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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1755.
Published online 2008 August 13. doi:  10.1107/S1600536808025543
PMCID: PMC2960633

(E,E)-2,5-Bis(4-tert-butyl­benzyl­idene)­cyclo­penta­none

Abstract

The asymmetric unit of the title compound, C27H32O, contains two and a half mol­ecules. In the crystal structure, one of the mol­ecules lies on a crystallographic twofold rotation axis. The dihedral angles between the benzene rings are 12.17 (6), 16.29 (11) and 51.24 (8)° for the three molecules. The dihedral angles between the benzene rings of each molecule in the asymmetric unit are 12.17 (6) and 16.29 (11)°

Related literature

For related literature, see: Began et al. (1999 [triangle]); Kawamori et al. (1999 [triangle]); Liang et al. (2008 [triangle]); Liang, Tian et al. (2007 [triangle]); Liang, Yang et al. (2007 [triangle]); Livingstone & Walker (2003 [triangle]); Poorichaya et al. (2007 [triangle]); Saiah (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1755-scheme1.jpg

Experimental

Crystal data

  • C27H32O
  • M r = 372.53
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1755-efi2.jpg
  • a = 41.246 (7) Å
  • b = 6.2930 (10) Å
  • c = 43.001 (7) Å
  • β = 94.243 (4)°
  • V = 11131 (3) Å3
  • Z = 20
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 (2) K
  • 0.50 × 0.41 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.761, T max = 1.000 (expected range = 0.752–0.989)
  • 28046 measured reflections
  • 10373 independent reflections
  • 4318 reflections with I > 2σ(I)
  • R int = 0.128

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.180
  • S = 0.86
  • 10373 reflections
  • 648 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025543/lh2667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025543/lh2667Isup2.hkl

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

Acknowledgments

This work was supported by a general grant from Zhejiang Administration of Chinese Traditional Medicine (grant Nos. 2007CA080 and 2007CA079 to GL).

supplementary crystallographic information

Comment

The title compound, (2E,5E)-2,5-bis(4-tert-butylbenzylidene)cyclopentanone (I), is one of the monocarbonyl analogues of curcumin designed and synthesized by our group. Curcumin has been found to possess a variety of pharmaceutical applications, for example, inhibiting the mutations and the formation of tumors, antioxidation, anti-inflammation, anti-virus, and decreasing total cholesterol and LDL cholesterol level (Began et al., 1999; Kawamori et al., 1999; Poorichaya et al., 2007). In previous studies, curcumin was found to be able to effect the activity of enzyme 11-beta-hydroxysteroid dehydrogenase type-1 (11-beta-HSD1), which catalyzes glucocorticoid conversion between active form (corticosterone in rodents) and inactive form (dehydrocortisone in rodents) and then regulates downstream target genes leading to increased hepatic glucose production and lipolysis in adipose tissue (Livingstone & Walker, 2003; Saiah, 2008). According to the structural disadvantages of curcumin responsible for its weak pharmacokinetic profiles, a series of mono-carbonyl analogues were designed and synthesized (Liang et al., 2008), and their 11-beta-HSD1-regulating activities in vitro were evaluated using intact Leydig cells. The title compound (I) showed an 11-beta-HSD1-regulating bioactivity with ED50 = 3029 nM on 11-beta-HSD1 oxidase and IC50 = 12278 nM against reductase of this enzyme, comparable to curcumin performs on 11-beta-HSD1 regulation (data not shown). Among these derivatives, some crystal structures are reported (Liang, Tian et al., 2007; Liang, Yang et al., 2007). In the present paper, we describe the crystal structure of compound (I). The geometrical parameters of title compound (I) are normal and there are three independent molecules. The dihedral angles between two benzene rings in each are 12.17 (6)°, 16.29 (11)°, 51.24 (8)°, respectively.

Experimental

To a solution of 15 mmol 4-tert-butybenzaldehyde in MeOH (10 ml) was added 7.5 mmol cyclopentanone. The solution was stirred at room temperature for 20 min, followed by added dropwise 2.0 mol/L NaOCH3 (3.75 ml, 7.5 mmol) in methanol. The mixture was stirred at room temperature for 1.5 h and monitored with TLC. When the reaction was complete, the residue was poured into saturated NH4Cl solution and filtered. The precipitate was washed and purified by chromatography over silica gel using CH2Cl2 / CH3OH as the eluent to afford the pure product (yield: 66.9%). Single crystals of (I) were grown in a CH2Cl2—CH3CH2OH mixture (5:1 v/v) by slow evaporation (mp 452–454 K). 1H-NMR (CDCl3): 1.35 (18H, s, CH3), 3.11 (4H, S, CH2—CH2), 7.47 (4H, d, J=8.4 Hz, Ar—H(2,6)), 7.56 (4H, d, J=8.4 Hz, Ar—H(3,5)), 7.59 (2H, s, CH). ESI-MS m/z: 373.69 (M+1), calcd for C27H32O: 372.53.

Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The three independent molecules of (I), showing 30% displacement ellipsoids for the non-hydrogen atoms [symmetry code: (A) -x+1, y, -z+1/2].
Fig. 2.
Reaction scheme.

