Methyl 2-butyl-4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zine-3-carboxyl-ate.

In the title compound, C(14)H(17)NO(5)S, the thia-zine ring adopts a half-chair conformation. The mol-ecule exhibits an intra-molecular O-H⋯O hydrogen bond, which forms a six-membered S(6) ring motif. The planes of the benzene and thia-zine rings are inclined at a dihedral angle of 15.30 (12)°.

Related literature

For the synthesis, see: Arshad et al. (2011a ▶). For biological activity of related compounds, see: Zia-ur-Rehman et al. (2006 ▶). For related structures, see: Arshad et al. (2011b ▶, 2012 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H17NO5S

M = 311.35

Monoclinic,

a = 25.173 (7) Å

b = 9.280 (2) Å

c = 12.531 (3) Å

β = 91.741 (3)°

V = 2926.0 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.44 × 0.31 × 0.25 mm

Data collection

Bruker SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.901, T max = 0.942

12490 measured reflections

3498 independent reflections

3132 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.210

S = 1.10

3498 reflections

193 parameters

H-atom parameters constrained

Δρmax = 1.70 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536812019733/im2370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019733/im2370Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019733/im2370Isup3.cml

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

C14H17NO5S	F(000) = 1312
Mr = 311.35	Dx = 1.414 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5544 reflections
a = 25.173 (7) Å	θ = 2.3–28.4°
b = 9.280 (2) Å	µ = 0.24 mm−1
c = 12.531 (3) Å	T = 100 K
β = 91.741 (3)°	Block, colorless
V = 2926.0 (13) Å3	0.44 × 0.31 × 0.25 mm
Z = 8

