3-[Hy-droxy(3-meth-oxy-phen-yl)methyl-idene]-2-(2-oxo-2-phenyl-eth-yl)-3,4-dihydro-2H-1λ(6),2-benzothia-zine-1,1,4-trione.

In the title mol-ecule, C(24)H(19)NO(6)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia-zine unit and the meth-oxy-phenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenyl-ethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The mol-ecular structure is consolidated by intra-molecular O-H⋯O and C-H⋯N inter-actions, and the crystal packing is stabilized by weak C-H⋯O hydrogen bonds.

Related literature

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ▶). For the biological activity of 1,2-benzothia­zine derivatives, see: Lombardino & Wiseman (1972 ▶); Gupta et al. (1993 ▶, 2002 ▶); Zia-ur-Rehman et al. (2006 ▶); Ahmad et al. (2010 ▶). For a related structure, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C24H19NO6S

M = 449.46

Orthorhombic,

a = 17.9615 (5) Å

b = 11.2633 (3) Å

c = 19.5904 (6) Å

V = 3963.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.14 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.971, T max = 0.984

8340 measured reflections

4543 independent reflections

3198 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.133

S = 1.10

4543 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.49 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009002/pk2393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009002/pk2393Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009002/pk2393Isup3.cml

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

C24H19NO6S	F(000) = 1872
Mr = 449.46	Dx = 1.507 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5006 reflections
a = 17.9615 (5) Å	θ = 1.0–27.5°
b = 11.2633 (3) Å	µ = 0.21 mm−1
c = 19.5904 (6) Å	T = 173 K
V = 3963.3 (2) Å3	Prism, yellow
Z = 8	0.14 × 0.10 × 0.08 mm

Nonius KappaCCD diffractometer	4543 independent reflections
Radiation source: fine-focus sealed tube	3198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω and φ scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −23→23
Tmin = 0.971, Tmax = 0.984	k = −14→14
8340 measured reflections	l = −25→25

