Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007888/ci6218sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007888/ci6218Isup2.hkl |
CCDC reference: 214634
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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.
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).
C23H17Cl2NO2S | Z = 4 |
Mr = 442.34 | F(000) = 912 |
Triclinic, P1 | Dx = 1.448 Mg m−3 |
Hall symbol: -P 1 | Melting point: 383 K K |
a = 8.0083 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7242 (2) Å | Cell parameters from 5639 reflections |
c = 21.9150 (4) Å | θ = 0.9–28.3° |
α = 86.474 (1)° | µ = 0.44 mm−1 |
β = 89.831 (1)° | T = 293 K |
γ = 81.037 (1)° | Parallelepiped, yellow |
V = 2028.60 (6) Å3 | 0.48 × 0.42 × 0.36 mm |
Siemens SMART CCD area-detector diffractometer | 9692 independent reflections |
Radiation source: fine-focus sealed tube | 7077 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 28.3°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.815, Tmax = 0.857 | k = −14→15 |
16575 measured reflections | l = −29→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C23H17Cl2NO2S | γ = 81.037 (1)° |
Mr = 442.34 | V = 2028.60 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.0083 (1) Å | Mo Kα radiation |
b = 11.7242 (2) Å | µ = 0.44 mm−1 |
c = 21.9150 (4) Å | T = 293 K |
α = 86.474 (1)° | 0.48 × 0.42 × 0.36 mm |
β = 89.831 (1)° |
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 = 0.857 | Rint = 0.038 |
16575 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
9692 reflections | Δρmin = −0.42 e Å−3 |
525 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.64035 (10) | 0.05312 (6) | 0.59489 (3) | 0.0822 (2) | |
Cl2A | 0.27984 (9) | 0.47404 (5) | 0.60557 (2) | 0.06842 (18) | |
S1A | −0.01089 (6) | 0.77117 (4) | 0.22510 (2) | 0.03785 (11) | |
O1A | −0.11130 (17) | 0.88264 (12) | 0.22634 (6) | 0.0512 (4) | |
O2A | −0.06369 (17) | 0.68788 (12) | 0.18750 (6) | 0.0489 (3) | |
N1A | 0.00317 (19) | 0.71381 (13) | 0.29667 (7) | 0.0384 (3) | |
C2A | 0.1067 (2) | 0.60747 (15) | 0.31367 (8) | 0.0370 (4) | |
C3A | 0.1401 (2) | 0.60135 (16) | 0.37473 (8) | 0.0386 (4) | |
C4A | 0.0569 (2) | 0.70933 (16) | 0.39868 (8) | 0.0405 (4) | |
C5A | −0.0239 (2) | 0.77852 (16) | 0.35002 (8) | 0.0381 (4) | |
C6A | −0.1175 (3) | 0.88725 (17) | 0.35693 (10) | 0.0511 (5) | |
H6A | −0.1716 | 0.9317 | 0.3240 | 0.061* | |
C7A | −0.1257 (3) | 0.9256 (2) | 0.41534 (11) | 0.0632 (6) | |
H7A | −0.1853 | 0.9985 | 0.4217 | 0.076* | |
C8A | −0.0485 (4) | 0.8593 (2) | 0.46445 (11) | 0.0696 (7) | |
H8A | −0.0581 | 0.8879 | 0.5032 | 0.084* | |
C9A | 0.0429 (3) | 0.75142 (19) | 0.45702 (9) | 0.0573 (6) | |
H9A | 0.0946 | 0.7072 | 0.4904 | 0.069* | |
C10A | 0.1985 (2) | 0.78568 (15) | 0.20565 (8) | 0.0359 (4) | |
C11A | 0.2941 (3) | 0.83860 (19) | 0.24477 (9) | 0.0487 (5) | |
H11A | 0.2495 | 0.8650 | 0.2815 | 0.058* | |
C12A | 0.4567 (3) | 0.8513 (2) | 0.22807 (11) | 0.0566 (5) | |
H12A | 0.5231 | 0.8860 | 0.2539 | 0.068* | |
C13A | 0.5210 (3) | 0.8130 (2) | 0.17370 (10) | 0.0559 (5) | |
H13A | 0.6305 | 0.8224 | 0.1628 | 0.067* | |
C14A | 0.4258 (3) | 0.7608 (2) | 0.13498 (10) | 0.0543 (5) | |
H14A | 0.4709 | 0.7350 | 0.0982 | 0.065* | |
