organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For applications of benzothia­zine derivatives in organic synthesis, see: Shafiq et al. (2008[Shafiq, M., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Arshad, M. N. (2008). Acta Cryst. E64, o389.], 2009a[Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Khan, M. H. (2009a). Acta Cryst. E65, o955.],b[Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Haider, Z. (2009b). Acta Cryst. E65, o1413.]); Lombardino (1972[Lombardino, J. G. (1972). J. Heterocycl. Chem. 9, 315-317.]); Arshad et al. (2008[Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NO4S

  • Mr = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.917, Tmax = 0.960

  • 13537 measured reflections

  • 5720 independent reflections

  • 3842 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −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 DA 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) [-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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

All of the hydrogen atoms were positioned geometrically [C—H = 0.93–0.96 Å] and refined using a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was applied for the methyl groups. PLATON and intensity statistic indicate nonmerohedral twinning. Applying the twin instruction [TWIN -1 0 0 0 -1 0 1 0 1] with a BASF parameter in SHELXLTL (Sheldrick, 2008) of 0.365 (1) in SHELXTL (Sheldrick, 2008), the R1 value drops to 0.043 (0.1886 without TWIN instruction).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
[Figure 2] 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
C10H13NO4SF(000) = 512
Mr = 243.27Dx = 1.378 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3745 reflections
a = 8.7476 (4) Åθ = 2.5–29.5°
b = 10.2081 (4) ŵ = 0.27 mm1
c = 13.8377 (7) ÅT = 296 K
β = 108.347 (3)°Block, colourless
V = 1172.84 (9) Å30.32 × 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 tube3842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.917, Tmax = 0.960k = 1313
13537 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-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 reflectionsΔρmax = 0.20 e Å3
296 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983), 2643 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (8)
Crystal data top
C10H13NO4SV = 1172.84 (9) Å3
Mr = 243.27Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.7476 (4) ŵ = 0.27 mm1
b = 10.2081 (4) ÅT = 296 K
c = 13.8377 (7) Å0.32 × 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)
Tmin = 0.917, Tmax = 0.960Rint = 0.041
13537 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.20 e Å3
S = 0.99Δρmin = 0.29 e Å3
5720 reflectionsAbsolute structure: Flack (1983), 2643 Friedel pairs
296 parametersAbsolute 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
xyzUiso*/Ueq
S110.34203 (10)1.01678 (10)0.09098 (6)0.0492 (2)
O130.4796 (4)0.9599 (3)0.1065 (2)0.0757 (9)
O110.3556 (4)0.8101 (3)0.1014 (3)0.0921 (12)
O120.1243 (4)0.7697 (2)0.1261 (2)0.0569 (8)
O140.1950 (3)0.9443 (3)0.1159 (2)0.0631 (8)
N110.3887 (3)1.0581 (3)0.0270 (2)0.0460 (7)
C110.2621 (5)1.0872 (4)0.0698 (3)0.0440 (10)
C120.2224 (5)1.2160 (4)0.0785 (3)0.0569 (12)
H120.27871.28170.05750.068*
C130.1001 (6)1.2502 (4)0.1178 (4)0.0679 (14)
H130.07721.33770.12560.081*
C140.0131 (5)1.1521 (4)0.1450 (3)0.0551 (11)
H140.07311.17330.16780.066*
C150.0540 (4)1.0221 (5)0.1385 (3)0.0503 (8)
H150.00340.95660.15860.060*
C160.1787 (4)0.9889 (3)0.1025 (3)0.0431 (9)
C170.2342 (5)0.8487 (4)0.1083 (3)0.0491 (10)
C180.1680 (6)0.6327 (4)0.1398 (3)0.0737 (14)
H18A0.27230.62430.18980.111*
H18B0.17080.59660.07630.111*
H18C0.08990.58640.16230.111*
C190.5524 (5)1.0955 (5)0.0835 (3)0.0745 (14)
H19A0.58621.04950.14720.112*
H19B0.55671.18820.09600.112*
H19C0.62251.07370.04470.112*
C200.3003 (6)1.1605 (4)0.1635 (3)0.0791 (15)
