#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/19/2221901.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_2221901
loop_
_publ_author_name
'Zhao, Zhen-Dong'
'Chen, Yu-Xiang'
'Wang, Yu-Min'
'Bi, Liang-Wu'
_publ_section_title
;1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic
 acid
;
_journal_coeditor_code           AT2789
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1429
_journal_paper_doi               10.1107/S1600536809019308
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H30 O2'
_chemical_formula_moiety         'C20 H30 O2'
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.44
_chemical_melting_point          436
_chemical_name_systematic
;
1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-
dodecahydrophenanthrene-1-carboxylic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.624(2)
_cell_length_b                   11.803(2)
_cell_length_c                   25.698(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     3525.7(11)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7031
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       quadrate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.045P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                2613
_reflns_number_total             6382
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2789.cif
_cod_data_source_block           I
_cod_original_cell_volume        3525.7(12)
_cod_database_code               2221901
_cod_database_fobs_code          2221901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O O1 0.7921(4) 0.8907(4) 0.96412(19) 0.0796(17) Uani d . 1 . .
O O2 0.6441(4) 1.0009(4) 0.97857(19) 0.0816(16) Uani d . 1 . .
H H2B 0.6765 1.0386 0.9561 0.122 Uiso calc R 1 . .
C C1 0.9481(9) 0.1236(8) 1.0193(3) 0.127 Uani d D 1 . .
H H1A 0.8843 0.0857 1.0060 0.152 Uiso calc R 1 . .
H H1B 1.0204 0.0899 1.0178 0.152 Uiso calc R 1 . .
C C2 0.9370(8) 0.2172(8) 1.0385(3) 0.110 Uani d D 1 . .
H H2A 1.0080 0.2437 1.0499 0.132 Uiso calc R 1 . .
C C3 0.7282(7) 0.2534(6) 1.0540(3) 0.088(3) Uani d . 1 . .
H H3A 0.7268 0.1988 1.0817 0.132 Uiso calc R 1 . .
H H3B 0.7082 0.2170 1.0218 0.132 Uiso calc R 1 . .
H H3C 0.6738 0.3126 1.0612 0.132 Uiso calc R 1 . .
C C4 0.8463(7) 0.3031(6) 1.0497(3) 0.064(2) Uani d . 1 . .
C C5 0.8871(7) 0.3611(6) 1.0991(3) 0.076(2) Uani d . 1 . .
H H5A 0.9652 0.3881 1.0942 0.091 Uiso calc R 1 . .
H H5B 0.8874 0.3070 1.1275 0.091 Uiso calc R 1 . .
C C6 0.8086(6) 0.4615(5) 1.1131(3) 0.069(2) Uani d . 1 . .
H H6A 0.7309 0.4342 1.1187 0.083 Uiso calc R 1 . .
H H6B 0.8352 0.4957 1.1452 0.083 Uiso calc R 1 . .
C C7 0.8077(5) 0.5512(5) 1.0699(2) 0.0449(16) Uani d . 1 . .
H H7A 0.8864 0.5808 1.0676 0.054 Uiso calc R 1 . .
C C8 0.7810(6) 0.4997(5) 1.0180(3) 0.0496(17) Uani d . 1 . .
C C9 0.8475(6) 0.3926(5) 1.0056(3) 0.066(2) Uani d . 1 . .
H H9A 0.9267 0.4127 0.9981 0.080 Uiso calc R 1 . .
H H9B 0.8154 0.3588 0.9744 0.080 Uiso calc R 1 . .
C C10 0.7276(6) 0.6559(5) 1.0837(2) 0.0461(16) Uani d . 1 . .
C C11 0.7174(6) 0.7258(5) 1.0326(2) 0.0469(16) Uani d . 1 . .
H H11A 0.7965 0.7339 1.0199 0.056 Uiso calc R 1 . .
C C12 0.6560(6) 0.6608(5) 0.9911(2) 0.0579(19) Uani d . 1 . .
H H12A 0.6586 0.7027 0.9586 0.070 Uiso calc R 1 . .
H H12B 0.5759 0.6510 1.0007 0.070 Uiso calc R 1 . .
C C13 0.7126(6) 0.5439(5) 0.9835(3) 0.0599(19) Uani d . 1 . .
