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

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ISSN: 2056-9890

Methyl 2-[(methyl­sulfon­yl)(prop­yl)amino]benzoate

aDepartment of Chemistry, Government College University, Lahore, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 December 2009; accepted 21 December 2009; online 24 December 2009)

The asymmetric unit of the title compound, C12H17NO4S, contains two mol­ecules, both of which show disorder of the two terminal C atoms of the propyl chain over two sets of sites with an occupancy ratio of 0.581 (6):0.419 (6). Intra­molecular C—H⋯O inter­actions help to establish the mol­ecular conformations: in one mol­ecule, the dihedral angle between the methyl ester group and the benzene ring is 41.0 (2)°, whereas in the other mol­ecule it is 36.12 (17)°. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O and C—H⋯π inter­actions.

Related literature

For related structures, 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. & Haider, Z. (2009a). Acta Cryst. E65, o1413.],b[Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Khan, M. H. (2009b). Acta Cryst. E65, o955.]).

[Scheme 1]

Experimental

Crystal data
  • C12H17NO4S

  • Mr = 271.33

  • Monoclinic, P 21 /c

  • a = 10.1762 (4) Å

  • b = 15.0178 (6) Å

  • c = 18.0900 (8) Å

  • β = 92.787 (2)°

  • V = 2761.3 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.25 × 0.12 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.968

  • 25991 measured reflections

  • 5409 independent reflections

  • 2607 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.193

  • S = 1.01

  • 5409 reflections

  • 328 parameters

  • 7 restraints

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O8i 0.93 2.59 3.483 (6) 161
C11A—H11C⋯O1 0.96 2.57 3.486 (15) 159
C16—H16⋯O4 0.93 2.51 3.429 (5) 168
C20—H20C⋯O3ii 0.96 2.57 3.172 (6) 121
C21—H21A⋯O1 0.97 2.55 3.192 (6) 124
C12—H12ACg2iii 0.96 2.84 3.660 (5) 144
C18—H18⋯Cg1iv 0.93 2.87 3.588 (5) 135
Symmetry codes: (i) x+1, y, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

In continuation to our work on the synthesis of benzothiazine derivatives, we have reported various molecules of this series (Shafiq et al., 2008, 2009a, 2009b). The title compound (I, Fig. 1, Fig. 2) is being reported here in this context.

The asymmtric unit of title compound consists of two molecules. In both molecules the two terminal C-atoms of propyl moiety are disordered over two set of sites with occupancy ratio of 0.581 (6):0.419 (6). The two molecules of asymmetric units differ from each other as the dihedral angle between methyl ester A (O2/C1/O1/C8) with benzene ring B (C2–C7) is 40.96 (21)°, whereas in the other molecule it is 36.12 (17)° between C (O6/C13/O5/C20) and D (C13–C19). The molecules are stabilized due to intra as well as intermolecular and C–H···π interactions (Table 1, Fig. 2).

Related literature top

For related structures, see: Shafiq et al. (2008, 2009a,b).

Experimental top

For the preparation of the title compound, the suspension of hexane-washed sodium hydride (50% in mineral oil) was prepared in dry dimethylformamide (3 ml). A solution of methyl N-methylsulfonylanthranilate (70 mg, 0.306 mmol) in dry dimethylformamide (5 ml) was added to the suspension and stirred for 45 min at room temperature. Then, a solution of propyl iodide (156.40 mg, 0.92 mmol) was added to it. The resulting white suspension was stirred for 2.5–3 h, added to ice and pH adjusted at 4–4.5 and kept in freezer. Solid product obtained was filtered and dried to obtain white prisms of title compound.

Refinement top

The two terminal C-atoms of each molecule are disordered over two set of sites. The disordered C-atoms were treated anisotropic with EADP and refined using DFIX.

