#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:42:56 +0300 (Mon, 04 May 2020) $
#$Revision: 251469 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557704.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557704
loop_
_publ_author_name
'Yuan, Shengheng'
'Hua, Pei'
'Zhao, Chao'
'Zhou, Huihao'
'Xu, Jiake'
'Xu, Jun'
'Gu, Qiong'
_publ_section_title
;
 Jatrophane Diterpenoids from Euphorbia esula as Inhibitors of
 RANKL-Induced Osteoclastogenesis.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              1005
_journal_page_last               1017
_journal_paper_doi               10.1021/acs.jnatprod.9b00929
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H44 O13'
_chemical_formula_sum            'C40 H44 O13'
_chemical_formula_weight         732.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.56320(10)
_cell_length_b                   16.50340(10)
_cell_length_c                   18.95250(10)
_cell_measurement_reflns_used    28675
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6020
_cell_measurement_theta_min      3.5400
_cell_volume                     3616.75(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -12.00  83.00   0.50    0.20    --   46.62-102.00  95.00  190
  2  ω   -173.00 -83.00   0.50    1.20    -- -100.00-102.00  95.00  180
  3  ω   -173.00 -83.00   0.50    1.20    -- -100.00-101.00-169.00  180
  4  ω     32.00 122.00   0.50    1.20    --  107.00 -32.00 -64.00  180
  5  ω     34.00 110.00   0.50    1.20    --  107.00-101.00-169.00  152
  6  ω   -119.00 -71.00   0.50    0.20    --  -46.62-125.00  60.00   96
  7  ω   -119.00 -71.00   0.50    0.20    --  -46.62-125.00   0.00   96
  8  ω   -119.00 -71.00   0.50    0.20    --  -46.62-125.00-120.00   96
  9  ω    -27.00  61.00   0.50    0.20    --   46.62 -38.00-150.00  176
 10  ω   -114.00 -27.00   0.50    1.20    -- -100.00  45.00 -30.00  174
 11  ω     93.00 178.00   0.50    1.20    --  107.00  45.00 -90.00  170
 12  ω     34.00 125.00   0.50    1.20    --  107.00 -61.00 -90.00  182
 13  ω     34.00 109.00   0.50    1.20    --  107.00 -94.00  30.00  150
 14  ω     92.00 178.00   0.50    1.20    --  107.00  30.00  60.00  172
 15  ω     34.00 131.00   0.50    1.20    --  107.00 -77.00-180.00  194
 16  ω     34.00 109.00   0.50    1.20    --  107.00 -94.00 120.00  150
 17  ω     34.00 131.00   0.50    1.20    --  107.00 -77.00 -90.00  194
 18  ω   -119.00 -85.00   0.50    0.20    --  -46.62 -77.00-150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584310000
_diffrn_orient_matrix_UB_12      0.0372541000
_diffrn_orient_matrix_UB_13      -0.0654769000
_diffrn_orient_matrix_UB_21      0.1130512000
_diffrn_orient_matrix_UB_22      0.0105050000
_diffrn_orient_matrix_UB_23      0.0420582000
_diffrn_orient_matrix_UB_31      0.0393744000
_diffrn_orient_matrix_UB_32      -0.0849732000
_diffrn_orient_matrix_UB_33      -0.0234416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.122
_diffrn_reflns_theta_min         3.551
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         7114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0418P)²+0.7133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6895
_reflns_number_total             7114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b00929_si_004.cif
_cod_data_source_block           yuanshh_190401
_cod_depositor_comments
'Adding full bibliography for 1557703--1557705.cif.'
_cod_database_code               1557704
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C5(H5), C3(H3), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C53(H53), C43(H43), C12(H12), C47(H47), C44(H44), C49(H49),
 C45(H45), C46(H46), C52(H52), C51(H51), C50(H50)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C29(H29A,H29B,H29C)
2.e Idealised tetrahedral OH refined as rotating group:
 O34(H34)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.447
_oxdiff_exptl_absorpt_empirical_full_min 0.524
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O19 O 0.48404(11) 0.43924(7) 0.60281(7) 0.0165(3) Uani 1 1 d . . . . .
O16 O 0.84421(11) 0.58438(8) 0.59347(7) 0.0181(3) Uani 1 1 d . . . . .
O30 O 0.34122(11) 0.58462(8) 0.62112(7) 0.0197(3) Uani 1 1 d . . . . .
