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

1,2-Benzothia-zines similar to the title compound, C(18)H(18)N(2)O(4)S, are well known in the literature for their biological activities and are used as medicines in the treatment of inflammation and rheumatoid arthritis. The thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. In the crystal, mol-ecules arrange themselves into centrosymmetric dimers by means of pairs of weak inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the synthesis of related mol­ecules, see: Siddiqui et al. (2007 ▶); Zia-ur-Rehman et al. (2005 ▶). For the biological activity of 1,2-benzothia­zine-1,1-dioxides, see: Turck et al. (1996 ▶); Zia-ur-Rehman et al. (2006 ▶, 2009 ▶). For related structures, see: Golič & Leban (1987 ▶). For the pharmacological background to 1,2-benzothia­zine-3-carboxamide 1,1-dioxide derivatives, see Gennari et al. (1994 ▶); Bihovsky et al. (2004 ▶).

Experimental

Crystal data

C18H18N2O4S

M = 358.40

Triclinic,

a = 7.5458 (4) Å

b = 8.0214 (3) Å

c = 14.4832 (7) Å

α = 89.864 (3)°

β = 79.530 (2)°

γ = 73.812 (3)°

V = 826.78 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 120 K

0.27 × 0.13 × 0.03 mm

Data collection

Bruker–Nonius CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.942, T max = 0.993

13798 measured reflections

3783 independent reflections

2808 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.05

3783 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.45 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010058/bt2906sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010058/bt2906Isup2.hkl

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

C18H18N2O4S	Z = 2
Mr = 358.40	F(000) = 376
Triclinic, P1	Dx = 1.440 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5458 (4) Å	Cell parameters from 8399 reflections
b = 8.0214 (3) Å	θ = 2.9–27.5°
c = 14.4832 (7) Å	µ = 0.22 mm−1
α = 89.864 (3)°	T = 120 K
β = 79.530 (2)°	Slab, colourless
γ = 73.812 (3)°	0.27 × 0.13 × 0.03 mm
V = 826.78 (7) Å3

Bruker–Nonius CCD camera on κ-goniostat diffractometer	3783 independent reflections
Radiation source: Bruker–Nonius FR591 Rotating Anode	2808 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans to fill the asymmetric unit	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −10→10
Tmin = 0.942, Tmax = 0.993	l = −18→18
13798 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2877P] where P = (Fo2 + 2Fc2)/3
3783 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6504 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command

