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In the title mol­ecule, C21H17NO3S2, the sulfonyl-bound and sulfinyl-bound phenyl rings form dihedral angles of 82.04 (5) and 26.26 (8)°, respectively, with the indole ring system. In the crystal structure C—H...O, C—H...π and π–π inter­actions form a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045934/sg2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045934/sg2076Isup2.hkl
Contains datablock I

CCDC reference: 630449

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.045
  • wR factor = 0.119
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-Phenylsulfinylmethyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C21H17NO3S2F(000) = 824
Mr = 395.48Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7239 reflections
a = 18.3174 (3) Åθ = 2.2–27.7°
b = 10.8625 (2) ŵ = 0.31 mm1
c = 9.6364 (1) ÅT = 100 K
β = 104.697 (1)°Plate, colourless
V = 1854.65 (5) Å30.33 × 0.27 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5242 independent reflections
Radiation source: fine-focus sealed tube4215 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 8.33 pixels mm-1θmax = 29.7°, θmin = 1.2°
ω scansh = 2525
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1511
Tmin = 0.864, Tmax = 0.982l = 1313
27648 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.9013P]
where P = (Fo2 + 2Fc2)/3
5242 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.62 e Å3
12 restraintsΔρmin = 0.38 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*/UeqOcc. (<1)
S10.42470 (2)0.15221 (4)0.23459 (5)0.02208 (12)
S2A0.04631 (3)0.18200 (7)0.24863 (7)0.0254 (2)0.869 (3)
O3A0.05758 (9)0.14533 (18)0.39087 (17)0.0349 (4)0.869 (3)
S2B0.0371 (2)0.1128 (5)0.3013 (5)0.0318 (15)0.131 (3)
O3B0.0533 (7)0.2469 (14)0.3214 (17)0.057 (4)0.131 (3)
O10.44181 (7)0.26558 (12)0.31090 (14)0.0304 (3)
O20.47059 (7)0.10669 (13)0.14654 (14)0.0277 (3)
N10.33823 (8)0.17339 (13)0.12760 (15)0.0209 (3)
C10.28349 (11)0.24569 (17)0.1699 (2)0.0254 (4)
H10.29400.30660.24300.031*
C20.21404 (10)0.21506 (17)0.0909 (2)0.0259 (4)
H20.16790.25200.09670.031*
C30.22219 (9)0.11678 (16)0.00344 (18)0.0205 (3)
C40.16996 (10)0.04567 (17)0.10336 (19)0.0238 (4)
C50.19754 (11)0.04525 (17)0.1765 (2)0.0265 (4)
H50.16310.09290.24630.032*
C60.27480 (10)0.06894 (17)0.15050 (19)0.0250 (4)
H60.29140.13270.20270.030*
C70.32808 (10)0.00216 (16)0.05062 (18)0.0214 (3)
H70.38060.01860.03260.026*
C80.29995 (9)0.09030 (15)0.02146 (17)0.0184 (3)
C90.41154 (9)0.03530 (16)0.35175 (18)0.0192 (3)