H-atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for aryl, methyl and ethylene H, respectively and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aryl and 1.5 for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) with the atom numbering scheme having atoms of greater occupancy ratio. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
[Figure 2] Fig. 2. View of (I) with the atom numbering scheme having atoms of smaller occupancy ratio. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
[Figure 3] Fig. 3. The partial packing of (I), which shows that the molecules are stacked in polymeric chains due to intermolecular H-bodings that extend along the crystallographic b axis.
Methyl 2-[(methylsulfonyl)(propyl)amino]benzoate top
Crystal data top
C12H17NO4SF(000) = 1152
Mr = 271.33Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2607 reflections
a = 10.1762 (4) Åθ = 2.0–26.0°
b = 15.0178 (6) ŵ = 0.24 mm1
c = 18.0900 (8) ÅT = 296 K
β = 92.787 (2)°Prismatic, white
V = 2761.3 (2) Å30.25 × 0.12 × 0.10 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5409 independent reflections
Radiation source: fine-focus sealed tube2607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
Detector resolution: 7.70 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1818
Tmin = 0.955, Tmax = 0.968l = 2222
25991 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0837P)2 + 1.0657P]
where P = (Fo2 + 2Fc2)/3
5409 reflections(Δ/σ)max < 0.001
328 parametersΔρmax = 0.50 e Å3
7 restraintsΔρmin = 0.40 e Å3
Crystal data top
C12H17NO4SV = 2761.3 (2) Å3
Mr = 271.33Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.1762 (4) ŵ = 0.24 mm1
b = 15.0178 (6) ÅT = 296 K
c = 18.0900 (8) Å0.25 × 0.12 × 0.10 mm
β = 92.787 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5409 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2607 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.968Rint = 0.078
25991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0627 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.01Δρmax = 0.50 e Å3
5409 reflectionsΔρmin = 0.40 e Å3
328 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.56276 (10)0.24818 (8)0.18894 (6)0.0513 (4)
O10.3570 (3)0.1598 (3)0.0442 (2)0.0822 (15)
O20.3266 (3)0.2903 (2)0.01117 (18)0.0740 (13)
O30.4772 (3)0.3112 (2)0.15293 (16)0.0706 (13)
O40.5151 (3)0.1951 (2)0.24718 (17)0.0744 (13)
N10.6139 (3)0.1809 (2)0.12571 (18)0.0499 (11)
C10.4009 (4)0.2243 (3)0.0166 (2)0.0544 (19)
C20.5427 (4)0.2403 (3)0.0037 (2)0.0444 (14)