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	0.31447 (7)	0.72556 (6)	0.43102 (3)	0.01788 (15)
O1	0.3403 (2)	0.73723 (17)	0.52605 (9)	0.0238 (3)
O2	0.1712 (2)	0.65260 (17)	0.41180 (10)	0.0212 (3)
O3	0.6047 (2)	0.46253 (18)	0.12076 (10)	0.0272 (4)
O4	0.4283 (2)	0.78465 (18)	0.13671 (9)	0.0239 (3)
H4	0.4834	0.6873	0.1088	0.036*
N1	0.5143 (2)	0.6143 (2)	0.36582 (11)	0.0176 (4)
N2	0.6598 (2)	0.3138 (2)	0.25259 (12)	0.0194 (4)
H2	0.6433	0.3259	0.3142	0.023*
C1	0.2807 (3)	0.9323 (2)	0.38337 (14)	0.0171 (4)
C2	0.1944 (3)	1.0828 (2)	0.43980 (15)	0.0201 (4)
H2A	0.1576	1.0773	0.5058	0.024*
C3	0.1629 (3)	1.2423 (2)	0.39801 (15)	0.0215 (5)
H3	0.1029	1.3468	0.4354	0.026*
C4	0.2191 (3)	1.2483 (3)	0.30167 (15)	0.0222 (5)
H4A	0.1977	1.3576	0.2737	0.027*
C5	0.3058 (3)	1.0979 (3)	0.24565 (14)	0.0202 (4)
H5	0.3424	1.1045	0.1797	0.024*
C6	0.3397 (3)	0.9359 (2)	0.28595 (14)	0.0177 (4)
C7	0.4321 (3)	0.7733 (2)	0.22839 (14)	0.0181 (4)
C8	0.5104 (3)	0.6205 (2)	0.26674 (13)	0.0176 (4)
C9	0.5948 (3)	0.4596 (3)	0.20776 (14)	0.0193 (4)
C10	0.7520 (3)	0.1427 (2)	0.21235 (14)	0.0180 (4)
C11	0.7367 (3)	0.0876 (3)	0.12370 (15)	0.0212 (4)
H11	0.6628	0.1666	0.0871	0.025*
C12	0.8283 (3)	−0.0820 (3)	0.08799 (14)	0.0201 (4)
C13	0.9391 (3)	−0.1984 (2)	0.14171 (14)	0.0190 (4)
C14	0.9516 (3)	−0.1413 (2)	0.23036 (14)	0.0198 (4)
H14	1.0254	−0.2197	0.2673	0.024*
C15	0.8592 (3)	0.0269 (2)	0.26607 (14)	0.0191 (4)
H15	0.8692	0.0628	0.3269	0.023*
C16	0.6865 (3)	0.6405 (3)	0.39200 (16)	0.0245 (5)
H16A	0.7975	0.5564	0.3557	0.037*
H16B	0.6829	0.6238	0.4593	0.037*
H16C	0.6924	0.7587	0.3782	0.037*
C17	0.8062 (3)	−0.1375 (3)	−0.00753 (15)	0.0282 (5)
H17A	0.7218	−0.0405	−0.0334	0.042*
H17B	0.7532	−0.2363	−0.0018	0.042*
H17C	0.9292	−0.1716	−0.0495	0.042*
C18	1.0438 (3)	−0.3820 (3)	0.10461 (16)	0.0273 (5)
H18A	1.1256	−0.4384	0.1478	0.041*
H18B	1.1202	−0.3793	0.0425	0.041*
H18C	0.9536	−0.4472	0.0995	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0253 (3)	0.0134 (2)	0.0139 (3)	−0.0045 (2)	−0.0023 (2)	0.00043 (18)
O1	0.0374 (9)	0.0178 (7)	0.0141 (8)	−0.0048 (7)	−0.0048 (7)	−0.0002 (6)
O2	0.0253 (8)	0.0165 (7)	0.0218 (8)	−0.0081 (6)	−0.0015 (6)	0.0003 (6)
O3	0.0358 (9)	0.0250 (8)	0.0154 (8)	−0.0022 (7)	−0.0013 (7)	−0.0013 (6)
O4	0.0338 (9)	0.0206 (7)	0.0137 (8)	−0.0032 (7)	−0.0027 (7)	0.0004 (6)
N1	0.0201 (9)	0.0172 (8)	0.0142 (9)	−0.0028 (7)	−0.0038 (7)	−0.0003 (7)
N2	0.0233 (10)	0.0179 (8)	0.0139 (9)	−0.0021 (7)	−0.0012 (7)	−0.0036 (7)
C1	0.0180 (10)	0.0165 (9)	0.0182 (11)	−0.0057 (8)	−0.0057 (8)	0.0011 (8)
C2	0.0251 (11)	0.0179 (9)	0.0182 (11)	−0.0074 (9)	−0.0038 (9)	−0.0006 (8)
C3	0.0246 (11)	0.0146 (9)	0.0254 (12)	−0.0050 (9)	−0.0060 (9)	−0.0013 (8)
C4	0.0267 (12)	0.0158 (10)	0.0267 (12)	−0.0078 (9)	−0.0088 (9)	0.0056 (8)
C5	0.0236 (11)	0.0224 (10)	0.0173 (11)	−0.0103 (9)	−0.0049 (9)	0.0048 (8)
C6	0.0179 (10)	0.0181 (10)	0.0184 (11)	−0.0066 (8)	−0.0045 (8)	0.0013 (8)
C7	0.0199 (11)	0.0203 (10)	0.0151 (10)	−0.0082 (9)	−0.0021 (8)	0.0014 (8)
C8	0.0204 (11)	0.0188 (10)	0.0131 (10)	−0.0057 (8)	−0.0020 (8)	0.0003 (8)
C9	0.0186 (11)	0.0220 (10)	0.0155 (11)	−0.0046 (9)	−0.0007 (8)	−0.0005 (8)
C10	0.0165 (10)	0.0183 (10)	0.0178 (11)	−0.0050 (8)	0.0000 (8)	−0.0022 (8)
C11	0.0225 (11)	0.0194 (10)	0.0209 (11)	−0.0033 (9)	−0.0066 (9)	0.0010 (8)
C12	0.0222 (11)	0.0223 (10)	0.0164 (11)	−0.0085 (9)	−0.0017 (9)	−0.0026 (8)
C13	0.0204 (11)	0.0172 (9)	0.0187 (11)	−0.0056 (8)	−0.0013 (9)	−0.0010 (8)
C14	0.0204 (11)	0.0194 (10)	0.0204 (11)	−0.0054 (9)	−0.0063 (9)	0.0019 (8)
C15	0.0215 (11)	0.0227 (10)	0.0143 (10)	−0.0084 (9)	−0.0033 (8)	−0.0013 (8)
C16	0.0247 (12)	0.0264 (11)	0.0249 (12)	−0.0087 (9)	−0.0090 (9)	0.0017 (9)
C17	0.0380 (14)	0.0252 (11)	0.0190 (11)	−0.0041 (10)	−0.0071 (10)	−0.0043 (9)
C18	0.0330 (13)	0.0203 (10)	0.0265 (12)	−0.0032 (10)	−0.0071 (10)	−0.0033 (9)

