A nonmerohedral twin of methyl 2-[meth­yl(methyl­sulfon­yl)amino]benzoate

Shafiq, M.; Khan, I.U.; Kia, R.; Arshad, M.N.; Aslam, M.

doi:10.1107/S1600536809037799

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2588

doi:10.1107/S1600536809037799

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A nonmerohedral twin of methyl 2-[methyl(methylsulfonyl)amino]benzoate

Muhammad Shafiq,^a Islam Ullah Khan,^a ^* Reza Kia,^b ‡ Muhammad Nadeem Arshad ^a and Maooz Aslam ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 13 September 2009; accepted 18 September 2009; online 30 September 2009)

The asymmetric unit of the title compound, C₁₀H₁₃NO₄S, comprises two crystallographically independent molecules. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds, which link molecules 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_r = 243.27
Monoclinic, P 2₁
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 (SADABS; 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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.083
S = 0.99
5720 reflections
296 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983), 2643 Friedel pairs
Flack parameter: 0.00 (8)

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⋯O13^iv	0.96	2.54	3.490 (6)	169
C30—H30A⋯O14^v	0.96	2.55	3.512 (5)	178
C30—H30B⋯O21ⁱⁱⁱ	0.96	2.42	3.181 (6)	136
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (v) x+1, y-1, z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Our group is actively involved in the synthesis and characterization by X-ray studies of various benzothiazine derivatives (Shafiq et al., 2009a; Shafiq et al., 2009b; Shafiq et al., 2008; Arshad et al., 2008). The crystal structure of the title compound is reported here.

In the molecule of the title compound, (Fig. 1), intermolecular C—H···O interactions (Table 1) link neighbouring molecules along the b axis (Fig. 2). The crystal was a nonmerohedral twin with a refined BASF parameter ratio of 0.344 (2)/0.656 (2).

Related literature top

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 top

The title compound was synthesized as reported earlier (Lombardino et al., 1972) and was recrystallized from a solution of Ethanol by slow evaporation at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed down the c-axis, showing linking of the molecules through intermolecular C—H···O interactions along the b-axis. Intermolecular interactions are drawn as dashed lines.

methyl 2-[methyl(methylsulfonyl)amino]benzoate top

Crystal data top

C₁₀H₁₃NO₄S	F(000) = 512
M_r = 243.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0315P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
5720 reflections	Δρ_max = 0.20 e Å⁻³
296 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2643 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₀H₁₃NO₄S	V = 1172.84 (9) Å³
M_r = 243.27	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.7476 (4) Å	µ = 0.27 mm⁻¹
b = 10.2081 (4) Å	T = 296 K
c = 13.8377 (7) Å	0.32 × 0.21 × 0.15 mm
β = 108.347 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5720 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3842 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.960	R_int = 0.041
13537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.20 e Å⁻³
S = 0.99	Δρ_min = −0.29 e Å⁻³
5720 reflections	Absolute structure: Flack (1983), 2643 Friedel pairs
296 parameters	Absolute structure parameter: 0.00 (8)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O13^iv	0.96	2.54	3.490 (6)	169
C30—H30A···O14^v	0.96	2.55	3.512 (5)	178
C30—H30B···O21ⁱⁱⁱ	0.96	2.42	3.181 (6)	136

Symmetry codes: (i) −x, y+1/2, −z; (ii) −x+1, y+1/2, −z; (iii) −x+2, y−1/2, −z+1; (iv) −x+1, y−1/2, −z; (v) x+1, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₄S
M_r	243.27
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.7476 (4), 10.2081 (4), 13.8377 (7)
β (°)	108.347 (3)
V (Å³)	1172.84 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.32 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.917, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13537, 5720, 3842
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.083, 0.99
No. of reflections	5720
No. of parameters	296
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29
Absolute structure	Flack (1983), 2643 Friedel pairs
Absolute structure parameter	0.00 (8)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O14ⁱ	0.93	2.58	3.248 (6)	128.9
C20—H20C···O11ⁱⁱ	0.96	2.29	3.240 (5)	170.8
C22—H22···O24ⁱⁱⁱ	0.93	2.51	3.391 (5)	159.1
C28—H28A···O13^iv	0.96	2.54	3.490 (6)	169.2
C30—H30A···O14^v	0.96	2.55	3.512 (5)	177.7
C30—H30B···O21ⁱⁱⁱ	0.96	2.42	3.181 (6)	135.8

Symmetry codes: (i) −x, y+1/2, −z; (ii) −x+1, y+1/2, −z; (iii) −x+2, y−1/2, −z+1; (iv) −x+1, y−1/2, −z; (v) x+1, y−1, z+1.

Footnotes

‡Additional correspondence author, e-mail: zsrkk@yahoo.com. Thomson Reuters Researcher ID: A-5471-2009.

Acknowledgements

We thank the GC University, Lahore, for supporting this work.

References

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