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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o560.
Published online 2008 February 6. doi:  10.1107/S1600536808002717
PMCID: PMC2960782

Ethyl 4-(3-bromo-2-thien­yl)-2-oxo-6-phenyl­cyclo­hex-3-ene-1-carboxyl­ate

Abstract

The title compound, C19H17BrO3S, crystallizes with two mol­ecules in the asymmetric unit. The methyl group of one mol­ecule is disordered approximately equally over two positions. The dihedral angles between the thio­phene and phenyl groups are 68.5 (2) and 67.5 (2)° in the two mol­ecules.

Related literature

For related structures, see Fischer et al. (2007a [triangle],b [triangle]). For related literature, see: House (1972 [triangle]); Tabba et al. (1995 [triangle]); Dimmock et al. (1999 [triangle]).

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Object name is e-64-0o560-scheme1.jpg

Experimental

Crystal data

  • C19H17BrO3S
  • M r = 405.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o560-efi1.jpg
  • a = 8.8925 (8) Å
  • b = 11.713 (2) Å
  • c = 16.853 (2) Å
  • α = 94.317 (11)°
  • β = 98.436 (10)°
  • γ = 90.235 (13)°
  • V = 1731.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.50 mm−1
  • T = 130 K
  • 0.30 × 0.17 × 0.05 mm

Data collection

  • Bruker Nonius KappaCCD diffractometer
  • Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997 [triangle]) T min = 0.638, T max = 0.843
  • 40436 measured reflections
  • 7898 independent reflections
  • 6074 reflections with I > 2σ(I)
  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.089
  • S = 1.04
  • 7898 reflections
  • 438 parameters
  • H-atom parameters constrained
  • Δρmax = 0.84 e Å−3
  • Δρmin = −0.54 e Å−3

Data collection: COLLECT (Nonius, 1999 [triangle]); cell refinement: DIRAX (Duisenberg, 1992 [triangle]); data reduction: EVALCCD (Duisenberg et al., 2003 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2007 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002717/pv2059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002717/pv2059Isup2.hkl

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

Acknowledgments

The Swedish research council (VR) is acknowledged for providing funding for the single-crystal diffractometer.

supplementary crystallographic information

Comment

Chalcones and the corresponding heterocyclic analogs are valuable intermediates in organic synthesis and exhibit a multitude of biological activities (Dimmock et al., 1999). An important feature of chalcones and their heteroanalogs is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (House, 1972). This type of reaction may be exploited with the goal of obtaining highly functionalized cyclohexene derivatives (Tabba et al., 1995). In view of the importance of these derivatives and continuing our efforts in this field (Fischer et al., 2007a; 2007b), a new derivative, the title compound, (I), has been prepared and its crystal structure is reported in this paper.

The structure of (I) contains two molecules in an asymmetric unit (Figs. 1 and 2). A methyl C-atom of methoxy group in the molecule 1, presented in Fig. 1 is disordered over two sites C19 and C19'. The geometry in the two molecules is unexceptional. The crystal packing is stabilized by van der Waals forces. The dihedral angles between the thiophene groups and phenyl groups in the two molecules are 68.5 (2) and 67.5 (2)°.

Experimental

(2E)-1-(3-Bromo-2-thienyl)-3-phenylprop-2-en-1-one (1.5 g, 5 mmol) and ethyl acetoacetate (0.65 g, 5 mmol) were refluxed for 2 hr in 10–15 ml e thanol in the presence of 0.8 ml 10% NaOH. The reaction mixture was cooled to room temperature and the reaction mass was filtered and recrystallized using methanol. Crystals were grown from acetone (m.p. 399–400 K).

Refinement

Hydrogen atoms were placed at calculated positions with C—H distances: 0.95, 0.98 and 0.99 Å for aromatic, methyl and methylene groups, respectively, and were included in the refinements in riding mode with Uiso = 1.2 and 1.5 time Ueq of the carrier atoms for non-methyl and methyl groups, respectively. A methyl C-atom of methoxy group in molecule 1 was disordered over two positions C19 and C19' with site occupation factors of 0.513 (6) and 0.487 (6), respectively.

Figures

Fig. 1.
The structure of molecule 1 in the asymmetric unit; displacement ellipsoids have been plotted at the 50% probability level. Only one of the conformational isomers is shown.
Fig. 2.
The structure of molecule 2 in the asymmetric unit; displacement ellipsoids have been plotted at the 50% probability level.

