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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o864–o865.
Published online 2010 March 17. doi:  10.1107/S1600536810009414
PMCID: PMC2983895

Methyl 4,6-bis­(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

Abstract

The 3-cyclo­hexene units adopt envelope conformations in each of the two independent mol­ecules that comprise the asymmetric unit of the title compound, C20H16F2O3. The dihedral angles between the two fluoro­phenyl rings are 79.7 (2) and 73.7 (2)° in the two mol­ecules. In one of the mol­ecules, two C—H groups of the cyclo­hexene ring are disordered over two sets of sites in a 0.818 (13):0.182 (13) ratio, the major and minor components corresponding to the two enanti­omeric forms of the mol­ecule. Weak inter­molecular C—H(...)O inter­actions help to stabilize the crystal structure.

Related literature

For background to the applications of cyclo­hexenones, see: Padmavathi et al. (1999 [triangle]; 2000 [triangle]; 2001a [triangle],b [triangle]); Hiromichi et al. (2002 [triangle]); Hoye & Tennakoon (2000 [triangle]); Kolesnick & Golde (1994 [triangle]); Tanaka et al. (1997 [triangle]). For related structures, see: Fischer et al. (2007a [triangle],b [triangle], 2008a [triangle],b [triangle]); Li et al. (2009 [triangle]); Ashalatha et al. (2009 [triangle]); Sreevidya et al. (2010 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o864-scheme1.jpg

Experimental

Crystal data

  • C20H16F2O3
  • M r = 342.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o864-efi1.jpg
  • a = 17.3774 (5) Å
  • b = 9.0629 (3) Å
  • c = 22.2238 (7) Å
  • V = 3500.02 (19) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.40 × 0.32 × 0.28 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.961, T max = 0.973
  • 38134 measured reflections
  • 5278 independent reflections
  • 2895 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.169
  • S = 1.02
  • 5278 reflections
  • 472 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009414/sj2744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009414/sj2744Isup2.hkl

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. SS thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals.

supplementary crystallographic information

Comment

Cyclohexenones are efficient synthons for building spiro compounds (Padmavathi et al., 2001a) or as intermediates in the synthesis of benzisoxazoles or carbazole derivatives (Padmavathi et al., 1999; 2000; 2001b). Cyclohexenone derivatives are well known lead molecules for the treatment of inflammation and autoimmune diseases (Kolesnick & Golde, 1994; Tanaka et al., 1997; Hoye & Tennakoon, 2000; Hiromichi et al., 2002).

The crystal structures of some cyclohexenone derivatives viz, (8RS,9SR)-ethyl 4-(3-bromothien-2-yl)-6-(2-furyl)-2-oxocyclohex-3- ene-1-carboxylate, (7RS,8SR)-ethyl 6-(1,3-benzodioxol-5-yl)-3-(3- bromo-2-thienyl)-2-oxocyclohex-3-ene-1-carboxylate, ethyl 4-(3-bromo -2-thienyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate, rac-ethyl 3-(3-bromo-2-thienyl)-2-oxo-6-(4-propoxyphenyl)cyclohex-3-ene-1- carboxylate (Fischer et al., 2007a,b; 2008a,b) and ethyl 6-(6-methoxy-2-naphthyl)-2-oxo-4-(2-thienyl)cyclohex-3-ene-1- carboxylate (Li et al., 2009) have been reported. In a continuation of our work on cyclohexenone derivatives (Ashalatha et al., 2009; Sreevidya et al., 2010) and in view of the importance of these derivatives, the title compound (I) is synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound consists of two crystallographically independent molecules, A and B (Fig. 1). The cyclohex-3-ene units in both molecules adopt envelope conformations with puckering parameters Q = 0.462 (4)Å, Θ = 128.3 (5)° and [var phi] = 165.2 (6)° for molecule A and Q = 0.488 (6)Å, Θ = 128.5 (6)° and [var phi] = 164.2 (7)° for molecule B (Cremer & Pople, 1975). The two fluorophenyl rings are inclined to each other forming dihedral angles of 79.7 (2)° (C1A–C6A:C13A–C18A) in molecule A and 73.7 (2)° (C1B–C6B:C13B–C18B) in molecule B.

The cyclohexene rings (C7–C12) are almost coplanar with C7A, C12A, C7B and C12B displaced by -0.322 (4)Å, 0.262 (4)Å, -0.339 (6)Å and 0.281 (5)Å. In molecule B, C7 and C12 are disordered over two sites with a 0.818 (13):0.182 (13) ratio and the minor disorder component shows displacements from the mean plane of C8B/C9B/C10B/C11B in the opposite sense to that of the major component: C7C = 0.33 (4)Å; C12C = -0.414 (18)Å. Atoms C7A, C12A, C7B and C12B are stereogenic centres. In molecule B, the major and minor disorder components correspond to the two enantiomeric forms of the molecule.