C15A | 0.2623 (3) | 0.74676 (17) | 0.15093 (9) | 0.0458 (5) | |
H15A | 0.1967 | 0.7116 | 0.1251 | 0.055* | |
C16A | 0.2373 (3) | 0.50213 (17) | 0.40726 (9) | 0.0446 (4) | |
H16A | 0.2920 | 0.4457 | 0.3830 | 0.053* | |
C17A | 0.2591 (3) | 0.48079 (18) | 0.46631 (9) | 0.0496 (5) | |
H17A | 0.2069 | 0.5371 | 0.4912 | 0.060* | |
C18A | 0.3565 (2) | 0.37798 (17) | 0.49714 (8) | 0.0412 (4) | |
C19A | 0.4378 (3) | 0.28500 (19) | 0.46518 (9) | 0.0515 (5) | |
H19A | 0.4333 | 0.2906 | 0.4227 | 0.062* | |
C20A | 0.5236 (3) | 0.1863 (2) | 0.49423 (10) | 0.0556 (6) | |
H20A | 0.5746 | 0.1257 | 0.4717 | 0.067* | |
C21A | 0.5335 (3) | 0.17784 (19) | 0.55716 (10) | 0.0519 (5) | |
C22A | 0.4594 (3) | 0.26661 (18) | 0.59111 (9) | 0.0493 (5) | |
H22A | 0.4679 | 0.2609 | 0.6335 | 0.059* | |
C23A | 0.3723 (2) | 0.36434 (17) | 0.56083 (8) | 0.0421 (4) | |
C24A | 0.1570 (3) | 0.51703 (17) | 0.26920 (9) | 0.0512 (5) | |
H24A | 0.2223 | 0.4503 | 0.2899 | 0.077* | |
H24B | 0.2235 | 0.5471 | 0.2373 | 0.077* | |
H24C | 0.0575 | 0.4955 | 0.2517 | 0.077* | |
Cl1B | 0.91221 (10) | 0.95938 (5) | −0.10054 (3) | 0.07259 (19) | |
Cl2B | 0.75804 (9) | 0.53408 (5) | −0.10649 (2) | 0.06452 (17) | |
S1B | 0.61297 (6) | 0.22578 (4) | 0.27038 (2) | 0.03728 (11) | |
O1B | 0.56164 (18) | 0.11490 (12) | 0.26710 (6) | 0.0496 (3) | |
O2B | 0.51873 (16) | 0.30829 (12) | 0.30764 (6) | 0.0482 (3) | |
N1B | 0.60940 (19) | 0.28541 (13) | 0.19921 (7) | 0.0380 (3) | |
C2B | 0.6649 (2) | 0.39289 (15) | 0.18431 (8) | 0.0363 (4) | |
C3B | 0.7000 (2) | 0.40160 (16) | 0.12346 (8) | 0.0367 (4) | |
C4B | 0.6709 (2) | 0.29390 (16) | 0.09808 (8) | 0.0378 (4) | |
C5B | 0.6172 (2) | 0.22316 (16) | 0.14524 (8) | 0.0377 (4) | |
C6B | 0.5757 (3) | 0.11443 (17) | 0.13588 (10) | 0.0508 (5) | |
H6B | 0.5381 | 0.0690 | 0.1677 | 0.061* | |
C7B | 0.5928 (3) | 0.07703 (19) | 0.07764 (10) | 0.0589 (6) | |
H7B | 0.5670 | 0.0046 | 0.0700 | 0.071* | |
C8B | 0.6477 (3) | 0.1450 (2) | 0.02995 (10) | 0.0617 (6) | |
H8B | 0.6584 | 0.1173 | −0.0090 | 0.074* | |
C9B | 0.6867 (3) | 0.25270 (18) | 0.03941 (9) | 0.0521 (5) | |
H9B | 0.7232 | 0.2977 | 0.0071 | 0.063* | |
C10B | 0.8271 (2) | 0.20869 (15) | 0.29253 (8) | 0.0369 (4) | |
C11B | 0.9500 (3) | 0.15581 (18) | 0.25458 (9) | 0.0492 (5) | |
H11B | 0.9206 | 0.1284 | 0.2178 | 0.059* | |
C12B | 1.1172 (3) | 0.1446 (2) | 0.27240 (11) | 0.0584 (6) | |
H12B | 1.2018 | 0.1100 | 0.2473 | 0.070* | |
C13B | 1.1591 (3) | 0.1845 (2) | 0.32698 (11) | 0.0580 (6) | |
H13B | 1.2721 | 0.1767 | 0.3385 | 0.070* | |
C14B | 1.0368 (3) | 0.2357 (2) | 0.36468 (10) | 0.0590 (6) | |
H14B | 1.0668 | 0.2619 | 0.4017 | 0.071* | |
C15B | 0.8689 (3) | 0.24823 (18) | 0.34768 (9) | 0.0480 (5) | |
H15B | 0.7850 | 0.2829 | 0.3730 | 0.058* | |
C16B | 0.7510 (2) | 0.50219 (16) | 0.09190 (8) | 0.0413 (4) | |
H16B | 0.7886 | 0.5551 | 0.1164 | 0.050* | |
C17B | 0.7507 (3) | 0.52798 (17) | 0.03269 (8) | 0.0477 (5) | |
H17B | 0.7167 | 0.4739 | 0.0081 | 0.057* | |
C18B | 0.7974 (2) | 0.63149 (16) | 0.00098 (8) | 0.0386 (4) | |
C19B | 0.8367 (3) | 0.72582 (17) | 0.03204 (8) | 0.0462 (5) | |
H19B | 0.8381 | 0.7207 | 0.0746 | 0.055* | |
C20B | 0.8731 (3) | 0.82486 (18) | 0.00189 (9) | 0.0490 (5) | |
H20B | 0.8985 | 0.8856 | 0.0237 | 0.059* | |
