Methyl 2-methyl-4-(oxiran-2-ylmeth-oxy)-2H-1,2-benzothia-zine-3-carboxyl-ate 1,1-dioxide.

In the title compound, C(14)H(15)NO(6)S, the thia-zine ring adopts a distorted half-chair conformation. The structure displays several cooperative weak inter-molecular C-H⋯O hydrogen-bonding inter-actions, giving rise to a two-dimensional sheet packing motif. The CH(2) group in the meth-oxy linker to the oxirane ring, and the CH group in that ring, exhibit twofold positional disorder. The three-membered oxirane ring is twisted approximately perpendicular with respect to thia-zine ring (dihedral angle = 60/86° for the major/minor disorder components). 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.

Related literature

For the synthesis of related mol­ecules, see: Zia-ur-Rehman et al. (2006 ▶, 2007 ▶, 2009 ▶). For the biological activity of 1,2-benzothia­zine 1,1-dioxides, see: Bihovsky et al. (2004 ▶); Fabiola et al. (1998 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶). For similar mol­ecules, see: Ahmad et al. (2008 ▶); Arshad et al. (2009 ▶). For reference bond-length data, see: Weast et al. (1984 ▶).

Experimental

Crystal data

C14H15NO6S

M = 325.33

Monoclinic,

a = 7.2007 (3) Å

b = 12.8435 (6) Å

c = 15.7820 (7) Å

β = 96.5250 (7)°

V = 1450.10 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 300 K

0.44 × 0.37 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.897, T max = 0.942

11439 measured reflections

4516 independent reflections

3651 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.155

S = 1.08

4516 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.27 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000668/bt5151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000668/bt5151Isup2.hkl

