Download citation
Download citation
link to html
In the title compound, C30H24ClNO3S, the phenyl­sulfon­yl, chloro­phen­yl and methoxy­phen­yl rings are each almost perpendicular to the indole ring system. The crystal packing shows centrosymmetrically related pairs of mol­ecules. Inter­molecular C—H...O inter­actions are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017472/bt6662sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017472/bt6662Isup2.hkl
Contains datablock I

CCDC reference: 277200

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.085
  • wR factor = 0.277
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94 PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C25 .. 10.70 su PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C28
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.277 PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.76 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C28 .. 6.15 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C17 - C25 ... 1.54 Ang.
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

3-[α-(4-Methoxyphenyl)-β-(4-chlorophenyl)vinyl]-2-methyl-1-phenylsulfonyl- 1H-indole top
Crystal data top
C30H24ClNO3SF(000) = 1072
Mr = 514.01Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5225 reflections
a = 13.6402 (9) Åθ = 2.3–25.6°
b = 10.4097 (6) ŵ = 0.26 mm1
c = 18.4430 (11) ÅT = 273 K
β = 99.756 (1)°Block, colourless
V = 2580.9 (3) Å30.24 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.0°, θmin = 2.3°
ω scansh = 1714
15377 measured reflectionsk = 1313
5533 independent reflectionsl = 2324
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)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.277H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1623P)2 + 1.4648P]
where P = (Fo2 + 2Fc2)/3
5533 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = 0.51 e Å3
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
S10.30984 (7)0.85500 (7)0.20721 (6)0.0676 (4)
Cl10.07037 (12)0.34662 (15)0.10709 (8)0.1114 (5)
O10.4143 (2)0.8614 (3)0.2226 (2)0.1022 (12)
O20.2522 (3)0.9572 (2)0.22978 (18)0.0935 (10)
O30.4508 (4)0.1867 (5)0.5500 (3)0.1487 (18)
N10.2763 (2)0.7239 (2)0.24790 (15)0.0560 (7)
C20.3202 (2)0.6006 (3)0.24180 (19)0.0540 (7)
C30.2578 (2)0.5116 (2)0.26004 (17)0.0480 (7)
C40.1706 (2)0.5734 (3)0.27728 (16)0.0475 (7)
C50.1810 (2)0.7052 (3)0.26764 (16)0.0493 (7)
C60.1076 (3)0.7913 (3)0.2801 (2)0.0709 (10)
H60.11490.87930.27410.085*
C70.0246 (4)0.7412 (5)0.3015 (3)0.0906 (14)
H70.02610.79660.30930.109*
C80.0132 (3)0.6107 (5)0.3118 (3)0.0858 (12)
H80.04450.58040.32640.103*
C90.0858 (3)0.5258 (4)0.3008 (2)0.0654 (9)
H90.07870.43830.30890.079*
C100.2716 (3)0.8276 (3)0.1138 (2)0.0616 (9)
C110.1715 (3)0.8342 (4)0.0859 (2)0.0764 (11)
H110.12580.85390.11640.092*
C120.1400 (5)0.8108 (6)0.0114 (3)0.1041 (17)