C21B | 0.8717 (3) | 0.83344 (17) | −0.06110 (9) | 0.0456 (4) | |
C22B | 0.8374 (2) | 0.74370 (17) | −0.09401 (8) | 0.0449 (4) | |
H22B | 0.8389 | 0.7494 | −0.1365 | 0.054* | |
C23B | 0.8008 (2) | 0.64491 (16) | −0.06269 (8) | 0.0402 (4) | |
C24B | 0.6684 (3) | 0.48223 (17) | 0.23001 (9) | 0.0511 (5) | |
H24D | 0.7118 | 0.5476 | 0.2111 | 0.077* | |
H24E | 0.7398 | 0.4498 | 0.2639 | 0.077* | |
H24F | 0.5559 | 0.5066 | 0.2444 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.1061 (5) | 0.0534 (4) | 0.0784 (4) | 0.0092 (4) | −0.0274 (4) | 0.0121 (3) |
Cl2A | 0.0991 (5) | 0.0614 (4) | 0.0418 (3) | 0.0012 (3) | 0.0063 (3) | −0.0155 (2) |
S1A | 0.0378 (2) | 0.0378 (2) | 0.0377 (2) | −0.00701 (19) | −0.00827 (17) | 0.00293 (17) |
O1A | 0.0454 (8) | 0.0453 (8) | 0.0585 (9) | 0.0032 (6) | −0.0097 (6) | 0.0071 (6) |
O2A | 0.0515 (8) | 0.0534 (9) | 0.0453 (8) | −0.0199 (7) | −0.0141 (6) | −0.0012 (6) |
N1A | 0.0417 (8) | 0.0352 (8) | 0.0364 (8) | −0.0012 (7) | −0.0001 (6) | 0.0004 (6) |
C2A | 0.0390 (9) | 0.0345 (9) | 0.0365 (9) | −0.0036 (8) | 0.0010 (7) | −0.0001 (7) |
C3A | 0.0422 (10) | 0.0379 (10) | 0.0356 (9) | −0.0064 (8) | 0.0011 (7) | −0.0010 (7) |
C4A | 0.0454 (10) | 0.0390 (10) | 0.0380 (10) | −0.0093 (8) | 0.0062 (8) | −0.0032 (7) |
C5A | 0.0375 (9) | 0.0374 (10) | 0.0398 (10) | −0.0062 (8) | 0.0063 (7) | −0.0034 (7) |
C6A | 0.0510 (12) | 0.0412 (11) | 0.0588 (13) | −0.0007 (9) | 0.0096 (9) | −0.0010 (9) |
C7A | 0.0765 (16) | 0.0445 (13) | 0.0658 (15) | 0.0024 (11) | 0.0200 (12) | −0.0115 (11) |
C8A | 0.103 (2) | 0.0555 (15) | 0.0507 (13) | −0.0093 (14) | 0.0193 (13) | −0.0152 (11) |
C9A | 0.0839 (16) | 0.0487 (12) | 0.0382 (11) | −0.0058 (11) | 0.0050 (10) | −0.0065 (9) |
C10A | 0.0385 (9) | 0.0327 (9) | 0.0363 (9) | −0.0074 (7) | −0.0055 (7) | 0.0035 (7) |
C11A | 0.0526 (12) | 0.0533 (12) | 0.0430 (11) | −0.0167 (10) | −0.0055 (9) | −0.0040 (9) |
C12A | 0.0520 (12) | 0.0596 (14) | 0.0621 (14) | −0.0237 (11) | −0.0160 (10) | 0.0051 (10) |
C13A | 0.0408 (11) | 0.0604 (14) | 0.0640 (14) | −0.0069 (10) | −0.0006 (10) | 0.0135 (11) |
C14A | 0.0507 (12) | 0.0590 (14) | 0.0504 (12) | −0.0016 (10) | 0.0051 (9) | 0.0004 (10) |
C15A | 0.0505 (11) | 0.0444 (11) | 0.0426 (11) | −0.0069 (9) | −0.0050 (8) | −0.0044 (8) |
C16A | 0.0548 (11) | 0.0392 (10) | 0.0379 (10) | −0.0018 (9) | −0.0006 (8) | −0.0020 (7) |
C17A | 0.0578 (12) | 0.0478 (12) | 0.0379 (10) | 0.0077 (10) | 0.0012 (9) | −0.0017 (8) |
C18A | 0.0449 (10) | 0.0435 (11) | 0.0338 (9) | −0.0033 (8) | −0.0027 (7) | −0.0011 (7) |
C19A | 0.0582 (12) | 0.0583 (13) | 0.0336 (10) | 0.0058 (11) | −0.0011 (8) | −0.0056 (8) |
C20A | 0.0602 (13) | 0.0513 (13) | 0.0507 (12) | 0.0081 (11) | −0.0030 (10) | −0.0096 (10) |
C21A | 0.0568 (12) | 0.0446 (12) | 0.0519 (12) | −0.0029 (10) | −0.0113 (9) | 0.0041 (9) |
C22A | 0.0634 (13) | 0.0514 (12) | 0.0337 (10) | −0.0126 (10) | −0.0063 (9) | 0.0035 (8) |
C23A | 0.0490 (11) | 0.0428 (11) | 0.0351 (9) | −0.0085 (9) | −0.0009 (8) | −0.0049 (7) |
C24A | 0.0678 (13) | 0.0410 (11) | 0.0409 (10) | 0.0052 (10) | −0.0044 (9) | −0.0050 (8) |
Cl1B | 0.1149 (5) | 0.0472 (3) | 0.0592 (4) | −0.0286 (3) | 0.0088 (3) | 0.0088 (2) |
Cl2B | 0.1043 (5) | 0.0525 (3) | 0.0417 (3) | −0.0232 (3) | −0.0030 (3) | −0.0141 (2) |
