15	−0.2 (3)
C1—C6—C7—O3	−162.66 (18)	N2—C11—C16—C15	−179.3 (2)
C5—C6—C7—C8	−160.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.88	2.26	2.987 (2)	140
C3—H3···O2ii	0.95	2.48	3.300 (3)	145
C13—H13···O4iii	0.95	2.48	3.339 (3)	151
N2—H2N···N1	0.88	2.27	2.724 (2)	112
O3—H3O···O4	0.84	1.79	2.534 (2)	146
C12—H12···O4	0.95	2.36	2.902 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.88	2.26	2.987 (2)	140
C3—H3⋯O2ii	0.95	2.48	3.300 (3)	145
C13—H13⋯O4iii	0.95	2.48	3.339 (3)	151
O3—H3O⋯O4	0.84	1.79	2.534 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) .