A nonmerohedral twin of methyl 2-[meth-yl(methyl-sulfon-yl)amino]benzoate.

The asymmetric unit of the title compound, C(10)H(13)NO(4)S, comprises two crystallographically independent mol-ecules. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds, which link mol-ecules along the b axis. The crystal is a nonmerohedral twin, the refined ratio of the twin components being 0.344 (2):0.656 (2).

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ▶). For applications of benzothia­zine derivatives in organic synthesis, see: Shafiq et al. (2008 ▶, 2009a ▶,b ▶); Lombardino (1972 ▶); Arshad et al. (2008 ▶).

Experimental

Crystal data

C10H13NO4S

M = 243.27

Monoclinic,

a = 8.7476 (4) Å

b = 10.2081 (4) Å

c = 13.8377 (7) Å

β = 108.347 (3)°

V = 1172.84 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.32 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.917, T max = 0.960

13537 measured reflections

5720 independent reflections

3842 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.083

S = 0.99

5720 reflections

296 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983), 2643 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037799/lh2905sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037799/lh2905Isup2.hkl

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

C10H13NO4S	F(000) = 512
Mr = 243.27	Dx = 1.378 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3745 reflections
a = 8.7476 (4) Å	θ = 2.5–29.5°
b = 10.2081 (4) Å	µ = 0.27 mm−1
c = 13.8377 (7) Å	T = 296 K
β = 108.347 (3)°	Block, colourless
V = 1172.84 (9) Å3	0.32 × 0.21 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5720 independent reflections
Radiation source: fine-focus sealed tube	3842 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.917, Tmax = 0.960	k = −13→13
13537 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0315P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
5720 reflections	Δρmax = 0.20 e Å−3
296 parameters	Δρmin = −0.29 e Å−3
1 restraint	Absolute structure: Flack (1983), 2643 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S11	0.34203 (10)	1.01678 (10)	−0.09098 (6)	0.0492 (2)
O13	0.4796 (4)	0.9599 (3)	−0.1065 (2)	0.0757 (9)
O11	0.3556 (4)	0.8101 (3)	0.1014 (3)	0.0921 (12)