H H13A 0.6972 0.5035 0.9533 0.072 Uiso calc R 1 . .
C C14 0.7876(6) 0.7254(5) 1.1253(2) 0.0577(18) Uani d . 1 . .
H H14A 0.8674 0.7364 1.1154 0.069 Uiso calc R 1 . .
H H14B 0.7864 0.6839 1.1579 0.069 Uiso calc R 1 . .
C C15 0.7310(7) 0.8406(5) 1.1333(3) 0.071(2) Uani d . 1 . .
H H15A 0.7709 0.8811 1.1607 0.086 Uiso calc R 1 . .
H H15B 0.6518 0.8298 1.1441 0.086 Uiso calc R 1 . .
C C16 0.7336(7) 0.9111(6) 1.0836(3) 0.071(2) Uani d . 1 . .
H H16A 0.8129 0.9255 1.0739 0.085 Uiso calc R 1 . .
H H16B 0.6968 0.9835 1.0900 0.085 Uiso calc R 1 . .
C C17 0.6704(6) 0.8497(5) 1.0371(2) 0.0523(18) Uani d . 1 . .
C C18 0.6102(5) 0.6120(6) 1.1030(3) 0.0601(19) Uani d . 1 . .
H H18A 0.5611 0.6751 1.1109 0.090 Uiso calc R 1 . .
H H18B 0.6211 0.5670 1.1337 0.090 Uiso calc R 1 . .
H H18C 0.5752 0.5665 1.0764 0.090 Uiso calc R 1 . .
C C19 0.5398(6) 0.8563(6) 1.0466(3) 0.071(2) Uani d . 1 . .
H H19A 0.5171 0.9341 1.0500 0.106 Uiso calc R 1 . .
H H19B 0.5210 0.8162 1.0780 0.106 Uiso calc R 1 . .
H H19C 0.4999 0.8225 1.0178 0.106 Uiso calc R 1 . .
C C20 0.7059(7) 0.9151(5) 0.9899(3) 0.0554(19) Uani d . 1 . .
O O3 0.3506(4) 1.4855(4) 1.11796(19) 0.0782(16) Uani d . 1 . .
H H3D 0.3267 1.5163 1.0915 0.117 Uiso calc R 1 . .
O O4 0.2231(4) 1.3579(4) 1.09334(19) 0.0715(15) Uani d . 1 . .
C C21 0.0730(7) 0.5800(8) 1.1914(4) 0.112(3) Uani d . 1 . .
H H21A 0.0778 0.5751 1.2275 0.135 Uiso calc R 1 . .
H H21B 0.0414 0.5207 1.1724 0.135 Uiso calc R 1 . .
C C22 0.1091(7) 0.6666(6) 1.1685(4) 0.087(3) Uani d . 1 . .
H H22A 0.1017 0.6661 1.1325 0.104 Uiso calc R 1 . .
C C23 0.1430(6) 0.7841(7) 1.2495(3) 0.090(3) Uani d . 1 . .
H H23A 0.0621 0.7856 1.2569 0.134 Uiso calc R 1 . .
H H23B 0.1774 0.8540 1.2606 0.134 Uiso calc R 1 . .
H H23C 0.1781 0.7222 1.2678 0.134 Uiso calc R 1 . .
C C24 0.1616(7) 0.7689(6) 1.1909(3) 0.064(2) Uani d . 1 . .
C C25 0.2897(6) 0.7684(5) 1.1787(3) 0.067(2) Uani d . 1 . .
H H25A 0.3248 0.7052 1.1968 0.081 Uiso calc R 1 . .
H H25B 0.2993 0.7553 1.1417 0.081 Uiso calc R 1 . .
C C26 0.3541(6) 0.8752(5) 1.1930(3) 0.065(2) Uani d . 1 . .
H H26A 0.4335 0.8676 1.1819 0.078 Uiso calc R 1 . .
H H26B 0.3539 0.8831 1.2306 0.078 Uiso calc R 1 . .
C C27 0.3037(5) 0.9826(5) 1.1690(2) 0.0489(17) Uani d . 1 . .
H H27A 0.3218 0.9779 1.1318 0.059 Uiso calc R 1 . .