Bruker SMART 1K diffractometer	3498 independent reflections
Radiation source: fine-focus sealed tube	3132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −32→33
Tmin = 0.901, Tmax = 0.942	k = −12→12
12490 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0839P)2 + 25.4705P] where P = (Fo2 + 2Fc2)/3
3498 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 1.70 e Å−3
0 restraints	Δρmin = −0.49 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	0.39425 (3)	0.14891 (9)	0.48843 (6)	0.0157 (2)
O1	0.28629 (10)	0.2661 (3)	0.23550 (19)	0.0204 (5)
H1O	0.3009	0.2796	0.1770	0.024*
O2	0.39702 (10)	0.3001 (3)	0.5114 (2)	0.0212 (5)
O3	0.42548 (10)	0.0508 (3)	0.55284 (19)	0.0218 (5)
O4	0.36673 (10)	0.3043 (3)	0.11802 (19)	0.0222 (5)
O5	0.44802 (10)	0.2584 (3)	0.19007 (19)	0.0202 (5)
N1	0.40931 (11)	0.1252 (3)	0.3631 (2)	0.0166 (6)
C1	0.32710 (13)	0.0977 (4)	0.4870 (3)	0.0164 (6)
C2	0.30543 (14)	0.0261 (4)	0.5729 (3)	0.0206 (7)
H2	0.3273	−0.0019	0.6325	0.025*
C3	0.25114 (15)	−0.0039 (4)	0.5702 (3)	0.0231 (7)
H3	0.2358	−0.0522	0.6286	0.028*
C4	0.21938 (14)	0.0363 (4)	0.4828 (3)	0.0215 (7)
H4	0.1824	0.0160	0.4818	0.026*
C5	0.24152 (13)	0.1063 (4)	0.3964 (3)	0.0191 (7)
H5	0.2195	0.1339	0.3370	0.023*
C6	0.29595 (13)	0.1362 (4)	0.3967 (3)	0.0173 (6)
C7	0.32050 (13)	0.2003 (4)	0.3037 (3)	0.0171 (6)
C8	0.37370 (13)	0.1909 (4)	0.2873 (2)	0.0167 (6)
C9	0.39560 (13)	0.2557 (3)	0.1903 (3)	0.0169 (6)
C10	0.47078 (15)	0.3216 (5)	0.0957 (3)	0.0273 (8)
H10A	0.4646	0.2573	0.0346	0.041*
H10B	0.5091	0.3351	0.1081	0.041*
H10C	0.4540	0.4151	0.0809	0.041*
C11	0.43520 (13)	−0.0124 (4)	0.3326 (3)	0.0182 (6)
H11A	0.4666	−0.0282	0.3805	0.022*
H11B	0.4480	−0.0028	0.2590	0.022*
C12	0.39938 (14)	−0.1447 (4)	0.3374 (3)	0.0195 (7)
H12A	0.3675	−0.1300	0.2906	0.023*
H12B	0.3876	−0.1584	0.4114	0.023*
C13	0.42921 (15)	−0.2787 (4)	0.3015 (3)	0.0227 (7)
H13A	0.4631	−0.2864	0.3432	0.027*
H13B	0.4378	−0.2683	0.2253	0.027*
C14	0.39715 (17)	−0.4169 (4)	0.3160 (4)	0.0340 (9)
H14A	0.3861	−0.4238	0.3902	0.051*
H14B	0.4191	−0.5004	0.2989	0.051*
H14C	0.3656	−0.4149	0.2682	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0160 (4)	0.0161 (4)	0.0148 (4)	0.0010 (3)	−0.0017 (3)	−0.0007 (3)
O1	0.0192 (12)	0.0225 (12)	0.0192 (12)	0.0038 (9)	−0.0023 (9)	0.0033 (9)
O2	0.0222 (12)	0.0166 (12)	0.0244 (12)	−0.0010 (9)	−0.0021 (9)	−0.0047 (9)
O3	0.0210 (12)	0.0254 (13)	0.0188 (11)	0.0036 (10)	−0.0032 (9)	0.0026 (9)
O4	0.0236 (13)	0.0227 (13)	0.0201 (12)	0.0006 (10)	−0.0020 (9)	0.0049 (9)
O5	0.0202 (12)	0.0226 (12)	0.0176 (11)	−0.0026 (9)	0.0000 (9)	0.0032 (9)
N1	0.0200 (14)	0.0180 (13)	0.0116 (12)	0.0010 (11)	−0.0013 (10)	0.0003 (10)
C1	0.0149 (14)	0.0163 (15)	0.0180 (15)	0.0021 (12)	−0.0008 (11)	−0.0025 (12)
C2	0.0224 (17)	0.0195 (16)	0.0199 (16)	0.0047 (13)	0.0011 (12)	0.0014 (12)
C3	0.0277 (18)	0.0184 (16)	0.0235 (17)	0.0050 (14)	0.0066 (13)	0.0026 (13)
C4	0.0177 (16)	0.0179 (16)	0.0290 (18)	−0.0012 (12)	0.0031 (13)	−0.0043 (13)
C5	0.0173 (15)	0.0169 (15)	0.0232 (16)	0.0008 (12)	−0.0005 (12)	−0.0033 (12)
C6	0.0193 (16)	0.0151 (15)	0.0175 (15)	0.0026 (12)	−0.0005 (11)	−0.0023 (11)
C7	0.0205 (16)	0.0142 (15)	0.0164 (15)	0.0020 (12)	−0.0037 (11)	−0.0017 (11)
C8	0.0208 (16)	0.0149 (14)	0.0142 (14)	0.0000 (12)	−0.0023 (11)	0.0006 (11)
C9	0.0199 (16)	0.0110 (14)	0.0197 (15)	−0.0006 (11)	−0.0008 (12)	−0.0005 (11)
C10	0.0236 (18)	0.036 (2)	0.0225 (17)	−0.0062 (16)	0.0038 (13)	0.0081 (15)
C11	0.0180 (15)	0.0179 (15)	0.0187 (15)	0.0017 (12)	0.0008 (11)	0.0009 (12)
C12	0.0215 (16)	0.0174 (16)	0.0196 (16)	0.0031 (12)	−0.0002 (12)	−0.0007 (12)
C13	0.0281 (18)	0.0206 (17)	0.0193 (16)	0.0060 (14)	0.0007 (13)	−0.0014 (13)
C14	0.034 (2)	0.0225 (19)	0.046 (2)	0.0012 (16)	−0.0062 (17)	−0.0043 (17)

