# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_taguchi20211130-2
_database_code_depnum_ccdc_archive 'CCDC 2257938'
loop_
_audit_author_name
_audit_author_address
'Kenichiro Nagai'
;School of Pharmacy, Kitasato University
Japan
;
_audit_update_record             
;
2023-04-21 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H38 O'
_chemical_formula_moiety         'C26 H38 O'
_chemical_formula_weight         366.59
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
_space_group_IT_number           5
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   49.6825(9)
_cell_length_b                   6.41808(12)
_cell_length_c                   13.2630(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.324(7)
_cell_angle_gamma                90.0000
_cell_volume                     4210.86(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17917
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616.00
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.951

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            23413
_diffrn_reflns_av_unetI/netI     0.1487
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7211
_reflns_number_gt                5135
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.858
_reflns_Friedel_fraction_full    0.861

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0912
_refine_ls_wR_factor_ref         0.2313
_refine_ls_wR_factor_gt          0.2112
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7211
_refine_ls_number_parameters     487
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0840P)²+7.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.26516(10) 0.3947(8) 0.4341(3) 0.0434(13) Uani 1 1 d . . . . .
H1 H 0.251782 0.319967 0.444182 0.052 Uiso 1 1 calc R U . . .
O2 O 0.24411(9) 0.6344(9) 0.1449(3) 0.0438(13) Uani 1 1 d . . . . .
H2 H 0.242748 0.607583 0.206172 0.053 Uiso 1 1 calc R U . . .
C3 C 0.30232(13) 0.2842(11) 0.1472(4) 0.0309(16) Uani 1 1 d . . . . .
C4 C 0.39839(13) 0.7063(12) 0.9201(4) 0.0333(17) Uani 1 1 d . . . . .
H4A H 0.396620 0.552787 0.922262 0.040 Uiso 1 1 calc R U . . .
H4B H 0.403758 0.756063 0.989709 0.040 Uiso 1 1 calc R U . . .
C5 C 0.27470(13) 0.4898(12) 0.5229(4) 0.0345(18) Uani 1 1 d . . . . .
C6 C 0.41266(13) 0.6752(12) 0.7411(4) 0.0317(17) Uani 1 1 d . . . . .
C7 C 0.26529(14) 0.5221(12) 0.1117(5) 0.0333(17) Uani 1 1 d . . . . .
C8 C 0.28078(13) 0.3950(12) 0.1796(4) 0.0328(17) Uani 1 1 d . . . . .
H8 H 0.276601 0.384252 0.247867 0.039 Uiso 1 1 calc R U . . .
C9 C 0.32028(13) 0.1267(12) 0.2030(4) 0.0321(16) Uani 1 1 d . . . . .
C10 C 0.29681(13) 0.6190(12) 0.5191(4) 0.0323(16) Uani 1 1 d . . . . .
H10 H 0.304767 0.638005 0.457362 0.039 Uiso 1 1 calc R U . . .
C11 C 0.33738(13) 0.8831(12) 0.7362(4) 0.0321(17) Uani 1 1 d . . . . .
C12 C 0.40433(14) 0.3342(12) 0.3293(4) 0.0335(17) Uani 1 1 d . . . . .
C13 C 0.30806(13) 0.2992(12) 0.0461(4) 0.0339(17) Uani 1 1 d . . . . .
C14 C 0.37401(13) 0.7003(12) 0.5950(4) 0.0329(17) Uani 1 1 d . . . . .
H14A H 0.389263 0.698998 0.551991 0.040 Uiso 1 1 calc R U . . .
H14B H 0.366183 0.558468 0.594960 0.040 Uiso 1 1 calc R U . . .
C15 C 0.42033(13) 0.7661(12) 0.8504(4) 0.0333(17) Uani 1 1 d . . . . .
H15 H 0.418455 0.920356 0.841863 0.040 Uiso 1 1 calc R U . . .
C16 C 0.35192(13) 0.3187(13) 0.3388(4) 0.0348(17) Uani 1 1 d . . . . .
H16A H 0.356900 0.322861 0.412811 0.042 Uiso 1 1 calc R U . . .
H16B H 0.346880 0.461607 0.316123 0.042 Uiso 1 1 calc R U . . .
C17 C 0.37604(13) 0.2459(12) 0.2857(4) 0.0306(16) Uani 1 1 d . . . . .
H17 H 0.377145 0.092333 0.298217 0.037 Uiso 1 1 calc R U . . .
C18 C 0.38421(12) 0.7635(12) 0.7035(4) 0.0322(17) Uani 1 1 d . . . . .
H18 H 0.386840 0.917792 0.700347 0.039 Uiso 1 1 calc R U . . .
C19 C 0.35190(14) 0.5049(12) 0.7786(4) 0.0346(17) Uani 1 1 d . . . . .
H19A H 0.345007 0.458030 0.710795 0.041 Uiso 1 1 calc R U . . .
H19B H 0.367372 0.418606 0.803640 0.041 Uiso 1 1 calc R U . . .
H19C H 0.337624 0.492336 0.824527 0.041 Uiso 1 1 calc R U . . .
C20 C 0.32791(13) 0.1745(12) 0.3161(4) 0.0385(19) Uani 1 1 d . . . . .
H20A H 0.312027 0.237426 0.344261 0.046 Uiso 1 1 calc R U . . .
H20B H 0.331840 0.041133 0.351995 0.046 Uiso 1 1 calc R U . . .
C21 C 0.29587(13) 0.6910(12) 0.6987(4) 0.0329(17) Uani 1 1 d . . . . .
C22 C 0.36228(14) 0.4947(11) 0.1351(4) 0.0349(17) Uani 1 1 d . . . . .
H22A H 0.346831 0.544804 0.169165 0.042 Uiso 1 1 calc R U . . .
H22B H 0.378003 0.583548 0.153726 0.042 Uiso 1 1 calc R U . . .
H22C H 0.357815 0.499652 0.061611 0.042 Uiso 1 1 calc R U . . .
C23 C 0.30735(13) 0.7213(11) 0.6067(4) 0.0313(16) Uani 1 1 d . . . . .
C24 C 0.35260(13) 0.8553(11) 0.5528(4) 0.0337(17) Uani 1 1 d . . . . .
H24A H 0.361358 0.991941 0.544359 0.040 Uiso 1 1 calc R U . . .
H24B H 0.345175 0.807441 0.484858 0.040 Uiso 1 1 calc R U . . .
C25 C 0.36885(14) 0.2689(12) 0.1679(4) 0.0333(17) Uani 1 1 d . . . . .
C26 C 0.39322(13) 0.1929(12) 0.1134(4) 0.0365(18) Uani 1 1 d . . . . .
H26A H 0.394786 0.039856 0.121155 0.044 Uiso 1 1 calc R U . . .
H26B H 0.389749 0.223624 0.040236 0.044 Uiso 1 1 calc R U . . .
C27 C 0.36084(13) 0.7333(12) 0.7739(4) 0.0306(16) Uani 1 1 d . . . . .
C28 C 0.37156(13) 0.8015(12) 0.8820(4) 0.0326(16) Uani 1 1 d . . . . .
H28A H 0.373408 0.955103 0.883198 0.039 Uiso 1 1 calc R U . . .
H28B H 0.358020 0.763579 0.929120 0.039 Uiso 1 1 calc R U . . .
C29 C 0.32956(14) 0.8841(12) 0.6180(4) 0.0345(17) Uani 1 1 d . . . . .
C30 C 0.27165(14) 0.5409(12) 0.0111(5) 0.0352(17) Uani 1 1 d . . . . .
H30 H 0.261413 0.630842 -0.034571 0.042 Uiso 1 1 calc R U . . .
C31 C 0.29294(13) 0.4273(12) -0.0209(5) 0.0366(18) Uani 1 1 d . . . . .
H31 H 0.297162 0.437587 -0.089094 0.044 Uiso 1 1 calc R U . . .
C32 C 0.42598(13) 0.2417(12) 0.2665(4) 0.0332(17) Uani 1 1 d . . . . .
H32 H 0.423072 0.087798 0.270274 0.040 Uiso 1 1 calc R U . . .
C33 C 0.34505(13) 0.1148(13) 0.1376(4) 0.0362(18) Uani 1 1 d . . . . .
C34 C 0.27366(13) 0.5618(12) 0.7012(5) 0.0350(17) Uani 1 1 d . . . . .
H34 H 0.265504 0.543966 0.762645 0.042 Uiso 1 1 calc R U . . .
C35 C 0.44979(14) 0.7343(13) 0.8960(5) 0.0396(19) Uani 1 1 d . . . . .