Crystal data

C19H17BrO3SZ = 4
Mr = 405.32F000 = 824
Triclinic, P1Dx = 1.555 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.8925 (8) ÅCell parameters from 44 reflections
b = 11.713 (2) Åθ = 6.3–19.4º
c = 16.853 (2) ŵ = 2.50 mm1
α = 94.317 (11)ºT = 130 K
β = 98.436 (10)ºPlate, colourless
γ = 90.235 (13)º0.30 × 0.17 × 0.05 mm
V = 1731.3 (4) Å3

Data collection

Bruker Nonius KappaCCD diffractometer6074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
[var phi] and ω scansθmax = 27.5º
Absorption correction: numerical(HABITUS; Herrendorf & Bärnighausen, 1997)θmin = 4.5º
Tmin = 0.638, Tmax = 0.843h = −11→11
40436 measured reflectionsk = −15→15
7898 independent reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042  w = 1/[σ2(Fo2) + (0.0305P)2 + 2.19P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.84 e Å3
7898 reflectionsΔρmin = −0.54 e Å3
438 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methods

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*/UeqOcc. (<1)
Br10.99977 (4)0.72535 (2)0.421420 (19)0.03009 (9)
S10.66855 (8)0.46246 (6)0.45787 (4)0.02458 (16)
O11.1493 (2)0.73022 (18)0.71856 (13)0.0311 (5)
O21.1039 (3)0.52832 (19)0.83761 (14)0.0368 (5)
O31.0313 (3)0.69989 (19)0.88526 (14)0.0408 (6)
C10.6729 (3)0.4794 (3)0.35854 (18)0.0263 (6)
C20.7753 (3)0.5611 (2)0.34871 (18)0.0236 (6)
C30.8510 (3)0.6105 (2)0.42277 (17)0.0212 (6)
C40.8073 (3)0.5679 (2)0.49033 (17)0.0203 (6)
C50.8539 (3)0.5935 (2)0.57634 (17)0.0197 (6)
C60.9826 (3)0.6524 (2)0.60774 (18)0.0214 (6)
C71.0306 (3)0.6775 (2)0.69339 (18)0.0225 (6)
C80.9305 (3)0.6373 (2)0.75173 (17)0.0213 (6)
C90.8343 (3)0.5321 (2)0.71617 (17)0.0208 (6)
C100.7514 (3)0.5522 (2)0.63266 (16)0.0206 (6)
C110.7227 (3)0.4959 (2)0.76997 (17)0.0209 (6)
C120.7020 (3)0.3799 (2)0.77736 (19)0.0285 (7)
C130.5923 (4)0.3416 (3)0.8206 (2)0.0361 (8)
C140.5035 (4)0.4191 (3)0.8572 (2)0.0374 (8)
C150.5246 (4)0.5351 (3)0.8508 (2)0.0350 (7)
C160.6338 (3)0.5729 (2)0.80828 (18)0.0263 (6)
C171.0313 (3)0.6139 (2)0.82876 (18)0.0251 (6)
C181.1320 (5)0.6868 (4)0.9614 (2)0.0555 (11)
C191.2037 (10)0.8086 (8)0.9813 (5)0.0623 (17)0.513 (6)
C19'1.0611 (10)0.5946 (9)1.0106 (5)0.0623 (17)0.487 (6)
Br20.50916 (3)0.75741 (2)0.418423 (18)0.02812 (9)
S20.16982 (8)1.01911 (6)0.45701 (4)0.02397 (16)
O40.6550 (2)0.81534 (18)0.71690 (13)0.0306 (5)
O50.6026 (2)1.03913 (17)0.84067 (13)0.0324 (5)
O60.5409 (2)0.86917 (17)0.88122 (12)0.0286 (5)
C200.1748 (3)0.9822 (3)0.35764 (18)0.0261 (6)
C210.2799 (3)0.9014 (2)0.34699 (18)0.0241 (6)
C220.3574 (3)0.8687 (2)0.42091 (17)0.0201 (6)
C230.3116 (3)0.9236 (2)0.48873 (17)0.0195 (6)
C240.3592 (3)0.9170 (2)0.57463 (17)0.0186 (6)
C250.4871 (3)0.8656 (2)0.60608 (17)0.0215 (6)
