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The title compound, C23H17Cl2NO2S, crystallizes with Z′ = 2 in space group P\overline 1. The dihedral angle between the indole moiety and the aromatic rings of the phenyl­sulfonyl and di­chloro­phenyl groups are 76.2 (1) and 7.6 (1)° in mol­ecule A, and 75.6 (1) and 11.6 (1)° in mol­ecule B. The dihedral angle between the two aromatic rings is 79.7 (1)° in mol­ecule A and 81.6 (1)° in mol­ecule B. The molecular structure and molecular packing in the crystal are stabilized by C—H...O weak interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007888/ci6218sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007888/ci6218Isup2.hkl
Contains datablock I

CCDC reference: 214634

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.121
  • Data-to-parameter ratio = 18.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The indole ring system is present in a number of natural products, many of which are found to possess antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al., 1984), antimicrobial (El-Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985) activities. Sivaraman et al. (1996) have studied the interaction of phenylsulfonyl indoles with the calf-thymus DNA, by spectroscopic methods. Indoles have been proved to dispaly high aldose reductose inhibitory activity (Rajeswaran et al., 1999). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives.

The asymmetric unit contains two molecules, A and B; the correponding bond lengths and angles of these two molecules agree with each other and no conformational changes are observed. Bond lengths and angles in the indole moiety are comparable with those observed in related N-phenylsulfonyl indole derivatives (Sankaranarayanan et al., 2000; Sankaranarayanan, Yogavel, Velmurugan, Sekar, Babu et al., 2003; Sankaranarayanan, Yogavel, Velmurugan, Sekar, Srinivasan et al., 2003; SethuSankar et al., 2002; Govindasamy et al., 1998). The lengthening of C—N bonds in the indole moiety is due to the electron-withdrawing character of the phenylsulfonyl group. The S1—N1 and S1—C10 bond distances are comparable with the mean values of 1.642 (24) and 1.758 (18) Å (Allen et al., 1987). In both the molecules, the angular dispostion of the bonds about the S atoms show significant deviation from that of a regular tetrahedron, with the largest deviation being in O—S—O angles. As previously reported, the widening of the O—S—O angle is presumbly the result of repulsive interaction between the SO bonds (Rodriguezh et al., 1985; Beddoes et al., 1986; Govindasamy et al., 1998; Sankaranarayanan et al., 2000, 2001; SethuSankar et al., 2002).

In both the moleules, the chlorophenyl ring is nearly coplanar with indole ring system, with a dihedral angle of 7.6 (1)° in molecule A and 11.6 (1)° in molecule B. The dihedral angle between the indole ring system and the sulfonyl bound phenyl ring is 76.2 (1)° in molecule A and 75.6 (1)° in molecule B. The sulfonylphenyl and dichlorophenyl rings are nearly orthogonal [dihedral angles 79.7 (1) and 81.5 (1)°]. Atom N1 deviates from the plane passing through C2, C5 and S1 by 0.186 (2) Å in molecule A and 0.179 (2) Å in molecule B, and the sum of the angles around N1 is 355.4 (1)° in molecule A and 355.7 (1)° in molecule B. This slight pyramidalization behaviour is also observed in the related indole derivatives (Sankaranarayanan et al., 2000, 2003a, 2003b; SethuSankar et al., 2002).

Both the molecular and crystal structures are stabilized by weak C—H···O interactions. In the molecular structure, the orientations of the indole and phenyl subtituents with respect to the sulfonyl group are influenced by C6—H6···O1 and C15—H15···O2 weak interactions (Table 2). In the crystal structure, the C19A—H19A···O2B and C19B—H19B···O2A(1 + x, y, z) interactions link the molecules to form helices along the a direction (Fig. 2).

Experimental top

To a suspension of NaOH (0.15 g, 6 mmol) in dry tetrahydrofuran (THF, 20 ml) at room temperature was slowly added the aryl phosphonium bromide (6 mmol) in dry THF (40 ml) under N2 and stirred for 1 h. Then a solution of the 1-phenylsulfonyl-2-methylindole-3-carbaldehyde (1 equivalent, 6 mmol) in dry THF (20 ml) was added. Stirring was continued for another 2 h. The red–brown solution was poured over ice (200 g) containing saturated NH4Cl solution. Then it was extracted with dichloromethane and the organic extract was washed with water (3 × 25 ml), dried over MgSO4 and filtered. Removal of solvent and chromatographic separation on a silica-gel column by elution with hexane–ethyl acetate (9:1) afforded the title compound.

Refinement top

The H atoms were fixed geometrically and treated as riding atoms on the parent C atoms, with aromatic C—H = 0.93 Å and methyl C—H = 0.96 Å. The rotating group refinement was used for the methyl groups.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 35% probability displacement elliposids and the atom-numbering scheme.
[Figure 2] Fig. 2. A stereoview of the molecular packing in the title compound, showing two anti-parallel helices along the a direction. For clarity, H atoms not involved in hydrogen bonding have been omitted.
