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

In the crystal structure of the title compound, C(18)H(18)N(2)O(4)S, the thia-zine ring adopts a distorted half-chair conformation. 1,2-Benzothia-zines of this kind have a wide range of biological activities and are mainly used as medicines in the treatment of inflammation and rheumatoid arthritis. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. The mol-ecules arrange themselves into centrosymmetric dimers by means of inter-molecular N-H⋯O hydrogen bonds. A weak inter-molcular C-H⋯O inter-action is also present.

Related literature

For the synthesis of related mol­ecules, see: Siddiqui, Ahmad, Khan et al. (2007 ▶); Zia-ur-Rehman et al. (2006 ▶); For the biological activity of 1,2-benzothia­zine-1,1-dioxides, see: Zia-ur-Rehman et al. (2009 ▶). For related structures, see: Siddiqui et al. (2008 ▶); Siddiqui, Ahmad, Siddiqui et al. (2007 ▶). For the pharmacological background to 1,2-benzothia­zine-3-carboxamide 1,1-dioxide derivatives, see Gennari et al. (1994 ▶); Lombardino & Wiseman (1972 ▶).

Experimental

Crystal data

C18H18N2O4S

M = 358.40

Monoclinic,

a = 10.2461 (3) Å

b = 8.5421 (2) Å

c = 19.8944 (5) Å

β = 104.832 (1)°

V = 1683.20 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 120 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker–Nonius CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.855, T max = 0.978

18371 measured reflections

3828 independent reflections

3000 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 1.06

3828 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.57 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/S1600536809006837/bt2887sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006837/bt2887Isup2.hkl

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

C18H18N2O4S	F(000) = 752
Mr = 358.40	Dx = 1.414 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10340 reflections
a = 10.2461 (3) Å	θ = 2.9–27.5°
b = 8.5421 (2) Å	µ = 0.22 mm−1
c = 19.8944 (5) Å	T = 120 K
β = 104.832 (1)°	Block, colourless
V = 1683.20 (8) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Bruker–Nonius CCD camera on κ-goniostat diffractometer	3828 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	3000 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans to fill the asymmetric unit	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→9
Tmin = 0.855, Tmax = 0.978	l = −25→24
18371 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.8901P] where P = (Fo2 + 2Fc2)/3
3828 reflections	(Δ/σ)max = 0.001
234 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

