Methyl 2-ethyl-4-hydr-oxy-2H-1,2-benzo-thia-zine-3-carboxyl-ate 1,1-dioxide.

In the title compound, C(12)H(13)NO(5)S, the thia-zine ring adopts a half chair conformation and an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, the mol-ecules are linked by C-H⋯O inter-actions, leading to zigzag chains along the b axis.

Related literature

For background to the biological properties of thia­zines, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶). For related structures, see: Arshad et al. (2009a ▶,b ▶). For graph-set notation, see: Bernstein, et al. (1995 ▶).

Experimental

Crystal data

C12H13NO5S

M = 283.29

Orthorhombic,

a = 7.2460 (6) Å

b = 20.548 (2) Å

c = 8.5710 (8) Å

V = 1276.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.24 × 0.14 × 0.10 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.938, T max = 0.974

14253 measured reflections

3148 independent reflections

1270 reflections with I > 2σ(I)

R int = 0.133

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.102

S = 0.95

3148 reflections

176 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1464 Friedel pairs

Flack parameter: 0.07 (12)

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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: X-SEED (Barbur, 2001 ▶); WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810012365/hb5390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012365/hb5390Isup2.hkl

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

C12H13NO5S	F(000) = 592
Mr = 283.29	Dx = 1.475 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 733 reflections
a = 7.2460 (6) Å	θ = 2.6–17.3°
b = 20.548 (2) Å	µ = 0.27 mm−1
c = 8.5710 (8) Å	T = 296 K
V = 1276.1 (2) Å3	Cut needle, colourless
Z = 4	0.24 × 0.14 × 0.10 mm

Bruker KAPPA APEXII CCD diffractometer	3148 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
graphite	Rint = 0.133
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.938, Tmax = 0.974	k = −26→27
14253 measured reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.0219P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 0.95	Δρmax = 0.22 e Å−3
3148 reflections	Δρmin = −0.25 e Å−3
176 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0062 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1464 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.07 (12)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.19292 (16)	0.06952 (6)	0.49242 (15)	0.0514 (4)
O1	0.0578 (4)	0.10023 (16)	0.3936 (4)	0.0648 (10)
O2	0.1809 (4)	0.00107 (13)	0.5198 (4)	0.0716 (10)
O3	0.3931 (4)	0.26033 (12)	0.5272 (4)	0.0532 (8)
H3	0.4444	0.2709	0.4458	0.080*
O4	0.5638 (4)	0.23848 (15)	0.2618 (4)	0.0563 (10)
O5	0.5818 (4)	0.13380 (14)	0.1843 (4)	0.0550 (9)
N1	0.3974 (4)	0.08716 (17)	0.4241 (4)	0.0413 (9)
C1	0.1976 (6)	0.1103 (2)	0.6695 (5)	0.0422 (11)
C2	0.1285 (6)	0.0824 (2)	0.8054 (6)	0.0536 (14)
H2	0.0732	0.0416	0.8027	0.064*
C3	0.1429 (6)	0.1160 (3)	0.9446 (6)	0.0560 (15)
H3A	0.1030	0.0970	1.0370	0.067*
C4	0.2163 (6)	0.1776 (2)	0.9459 (5)	0.0589 (15)
H4	0.2201	0.2009	1.0389	0.071*
C5	0.2849 (6)	0.2056 (2)	0.8105 (6)	0.0560 (14)
H5	0.3341	0.2474	0.8139	0.067*
C6	0.2811 (6)	0.1722 (2)	0.6708 (6)	0.0396 (11)
C7	0.3701 (5)	0.1955 (2)	0.5296 (6)	0.0406 (11)
C8	0.4294 (6)	0.1557 (2)	0.4160 (5)	0.0372 (11)
C9	0.5296 (6)	0.1805 (3)	0.2822 (5)	0.0471 (12)
C10	0.6951 (6)	0.1538 (2)	0.0543 (5)	0.0707 (16)
H10A	0.6288	0.1848	−0.0079	0.106*
H10B	0.7252	0.1165	−0.0083	0.106*
H10C	0.8066	0.1733	0.0926	0.106*
C11	0.5572 (6)	0.0441 (2)	0.4634 (5)	0.0548 (15)
H11A	0.6478	0.0475	0.3805	0.066*
H11B	0.5143	−0.0006	0.4657	0.066*
C12	0.6504 (6)	0.0588 (3)	0.6154 (7)	0.0840 (19)
H12A	0.6928	0.1031	0.6152	0.126*
H12B	0.7537	0.0301	0.6290	0.126*
H12C	0.5646	0.0527	0.6994	0.126*