3-[2-(2,4-Dichlorophenyl)vinyl]-2-methyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C23H17Cl2NO2SZ = 4
Mr = 442.34F(000) = 912
Triclinic, P1Dx = 1.448 Mg m3
Hall symbol: -P 1Melting point: 383 K K
a = 8.0083 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7242 (2) ÅCell parameters from 5639 reflections
c = 21.9150 (4) Åθ = 0.9–28.3°
α = 86.474 (1)°µ = 0.44 mm1
β = 89.831 (1)°T = 293 K
γ = 81.037 (1)°Parallelepiped, yellow
V = 2028.60 (6) Å30.48 × 0.42 × 0.36 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
9692 independent reflections
Radiation source: fine-focus sealed tube7077 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 28.3°, θmin = 0.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.815, Tmax = 0.857k = 1415
16575 measured reflectionsl = 2918
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) = 0.121H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.042P]
where P = (Fo2 + 2Fc2)/3
9692 reflections(Δ/σ)max = 0.001
525 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C23H17Cl2NO2Sγ = 81.037 (1)°
Mr = 442.34V = 2028.60 (6) Å3
Triclinic, P1Z = 4
a = 8.0083 (1) ÅMo Kα radiation
b = 11.7242 (2) ŵ = 0.44 mm1
c = 21.9150 (4) ÅT = 293 K
α = 86.474 (1)°0.48 × 0.42 × 0.36 mm
β = 89.831 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
9692 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7077 reflections with I > 2σ(I)
Tmin = 0.815, Tmax = 0.857Rint = 0.038
16575 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
9692 reflectionsΔρmin = 0.42 e Å3
525 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
Cl1A0.64035 (10)0.05312 (6)0.59489 (3)0.0822 (2)
Cl2A0.27984 (9)0.47404 (5)0.60557 (2)0.06842 (18)
S1A0.01089 (6)0.77117 (4)0.22510 (2)0.03785 (11)
O1A0.11130 (17)0.88264 (12)0.22634 (6)0.0512 (4)
O2A0.06369 (17)0.68788 (12)0.18750 (6)0.0489 (3)
N1A0.00317 (19)0.71381 (13)0.29667 (7)0.0384 (3)
C2A0.1067 (2)0.60747 (15)0.31367 (8)0.0370 (4)
C3A0.1401 (2)0.60135 (16)0.37473 (8)0.0386 (4)
C4A0.0569 (2)0.70933 (16)0.39868 (8)0.0405 (4)
C5A0.0239 (2)0.77852 (16)0.35002 (8)0.0381 (4)
C6A0.1175 (3)0.88725 (17)0.35693 (10)0.0511 (5)
H6A0.17160.93170.32400.061*
C7A0.1257 (3)0.9256 (2)0.41534 (11)0.0632 (6)
H7A0.18530.99850.42170.076*
C8A0.0485 (4)0.8593 (2)0.46445 (11)0.0696 (7)
H8A0.05810.88790.50320.084*
C9A0.0429 (3)0.75142 (19)0.45702 (9)0.0573 (6)
H9A0.09460.70720.49040.069*
C10A0.1985 (2)0.78568 (15)0.20565 (8)0.0359 (4)
C11A0.2941 (3)0.83860 (19)0.24477 (9)0.0487 (5)
H11A0.24950.86500.28150.058*
C12A0.4567 (3)0.8513 (2)0.22807 (11)0.0566 (5)
H12A0.52310.88600.25390.068*
C13A0.5210 (3)0.8130 (2)0.17370 (10)0.0559 (5)
H13A0.63050.82240.16280.067*
C14A0.4258 (3)0.7608 (2)0.13498 (10)0.0543 (5)
H14A0.47090.73500.09820.065*
C15A0.2623 (3)0.74676 (17)0.15093 (9)0.0458 (5)
H15A0.19670.71160.12510.055*
C16A0.2373 (3)0.50213 (17)0.40726 (9)0.0446 (4)
H16A0.29200.44570.38300.053*