O12	0.1243 (4)	0.7697 (2)	0.1261 (2)	0.0569 (8)
O14	0.1950 (3)	0.9443 (3)	−0.1159 (2)	0.0631 (8)
N11	0.3887 (3)	1.0581 (3)	0.0270 (2)	0.0460 (7)
C11	0.2621 (5)	1.0872 (4)	0.0698 (3)	0.0440 (10)
C12	0.2224 (5)	1.2160 (4)	0.0785 (3)	0.0569 (12)
H12	0.2787	1.2817	0.0575	0.068*
C13	0.1001 (6)	1.2502 (4)	0.1178 (4)	0.0679 (14)
H13	0.0772	1.3377	0.1256	0.081*
C14	0.0131 (5)	1.1521 (4)	0.1450 (3)	0.0551 (11)
H14	−0.0731	1.1733	0.1678	0.066*
C15	0.0540 (4)	1.0221 (5)	0.1385 (3)	0.0503 (8)
H15	−0.0034	0.9566	0.1586	0.060*
C16	0.1787 (4)	0.9889 (3)	0.1025 (3)	0.0431 (9)
C17	0.2342 (5)	0.8487 (4)	0.1083 (3)	0.0491 (10)
C18	0.1680 (6)	0.6327 (4)	0.1398 (3)	0.0737 (14)
H18A	0.2723	0.6243	0.1898	0.111*
H18B	0.1708	0.5966	0.0763	0.111*
H18C	0.0899	0.5864	0.1623	0.111*
C19	0.5524 (5)	1.0955 (5)	0.0835 (3)	0.0745 (14)
H19A	0.5862	1.0495	0.1472	0.112*
H19B	0.5567	1.1882	0.0960	0.112*
H19C	0.6225	1.0737	0.0447	0.112*
C20	0.3003 (6)	1.1605 (4)	−0.1635 (3)	0.0791 (15)
H20A	0.2236	1.2121	−0.1435	0.119*
H20B	0.2567	1.1385	−0.2343	0.119*
H20C	0.3978	1.2098	−0.1524	0.119*
S21	0.93347 (9)	0.01388 (10)	0.56230 (7)	0.0483 (2)
O21	0.7083 (4)	0.2046 (3)	0.3383 (3)	0.0857 (10)
O22	0.4802 (4)	0.2520 (3)	0.3686 (2)	0.0646 (9)
O23	0.8215 (4)	0.0862 (3)	0.5968 (2)	0.0686 (9)
O24	1.0850 (3)	0.0697 (3)	0.5679 (3)	0.0782 (10)
N21	0.8462 (3)	−0.0237 (2)	0.4449 (2)	0.0460 (7)
C21	0.6795 (4)	−0.0606 (4)	0.4145 (3)	0.0395 (9)
C22	0.6397 (5)	−0.1920 (4)	0.4206 (3)	0.0493 (10)
H22	0.7207	−0.2544	0.4423	0.059*
C23	0.4821 (5)	−0.2289 (4)	0.3946 (3)	0.0522 (11)
H23	0.4563	−0.3171	0.3963	0.063*
C24	0.3619 (5)	−0.1381 (4)	0.3663 (3)	0.0591 (11)
H24	0.2551	−0.1640	0.3515	0.071*
C25	0.3989 (4)	−0.0073 (4)	0.3595 (3)	0.0520 (10)
H25	0.3166	0.0544	0.3403	0.062*
C26	0.5591 (4)	0.0328 (4)	0.3811 (2)	0.0402 (8)
C27	0.5960 (5)	0.1720 (4)	0.3634 (3)	0.0488 (10)
C28	0.5045 (7)	0.3895 (4)	0.3499 (4)	0.0806 (15)
H28A	0.5186	0.3989	0.2842	0.121*
H28B	0.5987	0.4213	0.4014	0.121*
H28C	0.4123	0.4392	0.3518	0.121*
C29	0.9422 (6)	−0.0656 (6)	0.3808 (4)	0.0864 (17)
H29A	0.8828	−0.0498	0.3106	0.130*
H29B	0.9657	−0.1574	0.3909	0.130*
H29C	1.0411	−0.0169	0.3989	0.130*
C30	0.9703 (5)	−0.1321 (5)	0.6318 (3)	0.0742 (14)
H30A	1.0313	−0.1138	0.7013	0.111*
H30B	1.0302	−0.1907	0.6030	0.111*
H30C	0.8697	−0.1720	0.6293	0.111*

