2-(3-Oxo-3,4-dihydro-2H-1,4-benzo-thia-zin-4-yl)acetic acid monohydrate.

In the title compound, C(10)H(9)NO(3)S·H(2)O, the thio-morpholine ring exists in a conformation inter-mediate between twist-boat and half-chair. An inter-molecular O-H⋯O hydrogen bond links the acid and water mol-ecules together. In the crystal packing, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For the biological activity of 4H-benzo(1,4)thia­zine, see: Armenise et al. (1991 ▶); Gupta et al. (1993 ▶); Fringuelli et al. (2005 ▶). For medical applications of sulfone derivatives of 4H-benzo(1,4)thia­zine, see: Shinji & Koshiro (1995 ▶); Szule et al. (1988 ▶); Culbertson (1991 ▶). For a related structure, see: Zhang et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H9NO3S·H2O

M = 241.26

Monoclinic,

a = 7.5897 (1) Å

b = 9.2208 (2) Å

c = 15.6701 (3) Å

β = 94.336 (1)°

V = 1093.50 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.49 × 0.34 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.870, T max = 0.969

25955 measured reflections

4859 independent reflections

3833 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.128

S = 0.83

4859 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034977/sj2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034977/sj2641Isup2.hkl

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

C10H9NO3S·H2O	F(000) = 504
Mr = 241.26	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7672 reflections
a = 7.5897 (1) Å	θ = 3.4–33.1°
b = 9.2208 (2) Å	µ = 0.29 mm−1
c = 15.6701 (3) Å	T = 100 K
β = 94.336 (1)°	Block, colourless
V = 1093.50 (3) Å3	0.49 × 0.34 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4859 independent reflections
Radiation source: fine-focus sealed tube	3833 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 35.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.870, Tmax = 0.969	k = −14→13
25955 measured reflections	l = −23→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.83	w = 1/[σ2(Fo2) + (0.0915P)2 + 0.3956P] where P = (Fo2 + 2Fc2)/3
4859 reflections	(Δ/σ)max = 0.001?
157 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.25290 (3)	0.20298 (3)	0.368735 (18)	0.02391 (8)
O1W	0.17478 (12)	0.72939 (10)	0.31220 (6)	0.02515 (17)
O1	0.47141 (12)	0.56427 (9)	0.33767 (6)	0.02699 (18)
