#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/64/2226430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226430
loop_
_publ_author_name
'Suwancharoen, Sunisa'
'Tommeurd, Wantanee'
'Phurat, Chuttree'
'Muangsin, Nongnuj'
'Pornpakakul, Surachai'
_publ_section_title
;
 Acanthoic acid
;
_journal_coeditor_code           FJ2300
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1531
_journal_paper_doi               10.1107/S1600536810019483
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H30 O2'
_chemical_formula_moiety         'C20 H30 O2'
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.44
_chemical_name_systematic
;
(1R,4aR,7S,8aS,10aS)-1,4a,7-trimethyl-7-
vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic
acid
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8697(16)
_cell_length_b                   12.8697(16)
_cell_length_c                   21.768(2)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.24
_cell_measurement_theta_min      1.58
_cell_volume                     3605.4(7)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.878
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         Mo
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21616
_diffrn_reflns_theta_full        30.24
_diffrn_reflns_theta_max         30.24
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0853P)²+1.0669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                3830
_reflns_number_total             4824
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2300.cif
_cod_data_source_block           I
_cod_original_cell_volume        3605.5(7)
_cod_database_code               2226430
_cod_database_fobs_code          2226430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+3/4'
'y, -x, z+1/4'
'-x, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2020(3) 0.6538(3) 0.07071(16) 0.0369(7) Uani d . 1 . .
H H1A 0.133 0.6753 0.0833 0.044 Uiso calc R 1 . .
H H1B 0.208 0.6659 0.0269 0.044 Uiso calc R 1 . .
C C2 0.2143(3) 0.5365(3) 0.08320(18) 0.0395(8) Uani d . 1 . .
H H2A 0.1582 0.4991 0.0633 0.047 Uiso calc R 1 . .
H H2B 0.2793 0.5125 0.0657 0.047 Uiso calc R 1 . .
C C3 0.2130(3) 0.5131(3) 0.15123(18) 0.0389(7) Uani d . 1 . .
H H3A 0.2246 0.4393 0.157 0.047 Uiso calc R 1 . .
H H3B 0.1446 0.5293 0.1673 0.047 Uiso calc R 1 . .
C C4 0.2946(2) 0.5735(2) 0.18865(14) 0.0283(6) Uani d . 1 . .
C C5 0.2819(2) 0.6927(2) 0.17370(13) 0.0257(6) Uani d . 1 . .
H H5 0.2117 0.7103 0.1876 0.031 Uiso calc R 1 . .
C C6 0.3540(2) 0.7641(2) 0.21113(15) 0.0332(6) Uani d . 1 . .
H H6A 0.4256 0.7438 0.2041 0.04 Uiso calc R 1 . .
H H6B 0.3393 0.7553 0.2545 0.04 Uiso calc R 1 . .
C C7 0.3407(3) 0.8792(3) 0.19396(17) 0.0384(7) Uani d . 1 . .
H H7A 0.3387 0.9204 0.2313 0.046 Uiso calc R 1 . .
H H7B 0.4005 0.9015 0.1703 0.046 Uiso calc R 1 . .
C C8 0.2417(2) 0.9002(2) 0.15664(15) 0.0309(6) Uani d . 1 . .
H H8 0.182 0.8755 0.1805 0.037 Uiso calc R 1 . .
C C9 0.2483(2) 0.8366(2) 0.09816(14) 0.0307(6) Uani d . 1 . .
C C10 0.2833(2) 0.7217(2) 0.10447(13) 0.0261(6) Uani d . 1 . .
C C11 0.2242(3) 0.8779(3) 0.04395(17) 0.0439(8) Uani d . 1 . .
H H11 0.2322 0.8361 0.0094 0.053 Uiso calc R 1 . .
C C12 0.1851(4) 0.9870(3) 0.03404(18) 0.0535(10) Uani d . 1 . .
H H12A 0.1287 0.9856 0.0045 0.064 Uiso calc R 1 . .