In the crystal packing (Fig. 2), the molecules are linked through weak intermolecular C8A—H8AB···O2B; C8B—H8BB···O2A and C15B—H15B···O1B hydrogen bonds (see Table 1).

Experimental

A mixture of (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one (2.24g, 0.01mol) and methyl acetoacetate (0.01 mol) were refluxed for 2 hr in 10-15 ml of ethanol in presence of 0.8 ml 10% NaOH. The reaction mixture was cooled to room temperature and the solid product obtained was filtered and recrystallized from toluene (M.P.: 417K). Analytical data: found (calculated): C % : 70.08 (70.17); H% : 4.66 (4.71)

Refinement

Atoms C7B and C12B and their attached H atoms are disordered over two sets of sites with a 0.818 (13):0.182 (13) occupancy ratio. All hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.96Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. In the absence of large anomalous dispersion, 3128 Friedel pairs were merged for the final refinement.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Bonds to atoms of the minor disorder component are drawn as open lines and H atoms are omitted for clarity.
Fig. 2.
The crystal packing of the title compound, showing hydrogen-bonded network (dashed lines). H atoms not involved in hydrogen bond interactions and atoms of the minor disorder component are omitted for clarity.

Crystal data

C20H16F2O3F(000) = 1424
Mr = 342.33Dx = 1.299 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 7809 reflections
a = 17.3774 (5) Åθ = 2.5–21.9°
b = 9.0629 (3) ŵ = 0.10 mm1
c = 22.2238 (7) ÅT = 296 K
V = 3500.02 (19) Å3Block, colourless
Z = 80.40 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5278 independent reflections
Radiation source: fine-focus sealed tube2895 reflections with I > 2σ(I)
graphiteRint = 0.065
[var phi] and ω scansθmax = 30.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −24→24
Tmin = 0.961, Tmax = 0.973k = −12→12
38134 measured reflectionsl = −20→31