C36 C 0.33155(14) 0.1575(12) 0.0291(5) 0.0378(18) Uani 1 1 d . . . . .
H36A H 0.344329 0.226769 -0.013029 0.045 Uiso 1 1 calc R U . . .
H36B H 0.325152 0.026280 -0.004280 0.045 Uiso 1 1 calc R U . . .
C37 C 0.40990(13) 0.2513(12) 0.4397(4) 0.0353(18) Uani 1 1 d . . . . .
H37A H 0.397471 0.321532 0.483009 0.042 Uiso 1 1 calc R U . . .
H37B H 0.405901 0.100241 0.440335 0.042 Uiso 1 1 calc R U . . .
C38 C 0.43338(13) 0.7734(13) 0.6729(5) 0.0381(18) Uani 1 1 d . . . . .
H38A H 0.430159 0.715252 0.603654 0.046 Uiso 1 1 calc R U . . .
H38B H 0.430300 0.925642 0.668378 0.046 Uiso 1 1 calc R U . . .
C39 C 0.45620(14) 0.2717(14) 0.3080(5) 0.0407(19) Uani 1 1 d . . . . .
C40 C 0.31028(13) 0.8294(11) 0.7790(4) 0.0311(16) Uani 1 1 d . . . . .
H40A H 0.313419 0.754789 0.844371 0.037 Uiso 1 1 calc R U . . .
H40B H 0.299674 0.957067 0.789058 0.037 Uiso 1 1 calc R U . . .
C41 C 0.31520(14) 1.0918(12) 0.5887(5) 0.0401(19) Uani 1 1 d . . . . .
H41A H 0.300161 1.112585 0.630474 0.048 Uiso 1 1 calc R U . . .
H41B H 0.328079 1.207034 0.599833 0.048 Uiso 1 1 calc R U . . .
H41C H 0.308249 1.087722 0.517076 0.048 Uiso 1 1 calc R U . . .
C42 C 0.46864(14) 0.8208(14) 0.8194(5) 0.042(2) Uani 1 1 d . . . . .
H42A H 0.466837 0.974402 0.816697 0.051 Uiso 1 1 calc R U . . .
H42B H 0.487596 0.787956 0.843910 0.051 Uiso 1 1 calc R U . . .
C43 C 0.26316(14) 0.4576(12) 0.6139(5) 0.0376(18) Uani 1 1 d . . . . .
H43 H 0.248264 0.365456 0.616216 0.045 Uiso 1 1 calc R U . . .
C44 C 0.41403(14) 0.4354(12) 0.7341(5) 0.0359(18) Uani 1 1 d . . . . .
H44A H 0.432237 0.388124 0.758455 0.043 Uiso 1 1 calc R U . . .
H44B H 0.400845 0.373663 0.775852 0.043 Uiso 1 1 calc R U . . .
H44C H 0.409883 0.392148 0.663483 0.043 Uiso 1 1 calc R U . . .
C45 C 0.45490(14) 0.8667(13) 0.9921(5) 0.0419(19) Uani 1 1 d . . . . .
H45A H 0.450001 1.011867 0.976561 0.050 Uiso 1 1 calc R U . . .
H45B H 0.443896 0.813865 1.044154 0.050 Uiso 1 1 calc R U . . .
H45C H 0.474071 0.859059 1.017043 0.050 Uiso 1 1 calc R U . . .
C46 C 0.42002(14) 0.2927(12) 0.1533(4) 0.0374(18) Uani 1 1 d . . . . .
H46A H 0.419012 0.445560 0.143683 0.045 Uiso 1 1 calc R U . . .
H46B H 0.434758 0.238588 0.115191 0.045 Uiso 1 1 calc R U . . .
C47 C 0.43881(14) 0.2860(14) 0.4847(5) 0.047(2) Uani 1 1 d . . . . .
H47A H 0.441292 0.222380 0.552871 0.056 Uiso 1 1 calc R U . . .
H47B H 0.442244 0.437467 0.492089 0.056 Uiso 1 1 calc R U . . .
C48 C 0.46263(14) 0.7332(14) 0.7128(5) 0.046(2) Uani 1 1 d . . . . .
H48A H 0.474809 0.798953 0.667027 0.055 Uiso 1 1 calc R U . . .
H48B H 0.466149 0.581346 0.713633 0.055 Uiso 1 1 calc R U . . .
C49 C 0.45771(15) 0.5086(14) 0.9237(5) 0.047(2) Uani 1 1 d . . . . .
H49A H 0.454636 0.420343 0.863423 0.057 Uiso 1 1 calc R U . . .
H49B H 0.476862 0.503404 0.949067 0.057 Uiso 1 1 calc R U . . .
H49C H 0.446687 0.458210 0.976178 0.057 Uiso 1 1 calc R U . . .
C50 C 0.47432(14) 0.1329(15) 0.2477(5) 0.049(2) Uani 1 1 d . . . . .
H50A H 0.468116 -0.011889 0.249687 0.059 Uiso 1 1 calc R U . . .
H50B H 0.473304 0.180524 0.177225 0.059 Uiso 1 1 calc R U . . .
H50C H 0.493057 0.141755 0.277788 0.059 Uiso 1 1 calc R U . . .
C51 C 0.40414(14) 0.5760(12) 0.3355(5) 0.0398(19) Uani 1 1 d . . . . .
H51A H 0.389814 0.621214 0.376639 0.048 Uiso 1 1 calc R U . . .
H51B H 0.421660 0.625064 0.366572 0.048 Uiso 1 1 calc R U . . .
H51C H 0.400813 0.634253 0.267165 0.048 Uiso 1 1 calc R U . . .
C52 C 0.45906(14) 0.1919(14) 0.4185(5) 0.042(2) Uani 1 1 d . . . . .
H52A H 0.456853 0.038565 0.417868 0.051 Uiso 1 1 calc R U . . .
H52B H 0.477550 0.223224 0.449052 0.051 Uiso 1 1 calc R U . . .
C53 C 0.46670(15) 0.4956(14) 0.3025(5) 0.050(2) Uani 1 1 d . . . . .
H53A H 0.455567 0.588113 0.340265 0.061 Uiso 1 1 calc R U . . .
H53B H 0.485497 0.501525 0.332192 0.061 Uiso 1 1 calc R U . . .
H53C H 0.465744 0.540294 0.231629 0.061 Uiso 1 1 calc R U . . .
C54 C 0.30505(15) -0.0808(13) 0.1975(5) 0.0441(19) Uani 1 1 d . . . . .
H54A H 0.316225 -0.188169 0.233391 0.053 Uiso 1 1 calc R U . . .
H54B H 0.288096 -0.065544 0.229151 0.053 Uiso 1 1 calc R U . . .
H54C H 0.301066 -0.121651 0.126505 0.053 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C5 1.371(7) . ?
O1 H1 0.8400 . ?
O2 C7 1.381(8) . ?
O2 H2 0.8400 . ?
C3 C8 1.385(9) . ?
C3 C13 1.400(8) . ?
C3 C9 1.498(9) . ?
C4 C28 1.510(9) . ?
C4 C15 1.542(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.381(9) . ?
C5 C43 1.398(8) . ?
C6 C44 1.544(10) . ?
C6 C18 1.561(9) . ?
C6 C38 1.565(9) . ?
C6 C15 1.576(8) . ?
C7 C8 1.392(9) . ?
C7 C30 1.405(8) . ?
C8 H8 0.9500 . ?
C9 C54 1.530(10) . ?
C9 C20 1.543(8) . ?
C9 C33 1.572(9) . ?
C10 C23 1.393(9) . ?
C10 H10 0.9500 . ?
C11 C40 1.548(9) . ?
C11 C27 1.557(9) . ?
C11 C29 1.580(7) . ?
C12 C32 1.539(9) . ?
C12 C51 1.554(10) . ?
C12 C37 1.558(8) . ?
C12 C17 1.575(9) . ?
C13 C31 1.380(9) . ?
C13 C36 1.513(9) . ?
C14 C24 1.524(9) . ?
C14 C18 1.536(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C35 1.545(9) . ?
C15 H15 1.0000 . ?
C16 C20 1.518(10) . ?
C16 C17 1.519(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C25 1.578(8) . ?
C17 H17 1.0000 . ?
C18 C27 1.567(8) . ?
C18 H18 1.0000 . ?
C19 C27 1.534(10) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C34 1.383(9) . ?
C21 C23 1.408(8) . ?
C21 C40 1.514(9) . ?
C22 C25 1.539(10) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C29 1.517(10) . ?
C24 C29 1.509(9) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.545(9) . ?
C25 C33 1.565(10) . ?
C26 C46 1.527(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.546(8) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C41 1.545(10) . ?
