Methyl 3-hydr-oxy-4-oxo-3,4-dihydro-2H-1,2-benzothia-zine-3-carboxyl-ate 1,1-dioxide monohydrate.

In the mol-ecule of the title compound, C(10)H(9)NO(6)S·H(2)O, the benzothia-zine ring adopts an envelope conformation. An intra-molecular N-H⋯O hydrogen bond results in the formation of a nonplanar five-membered ring which has a twisted conformation. In the crystal structure, inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules to form a three-dimensional network. There is a π-π contact between the benzene rings [centroid-centroid distance = 3.972 (2) Å].

Related literature

For general background, see: Shafiq, Khan et al. (2008 ▶); Shafiq, Tahir et al. (2008 ▶); Tahir et al. (2008 ▶). For related literature, see: Antsyshkina et al. (2003 ▶); Allen (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H9NO6S·n class="Chemical">H2O

M = 289.26

Orthorhombic,

a = 7.7504 (5) Å

b = 14.5638 (9) Å

c = 21.0615 (14) Å

V = 2377.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 (2) K

0.24 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.934, T max = 0.958

14889 measured reflections

2998 independent reflections

1895 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 1.01

2998 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: n class="Gene">APEX2; 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030948/hk2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030948/hk2537Isup2.hkl

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

C10H9NO6S·H2O	F(000) = 1200
Mr = 289.26	Dx = 1.616 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2998 reflections
a = 7.7504 (5) Å	θ = 3.0–28.5°
b = 14.5638 (9) Å	µ = 0.30 mm−1
c = 21.0615 (14) Å	T = 296 K
V = 2377.3 (3) Å3	Prismatic, colourless
Z = 8	0.24 × 0.18 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
graphite	Rint = 0.065
Detector resolution: 7.40 pixels mm-1	θmax = 28.5°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→10
Tmin = 0.934, Tmax = 0.958	l = −28→27
14889 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0491P)2 + 1.1022P] where P = (Fo2 + 2Fc2)/3
2998 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.18084 (8)	0.12546 (4)	0.08206 (3)	0.0314 (2)
O1	0.0037 (3)	0.32676 (13)	0.21865 (9)	0.0568 (8)
O2	0.3475 (2)	0.15746 (13)	0.06338 (9)	0.0450 (7)
O3	0.1137 (3)	0.04539 (12)	0.05197 (9)	0.0450 (6)
O4	0.2024 (2)	0.33701 (12)	0.09947 (10)	0.0360 (6)
H4O	0.204 (4)	0.3501 (19)	0.0608 (14)	0.0432*
O5	−0.0985 (3)	0.42862 (12)	0.08273 (10)	0.0460 (7)
O6	−0.2498 (2)	0.30222 (13)	0.10613 (9)	0.0413 (6)
O7	0.7145 (3)	0.10998 (15)	0.02689 (11)	0.0481 (7)
H71	0.731 (4)	0.054 (2)	0.0226 (15)	0.0577*
H72	0.615 (5)	0.116 (2)	0.0412 (16)	0.0577*
N1	0.0398 (3)	0.20645 (14)	0.07099 (10)	0.0308 (6)
H1	−0.052 (4)	0.1857 (18)	0.0675 (13)	0.0370*
C1	0.1243 (3)	0.17959 (16)	0.20533 (12)	0.0298 (7)
C2	0.1294 (4)	0.16328 (19)	0.27020 (13)	0.0414 (9)
H2	0.09091	0.20830	0.29812	0.0497*
C3	0.1908 (4)	0.0814 (2)	0.29384 (14)	0.0518 (10)
H3	0.19348	0.07164	0.33746	0.0623*
C4	0.2479 (5)	0.0141 (2)	0.25324 (15)	0.0525 (10)
H4	0.28955	−0.04093	0.26959	0.0629*
C5	0.2440 (4)	0.02761 (18)	0.18834 (14)	0.0444 (9)
H5	0.28239	−0.01804	0.16088	0.0533*
C6	0.1824 (3)	0.10985 (16)	0.16477 (12)	0.0306 (7)
C7	0.0552 (3)	0.26875 (16)	0.18234 (12)	0.0319 (8)
C8	0.0514 (3)	0.28972 (15)	0.11076 (11)	0.0284 (7)
C9	−0.1075 (3)	0.35000 (17)	0.09736 (12)	0.0312 (8)
C10	−0.4122 (3)	0.3507 (2)	0.10026 (15)	0.0500 (10)
H10A	−0.50577	0.30900	0.10785	0.0750*
H10B	−0.42207	0.37576	0.05825	0.0750*
H10C	−0.41623	0.39963	0.13080	0.0750*

