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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1114.
Published online 2008 May 17. doi:  10.1107/S1600536808014402
PMCID: PMC2961406

(−)-Kolavenic acid

Abstract

In the two, almost identical, mol­ecules in the asymmetric unit of the title compound [systematic name: (E)-3-methyl-5-(1,2,4a,5-tetra­methyl-1,2,3,4,4a,7,8,8a-octa­hydro­naphthalen-1-yl)pent-2-enoic acid], C20H32O2, the rings are trans fused. The cyclo­hexane ring has a chair conformation and the cyclo­hexene ring a distorted half-boat conformation. The two independent mol­ecules are connected into a dimer via O—H(...)O hydrogen bonds. The dimers are associated into supra­molecular chains along c via C—H(...)O contacts.

Related literature

For related structures, see: Puliti & Mattia (2000 [triangle]). For related literature, see: Lopes et al. (1987 [triangle]); Bomm et al. (1999 [triangle]); Messiano et al. (2008 [triangle]); Nascimento et al. (2004 [triangle]). For ring structure analysis, see: Cremer & Pople (1975 [triangle]); Spek (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1114-scheme1.jpg

Experimental

Crystal data

  • C20H32O2
  • M r = 304.46
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1114-efi1.jpg
  • a = 12.5122 (3) Å
  • b = 15.5439 (4) Å
  • c = 19.1969 (4) Å
  • V = 3733.57 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 291 (2) K
  • 0.42 × 0.20 × 0.18 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 48366 measured reflections
  • 6240 independent reflections
  • 3146 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.134
  • S = 1.00
  • 6240 reflections
  • 407 parameters
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: APEX2, COSMO and BIS (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014402/ng2455sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014402/ng2455Isup2.hkl

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

Acknowledgments

We thank FAPESP, CNPq and CAPES for financial support. Professor R. A. Burrow of the Federal University of Santa Maria is gratefully acknowledged for the collection of the intensity data.

supplementary crystallographic information

Comment

The title compound (I), Fig. 1, was studied as a part of an on-going screen of natural insecticides from Aristolochia species, which has become a promising route for the discovery of new compounds and/or botanical preparations which could be used in crop protection against Anticarsia gemmatalis H. (Lepidoptera: Noctuidae). Larvae of this insect represent the major defoliator pest of soybean crops in Brazil.

There are two almost identical independent molecules in the asymmetric unit, in fact superimposition of them, excluding H atoms, gives a rmsd of 0.016 Å (Spek, 2003). The major difference between the molecules is manifested in the relative orientations of the carboxylic acid residues so that in one molecule the carbonyl-O102 atom is syn to the methyl-C118 group whereas the opposite is true for the second independent molecule. In each molecule the rings are trans fused and the cyclohexane ring is in an almost undistorted chair conformation. The cyclohexene ring is in a distorted half-boat conformation, the ring-puckering parameters (Cremer & Pople, 1975) are q2 = 0.400 (3) Å (0.406 (3) Å for the second molecule), q3 = -0.341 (3) Å (-0.336 (3) Å), Q = 0.525 (2) ° (0.527 (2) °), and [var phi]2 = 106.6 (4)° (107.3 (4) °). The absolute configuration was established based on the [αD] = -41.1° (c 1.0, CHCl3) and the results reported in Bomm et al. (1999).

The independent molecules in (I) are connected via cooperative O—H···O contacts that form the eight-membered {···H—O—C=O}2 synthon, Table 1. The resultant dimeric aggregates are linked into a supramolecular chain along the c-direction via C212—H21R···O202 contacts, Fig. 2.