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0821P)2 + 0.1221P] where P = (Fo2 + 2Fc2)/3
5278 reflections(Δ/σ)max = 0.001
472 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.14 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
F1A0.13044 (18)−0.1190 (4)0.76691 (10)0.1074 (9)
F2A−0.0040 (2)−0.1767 (4)0.23590 (14)0.1323 (12)
O1A0.40617 (15)0.0074 (3)0.44238 (14)0.0808 (8)
O2A0.39944 (18)−0.1519 (3)0.57537 (17)0.0913 (9)
O3A0.41115 (18)0.0919 (3)0.57886 (15)0.0886 (8)
C1A0.2085 (2)−0.2420 (4)0.62524 (16)0.0726 (9)
H1AA0.2232−0.32960.60670.087*
C2A0.1803 (3)−0.2447 (5)0.68369 (19)0.0818 (11)
H2AA0.1762−0.33290.70480.098*
C3A0.1588 (2)−0.1153 (5)0.70904 (16)0.0751 (11)
C4A0.1641 (3)0.0180 (5)0.6812 (2)0.0809 (11)
H4AA0.14960.10460.70060.097*
C5A0.1921 (3)0.0189 (5)0.62256 (19)0.0763 (11)
H5AA0.19570.10800.60200.092*
C6A0.21478 (19)−0.1097 (4)0.59429 (14)0.0601 (8)
C7A0.2441 (2)−0.1129 (4)0.52993 (16)0.0615 (8)
H7AA0.2645−0.21210.52260.074*
C8A0.1799 (2)−0.0870 (4)0.48469 (15)0.0610 (8)
H8AA0.1432−0.16730.48760.073*
H8AB0.15320.00350.49520.073*
C9A0.2075 (2)−0.0759 (4)0.42100 (15)0.0599 (8)
C10A0.2816 (2)−0.0426 (4)0.40906 (16)0.0650 (8)
H10A0.2969−0.03830.36900.078*
C11A0.3381 (2)−0.0134 (4)0.45435 (17)0.0640 (9)
C12A0.3102 (2)−0.0035 (4)0.51956 (16)0.0611 (8)
H12A0.29090.09660.52670.073*
C13A0.1514 (2)−0.1027 (4)0.37197 (16)0.0642 (8)
C14A0.0756 (2)−0.0588 (4)0.37815 (17)0.0698 (9)
H14A0.0596−0.01330.41350.084*
C15A0.0230 (2)−0.0822 (5)0.3320 (2)0.0818 (11)
H15A−0.0279−0.05170.33580.098*
C16A0.0481 (3)−0.1514 (6)0.2809 (2)0.0956 (14)
C17A0.1221 (3)−0.1967 (7)0.2727 (2)0.1112 (18)
H17A0.1371−0.24290.23720.133*
C18A0.1741 (3)−0.1723 (6)0.3184 (2)0.0933 (14)
H18A0.2250−0.20220.31370.112*
C19A0.3777 (2)−0.0302 (4)0.56085 (17)0.0634 (8)
C20A0.4811 (4)0.0706 (6)0.6153 (3)0.124 (2)
H20A0.50340.16490.62460.187*
H20B0.51760.01260.59310.187*
H20C0.46810.02060.65200.187*
F1B0.1337 (2)0.5160 (4)−0.19775 (12)0.1155 (10)
F2B0.2341 (2)0.2462 (4)0.32262 (14)0.1301 (11)
O1B−0.15225 (18)0.6114 (4)0.12515 (15)0.0933 (9)
O2B−0.1376 (3)0.7363 (4)−0.0131 (2)0.1300 (15)
O3B−0.1543 (2)0.4954 (3)−0.00956 (17)0.0966 (10)
C1B0.0509 (2)0.6346 (5)−0.05757 (19)0.0760 (10)
H1BA0.03770.7220−0.03820.091*
C2B0.0835 (2)0.6400 (5)−0.11435 (18)0.0781 (11)
H2BA0.09240.7299−0.13330.094*
C3B0.1021 (3)0.5116 (5)−0.14166 (17)0.0788 (11)
C4B0.0910 (3)0.3776 (5)−0.1145 (2)0.0861 (12)
H4BA0.10530.2906−0.13370.103*
C5B0.0582 (3)0.3747 (5)−0.0583 (2)0.0793 (11)
H5BA0.04980.2842−0.03970.095*
C6B0.0378 (2)0.5006 (4)−0.02920 (16)0.0640 (9)
C7B0.0036 (3)0.4823 (7)0.0331 (3)0.0566 (14)0.818 (13)
H7BA−0.02380.38780.03430.068*0.818 (13)
C7C0.0136 (17)0.552 (4)0.0413 (11)0.063 (7)0.182 (13)
H7CA0.01750.65960.04570.076*0.182 (13)
C8B0.06828 (19)0.4779 (4)0.08113 (15)0.0580 (8)
H8BA0.10010.39170.07410.070*
H8BB0.10060.56450.07630.070*
C9B0.0387 (2)0.4732 (4)0.14515 (16)0.0600 (8)
C10B−0.0333 (2)0.5192 (4)0.15751 (17)0.0681 (9)
H10B−0.05030.51330.19710.082*
C11B−0.0858 (2)0.5770 (5)0.11294 (19)0.0733 (10)
C12B−0.0537 (3)0.6048 (6)0.0490 (2)0.0618 (16)0.818 (13)
H12B−0.02530.69820.04990.074*0.818 (13)
C12C−0.0661 (11)0.504 (2)0.0472 (9)0.056 (6)0.182 (13)
H12C−0.07640.39880.04210.067*0.182 (13)
C13B0.0905 (2)0.4144 (4)0.19204 (16)0.0652 (8)
C14B0.1692 (2)0.4082 (4)0.18360 (18)0.0715 (9)
H14B0.19000.44120.14750.086*
C15B0.2173 (3)0.3544 (5)0.2275 (2)0.0835 (11)
H15B0.27020.35230.22130.100*
C16B0.1867 (3)0.3042 (6)0.2801 (2)0.0904 (13)
C17B0.1109 (3)0.3063 (8)0.2898 (2)0.118 (2)
H17B0.09110.27060.32580.142*
C18B0.0621 (3)0.3607 (7)0.2468 (2)0.1047 (17)
H18B0.00940.36200.25410.126*