O22 O 0.89252(12) 0.42543(8) 0.62604(7) 0.0195(3) Uani 1 1 d . . . . .
O26 O 0.35999(11) 0.45941(8) 0.73085(7) 0.0194(3) Uani 1 1 d . . . . .
O21 O 0.51301(12) 0.31745(8) 0.65366(7) 0.0220(3) Uani 1 1 d . . . . .
O34 O 0.51953(12) 0.70367(8) 0.73619(7) 0.0220(3) Uani 1 1 d . . . . .
H34 H 0.506078 0.741113 0.763424 0.033 Uiso 1 1 calc GR . . . .
O18 O 0.87402(13) 0.67872(8) 0.67777(8) 0.0259(3) Uani 1 1 d . . . . .
O36 O 1.03943(12) 0.51661(9) 0.69957(7) 0.0248(3) Uani 1 1 d . . . . .
O28 O 0.27414(13) 0.46290(9) 0.83756(8) 0.0286(3) Uani 1 1 d . . . . .
O32 O 0.41594(14) 0.58759(9) 0.51137(8) 0.0285(3) Uani 1 1 d . . . . .
O24 O 0.92833(14) 0.33116(9) 0.70853(8) 0.0310(3) Uani 1 1 d . . . . .
O35 O 0.52147(13) 0.41896(8) 0.82287(7) 0.0248(3) Uani 1 1 d . . . . .
C27 C 0.28629(17) 0.43089(12) 0.78107(10) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.66976(15) 0.50500(10) 0.60213(10) 0.0160(3) Uani 1 1 d . . . . .
C17 C 0.89175(16) 0.65387(11) 0.61886(10) 0.0184(4) Uani 1 1 d . . . . .
C20 C 0.46472(16) 0.35975(11) 0.61061(10) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.58878(16) 0.55098(11) 0.85267(10) 0.0190(4) Uani 1 1 d . . . . .
H10 H 0.580808 0.605084 0.831923 0.023 Uiso 1 1 calc R . . . .
C4 C 0.51399(16) 0.54628(11) 0.68933(9) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.44744(16) 0.61378(11) 0.65134(10) 0.0171(4) Uani 1 1 d . . . . .
H5 H 0.495423 0.642790 0.617004 0.021 Uiso 1 1 calc R . . . .
C42 C 0.96937(16) 0.69315(11) 0.56654(10) 0.0191(4) Uani 1 1 d . . . . .
C31 C 0.33516(18) 0.57587(11) 0.55044(10) 0.0213(4) Uani 1 1 d . . . . .
C48 C 0.37863(16) 0.32948(11) 0.55822(10) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.71233(17) 0.52282(12) 0.84587(10) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.732142 0.473551 0.866387 0.023 Uiso 1 1 calc R . . . .
C40 C 0.66913(17) 0.49884(12) 0.53280(10) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.56916(15) 0.47687(11) 0.64817(9) 0.0156(3) Uani 1 1 d . . . . .
H3 H 0.597711 0.436343 0.681714 0.019 Uiso 1 1 calc R . . . .
C15 C 0.84419(16) 0.47568(11) 0.67998(9) 0.0179(4) Uani 1 1 d . . . . .
H15 H 0.794058 0.443025 0.710477 0.022 Uiso 1 1 calc R . . . .
C53 C 0.35300(17) 0.37295(12) 0.49734(10) 0.0214(4) Uani 1 1 d . . . . .
H53 H 0.387625 0.422970 0.489323 0.026 Uiso 1 1 calc R . . . .
C43 C 1.05034(17) 0.74853(12) 0.59219(11) 0.0236(4) Uani 1 1 d . . . . .
H43 H 1.050963 0.762459 0.639737 0.028 Uiso 1 1 calc R . . . .
C1 C 0.77150(15) 0.54061(11) 0.64227(9) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.94304(16) 0.51263(11) 0.72435(10) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.43575(16) 0.52367(11) 0.75301(9) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.79466(17) 0.56373(12) 0.81254(10) 0.0195(4) Uani 1 1 d . . . . .
H12 H 0.774519 0.614026 0.794139 0.023 Uiso 1 1 calc R . . . .
C23 C 0.94064(17) 0.35528(12) 0.64953(11) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.51400(16) 0.49088(11) 0.81187(9) 0.0183(4) Uani 1 1 d . . . . .
C47 C 0.96615(17) 0.67428(11) 0.49497(10) 0.0208(4) Uani 1 1 d . . . . .