C30.5756 (4)0.2752 (3)0.0643 (2)0.0527 (16)
C40.7044 (5)0.2844 (3)0.0819 (3)0.0598 (17)
C50.8031 (4)0.2615 (3)0.0303 (3)0.0632 (19)
C60.7722 (4)0.2291 (3)0.0375 (3)0.0557 (16)
C70.6419 (4)0.2167 (3)0.0549 (2)0.0450 (14)
C80.1861 (4)0.2808 (4)0.0041 (3)0.097 (3)
C90.6872 (5)0.0997 (3)0.1507 (3)0.079 (2)
C10A0.6733 (13)0.0159 (9)0.1078 (9)0.132 (3)0.581 (6)
C11A0.5345 (13)0.0144 (10)0.1283 (8)0.132 (3)0.581 (6)
C120.6994 (4)0.3062 (3)0.2254 (3)0.0604 (17)
C11B0.616 (2)0.0690 (11)0.1372 (10)0.132 (3)0.419 (6)
C10B0.6124 (19)0.0243 (11)0.1107 (12)0.132 (3)0.419 (6)
S20.06182 (10)0.20113 (8)0.25426 (7)0.0580 (4)
O50.1063 (3)0.0120 (3)0.2656 (2)0.0812 (14)
O60.1371 (3)0.0088 (2)0.38509 (17)0.0717 (13)
O70.0179 (3)0.1979 (2)0.31664 (18)0.0755 (11)
O80.0053 (3)0.2294 (3)0.1850 (2)0.0885 (14)
N20.1202 (3)0.1019 (2)0.24272 (18)0.0494 (12)
C130.0629 (4)0.0033 (3)0.3280 (3)0.0556 (17)
C140.0786 (4)0.0076 (3)0.3503 (2)0.0449 (16)
C150.1667 (4)0.0543 (3)0.3081 (2)0.0448 (16)
C160.2983 (4)0.0561 (3)0.3294 (3)0.0548 (17)
C170.3441 (4)0.0123 (3)0.3916 (3)0.0661 (19)
C180.2600 (5)0.0339 (3)0.4335 (3)0.0649 (17)
C190.1271 (4)0.0351 (3)0.4137 (3)0.0569 (17)
C200.2745 (4)0.0294 (4)0.3686 (3)0.089 (2)
C210.1850 (5)0.0829 (4)0.1726 (3)0.082 (2)
C22A0.1036 (14)0.0153 (10)0.1341 (8)0.132 (3)0.581 (6)
C23A0.1593 (14)0.0270 (9)0.0668 (7)0.132 (3)0.581 (6)
C240.1951 (5)0.2699 (3)0.2772 (3)0.0776 (19)
C23B0.0401 (17)0.0269 (13)0.1068 (10)0.132 (3)0.419 (6)
C22B0.1746 (18)0.0121 (14)0.1428 (12)0.132 (3)0.419 (6)
H40.725160.305910.128070.0720*
H30.509050.292560.098370.0634*
H8A0.158630.222920.021370.1453*
H8B0.140590.325700.033090.1453*
H8C0.165840.287300.046920.1453*
H9A0.779990.114790.153690.0946*
H9B0.662480.086830.200680.0946*
H10A0.739890.027310.123390.1582*0.581 (6)
H10B0.677400.026450.055090.1582*0.581 (6)
H11A0.534810.026920.180350.1977*0.581 (6)
H11B0.510250.067090.100890.1977*0.581 (6)
H11C0.472230.032090.116400.1977*0.581 (6)
H12A0.740090.337730.186430.0906*
H12B0.761280.264930.247970.0906*
H12C0.672090.347780.261910.0906*
H50.890780.268020.041550.0756*
H60.839230.215240.072350.0665*
H10C0.520600.041920.107160.1582*0.419 (6)
H10D0.641970.023230.060520.1582*0.419 (6)
H11D0.612940.108700.095580.1977*0.419 (6)
H11E0.540810.079860.166380.1977*0.419 (6)
H11F0.694910.078980.166960.1977*0.419 (6)
H170.433320.014070.405440.0795*
H160.356610.087460.301220.0657*
H20A0.316110.019760.342910.1338*
H20B0.317340.039980.413940.1338*
H20C0.281190.081680.338120.1338*
H21A0.189630.136380.142770.0977*
