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

In the title compound, C(13)H(15)NO(5)S, the thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds, resulting in zigzag chains lying along the c axis.

Related literature

For the syntheses of related compounds, see: Bihovsky et al. (2004 ▶); Braun (1923 ▶); Lombardino et al. (1971 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of benzothia­zines, see: Turck et al. (1996 ▶); Zia-ur-Rehman et al. (2006 ▶). For related structures, see: Fabiola et al. (1998 ▶); Zia-ur-Rehman et al. (2007 ▶).

Experimental

Crystal data

C13H15NO5S

M = 297.32

Orthorhombic,

a = 12.4398 (6) Å

b = 8.7538 (5) Å

c = 12.7288 (7) Å

V = 1386.11 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.39 × 0.36 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.973

8843 measured reflections

3252 independent reflections

2540 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.03

3252 reflections

184 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1451 Friedel pairs

Flack parameter: −0.08 (8)

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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046236/is2482sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046236/is2482Isup2.hkl

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

C13H15NO5S	F(000) = 624
Mr = 297.32	Dx = 1.425 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2980 reflections
a = 12.4398 (6) Å	θ = 2.3–25.3°
b = 8.7538 (5) Å	µ = 0.25 mm−1
c = 12.7288 (7) Å	T = 296 K
V = 1386.11 (13) Å3	Rods, yellow
Z = 4	0.39 × 0.36 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	3252 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→10
Tmin = 0.908, Tmax = 0.973	k = −11→11
8843 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3252 reflections	Δρmax = 0.16 e Å−3
184 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 1451 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.08 (8)

