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

The asymmetric unit of the title compound, C(10)H(9)NO(5)S, contains two independent mol-ecules. The heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations, with the S atoms in each mol-ecule displaced by 0.455 (3) and 0.539 (3) Å and the N atoms displaced in the opposite direction by 0.214 (3) and 0.203 (3) Å, from the planes defined by the remaining ring atoms. The crystal structure is stabilized by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds involving both inter- and intra-molecular inter-actions.

Related literature

For related literature, see: Banerjee & Sarkar (2002 ▶); Cremer & Pople, 1975 ▶; Hirai et al. (1997 ▶); Khalil et al. (2000 ▶); Myung et al. (2002 ▶); Siddiqui et al. (2006 ▶, 2008 ▶).

Experimental

Crystal data

C10H9NO5S

M = 255.24

Triclinic,

a = 7.777 (2) Å

b = 10.932 (4) Å

c = 12.890 (4) Å

α = 105.569 (16)°

β = 94.588 (15)°

γ = 97.763 (16)°

V = 1038.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 173 (2) K

0.24 × 0.22 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.927, T max = 0.950

8716 measured reflections

4693 independent reflections

4191 reflections with (I) > 2.0 σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.03

4693 reflections

321 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL 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 datablocks Global, I. DOI: 10.1107/S1600536808028584/lh2686sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028584/lh2686Isup2.hkl

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

C10H9NO5S	Z = 4
Mr = 255.24	F(000) = 528
Triclinic, P1	Dx = 1.633 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.777 (2) Å	Cell parameters from 8716 reflections
b = 10.932 (4) Å	θ = 3.3–27.5°
c = 12.890 (4) Å	µ = 0.32 mm−1
α = 105.569 (16)°	T = 173 K
β = 94.588 (15)°	Block, colorless
γ = 97.763 (16)°	0.24 × 0.22 × 0.16 mm
V = 1038.2 (6) Å3

