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

In the title compound, C(18)H(17)NO(5)S, the thia-zine ring adopts a half-chair conformation and the dihedral angle between the aromatic rings is 79.41 (6)°. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions resulting in infinite sheets along the b and c axes.

Related literature

For related structures, see: Arshad et al. (2011a ▶); Ahmad et al. (2010 ▶); Khalid et al. (2010 ▶). For further synthetic details, see: Arshad et al. (2011b ▶). For graph-set notation, see: Bernstein, et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H17NO5S

M = 359.39

Monoclinic,

a = 9.018 (2) Å

b = 19.026 (4) Å

c = 10.193 (2) Å

β = 106.441 (3)°

V = 1677.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.37 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.922, T max = 0.982

19773 measured reflections

4066 independent reflections

2735 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.116

S = 1.01

4066 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.44 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 ▶); 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/S160053681104966X/hb6520sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104966X/hb6520Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104966X/hb6520Isup3.cml

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

C18H17NO5S	F(000) = 752
Mr = 359.39	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2258 reflections
a = 9.018 (2) Å	θ = 2.3–22.9°
b = 19.026 (4) Å	µ = 0.22 mm−1
c = 10.193 (2) Å	T = 100 K
β = 106.441 (3)°	Block, colorless
V = 1677.3 (7) Å3	0.37 × 0.23 × 0.08 mm
Z = 4

