(4-Hydr-oxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)(3-methoxy-phen-yl)methanone.

In the title compoud, C(16)H(13)NO(5)S, the heterocyclic thia-zine ring adopts a twist boat conformation with the S and N atoms displaced by 0.339 (5) and 0.322 (4) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. An intra-molecular O-H⋯O inter-action is present, forming a five-membered ring. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which result in chains along the b axis.

Related literature

For the biological activity of 1,2-benzothia­zine derivatives, see: Ikeda et al. (1992 ▶); Ahmad et al. (2010 ▶); Lombardino et al. (1971 ▶, 1973 ▶); Zia-ur-Rehman et al. (2006 ▶); Siddiqui et al. (2007 ▶). For comparison bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C16H13NO5S

M = 331.33

Monoclinic,

a = 8.1866 (3) Å

b = 7.2431 (3) Å

c = 25.2452 (9) Å

β = 95.5869 (18)°

V = 1489.84 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 295 K

0.16 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.962, T max = 0.976

5610 measured reflections

3399 independent reflections

2795 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.147

S = 1.09

3399 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.38 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 datablocks global, I. DOI: 10.1107/S1600536810011827/fl2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011827/fl2296Isup2.hkl

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

C16H13NO5S	F(000) = 688
Mr = 331.33	Dx = 1.477 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3461 reflections
a = 8.1866 (3) Å	θ = 1.0–27.5°
b = 7.2431 (3) Å	µ = 0.24 mm−1
c = 25.2452 (9) Å	T = 295 K
β = 95.5869 (18)°	Block, yellow
V = 1489.84 (10) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	3399 independent reflections
Radiation source: fine-focus sealed tube	2795 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
Tmin = 0.962, Tmax = 0.976	k = −9→9
5610 measured reflections	l = −32→32