Nonius KappaCCD diffractometer	4693 independent reflections
Radiation source: fine-focus sealed tube	4191 reflections with (I) > 2.0 σ(I)
graphite	Rint = 0.019
ω and φ scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
Tmin = 0.927, Tmax = 0.950	k = −14→13
8716 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.041P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
4693 reflections	(Δ/σ)max = 0.001
321 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.41 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	0.30114 (5)	0.07908 (3)	0.24748 (3)	0.01734 (10)
O1	0.23427 (16)	−0.14432 (12)	−0.08819 (9)	0.0293 (3)
H1O	0.263 (3)	−0.213 (2)	−0.0882 (18)	0.035*
O2	0.40121 (15)	0.17533 (10)	0.33806 (9)	0.0245 (2)
O3	0.14058 (14)	0.00794 (10)	0.26334 (9)	0.0218 (2)
O4	0.37308 (17)	−0.31701 (11)	−0.02096 (9)	0.0311 (3)
O5	0.49305 (15)	−0.26084 (10)	0.15392 (9)	0.0243 (2)
N1	0.42676 (17)	−0.02186 (12)	0.19684 (10)	0.0200 (3)
H1N	0.528 (3)	−0.0058 (18)	0.2220 (16)	0.024*
C1	0.25147 (19)	0.14330 (14)	0.13951 (12)	0.0192 (3)
C2	0.2150 (2)	0.26789 (15)	0.16002 (13)	0.0247 (3)
H2	0.2298	0.3231	0.2320	0.030*
C3	0.1567 (2)	0.31014 (17)	0.07309 (15)	0.0297 (4)
H3	0.1312	0.3951	0.0855	0.036*
C4	0.1354 (2)	0.22878 (18)	−0.03175 (14)	0.0303 (4)
H4	0.0919	0.2579	−0.0903	0.036*
C5	0.1764 (2)	0.10609 (17)	−0.05230 (13)	0.0251 (3)
H5	0.1628	0.0520	−0.1247	0.030*
C6	0.23809 (18)	0.06130 (15)	0.03369 (12)	0.0195 (3)
C7	0.28587 (19)	−0.06738 (15)	0.01323 (12)	0.0207 (3)
C8	0.37515 (19)	−0.10618 (14)	0.09083 (12)	0.0194 (3)
C9	0.4123 (2)	−0.23777 (15)	0.06838 (12)	0.0220 (3)
C10	0.5260 (3)	−0.39148 (16)	0.13991 (15)	0.0326 (4)
H10A	0.5654	−0.4022	0.2106	0.039*
H10B	0.6167	−0.4083	0.0917	0.039*
H10C	0.4183	−0.4522	0.1079	0.039*
S2	0.86977 (5)	0.34163 (3)	0.69700 (3)	0.01856 (10)
O6	0.98831 (15)	0.24939 (12)	0.36870 (9)	0.0243 (2)
H6O	0.932 (3)	0.180 (2)	0.3347 (17)	0.029*
O7	0.72248 (14)	0.39245 (11)	0.66203 (9)	0.0253 (2)
O8	0.89790 (15)	0.34412 (11)	0.80904 (9)	0.0252 (2)
O9	0.77047 (14)	0.03249 (11)	0.33635 (9)	0.0261 (2)
O10	0.70377 (16)	−0.02541 (11)	0.48543 (9)	0.0271 (3)
N2	0.86481 (19)	0.19551 (13)	0.62361 (10)	0.0237 (3)
H2N	0.869 (3)	0.138 (2)	0.6548 (16)	0.028*
C11	1.05550 (19)	0.41894 (14)	0.65790 (12)	0.0187 (3)
C12	1.1639 (2)	0.52218 (15)	0.73162 (13)	0.0235 (3)
H12	1.1443	0.5475	0.8056	0.028*
C13	1.3017 (2)	0.58800 (15)	0.69539 (14)	0.0268 (3)
H13	1.3775	0.6586	0.7448	0.032*
C14	1.3285 (2)	0.55026 (16)	0.58671 (14)	0.0263 (3)
H14	1.4209	0.5970	0.5621	0.032*
C15	1.2225 (2)	0.44570 (15)	0.51417 (13)	0.0226 (3)
H15	1.2436	0.4204	0.4404	0.027*
C16	1.08448 (19)	0.37690 (14)	0.54858 (12)	0.0188 (3)
C17	0.97645 (19)	0.26167 (14)	0.47423 (12)	0.0189 (3)