H H12B 0.2406 1.0289 0.0169 0.064 Uiso calc R 1 . .
C C13 0.1463(3) 1.0377(3) 0.09429(18) 0.0481(9) Uani d . 1 . .
C C14 0.2265(3) 1.0152(3) 0.14356(18) 0.0436(8) Uani d . 1 . .
H H14A 0.2055 1.0496 0.1812 0.052 Uiso calc R 1 . .
H H14B 0.2925 1.0447 0.131 0.052 Uiso calc R 1 . .
C C15 0.1282(5) 1.1516(4) 0.0829(2) 0.0853(19) Uani d . 1 . .
H H15 0.0933 1.1636 0.0461 0.102 Uiso calc R 1 . .
C C16 0.1472(8) 1.2286(4) 0.1089(3) 0.123(3) Uani d . 1 . .
H H16A 0.182 1.2263 0.1463 0.147 Uiso calc R 1 . .
H H16B 0.1275 1.2921 0.0922 0.147 Uiso calc R 1 . .
C C17 0.0409(3) 0.9895(4) 0.1120(2) 0.0610(12) Uani d . 1 . .
H H17A 0.0484 0.9156 0.1159 0.092 Uiso calc R 1 . .
H H17B -0.0093 1.0047 0.0806 0.092 Uiso calc R 1 . .
H H17C 0.018 1.0181 0.1504 0.092 Uiso calc R 1 . .
C C18 0.2726(3) 0.5543(3) 0.25738(17) 0.0429(8) Uani d . 1 . .
H H18A 0.2051 0.5811 0.2676 0.064 Uiso calc R 1 . .
H H18B 0.3243 0.5888 0.2817 0.064 Uiso calc R 1 . .
H H18C 0.2745 0.481 0.2656 0.064 Uiso calc R 1 . .
C C19 0.4032(2) 0.5295(2) 0.17572(14) 0.0312(6) Uani d . 1 . .
C C20 0.3915(2) 0.7082(2) 0.07483(14) 0.0332(7) Uani d . 1 . .
H H20A 0.3909 0.7371 0.0342 0.05 Uiso calc R 1 . .
H H20B 0.4083 0.6356 0.0726 0.05 Uiso calc R 1 . .
H H20C 0.4427 0.7434 0.0993 0.05 Uiso calc R 1 . .
O O1 0.42045(17) 0.46242(17) 0.13726(11) 0.0352(5) Uani d . 1 . .
O O2 0.47604(18) 0.5668(2) 0.21170(12) 0.0437(6) Uani d . 1 . .
H H2 0.532 0.5404 0.2027 0.066 Uiso calc R 1 . .
C C1' 0.8991(3) 0.6408(3) 0.09529(17) 0.0415(8) Uani d . 1 . .
H H1'1 0.9703 0.6216 0.086 0.05 Uiso calc R 1 . .
H H1'2 0.8959 0.716 0.0969 0.05 Uiso calc R 1 . .
C C2' 0.8713(3) 0.5981(3) 0.15830(16) 0.0468(9) Uani d . 1 . .
H H2'1 0.9222 0.6216 0.1881 0.056 Uiso calc R 1 . .
H H2'2 0.8039 0.6248 0.1706 0.056 Uiso calc R 1 . .
C C3' 0.8682(3) 0.4805(3) 0.15808(16) 0.0429(8) Uani d . 1 . .
H H3'1 0.8463 0.4564 0.1983 0.051 Uiso calc R 1 . .
H H3'2 0.9377 0.4542 0.1507 0.051 Uiso calc R 1 . .
C C4' 0.7945(2) 0.4360(2) 0.10933(15) 0.0322(6) Uani d . 1 . .
C C5' 0.8256(2) 0.4816(2) 0.04527(14) 0.0271(6) Uani d . 1 . .
H H5' 0.8981 0.4603 0.0397 0.033 Uiso calc R 1 . .