	U11	U22	U33	U12	U13	U23
S1	0.0554 (7)	0.0474 (7)	0.0516 (7)	−0.0144 (7)	0.0019 (9)	−0.0055 (8)
O1	0.051 (2)	0.083 (3)	0.060 (2)	−0.0095 (18)	−0.010 (2)	−0.003 (2)
O2	0.097 (2)	0.0399 (19)	0.078 (3)	−0.0283 (16)	0.014 (2)	−0.010 (2)
O3	0.065 (2)	0.033 (2)	0.061 (3)	−0.0045 (14)	0.0097 (19)	0.0007 (19)
O4	0.067 (2)	0.042 (2)	0.059 (2)	−0.0064 (17)	0.0121 (19)	0.0070 (18)
O5	0.068 (2)	0.048 (2)	0.050 (2)	0.0000 (17)	0.0208 (19)	−0.0001 (19)
N1	0.044 (2)	0.037 (2)	0.043 (2)	−0.0036 (17)	0.0052 (18)	−0.0020 (18)
C1	0.038 (3)	0.048 (3)	0.040 (3)	0.000 (2)	0.000 (2)	−0.006 (3)
C2	0.038 (3)	0.056 (4)	0.066 (4)	−0.003 (2)	0.009 (3)	0.005 (3)
C3	0.056 (3)	0.062 (4)	0.050 (4)	0.010 (3)	0.012 (3)	0.008 (3)
C4	0.062 (3)	0.075 (4)	0.039 (4)	0.017 (3)	0.006 (3)	−0.010 (3)
C5	0.061 (3)	0.051 (3)	0.056 (4)	0.002 (3)	0.003 (3)	−0.011 (3)
C6	0.039 (3)	0.035 (3)	0.045 (3)	0.002 (2)	−0.001 (3)	0.000 (3)
C7	0.044 (3)	0.033 (3)	0.045 (3)	−0.005 (2)	−0.003 (2)	−0.001 (3)
C8	0.040 (3)	0.027 (3)	0.045 (3)	−0.004 (2)	−0.005 (2)	0.002 (2)
C9	0.043 (3)	0.058 (3)	0.040 (3)	−0.003 (3)	−0.006 (3)	−0.001 (3)
C10	0.086 (4)	0.065 (4)	0.061 (4)	−0.004 (3)	0.036 (3)	0.002 (3)
C11	0.057 (3)	0.037 (3)	0.070 (4)	0.010 (2)	0.005 (3)	0.010 (3)
C12	0.069 (4)	0.102 (5)	0.081 (5)	0.019 (3)	−0.013 (3)	0.015 (4)