C260.5353 (3)0.8602 (2)0.69166 (18)0.0217 (6)
C270.4338 (3)0.9107 (2)0.75024 (16)0.0190 (6)
C280.3404 (3)1.0092 (2)0.71490 (16)0.0191 (6)
C290.2568 (3)0.9709 (2)0.63110 (16)0.0202 (6)
C300.2268 (3)1.0582 (2)0.76721 (17)0.0218 (6)
C310.1404 (3)0.9897 (3)0.80725 (19)0.0290 (7)
C320.0259 (4)1.0375 (3)0.8464 (2)0.0387 (8)
C33−0.0024 (4)1.1527 (3)0.8463 (2)0.0412 (9)
C340.0858 (4)1.2217 (3)0.8088 (2)0.0396 (8)
C350.1999 (4)1.1751 (3)0.76958 (18)0.0293 (7)
C360.5346 (3)0.9491 (2)0.82818 (18)0.0225 (6)
C370.6474 (4)0.8921 (3)0.9551 (2)0.0422 (9)
C380.6280 (6)0.7991 (4)1.0081 (3)0.0655 (13)
H10.61110.43690.31550.032*
H20.79400.58250.29770.028*
H61.04510.67880.57160.026*
H80.86080.70050.76400.026*
H90.90500.46730.70970.025*
H10A0.70060.48000.60830.025*
H10B0.67180.60950.63830.025*
H120.76320.32600.75260.034*
H130.57870.26200.82500.043*
H140.42840.39330.88650.045*
H150.46350.58880.87580.042*
H160.64840.65270.80520.032*
H18A1.21020.62890.95440.067*0.513 (6)
H18B1.07400.66511.00400.067*0.513 (6)
H19A1.27460.81031.03170.093*0.513 (6)
H19B1.12350.86400.98720.093*0.513 (6)
H19C1.25810.82830.93760.093*0.513 (6)
H18C1.14480.76110.99390.067*0.487 (6)
H18D1.23300.66180.95000.067*0.487 (6)
H19D1.12870.58561.06100.093*0.487 (6)
H19E1.04880.52110.97840.093*0.487 (6)
H19F0.96190.62031.02260.093*0.487 (6)
H200.11171.01430.31490.031*
H210.29920.87040.29580.029*
H250.54900.83100.57000.026*
H270.36270.84950.76110.023*
H280.41281.07230.70870.023*
H29A0.17610.91490.63660.024*
H29B0.20741.03790.60680.024*
H310.15930.91020.80800.035*
H32−0.03340.99000.87350.046*
H33−0.08231.18430.87200.049*
H340.06841.30160.80970.048*
H350.26061.22360.74400.035*
H37A0.62660.96710.98200.051*
H37B0.75270.89380.94290.051*
H38A0.52280.79681.01850.098*
H38B0.69610.81351.05920.098*
H38C0.65240.72570.98160.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03887 (18)0.02276 (15)0.02951 (18)−0.00756 (12)0.00681 (13)0.00493 (12)
S10.0186 (3)0.0318 (4)0.0222 (4)−0.0066 (3)0.0026 (3)−0.0035 (3)
O10.0262 (11)0.0335 (12)0.0313 (12)−0.0141 (9)0.0019 (9)−0.0072 (9)
O20.0390 (13)0.0326 (12)0.0364 (14)0.0065 (10)−0.0033 (10)0.0034 (10)
O30.0517 (14)0.0370 (13)0.0294 (13)−0.0003 (11)−0.0008 (11)−0.0113 (10)
C10.0234 (15)0.0328 (16)0.0213 (15)0.0020 (12)0.0015 (12)−0.0043 (12)
C20.0249 (14)0.0255 (14)0.0206 (15)0.0069 (12)0.0031 (12)0.0042 (12)
C30.0198 (13)0.0177 (13)0.0267 (16)0.0039 (11)0.0057 (11)0.0007 (11)
C40.0153 (13)0.0179 (13)0.0273 (16)0.0020 (10)0.0036 (11)−0.0022 (11)
C50.0190 (13)0.0163 (13)0.0241 (15)0.0027 (10)0.0046 (11)0.0010 (11)
C60.0168 (13)0.0217 (14)0.0263 (16)−0.0031 (11)0.0059 (11)0.0003 (11)
C70.0200 (14)0.0172 (13)0.0297 (16)−0.0018 (11)0.0040 (12)−0.0026 (11)
