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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o12.
Published online 2008 December 3. doi:  10.1107/S160053680804004X
PMCID: PMC2967933

Diethyl 2-[(2-benzyl-1-phenyl­sulfonyl-1H-indol-3-yl)methyl­ene]malonate

Abstract

In the title compound, C29H27NO6S, the sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 87.96 (6)°], while the benzyl­phenyl ring is oriented at an angle of 76.8 (7)°. An intra­molecular C—H(...)O hydrogen bond is observed. In the crystal structure, mol­ecules are linked into a zigzag C(10) chain along the b axis by inter­molecular C—H(...)O hydrogen bonds.

Related literature

For general background to indole derivatives and their biological activity, see: Andreani et al. (2001 [triangle]); Bassindale (1984 [triangle]); Quetin-Leclercq et al. (1995 [triangle]); Singh et al. (2000 [triangle]); Tsotinis et al. (1997 [triangle]); Wang & Ng (2002 [triangle]).

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Object name is e-65-00o12-scheme1.jpg

Experimental

Crystal data

  • C29H27NO6S
  • M r = 517.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o12-efi1.jpg
  • a = 10.8280 (9) Å
  • b = 13.7762 (11) Å
  • c = 17.6832 (16) Å
  • β = 91.341 (4)°
  • V = 2637.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 293 (2) K
  • 0.30 × 0.25 × 0.16 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.952, T max = 0.968
  • 34168 measured reflections
  • 7583 independent reflections
  • 4683 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.142
  • S = 1.02
  • 7583 reflections
  • 334 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); 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, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804004X/ci2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804004X/ci2729Isup2.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. VD thanks UGC, India, for financial support.

supplementary crystallographic information

Comment

Indole derivatives have been found to exhibit antibacterial, antifungal (Wang & Ng, 2002; Singh et al., 2000; Tsotinis et al., 1997; Quetin-Leclercq et al., 1995) and antitumour activities (Andreani et al., 2001).

The longer C—N distances [N1—C2 = 1.417 (2) Å and N1—C5 = 1.421 (2) Å] are indicative of the electronic withdrawing character of the phenylsulfonyl group. Atom S1 has a distorted tetrahedral configuration. The widening of the O1—S1—O2 angle to 120.09 (8)°, and the resultant narrowing of the N1—S1—C10 to 104.99 (8)°, from the ideal tetrahedral values, are attributed to the Thorpe- Ingold effect (Bassindale, 1984). The indole ring system is planar. The sum of bond angles around N1 (358.0°) indicates that N1 is in sp2 hybridization. The sulfonyl bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 87.96 (6)°. The benzylphenyl ring is oriented at an angle of 76.69 (5)° with respect to the indole ring system. The ester groups attached to the indole ring system assume extended conformations [C3—C23—C24—C25 = 178.7 (2)°, C23—C24—C25—O4 = -176.8 (2)°, C24—C25—O4—C26 =179.4 (2)°, C25—O4—C26—C27 = 172.6 (2)°]. An intramolecular C6—H6···O1 hydrogen bond is observed.

In the crystal structure, the molecules are linked into a zigzag C(10) chain along the b axis by intermolecular C—H···O hydrogen bonds (Table 1 and Fig.2).

Experimental

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)methylene)malonate (0.5 g, 0.96 mmol) in dry benzene (15 ml), ZnBr2 (0.43 g, 1.90 mmol) was added. The reaction mixture was then refluxed for 5 h under N2 atmosphere. It was then poured over ice-water (50 ml) containing 1 ml of concentrated HCl, extracted with chloroform (2 × 10 ml) and dried (Na2SO4). Removal of solvent followed by flash column chromatography (silica gel, 230–420 mesh, n-hexane/ethyl acetate 99:1) led to the isolation of diethyl-2-((2-benzyl-1-(phenylsulfonyl)-1H-indol-3-yl)methylene)malonate as a colourless solid. Single crystals were obtained by recrystallization from CDCl3.

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). The components of the anisotropic displacement parameters of C26 and C27 in the direction of the bond between them were restrained to be equal within an effective standard deviation of 0.001.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level. H atoms have been omitted for clarity.
Fig. 2.
Crystal packing of the title compound. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C29H27NO6SF(000) = 1088
Mr = 517.58Dx = 1.304 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7583 reflections
a = 10.8280 (9) Åθ = 2.2–29.9°
b = 13.7762 (11) ŵ = 0.17 mm1
c = 17.6832 (16) ÅT = 293 K
β = 91.341 (4)°Block, colourless
V = 2637.1 (4) Å30.30 × 0.25 × 0.16 mm
Z = 4

Data collection

Bruker Kappa APEXII area-detector diffractometer7583 independent reflections
Radiation source: fine-focus sealed tube4683 reflections with I > 2σ(I)
graphiteRint = 0.030
ω and [var phi] scansθmax = 29.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −15→12
Tmin = 0.952, Tmax = 0.968k = −14→19
34168 measured reflectionsl = −22→24

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0628P)2 + 0.5537P] where P = (Fo2 + 2Fc2)/3
7583 reflections(Δ/σ)max = 0.021
334 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = −0.27 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
C20.62844 (14)0.59182 (11)0.04158 (8)0.0397 (3)
C30.51591 (14)0.62397 (12)0.06343 (8)0.0413 (3)
C40.46420 (15)0.55336 (12)0.11419 (8)0.0429 (3)
C50.54970 (15)0.47797 (12)0.12226 (8)0.0433 (4)
C60.52568 (17)0.39664 (14)0.16628 (10)0.0546 (4)
H60.58240.34620.17070.066*
C70.41513 (19)0.39360 (15)0.20291 (10)0.0612 (5)
H70.39810.34090.23380.073*
C80.32872 (18)0.46698 (15)0.19496 (10)0.0597 (5)
H80.25460.46240.22020.072*
C90.35069 (16)0.54695 (13)0.15017 (10)0.0524 (4)
H90.29150.59540.14400.063*
C100.86326 (16)0.49835 (14)0.16366 (10)0.0524 (4)
C110.96281 (18)0.55897 (16)0.15389 (12)0.0648 (5)
H110.99270.57080.10590.078*
C121.0176 (2)0.60210 (19)0.21722 (15)0.0835 (7)
H121.08520.64300.21180.100*
C130.9725 (2)0.5846 (2)0.28747 (16)0.0986 (9)
H131.00730.61580.32940.118*
C140.8760 (3)0.5212 (3)0.29651 (13)0.1091 (10)
H140.84780.50800.34470.131*
C150.8210 (2)0.4773 (2)0.23443 (12)0.0856 (7)
H150.75600.43400.24030.103*
C160.71395 (15)0.64140 (12)−0.01088 (8)0.0446 (4)
H16A0.66520.6821−0.04490.053*
H16B0.75340.5923−0.04140.053*
C170.81366 (14)0.70333 (12)0.02598 (9)0.0426 (3)
C180.93068 (15)0.70523 (13)−0.00413 (10)0.0510 (4)
H180.94700.6673−0.04620.061*
C191.02346 (18)0.76232 (15)0.02708 (12)0.0647 (5)
H191.10140.76240.00610.078*
C201.00051 (19)0.81899 (17)0.08912 (13)0.0724 (6)
H201.06300.85700.11070.087*
C210.8847 (2)0.81906 (17)0.11901 (12)0.0741 (6)
H210.86860.85810.16050.089*
C220.79141 (16)0.76163 (14)0.08807 (10)0.0567 (5)
H220.71350.76220.10910.068*
C230.46256 (15)0.71538 (13)0.03676 (9)0.0477 (4)
H230.46940.7277−0.01470.057*
C240.40536 (15)0.78361 (12)0.07624 (9)0.0476 (4)
C250.36165 (19)0.87182 (15)0.03489 (12)0.0619 (5)
C260.2677 (3)1.02592 (18)0.04540 (15)0.1004 (9)
H26A0.33651.06360.02700.120*
H26B0.21221.01150.00300.120*
C270.2032 (3)1.0801 (2)0.10279 (18)0.1203 (12)
H27A0.17231.13970.08140.180*
H27B0.25911.09430.14420.180*
H27C0.13551.04210.12060.180*
C280.38732 (16)0.77720 (12)0.15970 (10)0.0502 (4)
C290.4911 (2)0.74032 (19)0.27630 (11)0.0809 (7)
H29A0.41250.71170.28920.097*
H29B0.50120.80040.30430.097*
C300.5929 (3)0.6728 (2)0.29586 (14)0.1064 (9)
H30A0.59240.65900.34910.160*
H30B0.67030.70200.28340.160*
H30C0.58210.61360.26790.160*
N10.65221 (12)0.50118 (10)0.07694 (7)0.0434 (3)
O10.76255 (13)0.34702 (9)0.10092 (8)0.0690 (4)
O20.85555 (12)0.46945 (10)0.01832 (7)0.0633 (4)
O30.3719 (2)0.88321 (13)−0.03157 (9)0.1094 (7)
O40.31220 (15)0.93642 (10)0.08018 (8)0.0764 (4)
O50.29041 (13)0.78452 (13)0.18992 (8)0.0796 (4)
O60.49406 (12)0.75941 (10)0.19517 (6)0.0585 (3)
S10.78964 (4)0.44550 (3)0.08437 (2)0.04989 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0459 (8)0.0424 (8)0.0309 (7)0.0023 (7)0.0020 (6)−0.0038 (6)
C30.0452 (8)0.0447 (8)0.0340 (7)0.0016 (7)0.0032 (6)−0.0048 (6)
C40.0464 (8)0.0455 (9)0.0370 (8)−0.0037 (7)0.0048 (6)−0.0059 (7)
C50.0489 (9)0.0456 (9)0.0355 (7)−0.0019 (7)0.0027 (6)−0.0039 (6)
C60.0612 (11)0.0529 (10)0.0498 (10)−0.0033 (8)0.0006 (8)0.0058 (8)
C70.0703 (12)0.0621 (12)0.0514 (10)−0.0159 (10)0.0063 (9)0.0086 (9)
C80.0590 (11)0.0694 (13)0.0512 (10)−0.0182 (10)0.0143 (8)−0.0059 (9)
C90.0486 (9)0.0565 (10)0.0524 (10)−0.0037 (8)0.0107 (8)−0.0101 (8)
C100.0457 (9)0.0609 (11)0.0506 (9)0.0128 (8)0.0012 (7)0.0029 (8)
C110.0536 (11)0.0751 (13)0.0653 (12)0.0044 (10)−0.0044 (9)0.0152 (10)
C120.0632 (13)0.0920 (17)0.0942 (18)−0.0040 (12)−0.0210 (13)0.0058 (14)
C130.0718 (16)0.141 (2)0.0823 (18)0.0089 (16)−0.0203 (13)−0.0306 (17)
C140.0797 (17)0.195 (3)0.0526 (13)−0.012 (2)0.0023 (12)−0.0129 (17)
C150.0687 (13)0.137 (2)0.0510 (12)−0.0199 (14)0.0061 (10)−0.0014 (13)
C160.0485 (9)0.0516 (9)0.0338 (7)0.0050 (7)0.0063 (6)−0.0001 (7)
C170.0439 (8)0.0426 (8)0.0415 (8)0.0067 (7)0.0062 (6)0.0043 (7)
C180.0505 (9)0.0530 (10)0.0499 (9)0.0071 (8)0.0113 (7)0.0025 (8)
C190.0500 (10)0.0672 (13)0.0775 (13)−0.0016 (9)0.0109 (9)0.0031 (11)
C200.0570 (11)0.0733 (14)0.0868 (15)−0.0107 (10)−0.0022 (10)−0.0109 (12)
C210.0729 (13)0.0775 (15)0.0720 (13)−0.0009 (11)0.0059 (11)−0.0294 (11)
C220.0480 (9)0.0650 (12)0.0575 (10)0.0042 (8)0.0101 (8)−0.0138 (9)
C230.0488 (9)0.0541 (10)0.0405 (8)0.0058 (8)0.0053 (7)0.0017 (7)
C240.0456 (8)0.0496 (9)0.0477 (9)0.0084 (7)0.0050 (7)0.0033 (7)
C250.0677 (12)0.0595 (11)0.0588 (11)0.0184 (10)0.0064 (9)0.0085 (9)
C260.132 (2)0.0731 (16)0.0966 (17)0.0495 (15)0.0213 (15)0.0311 (13)
C270.153 (3)0.0816 (18)0.128 (2)0.0647 (19)0.038 (2)0.0285 (16)
C280.0561 (10)0.0433 (9)0.0516 (9)0.0084 (8)0.0111 (8)−0.0023 (7)
C290.1101 (18)0.0912 (16)0.0414 (10)−0.0064 (14)−0.0021 (11)−0.0033 (10)
C300.152 (3)0.098 (2)0.0674 (15)0.0107 (19)−0.0347 (16)0.0001 (14)
N10.0451 (7)0.0462 (7)0.0392 (7)0.0041 (6)0.0041 (5)0.0004 (6)
O10.0787 (9)0.0475 (7)0.0809 (9)0.0133 (7)0.0053 (7)0.0002 (7)
O20.0642 (8)0.0748 (9)0.0517 (7)0.0226 (7)0.0178 (6)−0.0014 (6)
O30.1778 (19)0.0924 (12)0.0589 (10)0.0551 (13)0.0223 (11)0.0235 (8)
O40.0987 (11)0.0608 (9)0.0703 (9)0.0373 (8)0.0117 (8)0.0129 (7)
O50.0693 (9)0.1000 (12)0.0707 (9)0.0266 (8)0.0279 (7)0.0055 (8)
O60.0627 (8)0.0694 (8)0.0434 (6)−0.0004 (6)0.0007 (6)−0.0052 (6)
S10.0533 (3)0.0490 (3)0.0476 (2)0.01314 (19)0.00624 (18)−0.00205 (18)

Geometric parameters (Å, °)

C2—C31.361 (2)C18—H180.93
C2—N11.417 (2)C19—C201.374 (3)
C2—C161.492 (2)C19—H190.93
C3—C41.445 (2)C20—C211.372 (3)
C3—C231.459 (2)C20—H200.93
C4—C51.396 (2)C21—C221.386 (3)
C4—C91.400 (2)C21—H210.93
C5—C61.392 (2)C22—H220.93
C5—N11.421 (2)C23—C241.332 (2)
C6—C71.375 (3)C23—H230.93
C6—H60.93C24—C251.490 (2)
C7—C81.382 (3)C24—C281.496 (2)
C7—H70.93C25—O31.193 (2)
C8—C91.381 (3)C25—O41.319 (2)
C8—H80.93C26—C271.452 (4)
C9—H90.93C26—O41.455 (2)
C10—C151.373 (3)C26—H26A0.97
C10—C111.378 (3)C26—H26B0.97
C10—S11.7548 (18)C27—H27A0.96
C11—C121.389 (3)C27—H27B0.96
C11—H110.93C27—H27C0.96
C12—C131.367 (4)C28—O51.193 (2)
C12—H120.93C28—O61.325 (2)
C13—C141.373 (4)C29—O61.460 (2)
C13—H130.93C29—C301.477 (4)
C14—C151.377 (3)C29—H29A0.97
C14—H140.93C29—H29B0.97
C15—H150.93C30—H30A0.96
C16—C171.512 (2)C30—H30B0.96
C16—H16A0.97C30—H30C0.96
C16—H16B0.97N1—S11.6766 (13)
C17—C181.386 (2)O1—S11.4199 (14)
C17—C221.386 (2)O2—S11.4216 (13)
C18—C191.381 (3)
C3—C2—N1108.43 (13)C21—C20—C19119.47 (19)
C3—C2—C16126.91 (14)C21—C20—H20120.3
N1—C2—C16124.67 (13)C19—C20—H20120.3
C2—C3—C4108.64 (14)C20—C21—C22120.78 (19)
C2—C3—C23122.64 (15)C20—C21—H21119.6
C4—C3—C23128.71 (14)C22—C21—H21119.6
C5—C4—C9119.58 (15)C21—C22—C17120.34 (16)
C5—C4—C3107.37 (14)C21—C22—H22119.8
C9—C4—C3132.97 (16)C17—C22—H22119.8
C6—C5—C4121.58 (15)C24—C23—C3128.67 (15)
C6—C5—N1130.93 (16)C24—C23—H23115.7
C4—C5—N1107.45 (13)C3—C23—H23115.7
C7—C6—C5117.64 (18)C23—C24—C25117.68 (16)
C7—C6—H6121.2C23—C24—C28123.27 (15)
C5—C6—H6121.2C25—C24—C28119.02 (15)
C6—C7—C8121.64 (18)O3—C25—O4123.89 (18)
C6—C7—H7119.2O3—C25—C24123.70 (18)
C8—C7—H7119.2O4—C25—C24112.41 (16)
C9—C8—C7121.09 (17)C27—C26—O4107.5 (2)
C9—C8—H8119.5C27—C26—H26A110.2
C7—C8—H8119.5O4—C26—H26A110.2
C8—C9—C4118.42 (17)C27—C26—H26B110.2
C8—C9—H9120.8O4—C26—H26B110.2
C4—C9—H9120.8H26A—C26—H26B108.5
C15—C10—C11121.37 (19)C26—C27—H27A109.5
C15—C10—S1119.07 (16)C26—C27—H27B109.5
C11—C10—S1119.56 (15)H27A—C27—H27B109.5
C10—C11—C12118.6 (2)C26—C27—H27C109.5
C10—C11—H11120.7H27A—C27—H27C109.5
C12—C11—H11120.7H27B—C27—H27C109.5
C13—C12—C11120.2 (2)O5—C28—O6124.78 (17)
C13—C12—H12119.9O5—C28—C24124.99 (17)
C11—C12—H12119.9O6—C28—C24110.20 (14)
C12—C13—C14120.5 (2)O6—C29—C30108.07 (19)
C12—C13—H13119.8O6—C29—H29A110.1
C14—C13—H13119.8C30—C29—H29A110.1
C13—C14—C15120.2 (2)O6—C29—H29B110.1
C13—C14—H14119.9C30—C29—H29B110.1
C15—C14—H14119.9H29A—C29—H29B108.4
C10—C15—C14119.1 (2)C29—C30—H30A109.5
C10—C15—H15120.4C29—C30—H30B109.5
C14—C15—H15120.4H30A—C30—H30B109.5
C2—C16—C17115.95 (12)C29—C30—H30C109.5
C2—C16—H16A108.3H30A—C30—H30C109.5
C17—C16—H16A108.3H30B—C30—H30C109.5
C2—C16—H16B108.3C2—N1—C5108.11 (12)
C17—C16—H16B108.3C2—N1—S1126.11 (11)
H16A—C16—H16B107.4C5—N1—S1123.82 (11)
C18—C17—C22118.08 (16)C25—O4—C26116.75 (17)
C18—C17—C16119.68 (14)C28—O6—C29117.36 (16)
C22—C17—C16122.21 (14)O1—S1—O2120.08 (9)
C19—C18—C17121.36 (17)O1—S1—N1105.43 (8)
C19—C18—H18119.3O2—S1—N1106.92 (7)
C17—C18—H18119.3O1—S1—C10108.90 (9)
C20—C19—C18119.95 (18)O2—S1—C10109.44 (9)
C20—C19—H19120.0N1—S1—C10104.98 (7)
C18—C19—H19120.0
N1—C2—C3—C40.01 (17)C3—C2—N1—S1−164.69 (11)
C16—C2—C3—C4179.63 (14)C16—C2—N1—S115.7 (2)
N1—C2—C3—C23−179.53 (13)C6—C5—N1—C2177.89 (16)
C16—C2—C3—C230.1 (2)C4—C5—N1—C20.36 (16)
C2—C3—C4—C50.22 (17)C6—C5—N1—S1−17.2 (2)
C23—C3—C4—C5179.72 (15)C4—C5—N1—S1165.27 (11)
C2—C3—C4—C9−176.51 (17)O4—C25—O3—O30.0 (3)
C23—C3—C4—C93.0 (3)C24—C25—O3—O30.0 (3)
C9—C4—C5—C6−0.9 (2)O3—C25—O4—C260.4 (4)
C3—C4—C5—C6−178.16 (14)O3—C25—O4—C260.4 (4)
C9—C4—C5—N1176.89 (14)C24—C25—O4—C26179.4 (2)
C3—C4—C5—N1−0.35 (17)C27—C26—O4—C25172.6 (2)
C4—C5—C6—C7−1.1 (2)O5—C28—O6—C294.8 (3)
N1—C5—C6—C7−178.33 (16)C24—C28—O6—C29−173.44 (16)
C5—C6—C7—C81.8 (3)C30—C29—O6—C28148.87 (19)
C6—C7—C8—C9−0.5 (3)O1—O1—S1—O20.00 (10)
C7—C8—C9—C4−1.5 (3)O1—O1—S1—O20.00 (10)
C5—C4—C9—C82.2 (2)O1—O1—S1—O20.00 (10)
C3—C4—C9—C8178.61 (16)O1—O1—S1—N10.00 (9)
C15—C10—C11—C12−2.5 (3)O1—O1—S1—C100.00 (10)
S1—C10—C11—C12178.27 (16)O2—O2—S1—O10.00 (6)
C10—C11—C12—C13−0.3 (3)O2—O2—S1—O10.00 (6)
C11—C12—C13—C142.7 (4)O2—O2—S1—O10.00 (6)
C12—C13—C14—C15−2.3 (5)O2—O2—S1—O10.00 (6)
C11—C10—C15—C142.9 (4)O2—O2—S1—O20.00 (4)
S1—C10—C15—C14−177.9 (2)O2—O2—S1—O20.00 (4)
C13—C14—C15—C10−0.5 (5)O2—O2—S1—N10.00 (2)
C3—C2—C16—C1795.29 (18)O2—O2—S1—N10.00 (2)
N1—C2—C16—C17−85.15 (19)O2—O2—S1—C100.00 (5)
C2—C16—C17—C22−40.0 (2)O2—O2—S1—C100.00 (5)
C2—C16—C17—C18142.20 (15)C2—N1—S1—O1−161.77 (13)
C22—C17—C18—C190.9 (3)C5—N1—S1—O136.07 (15)
C16—C17—C18—C19178.73 (16)C2—N1—S1—O1−161.77 (13)
C17—C18—C19—C20−0.2 (3)C5—N1—S1—O136.07 (15)
C18—C19—C20—C21−0.7 (3)C2—N1—S1—O2−32.90 (15)
C19—C20—C21—C221.0 (4)C5—N1—S1—O2164.94 (13)
C20—C21—C22—C17−0.3 (3)C2—N1—S1—O2−32.90 (15)
C18—C17—C22—C21−0.6 (3)C5—N1—S1—O2164.94 (13)
C16—C17—C22—C21−178.43 (18)C2—N1—S1—O2−32.90 (15)
C2—C3—C23—C24−135.86 (19)C5—N1—S1—O2164.94 (13)
C4—C3—C23—C2444.7 (3)C2—N1—S1—C1083.29 (14)
C3—C23—C24—C25178.68 (17)C5—N1—S1—C10−78.86 (14)
C3—C23—C24—C280.9 (3)C15—C10—S1—O1−41.3 (2)
C23—C24—C25—O32.2 (3)C11—C10—S1—O1137.98 (16)
C28—C24—C25—O3−179.9 (2)C15—C10—S1—O1−41.3 (2)
C23—C24—C25—O32.2 (3)C11—C10—S1—O1137.98 (16)
C28—C24—C25—O3−179.9 (2)C15—C10—S1—O2−174.34 (17)
C23—C24—C25—O4−176.75 (17)C11—C10—S1—O24.93 (18)
C28—C24—C25—O41.1 (3)C15—C10—S1—O2−174.34 (17)
C23—C24—C28—O5−126.2 (2)C11—C10—S1—O24.93 (18)
C25—C24—C28—O556.1 (3)C15—C10—S1—O2−174.34 (17)
C23—C24—C28—O652.0 (2)C11—C10—S1—O24.93 (18)
C25—C24—C28—O6−125.73 (17)C15—C10—S1—N171.20 (19)
C3—C2—N1—C5−0.23 (16)C11—C10—S1—N1−109.53 (15)
C16—C2—N1—C5−179.86 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.332.919 (2)121
C7—H7···O5i0.932.593.317 (2)135

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2729).

References

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