C C28 0.1740(6) 0.9838(6) 1.1720(2) 0.0519(18) Uani d . 1 . .
C C29 0.1117(6) 0.8732(5) 1.1632(3) 0.066(2) Uani d . 1 . .
H H29A 0.1107 0.8581 1.1261 0.080 Uiso calc R 1 . .
H H29B 0.0325 0.8825 1.1743 0.080 Uiso calc R 1 . .
C C30 0.3612(5) 1.0954(5) 1.1883(3) 0.0486(17) Uani d . 1 . .
C C31 0.2935(5) 1.1915(5) 1.1639(2) 0.0467(17) Uani d . 1 . .
H H31A 0.2870 1.1711 1.1270 0.056 Uiso calc R 1 . .
C C32 0.1699(6) 1.1945(6) 1.1837(3) 0.0574(19) Uani d . 1 . .
H H32A 0.1690 1.2197 1.2196 0.069 Uiso calc R 1 . .
H H32B 0.1255 1.2480 1.1633 0.069 Uiso calc R 1 . .
C C33 0.1167(6) 1.0799(6) 1.1800(3) 0.067(2) Uani d . 1 . .
H H33A 0.0372 1.0752 1.1834 0.081 Uiso calc R 1 . .
C C34 0.4849(5) 1.0947(6) 1.1698(3) 0.061(2) Uani d . 1 . .
H H34A 0.4870 1.0785 1.1328 0.074 Uiso calc R 1 . .
H H34B 0.5266 1.0351 1.1877 0.074 Uiso calc R 1 . .
C C35 0.5446(6) 1.2105(6) 1.1803(3) 0.074(2) Uani d . 1 . .
H H35A 0.5418 1.2283 1.2171 0.089 Uiso calc R 1 . .
H H35B 0.6246 1.2073 1.1696 0.089 Uiso calc R 1 . .
C C36 0.4813(5) 1.3000(6) 1.1494(3) 0.061(2) Uani d . 1 . .
H H36A 0.4862 1.2810 1.1127 0.073 Uiso calc R 1 . .
H H36B 0.5199 1.3721 1.1543 0.073 Uiso calc R 1 . .
C C37 0.3535(6) 1.3142(5) 1.1640(2) 0.0509(17) Uani d . 1 . .
C C38 0.3546(6) 1.0973(5) 1.2479(2) 0.067(2) Uani d . 1 . .
H H38A 0.3887 1.1660 1.2607 0.101 Uiso calc R 1 . .
H H38B 0.3954 1.0334 1.2618 0.101 Uiso calc R 1 . .
H H38C 0.2755 1.0938 1.2586 0.101 Uiso calc R 1 . .
C C39 0.3395(7) 1.3764(5) 1.2144(3) 0.075(2) Uani d . 1 . .
H H39A 0.3785 1.4480 1.2124 0.112 Uiso calc R 1 . .
H H39B 0.3719 1.3322 1.2422 0.112 Uiso calc R 1 . .
H H39C 0.2592 1.3889 1.2210 0.112 Uiso calc R 1 . .
C C40 0.3037(6) 1.3882(6) 1.1227(3) 0.0529(18) Uani d . 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C20 O2 H2B . . 109.5 ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C4 . . 140.4(11) ?
C1 C2 H2A . . 109.8 ?
C4 C2 H2A . . 109.8 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C2 C4 C3 . . 113.4(7) ?
C2 C4 C5 . . 104.3(7) ?
C3 C4 C5 . . 113.7(6) ?
C2 C4 C9 . . 108.4(6) ?
C3 C4 C9 . . 109.2(6) ?
C5 C4 C9 . . 107.5(6) ?
C4 C5 C6 . . 111.0(6) ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C7 C6 C5 . . 111.5(5) ?
C7 C6 H6A . . 109.3 ?
C5 C6 H6A . . 109.3 ?
C7 C6 H6B . . 109.3 ?
C5 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C8 C7 C6 . . 111.4(5) ?
C8 C7 C10 . . 113.1(5) ?
C6 C7 C10 . . 112.3(5) ?
C8 C7 H7A . . 106.5 ?
C6 C7 H7A . . 106.5 ?
C10 C7 H7A . . 106.5 ?