H47 H 0.910778 0.638455 0.477840 0.025 Uiso 1 1 calc R . . . .
C6 C 0.41254(16) 0.66735(11) 0.71425(10) 0.0195(4) Uani 1 1 d . . . . .
C13 C 0.91838(17) 0.53622(12) 0.80165(10) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.37051(16) 0.60395(11) 0.76854(10) 0.0199(4) Uani 1 1 d . . . . .
H7A H 0.287730 0.595878 0.764135 0.024 Uiso 1 1 calc R . . . .
H7B H 0.387066 0.622250 0.816115 0.024 Uiso 1 1 calc R . . . .
C44 C 1.12988(19) 0.78261(13) 0.54610(12) 0.0280(4) Uani 1 1 d . . . . .
H44 H 1.184550 0.819149 0.562926 0.034 Uiso 1 1 calc R . . . .
C49 C 0.32654(17) 0.25451(12) 0.57031(11) 0.0236(4) Uani 1 1 d . . . . .
H49 H 0.343946 0.225371 0.610950 0.028 Uiso 1 1 calc R . . . .
C41 C 0.54608(18) 0.55245(13) 0.92973(10) 0.0231(4) Uani 1 1 d . . . . .
H41A H 0.546704 0.498411 0.948472 0.035 Uiso 1 1 calc GR . . . .
H41B H 0.468784 0.573606 0.931311 0.035 Uiso 1 1 calc GR . . . .
H41C H 0.596165 0.586259 0.957398 0.035 Uiso 1 1 calc GR . . . .
C45 C 1.12827(18) 0.76259(13) 0.47556(12) 0.0275(4) Uani 1 1 d . . . . .
H45 H 1.182809 0.785070 0.445268 0.033 Uiso 1 1 calc R . . . .
C46 C 1.04592(18) 0.70909(12) 0.44911(11) 0.0243(4) Uani 1 1 d . . . . .
H46 H 1.044222 0.696734 0.401245 0.029 Uiso 1 1 calc R . . . .
C52 C 0.27544(19) 0.34136(14) 0.44850(11) 0.0277(4) Uani 1 1 d . . . . .
H52 H 0.258265 0.370266 0.407706 0.033 Uiso 1 1 calc R . . . .
C37 C 0.94752(18) 0.45886(14) 0.84361(11) 0.0269(4) Uani 1 1 d . . . . .
H37A H 0.901247 0.414707 0.826579 0.040 Uiso 1 1 calc GR . . . .
H37B H 0.931557 0.467633 0.892730 0.040 Uiso 1 1 calc GR . . . .
H37C H 1.027924 0.446067 0.837662 0.040 Uiso 1 1 calc GR . . . .
C51 C 0.22357(19) 0.26673(15) 0.46050(12) 0.0312(5) Uani 1 1 d . . . . .
H51 H 0.171970 0.245693 0.427624 0.037 Uiso 1 1 calc R . . . .
C38 C 0.32235(18) 0.73172(12) 0.69857(11) 0.0249(4) Uani 1 1 d . . . . .
H38A H 0.303144 0.759938 0.741287 0.037 Uiso 1 1 calc GR . . . .
H38B H 0.254174 0.706494 0.679776 0.037 Uiso 1 1 calc GR . . . .
H38C H 0.352690 0.769427 0.664737 0.037 Uiso 1 1 calc GR . . . .
C50 C 0.24852(18) 0.22344(13) 0.52144(13) 0.0294(5) Uani 1 1 d . . . . .
H50 H 0.213101 0.173719 0.529574 0.035 Uiso 1 1 calc R . . . .
C39 C 1.00061(19) 0.60465(14) 0.82316(11) 0.0298(5) Uani 1 1 d . . . . .
H39A H 1.079024 0.588198 0.814689 0.045 Uiso 1 1 calc GR . . . .
H39B H 0.990631 0.616433 0.872387 0.045 Uiso 1 1 calc GR . . . .
H39C H 0.983725 0.652215 0.795880 0.045 Uiso 1 1 calc GR . . . .
C25 C 1.01006(19) 0.31600(12) 0.59263(11) 0.0259(4) Uani 1 1 d . . . . .
H25A H 0.960177 0.301638 0.554122 0.039 Uiso 1 1 calc GR . . . .
H25B H 1.046427 0.268081 0.610858 0.039 Uiso 1 1 calc GR . . . .