C30 C31 1.383(9) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C46 1.539(8) . ?
C32 C39 1.562(9) . ?
C32 H32 1.0000 . ?
C33 C36 1.554(8) . ?
C34 C43 1.396(9) . ?
C34 H34 0.9500 . ?
C35 C45 1.533(10) . ?
C35 C49 1.536(11) . ?
C35 C42 1.547(9) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C47 1.520(9) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C48 1.522(9) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C53 1.533(11) . ?
C39 C50 1.542(10) . ?
C39 C52 1.546(9) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C48 1.526(9) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C52 1.520(9) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?

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
C5 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C8 C3 C13 119.6(6) . . ?
C8 C3 C9 129.4(6) . . ?
C13 C3 C9 110.8(6) . . ?
C28 C4 C15 110.5(5) . . ?
C28 C4 H4A 109.5 . . ?
C15 C4 H4A 109.5 . . ?
C28 C4 H4B 109.5 . . ?
C15 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C10 116.7(6) . . ?
O1 C5 C43 122.6(6) . . ?
C10 C5 C43 120.7(6) . . ?
C44 C6 C18 112.7(6) . . ?
C44 C6 C38 109.4(6) . . ?
C18 C6 C38 107.1(5) . . ?
C44 C6 C15 114.6(6) . . ?
C18 C6 C15 107.1(5) . . ?
C38 C6 C15 105.5(5) . . ?
O2 C7 C8 119.5(6) . . ?
O2 C7 C30 120.2(6) . . ?
C8 C7 C30 120.3(6) . . ?
C3 C8 C7 119.8(6) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C3 C9 C54 107.1(5) . . ?
C3 C9 C20 115.3(6) . . ?
C54 C9 C20 107.2(6) . . ?
C3 C9 C33 102.8(5) . . ?
C54 C9 C33 109.9(6) . . ?
C20 C9 C33 114.3(5) . . ?
C5 C10 C23 119.4(6) . . ?
C5 C10 H10 120.3 . . ?
C23 C10 H10 120.3 . . ?
C40 C11 C27 113.3(6) . . ?
C40 C11 C29 102.9(5) . . ?
C27 C11 C29 115.4(5) . . ?
C32 C12 C51 114.9(6) . . ?
C32 C12 C37 107.7(6) . . ?
C51 C12 C37 107.0(6) . . ?
C32 C12 C17 107.9(5) . . ?
C51 C12 C17 111.7(6) . . ?
C37 C12 C17 107.3(5) . . ?
C31 C13 C3 120.6(6) . . ?
C31 C13 C36 130.1(6) . . ?
C3 C13 C36 109.2(6) . . ?
C24 C14 C18 109.3(6) . . ?
C24 C14 H14A 109.8 . . ?
C18 C14 H14A 109.8 . . ?
C24 C14 H14B 109.8 . . ?
C18 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C4 C15 C35 115.4(5) . . ?
C4 C15 C6 109.6(5) . . ?
C35 C15 C6 116.8(5) . . ?
C4 C15 H15 104.5 . . ?
C35 C15 H15 104.5 . . ?
C6 C15 H15 104.5 . . ?
C20 C16 C17 111.1(6) . . ?
C20 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C20 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C12 115.8(6) . . ?
C16 C17 C25 108.3(5) . . ?
C12 C17 C25 116.2(5) . . ?
C16 C17 H17 105.1 . . ?
C12 C17 H17 105.1 . . ?
C25 C17 H17 105.1 . . ?
C14 C18 C6 114.4(5) . . ?
C14 C18 C27 109.1(5) . . ?
C6 C18 C27 117.7(5) . . ?
C14 C18 H18 104.8 . . ?
C6 C18 H18 104.8 . . ?
C27 C18 H18 104.8 . . ?
C27 C19 H19A 109.5 . . ?
C27 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C27 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 C9 115.6(5) . . ?
C16 C20 H20A 108.4 . . ?
C9 C20 H20A 108.4 . . ?
C16 C20 H20B 108.4 . . ?
C9 C20 H20B 108.4 . . ?
H20A C20 H20B 107.4 . . ?
C34 C21 C23 119.4(6) . . ?
C34 C21 C40 131.4(6) . . ?
C23 C21 C40 109.0(6) . . ?
C25 C22 H22A 109.5 . . ?
C25 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C25 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 C21 120.4(6) . . ?
C10 C23 C29 128.4(6) . . ?
C21 C23 C29 111.0(5) . . ?
C29 C24 C14 114.2(5) . . ?
C29 C24 H24A 108.7 . . ?
C14 C24 H24A 108.7 . . ?
C29 C24 H24B 108.7 . . ?
C14 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C22 C25 C26 108.7(5) . . ?
C22 C25 C33 112.8(6) . . ?
C26 C25 C33 106.7(6) . . ?
C22 C25 C17 113.0(5) . . ?
C26 C25 C17 108.5(5) . . ?
C33 C25 C17 106.9(5) . . ?
C46 C26 C25 113.7(6) . . ?
C46 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C46 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C19 C27 C28 107.9(5) . . ?
C19 C27 C11 113.1(6) . . ?
C28 C27 C11 107.8(5) . . ?
C19 C27 C18 112.1(6) . . ?
C28 C27 C18 107.8(5) . . ?
C11 C27 C18 107.8(5) . . ?
C4 C28 C27 114.4(6) . . ?
C4 C28 H28A 108.7 . . ?
C27 C28 H28A 108.7 . . ?
C4 C28 H28B 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C24 C29 C23 116.3(6) . . ?
C24 C29 C41 108.6(6) . . ?
C23 C29 C41 104.8(5) . . ?
C24 C29 C11 116.0(5) . . ?
C23 C29 C11 101.8(5) . . ?
C41 C29 C11 108.6(5) . . ?
C31 C30 C7 119.5(6) . . ?
C31 C30 H30 120.3 . . ?
C7 C30 H30 120.3 . . ?
C13 C31 C30 120.2(6) . . ?
C13 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C12 C32 C46 111.4(6) . . ?
C12 C32 C39 117.3(5) . . ?
C46 C32 C39 114.1(5) . . ?
C12 C32 H32 104.1 . . ?
C46 C32 H32 104.1 . . ?
C39 C32 H32 104.1 . . ?
C36 C33 C25 112.1(6) . . ?
C36 C33 C9 102.1(5) . . ?
C25 C33 C9 116.1(6) . . ?
C21 C34 C43 120.3(6) . . ?
C21 C34 H34 119.8 . . ?
C43 C34 H34 119.8 . . ?
C45 C35 C49 107.8(6) . . ?
C45 C35 C15 109.3(6) . . ?
C49 C35 C15 115.5(7) . . ?
C45 C35 C42 106.4(6) . . ?
C49 C35 C42 109.8(6) . . ?
C15 C35 C42 107.7(5) . . ?
C13 C36 C33 104.0(5) . . ?
C13 C36 H36A 111.0 . . ?
C33 C36 H36A 111.0 . . ?
C13 C36 H36B 111.0 . . ?
C33 C36 H36B 111.0 . . ?
H36A C36 H36B 109.0 . . ?
C47 C37 C12 113.4(6) . . ?
C47 C37 H37A 108.9 . . ?
C12 C37 H37A 108.9 . . ?
C47 C37 H37B 108.9 . . ?
C12 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C48 C38 C6 112.9(6) . . ?
C48 C38 H38A 109.0 . . ?
C6 C38 H38A 109.0 . . ?
C48 C38 H38B 109.0 . . ?
C6 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C53 C39 C50 107.4(6) . . ?
C53 C39 C52 110.7(6) . . ?
C50 C39 C52 107.1(6) . . ?
C53 C39 C32 114.8(7) . . ?
C50 C39 C32 109.6(6) . . ?
C52 C39 C32 107.1(5) . . ?
C21 C40 C11 104.1(5) . . ?
C21 C40 H40A 110.9 . . ?
C11 C40 H40A 110.9 . . ?
C21 C40 H40B 110.9 . . ?
C11 C40 H40B 110.9 . . ?
H40A C40 H40B 109.0 . . ?
C29 C41 H41A 109.5 . . ?
C29 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C29 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C48 C42 C35 113.5(6) . . ?
C48 C42 H42A 108.9 . . ?
C35 C42 H42A 108.9 . . ?
C48 C42 H42B 108.9 . . ?
C35 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C34 C43 C5 119.6(7) . . ?
C34 C43 H43 120.2 . . ?
C5 C43 H43 120.2 . . ?
C6 C44 H44A 109.5 . . ?
C6 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C6 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C35 C45 H45A 109.5 . . ?
C35 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C35 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C26 C46 C32 109.3(5) . . ?