C80.0195 (13)0.0202 (13)0.0231 (15)−0.0019 (11)0.0009 (11)−0.0009 (11)
C90.0229 (14)0.0175 (13)0.0214 (15)−0.0033 (11)0.0027 (11)−0.0020 (11)
C100.0184 (13)0.0236 (14)0.0191 (15)−0.0044 (11)0.0020 (11)−0.0011 (11)
C110.0217 (14)0.0219 (14)0.0180 (14)−0.0040 (11)−0.0007 (11)0.0012 (11)
C120.0357 (17)0.0211 (14)0.0285 (17)−0.0019 (13)0.0047 (13)0.0012 (12)
C130.048 (2)0.0258 (16)0.0357 (19)−0.0106 (15)0.0062 (16)0.0073 (14)
C140.0434 (19)0.0421 (19)0.0288 (18)−0.0178 (16)0.0123 (15)0.0051 (15)
C150.0362 (18)0.0385 (18)0.0319 (19)−0.0043 (15)0.0127 (14)−0.0016 (14)
C160.0298 (16)0.0204 (14)0.0287 (17)−0.0031 (12)0.0044 (13)0.0023 (12)
C170.0242 (15)0.0249 (15)0.0253 (16)−0.0048 (12)0.0034 (12)−0.0022 (12)
C180.061 (3)0.070 (3)0.028 (2)−0.002 (2)−0.0077 (18)−0.0136 (19)
C190.061 (4)0.093 (5)0.031 (3)−0.031 (3)−0.003 (3)0.013 (3)
C18'0.061 (3)0.070 (3)0.028 (2)−0.002 (2)−0.0077 (18)−0.0136 (19)
C19'0.061 (4)0.093 (5)0.031 (3)−0.031 (3)−0.003 (3)0.013 (3)
Br20.03497 (17)0.02113 (15)0.02934 (17)0.00523 (12)0.00939 (13)−0.00052 (12)
S20.0190 (3)0.0310 (4)0.0221 (4)0.0037 (3)0.0031 (3)0.0031 (3)
O40.0284 (11)0.0332 (11)0.0313 (12)0.0125 (9)0.0048 (9)0.0088 (9)
O50.0354 (12)0.0249 (11)0.0342 (13)−0.0089 (9)−0.0044 (10)0.0040 (9)
O60.0309 (11)0.0289 (11)0.0246 (12)−0.0072 (9)−0.0035 (9)0.0083 (9)
C200.0233 (15)0.0327 (16)0.0220 (16)−0.0025 (12)0.0013 (12)0.0041 (12)
C210.0248 (14)0.0259 (14)0.0216 (15)−0.0086 (12)0.0060 (12)−0.0024 (12)
C220.0169 (13)0.0174 (13)0.0259 (16)−0.0049 (10)0.0043 (11)−0.0005 (11)
C230.0162 (13)0.0165 (13)0.0263 (15)−0.0050 (10)0.0049 (11)0.0023 (11)
C240.0186 (13)0.0147 (12)0.0232 (15)−0.0047 (10)0.0063 (11)0.0004 (11)
C250.0214 (14)0.0184 (13)0.0262 (16)−0.0001 (11)0.0089 (11)0.0010 (11)
C260.0199 (14)0.0160 (13)0.0301 (16)−0.0012 (11)0.0049 (12)0.0050 (11)
C270.0201 (13)0.0163 (13)0.0211 (15)−0.0036 (10)0.0034 (11)0.0036 (11)
C280.0183 (13)0.0182 (13)0.0204 (15)−0.0007 (10)0.0022 (11)0.0007 (11)
C290.0187 (13)0.0214 (13)0.0215 (15)0.0018 (11)0.0042 (11)0.0052 (11)
C300.0195 (13)0.0277 (14)0.0161 (14)0.0044 (11)−0.0021 (11)−0.0022 (11)
C310.0287 (16)0.0287 (16)0.0294 (17)−0.0021 (13)0.0065 (13)−0.0024 (13)
C320.0329 (18)0.056 (2)0.0289 (19)−0.0015 (16)0.0122 (14)−0.0029 (16)
C330.0376 (19)0.059 (2)0.0263 (18)0.0207 (17)0.0074 (15)−0.0065 (16)
C340.054 (2)0.0369 (18)0.0260 (18)0.0212 (16)0.0003 (16)−0.0033 (14)
C350.0348 (17)0.0294 (16)0.0230 (16)0.0075 (13)0.0020 (13)0.0019 (13)
C360.0186 (13)0.0240 (15)0.0252 (16)0.0005 (11)0.0033 (11)0.0033 (12)
C370.048 (2)0.044 (2)0.0289 (19)−0.0130 (16)−0.0134 (15)0.0074 (15)
C380.095 (3)0.053 (2)0.040 (2)−0.020 (2)−0.027 (2)0.0200 (19)