C18	0.8758 (2)	0.17361 (14)	0.51071 (12)	0.0202 (3)
C19	0.77841 (19)	0.05550 (15)	0.43550 (12)	0.0210 (3)
C20	0.6136 (2)	−0.14884 (16)	0.41616 (14)	0.0314 (4)
H20A	0.5696	−0.2026	0.4612	0.038*
H20B	0.6949	−0.1918	0.3703	0.038*
H20C	0.5154	−0.1354	0.3702	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.02110 (18)	0.01460 (17)	0.01551 (17)	0.00158 (13)	0.00185 (13)	0.00366 (13)
O1	0.0381 (7)	0.0269 (6)	0.0176 (5)	0.0025 (5)	−0.0021 (5)	0.0001 (5)
O2	0.0315 (6)	0.0189 (5)	0.0189 (5)	0.0002 (4)	−0.0004 (4)	0.0010 (4)
O3	0.0232 (5)	0.0212 (5)	0.0227 (5)	0.0017 (4)	0.0056 (4)	0.0091 (4)
O4	0.0415 (7)	0.0223 (6)	0.0243 (6)	0.0063 (5)	0.0025 (5)	−0.0023 (5)
O5	0.0300 (6)	0.0194 (5)	0.0242 (5)	0.0078 (4)	0.0048 (4)	0.0052 (4)
N1	0.0187 (6)	0.0191 (6)	0.0189 (6)	0.0035 (5)	−0.0025 (5)	0.0009 (5)
C1	0.0182 (7)	0.0201 (7)	0.0203 (7)	0.0006 (5)	0.0029 (5)	0.0087 (6)
C2	0.0268 (8)	0.0227 (8)	0.0274 (8)	0.0053 (6)	0.0072 (6)	0.0100 (6)
C3	0.0292 (8)	0.0280 (8)	0.0400 (9)	0.0088 (7)	0.0099 (7)	0.0196 (7)
C4	0.0251 (8)	0.0404 (10)	0.0338 (9)	0.0062 (7)	0.0037 (7)	0.0243 (8)
C5	0.0214 (7)	0.0342 (9)	0.0213 (7)	0.0020 (6)	0.0018 (6)	0.0119 (7)
C6	0.0153 (6)	0.0233 (7)	0.0200 (7)	−0.0004 (5)	0.0019 (5)	0.0081 (6)
C7	0.0200 (7)	0.0223 (7)	0.0169 (7)	−0.0005 (6)	0.0028 (5)	0.0026 (6)
C8	0.0200 (7)	0.0172 (7)	0.0179 (7)	0.0014 (5)	0.0017 (5)	0.0006 (5)
C9	0.0225 (7)	0.0201 (7)	0.0222 (7)	0.0022 (6)	0.0058 (6)	0.0037 (6)
C10	0.0453 (10)	0.0215 (8)	0.0359 (9)	0.0137 (7)	0.0117 (8)	0.0105 (7)
S2	0.02101 (18)	0.01819 (18)	0.01673 (17)	0.00130 (13)	0.00248 (13)	0.00623 (13)
O6	0.0270 (6)	0.0265 (6)	0.0175 (5)	0.0004 (5)	0.0052 (4)	0.0045 (4)
O7	0.0216 (5)	0.0304 (6)	0.0277 (6)	0.0065 (4)	0.0061 (4)	0.0128 (5)
O8	0.0328 (6)	0.0254 (6)	0.0168 (5)	0.0017 (5)	0.0022 (4)	0.0069 (4)
O9	0.0244 (5)	0.0298 (6)	0.0193 (5)	−0.0009 (5)	0.0018 (4)	0.0019 (4)
O10	0.0362 (6)	0.0198 (5)	0.0211 (5)	−0.0044 (5)	−0.0014 (5)	0.0044 (4)
N2	0.0358 (7)	0.0173 (6)	0.0172 (6)	−0.0004 (5)	0.0012 (5)	0.0065 (5)
C11	0.0184 (7)	0.0171 (7)	0.0224 (7)	0.0042 (5)	0.0023 (5)	0.0080 (6)
C12	0.0247 (7)	0.0204 (7)	0.0236 (7)	0.0028 (6)	0.0036 (6)	0.0032 (6)
C13	0.0240 (8)	0.0193 (7)	0.0326 (8)	−0.0013 (6)	0.0021 (6)	0.0024 (6)
C14	0.0209 (7)	0.0236 (8)	0.0358 (9)	0.0023 (6)	0.0085 (6)	0.0102 (7)
C15	0.0221 (7)	0.0222 (7)	0.0252 (7)	0.0054 (6)	0.0066 (6)	0.0077 (6)
C16	0.0185 (7)	0.0175 (7)	0.0217 (7)	0.0053 (5)	0.0019 (5)	0.0068 (6)
C17	0.0184 (7)	0.0211 (7)	0.0176 (7)	0.0055 (5)	0.0020 (5)	0.0051 (6)
C18	0.0228 (7)	0.0191 (7)	0.0174 (7)	0.0030 (6)	0.0004 (5)	0.0039 (6)
C19	0.0188 (7)	0.0219 (7)	0.0214 (7)	0.0039 (6)	0.0008 (5)	0.0048 (6)
C20	0.0410 (10)	0.0193 (8)	0.0267 (8)	−0.0059 (7)	−0.0052 (7)	0.0026 (6)

