N-[2-(Amino-carbon-yl)phen-yl]-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

In the title compound, C(17)H(15)N(3)O(5)S, the thia-zine ring adopts a distorted half-chair conformation. The mol-ecular structure is stabilized by intra-molecular N-H⋯O, N-H⋯N and O-H⋯O hydrogen bonding. Pairs of mol-ecules are bound together as centrosymmetric dimers through N-H⋯O hydrogen bonds.

Related literature

For the synthesis of related mol­ecules, see: Braun (1923 ▶); Ahmad et al. (2008 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of 1,2-benzothia­zine 1,1-dioxides, see: Bihovsky et al. (2004 ▶); Turck et al. (1996 ▶); Zia-ur-Rehman et al. (2006 ▶). For similar mol­ecules, see: Kojić-Prodić & Rużić-Toroš (1982 ▶); Siddiqui et al. (2009 ▶); Weast et al. (1984 ▶); Zia-ur-Rehman et al. (2007 ▶).

Experimental

Crystal data

C17H15N3O5S

M = 373.38

Monoclinic,

a = 8.1377 (6) Å

b = 7.0515 (6) Å

c = 29.069 (2) Å

β = 96.502 (3)°

V = 1657.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.39 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.915, T max = 0.975

16109 measured reflections

3753 independent reflections

3011 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.213

S = 1.09

3753 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038951/bt5073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038951/bt5073Isup2.hkl

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

C17H15N3O5S	F(000) = 776
Mr = 373.38	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6164 reflections
a = 8.1377 (6) Å	θ = 2.5–27.1°
b = 7.0515 (6) Å	µ = 0.23 mm−1
c = 29.069 (2) Å	T = 296 K
β = 96.502 (3)°	Needles, colourless
V = 1657.3 (2) Å3	0.39 × 0.25 × 0.11 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	3011 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
Tmin = 0.915, Tmax = 0.975	k = −9→9
16109 measured reflections	l = −32→37