C26 C46 H46A 109.8 . . ?
C32 C46 H46A 109.8 . . ?
C26 C46 H46B 109.8 . . ?
C32 C46 H46B 109.8 . . ?
H46A C46 H46B 108.3 . . ?
C37 C47 C52 111.5(6) . . ?
C37 C47 H47A 109.3 . . ?
C52 C47 H47A 109.3 . . ?
C37 C47 H47B 109.3 . . ?
C52 C47 H47B 109.3 . . ?
H47A C47 H47B 108.0 . . ?
C38 C48 C42 111.0(6) . . ?
C38 C48 H48A 109.4 . . ?
C42 C48 H48A 109.4 . . ?
C38 C48 H48B 109.4 . . ?
C42 C48 H48B 109.4 . . ?
H48A C48 H48B 108.0 . . ?
C35 C49 H49A 109.5 . . ?
C35 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C35 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C39 C50 H50A 109.5 . . ?
C39 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C39 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C12 C51 H51A 109.5 . . ?
C12 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C12 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C47 C52 C39 114.1(6) . . ?
C47 C52 H52A 108.7 . . ?
C39 C52 H52A 108.7 . . ?
C47 C52 H52B 108.7 . . ?
C39 C52 H52B 108.7 . . ?
H52A C52 H52B 107.6 . . ?
C39 C53 H53A 109.5 . . ?
C39 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C39 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C9 C54 H54A 109.5 . . ?
C9 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C9 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?

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
C13 C3 C8 C7 -0.8(10) . . . . ?
C9 C3 C8 C7 -174.6(7) . . . . ?
O2 C7 C8 C3 -179.0(6) . . . . ?
C30 C7 C8 C3 -1.0(10) . . . . ?
C8 C3 C9 C54 80.8(8) . . . . ?
C13 C3 C9 C54 -93.4(6) . . . . ?
C8 C3 C9 C20 -38.4(10) . . . . ?
C13 C3 C9 C20 147.4(6) . . . . ?
C8 C3 C9 C33 -163.4(7) . . . . ?
C13 C3 C9 C33 22.4(8) . . . . ?
O1 C5 C10 C23 179.6(6) . . . . ?
C43 C5 C10 C23 -1.2(11) . . . . ?
C8 C3 C13 C31 1.8(10) . . . . ?
C9 C3 C13 C31 176.6(6) . . . . ?
C8 C3 C13 C36 -177.6(6) . . . . ?
C9 C3 C13 C36 -2.8(8) . . . . ?
C28 C4 C15 C35 163.0(6) . . . . ?
C28 C4 C15 C6 -62.6(8) . . . . ?
C44 C6 C15 C4 -68.5(7) . . . . ?
C18 C6 C15 C4 57.3(7) . . . . ?
C38 C6 C15 C4 171.1(6) . . . . ?
C44 C6 C15 C35 65.1(8) . . . . ?
C18 C6 C15 C35 -169.0(6) . . . . ?
C38 C6 C15 C35 -55.2(8) . . . . ?
C20 C16 C17 C12 -160.9(5) . . . . ?
C20 C16 C17 C25 66.4(7) . . . . ?
C32 C12 C17 C16 179.6(6) . . . . ?
C51 C12 C17 C16 -53.2(8) . . . . ?
C37 C12 C17 C16 63.7(8) . . . . ?
C32 C12 C17 C25 -51.6(8) . . . . ?
C51 C12 C17 C25 75.7(7) . . . . ?
C37 C12 C17 C25 -167.4(6) . . . . ?
C24 C14 C18 C6 -158.2(6) . . . . ?
C24 C14 C18 C27 67.7(7) . . . . ?
C44 C6 C18 C14 -56.2(7) . . . . ?
C38 C6 C18 C14 64.1(8) . . . . ?
C15 C6 C18 C14 176.9(6) . . . . ?
C44 C6 C18 C27 73.8(7) . . . . ?
C38 C6 C18 C27 -165.8(6) . . . . ?
C15 C6 C18 C27 -53.1(8) . . . . ?
C17 C16 C20 C9 -50.6(8) . . . . ?
C3 C9 C20 C16 -84.6(7) . . . . ?
C54 C9 C20 C16 156.3(6) . . . . ?
C33 C9 C20 C16 34.2(9) . . . . ?
C5 C10 C23 C21 1.0(10) . . . . ?
C5 C10 C23 C29 -173.8(7) . . . . ?
C34 C21 C23 C10 -1.3(10) . . . . ?
C40 C21 C23 C10 -176.9(6) . . . . ?
C34 C21 C23 C29 174.3(6) . . . . ?
C40 C21 C23 C29 -1.3(8) . . . . ?
C18 C14 C24 C29 -54.2(8) . . . . ?
C16 C17 C25 C22 59.9(8) . . . . ?
C12 C17 C25 C22 -72.4(8) . . . . ?
C16 C17 C25 C26 -179.4(6) . . . . ?
C12 C17 C25 C26 48.2(8) . . . . ?
C16 C17 C25 C33 -64.7(7) . . . . ?
C12 C17 C25 C33 162.9(6) . . . . ?
C22 C25 C26 C46 71.8(7) . . . . ?
C33 C25 C26 C46 -166.3(6) . . . . ?
C17 C25 C26 C46 -51.4(8) . . . . ?
C40 C11 C27 C19 39.9(7) . . . . ?
C29 C11 C27 C19 -78.3(7) . . . . ?
C40 C11 C27 C28 -79.3(7) . . . . ?
C29 C11 C27 C28 162.4(6) . . . . ?
C40 C11 C27 C18 164.5(5) . . . . ?
C29 C11 C27 C18 46.2(7) . . . . ?
C14 C18 C27 C19 62.2(7) . . . . ?
C6 C18 C27 C19 -70.2(7) . . . . ?
C14 C18 C27 C28 -179.1(6) . . . . ?
C6 C18 C27 C28 48.5(8) . . . . ?
C14 C18 C27 C11 -62.9(7) . . . . ?
C6 C18 C27 C11 164.7(6) . . . . ?
C15 C4 C28 C27 59.8(8) . . . . ?
C19 C27 C28 C4 71.3(7) . . . . ?
C11 C27 C28 C4 -166.2(6) . . . . ?
C18 C27 C28 C4 -50.0(8) . . . . ?
C14 C24 C29 C23 -81.7(7) . . . . ?
C14 C24 C29 C41 160.5(6) . . . . ?
C14 C24 C29 C11 38.0(9) . . . . ?
C10 C23 C29 C24 -36.7(10) . . . . ?
C21 C23 C29 C24 148.1(6) . . . . ?
C10 C23 C29 C41 83.2(8) . . . . ?
C21 C23 C29 C41 -92.0(6) . . . . ?
C10 C23 C29 C11 -163.8(7) . . . . ?
C21 C23 C29 C11 21.1(7) . . . . ?
C40 C11 C29 C24 -158.9(6) . . . . ?
C27 C11 C29 C24 -35.0(9) . . . . ?
C40 C11 C29 C23 -31.6(7) . . . . ?
C27 C11 C29 C23 92.2(7) . . . . ?
C40 C11 C29 C41 78.5(7) . . . . ?
C27 C11 C29 C41 -157.6(6) . . . . ?
O2 C7 C30 C31 180.0(6) . . . . ?
C8 C7 C30 C31 1.9(10) . . . . ?
C3 C13 C31 C30 -0.8(11) . . . . ?
C36 C13 C31 C30 178.4(7) . . . . ?
C7 C30 C31 C13 -1.0(10) . . . . ?
C51 C12 C32 C46 -68.0(8) . . . . ?
C37 C12 C32 C46 172.8(6) . . . . ?
C17 C12 C32 C46 57.3(8) . . . . ?
C51 C12 C32 C39 66.2(8) . . . . ?
C37 C12 C32 C39 -53.0(8) . . . . ?
C17 C12 C32 C39 -168.5(6) . . . . ?
C22 C25 C33 C36 42.0(7) . . . . ?
C26 C25 C33 C36 -77.3(7) . . . . ?
C17 C25 C33 C36 166.7(6) . . . . ?
C22 C25 C33 C9 -74.8(7) . . . . ?
C26 C25 C33 C9 165.9(6) . . . . ?
C17 C25 C33 C9 49.9(8) . . . . ?
C3 C9 C33 C36 -32.0(7) . . . . ?
C54 C9 C33 C36 81.8(7) . . . . ?
C20 C9 C33 C36 -157.7(6) . . . . ?
C3 C9 C33 C25 90.3(7) . . . . ?
C54 C9 C33 C25 -155.9(6) . . . . ?