Crystal data

C27H32OF000 = 4040
Mr = 372.53Dx = 1.111 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2156 reflections
a = 41.246 (7) Åθ = 5.3–40.8º
b = 6.2930 (10) ŵ = 0.07 mm1
c = 43.001 (7) ÅT = 293 (2) K
β = 94.243 (4)ºPrism, yellow
V = 11131 (3) Å30.50 × 0.41 × 0.18 mm
Z = 20

Data collection

Bruker SMART CCD diffractometer10373 independent reflections
Radiation source: fine-focus sealed tube4318 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.128
T = 293(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2002)h = −49→36
Tmin = 0.761, Tmax = 1.000k = −7→7
28046 measured reflectionsl = −48→52

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068  w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.180(Δ/σ)max = 0.011
S = 0.86Δρmax = 0.20 e Å3
10373 reflectionsΔρmin = −0.18 e Å3
648 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00016 (4)
Secondary atom site location: difference Fourier map

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
O10.29393 (5)0.4048 (3)0.07533 (6)0.0780 (7)
O20.39495 (5)0.5016 (3)0.17171 (6)0.0781 (7)
O30.50000.4826 (5)0.25000.150 (2)
C10.29711 (7)0.5803 (5)0.06428 (7)0.0541 (8)
C20.27036 (7)0.7186 (5)0.05130 (7)0.0518 (8)
C30.28460 (7)0.9189 (5)0.03993 (7)0.0564 (8)
H3A0.27701.03960.05140.068*
H3B0.27820.93910.01800.068*
C40.32163 (7)0.9001 (5)0.04504 (7)0.0609 (9)
H4A0.33140.90100.02520.073*
H4B0.33051.01760.05760.073*
C50.32819 (7)0.6937 (4)0.06157 (7)0.0498 (8)
C60.35604 (7)0.6012 (5)0.07231 (7)0.0560 (8)
H60.35330.47100.08200.067*
C70.38955 (7)0.6671 (5)0.07152 (7)0.0504 (8)
C80.39985 (8)0.8547 (5)0.05871 (8)0.0693 (10)
H80.38440.95300.05120.083*
C90.43234 (8)0.9011 (5)0.05671 (7)0.0662 (10)
H90.43801.03080.04830.079*
C100.45680 (7)0.7603 (5)0.06689 (7)0.0501 (8)
C110.44633 (8)0.5780 (5)0.08082 (8)0.0676 (10)
H110.46180.48270.08930.081*
C120.41393 (8)0.5305 (5)0.08281 (8)0.0669 (10)
H120.40830.40320.09200.080*
C130.23963 (7)0.6558 (5)0.05233 (7)0.0569 (9)
H130.23730.51820.05970.068*
C140.20898 (7)0.7645 (5)0.04394 (7)0.0521 (8)
C150.20580 (8)0.9549 (5)0.02837 (8)0.0651 (9)
H150.22421.02050.02160.078*
C160.17589 (8)1.0512 (5)0.02251 (8)0.0691 (10)
H160.17461.17990.01190.083*
C170.14765 (7)0.9602 (5)0.03214 (7)0.0516 (8)
C180.15075 (8)0.7686 (5)0.04666 (8)0.0693 (10)
H180.13220.70160.05300.083*
C190.18059 (8)0.6705 (5)0.05234 (8)0.0683 (10)
H190.18160.53820.06200.082*
C200.49193 (7)0.8047 (5)0.06146 (7)0.0586 (9)
C210.50018 (8)1.0402 (6)0.06386 (8)0.0873 (12)
H21A0.48661.11790.04870.121*
H21B0.52261.06090.06000.121*
H21C0.49651.09050.08440.121*
C220.49753 (8)0.7297 (6)0.02807 (7)0.0924 (13)
H22A0.49350.57970.02640.129*
H22B0.51960.75890.02370.129*
H22C0.48300.80390.01340.129*
C230.51543 (7)0.6833 (5)0.08448 (8)0.0813 (11)
H23A0.51150.72280.10540.112*
H23B0.53740.71800.08060.112*
H23C0.51210.53330.08180.112*
C240.11478 (7)1.0750 (5)0.02828 (7)0.0600 (9)
C250.11316 (9)1.2364 (6)0.00167 (8)0.0994 (13)
H25A0.09171.2959−0.00090.129*
H25B0.11811.1670−0.01730.129*
H25C0.12861.34770.00650.129*
C260.08709 (8)0.9174 (6)0.02227 (10)0.1145 (16)
H26A0.08560.82920.04030.132*
H26B0.09120.83030.00460.132*
H26C0.06710.99330.01800.132*
C270.10989 (8)1.1952 (5)0.05843 (8)0.0823 (11)
H27A0.10921.09590.07530.113*
H27B0.08981.27290.05620.113*
H27C0.12761.29220.06280.113*
C280.39418 (8)0.6813 (5)0.16108 (7)0.0569 (9)
C290.36451 (8)0.8006 (5)0.14964 (7)0.0530 (8)
C300.37431 (7)1.0141 (5)0.13873 (7)0.0610 (9)
H30A0.36451.12460.15070.073*
H30B0.36731.03310.11690.073*
C310.41147 (7)1.0257 (5)0.14342 (7)0.0598 (9)
H31A0.42081.04780.12360.072*
H31B0.41801.14220.15720.072*
C320.42270 (8)0.8190 (5)0.15740 (7)0.0525 (8)
C330.45271 (8)0.7498 (5)0.16590 (7)0.0591 (9)
H330.45360.61320.17420.071*