C13 C8 C7 . . 124.8(6) ?
C13 C8 C9 . . 120.2(7) ?
C7 C8 C9 . . 114.8(6) ?
C8 C9 C4 . . 114.2(5) ?
C8 C9 H9A . . 108.7 ?
C4 C9 H9A . . 108.7 ?
C8 C9 H9B . . 108.7 ?
C4 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
C14 C10 C18 . . 111.2(6) ?
C14 C10 C11 . . 110.0(5) ?
C18 C10 C11 . . 112.4(5) ?
C14 C10 C7 . . 108.0(5) ?
C18 C10 C7 . . 109.3(5) ?
C11 C10 C7 . . 105.6(5) ?
C12 C11 C10 . . 111.5(5) ?
C12 C11 C17 . . 111.4(5) ?
C10 C11 C17 . . 117.4(5) ?
C12 C11 H11A . . 105.1 ?
C10 C11 H11A . . 105.1 ?
C17 C11 H11A . . 105.1 ?
C11 C12 C13 . . 110.2(5) ?
C11 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
C11 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C8 C13 C12 . . 122.3(6) ?
C8 C13 H13A . . 118.8 ?
C12 C13 H13A . . 118.8 ?
C10 C14 C15 . . 112.3(6) ?
C10 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
C10 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C14 C15 C16 . . 111.4(6) ?
C14 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
C14 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
C15 C16 C17 . . 112.0(6) ?
C15 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
C15 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C20 C17 C19 . . 112.0(6) ?
C20 C17 C11 . . 109.0(5) ?
C19 C17 C11 . . 113.8(6) ?
C20 C17 C16 . . 104.3(5) ?
C19 C17 C16 . . 108.4(6) ?
C11 C17 C16 . . 108.8(6) ?
C10 C18 H18A . . 109.5 ?
C10 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C10 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O1 C20 O2 . . 121.3(7) ?
O1 C20 C17 . . 122.6(6) ?
O2 C20 C17 . . 116.1(7) ?
C40 O3 H3D . . 109.5 ?
C22 C21 H21A . . 120.0 ?
C22 C21 H21B . . 120.0 ?
H21A C21 H21B . . 120.0 ?
C21 C22 C24 . . 128.7(9) ?
C21 C22 H22A . . 115.6 ?
C24 C22 H22A . . 115.6 ?
C24 C23 H23A . . 109.5 ?
C24 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C24 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C22 C24 C25 . . 108.8(7) ?
C22 C24 C23 . . 115.0(7) ?
C25 C24 C23 . . 109.9(6) ?
C22 C24 C29 . . 108.7(6) ?
C25 C24 C29 . . 106.1(6) ?
C23 C24 C29 . . 108.0(6) ?
C26 C25 C24 . . 115.6(6) ?
C26 C25 H25A . . 108.4 ?
C24 C25 H25A . . 108.4 ?
C26 C25 H25B . . 108.4 ?
C24 C25 H25B . . 108.4 ?
H25A C25 H25B . . 107.5 ?
C25 C26 C27 . . 113.8(6) ?
C25 C26 H26A . . 108.8 ?
C27 C26 H26A . . 108.8 ?
C25 C26 H26B . . 108.8 ?
C27 C26 H26B . . 108.8 ?
H26A C26 H26B . . 107.7 ?
C28 C27 C26 . . 111.7(6) ?
C28 C27 C30 . . 113.6(5) ?
C26 C27 C30 . . 114.4(5) ?
C28 C27 H27A . . 105.4 ?
C26 C27 H27A . . 105.4 ?
C30 C27 H27A . . 105.4 ?
C33 C28 C29 . . 121.3(6) ?
C33 C28 C27 . . 121.0(7) ?
C29 C28 C27 . . 117.6(6) ?
C28 C29 C24 . . 116.2(6) ?
C28 C29 H29A . . 108.2 ?
C24 C29 H29A . . 108.2 ?
C28 C29 H29B . . 108.2 ?
C24 C29 H29B . . 108.2 ?
H29A C29 H29B . . 107.4 ?
C34 C30 C31 . . 111.6(6) ?
C34 C30 C38 . . 111.1(6) ?
C31 C30 C38 . . 112.0(5) ?