S1B | 0.0387 (2) | 0.0383 (2) | 0.0348 (2) | −0.00751 (19) | 0.00735 (17) | 0.00117 (17) |
O1B | 0.0561 (8) | 0.0456 (8) | 0.0505 (8) | −0.0219 (7) | 0.0072 (6) | 0.0040 (6) |
O2B | 0.0449 (7) | 0.0540 (9) | 0.0433 (7) | 0.0000 (6) | 0.0134 (6) | −0.0027 (6) |
N1B | 0.0469 (9) | 0.0354 (8) | 0.0332 (8) | −0.0119 (7) | 0.0015 (6) | −0.0011 (6) |
C2B | 0.0406 (9) | 0.0340 (9) | 0.0351 (9) | −0.0093 (8) | −0.0003 (7) | −0.0004 (7) |
C3B | 0.0391 (9) | 0.0378 (10) | 0.0332 (9) | −0.0066 (8) | −0.0018 (7) | 0.0002 (7) |
C4B | 0.0402 (9) | 0.0376 (10) | 0.0352 (9) | −0.0049 (8) | −0.0021 (7) | −0.0019 (7) |
C5B | 0.0389 (9) | 0.0371 (10) | 0.0379 (9) | −0.0074 (8) | −0.0028 (7) | −0.0047 (7) |
C6B | 0.0632 (13) | 0.0431 (12) | 0.0496 (12) | −0.0190 (10) | −0.0022 (9) | −0.0034 (9) |
C7B | 0.0813 (16) | 0.0429 (12) | 0.0566 (13) | −0.0189 (11) | −0.0071 (11) | −0.0124 (10) |
C8B | 0.0946 (18) | 0.0486 (13) | 0.0434 (12) | −0.0120 (12) | −0.0032 (11) | −0.0133 (9) |
C9B | 0.0751 (14) | 0.0454 (12) | 0.0364 (10) | −0.0109 (11) | −0.0002 (9) | −0.0031 (8) |
C10B | 0.0402 (9) | 0.0315 (9) | 0.0383 (9) | −0.0048 (7) | 0.0050 (7) | 0.0023 (7) |
C11B | 0.0484 (11) | 0.0522 (12) | 0.0452 (11) | −0.0012 (9) | 0.0072 (9) | −0.0067 (9) |
C12B | 0.0444 (11) | 0.0574 (14) | 0.0694 (15) | 0.0030 (10) | 0.0123 (10) | 0.0011 (11) |
C13B | 0.0434 (11) | 0.0619 (14) | 0.0661 (15) | −0.0090 (10) | −0.0056 (10) | 0.0187 (11) |
C14B | 0.0614 (14) | 0.0663 (15) | 0.0510 (13) | −0.0172 (12) | −0.0097 (10) | 0.0025 (10) |
C15B | 0.0513 (11) | 0.0498 (12) | 0.0425 (11) | −0.0060 (9) | 0.0035 (9) | −0.0039 (8) |
C16B | 0.0507 (11) | 0.0373 (10) | 0.0377 (10) | −0.0123 (8) | 0.0002 (8) | −0.0027 (7) |
C17B | 0.0694 (13) | 0.0413 (11) | 0.0365 (10) | −0.0214 (10) | −0.0007 (9) | −0.0020 (8) |
C18B | 0.0450 (10) | 0.0390 (10) | 0.0328 (9) | −0.0101 (8) | 0.0011 (7) | −0.0008 (7) |
C19B | 0.0610 (12) | 0.0493 (12) | 0.0316 (9) | −0.0177 (10) | 0.0021 (8) | −0.0042 (8) |
C20B | 0.0660 (13) | 0.0422 (11) | 0.0425 (11) | −0.0183 (10) | 0.0029 (9) | −0.0073 (8) |
C21B | 0.0542 (11) | 0.0388 (10) | 0.0438 (11) | −0.0100 (9) | 0.0056 (8) | 0.0036 (8) |
C22B | 0.0557 (12) | 0.0454 (11) | 0.0327 (9) | −0.0065 (9) | 0.0033 (8) | 0.0015 (8) |
C23B | 0.0484 (10) | 0.0404 (10) | 0.0319 (9) | −0.0063 (8) | 0.0003 (7) | −0.0058 (7) |
C24B | 0.0765 (14) | 0.0417 (11) | 0.0381 (10) | −0.0184 (10) | 0.0049 (9) | −0.0039 (8) |
Cl1A—C21A | 1.738 (2) | Cl1B—C21B | 1.739 (2) |
Cl2A—C23A | 1.737 (2) | Cl2B—C23B | 1.738 (2) |
S1A—O1A | 1.426 (1) | S1B—O2B | 1.428 (1) |
S1A—O2A | 1.429 (1) | S1B—O1B | 1.429 (1) |
S1A—N1A | 1.665 (2) | S1B—N1B | 1.668 (2) |
S1A—C10A | 1.760 (2) | S1B—C10B | 1.761 (2) |
N1A—C2A | 1.415 (2) | N1B—C2B | 1.419 (2) |
N1A—C5A | 1.430 (2) | N1B—C5B | 1.424 (2) |
C2A—C3A | 1.361 (2) | C2B—C3B | 1.363 (2) |
C2A—C24A | 1.493 (2) | C2B—C24B | 1.497 (2) |
C3A—C16A | 1.445 (3) | C3B—C16B | 1.444 (3) |
C3A—C4A | 1.462 (2) | C3B—C4B | 1.462 (2) |
C4A—C9A | 1.397 (3) | C4B—C5B | 1.394 (3) |
C4A—C5A | 1.396 (3) | C4B—C9B | 1.400 (2) |
C5A—C6A | 1.391 (2) | C5B—C6B | 1.394 (3) |
C6A—C7A | 1.381 (3) | C6B—C7B | 1.374 (3) |
C6A—H6A | 0.93 | C6B—H6B | 0.93 |