C340.48430 (8)0.8524 (5)0.16440 (7)0.0572 (9)
C350.48909 (8)1.0564 (5)0.15346 (8)0.0651 (9)
H350.47121.14020.14740.078*
C360.51997 (9)1.1379 (5)0.15140 (8)0.0693 (10)
H360.52211.27660.14440.083*
C370.54771 (8)1.0213 (6)0.15933 (7)0.0596 (9)
C380.54279 (8)0.8225 (6)0.17108 (8)0.0700 (10)
H380.56080.74160.17780.084*
C390.51227 (8)0.7368 (5)0.17340 (7)0.0656 (9)
H390.51030.59960.18110.079*
C400.33520 (8)0.7134 (5)0.15129 (7)0.0575 (9)
H400.33540.57260.15790.069*
C410.30296 (8)0.8035 (5)0.14442 (7)0.0542 (8)
C420.29618 (8)0.9955 (5)0.13020 (7)0.0650 (9)
H420.31311.07150.12230.078*
C430.26539 (8)1.0797 (5)0.12713 (7)0.0621 (9)
H430.26211.21040.11730.075*
C440.23909 (7)0.9745 (5)0.13833 (6)0.0487 (8)
C450.24561 (8)0.7785 (5)0.15148 (8)0.0692 (10)
H450.22860.70130.15890.083*
C460.27610 (8)0.6926 (5)0.15411 (8)0.0697 (10)
H460.27910.55730.16250.084*
C470.58159 (8)1.1126 (6)0.15588 (8)0.0694 (10)
C480.58196 (9)1.2481 (8)0.12684 (10)0.116 (2)
H48A0.57041.37780.12980.133*
H48B0.57171.17210.10940.133*
H48C0.60401.28030.12290.133*
C490.60698 (9)0.9422 (7)0.15397 (13)0.115 (2)
H49A0.60920.86570.17330.132*
H49B0.62741.00630.15000.132*
H49C0.60050.84600.13730.132*
C500.59097 (9)1.2498 (6)0.18397 (10)0.1174 (16)
H50A0.59301.16270.20230.136*
H50B0.57451.35560.18610.136*
H50C0.61141.31810.18130.136*
C510.20573 (7)1.0771 (5)0.13858 (7)0.0539 (8)
C520.19933 (8)1.2366 (5)0.11190 (8)0.0842 (11)
H52A0.21551.34650.11360.116*
H52B0.17821.29840.11310.116*
H52C0.20031.16490.09230.116*
C530.17837 (8)0.9136 (6)0.13635 (9)0.0906 (12)
H53A0.17980.82950.11790.126*
H53B0.15780.98540.13540.126*
H53C0.18030.82300.15430.126*
C540.20421 (8)1.1991 (5)0.16945 (8)0.0819 (11)
H54A0.20711.10160.18660.113*
H54B0.18351.26760.16990.113*
H54C0.22111.30410.17110.113*
C550.50000.6744 (8)0.25000.0757 (15)
C560.47090 (8)0.8110 (5)0.24588 (7)0.0558 (8)
C570.48172 (6)1.0344 (4)0.24519 (7)0.0578 (9)
H57A0.47011.11930.25960.069*
H57B0.47761.09290.22440.069*
C580.44126 (8)0.7242 (5)0.24475 (7)0.0621 (9)
H580.44080.57660.24570.075*
C590.40947 (8)0.8272 (5)0.24219 (7)0.0541 (8)
C600.38304 (8)0.7181 (5)0.25263 (8)0.0692 (10)
H600.38610.58110.26040.083*
C610.35248 (8)0.8073 (5)0.25171 (8)0.0694 (10)
H610.33560.73050.25950.083*
C620.34621 (7)1.0063 (5)0.23968 (7)0.0508 (8)
C630.37253 (8)1.1119 (5)0.22831 (7)0.0576 (9)
H630.36921.24560.21940.069*
C640.40330 (8)1.0253 (5)0.22976 (7)0.0570 (9)
H640.42021.10270.22220.068*
C650.31284 (8)1.1083 (5)0.24011 (7)0.0554 (8)
C660.30633 (8)1.2711 (6)0.21395 (8)0.0984 (13)
H66A0.32201.38390.21640.128*
H66B0.28481.32820.21480.128*
H66C0.30811.20330.19420.128*
C670.28577 (8)0.9443 (6)0.23752 (10)0.1012 (14)
H67A0.28640.86870.21820.132*
H67B0.26521.01440.23810.132*
H67C0.28860.84610.25460.132*
C680.31128 (8)1.2240 (6)0.27122 (8)0.0887 (12)
H68A0.31411.12360.28800.123*
H68B0.29051.29220.27190.123*
H68C0.32821.32890.27330.123*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0684 (16)0.0598 (15)0.107 (2)−0.0006 (13)0.0149 (13)0.0237 (15)
O20.0815 (17)0.0480 (14)0.106 (2)0.0022 (13)0.0130 (14)0.0113 (14)
O30.081 (3)0.036 (2)0.332 (7)0.0000.016 (3)0.000
C10.059 (2)0.050 (2)0.055 (2)0.0021 (18)0.0105 (16)0.0025 (17)
C20.054 (2)0.053 (2)0.049 (2)0.0001 (18)0.0108 (15)−0.0013 (16)
C30.054 (2)0.058 (2)0.058 (2)−0.0018 (17)0.0104 (16)0.0071 (16)
C40.057 (2)0.062 (2)0.064 (2)0.0006 (17)0.0066 (16)0.0128 (18)
C50.051 (2)0.051 (2)0.0484 (19)0.0035 (17)0.0133 (15)0.0062 (15)
C60.064 (2)0.057 (2)0.048 (2)0.0030 (18)0.0105 (16)0.0040 (16)
C70.054 (2)0.053 (2)0.0443 (19)0.0046 (17)0.0059 (15)0.0060 (15)
C80.053 (2)0.069 (2)0.086 (3)0.0052 (19)0.0015 (18)0.022 (2)
C90.057 (2)0.066 (2)0.076 (3)−0.0001 (19)0.0036 (18)0.0237 (19)