H25C H 1.068246 0.353025 0.576311 0.039 Uiso 1 1 calc GR . . . .
C33 C 0.21665(19) 0.55016(14) 0.52908(12) 0.0283(4) Uani 1 1 d . . . . .
H33A H 0.197093 0.500509 0.552616 0.042 Uiso 1 1 calc GR . . . .
H33B H 0.214442 0.541970 0.478951 0.042 Uiso 1 1 calc GR . . . .
H33C H 0.162084 0.591452 0.541919 0.042 Uiso 1 1 calc GR . . . .
C29 C 0.2274(2) 0.35559(14) 0.75585(13) 0.0315(5) Uani 1 1 d . . . . .
H29A H 0.205614 0.362051 0.707297 0.047 Uiso 1 1 calc GR . . . .
H29B H 0.159528 0.345961 0.783815 0.047 Uiso 1 1 calc GR . . . .
H29C H 0.279178 0.310412 0.760264 0.047 Uiso 1 1 calc GR . . . .
H40A H 0.602(2) 0.4771(15) 0.5092(14) 0.025(6) Uiso 1 1 d . . . . .
H40B H 0.736(2) 0.5156(15) 0.5053(14) 0.026(6) Uiso 1 1 d . . . . .
H4 H 0.5803(19) 0.5755(13) 0.7109(12) 0.013(5) Uiso 1 1 d . . . . .
H1 H 0.7465(19) 0.5775(14) 0.6803(12) 0.015(5) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O19 C3 117.93(14) . . ?
C17 O16 C1 115.51(14) . . ?
C31 O30 C5 118.40(15) . . ?
C23 O22 C15 114.81(14) . . ?
C27 O26 C8 115.60(14) . . ?
C6 O34 H34 109.5 . . ?
O26 C27 C29 110.42(17) . . ?
O28 C27 O26 122.95(18) . . ?
O28 C27 C29 126.62(19) . . ?
C40 C2 C3 122.84(17) . . ?
C40 C2 C1 122.23(17) . . ?
C1 C2 C3 114.93(15) . . ?
O16 C17 C42 112.08(16) . . ?
O18 C17 O16 123.05(17) . . ?
O18 C17 C42 124.85(17) . . ?
O19 C20 C48 111.46(15) . . ?
O21 C20 O19 124.24(17) . . ?
O21 C20 C48 124.28(16) . . ?
C11 C10 H10 109.6 . . ?
C11 C10 C9 107.06(15) . . ?
C11 C10 C41 112.90(16) . . ?
C9 C10 H10 109.6 . . ?
C9 C10 C41 107.98(15) . . ?
C41 C10 H10 109.6 . . ?
C5 C4 C8 104.30(14) . . ?
C5 C4 H4 103.1(13) . . ?
C3 C4 C5 121.01(15) . . ?
C3 C4 C8 117.41(15) . . ?
C3 C4 H4 104.6(13) . . ?
C8 C4 H4 104.3(13) . . ?
O30 C5 C4 111.86(14) . . ?
O30 C5 H5 112.5 . . ?
O30 C5 C6 106.08(14) . . ?
C4 C5 H5 112.5 . . ?
C4 C5 C6 100.67(14) . . ?
C6 C5 H5 112.5 . . ?
C43 C42 C17 117.27(18) . . ?
C47 C42 C17 122.43(17) . . ?
C47 C42 C43 120.25(18) . . ?
O30 C31 C33 110.36(17) . . ?
O32 C31 O30 123.47(19) . . ?
O32 C31 C33 126.17(18) . . ?
C53 C48 C20 121.44(17) . . ?
C53 C48 C49 120.13(18) . . ?
C49 C48 C20 118.39(17) . . ?
C10 C11 H11 117.8 . . ?
C12 C11 C10 124.31(17) . . ?
C12 C11 H11 117.8 . . ?
C2 C40 H40A 119.6(15) . . ?
C2 C40 H40B 120.5(15) . . ?
H40A C40 H40B 120(2) . . ?
O19 C3 C2 108.01(14) . . ?
O19 C3 C4 109.98(14) . . ?
O19 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 C2 112.50(14) . . ?
C4 C3 H3 108.8 . . ?
O22 C15 H15 109.5 . . ?
O22 C15 C1 106.58(14) . . ?
O22 C15 C14 109.21(15) . . ?
C1 C15 H15 109.5 . . ?