Experimental

Compound (I), (-)-kolavenic acid, was obtained from the hexane extract of the roots of Aristolochia malmeana Hoehne (Aristolochiaceae). Colorless crystals were obtained from the slow evaporation of a MeOH solution of (I) held at 283 K; m.p. 370–371 K. NMR (CDCl3, p.p.m.): δ 0.93 (1H, t, w1/2 = 7.0 Hz, H-1a), 1.36 (1H, m, H-1b), 1.99 (1H, m, H-2a), 1.94 (1H, m, H-2b), 5.13 (1H, br s, H-3), 1.66 (1H, dt, J = 13.0, 3.0 Hz, H-6a), 1.12 (1H, ddd, J = 13.0, 12.0, 4.2 Hz, H-6b), 1.33 (1H, m, H-7a), 1.39 (1H, m, H-7b), 1.37 (1H, m, H-8), 1.27 (1H, dd, J = 12.0, 1.5 Hz, H-10), 1.34 (1H, ddd, J = 14.0, 13.0, 4.5 Hz, H-11a), 1.48 (1H, ddd, J = 14.0, 12.5, 5.0 Hz, H-11b), 1.97 (1H, td, J = 13.0, 4.5 Hz, H-12a), 1.90 (1H, ddd, J = 13.0, 12.5, 5.0 Hz, H-12b), 5.62 (1H, dq, J = 2.5, 1.0 Hz, H-14), 2.11 (3H, br d, J = 1.0 Hz, H-16), 0.76 (3H, d, J = 6.0 Hz, H-17), 1.53 (3H, br s, H-18), 0.94 (3H, s, H-19), 0.68 (3H, s, H-20). [αD] = -41.1° in agreement with Bomm et al. (1999) and Messiano et al. (2008).

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were averaged in the final refinement. The H atoms were refined in the riding-model approximation with C—H = 0.93 - 0.98 Å and (0.82 for O—H), and with Uiso(H) = 1.5Ueq(methyl-C) or 1.2Ueq(remaining-C and –O).

Figures

Fig. 1.
The molecular structures of the two independent molecules in (I) showing atom labelling scheme and displacement ellipsoids at the 35% probability level (arbitrary spheres for the H atoms).
Fig. 2.
View of a supramolecular chain in (I) with O—H···O and C—H···O interactions shown as orange-dashed lines. Color code: O (red), N (blue), C (grey) & H (green).