C100.052 (2)0.059 (2)0.0396 (18)0.0071 (17)0.0036 (14)−0.0024 (16)
C110.056 (2)0.070 (2)0.077 (3)0.0150 (19)0.0045 (18)0.017 (2)
C120.059 (2)0.060 (2)0.082 (3)0.0062 (19)0.0071 (19)0.0227 (19)
C130.055 (2)0.055 (2)0.062 (2)0.0012 (18)0.0118 (16)0.0019 (16)
C140.054 (2)0.053 (2)0.049 (2)−0.0008 (17)0.0067 (15)0.0050 (16)
C150.053 (2)0.070 (2)0.075 (3)−0.0006 (19)0.0177 (17)0.0171 (19)
C160.063 (2)0.070 (2)0.075 (3)0.005 (2)0.0118 (19)0.0223 (19)
C170.054 (2)0.056 (2)0.0454 (19)0.0002 (17)0.0033 (15)0.0007 (16)
C180.055 (2)0.076 (3)0.077 (3)−0.0073 (19)0.0105 (18)0.024 (2)
C190.055 (2)0.064 (2)0.086 (3)−0.0021 (19)0.0052 (19)0.0267 (19)
C200.053 (2)0.075 (2)0.048 (2)0.0003 (19)0.0033 (15)−0.0044 (18)
C210.068 (3)0.098 (3)0.097 (3)−0.013 (2)0.012 (2)−0.006 (2)
C220.072 (3)0.148 (4)0.060 (3)0.001 (2)0.0227 (19)−0.015 (2)
C230.058 (2)0.114 (3)0.072 (3)0.012 (2)0.0023 (18)0.010 (2)
C240.058 (2)0.067 (2)0.055 (2)0.0061 (18)−0.0008 (16)0.0030 (18)
C250.099 (3)0.126 (3)0.073 (3)0.041 (3)0.006 (2)0.031 (2)
C260.062 (3)0.101 (3)0.175 (5)−0.005 (2)−0.030 (3)−0.027 (3)
C270.074 (3)0.100 (3)0.074 (3)0.014 (2)0.012 (2)−0.008 (2)
C280.069 (2)0.049 (2)0.055 (2)0.0024 (19)0.0134 (17)−0.0054 (17)
C290.064 (2)0.048 (2)0.048 (2)0.0015 (18)0.0161 (16)−0.0042 (15)
C300.067 (2)0.059 (2)0.058 (2)0.0008 (18)0.0115 (17)0.0045 (17)
C310.062 (2)0.059 (2)0.059 (2)−0.0003 (18)0.0093 (16)0.0041 (17)
C320.061 (2)0.046 (2)0.052 (2)0.0036 (18)0.0117 (16)−0.0029 (16)
C330.073 (2)0.052 (2)0.054 (2)0.0012 (19)0.0167 (17)−0.0035 (16)
C340.065 (2)0.058 (2)0.049 (2)0.0037 (19)0.0109 (16)−0.0072 (17)
C350.060 (2)0.061 (2)0.075 (3)0.0040 (19)0.0121 (18)−0.0022 (19)
C360.075 (3)0.061 (2)0.074 (3)−0.006 (2)0.015 (2)0.0010 (19)
C370.065 (2)0.062 (2)0.052 (2)−0.001 (2)0.0042 (17)−0.0049 (17)
C380.058 (2)0.079 (3)0.072 (3)0.005 (2)−0.0030 (18)0.004 (2)
C390.065 (2)0.061 (2)0.071 (3)0.006 (2)0.0033 (18)0.0053 (18)
C400.069 (2)0.049 (2)0.056 (2)−0.0004 (18)0.0148 (17)0.0010 (16)
C410.064 (2)0.051 (2)0.049 (2)−0.0018 (18)0.0099 (16)0.0044 (16)
C420.060 (2)0.069 (2)0.068 (2)−0.0015 (19)0.0192 (17)0.0224 (19)
C430.069 (2)0.055 (2)0.064 (2)−0.0048 (19)0.0135 (18)0.0155 (17)
C440.059 (2)0.051 (2)0.0366 (18)−0.0042 (17)0.0027 (14)0.0015 (15)
C450.063 (2)0.063 (2)0.082 (3)−0.0110 (19)0.0137 (19)0.021 (2)
C460.068 (3)0.050 (2)0.091 (3)−0.007 (2)0.004 (2)0.0208 (19)
C470.055 (2)0.081 (3)0.071 (3)−0.008 (2)−0.0033 (18)−0.004 (2)
C480.093 (3)0.177 (6)0.095 (4)−0.069 (4)−0.007 (3)0.087 (4)
C490.070 (3)0.120 (4)0.180 (7)0.003 (3)0.057 (4)−0.020 (4)
C500.101 (3)0.139 (4)0.109 (4)−0.046 (3)−0.010 (3)−0.020 (3)
C510.058 (2)0.058 (2)0.046 (2)−0.0061 (17)0.0041 (15)0.0049 (16)
C520.083 (3)0.104 (3)0.065 (3)0.017 (2)0.0042 (19)0.029 (2)
C530.066 (3)0.096 (3)0.109 (3)−0.017 (2)−0.002 (2)0.005 (2)
C540.086 (3)0.093 (3)0.068 (3)0.014 (2)0.010 (2)−0.005 (2)
C550.076 (4)0.038 (3)0.114 (5)0.0000.017 (3)0.000
C560.065 (2)0.0397 (19)0.063 (2)−0.0012 (17)0.0130 (17)−0.0012 (16)
C570.063 (2)0.0414 (19)0.070 (2)−0.0032 (15)0.0114 (18)0.0011 (16)
C580.073 (3)0.0409 (19)0.073 (2)0.0005 (19)0.0110 (18)−0.0013 (17)
C590.070 (2)0.0397 (19)0.054 (2)−0.0034 (17)0.0093 (17)−0.0054 (16)
C600.075 (3)0.044 (2)0.090 (3)−0.006 (2)0.013 (2)0.0126 (18)
C610.066 (3)0.059 (2)0.085 (3)−0.0039 (19)0.0184 (19)0.015 (2)
C620.064 (2)0.047 (2)0.0414 (19)−0.0034 (17)0.0048 (15)−0.0054 (15)
C630.078 (3)0.047 (2)0.048 (2)−0.0015 (19)0.0051 (17)0.0064 (16)
C640.068 (2)0.050 (2)0.055 (2)−0.0060 (18)0.0155 (17)0.0035 (16)
C650.064 (2)0.057 (2)0.045 (2)−0.0012 (18)0.0024 (15)−0.0043 (16)
C660.101 (3)0.122 (3)0.071 (3)0.033 (3)0.004 (2)0.027 (2)
C670.069 (3)0.091 (3)0.142 (4)−0.006 (2)−0.006 (2)−0.011 (3)
C680.085 (3)0.112 (3)0.070 (3)0.021 (2)0.011 (2)−0.021 (2)