S1—O2	1.4318 (12)	S2—O7	1.4310 (12)
S1—O3	1.4386 (11)	S2—O8	1.4356 (12)
S1—N1	1.6139 (14)	S2—N2	1.6170 (15)
S1—C1	1.7581 (15)	S2—C11	1.7521 (15)
O1—C7	1.3462 (18)	O6—C17	1.3426 (18)
O1—H1O	0.81 (2)	O6—H6O	0.81 (2)
O4—C9	1.2273 (19)	O9—C19	1.2292 (19)
O5—C9	1.3246 (19)	O10—C19	1.3267 (19)
O5—C10	1.4513 (19)	O10—C20	1.4516 (19)
N1—C8	1.4192 (19)	N2—C18	1.4216 (19)
N1—H1N	0.81 (2)	N2—H2N	0.83 (2)
C1—C2	1.389 (2)	C11—C12	1.388 (2)
C1—C6	1.404 (2)	C11—C16	1.407 (2)
C2—C3	1.389 (2)	C12—C13	1.392 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.387 (3)	C13—C14	1.391 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.382 (3)	C14—C15	1.382 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.403 (2)	C15—C16	1.397 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.464 (2)	C16—C17	1.466 (2)
C7—C8	1.363 (2)	C17—C18	1.363 (2)
C8—C9	1.463 (2)	C18—C19	1.459 (2)
C10—H10A	0.9800	C20—H20A	0.9800
C10—H10B	0.9800	C20—H20B	0.9800
C10—H10C	0.9800	C20—H20C	0.9800
O2—S1—O3	119.12 (7)	O7—S2—O8	118.19 (7)
O2—S1—N1	107.80 (7)	O7—S2—N2	110.26 (8)
O3—S1—N1	108.47 (7)	O8—S2—N2	108.16 (7)
O2—S1—C1	111.19 (7)	O7—S2—C11	107.46 (7)
O3—S1—C1	106.82 (7)	O8—S2—C11	110.99 (7)
N1—S1—C1	102.09 (7)	N2—S2—C11	100.30 (7)
C7—O1—H1O	105.2 (16)	C17—O6—H6O	107.2 (14)
C9—O5—C10	116.20 (13)	C19—O10—C20	116.26 (13)
C8—N1—S1	118.66 (10)	C18—N2—S2	118.32 (11)
C8—N1—H1N	120.1 (14)	C18—N2—H2N	122.7 (14)
S1—N1—H1N	117.5 (14)	S2—N2—H2N	118.5 (14)
C2—C1—C6	122.02 (14)	C12—C11—C16	121.77 (14)
C2—C1—S1	120.29 (12)	C12—C11—S2	120.58 (12)
C6—C1—S1	117.53 (11)	C16—C11—S2	117.57 (11)
C1—C2—C3	118.62 (15)	C11—C12—C13	118.93 (15)
C1—C2—H2	120.7	C11—C12—H12	120.5
C3—C2—H2	120.7	C13—C12—H12	120.5
C4—C3—C2	120.26 (16)	C14—C13—C12	119.95 (15)
C4—C3—H3	119.9	C14—C13—H13	120.0
C2—C3—H3	119.9	C12—C13—H13	120.0
C5—C4—C3	121.02 (15)	C15—C14—C13	120.86 (15)
C5—C4—H4	119.5	C15—C14—H14	119.6
C3—C4—H4	119.5	C13—C14—H14	119.6
C4—C5—C6	120.04 (15)	C14—C15—C16	120.39 (15)
C4—C5—H5	120.0	C14—C15—H15	119.8
C6—C5—H5	120.0	C16—C15—H15	119.8
C5—C6—C1	117.94 (14)	C15—C16—C11	118.04 (14)
C5—C6—C7	120.79 (14)	C15—C16—C17	121.18 (14)
C1—C6—C7	121.28 (13)	C11—C16—C17	120.75 (13)
O1—C7—C8	122.72 (14)	O6—C17—C18	123.41 (14)
O1—C7—C6	114.65 (13)	O6—C17—C16	114.53 (13)
C8—C7—C6	122.63 (13)	C18—C17—C16	122.04 (13)
C7—C8—N1	120.81 (13)	C17—C18—N2	120.21 (13)
C7—C8—C9	120.74 (14)	C17—C18—C19	121.04 (14)
N1—C8—C9	118.38 (13)	N2—C18—C19	118.75 (13)
O4—C9—O5	124.32 (14)	O9—C19—O10	123.81 (14)
O4—C9—C8	122.83 (14)	O9—C19—C18	123.27 (14)
O5—C9—C8	112.84 (13)	O10—C19—C18	112.90 (13)
O5—C10—H10A	109.5	O10—C20—H20A	109.5