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + 10.1913P] where P = (Fo2 + 2Fc2)/3
4543 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.36 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	0.43448 (4)	0.23066 (7)	0.49448 (4)	0.02772 (19)
O1	0.42975 (13)	0.1891 (2)	0.42537 (11)	0.0321 (5)
O2	0.50593 (12)	0.2608 (2)	0.52165 (13)	0.0380 (6)
O3	0.19812 (12)	0.2130 (2)	0.52567 (12)	0.0334 (6)
O4	0.18789 (12)	0.3846 (2)	0.44712 (12)	0.0311 (5)
H4O	0.1754	0.3308	0.4745	0.047*
O5	0.20407 (13)	0.7401 (2)	0.31274 (12)	0.0350 (6)
O6	0.35370 (14)	0.3374 (2)	0.64057 (12)	0.0395 (6)
N1	0.38071 (14)	0.3469 (2)	0.50267 (13)	0.0248 (6)
C1	0.39090 (18)	0.1240 (3)	0.54646 (16)	0.0259 (7)
C2	0.4322 (2)	0.0323 (3)	0.57373 (17)	0.0358 (8)
H2	0.4841	0.0268	0.5650	0.043*
C3	0.3971 (2)	−0.0515 (3)	0.6140 (2)	0.0421 (9)
H3	0.4248	−0.1157	0.6325	0.051*
C4	0.3218 (2)	−0.0425 (3)	0.62739 (18)	0.0399 (9)
H4	0.2980	−0.0998	0.6555	0.048*
C5	0.2809 (2)	0.0502 (3)	0.59989 (17)	0.0325 (8)
H5	0.2292	0.0561	0.6096	0.039*
C6	0.31417 (18)	0.1342 (3)	0.55844 (16)	0.0264 (7)
C7	0.26845 (17)	0.2284 (3)	0.52620 (16)	0.0261 (7)
C8	0.30240 (16)	0.3262 (3)	0.49250 (16)	0.0231 (6)
C9	0.26011 (18)	0.3991 (3)	0.44929 (16)	0.0262 (7)
C10	0.28801 (17)	0.4937 (3)	0.40321 (16)	0.0256 (7)
C11	0.23700 (17)	0.5772 (3)	0.37964 (15)	0.0254 (7)
H11	0.1871	0.5756	0.3958	0.030*
C12	0.25855 (18)	0.6626 (3)	0.33282 (16)	0.0271 (7)
C13	0.33096 (19)	0.6660 (3)	0.30894 (17)	0.0331 (8)
H13	0.3459	0.7251	0.2772	0.040*
C14	0.3811 (2)	0.5824 (3)	0.33196 (19)	0.0386 (9)
H14	0.4307	0.5839	0.3152	0.046*
C15	0.36098 (19)	0.4962 (3)	0.37892 (18)	0.0343 (8)
H15	0.3964	0.4397	0.3944	0.041*
C16	0.2218 (2)	0.8229 (3)	0.25964 (18)	0.0384 (9)
H16A	0.1770	0.8679	0.2473	0.046*
H16B	0.2400	0.7797	0.2195	0.046*
H16C	0.2604	0.8776	0.2757	0.046*
C17	0.40483 (18)	0.4447 (3)	0.54746 (16)	0.0280 (7)
H17A	0.3794	0.5185	0.5330	0.034*
H17B	0.4590	0.4568	0.5414	0.034*
C18	0.38901 (17)	0.4240 (3)	0.62268 (17)	0.0269 (7)
C19	0.41875 (17)	0.5095 (3)	0.67386 (17)	0.0258 (7)
C20	0.45909 (18)	0.6100 (3)	0.65584 (17)	0.0286 (7)
H20	0.4641	0.6311	0.6091	0.034*
C21	0.49201 (19)	0.6796 (3)	0.70580 (18)	0.0334 (8)
H21	0.5206	0.7471	0.6932	0.040*
C22	0.4834 (2)	0.6511 (3)	0.77347 (18)	0.0359 (8)
H22	0.5068	0.6981	0.8075	0.043*
C23	0.4404 (2)	0.5534 (3)	0.79248 (18)	0.0362 (8)
H23	0.4326	0.5359	0.8394	0.043*
C24	0.40910 (18)	0.4825 (3)	0.74264 (17)	0.0299 (7)