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector	4066 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
graphite	Rint = 0.094
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.922, Tmax = 0.982	k = −25→25
19773 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2677P] where P = (Fo2 + 2Fc2)/3
4066 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.44 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	0.29319 (6)	0.07784 (3)	0.51969 (5)	0.01673 (14)
O3	0.30860 (16)	0.00885 (8)	0.46983 (15)	0.0214 (4)
O5	−0.10038 (17)	0.12689 (8)	0.61803 (15)	0.0231 (4)
O1	0.13070 (18)	0.28877 (8)	0.48807 (17)	0.0251 (4)
O4	−0.07394 (18)	0.24350 (9)	0.60086 (17)	0.0276 (4)
N1	0.10892 (18)	0.09548 (9)	0.48635 (17)	0.0154 (4)
O2	0.36535 (16)	0.09408 (8)	0.65995 (14)	0.0227 (4)
C1	0.3551 (2)	0.14133 (12)	0.4212 (2)	0.0170 (5)
C7	0.1578 (2)	0.22064 (12)	0.4703 (2)	0.0182 (5)
C8	0.0779 (2)	0.16750 (11)	0.5085 (2)	0.0177 (5)
C5	0.3377 (2)	0.26007 (12)	0.3379 (2)	0.0220 (5)
H5	0.2933	0.3057	0.3300	0.026*
C9	−0.0383 (2)	0.18329 (12)	0.5789 (2)	0.0207 (5)
C6	0.2849 (2)	0.20757 (11)	0.4087 (2)	0.0180 (5)
C2	0.4731 (2)	0.12640 (12)	0.3629 (2)	0.0214 (5)
H2	0.5193	0.0811	0.3720	0.026*
C17	−0.3703 (2)	0.07609 (13)	−0.0561 (2)	0.0235 (5)
H17	−0.4494	0.1074	−0.1035	0.028*
C18	−0.2463 (2)	0.10137 (12)	0.0471 (2)	0.0209 (5)
H18	−0.2404	0.1500	0.0694	0.025*
C11	−0.0022 (2)	0.05922 (11)	0.3704 (2)	0.0170 (5)
H11A	−0.1082	0.0670	0.3773	0.020*
H11B	0.0185	0.0081	0.3786	0.020*
C3	0.5220 (3)	0.17932 (13)	0.2911 (2)	0.0270 (6)
H3	0.6021	0.1701	0.2496	0.032*
C15	−0.2653 (3)	−0.03981 (13)	−0.0196 (2)	0.0247 (5)
H15	−0.2717	−0.0884	−0.0421	0.030*
C4	0.4549 (3)	0.24549 (13)	0.2793 (2)	0.0257 (5)
H4	0.4901	0.2813	0.2303	0.031*
C12	0.0052 (2)	0.08358 (12)	0.2302 (2)	0.0225 (5)
H12A	0.0047	0.1356	0.2273	0.027*
H12B	0.1029	0.0671	0.2146	0.027*
C14	−0.1420 (3)	−0.01493 (13)	0.0835 (2)	0.0249 (5)
H14	−0.0642	−0.0467	0.1314	0.030*
C13	−0.1300 (2)	0.05577 (12)	0.1181 (2)	0.0196 (5)
C16	−0.3799 (3)	0.00572 (13)	−0.0903 (2)	0.0239 (5)
H16	−0.4643	−0.0113	−0.1619	0.029*
C10	−0.2150 (3)	0.13972 (14)	0.6903 (3)	0.0314 (6)
H10A	−0.2992	0.1682	0.6329	0.047*
H10B	−0.1669	0.1649	0.7756	0.047*
H10C	−0.2564	0.0948	0.7111	0.047*
H1	0.057 (3)	0.2878 (14)	0.534 (3)	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0166 (2)	0.0155 (3)	0.0161 (3)	0.0009 (2)	0.0015 (2)	0.0007 (2)
O3	0.0204 (7)	0.0153 (8)	0.0269 (8)	0.0031 (6)	0.0042 (7)	−0.0005 (7)
O5	0.0245 (8)	0.0217 (9)	0.0271 (9)	−0.0026 (7)	0.0138 (7)	−0.0042 (7)
O1	0.0285 (9)	0.0147 (9)	0.0347 (10)	0.0009 (7)	0.0130 (8)	−0.0018 (7)
O4	0.0287 (9)	0.0193 (9)	0.0370 (10)	0.0027 (7)	0.0127 (8)	−0.0047 (7)
N1	0.0155 (8)	0.0138 (10)	0.0158 (9)	0.0005 (7)	0.0025 (7)	0.0009 (7)
O2	0.0237 (8)	0.0235 (9)	0.0171 (8)	−0.0012 (7)	−0.0005 (7)	0.0002 (7)
C1	0.0154 (9)	0.0186 (12)	0.0136 (10)	−0.0025 (9)	−0.0016 (8)	−0.0005 (9)
C7	0.0188 (10)	0.0161 (12)	0.0172 (11)	0.0004 (9)	0.0009 (9)	−0.0006 (9)
C8	0.0190 (10)	0.0174 (12)	0.0152 (10)	0.0025 (9)	0.0026 (9)	−0.0016 (9)
C5	0.0237 (11)	0.0182 (12)	0.0211 (12)	−0.0006 (9)	0.0018 (10)	0.0023 (9)
C9	0.0182 (10)	0.0210 (13)	0.0204 (11)	−0.0007 (9)	0.0015 (9)	−0.0017 (10)
C6	0.0175 (10)	0.0179 (12)	0.0158 (11)	−0.0035 (9)	0.0002 (9)	−0.0018 (9)
C2	0.0190 (10)	0.0219 (13)	0.0209 (11)	−0.0003 (9)	0.0020 (9)	−0.0029 (9)
C17	0.0217 (11)	0.0287 (14)	0.0186 (11)	0.0019 (10)	0.0035 (9)	0.0039 (10)
C18	0.0259 (11)	0.0193 (12)	0.0177 (11)	−0.0029 (10)	0.0067 (10)	−0.0004 (9)
C11	0.0162 (10)	0.0177 (12)	0.0160 (10)	−0.0016 (8)	0.0030 (9)	−0.0007 (8)
C3	0.0223 (11)	0.0353 (16)	0.0248 (12)	−0.0029 (10)	0.0089 (10)	−0.0019 (11)
C15	0.0301 (12)	0.0205 (13)	0.0243 (12)	0.0002 (10)	0.0089 (10)	−0.0030 (10)
C4	0.0256 (12)	0.0267 (14)	0.0245 (13)	−0.0067 (10)	0.0066 (10)	0.0046 (10)
C12	0.0227 (10)	0.0248 (13)	0.0182 (11)	−0.0036 (10)	0.0030 (9)	0.0031 (10)
C14	0.0243 (11)	0.0253 (14)	0.0234 (12)	0.0041 (10)	0.0040 (10)	0.0020 (10)
C13	0.0208 (11)	0.0247 (13)	0.0136 (10)	−0.0026 (9)	0.0053 (9)	0.0001 (9)
C16	0.0237 (11)	0.0287 (14)	0.0170 (11)	−0.0045 (10)	0.0017 (9)	−0.0036 (10)
C10	0.0303 (12)	0.0354 (16)	0.0360 (14)	−0.0049 (11)	0.0215 (12)	−0.0120 (12)