C C6' 0.7679(2) 0.4328(2) -0.00971(15) 0.0316(6) Uani d . 1 . .
H H6'1 0.7876 0.3603 -0.0131 0.038 Uiso calc R 1 . .
H H6'2 0.6937 0.4357 -0.0021 0.038 Uiso calc R 1 . .
C C7' 0.7919(2) 0.4880(2) -0.07080(14) 0.0299(6) Uani d . 1 . .
H H7'1 0.7984 0.4365 -0.1031 0.036 Uiso calc R 1 . .
H H7'2 0.7342 0.5333 -0.0813 0.036 Uiso calc R 1 . .
C C8' 0.8922(2) 0.5526(2) -0.06797(13) 0.0257(6) Uani d . 1 . .
H H8' 0.9494 0.5068 -0.0557 0.031 Uiso calc R 1 . .
C C9' 0.8790(2) 0.6354(2) -0.01921(15) 0.0301(6) Uani d . 1 . .
C C10' 0.8288(2) 0.6029(2) 0.04225(14) 0.0285(6) Uani d . 1 . .
C C11' 0.9096(3) 0.7328(2) -0.02861(17) 0.0402(8) Uani d . 1 . .
H H11' 0.8987 0.7801 0.003 0.048 Uiso calc R 1 . .
C C12' 0.9605(3) 0.7729(3) -0.08629(19) 0.0435(8) Uani d . 1 . .
H H12C 1.018 0.8177 -0.0751 0.052 Uiso calc R 1 . .
H H12D 0.9106 0.8144 -0.109 0.052 Uiso calc R 1 . .
C C13' 1.0012(2) 0.6844(3) -0.12842(16) 0.0355(7) Uani d . 1 . .
C C14' 0.9179(2) 0.5993(2) -0.13061(14) 0.0332(6) Uani d . 1 . .
H H14C 0.8549 0.6283 -0.1481 0.04 Uiso calc R 1 . .
H H14D 0.9414 0.5442 -0.1576 0.04 Uiso calc R 1 . .
C C15' 1.0229(3) 0.7320(3) -0.1906(2) 0.0536(10) Uani d . 1 . .
H H15' 1.0743 0.7829 -0.1908 0.064 Uiso calc R 1 . .
C C16' 0.9827(4) 0.7138(5) -0.2418(2) 0.0762(15) Uani d . 1 . .
H H16C 0.9307 0.664 -0.2453 0.091 Uiso calc R 1 . .
H H16D 1.0047 0.7502 -0.2763 0.091 Uiso calc R 1 . .
C C17' 1.1037(2) 0.6415(3) -0.10289(17) 0.0401(8) Uani d . 1 . .
H H17D 1.1267 0.5847 -0.128 0.06 Uiso calc R 1 . .
H H17E 1.0932 0.6176 -0.0616 0.06 Uiso calc R 1 . .
H H17F 1.1553 0.6954 -0.1031 0.06 Uiso calc R 1 . .
C C18' 0.8066(3) 0.3167(3) 0.10861(19) 0.0447(8) Uani d . 1 . .
H H18D 0.7936 0.2897 0.149 0.067 Uiso calc R 1 . .
H H18E 0.876 0.2989 0.0963 0.067 Uiso calc R 1 . .
H H18F 0.7579 0.2872 0.0801 0.067 Uiso calc R 1 . .
C C19' 0.6819(2) 0.4561(2) 0.12987(15) 0.0318(6) Uani d . 1 . .
C C20' 0.7191(2) 0.6510(2) 0.04652(16) 0.0338(7) Uani d . 1 . .
H H20D 0.723 0.7242 0.0383 0.051 Uiso calc R 1 . .
H H20E 0.6916 0.6401 0.087 0.051 Uiso calc R 1 . .
H H20F 0.6743 0.6185 0.0169 0.051 Uiso calc R 1 . .
