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

In the title compound, C(13)H(13)NO(5)S, the thia-zine ring adopts a distorted half-chair conformation. Intra-molecular O-H⋯O and C-H⋯O hydrogen bonds give rise to two six-membered hydrogen bonded rings. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds, resulting in a zigzag chain lying along the c axis.

Related literature

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

Experimental

Crystal data

C13H13NO5S

M = 295.30

Orthorhombic,

a = 12.4289 (10) Å

b = 8.3706 (8) Å

c = 13.0132 (11) Å

V = 1353.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.45 × 0.11 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.893, T max = 0.982

8404 measured reflections

2808 independent reflections

1763 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.103

S = 1.06

2808 reflections

183 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1046 Friedel pairs

Flack parameter: 0.07 (11)

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/S160053680904673X/is2483sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904673X/is2483Isup2.hkl

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

C13H13NO5S	F(000) = 616
Mr = 295.30	Dx = 1.449 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1619 reflections
a = 12.4289 (10) Å	θ = 3.1–21.7°
b = 8.3706 (8) Å	µ = 0.26 mm−1
c = 13.0132 (11) Å	T = 296 K
V = 1353.9 (2) Å3	Needle, colourless
Z = 4	0.45 × 0.11 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.893, Tmax = 0.982	k = −11→10
8404 measured reflections	l = −17→9

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.1044P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2808 reflections	Δρmax = 0.18 e Å−3
183 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 1046 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (11)

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	−0.11229 (6)	0.28643 (12)	0.49624 (9)	0.0550 (3)
O1	−0.12270 (18)	0.1530 (4)	0.5634 (3)	0.0733 (9)
O2	−0.19486 (15)	0.4041 (3)	0.4937 (3)	0.0714 (8)
O3	0.18469 (19)	0.0795 (3)	0.4129 (2)	0.0669 (9)
H3O	0.2303	0.0963	0.4571	0.100*
O4	0.26461 (18)	0.2122 (3)	0.5724 (2)	0.0658 (8)
O5	0.16238 (19)	0.3843 (3)	0.6600 (2)	0.0612 (7)
N1	0.0004 (2)	0.3754 (3)	0.5229 (2)	0.0490 (9)
C1	−0.0885 (3)	0.2109 (4)	0.3733 (3)	0.0487 (10)
C2	−0.1708 (3)	0.1997 (5)	0.3013 (4)	0.0647 (12)
H2	−0.2396	0.2360	0.3168	0.078*
C3	−0.1488 (4)	0.1344 (5)	0.2074 (4)	0.0737 (13)
H3A	−0.2034	0.1247	0.1590	0.088*
C4	−0.0462 (4)	0.0828 (5)	0.1837 (4)	0.0721 (12)
H4	−0.0319	0.0406	0.1191	0.087*
C5	0.0348 (3)	0.0935 (5)	0.2553 (3)	0.0602 (12)
H5	0.1032	0.0564	0.2391	0.072*
C6	0.0156 (3)	0.1588 (4)	0.3509 (3)	0.0468 (9)
C7	0.1002 (3)	0.1766 (4)	0.4281 (3)	0.0467 (9)
C8	0.0945 (2)	0.2785 (4)	0.5071 (4)	0.0450 (9)
C9	0.1819 (3)	0.2889 (4)	0.5819 (3)	0.0502 (9)
C10	0.2475 (4)	0.3995 (6)	0.7344 (4)	0.0867 (14)
H10A	0.3070	0.4555	0.7042	0.130*
H10B	0.2706	0.2951	0.7557	0.130*
H10C	0.2218	0.4579	0.7930	0.130*
C11	0.0106 (3)	0.5495 (4)	0.5090 (3)	0.0595 (10)
H11A	0.0695	0.5878	0.5513	0.071*
H11B	−0.0548	0.6004	0.5331	0.071*
C12	0.0304 (4)	0.5986 (7)	0.4006 (5)	0.1008 (19)
H12	0.0732	0.5271	0.3642	0.121*
C13	0.0036 (6)	0.7061 (11)	0.3530 (7)	0.161 (3)
H13A	−0.0395	0.7845	0.3826	0.194*
H13B	0.0249	0.7154	0.2848	0.194*

