N-Benzyl-4-hy-droxy-2-methyl-1,1-dioxo-2H-1λ(6),2-benzothia-zine-3-carboxamide.

In the title mol-ecule, C(17)H(16)N(2)O(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.546 (4) and 0.281 (4) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond. The two aromatic rings are inclined to one another by 42.32 (11)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked via a series of C-H⋯O inter-actions, leading to the formation of a three-dimensional network.

Related literature

For the biological activity of benzothia­zine derivatives, see: Lomabardino & Wiseman et al. (1972 ▶); Lazzeri et al. (2001 ▶). For the synthetic procedure, see: Siddiqui et al. (2008 ▶). For the structures of similar compounds, see: Siddiqui et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C17H16N2O4S

M = 344.38

Triclinic,

a = 8.785 (3) Å

b = 9.122 (3) Å

c = 11.425 (4) Å

α = 66.61 (2)°

β = 87.66 (2)°

γ = 69.38 (2)°

V = 781.2 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.16 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.964, T max = 0.977

6837 measured reflections

3592 independent reflections

3141 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.06

3592 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.42 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/S1600536812022805/su2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022805/su2428Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022805/su2428Isup3.cml

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

C17H16N2O4S	Z = 2
Mr = 344.38	F(000) = 360
Triclinic, P1	Dx = 1.464 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.785 (3) Å	Cell parameters from 3525 reflections
b = 9.122 (3) Å	θ = 1.0–27.5°
c = 11.425 (4) Å	µ = 0.23 mm−1
α = 66.61 (2)°	T = 173 K
β = 87.66 (2)°	Prism, colourless
γ = 69.38 (2)°	0.16 × 0.16 × 0.10 mm
V = 781.2 (5) Å3