C1 C15 C14 112.48(15) . . ?
C14 C15 H15 109.5 . . ?
C48 C53 H53 120.1 . . ?
C52 C53 C48 119.77(19) . . ?
C52 C53 H53 120.1 . . ?
C42 C43 H43 120.3 . . ?
C44 C43 C42 119.39(19) . . ?
C44 C43 H43 120.3 . . ?
O16 C1 C2 108.89(14) . . ?
O16 C1 C15 109.15(14) . . ?
O16 C1 H1 109.3(13) . . ?
C2 C1 C15 112.73(15) . . ?
C2 C1 H1 112.2(13) . . ?
C15 C1 H1 104.4(13) . . ?
O36 C14 C15 119.43(17) . . ?
O36 C14 C13 121.65(17) . . ?
C13 C14 C15 118.68(16) . . ?
O26 C8 C4 107.76(14) . . ?
O26 C8 C9 108.14(14) . . ?
O26 C8 C7 112.86(15) . . ?
C9 C8 C4 107.82(14) . . ?
C9 C8 C7 116.70(15) . . ?
C7 C8 C4 103.02(14) . . ?
C11 C12 H12 116.9 . . ?
C11 C12 C13 126.14(18) . . ?
C13 C12 H12 116.9 . . ?
O22 C23 C25 110.69(17) . . ?
O24 C23 O22 122.76(18) . . ?
O24 C23 C25 126.53(18) . . ?
O35 C9 C10 120.70(17) . . ?
O35 C9 C8 120.92(17) . . ?
C10 C9 C8 118.24(15) . . ?
C42 C47 H47 120.0 . . ?
C46 C47 C42 119.90(18) . . ?
C46 C47 H47 120.0 . . ?
O34 C6 C5 103.78(14) . . ?
O34 C6 C7 111.14(15) . . ?
O34 C6 C38 110.88(15) . . ?
C5 C6 C7 102.09(15) . . ?
C38 C6 C5 115.51(16) . . ?
C38 C6 C7 112.83(16) . . ?
C12 C13 C14 112.31(16) . . ?
C12 C13 C37 112.61(17) . . ?
C12 C13 C39 109.21(16) . . ?
C37 C13 C14 103.92(15) . . ?
C39 C13 C14 108.91(16) . . ?
C39 C13 C37 109.74(17) . . ?
C8 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
C6 C7 C8 107.37(15) . . ?
C6 C7 H7A 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.33(19) . . ?
C45 C44 H44 119.8 . . ?
C48 C49 H49 120.1 . . ?
C50 C49 C48 119.8(2) . . ?
C50 C49 H49 120.1 . . ?
C10 C41 H41A 109.5 . . ?
C10 C41 H41B 109.5 . . ?
C10 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C44 C45 H45 119.6 . . ?
C44 C45 C46 120.73(19) . . ?
C46 C45 H45 119.6 . . ?
C47 C46 C45 119.36(19) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C53 C52 H52 119.9 . . ?
C51 C52 C53 120.1(2) . . ?
C51 C52 H52 119.9 . . ?
C13 C37 H37A 109.5 . . ?
C13 C37 H37B 109.5 . . ?
C13 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C52 C51 H51 119.9 . . ?
C50 C51 C52 120.2(2) . . ?
C50 C51 H51 119.9 . . ?
C6 C38 H38A 109.5 . . ?
C6 C38 H38B 109.5 . . ?
C6 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C49 C50 H50 120.0 . . ?
C51 C50 C49 119.9(2) . . ?
C51 C50 H50 120.0 . . ?
C13 C39 H39A 109.5 . . ?
C13 C39 H39B 109.5 . . ?
C13 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O19 C20 1.339(2) . ?
O19 C3 1.447(2) . ?
O16 C17 1.360(2) . ?
O16 C1 1.444(2) . ?
O30 C5 1.438(2) . ?
O30 C31 1.349(2) . ?
O22 C15 1.430(2) . ?
O22 C23 1.359(2) . ?
O26 C27 1.361(2) . ?
O26 C8 1.438(2) . ?
O21 C20 1.210(2) . ?
O34 H34 0.8200 . ?
O34 C6 1.436(2) . ?
O18 C17 1.207(2) . ?
O36 C14 1.211(2) . ?
O28 C27 1.202(3) . ?
O32 C31 1.208(3) . ?
O24 C23 1.195(3) . ?
