Methyl 2-benzyl-4-hy-droxy-1,1-dioxo-1,2,3,4-tetra-hydro-1λ,2-benzothia-zine-3-carboxyl-ate.

In the title compound, C(17)H(15)NO(5)S, the benzene ring of the fused-ring system is twisted by 11.67 (6)° with respect to the thia-zine ring. The atoms of the four-atom methyl ester group and the phenyl ring of the benzyl unit are inclined at 16.50 (7) and 44.52 (3)° with respect to the thia-zine ring. An intra-molecular O-H⋯O hydrogen bond gives rise to a six-membered S(6) ring motif. In the crystal, mol-ecules are extended through a C-H⋯O inter-action along the a axis. C-H⋯π inter-actions are also observed.

Related literature

For the biological properties of benzothia­zines, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶). For a related structure, see: Arshad et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H15NO5S

M = 345.36

Monoclinic,

a = 9.4920 (15) Å

b = 10.9607 (17) Å

c = 15.050 (2) Å

β = 99.758 (2)°

V = 1543.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.43 × 0.25 × 0.19 mm

Data collection

Bruker SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.905, T max = 0.956

13430 measured reflections

3719 independent reflections

3297 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.06

3719 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.57 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: X-SEED (Barbour, 2001) ▶, WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020289/ng5172sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020289/ng5172Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020289/ng5172Isup3.cml

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

C17H15NO5S	F(000) = 720
Mr = 345.36	Dx = 1.487 Mg m−3
Monoclinic, P21/c	Melting point: 422 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4920 (15) Å	Cell parameters from 6007 reflections
b = 10.9607 (17) Å	θ = 2.3–28.3°
c = 15.050 (2) Å	µ = 0.24 mm−1
β = 99.758 (2)°	T = 173 K
V = 1543.1 (4) Å3	Block, colorless
Z = 4	0.43 × 0.25 × 0.19 mm

Bruker SMART 1K diffractometer	3719 independent reflections
Radiation source: fine-focus sealed tube	3297 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.905, Tmax = 0.956	k = −14→14
13430 measured reflections	l = −20→19

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) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.6338P] where P = (Fo2 + 2Fc2)/3
3719 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.81488 (4)	0.52594 (3)	0.28570 (2)	0.01595 (12)
O4	0.30241 (11)	0.50771 (10)	0.17813 (7)	0.0183 (2)
C1	0.83777 (15)	0.56206 (13)	0.17521 (10)	0.0157 (3)
O1	0.46409 (11)	0.60454 (10)	0.07788 (7)	0.0187 (2)
C2	0.97337 (16)	0.58108 (14)	0.15447 (10)	0.0188 (3)
H2	1.0565	0.5666	0.1981	0.023*
O5	0.40378 (11)	0.40446 (10)	0.30203 (7)	0.0177 (2)
C3	0.98459 (17)	0.62175 (14)	0.06835 (11)	0.0209 (3)
H3	1.0763	0.6351	0.0529	0.025*
O2	0.93353 (11)	0.45544 (11)	0.33020 (7)	0.0220 (3)
C4	0.86248 (17)	0.64307 (14)	0.00470 (10)	0.0204 (3)
H4	0.8715	0.6726	−0.0534	0.025*
O3	0.77720 (12)	0.63674 (10)	0.32661 (7)	0.0211 (2)
C5	0.72758 (16)	0.62151 (13)	0.02546 (10)	0.0176 (3)
H5	0.6448	0.6353	−0.0185	0.021*
N1	0.67339 (13)	0.43784 (11)	0.26853 (8)	0.0156 (3)
C6	0.71401 (15)	0.57923 (13)	0.11162 (10)	0.0152 (3)
C7	0.57231 (15)	0.55402 (13)	0.13462 (10)	0.0153 (3)
C8	0.55400 (15)	0.48728 (13)	0.20867 (10)	0.0150 (3)
C9	0.40936 (16)	0.46801 (13)	0.22778 (10)	0.0154 (3)
C11	0.69172 (16)	0.30226 (13)	0.26997 (10)	0.0169 (3)
H11A	0.6125	0.2651	0.2957	0.020*
H11B	0.7821	0.2818	0.3105	0.020*
C12	0.69472 (16)	0.24606 (13)	0.17890 (10)	0.0165 (3)
C13	0.56919 (17)	0.20116 (14)	0.12780 (11)	0.0212 (3)
H13	0.4816	0.2081	0.1500	0.025*
C14	0.5710 (2)	0.14639 (16)	0.04476 (12)	0.0307 (4)
H14	0.4848	0.1168	0.0101	0.037*
C15	0.6992 (2)	0.13497 (16)	0.01245 (12)	0.0340 (4)
H15	0.7007	0.0970	−0.0441	0.041*
C16	0.8247 (2)	0.17886 (16)	0.06271 (12)	0.0308 (4)
H16	0.9123	0.1703	0.0408	0.037*
C10	0.26012 (16)	0.38959 (15)	0.32309 (11)	0.0199 (3)
H10A	0.2184	0.4700	0.3303	0.030*
H10B	0.2652	0.3431	0.3792	0.030*
H10C	0.2003	0.3456	0.2739	0.030*
C17	0.82300 (18)	0.23540 (14)	0.14515 (11)	0.0225 (3)
H17	0.9091	0.2669	0.1787	0.027*
H1O	0.381 (3)	0.583 (2)	0.0989 (14)	0.034*