C19B−0.1188 (3)0.6222 (6)0.0055 (2)0.0869 (13)
C20B−0.2189 (4)0.5075 (7)−0.0513 (4)0.135 (2)
H20D−0.24670.4160−0.05200.202*
H20E−0.19980.5289−0.09090.202*
H20F−0.25250.5854−0.03850.202*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F1A0.116 (2)0.162 (3)0.0439 (12)−0.0081 (18)0.0163 (13)0.0076 (14)
F2A0.108 (2)0.193 (3)0.0960 (19)−0.007 (2)−0.0281 (18)−0.033 (2)
O1A0.0687 (16)0.0973 (19)0.0764 (18)−0.0123 (13)0.0137 (14)0.0075 (14)
O2A0.104 (2)0.0625 (15)0.108 (2)0.0139 (14)−0.0235 (19)0.0038 (16)
O3A0.105 (2)0.0661 (15)0.095 (2)0.0003 (14)−0.0244 (18)−0.0034 (15)
C1A0.090 (2)0.070 (2)0.058 (2)−0.0041 (19)0.0068 (18)0.0089 (17)
C2A0.100 (3)0.087 (3)0.059 (2)−0.009 (2)0.004 (2)0.017 (2)
C3A0.075 (2)0.109 (3)0.0412 (17)−0.015 (2)0.0014 (16)0.0091 (19)
C4A0.092 (3)0.086 (3)0.065 (2)−0.002 (2)0.017 (2)−0.010 (2)
C5A0.098 (3)0.070 (2)0.061 (2)−0.0042 (19)0.011 (2)0.0109 (18)
C6A0.065 (2)0.068 (2)0.0467 (17)−0.0039 (15)0.0049 (15)0.0042 (15)
C7A0.069 (2)0.0625 (17)0.0533 (18)0.0012 (15)0.0074 (16)0.0019 (15)
C8A0.064 (2)0.0695 (19)0.0497 (17)−0.0039 (16)0.0066 (15)0.0044 (16)
C9A0.064 (2)0.0624 (18)0.0537 (19)0.0051 (15)0.0086 (15)0.0026 (15)
C10A0.072 (2)0.076 (2)0.0466 (17)0.0029 (16)0.0103 (16)0.0098 (16)
C11A0.069 (2)0.0607 (18)0.062 (2)0.0013 (15)0.0136 (18)0.0079 (16)
C12A0.069 (2)0.0587 (18)0.055 (2)0.0046 (14)0.0013 (16)0.0045 (14)
C13A0.065 (2)0.078 (2)0.0495 (17)−0.0001 (16)0.0061 (15)−0.0003 (16)
C14A0.072 (2)0.084 (2)0.053 (2)0.0041 (18)0.0064 (17)−0.0032 (18)
C15A0.070 (2)0.104 (3)0.071 (2)0.003 (2)0.002 (2)0.002 (2)
C16A0.084 (3)0.129 (4)0.073 (3)−0.009 (3)−0.011 (2)−0.019 (3)
C17A0.100 (4)0.166 (5)0.068 (3)0.010 (3)−0.004 (3)−0.040 (3)
C18A0.076 (3)0.132 (4)0.071 (3)0.009 (2)0.009 (2)−0.026 (3)
C19A0.072 (2)0.0587 (19)0.059 (2)0.0005 (15)0.0010 (17)−0.0020 (16)
C20A0.136 (5)0.101 (3)0.136 (5)−0.009 (3)−0.069 (4)−0.003 (3)
F1B0.147 (3)0.147 (2)0.0525 (13)0.013 (2)0.0230 (15)0.0068 (14)
F2B0.118 (2)0.176 (3)0.0961 (19)0.005 (2)−0.0205 (18)0.050 (2)
O1B0.0784 (19)0.112 (2)0.090 (2)0.0279 (16)0.0214 (16)0.0041 (17)
O2B0.147 (3)0.084 (2)0.158 (4)0.013 (2)−0.034 (3)0.021 (2)
O3B0.115 (2)0.084 (2)0.092 (2)0.0142 (17)−0.0098 (19)0.0189 (16)
C1B0.094 (3)0.074 (2)0.060 (2)−0.0007 (19)0.006 (2)0.0019 (18)
C2B0.100 (3)0.077 (2)0.057 (2)−0.015 (2)0.004 (2)0.0165 (19)
C3B0.095 (3)0.098 (3)0.0426 (18)−0.009 (2)0.0042 (19)0.0066 (18)
C4B0.111 (3)0.082 (3)0.065 (2)0.002 (2)0.004 (2)−0.014 (2)
C5B0.092 (3)0.070 (2)0.076 (3)−0.0006 (19)0.014 (2)0.0053 (19)
C6B0.070 (2)0.071 (2)0.0512 (19)−0.0014 (16)0.0025 (16)0.0074 (16)
C7B0.073 (3)0.044 (3)0.053 (3)−0.003 (2)0.007 (2)0.001 (2)
C7C0.081 (16)0.066 (15)0.042 (10)−0.010 (14)−0.001 (9)−0.008 (12)
C8B0.0652 (19)0.0545 (15)0.0542 (19)−0.0027 (13)0.0111 (16)0.0033 (14)
C9B0.069 (2)0.0576 (17)0.0533 (18)−0.0107 (15)0.0103 (16)0.0011 (15)
C10B0.075 (2)0.073 (2)0.055 (2)−0.0031 (17)0.0146 (17)0.0001 (17)
C11B0.076 (3)0.077 (2)0.067 (2)0.0070 (19)0.010 (2)−0.0035 (19)
C12B0.069 (3)0.053 (3)0.063 (3)0.005 (2)0.015 (2)0.0016 (19)
C12C0.072 (13)0.036 (12)0.061 (11)−0.001 (8)0.002 (9)0.008 (7)
C13B0.073 (2)0.070 (2)0.0530 (18)−0.0125 (16)0.0081 (17)0.0045 (16)
C14B0.073 (2)0.089 (2)0.0526 (18)−0.0039 (19)0.0089 (17)0.0108 (18)
C15B0.078 (3)0.102 (3)0.070 (3)0.001 (2)0.004 (2)0.009 (2)
C16B0.089 (3)0.110 (3)0.072 (3)−0.001 (2)−0.010 (2)0.025 (2)
C17B0.107 (4)0.171 (6)0.076 (3)−0.018 (4)0.000 (3)0.052 (3)
C18B0.084 (3)0.158 (5)0.073 (3)−0.014 (3)0.009 (2)0.046 (3)
C19B0.089 (3)0.085 (3)0.087 (3)0.014 (2)0.004 (2)0.006 (2)
C20B0.134 (5)0.130 (4)0.142 (6)−0.020 (4)−0.060 (5)0.029 (4)