Geometric parameters (Å, °)

O1—C11.213 (3)C35—C361.382 (4)
O2—C281.219 (3)C35—H350.9300
O3—C551.207 (5)C36—C371.381 (4)
C1—C51.479 (4)C36—H360.9300
C1—C21.482 (4)C37—C381.370 (4)
C2—C131.331 (4)C37—C471.528 (4)
C2—C31.489 (4)C38—C391.380 (4)
C3—C41.532 (3)C38—H380.9300
C3—H3A0.9700C39—H390.9300
C3—H3B0.9700C40—C411.456 (4)
C4—C51.496 (4)C40—H400.9300
C4—H4A0.9700C41—C421.374 (4)
C4—H4B0.9700C41—C461.399 (4)
C5—C61.339 (4)C42—C431.374 (4)
C6—C71.446 (4)C42—H420.9300
C6—H60.9300C43—C441.387 (4)
C7—C121.383 (4)C43—H430.9300
C7—C81.383 (4)C44—C451.375 (4)
C8—C91.381 (4)C44—C511.521 (4)
C8—H80.9300C45—C461.366 (4)
C9—C101.389 (4)C45—H450.9300
C9—H90.9300C46—H460.9300
C10—C111.379 (4)C47—C491.505 (5)
C10—C201.511 (4)C47—C501.512 (4)
C11—C121.378 (4)C47—C481.513 (4)
C11—H110.9300C48—H48A0.9600
C12—H120.9300C48—H48B0.9600
C13—C141.459 (4)C48—H48C0.9600
C13—H130.9300C49—H49A0.9600
C14—C151.374 (4)C49—H49B0.9600
C14—C191.384 (4)C49—H49C0.9600
C15—C161.381 (4)C50—H50A0.9600
C15—H150.9300C50—H50B0.9600
C16—C171.388 (4)C50—H50C0.9600
C16—H160.9300C51—C531.524 (4)
C17—C181.359 (4)C51—C521.533 (4)
C17—C241.534 (4)C51—C541.539 (4)
C18—C191.383 (4)C52—H52A0.9600
C18—H180.9300C52—H52B0.9600
C19—H190.9300C52—H52C0.9600
C20—C211.523 (4)C53—H53A0.9600
C20—C231.536 (4)C53—H53B0.9600
C20—C221.545 (4)C53—H53C0.9600
C21—H21A0.9600C54—H54A0.9600
C21—H21B0.9600C54—H54B0.9600
C21—H21C0.9600C54—H54C0.9600
C22—H22A0.9600C55—C56i1.476 (4)
C22—H22B0.9600C55—C561.476 (4)
C22—H22C0.9600C56—C581.337 (4)
C23—H23A0.9600C56—C571.476 (4)
C23—H23B0.9600C57—C57i1.534 (5)
C23—H23C0.9600C57—H57A0.9700
C24—C261.520 (4)C57—H57B0.9700
C24—C271.527 (4)C58—C591.460 (4)
C24—C251.528 (4)C58—H580.9300
C25—H25A0.9600C59—C641.373 (4)
C25—H25B0.9600C59—C601.391 (4)
C25—H25C0.9600C60—C611.378 (4)
C26—H26A0.9600C60—H600.9300
C26—H26B0.9600C61—C621.372 (4)
C26—H26C0.9600C61—H610.9300
C27—H27A0.9600C62—C631.392 (4)
C27—H27B0.9600C62—C651.520 (4)
C27—H27C0.9600C63—C641.379 (4)
C28—C321.479 (4)C63—H630.9300
C28—C291.488 (4)C64—H640.9300
C29—C401.334 (4)C65—C671.518 (4)
C29—C301.489 (4)C65—C681.529 (4)
C30—C311.532 (4)C65—C661.530 (4)
C30—H30A0.9700C66—H66A0.9600
C30—H30B0.9700C66—H66B0.9600
C31—C321.492 (4)C66—H66C0.9600
C31—H31A0.9700C67—H67A0.9600
C31—H31B0.9700C67—H67B0.9600
C32—C331.337 (4)C67—H67C0.9600
C33—C341.460 (4)C68—H68A0.9600
C33—H330.9300C68—H68B0.9600
C34—C351.387 (4)C68—H68C0.9600
C34—C391.394 (4)
O1—C1—C5126.1 (3)C34—C35—H35119.3
O1—C1—C2125.7 (3)C37—C36—C35122.5 (3)
C5—C1—C2108.2 (3)C37—C36—H36118.7
C13—C2—C1119.8 (3)C35—C36—H36118.7
C13—C2—C3131.5 (3)C38—C37—C36115.7 (3)
C1—C2—C3108.7 (3)C38—C37—C47122.7 (3)
C2—C3—C4107.5 (2)C36—C37—C47121.6 (3)
C2—C3—H3A110.2C37—C38—C39123.0 (3)