Nonius KappaCCD diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	3141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→11
Tmin = 0.964, Tmax = 0.977	k = −11→11
6837 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.7103P] where P = (Fo2 + 2Fc2)/3
3592 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.42 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	0.62867 (5)	0.60505 (6)	0.34904 (4)	0.02296 (13)
O1	0.58802 (17)	0.69700 (17)	0.42959 (14)	0.0283 (3)
O2	0.50059 (16)	0.61698 (18)	0.26852 (14)	0.0293 (3)
O3	0.93624 (19)	0.2725 (2)	0.19251 (15)	0.0345 (3)
H3O	0.9365	0.1725	0.2308	0.052*
O4	0.88028 (17)	0.02644 (18)	0.36729 (14)	0.0309 (3)
N1	0.72650 (19)	0.40160 (19)	0.44128 (15)	0.0219 (3)
N2	0.71929 (19)	0.0748 (2)	0.51809 (16)	0.0253 (3)
H2N	0.6669	0.1466	0.5526	0.030*
C1	0.7810 (2)	0.6574 (2)	0.25555 (18)	0.0249 (4)
C2	0.8007 (3)	0.8122 (3)	0.22507 (19)	0.0296 (4)
H2	0.7324	0.8939	0.2550	0.036*
C3	0.9231 (3)	0.8447 (3)	0.1495 (2)	0.0357 (5)
H3	0.9389	0.9499	0.1275	0.043*
C4	1.0220 (3)	0.7253 (3)	0.1060 (2)	0.0375 (5)
H4	1.1040	0.7501	0.0534	0.045*
C5	1.0029 (3)	0.5700 (3)	0.1383 (2)	0.0323 (5)
H5	1.0714	0.4889	0.1079	0.039*
C6	0.8826 (2)	0.5329 (3)	0.21550 (18)	0.0262 (4)
C7	0.8691 (2)	0.3635 (3)	0.26145 (19)	0.0257 (4)
C8	0.7992 (2)	0.3010 (2)	0.36928 (19)	0.0235 (4)
C9	0.8009 (2)	0.1249 (2)	0.41831 (19)	0.0248 (4)
C10	0.8312 (3)	0.3639 (3)	0.55606 (19)	0.0291 (4)
H10A	0.8803	0.2394	0.6056	0.035*
H10B	0.7645	0.4172	0.6096	0.035*
H10C	0.9182	0.4100	0.5288	0.035*
C11	0.7160 (3)	−0.0979 (2)	0.5706 (2)	0.0287 (4)
H11A	0.8282	−0.1813	0.5792	0.034*
H11B	0.6461	−0.1068	0.5098	0.034*
C12	0.6520 (2)	−0.1446 (2)	0.69982 (19)	0.0272 (4)
C13	0.6713 (3)	−0.0783 (3)	0.7863 (2)	0.0317 (4)
H13	0.7232	0.0031	0.7634	0.038*
C14	0.6155 (3)	−0.1299 (3)	0.9056 (2)	0.0392 (5)
H14	0.6304	−0.0845	0.9641	0.047*
C15	0.5382 (3)	−0.2469 (3)	0.9401 (2)	0.0437 (6)
H15	0.4990	−0.2810	1.0216	0.052*
C16	0.5185 (3)	−0.3139 (3)	0.8547 (2)	0.0411 (5)
H16	0.4660	−0.3948	0.8779	0.049*
C17	0.5749 (3)	−0.2635 (3)	0.7358 (2)	0.0322 (5)
H17	0.5610	−0.3104	0.6780	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.0241 (2)	0.0199 (2)	0.0242 (2)	−0.00610 (17)	0.00430 (17)	−0.01015 (18)
O1	0.0335 (7)	0.0217 (7)	0.0312 (7)	−0.0075 (6)	0.0082 (6)	−0.0148 (6)
O2	0.0265 (7)	0.0291 (7)	0.0301 (7)	−0.0081 (6)	0.0004 (6)	−0.0116 (6)
O3	0.0401 (8)	0.0339 (8)	0.0351 (8)	−0.0121 (7)	0.0151 (7)	−0.0218 (7)
O4	0.0336 (7)	0.0250 (7)	0.0369 (8)	−0.0068 (6)	0.0096 (6)	−0.0192 (6)
N1	0.0251 (8)	0.0179 (7)	0.0232 (8)	−0.0065 (6)	0.0040 (6)	−0.0101 (6)
N2	0.0270 (8)	0.0200 (8)	0.0295 (9)	−0.0057 (6)	0.0052 (7)	−0.0134 (7)
C1	0.0275 (9)	0.0249 (9)	0.0208 (9)	−0.0096 (7)	0.0025 (7)	−0.0081 (7)
C2	0.0369 (11)	0.0266 (10)	0.0253 (10)	−0.0127 (8)	0.0026 (8)	−0.0096 (8)
C3	0.0484 (13)	0.0329 (11)	0.0288 (11)	−0.0236 (10)	0.0048 (9)	−0.0079 (9)
C4	0.0395 (12)	0.0447 (13)	0.0296 (11)	−0.0222 (10)	0.0101 (9)	−0.0112 (10)
C5	0.0322 (10)	0.0371 (11)	0.0269 (10)	−0.0121 (9)	0.0079 (8)	−0.0132 (9)
C6	0.0264 (9)	0.0275 (10)	0.0229 (9)	−0.0089 (8)	0.0032 (7)	−0.0093 (8)
C7	0.0228 (9)	0.0275 (10)	0.0284 (10)	−0.0058 (7)	0.0040 (7)	−0.0160 (8)
C8	0.0211 (8)	0.0222 (9)	0.0277 (9)	−0.0047 (7)	0.0037 (7)	−0.0136 (8)
C9	0.0228 (9)	0.0228 (9)	0.0291 (10)	−0.0054 (7)	0.0005 (7)	−0.0132 (8)
C10	0.0342 (10)	0.0256 (10)	0.0268 (10)	−0.0085 (8)	−0.0015 (8)	−0.0115 (8)
C11	0.0334 (10)	0.0208 (9)	0.0329 (10)	−0.0088 (8)	0.0039 (8)	−0.0131 (8)
C12	0.0263 (9)	0.0210 (9)	0.0279 (10)	−0.0036 (7)	−0.0025 (8)	−0.0075 (8)
C13	0.0317 (10)	0.0290 (10)	0.0344 (11)	−0.0085 (8)	0.0005 (8)	−0.0150 (9)
C14	0.0449 (13)	0.0403 (13)	0.0286 (11)	−0.0094 (10)	−0.0024 (9)	−0.0150 (10)
C15	0.0461 (13)	0.0460 (14)	0.0266 (11)	−0.0137 (11)	0.0029 (10)	−0.0053 (10)
C16	0.0466 (13)	0.0376 (12)	0.0328 (12)	−0.0200 (11)	−0.0012 (10)	−0.0037 (10)
C17	0.0370 (11)	0.0266 (10)	0.0282 (10)	−0.0102 (9)	−0.0035 (8)	−0.0072 (8)