Geometric parameters (Å, °)

F1A—C3A1.378 (4)O3B—C19B1.346 (6)
F2A—C16A1.368 (5)O3B—C20B1.461 (7)
O1A—C11A1.227 (4)C1B—C2B1.384 (6)
O2A—C19A1.210 (4)C1B—C6B1.388 (6)
O3A—C19A1.312 (4)C1B—H1BA0.9300
O3A—C20A1.474 (6)C2B—C3B1.352 (6)
C1A—C6A1.387 (5)C2B—H2BA0.9300
C1A—C2A1.388 (6)C3B—C4B1.370 (7)
C1A—H1AA0.9300C4B—C5B1.373 (6)
C2A—C3A1.353 (7)C4B—H4BA0.9300
C2A—H2AA0.9300C5B—C6B1.359 (6)
C3A—C4A1.360 (6)C5B—H5BA0.9300
C4A—C5A1.392 (6)C6B—C7B1.516 (6)
C4A—H4AA0.9300C6B—C7C1.69 (3)
C5A—C6A1.381 (6)C7B—C12B1.532 (8)
C5A—H5AA0.9300C7B—C8B1.551 (7)
C6A—C7A1.519 (5)C7B—H7BA0.9800
C7A—C8A1.521 (5)C7C—C12C1.46 (4)
C7A—C12A1.535 (5)C7C—C8B1.46 (3)
C7A—H7AA0.9800C7C—H7CA0.9800
C8A—C9A1.498 (5)C8B—C9B1.514 (5)
C8A—H8AA0.9700C8B—H8BA0.9700
C8A—H8AB0.9700C8B—H8BB0.9700
C9A—C10A1.350 (5)C9B—C10B1.346 (5)
C9A—C13A1.482 (5)C9B—C13B1.477 (5)
C10A—C11A1.430 (5)C10B—C11B1.445 (6)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.531 (5)C11B—C12B1.548 (6)
C12A—C19A1.509 (5)C11B—C12C1.64 (2)
C12A—H12A0.9800C12B—C19B1.496 (7)
C13A—C14A1.383 (5)C12B—H12B0.9800
C13A—C18A1.404 (6)C12C—C19B1.685 (19)
C14A—C15A1.389 (6)C12C—H12C0.9800
C14A—H14A0.9300C13B—C14B1.380 (5)
C15A—C16A1.370 (7)C13B—C18B1.401 (6)
C15A—H15A0.9300C14B—C15B1.374 (6)
C16A—C17A1.362 (7)C14B—H14B0.9300
C17A—C18A1.378 (7)C15B—C16B1.363 (6)
C17A—H17A0.9300C15B—H15B0.9300
C18A—H18A0.9300C16B—C17B1.335 (7)
C20A—H20A0.9600C17B—C18B1.368 (7)
C20A—H20B0.9600C17B—H17B0.9300
C20A—H20C0.9600C18B—H18B0.9300
F1B—C3B1.363 (5)C20B—H20D0.9600
F2B—C16B1.359 (5)C20B—H20E0.9600
O1B—C11B1.227 (5)C20B—H20F0.9600
O2B—C19B1.160 (5)
C19A—O3A—C20A115.0 (3)C6B—C5B—C4B121.7 (4)
C6A—C1A—C2A120.5 (4)C6B—C5B—H5BA119.1
C6A—C1A—H1AA119.8C4B—C5B—H5BA119.1
C2A—C1A—H1AA119.8C5B—C6B—C1B118.4 (4)
C3A—C2A—C1A118.2 (4)C5B—C6B—C7B116.5 (4)
C3A—C2A—H2AA120.9C1B—C6B—C7B125.1 (4)
C1A—C2A—H2AA120.9C5B—C6B—C7C137.7 (12)
C2A—C3A—C4A124.2 (4)C1B—C6B—C7C102.7 (12)
C2A—C3A—F1A117.8 (4)C7B—C6B—C7C23.8 (10)
C4A—C3A—F1A118.0 (4)C6B—C7B—C12B112.7 (4)
C3A—C4A—C5A117.0 (4)C6B—C7B—C8B110.3 (4)
C3A—C4A—H4AA121.5C12B—C7B—C8B109.4 (5)
C5A—C4A—H4AA121.5C6B—C7B—H7BA108.1
C6A—C5A—C4A121.4 (4)C12B—C7B—H7BA108.1
C6A—C5A—H5AA119.3C8B—C7B—H7BA108.1
C4A—C5A—H5AA119.3C12C—C7C—C8B115 (2)
C5A—C6A—C1A118.8 (3)C12C—C7C—C6B103.7 (19)