C7A—C8A | 1.377 (4) | C7B—C8B | 1.387 (3) |
C7A—H7A | 0.93 | C7B—H7B | 0.93 |
C8A—C9A | 1.378 (3) | C8B—C9B | 1.375 (3) |
C8A—H8A | 0.93 | C8B—H8B | 0.93 |
C9A—H9A | 0.93 | C9B—H9B | 0.93 |
C10A—C15A | 1.378 (2) | C10B—C11B | 1.383 (2) |
C10A—C11A | 1.387 (3) | C10B—C15B | 1.381 (3) |
C11A—C12A | 1.379 (3) | C11B—C12B | 1.380 (3) |
C11A—H11A | 0.93 | C11B—H11B | 0.93 |
C12A—C13A | 1.370 (3) | C12B—C13B | 1.372 (3) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C13A—C14A | 1.374 (3) | C13B—C14B | 1.369 (3) |
C13A—H13A | 0.93 | C13B—H13B | 0.93 |
C14A—C15A | 1.386 (3) | C14B—C15B | 1.379 (3) |
C14A—H14A | 0.93 | C14B—H14B | 0.93 |
C15A—H15A | 0.93 | C15B—H15B | 0.93 |
C16A—C17A | 1.310 (3) | C16B—C17B | 1.314 (3) |
C16A—H16A | 0.93 | C16B—H16B | 0.93 |
C17A—C18A | 1.459 (3) | C17B—C18B | 1.460 (3) |
C17A—H17A | 0.93 | C17B—H17B | 0.93 |
C18A—C23A | 1.399 (2) | C18B—C23B | 1.395 (2) |
C18A—C19A | 1.405 (2) | C18B—C19B | 1.410 (2) |
C19A—C20A | 1.372 (3) | C19B—C20B | 1.371 (3) |
C19A—H19A | 0.93 | C19B—H19B | 0.93 |
C20A—C21A | 1.378 (3) | C20B—C21B | 1.378 (3) |
C20A—H20A | 0.93 | C20B—H20B | 0.93 |
C21A—C22A | 1.374 (3) | C21B—C22B | 1.374 (3) |
C22A—C23A | 1.378 (3) | C22B—C23B | 1.380 (3) |
C22A—H22A | 0.93 | C22B—H22B | 0.93 |
C24A—H24A | 0.96 | C24B—H24D | 0.96 |
C24A—H24B | 0.96 | C24B—H24E | 0.96 |
C24A—H24C | 0.96 | C24B—H24F | 0.96 |
O1A—S1A—O2A | 119.03 (8) | O2B—S1B—O1B | 118.9 (1) |
O1A—S1A—N1A | 107.11 (8) | O2B—S1B—N1B | 107.5 (1) |
O2A—S1A—N1A | 107.58 (8) | O1B—S1B—N1B | 107.1 (1) |
O1A—S1A—C10A | 109.81 (9) | O2B—S1B—C10B | 108.3 (1) |
O2A—S1A—C10A | 108.00 (8) | O1B—S1B—C10B | 109.8 (1) |
N1A—S1A—C10A | 104.33 (8) | N1B—S1B—C10B | 104.3 (1) |
C2A—N1A—C5A | 107.8 (1) | C2B—N1B—C5B | 107.9 (1) |
C2A—N1A—S1A | 122.8 (1) | C2B—N1B—S1B | 122.8 (1) |
C5A—N1A—S1A | 124.8 (1) | C5B—N1B—S1B | 125.0 (1) |
C3A—C2A—N1A | 109.7 (1) | C3B—C2B—N1B | 109.5 (2) |
C3A—C2A—C24A | 128.0 (2) | C3B—C2B—C24B | 127.9 (2) |
N1A—C2A—C24A | 122.2 (2) | N1B—C2B—C24B | 122.5 (2) |
C2A—C3A—C16A | 123.8 (2) | C2B—C3B—C16B | 124.4 (2) |
C2A—C3A—C4A | 107.3 (2) | C2B—C3B—C4B | 107.2 (2) |
C16A—C3A—C4A | 128.8 (2) | C16B—C3B—C4B | 128.4 (2) |
C9A—C4A—C5A | 118.3 (2) | C5B—C4B—C9B | 118.5 (2) |
C9A—C4A—C3A | 133.7 (2) | C5B—C4B—C3B | 108.2 (2) |
C5A—C4A—C3A | 108.0 (2) | C9B—C4B—C3B | 133.4 (2) |
C6A—C5A—C4A | 123.1 (2) | C6B—C5B—C4B | 122.5 (2) |
C6A—C5A—N1A | 129.7 (2) | C6B—C5B—N1B | 130.2 (2) |
C4A—C5A—N1A | 107.1 (2) | C4B—C5B—N1B | 107.2 (2) |
C7A—C6A—C5A | 116.3 (2) | C7B—C6B—C5B | 117.3 (2) |
C7A—C6A—H6A | 121.8 | C7B—C6B—H6B | 121.4 |
C5A—C6A—H6A | 121.8 | C5B—C6B—H6B | 121.4 |
C8A—C7A—C6A | 122.1 (2) | C6B—C7B—C8B | 121.5 (2) |
C8A—C7A—H7A | 118.9 | C6B—C7B—H7B | 119.3 |
C6A—C7A—H7A | 118.9 | C8B—C7B—H7B | 119.3 |
C7A—C8A—C9A | 120.9 (2) | C9B—C8B—C7B | 120.9 (2) |
C7A—C8A—H8A | 119.5 | C9B—C8B—H8B | 119.5 |
C9A—C8A—H8A | 119.5 | C7B—C8B—H8B | 119.5 |
C8A—C9A—C4A | 119.2 (2) | C8B—C9B—C4B | 119.3 (2) |
C8A—C9A—H9A | 120.4 | C8B—C9B—H9B | 120.3 |
C4A—C9A—H9A | 120.4 | C4B—C9B—H9B | 120.3 |
C15A—C10A—C11A | 121.4 (2) | C11B—C10B—C15B | 121.3 (3) |
C15A—C10A—S1A | 119.1 (1) | C11B—C10B—S1B | 119.5 (3) |
C11A—C10A—S1A | 119.5 (1) | C15B—C10B—S1B | 119.2 (1) |
