Methyl 2-(but-3-en-yl)-4-hy-droxy-1,1-dioxo-2H-1λ(6),2-benzothia-zine-3-carboxyl-ate.

In the title compound, C(14)H(15)NO(5)S, the thia-zine ring adopts a sofa conformation and an intra-molecular O-H⋯O hydrogen bond forms an S(6) ring. In the crystal, molecules are linked viaC-H⋯O inter-actions.

Related literature

For the synthesis, see: Arshad et al. (2011b ▶); Zia-ur-Rehman, et al. (2006 ▶). For related structures, see: Arshad et al. (2011a ▶, 2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H15NO5S

M = 309.33

Orthorhombic,

a = 25.265 (8) Å

b = 8.929 (3) Å

c = 12.584 (4) Å

V = 2839.0 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.41 × 0.36 × 0.19 mm

Data collection

Bruker SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.905, T max = 0.954

22868 measured reflections

3445 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.05

3445 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 X-SEED (Barbour 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022908/bt5926sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022908/bt5926Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022908/bt5926Isup3.cml

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

C14H15NO5S	F(000) = 1296
Mr = 309.33	Dx = 1.447 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4741 reflections
a = 25.265 (8) Å	θ = 2.4–27.3°
b = 8.929 (3) Å	µ = 0.25 mm−1
c = 12.584 (4) Å	T = 100 K
V = 2839.0 (15) Å3	Block, colorless
Z = 8	0.41 × 0.36 × 0.19 mm

Bruker SMART 1K diffractometer	3445 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −33→32
Tmin = 0.905, Tmax = 0.954	k = −11→11
22868 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.393P] where P = (Fo2 + 2Fc2)/3
3445 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.52 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	0.383769 (17)	0.36570 (5)	0.46460 (3)	0.01998 (13)
O1	0.28657 (5)	0.22258 (15)	0.20949 (10)	0.0233 (3)
O2	0.38708 (5)	0.20923 (14)	0.48963 (10)	0.0237 (3)
O3	0.41184 (5)	0.47125 (15)	0.52964 (10)	0.0252 (3)
O4	0.37180 (5)	0.18207 (15)	0.10068 (10)	0.0242 (3)
O5	0.44900 (5)	0.25535 (14)	0.17283 (10)	0.0218 (3)
N1	0.40302 (6)	0.38813 (17)	0.34120 (11)	0.0193 (3)
C1	0.31660 (7)	0.4152 (2)	0.45726 (14)	0.0206 (4)
C2	0.29195 (7)	0.4945 (2)	0.53786 (14)	0.0234 (4)
H2	0.3113	0.5258	0.5987	0.028*
C3	0.23838 (7)	0.5274 (2)	0.52817 (15)	0.0260 (4)
H3	0.2210	0.5839	0.5819	0.031*
C4	0.21024 (7)	0.4782 (2)	0.44037 (15)	0.0256 (4)
H4	0.1734	0.4989	0.4354	0.031*
C5	0.23497 (7)	0.3991 (2)	0.35976 (15)	0.0233 (4)
H5	0.2151	0.3656	0.3003	0.028*
C6	0.28911 (7)	0.36857 (19)	0.36578 (14)	0.0194 (4)
C7	0.31751 (7)	0.29795 (19)	0.27785 (14)	0.0198 (4)
C8	0.37096 (7)	0.3116 (2)	0.26458 (14)	0.0190 (4)
C9	0.39673 (7)	0.2439 (2)	0.17199 (14)	0.0202 (4)
C10	0.47565 (8)	0.1946 (2)	0.08044 (15)	0.0271 (4)
H10A	0.4664	0.0886	0.0725	0.041*
H10B	0.5140	0.2044	0.0894	0.041*
H10C	0.4645	0.2496	0.0169	0.041*
C11	0.42697 (7)	0.5340 (2)	0.30952 (15)	0.0228 (4)
H11A	0.4436	0.5221	0.2387	0.027*
H11B	0.4554	0.5591	0.3606	0.027*
C12	0.38804 (8)	0.6648 (2)	0.30478 (16)	0.0272 (4)
H12A	0.3576	0.6377	0.2591	0.033*
H12B	0.3745	0.6864	0.3770	0.033*
C13	0.41478 (8)	0.8014 (2)	0.26092 (17)	0.0316 (5)
H13	0.4245	0.8001	0.1880	0.038*
C14	0.42573 (8)	0.9223 (2)	0.31568 (17)	0.0306 (5)
H14A	0.4166	0.9276	0.3888	0.037*
H14B	0.4428	1.0045	0.2823	0.037*
H1O	0.3066 (11)	0.199 (3)	0.159 (2)	0.046*