S1—O2	1.429 (3)	C4—C5	1.388 (6)
S1—O1	1.441 (3)	C4—H4	0.9300
S1—N1	1.634 (3)	C5—C6	1.381 (6)
S1—C1	1.734 (5)	C5—H5	0.9300
O3—C7	1.343 (4)	C6—C7	1.452 (6)
O3—H3	0.8200	C7—C8	1.343 (5)
O4—C9	1.229 (5)	C8—C9	1.450 (6)
O5—C9	1.330 (5)	C10—H10A	0.9600
O5—C10	1.444 (5)	C10—H10B	0.9600
N1—C8	1.428 (5)	C10—H10C	0.9600
N1—C11	1.495 (5)	C11—C12	1.499 (6)
C1—C2	1.392 (6)	C11—H11A	0.9700
C1—C6	1.408 (5)	C11—H11B	0.9700
C2—C3	1.383 (6)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.372 (6)	C12—H12C	0.9600
C3—H3A	0.9300
O2—S1—O1	119.1 (2)	C1—C6—C7	118.8 (4)
O2—S1—N1	109.44 (18)	C8—C7—O3	123.6 (4)
O1—S1—N1	107.97 (19)	C8—C7—C6	123.0 (4)
O2—S1—C1	109.4 (2)	O3—C7—C6	113.3 (4)
O1—S1—C1	108.4 (2)	C7—C8—N1	120.9 (4)
N1—S1—C1	100.9 (2)	C7—C8—C9	121.3 (4)
C7—O3—H3	109.5	N1—C8—C9	117.9 (4)
C9—O5—C10	116.3 (3)	O4—C9—O5	123.6 (4)
C8—N1—C11	117.9 (3)	O4—C9—C8	123.7 (4)
C8—N1—S1	112.5 (3)	O5—C9—C8	112.7 (4)
C11—N1—S1	119.4 (3)	O5—C10—H10A	109.5
C2—C1—C6	121.3 (4)	O5—C10—H10B	109.5
C2—C1—S1	121.8 (4)	H10A—C10—H10B	109.5
C6—C1—S1	116.9 (4)	O5—C10—H10C	109.5
C3—C2—C1	119.3 (4)	H10A—C10—H10C	109.5
C3—C2—H2	120.4	H10B—C10—H10C	109.5
C1—C2—H2	120.4	N1—C11—C12	115.2 (4)
C4—C3—C2	119.8 (5)	N1—C11—H11A	108.5
C4—C3—H3A	120.1	C12—C11—H11A	108.5
C2—C3—H3A	120.1	N1—C11—H11B	108.5
C3—C4—C5	120.9 (4)	C12—C11—H11B	108.5
C3—C4—H4	119.5	H11A—C11—H11B	107.5
C5—C4—H4	119.5	C11—C12—H12A	109.5
C6—C5—C4	120.8 (4)	C11—C12—H12B	109.5
C6—C5—H5	119.6	H12A—C12—H12B	109.5
C4—C5—H5	119.6	C11—C12—H12C	109.5
C5—C6—C1	117.7 (4)	H12A—C12—H12C	109.5
C5—C6—C7	123.3 (4)	H12B—C12—H12C	109.5
O2—S1—N1—C8	−171.2 (3)	S1—C1—C6—C7	−4.9 (5)
O1—S1—N1—C8	57.8 (3)	C5—C6—C7—C8	153.4 (4)
C1—S1—N1—C8	−55.9 (3)	C1—C6—C7—C8	−21.9 (6)
O2—S1—N1—C11	−26.6 (4)	C5—C6—C7—O3	−24.2 (6)
O1—S1—N1—C11	−157.6 (3)	C1—C6—C7—O3	160.5 (4)
C1—S1—N1—C11	88.7 (3)	O3—C7—C8—N1	−178.8 (4)
O2—S1—C1—C2	−22.5 (4)	C6—C7—C8—N1	3.8 (6)
O1—S1—C1—C2	108.9 (4)	O3—C7—C8—C9	2.0 (6)
N1—S1—C1—C2	−137.8 (4)	C6—C7—C8—C9	−175.4 (4)
O2—S1—C1—C6	155.2 (3)	C11—N1—C8—C7	−105.7 (4)
O1—S1—C1—C6	−73.4 (4)	S1—N1—C8—C7	39.5 (5)
N1—S1—C1—C6	39.9 (4)	C11—N1—C8—C9	73.6 (5)
C6—C1—C2—C3	−0.3 (7)	S1—N1—C8—C9	−141.2 (3)
S1—C1—C2—C3	177.3 (3)	C10—O5—C9—O4	4.3 (7)
C1—C2—C3—C4	3.3 (7)	C10—O5—C9—C8	−175.3 (4)
C2—C3—C4—C5	−3.2 (7)	C7—C8—C9—O4	−1.5 (7)
C3—C4—C5—C6	0.0 (7)	N1—C8—C9—O4	179.3 (4)
C4—C5—C6—C1	2.9 (6)	C7—C8—C9—O5	178.1 (4)
C4—C5—C6—C7	−172.4 (4)	N1—C8—C9—O5	−1.1 (5)
C2—C1—C6—C5	−2.8 (6)	C8—N1—C11—C12	57.6 (5)
S1—C1—C6—C5	179.5 (3)	S1—N1—C11—C12	−85.1 (4)
C2—C1—C6—C7	172.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.92	2.628 (5)	144
C4—H4···O4i	0.93	2.55	3.395 (5)	152
C10—H10B···O2ii	0.96	2.52	3.320 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.92	2.628 (5)	144
C4—H4⋯O4i	0.93	2.55	3.395 (5)	152
C10—H10B⋯O2ii	0.96	2.52	3.320 (5)	141

Symmetry codes: (i) ; (ii) .