O O1' 0.66053(17) 0.4932(2) 0.17988(11) 0.0402(5) Uani d . 1 . .
O O2' 0.61042(16) 0.42401(18) 0.09132(11) 0.0362(5) Uani d . 1 . .
H H2' 0.5527 0.4336 0.1063 0.054 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 113.6(3) ?
C2 C1 H1A . . 108.9 ?
C10 C1 H1A . . 108.9 ?
C2 C1 H1B . . 108.9 ?
C10 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C3 C2 C1 . . 111.5(3) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108 ?
C2 C3 C4 . . 114.2(3) ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3B . . 108.7 ?
C4 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
C19 C4 C3 . . 109.8(3) ?
C19 C4 C18 . . 106.6(2) ?
C3 C4 C18 . . 107.9(3) ?
C19 C4 C5 . . 114.6(2) ?
C3 C4 C5 . . 108.1(2) ?
C18 C4 C5 . . 109.7(2) ?
C6 C5 C10 . . 111.3(2) ?
C6 C5 C4 . . 114.2(2) ?
C10 C5 C4 . . 115.6(2) ?
C6 C5 H5 . . 104.8 ?
C10 C5 H5 . . 104.8 ?
C4 C5 H5 . . 104.8 ?
C5 C6 C7 . . 112.3(2) ?
C5 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C8 C7 C6 . . 113.0(2) ?
C8 C7 H7A . . 109 ?
C6 C7 H7A . . 109 ?
C8 C7 H7B . . 109 ?
C6 C7 H7B . . 109 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C14 . . 112.0(3) ?
C9 C8 C7 . . 107.7(3) ?
C14 C8 C7 . . 112.1(3) ?
C9 C8 H8 . . 108.3 ?
C14 C8 H8 . . 108.3 ?
C7 C8 H8 . . 108.3 ?
C11 C9 C8 . . 121.1(3) ?
C11 C9 C10 . . 121.8(3) ?
C8 C9 C10 . . 117.1(3) ?
C20 C10 C1 . . 110.3(3) ?
C20 C10 C9 . . 109.4(2) ?
C1 C10 C9 . . 107.5(2) ?
C20 C10 C5 . . 112.8(2) ?
C1 C10 C5 . . 108.5(2) ?
C9 C10 C5 . . 108.1(2) ?
C9 C11 C12 . . 125.2(3) ?
C9 C11 H11 . . 117.4 ?
C12 C11 H11 . . 117.4 ?
C11 C12 C13 . . 112.3(3) ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12B . . 109.1 ?
C13 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.9 ?
C15 C13 C14 . . 114.1(4) ?
C15 C13 C17 . . 107.3(4) ?
C14 C13 C17 . . 110.2(3) ?
C15 C13 C12 . . 108.7(3) ?
C14 C13 C12 . . 107.4(3) ?
C17 C13 C12 . . 109.0(4) ?
C13 C14 C8 . . 114.0(3) ?
C13 C14 H14A . . 108.8 ?
C8 C14 H14A . . 108.8 ?
C13 C14 H14B . . 108.8 ?
C8 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C16 C15 C13 . . 135.5(7) ?
C16 C15 H15 . . 112.2 ?
C13 C15 H15 . . 112.2 ?
C15 C16 H16A . . 120 ?
C15 C16 H16B . . 120 ?
H16A C16 H16B . . 120 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C4 C18 H18A . . 109.5 ?
C4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O1 C19 O2 . . 122.5(3) ?
O1 C19 C4 . . 123.5(3) ?
O2 C19 C4 . . 114.0(3) ?
C10 C20 H20A . . 109.5 ?
C10 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C10 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 O2 H2 . . 109.5 ?
C2' C1' C10' . . 115.0(3) ?
C2' C1' H1'1 . . 108.5 ?
C10' C1' H1'1 . . 108.5 ?
C2' C1' H1'2 . . 108.5 ?
C10' C1' H1'2 . . 108.5 ?