H21B0.273590.060690.182760.0977*
H22A0.019940.042380.119180.1582*0.581 (6)
H22B0.085910.031540.169170.1582*0.581 (6)
H23A0.147960.012660.025390.1977*0.581 (6)
H23B0.114140.081890.055890.1977*0.581 (6)
H23C0.251330.038670.076390.1977*0.581 (6)
H24A0.253460.270950.237050.1170*
H24B0.241250.247530.320890.1170*
H24C0.164320.329100.286290.1170*
H180.291790.064540.475300.0778*
H190.069430.065030.443340.0684*
H22C0.240980.021770.106900.1582*0.419 (6)
H22D0.189820.054150.182950.1582*0.419 (6)
H23D0.024740.022400.143400.1977*0.419 (6)
H23E0.036150.084990.084740.1977*0.419 (6)
H23F0.023120.017420.069250.1977*0.419 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0426 (6)0.0712 (8)0.0403 (6)0.0018 (5)0.0048 (4)0.0047 (6)
O10.0583 (19)0.100 (3)0.088 (3)0.0200 (19)0.0010 (18)0.031 (2)
O20.0456 (17)0.096 (3)0.080 (2)0.0064 (17)0.0020 (16)0.028 (2)
O30.0594 (18)0.098 (3)0.054 (2)0.0344 (17)0.0012 (15)0.0018 (18)
O40.0695 (19)0.106 (3)0.0490 (19)0.0232 (18)0.0167 (16)0.0120 (19)
N10.0535 (19)0.056 (2)0.040 (2)0.0046 (17)0.0007 (16)0.0079 (17)
C10.049 (3)0.072 (4)0.042 (3)0.005 (2)0.000 (2)0.008 (2)
C20.048 (2)0.048 (3)0.037 (2)0.0028 (19)0.0003 (19)0.001 (2)
C30.061 (3)0.059 (3)0.038 (2)0.007 (2)0.001 (2)0.001 (2)
C40.074 (3)0.064 (3)0.043 (3)0.015 (2)0.018 (2)0.005 (2)
C50.051 (3)0.083 (4)0.057 (3)0.007 (2)0.018 (2)0.008 (3)
C60.051 (2)0.067 (3)0.049 (3)0.004 (2)0.003 (2)0.003 (2)
C70.048 (2)0.050 (3)0.037 (2)0.0003 (19)0.0030 (19)0.0008 (19)
C80.049 (3)0.143 (6)0.099 (5)0.006 (3)0.001 (3)0.022 (4)
C90.106 (4)0.059 (4)0.072 (4)0.008 (3)0.005 (3)0.012 (3)
C10A0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C11A0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C120.063 (3)0.064 (3)0.054 (3)0.006 (2)0.000 (2)0.000 (2)
C11B0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C10B0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
S20.0460 (6)0.0661 (8)0.0621 (8)0.0074 (5)0.0061 (5)0.0158 (6)
O50.065 (2)0.116 (3)0.062 (2)0.028 (2)0.0037 (18)0.012 (2)
O60.0513 (18)0.103 (3)0.062 (2)0.0208 (17)0.0156 (16)0.0030 (19)
O70.0662 (19)0.086 (2)0.077 (2)0.0189 (17)0.0312 (18)0.0109 (19)
O80.076 (2)0.114 (3)0.074 (2)0.023 (2)0.0118 (19)0.035 (2)
N20.051 (2)0.057 (2)0.041 (2)0.0002 (17)0.0104 (16)0.0067 (17)
C130.055 (3)0.060 (3)0.052 (3)0.016 (2)0.004 (3)0.004 (2)
C140.048 (2)0.044 (3)0.043 (3)0.0025 (19)0.004 (2)0.002 (2)
C150.047 (2)0.044 (3)0.044 (3)0.0004 (19)0.0072 (19)0.001 (2)
C160.048 (3)0.049 (3)0.068 (3)0.000 (2)0.010 (2)0.006 (2)
C170.048 (3)0.063 (3)0.086 (4)0.003 (2)0.010 (3)0.001 (3)