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0335P)2 + 9.427P] where P = (Fo2 + 2Fc2)/3
3753 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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	0.35684 (14)	0.5031 (2)	0.33289 (4)	0.0343 (3)
O2	0.2977 (5)	0.6850 (5)	0.34450 (12)	0.0427 (9)
O3	0.5306 (4)	0.4668 (7)	0.33922 (13)	0.0538 (11)
O4	−0.1641 (4)	0.3152 (6)	0.38428 (12)	0.0480 (10)
O5	0.3670 (4)	0.3198 (6)	0.47838 (12)	0.0484 (10)
N1	0.2640 (5)	0.3427 (6)	0.36214 (13)	0.0310 (9)
N2	0.0743 (5)	0.2848 (6)	0.43247 (12)	0.0306 (8)
H2	0.1801	0.2826	0.4328	0.037*
N3	0.3804 (6)	0.4241 (8)	0.55160 (15)	0.0534 (13)
H3A	0.4817	0.4585	0.5513	0.064*
H3B	0.3319	0.4407	0.5761	0.064*
O1	−0.1513 (4)	0.3895 (6)	0.29823 (12)	0.0436 (9)
H1	−0.1968	0.3747	0.3218	0.065*
C1	0.2765 (6)	0.4493 (7)	0.27578 (16)	0.0329 (10)
C2	0.1069 (6)	0.4046 (7)	0.26901 (16)	0.0322 (10)
C3	0.0347 (8)	0.3766 (8)	0.22406 (17)	0.0445 (13)
H3	−0.0780	0.3516	0.2183	0.053*
C4	0.1301 (9)	0.3861 (9)	0.18781 (19)	0.0577 (17)
H4	0.0805	0.3685	0.1577	0.069*
C5	0.2966 (9)	0.4210 (10)	0.19540 (19)	0.0580 (17)
H5	0.3594	0.4221	0.1706	0.070*
C6	0.3718 (7)	0.4546 (9)	0.23979 (19)	0.0470 (14)
H6	0.4845	0.4802	0.2451	0.056*
C7	0.0124 (6)	0.3801 (7)	0.30885 (16)	0.0314 (10)
C8	0.0874 (6)	0.3479 (7)	0.35254 (16)	0.0308 (10)
C9	−0.0106 (6)	0.3133 (7)	0.39093 (15)	0.0315 (10)
C10	0.0150 (6)	0.2579 (6)	0.47583 (15)	0.0287 (9)
C11	0.1236 (6)	0.2888 (7)	0.51660 (16)	0.0323 (10)
C12	0.0636 (7)	0.2643 (7)	0.55876 (17)	0.0402 (12)
H12	0.1350	0.2810	0.5858	0.048*
C13	−0.0980 (7)	0.2160 (8)	0.56205 (18)	0.0441 (13)
H13	−0.1358	0.2046	0.5909	0.053*
C14	−0.2039 (7)	0.1845 (8)	0.5223 (2)	0.0448 (13)
H14	−0.3134	0.1514	0.5245	0.054*
C15	−0.1485 (6)	0.2019 (7)	0.47945 (17)	0.0374 (11)
H15	−0.2197	0.1764	0.4528	0.045*
C16	0.2986 (6)	0.3449 (8)	0.51412 (16)	0.0368 (11)
C17	0.3393 (7)	0.1508 (9)	0.3632 (2)	0.0521 (15)
H17A	0.3025	0.0790	0.3882	0.078*
H17B	0.4576	0.1619	0.3678	0.078*
H17C	0.3065	0.0873	0.3344	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0273 (5)	0.0450 (7)	0.0309 (6)	−0.0003 (5)	0.0047 (4)	0.0006 (5)
O2	0.048 (2)	0.041 (2)	0.0391 (19)	−0.0070 (17)	0.0065 (16)	−0.0037 (16)
O3	0.0284 (18)	0.084 (3)	0.049 (2)	0.000 (2)	0.0067 (16)	0.010 (2)
O4	0.0289 (18)	0.079 (3)	0.0368 (19)	0.0027 (19)	0.0076 (14)	0.0050 (19)
O5	0.0350 (19)	0.075 (3)	0.0354 (19)	−0.0012 (19)	0.0067 (15)	−0.0072 (19)
N1	0.0278 (19)	0.038 (2)	0.0276 (19)	0.0065 (17)	0.0039 (15)	0.0006 (16)
N2	0.0260 (19)	0.039 (2)	0.0280 (19)	0.0001 (17)	0.0063 (15)	0.0053 (17)
N3	0.042 (3)	0.082 (4)	0.036 (2)	−0.006 (3)	0.0011 (19)	−0.009 (2)
O1	0.0307 (18)	0.065 (3)	0.0335 (18)	−0.0013 (18)	−0.0011 (14)	0.0024 (18)
C1	0.040 (3)	0.032 (2)	0.028 (2)	0.001 (2)	0.0079 (19)	0.0016 (18)
C2	0.037 (2)	0.031 (2)	0.029 (2)	−0.001 (2)	0.0064 (19)	0.0005 (19)
C3	0.063 (4)	0.042 (3)	0.029 (2)	−0.005 (3)	0.005 (2)	−0.002 (2)
C4	0.087 (5)	0.056 (4)	0.029 (3)	−0.013 (3)	0.004 (3)	−0.005 (3)
C5	0.076 (4)	0.071 (4)	0.031 (3)	−0.005 (4)	0.024 (3)	−0.004 (3)
C6	0.046 (3)	0.057 (4)	0.041 (3)	−0.003 (3)	0.016 (2)	−0.001 (3)
C7	0.030 (2)	0.034 (2)	0.030 (2)	0.0008 (19)	0.0067 (18)	−0.0015 (19)
C8	0.028 (2)	0.034 (2)	0.030 (2)	0.0032 (19)	0.0029 (17)	0.0000 (19)
C9	0.034 (2)	0.032 (2)	0.029 (2)	0.0000 (19)	0.0034 (18)	−0.0003 (19)
C10	0.032 (2)	0.026 (2)	0.028 (2)	0.0039 (18)	0.0082 (18)	0.0025 (18)
C11	0.039 (3)	0.028 (2)	0.031 (2)	0.004 (2)	0.0072 (19)	0.0029 (19)
C12	0.058 (3)	0.035 (3)	0.029 (2)	0.002 (2)	0.011 (2)	0.001 (2)
C13	0.063 (4)	0.039 (3)	0.035 (3)	0.000 (3)	0.023 (2)	0.003 (2)
C14	0.045 (3)	0.039 (3)	0.054 (3)	−0.002 (2)	0.021 (3)	0.005 (3)
C15	0.036 (3)	0.039 (3)	0.039 (3)	0.000 (2)	0.012 (2)	0.007 (2)
C16	0.034 (3)	0.044 (3)	0.031 (2)	0.006 (2)	−0.0011 (19)	0.003 (2)
C17	0.052 (3)	0.049 (3)	0.058 (4)	0.020 (3)	0.020 (3)	0.014 (3)