H1'1 C1' H1'2 . . 107.5 ?
C3' C2' C1' . . 111.4(3) ?
C3' C2' H2'1 . . 109.4 ?
C1' C2' H2'1 . . 109.4 ?
C3' C2' H2'2 . . 109.4 ?
C1' C2' H2'2 . . 109.4 ?
H2'1 C2' H2'2 . . 108 ?
C2' C3' C4' . . 113.1(3) ?
C2' C3' H3'1 . . 109 ?
C4' C3' H3'1 . . 109 ?
C2' C3' H3'2 . . 109 ?
C4' C3' H3'2 . . 109 ?
H3'1 C3' H3'2 . . 107.8 ?
C3' C4' C19' . . 108.6(3) ?
C3' C4' C18' . . 108.4(3) ?
C19' C4' C18' . . 105.4(3) ?
C3' C4' C5' . . 108.6(2) ?
C19' C4' C5' . . 115.9(3) ?
C18' C4' C5' . . 109.8(3) ?
C6' C5' C10' . . 112.8(2) ?
C6' C5' C4' . . 114.6(2) ?
C10' C5' C4' . . 114.8(2) ?
C6' C5' H5' . . 104.4 ?
C10' C5' H5' . . 104.4 ?
C4' C5' H5' . . 104.4 ?
C7' C6' C5' . . 112.7(2) ?
C7' C6' H6'1 . . 109 ?
C5' C6' H6'1 . . 109 ?
C7' C6' H6'2 . . 109 ?
C5' C6' H6'2 . . 109 ?
H6'1 C6' H6'2 . . 107.8 ?
C8' C7' C6' . . 112.5(2) ?
C8' C7' H7'1 . . 109.1 ?
C6' C7' H7'1 . . 109.1 ?
C8' C7' H7'2 . . 109.1 ?
C6' C7' H7'2 . . 109.1 ?
H7'1 C7' H7'2 . . 107.8 ?
C9' C8' C14' . . 111.9(2) ?
C9' C8' C7' . . 108.4(2) ?
C14' C8' C7' . . 111.1(2) ?
C9' C8' H8' . . 108.5 ?
C14' C8' H8' . . 108.5 ?
C7' C8' H8' . . 108.5 ?
C11' C9' C8' . . 121.5(3) ?
C11' C9' C10' . . 120.9(3) ?
C8' C9' C10' . . 117.6(2) ?
C20' C10' C9' . . 109.0(3) ?
C20' C10' C1' . . 111.3(2) ?
C9' C10' C1' . . 108.5(2) ?
C20' C10' C5' . . 111.9(2) ?
C9' C10' C5' . . 108.6(2) ?
C1' C10' C5' . . 107.4(3) ?
C9' C11' C12' . . 125.5(3) ?
C9' C11' H11' . . 117.3 ?
C12' C11' H11' . . 117.3 ?
C11' C12' C13' . . 112.8(3) ?
C11' C12' H12C . . 109 ?
C13' C12' H12C . . 109 ?
C11' C12' H12D . . 109 ?
C13' C12' H12D . . 109 ?
H12C C12' H12D . . 107.8 ?
C15' C13' C17' . . 108.1(3) ?
C15' C13' C14' . . 113.0(3) ?
C17' C13' C14' . . 110.8(3) ?
C15' C13' C12' . . 107.1(3) ?
C17' C13' C12' . . 109.9(3) ?
C14' C13' C12' . . 107.8(3) ?
C8' C14' C13' . . 113.9(3) ?
C8' C14' H14C . . 108.8 ?
C13' C14' H14C . . 108.8 ?
C8' C14' H14D . . 108.8 ?
C13' C14' H14D . . 108.8 ?
H14C C14' H14D . . 107.7 ?
C16' C15' C13' . . 130.2(4) ?
C16' C15' H15' . . 114.9 ?
C13' C15' H15' . . 114.9 ?