H20A0.22361.21210.14350.119*
H20B0.25671.13850.23430.119*
H20C0.39781.20980.15240.119*
S210.93347 (9)0.01388 (10)0.56230 (7)0.0483 (2)
O210.7083 (4)0.2046 (3)0.3383 (3)0.0857 (10)
O220.4802 (4)0.2520 (3)0.3686 (2)0.0646 (9)
O230.8215 (4)0.0862 (3)0.5968 (2)0.0686 (9)
O241.0850 (3)0.0697 (3)0.5679 (3)0.0782 (10)
N210.8462 (3)0.0237 (2)0.4449 (2)0.0460 (7)
C210.6795 (4)0.0606 (4)0.4145 (3)0.0395 (9)
C220.6397 (5)0.1920 (4)0.4206 (3)0.0493 (10)
H220.72070.25440.44230.059*
C230.4821 (5)0.2289 (4)0.3946 (3)0.0522 (11)
H230.45630.31710.39630.063*
C240.3619 (5)0.1381 (4)0.3663 (3)0.0591 (11)
H240.25510.16400.35150.071*
C250.3989 (4)0.0073 (4)0.3595 (3)0.0520 (10)
H250.31660.05440.34030.062*
C260.5591 (4)0.0328 (4)0.3811 (2)0.0402 (8)
C270.5960 (5)0.1720 (4)0.3634 (3)0.0488 (10)
C280.5045 (7)0.3895 (4)0.3499 (4)0.0806 (15)
H28A0.51860.39890.28420.121*
H28B0.59870.42130.40140.121*
H28C0.41230.43920.35180.121*
C290.9422 (6)0.0656 (6)0.3808 (4)0.0864 (17)
H29A0.88280.04980.31060.130*
H29B0.96570.15740.39090.130*
H29C1.04110.01690.39890.130*
C300.9703 (5)0.1321 (5)0.6318 (3)0.0742 (14)
H30A1.03130.11380.70130.111*
H30B1.03020.19070.60300.111*
H30C0.86970.17200.62930.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0494 (5)0.0530 (6)0.0502 (5)0.0082 (6)0.0229 (4)0.0054 (6)
O130.079 (2)0.082 (2)0.084 (2)0.0002 (16)0.0516 (19)0.0212 (17)
O110.092 (3)0.0563 (18)0.157 (4)0.0362 (18)0.081 (3)0.038 (2)
O120.0624 (19)0.0402 (17)0.070 (2)0.0011 (14)0.0241 (16)0.0016 (13)
O140.0620 (18)0.0702 (18)0.0598 (17)0.0278 (15)0.0230 (16)0.0191 (14)
N110.0370 (16)0.0516 (18)0.0512 (17)0.0085 (14)0.0165 (15)0.0038 (12)
C110.045 (2)0.045 (2)0.041 (2)0.0018 (19)0.0122 (18)0.0017 (15)
C120.058 (3)0.041 (2)0.073 (3)0.001 (2)0.023 (2)0.007 (2)
C130.066 (3)0.056 (3)0.082 (4)0.012 (3)0.023 (3)0.017 (2)
C140.050 (2)0.062 (3)0.058 (2)0.008 (2)0.024 (2)0.010 (2)
C150.0497 (19)0.053 (2)0.054 (2)0.003 (3)0.0241 (16)0.002 (2)
C160.047 (2)0.042 (2)0.0415 (18)0.0067 (17)0.0166 (17)0.0016 (16)
C170.055 (3)0.050 (2)0.045 (2)0.013 (2)0.021 (2)0.0116 (18)
C180.091 (4)0.042 (2)0.087 (3)0.002 (2)0.025 (3)0.010 (2)
C190.043 (2)0.106 (4)0.074 (3)0.017 (2)0.018 (2)0.035 (3)
C200.078 (4)0.077 (3)0.075 (3)0.022 (3)0.013 (3)0.024 (3)
S210.0360 (5)0.0431 (5)0.0628 (5)0.0009 (5)0.0111 (4)0.0045 (6)
O210.071 (2)0.0638 (18)0.134 (3)0.0058 (17)0.048 (2)0.026 (2)
O220.077 (2)0.0438 (17)0.080 (2)0.0108 (16)0.0350 (19)0.0115 (14)
O230.0614 (19)0.0662 (18)0.075 (2)0.0129 (16)0.0176 (16)0.0248 (14)
O240.0447 (17)0.071 (2)0.107 (2)0.0199 (14)0.0075 (17)0.0016 (16)
N210.0432 (17)0.0425 (17)0.0579 (17)0.0006 (13)0.0240 (16)0.0025 (12)
C210.039 (2)0.041 (2)0.044 (2)0.0028 (17)0.0205 (18)0.0020 (15)
C220.059 (3)0.038 (2)0.048 (2)0.006 (2)0.014 (2)0.0005 (16)
C230.054 (3)0.038 (2)0.065 (3)0.006 (2)0.019 (2)0.0047 (19)
C240.046 (2)0.058 (3)0.073 (3)0.017 (2)0.017 (2)0.009 (2)
C250.0394 (19)0.055 (3)0.059 (2)0.004 (2)0.0128 (17)0.003 (2)
C260.0406 (19)0.042 (2)0.0377 (16)0.0059 (19)0.0124 (15)0.0013 (16)
C270.051 (3)0.047 (2)0.050 (2)0.001 (2)0.020 (2)0.0028 (18)
C280.115 (4)0.041 (2)0.098 (3)0.012 (3)0.050 (3)0.015 (2)
C290.068 (3)0.109 (4)0.107 (4)0.010 (3)0.061 (3)0.026 (3)
C300.066 (3)0.080 (3)0.064 (3)0.007 (3)0.002 (2)0.014 (3)
Geometric parameters (Å, º) top
S11—O131.412 (3)S21—O241.422 (3)
S11—O141.429 (3)S21—O231.424 (3)
S11—N111.609 (3)S21—N211.609 (3)
S11—C201.750 (4)S21—C301.748 (5)
O11—C171.166 (5)O21—C271.189 (4)
O12—C171.335 (5)O22—C271.320 (4)
O12—C181.446 (5)O22—C281.455 (5)
N11—C111.441 (5)N21—C211.435 (4)
N11—C191.450 (5)N21—C291.464 (5)
C11—C121.375 (5)C21—C261.388 (5)
C11—C161.398 (5)C21—C221.394 (5)
C12—C131.389 (6)C22—C231.364 (6)
C12—H120.9300C22—H220.9300
C13—C141.380 (6)C23—C241.363 (6)
C13—H130.9300C23—H230.9300
C14—C151.385 (6)C24—C251.383 (6)
C14—H140.9300C24—H240.9300
C15—C161.377 (5)C25—C261.399 (5)