S1—O2	1.4293 (15)	C5—H5	0.9500
S1—O1	1.4328 (14)	C6—C7	1.468 (3)
S1—N1	1.6404 (17)	C7—C8	1.359 (3)
S1—C1	1.757 (2)	C8—C9	1.471 (3)
O3—C7	1.340 (2)	C10—H10A	0.9800
O3—H3O	0.8400	C10—H10B	0.9800
O4—C9	1.255 (2)	C10—H10C	0.9800
N1—C8	1.439 (2)	C11—C12	1.510 (3)
N1—C10	1.484 (2)	C11—H11A	0.9900
N2—C9	1.331 (3)	C11—H11B	0.9900
N2—C11	1.457 (2)	C12—C13	1.390 (3)
N2—H2N	0.8800	C12—C17	1.394 (3)
C1—C2	1.387 (3)	C13—C14	1.385 (3)
C1—C6	1.400 (3)	C13—H13	0.9500
C2—C3	1.391 (3)	C14—C15	1.382 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.385 (3)	C15—C16	1.385 (4)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.385 (3)	C16—C17	1.383 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.396 (3)	C17—H17	0.9500
O2—S1—O1	119.07 (9)	C7—C8—C9	120.57 (17)
O2—S1—N1	108.07 (9)	N1—C8—C9	117.91 (16)
O1—S1—N1	107.75 (9)	O4—C9—N2	122.22 (18)
O2—S1—C1	109.30 (9)	O4—C9—C8	119.70 (18)
O1—S1—C1	109.51 (9)	N2—C9—C8	118.07 (16)
N1—S1—C1	101.71 (9)	N1—C10—H10A	109.5
C7—O3—H3O	109.5	N1—C10—H10B	109.5
C8—N1—C10	115.28 (15)	H10A—C10—H10B	109.5
C8—N1—S1	112.70 (13)	N1—C10—H10C	109.5
C10—N1—S1	116.38 (12)	H10A—C10—H10C	109.5
C9—N2—C11	120.56 (16)	H10B—C10—H10C	109.5
C9—N2—H2N	119.7	N2—C11—C12	112.69 (16)
C11—N2—H2N	119.7	N2—C11—H11A	109.1
C2—C1—C6	122.04 (18)	C12—C11—H11A	109.1
C2—C1—S1	121.72 (15)	N2—C11—H11B	109.1
C6—C1—S1	116.23 (15)	C12—C11—H11B	109.1
C1—C2—C3	118.22 (19)	H11A—C11—H11B	107.8
C1—C2—H2	120.9	C13—C12—C17	118.52 (19)
C3—C2—H2	120.9	C13—C12—C11	122.75 (18)
C4—C3—C2	120.6 (2)	C17—C12—C11	118.69 (18)
C4—C3—H3	119.7	C14—C13—C12	120.5 (2)
C2—C3—H3	119.7	C14—C13—H13	119.7
C3—C4—C5	120.8 (2)	C12—C13—H13	119.7
C3—C4—H4	119.6	C15—C14—C13	120.6 (2)
C5—C4—H4	119.6	C15—C14—H14	119.7
C4—C5—C6	119.8 (2)	C13—C14—H14	119.7
C4—C5—H5	120.1	C14—C15—C16	119.4 (2)
C6—C5—H5	120.1	C14—C15—H15	120.3
C5—C6—C1	118.45 (19)	C16—C15—H15	120.3
C5—C6—C7	121.20 (18)	C17—C16—C15	120.3 (2)