C34 C30 C27 . . 107.5(5) ?
C31 C30 C27 . . 106.5(5) ?
C38 C30 C27 . . 107.9(5) ?
C30 C31 C32 . . 111.6(6) ?
C30 C31 C37 . . 116.7(5) ?
C32 C31 C37 . . 112.7(5) ?
C30 C31 H31A . . 104.8 ?
C32 C31 H31A . . 104.8 ?
C37 C31 H31A . . 104.8 ?
C33 C32 C31 . . 110.4(6) ?
C33 C32 H32A . . 109.6 ?
C31 C32 H32A . . 109.6 ?
C33 C32 H32B . . 109.6 ?
C31 C32 H32B . . 109.6 ?
H32A C32 H32B . . 108.1 ?
C28 C33 C32 . . 125.2(7) ?
C28 C33 H33A . . 117.4 ?
C32 C33 H33A . . 117.4 ?
C30 C34 C35 . . 111.4(6) ?
C30 C34 H34A . . 109.3 ?
C35 C34 H34A . . 109.3 ?
C30 C34 H34B . . 109.3 ?
C35 C34 H34B . . 109.3 ?
H34A C34 H34B . . 108.0 ?
C36 C35 C34 . . 107.8(6) ?
C36 C35 H35A . . 110.1 ?
C34 C35 H35A . . 110.1 ?
C36 C35 H35B . . 110.1 ?
C34 C35 H35B . . 110.1 ?
H35A C35 H35B . . 108.5 ?
C35 C36 C37 . . 114.6(6) ?
C35 C36 H36A . . 108.6 ?
C37 C36 H36A . . 108.6 ?
C35 C36 H36B . . 108.6 ?
C37 C36 H36B . . 108.6 ?
H36A C36 H36B . . 107.6 ?
C40 C37 C39 . . 106.6(5) ?
C40 C37 C36 . . 105.3(6) ?
C39 C37 C36 . . 111.6(6) ?
C40 C37 C31 . . 111.0(5) ?
C39 C37 C31 . . 113.4(6) ?
C36 C37 C31 . . 108.6(5) ?
C30 C38 H38A . . 109.5 ?
C30 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C30 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
O4 C40 O3 . . 121.1(7) ?
O4 C40 C37 . . 123.4(7) ?
O3 C40 C37 . . 115.4(6) ?
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
O1 C20 . 1.235(7) ?
O2 C20 . 1.276(7) ?
O2 H2B . 0.8200 ?
C1 C2 . 1.217(8) ?
C1 H1A . 0.9300 ?
C1 H1B . 0.9300 ?
C2 C4 . 1.491(10) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.496(9) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.518(10) ?
C4 C9 . 1.549(9) ?
C5 C6 . 1.538(9) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.534(8) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.498(8) ?
C7 C10 . 1.587(8) ?
C7 H7A . 0.9800 ?
C8 C13 . 1.299(8) ?
C8 C9 . 1.516(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C14 . 1.517(8) ?
C10 C18 . 1.542(8) ?
C10 C11 . 1.555(7) ?
C11 C12 . 1.496(8) ?
C11 C17 . 1.565(8) ?
C11 H11A . 0.9800 ?
C12 C13 . 1.541(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9300 ?
C14 C15 . 1.524(8) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.525(9) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.578(9) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C20 . 1.496(9) ?
C17 C19 . 1.540(8) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
O3 C40 . 1.278(7) ?
O3 H3D . 0.8200 ?
O4 C40 . 1.256(7) ?
C21 C22 . 1.252(10) ?
C21 H21A . 0.9300 ?
C21 H21B . 0.9300 ?
C22 C24 . 1.470(9) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.532(10) ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C24 C25 . 1.522(10) ?
C24 C29 . 1.536(9) ?
C25 C26 . 1.511(8) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 C27 . 1.528(8) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 C28 . 1.510(8) ?
C27 C30 . 1.570(8) ?
C27 H27A . 0.9800 ?
C28 C33 . 1.331(8) ?
C28 C29 . 1.510(8) ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C30 C34 . 1.514(8) ?
C30 C31 . 1.516(8) ?
C30 C38 . 1.536(8) ?
C31 C32 . 1.525(8) ?
C31 C37 . 1.607(8) ?