C15—H150.9300C25—H250.9300
C16—C171.505 (5)C26—C271.495 (5)
C18—H18A0.9600C28—H28A0.9600
C18—H18B0.9600C28—H28B0.9600
C18—H18C0.9600C28—H28C0.9600
C19—H19A0.9600C29—H29A0.9600
C19—H19B0.9600C29—H29B0.9600
C19—H19C0.9600C29—H29C0.9600
C20—H20A0.9600C30—H30A0.9600
C20—H20B0.9600C30—H30B0.9600
C20—H20C0.9600C30—H30C0.9600
O13—S11—O14119.71 (18)O24—S21—O23120.1 (2)
O13—S11—N11107.81 (17)O24—S21—N21106.75 (18)
O14—S11—N11107.60 (15)O23—S21—N21107.73 (16)
O13—S11—C20106.9 (2)O24—S21—C30107.7 (2)
O14—S11—C20106.7 (2)O23—S21—C30106.6 (2)
N11—S11—C20107.6 (2)N21—S21—C30107.4 (2)
C17—O12—C18115.6 (3)C27—O22—C28115.4 (3)
C11—N11—C19118.7 (3)C21—N21—C29118.1 (3)
C11—N11—S11119.2 (2)C21—N21—S21118.3 (2)
C19—N11—S11120.5 (3)C29—N21—S21120.1 (3)
C12—C11—C16119.1 (4)C26—C21—C22120.2 (3)
C12—C11—N11118.8 (4)C26—C21—N21120.8 (3)
C16—C11—N11122.1 (3)C22—C21—N21119.0 (3)
C11—C12—C13121.4 (4)C23—C22—C21120.0 (4)
C11—C12—H12119.3C23—C22—H22120.0
C13—C12—H12119.3C21—C22—H22120.0
C14—C13—C12119.0 (4)C24—C23—C22120.8 (4)
C14—C13—H13120.5C24—C23—H23119.6
C12—C13—H13120.5C22—C23—H23119.6
C13—C14—C15120.1 (4)C23—C24—C25120.0 (4)
C13—C14—H14120.0C23—C24—H24120.0
C15—C14—H14120.0C25—C24—H24120.0
C16—C15—C14120.7 (4)C24—C25—C26120.5 (4)
C16—C15—H15119.7C24—C25—H25119.7
C14—C15—H15119.7C26—C25—H25119.7
C15—C16—C11119.6 (3)C21—C26—C25118.3 (4)
C15—C16—C17119.6 (4)C21—C26—C27121.8 (3)
C11—C16—C17120.5 (3)C25—C26—C27119.8 (4)
O11—C17—O12122.6 (4)O21—C27—O22124.2 (4)
O11—C17—C16127.2 (4)O21—C27—C26123.7 (4)
O12—C17—C16110.2 (3)O22—C27—C26111.7 (3)
O12—C18—H18A109.5O22—C28—H28A109.5
O12—C18—H18B109.5O22—C28—H28B109.5
H18A—C18—H18B109.5H28A—C28—H28B109.5
O12—C18—H18C109.5O22—C28—H28C109.5
H18A—C18—H18C109.5H28A—C28—H28C109.5
H18B—C18—H18C109.5H28B—C28—H28C109.5
N11—C19—H19A109.5N21—C29—H29A109.5
N11—C19—H19B109.5N21—C29—H29B109.5
H19A—C19—H19B109.5H29A—C29—H29B109.5
N11—C19—H19C109.5N21—C29—H29C109.5
H19A—C19—H19C109.5H29A—C29—H29C109.5
H19B—C19—H19C109.5H29B—C29—H29C109.5
S11—C20—H20A109.5S21—C30—H30A109.5
S11—C20—H20B109.5S21—C30—H30B109.5
H20A—C20—H20B109.5H30A—C30—H30B109.5
S11—C20—H20C109.5S21—C30—H30C109.5
H20A—C20—H20C109.5H30A—C30—H30C109.5
H20B—C20—H20C109.5H30B—C30—H30C109.5
O13—S11—N11—C11164.2 (3)O24—S21—N21—C21169.1 (3)
O14—S11—N11—C1133.8 (3)O23—S21—N21—C2138.9 (3)
C20—S11—N11—C1180.8 (3)C30—S21—N21—C2175.5 (3)
O13—S11—N11—C1930.1 (4)O24—S21—N21—C2932.8 (3)
O14—S11—N11—C19160.5 (3)O23—S21—N21—C29163.0 (3)
C20—S11—N11—C1984.9 (4)C30—S21—N21—C2982.6 (3)
C19—N11—C11—C1267.4 (5)C29—N21—C21—C26111.5 (4)
S11—N11—C11—C1298.6 (4)S21—N21—C21—C2689.9 (3)
C19—N11—C11—C16112.7 (4)C29—N21—C21—C2269.5 (5)
S11—N11—C11—C1681.3 (4)S21—N21—C21—C2289.1 (3)
C16—C11—C12—C130.8 (6)C26—C21—C22—C230.7 (6)
N11—C11—C12—C13179.1 (4)N21—C21—C22—C23178.3 (3)
C11—C12—C13—C142.5 (7)C21—C22—C23—C242.5 (7)
C12—C13—C14—C153.7 (7)C22—C23—C24—C252.7 (7)
C13—C14—C15—C161.7 (6)C23—C24—C25—C260.2 (6)
C14—C15—C16—C111.6 (5)C22—C21—C26—C253.5 (5)
C14—C15—C16—C17172.4 (3)N21—C21—C26—C25175.5 (3)
C12—C11—C16—C152.8 (5)C22—C21—C26—C27173.6 (3)
N11—C11—C16—C15177.1 (3)N21—C21—C26—C277.4 (5)
C12—C11—C16—C17171.1 (4)C24—C25—C26—C213.3 (5)
N11—C11—C16—C179.0 (5)C24—C25—C26—C27173.9 (4)
C18—O12—C17—O112.1 (6)C28—O22—C27—O215.3 (6)
C18—O12—C17—C16176.3 (3)C28—O22—C27—C26178.7 (4)
C15—C16—C17—O11162.8 (4)C21—C26—C27—O2129.6 (6)
C11—C16—C17—O1111.2 (7)C25—C26—C27—O21147.4 (4)
C15—C16—C17—O1215.5 (5)C21—C26—C27—O22157.0 (3)
C11—C16—C17—O12170.6 (3)C25—C26—C27—O2226.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O14i0.932.583.248 (6)129
C20—H20C···O11ii0.962.293.240 (5)171
C22—H22···O24iii0.932.513.391 (5)159
C28—H28A···O13iv0.962.543.490 (6)169
C30—H30A···O14v0.962.553.512 (5)178
C30—H30B···O21iii0.962.423.181 (6)136
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y+1/2, z; (iii) x+2, y1/2, z+1; (iv) x+1, y1/2, z; (v) x+1, y1, z+1.