Crystal data

C20H32O2F000 = 1344
Mr = 304.46Dx = 1.083 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9536 reflections
a = 12.5122 (3) Åθ = 2.3–21.8º
b = 15.5439 (4) ŵ = 0.07 mm1
c = 19.1969 (4) ÅT = 291 (2) K
V = 3733.57 (15) Å3Irregular, colourless
Z = 80.42 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer3146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Monochromator: graphiteθmax = 30.5º
T = 291(2) Kθmin = 2.7º
[var phi] and ω scansh = −17→17
Absorption correction: nonek = −22→21
48366 measured reflectionsl = −27→23
6240 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050  w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.11 e Å3
6240 reflectionsΔρmin = −0.12 e Å3
407 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Friedel pairs were merged
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
O1011.0346 (2)1.00268 (16)0.40732 (10)0.0971 (7)
H1011.05831.01090.44660.117*
O1020.92225 (17)0.92145 (12)0.46736 (8)0.0785 (5)
C1010.76320 (18)0.77650 (14)0.14588 (11)0.0507 (5)
C1020.65232 (18)0.81476 (17)0.12872 (11)0.0595 (6)
H1020.65140.87300.14840.071*
C1030.63223 (19)0.82452 (18)0.05042 (12)0.0629 (6)
H10C0.62960.76790.02930.076*
H10D0.56330.85170.04330.076*
C1040.71754 (19)0.87743 (17)0.01459 (11)0.0598 (6)
H10A0.71740.93510.03380.072*
H10B0.70090.8817−0.03460.072*
C1050.83006 (17)0.83772 (14)0.02341 (10)0.0517 (5)
C1060.9156 (2)0.89798 (18)−0.00476 (12)0.0668 (7)
C1071.0092 (2)0.90785 (19)0.02659 (14)0.0747 (8)
H1071.05810.94480.00560.090*
C1081.0430 (2)0.86495 (19)0.09252 (15)0.0764 (8)
H10G1.04940.90790.12900.092*
H10H1.11280.83910.08580.092*
C1090.96454 (18)0.79603 (17)0.11559 (13)0.0628 (6)
H10E0.97500.78370.16460.075*
H10F0.97740.74360.08960.075*
C1100.85005 (16)0.82610 (14)0.10350 (10)0.0473 (5)
H1100.84820.88470.12230.057*
C1110.7674 (2)0.67820 (15)0.13196 (13)0.0672 (7)
H11E0.73900.66630.08650.101*
H11F0.72560.64870.16650.101*
H11G0.84010.65880.13430.101*
C1120.5582 (2)0.7661 (2)0.16212 (15)0.0902 (9)
H11N0.55480.70890.14340.135*
H11O0.49270.79580.15210.135*
H11P0.56840.76320.21160.135*
C1130.8360 (2)0.75442 (18)−0.01978 (12)0.0678 (7)
H11H0.90040.7239−0.00840.102*
H11I0.83600.7685−0.06850.102*
H11J0.77530.7189−0.00940.102*
C1140.8941 (3)0.9435 (2)−0.07248 (15)0.1023 (11)
H11Q0.95530.9772−0.08520.153*
H11R0.83310.9804−0.06730.153*
H11S0.88010.9018−0.10820.153*
C1150.7858 (2)0.78741 (15)0.22501 (11)0.0609 (6)
H11A0.73460.75250.25040.073*
H11B0.85620.76420.23460.073*
C1160.7812 (3)0.87882 (18)0.25429 (12)0.0834 (9)
H11C0.82470.91610.22530.100*
H11D0.70810.89940.25190.100*
C1170.8197 (3)0.88539 (18)0.32881 (11)0.0705 (7)
C1180.7538 (3)0.8379 (2)0.38179 (14)0.0987 (10)
H11K0.77050.85880.42760.148*
