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ISSN: 2056-9890

3-(4-Meth­oxy­benz­yl)-2-methyl-1-phenyl­sulfonyl-1H-indole

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 13 March 2009; accepted 18 March 2009; online 25 March 2009)

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C23H21NO3S. The indole ring system is approximately perpendicular to the sulfonyl phenyl ring in both mol­ecules [dihedral angles = 85.42 (8) and 88.30 (9)°]. C—H⋯O inter­actions between mol­ecules stabilize the crystal structure.

Related literature

For the Thorpe–Ingold effect, see: Bassindale (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.]). For bond-length data, 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 the biological activity of sulfur-containing compounds, see: De-Benedetti et al, (1985[De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1532.]); Krishnaiah et al. (1995[Krishnaiah, M., Narayana Raju, K. V., Lu, I.-L., Chen, Y.-S. & Narasinga Rao, S. (1995). Acta Cryst. C51, 2429-2430.]).

[Scheme 1]

Experimental

Crystal data
  • C23H21NO3S

  • Mr = 391.47

  • Triclinic, [P \overline 1]

  • a = 11.4366 (4) Å

  • b = 13.6021 (5) Å

  • c = 14.0001 (5) Å

  • α = 74.154 (1)°

  • β = 67.773 (2)°

  • γ = 88.848 (2)°

  • V = 1930.96 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.963, Tmax = 0.970

  • 45568 measured reflections

  • 10459 independent reflections

  • 7561 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.140

  • S = 1.07

  • 10459 reflections

  • 509 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C11A—H11A⋯O1Bi 0.93 2.52 3.397 (2) 157
C11B—H11B⋯O1Aii 0.93 2.49 3.337 (2) 151
C15A—H15A⋯O3Biii 0.93 2.53 3.398 (2) 155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x-1, y-1, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SAINT and APEX2. 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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Many sulfur-containing compounds, such as sulfates, sulfones and sulfonamides, exhibit insecticidal, germicidal, antimicrobial and antibacterial activities (De-Benedetti et al., 1985; Krishnaiah et al., 1995).

The asymmetric unit contains two crystallographically independent molecules, A and B (Fig. 1). As a result of the electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1—C2 [1.4268 (24) Å and 1.4315 (25) Å] and N1—C5 [1.4180 (23) Å and 1.4160 (24) Å] in molecules A and B are longer than the mean value of 1.355 (14) Å (Allen et al., 1987). Atom S has a tetrahedral geometry, with the O—S—O and N—S—C angles deviating significantly from ideal value, and this may be attributed to the Thorpe-Ingold effect (Bassindale, 1984). The mean plane of the planar indole ring system and the sulfonyl bound phenyl ring are approximately perpendicular to each other in both the molecules A [85.41 (8)°] and B [88.30 (9)°]. The benzylphenyl rings are oriented at angles of 66.73 (8)° and 71.93 (8)° in molecules A & B, respectively.

In the crystal structure, C—H···O interactions (Table 2) link the molecules into linear chain extending along the a axis.

Related literature top

For the Thorpe–Ingold effect, see: Bassindale (1984). For bond-length data, see: Allen et al. (1987). For the biological activity of sulfur-containing compounds, see: De-Benedetti et al., (1985); Krishnaiah et al. (1995).