	U11	U22	U33	U12	U13	U23
S1	0.01167 (19)	0.0206 (2)	0.0152 (2)	−0.00077 (12)	0.00123 (13)	0.00070 (13)
O4	0.0117 (5)	0.0229 (5)	0.0201 (5)	0.0010 (4)	0.0018 (4)	−0.0008 (4)
C1	0.0153 (7)	0.0163 (7)	0.0155 (7)	0.0000 (5)	0.0030 (5)	0.0000 (5)
O1	0.0134 (5)	0.0227 (6)	0.0193 (5)	0.0025 (4)	0.0007 (4)	0.0035 (4)
C2	0.0148 (7)	0.0206 (7)	0.0210 (7)	0.0001 (5)	0.0030 (5)	0.0004 (6)
O5	0.0134 (5)	0.0198 (5)	0.0207 (5)	0.0004 (4)	0.0051 (4)	0.0023 (4)
C3	0.0174 (7)	0.0230 (8)	0.0240 (8)	−0.0024 (6)	0.0085 (6)	−0.0010 (6)
O2	0.0121 (5)	0.0308 (6)	0.0219 (6)	0.0010 (4)	−0.0002 (4)	0.0060 (4)
C4	0.0236 (8)	0.0207 (7)	0.0181 (7)	−0.0009 (6)	0.0066 (6)	0.0007 (6)
O3	0.0199 (5)	0.0238 (6)	0.0196 (5)	−0.0038 (4)	0.0033 (4)	−0.0037 (4)
C5	0.0175 (7)	0.0179 (7)	0.0169 (7)	0.0004 (5)	0.0015 (5)	−0.0009 (5)
N1	0.0122 (6)	0.0165 (6)	0.0178 (6)	0.0004 (4)	0.0018 (5)	0.0015 (5)
C6	0.0147 (7)	0.0142 (7)	0.0169 (7)	0.0005 (5)	0.0030 (5)	−0.0012 (5)
C7	0.0136 (7)	0.0152 (6)	0.0169 (7)	0.0013 (5)	0.0018 (5)	−0.0021 (5)
C8	0.0119 (7)	0.0149 (7)	0.0176 (7)	0.0016 (5)	0.0010 (5)	−0.0008 (5)
C9	0.0153 (7)	0.0137 (7)	0.0172 (7)	−0.0004 (5)	0.0028 (5)	−0.0028 (5)
C11	0.0161 (7)	0.0174 (7)	0.0173 (7)	0.0025 (5)	0.0028 (5)	0.0033 (5)
C12	0.0178 (7)	0.0134 (7)	0.0186 (7)	0.0017 (5)	0.0039 (5)	0.0031 (5)
C13	0.0195 (7)	0.0174 (7)	0.0250 (8)	0.0022 (6)	−0.0012 (6)	0.0029 (6)
C14	0.0420 (10)	0.0189 (8)	0.0259 (8)	0.0036 (7)	−0.0092 (7)	0.0020 (6)
C15	0.0651 (13)	0.0198 (8)	0.0181 (8)	0.0076 (8)	0.0103 (8)	0.0023 (6)
C16	0.0448 (11)	0.0209 (8)	0.0330 (9)	0.0054 (7)	0.0244 (8)	0.0064 (7)
C10	0.0140 (7)	0.0219 (8)	0.0249 (8)	−0.0017 (5)	0.0066 (6)	0.0006 (6)
C17	0.0228 (8)	0.0185 (7)	0.0286 (8)	−0.0006 (6)	0.0110 (6)	0.0033 (6)