H11L0.76950.77750.37920.148*
H11M0.67930.84700.37240.148*
C1190.9048 (3)0.93132 (18)0.34285 (12)0.0740 (8)
H1190.93870.95510.30430.089*
C1200.9549 (2)0.95094 (17)0.41065 (12)0.0661 (7)
O2011.01800 (18)0.96623 (14)0.58806 (10)0.0910 (6)
H2011.00010.94860.54950.109*
O2021.13450 (18)1.03856 (14)0.52400 (10)0.0910 (6)
C2011.19128 (18)1.20921 (15)0.85454 (11)0.0546 (6)
C2021.2484 (2)1.15676 (16)0.91200 (12)0.0658 (7)
H2021.29471.11540.88800.079*
C2031.3211 (2)1.21238 (19)0.95685 (12)0.0782 (8)
H20E1.27781.25350.98230.094*
H20F1.35711.17610.99060.094*
C2041.4038 (2)1.26039 (17)0.91493 (12)0.0706 (7)
H20A1.45091.21920.89260.085*
H20B1.44681.29520.94620.085*
C2051.3545 (2)1.31906 (15)0.85873 (10)0.0560 (6)
C2061.4416 (2)1.35422 (15)0.81050 (13)0.0636 (6)
C2071.4261 (2)1.36223 (17)0.74262 (13)0.0719 (7)
H2071.48241.38440.71650.086*
C2081.3270 (2)1.33897 (19)0.70427 (12)0.0768 (8)
H20G1.34201.29080.67370.092*
H20H1.30541.38720.67550.092*
C2091.2348 (2)1.31491 (18)0.75260 (12)0.0658 (6)
H20C1.18241.28140.72720.079*
H20D1.20021.36670.76950.079*
C2101.27730 (17)1.26243 (14)0.81438 (10)0.0496 (5)
H2101.32371.21900.79310.060*
C2111.1011 (2)1.2658 (2)0.88417 (15)0.0793 (8)
H21H1.07771.30570.84920.119*
H21I1.12701.29690.92390.119*
H21J1.04221.23000.89790.119*
C2121.1724 (3)1.1040 (3)0.95738 (18)0.1120 (12)
H21Q1.13141.14200.98640.168*
H21R1.21291.06550.98610.168*
H21S1.12501.07150.92810.168*
C2131.3019 (3)1.39861 (18)0.89400 (14)0.0816 (8)
H21E1.35661.43480.91330.122*
H21F1.25501.37970.93050.122*
H21G1.26191.43040.86000.122*
C2141.5467 (3)1.3827 (2)0.84228 (17)0.0938 (10)
H21N1.58921.41080.80750.141*
H21O1.58441.33330.85960.141*
H21P1.53301.42180.87990.141*
C2151.1350 (2)1.14633 (17)0.80335 (13)0.0666 (7)
H21A1.07931.11680.82910.080*
H21B1.09981.18080.76800.080*
C2161.2006 (2)1.07826 (18)0.76594 (14)0.0746 (7)
H21C1.26201.10520.74410.089*
H21D1.22671.03670.79960.089*
C2171.1357 (2)1.03233 (16)0.71123 (14)0.0678 (7)
C2181.0479 (3)0.9751 (2)0.73784 (15)0.1064 (12)
H21K1.04570.92330.71070.160*
H21L0.98071.00450.73410.160*
H21M1.06130.96100.78570.160*
C2191.1563 (2)1.04597 (17)0.64412 (14)0.0721 (7)
H2191.21551.08050.63530.087*
C2201.1003 (2)1.01506 (17)0.58192 (14)0.0679 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1010.1228 (18)0.1026 (16)0.0661 (11)−0.0288 (16)−0.0021 (12)0.0042 (11)
O1020.1089 (14)0.0789 (12)0.0478 (8)−0.0094 (11)−0.0006 (9)0.0002 (8)
C1010.0526 (13)0.0479 (13)0.0516 (11)0.0024 (11)0.0030 (9)−0.0041 (10)
C1020.0501 (13)0.0707 (16)0.0576 (12)0.0062 (13)0.0043 (10)−0.0132 (11)
C1030.0501 (13)0.0779 (17)0.0608 (12)0.0097 (13)−0.0028 (10)−0.0154 (12)
C1040.0632 (15)0.0679 (16)0.0484 (11)0.0089 (13)−0.0080 (10)−0.0058 (11)