S1—O2	1.433 (3)	C5—H5	0.9500
S1—O3	1.435 (2)	C6—C7	1.462 (5)
S1—N1	1.642 (3)	C7—C8	1.364 (5)
S1—C1	1.756 (3)	C8—C9	1.478 (5)
O1—C7	1.341 (4)	C10—H10A	0.9800
O1—H1O	0.8400	C10—H10B	0.9800
O4—C9	1.230 (4)	C10—H10C	0.9800
O5—C9	1.320 (4)	C11—C12	1.526 (5)
O5—C10	1.453 (4)	C11—H11A	0.9900
N1—C8	1.423 (4)	C11—H11B	0.9900
N1—C11	1.489 (4)	C12—C13	1.527 (5)
C1—C2	1.390 (5)	C12—H12A	0.9900
C1—C6	1.404 (4)	C12—H12B	0.9900
C2—C3	1.394 (5)	C13—C14	1.528 (6)
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.388 (5)	C13—H13B	0.9900
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.393 (5)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.398 (5)
O2—S1—O3	119.06 (15)	N1—C8—C9	118.7 (3)
O2—S1—N1	108.17 (15)	O4—C9—O5	124.0 (3)
O3—S1—N1	108.32 (15)	O4—C9—C8	121.9 (3)
O2—S1—C1	107.95 (15)	O5—C9—C8	114.1 (3)
O3—S1—C1	110.17 (16)	O5—C10—H10A	109.5
N1—S1—C1	101.78 (15)	O5—C10—H10B	109.5
C7—O1—H1O	109.5	H10A—C10—H10B	109.5
C9—O5—C10	115.4 (3)	O5—C10—H10C	109.5
C8—N1—C11	117.9 (3)	H10A—C10—H10C	109.5
C8—N1—S1	114.9 (2)	H10B—C10—H10C	109.5
C11—N1—S1	118.5 (2)	N1—C11—C12	114.6 (3)
C2—C1—C6	121.6 (3)	N1—C11—H11A	108.6
C2—C1—S1	121.5 (2)	C12—C11—H11A	108.6
C6—C1—S1	117.0 (3)	N1—C11—H11B	108.6
C1—C2—C3	119.0 (3)	C12—C11—H11B	108.6
C1—C2—H2	120.5	H11A—C11—H11B	107.6
C3—C2—H2	120.5	C11—C12—C13	110.3 (3)
C4—C3—C2	120.4 (3)	C11—C12—H12A	109.6
C4—C3—H3	119.8	C13—C12—H12A	109.6
C2—C3—H3	119.8	C11—C12—H12B	109.6
C3—C4—C5	120.3 (3)	C13—C12—H12B	109.6
C3—C4—H4	119.9	H12A—C12—H12B	108.1
C5—C4—H4	119.9	C12—C13—C14	112.4 (3)
C4—C5—C6	120.4 (3)	C12—C13—H13A	109.1
C4—C5—H5	119.8	C14—C13—H13A	109.1
C6—C5—H5	119.8	C12—C13—H13B	109.1
C5—C6—C1	118.3 (3)	C14—C13—H13B	109.1
C5—C6—C7	121.1 (3)	H13A—C13—H13B	107.8
C1—C6—C7	120.5 (3)	C13—C14—H14A	109.5
O1—C7—C8	123.2 (3)	C13—C14—H14B	109.5
O1—C7—C6	114.4 (3)	H14A—C14—H14B	109.5
C8—C7—C6	122.3 (3)	C13—C14—H14C	109.5
C7—C8—N1	121.9 (3)	H14A—C14—H14C	109.5
C7—C8—C9	119.3 (3)	H14B—C14—H14C	109.5
O2—S1—N1—C8	−63.0 (3)	C5—C6—C7—O1	19.3 (5)
O3—S1—N1—C8	166.7 (2)	C1—C6—C7—O1	−163.4 (3)
C1—S1—N1—C8	50.6 (3)	C5—C6—C7—C8	−159.5 (3)
O2—S1—N1—C11	150.0 (2)	C1—C6—C7—C8	17.9 (5)
O3—S1—N1—C11	19.7 (3)	O1—C7—C8—N1	177.6 (3)
C1—S1—N1—C11	−96.5 (3)	C6—C7—C8—N1	−3.8 (5)
O2—S1—C1—C2	−102.1 (3)	O1—C7—C8—C9	0.1 (5)
O3—S1—C1—C2	29.5 (3)	C6—C7—C8—C9	178.7 (3)
N1—S1—C1—C2	144.2 (3)	C11—N1—C8—C7	112.4 (4)
O2—S1—C1—C6	76.0 (3)	S1—N1—C8—C7	−34.9 (4)
O3—S1—C1—C6	−152.4 (2)	C11—N1—C8—C9	−70.1 (4)
N1—S1—C1—C6	−37.7 (3)	S1—N1—C8—C9	142.7 (3)
C6—C1—C2—C3	−2.0 (5)	C10—O5—C9—O4	−1.1 (5)
S1—C1—C2—C3	176.0 (3)	C10—O5—C9—C8	−179.9 (3)
C1—C2—C3—C4	0.4 (5)	C7—C8—C9—O4	−8.0 (5)
C2—C3—C4—C5	0.4 (5)	N1—C8—C9—O4	174.3 (3)
C3—C4—C5—C6	0.3 (5)	C7—C8—C9—O5	170.8 (3)
C4—C5—C6—C1	−1.8 (5)	N1—C8—C9—O5	−6.8 (4)
C4—C5—C6—C7	175.6 (3)	C8—N1—C11—C12	−76.7 (4)
C2—C1—C6—C5	2.7 (5)	S1—N1—C11—C12	69.3 (3)
S1—C1—C6—C5	−175.4 (3)	N1—C11—C12—C13	178.3 (3)
C2—C1—C6—C7	−174.8 (3)	C11—C12—C13—C14	174.0 (3)
S1—C1—C6—C7	7.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.84	1.85	2.564 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.84	1.85	2.564 (4)	142