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)] = 0.056	Hydrogen site location: difference Fourier map
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.051P)2 + 1.1474P] where P = (Fo2 + 2Fc2)/3
3399 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.30794 (7)	0.18400 (11)	0.10208 (2)	0.0519 (2)
O1	0.1907 (2)	0.3174 (4)	0.08123 (8)	0.0825 (8)
O2	0.2664 (3)	−0.0070 (3)	0.09981 (8)	0.0780 (7)
O3	0.7829 (2)	0.0710 (3)	0.18344 (8)	0.0532 (5)
H3O	0.772 (4)	0.058 (4)	0.2194 (12)	0.064*
O4	0.6461 (2)	0.0579 (3)	0.26917 (7)	0.0502 (4)
O5	0.2363 (2)	0.2043 (3)	0.40084 (7)	0.0639 (6)
N1	0.3602 (2)	0.2363 (3)	0.16357 (7)	0.0405 (4)
H1N	0.350 (3)	0.347 (4)	0.1721 (11)	0.049*
C1	0.4921 (3)	0.2116 (3)	0.07263 (9)	0.0443 (5)
C2	0.4907 (4)	0.2573 (4)	0.01952 (10)	0.0608 (7)
H2	0.3919	0.2803	−0.0008	0.073*
C3	0.6372 (4)	0.2684 (5)	−0.00311 (11)	0.0669 (8)
H3	0.6374	0.2979	−0.0390	0.080*
C4	0.7820 (4)	0.2361 (5)	0.02714 (12)	0.0686 (8)
H4	0.8802	0.2442	0.0116	0.082*
C5	0.7853 (3)	0.1919 (4)	0.08025 (11)	0.0561 (7)
H5	0.8850	0.1703	0.1002	0.067*
C6	0.6392 (3)	0.1796 (3)	0.10413 (9)	0.0415 (5)
C7	0.6420 (3)	0.1356 (3)	0.16109 (9)	0.0396 (5)
C8	0.5064 (3)	0.1554 (3)	0.18882 (8)	0.0382 (5)
C9	0.5114 (3)	0.0999 (3)	0.24377 (9)	0.0407 (5)
C10	0.3583 (3)	0.0867 (3)	0.27107 (9)	0.0399 (5)
C11	0.3629 (3)	0.1488 (3)	0.32355 (9)	0.0433 (5)
H11	0.4583	0.2005	0.3403	0.052*
C12	0.2229 (3)	0.1324 (4)	0.35052 (9)	0.0485 (6)
C13	0.0846 (3)	0.0446 (4)	0.32655 (11)	0.0550 (7)
H13	−0.0078	0.0308	0.3449	0.066*
C14	0.0844 (3)	−0.0224 (4)	0.27528 (11)	0.0529 (6)
H14	−0.0076	−0.0845	0.2598	0.063*
C15	0.2183 (3)	0.0011 (3)	0.24657 (10)	0.0469 (5)
H15	0.2150	−0.0395	0.2115	0.056*
C16	0.0876 (4)	0.2197 (6)	0.42631 (13)	0.0785 (10)
H16A	0.1089	0.2871	0.4590	0.094*
H16B	0.0480	0.0985	0.4337	0.094*
H16C	0.0063	0.2837	0.4032	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0374 (3)	0.0828 (5)	0.0356 (3)	−0.0035 (3)	0.0039 (2)	−0.0057 (3)
O1	0.0477 (11)	0.150 (2)	0.0493 (11)	0.0280 (13)	0.0017 (8)	0.0181 (13)
O2	0.0722 (14)	0.0964 (17)	0.0683 (13)	−0.0391 (13)	0.0216 (11)	−0.0321 (12)
O3	0.0387 (9)	0.0667 (12)	0.0545 (10)	0.0061 (8)	0.0054 (8)	0.0077 (9)
O4	0.0439 (9)	0.0615 (11)	0.0446 (9)	0.0019 (8)	0.0011 (7)	0.0117 (8)
O5	0.0547 (11)	0.0942 (16)	0.0447 (10)	0.0029 (10)	0.0150 (8)	−0.0049 (10)
N1	0.0389 (10)	0.0488 (11)	0.0340 (9)	0.0058 (9)	0.0049 (7)	−0.0035 (8)
C1	0.0439 (12)	0.0530 (14)	0.0371 (11)	−0.0021 (10)	0.0091 (9)	−0.0066 (10)
C2	0.0648 (17)	0.080 (2)	0.0387 (12)	0.0017 (15)	0.0090 (12)	−0.0008 (13)
C3	0.082 (2)	0.079 (2)	0.0431 (13)	0.0001 (17)	0.0238 (14)	0.0016 (14)
C4	0.0667 (18)	0.085 (2)	0.0598 (17)	−0.0013 (16)	0.0357 (15)	0.0012 (16)
C5	0.0465 (14)	0.0649 (17)	0.0596 (15)	−0.0009 (12)	0.0182 (12)	−0.0007 (13)
C6	0.0422 (12)	0.0427 (12)	0.0411 (11)	−0.0013 (10)	0.0112 (9)	−0.0045 (9)
C7	0.0359 (11)	0.0392 (11)	0.0438 (11)	0.0000 (9)	0.0051 (9)	−0.0015 (9)
C8	0.0367 (11)	0.0422 (11)	0.0357 (10)	0.0031 (9)	0.0032 (8)	−0.0006 (9)
C9	0.0429 (12)	0.0388 (11)	0.0404 (11)	0.0004 (9)	0.0040 (9)	0.0012 (9)
C10	0.0414 (12)	0.0406 (11)	0.0380 (11)	0.0027 (9)	0.0053 (9)	0.0060 (9)
C11	0.0399 (12)	0.0490 (13)	0.0411 (11)	0.0017 (10)	0.0043 (9)	0.0062 (10)
C12	0.0480 (13)	0.0568 (15)	0.0417 (12)	0.0070 (11)	0.0096 (10)	0.0082 (11)
C13	0.0397 (13)	0.0709 (18)	0.0553 (15)	0.0020 (12)	0.0093 (11)	0.0165 (13)
C14	0.0392 (12)	0.0593 (16)	0.0585 (15)	−0.0052 (11)	−0.0035 (11)	0.0105 (12)
C15	0.0489 (13)	0.0491 (13)	0.0418 (12)	−0.0015 (11)	−0.0002 (10)	0.0061 (10)
C16	0.069 (2)	0.106 (3)	0.0654 (19)	0.0085 (19)	0.0307 (16)	−0.0085 (18)