C17A0.2591 (3)0.48079 (18)0.46631 (9)0.0496 (5)
H17A0.20690.53710.49120.060*
C18A0.3565 (2)0.37798 (17)0.49714 (8)0.0412 (4)
C19A0.4378 (3)0.28500 (19)0.46518 (9)0.0515 (5)
H19A0.43330.29060.42270.062*
C20A0.5236 (3)0.1863 (2)0.49423 (10)0.0556 (6)
H20A0.57460.12570.47170.067*
C21A0.5335 (3)0.17784 (19)0.55716 (10)0.0519 (5)
C22A0.4594 (3)0.26661 (18)0.59111 (9)0.0493 (5)
H22A0.46790.26090.63350.059*
C23A0.3723 (2)0.36434 (17)0.56083 (8)0.0421 (4)
C24A0.1570 (3)0.51703 (17)0.26920 (9)0.0512 (5)
H24A0.22230.45030.28990.077*
H24B0.22350.54710.23730.077*
H24C0.05750.49550.25170.077*
Cl1B0.91221 (10)0.95938 (5)0.10054 (3)0.07259 (19)
Cl2B0.75804 (9)0.53408 (5)0.10649 (2)0.06452 (17)
S1B0.61297 (6)0.22578 (4)0.27038 (2)0.03728 (11)
O1B0.56164 (18)0.11490 (12)0.26710 (6)0.0496 (3)
O2B0.51873 (16)0.30829 (12)0.30764 (6)0.0482 (3)
N1B0.60940 (19)0.28541 (13)0.19921 (7)0.0380 (3)
C2B0.6649 (2)0.39289 (15)0.18431 (8)0.0363 (4)
C3B0.7000 (2)0.40160 (16)0.12346 (8)0.0367 (4)
C4B0.6709 (2)0.29390 (16)0.09808 (8)0.0378 (4)
C5B0.6172 (2)0.22316 (16)0.14524 (8)0.0377 (4)
C6B0.5757 (3)0.11443 (17)0.13588 (10)0.0508 (5)
H6B0.53810.06900.16770.061*
C7B0.5928 (3)0.07703 (19)0.07764 (10)0.0589 (6)
H7B0.56700.00460.07000.071*
C8B0.6477 (3)0.1450 (2)0.02995 (10)0.0617 (6)
H8B0.65840.11730.00900.074*
C9B0.6867 (3)0.25270 (18)0.03941 (9)0.0521 (5)
H9B0.72320.29770.00710.063*
C10B0.8271 (2)0.20869 (15)0.29253 (8)0.0369 (4)
C11B0.9500 (3)0.15581 (18)0.25458 (9)0.0492 (5)
H11B0.92060.12840.21780.059*
C12B1.1172 (3)0.1446 (2)0.27240 (11)0.0584 (6)
H12B1.20180.11000.24730.070*
C13B1.1591 (3)0.1845 (2)0.32698 (11)0.0580 (6)
H13B1.27210.17670.33850.070*
C14B1.0368 (3)0.2357 (2)0.36468 (10)0.0590 (6)
H14B1.06680.26190.40170.071*
C15B0.8689 (3)0.24823 (18)0.34768 (9)0.0480 (5)
H15B0.78500.28290.37300.058*
C16B0.7510 (2)0.50219 (16)0.09190 (8)0.0413 (4)
H16B0.78860.55510.11640.050*
C17B0.7507 (3)0.52798 (17)0.03269 (8)0.0477 (5)
H17B0.71670.47390.00810.057*
C18B0.7974 (2)0.63149 (16)0.00098 (8)0.0386 (4)
C19B0.8367 (3)0.72582 (17)0.03204 (8)0.0462 (5)
H19B0.83810.72070.07460.055*
C20B0.8731 (3)0.82486 (18)0.00189 (9)0.0490 (5)
H20B0.89850.88560.02370.059*
C21B0.8717 (3)0.83344 (17)0.06110 (9)0.0456 (4)
C22B0.8374 (2)0.74370 (17)0.09401 (8)0.0449 (4)
H22B0.83890.74940.13650.054*
C23B0.8008 (2)0.64491 (16)0.06269 (8)0.0402 (4)
C24B0.6684 (3)0.48223 (17)0.23001 (9)0.0511 (5)
H24D0.71180.54760.21110.077*
H24E0.73980.44980.26390.077*
H24F0.55590.50660.24440.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.1061 (5)0.0534 (4)0.0784 (4)0.0092 (4)0.0274 (4)0.0121 (3)
Cl2A0.0991 (5)0.0614 (4)0.0418 (3)0.0012 (3)0.0063 (3)0.0155 (2)
S1A0.0378 (2)0.0378 (2)0.0377 (2)0.00701 (19)0.00827 (17)0.00293 (17)
O1A0.0454 (8)0.0453 (8)0.0585 (9)0.0032 (6)0.0097 (6)0.0071 (6)
O2A0.0515 (8)0.0534 (9)0.0453 (8)0.0199 (7)0.0141 (6)0.0012 (6)
N1A0.0417 (8)0.0352 (8)0.0364 (8)0.0012 (7)0.0001 (6)0.0004 (6)