S1—O2	1.4270 (15)	C17—C18	1.386 (3)
S1—O3	1.4285 (16)	C17—H17	0.9500
S1—N1	1.6339 (17)	C18—C13	1.395 (3)
S1—C1	1.760 (2)	C18—H18	0.9500
O5—C9	1.323 (3)	C11—C12	1.521 (3)
O5—C10	1.449 (3)	C11—H11A	0.9900
O1—C7	1.341 (3)	C11—H11B	0.9900
O1—H1	0.92 (3)	C3—C4	1.387 (3)
O4—C9	1.227 (3)	C3—H3	0.9500
N1—C8	1.429 (3)	C15—C14	1.379 (3)
N1—C11	1.485 (3)	C15—C16	1.384 (3)
C1—C2	1.387 (3)	C15—H15	0.9500
C1—C6	1.400 (3)	C4—H4	0.9500
C7—C8	1.361 (3)	C12—C13	1.511 (3)
C7—C6	1.475 (3)	C12—H12A	0.9900
C8—C9	1.459 (3)	C12—H12B	0.9900
C5—C4	1.382 (3)	C14—C13	1.387 (3)
C5—C6	1.392 (3)	C14—H14	0.9500
C5—H5	0.9500	C16—H16	0.9500
C2—C3	1.389 (3)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C17—C16	1.380 (3)	C10—H10C	0.9800
O2—S1—O3	119.52 (9)	C13—C18—H18	119.9
O2—S1—N1	108.21 (9)	N1—C11—C12	114.02 (17)
O3—S1—N1	108.08 (9)	N1—C11—H11A	108.7
O2—S1—C1	107.13 (9)	C12—C11—H11A	108.7
O3—S1—C1	110.45 (10)	N1—C11—H11B	108.7
N1—S1—C1	102.04 (9)	C12—C11—H11B	108.7
C9—O5—C10	116.10 (18)	H11A—C11—H11B	107.6
C7—O1—H1	103.7 (17)	C4—C3—C2	120.5 (2)
C8—N1—C11	116.93 (16)	C4—C3—H3	119.7
C8—N1—S1	113.41 (13)	C2—C3—H3	119.7
C11—N1—S1	119.16 (14)	C14—C15—C16	120.3 (2)
C2—C1—C6	121.8 (2)	C14—C15—H15	119.9
C2—C1—S1	120.63 (17)	C16—C15—H15	119.9
C6—C1—S1	117.50 (16)	C5—C4—C3	120.9 (2)
O1—C7—C8	123.2 (2)	C5—C4—H4	119.6
O1—C7—C6	114.46 (19)	C3—C4—H4	119.6
C8—C7—C6	122.3 (2)	C13—C12—C11	111.30 (18)
C7—C8—N1	121.54 (19)	C13—C12—H12A	109.4
C7—C8—C9	120.0 (2)	C11—C12—H12A	109.4
N1—C8—C9	118.38 (19)	C13—C12—H12B	109.4
C4—C5—C6	119.7 (2)	C11—C12—H12B	109.4
C4—C5—H5	120.1	H12A—C12—H12B	108.0
C6—C5—H5	120.1	C15—C14—C13	121.0 (2)
O4—C9—O5	123.2 (2)	C15—C14—H14	119.5
O4—C9—C8	122.9 (2)	C13—C14—H14	119.5
O5—C9—C8	113.92 (19)	C14—C13—C18	118.5 (2)
C5—C6—C1	118.8 (2)	C14—C13—C12	121.3 (2)
C5—C6—C7	121.3 (2)	C18—C13—C12	120.1 (2)
C1—C6—C7	119.92 (19)	C17—C16—C15	119.4 (2)
C1—C2—C3	118.3 (2)	C17—C16—H16	120.3
C1—C2—H2	120.8	C15—C16—H16	120.3