O2	0.94362 (11)	0.62615 (9)	0.40417 (6)	0.02360 (16)
O3	0.90204 (12)	0.44113 (9)	0.31220 (6)	0.02548 (17)
C1	0.46033 (14)	0.11958 (11)	0.38793 (6)	0.01900 (18)
C2	0.47444 (16)	−0.03074 (12)	0.39590 (7)	0.0233 (2)
H2A	0.3733	−0.0879	0.3900	0.028*
C3	0.63845 (17)	−0.09543 (12)	0.41263 (7)	0.0247 (2)
H3A	0.6469	−0.1955	0.4193	0.030*
C4	0.78984 (16)	−0.01067 (12)	0.41946 (7)	0.0246 (2)
H4A	0.8999	−0.0544	0.4296	0.030*
C5	0.77815 (14)	0.13934 (12)	0.41127 (7)	0.02197 (19)
H5A	0.8801	0.1956	0.4156	0.026*
C6	0.61270 (13)	0.20523 (11)	0.39649 (6)	0.01770 (17)
N1	0.59863 (11)	0.35987 (9)	0.39215 (6)	0.01904 (16)
C7	0.46962 (14)	0.43038 (12)	0.34290 (7)	0.02067 (19)
C8	0.32911 (14)	0.33868 (13)	0.29697 (7)	0.0234 (2)
H8A	0.3764	0.2918	0.2482	0.028*
H8B	0.2309	0.3995	0.2760	0.028*
C9	0.73286 (14)	0.45083 (11)	0.43631 (7)	0.02047 (18)
H9A	0.7934	0.3959	0.4825	0.025*
H9B	0.6764	0.5333	0.4613	0.025*
C10	0.86713 (13)	0.50482 (11)	0.37642 (7)	0.01941 (18)
H1O2	1.028 (3)	0.652 (3)	0.3672 (15)	0.064 (7)*
H2W1	0.155 (3)	0.784 (2)	0.2691 (15)	0.056 (6)*
H1W1	0.270 (3)	0.672 (2)	0.3095 (13)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01398 (12)	0.03081 (15)	0.02713 (14)	−0.00430 (9)	0.00291 (9)	0.00246 (9)
O1W	0.0185 (4)	0.0229 (4)	0.0340 (4)	0.0004 (3)	0.0017 (3)	0.0072 (3)
O1	0.0224 (4)	0.0214 (4)	0.0371 (5)	0.0033 (3)	0.0020 (3)	0.0071 (3)
O2	0.0222 (4)	0.0184 (3)	0.0304 (4)	−0.0051 (3)	0.0030 (3)	−0.0026 (3)
O3	0.0231 (4)	0.0232 (4)	0.0306 (4)	−0.0046 (3)	0.0049 (3)	−0.0046 (3)
C1	0.0179 (4)	0.0209 (4)	0.0184 (4)	−0.0039 (3)	0.0028 (3)	−0.0002 (3)
C2	0.0279 (5)	0.0217 (5)	0.0208 (4)	−0.0064 (4)	0.0046 (4)	−0.0016 (3)
C3	0.0358 (6)	0.0175 (4)	0.0211 (4)	−0.0004 (4)	0.0050 (4)	−0.0006 (3)
C4	0.0264 (5)	0.0226 (5)	0.0251 (5)	0.0052 (4)	0.0030 (4)	0.0020 (4)
C5	0.0169 (4)	0.0206 (4)	0.0284 (5)	0.0016 (3)	0.0019 (3)	0.0028 (4)
C6	0.0162 (4)	0.0169 (4)	0.0201 (4)	−0.0009 (3)	0.0022 (3)	0.0013 (3)
N1	0.0136 (3)	0.0176 (4)	0.0256 (4)	−0.0004 (3)	−0.0006 (3)	0.0029 (3)
C7	0.0150 (4)	0.0233 (5)	0.0239 (4)	0.0020 (3)	0.0027 (3)	0.0048 (3)
C8	0.0169 (4)	0.0296 (5)	0.0233 (5)	−0.0003 (4)	−0.0008 (3)	0.0047 (4)
C9	0.0172 (4)	0.0196 (4)	0.0243 (4)	−0.0020 (3)	−0.0001 (3)	0.0002 (3)
C10	0.0147 (4)	0.0169 (4)	0.0262 (5)	0.0000 (3)	−0.0009 (3)	0.0000 (3)