C1050.0519 (13)0.0542 (14)0.0489 (10)−0.0026 (11)0.0019 (9)−0.0062 (10)
C1060.0736 (18)0.0674 (17)0.0595 (13)−0.0055 (14)0.0091 (12)−0.0003 (11)
C1070.0674 (18)0.0759 (19)0.0808 (17)−0.0213 (15)0.0112 (14)0.0013 (15)
C1080.0547 (15)0.087 (2)0.0875 (18)−0.0099 (15)−0.0005 (13)−0.0076 (15)
C1090.0517 (14)0.0677 (17)0.0690 (13)0.0005 (13)−0.0041 (11)0.0012 (12)
C1100.0466 (12)0.0445 (12)0.0508 (10)0.0026 (10)−0.0005 (9)−0.0047 (9)
C1110.0730 (17)0.0517 (15)0.0769 (15)−0.0064 (13)0.0081 (13)−0.0040 (12)
C1120.0582 (16)0.130 (3)0.0824 (18)−0.0045 (18)0.0165 (14)−0.0002 (18)
C1130.0678 (16)0.0763 (17)0.0595 (13)−0.0024 (14)0.0094 (12)−0.0217 (12)
C1140.116 (3)0.114 (3)0.0773 (18)−0.026 (2)0.0037 (17)0.0291 (18)
C1150.0730 (16)0.0609 (15)0.0486 (11)0.0045 (13)−0.0012 (10)0.0023 (10)
C1160.134 (3)0.0673 (17)0.0486 (12)0.0166 (18)−0.0167 (14)−0.0087 (11)
C1170.103 (2)0.0588 (16)0.0491 (12)0.0123 (17)−0.0046 (13)−0.0020 (11)
C1180.115 (2)0.126 (3)0.0552 (14)−0.016 (2)0.0099 (15)−0.0095 (16)
C1190.117 (2)0.0600 (16)0.0451 (11)0.0014 (18)0.0042 (13)0.0016 (11)
C1200.092 (2)0.0499 (14)0.0563 (13)0.0022 (15)0.0011 (13)0.0026 (11)
O2010.1098 (16)0.0939 (15)0.0694 (11)−0.0434 (13)−0.0103 (11)−0.0026 (11)
O2020.1104 (16)0.0877 (14)0.0749 (11)−0.0261 (13)0.0126 (11)−0.0057 (10)
C2010.0578 (13)0.0531 (14)0.0528 (11)0.0057 (12)−0.0021 (10)0.0010 (10)
C2020.0770 (17)0.0646 (16)0.0557 (12)−0.0001 (14)−0.0019 (12)0.0094 (11)
C2030.101 (2)0.088 (2)0.0464 (11)0.0010 (17)−0.0109 (13)0.0033 (12)
C2040.0850 (17)0.0684 (16)0.0584 (12)−0.0051 (15)−0.0223 (13)−0.0048 (12)
C2050.0695 (15)0.0471 (13)0.0513 (10)0.0029 (12)−0.0058 (11)−0.0102 (9)
C2060.0709 (16)0.0483 (14)0.0717 (15)0.0015 (13)−0.0016 (12)−0.0070 (11)
C2070.0831 (19)0.0599 (16)0.0726 (16)−0.0003 (14)0.0096 (14)0.0064 (12)
C2080.088 (2)0.086 (2)0.0563 (13)0.0049 (17)−0.0013 (13)0.0107 (13)
C2090.0720 (16)0.0679 (16)0.0577 (13)0.0086 (14)−0.0099 (11)0.0063 (12)
C2100.0562 (13)0.0474 (13)0.0452 (10)0.0077 (11)−0.0029 (9)−0.0053 (9)
C2110.0693 (16)0.084 (2)0.0841 (16)0.0134 (16)0.0101 (14)−0.0062 (15)
C2120.103 (2)0.129 (3)0.105 (2)−0.019 (2)0.0017 (19)0.051 (2)
C2130.104 (2)0.0619 (16)0.0795 (16)0.0050 (16)0.0102 (16)−0.0254 (13)
C2140.091 (2)0.085 (2)0.105 (2)−0.0210 (19)−0.0075 (18)−0.0182 (18)
C2150.0614 (15)0.0675 (16)0.0710 (14)−0.0013 (14)−0.0095 (12)−0.0035 (12)
C2160.0775 (18)0.0654 (17)0.0807 (16)−0.0008 (15)−0.0161 (14)−0.0152 (13)
C2170.0700 (16)0.0535 (15)0.0798 (16)−0.0062 (14)−0.0103 (13)−0.0049 (12)
C2180.141 (3)0.101 (2)0.0775 (18)−0.054 (2)−0.020 (2)0.0130 (17)
C2190.0713 (17)0.0640 (17)0.0810 (16)−0.0178 (14)0.0026 (14)−0.0170 (13)
C2200.0780 (18)0.0523 (15)0.0736 (16)−0.0091 (14)0.0035 (14)−0.0079 (12)