C12A—C11A—C10A | 118.6 (2) | C12B—C11B—C10B | 118.6 (2) |
C12A—C11A—H11A | 120.7 | C12B—C11B—H11B | 120.7 |
C10A—C11A—H11A | 120.7 | C10B—C11B—H11B | 120.7 |
C13A—C12A—C11A | 120.3 (2) | C13B—C12B—C11B | 120.2 (2) |
C13A—C12A—H12A | 119.8 | C13B—C12B—H12B | 119.9 |
C11A—C12A—H12A | 119.8 | C11B—C12B—H12B | 119.9 |
C12A—C13A—C14A | 120.9 (2) | C12B—C13B—C14B | 120.9 (2) |
C12A—C13A—H13A | 119.5 | C12B—C13B—H13B | 119.5 |
C14A—C13A—H13A | 119.5 | C14B—C13B—H13B | 119.5 |
C13A—C14A—C15A | 119.7 (2) | C13B—C14B—C15B | 119.9 (2) |
C13A—C14A—H14A | 120.1 | C13B—C14B—H14B | 120.1 |
C15A—C14A—H14A | 120.1 | C15B—C14B—H14B | 120.1 |
C10A—C15A—C14A | 119.0 (2) | C14B—C15B—C10B | 119.1 (2) |
C10A—C15A—H15A | 120.5 | C14B—C15B—H15B | 120.5 |
C14A—C15A—H15A | 120.5 | C10B—C15B—H15B | 120.5 |
C17A—C16A—C3A | 128.9 (2) | C17B—C16B—C3B | 127.8 (2) |
C17A—C16A—H16A | 115.6 | C17B—C16B—H16B | 116.1 |
C3A—C16A—H16A | 115.6 | C3B—C16B—H16B | 116.1 |
C16A—C17A—C18A | 126.9 (2) | C16B—C17B—C18B | 127.7 (2) |
C16A—C17A—H17A | 116.6 | C16B—C17B—H17B | 116.1 |
C18A—C17A—H17A | 116.6 | C18B—C17B—H17B | 116.1 |
C23A—C18A—C19A | 115.4 (2) | C23B—C18B—C19B | 115.4 (2) |
C23A—C18A—C17A | 122.1 (2) | C23B—C18B—C17B | 121.8 (2) |
C19A—C18A—C17A | 122.5 (2) | C19B—C18B—C17B | 122.8 (2) |
C20A—C19A—C18A | 122.5 (2) | C20B—C19B—C18B | 122.5 (2) |
C20A—C19A—H19A | 118.7 | C20B—C19B—H19B | 118.8 |
C18A—C19A—H19A | 118.7 | C18B—C19B—H19B | 118.8 |
C19A—C20A—C21A | 119.2 (2) | C19B—C20B—C21B | 119.3 (2) |
C19A—C20A—H20A | 120.4 | C19B—C20B—H20B | 120.4 |
C21A—C20A—H20A | 120.4 | C21B—C20B—H20B | 120.4 |
C22A—C21A—C20A | 121.1 (2) | C22B—C21B—C20B | 121.1 (2) |
C22A—C21A—Cl1A | 118.9 (2) | C22B—C21B—Cl1B | 118.7 (2) |
C20A—C21A—Cl1A | 120.0 (2) | C20B—C21B—Cl1B | 120.3 (2) |
C21A—C22A—C23A | 118.5 (2) | C21B—C22B—C23B | 118.6 (2) |
C21A—C22A—H22A | 120.8 | C21B—C22B—H22B | 120.7 |
C23A—C22A—H22A | 120.8 | C23B—C22B—H22B | 120.7 |
C22A—C23A—C18A | 123.2 (2) | C22B—C23B—C18B | 123.1 (2) |
C22A—C23A—Cl2A | 116.9 (1) | C22B—C23B—Cl2B | 116.8 (2) |
C18A—C23A—Cl2A | 119.9 (2) | C18B—C23B—Cl2B | 120.1 (2) |
C2A—C24A—H24A | 109.5 | C2B—C24B—H24D | 109.5 |
C2A—C24A—H24B | 109.5 | C2B—C24B—H24E | 109.5 |
H24A—C24A—H24B | 109.5 | H24D—C24B—H24E | 109.5 |
C2A—C24A—H24C | 109.5 | C2B—C24B—H24F | 109.5 |
H24A—C24A—H24C | 109.5 | H24D—C24B—H24F | 109.5 |
H24B—C24A—H24C | 109.5 | H24E—C24B—H24F | 109.5 |
O1A—S1A—N1A—C2A | −174.03 (14) | O2B—S1B—N1B—C2B | 55.83 (16) |
O2A—S1A—N1A—C2A | 56.90 (16) | O1B—S1B—N1B—C2B | −175.35 (13) |
C10A—S1A—N1A—C2A | −57.64 (16) | C10B—S1B—N1B—C2B | −58.98 (15) |
O1A—S1A—N1A—C5A | −21.06 (17) | O2B—S1B—N1B—C5B | −150.15 (14) |
O2A—S1A—N1A—C5A | −150.12 (14) | O1B—S1B—N1B—C5B | −21.33 (16) |
C10A—S1A—N1A—C5A | 95.3 (2) | C10B—S1B—N1B—C5B | 95.0 (2) |
C5A—N1A—C2A—C3A | 2.0 (2) | C5B—N1B—C2B—C3B | 2.3 (2) |
S1A—N1A—C2A—C3A | 158.97 (14) | S1B—N1B—C2B—C3B | 160.17 (13) |
C5A—N1A—C2A—C24A | 178.55 (18) | C5B—N1B—C2B—C24B | 178.23 (17) |
S1A—N1A—C2A—C24A | −24.5 (2) | S1B—N1B—C2B—C24B | −23.9 (2) |
N1A—C2A—C3A—C16A | 177.63 (17) | N1B—C2B—C3B—C16B | 176.58 (16) |
C24A—C2A—C3A—C16A | 1.4 (3) | C24B—C2B—C3B—C16B | 1.0 (3) |
N1A—C2A—C3A—C4A | −0.9 (2) | N1B—C2B—C3B—C4B | −1.7 (2) |
C24A—C2A—C3A—C4A | −177.16 (19) | C24B—C2B—C3B—C4B | −177.29 (18) |