C15' C16' H16C . . 120 ?
C15' C16' H16D . . 120 ?
H16C C16' H16D . . 120 ?
C13' C17' H17D . . 109.5 ?
C13' C17' H17E . . 109.5 ?
H17D C17' H17E . . 109.5 ?
C13' C17' H17F . . 109.5 ?
H17D C17' H17F . . 109.5 ?
H17E C17' H17F . . 109.5 ?
C4' C18' H18D . . 109.5 ?
C4' C18' H18E . . 109.5 ?
H18D C18' H18E . . 109.5 ?
C4' C18' H18F . . 109.5 ?
H18D C18' H18F . . 109.5 ?
H18E C18' H18F . . 109.5 ?
O1' C19' O2' . . 122.4(3) ?
O1' C19' C4' . . 122.5(3) ?
O2' C19' C4' . . 114.9(3) ?
C10' C20' H20D . . 109.5 ?
C10' C20' H20E . . 109.5 ?
H20D C20' H20E . . 109.5 ?
C10' C20' H20F . . 109.5 ?
H20D C20' H20F . . 109.5 ?
H20E C20' H20F . . 109.5 ?
C19' O2' H2' . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.542(5) ?
C1 C10 . 1.548(4) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.511(6) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.540(4) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C19 . 1.534(4) ?
C4 C18 . 1.543(4) ?
C4 C5 . 1.577(4) ?
C5 C6 . 1.539(4) ?
C5 C10 . 1.553(4) ?
C5 H5 . 0.98 ?
C6 C7 . 1.537(5) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.535(5) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.515(4) ?
C8 C14 . 1.520(4) ?
C8 H8 . 0.98 ?
C9 C11 . 1.331(5) ?
C9 C10 . 1.552(4) ?
C10 C20 . 1.545(4) ?
C11 C12 . 1.507(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.548(5) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C15 . 1.505(5) ?
C13 C14 . 1.516(6) ?
C13 C17 . 1.540(6) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.167(8) ?
C15 H15 . 0.93 ?
C16 H16A . 0.93 ?
C16 H16B . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 O1 . 1.223(4) ?
C19 O2 . 1.313(4) ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
O2 H2 . 0.82 ?
C1' C2' . 1.520(5) ?
C1' C10' . 1.545(4) ?
C1' H1'1 . 0.97 ?
C1' H1'2 . 0.97 ?
C2' C3' . 1.514(6) ?
C2' H2'1 . 0.97 ?
C2' H2'2 . 0.97 ?
C3' C4' . 1.534(5) ?
C3' H3'1 . 0.97 ?
C3' H3'2 . 0.97 ?
C4' C19' . 1.538(4) ?
C4' C18' . 1.544(5) ?
C4' C5' . 1.565(4) ?
C5' C6' . 1.542(4) ?
C5' C10' . 1.563(4) ?
C5' H5' . 0.98 ?
C6' C7' . 1.539(4) ?
C6' H6'1 . 0.97 ?
C6' H6'2 . 0.97 ?
C7' C8' . 1.536(4) ?
C7' H7'1 . 0.97 ?
C7' H7'2 . 0.97 ?
C8' C9' . 1.514(4) ?
C8' C14' . 1.526(4) ?
C8' H8' . 0.98 ?
C9' C11' . 1.329(4) ?
C9' C10' . 1.544(4) ?
C10' C20' . 1.545(4) ?
C11' C12' . 1.507(5) ?
C11' H11' . 0.93 ?
C12' C13' . 1.553(5) ?
C12' H12C . 0.97 ?
C12' H12D . 0.97 ?
C13' C15' . 1.511(5) ?
C13' C17' . 1.534(5) ?
C13' C14' . 1.534(5) ?
C14' H14C . 0.97 ?
C14' H14D . 0.97 ?
C15' C16' . 1.251(7) ?
C15' H15' . 0.93 ?
C16' H16C . 0.93 ?