S1—O2	1.424 (4)	C4—C5	1.371 (9)
S1—O3	1.428 (4)	C4—H4	0.9300
S1—N1	1.648 (4)	C5—C6	1.384 (8)
S1—C1	1.755 (5)	C5—H5	0.9300
O4—C9	1.242 (6)	C6—H6	0.9300
O5—C16	1.246 (6)	C7—C8	1.364 (6)
N1—C8	1.433 (6)	C8—C9	1.464 (6)
N1—C17	1.484 (7)	C10—C15	1.403 (6)
N2—C9	1.337 (6)	C10—C11	1.413 (6)
N2—C10	1.412 (5)	C11—C12	1.380 (6)
N2—H2	0.8600	C11—C16	1.488 (7)
N3—C16	1.333 (6)	C12—C13	1.372 (8)
N3—H3A	0.8600	C12—H12	0.9300
N3—H3B	0.8600	C13—C14	1.378 (8)
O1—C7	1.335 (5)	C13—H13	0.9300
O1—H1	0.8200	C14—C15	1.379 (7)
C1—C6	1.372 (7)	C14—H14	0.9300
C1—C2	1.407 (7)	C15—H15	0.9300
C2—C3	1.385 (7)	C17—H17A	0.9600
C2—C7	1.471 (6)	C17—H17B	0.9600
C3—C4	1.379 (8)	C17—H17C	0.9600
C3—H3	0.9300
O2—S1—O3	119.2 (3)	O1—C7—C2	114.2 (4)
O2—S1—N1	108.0 (2)	C8—C7—C2	122.3 (4)
O3—S1—N1	108.4 (2)	C7—C8—N1	121.2 (4)
O2—S1—C1	108.6 (2)	C7—C8—C9	120.8 (4)
O3—S1—C1	109.9 (2)	N1—C8—C9	117.9 (4)
N1—S1—C1	101.3 (2)	O4—C9—N2	123.4 (4)
C8—N1—C17	115.4 (4)	O4—C9—C8	120.3 (4)
C8—N1—S1	113.0 (3)	N2—C9—C8	116.3 (4)
C17—N1—S1	115.1 (3)	C15—C10—N2	121.8 (4)
C9—N2—C10	129.2 (4)	C15—C10—C11	119.3 (4)
C9—N2—H2	115.4	N2—C10—C11	118.9 (4)
C10—N2—H2	115.4	C12—C11—C10	118.4 (5)
C16—N3—H3A	120.0	C12—C11—C16	120.9 (5)
C16—N3—H3B	120.0	C10—C11—C16	120.8 (4)
H3A—N3—H3B	120.0	C13—C12—C11	122.1 (5)
C7—O1—H1	109.5	C13—C12—H12	119.0
C6—C1—C2	122.0 (5)	C11—C12—H12	119.0
C6—C1—S1	122.2 (4)	C12—C13—C14	119.7 (5)
C2—C1—S1	115.8 (3)	C12—C13—H13	120.2
C3—C2—C1	118.0 (5)	C14—C13—H13	120.2
C3—C2—C7	121.5 (5)	C13—C14—C15	120.4 (5)
C1—C2—C7	120.5 (4)	C13—C14—H14	119.8
C4—C3—C2	119.9 (6)	C15—C14—H14	119.8
C4—C3—H3	120.1	C14—C15—C10	120.2 (5)
C2—C3—H3	120.1	C14—C15—H15	119.9
C5—C4—C3	121.2 (5)	C10—C15—H15	119.9
C5—C4—H4	119.4	O5—C16—N3	120.8 (5)
C3—C4—H4	119.4	O5—C16—C11	121.6 (4)
C4—C5—C6	120.4 (5)	N3—C16—C11	117.6 (4)
C4—C5—H5	119.8	N1—C17—H17A	109.5
C6—C5—H5	119.8	N1—C17—H17B	109.5