H120.07300.81510.00910.125*
C130.2102 (7)0.7813 (7)0.0312 (3)0.127 (2)
H130.18940.76690.08120.152*
C140.3069 (6)0.7723 (8)0.0038 (4)0.131 (2)
H140.35180.74920.03430.158*
C150.3404 (4)0.7969 (5)0.0693 (3)0.1006 (16)
H150.40790.79310.08860.121*
C160.4185 (3)0.5790 (4)0.2193 (3)0.0945 (15)
H16A0.43740.49070.22740.142*
H16B0.46740.63320.24790.142*
H16C0.41410.59920.16810.142*
C170.2766 (3)0.3709 (3)0.2665 (2)0.0644 (9)
C180.2556 (3)0.2917 (3)0.2105 (2)0.0675 (9)
H180.27240.20630.22080.081*
C190.2103 (3)0.3176 (3)0.1353 (2)0.0589 (8)
C200.1742 (3)0.4323 (3)0.1024 (2)0.0705 (10)
H200.17860.50700.13040.085*
C210.1326 (3)0.4376 (4)0.0302 (2)0.0792 (11)
H210.10870.51550.00970.095*
C220.1253 (3)0.3287 (4)0.0134 (2)0.0720 (10)
C230.1577 (3)0.2153 (4)0.0159 (3)0.0861 (13)
H230.15190.14140.01280.103*
C240.1993 (3)0.2101 (3)0.0885 (3)0.0783 (11)
H240.22170.13100.10810.094*
C250.3242 (3)0.3208 (3)0.3432 (2)0.0628 (8)
C260.3401 (5)0.1957 (5)0.3608 (3)0.1055 (17)
H260.32130.13410.32460.127*
C270.3827 (5)0.1556 (5)0.4300 (4)0.1158 (19)
H270.39330.06830.43890.139*
C280.4099 (3)0.2420 (5)0.4864 (3)0.0836 (12)
C290.3942 (4)0.3686 (4)0.4700 (2)0.0811 (11)
H290.41250.43030.50620.097*
C300.3516 (3)0.4060 (4)0.4003 (2)0.0727 (10)
H300.34060.49310.39110.087*
C310.4708 (4)0.2690 (6)0.6074 (3)0.119 (2)
H31A0.51960.33040.59790.179*
H31B0.49620.22190.65130.179*
H31C0.41100.31300.61370.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0798 (6)0.0351 (4)0.0797 (7)0.0141 (3)0.0093 (5)0.0098 (3)
Cl10.1192 (11)0.1329 (12)0.0748 (8)0.0042 (8)0.0046 (8)0.0144 (7)
O10.086 (2)0.0754 (18)0.130 (3)0.0372 (15)0.0237 (19)0.0312 (17)
O20.144 (3)0.0327 (11)0.098 (2)0.0005 (13)0.0032 (19)0.0024 (12)
O30.130 (4)0.179 (5)0.129 (4)0.005 (3)0.003 (3)0.066 (4)
N10.0671 (16)0.0333 (11)0.0642 (17)0.0003 (10)0.0018 (14)0.0066 (10)
C20.0523 (16)0.0393 (13)0.068 (2)0.0066 (11)0.0029 (15)0.0102 (13)
C30.0518 (15)0.0341 (12)0.0557 (18)0.0028 (10)0.0022 (13)0.0003 (11)
C40.0530 (16)0.0430 (14)0.0439 (16)0.0015 (11)0.0008 (13)0.0063 (11)
C50.0645 (18)0.0418 (13)0.0388 (15)0.0076 (12)0.0004 (14)0.0020 (11)
C60.095 (3)0.0513 (17)0.066 (2)0.0241 (17)0.013 (2)0.0002 (15)
C70.091 (3)0.092 (3)0.095 (3)0.037 (2)0.032 (3)0.002 (2)
C80.070 (2)0.092 (3)0.100 (3)0.008 (2)0.030 (2)0.007 (2)
C90.0611 (19)0.0621 (19)0.073 (2)0.0036 (15)0.0114 (18)0.0065 (16)
C100.068 (2)0.0476 (16)0.068 (2)0.0071 (14)0.0078 (18)0.0183 (14)
C110.074 (2)0.080 (3)0.072 (3)0.0058 (19)0.003 (2)0.0129 (19)
C120.112 (4)0.118 (4)0.073 (3)0.028 (3)0.011 (3)0.023 (3)
C130.183 (7)0.138 (5)0.057 (3)0.029 (5)0.017 (4)0.015 (3)
C140.156 (6)0.164 (6)0.084 (4)0.007 (5)0.049 (4)0.030 (4)
C150.093 (3)0.114 (4)0.101 (4)0.005 (3)0.036 (3)0.038 (3)
C160.066 (2)0.070 (2)0.153 (5)0.0094 (19)0.032 (3)0.037 (3)
C170.062 (2)0.0353 (13)0.101 (3)0.0027 (12)0.0283 (19)0.0025 (15)