C100.37991 (10)0.06663 (17)0.46335 (19)0.0255 (4)
H100.36750.14980.47770.031*
C110.36677 (11)0.02547 (18)0.5535 (2)0.0282 (4)
H110.34550.00560.63090.034*
C120.38466 (10)0.14656 (17)0.5308 (2)0.0252 (4)
H120.37470.20960.59190.030*
C130.41692 (10)0.17641 (17)0.4198 (2)0.0238 (4)
H130.42950.25960.40600.029*
C140.43090 (9)0.08558 (16)0.32890 (19)0.0212 (3)
H140.45320.10530.25280.025*
C150.08644 (10)0.06077 (19)0.1225 (2)0.0295 (4)
H15A0.07660.07970.02840.035*0.869 (3)
H15B0.06100.01790.15690.035*0.869 (3)
H15C0.07780.11860.05300.035*0.131 (3)
H15D0.06560.01700.10450.035*0.131 (3)
C160.05031 (10)0.1438 (2)0.2527 (2)0.0320 (4)
C170.09167 (12)0.0668 (2)0.3574 (2)0.0392 (5)
H170.06990.03260.42830.047*
C180.16650 (12)0.0401 (2)0.3569 (3)0.0423 (5)
H180.19600.01290.42790.051*
C190.19744 (11)0.0910 (2)0.2530 (2)0.0356 (5)
H190.24820.07330.25300.043*
C200.15439 (11)0.16768 (19)0.1492 (2)0.0333 (5)
H200.17570.20210.07770.040*
C210.08023 (11)0.19452 (19)0.1490 (2)0.0324 (4)
H210.05060.24720.07790.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0189 (2)0.0238 (2)0.0215 (2)0.00450 (16)0.00141 (16)0.00330 (17)
S2A0.0157 (2)0.0293 (4)0.0291 (3)0.0031 (2)0.0019 (2)0.0048 (3)
O3A0.0221 (8)0.0562 (12)0.0267 (9)0.0076 (7)0.0067 (7)0.0054 (8)
S2B0.0169 (17)0.048 (3)0.029 (2)0.0025 (17)0.0031 (14)0.000 (2)
O3B0.038 (6)0.063 (7)0.074 (8)0.003 (5)0.021 (5)0.039 (6)
O10.0313 (7)0.0254 (7)0.0297 (7)0.0095 (5)0.0010 (6)0.0015 (6)
O20.0192 (6)0.0368 (7)0.0272 (7)0.0027 (5)0.0061 (5)0.0063 (6)
N10.0201 (7)0.0217 (7)0.0191 (7)0.0003 (5)0.0017 (6)0.0001 (6)
C10.0314 (10)0.0217 (9)0.0236 (9)0.0048 (7)0.0079 (7)0.0008 (7)
C20.0238 (9)0.0275 (9)0.0278 (9)0.0062 (7)0.0092 (7)0.0015 (7)
C30.0184 (8)0.0228 (8)0.0208 (8)0.0024 (6)0.0057 (6)0.0046 (7)
C40.0178 (8)0.0279 (9)0.0242 (9)0.0002 (7)0.0028 (7)0.0040 (7)
C50.0255 (9)0.0263 (9)0.0246 (9)0.0050 (7)0.0009 (7)0.0009 (7)
C60.0288 (9)0.0235 (9)0.0227 (9)0.0024 (7)0.0067 (7)0.0021 (7)
C70.0202 (8)0.0233 (8)0.0211 (8)0.0029 (7)0.0058 (6)0.0025 (7)
C80.0187 (8)0.0183 (8)0.0174 (8)0.0002 (6)0.0033 (6)0.0032 (6)
C90.0146 (7)0.0226 (8)0.0183 (8)0.0033 (6)0.0001 (6)0.0021 (6)
C100.0290 (9)0.0223 (9)0.0247 (9)0.0006 (7)0.0060 (7)0.0014 (7)
C110.0291 (9)0.0341 (10)0.0234 (9)0.0004 (8)0.0101 (7)0.0016 (8)
C120.0207 (8)0.0291 (9)0.0248 (9)0.0023 (7)0.0041 (7)0.0062 (7)
C130.0188 (8)0.0221 (8)0.0297 (9)0.0009 (7)0.0044 (7)0.0027 (7)
C140.0150 (8)0.0256 (9)0.0225 (8)0.0011 (6)0.0042 (6)0.0013 (7)
C150.0181 (9)0.0360 (10)0.0323 (10)0.0002 (7)0.0026 (7)0.0067 (8)