Experimental top

1-Phenylsulfonyl-2-methyl-3-bromomethylindole (2 g, 5.49 mmol) was dissolved in dry CH3CN (20 ml). To this anisole (0.89 ml, 8.23 mmol), ZnBr2 (2.47 g, 10.96 mmol) were added and refluxed for 12 h. The reaction mixture was quenched with ice containing few drops of conc. HCl, extracted with CHCl3 (3 × 5 ml) and dried Na2SO4. The solvent was removed under vacuo. Then crude was recrystallized from CDCl3 to get the diffraction quality crystals.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(Cmethyl) and 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP plot of the molecule showing that the thermal ellipsoids are drawn at 20% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The molecular packing of the compound viewed down the a axis is shown. Dashed lines indicate hydrogen bonds.
3-(4-Methoxybenzyl)-2-methyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C23H21NO3SZ = 4
Mr = 391.47F(000) = 824
Triclinic, P1Dx = 1.347 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4366 (4) ÅCell parameters from 10459 reflections
b = 13.6021 (5) Åθ = 1.6–29.3°
c = 14.0001 (5) ŵ = 0.19 mm1
α = 74.154 (1)°T = 293 K
β = 67.773 (2)°Block, white
γ = 88.848 (2)°0.20 × 0.20 × 0.18 mm
V = 1930.96 (12) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
10459 independent reflections
Radiation source: fine-focus sealed tube7561 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and ϕ scansθmax = 29.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1515
Tmin = 0.963, Tmax = 0.970k = 1818
45568 measured reflectionsl = 1919
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.438P]
where P = (Fo2 + 2Fc2)/3
10459 reflections(Δ/σ)max = 0.017
509 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C23H21NO3Sγ = 88.848 (2)°
Mr = 391.47V = 1930.96 (12) Å3
Triclinic, P1Z = 4
a = 11.4366 (4) ÅMo Kα radiation
b = 13.6021 (5) ŵ = 0.19 mm1
c = 14.0001 (5) ÅT = 293 K
α = 74.154 (1)°0.20 × 0.20 × 0.18 mm
β = 67.773 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
10459 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
7561 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.970Rint = 0.029
45568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.07Δρmax = 0.26 e Å3
10459 reflectionsΔρmin = 0.29 e Å3
509 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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*/Ueq
N1A0.17038 (13)0.14863 (11)1.12497 (11)0.0443 (3)
C2A0.05288 (16)0.20836 (13)1.05543 (14)0.0466 (4)
C3A0.00977 (16)0.18342 (13)0.96228 (13)0.0454 (4)
C4A0.09665 (15)0.10399 (12)0.97011 (13)0.0424 (3)
C5A0.19475 (15)0.08125 (12)1.07183 (13)0.0405 (3)
C6A0.29250 (17)0.00611 (13)1.10475 (14)0.0480 (4)
H6A0.35690.00881.17300.058*
C7A0.2910 (2)0.04618 (14)1.03236 (17)0.0561 (4)
H7A0.35590.09701.05210.067*
C8A0.1947 (2)0.02427 (15)0.93107 (17)0.0604 (5)
H8A0.19580.06070.88400.072*