C31 H31A . 0.9800 ?
C32 C33 . 1.491(9) ?
C32 H32A . 0.9700 ?
C32 H32B . 0.9700 ?
C33 H33A . 0.9300 ?
C34 C35 . 1.556(8) ?
C34 H34A . 0.9700 ?
C34 H34B . 0.9700 ?
C35 C36 . 1.514(9) ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
C36 C37 . 1.541(9) ?
C36 H36A . 0.9700 ?
C36 H36B . 0.9700 ?
C37 C40 . 1.491(8) ?
C37 C39 . 1.498(8) ?
C38 H38A . 0.9600 ?
C38 H38B . 0.9600 ?
C38 H38C . 0.9600 ?
C39 H39A . 0.9600 ?
C39 H39B . 0.9600 ?
C39 H39C . 0.9600 ?
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
_geom_hbond_publ_flag
O2 H2B O4 4_577 0.82 1.84 2.653(7) 168 yes
O3 H3D O1 4_477 0.82 1.85 2.655(7) 168 yes
C11 H11A O1 . 0.98 2.34 2.764(7) 105 yes
C32 H32B O4 . 0.97 2.49 3.081(9) 119 yes
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
C1 C2 C4 C3 . . . . 24.1(17) ?
C1 C2 C4 C5 . . . . 148.3(13) ?
C1 C2 C4 C9 . . . . -97.4(14) ?
C2 C4 C5 C6 . . . . 174.2(6) ?
C3 C4 C5 C6 . . . . -61.8(7) ?
C9 C4 C5 C6 . . . . 59.2(8) ?
C4 C5 C6 C7 . . . . -60.6(8) ?
C5 C6 C7 C8 . . . . 52.2(8) ?
C5 C6 C7 C10 . . . . -179.8(6) ?
C6 C7 C8 C13 . . . . 137.7(7) ?
C10 C7 C8 C13 . . . . 10.1(9) ?
C6 C7 C8 C9 . . . . -46.6(7) ?
C10 C7 C8 C9 . . . . -174.3(5) ?
C13 C8 C9 C4 . . . . -135.3(7) ?
C7 C8 C9 C4 . . . . 48.8(8) ?
C2 C4 C9 C8 . . . . -165.8(6) ?
C3 C4 C9 C8 . . . . 70.2(8) ?
C5 C4 C9 C8 . . . . -53.6(8) ?
C8 C7 C10 C14 . . . . -159.8(5) ?
C6 C7 C10 C14 . . . . 73.1(6) ?
C8 C7 C10 C18 . . . . 79.1(6) ?
C6 C7 C10 C18 . . . . -48.0(7) ?
C8 C7 C10 C11 . . . . -42.0(7) ?
C6 C7 C10 C11 . . . . -169.2(5) ?
C14 C10 C11 C12 . . . . -178.6(5) ?
C18 C10 C11 C12 . . . . -54.0(7) ?
C7 C10 C11 C12 . . . . 65.1(7) ?
C14 C10 C11 C17 . . . . -48.3(8) ?
C18 C10 C11 C17 . . . . 76.3(7) ?
C7 C10 C11 C17 . . . . -164.6(5) ?
C10 C11 C12 C13 . . . . -52.7(7) ?
C17 C11 C12 C13 . . . . 173.9(5) ?
C7 C8 C13 C12 . . . . 4.0(10) ?
C9 C8 C13 C12 . . . . -171.4(6) ?
C11 C12 C13 C8 . . . . 17.2(9) ?
C18 C10 C14 C15 . . . . -72.3(7) ?
C11 C10 C14 C15 . . . . 53.0(8) ?
C7 C10 C14 C15 . . . . 167.9(5) ?
C10 C14 C15 C16 . . . . -60.5(8) ?
C14 C15 C16 C17 . . . . 58.8(9) ?
C12 C11 C17 C20 . . . . -70.0(7) ?
C10 C11 C17 C20 . . . . 159.7(6) ?
C12 C11 C17 C19 . . . . 55.8(7) ?
C10 C11 C17 C19 . . . . -74.5(8) ?
C12 C11 C17 C16 . . . . 176.8(5) ?
C10 C11 C17 C16 . . . . 46.5(8) ?