C4—C3—H3A110.2C37—C38—H38118.5
C2—C3—H3B110.2C39—C38—H38118.5
C4—C3—H3B110.2C38—C39—C34121.1 (3)
H3A—C3—H3B108.5C38—C39—H39119.4
C5—C4—C3106.2 (2)C34—C39—H39119.4
C5—C4—H4A110.5C29—C40—C41130.3 (3)
C3—C4—H4A110.5C29—C40—H40114.9
C5—C4—H4B110.5C41—C40—H40114.9
C3—C4—H4B110.5C42—C41—C46115.6 (3)
H4A—C4—H4B108.7C42—C41—C40125.9 (3)
C6—C5—C1119.3 (3)C46—C41—C40118.5 (3)
C6—C5—C4131.4 (3)C43—C42—C41122.6 (3)
C1—C5—C4109.2 (3)C43—C42—H42118.7
C5—C6—C7131.6 (3)C41—C42—H42118.7
C5—C6—H6114.2C42—C43—C44121.6 (3)
C7—C6—H6114.2C42—C43—H43119.2
C12—C7—C8115.7 (3)C44—C43—H43119.2
C12—C7—C6119.0 (3)C45—C44—C43115.9 (3)
C8—C7—C6125.2 (3)C45—C44—C51121.8 (3)
C9—C8—C7122.3 (3)C43—C44—C51122.1 (3)
C9—C8—H8118.9C46—C45—C44122.7 (3)
C7—C8—H8118.9C46—C45—H45118.7
C8—C9—C10122.1 (3)C44—C45—H45118.7
C8—C9—H9119.0C45—C46—C41121.5 (3)
C10—C9—H9119.0C45—C46—H46119.2
C11—C10—C9115.1 (3)C41—C46—H46119.2
C11—C10—C20123.8 (3)C49—C47—C50108.2 (3)
C9—C10—C20121.1 (3)C49—C47—C48107.9 (4)
C12—C11—C10122.9 (3)C50—C47—C48108.7 (3)
C12—C11—H11118.5C49—C47—C37112.5 (3)
C10—C11—H11118.5C50—C47—C37108.6 (3)
C11—C12—C7121.8 (3)C48—C47—C37110.9 (3)
C11—C12—H12119.1C47—C48—H48A109.5
C7—C12—H12119.1C47—C48—H48B109.5
C2—C13—C14131.5 (3)H48A—C48—H48B109.5
C2—C13—H13114.3C47—C48—H48C109.5
C14—C13—H13114.3H48A—C48—H48C109.5
C15—C14—C19116.6 (3)H48B—C48—H48C109.5
C15—C14—C13125.4 (3)C47—C49—H49A109.5
C19—C14—C13118.0 (3)C47—C49—H49B109.5
C14—C15—C16121.6 (3)H49A—C49—H49B109.5
C14—C15—H15119.2C47—C49—H49C109.5
C16—C15—H15119.2H49A—C49—H49C109.5
C15—C16—C17121.5 (3)H49B—C49—H49C109.5
C15—C16—H16119.3C47—C50—H50A109.5
C17—C16—H16119.3C47—C50—H50B109.5
C18—C17—C16116.8 (3)H50A—C50—H50B109.5
C18—C17—C24121.3 (3)C47—C50—H50C109.5
C16—C17—C24121.8 (3)H50A—C50—H50C109.5
C17—C18—C19122.0 (3)H50B—C50—H50C109.5
C17—C18—H18119.0C44—C51—C53112.3 (3)
C19—C18—H18119.0C44—C51—C52112.2 (3)
C18—C19—C14121.5 (3)C53—C51—C52108.0 (3)
C18—C19—H19119.3C44—C51—C54108.2 (2)
C14—C19—H19119.3C53—C51—C54108.3 (3)
C10—C20—C21112.4 (3)C52—C51—C54107.6 (3)
C10—C20—C23112.0 (3)C51—C52—H52A109.5
C21—C20—C23108.2 (3)C51—C52—H52B109.5
C10—C20—C22107.4 (2)H52A—C52—H52B109.5
C21—C20—C22108.2 (3)C51—C52—H52C109.5
C23—C20—C22108.4 (3)H52A—C52—H52C109.5
C20—C21—H21A109.5H52B—C52—H52C109.5
C20—C21—H21B109.5C51—C53—H53A109.5
H21A—C21—H21B109.5C51—C53—H53B109.5
C20—C21—H21C109.5H53A—C53—H53B109.5
H21A—C21—H21C109.5C51—C53—H53C109.5
H21B—C21—H21C109.5H53A—C53—H53C109.5
C20—C22—H22A109.5H53B—C53—H53C109.5
C20—C22—H22B109.5C51—C54—H54A109.5
H22A—C22—H22B109.5C51—C54—H54B109.5
C20—C22—H22C109.5H54A—C54—H54B109.5
H22A—C22—H22C109.5C51—C54—H54C109.5
H22B—C22—H22C109.5H54A—C54—H54C109.5
C20—C23—H23A109.5H54B—C54—H54C109.5