C20 C9 C33 C25 -35.4(9) . . . . ?
C23 C21 C34 C43 1.9(10) . . . . ?
C40 C21 C34 C43 176.3(7) . . . . ?
C4 C15 C35 C45 -59.7(9) . . . . ?
C6 C15 C35 C45 169.3(6) . . . . ?
C4 C15 C35 C49 62.0(8) . . . . ?
C6 C15 C35 C49 -69.0(8) . . . . ?
C4 C15 C35 C42 -174.9(6) . . . . ?
C6 C15 C35 C42 54.1(9) . . . . ?
C31 C13 C36 C33 162.3(8) . . . . ?
C3 C13 C36 C33 -18.4(8) . . . . ?
C25 C33 C36 C13 -94.2(7) . . . . ?
C9 C33 C36 C13 30.7(7) . . . . ?
C32 C12 C37 C47 52.3(8) . . . . ?
C51 C12 C37 C47 -71.9(8) . . . . ?
C17 C12 C37 C47 168.2(6) . . . . ?
C44 C6 C38 C48 -68.2(8) . . . . ?
C18 C6 C38 C48 169.3(6) . . . . ?
C15 C6 C38 C48 55.5(8) . . . . ?
C12 C32 C39 C53 -70.4(8) . . . . ?
C46 C32 C39 C53 62.6(8) . . . . ?
C12 C32 C39 C50 168.7(6) . . . . ?
C46 C32 C39 C50 -58.3(9) . . . . ?
C12 C32 C39 C52 52.9(9) . . . . ?
C46 C32 C39 C52 -174.1(6) . . . . ?
C34 C21 C40 C11 165.5(7) . . . . ?
C23 C21 C40 C11 -19.6(7) . . . . ?
C27 C11 C40 C21 -93.7(6) . . . . ?
C29 C11 C40 C21 31.5(7) . . . . ?
C45 C35 C42 C48 -169.6(6) . . . . ?
C49 C35 C42 C48 74.1(8) . . . . ?
C15 C35 C42 C48 -52.5(9) . . . . ?
C21 C34 C43 C5 -2.1(11) . . . . ?
O1 C5 C43 C34 -179.1(7) . . . . ?
C10 C5 C43 C34 1.8(11) . . . . ?
C25 C26 C46 C32 59.9(8) . . . . ?
C12 C32 C46 C26 -62.7(8) . . . . ?
C39 C32 C46 C26 161.5(6) . . . . ?
C12 C37 C47 C52 -55.5(9) . . . . ?
C6 C38 C48 C42 -58.9(9) . . . . ?
C35 C42 C48 C38 56.7(9) . . . . ?
C37 C47 C52 C39 56.1(9) . . . . ?
C53 C39 C52 C47 73.4(8) . . . . ?
C50 C39 C52 C47 -169.8(6) . . . . ?
C32 C39 C52 C47 -52.3(9) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_taguchi20211203-1
_database_code_depnum_ccdc_archive 'CCDC 2257940'
loop_
_audit_author_name
_audit_author_address
'Kenichiro Nagai'
;School of Pharmacy, Kitasato University
Japan
;
_audit_update_record             
;
2023-04-21 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H40 O'
_chemical_formula_moiety         'C27 H40 O'
_chemical_formula_weight         380.61
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   13.3948(3)
_cell_length_b                   6.52070(14)
_cell_length_c                   13.5565(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.239(8)
_cell_angle_gamma                90.0000
_cell_volume                     1103.65(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420.00
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.951

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12436
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3832
_reflns_number_gt                2859
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_fraction_full    0.892

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1478
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0633P)²+0.4368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.9513(3) 0.7492(6) 0.6860(3) 0.0388(10) Uani 1 1 d . . . . .
C2 C 0.8157(4) 0.5623(9) 0.5593(4) 0.0332(13) Uani 1 1 d . . . . .
H2 H 0.805860 0.488739 0.615599 0.040 Uiso 1 1 calc R U . . .
C3 C 0.6358(4) 0.3625(8) 0.2938(4) 0.0274(12) Uani 1 1 d . . . . .
H3 H 0.685095 0.253088 0.286662 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3171(4) 0.4029(9) 0.1687(4) 0.0303(13) Uani 1 1 d . . . . .
C5 C 0.7523(4) 0.5215(8) 0.4552(4) 0.0281(12) Uani 1 1 d . . . . .
C6 C 0.5078(4) 0.3437(9) 0.1034(3) 0.0289(13) Uani 1 1 d . . . . .
H6A H 0.531883 0.485534 0.098492 0.035 Uiso 1 1 calc R U . . .
H6B H 0.554693 0.249450 0.082597 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7655(4) 0.6301(8) 0.3729(4) 0.0316(13) Uani 1 1 d . . . . .
C8 C 0.3924(4) 0.3188(8) 0.0256(4) 0.0297(13) Uani 1 1 d . . . . .
H8A H 0.369573 0.174459 0.025696 0.036 Uiso 1 1 calc R U . . .
H8B H 0.388660 0.353129 -0.046756 0.036 Uiso 1 1 calc R U . . .
C9 C 0.8943(4) 0.7134(9) 0.5801(4) 0.0319(13) Uani 1 1 d . . . . .
C10 C 0.4375(4) 0.4259(8) 0.2471(4) 0.0263(12) Uani 1 1 d . . . . .
H10 H 0.456365 0.572486 0.240816 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5209(4) 0.2996(8) 0.2185(4) 0.0280(12) Uani 1 1 d . . . . .
C12 C 0.6561(4) 0.3786(8) 0.4151(4) 0.0276(12) Uani 1 1 d . . . . .
C13 C 0.8461(4) 0.7745(8) 0.3938(4) 0.0326(13) Uani 1 1 d . . . . .
H13 H 0.856897 0.845035 0.337119 0.039 Uiso 1 1 calc R U . . .
C14 C 0.9114(4) 0.8162(8) 0.4977(4) 0.0346(13) Uani 1 1 d . . . . .
H14 H 0.967342 0.914289 0.512337 0.041 Uiso 1 1 calc R U . . .
C15 C 0.6805(4) 0.5694(8) 0.2690(4) 0.0292(12) Uani 1 1 d . . . . .
H15A H 0.711668 0.550851 0.213605 0.035 Uiso 1 1 calc R U . . .
H15B H 0.623299 0.674411 0.245018 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5618(4) 0.4846(9) 0.4336(4) 0.0310(13) Uani 1 1 d . . . . .
H16A H 0.570201 0.468434 0.508787 0.037 Uiso 1 1 calc R U . . .
H16B H 0.563613 0.633093 0.419120 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3167(4) 0.4599(8) 0.0567(4) 0.0257(12) Uani 1 1 d . . . . .
H17 H 0.351148 0.598256 0.065873 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1413(4) 0.2911(9) -0.0693(4) 0.0374(14) Uani 1 1 d . . . . .
H18A H 0.130451 0.224829 -0.009084 0.045 Uiso 1 1 calc R U . . .
H18B H 0.071573 0.322989 -0.123785 0.045 Uiso 1 1 calc R U . . .
H18C H 0.180985 0.198550 -0.098745 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5126(4) 0.0655(8) 0.2298(4) 0.0344(13) Uani 1 1 d . . . . .
H19A H 0.520705 0.032262 0.302785 0.041 Uiso 1 1 calc R U . . .
H19B H 0.442598 0.017866 0.181483 0.041 Uiso 1 1 calc R U . . .
H19C H 0.569356 -0.002346 0.212259 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4532(4) 0.3972(9) 0.3635(4) 0.0326(13) Uani 1 1 d . . . . .
H20A H 0.449903 0.249462 0.378893 0.039 Uiso 1 1 calc R U . . .
H20B H 0.395225 0.468212 0.379005 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2490(4) 0.5659(9) 0.1986(4) 0.0360(14) Uani 1 1 d . . . . .
H21A H 0.242546 0.526225 0.266586 0.043 Uiso 1 1 calc R U . . .
H21B H 0.286764 0.699206 0.209428 0.043 Uiso 1 1 calc R U . . .
C22 C 0.2050(4) 0.4898(9) -0.0323(4) 0.0320(13) Uani 1 1 d . . . . .
C23 C 0.6813(4) 0.1703(8) 0.4721(4) 0.0343(14) Uani 1 1 d . . . . .
H23A H 0.618298 0.081175 0.444989 0.041 Uiso 1 1 calc R U . . .
H23B H 0.741620 0.106089 0.459251 0.041 Uiso 1 1 calc R U . . .
H23C H 0.700001 0.191076 0.548255 0.041 Uiso 1 1 calc R U . . .