	U11	U22	U33	U12	U13	U23
S1	0.0183 (2)	0.0232 (2)	0.0185 (2)	−0.00070 (17)	−0.00184 (16)	−0.00094 (17)
O1	0.0193 (6)	0.0285 (7)	0.0221 (7)	−0.0037 (5)	−0.0026 (5)	−0.0032 (5)
O2	0.0240 (7)	0.0246 (7)	0.0227 (7)	0.0010 (5)	−0.0039 (5)	0.0011 (5)
O3	0.0231 (7)	0.0310 (7)	0.0217 (7)	−0.0030 (5)	−0.0018 (5)	−0.0041 (6)
O4	0.0211 (6)	0.0284 (7)	0.0230 (7)	−0.0001 (5)	−0.0031 (5)	−0.0043 (6)
O5	0.0174 (6)	0.0261 (7)	0.0219 (6)	0.0018 (5)	−0.0002 (5)	−0.0021 (5)
N1	0.0171 (7)	0.0230 (8)	0.0178 (7)	−0.0020 (6)	−0.0010 (6)	−0.0018 (6)
C1	0.0194 (8)	0.0202 (9)	0.0221 (9)	−0.0026 (7)	0.0016 (7)	0.0027 (7)
C2	0.0250 (9)	0.0250 (10)	0.0201 (9)	−0.0023 (8)	0.0012 (7)	−0.0004 (7)
C3	0.0264 (9)	0.0256 (10)	0.0260 (10)	0.0012 (8)	0.0076 (7)	0.0014 (8)
C4	0.0193 (9)	0.0278 (10)	0.0297 (10)	0.0015 (7)	0.0036 (7)	0.0062 (8)
C5	0.0192 (9)	0.0267 (10)	0.0241 (9)	−0.0029 (7)	−0.0001 (7)	0.0043 (8)
C6	0.0189 (8)	0.0187 (9)	0.0205 (9)	−0.0026 (7)	0.0001 (7)	0.0028 (7)
C7	0.0200 (8)	0.0194 (9)	0.0198 (9)	−0.0010 (7)	−0.0022 (7)	0.0018 (7)
C8	0.0186 (8)	0.0194 (8)	0.0189 (9)	−0.0013 (7)	−0.0025 (7)	−0.0004 (7)
C9	0.0196 (9)	0.0196 (9)	0.0213 (9)	0.0006 (7)	−0.0008 (7)	0.0027 (7)
C10	0.0241 (9)	0.0319 (11)	0.0253 (10)	0.0034 (8)	0.0040 (8)	−0.0036 (8)
C11	0.0210 (9)	0.0243 (10)	0.0230 (9)	−0.0048 (7)	0.0010 (7)	−0.0020 (8)
C12	0.0281 (10)	0.0249 (10)	0.0286 (10)	−0.0031 (8)	−0.0032 (8)	−0.0006 (8)
C13	0.0398 (12)	0.0307 (11)	0.0242 (10)	−0.0041 (9)	−0.0020 (9)	0.0037 (9)
C14	0.0343 (11)	0.0261 (10)	0.0313 (11)	−0.0013 (8)	−0.0053 (8)	0.0042 (9)