C20—C23—H23B109.5O3—C55—C56i125.6 (2)
H23A—C23—H23B109.5O3—C55—C56125.6 (2)
C20—C23—H23C109.5C56i—C55—C56108.8 (4)
H23A—C23—H23C109.5C58—C56—C55120.0 (3)
H23B—C23—H23C109.5C58—C56—C57131.7 (3)
C26—C24—C27108.8 (3)C55—C56—C57108.2 (3)
C26—C24—C25108.4 (3)C56—C57—C57i106.69 (17)
C27—C24—C25107.8 (3)C56—C57—H57A110.4
C26—C24—C17111.0 (3)C57i—C57—H57A110.4
C27—C24—C17108.2 (2)C56—C57—H57B110.4
C25—C24—C17112.5 (3)C57i—C57—H57B110.4
C24—C25—H25A109.5H57A—C57—H57B108.6
C24—C25—H25B109.5C56—C58—C59129.4 (3)
H25A—C25—H25B109.5C56—C58—H58115.3
C24—C25—H25C109.5C59—C58—H58115.3
H25A—C25—H25C109.5C64—C59—C60116.6 (3)
H25B—C25—H25C109.5C64—C59—C58124.9 (3)
C24—C26—H26A109.5C60—C59—C58118.5 (3)
C24—C26—H26B109.5C61—C60—C59121.8 (3)
H26A—C26—H26B109.5C61—C60—H60119.1
C24—C26—H26C109.5C59—C60—H60119.1
H26A—C26—H26C109.5C62—C61—C60122.0 (3)
H26B—C26—H26C109.5C62—C61—H61119.0
C24—C27—H27A109.5C60—C61—H61119.0
C24—C27—H27B109.5C61—C62—C63116.0 (3)
H27A—C27—H27B109.5C61—C62—C65121.8 (3)
C24—C27—H27C109.5C63—C62—C65122.2 (3)
H27A—C27—H27C109.5C64—C63—C62122.3 (3)
H27B—C27—H27C109.5C64—C63—H63118.8
O2—C28—C32125.8 (3)C62—C63—H63118.8
O2—C28—C29126.2 (3)C59—C64—C63121.3 (3)
C32—C28—C29108.1 (3)C59—C64—H64119.3
C40—C29—C28120.1 (3)C63—C64—H64119.3
C40—C29—C30131.0 (3)C67—C65—C62111.9 (3)
C28—C29—C30108.9 (3)C67—C65—C68108.0 (3)
C29—C30—C31107.1 (2)C62—C65—C68108.0 (2)
C29—C30—H30A110.3C67—C65—C66108.2 (3)
C31—C30—H30A110.3C62—C65—C66112.6 (3)
C29—C30—H30B110.3C68—C65—C66107.9 (3)
C31—C30—H30B110.3C65—C66—H66A109.5
H30A—C30—H30B108.6C65—C66—H66B109.5
C32—C31—C30106.8 (2)H66A—C66—H66B109.5
C32—C31—H31A110.4C65—C66—H66C109.5
C30—C31—H31A110.4H66A—C66—H66C109.5
C32—C31—H31B110.4H66B—C66—H66C109.5
C30—C31—H31B110.4C65—C67—H67A109.5
H31A—C31—H31B108.6C65—C67—H67B109.5
C33—C32—C28120.5 (3)H67A—C67—H67B109.5
C33—C32—C31130.4 (3)C65—C67—H67C109.5
C28—C32—C31109.1 (3)H67A—C67—H67C109.5
C32—C33—C34130.9 (3)H67B—C67—H67C109.5
C32—C33—H33114.5C65—C68—H68A109.5
C34—C33—H33114.5C65—C68—H68B109.5
C35—C34—C39116.2 (3)H68A—C68—H68B109.5
C35—C34—C33125.1 (3)C65—C68—H68C109.5
C39—C34—C33118.7 (3)H68A—C68—H68C109.5
C36—C35—C34121.4 (3)H68B—C68—H68C109.5
C36—C35—H35119.3
O1—C1—C2—C132.8 (5)C28—C32—C33—C34179.3 (3)
C5—C1—C2—C13−177.0 (3)C31—C32—C33—C340.0 (5)
O1—C1—C2—C3−179.5 (3)C32—C33—C34—C351.1 (5)
C5—C1—C2—C30.8 (3)C32—C33—C34—C39−176.3 (3)
C13—C2—C3—C4179.5 (3)C39—C34—C35—C360.7 (5)
C1—C2—C3—C42.1 (3)C33—C34—C35—C36−176.8 (3)
C2—C3—C4—C5−4.1 (3)C34—C35—C36—C371.4 (5)
O1—C1—C5—C6−0.8 (5)C35—C36—C37—C38−3.4 (5)
C2—C1—C5—C6178.9 (3)C35—C36—C37—C47178.0 (3)
O1—C1—C5—C4176.9 (3)C36—C37—C38—C393.5 (5)
C2—C1—C5—C4−3.4 (3)C47—C37—C38—C39−178.0 (3)
C3—C4—C5—C6−178.1 (3)C37—C38—C39—C34−1.5 (5)