H24	0.3808	0.4148	0.7554	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0271 (4)	0.0275 (4)	0.0285 (4)	0.0017 (3)	−0.0005 (3)	0.0012 (3)
O1	0.0348 (12)	0.0336 (12)	0.0277 (12)	0.0028 (11)	0.0035 (10)	−0.0028 (10)
O2	0.0287 (12)	0.0381 (13)	0.0473 (15)	0.0006 (11)	−0.0057 (11)	0.0028 (12)
O3	0.0288 (12)	0.0310 (12)	0.0403 (14)	−0.0025 (10)	0.0033 (10)	0.0038 (11)
O4	0.0265 (12)	0.0304 (12)	0.0364 (14)	−0.0029 (10)	0.0013 (10)	0.0082 (11)
O5	0.0405 (13)	0.0301 (12)	0.0344 (13)	0.0050 (11)	−0.0015 (11)	0.0086 (11)
O6	0.0571 (16)	0.0347 (13)	0.0266 (13)	−0.0163 (12)	0.0024 (12)	0.0024 (11)
N1	0.0243 (13)	0.0251 (13)	0.0251 (14)	0.0001 (11)	−0.0001 (11)	0.0012 (11)
C1	0.0338 (17)	0.0226 (15)	0.0215 (16)	−0.0026 (13)	−0.0043 (14)	0.0000 (13)
C2	0.044 (2)	0.0330 (18)	0.0306 (19)	0.0050 (17)	−0.0093 (16)	−0.0002 (15)
C3	0.055 (2)	0.0300 (19)	0.041 (2)	0.0033 (18)	−0.0148 (19)	0.0066 (17)
C4	0.060 (2)	0.0301 (18)	0.0298 (19)	−0.0086 (18)	−0.0089 (18)	0.0080 (16)
C5	0.0401 (19)	0.0301 (17)	0.0272 (18)	−0.0087 (15)	−0.0016 (15)	−0.0010 (14)
C6	0.0362 (18)	0.0205 (15)	0.0225 (16)	−0.0017 (13)	−0.0057 (14)	−0.0018 (13)
C7	0.0269 (16)	0.0242 (15)	0.0271 (17)	−0.0025 (13)	0.0007 (13)	−0.0045 (13)
C8	0.0244 (15)	0.0232 (14)	0.0217 (16)	−0.0002 (12)	0.0008 (13)	−0.0006 (13)
C9	0.0290 (17)	0.0252 (15)	0.0245 (16)	−0.0010 (13)	0.0012 (13)	−0.0056 (13)
C10	0.0298 (17)	0.0243 (15)	0.0226 (16)	−0.0006 (13)	−0.0020 (13)	−0.0016 (13)
C11	0.0271 (16)	0.0255 (15)	0.0234 (16)	−0.0030 (13)	−0.0001 (13)	−0.0045 (13)
C12	0.0315 (17)	0.0230 (15)	0.0268 (16)	0.0015 (14)	−0.0067 (14)	−0.0028 (13)
C13	0.0372 (19)	0.0336 (18)	0.0284 (18)	−0.0043 (16)	0.0039 (15)	0.0054 (15)
C14	0.0329 (18)	0.042 (2)	0.041 (2)	0.0014 (16)	0.0088 (17)	0.0093 (17)
C15	0.0319 (18)	0.0355 (18)	0.036 (2)	0.0035 (15)	0.0008 (15)	0.0071 (16)
C16	0.055 (2)	0.0279 (17)	0.032 (2)	0.0025 (17)	−0.0058 (17)	0.0035 (15)
C17	0.0265 (16)	0.0281 (16)	0.0294 (18)	−0.0049 (14)	0.0008 (14)	0.0001 (14)
C18	0.0262 (16)	0.0272 (16)	0.0274 (17)	−0.0004 (13)	0.0020 (14)	0.0033 (14)
C19	0.0216 (15)	0.0253 (15)	0.0305 (18)	0.0028 (13)	−0.0022 (13)	−0.0005 (13)
C20	0.0309 (17)	0.0276 (16)	0.0271 (17)	0.0010 (14)	0.0016 (14)	0.0027 (14)
C21	0.0349 (18)	0.0244 (16)	0.041 (2)	−0.0004 (14)	−0.0003 (16)	−0.0031 (15)
C22	0.0378 (19)	0.0350 (18)	0.035 (2)	0.0003 (16)	−0.0092 (16)	−0.0066 (16)
C23	0.040 (2)	0.044 (2)	0.0246 (17)	0.0019 (17)	−0.0032 (15)	−0.0015 (15)
C24	0.0279 (16)	0.0306 (16)	0.0312 (18)	0.0000 (14)	−0.0010 (14)	0.0048 (15)