C16' H16D . 0.93 ?
C17' H17D . 0.96 ?
C17' H17E . 0.96 ?
C17' H17F . 0.96 ?
C18' H18D . 0.96 ?
C18' H18E . 0.96 ?
C18' H18F . 0.96 ?
C19' O1' . 1.220(4) ?
C19' O2' . 1.312(4) ?
C20' H20D . 0.96 ?
C20' H20E . 0.96 ?
C20' H20F . 0.96 ?
O2' H2' . 0.82 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2' H2' O1 . 0.82 1.87 2.687(3) 177
O2 H2 O1' . 0.82 1.83 2.649(3) 175
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . 54.8(4) ?
C1 C2 C3 C4 . . . . -55.4(4) ?
C2 C3 C4 C19 . . . . -72.7(3) ?
C2 C3 C4 C18 . . . . 171.5(3) ?
C2 C3 C4 C5 . . . . 52.9(3) ?
C19 C4 C5 C6 . . . . -61.0(3) ?
C3 C4 C5 C6 . . . . 176.2(3) ?
C18 C4 C5 C6 . . . . 58.8(3) ?
C19 C4 C5 C10 . . . . 70.1(3) ?
C3 C4 C5 C10 . . . . -52.7(3) ?
C18 C4 C5 C10 . . . . -170.1(3) ?
C10 C5 C6 C7 . . . . 45.5(3) ?
C4 C5 C6 C7 . . . . 178.7(2) ?
C5 C6 C7 C8 . . . . 14.7(4) ?
C6 C7 C8 C9 . . . . -59.8(3) ?
C6 C7 C8 C14 . . . . 176.4(3) ?
C14 C8 C9 C11 . . . . -11.1(4) ?
C7 C8 C9 C11 . . . . -134.9(3) ?
C14 C8 C9 C10 . . . . 169.4(3) ?
C7 C8 C9 C10 . . . . 45.6(3) ?
C2 C1 C10 C20 . . . . 71.9(4) ?
C2 C1 C10 C9 . . . . -169.0(3) ?
C2 C1 C10 C5 . . . . -52.2(3) ?
C11 C9 C10 C20 . . . . 68.8(4) ?
C8 C9 C10 C20 . . . . -111.7(3) ?
C11 C9 C10 C1 . . . . -51.0(4) ?
C8 C9 C10 C1 . . . . 128.5(3) ?
C11 C9 C10 C5 . . . . -168.0(3) ?
C8 C9 C10 C5 . . . . 11.6(3) ?
C6 C5 C10 C20 . . . . 62.5(3) ?
C4 C5 C10 C20 . . . . -70.0(3) ?
C6 C5 C10 C1 . . . . -174.9(2) ?
C4 C5 C10 C1 . . . . 52.6(3) ?
C6 C5 C10 C9 . . . . -58.7(3) ?
C4 C5 C10 C9 . . . . 168.9(2) ?
C8 C9 C11 C12 . . . . -2.4(6) ?
C10 C9 C11 C12 . . . . 177.1(3) ?
C9 C11 C12 C13 . . . . -16.0(6) ?
C11 C12 C13 C15 . . . . 169.3(4) ?
C11 C12 C13 C14 . . . . 45.4(5) ?
C11 C12 C13 C17 . . . . -74.0(4) ?
C15 C13 C14 C8 . . . . 177.8(3) ?
C17 C13 C14 C8 . . . . 57.1(4) ?
C12 C13 C14 C8 . . . . -61.6(4) ?
C9 C8 C14 C13 . . . . 44.4(4) ?
C7 C8 C14 C13 . . . . 165.6(3) ?
C14 C13 C15 C16 . . . . -15.6(10) ?
C17 C13 C15 C16 . . . . 106.8(9) ?
C12 C13 C15 C16 . . . . -135.4(8) ?
C3 C4 C19 O1 . . . . 5.7(4) ?