C9A0.09766 (19)0.05022 (14)0.89889 (15)0.0531 (4)
H9A0.03350.06460.83050.064*
C10A0.17349 (15)0.03061 (12)1.31777 (11)0.0402 (3)
C11A0.06498 (17)0.05180 (15)1.33280 (14)0.0506 (4)
H11A0.02770.11871.30960.061*
C12A0.0135 (2)0.02814 (18)1.38270 (16)0.0625 (5)
H12A0.05970.01541.39320.075*
C13A0.0695 (2)0.12693 (18)1.41720 (16)0.0658 (6)
H13A0.03400.18041.45110.079*
C14A0.1772 (2)0.14712 (15)1.40197 (15)0.0593 (5)
H14A0.21420.21411.42540.071*
C15A0.23062 (16)0.06838 (13)1.35205 (13)0.0463 (4)
H15A0.30370.08151.34160.056*
C16A0.0059 (2)0.28689 (17)1.08363 (18)0.0683 (6)
H16A0.08190.32001.02350.102*
H16B0.02650.25441.14460.102*
H16C0.05260.33701.10100.102*
C17A0.11050 (17)0.22932 (15)0.86645 (15)0.0566 (5)
H17A0.17470.24250.89220.068*
H17B0.14010.17920.82700.068*
C18A0.09861 (16)0.32724 (14)0.79008 (14)0.0478 (4)
C19A0.02228 (18)0.32887 (14)0.73256 (15)0.0525 (4)
H19A0.02610.26920.74480.063*
C20A0.01679 (19)0.41685 (14)0.65795 (16)0.0549 (4)
H20A0.03480.41620.62030.066*
C21A0.08779 (17)0.50612 (13)0.63898 (14)0.0479 (4)
C22A0.15963 (18)0.50785 (15)0.69830 (16)0.0575 (5)
H22A0.20430.56850.68870.069*
C23A0.16458 (18)0.41830 (16)0.77235 (16)0.0578 (5)
H23A0.21420.41970.81150.069*
C24A0.1586 (2)0.67909 (16)0.5325 (2)0.0744 (6)
H24A0.24520.66340.51430.112*
H24B0.13320.70720.59240.112*
H24C0.15080.72820.47180.112*
O1A0.37088 (12)0.09840 (11)1.28435 (10)0.0568 (3)
O2A0.21330 (15)0.22300 (10)1.27677 (11)0.0620 (4)
O3A0.07983 (15)0.58831 (10)0.56047 (12)0.0646 (4)
S1A0.24227 (4)0.13171 (3)1.25612 (3)0.04469 (11)
N1B0.69123 (14)0.70806 (11)0.13816 (11)0.0464 (3)
C2B0.57402 (17)0.73507 (14)0.06982 (14)0.0476 (4)
C3B0.52747 (16)0.65959 (14)0.02341 (14)0.0477 (4)
C4B0.61181 (17)0.58004 (13)0.01765 (14)0.0472 (4)
C5B0.71146 (16)0.60928 (13)0.08345 (14)0.0444 (4)
C6B0.80826 (19)0.54755 (15)0.11375 (17)0.0550 (4)
H6B0.87390.56720.18150.066*
C7B0.8031 (2)0.45559 (16)0.0391 (2)0.0670 (6)
H7B0.86680.41230.05700.080*
C8B0.7064 (3)0.42618 (16)0.0611 (2)0.0722 (6)
H8B0.70630.36370.10940.087*
C9B0.6102 (2)0.48702 (15)0.09113 (17)0.0621 (5)
H9B0.54530.46660.15920.075*
C10B0.68658 (15)0.69410 (13)0.32679 (12)0.0419 (3)
C11B0.57731 (17)0.72794 (15)0.33924 (14)0.0510 (4)
H11B0.54330.78460.31740.061*
C12B0.5192 (2)0.67717 (18)0.38412 (18)0.0658 (5)
H12B0.44530.69930.39280.079*
C13B0.5700 (2)0.59387 (19)0.41614 (19)0.0727 (6)
H13B0.53030.55950.44630.087*
C14B0.6788 (2)0.56071 (18)0.40416 (18)0.0699 (6)
H14B0.71230.50410.42630.084*
C15B0.73916 (19)0.61057 (15)0.35946 (15)0.0548 (4)
H15B0.81330.58850.35150.066*
C16B0.5195 (2)0.83354 (18)0.09892 (18)0.0675 (6)
H16D0.44430.83740.03900.101*
H16E0.49850.83700.15990.101*
H16F0.58060.88980.11670.101*
C17B0.40745 (18)0.65872 (17)0.11788 (16)0.0598 (5)
H17C0.37680.58810.16000.072*
H17D0.34360.68790.09140.072*
C18B0.42235 (16)0.71719 (14)0.19031 (14)0.0488 (4)
C19B0.35364 (17)0.79902 (16)0.20903 (15)0.0552 (4)