Geometric parameters (Å, °)

Br1—C31.888 (3)C30—C311.385 (4)
S1—C11.706 (3)C30—C351.392 (4)
S1—C41.743 (3)C31—C321.393 (4)
O1—C71.225 (3)C32—C331.376 (5)
O2—C171.201 (3)C33—C341.374 (5)
O3—C171.333 (4)C34—C351.386 (4)
O3—C181.474 (4)C37—C381.486 (5)
C1—C21.355 (4)C1—H10.9500
C2—C31.410 (4)C2—H20.9500
C3—C41.382 (4)C6—H60.9500
C4—C51.455 (4)C8—H81.0000
C5—C61.353 (4)C9—H91.0000
C5—C101.512 (4)C10—H10A0.9900
C6—C71.451 (4)C10—H10B0.9900
C7—C81.519 (4)C12—H120.9500
C8—C171.511 (4)C13—H130.9500
C8—C91.530 (4)C14—H140.9500
C9—C111.520 (4)C15—H150.9500
C9—C101.526 (4)C16—H160.9500
C11—C121.389 (4)C18—H18A0.9900
C11—C161.390 (4)C18—H18B0.9900
C12—C131.394 (4)C19—H19A0.9800
C13—C141.378 (5)C19—H19B0.9800
C14—C151.386 (5)C19—H19C0.9800
C15—C161.380 (4)C19'—H19D0.9800
C18—C191.554 (9)C19'—H19E0.9800
Br2—C221.883 (3)C19'—H19F0.9800
S2—C201.704 (3)C20—H200.9500
S2—C231.741 (3)C21—H210.9500
O4—C261.223 (3)C25—H250.9500
O5—C361.203 (3)C27—H271.0000
O6—C361.339 (3)C28—H281.0000
O6—C371.457 (4)C29—H29A0.9900
C20—C211.358 (4)C29—H29B0.9900
C21—C221.414 (4)C31—H310.9500
C22—C231.384 (4)C32—H320.9500
C23—C241.455 (4)C33—H330.9500
C24—C251.351 (4)C34—H340.9500
C24—C291.520 (4)C35—H350.9500
C25—C261.449 (4)C37—H37A0.9900
C26—C271.524 (4)C37—H37B0.9900
C27—C361.515 (4)C38—H38A0.9800
C27—C281.534 (4)C38—H38B0.9800
C28—C301.525 (4)C38—H38C0.9800
C28—C291.530 (4)
C1—S1—C493.37 (14)C5—C6—H6118.1
C17—O3—C18115.6 (3)C7—C6—H6118.1
C2—C1—S1111.6 (2)C17—C8—H8108.4
C1—C2—C3112.3 (3)C7—C8—H8108.4
C4—C3—C2115.1 (2)C9—C8—H8108.4
C4—C3—Br1126.4 (2)C11—C9—H9107.5
C2—C3—Br1118.5 (2)C10—C9—H9107.5
C3—C4—C5133.4 (2)C8—C9—H9107.5
C3—C4—S1107.7 (2)C5—C10—H10A108.8
C5—C4—S1118.9 (2)C9—C10—H10A108.8
C6—C5—C4123.3 (3)C5—C10—H10B108.8
C6—C5—C10119.0 (3)C9—C10—H10B108.8
C4—C5—C10117.7 (2)H10A—C10—H10B107.7
C5—C6—C7123.8 (3)C11—C12—H12119.6
O1—C7—C6121.0 (3)C13—C12—H12119.6
O1—C7—C8120.3 (3)C14—C13—H13120.0
C6—C7—C8118.6 (2)C12—C13—H13120.0
C17—C8—C7108.0 (2)C13—C14—H14120.2
C17—C8—C9111.7 (2)C15—C14—H14120.2
C7—C8—C9111.9 (2)C16—C15—H15119.8
C11—C9—C10110.4 (2)C14—C15—H15119.8
C11—C9—C8113.2 (2)C15—C16—H16119.6