Experimental. SADABS was used to perform the Absorption correction Parameter refinement on 11612 reflections reduced R(int) from 0.0681 to 0.0328 Ratio of minimum to maximum apparent transmission: 0.867291 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	0.65769 (5)	0.38059 (5)	0.08727 (2)	0.01787 (14)
O2	0.85778 (13)	0.51574 (15)	−0.10128 (6)	0.0190 (3)
O1	0.93907 (13)	0.27205 (16)	−0.03046 (7)	0.0208 (3)
H1O	0.9310	0.3360	−0.0633	0.031*
N2	0.70234 (16)	0.67387 (18)	−0.06965 (8)	0.0162 (3)
N1	0.73387 (15)	0.51959 (17)	0.05471 (8)	0.0155 (3)
O3	0.55860 (13)	0.31248 (15)	0.03050 (7)	0.0207 (3)
O4	0.61656 (14)	0.44317 (17)	0.14534 (7)	0.0255 (3)
C6	0.88260 (18)	0.2273 (2)	0.07631 (9)	0.0173 (4)
C9	0.78894 (18)	0.5530 (2)	−0.05975 (9)	0.0154 (4)
C10	0.67298 (17)	0.7818 (2)	−0.12596 (9)	0.0166 (4)
C7	0.87323 (18)	0.3265 (2)	0.01508 (9)	0.0162 (4)
C1	0.78842 (19)	0.2430 (2)	0.11619 (9)	0.0187 (4)
C18	0.8113 (2)	0.6356 (2)	0.10495 (10)	0.0226 (4)
H18A	0.8911	0.5851	0.1348	0.034*
H18B	0.7542	0.6764	0.1336	0.034*
H18C	0.8397	0.7220	0.0795	0.034*
C5	0.98373 (19)	0.1138 (2)	0.09600 (10)	0.0216 (4)
H5	1.0480	0.1000	0.0695	0.026*
C8	0.80079 (18)	0.4615 (2)	0.00417 (9)	0.0151 (4)
C14	0.61045 (19)	1.0447 (2)	−0.16562 (11)	0.0226 (4)
C16	0.6568 (2)	0.9831 (2)	−0.03662 (10)	0.0233 (4)
H16A	0.5896	0.9260	−0.0190	0.035*
H16B	0.6410	1.0959	−0.0344	0.035*
H16C	0.7475	0.9578	−0.0082	0.035*
C4	0.9901 (2)	0.0215 (2)	0.15404 (11)	0.0266 (5)
H4	1.0594	−0.0549	0.1672	0.032*
C15	0.64525 (18)	0.9363 (2)	−0.11082 (10)	0.0181 (4)
C12	0.6398 (2)	0.8437 (2)	−0.24637 (10)	0.0246 (4)
H12	0.6402	0.8140	−0.2923	0.030*
C11	0.67017 (19)	0.7340 (2)	−0.19320 (9)	0.0203 (4)
H11	0.6887	0.6283	−0.2025	0.024*
C3	0.8966 (2)	0.0393 (2)	0.19319 (11)	0.0294 (5)
H3	0.9024	−0.0246	0.2329	0.035*
C13	0.6091 (2)	0.9960 (2)	−0.23262 (10)	0.0248 (4)
H13	0.5865	1.0692	−0.2697	0.030*
C2	0.7944 (2)	0.1507 (2)	0.17439 (10)	0.0258 (4)
H2	0.7299	0.1633	0.2009	0.031*
C17	0.5769 (2)	1.2125 (3)	−0.15299 (12)	0.0350 (5)
H17A	0.5529	1.2691	−0.1973	0.052*
H17B	0.6555	1.2624	−0.1217	0.052*
H17C	0.5006	1.2151	−0.1317	0.052*
H1N	0.657 (2)	0.683 (3)	−0.0397 (12)	0.026 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0187 (2)	0.0193 (3)	0.0181 (2)	−0.00080 (18)	0.00918 (18)	−0.00048 (18)
O2	0.0210 (7)	0.0221 (7)	0.0160 (6)	0.0015 (5)	0.0085 (5)	0.0000 (5)
O1	0.0218 (7)	0.0229 (7)	0.0208 (7)	0.0045 (6)	0.0112 (6)	0.0014 (5)
N2	0.0159 (8)	0.0182 (8)	0.0155 (8)	0.0018 (6)	0.0062 (6)	0.0012 (6)
N1	0.0162 (8)	0.0170 (8)	0.0151 (7)	−0.0005 (6)	0.0073 (6)	−0.0023 (6)
O3	0.0156 (7)	0.0230 (7)	0.0245 (7)	−0.0022 (5)	0.0072 (5)	−0.0032 (6)
O4	0.0325 (8)	0.0269 (8)	0.0232 (7)	0.0000 (6)	0.0183 (6)	−0.0027 (6)
C6	0.0168 (9)	0.0173 (9)	0.0163 (9)	−0.0034 (7)	0.0018 (7)	−0.0016 (7)
C9	0.0157 (9)	0.0163 (9)	0.0136 (8)	−0.0038 (7)	0.0028 (7)	−0.0017 (7)
C10	0.0121 (8)	0.0192 (9)	0.0170 (9)	−0.0021 (7)	0.0013 (7)	0.0026 (7)
C7	0.0130 (8)	0.0187 (9)	0.0171 (9)	−0.0023 (7)	0.0041 (7)	−0.0018 (7)
C1	0.0223 (9)	0.0172 (9)	0.0161 (9)	−0.0019 (7)	0.0037 (7)	−0.0020 (7)
C18	0.0263 (10)	0.0227 (10)	0.0197 (10)	−0.0050 (8)	0.0075 (8)	−0.0057 (8)
C5	0.0192 (10)	0.0194 (10)	0.0243 (10)	0.0010 (7)	0.0020 (8)	−0.0008 (8)
C8	0.0147 (8)	0.0179 (9)	0.0134 (9)	−0.0015 (7)	0.0049 (7)	−0.0016 (7)
C14	0.0180 (9)	0.0190 (10)	0.0273 (10)	−0.0014 (8)	−0.0003 (8)	0.0024 (8)
C16	0.0267 (11)	0.0192 (10)	0.0250 (10)	0.0004 (8)	0.0083 (9)	−0.0035 (8)
C4	0.0292 (11)	0.0210 (10)	0.0246 (10)	0.0028 (8)	−0.0023 (9)	0.0033 (8)
C15	0.0140 (9)	0.0193 (9)	0.0199 (9)	−0.0028 (7)	0.0025 (7)	−0.0007 (7)
C12	0.0275 (11)	0.0277 (11)	0.0163 (9)	−0.0036 (8)	0.0015 (8)	0.0010 (8)
C11	0.0235 (10)	0.0196 (10)	0.0168 (9)	−0.0011 (8)	0.0034 (8)	−0.0005 (7)
C3	0.0429 (13)	0.0229 (11)	0.0187 (10)	−0.0008 (9)	0.0013 (9)	0.0054 (8)
C13	0.0250 (11)	0.0249 (11)	0.0211 (10)	−0.0024 (8)	−0.0005 (8)	0.0073 (8)
C2	0.0353 (12)	0.0248 (10)	0.0190 (10)	−0.0030 (9)	0.0101 (9)	0.0017 (8)
C17	0.0428 (14)	0.0220 (11)	0.0361 (13)	0.0039 (9)	0.0029 (11)	0.0019 (9)