C2A—C3A—C4A—C9A | 178.3 (2) | C2B—C3B—C4B—C5B | 0.4 (2) |
C16A—C3A—C4A—C9A | −0.2 (4) | C16B—C3B—C4B—C5B | −177.76 (18) |
C2A—C3A—C4A—C5A | −0.6 (2) | C2B—C3B—C4B—C9B | −179.4 (2) |
C16A—C3A—C4A—C5A | −179.03 (19) | C16B—C3B—C4B—C9B | 2.4 (3) |
C9A—C4A—C5A—C6A | 0.0 (3) | C9B—C4B—C5B—C6B | −1.3 (3) |
C3A—C4A—C5A—C6A | 179.11 (18) | C3B—C4B—C5B—C6B | 178.85 (17) |
C9A—C4A—C5A—N1A | −177.27 (18) | C9B—C4B—C5B—N1B | −179.12 (16) |
C3A—C4A—C5A—N1A | 1.8 (2) | C3B—C4B—C5B—N1B | 1.02 (19) |
C2A—N1A—C5A—C6A | −179.43 (19) | C2B—N1B—C5B—C6B | −179.63 (19) |
S1A—N1A—C5A—C6A | 24.2 (3) | S1B—N1B—C5B—C6B | 23.1 (3) |
C2A—N1A—C5A—C4A | −2.4 (2) | C2B—N1B—C5B—C4B | −2.02 (19) |
S1A—N1A—C5A—C4A | −158.70 (14) | S1B—N1B—C5B—C4B | −159.27 (13) |
C4A—C5A—C6A—C7A | 0.8 (3) | C4B—C5B—C6B—C7B | 1.3 (3) |
N1A—C5A—C6A—C7A | 177.4 (2) | N1B—C5B—C6B—C7B | 178.55 (19) |
C5A—C6A—C7A—C8A | −1.2 (4) | C5B—C6B—C7B—C8B | −0.5 (3) |
C6A—C7A—C8A—C9A | 0.8 (4) | C6B—C7B—C8B—C9B | −0.2 (4) |
C7A—C8A—C9A—C4A | 0.1 (4) | C7B—C8B—C9B—C4B | 0.2 (4) |
C5A—C4A—C9A—C8A | −0.5 (3) | C5B—C4B—C9B—C8B | 0.5 (3) |
C3A—C4A—C9A—C8A | −179.3 (2) | C3B—C4B—C9B—C8B | −179.6 (2) |
O1A—S1A—C10A—C15A | −113.71 (16) | O2B—S1B—C10B—C11B | −164.44 (16) |
O2A—S1A—C10A—C15A | 17.5 (2) | O1B—S1B—C10B—C11B | 64.30 (18) |
N1A—S1A—C10A—C15A | 131.78 (15) | N1B—S1B—C10B—C11B | −50.16 (18) |
O1A—S1A—C10A—C11A | 64.59 (17) | O2B—S1B—C10B—C15B | 15.7 (2) |
O2A—S1A—C10A—C11A | −164.16 (16) | O1B—S1B—C10B—C15B | −115.54 (16) |
N1A—S1A—C10A—C11A | −49.91 (17) | N1B—S1B—C10B—C15B | 130.00 (15) |
C15A—C10A—C11A—C12A | −0.4 (3) | C15B—C10B—C11B—C12B | −1.0 (3) |
S1A—C10A—C11A—C12A | −178.67 (16) | S1B—C10B—C11B—C12B | 179.15 (17) |
C10A—C11A—C12A—C13A | 0.5 (3) | C10B—C11B—C12B—C13B | 0.6 (3) |
C11A—C12A—C13A—C14A | −0.4 (3) | C11B—C12B—C13B—C14B | 0.1 (4) |
C12A—C13A—C14A—C15A | 0.1 (3) | C12B—C13B—C14B—C15B | −0.4 (4) |
C11A—C10A—C15A—C14A | 0.2 (3) | C13B—C14B—C15B—C10B | 0.0 (3) |
S1A—C10A—C15A—C14A | 178.43 (16) | C11B—C10B—C15B—C14B | 0.7 (3) |
C13A—C14A—C15A—C10A | 0.0 (3) | S1B—C10B—C15B—C14B | −179.43 (17) |
C2A—C3A—C16A—C17A | −170.4 (2) | C2B—C3B—C16B—C17B | −163.5 (2) |
C4A—C3A—C16A—C17A | 7.8 (4) | C4B—C3B—C16B—C17B | 14.4 (3) |
C3A—C16A—C17A—C18A | 178.8 (2) | C3B—C16B—C17B—C18B | 177.92 (19) |
C16A—C17A—C18A—C23A | 179.6 (2) | C16B—C17B—C18B—C23B | 176.1 (2) |
C16A—C17A—C18A—C19A | −1.7 (4) | C16B—C17B—C18B—C19B | −5.9 (3) |
C23A—C18A—C19A—C20A | 1.5 (3) | C23B—C18B—C19B—C20B | 1.1 (3) |
C17A—C18A—C19A—C20A | −177.3 (2) | C17B—C18B—C19B—C20B | −177.0 (2) |
C18A—C19A—C20A—C21A | −1.1 (4) | C18B—C19B—C20B—C21B | −0.1 (3) |
C19A—C20A—C21A—C22A | −0.2 (4) | C19B—C20B—C21B—C22B | −1.2 (3) |
C19A—C20A—C21A—Cl1A | 179.54 (18) | C19B—C20B—C21B—Cl1B | 178.40 (16) |
C20A—C21A—C22A—C23A | 0.9 (3) | C20B—C21B—C22B—C23B | 1.3 (3) |
Cl1A—C21A—C22A—C23A | −178.82 (17) | Cl1B—C21B—C22B—C23B | −178.28 (15) |
C21A—C22A—C23A—C18A | −0.4 (3) | C21B—C22B—C23B—C18B | −0.2 (3) |
C21A—C22A—C23A—Cl2A | 179.70 (17) | C21B—C22B—C23B—Cl2B | 179.90 (15) |
C19A—C18A—C23A—C22A | −0.7 (3) | C19B—C18B—C23B—C22B | −1.0 (3) |
C17A—C18A—C23A—C22A | 178.0 (2) | C17B—C18B—C23B—C22B | 177.18 (19) |