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

C14H15NO6S	F(000) = 680
Mr = 325.33	Dx = 1.490 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4610 reflections
a = 7.2007 (3) Å	θ = 2.6–31.4°
b = 12.8435 (6) Å	µ = 0.25 mm−1
c = 15.7820 (7) Å	T = 300 K
β = 96.5250 (7)°	Block, colourless
V = 1450.10 (11) Å3	0.44 × 0.37 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	4516 independent reflections
Radiation source: fine-focus sealed tube	3651 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω rotation with narrow frames scans	θmax = 31.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.897, Tmax = 0.942	k = −18→14
11439 measured reflections	l = −22→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.4338P] where P = (Fo2 + 2Fc2)/3
4516 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.26 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	Occ. (<1)
S1	0.34508 (6)	0.47351 (3)	0.61034 (2)	0.04004 (14)
O1	0.53323 (19)	0.44619 (11)	0.64070 (9)	0.0512 (3)
O2	0.2622 (2)	0.43268 (12)	0.53097 (8)	0.0601 (4)
N2	0.2133 (2)	0.44064 (11)	0.68409 (9)	0.0387 (3)
C3	0.2671 (2)	0.48744 (13)	0.76543 (10)	0.0373 (3)
C4	0.3247 (2)	0.58822 (13)	0.76958 (10)	0.0368 (3)
C5	0.3205 (2)	0.65332 (13)	0.69280 (10)	0.0366 (3)
C6	0.3032 (3)	0.76159 (14)	0.69774 (14)	0.0481 (4)
H6	0.3046	0.7937	0.7506	0.058*
C7	0.2842 (3)	0.82078 (16)	0.62423 (17)	0.0594 (5)
H7	0.2724	0.8927	0.6283	0.071*
C8	0.2823 (3)	0.77530 (17)	0.54444 (16)	0.0571 (5)
H8	0.2684	0.8163	0.4956	0.069*
C9	0.3014 (3)	0.66804 (16)	0.53801 (12)	0.0465 (4)
H9	0.3006	0.6364	0.4850	0.056*
C10	0.3215 (2)	0.60897 (13)	0.61187 (10)	0.0364 (3)
C11	0.0099 (3)	0.43184 (18)	0.65850 (14)	0.0550 (5)
H11A	−0.0408	0.4996	0.6443	0.082*
H11B	−0.0493	0.4034	0.7048	0.082*
H11C	−0.0121	0.3869	0.6098	0.082*
C12	0.2533 (3)	0.42003 (16)	0.84103 (11)	0.0456 (4)
O3	0.2713 (3)	0.44879 (15)	0.91356 (10)	0.0813 (6)
O4	0.2175 (2)	0.32170 (12)	0.81730 (9)	0.0546 (3)
C13	0.2062 (3)	0.2467 (2)	0.88466 (17)	0.0661 (6)
H13A	0.1027	0.2636	0.9154	0.099*
H13B	0.3199	0.2482	0.9229	0.099*
H13C	0.1885	0.1783	0.8605	0.099*
O5	0.37071 (18)	0.63669 (11)	0.84539 (8)	0.0469 (3)
C14	0.5579 (4)	0.6871 (3)	0.8572 (2)	0.0451 (8)	0.646 (6)
H14A	0.5811	0.7217	0.8049	0.054*	0.646 (6)
H14B	0.5605	0.7392	0.9018	0.054*	0.646 (6)
C15	0.7068 (5)	0.6087 (3)	0.8807 (2)	0.0500 (8)	0.646 (6)
H15	0.6875	0.5604	0.9270	0.060*	0.646 (6)
C16	0.8933 (4)	0.6281 (2)	0.8656 (2)	0.0836 (8)
H16A	0.9917	0.5941	0.9028	0.100*	0.646 (6)
H16B	0.9238	0.6977	0.8477	0.100*	0.646 (6)
H16C	0.9273	0.5999	0.9223	0.100*	0.354 (6)
H16D	0.9886	0.6711	0.8444	0.100*	0.354 (6)
O6	0.7826 (3)	0.56506 (15)	0.80605 (13)	0.0782 (5)
C14X	0.5510 (8)	0.6227 (7)	0.8916 (4)	0.057 (2)	0.354 (6)
H14C	0.5688	0.5497	0.9059	0.069*	0.354 (6)
H14D	0.5578	0.6618	0.9444	0.069*	0.354 (6)
C15X	0.7008 (8)	0.6571 (6)	0.8428 (5)	0.0577 (19)	0.354 (6)
H15X	0.6761	0.7179	0.8057	0.069*	0.354 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0542 (3)	0.0363 (2)	0.0306 (2)	0.00076 (16)	0.00890 (16)	−0.00584 (14)
O1	0.0530 (7)	0.0515 (7)	0.0514 (8)	0.0115 (6)	0.0160 (6)	−0.0025 (6)
O2	0.0911 (11)	0.0555 (8)	0.0335 (6)	−0.0064 (7)	0.0059 (7)	−0.0133 (6)
N2	0.0468 (7)	0.0380 (7)	0.0313 (6)	−0.0071 (6)	0.0045 (5)	−0.0030 (5)
C3	0.0402 (8)	0.0430 (8)	0.0289 (7)	−0.0018 (6)	0.0050 (6)	−0.0006 (6)
C4	0.0378 (7)	0.0428 (8)	0.0304 (7)	−0.0006 (6)	0.0065 (5)	−0.0093 (6)
C5	0.0362 (7)	0.0358 (7)	0.0384 (8)	−0.0005 (6)	0.0070 (6)	−0.0037 (6)
C6	0.0459 (9)	0.0390 (8)	0.0603 (11)	0.0014 (7)	0.0103 (8)	−0.0083 (8)
C7	0.0552 (11)	0.0375 (9)	0.0866 (16)	0.0056 (8)	0.0125 (10)	0.0097 (10)
C8	0.0519 (10)	0.0546 (11)	0.0655 (13)	0.0047 (9)	0.0095 (9)	0.0221 (10)
C9	0.0444 (9)	0.0561 (10)	0.0393 (8)	−0.0004 (8)	0.0062 (7)	0.0092 (8)
C10	0.0398 (7)	0.0362 (7)	0.0336 (7)	−0.0002 (6)	0.0064 (6)	−0.0001 (6)
C11	0.0496 (10)	0.0624 (12)	0.0509 (11)	−0.0095 (9)	−0.0028 (8)	−0.0024 (9)
C12	0.0443 (9)	0.0565 (10)	0.0362 (8)	−0.0017 (8)	0.0059 (6)	0.0082 (7)
O3	0.1263 (17)	0.0833 (12)	0.0346 (7)	−0.0132 (11)	0.0108 (9)	0.0083 (7)
O4	0.0625 (8)	0.0499 (8)	0.0511 (8)	−0.0061 (6)	0.0045 (6)	0.0157 (6)
C13	0.0581 (12)	0.0672 (14)	0.0722 (15)	−0.0055 (10)	0.0040 (10)	0.0354 (12)
O5	0.0506 (7)	0.0567 (8)	0.0339 (6)	−0.0054 (6)	0.0068 (5)	−0.0157 (5)
C14	0.0521 (16)	0.0411 (16)	0.0413 (15)	−0.0052 (11)	0.0025 (11)	−0.0107 (13)
C15	0.0631 (19)	0.0476 (18)	0.0383 (15)	0.0020 (14)	0.0021 (12)	−0.0019 (13)
C16	0.0560 (13)	0.0798 (17)	0.112 (2)	0.0020 (12)	−0.0028 (14)	−0.0217 (17)
O6	0.0746 (11)	0.0750 (11)	0.0880 (13)	0.0021 (9)	0.0224 (10)	−0.0291 (10)
C14X	0.043 (3)	0.092 (6)	0.035 (3)	0.005 (3)	−0.003 (2)	−0.016 (3)
C15X	0.049 (3)	0.057 (4)	0.067 (4)	−0.002 (3)	0.007 (3)	−0.010 (3)