C5A—C6A—C7A122.7 (3)C8B—C7C—C6B105.8 (18)
C1A—C6A—C7A118.5 (3)C12C—C7C—H7CA110.6
C6A—C7A—C8A111.9 (3)C8B—C7C—H7CA110.6
C6A—C7A—C12A112.4 (3)C6B—C7C—H7CA110.6
C8A—C7A—C12A110.5 (3)C7C—C8B—C9B111.2 (10)
C6A—C7A—H7AA107.3C7C—C8B—C7B26.0 (12)
C8A—C7A—H7AA107.3C9B—C8B—C7B113.6 (3)
C12A—C7A—H7AA107.3C7C—C8B—H8BA130.1
C9A—C8A—C7A113.6 (3)C9B—C8B—H8BA108.8
C9A—C8A—H8AA108.8C7B—C8B—H8BA108.8
C7A—C8A—H8AA108.8C7C—C8B—H8BB86.3
C9A—C8A—H8AB108.8C9B—C8B—H8BB108.8
C7A—C8A—H8AB108.8C7B—C8B—H8BB108.8
H8AA—C8A—H8AB107.7H8BA—C8B—H8BB107.7
C10A—C9A—C13A121.3 (3)C10B—C9B—C13B122.3 (3)
C10A—C9A—C8A120.4 (3)C10B—C9B—C8B119.9 (3)
C13A—C9A—C8A118.3 (3)C13B—C9B—C8B117.8 (3)
C9A—C10A—C11A123.9 (3)C9B—C10B—C11B124.0 (3)
C9A—C10A—H10A118.0C9B—C10B—H10B118.0
C11A—C10A—H10A118.0C11B—C10B—H10B118.0
O1A—C11A—C10A122.5 (3)O1B—C11B—C10B122.3 (4)
O1A—C11A—C12A120.1 (4)O1B—C11B—C12B120.0 (4)
C10A—C11A—C12A117.4 (3)C10B—C11B—C12B117.5 (3)
C19A—C12A—C11A108.7 (3)O1B—C11B—C12C119.8 (8)
C19A—C12A—C7A112.7 (3)C10B—C11B—C12C109.5 (7)
C11A—C12A—C7A109.9 (3)C12B—C11B—C12C34.0 (7)
C19A—C12A—H12A108.5C19B—C12B—C7B114.8 (5)
C11A—C12A—H12A108.5C19B—C12B—C11B109.7 (4)
C7A—C12A—H12A108.5C7B—C12B—C11B109.1 (4)
C14A—C13A—C18A118.8 (4)C19B—C12B—H12B107.7
C14A—C13A—C9A120.4 (3)C7B—C12B—H12B107.7
C18A—C13A—C9A120.8 (3)C11B—C12B—H12B107.7
C13A—C14A—C15A120.6 (4)C7C—C12C—C11B99.1 (17)
C13A—C14A—H14A119.7C7C—C12C—C19B106.2 (19)
C15A—C14A—H14A119.7C11B—C12C—C19B97.0 (11)
C16A—C15A—C14A118.2 (4)C7C—C12C—H12C117.1
C16A—C15A—H15A120.9C11B—C12C—H12C117.1
C14A—C15A—H15A120.9C19B—C12C—H12C117.1
C17A—C16A—F2A118.5 (4)C14B—C13B—C18B116.9 (4)
C17A—C16A—C15A123.3 (4)C14B—C13B—C9B121.5 (3)
F2A—C16A—C15A118.2 (4)C18B—C13B—C9B121.6 (4)
C16A—C17A—C18A118.2 (4)C15B—C14B—C13B121.4 (4)
C16A—C17A—H17A120.9C15B—C14B—H14B119.3
C18A—C17A—H17A120.9C13B—C14B—H14B119.3
C17A—C18A—C13A120.8 (4)C16B—C15B—C14B119.4 (4)
C17A—C18A—H18A119.6C16B—C15B—H15B120.3
C13A—C18A—H18A119.6C14B—C15B—H15B120.3
O2A—C19A—O3A123.3 (4)C17B—C16B—F2B119.5 (4)
O2A—C19A—C12A123.4 (3)C17B—C16B—C15B121.2 (4)
O3A—C19A—C12A113.2 (3)F2B—C16B—C15B119.3 (4)
O3A—C20A—H20A109.5C16B—C17B—C18B120.3 (4)
O3A—C20A—H20B109.5C16B—C17B—H17B119.9
H20A—C20A—H20B109.5C18B—C17B—H17B119.9
O3A—C20A—H20C109.5C17B—C18B—C13B120.9 (4)