Geometric parameters (Å, °)

O101—C1201.283 (3)O201—C2201.285 (3)
O101—H1010.8200O201—H2010.8200
O102—C1201.250 (3)O202—C2201.246 (3)
C101—C1021.545 (3)C201—C2111.540 (3)
C101—C1111.552 (3)C201—C2021.547 (3)
C101—C1151.554 (3)C201—C2151.555 (3)
C101—C1101.561 (3)C201—C2101.561 (3)
C102—C1031.532 (3)C202—C2031.522 (4)
C102—C1121.540 (4)C202—C2121.528 (4)
C102—H1020.9800C202—H2020.9800
C103—C1041.513 (4)C203—C2041.509 (4)
C103—H10C0.9700C203—H20E0.9700
C103—H10D0.9700C203—H20F0.9700
C104—C1051.546 (3)C204—C2051.542 (3)
C104—H10A0.9700C204—H20A0.9700
C104—H10B0.9700C204—H20B0.9700
C105—C1061.522 (4)C205—C2061.531 (3)
C105—C1131.539 (3)C205—C2131.555 (3)
C105—C1101.568 (3)C205—C2101.560 (3)
C106—C1071.325 (4)C206—C2071.323 (3)
C106—C1141.504 (4)C206—C2141.516 (4)
C107—C1081.492 (4)C207—C2081.487 (4)
C107—H1070.9300C207—H2070.9300
C108—C1091.519 (4)C208—C2091.526 (4)
C108—H10G0.9700C208—H20G0.9700
C108—H10H0.9700C208—H20H0.9700
C109—C1101.525 (3)C209—C2101.534 (3)
C109—H10E0.9700C209—H20C0.9700
C109—H10F0.9700C209—H20D0.9700
C110—H1100.9800C210—H2100.9800
C111—H11E0.9600C211—H21H0.9600
C111—H11F0.9600C211—H21I0.9600
C111—H11G0.9600C211—H21J0.9600
C112—H11N0.9600C212—H21Q0.9600
C112—H11O0.9600C212—H21R0.9600
C112—H11P0.9600C212—H21S0.9600
C113—H11H0.9600C213—H21E0.9600
C113—H11I0.9600C213—H21F0.9600
C113—H11J0.9600C213—H21G0.9600
C114—H11Q0.9600C214—H21N0.9600
C114—H11R0.9600C214—H21O0.9600
C114—H11S0.9600C214—H21P0.9600
C115—C1161.529 (4)C215—C2161.519 (3)
C115—H11A0.9700C215—H21A0.9700
C115—H11B0.9700C215—H21B0.9700
C116—C1171.513 (3)C216—C2171.507 (3)
C116—H11C0.9700C216—H21C0.9700
C116—H11D0.9700C216—H21D0.9700
C117—C1191.310 (4)C217—C2191.331 (4)
C117—C1181.503 (4)C217—C2181.503 (4)
C118—H11K0.9600C218—H21K0.9600
C118—H11L0.9600C218—H21L0.9600
C118—H11M0.9600C218—H21M0.9600
C119—C1201.476 (4)C219—C2201.465 (4)
C119—H1190.9300C219—H2190.9300
C120—O101—H101109.5C220—O201—H201109.5
C102—C101—C111111.9 (2)C211—C201—C202112.09 (19)
C102—C101—C115109.25 (18)C211—C201—C215105.1 (2)
C111—C101—C115105.63 (19)C202—C201—C215109.19 (19)
C102—C101—C110108.90 (17)C211—C201—C210112.66 (19)
C111—C101—C110111.90 (18)C202—C201—C210108.25 (18)
C115—C101—C110109.20 (18)C215—C201—C210109.47 (18)
C103—C102—C112109.4 (2)C203—C202—C212110.8 (2)
C103—C102—C101113.24 (18)C203—C202—C201112.3 (2)
C112—C102—C101114.1 (2)C212—C202—C201113.7 (2)
C103—C102—H102106.5C203—C202—H202106.5
C112—C102—H102106.5C212—C202—H202106.5
C101—C102—H102106.5C201—C202—H202106.5
C104—C103—C102112.6 (2)C204—C203—C202112.92 (19)
C104—C103—H10C109.1C204—C203—H20E109.0
C102—C103—H10C109.1C202—C203—H20E109.0
C104—C103—H10D109.1C204—C203—H20F109.0
C102—C103—H10D109.1C202—C203—H20F109.0
H10C—C103—H10D107.8H20E—C203—H20F107.8
C103—C104—C105112.06 (19)C203—C204—C205113.0 (2)
C103—C104—H10A109.2C203—C204—H20A109.0
C105—C104—H10A109.2C205—C204—H20A109.0
C103—C104—H10B109.2C203—C204—H20B109.0
C105—C104—H10B109.2C205—C204—H20B109.0
H10A—C104—H10B107.9H20A—C204—H20B107.8
C106—C105—C113107.00 (18)C206—C205—C204110.4 (2)
C106—C105—C104110.85 (19)C206—C205—C213106.3 (2)
C113—C105—C104108.70 (18)C204—C205—C213109.56 (19)