C2A0.0390 (9)0.0345 (9)0.0365 (9)0.0036 (8)0.0010 (7)0.0001 (7)
C3A0.0422 (10)0.0379 (10)0.0356 (9)0.0064 (8)0.0011 (7)0.0010 (7)
C4A0.0454 (10)0.0390 (10)0.0380 (10)0.0093 (8)0.0062 (8)0.0032 (7)
C5A0.0375 (9)0.0374 (10)0.0398 (10)0.0062 (8)0.0063 (7)0.0034 (7)
C6A0.0510 (12)0.0412 (11)0.0588 (13)0.0007 (9)0.0096 (9)0.0010 (9)
C7A0.0765 (16)0.0445 (13)0.0658 (15)0.0024 (11)0.0200 (12)0.0115 (11)
C8A0.103 (2)0.0555 (15)0.0507 (13)0.0093 (14)0.0193 (13)0.0152 (11)
C9A0.0839 (16)0.0487 (12)0.0382 (11)0.0058 (11)0.0050 (10)0.0065 (9)
C10A0.0385 (9)0.0327 (9)0.0363 (9)0.0074 (7)0.0055 (7)0.0035 (7)
C11A0.0526 (12)0.0533 (12)0.0430 (11)0.0167 (10)0.0055 (9)0.0040 (9)
C12A0.0520 (12)0.0596 (14)0.0621 (14)0.0237 (11)0.0160 (10)0.0051 (10)
C13A0.0408 (11)0.0604 (14)0.0640 (14)0.0069 (10)0.0006 (10)0.0135 (11)
C14A0.0507 (12)0.0590 (14)0.0504 (12)0.0016 (10)0.0051 (9)0.0004 (10)
C15A0.0505 (11)0.0444 (11)0.0426 (11)0.0069 (9)0.0050 (8)0.0044 (8)
C16A0.0548 (11)0.0392 (10)0.0379 (10)0.0018 (9)0.0006 (8)0.0020 (7)
C17A0.0578 (12)0.0478 (12)0.0379 (10)0.0077 (10)0.0012 (9)0.0017 (8)
C18A0.0449 (10)0.0435 (11)0.0338 (9)0.0033 (8)0.0027 (7)0.0011 (7)
C19A0.0582 (12)0.0583 (13)0.0336 (10)0.0058 (11)0.0011 (8)0.0056 (8)
C20A0.0602 (13)0.0513 (13)0.0507 (12)0.0081 (11)0.0030 (10)0.0096 (10)
C21A0.0568 (12)0.0446 (12)0.0519 (12)0.0029 (10)0.0113 (9)0.0041 (9)
C22A0.0634 (13)0.0514 (12)0.0337 (10)0.0126 (10)0.0063 (9)0.0035 (8)
C23A0.0490 (11)0.0428 (11)0.0351 (9)0.0085 (9)0.0009 (8)0.0049 (7)
C24A0.0678 (13)0.0410 (11)0.0409 (10)0.0052 (10)0.0044 (9)0.0050 (8)
Cl1B0.1149 (5)0.0472 (3)0.0592 (4)0.0286 (3)0.0088 (3)0.0088 (2)
Cl2B0.1043 (5)0.0525 (3)0.0417 (3)0.0232 (3)0.0030 (3)0.0141 (2)
S1B0.0387 (2)0.0383 (2)0.0348 (2)0.00751 (19)0.00735 (17)0.00117 (17)
O1B0.0561 (8)0.0456 (8)0.0505 (8)0.0219 (7)0.0072 (6)0.0040 (6)
O2B0.0449 (7)0.0540 (9)0.0433 (7)0.0000 (6)0.0134 (6)0.0027 (6)
N1B0.0469 (9)0.0354 (8)0.0332 (8)0.0119 (7)0.0015 (6)0.0011 (6)
C2B0.0406 (9)0.0340 (9)0.0351 (9)0.0093 (8)0.0003 (7)0.0004 (7)
C3B0.0391 (9)0.0378 (10)0.0332 (9)0.0066 (8)0.0018 (7)0.0002 (7)
C4B0.0402 (9)0.0376 (10)0.0352 (9)0.0049 (8)0.0021 (7)0.0019 (7)
C5B0.0389 (9)0.0371 (10)0.0379 (9)0.0074 (8)0.0028 (7)0.0047 (7)
C6B0.0632 (13)0.0431 (12)0.0496 (12)0.0190 (10)0.0022 (9)0.0034 (9)
C7B0.0813 (16)0.0429 (12)0.0566 (13)0.0189 (11)0.0071 (11)0.0124 (10)
C8B0.0946 (18)0.0486 (13)0.0434 (12)0.0120 (12)0.0032 (11)0.0133 (9)
C9B0.0751 (14)0.0454 (12)0.0364 (10)0.0109 (11)0.0002 (9)0.0031 (8)
C10B0.0402 (9)0.0315 (9)0.0383 (9)0.0048 (7)0.0050 (7)0.0023 (7)
C11B0.0484 (11)0.0522 (12)0.0452 (11)0.0012 (9)0.0072 (9)0.0067 (9)
C12B0.0444 (11)0.0574 (14)0.0694 (15)0.0030 (10)0.0123 (10)0.0011 (11)
C13B0.0434 (11)0.0619 (14)0.0661 (15)0.0090 (10)0.0056 (10)0.0187 (11)
C14B0.0614 (14)0.0663 (15)0.0510 (13)0.0172 (12)0.0097 (10)0.0025 (10)
C15B0.0513 (11)0.0498 (12)0.0425 (11)0.0060 (9)0.0035 (9)0.0039 (8)