	U11	U22	U33	U12	U13	U23
S11	0.0494 (5)	0.0530 (6)	0.0502 (5)	−0.0082 (6)	0.0229 (4)	−0.0054 (6)
O13	0.079 (2)	0.082 (2)	0.084 (2)	0.0002 (16)	0.0516 (19)	−0.0212 (17)
O11	0.092 (3)	0.0563 (18)	0.157 (4)	0.0362 (18)	0.081 (3)	0.038 (2)
O12	0.0624 (19)	0.0402 (17)	0.070 (2)	−0.0011 (14)	0.0241 (16)	−0.0016 (13)
O14	0.0620 (18)	0.0702 (18)	0.0598 (17)	−0.0278 (15)	0.0230 (16)	−0.0191 (14)
N11	0.0370 (16)	0.0516 (18)	0.0512 (17)	−0.0085 (14)	0.0165 (15)	−0.0038 (12)
C11	0.045 (2)	0.045 (2)	0.041 (2)	−0.0018 (19)	0.0122 (18)	−0.0017 (15)
C12	0.058 (3)	0.041 (2)	0.073 (3)	−0.001 (2)	0.023 (2)	−0.007 (2)
C13	0.066 (3)	0.056 (3)	0.082 (4)	0.012 (3)	0.023 (3)	−0.017 (2)
C14	0.050 (2)	0.062 (3)	0.058 (2)	0.008 (2)	0.024 (2)	−0.010 (2)
C15	0.0497 (19)	0.053 (2)	0.054 (2)	−0.003 (3)	0.0241 (16)	−0.002 (2)
C16	0.047 (2)	0.042 (2)	0.0415 (18)	0.0067 (17)	0.0166 (17)	0.0016 (16)
C17	0.055 (3)	0.050 (2)	0.045 (2)	0.013 (2)	0.021 (2)	0.0116 (18)
C18	0.091 (4)	0.042 (2)	0.087 (3)	−0.002 (2)	0.025 (3)	0.010 (2)
C19	0.043 (2)	0.106 (4)	0.074 (3)	−0.017 (2)	0.018 (2)	−0.035 (3)
C20	0.078 (4)	0.077 (3)	0.075 (3)	−0.022 (3)	0.013 (3)	0.024 (3)
S21	0.0360 (5)	0.0431 (5)	0.0628 (5)	−0.0009 (5)	0.0111 (4)	−0.0045 (6)
O21	0.071 (2)	0.0638 (18)	0.134 (3)	−0.0058 (17)	0.048 (2)	0.026 (2)
O22	0.077 (2)	0.0438 (17)	0.080 (2)	0.0108 (16)	0.0350 (19)	0.0115 (14)
O23	0.0614 (19)	0.0662 (18)	0.075 (2)	0.0129 (16)	0.0176 (16)	−0.0248 (14)
O24	0.0447 (17)	0.071 (2)	0.107 (2)	−0.0199 (14)	0.0075 (17)	−0.0016 (16)
N21	0.0432 (17)	0.0425 (17)	0.0579 (17)	0.0006 (13)	0.0240 (16)	0.0025 (12)
C21	0.039 (2)	0.041 (2)	0.044 (2)	−0.0028 (17)	0.0205 (18)	−0.0020 (15)
C22	0.059 (3)	0.038 (2)	0.048 (2)	0.006 (2)	0.014 (2)	−0.0005 (16)
C23	0.054 (3)	0.038 (2)	0.065 (3)	−0.006 (2)	0.019 (2)	−0.0047 (19)
C24	0.046 (2)	0.058 (3)	0.073 (3)	−0.017 (2)	0.017 (2)	−0.009 (2)
C25	0.0394 (19)	0.055 (3)	0.059 (2)	0.004 (2)	0.0128 (17)	0.003 (2)
C26	0.0406 (19)	0.042 (2)	0.0377 (16)	−0.0059 (19)	0.0124 (15)	0.0013 (16)
C27	0.051 (3)	0.047 (2)	0.050 (2)	−0.001 (2)	0.020 (2)	0.0028 (18)
C28	0.115 (4)	0.041 (2)	0.098 (3)	0.012 (3)	0.050 (3)	0.015 (2)
C29	0.068 (3)	0.109 (4)	0.107 (4)	−0.010 (3)	0.061 (3)	−0.026 (3)
C30	0.066 (3)	0.080 (3)	0.064 (3)	0.007 (3)	0.002 (2)	0.014 (3)