C24 C 0.2189(4) 0.5847(9) -0.1300(4) 0.0387(15) Uani 1 1 d . . . . .
H24A H 0.259455 0.712779 -0.109965 0.046 Uiso 1 1 calc R U . . .
H24B H 0.257698 0.488706 -0.158724 0.046 Uiso 1 1 calc R U . . .
H24C H 0.148286 0.613145 -0.183764 0.046 Uiso 1 1 calc R U . . .
C25 C 0.1410(4) 0.6445(9) 0.0067(4) 0.0377(15) Uani 1 1 d . . . . .
H25A H 0.066696 0.650381 -0.045293 0.045 Uiso 1 1 calc R U . . .
H25B H 0.173034 0.782260 0.009862 0.045 Uiso 1 1 calc R U . . .
C26 C 1.0131(4) 0.9332(9) 0.7113(4) 0.0441(16) Uani 1 1 d . . . . .
H26A H 1.049916 0.942702 0.788150 0.053 Uiso 1 1 calc R U . . .
H26B H 1.066148 0.931426 0.676987 0.053 Uiso 1 1 calc R U . . .
H26C H 0.965731 1.051798 0.686109 0.053 Uiso 1 1 calc R U . . .
C27 C 0.1376(4) 0.5923(10) 0.1161(4) 0.0427(16) Uani 1 1 d . . . . .
H27A H 0.100166 0.703455 0.138547 0.051 Uiso 1 1 calc R U . . .
H27B H 0.096482 0.464144 0.111029 0.051 Uiso 1 1 calc R U . . .
C28 C 0.2711(4) 0.1889(8) 0.1769(4) 0.0367(14) Uani 1 1 d . . . . .
H28A H 0.313299 0.083443 0.158162 0.044 Uiso 1 1 calc R U . . .
H28B H 0.274427 0.166331 0.249436 0.044 Uiso 1 1 calc R U . . .
H28C H 0.196459 0.181361 0.128109 0.044 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C9 1.380(6) . ?
O1 C26 1.428(6) . ?
C2 C5 1.385(6) . ?
C2 C9 1.394(7) . ?
C2 H2 0.9500 . ?
C3 C15 1.561(7) . ?
C3 C11 1.562(7) . ?
C3 C12 1.570(6) . ?
C3 H3 1.0000 . ?
C4 C28 1.545(7) . ?
C4 C21 1.548(7) . ?
C4 C17 1.562(6) . ?
C4 C10 1.584(7) . ?
C5 C7 1.384(6) . ?
C5 C12 1.522(7) . ?
C6 C8 1.532(6) . ?
C6 C11 1.533(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C13 1.383(7) . ?
C7 C15 1.509(7) . ?
C8 C17 1.536(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.391(7) . ?
C10 C20 1.527(6) . ?
C10 C11 1.545(6) . ?
C10 H10 1.0000 . ?
C11 C19 1.542(7) . ?
C12 C16 1.538(6) . ?
C12 C23 1.538(7) . ?
C13 C14 1.389(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C20 1.530(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.557(6) . ?
C17 H17 1.0000 . ?
C18 C22 1.533(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C27 1.515(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C24 1.532(7) . ?
C22 C25 1.537(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.538(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C9 O1 C26 116.5(4) . . ?
C5 C2 C9 118.7(5) . . ?
C5 C2 H2 120.6 . . ?
C9 C2 H2 120.6 . . ?
C15 C3 C11 116.8(4) . . ?
C15 C3 C12 103.5(4) . . ?
C11 C3 C12 117.2(4) . . ?
C15 C3 H3 106.2 . . ?
C11 C3 H3 106.2 . . ?
C12 C3 H3 106.2 . . ?
C28 C4 C21 108.2(4) . . ?
C28 C4 C17 115.0(4) . . ?
C21 C4 C17 107.3(4) . . ?
C28 C4 C10 111.9(4) . . ?
C21 C4 C10 108.3(4) . . ?
C17 C4 C10 105.9(4) . . ?
C7 C5 C2 120.9(5) . . ?
C7 C5 C12 111.3(4) . . ?
C2 C5 C12 127.5(5) . . ?
C8 C6 C11 113.3(4) . . ?
C8 C6 H6A 108.9 . . ?
C11 C6 H6A 108.9 . . ?
C8 C6 H6B 108.9 . . ?
C11 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C13 C7 C5 120.1(5) . . ?
C13 C7 C15 129.7(5) . . ?
C5 C7 C15 110.2(4) . . ?
C6 C8 C17 110.5(4) . . ?
C6 C8 H8A 109.6 . . ?
C17 C8 H8A 109.6 . . ?
C6 C8 H8B 109.6 . . ?
C17 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 C14 124.4(5) . . ?
O1 C9 C2 114.9(4) . . ?
C14 C9 C2 120.7(5) . . ?
C20 C10 C11 110.6(4) . . ?
C20 C10 C4 114.0(4) . . ?
C11 C10 C4 115.7(4) . . ?
C20 C10 H10 105.1 . . ?
C11 C10 H10 105.1 . . ?
C4 C10 H10 105.1 . . ?
C6 C11 C19 107.5(4) . . ?
C6 C11 C10 109.2(4) . . ?
C19 C11 C10 114.7(4) . . ?
C6 C11 C3 109.7(4) . . ?
C19 C11 C3 106.5(4) . . ?
C10 C11 C3 109.1(4) . . ?
C5 C12 C16 107.8(4) . . ?
C5 C12 C23 111.0(4) . . ?
C16 C12 C23 111.0(4) . . ?
C5 C12 C3 102.6(4) . . ?
C16 C12 C3 111.1(4) . . ?
C23 C12 C3 113.0(4) . . ?
C7 C13 C14 119.9(5) . . ?
C7 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C7 C15 C3 104.1(4) . . ?
C7 C15 H15A 110.9 . . ?
C3 C15 H15A 110.9 . . ?
C7 C15 H15B 110.9 . . ?
C3 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C20 C16 C12 112.6(4) . . ?
C20 C16 H16A 109.1 . . ?
C12 C16 H16A 109.1 . . ?
C20 C16 H16B 109.1 . . ?
C12 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C8 C17 C22 114.0(4) . . ?
C8 C17 C4 110.7(4) . . ?
C22 C17 C4 116.6(4) . . ?
C8 C17 H17 104.7 . . ?
C22 C17 H17 104.7 . . ?
C4 C17 H17 104.7 . . ?
C22 C18 H18A 109.5 . . ?
C22 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C22 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 C16 109.9(4) . . ?
C10 C20 H20A 109.7 . . ?
C16 C20 H20A 109.7 . . ?
C10 C20 H20B 109.7 . . ?
C16 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C27 C21 C4 113.6(4) . . ?
C27 C21 H21A 108.8 . . ?
C4 C21 H21A 108.8 . . ?
C27 C21 H21B 108.8 . . ?
C4 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C24 C22 C18 106.6(4) . . ?
C24 C22 C25 106.8(4) . . ?
C18 C22 C25 110.6(4) . . ?
C24 C22 C17 109.7(4) . . ?
C18 C22 C17 114.4(5) . . ?
C25 C22 C17 108.4(4) . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 C27 113.7(5) . . ?
C22 C25 H25A 108.8 . . ?
C27 C25 H25A 108.8 . . ?
C22 C25 H25B 108.8 . . ?
C27 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C27 C25 111.9(4) . . ?
C21 C27 H27A 109.2 . . ?
C25 C27 H27A 109.2 . . ?
C21 C27 H27B 109.2 . . ?
C25 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
C9 C2 C5 C7 -0.8(7) . . . . ?
C9 C2 C5 C12 -173.9(5) . . . . ?
C2 C5 C7 C13 3.2(7) . . . . ?
C12 C5 C7 C13 177.4(4) . . . . ?
C2 C5 C7 C15 -174.9(4) . . . . ?
C12 C5 C7 C15 -0.8(6) . . . . ?
C11 C6 C8 C17 57.6(6) . . . . ?
C26 O1 C9 C14 15.0(7) . . . . ?
C26 O1 C9 C2 -165.2(5) . . . . ?
C5 C2 C9 O1 177.8(4) . . . . ?
C5 C2 C9 C14 -2.3(7) . . . . ?
C28 C4 C10 C20 -59.7(5) . . . . ?
C21 C4 C10 C20 59.4(5) . . . . ?
C17 C4 C10 C20 174.2(4) . . . . ?
C28 C4 C10 C11 70.3(5) . . . . ?
C21 C4 C10 C11 -170.5(4) . . . . ?
C17 C4 C10 C11 -55.8(5) . . . . ?
C8 C6 C11 C19 73.7(5) . . . . ?