C180.078 (3)0.056 (3)0.059 (3)0.007 (3)0.013 (3)0.007 (2)
C190.065 (3)0.054 (3)0.052 (3)0.006 (2)0.005 (2)0.006 (2)
C200.054 (3)0.119 (5)0.096 (4)0.029 (3)0.014 (3)0.009 (4)
C210.103 (4)0.089 (4)0.054 (3)0.002 (3)0.017 (3)0.001 (3)
C22A0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C23A0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C240.070 (3)0.055 (3)0.108 (4)0.002 (2)0.006 (3)0.008 (3)
C23B0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
C22B0.156 (6)0.125 (5)0.116 (4)0.008 (4)0.018 (4)0.031 (4)
Geometric parameters (Å, º) top
S1—O31.422 (3)C11A—H11B0.9600
S1—O41.425 (3)C11A—H11C0.9600
S1—N11.630 (3)C11A—H11A0.9600
S1—C121.743 (5)C11B—H11D0.9600
S2—O71.422 (3)C11B—H11E0.9600
S2—O81.418 (4)C11B—H11F0.9600
S2—N21.622 (3)C12—H12C0.9600
S2—C241.739 (5)C12—H12A0.9600
O1—C11.187 (6)C12—H12B0.9600
O2—C11.330 (5)C13—C141.485 (6)
O2—C81.449 (5)C14—C151.395 (6)
O5—C131.199 (6)C14—C191.384 (6)
O6—C131.311 (6)C15—C161.376 (6)
O6—C201.449 (5)C16—C171.366 (7)
N1—C71.431 (5)C17—C181.361 (7)
N1—C91.488 (6)C18—C191.382 (7)
N2—C211.486 (6)C21—C22A1.465 (16)
N2—C151.442 (5)C21—C22B1.53 (2)
C1—C21.492 (6)C22A—C23A1.51 (2)
C2—C31.393 (5)C22B—C23B1.50 (3)
C2—C71.383 (6)C16—H160.9300
C3—C41.371 (7)C17—H170.9300
C4—C51.381 (7)C18—H180.9300
C5—C61.370 (7)C19—H190.9300
C6—C71.390 (6)C20—H20A0.9600
C9—C10A1.482 (15)C20—H20B0.9600
C9—C10B1.527 (19)C20—H20C0.9600
C10A—C11A1.546 (19)C21—H21A0.9700
C10B—C11B1.48 (2)C21—H21B0.9700
C3—H30.9300C22A—H22A0.9700
C4—H40.9300C22A—H22B0.9700
C5—H50.9300C22B—H22D0.9700
C6—H60.9300C22B—H22C0.9700
C8—H8C0.9600C23A—H23B0.9600
C8—H8A0.9600C23A—H23C0.9600
C8—H8B0.9600C23A—H23A0.9600
C9—H9B0.9700C23B—H23D0.9600
C9—H9A0.9700C23B—H23F0.9600
C10A—H10A0.9700C23B—H23E0.9600
C10A—H10B0.9700C24—H24B0.9600
C10B—H10C0.9700C24—H24C0.9600
C10B—H10D0.9700C24—H24A0.9600
O3—S1—O4119.22 (19)H11D—C11B—H11F110.00
O3—S1—N1107.47 (17)H11E—C11B—H11F109.00
O3—S1—C12107.5 (2)C10B—C11B—H11D110.00
O4—S1—N1107.69 (18)H11D—C11B—H11E109.00
O4—S1—C12107.1 (2)H12B—C12—H12C109.00
N1—S1—C12107.4 (2)S1—C12—H12A109.00
O7—S2—O8119.26 (19)S1—C12—H12B109.00
O7—S2—N2107.31 (18)S1—C12—H12C109.00
O7—S2—C24107.4 (2)H12A—C12—H12B109.00
O8—S2—N2107.3 (2)H12A—C12—H12C110.00
O8—S2—C24108.1 (2)O5—C13—O6122.3 (4)
N2—S2—C24106.9 (2)O5—C13—C14125.1 (4)
C1—O2—C8116.0 (4)O6—C13—C14112.4 (4)
C13—O6—C20116.0 (4)C13—C14—C15123.2 (4)
S1—N1—C7118.7 (3)C13—C14—C19118.4 (4)
S1—N1—C9117.8 (3)C15—C14—C19118.3 (4)
C7—N1—C9117.5 (3)N2—C15—C14120.3 (3)
S2—N2—C15117.2 (3)N2—C15—C16119.8 (4)