C19A—C18A—C23A—Cl2A | 179.14 (16) | C19B—C18B—C23B—Cl2B | 178.96 (14) |
C17A—C18A—C23A—Cl2A | −2.1 (3) | C17B—C18B—C23B—Cl2B | −2.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O1A | 0.93 | 2.28 | 2.866 (3) | 120 |
C6B—H6B···O1B | 0.93 | 2.29 | 2.878 (2) | 121 |
C15A—H15A···O2A | 0.93 | 2.53 | 2.901 (3) | 104 |
C15B—H15B···O2B | 0.93 | 2.54 | 2.907 (2) | 104 |
C17A—H17A···Cl2A | 0.93 | 2.61 | 3.052 (2) | 110 |
C17B—H17B···Cl2B | 0.93 | 2.60 | 3.047 (2) | 110 |
C19A—H19A···O2B | 0.93 | 2.61 | 3.513 (2) | 163 |
C19B—H19B···O2Ai | 0.93 | 2.59 | 3.487 (2) | 163 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H17Cl2NO2S |
Mr | 442.34 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 2028.60 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.44 |
Crystal size (mm) | 0.48 × 0.42 × 0.36 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.815, 0.857 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16575, 9692, 7077 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.121, 1.04 |
No. of reflections | 9692 |
No. of parameters | 525 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
Cl1A—C21A | 1.738 (2) | Cl1B—C21B | 1.739 (2) |
Cl2A—C23A | 1.737 (2) | Cl2B—C23B | 1.738 (2) |
S1A—O1A | 1.426 (1) | S1B—O2B | 1.428 (1) |
S1A—O2A | 1.429 (1) | S1B—O1B | 1.429 (1) |
S1A—N1A | 1.665 (2) | S1B—N1B | 1.668 (2) |
S1A—C10A | 1.760 (2) | S1B—C10B | 1.761 (2) |
N1A—C2A | 1.415 (2) | N1B—C2B | 1.419 (2) |
N1A—C5A | 1.430 (2) | N1B—C5B | 1.424 (2) |
C3A—C16A | 1.445 (3) | C3B—C16B | 1.444 (3) |
C16A—C17A | 1.310 (3) | C16B—C17B | 1.314 (3) |
C17A—C18A | 1.459 (3) | C17B—C18B | 1.460 (3) |
O1A—S1A—O2A | 119.03 (8) | O2B—S1B—O1B | 118.9 (1) |
O1A—S1A—N1A | 107.11 (8) | O2B—S1B—N1B | 107.5 (1) |
O2A—S1A—N1A | 107.58 (8) | O1B—S1B—N1B | 107.1 (1) |
O1A—S1A—C10A | 109.81 (9) | O2B—S1B—C10B | 108.3 (1) |
O2A—S1A—C10A | 108.00 (8) | O1B—S1B—C10B | 109.8 (1) |
N1A—S1A—C10A | 104.33 (8) | N1B—S1B—C10B | 104.3 (1) |
C2A—N1A—C5A | 107.8 (1) | C2B—N1B—C5B | 107.9 (1) |
C2A—N1A—S1A | 122.8 (1) | C2B—N1B—S1B | 122.8 (1) |
C5A—N1A—S1A | 124.8 (1) | C5B—N1B—S1B | 125.0 (1) |
C3A—C2A—C24A | 128.0 (2) | C3B—C2B—C24B | 127.9 (2) |
N1A—C2A—C24A | 122.2 (2) | N1B—C2B—C24B | 122.5 (2) |
C2A—C3A—C16A | 123.8 (2) | C2B—C3B—C16B | 124.4 (2) |
C16A—C3A—C4A | 128.8 (2) | C16B—C3B—C4B | 128.4 (2) |
C17A—C16A—C3A | 128.9 (2) | C17B—C16B—C3B | 127.8 (2) |
C16A—C17A—C18A | 126.9 (2) | C16B—C17B—C18B | 127.7 (2) |
C10A—S1A—N1A—C5A | 95.3 (2) | C10B—S1B—N1B—C5B | 95.0 (2) |
S1A—N1A—C5A—C6A | 24.2 (3) | S1B—N1B—C5B—C6B | 23.1 (3) |
O2A—S1A—C10A—C15A | 17.5 (2) | O2B—S1B—C10B—C15B | 15.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O1A | 0.93 | 2.28 | 2.866 (3) | 120 |
C6B—H6B···O1B | 0.93 | 2.29 | 2.878 (2) | 121 |
C15A—H15A···O2A | 0.93 | 2.53 | 2.901 (3) | 104 |
C15B—H15B···O2B | 0.93 | 2.54 | 2.907 (2) | 104 |
C17A—H17A···Cl2A | 0.93 | 2.61 | 3.052 (2) | 110 |
C17B—H17B···Cl2B | 0.93 | 2.60 | 3.047 (2) | 110 |
C19A—H19A···O2B | 0.93 | 2.61 | 3.513 (2) | 163 |
C19B—H19B···O2Ai | 0.93 | 2.59 | 3.487 (2) | 163 |
Symmetry code: (i) x+1, y, z. |
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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 S═O 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).