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
C1	0.58950 (17)	0.7963 (3)	0.8319 (2)	0.0442 (5)
C2	0.66903 (18)	0.8114 (3)	0.7577 (2)	0.0565 (6)
H2	0.7391	0.7816	0.7726	0.068*
C3	0.6434 (2)	0.8714 (3)	0.6609 (3)	0.0703 (8)
H3	0.6967	0.8829	0.6103	0.084*
C4	0.5396 (2)	0.9145 (3)	0.6385 (2)	0.0622 (7)
H4	0.5230	0.9536	0.5725	0.075*
C5	0.45981 (19)	0.9001 (3)	0.71319 (19)	0.0509 (6)
H5	0.3900	0.9308	0.6976	0.061*
C6	0.48305 (15)	0.8403 (3)	0.81103 (17)	0.0407 (5)
C7	0.39979 (15)	0.8187 (3)	0.89165 (18)	0.0398 (5)
C8	0.40966 (15)	0.7206 (2)	0.97246 (19)	0.0389 (5)
C9	0.32273 (17)	0.7043 (3)	1.04807 (18)	0.0443 (5)
C10	0.2568 (3)	0.5866 (3)	1.2006 (3)	0.0755 (8)
H10A	0.1955	0.5455	1.1645	0.113*
H10B	0.2378	0.6825	1.2322	0.113*
H10C	0.2794	0.5165	1.2542	0.113*
C11	0.50112 (17)	0.4660 (3)	0.9658 (2)	0.0493 (5)
H11A	0.4465	0.4214	1.0107	0.059*
H11B	0.5695	0.4204	0.9848	0.059*
C12	0.4761 (2)	0.4257 (3)	0.8530 (2)	0.0589 (7)
H12A	0.5279	0.4748	0.8072	0.071*
H12B	0.4052	0.4639	0.8350	0.071*
C13	0.4794 (3)	0.2548 (3)	0.8355 (3)	0.0812 (10)
H13A	0.4297	0.2057	0.8823	0.122*
H13B	0.5507	0.2178	0.8490	0.122*
H13C	0.4600	0.2325	0.7641	0.122*
N1	0.50637 (13)	0.6325 (2)	0.98684 (13)	0.0423 (5)
O1	0.70303 (11)	0.6188 (2)	0.95391 (16)	0.0633 (5)
O2	0.62415 (13)	0.8534 (2)	1.02728 (17)	0.0676 (6)
O3	0.31275 (12)	0.90699 (18)	0.87688 (13)	0.0532 (4)
H3A	0.2671	0.8861	0.9211	0.080*
O4	0.23788 (13)	0.7728 (2)	1.03972 (15)	0.0586 (5)
O5	0.34308 (13)	0.60963 (19)	1.12699 (13)	0.0547 (4)
S1	0.61649 (4)	0.72551 (7)	0.95848 (6)	0.04848 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0361 (10)	0.0384 (12)	0.0580 (13)	−0.0019 (9)	0.0015 (10)	−0.0081 (10)
C2	0.0407 (13)	0.0523 (15)	0.0765 (17)	−0.0002 (11)	0.0107 (12)	−0.0006 (13)
C3	0.0666 (18)	0.0632 (18)	0.081 (2)	0.0040 (15)	0.0342 (15)	0.0044 (15)
C4	0.0709 (17)	0.0561 (17)	0.0595 (16)	0.0069 (13)	0.0155 (14)	0.0104 (13)
C5	0.0502 (13)	0.0437 (14)	0.0587 (15)	0.0032 (10)	0.0017 (11)	0.0047 (11)
C6	0.0369 (10)	0.0354 (12)	0.0499 (13)	−0.0005 (9)	0.0016 (9)	−0.0056 (10)
C7	0.0322 (10)	0.0402 (12)	0.0471 (12)	0.0021 (8)	−0.0027 (9)	−0.0072 (9)
C8	0.0315 (8)	0.0412 (11)	0.0439 (14)	0.0042 (8)	−0.0029 (9)	−0.0057 (10)
C9	0.0403 (12)	0.0447 (12)	0.0480 (12)	0.0016 (10)	0.0004 (10)	−0.0040 (11)
C10	0.0678 (16)	0.095 (2)	0.0642 (17)	0.0176 (16)	0.0203 (13)	0.0219 (18)
C11	0.0443 (10)	0.0444 (12)	0.0592 (13)	0.0112 (9)	−0.0031 (11)	0.0016 (13)
C12	0.0590 (14)	0.0499 (16)	0.0677 (17)	−0.0024 (11)	−0.0011 (13)	−0.0091 (12)
C13	0.077 (2)	0.059 (2)	0.107 (3)	−0.0003 (14)	0.0020 (18)	−0.0210 (19)
N1	0.0350 (9)	0.0465 (11)	0.0455 (12)	0.0077 (7)	−0.0061 (7)	−0.0044 (8)
O1	0.0354 (7)	0.0806 (12)	0.0740 (11)	0.0161 (7)	−0.0059 (9)	−0.0045 (11)
O2	0.0468 (10)	0.0802 (14)	0.0760 (12)	−0.0004 (8)	−0.0149 (8)	−0.0329 (11)
O3	0.0378 (8)	0.0548 (10)	0.0669 (11)	0.0137 (7)	0.0065 (7)	0.0114 (8)
O4	0.0413 (9)	0.0678 (11)	0.0669 (11)	0.0144 (8)	0.0100 (8)	0.0109 (9)
O5	0.0484 (9)	0.0677 (11)	0.0480 (9)	0.0105 (8)	0.0071 (7)	0.0092 (8)
S1	0.0309 (2)	0.0583 (3)	0.0562 (3)	0.0046 (2)	−0.0086 (3)	−0.0146 (3)