S1—O2	1.425 (2)	C5—C6	1.394 (3)
S1—O1	1.426 (2)	C5—H5	0.9300
S1—N1	1.6145 (19)	C6—C7	1.471 (3)
S1—C1	1.756 (2)	C7—C8	1.377 (3)
O3—C7	1.319 (3)	C8—C9	1.441 (3)
O3—H3O	0.92 (3)	C9—C10	1.491 (3)
O4—C9	1.257 (3)	C10—C15	1.394 (3)
O5—C12	1.367 (3)	C10—C11	1.396 (3)
O5—C16	1.436 (3)	C11—C12	1.394 (3)
N1—C8	1.426 (3)	C11—H11	0.9300
N1—H1N	0.84 (3)	C12—C13	1.385 (4)
C1—C2	1.380 (3)	C13—C14	1.382 (4)
C1—C6	1.396 (3)	C13—H13	0.9300
C2—C3	1.381 (4)	C14—C15	1.382 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.366 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.376 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
O2—S1—O1	119.57 (16)	C8—C7—C6	122.5 (2)
O2—S1—N1	107.85 (12)	C7—C8—N1	119.92 (19)
O1—S1—N1	107.56 (13)	C7—C8—C9	120.8 (2)
O2—S1—C1	107.77 (12)	N1—C8—C9	119.30 (19)
O1—S1—C1	109.96 (13)	O4—C9—C8	120.0 (2)
N1—S1—C1	102.85 (11)	O4—C9—C10	118.9 (2)
C7—O3—H3O	107.2 (19)	C8—C9—C10	121.1 (2)
C12—O5—C16	116.8 (2)	C15—C10—C11	120.6 (2)
C8—N1—S1	117.75 (15)	C15—C10—C9	121.0 (2)
C8—N1—H1N	112.5 (19)	C11—C10—C9	118.1 (2)
S1—N1—H1N	116.6 (19)	C12—C11—C10	119.2 (2)
C2—C1—C6	121.2 (2)	C12—C11—H11	120.4
C2—C1—S1	120.8 (2)	C10—C11—H11	120.4
C6—C1—S1	117.92 (17)	O5—C12—C13	124.7 (2)
C1—C2—C3	119.4 (3)	O5—C12—C11	115.2 (2)
C1—C2—H2	120.3	C13—C12—C11	120.1 (2)
C3—C2—H2	120.3	C14—C13—C12	119.8 (2)
C4—C3—C2	120.0 (3)	C14—C13—H13	120.1
C4—C3—H3	120.0	C12—C13—H13	120.1
C2—C3—H3	120.0	C15—C14—C13	121.3 (2)
C3—C4—C5	121.2 (3)	C15—C14—H14	119.3
C3—C4—H4	119.4	C13—C14—H14	119.3
C5—C4—H4	119.4	C14—C15—C10	118.8 (2)
C4—C5—C6	120.0 (3)	C14—C15—H15	120.6
C4—C5—H5	120.0	C10—C15—H15	120.6
C6—C5—H5	120.0	O5—C16—H16A	109.5
C5—C6—C1	118.2 (2)	O5—C16—H16B	109.5
C5—C6—C7	120.3 (2)	H16A—C16—H16B	109.5
C1—C6—C7	121.6 (2)	O5—C16—H16C	109.5
O3—C7—C8	122.3 (2)	H16A—C16—H16C	109.5
O3—C7—C6	115.16 (19)	H16B—C16—H16C	109.5
O2—S1—N1—C8	66.4 (2)	C6—C7—C8—N1	−5.7 (3)
O1—S1—N1—C8	−163.37 (18)	O3—C7—C8—C9	−2.0 (4)
C1—S1—N1—C8	−47.3 (2)	C6—C7—C8—C9	176.1 (2)
O2—S1—C1—C2	94.1 (3)	S1—N1—C8—C7	39.2 (3)
O1—S1—C1—C2	−37.8 (3)	S1—N1—C8—C9	−142.49 (19)
N1—S1—C1—C2	−152.2 (2)	C7—C8—C9—O4	10.3 (4)
O2—S1—C1—C6	−83.7 (2)	N1—C8—C9—O4	−167.9 (2)
O1—S1—C1—C6	144.4 (2)	C7—C8—C9—C10	−168.2 (2)
N1—S1—C1—C6	30.0 (2)	N1—C8—C9—C10	13.6 (3)
C6—C1—C2—C3	1.1 (4)	O4—C9—C10—C15	−133.0 (2)
S1—C1—C2—C3	−176.6 (2)	C8—C9—C10—C15	45.5 (3)
C1—C2—C3—C4	−0.6 (5)	O4—C9—C10—C11	41.8 (3)
C2—C3—C4—C5	0.1 (5)	C8—C9—C10—C11	−139.7 (2)
C3—C4—C5—C6	−0.1 (5)	C15—C10—C11—C12	−3.1 (4)
C4—C5—C6—C1	0.5 (4)	C9—C10—C11—C12	−177.9 (2)
C4—C5—C6—C7	−178.9 (3)	C16—O5—C12—C13	−12.1 (4)
C2—C1—C6—C5	−1.1 (4)	C16—O5—C12—C11	169.3 (3)
S1—C1—C6—C5	176.7 (2)	C10—C11—C12—O5	−177.2 (2)
C2—C1—C6—C7	178.4 (2)	C10—C11—C12—C13	4.2 (4)
S1—C1—C6—C7	−3.8 (3)	O5—C12—C13—C14	179.8 (2)
C5—C6—C7—O3	−14.2 (3)	C11—C12—C13—C14	−1.7 (4)
C1—C6—C7—O3	166.3 (2)	C12—C13—C14—C15	−1.9 (4)
C5—C6—C7—C8	167.5 (2)	C13—C14—C15—C10	3.0 (4)
C1—C6—C7—C8	−11.9 (4)	C11—C10—C15—C14	−0.4 (4)
O3—C7—C8—N1	176.2 (2)	C9—C10—C15—C14	174.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.92 (3)	1.70 (3)	2.534 (2)	148 (3)
N1—H1N···O4i	0.84 (3)	2.13 (3)	2.886 (3)	151 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.92 (3)	1.70 (3)	2.534 (2)	148 (3)
N1—H1N⋯O4i	0.84 (3)	2.13 (3)	2.886 (3)	151 (3)

Symmetry code: (i) .