S1—O2	1.4249 (14)	C12—O4	1.334 (3)
S1—O1	1.4285 (15)	O4—C13	1.444 (2)
S1—N2	1.6384 (14)	C13—H13A	0.9600
S1—C10	1.7484 (17)	C13—H13B	0.9600
N2—C3	1.430 (2)	C13—H13C	0.9600
N2—C11	1.478 (2)	O5—C14X	1.426 (6)
C3—C4	1.358 (2)	O5—C14	1.488 (3)
C3—C12	1.487 (2)	C14—C15	1.486 (5)
C4—O5	1.3559 (18)	C14—H14A	0.9700
C4—C5	1.470 (2)	C14—H14B	0.9700
C5—C6	1.399 (2)	C15—C16	1.413 (5)
C5—C10	1.399 (2)	C15—O6	1.465 (4)
C6—C7	1.381 (3)	C15—H15	0.9800
C6—H6	0.9300	C16—O6	1.416 (3)
C7—C8	1.387 (3)	C16—C15X	1.441 (7)
C7—H7	0.9300	C16—H16A	0.9700
C8—C9	1.389 (3)	C16—H16B	0.9700
C8—H8	0.9300	C16—H16C	0.9699
C9—C10	1.385 (2)	C16—H16D	0.9701
C9—H9	0.9300	O6—C15X	1.469 (7)
C11—H11A	0.9600	C14X—C15X	1.462 (11)
C11—H11B	0.9600	C14X—H14C	0.9700
C11—H11C	0.9600	C14X—H14D	0.9700
C12—O3	1.196 (2)	C15X—H15X	0.9800
O2—S1—O1	119.39 (9)	H13B—C13—H13C	109.5
O2—S1—N2	108.14 (9)	C4—O5—C14X	120.7 (3)
O1—S1—N2	107.59 (8)	C4—O5—C14	115.97 (16)
O2—S1—C10	110.29 (9)	C15—C14—O5	110.7 (3)
O1—S1—C10	109.25 (8)	C15—C14—H14A	109.5
N2—S1—C10	100.47 (7)	O5—C14—H14A	109.5
C3—N2—C11	115.86 (14)	C15—C14—H14B	109.5
C3—N2—S1	114.17 (11)	O5—C14—H14B	109.5
C11—N2—S1	117.46 (12)	H14A—C14—H14B	108.1
C4—C3—N2	119.59 (14)	C16—C15—O6	58.9 (2)
C4—C3—C12	124.33 (15)	C16—C15—C14	120.8 (4)
N2—C3—C12	116.07 (15)	O6—C15—C14	112.5 (3)
O5—C4—C3	121.52 (15)	C16—C15—H15	117.0
O5—C4—C5	116.50 (15)	O6—C15—H15	117.0
C3—C4—C5	121.65 (14)	C14—C15—H15	117.0
C6—C5—C10	117.72 (16)	C15—C16—O6	62.37 (18)
C6—C5—C4	120.88 (15)	O6—C16—C15X	61.9 (3)
C10—C5—C4	121.28 (14)	C15—C16—H16A	117.5
C7—C6—C5	120.10 (19)	O6—C16—H16A	117.5
C7—C6—H6	120.0	C15X—C16—H16A	152.0
C5—C6—H6	120.0	C15—C16—H16B	117.5
C6—C7—C8	121.39 (19)	O6—C16—H16B	117.5
C6—C7—H7	119.3	C15X—C16—H16B	86.1
C8—C7—H7	119.3	H16A—C16—H16B	114.6
C7—C8—C9	119.55 (19)	C15—C16—H16C	85.6
C7—C8—H8	120.2	O6—C16—H16C	117.6
C9—C8—H8	120.2	C15X—C16—H16C	117.5
C10—C9—C8	118.92 (18)	H16B—C16—H16C	124.8
C10—C9—H9	120.5	C15—C16—H16D	151.9
C8—C9—H9	120.5	O6—C16—H16D	117.6
C9—C10—C5	122.31 (16)	C15X—C16—H16D	117.7
C9—C10—S1	122.33 (13)	H16A—C16—H16D	88.2
C5—C10—S1	115.35 (12)	H16C—C16—H16D	114.7
N2—C11—H11A	109.5	C16—O6—C15	58.70 (19)
N2—C11—H11B	109.5	C16—O6—C15X	59.9 (3)
H11A—C11—H11B	109.5	O5—C14X—C15X	112.1 (6)
N2—C11—H11C	109.5	O5—C14X—H14C	109.2
H11A—C11—H11C	109.5	C15X—C14X—H14C	109.2