S1—O1	1.4317 (14)	C7—C8	1.368 (3)
S1—O2	1.4326 (14)	C8—C9	1.467 (3)
S1—N1	1.6427 (17)	C10—C15	1.389 (3)
S1—C1	1.7646 (19)	C10—C11	1.394 (3)
O3—C9	1.249 (2)	C11—C12	1.395 (3)
O4—C7	1.336 (2)	C11—H11	0.9500
O4—H4	0.8400	C12—C13	1.405 (3)
N1—C8	1.441 (2)	C12—C17	1.506 (3)
N1—C16	1.485 (3)	C13—C14	1.392 (3)
N2—C9	1.350 (3)	C13—C18	1.511 (3)
N2—C10	1.425 (2)	C14—C15	1.387 (3)
N2—H2	0.8800	C14—H14	0.9500
C1—C2	1.387 (3)	C15—H15	0.9500
C1—C6	1.403 (3)	C16—H16A	0.9800
C2—C3	1.392 (3)	C16—H16B	0.9800
C2—H2A	0.9500	C16—H16C	0.9800
C3—C4	1.388 (3)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.383 (3)	C17—H17C	0.9800
C4—H4A	0.9500	C18—H18A	0.9800
C5—C6	1.400 (3)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.473 (3)
O1—S1—O2	118.91 (8)	O3—C9—C8	120.03 (18)
O1—S1—N1	108.79 (9)	N2—C9—C8	116.48 (17)
O2—S1—N1	107.59 (8)	C15—C10—C11	119.54 (18)
O1—S1—C1	109.51 (9)	C15—C10—N2	117.23 (17)
O2—S1—C1	108.75 (9)	C11—C10—N2	123.23 (18)
N1—S1—C1	101.94 (9)	C10—C11—C12	120.92 (19)
C7—O4—H4	109.5	C10—C11—H11	119.5
C8—N1—C16	114.78 (16)	C12—C11—H11	119.5
C8—N1—S1	112.57 (13)	C11—C12—C13	119.55 (18)
C16—N1—S1	115.69 (13)	C11—C12—C17	119.35 (18)
C9—N2—C10	127.93 (17)	C13—C12—C17	121.10 (18)
C9—N2—H2	116.0	C14—C13—C12	118.72 (18)
C10—N2—H2	116.0	C14—C13—C18	120.17 (18)
C2—C1—C6	122.11 (18)	C12—C13—C18	121.12 (18)
C2—C1—S1	121.06 (15)	C15—C14—C13	121.66 (19)
C6—C1—S1	116.80 (14)	C15—C14—H14	119.2
C1—C2—C3	118.78 (19)	C13—C14—H14	119.2
C1—C2—H2A	120.6	C14—C15—C10	119.61 (18)
C3—C2—H2A	120.6	C14—C15—H15	120.2
C4—C3—C2	119.89 (18)	C10—C15—H15	120.2
C4—C3—H3	120.1	N1—C16—H16A	109.5
C2—C3—H3	120.1	N1—C16—H16B	109.5
C5—C4—C3	121.17 (18)	H16A—C16—H16B	109.5
C5—C4—H4A	119.4	N1—C16—H16C	109.5
C3—C4—H4A	119.4	H16A—C16—H16C	109.5
C4—C5—C6	120.08 (19)	H16B—C16—H16C	109.5
C4—C5—H5	120.0	C12—C17—H17A	109.5
C6—C5—H5	120.0	C12—C17—H17B	109.5
C5—C6—C1	117.96 (18)	H17A—C17—H17B	109.5
C5—C6—C7	121.49 (18)	C12—C17—H17C	109.5