S1—O2	1.430 (2)	C10—C15	1.395 (4)
S1—O1	1.435 (2)	C11—C12	1.385 (4)
S1—N1	1.635 (3)	C11—H11	0.9500
S1—C1	1.759 (3)	C12—C13	1.383 (5)
O3—C7	1.275 (4)	C13—C14	1.379 (5)
O4—C9	1.308 (4)	C13—H13	0.9500
O4—H4O	0.8400	C14—C15	1.385 (5)
O5—C12	1.369 (4)	C14—H14	0.9500
O5—C16	1.432 (4)	C15—H15	0.9500
O6—C18	1.215 (4)	C16—H16A	0.9800
N1—C8	1.440 (4)	C16—H16B	0.9800
N1—C17	1.473 (4)	C16—H16C	0.9800
C1—C2	1.380 (4)	C17—C18	1.519 (4)
C1—C6	1.403 (4)	C17—H17A	0.9900
C2—C3	1.383 (5)	C17—H17B	0.9900
C2—H2	0.9500	C18—C19	1.489 (4)
C3—C4	1.381 (5)	C19—C20	1.389 (4)
C3—H3	0.9500	C19—C24	1.392 (4)
C4—C5	1.385 (5)	C20—C21	1.386 (5)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.383 (4)	C21—C22	1.373 (5)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.483 (4)	C22—C23	1.395 (5)
C7—C8	1.421 (4)	C22—H22	0.9500
C8—C9	1.403 (4)	C23—C24	1.381 (5)
C9—C10	1.483 (4)	C23—H23	0.9500
C10—C11	1.392 (4)	C24—H24	0.9500
O2—S1—O1	118.80 (15)	O5—C12—C11	115.7 (3)
O2—S1—N1	107.66 (14)	C13—C12—C11	120.4 (3)
O1—S1—N1	108.60 (14)	C14—C13—C12	119.0 (3)
O2—S1—C1	110.25 (15)	C14—C13—H13	120.5
O1—S1—C1	107.29 (14)	C12—C13—H13	120.5
N1—S1—C1	103.14 (14)	C13—C14—C15	121.7 (3)
C9—O4—H4O	109.5	C13—C14—H14	119.2
C12—O5—C16	117.7 (3)	C15—C14—H14	119.2
C8—N1—C17	119.4 (2)	C14—C15—C10	119.1 (3)
C8—N1—S1	115.7 (2)	C14—C15—H15	120.4
C17—N1—S1	118.9 (2)	C10—C15—H15	120.4
C2—C1—C6	121.7 (3)	O5—C16—H16A	109.5
C2—C1—S1	119.7 (3)	O5—C16—H16B	109.5
C6—C1—S1	118.6 (2)	H16A—C16—H16B	109.5
C1—C2—C3	119.1 (3)	O5—C16—H16C	109.5
C1—C2—H2	120.4	H16A—C16—H16C	109.5
C3—C2—H2	120.4	H16B—C16—H16C	109.5
C4—C3—C2	120.3 (3)	N1—C17—C18	114.1 (3)
C4—C3—H3	119.8	N1—C17—H17A	108.7
C2—C3—H3	119.8	C18—C17—H17A	108.7
C3—C4—C5	120.1 (3)	N1—C17—H17B	108.7
C3—C4—H4	120.0	C18—C17—H17B	108.7
C5—C4—H4	120.0	H17A—C17—H17B	107.6
C6—C5—C4	121.0 (3)	O6—C18—C19	120.8 (3)
C6—C5—H5	119.5	O6—C18—C17	120.0 (3)
C4—C5—H5	119.5	C19—C18—C17	119.2 (3)
C5—C6—C1	117.8 (3)	C20—C19—C24	119.3 (3)
C5—C6—C7	120.0 (3)	C20—C19—C18	122.9 (3)
C1—C6—C7	122.1 (3)	C24—C19—C18	117.7 (3)
O3—C7—C8	121.8 (3)	C21—C20—C19	120.2 (3)
O3—C7—C6	117.0 (3)	C21—C20—H20	119.9
C8—C7—C6	121.0 (3)	C19—C20—H20	119.9
C9—C8—C7	120.1 (3)	C22—C21—C20	120.1 (3)
C9—C8—N1	121.2 (3)	C22—C21—H21	120.0
C7—C8—N1	118.7 (3)	C20—C21—H21	120.0
O4—C9—C8	118.9 (3)	C21—C22—C23	120.3 (3)
O4—C9—C10	113.9 (3)	C21—C22—H22	119.8
C8—C9—C10	127.2 (3)	C23—C22—H22	119.8
C11—C10—C15	119.4 (3)	C24—C23—C22	119.5 (3)
C11—C10—C9	117.7 (3)	C24—C23—H23	120.2