C18 C4 C19 O1 . . . . 122.2(3) ?
C5 C4 C19 O1 . . . . -116.2(3) ?
C3 C4 C19 O2 . . . . -171.4(3) ?
C18 C4 C19 O2 . . . . -54.8(3) ?
C5 C4 C19 O2 . . . . 66.8(3) ?
C10' C1' C2' C3' . . . . 54.7(4) ?
C1' C2' C3' C4' . . . . -55.4(4) ?
C2' C3' C4' C19' . . . . -72.1(3) ?
C2' C3' C4' C18' . . . . 173.9(3) ?
C2' C3' C4' C5' . . . . 54.7(3) ?
C3' C4' C5' C6' . . . . 172.2(3) ?
C19' C4' C5' C6' . . . . -65.4(3) ?
C18' C4' C5' C6' . . . . 53.8(3) ?
C3' C4' C5' C10' . . . . -55.0(3) ?
C19' C4' C5' C10' . . . . 67.5(3) ?
C18' C4' C5' C10' . . . . -173.3(3) ?
C10' C5' C6' C7' . . . . 39.9(3) ?
C4' C5' C6' C7' . . . . 173.7(2) ?
C5' C6' C7' C8' . . . . 19.4(4) ?
C6' C7' C8' C9' . . . . -61.1(3) ?
C6' C7' C8' C14' . . . . 175.6(2) ?
C14' C8' C9' C11' . . . . -13.8(4) ?
C7' C8' C9' C11' . . . . -136.6(3) ?
C14' C8' C9' C10' . . . . 166.3(3) ?
C7' C8' C9' C10' . . . . 43.5(3) ?
C11' C9' C10' C20' . . . . 71.0(4) ?
C8' C9' C10' C20' . . . . -109.2(3) ?
C11' C9' C10' C1' . . . . -50.4(4) ?
C8' C9' C10' C1' . . . . 129.4(3) ?
C11' C9' C10' C5' . . . . -166.9(3) ?
C8' C9' C10' C5' . . . . 13.0(3) ?
C2' C1' C10' C20' . . . . 70.8(4) ?
C2' C1' C10' C9' . . . . -169.3(3) ?
C2' C1' C10' C5' . . . . -52.1(4) ?
C6' C5' C10' C20' . . . . 64.1(3) ?
C4' C5' C10' C20' . . . . -69.6(3) ?
C6' C5' C10' C9' . . . . -56.3(3) ?
C4' C5' C10' C9' . . . . 170.0(2) ?
C6' C5' C10' C1' . . . . -173.5(2) ?
C4' C5' C10' C1' . . . . 52.8(3) ?
C8' C9' C11' C12' . . . . -0.6(6) ?
C10' C9' C11' C12' . . . . 179.2(3) ?
C9' C11' C12' C13' . . . . -15.2(5) ?
C11' C12' C13' C15' . . . . 165.0(3) ?
C11' C12' C13' C17' . . . . -77.8(4) ?
C11' C12' C13' C14' . . . . 43.1(4) ?
C9' C8' C14' C13' . . . . 45.2(3) ?
C7' C8' C14' C13' . . . . 166.5(3) ?
C15' C13' C14' C8' . . . . -178.1(3) ?
C17' C13' C14' C8' . . . . 60.3(4) ?
C12' C13' C14' C8' . . . . -60.0(4) ?
C17' C13' C15' C16' . . . . 124.4(5) ?
C14' C13' C15' C16' . . . . 1.3(6) ?
C12' C13' C15' C16' . . . . -117.2(5) ?
C3' C4' C19' O1' . . . . -6.0(4) ?
C18' C4' C19' O1' . . . . 110.0(4) ?
C5' C4' C19' O1' . . . . -128.4(3) ?
C3' C4' C19' O2' . . . . 178.4(3) ?
C18' C4' C19' O2' . . . . -65.6(3) ?
C5' C4' C19' O2' . . . . 55.9(4) ?