S1—O2	1.4346 (14)	C5—C6	1.397 (2)
S1—O3	1.4356 (13)	C5—H5	0.9500
S1—N1	1.6396 (16)	C6—C7	1.462 (2)
S1—C1	1.7561 (19)	C7—C8	1.366 (2)
O1—C7	1.343 (2)	C8—C9	1.465 (3)
O1—H1O	0.84 (3)	C10—H10A	0.9800
O4—C9	1.227 (2)	C10—H10B	0.9800
O5—C9	1.325 (2)	C10—H10C	0.9800
O5—C10	1.449 (2)	C11—C12	1.528 (3)
N1—C8	1.433 (2)	C11—H11A	0.9900
N1—C11	1.490 (2)	C11—H11B	0.9900
C1—C2	1.385 (3)	C12—C13	1.499 (3)
C1—C6	1.407 (2)	C12—H12A	0.9900
C2—C3	1.391 (3)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.310 (3)
C3—C4	1.386 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—H14A	0.9500
C4—C5	1.385 (3)	C14—H14B	0.9500
C4—H4	0.9500
O2—S1—O3	119.04 (8)	C8—C7—C6	122.63 (16)
O2—S1—N1	108.04 (8)	C7—C8—N1	121.29 (16)
O3—S1—N1	108.25 (8)	C7—C8—C9	119.96 (16)
O2—S1—C1	108.24 (8)	N1—C8—C9	118.73 (15)
O3—S1—C1	110.00 (8)	O4—C9—O5	123.51 (17)
N1—S1—C1	101.90 (8)	O4—C9—C8	122.61 (16)
C7—O1—H1O	104.9 (18)	O5—C9—C8	113.87 (15)
C9—O5—C10	115.33 (14)	O5—C10—H10A	109.5
C8—N1—C11	117.79 (14)	O5—C10—H10B	109.5
C8—N1—S1	114.29 (12)	H10A—C10—H10B	109.5
C11—N1—S1	118.72 (12)	O5—C10—H10C	109.5
C2—C1—C6	121.90 (17)	H10A—C10—H10C	109.5
C2—C1—S1	121.65 (14)	H10B—C10—H10C	109.5
C6—C1—S1	116.46 (13)	N1—C11—C12	114.66 (15)
C1—C2—C3	118.80 (17)	N1—C11—H11A	108.6
C1—C2—H2	120.6	C12—C11—H11A	108.6
C3—C2—H2	120.6	N1—C11—H11B	108.6
C4—C3—C2	120.14 (17)	C12—C11—H11B	108.6
C4—C3—H3	119.9	H11A—C11—H11B	107.6
C2—C3—H3	119.9	C13—C12—C11	110.25 (17)
C5—C4—C3	120.96 (17)	C13—C12—H12A	109.6
C5—C4—H4	119.5	C11—C12—H12A	109.6
C3—C4—H4	119.5	C13—C12—H12B	109.6
C4—C5—C6	120.12 (18)	C11—C12—H12B	109.6
C4—C5—H5	119.9	H12A—C12—H12B	108.1
C6—C5—H5	119.9	C14—C13—C12	124.9 (2)
C5—C6—C1	118.02 (17)	C14—C13—H13	117.6
C5—C6—C7	121.60 (16)	C12—C13—H13	117.6
C1—C6—C7	120.29 (16)	C13—C14—H14A	120.0
O1—C7—C8	122.81 (16)	C13—C14—H14B	120.0
O1—C7—C6	114.53 (15)	H14A—C14—H14B	120.0
O2—S1—N1—C8	61.69 (14)	C5—C6—C7—O1	−20.8 (2)
O3—S1—N1—C8	−168.15 (12)	C1—C6—C7—O1	162.66 (16)
C1—S1—N1—C8	−52.19 (14)	C5—C6—C7—C8	157.21 (18)
O2—S1—N1—C11	−152.15 (12)	C1—C6—C7—C8	−19.3 (3)
O3—S1—N1—C11	−21.99 (15)	O1—C7—C8—N1	−177.64 (15)
C1—S1—N1—C11	93.96 (14)	C6—C7—C8—N1	4.5 (3)
O2—S1—C1—C2	104.25 (16)	O1—C7—C8—C9	0.7 (3)
O3—S1—C1—C2	−27.34 (18)	C6—C7—C8—C9	−177.14 (16)
N1—S1—C1—C2	−142.01 (15)	C11—N1—C8—C7	−110.93 (19)
O2—S1—C1—C6	−75.07 (15)	S1—N1—C8—C7	35.6 (2)
O3—S1—C1—C6	153.34 (13)	C11—N1—C8—C9	70.7 (2)
N1—S1—C1—C6	38.67 (15)	S1—N1—C8—C9	−142.81 (14)
C6—C1—C2—C3	0.6 (3)	C10—O5—C9—O4	2.4 (3)
S1—C1—C2—C3	−178.67 (14)	C10—O5—C9—C8	−177.74 (15)
C1—C2—C3—C4	1.6 (3)	C7—C8—C9—O4	4.8 (3)
C2—C3—C4—C5	−1.7 (3)	N1—C8—C9—O4	−176.84 (16)
C3—C4—C5—C6	−0.3 (3)	C7—C8—C9—O5	−175.05 (16)
C4—C5—C6—C1	2.4 (3)	N1—C8—C9—O5	3.3 (2)
C4—C5—C6—C7	−174.17 (17)	C8—N1—C11—C12	74.1 (2)
C2—C1—C6—C5	−2.6 (3)	S1—N1—C11—C12	−70.88 (19)
S1—C1—C6—C5	176.72 (14)	N1—C11—C12—C13	−173.83 (15)
C2—C1—C6—C7	174.05 (17)	C11—C12—C13—C14	−111.0 (2)
S1—C1—C6—C7	−6.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.95	2.52	3.269 (2)	136
O1—H1O···O4	0.84 (3)	1.81 (3)	2.577 (2)	151 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.95	2.52	3.269 (2)	136
O1—H1O⋯O4	0.84 (3)	1.81 (3)	2.577 (2)	151 (3)

Symmetry code: (i) .