C8 C6 C11 C10 -51.3(6) . . . . ?
C8 C6 C11 C3 -170.9(4) . . . . ?
C20 C10 C11 C6 -176.1(4) . . . . ?
C4 C10 C11 C6 52.3(5) . . . . ?
C20 C10 C11 C19 63.2(6) . . . . ?
C4 C10 C11 C19 -68.4(6) . . . . ?
C20 C10 C11 C3 -56.2(5) . . . . ?
C4 C10 C11 C3 172.2(4) . . . . ?
C15 C3 C11 C6 42.3(5) . . . . ?
C12 C3 C11 C6 165.9(4) . . . . ?
C15 C3 C11 C19 158.4(4) . . . . ?
C12 C3 C11 C19 -78.1(5) . . . . ?
C15 C3 C11 C10 -77.3(5) . . . . ?
C12 C3 C11 C10 46.3(6) . . . . ?
C7 C5 C12 C16 -99.2(5) . . . . ?
C2 C5 C12 C16 74.4(6) . . . . ?
C7 C5 C12 C23 139.1(4) . . . . ?
C2 C5 C12 C23 -47.3(7) . . . . ?
C7 C5 C12 C3 18.2(5) . . . . ?
C2 C5 C12 C3 -168.2(5) . . . . ?
C15 C3 C12 C5 -27.2(5) . . . . ?
C11 C3 C12 C5 -157.3(4) . . . . ?
C15 C3 C12 C16 87.7(5) . . . . ?
C11 C3 C12 C16 -42.3(6) . . . . ?
C15 C3 C12 C23 -146.8(4) . . . . ?
C11 C3 C12 C23 83.2(5) . . . . ?
C5 C7 C13 C14 -2.5(7) . . . . ?
C15 C7 C13 C14 175.2(5) . . . . ?
C7 C13 C14 C9 -0.6(7) . . . . ?
O1 C9 C14 C13 -177.1(5) . . . . ?
C2 C9 C14 C13 3.0(8) . . . . ?
C13 C7 C15 C3 164.9(5) . . . . ?
C5 C7 C15 C3 -17.2(5) . . . . ?
C11 C3 C15 C7 157.6(4) . . . . ?
C12 C3 C15 C7 27.3(5) . . . . ?
C5 C12 C16 C20 159.5(4) . . . . ?
C23 C12 C16 C20 -78.7(5) . . . . ?
C3 C12 C16 C20 47.9(6) . . . . ?
C6 C8 C17 C22 164.5(4) . . . . ?
C6 C8 C17 C4 -61.7(5) . . . . ?
C28 C4 C17 C8 -65.5(5) . . . . ?
C21 C4 C17 C8 174.0(4) . . . . ?
C10 C4 C17 C8 58.6(5) . . . . ?
C28 C4 C17 C22 67.0(6) . . . . ?
C21 C4 C17 C22 -53.5(6) . . . . ?
C10 C4 C17 C22 -168.9(4) . . . . ?
C11 C10 C20 C16 64.7(6) . . . . ?
C4 C10 C20 C16 -162.8(4) . . . . ?
C12 C16 C20 C10 -60.3(6) . . . . ?
C28 C4 C21 C27 -71.2(5) . . . . ?
C17 C4 C21 C27 53.5(6) . . . . ?
C10 C4 C21 C27 167.4(4) . . . . ?
C8 C17 C22 C24 -60.0(6) . . . . ?
C4 C17 C22 C24 169.1(5) . . . . ?
C8 C17 C22 C18 59.8(5) . . . . ?
C4 C17 C22 C18 -71.2(5) . . . . ?
C8 C17 C22 C25 -176.3(4) . . . . ?
C4 C17 C22 C25 52.8(6) . . . . ?
C24 C22 C25 C27 -169.2(4) . . . . ?
C18 C22 C25 C27 75.1(5) . . . . ?
C17 C22 C25 C27 -51.1(6) . . . . ?
C4 C21 C27 C25 -55.9(6) . . . . ?
C22 C25 C27 C21 54.5(6) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20211011
_database_code_depnum_ccdc_archive 'CCDC 2257939'
loop_
_audit_author_name
_audit_author_address
'Kenichiro Nagai'
;School of Pharmacy, Kitasato University
Japan
;
_audit_update_record             
;
2023-04-21 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H40 O2'
_chemical_formula_moiety         'C27 H40 O2'
_chemical_formula_weight         396.61
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.4265(2)
_cell_length_b                   14.3062(3)
_cell_length_c                   27.6040(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4512.40(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    29248
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      68.08
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744.00
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.947

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            53013
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_theta_max         68.157
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8238
_reflns_number_gt                5698
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1282
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8238
_refine_ls_number_parameters     523
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0646P)²+1.7146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(12)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.5699(3) 0.5773(2) 0.49527(11) 0.0276(8) Uani 1 1 d . . . . .
H1 H 0.509772 0.605148 0.485307 0.033 Uiso 1 1 calc R U . . .
O2 O 0.3074(3) 0.8623(2) 0.50651(12) 0.0305(8) Uani 1 1 d . . . . .
O3 O 0.4144(3) 0.8836(2) 0.30404(12) 0.0333(8) Uani 1 1 d . . . . .
O4 O 0.4054(3) 0.6141(2) 0.41975(13) 0.0382(9) Uani 1 1 d . . . . .
H4 H 0.367895 0.652818 0.436541 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4065(4) 0.7217(3) 0.53657(17) 0.0257(11) Uani 1 1 d . . . . .
H5 H 0.450661 0.714797 0.507625 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5400(4) 0.5198(3) 0.53589(16) 0.0242(11) Uani 1 1 d . . . . .
H6 H 0.612489 0.484759 0.544910 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3528(4) 0.4414(3) 0.60137(17) 0.0267(11) Uani 1 1 d . . . . .
C8 C 0.4186(4) 0.6581(3) 0.57451(17) 0.0256(11) Uani 1 1 d . . . . .
C9 C 0.3555(4) 0.6696(3) 0.61711(18) 0.0282(11) Uani 1 1 d . . . . .
C10 C 0.3280(4) 0.7956(3) 0.54216(17) 0.0268(11) Uani 1 1 d . . . . .
C11 C 0.3361(4) 0.7420(3) 0.34141(18) 0.0282(11) Uani 1 1 d . . . . .
H11 H 0.395910 0.740187 0.365284 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3193(4) 0.1246(3) 0.59006(17) 0.0273(11) Uani 1 1 d . . . . .
C13 C 0.3608(4) 0.3069(3) 0.33284(17) 0.0269(11) Uani 1 1 d . . . . .
C14 C 0.6181(4) 0.6178(3) 0.60275(18) 0.0289(12) Uani 1 1 d . . . . .
H14A H 0.675171 0.567441 0.607373 0.035 Uiso 1 1 calc R U . . .
H14B H 0.650431 0.664735 0.580659 0.035 Uiso 1 1 calc R U . . .
H14C H 0.600653 0.646938 0.634058 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4516(4) 0.4478(3) 0.52005(17) 0.0241(11) Uani 1 1 d . . . . .
H15A H 0.484249 0.410076 0.493176 0.029 Uiso 1 1 calc R U . . .
H15B H 0.380038 0.479362 0.508174 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3341(4) 0.8127(3) 0.30673(18) 0.0281(11) Uani 1 1 d . . . . .
C17 C 0.5041(4) 0.5769(3) 0.58090(17) 0.0243(11) Uani 1 1 d . . . . .
C18 C 0.3478(4) 0.2308(3) 0.59544(17) 0.0256(11) Uani 1 1 d . . . . .
H18 H 0.425179 0.231911 0.612352 0.031 Uiso 1 1 calc R U . . .
C19 C 0.4208(4) 0.3840(3) 0.56253(16) 0.0226(10) Uani 1 1 d . . . . .
H19 H 0.497642 0.369325 0.578095 0.027 Uiso 1 1 calc R U . . .
C20 C 0.4406(4) 0.5165(3) 0.62027(17) 0.0256(11) Uani 1 1 d . . . . .
H20 H 0.501673 0.483935 0.639960 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3052(4) 0.4018(3) 0.34910(17) 0.0257(11) Uani 1 1 d . . . . .
H21 H 0.251341 0.384987 0.376283 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3917(4) 0.4726(3) 0.37119(18) 0.0286(12) Uani 1 1 d . . . . .
H22A H 0.448893 0.439260 0.391877 0.034 Uiso 1 1 calc R U . . .
H22B H 0.435387 0.504325 0.344935 0.034 Uiso 1 1 calc R U . . .
C23 C 0.1525(4) 0.5258(3) 0.34209(18) 0.0284(12) Uani 1 1 d . . . . .