C1—C2	1.374 (3)	C10—O5	1.439 (3)
C1—C6	1.404 (3)	C10—H10A	0.9600
C1—S1	1.759 (3)	C10—H10B	0.9600
C2—C3	1.376 (4)	C10—H10C	0.9600
C2—H2	0.9300	C11—N1	1.483 (3)
C3—C4	1.375 (4)	C11—C12	1.511 (4)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.380 (3)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.513 (4)
C5—C6	1.382 (3)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.470 (3)	C13—H13A	0.9600
C7—O3	1.344 (2)	C13—H13B	0.9600
C7—C8	1.346 (3)	C13—H13C	0.9600
C8—N1	1.441 (3)	N1—S1	1.6339 (19)
C8—C9	1.455 (3)	O1—S1	1.4268 (15)
C9—O4	1.219 (3)	O2—S1	1.425 (2)
C9—O5	1.327 (3)	O3—H3A	0.8200
C2—C1—C6	121.5 (2)	H10A—C10—H10C	109.5
C2—C1—S1	121.76 (19)	H10B—C10—H10C	109.5
C6—C1—S1	116.72 (17)	N1—C11—C12	114.2 (2)
C1—C2—C3	119.0 (2)	N1—C11—H11A	108.7
C1—C2—H2	120.5	C12—C11—H11A	108.7
C3—C2—H2	120.5	N1—C11—H11B	108.7
C4—C3—C2	120.5 (2)	C12—C11—H11B	108.7
C4—C3—H3	119.7	H11A—C11—H11B	107.6
C2—C3—H3	119.7	C11—C12—C13	111.4 (2)
C3—C4—C5	120.5 (3)	C11—C12—H12A	109.3
C3—C4—H4	119.8	C13—C12—H12A	109.3
C5—C4—H4	119.8	C11—C12—H12B	109.3
C4—C5—C6	120.4 (2)	C13—C12—H12B	109.3
C4—C5—H5	119.8	H12A—C12—H12B	108.0
C6—C5—H5	119.8	C12—C13—H13A	109.5
C5—C6—C1	118.1 (2)	C12—C13—H13B	109.5
C5—C6—C7	122.04 (19)	H13A—C13—H13B	109.5
C1—C6—C7	119.8 (2)	C12—C13—H13C	109.5
O3—C7—C8	123.2 (2)	H13A—C13—H13C	109.5
O3—C7—C6	113.3 (2)	H13B—C13—H13C	109.5
C8—C7—C6	123.46 (18)	C8—N1—C11	117.79 (16)
C7—C8—N1	120.99 (19)	C8—N1—S1	113.92 (15)
C7—C8—C9	120.03 (18)	C11—N1—S1	119.13 (14)
N1—C8—C9	118.98 (19)	C7—O3—H3A	109.5
O4—C9—O5	122.6 (2)	C9—O5—C10	115.99 (19)
O4—C9—C8	122.6 (2)	O2—S1—O1	119.30 (11)
O5—C9—C8	114.85 (18)	O2—S1—N1	108.17 (11)
O5—C10—H10A	109.5	O1—S1—N1	108.37 (10)
O5—C10—H10B	109.5	O2—S1—C1	107.40 (13)
H10A—C10—H10B	109.5	O1—S1—C1	109.72 (11)
O5—C10—H10C	109.5	N1—S1—C1	102.59 (9)
C6—C1—C2—C3	0.1 (4)	N1—C8—C9—O5	1.8 (3)
S1—C1—C2—C3	−178.3 (2)	N1—C11—C12—C13	176.1 (2)
C1—C2—C3—C4	−0.5 (4)	C7—C8—N1—C11	−108.9 (2)
C2—C3—C4—C5	0.9 (4)	C9—C8—N1—C11	72.3 (3)
C3—C4—C5—C6	−0.9 (4)	C7—C8—N1—S1	37.8 (3)
C4—C5—C6—C1	0.5 (3)	C9—C8—N1—S1	−141.04 (17)
C4—C5—C6—C7	−178.1 (2)	C12—C11—N1—C8	63.6 (3)
C2—C1—C6—C5	−0.1 (3)	C12—C11—N1—S1	−81.3 (2)
S1—C1—C6—C5	178.34 (18)	O4—C9—O5—C10	2.7 (3)
C2—C1—C6—C7	178.5 (2)	C8—C9—O5—C10	−177.5 (2)
S1—C1—C6—C7	−3.0 (3)	C8—N1—S1—O2	61.60 (18)
C5—C6—C7—O3	−21.8 (3)	C11—N1—S1—O2	−152.19 (18)
C1—C6—C7—O3	159.7 (2)	C8—N1—S1—O1	−167.73 (15)
C5—C6—C7—C8	158.4 (2)	C11—N1—S1—O1	−21.5 (2)
C1—C6—C7—C8	−20.2 (3)	C8—N1—S1—C1	−51.72 (16)
O3—C7—C8—N1	−177.71 (19)	C11—N1—S1—C1	94.49 (18)
C6—C7—C8—N1	2.1 (3)	C2—C1—S1—O2	100.0 (2)
O3—C7—C8—C9	1.1 (3)	C6—C1—S1—O2	−78.46 (19)
C6—C7—C8—C9	−179.1 (2)	C2—C1—S1—O1	−31.1 (2)
C7—C8—C9—O4	2.6 (3)	C6—C1—S1—O1	150.46 (17)
N1—C8—C9—O4	−178.5 (2)	C2—C1—S1—N1	−146.1 (2)
C7—C8—C9—O5	−177.1 (2)	C6—C1—S1—N1	35.43 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.84	2.558 (2)	145
C3—H3···O2i	0.93	2.48	3.358 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.84	2.558 (2)	145
C3—H3⋯O2i	0.93	2.48	3.358 (3)	158

Symmetry code: (i) .