H19B0.29790.81950.17470.066*
C20B0.36479 (18)0.85184 (15)0.27728 (15)0.0543 (4)
H20B0.31780.90730.28790.065*
C21B0.44567 (17)0.82183 (13)0.32917 (13)0.0472 (4)
C22B0.51781 (18)0.74128 (15)0.30985 (15)0.0530 (4)
H22B0.57490.72210.34290.064*
C23B0.50558 (17)0.68950 (14)0.24221 (16)0.0534 (4)
H23B0.55380.63480.23080.064*
C24B0.3822 (2)0.94124 (19)0.43162 (19)0.0734 (6)
H24D0.29570.91150.46610.110*
H24E0.39150.99700.36920.110*
H24F0.40430.96630.48090.110*
O1B0.88915 (12)0.73377 (12)0.29917 (11)0.0627 (4)
O2B0.73674 (15)0.86335 (10)0.29267 (12)0.0632 (4)
O3B0.46289 (14)0.86603 (12)0.40024 (12)0.0656 (4)
S1B0.76171 (4)0.75867 (3)0.26991 (3)0.04760 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0514 (8)0.0460 (7)0.0356 (7)0.0003 (6)0.0189 (6)0.0089 (6)
C2A0.0511 (9)0.0450 (9)0.0435 (9)0.0003 (7)0.0261 (7)0.0011 (7)
C3A0.0432 (8)0.0452 (9)0.0431 (9)0.0070 (7)0.0191 (7)0.0021 (7)
C4A0.0449 (8)0.0406 (8)0.0411 (8)0.0119 (7)0.0190 (7)0.0080 (6)
C5A0.0462 (8)0.0402 (8)0.0385 (8)0.0092 (6)0.0219 (7)0.0090 (6)
C6A0.0493 (9)0.0460 (9)0.0466 (9)0.0026 (7)0.0198 (7)0.0081 (7)
C7A0.0659 (12)0.0457 (9)0.0635 (12)0.0020 (8)0.0337 (10)0.0135 (8)
C8A0.0823 (14)0.0525 (10)0.0584 (11)0.0132 (10)0.0346 (11)0.0247 (9)
C9A0.0631 (11)0.0506 (10)0.0447 (9)0.0145 (8)0.0185 (8)0.0161 (8)
C10A0.0430 (8)0.0478 (9)0.0277 (7)0.0072 (7)0.0109 (6)0.0120 (6)
C11A0.0520 (10)0.0601 (11)0.0414 (9)0.0046 (8)0.0189 (7)0.0163 (8)
C12A0.0565 (11)0.0848 (15)0.0520 (11)0.0137 (10)0.0292 (9)0.0171 (10)
C13A0.0696 (13)0.0728 (14)0.0492 (11)0.0231 (11)0.0267 (10)0.0043 (9)
C14A0.0681 (12)0.0515 (10)0.0433 (9)0.0059 (9)0.0136 (9)0.0016 (8)
C15A0.0454 (9)0.0519 (9)0.0361 (8)0.0036 (7)0.0115 (7)0.0101 (7)
C16A0.0794 (14)0.0687 (13)0.0589 (12)0.0191 (11)0.0371 (11)0.0049 (10)
C17A0.0441 (9)0.0582 (11)0.0525 (10)0.0067 (8)0.0140 (8)0.0005 (8)
C18A0.0403 (8)0.0527 (10)0.0405 (8)0.0029 (7)0.0101 (7)0.0058 (7)
C19A0.0583 (10)0.0451 (9)0.0539 (10)0.0014 (8)0.0237 (8)0.0106 (8)
C20A0.0641 (11)0.0538 (10)0.0548 (10)0.0045 (9)0.0321 (9)0.0147 (8)
C21A0.0503 (9)0.0454 (9)0.0428 (9)0.0052 (7)0.0141 (7)0.0106 (7)
C22A0.0549 (10)0.0527 (10)0.0586 (11)0.0101 (8)0.0213 (9)0.0064 (8)
C23A0.0505 (10)0.0658 (12)0.0554 (11)0.0063 (9)0.0265 (9)0.0052 (9)
C24A0.0725 (14)0.0504 (11)0.0785 (15)0.0012 (10)0.0214 (12)0.0043 (10)
O1A0.0454 (7)0.0710 (9)0.0518 (7)0.0162 (6)0.0166 (6)0.0182 (6)
O2A0.0857 (10)0.0498 (7)0.0597 (8)0.0162 (7)0.0311 (7)0.0263 (6)
O3A0.0790 (9)0.0495 (7)0.0606 (8)0.0022 (7)0.0321 (7)0.0012 (6)
S1A0.0505 (2)0.0463 (2)0.0390 (2)0.01163 (17)0.01780 (17)0.01493 (16)
N1B0.0526 (8)0.0511 (8)0.0422 (7)0.0124 (6)0.0233 (6)0.0175 (6)
C2B0.0517 (9)0.0569 (10)0.0483 (9)0.0147 (8)0.0282 (8)0.0251 (8)
C3B0.0480 (9)0.0562 (10)0.0476 (9)0.0040 (7)0.0222 (7)0.0230 (8)
C4B0.0534 (9)0.0468 (9)0.0490 (9)0.0009 (7)0.0256 (8)0.0173 (7)
