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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o248.
Published online 2009 December 24. doi:  10.1107/S1600536809054920
PMCID: PMC2980136

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

Abstract

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 [triangle], 2009a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o248-scheme1.jpg

Experimental

Crystal data

  • C12H17NO4S
  • M r = 271.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o248-efi1.jpg
  • 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 [triangle]) T min = 0.955, T max = 0.968
  • 25991 measured reflections
  • 5409 independent reflections
  • 2607 reflections with I > 2σ(I)
  • R int = 0.078

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054920/hb5288sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054920/hb5288Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.
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.
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.

Crystal data

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

Bruker Kappa APEXII CCD diffractometer5409 independent reflections
Radiation source: fine-focus sealed tube2607 reflections with I > 2σ(I)
graphiteRint = 0.078
Detector resolution: 7.70 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −18→18
Tmin = 0.955, Tmax = 0.968l = −22→22
25991 measured reflections

Refinement

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 = 1.01w = 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

Special details

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)

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)
O5−0.1063 (3)−0.0120 (3)0.2656 (2)0.0812 (14)
O6−0.1371 (3)−0.0088 (2)0.38509 (17)0.0717 (13)
O7−0.0179 (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)
C13−0.0629 (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)
C20−0.2745 (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)
H40.725160.30591−0.128070.0720*
H30.509050.29256−0.098370.0634*
H8A0.158630.22292−0.021370.1453*
H8B0.140590.32570−0.033090.1453*
H8C0.165840.287300.046920.1453*
H9A0.779990.114790.153690.0946*
H9B0.662480.086830.200680.0946*
H10A0.73989−0.027310.123390.1582*0.581 (6)
H10B0.677400.026450.055090.1582*0.581 (6)
H11A0.53481−0.026920.180350.1977*0.581 (6)
H11B0.51025−0.067090.100890.1977*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*
H50.890780.26802−0.041550.0756*
H60.839230.215240.072350.0665*
H10C0.520600.041920.107160.1582*0.419 (6)
H10D0.641970.023230.060520.1582*0.419 (6)
H11D0.61294−0.108700.095580.1977*0.419 (6)
H11E0.54081−0.079860.166380.1977*0.419 (6)
H11F0.69491−0.078980.166960.1977*0.419 (6)
H170.433320.014070.405440.0795*
H160.356610.087460.301220.0657*
H20A−0.316110.019760.342910.1338*
H20B−0.31734−0.039980.413940.1338*
H20C−0.28119−0.081680.338120.1338*
H21A0.189630.136380.142770.0977*
H21B0.273590.060690.182760.0977*
H22A0.019940.042380.119180.1582*0.581 (6)
H22B0.08591−0.031540.169170.1582*0.581 (6)
H23A0.147960.012660.025390.1977*0.581 (6)
H23B0.11414−0.081890.055890.1977*0.581 (6)
H23C0.25133−0.038670.076390.1977*0.581 (6)
H24A0.253460.270950.237050.1170*
H24B0.241250.247530.320890.1170*
H24C0.164320.329100.286290.1170*
H180.29179−0.064540.475300.0778*
H190.06943−0.065030.443340.0684*
H22C0.24098−0.021770.106900.1582*0.419 (6)
H22D0.18982−0.054150.182950.1582*0.419 (6)
H23D−0.02474−0.022400.143400.1977*0.419 (6)
H23E0.03615−0.084990.084740.1977*0.419 (6)
H23F0.023120.017420.069250.1977*0.419 (6)

Atomic displacement parameters (Å2)

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, °)

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—C7−40.1 (7)
O3—S1—N1—C9−170.0 (3)O2—C1—C2—C3−40.3 (5)
O4—S1—N1—C7167.6 (3)C1—C2—C7—C6176.5 (4)
O4—S1—N1—C9−40.4 (3)C1—C2—C3—C4−174.5 (4)
C12—S1—N1—C7−77.4 (3)C7—C2—C3—C41.7 (7)
C12—S1—N1—C974.6 (3)C1—C2—C7—N1−4.3 (7)
C24—S2—N2—C21−76.9 (4)C3—C2—C7—N1179.7 (4)
O8—S2—N2—C15−171.7 (3)C3—C2—C7—C60.6 (7)
O7—S2—N2—C15−42.4 (3)C2—C3—C4—C5−2.2 (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—C2−2.1 (7)
C8—O2—C1—C2178.1 (4)C5—C6—C7—N1178.7 (4)
C8—O2—C1—O11.8 (6)N1—C9—C10A—C11A−74.2 (11)
C20—O6—C13—O52.2 (7)O5—C13—C14—C1535.4 (7)
C20—O6—C13—C14−173.4 (4)O5—C13—C14—C19−140.6 (5)
S1—N1—C7—C6103.8 (4)O6—C13—C14—C15−149.2 (4)
C9—N1—C7—C2132.5 (4)O6—C13—C14—C1934.9 (6)
C9—N1—C7—C6−48.3 (5)C13—C14—C15—N25.8 (6)
S1—N1—C9—C10A146.0 (7)C13—C14—C15—C16−175.2 (4)
C7—N1—C9—C10A−61.7 (8)C19—C14—C15—N2−178.3 (4)
S1—N1—C7—C2−75.4 (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—C18−2.0 (7)
S2—N2—C15—C16−95.7 (4)N2—C15—C16—C17179.3 (4)
C21—N2—C15—C14−127.0 (4)C14—C15—C16—C170.2 (7)
C21—N2—C15—C1653.9 (6)C15—C16—C17—C180.0 (7)
S2—N2—C21—C22A−115.6 (7)C16—C17—C18—C19−1.2 (7)
O1—C1—C2—C3135.9 (5)C17—C18—C19—C142.2 (7)
O2—C1—C2—C7143.7 (4)N2—C21—C22A—C23A−170.3 (10)

Hydrogen-bond geometry (Å, °)

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, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5288).

References

  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Haider, Z. (2009a). Acta Cryst. E65, o1413. [PMC free article] [PubMed]
  • Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Khan, M. H. (2009b). Acta Cryst. E65, o955. [PMC free article] [PubMed]
  • Shafiq, M., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Arshad, M. N. (2008). Acta Cryst. E64, o389. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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