O5—C10—H10B	109.5	O10—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
O5—C10—H10C	109.5	O10—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5
O2—S1—N1—C8	−163.59 (11)	O7—S2—N2—C18	62.59 (13)
O3—S1—N1—C8	66.16 (13)	O8—S2—N2—C18	−166.78 (11)
C1—S1—N1—C8	−46.39 (13)	C11—S2—N2—C18	−50.50 (13)
O2—S1—C1—C2	−36.33 (14)	O7—S2—C11—C12	98.46 (13)
O3—S1—C1—C2	95.16 (13)	O8—S2—C11—C12	−32.17 (15)
N1—S1—C1—C2	−151.06 (12)	N2—S2—C11—C12	−146.32 (13)
O2—S1—C1—C6	148.12 (11)	O7—S2—C11—C16	−78.25 (13)
O3—S1—C1—C6	−80.39 (12)	O8—S2—C11—C16	151.13 (11)
N1—S1—C1—C6	33.39 (13)	N2—S2—C11—C16	36.98 (13)
C6—C1—C2—C3	2.7 (2)	C16—C11—C12—C13	1.9 (2)
S1—C1—C2—C3	−172.61 (12)	S2—C11—C12—C13	−174.65 (12)
C1—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	0.3 (2)
C2—C3—C4—C5	−1.9 (3)	C12—C13—C14—C15	−1.7 (2)
C3—C4—C5—C6	1.0 (2)	C13—C14—C15—C16	0.9 (2)
C4—C5—C6—C1	1.7 (2)	C14—C15—C16—C11	1.2 (2)
C4—C5—C6—C7	−178.64 (14)	C14—C15—C16—C17	−176.71 (14)
C2—C1—C6—C5	−3.6 (2)	C12—C11—C16—C15	−2.7 (2)
S1—C1—C6—C5	171.83 (11)	S2—C11—C16—C15	174.00 (11)
C2—C1—C6—C7	176.74 (14)	C12—C11—C16—C17	175.28 (14)
S1—C1—C6—C7	−7.80 (18)	S2—C11—C16—C17	−8.05 (18)
C5—C6—C7—O1	−12.3 (2)	C15—C16—C17—O6	−17.4 (2)
C1—C6—C7—O1	167.33 (13)	C11—C16—C17—O6	164.76 (13)
C5—C6—C7—C8	167.84 (14)	C15—C16—C17—C18	161.26 (14)
C1—C6—C7—C8	−12.5 (2)	C11—C16—C17—C18	−16.6 (2)
O1—C7—C8—N1	−179.89 (14)	O6—C17—C18—N2	−177.69 (13)
C6—C7—C8—N1	0.0 (2)	C16—C17—C18—N2	3.8 (2)
O1—C7—C8—C9	−3.0 (2)	O6—C17—C18—C19	2.6 (2)
C6—C7—C8—C9	176.87 (13)	C16—C17—C18—C19	−175.92 (13)
S1—N1—C8—C7	34.08 (19)	S2—N2—C18—C17	34.94 (19)
S1—N1—C8—C9	−142.91 (12)	S2—N2—C18—C19	−145.32 (12)
C10—O5—C9—O4	−3.7 (2)	C20—O10—C19—O9	2.1 (2)
C10—O5—C9—C8	176.75 (13)	C20—O10—C19—C18	−176.20 (13)
C7—C8—C9—O4	3.3 (2)	C17—C18—C19—O9	−5.4 (2)
N1—C8—C9—O4	−179.71 (14)	N2—C18—C19—O9	174.86 (14)
C7—C8—C9—O5	−177.16 (13)	C17—C18—C19—O10	172.87 (14)
N1—C8—C9—O5	−0.17 (19)	N2—C18—C19—O10	−6.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.81 (2)	1.86 (2)	2.600 (2)	152 (2)
N1—H1N···O9	0.81 (2)	2.22 (2)	2.994 (2)	162 (2)
O6—H6O···O9	0.81 (2)	1.91 (2)	2.634 (2)	147 (2)
N2—H2N···O3i	0.83 (2)	2.13 (2)	2.966 (2)	175 (2)
C4—H4···O8ii	0.95	2.36	3.259 (2)	158
C20—H20A···O2i	0.98	2.51	3.267 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.81 (2)	1.86 (2)	2.600 (2)	152 (2)
N1—H1N⋯O9	0.81 (2)	2.22 (2)	2.994 (2)	162 (2)
O6—H6O⋯O9	0.81 (2)	1.91 (2)	2.634 (2)	147 (2)
N2—H2N⋯O3i	0.83 (2)	2.13 (2)	2.966 (2)	175 (2)
C4—H4⋯O8ii	0.95	2.36	3.259 (2)	158
C20—H20A⋯O2i	0.98	2.51	3.267 (2)	134

Symmetry codes: (i) ; (ii) .