	U11	U22	U33	U12	U13	U23
S1	0.0315 (3)	0.0292 (3)	0.0334 (3)	0.0025 (3)	0.0002 (3)	−0.0061 (3)
O1	0.0826 (16)	0.0444 (11)	0.0433 (12)	0.0237 (12)	−0.0002 (11)	−0.0134 (9)
O2	0.0328 (11)	0.0479 (11)	0.0544 (12)	0.0054 (9)	0.0128 (9)	−0.0020 (9)
O3	0.0591 (13)	0.0327 (9)	0.0433 (11)	0.0012 (9)	−0.0078 (10)	−0.0121 (8)
O4	0.0240 (9)	0.0376 (10)	0.0463 (11)	−0.0060 (8)	−0.0014 (8)	−0.0029 (9)
O5	0.0406 (12)	0.0312 (10)	0.0662 (14)	0.0041 (8)	−0.0023 (10)	0.0090 (9)
O6	0.0220 (9)	0.0402 (10)	0.0618 (13)	−0.0003 (8)	0.0007 (9)	0.0062 (9)
O7	0.0453 (13)	0.0400 (10)	0.0590 (14)	−0.0025 (10)	−0.0070 (10)	0.0005 (10)
N1	0.0258 (11)	0.0296 (10)	0.0370 (12)	−0.0008 (9)	−0.0049 (10)	−0.0052 (9)
C1	0.0261 (12)	0.0291 (12)	0.0342 (13)	0.0004 (10)	−0.0018 (10)	−0.0021 (10)
C2	0.0470 (16)	0.0411 (15)	0.0362 (14)	0.0006 (13)	0.0007 (13)	−0.0049 (12)
C3	0.063 (2)	0.0559 (18)	0.0364 (15)	0.0002 (17)	−0.0064 (15)	0.0089 (14)
C4	0.067 (2)	0.0393 (15)	0.0513 (18)	0.0054 (15)	−0.0086 (16)	0.0110 (14)
C5	0.0503 (17)	0.0342 (14)	0.0487 (17)	0.0069 (13)	−0.0052 (14)	−0.0021 (13)
C6	0.0269 (12)	0.0317 (12)	0.0332 (13)	0.0008 (11)	−0.0037 (11)	−0.0016 (10)
C7	0.0284 (13)	0.0296 (12)	0.0377 (14)	0.0005 (10)	−0.0013 (11)	−0.0055 (11)
C8	0.0240 (12)	0.0257 (11)	0.0356 (14)	−0.0001 (10)	−0.0027 (10)	−0.0041 (10)
C9	0.0272 (13)	0.0331 (13)	0.0332 (14)	−0.0001 (11)	−0.0003 (10)	−0.0017 (10)
C10	0.0234 (14)	0.0674 (19)	0.0591 (19)	0.0118 (14)	−0.0015 (13)	0.0030 (16)