C3—C2—H2	120.8	O5—C10—H10A	109.5
C16—C17—C18	120.5 (2)	O5—C10—H10B	109.5
C16—C17—H17	119.8	H10A—C10—H10B	109.5
C18—C17—H17	119.8	O5—C10—H10C	109.5
C17—C18—C13	120.3 (2)	H10A—C10—H10C	109.5
C17—C18—H18	119.9	H10B—C10—H10C	109.5
O2—S1—N1—C8	59.99 (16)	C4—C5—C6—C7	−178.7 (2)
O3—S1—N1—C8	−169.24 (14)	C2—C1—C6—C5	−1.3 (3)
C1—S1—N1—C8	−52.79 (16)	S1—C1—C6—C5	176.40 (16)
O2—S1—N1—C11	−156.23 (15)	C2—C1—C6—C7	178.87 (19)
O3—S1—N1—C11	−25.46 (18)	S1—C1—C6—C7	−3.5 (3)
C1—S1—N1—C11	90.99 (17)	O1—C7—C6—C5	−18.7 (3)
O2—S1—C1—C2	99.50 (18)	C8—C7—C6—C5	162.8 (2)
O3—S1—C1—C2	−32.19 (19)	O1—C7—C6—C1	161.14 (18)
N1—S1—C1—C2	−146.92 (17)	C8—C7—C6—C1	−17.4 (3)
O2—S1—C1—C6	−78.19 (17)	C6—C1—C2—C3	0.3 (3)
O3—S1—C1—C6	150.11 (15)	S1—C1—C2—C3	−177.31 (16)
N1—S1—C1—C6	35.39 (18)	C16—C17—C18—C13	−0.4 (3)
O1—C7—C8—N1	179.24 (18)	C8—N1—C11—C12	71.0 (2)
C6—C7—C8—N1	−2.4 (3)	S1—N1—C11—C12	−71.6 (2)
O1—C7—C8—C9	−3.3 (3)	C1—C2—C3—C4	0.5 (3)
C6—C7—C8—C9	175.06 (18)	C6—C5—C4—C3	−0.6 (3)
C11—N1—C8—C7	−103.1 (2)	C2—C3—C4—C5	−0.4 (3)
S1—N1—C8—C7	41.5 (2)	N1—C11—C12—C13	−168.72 (18)
C11—N1—C8—C9	79.4 (2)	C16—C15—C14—C13	−0.1 (3)
S1—N1—C8—C9	−136.00 (16)	C15—C14—C13—C18	0.5 (3)
C10—O5—C9—O4	−0.2 (3)	C15—C14—C13—C12	−179.6 (2)
C10—O5—C9—C8	179.15 (18)	C17—C18—C13—C14	−0.2 (3)
C7—C8—C9—O4	3.4 (3)	C17—C18—C13—C12	179.85 (19)
N1—C8—C9—O4	−179.04 (19)	C11—C12—C13—C14	−70.4 (3)
C7—C8—C9—O5	−175.93 (18)	C11—C12—C13—C18	109.5 (2)
N1—C8—C9—O5	1.6 (3)	C18—C17—C16—C15	0.8 (3)
C4—C5—C6—C1	1.4 (3)	C14—C15—C16—C17	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.95	2.55	3.391 (3)	147
C17—H17···O2ii	0.95	2.53	3.205 (3)	128
C18—H18···O4iii	0.95	2.49	3.308 (3)	145
O1—H1···O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.95	2.55	3.391 (3)	147
C17—H17⋯O2ii	0.95	2.53	3.205 (3)	128
C18—H18⋯O4iii	0.95	2.49	3.308 (3)	145
O1—H1⋯O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)

Symmetry codes: (i) ; (ii) ; (iii) .