	U11	U22	U33	U12	U13	U23
S1	0.0376 (4)	0.0683 (6)	0.0593 (6)	0.0050 (4)	0.0069 (5)	0.0078 (7)
O1	0.0553 (15)	0.088 (2)	0.076 (2)	−0.0060 (14)	0.0169 (15)	0.0296 (19)
O2	0.0418 (12)	0.0919 (19)	0.080 (2)	0.0220 (12)	0.0017 (16)	−0.0075 (19)
O3	0.0477 (15)	0.0674 (19)	0.086 (3)	0.0147 (14)	−0.0021 (13)	−0.0186 (15)
O4	0.0474 (14)	0.0682 (17)	0.082 (2)	0.0146 (13)	−0.0103 (13)	−0.0130 (18)
O5	0.0537 (14)	0.0741 (19)	0.0557 (19)	0.0121 (13)	−0.0078 (13)	−0.0097 (16)
N1	0.0439 (14)	0.0501 (18)	0.053 (3)	0.0077 (13)	0.0021 (12)	0.0005 (16)
C1	0.046 (2)	0.037 (2)	0.064 (3)	−0.0039 (16)	−0.0024 (18)	0.006 (2)
C2	0.055 (2)	0.055 (3)	0.084 (4)	0.005 (2)	−0.012 (2)	−0.001 (3)
C3	0.074 (3)	0.072 (3)	0.075 (4)	0.001 (2)	−0.025 (2)	−0.010 (3)
C4	0.092 (3)	0.064 (3)	0.060 (3)	−0.005 (2)	−0.011 (3)	−0.016 (2)
C5	0.057 (2)	0.052 (3)	0.072 (4)	−0.0030 (18)	0.001 (2)	−0.013 (2)
C6	0.0473 (19)	0.039 (2)	0.054 (3)	−0.0024 (15)	−0.0026 (18)	−0.0014 (19)
C7	0.0384 (18)	0.043 (2)	0.059 (3)	0.0018 (15)	0.0066 (18)	0.0058 (19)
C8	0.0376 (15)	0.0445 (19)	0.053 (3)	0.0037 (15)	0.005 (2)	0.001 (2)
C9	0.048 (2)	0.046 (2)	0.057 (3)	0.0034 (18)	0.0015 (19)	0.005 (2)
C10	0.077 (2)	0.113 (4)	0.070 (3)	0.024 (3)	−0.031 (2)	−0.027 (3)
C11	0.061 (2)	0.050 (2)	0.068 (3)	0.0065 (17)	−0.002 (2)	0.001 (2)
C12	0.093 (4)	0.070 (4)	0.139 (6)	0.008 (3)	0.010 (3)	0.036 (4)
C13	0.211 (9)	0.131 (7)	0.142 (7)	−0.031 (6)	−0.035 (6)	0.050 (5)