S1—O2	1.4284 (17)	C1—C7	1.486 (3)
S1—O3	1.426 (2)	C1—C6	1.402 (3)
S1—N1	1.625 (2)	C2—C3	1.377 (4)
S1—C6	1.757 (3)	C3—C4	1.374 (4)
O1—C7	1.207 (3)	C4—C5	1.381 (4)
O4—C8	1.379 (3)	C5—C6	1.382 (4)
O5—C9	1.188 (3)	C7—C8	1.539 (3)
O6—C9	1.317 (3)	C8—C9	1.539 (3)
O6—C10	1.449 (3)	C2—H2	0.9300
O4—H4O	0.84 (3)	C3—H3	0.9300
O7—H71	0.83 (3)	C4—H4	0.9300
O7—H72	0.83 (4)	C5—H5	0.9300
N1—C8	1.477 (3)	C10—H10C	0.9600
N1—H1	0.78 (3)	C10—H10A	0.9600
C1—C2	1.387 (4)	C10—H10B	0.9600
S1···H10Bi	3.0600	N1···O6	2.744 (3)
O1···O4	2.949 (3)	N1···O7xii	3.032 (3)
O1···O6	3.099 (3)	C3···C5x	3.570 (4)
O1···C4ii	3.406 (4)	C4···O1ix	3.418 (4)
O1···C4iii	3.418 (4)	C4···O1xiii	3.405 (4)
O2···O4	2.946 (3)	C5···C3xi	3.570 (4)
O2···O7	3.027 (3)	C5···O4ix	3.374 (3)
O2···C9i	3.405 (3)	C9···O2vii	3.405 (3)
O3···C10iv	3.393 (3)	C10···O4xii	2.994 (3)
O3···O7v	3.107 (3)	C10···O3xiv	3.393 (3)
O3···O3vi	3.106 (3)	C10···H4Oxii	3.09 (3)
O4···O5	2.710 (3)	C10···H2x	2.9800
O4···C5iii	3.374 (3)	H1···O6	2.43 (3)
O4···O7vii	2.773 (3)	H1···O7xii	2.29 (3)
O4···O2	2.946 (3)	H2···H10Axi	2.5800
O4···O1	2.949 (3)	H2···O1	2.5000
O4···C10viii	2.994 (3)	H2···O6xi	2.7300
O5···O7iii	3.028 (3)	H2···C10xi	2.9800
O5···O4	2.710 (3)	H3···O7x	2.9200
O6···N1	2.744 (3)	H3···O5xiii	2.7800
O6···O1	3.099 (3)	H4···H10Cxiii	2.4700
O7···N1viii	3.032 (3)	H4···O1ix	2.7300
O7···O5ix	3.028 (3)	H4O···C10viii	3.09 (3)
O7···O4i	2.773 (3)	H4O···H10Aviii	2.5300
O7···O3v	3.107 (3)	H4O···O5	2.65 (3)
O7···O2	3.027 (3)	H4O···O7vii	1.94 (3)
O1···H4iii	2.7300	H4O···H71vii	2.25 (4)
O1···H2	2.5000	H4O···H72vii	2.31 (4)
O2···H72	2.21 (4)	H5···O3	2.8000
O2···H10Aviii	2.6500	H5···O4ix	2.4800
O3···H10Bi	2.6000	H10A···O2xii	2.6500
O3···H5	2.8000	H10A···O4xii	2.3100
O3···H71v	2.45 (3)	H10A···H2x	2.5800
O3···H10Biv	2.8900	H10A···H4Oxii	2.5300
O4···H5iii	2.4800	H10B···S1vii	3.0600
O4···H10Aviii	2.3100	H10B···O3vii	2.6000
O5···H4O	2.65 (3)	H10B···O5	2.6700
O5···H10B	2.6700	H10B···O3xiv	2.8900
O5···H3ii	2.7800	H10C···O5	2.7000
O5···H72iii	2.87 (3)	H10C···H4ii	2.4700
O5···H10C	2.7000	H71···H4Oi	2.25 (4)
O5···H71iii	2.45 (3)	H71···O3v	2.45 (3)
O6···H2x	2.7300	H71···O5ix	2.45 (3)
O6···H1	2.43 (3)	H72···O2	2.21 (4)
O7···H1viii	2.29 (3)	H72···H4Oi	2.31 (5)
O7···H4Oi	1.94 (3)	H72···O5ix	2.87 (3)
O7···H3xi	2.9200
O2—S1—O3	118.33 (12)	O1—C7—C8	118.4 (2)
O2—S1—N1	109.39 (11)	O4—C8—N1	111.36 (19)
O2—S1—C6	108.01 (11)	O4—C8—C7	104.59 (19)
O3—S1—N1	106.53 (12)	O4—C8—C9	111.27 (18)
O3—S1—C6	109.72 (11)	N1—C8—C7	113.20 (18)