C160.0169 (8)0.0452 (12)0.0322 (10)0.0027 (8)0.0034 (7)0.0156 (9)
C170.0270 (10)0.0546 (14)0.0353 (11)0.0064 (9)0.0067 (9)0.0040 (10)
C180.0279 (11)0.0496 (14)0.0441 (13)0.0018 (10)0.0005 (9)0.0013 (11)
C190.0201 (9)0.0391 (12)0.0475 (12)0.0010 (8)0.0081 (9)0.0167 (10)
C200.0259 (10)0.0365 (11)0.0396 (11)0.0077 (8)0.0123 (8)0.0146 (9)
C210.0235 (9)0.0361 (11)0.0348 (11)0.0031 (8)0.0020 (8)0.0129 (9)
Geometric parameters (Å, º) top
S1—O21.4259 (14)C9—C101.387 (2)
S1—O11.4277 (14)C9—C141.392 (2)
S1—N11.6721 (15)C10—C111.386 (3)
S1—C91.7560 (17)C10—H100.95
S2A—O3A1.4912 (19)C11—C121.386 (3)
S2A—C161.8083 (19)C11—H110.95
S2A—C151.816 (2)C12—C131.385 (3)
S2B—O3B1.510 (16)C12—H120.95
S2B—C161.810 (4)C13—C141.386 (2)
S2B—C151.820 (4)C13—H130.95
N1—C81.410 (2)C14—H140.95
N1—C11.413 (2)C15—H15A0.99
C1—C21.348 (3)C15—H15B0.99
C1—H10.95C15—H15C0.96
C2—C31.434 (2)C15—H15D0.96
C2—H20.95C16—C211.372 (3)
C3—C41.404 (2)C16—C171.380 (3)
C3—C81.413 (2)C17—C181.402 (3)
C4—C51.381 (3)C17—H170.95
C4—C151.503 (2)C18—C191.385 (3)
C5—C61.397 (3)C18—H180.95
C5—H50.95C19—C201.385 (3)
C6—C71.389 (3)C19—H190.95
C6—H60.95C20—C211.389 (3)
C7—C81.392 (2)C20—H200.95
C7—H70.95C21—H210.95
O2—S1—O1121.34 (8)C13—C12—C11120.54 (17)
O2—S1—N1106.86 (8)C13—C12—H12119.7
O1—S1—N1104.41 (8)C11—C12—H12119.7
O2—S1—C9109.25 (8)C12—C13—C14120.32 (17)
O1—S1—C9109.91 (8)C12—C13—H13119.8
N1—S1—C9103.47 (8)C14—C13—H13119.8
O3A—S2A—C16106.35 (10)C13—C14—C9118.44 (16)
O3A—S2A—C15107.12 (11)C13—C14—H14120.8
C16—S2A—C1594.37 (9)C9—C14—H14120.8
O3B—S2B—C1694.0 (6)C4—C15—S2A112.84 (13)
O3B—S2B—C15110.8 (7)C4—C15—S2B113.32 (18)
C16—S2B—C1594.2 (2)C4—C15—H15A109.0
C8—N1—C1107.84 (14)S2A—C15—H15A109.0
C8—N1—S1125.32 (12)S2B—C15—H15A129.8
C1—N1—S1121.95 (12)C4—C15—H15B109.0
C2—C1—N1109.69 (16)S2A—C15—H15B109.0
C2—C1—H1125.2S2B—C15—H15B82.7
N1—C1—H1125.2H15A—C15—H15B107.8
C1—C2—C3107.86 (16)C4—C15—H15C109.2
C1—C2—H2126.1S2A—C15—H15C83.3
C3—C2—H2126.1S2B—C15—H15C109.1
C4—C3—C8119.12 (16)H15B—C15—H15C130.6
C4—C3—C2132.98 (16)C4—C15—H15D108.7
C8—C3—C2107.84 (15)S2A—C15—H15D130.3
C5—C4—C3118.00 (16)S2B—C15—H15D108.7
C5—C4—C15120.53 (17)H15A—C15—H15D81.0
C3—C4—C15121.31 (17)H15C—C15—H15D107.8
C4—C5—C6121.68 (17)C21—C16—C17121.96 (19)
C4—C5—H5119.2C21—C16—S2A117.51 (17)
C6—C5—H5119.2C17—C16—S2A120.53 (17)
C7—C6—C5122.00 (17)C21—C16—S2B143.7 (2)
C7—C6—H6119.0C17—C16—S2B93.2 (2)
C5—C6—H6119.0C16—C17—C18118.6 (2)
C6—C7—C8116.02 (16)C16—C17—H17120.7
C6—C7—H7122.0C18—C17—H17120.7
C8—C7—H7122.0C19—C18—C17120.0 (2)
C7—C8—N1130.14 (15)C19—C18—H18120.0
C7—C8—C3123.16 (16)C17—C18—H18120.0