C16B0.0507 (11)0.0373 (10)0.0377 (10)0.0123 (8)0.0002 (8)0.0027 (7)
C17B0.0694 (13)0.0413 (11)0.0365 (10)0.0214 (10)0.0007 (9)0.0020 (8)
C18B0.0450 (10)0.0390 (10)0.0328 (9)0.0101 (8)0.0011 (7)0.0008 (7)
C19B0.0610 (12)0.0493 (12)0.0316 (9)0.0177 (10)0.0021 (8)0.0042 (8)
C20B0.0660 (13)0.0422 (11)0.0425 (11)0.0183 (10)0.0029 (9)0.0073 (8)
C21B0.0542 (11)0.0388 (10)0.0438 (11)0.0100 (9)0.0056 (8)0.0036 (8)
C22B0.0557 (12)0.0454 (11)0.0327 (9)0.0065 (9)0.0033 (8)0.0015 (8)
C23B0.0484 (10)0.0404 (10)0.0319 (9)0.0063 (8)0.0003 (7)0.0058 (7)
C24B0.0765 (14)0.0417 (11)0.0381 (10)0.0184 (10)0.0049 (9)0.0039 (8)
Geometric parameters (Å, º) top
Cl1A—C21A1.738 (2)Cl1B—C21B1.739 (2)
Cl2A—C23A1.737 (2)Cl2B—C23B1.738 (2)
S1A—O1A1.426 (1)S1B—O2B1.428 (1)
S1A—O2A1.429 (1)S1B—O1B1.429 (1)
S1A—N1A1.665 (2)S1B—N1B1.668 (2)
S1A—C10A1.760 (2)S1B—C10B1.761 (2)
N1A—C2A1.415 (2)N1B—C2B1.419 (2)
N1A—C5A1.430 (2)N1B—C5B1.424 (2)
C2A—C3A1.361 (2)C2B—C3B1.363 (2)
C2A—C24A1.493 (2)C2B—C24B1.497 (2)
C3A—C16A1.445 (3)C3B—C16B1.444 (3)
C3A—C4A1.462 (2)C3B—C4B1.462 (2)
C4A—C9A1.397 (3)C4B—C5B1.394 (3)
C4A—C5A1.396 (3)C4B—C9B1.400 (2)
C5A—C6A1.391 (2)C5B—C6B1.394 (3)
C6A—C7A1.381 (3)C6B—C7B1.374 (3)
C6A—H6A0.93C6B—H6B0.93
C7A—C8A1.377 (4)C7B—C8B1.387 (3)
C7A—H7A0.93C7B—H7B0.93
C8A—C9A1.378 (3)C8B—C9B1.375 (3)
C8A—H8A0.93C8B—H8B0.93
C9A—H9A0.93C9B—H9B0.93
C10A—C15A1.378 (2)C10B—C11B1.383 (2)
C10A—C11A1.387 (3)C10B—C15B1.381 (3)
C11A—C12A1.379 (3)C11B—C12B1.380 (3)
C11A—H11A0.93C11B—H11B0.93
C12A—C13A1.370 (3)C12B—C13B1.372 (3)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.374 (3)C13B—C14B1.369 (3)
C13A—H13A0.93C13B—H13B0.93
C14A—C15A1.386 (3)C14B—C15B1.379 (3)
C14A—H14A0.93C14B—H14B0.93
C15A—H15A0.93C15B—H15B0.93
C16A—C17A1.310 (3)C16B—C17B1.314 (3)
C16A—H16A0.93C16B—H16B0.93
C17A—C18A1.459 (3)C17B—C18B1.460 (3)
C17A—H17A0.93C17B—H17B0.93
C18A—C23A1.399 (2)C18B—C23B1.395 (2)
C18A—C19A1.405 (2)C18B—C19B1.410 (2)
C19A—C20A1.372 (3)C19B—C20B1.371 (3)
C19A—H19A0.93C19B—H19B0.93
C20A—C21A1.378 (3)C20B—C21B1.378 (3)
C20A—H20A0.93C20B—H20B0.93
C21A—C22A1.374 (3)C21B—C22B1.374 (3)
C22A—C23A1.378 (3)C22B—C23B1.380 (3)
C22A—H22A0.93C22B—H22B0.93
C24A—H24A0.96C24B—H24D0.96
C24A—H24B0.96C24B—H24E0.96
C24A—H24C0.96C24B—H24F0.96
O1A—S1A—O2A119.03 (8)O2B—S1B—O1B118.9 (1)
O1A—S1A—N1A107.11 (8)O2B—S1B—N1B107.5 (1)
O2A—S1A—N1A107.58 (8)O1B—S1B—N1B107.1 (1)
O1A—S1A—C10A109.81 (9)O2B—S1B—C10B108.3 (1)
O2A—S1A—C10A108.00 (8)O1B—S1B—C10B109.8 (1)
N1A—S1A—C10A104.33 (8)N1B—S1B—C10B104.3 (1)
C2A—N1A—C5A107.8 (1)C2B—N1B—C5B107.9 (1)
C2A—N1A—S1A122.8 (1)C2B—N1B—S1B122.8 (1)
C5A—N1A—S1A124.8 (1)C5B—N1B—S1B125.0 (1)
C3A—C2A—N1A109.7 (1)C3B—C2B—N1B109.5 (2)
C3A—C2A—C24A128.0 (2)C3B—C2B—C24B127.9 (2)
N1A—C2A—C24A122.2 (2)N1B—C2B—C24B122.5 (2)
C2A—C3A—C16A123.8 (2)C2B—C3B—C16B124.4 (2)
C2A—C3A—C4A107.3 (2)C2B—C3B—C4B107.2 (2)
C16A—C3A—C4A128.8 (2)C16B—C3B—C4B128.4 (2)