C3—C4—C5—C14.6 (3)C35—C34—C39—C38−0.6 (5)
C1—C5—C6—C7176.5 (3)C33—C34—C39—C38177.0 (3)
C4—C5—C6—C7−0.5 (6)C28—C29—C40—C41173.8 (3)
C5—C6—C7—C12−175.7 (3)C30—C29—C40—C41−3.6 (6)
C5—C6—C7—C80.7 (5)C29—C40—C41—C4210.0 (5)
C12—C7—C8—C91.3 (5)C29—C40—C41—C46−167.0 (3)
C6—C7—C8—C9−175.2 (3)C46—C41—C42—C433.5 (5)
C7—C8—C9—C101.3 (5)C40—C41—C42—C43−173.6 (3)
C8—C9—C10—C11−3.8 (5)C41—C42—C43—C440.0 (5)
C8—C9—C10—C20173.7 (3)C42—C43—C44—C45−2.4 (5)
C9—C10—C11—C124.1 (5)C42—C43—C44—C51172.6 (3)
C20—C10—C11—C12−173.4 (3)C43—C44—C45—C461.3 (5)
C10—C11—C12—C7−1.7 (5)C51—C44—C45—C46−173.7 (3)
C8—C7—C12—C11−1.1 (5)C44—C45—C46—C412.2 (5)
C6—C7—C12—C11175.6 (3)C42—C41—C46—C45−4.5 (5)
C1—C2—C13—C14174.1 (3)C40—C41—C46—C45172.8 (3)
C3—C2—C13—C14−3.0 (6)C38—C37—C47—C4923.2 (5)
C2—C13—C14—C1510.0 (5)C36—C37—C47—C49−158.4 (4)
C2—C13—C14—C19−169.6 (3)C38—C37—C47—C50−96.5 (4)
C19—C14—C15—C162.4 (5)C36—C37—C47—C5081.9 (4)
C13—C14—C15—C16−177.2 (3)C38—C37—C47—C48144.1 (4)
C14—C15—C16—C170.1 (5)C36—C37—C47—C48−37.5 (5)
C15—C16—C17—C18−2.2 (5)C45—C44—C51—C53−33.2 (4)
C15—C16—C17—C24174.6 (3)C43—C44—C51—C53152.1 (3)
C16—C17—C18—C191.5 (5)C45—C44—C51—C52−155.1 (3)
C24—C17—C18—C19−175.2 (3)C43—C44—C51—C5230.2 (4)
C17—C18—C19—C141.1 (5)C45—C44—C51—C5486.3 (4)
C15—C14—C19—C18−3.0 (5)C43—C44—C51—C54−88.4 (3)
C13—C14—C19—C18176.6 (3)O3—C55—C56—C586.5 (3)
C11—C10—C20—C21−147.0 (3)C56i—C55—C56—C58−173.5 (3)
C9—C10—C20—C2135.7 (4)O3—C55—C56—C57−176.10 (15)
C11—C10—C20—C23−24.8 (4)C56i—C55—C56—C573.90 (15)
C9—C10—C20—C23157.9 (3)C58—C56—C57—C57i167.2 (3)
C11—C10—C20—C2294.1 (4)C55—C56—C57—C57i−9.8 (4)
C9—C10—C20—C22−83.2 (4)C55—C56—C58—C59177.1 (3)
C18—C17—C24—C26−36.4 (4)C57—C56—C58—C590.4 (6)
C16—C17—C24—C26147.1 (3)C56—C58—C59—C6424.2 (5)
C18—C17—C24—C2783.0 (4)C56—C58—C59—C60−156.7 (3)
C16—C17—C24—C27−93.6 (4)C64—C59—C60—C61−2.5 (5)
C18—C17—C24—C25−158.0 (3)C58—C59—C60—C61178.3 (3)
C16—C17—C24—C2525.4 (4)C59—C60—C61—C621.8 (5)
O2—C28—C29—C401.9 (5)C60—C61—C62—C630.3 (5)
C32—C28—C29—C40−178.0 (3)C60—C61—C62—C65−177.1 (3)
O2—C28—C29—C30179.8 (3)C61—C62—C63—C64−1.7 (4)
C32—C28—C29—C300.0 (3)C65—C62—C63—C64175.7 (3)
C40—C29—C30—C31178.1 (3)C60—C59—C64—C631.1 (5)
C28—C29—C30—C310.5 (3)C58—C59—C64—C63−179.7 (3)
C29—C30—C31—C32−0.7 (3)C62—C63—C64—C591.0 (5)
O2—C28—C32—C330.3 (5)C61—C62—C65—C67−31.6 (4)
C29—C28—C32—C33−179.9 (3)C63—C62—C65—C67151.2 (3)
O2—C28—C32—C31179.7 (3)C61—C62—C65—C6887.2 (4)
C29—C28—C32—C31−0.4 (3)C63—C62—C65—C68−90.0 (3)
C30—C31—C32—C33−179.9 (3)C61—C62—C65—C66−153.7 (3)
C30—C31—C32—C280.7 (3)C63—C62—C65—C6629.0 (4)

Symmetry codes: (i) −x+1, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2667).

References

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