C180.086 (3)0.0442 (16)0.073 (2)0.0071 (15)0.016 (2)0.0045 (15)
C190.0586 (18)0.0535 (16)0.065 (2)0.0034 (14)0.0115 (16)0.0098 (14)
C200.099 (3)0.0426 (16)0.061 (2)0.0061 (16)0.011 (2)0.0027 (14)
C210.099 (3)0.0554 (19)0.075 (3)0.0005 (19)0.009 (2)0.0067 (17)
C220.067 (2)0.085 (3)0.063 (2)0.0045 (18)0.0097 (19)0.0119 (18)
C230.091 (3)0.073 (3)0.093 (3)0.000 (2)0.012 (3)0.028 (2)
C240.089 (3)0.0440 (17)0.104 (3)0.0095 (16)0.021 (2)0.0060 (18)
C250.0581 (19)0.0638 (19)0.066 (2)0.0035 (15)0.0088 (17)0.0032 (16)
C260.148 (5)0.067 (3)0.091 (3)0.004 (3)0.010 (3)0.001 (2)
C270.150 (5)0.064 (3)0.123 (5)0.002 (3)0.007 (4)0.022 (3)
C280.073 (2)0.098 (3)0.075 (3)0.002 (2)0.000 (2)0.035 (2)
C290.089 (3)0.087 (3)0.063 (3)0.004 (2)0.002 (2)0.003 (2)
C300.090 (3)0.064 (2)0.061 (2)0.0024 (19)0.000 (2)0.0048 (17)
C310.078 (3)0.169 (6)0.101 (4)0.017 (3)0.010 (3)0.066 (4)
Geometric parameters (Å, º) top
S1—O11.407 (3)C14—H140.9300
S1—O21.426 (3)C15—H150.9300
S1—N11.658 (2)C16—H16A0.9600
S1—C101.738 (4)C16—H16B0.9600
Cl1—C221.773 (4)C16—H16C0.9600
O3—C281.340 (6)C17—C181.314 (5)
O3—C311.353 (4)C17—C251.544 (6)
N1—C51.421 (4)C18—C191.444 (5)
N1—C21.429 (4)C18—H180.9300
C2—C31.339 (4)C19—C201.392 (5)
C2—C161.485 (5)C19—C241.406 (5)
C3—C41.434 (4)C20—C211.357 (6)
C3—C171.488 (4)C20—H200.9300
C4—C51.394 (4)C21—C221.382 (6)
C4—C91.394 (5)C21—H210.9300
C5—C61.391 (4)C22—C231.342 (6)
C6—C71.365 (6)C23—C241.364 (6)
C6—H60.9300C23—H230.9300
C7—C81.384 (7)C24—H240.9300
C7—H70.9300C25—C261.351 (6)
C8—C91.368 (5)C25—C301.379 (5)
C8—H80.9300C26—C271.374 (8)
C9—H90.9300C26—H260.9300
C10—C111.376 (5)C27—C281.378 (8)
C10—C151.384 (6)C27—H270.9300
C11—C121.391 (7)C28—C291.362 (6)
C11—H110.9300C29—C301.374 (6)
C12—C131.371 (9)C29—H290.9300
C12—H120.9300C30—H300.9300
C13—C141.334 (9)C31—H31A0.9600
C13—H130.9300C31—H31B0.9600
C14—C151.373 (9)C31—H31C0.9600
O1—S1—O2119.7 (2)C2—C16—H16B109.5
O1—S1—N1107.2 (2)H16A—C16—H16B109.5
O2—S1—N1105.9 (2)C2—C16—H16C109.5
O1—S1—C10109.4 (2)H16A—C16—H16C109.5
O2—S1—C10108.9 (2)H16B—C16—H16C109.5
N1—S1—C10104.8 (1)C18—C17—C3122.9 (4)
C28—O3—C31114.3 (5)C18—C17—C25120.7 (3)
C5—N1—C2108.1 (2)C3—C17—C25116.4 (3)
C5—N1—S1124.3 (2)C17—C18—C19129.6 (3)
C2—N1—S1123.5 (2)C17—C18—H18115.2
C3—C2—N1108.0 (3)C19—C18—H18115.2
C3—C2—C16127.4 (3)C20—C19—C24114.9 (3)
N1—C2—C16124.6 (3)C20—C19—C18129.9 (3)
C2—C3—C4109.4 (2)C24—C19—C18115.2 (3)
C2—C3—C17126.4 (3)C21—C20—C19121.5 (3)
C4—C3—C17124.2 (3)C21—C20—H20119.3
C5—C4—C9119.8 (3)C19—C20—H20119.3
C5—C4—C3107.9 (3)C20—C21—C22120.9 (4)
C9—C4—C3132.3 (3)C20—C21—H21119.6
C4—C5—C6121.4 (3)C22—C21—H21119.6
C4—C5—N1106.6 (2)C23—C22—C21120.1 (4)
C6—C5—N1131.9 (3)C23—C22—Cl1122.7 (3)
C7—C6—C5117.2 (3)C21—C22—Cl1117.2 (3)
C7—C6—H6121.4C22—C23—C24119.0 (4)
C5—C6—H6121.4C22—C23—H23120.5
C6—C7—C8122.2 (4)C24—C23—H23120.5
C6—C7—H7118.9C23—C24—C19123.7 (3)
C8—C7—H7118.9C23—C24—H24118.1