O35 C9 1.208(2) . ?
C27 C29 1.496(3) . ?
C2 C40 1.318(3) . ?
C2 C3 1.526(2) . ?
C2 C1 1.519(3) . ?
C17 C42 1.486(3) . ?
C20 C48 1.492(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.508(3) . ?
C10 C9 1.526(3) . ?
C10 C41 1.542(3) . ?
C4 C5 1.534(3) . ?
C4 C3 1.526(2) . ?
C4 C8 1.554(2) . ?
C4 H4 0.99(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.538(3) . ?
C42 C43 1.396(3) . ?
C42 C47 1.392(3) . ?
C31 C33 1.491(3) . ?
C48 C53 1.390(3) . ?
C48 C49 1.395(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.327(3) . ?
C40 H40A 0.97(3) . ?
C40 H40B 0.97(3) . ?
C3 H3 0.9800 . ?
C15 H15 0.9800 . ?
C15 C1 1.538(2) . ?
C15 C14 1.544(3) . ?
C53 H53 0.9300 . ?
C53 C52 1.390(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.388(3) . ?
C1 H1 0.99(2) . ?
C14 C13 1.543(3) . ?
C8 C9 1.535(3) . ?
C8 C7 1.553(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.515(3) . ?
C23 C25 1.493(3) . ?
C47 H47 0.9300 . ?
C47 C46 1.392(3) . ?
C6 C7 1.546(3) . ?
C6 C38 1.518(3) . ?
C13 C37 1.541(3) . ?
C13 C39 1.532(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C44 H44 0.9300 . ?
C44 C45 1.377(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.391(3) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C45 H45 0.9300 . ?
C45 C46 1.392(3) . ?
C46 H46 0.9300 . ?
C52 H52 0.9300 . ?
C52 C51 1.389(3) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C51 H51 0.9300 . ?
C51 C50 1.388(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C50 H50 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O19 C20 C48 C53 18.7(2) . . . . ?
O19 C20 C48 C49 -163.55(16) . . . . ?
O16 C17 C42 C43 -160.10(16) . . . . ?
O16 C17 C42 C47 17.5(2) . . . . ?
O30 C5 C6 O34 -172.24(13) . . . . ?
O30 C5 C6 C7 72.15(17) . . . . ?
O30 C5 C6 C38 -50.7(2) . . . . ?
O22 C15 C1 O16 -57.31(18) . . . . ?
O22 C15 C1 C2 63.83(19) . . . . ?
O22 C15 C14 O36 21.2(2) . . . . ?
O22 C15 C14 C13 -153.24(15) . . . . ?
O26 C8 C9 O35 14.2(2) . . . . ?
O26 C8 C9 C10 -170.17(15) . . . . ?
O26 C8 C7 C6 -115.62(16) . . . . ?
O21 C20 C48 C53 -159.75(19) . . . . ?
O21 C20 C48 C49 18.0(3) . . . . ?
O34 C6 C7 C8 -82.57(17) . . . . ?
O18 C17 C42 C43 18.2(3) . . . . ?
O18 C17 C42 C47 -164.13(19) . . . . ?
O36 C14 C13 C12 153.74(18) . . . . ?
O36 C14 C13 C37 -84.3(2) . . . . ?
O36 C14 C13 C39 32.6(3) . . . . ?
C27 O26 C8 C4 178.82(15) . . . . ?
C27 O26 C8 C9 62.52(19) . . . . ?
C27 O26 C8 C7 -68.1(2) . . . . ?
C17 O16 C1 C2 142.47(15) . . . . ?
C17 O16 C1 C15 -94.09(17) . . . . ?
C17 C42 C43 C44 175.64(18) . . . . ?
C17 C42 C47 C46 -175.83(17) . . . . ?
C20 O19 C3 C2 114.12(16) . . . . ?
C20 O19 C3 C4 -122.76(16) . . . . ?
C20 C48 C53 C52 177.65(18) . . . . ?
C20 C48 C49 C50 -178.08(18) . . . . ?
C10 C11 C12 C13 -177.16(17) . . . . ?
C4 C5 C6 O34 71.11(16) . . . . ?
C4 C5 C6 C7 -44.51(17) . . . . ?
C4 C5 C6 C38 -167.32(16) . . . . ?
C4 C8 C9 O35 -102.1(2) . . . . ?
C4 C8 C9 C10 73.57(19) . . . . ?