Experimental details

Crystal data
Chemical formulaC10H13NO4S
Mr243.27
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)8.7476 (4), 10.2081 (4), 13.8377 (7)
β (°) 108.347 (3)
V3)1172.84 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.32 × 0.21 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.917, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
13537, 5720, 3842
Rint0.041
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.083, 0.99
No. of reflections5720
No. of parameters296
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.29
Absolute structureFlack (1983), 2643 Friedel pairs
Absolute structure parameter0.00 (8)

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O14i0.932.583.248 (6)128.9
C20—H20C···O11ii0.962.293.240 (5)170.8
C22—H22···O24iii0.932.513.391 (5)159.1
C28—H28A···O13iv0.962.543.490 (6)169.2
C30—H30A···O14v0.962.553.512 (5)177.7
C30—H30B···O21iii0.962.423.181 (6)135.8
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y+1/2, z; (iii) x+2, y1/2, z+1; (iv) x+1, y1/2, z; (v) x+1, y1, 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

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationArshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLombardino, J. G. (1972). J. Heterocycl. Chem. 9, 315–317.  CrossRef CAS Google Scholar
First citationShafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Haider, Z. (2009b). Acta Cryst. E65, o1413.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Khan, M. H. (2009a). Acta Cryst. E65, o955.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShafiq, M., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Arshad, M. N. (2008). Acta Cryst. E64, o389.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds