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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o847.
Published online 2009 March 25. doi:  10.1107/S1600536809010046
PMCID: PMC2968905

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

Abstract

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 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the biological activity of sulfur-containing compounds, see: De-Benedetti et al, (1985 [triangle]); Krishnaiah et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o847-scheme1.jpg

Experimental

Crystal data

  • C23H21NO3S
  • M r = 391.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o847-efi1.jpg
  • 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 [triangle]) T min = 0.963, T max = 0.970
  • 45568 measured reflections
  • 10459 independent reflections
  • 7561 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010046/bt2902sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010046/bt2902Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

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.
Fig. 2.
The molecular packing of the compound viewed down the a axis is shown. Dashed lines indicate hydrogen bonds.

Crystal data

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

Bruker Kappa APEXII diffractometer10459 independent reflections
Radiation source: fine-focus sealed tube7561 reflections with I > 2σ(I)
graphiteRint = 0.029
ω and [var phi] scansθmax = 29.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −15→15
Tmin = 0.963, Tmax = 0.970k = −18→18
45568 measured reflectionsl = −19→19

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.07w = 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

Special details

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)

xyzUiso*/Ueq
N1A−0.17038 (13)0.14863 (11)1.12497 (11)0.0443 (3)
C2A−0.05288 (16)0.20836 (13)1.05543 (14)0.0466 (4)
C3A−0.00977 (16)0.18342 (13)0.96228 (13)0.0454 (4)
C4A−0.09665 (15)0.10399 (12)0.97011 (13)0.0424 (3)
C5A−0.19475 (15)0.08125 (12)1.07183 (13)0.0405 (3)
C6A−0.29250 (17)0.00611 (13)1.10475 (14)0.0480 (4)
H6A−0.3569−0.00881.17300.058*
C7A−0.2910 (2)−0.04618 (14)1.03236 (17)0.0561 (4)
H7A−0.3559−0.09701.05210.067*
C8A−0.1947 (2)−0.02427 (15)0.93107 (17)0.0604 (5)
H8A−0.1958−0.06070.88400.072*
C9A−0.09766 (19)0.05022 (14)0.89889 (15)0.0531 (4)
H9A−0.03350.06460.83050.064*
C10A−0.17349 (15)0.03061 (12)1.31777 (11)0.0402 (3)
C11A−0.06498 (17)0.05180 (15)1.33280 (14)0.0506 (4)
H11A−0.02770.11871.30960.061*
C12A−0.0135 (2)−0.02814 (18)1.38270 (16)0.0625 (5)
H12A0.0597−0.01541.39320.075*
C13A−0.0695 (2)−0.12693 (18)1.41720 (16)0.0658 (6)
H13A−0.0340−0.18041.45110.079*
C14A−0.1772 (2)−0.14712 (15)1.40197 (15)0.0593 (5)
H14A−0.2142−0.21411.42540.071*
C15A−0.23062 (16)−0.06838 (13)1.35205 (13)0.0463 (4)
H15A−0.3037−0.08151.34160.056*
C16A0.0059 (2)0.28689 (17)1.08363 (18)0.0683 (6)
H16A0.08190.32001.02350.102*
H16B0.02650.25441.14460.102*
H16C−0.05260.33701.10100.102*
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)
H19A−0.02610.26920.74480.063*
C20A0.01679 (19)0.41685 (14)0.65795 (16)0.0549 (4)
H20A−0.03480.41620.62030.066*
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*
O1A−0.37088 (12)0.09840 (11)1.28435 (10)0.0568 (3)
O2A−0.21330 (15)0.22300 (10)1.27677 (11)0.0620 (4)
O3A0.07983 (15)0.58831 (10)0.56047 (12)0.0646 (4)
S1A−0.24227 (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)
H6B0.87390.5672−0.18150.066*
C7B0.8031 (2)0.45559 (16)−0.0391 (2)0.0670 (6)
H7B0.86680.4123−0.05700.080*
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)
H11B0.54330.7846−0.31740.061*
C12B0.5192 (2)0.67717 (18)−0.38412 (18)0.0658 (5)
H12B0.44530.6993−0.39280.079*
C13B0.5700 (2)0.59387 (19)−0.41614 (19)0.0727 (6)
H13B0.53030.5595−0.44630.087*
C14B0.6788 (2)0.56071 (18)−0.40416 (18)0.0699 (6)
H14B0.71230.5041−0.42630.084*
C15B0.73916 (19)0.61057 (15)−0.35946 (15)0.0548 (4)
H15B0.81330.5885−0.35150.066*
C16B0.5195 (2)0.83354 (18)−0.09892 (18)0.0675 (6)
H16D0.44430.8374−0.03900.101*
H16E0.49850.8370−0.15990.101*
H16F0.58060.8898−0.11670.101*
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)

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, °)