C1—C6—C7	120.22 (17)	C17—C16—H16	119.9
O3—C7—C8	122.42 (18)	C15—C16—H16	119.9
O3—C7—C6	115.26 (17)	C16—C17—C12	120.7 (2)
C8—C7—C6	122.27 (17)	C16—C17—H17	119.6
C7—C8—N1	121.49 (17)	C12—C17—H17	119.6
O2—S1—N1—C8	60.59 (14)	C1—C6—C7—C8	−20.3 (3)
O1—S1—N1—C8	−169.54 (12)	O3—C7—C8—N1	−179.44 (17)
C1—S1—N1—C8	−54.42 (14)	C6—C7—C8—N1	3.3 (3)
O2—S1—N1—C10	−163.02 (13)	O3—C7—C8—C9	2.6 (3)
O1—S1—N1—C10	−33.15 (16)	C6—C7—C8—C9	−174.66 (17)
C1—S1—N1—C10	81.97 (15)	C10—N1—C8—C7	−98.7 (2)
O2—S1—C1—C2	106.46 (17)	S1—N1—C8—C7	38.2 (2)
O1—S1—C1—C2	−25.63 (19)	C10—N1—C8—C9	79.3 (2)
N1—S1—C1—C2	−139.44 (17)	S1—N1—C8—C9	−143.81 (14)
O2—S1—C1—C6	−74.54 (17)	C11—N2—C9—O4	−1.5 (3)
O1—S1—C1—C6	153.38 (15)	C11—N2—C9—C8	179.79 (17)
N1—S1—C1—C6	39.56 (17)	C7—C8—C9—O4	6.6 (3)
C6—C1—C2—C3	1.7 (3)	N1—C8—C9—O4	−171.38 (17)
S1—C1—C2—C3	−179.35 (16)	C7—C8—C9—N2	−174.66 (18)
C1—C2—C3—C4	0.1 (3)	N1—C8—C9—N2	7.3 (3)
C2—C3—C4—C5	−0.9 (3)	C9—N2—C11—C12	166.82 (17)
C3—C4—C5—C6	0.0 (3)	N2—C11—C12—C13	−30.1 (3)
C4—C5—C6—C1	1.7 (3)	N2—C11—C12—C17	152.07 (18)
C4—C5—C6—C7	−174.19 (19)	C17—C12—C13—C14	0.2 (3)
C2—C1—C6—C5	−2.6 (3)	C11—C12—C13—C14	−177.66 (19)
S1—C1—C6—C5	178.41 (15)	C12—C13—C14—C15	−0.6 (3)
C2—C1—C6—C7	173.33 (18)	C13—C14—C15—C16	0.7 (4)
S1—C1—C6—C7	−5.7 (2)	C14—C15—C16—C17	−0.3 (4)
C5—C6—C7—O3	−21.9 (3)	C15—C16—C17—C12	−0.1 (3)
C1—C6—C7—O3	162.27 (18)	C13—C12—C17—C16	0.2 (3)
C5—C6—C7—C8	155.6 (2)	C11—C12—C17—C16	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.84	1.79	2.531 (2)	146
N2—H2N···O1i	0.88	2.24	2.980 (2)	141
C10—H10A···O4ii	0.98	2.50	3.349 (3)	144
C11—H11B···O1iii	0.99	2.51	3.374 (3)	146
C15—H15···O2iv	0.95	2.59	3.496 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.84	1.79	2.531 (2)	146
N2—H2N⋯O1i	0.88	2.24	2.980 (2)	141
C10—H10A⋯O4ii	0.98	2.50	3.349 (3)	144
C11—H11B⋯O1iii	0.99	2.51	3.374 (3)	146
C15—H15⋯O2iv	0.95	2.59	3.496 (3)	158

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