C4 C8 C7 C6 0.30(19) . . . . ?
C5 O30 C31 O32 3.6(3) . . . . ?
C5 O30 C31 C33 -176.46(15) . . . . ?
C5 C4 C3 O19 -53.0(2) . . . . ?
C5 C4 C3 C2 67.4(2) . . . . ?
C5 C4 C8 O26 91.09(16) . . . . ?
C5 C4 C8 C9 -152.40(14) . . . . ?
C5 C4 C8 C7 -28.43(17) . . . . ?
C5 C6 C7 C8 27.56(18) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C42 C47 C46 C45 0.0(3) . . . . ?
C31 O30 C5 C4 -106.91(18) . . . . ?
C31 O30 C5 C6 144.23(16) . . . . ?
C48 C53 C52 C51 0.1(3) . . . . ?
C48 C49 C50 C51 0.6(3) . . . . ?
C11 C10 C9 O35 52.1(2) . . . . ?
C11 C10 C9 C8 -123.61(17) . . . . ?
C11 C12 C13 C14 108.1(2) . . . . ?
C11 C12 C13 C37 -8.8(3) . . . . ?
C11 C12 C13 C39 -130.9(2) . . . . ?
C40 C2 C3 O19 4.1(2) . . . . ?
C40 C2 C3 C4 -117.4(2) . . . . ?
C40 C2 C1 O16 15.9(2) . . . . ?
C40 C2 C1 C15 -105.4(2) . . . . ?
C3 O19 C20 O21 0.8(3) . . . . ?
C3 O19 C20 C48 -177.62(14) . . . . ?
C3 C2 C1 O16 -164.24(14) . . . . ?
C3 C2 C1 C15 74.47(19) . . . . ?
C3 C4 C5 O30 68.6(2) . . . . ?
C3 C4 C5 C6 -179.06(16) . . . . ?
C3 C4 C8 O26 -45.9(2) . . . . ?
C3 C4 C8 C9 70.63(19) . . . . ?
C3 C4 C8 C7 -165.40(15) . . . . ?
C15 O22 C23 O24 11.0(3) . . . . ?
C15 O22 C23 C25 -167.90(16) . . . . ?
C15 C14 C13 C12 -32.0(2) . . . . ?
C15 C14 C13 C37 90.02(19) . . . . ?
C15 C14 C13 C39 -153.07(17) . . . . ?
C53 C48 C49 C50 -0.2(3) . . . . ?
C53 C52 C51 C50 0.3(3) . . . . ?
C43 C42 C47 C46 1.7(3) . . . . ?
C43 C44 C45 C46 1.1(3) . . . . ?
C1 O16 C17 O18 -1.0(2) . . . . ?
C1 O16 C17 C42 177.42(14) . . . . ?
C1 C2 C3 O19 -175.71(14) . . . . ?
C1 C2 C3 C4 62.72(19) . . . . ?
C1 C15 C14 O36 -96.9(2) . . . . ?
C1 C15 C14 C13 88.7(2) . . . . ?
C14 C15 C1 O16 62.34(19) . . . . ?
C14 C15 C1 C2 -176.53(15) . . . . ?
C8 O26 C27 O28 8.8(3) . . . . ?
C8 O26 C27 C29 -170.14(16) . . . . ?
C8 C4 C5 O30 -66.38(18) . . . . ?
C8 C4 C5 C6 45.91(17) . . . . ?
C8 C4 C3 O19 76.49(19) . . . . ?
C8 C4 C3 C2 -163.07(15) . . . . ?
C23 O22 C15 C1 -167.53(15) . . . . ?
C23 O22 C15 C14 70.72(19) . . . . ?
C9 C10 C11 C12 114.7(2) . . . . ?
C9 C8 C7 C6 118.20(17) . . . . ?
C47 C42 C43 C44 -2.0(3) . . . . ?
C7 C8 C9 O35 142.67(18) . . . . ?
C7 C8 C9 C10 -41.7(2) . . . . ?
C44 C45 C46 C47 -1.4(3) . . . . ?
C49 C48 C53 C52 -0.1(3) . . . . ?
C41 C10 C11 C12 -126.6(2) . . . . ?
C41 C10 C9 O35 -69.8(2) . . . . ?
C41 C10 C9 C8 114.55(18) . . . . ?
C52 C51 C50 C49 -0.6(3) . . . . ?
C38 C6 C7 C8 152.18(16) . . . . ?