N1—S1—C6	103.94 (11)	N1—C8—C9	108.41 (19)
C9—O6—C10	117.3 (2)	C7—C8—C9	107.96 (19)
C8—O4—H4O	107 (2)	O5—C9—C8	123.4 (2)
H71—O7—H72	107 (3)	O6—C9—C8	110.1 (2)
S1—N1—C8	118.28 (17)	O5—C9—O6	126.5 (2)
C8—N1—H1	115 (2)	C3—C2—H2	120.00
S1—N1—H1	110 (2)	C1—C2—H2	120.00
C2—C1—C6	117.8 (2)	C2—C3—H3	120.00
C2—C1—C7	118.7 (2)	C4—C3—H3	120.00
C6—C1—C7	123.4 (2)	C5—C4—H4	120.00
C1—C2—C3	120.9 (3)	C3—C4—H4	120.00
C2—C3—C4	120.3 (3)	C4—C5—H5	120.00
C3—C4—C5	120.5 (3)	C6—C5—H5	120.00
C4—C5—C6	119.1 (3)	O6—C10—H10B	109.00
S1—C6—C5	118.1 (2)	O6—C10—H10C	109.00
S1—C6—C1	120.56 (18)	O6—C10—H10A	110.00
C1—C6—C5	121.4 (2)	H10A—C10—H10C	109.00
O1—C7—C1	121.6 (2)	H10B—C10—H10C	109.00
C1—C7—C8	120.0 (2)	H10A—C10—H10B	110.00
O2—S1—N1—C8	−67.0 (2)	C2—C1—C7—C8	178.7 (2)
O3—S1—N1—C8	163.98 (18)	C6—C1—C7—O1	178.8 (2)
C6—S1—N1—C8	48.1 (2)	C6—C1—C7—C8	−2.4 (3)
O2—S1—C6—C1	94.5 (2)	C1—C2—C3—C4	−0.2 (5)
O2—S1—C6—C5	−84.8 (2)	C2—C3—C4—C5	−0.2 (5)
O3—S1—C6—C1	−135.2 (2)	C3—C4—C5—C6	0.2 (5)
O3—S1—C6—C5	45.5 (2)	C4—C5—C6—S1	179.4 (2)
N1—S1—C6—C1	−21.6 (2)	C4—C5—C6—C1	0.1 (4)
N1—S1—C6—C5	159.1 (2)	O1—C7—C8—O4	84.6 (3)
C10—O6—C9—O5	−3.0 (4)	O1—C7—C8—N1	−154.0 (2)
C10—O6—C9—C8	175.4 (2)	O1—C7—C8—C9	−33.9 (3)
S1—N1—C8—O4	64.3 (2)	C1—C7—C8—O4	−94.2 (2)
S1—N1—C8—C7	−53.3 (3)	C1—C7—C8—N1	27.2 (3)
S1—N1—C8—C9	−173.01 (16)	C1—C7—C8—C9	147.2 (2)
C6—C1—C2—C3	0.5 (4)	O4—C8—C9—O5	−4.0 (3)
C7—C1—C2—C3	179.4 (3)	O4—C8—C9—O6	177.6 (2)
C2—C1—C6—S1	−179.7 (2)	N1—C8—C9—O5	−126.8 (3)
C2—C1—C6—C5	−0.4 (4)	N1—C8—C9—O6	54.8 (3)
C7—C1—C6—S1	1.4 (3)	C7—C8—C9—O5	110.2 (3)
C7—C1—C6—C5	−179.3 (2)	C7—C8—C9—O6	−68.2 (2)
C2—C1—C7—O1	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.78 (3)	2.43 (3)	2.744 (3)	106 (2)
N1—H1···O7xii	0.78 (3)	2.29 (3)	3.032 (3)	162 (3)
O4—H4O···O7vii	0.84 (3)	1.94 (3)	2.773 (3)	175 (2)
O7—H71···O3v	0.83 (3)	2.45 (3)	3.107 (3)	137 (3)
O7—H71···O5ix	0.83 (3)	2.45 (3)	3.028 (3)	128 (3)
O7—H72···O2	0.83 (4)	2.21 (4)	3.027 (3)	167 (3)
C5—H5···O4ix	0.9300	2.4800	3.374 (3)	162.00
C10—H10A···O4xii	0.9600	2.3100	2.994 (3)	128.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.78 (3)	2.43 (3)	2.744 (3)	106 (2)
N1—H1⋯O7i	0.78 (3)	2.29 (3)	3.032 (3)	162 (3)
O4—H4O⋯O7ii	0.84 (3)	1.94 (3)	2.773 (3)	175 (2)
O7—H71⋯O3iii	0.83 (3)	2.45 (3)	3.107 (3)	137 (3)
O7—H71⋯O5iv	0.83 (3)	2.45 (3)	3.028 (3)	128 (3)
O7—H72⋯O2	0.83 (4)	2.21 (4)	3.027 (3)	167 (3)
C5—H5⋯O4iv	0.9300	2.4800	3.374 (3)	162.00
C10—H10A⋯O4i	0.9600	2.3100	2.994 (3)	128.00

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