C10—C9—C8110.5 (2)C11—C16—H16119.6
C5—C10—C9113.8 (2)O3—C18—H18A111.4
C12—C11—C16118.4 (3)C19—C18—H18A111.4
C12—C11—C9118.4 (3)O3—C18—H18B111.4
C16—C11—C9123.0 (2)C19—C18—H18B111.4
C11—C12—C13120.7 (3)H18A—C18—H18B109.2
C14—C13—C12120.0 (3)C18—C19—H19A109.5
C13—C14—C15119.6 (3)C18—C19—H19B109.5
C16—C15—C14120.4 (3)H19A—C19—H19B109.5
C15—C16—C11120.8 (3)C18—C19—H19C109.5
O2—C17—O3124.2 (3)H19A—C19—H19C109.5
O2—C17—C8123.9 (3)H19B—C19—H19C109.5
O3—C17—C8111.8 (3)H19D—C19'—H19E109.5
O3—C18—C19102.0 (4)H19D—C19'—H19F109.5
C20—S2—C2393.22 (14)H19E—C19'—H19F109.5
C36—O6—C37116.0 (2)C21—C20—H20124.1
C21—C20—S2111.8 (2)S2—C20—H20124.1
C20—C21—C22112.2 (3)C20—C21—H21123.9
C23—C22—C21114.8 (3)C22—C21—H21123.9
C23—C22—Br2126.7 (2)C24—C25—H25118.1
C21—C22—Br2118.4 (2)C26—C25—H25118.1
C22—C23—C24133.3 (3)C36—C27—H27108.7
C22—C23—S2107.9 (2)C26—C27—H27108.7
C24—C23—S2118.8 (2)C28—C27—H27108.7
C25—C24—C23123.8 (2)C30—C28—H28107.6
C25—C24—C29119.0 (3)C29—C28—H28107.6
C23—C24—C29117.1 (2)C27—C28—H28107.6
C24—C25—C26123.8 (3)C24—C29—H29A108.9
O4—C26—C25120.9 (3)C28—C29—H29A108.9
O4—C26—C27120.3 (3)C24—C29—H29B108.9
C25—C26—C27118.8 (2)C28—C29—H29B108.9
C36—C27—C26107.7 (2)H29A—C29—H29B107.7
C36—C27—C28112.0 (2)C30—C31—H31120.0
C26—C27—C28111.1 (2)C32—C31—H31120.0
C30—C28—C29109.2 (2)C33—C32—H32119.6
C30—C28—C27114.3 (2)C31—C32—H32119.6
C29—C28—C27110.2 (2)C34—C33—H33120.2
C24—C29—C28113.6 (2)C32—C33—H33120.2
C31—C30—C35118.6 (3)C33—C34—H34119.9
C31—C30—C28122.5 (3)C35—C34—H34119.9
C35—C30—C28118.7 (3)C34—C35—H35119.6
C30—C31—C32120.0 (3)C30—C35—H35119.6
C33—C32—C31120.7 (3)O6—C37—H37A110.2
C34—C33—C32119.6 (3)C38—C37—H37A110.2
C33—C34—C35120.2 (3)O6—C37—H37B110.2
C34—C35—C30120.8 (3)C38—C37—H37B110.2
O5—C36—O6124.0 (3)H37A—C37—H37B108.5
O5—C36—C27124.5 (3)C37—C38—H38A109.5
O6—C36—C27111.4 (2)C37—C38—H38B109.5
O6—C37—C38107.5 (3)H38A—C38—H38B109.5
C2—C1—H1124.2C37—C38—H38C109.5
S1—C1—H1124.2H38A—C38—H38C109.5
C1—C2—H2123.9H38B—C38—H38C109.5
C3—C2—H2123.9

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2059).

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