S2—N2—C21117.9 (3)C14—C15—C16120.0 (4)
C15—N2—C21117.6 (3)C15—C16—C17120.7 (4)
O1—C1—O2123.3 (4)C16—C17—C18120.4 (4)
O1—C1—C2125.7 (4)C17—C18—C19119.8 (5)
O2—C1—C2110.9 (4)C14—C19—C18120.9 (4)
C1—C2—C3118.3 (3)N2—C21—C22A106.0 (7)
C1—C2—C7122.3 (3)N2—C21—C22B117.1 (9)
C3—C2—C7119.3 (4)C21—C22A—C23A116.7 (11)
C2—C3—C4121.1 (4)C21—C22B—C23B109.7 (14)
C3—C4—C5119.4 (5)C15—C16—H16120.00
C4—C5—C6120.2 (4)C17—C16—H16120.00
C5—C6—C7120.9 (4)C16—C17—H17120.00
C2—C7—C6119.2 (4)C18—C17—H17120.00
N1—C7—C6119.1 (4)C17—C18—H18120.00
N1—C7—C2121.7 (4)C19—C18—H18120.00
N1—C9—C10A120.2 (7)C14—C19—H19119.00
N1—C9—C10B103.5 (8)C18—C19—H19120.00
C9—C10A—C11A100.9 (10)O6—C20—H20A110.00
C9—C10B—C11B123.0 (16)O6—C20—H20B109.00
C2—C3—H3119.00O6—C20—H20C109.00
C4—C3—H3119.00H20A—C20—H20B109.00
C3—C4—H4120.00H20A—C20—H20C109.00
C5—C4—H4120.00H20B—C20—H20C109.00
C6—C5—H5120.00N2—C21—H21A111.00
C4—C5—H5120.00N2—C21—H21B111.00
C5—C6—H6120.00C22A—C21—H21A111.00
C7—C6—H6120.00C22A—C21—H21B111.00
O2—C8—H8B110.00H21A—C21—H21B109.00
O2—C8—H8A109.00C22B—C21—H21A126.00
H8B—C8—H8C109.00C22B—C21—H21B78.00
H8A—C8—H8C109.00C21—C22A—H22A108.00
O2—C8—H8C109.00C21—C22A—H22B108.00
H8A—C8—H8B109.00C23A—C22A—H22A108.00
N1—C9—H9A107.00C23A—C22A—H22B108.00
N1—C9—H9B107.00H22A—C22A—H22B107.00
C10A—C9—H9A107.00C23B—C22B—H22D110.00
C10A—C9—H9B107.00H22C—C22B—H22D108.00
C10B—C9—H9A131.00C21—C22B—H22C110.00
C10B—C9—H9B99.00C21—C22B—H22D110.00
H9A—C9—H9B107.00C23B—C22B—H22C110.00
C9—C10A—H10A112.00C22A—C23A—H23C109.00
C11A—C10A—H10A112.00H23A—C23A—H23B110.00
C11A—C10A—H10B112.00H23A—C23A—H23C109.00
C9—C10A—H10B112.00C22A—C23A—H23A109.00
H10A—C10A—H10B109.00C22A—C23A—H23B109.00
C9—C10B—H10C107.00H23B—C23A—H23C109.00
C9—C10B—H10D107.00C22B—C23B—H23D109.00
H10C—C10B—H10D107.00C22B—C23B—H23E109.00
C11B—C10B—H10D106.00H23D—C23B—H23F109.00
C11B—C10B—H10C107.00H23E—C23B—H23F109.00
H11A—C11A—H11C109.00C22B—C23B—H23F109.00
H11B—C11A—H11C109.00H23D—C23B—H23E110.00
C10A—C11A—H11B109.00S2—C24—H24C110.00
C10A—C11A—H11A109.00H24B—C24—H24C110.00
H11A—C11A—H11B109.00H24A—C24—H24B109.00
C10A—C11A—H11C109.00H24A—C24—H24C109.00
C10B—C11B—H11E109.00S2—C24—H24A109.00
C10B—C11B—H11F110.00S2—C24—H24B109.00
O3—S1—N1—C738.0 (3)O1—C1—C2—C740.1 (7)
O3—S1—N1—C9170.0 (3)O2—C1—C2—C340.3 (5)
O4—S1—N1—C7167.6 (3)C1—C2—C7—C6176.5 (4)
O4—S1—N1—C940.4 (3)C1—C2—C3—C4174.5 (4)
C12—S1—N1—C777.4 (3)C7—C2—C3—C41.7 (7)
C12—S1—N1—C974.6 (3)C1—C2—C7—N14.3 (7)
C24—S2—N2—C2176.9 (4)C3—C2—C7—N1179.7 (4)
O8—S2—N2—C15171.7 (3)C3—C2—C7—C60.6 (7)