S1—O3	1.4341 (12)	C6—C7	1.471 (2)
S1—O2	1.4347 (11)	C7—C8	1.369 (2)
S1—N1	1.6387 (13)	C8—C9	1.465 (2)
S1—C1	1.7583 (15)	C11—C12	1.507 (2)
O4—C9	1.2333 (18)	C11—H11A	0.9900
C1—C2	1.391 (2)	C11—H11B	0.9900
C1—C6	1.397 (2)	C12—C13	1.394 (2)
O1—C7	1.3393 (17)	C12—C17	1.401 (2)
O1—H1O	0.93 (2)	C13—C14	1.389 (2)
C2—C3	1.392 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.391 (3)
O5—C9	1.3254 (18)	C14—H14	0.9500
O5—C10	1.4606 (17)	C15—C16	1.384 (3)
C3—C4	1.393 (2)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.389 (2)
C4—C5	1.389 (2)	C16—H16	0.9500
C4—H4	0.9500	C10—H10A	0.9800
C5—C6	1.403 (2)	C10—H10B	0.9800
C5—H5	0.9500	C10—H10C	0.9800
N1—C8	1.4295 (18)	C17—H17	0.9500
N1—C11	1.4959 (19)
O3—S1—O2	119.27 (7)	N1—C8—C9	119.40 (13)
O3—S1—N1	108.02 (6)	O4—C9—O5	123.35 (13)
O2—S1—N1	108.29 (7)	O4—C9—C8	122.20 (13)
O3—S1—C1	107.16 (7)	O5—C9—C8	114.46 (13)
O2—S1—C1	110.47 (7)	N1—C11—C12	114.38 (12)
N1—S1—C1	102.29 (7)	N1—C11—H11A	108.7
C2—C1—C6	121.94 (13)	C12—C11—H11A	108.7
C2—C1—S1	120.90 (11)	N1—C11—H11B	108.7
C6—C1—S1	117.00 (11)	C12—C11—H11B	108.7
C7—O1—H1O	106.1 (14)	H11A—C11—H11B	107.6
C1—C2—C3	118.48 (14)	C13—C12—C17	118.98 (14)
C1—C2—H2	120.8	C13—C12—C11	119.99 (13)
C3—C2—H2	120.8	C17—C12—C11	121.01 (14)
C9—O5—C10	114.45 (11)	C14—C13—C12	120.60 (15)
C2—C3—C4	120.55 (14)	C14—C13—H13	119.7
C2—C3—H3	119.7	C12—C13—H13	119.7
C4—C3—H3	119.7	C13—C14—C15	119.92 (17)
C5—C4—C3	120.55 (14)	C13—C14—H14	120.0
C5—C4—H4	119.7	C15—C14—H14	120.0
C3—C4—H4	119.7	C16—C15—C14	120.03 (16)
C4—C5—C6	119.77 (14)	C16—C15—H15	120.0
C4—C5—H5	120.1	C14—C15—H15	120.0
C6—C5—H5	120.1	C15—C16—C17	120.24 (16)
C8—N1—C11	117.62 (11)	C15—C16—H16	119.9
C8—N1—S1	114.65 (10)	C17—C16—H16	119.9
C11—N1—S1	119.53 (10)	O5—C10—H10A	109.5
C1—C6—C5	118.65 (13)	O5—C10—H10B	109.5
C1—C6—C7	120.66 (13)	H10A—C10—H10B	109.5
C5—C6—C7	120.68 (13)	O5—C10—H10C	109.5