C15—C10—C9	122.7 (3)	C22—C23—H23	120.2
C12—C11—C10	120.4 (3)	C23—C24—C19	120.5 (3)
C12—C11—H11	119.8	C23—C24—H24	119.8
C10—C11—H11	119.8	C19—C24—H24	119.8
O5—C12—C13	123.9 (3)
O2—S1—N1—C8	−166.6 (2)	N1—C8—C9—O4	−172.9 (3)
O1—S1—N1—C8	63.6 (2)	C7—C8—C9—C10	−171.0 (3)
C1—S1—N1—C8	−50.0 (3)	N1—C8—C9—C10	7.8 (5)
O2—S1—N1—C17	−13.9 (3)	O4—C9—C10—C11	18.6 (4)
O1—S1—N1—C17	−143.8 (2)	C8—C9—C10—C11	−162.1 (3)
C1—S1—N1—C17	102.6 (2)	O4—C9—C10—C15	−156.3 (3)
O2—S1—C1—C2	−40.4 (3)	C8—C9—C10—C15	23.0 (5)
O1—S1—C1—C2	90.4 (3)	C15—C10—C11—C12	−0.4 (5)
N1—S1—C1—C2	−155.1 (3)	C9—C10—C11—C12	−175.5 (3)
O2—S1—C1—C6	140.3 (2)	C16—O5—C12—C13	5.5 (5)
O1—S1—C1—C6	−88.9 (3)	C16—O5—C12—C11	−174.2 (3)
N1—S1—C1—C6	25.6 (3)	C10—C11—C12—O5	179.7 (3)
C6—C1—C2—C3	−0.1 (5)	C10—C11—C12—C13	0.0 (5)
S1—C1—C2—C3	−179.4 (3)	O5—C12—C13—C14	−179.1 (3)
C1—C2—C3—C4	−0.9 (5)	C11—C12—C13—C14	0.6 (5)
C2—C3—C4—C5	0.7 (6)	C12—C13—C14—C15	−0.8 (6)
C3—C4—C5—C6	0.5 (5)	C13—C14—C15—C10	0.4 (6)
C4—C5—C6—C1	−1.4 (5)	C11—C10—C15—C14	0.2 (5)
C4—C5—C6—C7	176.3 (3)	C9—C10—C15—C14	175.1 (3)
C2—C1—C6—C5	1.2 (5)	C8—N1—C17—C18	69.8 (4)
S1—C1—C6—C5	−179.5 (2)	S1—N1—C17—C18	−81.8 (3)
C2—C1—C6—C7	−176.4 (3)	N1—C17—C18—O6	−5.8 (4)
S1—C1—C6—C7	2.9 (4)	N1—C17—C18—C19	172.8 (3)
C5—C6—C7—O3	−15.2 (4)	O6—C18—C19—C20	−179.7 (3)
C1—C6—C7—O3	162.4 (3)	C17—C18—C19—C20	1.7 (5)
C5—C6—C7—C8	169.9 (3)	O6—C18—C19—C24	4.3 (5)
C1—C6—C7—C8	−12.5 (5)	C17—C18—C19—C24	−174.3 (3)
O3—C7—C8—C9	−9.3 (5)	C24—C19—C20—C21	2.7 (5)
C6—C7—C8—C9	165.3 (3)	C18—C19—C20—C21	−173.2 (3)
O3—C7—C8—N1	171.9 (3)	C19—C20—C21—C22	−1.5 (5)
C6—C7—C8—N1	−13.5 (4)	C20—C21—C22—C23	−1.3 (5)
C17—N1—C8—C9	76.6 (4)	C21—C22—C23—C24	2.8 (5)
S1—N1—C8—C9	−130.9 (3)	C22—C23—C24—C19	−1.6 (5)
C17—N1—C8—C7	−104.6 (3)	C20—C19—C24—C23	−1.2 (5)
S1—N1—C8—C7	47.9 (3)	C18—C19—C24—C23	175.0 (3)
C7—C8—C9—O4	8.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1i	0.95	2.59	3.281 (4)	130
C11—H11···O1ii	0.95	2.53	3.371 (4)	148
C16—H16B···O6iii	0.98	2.64	3.246 (4)	120
C24—H24···O5iv	0.95	2.57	3.508 (4)	167
O4—H4O···O3	0.84	1.71	2.478 (3)	151
C15—H15···N1	0.95	2.38	2.972 (4)	120
C17—H17B···O2	0.99	2.39	2.800 (4)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1i	0.95	2.59	3.281 (4)	130
C11—H11⋯O1ii	0.95	2.53	3.371 (4)	148
C16—H16B⋯O6iii	0.98	2.64	3.246 (4)	120
C24—H24⋯O5iv	0.95	2.57	3.508 (4)	167
O4—H4O⋯O3	0.84	1.71	2.478 (3)	151
C15—H15⋯N1	0.95	2.38	2.972 (4)	120

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