S1—O4	1.4308 (13)	C5—C4	1.386 (3)
S1—O3	1.4345 (14)	C5—H5	0.9500
S1—N1	1.6424 (15)	C14—C13	1.393 (3)
S1—C1	1.7639 (19)	C14—C15	1.405 (3)
O2—C9	1.257 (2)	C14—C17	1.510 (3)
O1—C7	1.344 (2)	C16—C15	1.504 (3)
O1—H1O	0.8400	C16—H16A	0.9800
N2—C9	1.343 (2)	C16—H16B	0.9800
N2—C10	1.422 (2)	C16—H16C	0.9800
N2—H1N	0.85 (2)	C4—C3	1.389 (3)
N1—C8	1.442 (2)	C4—H4	0.9500
N1—C18	1.485 (2)	C12—C13	1.383 (3)
C6—C5	1.400 (3)	C12—C11	1.388 (3)
C6—C1	1.404 (3)	C12—H12	0.9500
C6—C7	1.467 (3)	C11—H11	0.9500
C9—C8	1.471 (2)	C3—C2	1.394 (3)
C10—C11	1.392 (3)	C3—H3	0.9500
C10—C15	1.399 (3)	C13—H13	0.9500
C7—C8	1.359 (3)	C2—H2	0.9500
C1—C2	1.389 (3)	C17—H17A	0.9800
C18—H18A	0.9800	C17—H17B	0.9800
C18—H18B	0.9800	C17—H17C	0.9800
C18—H18C	0.9800
O4—S1—O3	119.46 (8)	C7—C8—C9	120.66 (16)
O4—S1—N1	108.44 (8)	N1—C8—C9	118.12 (15)
O3—S1—N1	107.14 (8)	C13—C14—C15	118.96 (18)
O4—S1—C1	109.98 (9)	C13—C14—C17	119.71 (18)
O3—S1—C1	108.17 (8)	C15—C14—C17	121.33 (18)
N1—S1—C1	102.26 (8)	C15—C16—H16A	109.5
C7—O1—H1O	109.5	C15—C16—H16B	109.5
C9—N2—C10	127.78 (16)	H16A—C16—H16B	109.5
C9—N2—H1N	115.6 (16)	C15—C16—H16C	109.5
C10—N2—H1N	116.6 (16)	H16A—C16—H16C	109.5
C8—N1—C18	115.56 (14)	H16B—C16—H16C	109.5
C8—N1—S1	112.65 (12)	C5—C4—C3	120.83 (19)
C18—N1—S1	116.30 (12)	C5—C4—H4	119.6
C5—C6—C1	118.36 (17)	C3—C4—H4	119.6
C5—C6—C7	121.28 (17)	C10—C15—C14	118.67 (17)
C1—C6—C7	120.36 (17)	C10—C15—C16	119.51 (17)
O2—C9—N2	123.99 (16)	C14—C15—C16	121.80 (17)
O2—C9—C8	119.87 (16)	C13—C12—C11	120.17 (18)
N2—C9—C8	116.14 (15)	C13—C12—H12	119.9
C11—C10—C15	121.91 (17)	C11—C12—H12	119.9
C11—C10—N2	120.98 (17)	C12—C11—C10	118.68 (18)
C15—C10—N2	117.10 (16)	C12—C11—H11	120.7
O1—C7—C8	122.29 (16)	C10—C11—H11	120.7
O1—C7—C6	114.99 (16)	C4—C3—C2	120.22 (19)
C8—C7—C6	122.71 (16)	C4—C3—H3	119.9
C2—C1—C6	121.79 (18)	C2—C3—H3	119.9
C2—C1—S1	121.16 (15)	C12—C13—C14	121.55 (18)
C6—C1—S1	117.01 (14)	C12—C13—H13	119.2
N1—C18—H18A	109.5	C14—C13—H13	119.2
N1—C18—H18B	109.5	C1—C2—C3	118.73 (19)