S11—O13	1.412 (3)	S21—O24	1.422 (3)
S11—O14	1.429 (3)	S21—O23	1.424 (3)
S11—N11	1.609 (3)	S21—N21	1.609 (3)
S11—C20	1.750 (4)	S21—C30	1.748 (5)
O11—C17	1.166 (5)	O21—C27	1.189 (4)
O12—C17	1.335 (5)	O22—C27	1.320 (4)
O12—C18	1.446 (5)	O22—C28	1.455 (5)
N11—C11	1.441 (5)	N21—C21	1.435 (4)
N11—C19	1.450 (5)	N21—C29	1.464 (5)
C11—C12	1.375 (5)	C21—C26	1.388 (5)
C11—C16	1.398 (5)	C21—C22	1.394 (5)
C12—C13	1.389 (6)	C22—C23	1.364 (6)
C12—H12	0.9300	C22—H22	0.9300
C13—C14	1.380 (6)	C23—C24	1.363 (6)
C13—H13	0.9300	C23—H23	0.9300
C14—C15	1.385 (6)	C24—C25	1.383 (6)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.377 (5)	C25—C26	1.399 (5)
C15—H15	0.9300	C25—H25	0.9300
C16—C17	1.505 (5)	C26—C27	1.495 (5)
C18—H18A	0.9600	C28—H28A	0.9600
C18—H18B	0.9600	C28—H28B	0.9600
C18—H18C	0.9600	C28—H28C	0.9600
C19—H19A	0.9600	C29—H29A	0.9600
C19—H19B	0.9600	C29—H29B	0.9600
C19—H19C	0.9600	C29—H29C	0.9600
C20—H20A	0.9600	C30—H30A	0.9600
C20—H20B	0.9600	C30—H30B	0.9600
C20—H20C	0.9600	C30—H30C	0.9600
O13—S11—O14	119.71 (18)	O24—S21—O23	120.1 (2)
O13—S11—N11	107.81 (17)	O24—S21—N21	106.75 (18)
O14—S11—N11	107.60 (15)	O23—S21—N21	107.73 (16)
O13—S11—C20	106.9 (2)	O24—S21—C30	107.7 (2)
O14—S11—C20	106.7 (2)	O23—S21—C30	106.6 (2)
N11—S11—C20	107.6 (2)	N21—S21—C30	107.4 (2)
C17—O12—C18	115.6 (3)	C27—O22—C28	115.4 (3)
C11—N11—C19	118.7 (3)	C21—N21—C29	118.1 (3)
C11—N11—S11	119.2 (2)	C21—N21—S21	118.3 (2)
C19—N11—S11	120.5 (3)	C29—N21—S21	120.1 (3)
C12—C11—C16	119.1 (4)	C26—C21—C22	120.2 (3)
C12—C11—N11	118.8 (4)	C26—C21—N21	120.8 (3)
C16—C11—N11	122.1 (3)	C22—C21—N21	119.0 (3)
C11—C12—C13	121.4 (4)	C23—C22—C21	120.0 (4)
C11—C12—H12	119.3	C23—C22—H22	120.0
C13—C12—H12	119.3	C21—C22—H22	120.0
C14—C13—C12	119.0 (4)	C24—C23—C22	120.8 (4)
C14—C13—H13	120.5	C24—C23—H23	119.6
C12—C13—H13	120.5	C22—C23—H23	119.6
C13—C14—C15	120.1 (4)	C23—C24—C25	120.0 (4)
C13—C14—H14	120.0	C23—C24—H24	120.0
C15—C14—H14	120.0	C25—C24—H24	120.0
C16—C15—C14	120.7 (4)	C24—C25—C26	120.5 (4)
C16—C15—H15	119.7	C24—C25—H25	119.7
C14—C15—H15	119.7	C26—C25—H25	119.7
C15—C16—C11	119.6 (3)	C21—C26—C25	118.3 (4)
C15—C16—C17	119.6 (4)	C21—C26—C27	121.8 (3)
C11—C16—C17	120.5 (3)	C25—C26—C27	119.8 (4)
O11—C17—O12	122.6 (4)	O21—C27—O22	124.2 (4)
O11—C17—C16	127.2 (4)	O21—C27—C26	123.7 (4)
O12—C17—C16	110.2 (3)	O22—C27—C26	111.7 (3)
O12—C18—H18A	109.5	O22—C28—H28A	109.5
O12—C18—H18B	109.5	O22—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
O12—C18—H18C	109.5	O22—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5