C15 C16 C17 C20 . . . . -166.5(6) ?
C15 C16 C17 C19 . . . . 74.0(7) ?
C15 C16 C17 C11 . . . . -50.2(8) ?
C19 C17 C20 O1 . . . . -152.8(7) ?
C11 C17 C20 O1 . . . . -26.0(10) ?
C16 C17 C20 O1 . . . . 90.1(8) ?
C19 C17 C20 O2 . . . . 29.6(9) ?
C11 C17 C20 O2 . . . . 156.4(6) ?
C16 C17 C20 O2 . . . . -87.4(7) ?
C21 C22 C24 C25 . . . . 107.4(11) ?
C21 C22 C24 C23 . . . . -16.4(14) ?
C21 C22 C24 C29 . . . . -137.6(10) ?
C22 C24 C25 C26 . . . . 172.6(6) ?
C23 C24 C25 C26 . . . . -60.7(9) ?
C29 C24 C25 C26 . . . . 55.8(8) ?
C24 C25 C26 C27 . . . . -55.4(9) ?
C25 C26 C27 C28 . . . . 42.9(8) ?
C25 C26 C27 C30 . . . . 173.7(6) ?
C26 C27 C28 C33 . . . . 144.3(7) ?
C30 C27 C28 C33 . . . . 13.1(9) ?
C26 C27 C28 C29 . . . . -38.6(8) ?
C30 C27 C28 C29 . . . . -169.8(5) ?
C33 C28 C29 C24 . . . . -138.2(7) ?
C27 C28 C29 C24 . . . . 44.7(9) ?
C22 C24 C29 C28 . . . . -166.6(7) ?
C25 C24 C29 C28 . . . . -49.7(8) ?
C23 C24 C29 C28 . . . . 68.1(8) ?
C28 C27 C30 C34 . . . . -165.1(5) ?
C26 C27 C30 C34 . . . . 65.1(7) ?
C28 C27 C30 C31 . . . . -45.4(7) ?
C26 C27 C30 C31 . . . . -175.2(6) ?
C28 C27 C30 C38 . . . . 75.0(6) ?
C26 C27 C30 C38 . . . . -54.8(7) ?
C34 C30 C31 C32 . . . . -178.2(5) ?
C38 C30 C31 C32 . . . . -52.9(7) ?
C27 C30 C31 C32 . . . . 64.8(7) ?
C34 C30 C31 C37 . . . . -46.6(8) ?
C38 C30 C31 C37 . . . . 78.7(7) ?
C27 C30 C31 C37 . . . . -163.6(5) ?
C30 C31 C32 C33 . . . . -49.6(7) ?
C37 C31 C32 C33 . . . . 176.9(5) ?
C29 C28 C33 C32 . . . . -173.5(7) ?
C27 C28 C33 C32 . . . . 3.5(11) ?
C31 C32 C33 C28 . . . . 14.2(10) ?
C31 C30 C34 C35 . . . . 55.7(8) ?
C38 C30 C34 C35 . . . . -70.2(7) ?
C27 C30 C34 C35 . . . . 172.0(5) ?
C30 C34 C35 C36 . . . . -62.2(8) ?
C34 C35 C36 C37 . . . . 61.0(8) ?
C35 C36 C37 C40 . . . . -169.2(6) ?
C35 C36 C37 C39 . . . . 75.5(8) ?
C35 C36 C37 C31 . . . . -50.3(7) ?
C30 C31 C37 C40 . . . . 157.9(6) ?
C32 C31 C37 C40 . . . . -71.0(7) ?
C30 C31 C37 C39 . . . . -82.1(7) ?
C32 C31 C37 C39 . . . . 49.0(8) ?
C30 C31 C37 C36 . . . . 42.5(7) ?
C32 C31 C37 C36 . . . . 173.6(5) ?
C39 C37 C40 O4 . . . . -121.8(7) ?
C36 C37 C40 O4 . . . . 119.5(7) ?
C31 C37 C40 O4 . . . . 2.2(9) ?
C39 C37 C40 O3 . . . . 59.8(8) ?
C36 C37 C40 O3 . . . . -58.9(7) ?
C31 C37 C40 O3 . . . . -176.3(6) ?