C9A—C4A—C5A118.3 (2)C5B—C4B—C9B118.5 (2)
C9A—C4A—C3A133.7 (2)C5B—C4B—C3B108.2 (2)
C5A—C4A—C3A108.0 (2)C9B—C4B—C3B133.4 (2)
C6A—C5A—C4A123.1 (2)C6B—C5B—C4B122.5 (2)
C6A—C5A—N1A129.7 (2)C6B—C5B—N1B130.2 (2)
C4A—C5A—N1A107.1 (2)C4B—C5B—N1B107.2 (2)
C7A—C6A—C5A116.3 (2)C7B—C6B—C5B117.3 (2)
C7A—C6A—H6A121.8C7B—C6B—H6B121.4
C5A—C6A—H6A121.8C5B—C6B—H6B121.4
C8A—C7A—C6A122.1 (2)C6B—C7B—C8B121.5 (2)
C8A—C7A—H7A118.9C6B—C7B—H7B119.3
C6A—C7A—H7A118.9C8B—C7B—H7B119.3
C7A—C8A—C9A120.9 (2)C9B—C8B—C7B120.9 (2)
C7A—C8A—H8A119.5C9B—C8B—H8B119.5
C9A—C8A—H8A119.5C7B—C8B—H8B119.5
C8A—C9A—C4A119.2 (2)C8B—C9B—C4B119.3 (2)
C8A—C9A—H9A120.4C8B—C9B—H9B120.3
C4A—C9A—H9A120.4C4B—C9B—H9B120.3
C15A—C10A—C11A121.4 (2)C11B—C10B—C15B121.3 (3)
C15A—C10A—S1A119.1 (1)C11B—C10B—S1B119.5 (3)
C11A—C10A—S1A119.5 (1)C15B—C10B—S1B119.2 (1)
C12A—C11A—C10A118.6 (2)C12B—C11B—C10B118.6 (2)
C12A—C11A—H11A120.7C12B—C11B—H11B120.7
C10A—C11A—H11A120.7C10B—C11B—H11B120.7
C13A—C12A—C11A120.3 (2)C13B—C12B—C11B120.2 (2)
C13A—C12A—H12A119.8C13B—C12B—H12B119.9
C11A—C12A—H12A119.8C11B—C12B—H12B119.9
C12A—C13A—C14A120.9 (2)C12B—C13B—C14B120.9 (2)
C12A—C13A—H13A119.5C12B—C13B—H13B119.5
C14A—C13A—H13A119.5C14B—C13B—H13B119.5
C13A—C14A—C15A119.7 (2)C13B—C14B—C15B119.9 (2)
C13A—C14A—H14A120.1C13B—C14B—H14B120.1
C15A—C14A—H14A120.1C15B—C14B—H14B120.1
C10A—C15A—C14A119.0 (2)C14B—C15B—C10B119.1 (2)
C10A—C15A—H15A120.5C14B—C15B—H15B120.5
C14A—C15A—H15A120.5C10B—C15B—H15B120.5
C17A—C16A—C3A128.9 (2)C17B—C16B—C3B127.8 (2)
C17A—C16A—H16A115.6C17B—C16B—H16B116.1
C3A—C16A—H16A115.6C3B—C16B—H16B116.1
C16A—C17A—C18A126.9 (2)C16B—C17B—C18B127.7 (2)
C16A—C17A—H17A116.6C16B—C17B—H17B116.1
C18A—C17A—H17A116.6C18B—C17B—H17B116.1
C23A—C18A—C19A115.4 (2)C23B—C18B—C19B115.4 (2)
C23A—C18A—C17A122.1 (2)C23B—C18B—C17B121.8 (2)
C19A—C18A—C17A122.5 (2)C19B—C18B—C17B122.8 (2)
C20A—C19A—C18A122.5 (2)C20B—C19B—C18B122.5 (2)
C20A—C19A—H19A118.7C20B—C19B—H19B118.8
C18A—C19A—H19A118.7C18B—C19B—H19B118.8
C19A—C20A—C21A119.2 (2)C19B—C20B—C21B119.3 (2)
C19A—C20A—H20A120.4C19B—C20B—H20B120.4
C21A—C20A—H20A120.4C21B—C20B—H20B120.4
C22A—C21A—C20A121.1 (2)C22B—C21B—C20B121.1 (2)
C22A—C21A—Cl1A118.9 (2)C22B—C21B—Cl1B118.7 (2)
C20A—C21A—Cl1A120.0 (2)C20B—C21B—Cl1B120.3 (2)
C21A—C22A—C23A118.5 (2)C21B—C22B—C23B118.6 (2)
C21A—C22A—H22A120.8C21B—C22B—H22B120.7
C23A—C22A—H22A120.8C23B—C22B—H22B120.7
C22A—C23A—C18A123.2 (2)C22B—C23B—C18B123.1 (2)
C22A—C23A—Cl2A116.9 (1)C22B—C23B—Cl2B116.8 (2)
C18A—C23A—Cl2A119.9 (2)C18B—C23B—Cl2B120.1 (2)
C2A—C24A—H24A109.5C2B—C24B—H24D109.5
C2A—C24A—H24B109.5C2B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C2A—C24A—H24C109.5C2B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
O1A—S1A—N1A—C2A174.03 (14)O2B—S1B—N1B—C2B55.83 (16)
O2A—S1A—N1A—C2A56.90 (16)O1B—S1B—N1B—C2B175.35 (13)
C10A—S1A—N1A—C2A57.64 (16)C10B—S1B—N1B—C2B58.98 (15)
O1A—S1A—N1A—C5A21.06 (17)O2B—S1B—N1B—C5B150.15 (14)