C1—C6—C5	118.5 (5)	H17A—C17—H17B	109.5
C1—C6—H6	120.7	N1—C17—H17C	109.5
C5—C6—H6	120.7	H17A—C17—H17C	109.5
O1—C7—C8	123.6 (4)	H17B—C17—H17C	109.5
O2—S1—N1—C8	58.6 (4)	O1—C7—C8—C9	2.6 (8)
O3—S1—N1—C8	−171.0 (3)	C2—C7—C8—C9	−176.4 (4)
C1—S1—N1—C8	−55.4 (4)	C17—N1—C8—C7	−96.6 (6)
O2—S1—N1—C17	−165.8 (4)	S1—N1—C8—C7	38.8 (6)
O3—S1—N1—C17	−35.4 (4)	C17—N1—C8—C9	82.0 (5)
C1—S1—N1—C17	80.2 (4)	S1—N1—C8—C9	−142.6 (4)
O2—S1—C1—C6	106.1 (5)	C10—N2—C9—O4	−2.0 (8)
O3—S1—C1—C6	−25.9 (5)	C10—N2—C9—C8	176.5 (4)
N1—S1—C1—C6	−140.4 (5)	C7—C8—C9—O4	−0.9 (8)
O2—S1—C1—C2	−72.5 (4)	N1—C8—C9—O4	−179.6 (5)
O3—S1—C1—C2	155.5 (4)	C7—C8—C9—N2	−179.5 (5)
N1—S1—C1—C2	41.0 (4)	N1—C8—C9—N2	1.9 (7)
C6—C1—C2—C3	−3.9 (8)	C9—N2—C10—C15	19.3 (8)
S1—C1—C2—C3	174.7 (4)	C9—N2—C10—C11	−160.5 (5)
C6—C1—C2—C7	173.4 (5)	C15—C10—C11—C12	−0.6 (7)
S1—C1—C2—C7	−8.0 (6)	N2—C10—C11—C12	179.2 (4)
C1—C2—C3—C4	2.4 (8)	C15—C10—C11—C16	178.9 (4)
C7—C2—C3—C4	−174.9 (5)	N2—C10—C11—C16	−1.3 (7)
C2—C3—C4—C5	0.7 (10)	C10—C11—C12—C13	−1.7 (8)
C3—C4—C5—C6	−2.4 (11)	C16—C11—C12—C13	178.8 (5)
C2—C1—C6—C5	2.2 (9)	C11—C12—C13—C14	2.2 (8)
S1—C1—C6—C5	−176.3 (5)	C12—C13—C14—C15	−0.2 (8)
C4—C5—C6—C1	0.9 (10)	C13—C14—C15—C10	−2.1 (8)
C3—C2—C7—O1	−20.1 (7)	N2—C10—C15—C14	−177.3 (5)
C1—C2—C7—O1	162.7 (5)	C11—C10—C15—C14	2.5 (7)
C3—C2—C7—C8	159.0 (5)	C12—C11—C16—O5	160.7 (5)
C1—C2—C7—C8	−18.2 (7)	C10—C11—C16—O5	−18.7 (8)
O1—C7—C8—N1	−178.8 (4)	C12—C11—C16—N3	−19.5 (7)
C2—C7—C8—N1	2.1 (7)	C10—C11—C16—N3	161.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.85	2.569 (5)	145
N2—H2···O5	0.86	1.92	2.607 (5)	136
N2—H2···N1	0.86	2.28	2.728 (5)	113
N3—H3A···O5i	0.86	2.22	2.941 (6)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.85	2.569 (5)	145
N2—H2⋯O5	0.86	1.92	2.607 (5)	136
N2—H2⋯N1	0.86	2.28	2.728 (5)	113
N3—H3A⋯O5i	0.86	2.22	2.941 (6)	141

Symmetry code: (i) .