O7—S2—N2—C1542.4 (3)C2—C3—C4—C52.2 (7)
O7—S2—N2—C21168.1 (3)C3—C4—C5—C60.6 (7)
O8—S2—N2—C2138.8 (4)C4—C5—C6—C71.6 (7)
C24—S2—N2—C1572.6 (3)C5—C6—C7—C22.1 (7)
C8—O2—C1—C2178.1 (4)C5—C6—C7—N1178.7 (4)
C8—O2—C1—O11.8 (6)N1—C9—C10A—C11A74.2 (11)
C20—O6—C13—O52.2 (7)O5—C13—C14—C1535.4 (7)
C20—O6—C13—C14173.4 (4)O5—C13—C14—C19140.6 (5)
S1—N1—C7—C6103.8 (4)O6—C13—C14—C15149.2 (4)
C9—N1—C7—C2132.5 (4)O6—C13—C14—C1934.9 (6)
C9—N1—C7—C648.3 (5)C13—C14—C15—N25.8 (6)
S1—N1—C9—C10A146.0 (7)C13—C14—C15—C16175.2 (4)
C7—N1—C9—C10A61.7 (8)C19—C14—C15—N2178.3 (4)
S1—N1—C7—C275.4 (5)C19—C14—C15—C160.8 (6)
C15—N2—C21—C22A95.0 (7)C13—C14—C19—C18174.2 (4)
S2—N2—C15—C1483.4 (4)C15—C14—C19—C182.0 (7)
S2—N2—C15—C1695.7 (4)N2—C15—C16—C17179.3 (4)
C21—N2—C15—C14127.0 (4)C14—C15—C16—C170.2 (7)
C21—N2—C15—C1653.9 (6)C15—C16—C17—C180.0 (7)
S2—N2—C21—C22A115.6 (7)C16—C17—C18—C191.2 (7)
O1—C1—C2—C3135.9 (5)C17—C18—C19—C142.2 (7)
O2—C1—C2—C7143.7 (4)N2—C21—C22A—C23A170.3 (10)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C6—H6···O8i0.932.593.483 (6)161
C11A—H11C···O10.962.573.486 (15)159
C16—H16···O40.932.513.429 (5)168
C20—H20C···O3ii0.962.573.172 (6)121
C21—H21A···O10.972.553.192 (6)124
C12—H12A···Cg2iii0.962.843.660 (5)144
C18—H18···Cg1iv0.932.873.588 (5)135
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H17NO4S
Mr271.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)10.1762 (4), 15.0178 (6), 18.0900 (8)
β (°) 92.787 (2)
V3)2761.3 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.25 × 0.12 × 0.10
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.955, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
25991, 5409, 2607
Rint0.078
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.193, 1.01
No. of reflections5409
No. of parameters328
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C6—H6···O8i0.932.593.483 (6)161
C11A—H11C···O10.962.573.486 (15)159
C16—H16···O40.932.513.429 (5)168
C20—H20C···O3ii0.962.573.172 (6)121
C21—H21A···O10.972.553.192 (6)124
C12—H12A···Cg2iii0.962.843.660 (5)144
C18—H18···Cg1iv0.932.873.588 (5)135
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y1/2, z+1/2.
 

Acknowledgements

MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).

References

First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationShafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Haider, Z. (2009a). 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. (2009b). 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

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