S1—C1	1.7575 (11)	C4—C5	1.3914 (16)
S1—C8	1.8064 (12)	C4—H4A	0.9300
O1W—H2W1	0.85 (2)	C5—C6	1.3984 (15)
O1W—H1W1	0.90 (2)	C5—H5A	0.9300
O1—C7	1.2374 (13)	C6—N1	1.4311 (13)
O2—C10	1.3189 (13)	N1—C7	1.3648 (13)
O2—H1O2	0.93 (3)	N1—C9	1.4539 (13)
O3—C10	1.2116 (14)	C7—C8	1.5014 (16)
C1—C2	1.3951 (15)	C8—H8A	0.9700
C1—C6	1.3985 (14)	C8—H8B	0.9700
C2—C3	1.3873 (17)	C9—C10	1.5205 (16)
C2—H2A	0.9300	C9—H9A	0.9700
C3—C4	1.3871 (17)	C9—H9B	0.9700
C3—H3A	0.9300
C1—S1—C8	94.86 (5)	C7—N1—C6	123.32 (9)
H2W1—O1W—H1W1	114 (2)	C7—N1—C9	116.19 (8)
C10—O2—H1O2	108.8 (14)	C6—N1—C9	120.33 (8)
C2—C1—C6	119.68 (10)	O1—C7—N1	120.11 (10)
C2—C1—S1	120.78 (8)	O1—C7—C8	122.76 (10)
C6—C1—S1	119.53 (8)	N1—C7—C8	117.12 (9)
C3—C2—C1	120.38 (10)	C7—C8—S1	109.94 (7)
C3—C2—H2A	119.8	C7—C8—H8A	109.7
C1—C2—H2A	119.8	S1—C8—H8A	109.7
C4—C3—C2	119.90 (10)	C7—C8—H8B	109.7
C4—C3—H3A	120.0	S1—C8—H8B	109.7
C2—C3—H3A	120.0	H8A—C8—H8B	108.2
C3—C4—C5	120.42 (11)	N1—C9—C10	111.92 (9)
C3—C4—H4A	119.8	N1—C9—H9A	109.2
C5—C4—H4A	119.8	C10—C9—H9A	109.2
C4—C5—C6	119.83 (10)	N1—C9—H9B	109.2
C4—C5—H5A	120.1	C10—C9—H9B	109.2
C6—C5—H5A	120.1	H9A—C9—H9B	107.9
C1—C6—C5	119.75 (9)	O3—C10—O2	124.51 (10)
C1—C6—N1	119.99 (9)	O3—C10—C9	123.56 (9)
C5—C6—N1	120.24 (9)	O2—C10—C9	111.90 (9)
C8—S1—C1—C2	−142.00 (9)	C5—C6—N1—C7	149.31 (11)
C8—S1—C1—C6	38.91 (9)	C1—C6—N1—C9	152.60 (10)
C6—C1—C2—C3	0.30 (16)	C5—C6—N1—C9	−25.91 (14)
S1—C1—C2—C3	−178.80 (8)	C6—N1—C7—O1	−175.33 (10)
C1—C2—C3—C4	−1.55 (16)	C9—N1—C7—O1	0.07 (15)
C2—C3—C4—C5	1.24 (17)	C6—N1—C7—C8	4.85 (15)
C3—C4—C5—C6	0.33 (17)	C9—N1—C7—C8	−179.75 (9)
C2—C1—C6—C5	1.27 (15)	O1—C7—C8—S1	−134.43 (10)
S1—C1—C6—C5	−179.63 (8)	N1—C7—C8—S1	45.39 (12)
C2—C1—C6—N1	−177.25 (9)	C1—S1—C8—C7	−60.65 (8)
S1—C1—C6—N1	1.86 (13)	C7—N1—C9—C10	−77.23 (12)
C4—C5—C6—C1	−1.58 (16)	C6—N1—C9—C10	98.32 (11)
C4—C5—C6—N1	176.93 (10)	N1—C9—C10—O3	−26.48 (14)
C1—C6—N1—C7	−32.18 (15)	N1—C9—C10—O2	155.33 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1Wi	0.93 (2)	1.62 (2)	2.5384 (13)	168 (3)
O1W—H2W1···O3ii	0.85 (2)	1.96 (2)	2.7893 (13)	168 (2)
O1W—H1W1···O1	0.90 (2)	1.85 (2)	2.7221 (13)	163.4 (19)
C2—H2A···O1Wiii	0.93	2.51	3.3666 (15)	153
C9—H9A···O2iv	0.97	2.58	3.4429 (14)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1Wi	0.93 (2)	1.62 (2)	2.5384 (13)	168 (3)
O1W—H2W1⋯O3ii	0.85 (2)	1.96 (2)	2.7893 (13)	168 (2)
O1W—H1W1⋯O1	0.90 (2)	1.85 (2)	2.7221 (13)	163.4 (19)
C2—H2A⋯O1Wiii	0.93	2.51	3.3666 (15)	153
C9—H9A⋯O2iv	0.97	2.58	3.4429 (14)	149

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