O2A—S1A—N1A—C5A150.12 (14)O1B—S1B—N1B—C5B21.33 (16)
C10A—S1A—N1A—C5A95.3 (2)C10B—S1B—N1B—C5B95.0 (2)
C5A—N1A—C2A—C3A2.0 (2)C5B—N1B—C2B—C3B2.3 (2)
S1A—N1A—C2A—C3A158.97 (14)S1B—N1B—C2B—C3B160.17 (13)
C5A—N1A—C2A—C24A178.55 (18)C5B—N1B—C2B—C24B178.23 (17)
S1A—N1A—C2A—C24A24.5 (2)S1B—N1B—C2B—C24B23.9 (2)
N1A—C2A—C3A—C16A177.63 (17)N1B—C2B—C3B—C16B176.58 (16)
C24A—C2A—C3A—C16A1.4 (3)C24B—C2B—C3B—C16B1.0 (3)
N1A—C2A—C3A—C4A0.9 (2)N1B—C2B—C3B—C4B1.7 (2)
C24A—C2A—C3A—C4A177.16 (19)C24B—C2B—C3B—C4B177.29 (18)
C2A—C3A—C4A—C9A178.3 (2)C2B—C3B—C4B—C5B0.4 (2)
C16A—C3A—C4A—C9A0.2 (4)C16B—C3B—C4B—C5B177.76 (18)
C2A—C3A—C4A—C5A0.6 (2)C2B—C3B—C4B—C9B179.4 (2)
C16A—C3A—C4A—C5A179.03 (19)C16B—C3B—C4B—C9B2.4 (3)
C9A—C4A—C5A—C6A0.0 (3)C9B—C4B—C5B—C6B1.3 (3)
C3A—C4A—C5A—C6A179.11 (18)C3B—C4B—C5B—C6B178.85 (17)
C9A—C4A—C5A—N1A177.27 (18)C9B—C4B—C5B—N1B179.12 (16)
C3A—C4A—C5A—N1A1.8 (2)C3B—C4B—C5B—N1B1.02 (19)
C2A—N1A—C5A—C6A179.43 (19)C2B—N1B—C5B—C6B179.63 (19)
S1A—N1A—C5A—C6A24.2 (3)S1B—N1B—C5B—C6B23.1 (3)
C2A—N1A—C5A—C4A2.4 (2)C2B—N1B—C5B—C4B2.02 (19)
S1A—N1A—C5A—C4A158.70 (14)S1B—N1B—C5B—C4B159.27 (13)
C4A—C5A—C6A—C7A0.8 (3)C4B—C5B—C6B—C7B1.3 (3)
N1A—C5A—C6A—C7A177.4 (2)N1B—C5B—C6B—C7B178.55 (19)
C5A—C6A—C7A—C8A1.2 (4)C5B—C6B—C7B—C8B0.5 (3)
C6A—C7A—C8A—C9A0.8 (4)C6B—C7B—C8B—C9B0.2 (4)
C7A—C8A—C9A—C4A0.1 (4)C7B—C8B—C9B—C4B0.2 (4)
C5A—C4A—C9A—C8A0.5 (3)C5B—C4B—C9B—C8B0.5 (3)
C3A—C4A—C9A—C8A179.3 (2)C3B—C4B—C9B—C8B179.6 (2)
O1A—S1A—C10A—C15A113.71 (16)O2B—S1B—C10B—C11B164.44 (16)
O2A—S1A—C10A—C15A17.5 (2)O1B—S1B—C10B—C11B64.30 (18)
N1A—S1A—C10A—C15A131.78 (15)N1B—S1B—C10B—C11B50.16 (18)
O1A—S1A—C10A—C11A64.59 (17)O2B—S1B—C10B—C15B15.7 (2)
O2A—S1A—C10A—C11A164.16 (16)O1B—S1B—C10B—C15B115.54 (16)
N1A—S1A—C10A—C11A49.91 (17)N1B—S1B—C10B—C15B130.00 (15)
C15A—C10A—C11A—C12A0.4 (3)C15B—C10B—C11B—C12B1.0 (3)
S1A—C10A—C11A—C12A178.67 (16)S1B—C10B—C11B—C12B179.15 (17)
C10A—C11A—C12A—C13A0.5 (3)C10B—C11B—C12B—C13B0.6 (3)
C11A—C12A—C13A—C14A0.4 (3)C11B—C12B—C13B—C14B0.1 (4)
C12A—C13A—C14A—C15A0.1 (3)C12B—C13B—C14B—C15B0.4 (4)
C11A—C10A—C15A—C14A0.2 (3)C13B—C14B—C15B—C10B0.0 (3)
S1A—C10A—C15A—C14A178.43 (16)C11B—C10B—C15B—C14B0.7 (3)
C13A—C14A—C15A—C10A0.0 (3)S1B—C10B—C15B—C14B179.43 (17)
C2A—C3A—C16A—C17A170.4 (2)C2B—C3B—C16B—C17B163.5 (2)
C4A—C3A—C16A—C17A7.8 (4)C4B—C3B—C16B—C17B14.4 (3)
C3A—C16A—C17A—C18A178.8 (2)C3B—C16B—C17B—C18B177.92 (19)
C16A—C17A—C18A—C23A179.6 (2)C16B—C17B—C18B—C23B176.1 (2)
C16A—C17A—C18A—C19A1.7 (4)C16B—C17B—C18B—C19B5.9 (3)
C23A—C18A—C19A—C20A1.5 (3)C23B—C18B—C19B—C20B1.1 (3)
C17A—C18A—C19A—C20A177.3 (2)C17B—C18B—C19B—C20B177.0 (2)
C18A—C19A—C20A—C21A1.1 (4)C18B—C19B—C20B—C21B0.1 (3)
C19A—C20A—C21A—C22A0.2 (4)C19B—C20B—C21B—C22B1.2 (3)
C19A—C20A—C21A—Cl1A179.54 (18)C19B—C20B—C21B—Cl1B178.40 (16)
C20A—C21A—C22A—C23A0.9 (3)C20B—C21B—C22B—C23B1.3 (3)
Cl1A—C21A—C22A—C23A178.82 (17)Cl1B—C21B—C22B—C23B178.28 (15)
C21A—C22A—C23A—C18A0.4 (3)C21B—C22B—C23B—C18B0.2 (3)