C106—C105—C110107.88 (18)C206—C205—C210108.19 (17)
C113—C105—C110115.05 (19)C204—C205—C210107.22 (19)
C104—C105—C110107.37 (16)C213—C205—C210115.1 (2)
C107—C106—C114119.8 (3)C207—C206—C214119.7 (3)
C107—C106—C105122.1 (2)C207—C206—C205121.7 (2)
C114—C106—C105118.1 (2)C214—C206—C205118.6 (2)
C106—C107—C108125.7 (2)C206—C207—C208125.9 (3)
C106—C107—H107117.1C206—C207—H207117.0
C108—C107—H107117.1C208—C207—H207117.0
C107—C108—C109112.3 (2)C207—C208—C209112.9 (2)
C107—C108—H10G109.2C207—C208—H20G109.0
C109—C108—H10G109.2C209—C208—H20G109.0
C107—C108—H10H109.2C207—C208—H20H109.0
C109—C108—H10H109.2C209—C208—H20H109.0
H10G—C108—H10H107.9H20G—C208—H20H107.8
C108—C109—C110110.3 (2)C208—C209—C210109.8 (2)
C108—C109—H10E109.6C208—C209—H20C109.7
C110—C109—H10E109.6C210—C209—H20C109.7
C108—C109—H10F109.6C208—C209—H20D109.7
C110—C109—H10F109.6C210—C209—H20D109.7
H10E—C109—H10F108.1H20C—C209—H20D108.2
C109—C110—C101115.04 (18)C209—C210—C205109.65 (19)
C109—C110—C105109.55 (17)C209—C210—C201115.13 (18)
C101—C110—C105117.18 (17)C205—C210—C201117.16 (17)
C109—C110—H110104.5C209—C210—H210104.4
C101—C110—H110104.5C205—C210—H210104.4
C105—C110—H110104.5C201—C210—H210104.4
C101—C111—H11E109.5C201—C211—H21H109.5
C101—C111—H11F109.5C201—C211—H21I109.5
H11E—C111—H11F109.5H21H—C211—H21I109.5
C101—C111—H11G109.5C201—C211—H21J109.5
H11E—C111—H11G109.5H21H—C211—H21J109.5
H11F—C111—H11G109.5H21I—C211—H21J109.5
C102—C112—H11N109.5C202—C212—H21Q109.5
C102—C112—H11O109.5C202—C212—H21R109.5
H11N—C112—H11O109.5H21Q—C212—H21R109.5
C102—C112—H11P109.5C202—C212—H21S109.5
H11N—C112—H11P109.5H21Q—C212—H21S109.5
H11O—C112—H11P109.5H21R—C212—H21S109.5
C105—C113—H11H109.5C205—C213—H21E109.5
C105—C113—H11I109.5C205—C213—H21F109.5
H11H—C113—H11I109.5H21E—C213—H21F109.5
C105—C113—H11J109.5C205—C213—H21G109.5
H11H—C113—H11J109.5H21E—C213—H21G109.5
H11I—C113—H11J109.5H21F—C213—H21G109.5
C106—C114—H11Q109.5C206—C214—H21N109.5
C106—C114—H11R109.5C206—C214—H21O109.5
H11Q—C114—H11R109.5H21N—C214—H21O109.5
C106—C114—H11S109.5C206—C214—H21P109.5
H11Q—C114—H11S109.5H21N—C214—H21P109.5
H11R—C114—H11S109.5H21O—C214—H21P109.5
C116—C115—C101116.98 (19)C216—C215—C201119.5 (2)
C116—C115—H11A108.1C216—C215—H21A107.5
C101—C115—H11A108.1C201—C215—H21A107.5
C116—C115—H11B108.1C216—C215—H21B107.5
C101—C115—H11B108.1C201—C215—H21B107.5
H11A—C115—H11B107.3H21A—C215—H21B107.0
C117—C116—C115113.5 (2)C217—C216—C215111.6 (2)
C117—C116—H11C108.9C217—C216—H21C109.3
C115—C116—H11C108.9C215—C216—H21C109.3
C117—C116—H11D108.9C217—C216—H21D109.3
C115—C116—H11D108.9C215—C216—H21D109.3
H11C—C116—H11D107.7H21C—C216—H21D108.0
C119—C117—C118125.1 (2)C219—C217—C218124.4 (2)
C119—C117—C116119.3 (3)C219—C217—C216119.6 (2)
C118—C117—C116115.6 (3)C218—C217—C216115.9 (2)
C117—C118—H11K109.5C217—C218—H21K109.5
C117—C118—H11L109.5C217—C218—H21L109.5
H11K—C118—H11L109.5H21K—C218—H21L109.5
C117—C118—H11M109.5C217—C218—H21M109.5
H11K—C118—H11M109.5H21K—C218—H21M109.5
H11L—C118—H11M109.5H21L—C218—H21M109.5
C117—C119—C120129.7 (2)C217—C219—C220130.1 (3)
C117—C119—H119115.1C217—C219—H219115.0
C120—C119—H119115.1C220—C219—H219115.0