H20A—C20A—H20C109.5C17B—C18B—H18B119.5
H20B—C20A—H20C109.5C13B—C18B—H18B119.5
C19B—O3B—C20B116.5 (4)O2B—C19B—O3B122.9 (5)
C2B—C1B—C6B120.8 (4)O2B—C19B—C12B122.4 (5)
C2B—C1B—H1BA119.6O3B—C19B—C12B114.6 (4)
C6B—C1B—H1BA119.6O2B—C19B—C12C156.0 (9)
C3B—C2B—C1B118.5 (4)O3B—C19B—C12C81.1 (8)
C3B—C2B—H2BA120.8C12B—C19B—C12C33.6 (7)
C1B—C2B—H2BA120.8O3B—C20B—H20D109.5
C2B—C3B—F1B118.8 (4)O3B—C20B—H20E109.5
C2B—C3B—C4B122.1 (4)H20D—C20B—H20E109.5
F1B—C3B—C4B119.1 (4)O3B—C20B—H20F109.5
C3B—C4B—C5B118.4 (4)H20D—C20B—H20F109.5
C3B—C4B—H4BA120.8H20E—C20B—H20F109.5
C5B—C4B—H4BA120.8
C6A—C1A—C2A—C3A0.5 (6)C7B—C6B—C7C—C12C−46 (2)
C1A—C2A—C3A—C4A−0.9 (7)C5B—C6B—C7C—C8B43 (3)
C1A—C2A—C3A—F1A179.6 (4)C1B—C6B—C7C—C8B−123.0 (17)
C2A—C3A—C4A—C5A1.2 (7)C7B—C6B—C7C—C8B75 (3)
F1A—C3A—C4A—C5A−179.3 (4)C12C—C7C—C8B—C9B−48 (3)
C3A—C4A—C5A—C6A−1.0 (7)C6B—C7C—C8B—C9B−161.5 (11)
C4A—C5A—C6A—C1A0.6 (6)C12C—C7C—C8B—C7B53 (3)
C4A—C5A—C6A—C7A178.8 (4)C6B—C7C—C8B—C7B−61 (2)
C2A—C1A—C6A—C5A−0.3 (6)C6B—C7B—C8B—C7C85 (3)
C2A—C1A—C6A—C7A−178.5 (4)C12B—C7B—C8B—C7C−40 (3)
C5A—C6A—C7A—C8A−72.1 (5)C6B—C7B—C8B—C9B175.0 (3)
C1A—C6A—C7A—C8A106.0 (4)C12B—C7B—C8B—C9B50.5 (5)
C5A—C6A—C7A—C12A52.9 (5)C7C—C8B—C9B—C10B7.0 (15)
C1A—C6A—C7A—C12A−128.9 (4)C7B—C8B—C9B—C10B−21.0 (5)
C6A—C7A—C8A—C9A174.9 (3)C7C—C8B—C9B—C13B−174.2 (15)
C12A—C7A—C8A—C9A48.8 (4)C7B—C8B—C9B—C13B157.7 (4)
C7A—C8A—C9A—C10A−20.7 (4)C13B—C9B—C10B—C11B−179.9 (4)
C7A—C8A—C9A—C13A159.1 (3)C8B—C9B—C10B—C11B−1.2 (5)
C13A—C9A—C10A—C11A179.0 (3)C9B—C10B—C11B—O1B176.5 (4)
C8A—C9A—C10A—C11A−1.1 (5)C9B—C10B—C11B—C12B−7.6 (6)
C9A—C10A—C11A—O1A175.3 (4)C9B—C10B—C11B—C12C28.6 (9)
C9A—C10A—C11A—C12A−6.8 (5)C6B—C7B—C12B—C19B56.2 (7)
O1A—C11A—C12A—C19A−23.2 (4)C8B—C7B—C12B—C19B179.2 (4)
C10A—C11A—C12A—C19A158.8 (3)C6B—C7B—C12B—C11B179.8 (4)
O1A—C11A—C12A—C7A−147.0 (3)C8B—C7B—C12B—C11B−57.2 (6)
C10A—C11A—C12A—C7A35.0 (4)O1B—C11B—C12B—C19B−20.0 (6)
C6A—C7A—C12A—C19A57.7 (4)C10B—C11B—C12B—C19B163.9 (4)
C8A—C7A—C12A—C19A−176.5 (3)C12C—C11B—C12B—C19B79.6 (13)
C6A—C7A—C12A—C11A179.2 (3)O1B—C11B—C12B—C7B−146.6 (5)
C8A—C7A—C12A—C11A−55.1 (4)C10B—C11B—C12B—C7B37.4 (6)
C10A—C9A—C13A—C14A−144.8 (4)C12C—C11B—C12B—C7B−47.0 (12)
C8A—C9A—C13A—C14A35.4 (5)C8B—C7C—C12C—C11B71 (2)
C10A—C9A—C13A—C18A35.0 (6)C6B—C7C—C12C—C11B−173.6 (13)