C5B0.0511 (9)0.0459 (9)0.0484 (9)0.0071 (7)0.0293 (8)0.0185 (7)
C6B0.0573 (10)0.0612 (11)0.0608 (11)0.0167 (9)0.0310 (9)0.0287 (9)
C7B0.0820 (14)0.0573 (12)0.0873 (16)0.0295 (11)0.0520 (13)0.0342 (11)
C8B0.1045 (18)0.0479 (11)0.0780 (15)0.0154 (11)0.0527 (14)0.0150 (10)
C9B0.0813 (14)0.0501 (10)0.0571 (11)0.0019 (10)0.0320 (10)0.0107 (9)
C10B0.0437 (8)0.0461 (8)0.0327 (7)0.0005 (7)0.0122 (6)0.0100 (6)
C11B0.0528 (10)0.0558 (10)0.0466 (9)0.0073 (8)0.0210 (8)0.0157 (8)
C12B0.0623 (12)0.0802 (14)0.0649 (13)0.0040 (10)0.0337 (10)0.0230 (11)
C13B0.0859 (16)0.0802 (15)0.0667 (13)0.0046 (12)0.0369 (12)0.0324 (12)
C14B0.0872 (16)0.0659 (13)0.0640 (13)0.0103 (11)0.0261 (12)0.0352 (11)
C15B0.0572 (10)0.0589 (11)0.0484 (10)0.0116 (9)0.0176 (8)0.0201 (8)
C16B0.0811 (14)0.0768 (14)0.0602 (12)0.0369 (12)0.0388 (11)0.0296 (11)
C17B0.0474 (10)0.0760 (13)0.0584 (11)0.0003 (9)0.0168 (9)0.0281 (10)
C18B0.0410 (8)0.0593 (10)0.0421 (9)0.0012 (7)0.0108 (7)0.0157 (8)
C19B0.0485 (9)0.0699 (12)0.0487 (10)0.0126 (9)0.0202 (8)0.0176 (9)
C20B0.0525 (10)0.0555 (10)0.0496 (10)0.0127 (8)0.0139 (8)0.0156 (8)
C21B0.0476 (9)0.0491 (9)0.0382 (8)0.0023 (7)0.0105 (7)0.0104 (7)
C22B0.0511 (10)0.0589 (11)0.0530 (10)0.0079 (8)0.0243 (8)0.0163 (8)
C23B0.0520 (10)0.0530 (10)0.0575 (11)0.0117 (8)0.0212 (8)0.0201 (8)
C24B0.0702 (13)0.0791 (15)0.0656 (13)0.0018 (11)0.0072 (11)0.0397 (12)
O1B0.0448 (7)0.0811 (10)0.0611 (8)0.0019 (6)0.0182 (6)0.0214 (7)
O2B0.0816 (10)0.0444 (7)0.0637 (8)0.0023 (6)0.0316 (7)0.0104 (6)
O3B0.0721 (9)0.0721 (9)0.0626 (9)0.0086 (7)0.0270 (7)0.0338 (7)
S1B0.0492 (2)0.0500 (2)0.0440 (2)0.00122 (18)0.01884 (18)0.01247 (18)
Geometric parameters (Å, º) top
N1A—C5A1.418 (2)N1B—C5B1.416 (2)
N1A—C2A1.427 (2)N1B—C2B1.432 (2)
N1A—S1A1.6538 (14)N1B—S1B1.6522 (15)
C2A—C3A1.344 (2)C2B—C3B1.344 (3)
C2A—C16A1.487 (3)C2B—C16B1.486 (3)
C3A—C4A1.436 (2)C3B—C4B1.433 (2)
C3A—C17A1.504 (2)C3B—C17B1.501 (3)
C4A—C9A1.392 (2)C4B—C9B1.391 (3)
C4A—C5A1.395 (2)C4B—C5B1.397 (3)
C5A—C6A1.381 (2)C5B—C6B1.383 (2)
C6A—C7A1.383 (3)C6B—C7B1.379 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.383 (3)C7B—C8B1.374 (4)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.371 (3)C8B—C9B1.370 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.383 (2)C10B—C11B1.379 (2)
C10A—C15A1.384 (2)C10B—C15B1.382 (2)
C10A—S1A1.7541 (16)C10B—S1B1.7531 (17)
C11A—C12A1.374 (3)C11B—C12B1.373 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.377 (3)C12B—C13B1.370 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.372 (3)C13B—C14B1.368 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.377 (3)C14B—C15B1.381 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—C18A1.504 (2)C17B—C18B1.506 (3)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—C23A1.376 (3)C18B—C19B1.376 (3)
C18A—C19A1.390 (2)C18B—C23B1.391 (3)