H11B—C11—H11C	109.5	O5—C14X—H14D	109.2
O3—C12—O4	123.89 (18)	C15X—C14X—H14D	109.2
O3—C12—C3	125.4 (2)	H14C—C14X—H14D	107.9
O4—C12—C3	110.75 (15)	C16—C15X—C14X	122.4 (8)
C12—O4—C13	116.76 (18)	C16—C15X—O6	58.2 (3)
O4—C13—H13A	109.5	C14X—C15X—O6	108.5 (7)
O4—C13—H13B	109.5	C16—C15X—H15X	117.4
H13A—C13—H13B	109.5	C14X—C15X—H15X	117.4
O4—C13—H13C	109.5	O6—C15X—H15X	117.4
H13A—C13—H13C	109.5
O2—S1—N2—C3	−172.61 (13)	N2—S1—C10—C5	39.59 (14)
O1—S1—N2—C3	57.18 (14)	C4—C3—C12—O3	8.5 (3)
C10—S1—N2—C3	−57.04 (13)	N2—C3—C12—O3	−170.9 (2)
O2—S1—N2—C11	−32.06 (16)	C4—C3—C12—O4	−171.60 (16)
O1—S1—N2—C11	−162.27 (14)	N2—C3—C12—O4	9.0 (2)
C10—S1—N2—C11	83.50 (14)	O3—C12—O4—C13	−2.0 (3)
C11—N2—C3—C4	−101.63 (19)	C3—C12—O4—C13	178.12 (16)
S1—N2—C3—C4	39.6 (2)	C3—C4—O5—C14X	81.6 (5)
C11—N2—C3—C12	77.8 (2)	C5—C4—O5—C14X	−104.9 (5)
S1—N2—C3—C12	−141.04 (13)	C3—C4—O5—C14	126.8 (2)
N2—C3—C4—O5	177.68 (14)	C5—C4—O5—C14	−59.7 (2)
C12—C3—C4—O5	−1.7 (3)	C4—O5—C14—C15	−79.8 (3)
N2—C3—C4—C5	4.5 (2)	C14X—O5—C14—C15	27.8 (4)
C12—C3—C4—C5	−174.86 (15)	O5—C14—C15—C16	157.0 (3)
O5—C4—C5—C6	−20.4 (2)	O5—C14—C15—O6	90.8 (3)
C3—C4—C5—C6	153.18 (17)	C14—C15—C16—O6	−99.3 (3)
O5—C4—C5—C10	163.78 (14)	O6—C15—C16—C15X	79.6 (5)
C3—C4—C5—C10	−22.7 (2)	C14—C15—C16—C15X	−19.7 (5)
C10—C5—C6—C7	1.3 (3)	C15X—C16—O6—C15	−39.9 (4)
C4—C5—C6—C7	−174.71 (17)	C15—C16—O6—C15X	39.9 (4)
C5—C6—C7—C8	−0.2 (3)	C14—C15—O6—C16	113.4 (4)
C6—C7—C8—C9	−0.5 (3)	C16—C15—O6—C15X	−81.5 (5)
C7—C8—C9—C10	0.1 (3)	C14—C15—O6—C15X	31.9 (5)
C8—C9—C10—C5	1.0 (3)	C4—O5—C14X—C15X	60.1 (8)
C8—C9—C10—S1	179.64 (14)	C14—O5—C14X—C15X	−34.6 (5)
C6—C5—C10—C9	−1.7 (2)	C15—C16—C15X—C14X	11.7 (5)
C4—C5—C10—C9	174.28 (15)	O6—C16—C15X—C14X	92.8 (6)
C6—C5—C10—S1	179.57 (13)	C15—C16—C15X—O6	−81.2 (5)
C4—C5—C10—S1	−4.4 (2)	O5—C14X—C15X—C16	−164.2 (5)
O2—S1—C10—C9	−25.20 (17)	O5—C14X—C15X—O6	−100.7 (7)
O1—S1—C10—C9	107.90 (15)	C15—O6—C15X—C16	77.6 (5)
N2—S1—C10—C9	−139.14 (15)	C16—O6—C15X—C14X	−117.2 (7)
O2—S1—C10—C5	153.53 (13)	C15—O6—C15X—C14X	−39.7 (5)
O1—S1—C10—C5	−73.37 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O6i	0.93	2.49	3.377 (3)	158
C15—H15···O3ii	0.98	2.50	3.317 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O6i	0.93	2.49	3.377 (3)	158
C15—H15⋯O3ii	0.98	2.50	3.317 (4)	140

Symmetry codes: (i) ; (ii) .