C8A—C9A—C13A—C18A−144.9 (4)C8B—C7C—C12C—C19B171.4 (15)
C18A—C13A—C14A—C15A−0.5 (6)C6B—C7C—C12C—C19B−74 (2)
C9A—C13A—C14A—C15A179.3 (4)O1B—C11B—C12C—C7C152.4 (16)
C13A—C14A—C15A—C16A0.9 (7)C10B—C11B—C12C—C7C−58.7 (19)
C14A—C15A—C16A—C17A−0.8 (8)C12B—C11B—C12C—C7C51.8 (17)
C14A—C15A—C16A—F2A178.9 (4)O1B—C11B—C12C—C19B44.7 (12)
F2A—C16A—C17A—C18A−179.4 (6)C10B—C11B—C12C—C19B−166.5 (6)
C15A—C16A—C17A—C18A0.4 (10)C12B—C11B—C12C—C19B−55.9 (9)
C16A—C17A—C18A—C13A0.1 (9)C10B—C9B—C13B—C14B−160.8 (4)
C14A—C13A—C18A—C17A0.0 (8)C8B—C9B—C13B—C14B20.5 (5)
C9A—C13A—C18A—C17A−179.7 (5)C10B—C9B—C13B—C18B20.0 (6)
C20A—O3A—C19A—O2A3.9 (7)C8B—C9B—C13B—C18B−158.7 (4)
C20A—O3A—C19A—C12A−175.3 (5)C18B—C13B—C14B—C15B−1.2 (7)
C11A—C12A—C19A—O2A−84.5 (4)C9B—C13B—C14B—C15B179.5 (4)
C7A—C12A—C19A—O2A37.7 (5)C13B—C14B—C15B—C16B0.9 (7)
C11A—C12A—C19A—O3A94.8 (4)C14B—C15B—C16B—C17B0.0 (8)
C7A—C12A—C19A—O3A−143.1 (3)C14B—C15B—C16B—F2B177.7 (4)
C6B—C1B—C2B—C3B0.1 (7)F2B—C16B—C17B—C18B−178.3 (6)
C1B—C2B—C3B—F1B179.5 (4)C15B—C16B—C17B—C18B−0.6 (10)
C1B—C2B—C3B—C4B−1.2 (7)C16B—C17B—C18B—C13B0.3 (10)
C2B—C3B—C4B—C5B1.5 (7)C14B—C13B—C18B—C17B0.6 (8)
F1B—C3B—C4B—C5B−179.2 (4)C9B—C13B—C18B—C17B179.9 (5)
C3B—C4B—C5B—C6B−0.8 (7)C20B—O3B—C19B—O2B0.0 (8)
C4B—C5B—C6B—C1B−0.1 (7)C20B—O3B—C19B—C12B179.3 (5)
C4B—C5B—C6B—C7B−178.9 (5)C20B—O3B—C19B—C12C179.3 (8)
C4B—C5B—C6B—C7C−165.1 (15)C7B—C12B—C19B—O2B−132.9 (6)
C2B—C1B—C6B—C5B0.5 (6)C11B—C12B—C19B—O2B103.9 (6)
C2B—C1B—C6B—C7B179.1 (4)C7B—C12B—C19B—O3B47.9 (6)
C2B—C1B—C6B—C7C170.2 (10)C11B—C12B—C19B—O3B−75.4 (5)
C5B—C6B—C7B—C12B−150.1 (5)C7B—C12B—C19B—C12C47.8 (13)
C1B—C6B—C7B—C12B31.3 (7)C11B—C12B—C19B—C12C−75.5 (13)
C7C—C6B—C7B—C12B53 (2)C7C—C12C—C19B—O2B−43 (3)
C5B—C6B—C7B—C8B87.4 (5)C11B—C12C—C19B—O2B59 (2)
C1B—C6B—C7B—C8B−91.2 (5)C7C—C12C—C19B—O3B138.5 (18)
C7C—C6B—C7B—C8B−69 (3)C11B—C12C—C19B—O3B−119.8 (9)
C5B—C6B—C7C—C12C−78 (2)C7C—C12C—C19B—C12B−41.6 (15)
C1B—C6B—C7C—C12C115 (2)C11B—C12C—C19B—C12B60.1 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O2Bi0.972.383.263 (5)151
C8B—H8BB···O2Aii0.972.573.404 (5)144
C15B—H15B···O1Biii0.932.553.226 (6)130

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2744).

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