C19A—C20A1.375 (3)C19B—C20B1.384 (3)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.380 (3)C20B—C21B1.372 (3)
C20A—H20A0.9300C20B—H20B0.9300
C21A—O3A1.366 (2)C21B—O3B1.367 (2)
C21A—C22A1.376 (3)C21B—C22B1.382 (3)
C22A—C23A1.383 (3)C22B—C23B1.372 (3)
C22A—H22A0.9300C22B—H22B0.9300
C23A—H23A0.9300C23B—H23B0.9300
C24A—O3A1.415 (3)C24B—O3B1.412 (3)
C24A—H24A0.9600C24B—H24D0.9600
C24A—H24B0.9600C24B—H24E0.9600
C24A—H24C0.9600C24B—H24F0.9600
O1A—S1A1.4192 (14)O1B—S1B1.4181 (14)
O2A—S1A1.4213 (14)O2B—S1B1.4197 (14)
C5A—N1A—C2A107.88 (13)C5B—N1B—C2B107.57 (14)
C5A—N1A—S1A123.21 (11)C5B—N1B—S1B123.08 (12)
C2A—N1A—S1A126.23 (12)C2B—N1B—S1B125.78 (12)
C3A—C2A—N1A108.60 (15)C3B—C2B—N1B108.71 (15)
C3A—C2A—C16A127.44 (17)C3B—C2B—C16B127.32 (17)
N1A—C2A—C16A123.93 (17)N1B—C2B—C16B123.92 (17)
C2A—C3A—C4A108.57 (15)C2B—C3B—C4B108.57 (16)
C2A—C3A—C17A125.91 (17)C2B—C3B—C17B125.76 (17)
C4A—C3A—C17A125.51 (16)C4B—C3B—C17B125.67 (17)
C9A—C4A—C5A119.20 (16)C9B—C4B—C5B119.45 (17)
C9A—C4A—C3A132.64 (16)C9B—C4B—C3B132.38 (18)
C5A—C4A—C3A108.16 (15)C5B—C4B—C3B108.17 (15)
C6A—C5A—C4A122.07 (16)C6B—C5B—C4B121.90 (17)
C6A—C5A—N1A131.23 (15)C6B—C5B—N1B131.17 (17)
C4A—C5A—N1A106.70 (14)C4B—C5B—N1B106.90 (14)
C5A—C6A—C7A117.48 (17)C7B—C6B—C5B117.0 (2)
C5A—C6A—H6A121.3C7B—C6B—H6B121.5
C7A—C6A—H6A121.3C5B—C6B—H6B121.5
C6A—C7A—C8A121.15 (18)C8B—C7B—C6B121.8 (2)
C6A—C7A—H7A119.4C8B—C7B—H7B119.1
C8A—C7A—H7A119.4C6B—C7B—H7B119.1
C9A—C8A—C7A121.13 (18)C9B—C8B—C7B121.3 (2)
C9A—C8A—H8A119.4C9B—C8B—H8B119.4
C7A—C8A—H8A119.4C7B—C8B—H8B119.4
C8A—C9A—C4A118.97 (17)C8B—C9B—C4B118.5 (2)
C8A—C9A—H9A120.5C8B—C9B—H9B120.7
C4A—C9A—H9A120.5C4B—C9B—H9B120.7
C11A—C10A—C15A121.56 (16)C11B—C10B—C15B121.21 (17)
C11A—C10A—S1A119.34 (13)C11B—C10B—S1B119.68 (13)
C15A—C10A—S1A119.10 (13)C15B—C10B—S1B119.10 (14)
C12A—C11A—C10A118.55 (18)C12B—C11B—C10B119.37 (18)
C12A—C11A—H11A120.7C12B—C11B—H11B120.3
C10A—C11A—H11A120.7C10B—C11B—H11B120.3
C11A—C12A—C13A120.43 (19)C13B—C12B—C11B119.9 (2)
C11A—C12A—H12A119.8C13B—C12B—H12B120.1
C13A—C12A—H12A119.8C11B—C12B—H12B120.1
C14A—C13A—C12A120.55 (19)C14B—C13B—C12B120.6 (2)
C14A—C13A—H13A119.7C14B—C13B—H13B119.7
C12A—C13A—H13A119.7C12B—C13B—H13B119.7
C13A—C14A—C15A120.16 (19)C13B—C14B—C15B120.6 (2)
C13A—C14A—H14A119.9C13B—C14B—H14B119.7
C15A—C14A—H14A119.9C15B—C14B—H14B119.7
C14A—C15A—C10A118.75 (17)C14B—C15B—C10B118.32 (19)
C14A—C15A—H15A120.6C14B—C15B—H15B120.8
C10A—C15A—H15A120.6C10B—C15B—H15B120.8
C2A—C16A—H16A109.5C2B—C16B—H16D109.5
C2A—C16A—H16B109.5C2B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C2A—C16A—H16C109.5C2B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C18A—C17A—C3A115.02 (15)C3B—C17B—C18B113.98 (15)
C18A—C17A—H17A108.5C3B—C17B—H17C108.8
C3A—C17A—H17A108.5C18B—C17B—H17C108.8
C18A—C17A—H17B108.5C3B—C17B—H17D108.8
C3A—C17A—H17B108.5C18B—C17B—H17D108.8
H17A—C17A—H17B107.5H17C—C17B—H17D107.7
C23A—C18A—C19A117.21 (16)C19B—C18B—C23B117.28 (17)