O1—C7—C8	123.41 (13)	H10A—C10—H10C	109.5
O1—C7—C6	113.92 (12)	H10B—C10—H10C	109.5
C8—C7—C6	122.65 (13)	C16—C17—C12	120.22 (16)
C7—C8—N1	121.28 (13)	C16—C17—H17	119.9
C7—C8—C9	119.31 (13)	C12—C17—H17	119.9
O3—S1—C1—C2	98.81 (13)	O1—C7—C8—N1	−178.36 (13)
O2—S1—C1—C2	−32.60 (15)	C6—C7—C8—N1	0.0 (2)
N1—S1—C1—C2	−147.69 (13)	O1—C7—C8—C9	0.5 (2)
O3—S1—C1—C6	−76.69 (13)	C6—C7—C8—C9	178.95 (13)
O2—S1—C1—C6	151.90 (11)	C11—N1—C8—C7	−111.02 (15)
N1—S1—C1—C6	36.80 (13)	S1—N1—C8—C7	37.42 (17)
C6—C1—C2—C3	1.9 (2)	C11—N1—C8—C9	70.08 (17)
S1—C1—C2—C3	−173.42 (11)	S1—N1—C8—C9	−141.49 (11)
C1—C2—C3—C4	0.1 (2)	C10—O5—C9—O4	−2.7 (2)
C2—C3—C4—C5	−1.4 (2)	C10—O5—C9—C8	177.58 (12)
C3—C4—C5—C6	0.7 (2)	C7—C8—C9—O4	1.7 (2)
O3—S1—N1—C8	61.81 (11)	N1—C8—C9—O4	−179.41 (13)
O2—S1—N1—C8	−167.73 (10)	C7—C8—C9—O5	−178.62 (13)
C1—S1—N1—C8	−51.05 (11)	N1—C8—C9—O5	0.31 (19)
O3—S1—N1—C11	−150.40 (10)	C8—N1—C11—C12	54.00 (17)
O2—S1—N1—C11	−19.94 (13)	S1—N1—C11—C12	−92.85 (14)
C1—S1—N1—C11	96.74 (11)	N1—C11—C12—C13	−93.63 (16)
C2—C1—C6—C5	−2.5 (2)	N1—C11—C12—C17	87.87 (17)
S1—C1—C6—C5	172.92 (11)	C17—C12—C13—C14	0.1 (2)
C2—C1—C6—C7	177.73 (14)	C11—C12—C13—C14	−178.38 (14)
S1—C1—C6—C7	−6.82 (19)	C12—C13—C14—C15	0.6 (2)
C4—C5—C6—C1	1.2 (2)	C13—C14—C15—C16	−0.4 (3)
C4—C5—C6—C7	−179.06 (14)	C14—C15—C16—C17	−0.6 (3)
C1—C6—C7—O1	162.79 (13)	C15—C16—C17—C12	1.4 (2)
C5—C6—C7—O1	−16.94 (19)	C13—C12—C17—C16	−1.2 (2)
C1—C6—C7—C8	−15.8 (2)	C11—C12—C17—C16	177.36 (14)
C5—C6—C7—C8	164.52 (14)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.95	2.49	3.1861 (19)	130
O1—H1O···O4	0.93 (2)	1.72 (2)	2.5580 (15)	149 (2)
C10—H10B···Cg1ii	0.80	2.94	3.6391 (18)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.95	2.49	3.1861 (19)	130
O1—H1O⋯O4	0.93 (2)	1.72 (2)	2.5580 (15)	149 (2)
C10—H10B⋯Cg1ii	0.80	2.94	3.6391 (18)	130

Symmetry codes: (i) ; (ii) .