N1—C8—C3106.70 (14)C20—C19—C18120.03 (19)
C10—C9—C14121.82 (16)C20—C19—H19120.0
C10—C9—S1118.26 (13)C18—C19—H19120.0
C14—C9—S1119.90 (13)C19—C20—C21120.3 (2)
C11—C10—C9118.83 (17)C19—C20—H20119.8
C11—C10—H10120.6C21—C20—H20119.8
C9—C10—H10120.6C16—C21—C20119.1 (2)
C10—C11—C12120.03 (17)C16—C21—H21120.5
C10—C11—H11120.0C20—C21—H21120.5
C12—C11—H11120.0
O2—S1—N1—C844.03 (16)C11—C12—C13—C140.8 (3)
O1—S1—N1—C8173.74 (14)C12—C13—C14—C90.2 (3)
C9—S1—N1—C871.23 (15)C10—C9—C14—C130.9 (3)
O2—S1—N1—C1163.81 (14)S1—C9—C14—C13177.39 (13)
O1—S1—N1—C134.10 (16)C5—C4—C15—S2A98.57 (19)
C9—S1—N1—C180.93 (15)C3—C4—C15—S2A86.2 (2)
C8—N1—C1—C22.7 (2)C5—C4—C15—S2B67.4 (3)
S1—N1—C1—C2159.14 (13)C3—C4—C15—S2B117.4 (3)
N1—C1—C2—C32.0 (2)O3A—S2A—C15—C462.67 (17)
C1—C2—C3—C4176.66 (19)C16—S2A—C15—C4171.28 (16)
C1—C2—C3—C80.5 (2)O3A—S2A—C15—S2B34.5 (3)
C8—C3—C4—C52.0 (2)C16—S2A—C15—S2B74.1 (3)
C2—C3—C4—C5178.92 (19)O3B—S2B—C15—C473.3 (7)
C8—C3—C4—C15173.37 (16)C16—S2B—C15—C4169.1 (2)
C2—C3—C4—C153.6 (3)O3B—S2B—C15—S2A22.0 (6)
C3—C4—C5—C61.6 (3)C16—S2B—C15—S2A73.9 (3)
C15—C4—C5—C6173.80 (17)O3A—S2A—C16—C21164.83 (16)
C4—C5—C6—C70.4 (3)C15—S2A—C16—C2185.90 (17)
C5—C6—C7—C80.4 (3)O3A—S2A—C16—C1715.0 (2)
C6—C7—C8—N1179.97 (16)C15—S2A—C16—C1794.31 (19)
C6—C7—C8—C30.1 (2)O3A—S2A—C16—S2B35.0 (3)
C1—N1—C8—C7177.75 (17)C15—S2A—C16—S2B74.3 (3)
S1—N1—C8—C722.3 (3)O3B—S2B—C16—C2168.0 (7)
C1—N1—C8—C32.30 (18)C15—S2B—C16—C2143.2 (5)
S1—N1—C8—C3157.71 (12)O3B—S2B—C16—C17125.4 (6)
C4—C3—C8—C71.3 (3)C15—S2B—C16—C17123.4 (2)
C2—C3—C8—C7178.93 (16)O3B—S2B—C16—S2A37.4 (6)
C4—C3—C8—N1178.77 (15)C15—S2B—C16—S2A73.8 (3)
C2—C3—C8—N11.12 (18)C21—C16—C17—C180.1 (3)
O2—S1—C9—C10168.77 (13)S2A—C16—C17—C18179.72 (17)
O1—S1—C9—C1033.34 (16)S2B—C16—C17—C18170.8 (2)
N1—S1—C9—C1077.69 (15)C16—C17—C18—C190.1 (3)
O2—S1—C9—C1412.91 (16)C17—C18—C19—C200.3 (3)
O1—S1—C9—C14148.34 (13)C18—C19—C20—C210.3 (3)
N1—S1—C9—C14100.63 (14)C17—C16—C21—C200.1 (3)
C14—C9—C10—C110.5 (3)S2A—C16—C21—C20179.71 (15)
S1—C9—C10—C11177.76 (14)S2B—C16—C21—C20164.3 (3)
C9—C10—C11—C120.5 (3)C19—C20—C21—C160.1 (3)
C10—C11—C12—C131.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3Ai0.952.343.286 (3)176
C7—H7···O20.952.473.051 (2)119
C13—H13···O2ii0.952.493.298 (2)143
C14—H14···O20.952.572.937 (2)103
C14—H14···O1ii0.952.583.385 (2)143
C17—H17···O3A0.952.582.959 (3)104
C1—H1···Cg1i0.952.803.669 (2)152
C19—H19···Cg2iii0.952.893.689 (2)142
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y, z.
 

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