C23A—C18A—C17A121.64 (17)C19B—C18B—C17B121.71 (17)
C19A—C18A—C17A121.14 (17)C23B—C18B—C17B121.01 (17)
C20A—C19A—C18A121.41 (17)C18B—C19B—C20B122.09 (17)
C20A—C19A—H19A119.3C18B—C19B—H19B119.0
C18A—C19A—H19A119.3C20B—C19B—H19B119.0
C19A—C20A—C21A120.03 (17)C21B—C20B—C19B119.55 (17)
C19A—C20A—H20A120.0C21B—C20B—H20B120.2
C21A—C20A—H20A120.0C19B—C20B—H20B120.2
O3A—C21A—C22A124.57 (17)O3B—C21B—C20B125.15 (17)
O3A—C21A—C20A115.69 (16)O3B—C21B—C22B115.42 (16)
C22A—C21A—C20A119.73 (17)C20B—C21B—C22B119.43 (17)
C21A—C22A—C23A119.22 (18)C23B—C22B—C21B120.35 (17)
C21A—C22A—H22A120.4C23B—C22B—H22B119.8
C23A—C22A—H22A120.4C21B—C22B—H22B119.8
C18A—C23A—C22A122.29 (18)C22B—C23B—C18B121.26 (17)
C18A—C23A—H23A118.9C22B—C23B—H23B119.4
C22A—C23A—H23A118.9C18B—C23B—H23B119.4
O3A—C24A—H24A109.5O3B—C24B—H24D109.5
O3A—C24A—H24B109.5O3B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
O3A—C24A—H24C109.5O3B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C21A—O3A—C24A117.59 (16)C21B—O3B—C24B117.74 (17)
O1A—S1A—O2A119.34 (9)O1B—S1B—O2B119.31 (9)
O1A—S1A—N1A106.26 (8)O1B—S1B—N1B106.45 (8)
O2A—S1A—N1A107.20 (8)O2B—S1B—N1B106.90 (8)
O1A—S1A—C10A108.19 (8)O1B—S1B—C10B108.35 (8)
O2A—S1A—C10A108.93 (8)O2B—S1B—C10B109.11 (8)
N1A—S1A—C10A106.17 (7)N1B—S1B—C10B105.93 (7)
C5A—N1A—C2A—C3A2.93 (18)C5B—N1B—C2B—C3B2.57 (18)
S1A—N1A—C2A—C3A164.68 (12)S1B—N1B—C2B—C3B161.65 (12)
C5A—N1A—C2A—C16A179.01 (16)C5B—N1B—C2B—C16B179.91 (16)
S1A—N1A—C2A—C16A17.3 (2)S1B—N1B—C2B—C16B20.8 (2)
N1A—C2A—C3A—C4A1.80 (18)N1B—C2B—C3B—C4B1.20 (19)
C16A—C2A—C3A—C4A179.77 (17)C16B—C2B—C3B—C4B178.62 (17)
N1A—C2A—C3A—C17A179.27 (15)N1B—C2B—C3B—C17B178.69 (15)
C16A—C2A—C3A—C17A1.3 (3)C16B—C2B—C3B—C17B1.3 (3)
C2A—C3A—C4A—C9A179.35 (17)C2B—C3B—C4B—C9B178.77 (19)
C17A—C3A—C4A—C9A0.4 (3)C17B—C3B—C4B—C9B1.1 (3)
C2A—C3A—C4A—C5A0.01 (18)C2B—C3B—C4B—C5B0.62 (19)
C17A—C3A—C4A—C5A178.93 (15)C17B—C3B—C4B—C5B179.49 (16)
C9A—C4A—C5A—C6A0.7 (2)C9B—C4B—C5B—C6B1.1 (3)
C3A—C4A—C5A—C6A178.74 (14)C3B—C4B—C5B—C6B179.45 (15)
C9A—C4A—C5A—N1A178.75 (14)C9B—C4B—C5B—N1B177.29 (15)
C3A—C4A—C5A—N1A1.80 (17)C3B—C4B—C5B—N1B2.18 (18)
C2A—N1A—C5A—C6A177.74 (16)C2B—N1B—C5B—C6B178.96 (17)
S1A—N1A—C5A—C6A15.3 (2)S1B—N1B—C5B—C6B19.2 (3)
C2A—N1A—C5A—C4A2.87 (17)C2B—N1B—C5B—C4B2.89 (18)
S1A—N1A—C5A—C4A165.29 (11)S1B—N1B—C5B—C4B162.66 (12)
C4A—C5A—C6A—C7A0.6 (2)C4B—C5B—C6B—C7B0.6 (3)
N1A—C5A—C6A—C7A178.69 (16)N1B—C5B—C6B—C7B177.29 (17)
C5A—C6A—C7A—C8A0.4 (3)C5B—C6B—C7B—C8B0.1 (3)
C6A—C7A—C8A—C9A0.2 (3)C6B—C7B—C8B—C9B0.3 (4)
C7A—C8A—C9A—C4A0.3 (3)C7B—C8B—C9B—C4B0.1 (3)
C5A—C4A—C9A—C8A0.5 (2)C5B—C4B—C9B—C8B0.8 (3)
C3A—C4A—C9A—C8A178.78 (17)C3B—C4B—C9B—C8B179.87 (19)
C15A—C10A—C11A—C12A0.2 (2)C15B—C10B—C11B—C12B0.5 (3)
S1A—C10A—C11A—C12A179.03 (14)S1B—C10B—C11B—C12B179.83 (15)
C10A—C11A—C12A—C13A0.3 (3)C10B—C11B—C12B—C13B0.1 (3)
C11A—C12A—C13A—C14A0.2 (3)C11B—C12B—C13B—C14B0.2 (4)