C1—C6—C7	120.55 (17)	H17A—C17—H17C	109.5
O4—C7—C8	122.55 (18)	H17B—C17—H17C	109.5
O4—C7—C6	115.15 (17)	C13—C18—H18A	109.5
C8—C7—C6	122.27 (18)	C13—C18—H18B	109.5
C7—C8—N1	120.84 (17)	H18A—C18—H18B	109.5
C7—C8—C9	120.78 (18)	C13—C18—H18C	109.5
N1—C8—C9	118.37 (16)	H18A—C18—H18C	109.5
O3—C9—N2	123.49 (18)	H18B—C18—H18C	109.5
O1—S1—N1—C8	−170.25 (12)	C6—C7—C8—N1	−3.3 (3)
O2—S1—N1—C8	59.69 (14)	O4—C7—C8—C9	−0.2 (3)
C1—S1—N1—C8	−54.62 (14)	C6—C7—C8—C9	177.62 (17)
O1—S1—N1—C16	−35.53 (16)	C16—N1—C8—C7	−91.7 (2)
O2—S1—N1—C16	−165.58 (13)	S1—N1—C8—C7	43.5 (2)
C1—S1—N1—C16	80.10 (15)	C16—N1—C8—C9	87.5 (2)
O1—S1—C1—C2	−31.1 (2)	S1—N1—C8—C9	−137.36 (16)
O2—S1—C1—C2	100.31 (18)	C10—N2—C9—O3	1.4 (3)
N1—S1—C1—C2	−146.23 (17)	C10—N2—C9—C8	−178.11 (17)
O1—S1—C1—C6	150.83 (15)	C7—C8—C9—O3	3.8 (3)
O2—S1—C1—C6	−77.72 (17)	N1—C8—C9—O3	−175.38 (18)
N1—S1—C1—C6	35.73 (17)	C7—C8—C9—N2	−176.68 (18)
C6—C1—C2—C3	1.0 (3)	N1—C8—C9—N2	4.2 (3)
S1—C1—C2—C3	−176.88 (15)	C9—N2—C10—C15	159.47 (19)
C1—C2—C3—C4	−0.6 (3)	C9—N2—C10—C11	−21.5 (3)
C2—C3—C4—C5	0.3 (3)	C15—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	−0.5 (3)	N2—C10—C11—C12	−179.32 (18)
C4—C5—C6—C1	0.9 (3)	C10—C11—C12—C13	−0.7 (3)
C4—C5—C6—C7	−179.85 (18)	C10—C11—C12—C17	179.17 (19)
C2—C1—C6—C5	−1.2 (3)	C11—C12—C13—C14	1.1 (3)
S1—C1—C6—C5	176.80 (15)	C17—C12—C13—C14	−178.73 (19)
C2—C1—C6—C7	179.56 (19)	C11—C12—C13—C18	−178.68 (19)
S1—C1—C6—C7	−2.4 (3)	C17—C12—C13—C18	1.5 (3)
C5—C6—C7—O4	−19.6 (3)	C12—C13—C14—C15	−0.6 (3)
C1—C6—C7—O4	159.62 (18)	C18—C13—C14—C15	179.19 (19)
C5—C6—C7—C8	162.50 (19)	C13—C14—C15—C10	−0.4 (3)
C1—C6—C7—C8	−18.3 (3)	C11—C10—C15—C14	0.8 (3)
O4—C7—C8—N1	178.98 (17)	N2—C10—C15—C14	179.89 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.84	1.80	2.545 (2)	146
N2—H2···O1i	0.88	2.39	3.231 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.84	1.80	2.545 (2)	146
N2—H2⋯O1i	0.88	2.39	3.231 (2)	161

Symmetry code: (i) .