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—C16A−179.01 (16)C5B—N1B—C2B—C16B−179.91 (16)
S1A—N1A—C2A—C16A−17.3 (2)S1B—N1B—C2B—C16B−20.8 (2)
N1A—C2A—C3A—C4A−1.80 (18)N1B—C2B—C3B—C4B−1.20 (19)
C16A—C2A—C3A—C4A−179.77 (17)C16B—C2B—C3B—C4B−178.62 (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—C9A−179.35 (17)C2B—C3B—C4B—C9B178.77 (19)
C17A—C3A—C4A—C9A−0.4 (3)C17B—C3B—C4B—C9B−1.1 (3)
C2A—C3A—C4A—C5A−0.01 (18)C2B—C3B—C4B—C5B−0.62 (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—C6A−178.74 (14)C3B—C4B—C5B—C6B−179.45 (15)
C9A—C4A—C5A—N1A−178.75 (14)C9B—C4B—C5B—N1B−177.29 (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—C4A−2.87 (17)C2B—N1B—C5B—C4B−2.89 (18)
S1A—N1A—C5A—C4A−165.29 (11)S1B—N1B—C5B—C4B−162.66 (12)
C4A—C5A—C6A—C7A−0.6 (2)C4B—C5B—C6B—C7B−0.6 (3)
N1A—C5A—C6A—C7A178.69 (16)N1B—C5B—C6B—C7B177.29 (17)
C5A—C6A—C7A—C8A0.4 (3)C5B—C6B—C7B—C8B−0.1 (3)
C6A—C7A—C8A—C9A−0.2 (3)C6B—C7B—C8B—C9B0.3 (4)
C7A—C8A—C9A—C4A0.3 (3)C7B—C8B—C9B—C4B0.1 (3)
C5A—C4A—C9A—C8A−0.5 (2)C5B—C4B—C9B—C8B−0.8 (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—C13A−0.3 (3)C10B—C11B—C12B—C13B−0.1 (3)
C11A—C12A—C13A—C14A0.2 (3)C11B—C12B—C13B—C14B−0.2 (4)
C12A—C13A—C14A—C15A−0.1 (3)C12B—C13B—C14B—C15B0.1 (4)
C13A—C14A—C15A—C10A0.1 (3)C13B—C14B—C15B—C10B0.4 (3)
C11A—C10A—C15A—C14A−0.2 (2)C11B—C10B—C15B—C14B−0.7 (3)
S1A—C10A—C15A—C14A−178.95 (13)S1B—C10B—C15B—C14B−179.95 (15)
C2A—C3A—C17A—C18A−85.4 (2)C2B—C3B—C17B—C18B−82.4 (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—C19A−64.6 (2)C3B—C17B—C18B—C23B−60.4 (3)
C23A—C18A—C19A—C20A2.5 (3)C23B—C18B—C19B—C20B−0.6 (3)
C17A—C18A—C19A—C20A−176.14 (18)C17B—C18B—C19B—C20B178.61 (17)
C18A—C19A—C20A—C21A−0.1 (3)C18B—C19B—C20B—C21B−0.6 (3)
C19A—C20A—C21A—O3A177.53 (17)C19B—C20B—C21B—O3B−178.41 (17)
C19A—C20A—C21A—C22A−2.8 (3)C19B—C20B—C21B—C22B2.0 (3)
O3A—C21A—C22A—C23A−177.08 (18)O3B—C21B—C22B—C23B178.21 (17)
C20A—C21A—C22A—C23A3.3 (3)C20B—C21B—C22B—C23B−2.2 (3)
C19A—C18A—C23A—C22A−2.0 (3)C21B—C22B—C23B—C18B0.9 (3)
C17A—C18A—C23A—C22A176.63 (18)C19B—C18B—C23B—C22B0.5 (3)
C21A—C22A—C23A—C18A−0.9 (3)C17B—C18B—C23B—C22B−178.77 (18)
C22A—C21A—O3A—C24A5.2 (3)C20B—C21B—O3B—C24B7.0 (3)
C20A—C21A—O3A—C24A−175.18 (18)C22B—C21B—O3B—C24B−173.44 (18)
C5A—N1A—S1A—O1A−40.19 (15)C5B—N1B—S1B—O1B−41.21 (15)
C2A—N1A—S1A—O1A160.69 (14)C2B—N1B—S1B—O1B162.76 (14)
C5A—N1A—S1A—O2A−168.85 (13)C5B—N1B—S1B—O2B−169.76 (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—C10A−84.28 (15)C2B—N1B—S1B—C10B−82.05 (15)
C11A—C10A—S1A—O1A−159.14 (13)C11B—C10B—S1B—O1B−160.15 (14)
C15A—C10A—S1A—O1A19.67 (15)C15B—C10B—S1B—O1B19.15 (16)
C11A—C10A—S1A—O2A−27.99 (15)C11B—C10B—S1B—O2B−28.80 (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—N1A−94.04 (13)C15B—C10B—S1B—N1B−94.74 (15)

Hydrogen-bond geometry (Å, °)

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) x−1, y−1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2902).

References

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  • Bruker (2004). SAINT and APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527–1532.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Krishnaiah, M., Narayana Raju, K. V., Lu, I.-L., Chen, Y.-S. & Narasinga Rao, S. (1995). Acta Cryst. C51, 2429–2430.
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