C12A—C13A—C14A—C15A0.1 (3)C12B—C13B—C14B—C15B0.1 (4)
C13A—C14A—C15A—C10A0.1 (3)C13B—C14B—C15B—C10B0.4 (3)
C11A—C10A—C15A—C14A0.2 (2)C11B—C10B—C15B—C14B0.7 (3)
S1A—C10A—C15A—C14A178.95 (13)S1B—C10B—C15B—C14B179.95 (15)
C2A—C3A—C17A—C18A85.4 (2)C2B—C3B—C17B—C18B82.4 (2)
C4A—C3A—C17A—C18A95.9 (2)C4B—C3B—C17B—C18B97.4 (2)
C3A—C17A—C18A—C23A116.8 (2)C3B—C17B—C18B—C19B120.4 (2)
C3A—C17A—C18A—C19A64.6 (2)C3B—C17B—C18B—C23B60.4 (3)
C23A—C18A—C19A—C20A2.5 (3)C23B—C18B—C19B—C20B0.6 (3)
C17A—C18A—C19A—C20A176.14 (18)C17B—C18B—C19B—C20B178.61 (17)
C18A—C19A—C20A—C21A0.1 (3)C18B—C19B—C20B—C21B0.6 (3)
C19A—C20A—C21A—O3A177.53 (17)C19B—C20B—C21B—O3B178.41 (17)
C19A—C20A—C21A—C22A2.8 (3)C19B—C20B—C21B—C22B2.0 (3)
O3A—C21A—C22A—C23A177.08 (18)O3B—C21B—C22B—C23B178.21 (17)
C20A—C21A—C22A—C23A3.3 (3)C20B—C21B—C22B—C23B2.2 (3)
C19A—C18A—C23A—C22A2.0 (3)C21B—C22B—C23B—C18B0.9 (3)
C17A—C18A—C23A—C22A176.63 (18)C19B—C18B—C23B—C22B0.5 (3)
C21A—C22A—C23A—C18A0.9 (3)C17B—C18B—C23B—C22B178.77 (18)
C22A—C21A—O3A—C24A5.2 (3)C20B—C21B—O3B—C24B7.0 (3)
C20A—C21A—O3A—C24A175.18 (18)C22B—C21B—O3B—C24B173.44 (18)
C5A—N1A—S1A—O1A40.19 (15)C5B—N1B—S1B—O1B41.21 (15)
C2A—N1A—S1A—O1A160.69 (14)C2B—N1B—S1B—O1B162.76 (14)
C5A—N1A—S1A—O2A168.85 (13)C5B—N1B—S1B—O2B169.76 (13)
C2A—N1A—S1A—O2A32.03 (16)C2B—N1B—S1B—O2B34.21 (17)
C5A—N1A—S1A—C10A74.84 (14)C5B—N1B—S1B—C10B73.98 (15)
C2A—N1A—S1A—C10A84.28 (15)C2B—N1B—S1B—C10B82.05 (15)
C11A—C10A—S1A—O1A159.14 (13)C11B—C10B—S1B—O1B160.15 (14)
C15A—C10A—S1A—O1A19.67 (15)C15B—C10B—S1B—O1B19.15 (16)
C11A—C10A—S1A—O2A27.99 (15)C11B—C10B—S1B—O2B28.80 (16)
C15A—C10A—S1A—O2A150.82 (13)C15B—C10B—S1B—O2B150.50 (14)
C11A—C10A—S1A—N1A87.15 (14)C11B—C10B—S1B—N1B85.96 (15)
C15A—C10A—S1A—N1A94.04 (13)C15B—C10B—S1B—N1B94.74 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11A—H11A···O1Bi0.932.523.397 (2)157
C11B—H11B···O1Aii0.932.493.337 (2)151
C15A—H15A···O3Biii0.932.533.398 (2)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x1, y1, z+1.

Experimental details

Crystal data
Chemical formulaC23H21NO3S
Mr391.47
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.4366 (4), 13.6021 (5), 14.0001 (5)
α, β, γ (°)74.154 (1), 67.773 (2), 88.848 (2)
V3)1930.96 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.963, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
45568, 10459, 7561
Rint0.029
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.140, 1.07
No. of reflections10459
No. of parameters509
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11A—H11A···O1Bi0.932.523.397 (2)157.4
C11B—H11B···O1Aii0.932.493.337 (2)150.8
C15A—H15A···O3Biii0.932.533.398 (2)155.2
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x1, y1, z+1.
 

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT– Madras, Chennai, India, for his help with the data collection.

References

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