H18A—C18—H18B	109.5	C1—C2—H2	120.6
N1—C18—H18C	109.5	C3—C2—H2	120.6
H18A—C18—H18C	109.5	C14—C17—H17A	109.5
H18B—C18—H18C	109.5	C14—C17—H17B	109.5
C4—C5—C6	120.06 (18)	H17A—C17—H17B	109.5
C4—C5—H5	120.0	C14—C17—H17C	109.5
C6—C5—H5	120.0	H17A—C17—H17C	109.5
C7—C8—N1	121.22 (16)	H17B—C17—H17C	109.5
O4—S1—N1—C8	169.35 (12)	C6—C7—C8—C9	−176.92 (16)
O3—S1—N1—C8	−60.45 (14)	C18—N1—C8—C7	94.4 (2)
C1—S1—N1—C8	53.19 (14)	S1—N1—C8—C7	−42.6 (2)
O4—S1—N1—C18	32.66 (15)	C18—N1—C8—C9	−85.4 (2)
O3—S1—N1—C18	162.85 (13)	S1—N1—C8—C9	137.60 (14)
C1—S1—N1—C18	−83.51 (14)	O2—C9—C8—C7	−7.7 (3)
C10—N2—C9—O2	−1.0 (3)	N2—C9—C8—C7	172.23 (16)
C10—N2—C9—C8	179.07 (16)	O2—C9—C8—N1	172.09 (16)
C9—N2—C10—C11	35.7 (3)	N2—C9—C8—N1	−8.0 (2)
C9—N2—C10—C15	−145.22 (18)	C6—C5—C4—C3	0.3 (3)
C5—C6—C7—O1	18.7 (2)	C11—C10—C15—C14	1.6 (3)
C1—C6—C7—O1	−160.50 (16)	N2—C10—C15—C14	−177.46 (16)
C5—C6—C7—C8	−162.85 (18)	C11—C10—C15—C16	−176.85 (17)
C1—C6—C7—C8	18.0 (3)	N2—C10—C15—C16	4.1 (2)
C5—C6—C1—C2	0.7 (3)	C13—C14—C15—C10	−2.1 (3)
C7—C6—C1—C2	179.90 (17)	C17—C14—C15—C10	178.91 (18)
C5—C6—C1—S1	−176.97 (14)	C13—C14—C15—C16	176.29 (18)
C7—C6—C1—S1	2.2 (2)	C17—C14—C15—C16	−2.7 (3)
O4—S1—C1—C2	32.47 (18)	C13—C12—C11—C10	−2.0 (3)
O3—S1—C1—C2	−99.61 (17)	C15—C10—C11—C12	0.5 (3)
N1—S1—C1—C2	147.51 (16)	N2—C10—C11—C12	179.45 (17)
O4—S1—C1—C6	−149.86 (14)	C5—C4—C3—C2	0.1 (3)
O3—S1—C1—C6	78.06 (16)	C11—C12—C13—C14	1.4 (3)
N1—S1—C1—C6	−34.82 (16)	C15—C14—C13—C12	0.6 (3)
C1—C6—C5—C4	−0.7 (3)	C17—C14—C13—C12	179.7 (2)
C7—C6—C5—C4	−179.94 (17)	C6—C1—C2—C3	−0.2 (3)
O1—C7—C8—N1	−178.38 (15)	S1—C1—C2—C3	177.33 (16)
C6—C7—C8—N1	3.3 (3)	C4—C3—C2—C1	−0.2 (3)
O1—C7—C8—C9	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.84	1.79	2.5320 (18)	147
N2—H1N···O3i	0.85 (2)	2.26 (2)	2.972 (2)	141 (2)
C3—H3···O4ii	0.95	2.49	3.352 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2	0.84	1.79	2.5320 (18)	147
N2—H1N⋯O3i	0.85 (2)	2.26 (2)	2.972 (2)	141 (2)
C3—H3⋯O4ii	0.95	2.49	3.352 (3)	150

Symmetry codes: (i) ; (ii) .