S1—O2	1.423 (2)	C4—C5	1.375 (5)
S1—O1	1.424 (3)	C4—H4	0.9300
S1—N1	1.625 (3)	C5—C6	1.380 (5)
S1—C1	1.746 (4)	C5—H5	0.9300
O3—C7	1.343 (4)	C6—C7	1.462 (5)
O3—H3O	0.8200	C7—C8	1.338 (5)
O4—C9	1.218 (4)	C8—C9	1.461 (5)
O5—C9	1.315 (4)	C10—H10A	0.9600
O5—C10	1.440 (5)	C10—H10B	0.9600
N1—C8	1.438 (4)	C10—H10C	0.9600
N1—C11	1.473 (4)	C11—C12	1.490 (7)
C1—C2	1.390 (5)	C11—H11A	0.9700
C1—C6	1.396 (5)	C11—H11B	0.9700
C2—C3	1.366 (6)	C12—C13	1.142 (8)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.380 (6)	C13—H13A	0.9300
C3—H3A	0.9300	C13—H13B	0.9300
O2—S1—O1	119.46 (17)	C1—C6—C7	119.4 (3)
O2—S1—N1	108.03 (15)	C8—C7—O3	122.7 (3)
O1—S1—N1	107.87 (16)	C8—C7—C6	123.7 (3)
O2—S1—C1	110.57 (18)	O3—C7—C6	113.5 (3)
O1—S1—C1	107.1 (2)	C7—C8—N1	120.8 (3)
N1—S1—C1	102.48 (15)	C7—C8—C9	120.7 (3)
C7—O3—H3O	109.5	N1—C8—C9	118.4 (3)
C9—O5—C10	116.0 (3)	O4—C9—O5	123.6 (3)
C8—N1—C11	118.1 (3)	O4—C9—C8	121.9 (4)
C8—N1—S1	114.3 (2)	O5—C9—C8	114.4 (3)
C11—N1—S1	120.1 (2)	O5—C10—H10A	109.5
C2—C1—C6	121.4 (4)	O5—C10—H10B	109.5
C2—C1—S1	121.2 (3)	H10A—C10—H10B	109.5
C6—C1—S1	117.5 (3)	O5—C10—H10C	109.5
C3—C2—C1	118.8 (4)	H10A—C10—H10C	109.5
C3—C2—H2	120.6	H10B—C10—H10C	109.5
C1—C2—H2	120.6	N1—C11—C12	113.8 (4)
C2—C3—C4	120.7 (4)	N1—C11—H11A	108.8
C2—C3—H3A	119.7	C12—C11—H11A	108.8
C4—C3—H3A	119.7	N1—C11—H11B	108.8
C5—C4—C3	120.3 (4)	C12—C11—H11B	108.8
C5—C4—H4	119.9	H11A—C11—H11B	107.7
C3—C4—H4	119.9	C13—C12—C11	133.1 (7)
C4—C5—C6	120.7 (4)	C13—C12—H12	113.5
C4—C5—H5	119.7	C11—C12—H12	113.5
C6—C5—H5	119.7	C12—C13—H13A	120.0
C5—C6—C1	118.1 (3)	C12—C13—H13B	120.0
C5—C6—C7	122.4 (3)	H13A—C13—H13B	120.0
O2—S1—N1—C8	−167.6 (2)	S1—C1—C6—C7	−2.9 (5)
O1—S1—N1—C8	62.0 (3)	C5—C6—C7—C8	159.4 (4)
C1—S1—N1—C8	−50.8 (3)	C1—C6—C7—C8	−19.9 (6)
O2—S1—N1—C11	−18.4 (4)	C5—C6—C7—O3	−21.1 (5)
O1—S1—N1—C11	−148.8 (3)	C1—C6—C7—O3	159.6 (3)
C1—S1—N1—C11	98.4 (3)	O3—C7—C8—N1	−177.3 (3)
O2—S1—C1—C2	−31.7 (4)	C6—C7—C8—N1	2.2 (6)
O1—S1—C1—C2	100.0 (3)	O3—C7—C8—C9	0.0 (6)
N1—S1—C1—C2	−146.6 (3)	C6—C7—C8—C9	179.5 (3)
O2—S1—C1—C6	149.8 (3)	C11—N1—C8—C7	−112.6 (4)
O1—S1—C1—C6	−78.6 (3)	S1—N1—C8—C7	37.3 (4)
N1—S1—C1—C6	34.8 (3)	C11—N1—C8—C9	70.1 (4)
C6—C1—C2—C3	0.8 (6)	S1—N1—C8—C9	−140.1 (3)
S1—C1—C2—C3	−177.7 (3)	C10—O5—C9—O4	2.4 (5)
C1—C2—C3—C4	−1.0 (6)	C10—O5—C9—C8	−179.0 (3)
C2—C3—C4—C5	1.3 (7)	C7—C8—C9—O4	3.8 (6)
C3—C4—C5—C6	−1.3 (6)	N1—C8—C9—O4	−178.8 (3)
C4—C5—C6—C1	1.1 (6)	C7—C8—C9—O5	−174.8 (3)
C4—C5—C6—C7	−178.2 (4)	N1—C8—C9—O5	2.6 (5)
C2—C1—C6—C5	−0.8 (6)	C8—N1—C11—C12	68.0 (4)
S1—C1—C6—C5	177.7 (3)	S1—N1—C11—C12	−80.1 (4)
C2—C1—C6—C7	178.5 (3)	N1—C11—C12—C13	144.7 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.82	1.84	2.555 (4)	146
C11—H11A···O5	0.97	2.50	3.055 (4)	116
C3—H3A···O1i	0.93	2.51	3.406 (6)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.82	1.84	2.555 (4)	146
C11—H11A⋯O5	0.97	2.50	3.055 (4)	116
C3—H3A⋯O1i	0.93	2.51	3.406 (6)	163

Symmetry code: (i) .