N11—C19—H19A	109.5	N21—C29—H29A	109.5
N11—C19—H19B	109.5	N21—C29—H29B	109.5
H19A—C19—H19B	109.5	H29A—C29—H29B	109.5
N11—C19—H19C	109.5	N21—C29—H29C	109.5
H19A—C19—H19C	109.5	H29A—C29—H29C	109.5
H19B—C19—H19C	109.5	H29B—C29—H29C	109.5
S11—C20—H20A	109.5	S21—C30—H30A	109.5
S11—C20—H20B	109.5	S21—C30—H30B	109.5
H20A—C20—H20B	109.5	H30A—C30—H30B	109.5
S11—C20—H20C	109.5	S21—C30—H30C	109.5
H20A—C20—H20C	109.5	H30A—C30—H30C	109.5
H20B—C20—H20C	109.5	H30B—C30—H30C	109.5
O13—S11—N11—C11	−164.2 (3)	O24—S21—N21—C21	−169.1 (3)
O14—S11—N11—C11	−33.8 (3)	O23—S21—N21—C21	−38.9 (3)
C20—S11—N11—C11	80.8 (3)	C30—S21—N21—C21	75.5 (3)
O13—S11—N11—C19	30.1 (4)	O24—S21—N21—C29	32.8 (3)
O14—S11—N11—C19	160.5 (3)	O23—S21—N21—C29	163.0 (3)
C20—S11—N11—C19	−84.9 (4)	C30—S21—N21—C29	−82.6 (3)
C19—N11—C11—C12	67.4 (5)	C29—N21—C21—C26	−111.5 (4)
S11—N11—C11—C12	−98.6 (4)	S21—N21—C21—C26	89.9 (3)
C19—N11—C11—C16	−112.7 (4)	C29—N21—C21—C22	69.5 (5)
S11—N11—C11—C16	81.3 (4)	S21—N21—C21—C22	−89.1 (3)
C16—C11—C12—C13	−0.8 (6)	C26—C21—C22—C23	−0.7 (6)
N11—C11—C12—C13	179.1 (4)	N21—C21—C22—C23	178.3 (3)
C11—C12—C13—C14	−2.5 (7)	C21—C22—C23—C24	−2.5 (7)
C12—C13—C14—C15	3.7 (7)	C22—C23—C24—C25	2.7 (7)
C13—C14—C15—C16	−1.7 (6)	C23—C24—C25—C26	0.2 (6)
C14—C15—C16—C11	−1.6 (5)	C22—C21—C26—C25	3.5 (5)
C14—C15—C16—C17	172.4 (3)	N21—C21—C26—C25	−175.5 (3)
C12—C11—C16—C15	2.8 (5)	C22—C21—C26—C27	−173.6 (3)
N11—C11—C16—C15	−177.1 (3)	N21—C21—C26—C27	7.4 (5)
C12—C11—C16—C17	−171.1 (4)	C24—C25—C26—C21	−3.3 (5)
N11—C11—C16—C17	9.0 (5)	C24—C25—C26—C27	173.9 (4)
C18—O12—C17—O11	2.1 (6)	C28—O22—C27—O21	−5.3 (6)
C18—O12—C17—C16	−176.3 (3)	C28—O22—C27—C26	−178.7 (4)
C15—C16—C17—O11	−162.8 (4)	C21—C26—C27—O21	29.6 (6)
C11—C16—C17—O11	11.2 (7)	C25—C26—C27—O21	−147.4 (4)
C15—C16—C17—O12	15.5 (5)	C21—C26—C27—O22	−157.0 (3)
C11—C16—C17—O12	−170.6 (3)	C25—C26—C27—O22	26.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O14i	0.93	2.58	3.248 (6)	129
C20—H20C···O11ii	0.96	2.29	3.240 (5)	171
C22—H22···O24iii	0.93	2.51	3.391 (5)	159
C28—H28A···O13iv	0.96	2.54	3.490 (6)	169
C30—H30A···O14v	0.96	2.55	3.512 (5)	178
C30—H30B···O21iii	0.96	2.42	3.181 (6)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O14i	0.93	2.58	3.248 (6)	129
C20—H20C⋯O11ii	0.96	2.29	3.240 (5)	171
C22—H22⋯O24iii	0.93	2.51	3.391 (5)	159
C28—H28A⋯O13iv	0.96	2.54	3.490 (6)	169
C30—H30A⋯O14v	0.96	2.55	3.512 (5)	178
C30—H30B⋯O21iii	0.96	2.42	3.181 (6)	136

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