C21A—C22A—C23A—Cl2A179.70 (17)C21B—C22B—C23B—Cl2B179.90 (15)
C19A—C18A—C23A—C22A0.7 (3)C19B—C18B—C23B—C22B1.0 (3)
C17A—C18A—C23A—C22A178.0 (2)C17B—C18B—C23B—C22B177.18 (19)
C19A—C18A—C23A—Cl2A179.14 (16)C19B—C18B—C23B—Cl2B178.96 (14)
C17A—C18A—C23A—Cl2A2.1 (3)C17B—C18B—C23B—Cl2B2.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O1A0.932.282.866 (3)120
C6B—H6B···O1B0.932.292.878 (2)121
C15A—H15A···O2A0.932.532.901 (3)104
C15B—H15B···O2B0.932.542.907 (2)104
C17A—H17A···Cl2A0.932.613.052 (2)110
C17B—H17B···Cl2B0.932.603.047 (2)110
C19A—H19A···O2B0.932.613.513 (2)163
C19B—H19B···O2Ai0.932.593.487 (2)163
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC23H17Cl2NO2S
Mr442.34
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.0083 (1), 11.7242 (2), 21.9150 (4)
α, β, γ (°)86.474 (1), 89.831 (1), 81.037 (1)
V3)2028.60 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.48 × 0.42 × 0.36
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.815, 0.857
No. of measured, independent and
observed [I > 2σ(I)] reflections
16575, 9692, 7077
Rint0.038
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.04
No. of reflections9692
No. of parameters525
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.42

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
Cl1A—C21A1.738 (2)Cl1B—C21B1.739 (2)
Cl2A—C23A1.737 (2)Cl2B—C23B1.738 (2)
S1A—O1A1.426 (1)S1B—O2B1.428 (1)
S1A—O2A1.429 (1)S1B—O1B1.429 (1)
S1A—N1A1.665 (2)S1B—N1B1.668 (2)
S1A—C10A1.760 (2)S1B—C10B1.761 (2)
N1A—C2A1.415 (2)N1B—C2B1.419 (2)
N1A—C5A1.430 (2)N1B—C5B1.424 (2)
C3A—C16A1.445 (3)C3B—C16B1.444 (3)
C16A—C17A1.310 (3)C16B—C17B1.314 (3)
C17A—C18A1.459 (3)C17B—C18B1.460 (3)
O1A—S1A—O2A119.03 (8)O2B—S1B—O1B118.9 (1)
O1A—S1A—N1A107.11 (8)O2B—S1B—N1B107.5 (1)
O2A—S1A—N1A107.58 (8)O1B—S1B—N1B107.1 (1)
O1A—S1A—C10A109.81 (9)O2B—S1B—C10B108.3 (1)
O2A—S1A—C10A108.00 (8)O1B—S1B—C10B109.8 (1)
N1A—S1A—C10A104.33 (8)N1B—S1B—C10B104.3 (1)
C2A—N1A—C5A107.8 (1)C2B—N1B—C5B107.9 (1)
C2A—N1A—S1A122.8 (1)C2B—N1B—S1B122.8 (1)
C5A—N1A—S1A124.8 (1)C5B—N1B—S1B125.0 (1)
C3A—C2A—C24A128.0 (2)C3B—C2B—C24B127.9 (2)
N1A—C2A—C24A122.2 (2)N1B—C2B—C24B122.5 (2)
C2A—C3A—C16A123.8 (2)C2B—C3B—C16B124.4 (2)
C16A—C3A—C4A128.8 (2)C16B—C3B—C4B128.4 (2)
C17A—C16A—C3A128.9 (2)C17B—C16B—C3B127.8 (2)
C16A—C17A—C18A126.9 (2)C16B—C17B—C18B127.7 (2)
C10A—S1A—N1A—C5A95.3 (2)C10B—S1B—N1B—C5B95.0 (2)
S1A—N1A—C5A—C6A24.2 (3)S1B—N1B—C5B—C6B23.1 (3)
O2A—S1A—C10A—C15A17.5 (2)O2B—S1B—C10B—C15B15.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O1A0.932.282.866 (3)120
C6B—H6B···O1B0.932.292.878 (2)121
C15A—H15A···O2A0.932.532.901 (3)104
C15B—H15B···O2B0.932.542.907 (2)104
C17A—H17A···Cl2A0.932.613.052 (2)110
C17B—H17B···Cl2B0.932.603.047 (2)110
C19A—H19A···O2B0.932.613.513 (2)163
C19B—H19B···O2Ai0.932.593.487 (2)163
Symmetry code: (i) x+1, y, z.
 

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