O102—C120—O101121.8 (2)O202—C220—O201122.0 (2)
O102—C120—C119123.6 (3)O202—C220—C219117.8 (2)
O101—C120—C119114.6 (2)O201—C220—C219120.1 (2)
C111—C101—C102—C103−75.5 (3)C211—C201—C202—C203−73.9 (3)
C115—C101—C102—C103167.9 (2)C215—C201—C202—C203170.1 (2)
C110—C101—C102—C10348.7 (3)C210—C201—C202—C20351.0 (3)
C111—C101—C102—C11250.5 (3)C211—C201—C202—C21252.9 (3)
C115—C101—C102—C112−66.1 (3)C215—C201—C202—C212−63.1 (3)
C110—C101—C102—C112174.7 (2)C210—C201—C202—C212177.8 (2)
C112—C102—C103—C104175.9 (2)C212—C202—C203—C204175.3 (3)
C101—C102—C103—C104−55.6 (3)C201—C202—C203—C204−56.3 (3)
C102—C103—C104—C10559.0 (3)C202—C203—C204—C20557.8 (3)
C103—C104—C105—C106−172.56 (19)C203—C204—C205—C206−170.7 (2)
C103—C104—C105—C11370.1 (2)C203—C204—C205—C21372.6 (3)
C103—C104—C105—C110−55.0 (2)C203—C204—C205—C210−53.0 (3)
C113—C105—C106—C107−100.2 (3)C204—C205—C206—C207141.0 (2)
C104—C105—C106—C107141.4 (3)C213—C205—C206—C207−100.2 (3)
C110—C105—C106—C10724.1 (3)C210—C205—C206—C20724.0 (3)
C113—C105—C106—C11476.4 (3)C204—C205—C206—C214−40.7 (3)
C104—C105—C106—C114−42.0 (3)C213—C205—C206—C21478.1 (3)
C110—C105—C106—C114−159.3 (2)C210—C205—C206—C214−157.8 (2)
C114—C106—C107—C108−178.1 (3)C214—C206—C207—C208−178.7 (3)
C105—C106—C107—C108−1.5 (4)C205—C206—C207—C208−0.4 (4)
C106—C107—C108—C1099.1 (4)C206—C207—C208—C2097.9 (4)
C107—C108—C109—C110−40.1 (3)C207—C208—C209—C210−39.0 (3)
C108—C109—C110—C101−161.0 (2)C208—C209—C210—C20564.0 (3)
C108—C109—C110—C10564.5 (3)C208—C209—C210—C201−161.3 (2)
C102—C101—C110—C109179.40 (19)C206—C205—C210—C209−54.8 (2)
C111—C101—C110—C109−56.4 (3)C204—C205—C210—C209−173.93 (19)
C115—C101—C110—C10960.2 (2)C213—C205—C210—C20963.9 (3)
C102—C101—C110—C105−49.7 (2)C206—C205—C210—C201171.57 (18)
C111—C101—C110—C10574.5 (2)C204—C205—C210—C20152.4 (3)
C115—C101—C110—C105−168.90 (19)C213—C205—C210—C201−69.7 (3)
C106—C105—C110—C109−54.5 (2)C211—C201—C210—C209−58.6 (3)
C113—C105—C110—C10964.8 (2)C202—C201—C210—C209176.90 (19)
C104—C105—C110—C109−174.01 (18)C215—C201—C210—C20958.0 (2)
C106—C105—C110—C101172.11 (18)C211—C201—C210—C20572.6 (2)
C113—C105—C110—C101−68.6 (2)C202—C201—C210—C205−52.0 (2)
C104—C105—C110—C10152.6 (2)C215—C201—C210—C205−170.88 (19)
C102—C101—C115—C116−56.7 (3)C211—C201—C215—C216−178.0 (2)
C111—C101—C115—C116−177.1 (2)C202—C201—C215—C216−57.6 (3)
C110—C101—C115—C11662.3 (3)C210—C201—C215—C21660.8 (3)
C101—C115—C116—C117−171.6 (2)C201—C215—C216—C217−171.8 (2)
C115—C116—C117—C119116.5 (3)C215—C216—C217—C219109.5 (3)
C115—C116—C117—C118−64.2 (4)C215—C216—C217—C218−68.7 (3)
C118—C117—C119—C120−2.4 (5)C218—C217—C219—C2203.3 (5)
C116—C117—C119—C120176.8 (3)C216—C217—C219—C220−174.7 (3)
C117—C119—C120—O1022.9 (5)C217—C219—C220—O202178.5 (3)
C117—C119—C120—O101−175.8 (3)C217—C219—C220—O201−0.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O101—H101···O2020.821.822.625 (3)168
O201—H201···O1020.821.902.700 (2)164
C212—H21R···O202i0.962.603.519 (4)159

Symmetry codes: (i) −x+5/2, −y+2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2455).

References

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