C9—C8—C7120.9 (4)C19—C24—H24118.1
C9—C8—H8119.5C26—C25—C30115.1 (4)
C7—C8—H8119.5C26—C25—C17124.9 (4)
C8—C9—C4118.4 (4)C30—C25—C17120.0 (3)
C8—C9—H9120.8C25—C26—C27122.9 (5)
C4—C9—H9120.8C25—C26—H26118.6
C11—C10—C15121.4 (4)C27—C26—H26118.6
C11—C10—S1118.3 (3)C26—C27—C28121.3 (4)
C15—C10—S1120.3 (4)C26—C27—H27119.3
C12—C11—C10118.7 (5)C28—C27—H27119.3
C12—C11—H11120.7O3—C28—C29129.6 (5)
C10—C11—H11120.7O3—C28—C27113.5 (5)
C13—C12—C11118.5 (5)C29—C28—C27116.9 (4)
C13—C12—H12120.8C28—C29—C30120.5 (4)
C11—C12—H12120.8C28—C29—H29119.7
C14—C13—C12122.7 (6)C30—C29—H29119.7
C14—C13—H13118.6C25—C30—C29123.3 (4)
C12—C13—H13118.6C25—C30—H30118.3
C13—C14—C15120.1 (6)C29—C30—H30118.3
C13—C14—H14120.0O3—C31—H31A109.5
C15—C14—H14120.0O3—C31—H31B109.5
C10—C15—C14118.6 (5)H31A—C31—H31B109.5
C10—C15—H15120.7O3—C31—H31C109.5
C14—C15—H15120.7H31A—C31—H31C109.5
C2—C16—H16A109.5H31B—C31—H31C109.5
O1—S1—N1—C5157.2 (3)C10—C11—C12—C130.5 (7)
O2—S1—N1—C528.3 (3)C11—C12—C13—C141.0 (10)
C10—S1—N1—C586.7 (3)C12—C13—C14—C152.1 (11)
O1—S1—N1—C248.4 (3)C11—C10—C15—C140.3 (7)
O2—S1—N1—C2177.3 (3)S1—C10—C15—C14178.1 (4)
C10—S1—N1—C267.7 (3)C13—C14—C15—C101.7 (10)
C5—N1—C2—C32.7 (4)C2—C3—C17—C1888.1 (5)
S1—N1—C2—C3160.6 (2)C4—C3—C17—C1896.0 (4)
C5—N1—C2—C16177.6 (4)C2—C3—C17—C2591.0 (4)
S1—N1—C2—C1619.7 (5)C4—C3—C17—C2584.9 (4)
N1—C2—C3—C41.0 (4)C3—C17—C18—C191.8 (6)
C16—C2—C3—C4179.2 (4)C25—C17—C18—C19179.1 (3)
N1—C2—C3—C17175.4 (3)C17—C18—C19—C202.0 (7)
C16—C2—C3—C174.3 (6)C17—C18—C19—C24179.3 (4)
C2—C3—C4—C51.0 (4)C24—C19—C20—C210.6 (6)
C17—C3—C4—C5177.6 (3)C18—C19—C20—C21179.3 (4)
C2—C3—C4—C9178.2 (3)C19—C20—C21—C220.4 (7)
C17—C3—C4—C91.6 (6)C20—C21—C22—C231.3 (7)
C9—C4—C5—C60.9 (5)C20—C21—C22—Cl1179.6 (3)
C3—C4—C5—C6179.8 (3)C21—C22—C23—C241.2 (7)
C9—C4—C5—N1176.7 (3)Cl1—C22—C23—C24179.8 (3)
C3—C4—C5—N12.6 (3)C22—C23—C24—C190.2 (7)
C2—N1—C5—C43.3 (3)C20—C19—C24—C230.7 (6)
S1—N1—C5—C4161.0 (2)C18—C19—C24—C23179.6 (4)
C2—N1—C5—C6179.6 (4)C18—C17—C25—C265.9 (6)
S1—N1—C5—C621.8 (5)C3—C17—C25—C26175.0 (4)
C4—C5—C6—C70.6 (5)C18—C17—C25—C30175.9 (4)
N1—C5—C6—C7177.4 (4)C3—C17—C25—C303.2 (5)
C5—C6—C7—C81.1 (7)C30—C25—C26—C271.6 (8)
C6—C7—C8—C90.0 (8)C17—C25—C26—C27179.9 (5)
C7—C8—C9—C41.5 (7)C25—C26—C27—C281.5 (10)
C5—C4—C9—C81.9 (5)C31—O3—C28—C296.6 (8)
C3—C4—C9—C8179.0 (4)C31—O3—C28—C27175.1 (5)
O1—S1—C10—C11172.0 (3)C26—C27—C28—O3179.7 (6)
O2—S1—C10—C1139.5 (3)C26—C27—C28—C291.1 (9)
N1—S1—C10—C1173.4 (3)O3—C28—C29—C30179.3 (5)
O1—S1—C10—C159.6 (4)C27—C28—C29—C301.0 (7)
O2—S1—C10—C15142.1 (3)C26—C25—C30—C291.6 (6)
N1—S1—C10—C15105.0 (3)C17—C25—C30—C29179.9 (4)
C15—C10—C11—C120.8 (6)C28—C29—C30—C251.3 (7)
S1—C10—C11—C12179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.312.889 (5)120
C16—H16A···O1i0.962.473.264 (5)140
C31—H31B···O1ii0.962.593.531 (6)168
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds