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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2530.
Published online 2009 September 26. doi:  10.1107/S1600536809038148
PMCID: PMC2970320

5-(4-Bromo­phen­yl)-2-(3,4-methyl­ene­dioxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran

Abstract

The title compound, C22H15BrO3S, crystallizes with four mol­ecules in the asymmetric unit. The 4-bromo­phenyl rings are rotated out of the benzofuran planes, with dihedral angles for the four mol­ecules of 20.8 (2), 17.8 (2), 23.5 (4) and 23.9 (4)°. The dihedral angles between the 3,4-methyl­ene­dioxy­phenyl ring and the benzofuran plane are 13.5 (2), 7.1 (2), 18.6 (3) and 14.2 (3)° in the four mol­ecules. The crystal structure is stabilized by weak nonclassical inter­molecular C—H(...)O hydrogen bonds. The crystal structure also exhibits inter­molecular aromatic π–π inter­actions between the benzene and furan rings and between the 4-bromo­phenyl and 3,4-methyl­enedioxy­phenyl rings from mol­ecules of the same type; the centroid–centroid distances are 3.92 (1) and 3.79 (1), 3.91 (1), 3.77 (1) and 3.77 (1), and 3.79 (1) and 3.75 (1)Å in the four mol­ecules.

Related literature

For the crystal structures of similar 3-methyl­sulfanyl-2-phenyl-1-benzofuran derivatives, see: Choi, Seo et al. (2006 [triangle]); Choi, Woo et al. (2006 [triangle]). For natural products of benzofuran ring systems, see: Akgul & Anil (2003 [triangle]); von Reuss & König (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2530-scheme1.jpg

Experimental

Crystal data

  • C22H15BrO3S
  • M r = 439.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2530-efi1.jpg
  • a = 12.3757 (8) Å
  • b = 16.067 (1) Å
  • c = 19.587 (1) Å
  • α = 84.078 (1)°
  • β = 88.6573 (9)°
  • γ = 68.0552 (9)°
  • V = 3592.7 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.43 mm−1
  • T = 173 K
  • 0.24 × 0.16 × 0.12 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.594, T max = 0.760
  • 26887 measured reflections
  • 12562 independent reflections
  • 6573 reflections with I > 2σ(I)
  • R int = 0.094

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.150
  • S = 1.06
  • 12562 reflections
  • 973 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.73 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; 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]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038148/pb2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038148/pb2008Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Molecules containing benzofuran skeleton constitute a major group of naturally-occurring compounds that are of considerable interest because of their biological activities (Akgul & Anil, 2003; von Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 3-methylsulfanyl-2-phenyl-1-benzofuran analogues (Choi, Seo et al., 2006; Choi, Woo et al., 2006), we report the crystal structure of the title compound, which has four unique molecules in the asymmetric unit (further marked as A, B, C and D) (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.018 (6) Å for A, 0.011 (6) Å for B, 0.010 (6) Å for C and 0.022 (6) Å for D, respectively, from the least-squares plane defined by the nine constituent atoms. The 4-bromophenyl rings are rotated out of the benzofuran planes, with dihedral angles of 20.8 (2), 6.7 (2), 23.5 (4) and 23.9 (4)° in the molecules A, B, C and D, respectively. The dihedral angles between the 3,4-methylenedioxyphenyl ring and the benzofuran plane are 13.5 (2), 7.1 (2), 18.6 (3) and 14.2 (3)° for the molecules A, B, C and D, respectively.

The molecular packing (Fig. 2) is stabilized by weak non-classical C–H···O hydrogen bonds; the first between the methylene H atom and the furan O atom, with a C12–H12A···O4, the second between the 4-bromophenyl H atom and the oxygen of the methylenedioxy group, with a C21–H21···O6i, the third between the methylene H atom and the furan O atom, with a C57–H57A···O10ii, the fourth between the 4-bromophenyl H atom and the oxygen of the methylenedioxy group, with a C65–H65···O11iii, the fifth between the methylene H atom and the furan O atom, with a C79–H79B···O7iv, respectively (Table 1).

The crystal packing (Fig. 3) exhibits aromatic π–π interactions between the benzene/the furan rings and the 4-bromophenyl/the 3,4-methylenedioxyphenyl rings from two A molecules [Cg1···Cg2v = 3.92 (1) Å, Cg3···Cg4v = 3.79 (1) Å] (Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2-C7 benzene ring, the C1/C2/C7/O1/C8 furan ring, the C16-C21 phenyl ring and the C9/C10/C11/C13/C14/C15 phenyl ring, respectively). The crystal packing (Fig. 3) also exhibits aromatic π–π interactions between the benzene/the furan rings and the 4-bromophenyl/the 3,4-methylenedioxyphenyl rings from two B molecules [Cg5···Cg6vi = 4.22 (1) Å, Cg7···Cg8vi = 3.91 (1) Å] (Cg5, Cg6, Cg7 and Cg8 are the centroids of the C24-C29 benzene ring, the C23/C24/C29/O4/C30 furan ring, the C38-C43 phenyl ring and the C31/C32/C33/C34/C36/C37 phenyl ring, respectively). The crystal packing (Fig. 4) exhibits aromatic π–π interactions between the benzene/the furan rings and the 4-bromophenyl/the 3,4-methylenedioxyphenyl rings from two C molecules [Cg9···Cg10vii = 3.77 (1) Å, Cg11···Cg12vii = 3.77 (1) Å] (Cg9, Cg10, Cg11 and Cg12 are the centroids of the C46-C51 benzene ring, the C45/C46/C51/O7/C52 furan ring, the C60-C65 phenyl ring and the C53/C54/C55/C56/C58/C59 phenyl ring, respectively). The crystal packing (Fig. 4) exhibits aromatic π–π interactions between the benzene/the furan rings and the 4-bromophenyl/the 3,4-methylenedioxyphenyl rings from two D molecules [Cg13···Cg14viii = 3.79 (1) Å, Cg15···Cg16viii = 3.75 (1) Å] (Cg13, Cg14, Cg15 and Cg16 are the centroids of the C68-C73 benzene ring, the C67/C68/C73/O10/C74 furan ring, the C82-C87 phenyl ring and the C75/C76/C77/C78/C80/C81 phenyl ring, respectively).

Experimental

Zinc chloride (409 mg, 3.0 mmol) was added to a stirred solution of 4'-bromo-[1,1'-biphenyl]-4-ol (747 mg, 3.0 mmol) and 2-chloro-2-methylsulfanyl-(3',4'-methylenedioxy)acetophenone (733 mg, 3.0 mmol) in dichloromethane (40 ml) at room temperature, and stirring was continued at the same temperature for 40 min. The reaction was quenched by the addition of water and the organic layer separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (carbon tetrachloride) to afford the title compound as a colorless solid [yield 62%, m.p. 456-457 K; Rf = 0.35 (carbon tetrachloride)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in tetrahydrofuran at room temperature. Spectroscopic analysis: 1H NMR ( CDCl3, 400 MHz) δ 2.38 (s, 3H), 6.04 (s, 2H), 6.94 (d, J = 8.6 Hz, 1H), 7.49 (d, J = 1.96 Hz, 1H), 7.50-7.54 (m, 3H), 7.56-7.59 (m, 2H), 7.81 (d, J = 1.56 Hz, 1H), 7.84-7.87 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 18.4, 101.4, 107.5, 107.9, 108.5, 111.4, 117.9, 121.2, 121.9, 124.1, 124.2, 129.1, 131.8, 131.9, 135.6, 140.4, 147.8, 148.4, 153.1, 156.1; EI-MS 438 [M+], 440 [M+2]

Refinement

All H atoms were geometrically positioned and refined using a riding model, with C–H = 0.95 Å for the aryl, 0.99 Å for the methylene, and 0.98 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
Fig. 2.
C-H···O hydrogen bonds (dotted lines) in the title compound. [Symmetry codes: (i) - x + 2, - y + 1, - z; (ii) - x + 1, - y + 1, - z + 1; (iii) x, y + 1, z; (iv) - x, - y + 1, - z + 1.]
Fig. 3.
π–π interaction (dotted lines) of molecule A and B in the title compound. Cg denotes the ring centroids. [Symmetry codes: (v) - x + 1, - y + 1, - z; (vi) - x + 2, - y + 1, - z + 1.]
Fig. 4.
π–π interaction (dotted lines) of molecule C and D in the title compound. Cg denotes the ring centroids. [Symmetry codes: (vii) - x, - y + 2, - z + 1; (viii) - x + 1, - y, - z + 2.]

Crystal data

C22H15BrO3SZ = 8
Mr = 439.31F(000) = 1776
Triclinic, P1Dx = 1.624 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3757 (8) ÅCell parameters from 3903 reflections
b = 16.067 (1) Åθ = 2.7–22.5°
c = 19.587 (1) ŵ = 2.42 mm1
α = 84.078 (1)°T = 173 K
β = 88.6573 (9)°Block, colorless
γ = 68.0552 (9)°0.24 × 0.16 × 0.12 mm
V = 3592.7 (4) Å3

Data collection

Bruker SMART CCD diffractometer12562 independent reflections
Radiation source: fine-focus sealed tube6573 reflections with I > 2σ(I)
graphiteRint = 0.094
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 1.1°
[var phi] and ω scansh = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)k = −19→19
Tmin = 0.594, Tmax = 0.760l = −23→23
26887 measured reflections

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)] = 0.061Hydrogen site location: difference Fourier map
wR(F2) = 0.150H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + 15.1547P] where P = (Fo2 + 2Fc2)/3
12562 reflections(Δ/σ)max < 0.001
973 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = −0.73 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br10.50384 (8)0.59231 (7)−0.45348 (5)0.0387 (3)
Br20.98757 (8)0.61526 (7)0.94332 (5)0.0377 (3)
Br30.08943 (8)0.90050 (7)0.95449 (5)0.0389 (3)
Br40.42898 (8)0.09093 (7)1.43447 (4)0.0381 (3)
S10.70263 (18)0.55819 (14)0.03947 (11)0.0276 (5)
O10.3585 (4)0.6481 (4)0.0621 (3)0.0292 (14)
O20.5119 (5)0.6257 (4)0.3701 (3)0.0353 (15)
O30.6786 (5)0.5523 (4)0.3112 (3)0.0407 (16)
C10.5504 (7)0.5988 (5)0.0350 (4)0.0208 (19)
C20.4815 (7)0.6134 (5)−0.0271 (4)0.023 (2)
C30.5089 (7)0.6079 (5)−0.0969 (4)0.025 (2)
H30.58760.5893−0.11110.030*
C40.4193 (7)0.6301 (5)−0.1448 (4)0.025 (2)
C50.3025 (7)0.6563 (5)−0.1211 (4)0.029 (2)
H50.24150.6683−0.15380.035*
C60.2738 (7)0.6649 (5)−0.0528 (4)0.029 (2)
H60.19540.6845−0.03790.035*
C70.3664 (7)0.6433 (6)−0.0078 (4)0.029 (2)
C80.4726 (7)0.6201 (5)0.0877 (4)0.027 (2)
C90.4809 (7)0.6233 (5)0.1615 (4)0.024 (2)
C100.5869 (7)0.5820 (6)0.1977 (4)0.027 (2)
H100.65720.55140.17500.032*
C110.5854 (7)0.5875 (6)0.2657 (5)0.030 (2)
C120.6349 (7)0.5768 (7)0.3773 (5)0.043 (3)
H12A0.67290.61480.39500.051*
H12B0.65130.52210.41000.051*
C130.4852 (7)0.6319 (5)0.3001 (4)0.0230 (19)
C140.3804 (8)0.6730 (6)0.2674 (4)0.032 (2)
H140.31200.70440.29130.038*
C150.3779 (7)0.6670 (6)0.1973 (4)0.032 (2)
H150.30560.69280.17290.039*
C160.4390 (7)0.6245 (5)−0.2201 (4)0.0224 (19)
C170.3524 (7)0.6734 (6)−0.2691 (4)0.028 (2)
H170.27940.7136−0.25470.034*
C180.3712 (7)0.6640 (6)−0.3376 (5)0.034 (2)
H180.31010.6952−0.37010.040*
C190.4777 (7)0.6098 (6)−0.3593 (4)0.031 (2)
C200.5679 (7)0.5649 (5)−0.3125 (4)0.028 (2)
H200.64300.5297−0.32780.034*
C210.5474 (7)0.5717 (5)−0.2431 (4)0.028 (2)
H210.60860.5397−0.21080.033*
C220.7251 (7)0.6617 (6)0.0456 (5)0.040 (2)
H22A0.80880.64910.04840.061*
H22B0.68730.68860.08690.061*
H22C0.69130.70380.00490.061*
S21.19277 (18)0.55578 (15)0.45491 (11)0.0297 (5)
O40.8489 (4)0.6558 (4)0.4222 (3)0.0278 (14)
O51.0111 (5)0.6096 (4)0.1168 (3)0.0326 (15)
O61.1794 (5)0.5482 (4)0.1839 (3)0.0402 (16)
C231.0399 (7)0.6017 (5)0.4537 (4)0.0224 (19)
C240.9693 (7)0.6214 (5)0.5151 (4)0.0232 (19)
C250.9937 (7)0.6146 (5)0.5844 (4)0.028 (2)
H251.07220.59320.60040.034*
C260.9024 (7)0.6393 (5)0.6310 (4)0.0235 (19)
C270.7873 (7)0.6691 (6)0.6048 (4)0.031 (2)
H270.72500.68410.63620.037*
C280.7610 (7)0.6775 (6)0.5356 (4)0.032 (2)
H280.68300.69880.51880.038*
C290.8547 (7)0.6531 (5)0.4927 (4)0.026 (2)
C300.9640 (7)0.6234 (5)0.4002 (4)0.026 (2)
C310.9733 (7)0.6229 (5)0.3258 (4)0.025 (2)
C320.8737 (7)0.6596 (6)0.2840 (5)0.031 (2)
H320.80020.68620.30480.038*
C330.8777 (7)0.6586 (6)0.2127 (4)0.028 (2)
H330.80890.68300.18490.034*
C340.9845 (7)0.6211 (5)0.1851 (4)0.026 (2)
C351.1354 (7)0.5715 (7)0.1157 (5)0.045 (3)
H35A1.16150.51710.09060.054*
H35B1.16540.61570.09180.054*
C361.0832 (7)0.5839 (5)0.2255 (4)0.026 (2)
C371.0819 (7)0.5830 (5)0.2946 (4)0.027 (2)
H371.15180.55630.32120.032*
C380.9236 (7)0.6350 (5)0.7062 (4)0.0220 (19)
C391.0321 (7)0.5840 (6)0.7365 (4)0.029 (2)
H391.09430.55210.70830.034*
C401.0520 (7)0.5785 (5)0.8059 (4)0.029 (2)
H401.12690.54320.82510.035*
C410.9627 (7)0.6243 (5)0.8475 (4)0.025 (2)
C420.8536 (7)0.6781 (6)0.8188 (4)0.034 (2)
H420.79200.71090.84690.041*
C430.8366 (7)0.6828 (6)0.7496 (4)0.032 (2)
H430.76250.72020.73030.038*
C441.2242 (8)0.6572 (6)0.4457 (6)0.054 (3)
H44A1.30880.64120.44560.082*
H44B1.19070.69280.48410.082*
H44C1.19030.69280.40240.082*
S30.26939 (18)0.93222 (15)0.45490 (11)0.0268 (5)
O7−0.0074 (4)0.8653 (3)0.4399 (3)0.0220 (13)
O80.1301 (5)0.8741 (4)0.1293 (3)0.0356 (15)
O90.2265 (5)0.9503 (4)0.1814 (3)0.0399 (16)
C450.1473 (6)0.9008 (5)0.4627 (4)0.0184 (18)
C460.0944 (7)0.8877 (5)0.5277 (4)0.0205 (19)
C470.1165 (7)0.8896 (5)0.5959 (4)0.024 (2)
H470.18080.90360.60890.028*
C480.0439 (6)0.8710 (5)0.6462 (4)0.0199 (18)
C49−0.0528 (6)0.8520 (5)0.6248 (4)0.0212 (19)
H49−0.10380.84130.65850.025*
C50−0.0743 (7)0.8485 (5)0.5572 (4)0.024 (2)
H50−0.13860.83480.54370.029*
C510.0002 (7)0.8655 (5)0.5095 (4)0.025 (2)
C520.0862 (6)0.8874 (5)0.4125 (4)0.0212 (19)
C530.0951 (6)0.8823 (5)0.3379 (4)0.0206 (19)
C540.0372 (7)0.8371 (5)0.3053 (4)0.025 (2)
H54−0.00830.81000.33200.030*
C550.0443 (7)0.8308 (6)0.2350 (4)0.029 (2)
H550.00410.80060.21310.034*
C560.1115 (7)0.8699 (5)0.1987 (4)0.024 (2)
C570.2121 (8)0.9185 (8)0.1186 (4)0.050 (3)
H57A0.28780.87570.10400.060*
H57B0.18250.96960.08230.060*
C580.1688 (7)0.9152 (5)0.2306 (4)0.0226 (19)
C590.1631 (7)0.9225 (5)0.2981 (4)0.026 (2)
H590.20350.95370.31870.031*
C600.0611 (6)0.8750 (5)0.7200 (4)0.0212 (19)
C610.0161 (7)0.8278 (5)0.7701 (4)0.026 (2)
H61−0.02170.79050.75620.032*
C620.0257 (8)0.8349 (6)0.8384 (4)0.035 (2)
H62−0.00730.80390.87130.042*
C630.0827 (7)0.8866 (6)0.8599 (4)0.027 (2)
C640.1315 (7)0.9312 (6)0.8122 (4)0.028 (2)
H640.17260.96570.82690.034*
C650.1204 (7)0.9255 (5)0.7438 (4)0.026 (2)
H650.15400.95670.71150.031*
C660.3844 (7)0.8217 (6)0.4697 (5)0.045 (3)
H66A0.46030.82780.46690.068*
H66B0.37900.78380.43470.068*
H66C0.37610.79370.51530.068*
S40.23241 (18)0.06678 (15)0.94641 (11)0.0272 (5)
O100.5046 (4)0.1399 (4)0.9101 (3)0.0260 (13)
O110.2639 (5)0.0615 (4)0.6721 (3)0.0390 (16)
O120.3684 (5)0.1314 (4)0.6048 (3)0.0318 (15)
C670.3528 (6)0.1008 (5)0.9437 (4)0.0207 (19)
C680.4092 (7)0.1112 (5)1.0048 (4)0.024 (2)
C690.3869 (7)0.1089 (5)1.0745 (4)0.0231 (19)
H690.32280.09491.09200.028*
C700.4605 (7)0.1275 (5)1.1188 (4)0.0232 (19)
C710.5530 (7)0.1510 (5)1.0910 (4)0.025 (2)
H710.60230.16381.12120.030*
C720.5741 (6)0.1559 (5)1.0216 (4)0.027 (2)
H720.63640.17181.00340.032*
C730.4992 (6)0.1362 (5)0.9795 (4)0.0209 (19)
C740.4106 (7)0.1194 (5)0.8889 (4)0.024 (2)
C750.4005 (7)0.1234 (5)0.8139 (4)0.0231 (19)
C760.4619 (7)0.1663 (6)0.7723 (4)0.031 (2)
H760.50870.19190.79340.037*
C770.4563 (7)0.1724 (5)0.7009 (4)0.029 (2)
H770.49980.20010.67280.035*
C780.3859 (7)0.1370 (5)0.6735 (4)0.025 (2)
C790.2758 (8)0.0978 (7)0.6031 (4)0.041 (2)
H79A0.29500.05020.57150.049*
H79B0.20220.14710.58710.049*
C800.3247 (7)0.0941 (5)0.7139 (4)0.026 (2)
C810.3293 (7)0.0861 (5)0.7832 (4)0.028 (2)
H810.28640.05680.81010.033*
C820.4455 (6)0.1239 (5)1.1945 (4)0.0208 (19)
C830.4896 (7)0.1713 (6)1.2348 (4)0.030 (2)
H830.52610.20931.21290.036*
C840.4817 (7)0.1646 (6)1.3051 (4)0.033 (2)
H840.51080.19831.33140.039*
C850.4309 (7)0.1082 (6)1.3366 (4)0.027 (2)
C860.3821 (7)0.0630 (5)1.2990 (4)0.028 (2)
H860.34410.02651.32140.034*
C870.3887 (7)0.0711 (5)1.2290 (4)0.026 (2)
H870.35420.04041.20320.031*
C880.1155 (7)0.1741 (6)0.9358 (5)0.048 (3)
H88A0.04110.16550.93630.072*
H88B0.12310.20650.89190.072*
H88C0.11800.20920.97340.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0384 (6)0.0440 (6)0.0303 (5)−0.0108 (5)0.0001 (4)−0.0061 (5)
Br20.0373 (6)0.0498 (6)0.0261 (5)−0.0166 (5)0.0002 (4)−0.0027 (5)
Br30.0489 (6)0.0550 (7)0.0248 (5)−0.0313 (5)0.0044 (5)−0.0127 (5)
Br40.0449 (6)0.0502 (6)0.0241 (5)−0.0239 (5)−0.0008 (4)−0.0008 (4)
S10.0227 (12)0.0264 (13)0.0307 (13)−0.0048 (10)0.0014 (10)−0.0068 (10)
O10.023 (3)0.042 (4)0.028 (3)−0.018 (3)0.003 (3)−0.006 (3)
O20.037 (4)0.046 (4)0.025 (3)−0.017 (3)0.002 (3)−0.007 (3)
O30.034 (4)0.061 (5)0.028 (4)−0.018 (3)0.000 (3)−0.003 (3)
C10.024 (5)0.016 (4)0.026 (5)−0.010 (4)−0.001 (4)−0.004 (4)
C20.030 (5)0.014 (5)0.026 (5)−0.007 (4)0.004 (4)−0.007 (4)
C30.023 (5)0.015 (5)0.032 (5)−0.001 (4)0.006 (4)−0.006 (4)
C40.026 (5)0.020 (5)0.030 (5)−0.009 (4)0.003 (4)−0.004 (4)
C50.024 (5)0.030 (5)0.036 (6)−0.012 (4)0.000 (4)−0.008 (4)
C60.017 (5)0.028 (5)0.045 (6)−0.010 (4)0.000 (4)−0.008 (4)
C70.015 (5)0.035 (5)0.039 (6)−0.010 (4)0.009 (4)−0.016 (4)
C80.019 (5)0.027 (5)0.037 (6)−0.010 (4)−0.004 (4)−0.009 (4)
C90.025 (5)0.021 (5)0.027 (5)−0.008 (4)0.000 (4)−0.003 (4)
C100.021 (5)0.033 (5)0.030 (5)−0.013 (4)0.010 (4)−0.011 (4)
C110.022 (5)0.026 (5)0.043 (6)−0.012 (4)−0.005 (4)−0.002 (4)
C120.028 (5)0.067 (7)0.034 (6)−0.021 (5)0.001 (5)−0.004 (5)
C130.026 (5)0.022 (5)0.023 (5)−0.010 (4)0.001 (4)−0.004 (4)
C140.035 (5)0.038 (6)0.026 (5)−0.016 (5)0.008 (4)−0.009 (4)
C150.029 (5)0.028 (5)0.036 (6)−0.007 (4)0.000 (4)−0.005 (4)
C160.023 (5)0.019 (5)0.030 (5)−0.013 (4)−0.002 (4)−0.005 (4)
C170.024 (5)0.031 (5)0.028 (5)−0.006 (4)−0.005 (4)−0.007 (4)
C180.030 (5)0.032 (6)0.034 (6)−0.006 (4)−0.001 (4)−0.007 (4)
C190.031 (5)0.027 (5)0.034 (5)−0.010 (4)0.003 (4)−0.005 (4)
C200.023 (5)0.027 (5)0.036 (5)−0.011 (4)0.008 (4)−0.006 (4)
C210.024 (5)0.029 (5)0.026 (5)−0.005 (4)−0.007 (4)0.002 (4)
C220.029 (5)0.040 (6)0.065 (7)−0.025 (5)0.008 (5)−0.016 (5)
S20.0232 (12)0.0299 (13)0.0319 (13)−0.0052 (10)−0.0029 (10)−0.0023 (10)
O40.019 (3)0.039 (4)0.030 (3)−0.016 (3)0.005 (3)−0.007 (3)
O50.025 (3)0.039 (4)0.026 (3)−0.004 (3)0.001 (3)−0.001 (3)
O60.025 (3)0.056 (4)0.027 (4)0.000 (3)0.000 (3)−0.010 (3)
C230.022 (5)0.021 (5)0.026 (5)−0.009 (4)−0.005 (4)−0.004 (4)
C240.028 (5)0.021 (5)0.024 (5)−0.011 (4)0.001 (4)−0.007 (4)
C250.019 (5)0.025 (5)0.045 (6)−0.013 (4)−0.002 (4)−0.001 (4)
C260.029 (5)0.010 (4)0.031 (5)−0.007 (4)0.003 (4)−0.003 (4)
C270.026 (5)0.045 (6)0.029 (5)−0.020 (4)0.003 (4)−0.009 (4)
C280.018 (5)0.048 (6)0.035 (6)−0.020 (4)0.006 (4)−0.006 (5)
C290.031 (5)0.027 (5)0.024 (5)−0.017 (4)−0.001 (4)−0.003 (4)
C300.028 (5)0.021 (5)0.031 (5)−0.010 (4)0.008 (4)−0.008 (4)
C310.027 (5)0.019 (5)0.029 (5)−0.009 (4)0.002 (4)0.000 (4)
C320.018 (5)0.030 (5)0.043 (6)−0.006 (4)0.001 (4)−0.001 (4)
C330.016 (5)0.040 (6)0.024 (5)−0.005 (4)−0.007 (4)0.001 (4)
C340.030 (5)0.030 (5)0.016 (5)−0.009 (4)−0.001 (4)−0.008 (4)
C350.028 (5)0.069 (7)0.035 (6)−0.014 (5)0.008 (5)−0.006 (5)
C360.022 (5)0.026 (5)0.026 (5)−0.005 (4)0.001 (4)0.001 (4)
C370.018 (5)0.028 (5)0.031 (5)−0.004 (4)−0.005 (4)−0.004 (4)
C380.029 (5)0.020 (5)0.021 (5)−0.015 (4)−0.005 (4)0.004 (4)
C390.038 (5)0.028 (5)0.024 (5)−0.014 (4)0.008 (4)−0.008 (4)
C400.024 (5)0.026 (5)0.034 (5)−0.007 (4)−0.004 (4)0.004 (4)
C410.028 (5)0.024 (5)0.029 (5)−0.014 (4)0.007 (4)−0.005 (4)
C420.028 (5)0.037 (6)0.032 (6)−0.007 (4)0.002 (4)−0.001 (4)
C430.022 (5)0.039 (6)0.029 (5)−0.007 (4)−0.002 (4)0.004 (4)
C440.030 (6)0.042 (7)0.092 (9)−0.017 (5)−0.017 (6)0.011 (6)
S30.0297 (12)0.0319 (13)0.0274 (12)−0.0214 (11)0.0014 (10)−0.0031 (10)
O70.017 (3)0.031 (3)0.020 (3)−0.013 (3)0.000 (2)−0.001 (3)
O80.040 (4)0.056 (4)0.018 (3)−0.024 (3)0.010 (3)−0.012 (3)
O90.048 (4)0.065 (5)0.023 (3)−0.039 (4)0.006 (3)−0.008 (3)
C450.022 (4)0.017 (4)0.017 (4)−0.009 (4)0.001 (4)−0.002 (3)
C460.021 (5)0.018 (5)0.023 (5)−0.008 (4)−0.004 (4)−0.002 (4)
C470.017 (4)0.023 (5)0.034 (5)−0.011 (4)−0.001 (4)−0.008 (4)
C480.019 (4)0.013 (4)0.028 (5)−0.005 (4)−0.003 (4)0.000 (4)
C490.016 (4)0.022 (5)0.030 (5)−0.013 (4)0.005 (4)0.001 (4)
C500.021 (5)0.032 (5)0.025 (5)−0.016 (4)0.002 (4)−0.005 (4)
C510.021 (5)0.028 (5)0.021 (5)−0.005 (4)0.003 (4)−0.004 (4)
C520.016 (4)0.017 (5)0.028 (5)−0.005 (4)0.011 (4)0.005 (4)
C530.020 (4)0.021 (5)0.023 (5)−0.009 (4)0.004 (4)−0.005 (4)
C540.023 (5)0.030 (5)0.028 (5)−0.016 (4)0.001 (4)−0.005 (4)
C550.031 (5)0.031 (5)0.029 (5)−0.016 (4)−0.004 (4)−0.006 (4)
C560.031 (5)0.021 (5)0.019 (5)−0.008 (4)−0.001 (4)−0.002 (4)
C570.045 (6)0.097 (9)0.022 (5)−0.040 (6)0.016 (5)−0.019 (5)
C580.023 (5)0.027 (5)0.020 (5)−0.012 (4)0.000 (4)−0.001 (4)
C590.021 (5)0.031 (5)0.027 (5)−0.011 (4)−0.004 (4)−0.004 (4)
C600.019 (4)0.015 (5)0.029 (5)−0.007 (4)0.006 (4)0.001 (4)
C610.027 (5)0.034 (5)0.028 (5)−0.022 (4)−0.005 (4)−0.004 (4)
C620.049 (6)0.042 (6)0.025 (5)−0.031 (5)−0.002 (5)0.005 (4)
C630.034 (5)0.030 (5)0.020 (5)−0.015 (4)−0.001 (4)−0.007 (4)
C640.028 (5)0.036 (6)0.028 (5)−0.020 (4)−0.005 (4)−0.004 (4)
C650.027 (5)0.028 (5)0.028 (5)−0.016 (4)0.006 (4)−0.005 (4)
C660.017 (5)0.044 (6)0.076 (8)−0.012 (5)0.008 (5)−0.013 (5)
S40.0304 (12)0.0308 (13)0.0290 (12)−0.0212 (11)0.0007 (10)−0.0028 (10)
O100.028 (3)0.033 (4)0.025 (3)−0.019 (3)0.004 (3)−0.009 (3)
O110.049 (4)0.061 (5)0.022 (3)−0.038 (4)−0.003 (3)−0.002 (3)
O120.034 (4)0.051 (4)0.018 (3)−0.026 (3)−0.001 (3)−0.003 (3)
C670.020 (4)0.018 (5)0.021 (5)−0.004 (4)−0.004 (4)−0.003 (4)
C680.021 (5)0.016 (5)0.034 (5)−0.006 (4)0.003 (4)0.001 (4)
C690.021 (5)0.016 (5)0.031 (5)−0.006 (4)0.004 (4)0.000 (4)
C700.026 (5)0.016 (5)0.026 (5)−0.006 (4)−0.006 (4)−0.001 (4)
C710.026 (5)0.025 (5)0.031 (5)−0.014 (4)0.002 (4)−0.013 (4)
C720.012 (4)0.034 (5)0.037 (5)−0.010 (4)0.005 (4)−0.004 (4)
C730.016 (4)0.024 (5)0.023 (5)−0.007 (4)−0.004 (4)−0.001 (4)
C740.017 (4)0.028 (5)0.032 (5)−0.012 (4)−0.003 (4)−0.005 (4)
C750.022 (5)0.022 (5)0.026 (5)−0.010 (4)0.000 (4)−0.004 (4)
C760.033 (5)0.030 (5)0.034 (5)−0.017 (4)0.007 (4)−0.010 (4)
C770.040 (5)0.032 (5)0.027 (5)−0.026 (5)0.011 (4)−0.006 (4)
C780.024 (5)0.030 (5)0.021 (5)−0.010 (4)0.005 (4)−0.007 (4)
C790.044 (6)0.068 (7)0.027 (5)−0.036 (6)0.002 (5)−0.010 (5)
C800.024 (5)0.021 (5)0.035 (5)−0.011 (4)0.001 (4)−0.009 (4)
C810.022 (5)0.030 (5)0.033 (5)−0.011 (4)−0.002 (4)−0.006 (4)
C820.018 (4)0.016 (5)0.027 (5)−0.004 (4)−0.004 (4)−0.004 (4)
C830.040 (5)0.028 (5)0.025 (5)−0.016 (4)0.004 (4)−0.005 (4)
C840.046 (6)0.032 (6)0.032 (5)−0.029 (5)0.001 (4)−0.003 (4)
C850.033 (5)0.030 (5)0.024 (5)−0.019 (4)0.002 (4)−0.001 (4)
C860.034 (5)0.026 (5)0.028 (5)−0.017 (4)0.001 (4)0.003 (4)
C870.033 (5)0.019 (5)0.026 (5)−0.009 (4)−0.002 (4)−0.006 (4)
C880.023 (5)0.040 (6)0.078 (8)−0.011 (5)−0.016 (5)0.008 (6)

Geometric parameters (Å, °)

Br1—C191.897 (9)C44—H44B0.9800
Br2—C411.890 (8)C44—H44C0.9800
Br3—C631.895 (8)S3—C451.763 (8)
Br4—C851.909 (8)S3—C661.813 (9)
S1—C11.749 (8)O7—C511.370 (9)
S1—C221.802 (8)O7—C521.412 (8)
O1—C71.378 (9)O8—C561.373 (9)
O1—C81.399 (9)O8—C571.443 (10)
O2—C131.403 (9)O9—C581.383 (9)
O2—C121.431 (9)O9—C571.419 (10)
O3—C111.379 (9)C45—C521.337 (10)
O3—C121.428 (10)C45—C461.450 (10)
C1—C81.376 (10)C46—C471.376 (10)
C1—C21.450 (10)C46—C511.403 (10)
C2—C71.379 (10)C47—C481.401 (10)
C2—C31.405 (11)C47—H470.9500
C3—C41.386 (11)C48—C491.423 (10)
C3—H30.9500C48—C601.477 (11)
C4—C51.427 (10)C49—C501.367 (10)
C4—C161.496 (11)C49—H490.9500
C5—C61.383 (11)C50—C511.377 (10)
C5—H50.9500C50—H500.9500
C6—C71.378 (11)C52—C531.471 (10)
C6—H60.9500C53—C541.396 (10)
C8—C91.458 (11)C53—C591.417 (10)
C9—C101.400 (11)C54—C551.389 (11)
C9—C151.414 (11)C54—H540.9500
C10—C111.343 (11)C55—C561.363 (11)
C10—H100.9500C55—H550.9500
C11—C131.379 (11)C56—C581.386 (10)
C12—H12A0.9900C57—H57A0.9900
C12—H12B0.9900C57—H57B0.9900
C13—C141.357 (11)C58—C591.337 (10)
C14—C151.388 (11)C59—H590.9500
C14—H140.9500C60—C651.398 (10)
C15—H150.9500C60—C611.409 (10)
C16—C211.387 (10)C61—C621.366 (11)
C16—C171.396 (10)C61—H610.9500
C17—C181.371 (11)C62—C631.374 (11)
C17—H170.9500C62—H620.9500
C18—C191.366 (11)C63—C641.383 (11)
C18—H180.9500C64—C651.365 (11)
C19—C201.384 (11)C64—H640.9500
C20—C211.385 (11)C65—H650.9500
C20—H200.9500C66—H66A0.9800
C21—H210.9500C66—H66B0.9800
C22—H22A0.9800C66—H66C0.9800
C22—H22B0.9800S4—C671.766 (8)
C22—H22C0.9800S4—C881.785 (9)
S2—C231.755 (8)O10—C731.356 (9)
S2—C441.803 (9)O10—C741.403 (8)
O4—C291.379 (9)O11—C801.386 (9)
O4—C301.396 (9)O11—C791.443 (9)
O5—C341.385 (9)O12—C781.385 (9)
O5—C351.428 (9)O12—C791.439 (9)
O6—C361.396 (9)C67—C741.346 (10)
O6—C351.414 (10)C67—C681.455 (11)
C23—C301.351 (11)C68—C691.387 (11)
C23—C241.461 (10)C68—C731.383 (10)
C24—C251.382 (11)C69—C701.402 (10)
C24—C291.381 (11)C69—H690.9500
C25—C261.398 (10)C70—C711.414 (10)
C25—H250.9500C70—C821.489 (11)
C26—C271.413 (11)C71—C721.377 (11)
C26—C381.493 (11)C71—H710.9500
C27—C281.382 (11)C72—C731.396 (10)
C27—H270.9500C72—H720.9500
C28—C291.373 (10)C74—C751.470 (11)
C28—H280.9500C75—C761.401 (11)
C30—C311.460 (11)C75—C811.410 (10)
C31—C321.394 (11)C76—C771.394 (11)
C31—C371.410 (10)C76—H760.9500
C32—C331.398 (11)C77—C781.351 (10)
C32—H320.9500C77—H770.9500
C33—C341.357 (10)C78—C801.387 (11)
C33—H330.9500C79—H79A0.9900
C34—C361.370 (10)C79—H79B0.9900
C35—H35A0.9900C80—C811.351 (11)
C35—H35B0.9900C81—H810.9500
C36—C371.351 (11)C82—C871.405 (10)
C37—H370.9500C82—C831.398 (10)
C38—C431.395 (11)C83—C841.375 (11)
C38—C391.394 (11)C83—H830.9500
C39—C401.376 (11)C84—C851.374 (11)
C39—H390.9500C84—H840.9500
C40—C411.379 (11)C85—C861.377 (10)
C40—H400.9500C86—C871.366 (11)
C41—C421.397 (11)C86—H860.9500
C42—C431.365 (11)C87—H870.9500
C42—H420.9500C88—H88A0.9800
C43—H430.9500C88—H88B0.9800
C44—H44A0.9800C88—H88C0.9800
C1—S1—C22100.3 (4)C45—S3—C6699.4 (4)
C7—O1—C8106.8 (6)C51—O7—C52105.6 (6)
C13—O2—C12106.1 (6)C56—O8—C57105.2 (6)
C11—O3—C12107.0 (6)C58—O9—C57106.5 (6)
C8—C1—C2106.3 (7)C52—C45—C46108.5 (7)
C8—C1—S1128.4 (6)C52—C45—S3127.8 (6)
C2—C1—S1125.3 (6)C46—C45—S3123.6 (6)
C7—C2—C3119.6 (8)C47—C46—C51119.3 (7)
C7—C2—C1106.6 (7)C47—C46—C45136.6 (7)
C3—C2—C1133.7 (8)C51—C46—C45104.0 (7)
C4—C3—C2119.0 (7)C46—C47—C48119.8 (7)
C4—C3—H3120.5C46—C47—H47120.1
C2—C3—H3120.5C48—C47—H47120.1
C3—C4—C5118.6 (7)C47—C48—C49118.6 (7)
C3—C4—C16123.3 (7)C47—C48—C60122.2 (7)
C5—C4—C16118.1 (7)C49—C48—C60119.1 (7)
C6—C5—C4123.0 (8)C50—C49—C48122.0 (7)
C6—C5—H5118.5C50—C49—H49119.0
C4—C5—H5118.5C48—C49—H49119.0
C7—C6—C5115.6 (8)C49—C50—C51117.7 (7)
C7—C6—H6122.2C49—C50—H50121.2
C5—C6—H6122.2C51—C50—H50121.2
C6—C7—O1125.7 (7)O7—C51—C50126.1 (7)
C6—C7—C2124.0 (8)O7—C51—C46111.4 (7)
O1—C7—C2110.3 (7)C50—C51—C46122.6 (7)
C1—C8—O1110.0 (7)C45—C52—O7110.4 (7)
C1—C8—C9135.6 (7)C45—C52—C53137.6 (7)
O1—C8—C9114.3 (7)O7—C52—C53111.8 (7)
C10—C9—C15119.6 (7)C54—C53—C59119.0 (7)
C10—C9—C8121.7 (7)C54—C53—C52120.5 (7)
C15—C9—C8118.7 (7)C59—C53—C52120.5 (7)
C11—C10—C9117.3 (8)C55—C54—C53121.8 (8)
C11—C10—H10121.3C55—C54—H54119.1
C9—C10—H10121.3C53—C54—H54119.1
C10—C11—C13122.9 (8)C56—C55—C54117.3 (8)
C10—C11—O3127.3 (8)C56—C55—H55121.4
C13—C11—O3109.8 (7)C54—C55—H55121.4
O3—C12—O2107.8 (7)C55—C56—O8128.0 (7)
O3—C12—H12A110.2C55—C56—C58121.3 (7)
O2—C12—H12A110.2O8—C56—C58110.6 (7)
O3—C12—H12B110.2O9—C57—O8108.1 (6)
O2—C12—H12B110.2O9—C57—H57A110.1
H12A—C12—H12B108.5O8—C57—H57A110.1
C14—C13—C11122.0 (8)O9—C57—H57B110.1
C14—C13—O2128.7 (7)O8—C57—H57B110.1
C11—C13—O2109.3 (7)H57A—C57—H57B108.4
C13—C14—C15116.9 (8)C59—C58—O9128.5 (7)
C13—C14—H14121.6C59—C58—C56122.7 (8)
C15—C14—H14121.6O9—C58—C56108.9 (7)
C14—C15—C9121.3 (8)C58—C59—C53117.9 (8)
C14—C15—H15119.4C58—C59—H59121.0
C9—C15—H15119.4C53—C59—H59121.0
C21—C16—C17118.1 (8)C65—C60—C61116.7 (7)
C21—C16—C4119.8 (7)C65—C60—C48122.7 (7)
C17—C16—C4122.1 (7)C61—C60—C48120.6 (7)
C18—C17—C16120.8 (8)C62—C61—C60121.2 (7)
C18—C17—H17119.6C62—C61—H61119.4
C16—C17—H17119.6C60—C61—H61119.4
C17—C18—C19120.2 (8)C61—C62—C63120.5 (8)
C17—C18—H18119.9C61—C62—H62119.8
C19—C18—H18119.9C63—C62—H62119.8
C18—C19—C20120.4 (8)C62—C63—C64119.8 (7)
C18—C19—Br1120.8 (7)C62—C63—Br3120.2 (6)
C20—C19—Br1118.7 (6)C64—C63—Br3120.0 (6)
C21—C20—C19119.3 (8)C65—C64—C63119.9 (8)
C21—C20—H20120.4C65—C64—H64120.1
C19—C20—H20120.4C63—C64—H64120.1
C20—C21—C16121.0 (8)C64—C65—C60121.9 (8)
C20—C21—H21119.5C64—C65—H65119.1
C16—C21—H21119.5C60—C65—H65119.1
S1—C22—H22A109.5S3—C66—H66A109.5
S1—C22—H22B109.5S3—C66—H66B109.5
H22A—C22—H22B109.5H66A—C66—H66B109.5
S1—C22—H22C109.5S3—C66—H66C109.5
H22A—C22—H22C109.5H66A—C66—H66C109.5
H22B—C22—H22C109.5H66B—C66—H66C109.5
C23—S2—C44100.7 (4)C67—S4—C88100.3 (4)
C29—O4—C30106.1 (6)C73—O10—C74105.6 (6)
C34—O5—C35104.7 (6)C80—O11—C79105.7 (6)
C36—O6—C35105.6 (6)C78—O12—C79105.6 (6)
C30—C23—C24106.2 (7)C74—C67—C68107.5 (7)
C30—C23—S2129.9 (6)C74—C67—S4129.2 (6)
C24—C23—S2123.9 (6)C68—C67—S4123.3 (6)
C25—C24—C29119.4 (8)C69—C68—C73120.0 (8)
C25—C24—C23134.7 (8)C69—C68—C67135.7 (8)
C29—C24—C23106.0 (7)C73—C68—C67104.1 (7)
C24—C25—C26119.8 (8)C68—C69—C70119.0 (7)
C24—C25—H25120.1C68—C69—H69120.5
C26—C25—H25120.1C70—C69—H69120.5
C25—C26—C27117.9 (8)C69—C70—C71119.2 (7)
C25—C26—C38122.1 (7)C69—C70—C82122.7 (7)
C27—C26—C38120.0 (7)C71—C70—C82118.1 (7)
C28—C27—C26123.2 (8)C72—C71—C70122.4 (7)
C28—C27—H27118.4C72—C71—H71118.8
C26—C27—H27118.4C70—C71—H71118.8
C27—C28—C29115.9 (8)C71—C72—C73116.5 (7)
C27—C28—H28122.1C71—C72—H72121.8
C29—C28—H28122.1C73—C72—H72121.8
O4—C29—C28125.7 (7)O10—C73—C68112.3 (7)
O4—C29—C24110.5 (7)O10—C73—C72124.8 (7)
C28—C29—C24123.8 (8)C68—C73—C72123.0 (8)
C23—C30—O4111.3 (7)C67—C74—O10110.4 (7)
C23—C30—C31135.6 (8)C67—C74—C75136.4 (7)
O4—C30—C31113.1 (7)O10—C74—C75113.2 (7)
C32—C31—C37118.3 (8)C76—C75—C81119.6 (8)
C32—C31—C30120.3 (7)C76—C75—C74118.9 (7)
C37—C31—C30121.3 (7)C81—C75—C74121.5 (7)
C31—C32—C33122.5 (8)C77—C76—C75122.0 (8)
C31—C32—H32118.8C77—C76—H76119.0
C33—C32—H32118.8C75—C76—H76119.0
C34—C33—C32116.8 (8)C78—C77—C76116.5 (8)
C34—C33—H33121.6C78—C77—H77121.7
C32—C33—H33121.6C76—C77—H77121.7
C33—C34—C36121.5 (8)C77—C78—O12127.9 (7)
C33—C34—O5127.8 (7)C77—C78—C80122.3 (8)
C36—C34—O5110.7 (7)O12—C78—C80109.7 (7)
O6—C35—O5109.2 (7)O12—C79—O11107.0 (6)
O6—C35—H35A109.8O12—C79—H79A110.3
O5—C35—H35A109.8O11—C79—H79A110.3
O6—C35—H35B109.8O12—C79—H79B110.3
O5—C35—H35B109.8O11—C79—H79B110.3
H35A—C35—H35B108.3H79A—C79—H79B108.6
C37—C36—C34123.0 (8)C81—C80—O11127.9 (8)
C37—C36—O6127.8 (7)C81—C80—C78122.6 (8)
C34—C36—O6109.1 (7)O11—C80—C78109.5 (7)
C36—C37—C31117.8 (8)C80—C81—C75117.0 (8)
C36—C37—H37121.1C80—C81—H81121.5
C31—C37—H37121.1C75—C81—H81121.5
C43—C38—C39116.5 (7)C87—C82—C83117.0 (7)
C43—C38—C26121.9 (7)C87—C82—C70121.6 (7)
C39—C38—C26121.5 (7)C83—C82—C70121.4 (7)
C40—C39—C38122.0 (8)C84—C83—C82121.9 (8)
C40—C39—H39119.0C84—C83—H83119.1
C38—C39—H39119.0C82—C83—H83119.1
C39—C40—C41119.7 (8)C83—C84—C85118.8 (8)
C39—C40—H40120.1C83—C84—H84120.6
C41—C40—H40120.1C85—C84—H84120.6
C40—C41—C42119.9 (8)C84—C85—C86121.3 (8)
C40—C41—Br2120.3 (6)C84—C85—Br4119.6 (6)
C42—C41—Br2119.9 (6)C86—C85—Br4119.1 (6)
C43—C42—C41119.1 (8)C87—C86—C85119.5 (8)
C43—C42—H42120.5C87—C86—H86120.3
C41—C42—H42120.5C85—C86—H86120.3
C42—C43—C38122.7 (8)C86—C87—C82121.5 (8)
C42—C43—H43118.6C86—C87—H87119.3
C38—C43—H43118.6C82—C87—H87119.3
S2—C44—H44A109.5S4—C88—H88A109.5
S2—C44—H44B109.5S4—C88—H88B109.5
H44A—C44—H44B109.5H88A—C88—H88B109.5
S2—C44—H44C109.5S4—C88—H88C109.5
H44A—C44—H44C109.5H88A—C88—H88C109.5
H44B—C44—H44C109.5H88B—C88—H88C109.5
C22—S1—C1—C8−80.2 (8)C66—S3—C45—C52−96.5 (8)
C22—S1—C1—C2102.2 (7)C66—S3—C45—C4685.5 (7)
C8—C1—C2—C70.5 (9)C52—C45—C46—C47178.3 (9)
S1—C1—C2—C7178.5 (6)S3—C45—C46—C47−3.4 (14)
C8—C1—C2—C3176.4 (8)C52—C45—C46—C510.4 (9)
S1—C1—C2—C3−5.6 (13)S3—C45—C46—C51178.8 (6)
C7—C2—C3—C4−2.1 (12)C51—C46—C47—C48−1.1 (12)
C1—C2—C3—C4−177.5 (8)C45—C46—C47—C48−178.7 (8)
C2—C3—C4—C5−1.0 (11)C46—C47—C48—C49−1.1 (11)
C2—C3—C4—C16−178.6 (7)C46—C47—C48—C60−178.0 (7)
C3—C4—C5—C63.3 (12)C47—C48—C49—C502.1 (11)
C16—C4—C5—C6−179.0 (7)C60—C48—C49—C50179.1 (7)
C4—C5—C6—C7−2.3 (12)C48—C49—C50—C51−0.9 (12)
C5—C6—C7—O1179.1 (7)C52—O7—C51—C50179.2 (8)
C5—C6—C7—C2−1.0 (13)C52—O7—C51—C460.6 (8)
C8—O1—C7—C6179.9 (8)C49—C50—C51—O7−179.9 (7)
C8—O1—C7—C2−0.1 (9)C49—C50—C51—C46−1.4 (12)
C3—C2—C7—C63.2 (13)C47—C46—C51—O7−178.9 (7)
C1—C2—C7—C6179.8 (8)C45—C46—C51—O7−0.6 (9)
C3—C2—C7—O1−176.8 (7)C47—C46—C51—C502.4 (12)
C1—C2—C7—O1−0.3 (9)C45—C46—C51—C50−179.3 (7)
C2—C1—C8—O1−0.6 (9)C46—C45—C52—O7−0.1 (9)
S1—C1—C8—O1−178.5 (5)S3—C45—C52—O7−178.4 (5)
C2—C1—C8—C9−177.9 (9)C46—C45—C52—C53−173.8 (9)
S1—C1—C8—C94.2 (14)S3—C45—C52—C537.9 (15)
C7—O1—C8—C10.4 (9)C51—O7—C52—C45−0.3 (8)
C7—O1—C8—C9178.4 (7)C51—O7—C52—C53175.2 (6)
C1—C8—C9—C10−15.1 (15)C45—C52—C53—C54157.6 (9)
O1—C8—C9—C10167.6 (7)O7—C52—C53—C54−16.0 (10)
C1—C8—C9—C15166.8 (9)C45—C52—C53—C59−21.9 (14)
O1—C8—C9—C15−10.4 (11)O7—C52—C53—C59164.4 (7)
C15—C9—C10—C11−1.0 (12)C59—C53—C54—C55−0.2 (12)
C8—C9—C10—C11−179.1 (8)C52—C53—C54—C55−179.7 (7)
C9—C10—C11—C13−0.3 (13)C53—C54—C55—C560.7 (12)
C9—C10—C11—O3180.0 (7)C54—C55—C56—O8−178.6 (8)
C12—O3—C11—C10178.9 (9)C54—C55—C56—C58−1.0 (12)
C12—O3—C11—C13−0.8 (9)C57—O8—C56—C55−177.2 (9)
C11—O3—C12—O21.6 (9)C57—O8—C56—C585.0 (9)
C13—O2—C12—O3−1.8 (9)C58—O9—C57—O88.2 (10)
C10—C11—C13—C140.2 (13)C56—O8—C57—O9−8.1 (10)
O3—C11—C13—C14179.9 (7)C57—O9—C58—C59176.1 (9)
C10—C11—C13—O2180.0 (8)C57—O9—C58—C56−5.2 (9)
O3—C11—C13—O2−0.3 (9)C55—C56—C58—C590.8 (13)
C12—O2—C13—C14−179.0 (9)O8—C56—C58—C59178.9 (8)
C12—O2—C13—C111.3 (9)C55—C56—C58—O9−178.0 (7)
C11—C13—C14—C151.3 (12)O8—C56—C58—O90.1 (9)
O2—C13—C14—C15−178.5 (8)O9—C58—C59—C53178.2 (7)
C13—C14—C15—C9−2.6 (12)C56—C58—C59—C53−0.3 (12)
C10—C9—C15—C142.6 (12)C54—C53—C59—C580.0 (12)
C8—C9—C15—C14−179.3 (8)C52—C53—C59—C58179.5 (7)
C3—C4—C16—C2119.7 (12)C47—C48—C60—C6522.7 (12)
C5—C4—C16—C21−157.9 (7)C49—C48—C60—C65−154.2 (7)
C3—C4—C16—C17−158.3 (8)C47—C48—C60—C61−158.1 (8)
C5—C4—C16—C1724.1 (11)C49—C48—C60—C6125.0 (11)
C21—C16—C17—C184.9 (12)C65—C60—C61—C622.9 (12)
C4—C16—C17—C18−177.1 (8)C48—C60—C61—C62−176.3 (8)
C16—C17—C18—C19−3.3 (13)C60—C61—C62—C63−1.8 (13)
C17—C18—C19—C20−0.8 (13)C61—C62—C63—C64−0.5 (13)
C17—C18—C19—Br1177.6 (6)C61—C62—C63—Br3177.1 (7)
C18—C19—C20—C213.2 (13)C62—C63—C64—C651.6 (13)
Br1—C19—C20—C21−175.2 (6)Br3—C63—C64—C65−176.0 (6)
C19—C20—C21—C16−1.6 (12)C63—C64—C65—C60−0.4 (13)
C17—C16—C21—C20−2.4 (12)C61—C60—C65—C64−1.8 (12)
C4—C16—C21—C20179.5 (7)C48—C60—C65—C64177.4 (7)
C44—S2—C23—C3090.9 (9)C88—S4—C67—C74−86.5 (8)
C44—S2—C23—C24−91.2 (7)C88—S4—C67—C6895.1 (7)
C30—C23—C24—C25−179.7 (9)C74—C67—C68—C69173.8 (9)
S2—C23—C24—C252.0 (14)S4—C67—C68—C69−7.5 (13)
C30—C23—C24—C290.5 (9)C74—C67—C68—C730.0 (9)
S2—C23—C24—C29−177.8 (6)S4—C67—C68—C73178.7 (6)
C29—C24—C25—C260.3 (12)C73—C68—C69—C70−3.3 (11)
C23—C24—C25—C26−179.4 (8)C67—C68—C69—C70−176.4 (8)
C24—C25—C26—C271.2 (12)C68—C69—C70—C712.0 (11)
C24—C25—C26—C38−178.8 (7)C68—C69—C70—C82−178.0 (7)
C25—C26—C27—C28−2.0 (12)C69—C70—C71—C72−0.3 (12)
C38—C26—C27—C28177.9 (8)C82—C70—C71—C72179.8 (7)
C26—C27—C28—C291.3 (13)C70—C71—C72—C73−0.1 (12)
C30—O4—C29—C28−178.6 (8)C74—O10—C73—C682.2 (9)
C30—O4—C29—C240.8 (9)C74—O10—C73—C72−177.2 (7)
C27—C28—C29—O4179.8 (8)C69—C68—C73—O10−176.4 (7)
C27—C28—C29—C240.4 (12)C67—C68—C73—O10−1.4 (9)
C25—C24—C29—O4179.3 (7)C69—C68—C73—C723.0 (12)
C23—C24—C29—O4−0.9 (9)C67—C68—C73—C72178.0 (7)
C25—C24—C29—C28−1.2 (13)C71—C72—C73—O10178.1 (7)
C23—C24—C29—C28178.6 (7)C71—C72—C73—C68−1.2 (12)
C24—C23—C30—O40.0 (9)C68—C67—C74—O101.3 (9)
S2—C23—C30—O4178.1 (6)S4—C67—C74—O10−177.3 (6)
C24—C23—C30—C31178.3 (9)C68—C67—C74—C75−179.0 (9)
S2—C23—C30—C31−3.5 (15)S4—C67—C74—C752.5 (15)
C29—O4—C30—C23−0.5 (9)C73—O10—C74—C67−2.1 (8)
C29—O4—C30—C31−179.3 (7)C73—O10—C74—C75178.1 (6)
C23—C30—C31—C32−173.2 (9)C67—C74—C75—C76165.1 (9)
O4—C30—C31—C325.2 (11)O10—C74—C75—C76−15.2 (11)
C23—C30—C31—C379.0 (15)C67—C74—C75—C81−14.0 (15)
O4—C30—C31—C37−172.6 (7)O10—C74—C75—C81165.7 (7)
C37—C31—C32—C33−0.4 (12)C81—C75—C76—C77−0.9 (12)
C30—C31—C32—C33−178.3 (8)C74—C75—C76—C77180.0 (8)
C31—C32—C33—C34−1.0 (13)C75—C76—C77—C781.7 (13)
C32—C33—C34—C361.6 (13)C76—C77—C78—O12−177.4 (8)
C32—C33—C34—O5177.8 (8)C76—C77—C78—C80−1.9 (13)
C35—O5—C34—C33177.0 (9)C79—O12—C78—C77−173.5 (9)
C35—O5—C34—C36−6.4 (9)C79—O12—C78—C8010.6 (9)
C36—O6—C35—O5−8.3 (9)C78—O12—C79—O11−15.5 (9)
C34—O5—C35—O69.1 (9)C80—O11—C79—O1214.7 (9)
C33—C34—C36—C37−1.0 (13)C79—O11—C80—C81172.8 (9)
O5—C34—C36—C37−177.8 (7)C79—O11—C80—C78−8.4 (9)
C33—C34—C36—O6178.2 (7)C77—C78—C80—C811.3 (13)
O5—C34—C36—O61.4 (9)O12—C78—C80—C81177.5 (7)
C35—O6—C36—C37−176.6 (9)C77—C78—C80—O11−177.6 (7)
C35—O6—C36—C344.3 (9)O12—C78—C80—O11−1.4 (9)
C34—C36—C37—C31−0.4 (13)O11—C80—C81—C75178.3 (7)
O6—C36—C37—C31−179.4 (7)C78—C80—C81—C75−0.3 (12)
C32—C31—C37—C361.1 (12)C76—C75—C81—C800.2 (12)
C30—C31—C37—C36178.9 (8)C74—C75—C81—C80179.3 (7)
C25—C26—C38—C43160.9 (8)C69—C70—C82—C8724.2 (12)
C27—C26—C38—C43−19.1 (12)C71—C70—C82—C87−155.9 (7)
C25—C26—C38—C39−18.0 (12)C69—C70—C82—C83−157.2 (8)
C27—C26—C38—C39162.0 (8)C71—C70—C82—C8322.7 (11)
C43—C38—C39—C402.1 (12)C87—C82—C83—C842.2 (12)
C26—C38—C39—C40−179.0 (7)C70—C82—C83—C84−176.5 (8)
C38—C39—C40—C410.0 (12)C82—C83—C84—C851.3 (13)
C39—C40—C41—C42−1.8 (12)C83—C84—C85—C86−3.9 (13)
C39—C40—C41—Br2178.6 (6)C83—C84—C85—Br4175.5 (6)
C40—C41—C42—C431.3 (13)C84—C85—C86—C873.0 (13)
Br2—C41—C42—C43−179.0 (6)Br4—C85—C86—C87−176.5 (6)
C41—C42—C43—C380.9 (13)C85—C86—C87—C820.7 (12)
C39—C38—C43—C42−2.5 (12)C83—C82—C87—C86−3.2 (12)
C26—C38—C43—C42178.5 (8)C70—C82—C87—C86175.5 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C12—H12A···O40.992.583.50 (1)154
C21—H21···O6i0.952.513.37 (1)150
C57—H57A···O10ii0.992.503.32 (1)141
C65—H65···O11iii0.952.583.47 (1)156
C79—H79B···O7iv0.992.563.26 (1)128

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PB2008).

References

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