H23 H 0.096798 0.489790 0.362893 0.034 Uiso 1 1 calc R U . . .
C24 C 0.4651(4) 0.2336(3) 0.51880(19) 0.0296(12) Uani 1 1 d . . . . .
H24A H 0.474173 0.263698 0.486717 0.036 Uiso 1 1 calc R U . . .
H24B H 0.540539 0.239443 0.536149 0.036 Uiso 1 1 calc R U . . .
C25 C 0.2610(4) 0.2968(3) 0.51527(18) 0.0292(12) Uani 1 1 d . . . . .
H25A H 0.199616 0.330058 0.533090 0.035 Uiso 1 1 calc R U . . .
H25B H 0.281736 0.332283 0.486141 0.035 Uiso 1 1 calc R U . . .
H25C H 0.232434 0.234781 0.505919 0.035 Uiso 1 1 calc R U . . .
C26 C 0.1998(4) 0.2971(3) 0.26919(18) 0.0299(12) Uani 1 1 d . . . . .
H26A H 0.257470 0.314900 0.244052 0.036 Uiso 1 1 calc R U . . .
H26B H 0.140915 0.255457 0.254193 0.036 Uiso 1 1 calc R U . . .
C27 C 0.1590(5) 0.7481(3) 0.27121(18) 0.0315(12) Uani 1 1 d . . . . .
H27 H 0.098656 0.750338 0.247551 0.038 Uiso 1 1 calc R U . . .
C28 C 0.1614(4) 0.6767(3) 0.30538(18) 0.0295(11) Uani 1 1 d . . . . .
C29 C 0.2805(5) 0.7445(4) 0.62290(19) 0.0340(13) Uani 1 1 d . . . . .
H29 H 0.239821 0.752987 0.652583 0.041 Uiso 1 1 calc R U . . .
C30 C 0.2492(4) 0.6741(3) 0.34054(17) 0.0275(11) Uani 1 1 d . . . . .
C31 C 0.3696(4) 0.2862(3) 0.54769(17) 0.0231(11) Uani 1 1 d . . . . .
C32 C 0.4373(4) 0.1288(3) 0.51137(18) 0.0308(12) Uani 1 1 d . . . . .
H32A H 0.366691 0.122498 0.490848 0.037 Uiso 1 1 calc R U . . .
H32B H 0.503363 0.098489 0.494315 0.037 Uiso 1 1 calc R U . . .
C33 C 0.3268(5) 0.5448(3) 0.40128(18) 0.0310(12) Uani 1 1 d . . . . .
H33 H 0.293280 0.511230 0.429868 0.037 Uiso 1 1 calc R U . . .
C34 C 0.2242(4) 0.5940(3) 0.37559(18) 0.0289(12) Uani 1 1 d . . . . .
C35 C 0.3835(5) 0.5931(3) 0.65250(18) 0.0305(12) Uani 1 1 d . . . . .
H35A H 0.311632 0.569493 0.668347 0.037 Uiso 1 1 calc R U . . .
H35B H 0.438635 0.615215 0.677680 0.037 Uiso 1 1 calc R U . . .
C36 C 0.2268(4) 0.4543(3) 0.31197(18) 0.0280(12) Uani 1 1 d . . . . .
C37 C 0.2905(4) 0.1415(3) 0.30103(18) 0.0290(12) Uani 1 1 d . . . . .
C38 C 0.1400(5) 0.3846(3) 0.28910(18) 0.0312(12) Uani 1 1 d . . . . .
H38A H 0.081888 0.365729 0.313830 0.037 Uiso 1 1 calc R U . . .
H38B H 0.097427 0.416052 0.262481 0.037 Uiso 1 1 calc R U . . .
C39 C 0.2618(4) 0.2461(3) 0.31082(18) 0.0275(11) Uani 1 1 d . . . . .
H39 H 0.201409 0.243721 0.337014 0.033 Uiso 1 1 calc R U . . .
C40 C 0.2664(4) 0.2845(3) 0.62928(18) 0.0298(12) Uani 1 1 d . . . . .
H40A H 0.249977 0.246341 0.658410 0.036 Uiso 1 1 calc R U . . .
H40B H 0.191242 0.296881 0.612642 0.036 Uiso 1 1 calc R U . . .
C41 C 0.1429(5) 0.6315(3) 0.41592(18) 0.0351(13) Uani 1 1 d . . . . .
H41A H 0.125551 0.581273 0.438936 0.042 Uiso 1 1 calc R U . . .
H41B H 0.181832 0.683042 0.432900 0.042 Uiso 1 1 calc R U . . .
H41C H 0.069850 0.654130 0.401470 0.042 Uiso 1 1 calc R U . . .
C42 C 0.2457(5) 0.8161(4) 0.27205(18) 0.0323(13) Uani 1 1 d . . . . .
H42 H 0.244665 0.865216 0.248868 0.039 Uiso 1 1 calc R U . . .
C43 C 0.2650(4) 0.8075(4) 0.58513(18) 0.0315(12) Uani 1 1 d . . . . .
H43 H 0.211908 0.858223 0.588482 0.038 Uiso 1 1 calc R U . . .
C44 C 0.2382(4) 0.4850(3) 0.58199(18) 0.0297(12) Uani 1 1 d . . . . .
H44A H 0.256061 0.526023 0.554550 0.036 Uiso 1 1 calc R U . . .
H44B H 0.185274 0.435126 0.571381 0.036 Uiso 1 1 calc R U . . .
H44C H 0.200734 0.521354 0.607755 0.036 Uiso 1 1 calc R U . . .
C45 C 0.3224(5) 0.3772(3) 0.64447(17) 0.0310(12) Uani 1 1 d . . . . .
H45A H 0.394791 0.363911 0.662923 0.037 Uiso 1 1 calc R U . . .
H45B H 0.267970 0.410686 0.666330 0.037 Uiso 1 1 calc R U . . .
C46 C 0.4373(5) 0.1539(3) 0.36976(19) 0.0337(13) Uani 1 1 d . . . . .
H46A H 0.504122 0.151296 0.346978 0.040 Uiso 1 1 calc R U . . .
H46B H 0.462059 0.124453 0.400560 0.040 Uiso 1 1 calc R U . . .
C47 C 0.3895(5) 0.8660(4) 0.46754(18) 0.0364(13) Uani 1 1 d . . . . .
H47A H 0.366356 0.915167 0.444742 0.044 Uiso 1 1 calc R U . . .
H47B H 0.467567 0.879767 0.480368 0.044 Uiso 1 1 calc R U . . .
H47C H 0.390849 0.805641 0.450759 0.044 Uiso 1 1 calc R U . . .
C48 C 0.4168(4) 0.0801(3) 0.55933(18) 0.0299(12) Uani 1 1 d . . . . .
H48A H 0.490500 0.080805 0.578160 0.036 Uiso 1 1 calc R U . . .
H48B H 0.396329 0.013947 0.552993 0.036 Uiso 1 1 calc R U . . .
C49 C 0.0808(4) 0.5942(3) 0.31046(19) 0.0324(12) Uani 1 1 d . . . . .
H49A H 0.062521 0.566369 0.278492 0.039 Uiso 1 1 calc R U . . .
H49B H 0.006828 0.612116 0.326668 0.039 Uiso 1 1 calc R U . . .
C50 C 0.3354(5) 0.0999(3) 0.34879(18) 0.0316(12) Uani 1 1 d . . . . .
H50A H 0.270716 0.099071 0.372646 0.038 Uiso 1 1 calc R U . . .
H50B H 0.359912 0.034402 0.343111 0.038 Uiso 1 1 calc R U . . .
C51 C 0.1985(4) 0.1041(4) 0.56765(19) 0.0332(12) Uani 1 1 d . . . . .
H51A H 0.193755 0.133008 0.535520 0.040 Uiso 1 1 calc R U . . .
H51B H 0.187842 0.036417 0.564659 0.040 Uiso 1 1 calc R U . . .
H51C H 0.137174 0.129981 0.588530 0.040 Uiso 1 1 calc R U . . .
C52 C 0.5105(5) 0.8802(4) 0.33637(19) 0.0406(14) Uani 1 1 d . . . . .
H52A H 0.561197 0.934469 0.330862 0.049 Uiso 1 1 calc R U . . .
H52B H 0.481827 0.881142 0.369821 0.049 Uiso 1 1 calc R U . . .
H52C H 0.555148 0.822710 0.330798 0.049 Uiso 1 1 calc R U . . .
C53 C 0.2956(4) 0.5016(4) 0.27111(18) 0.0325(12) Uani 1 1 d . . . . .
H53A H 0.351281 0.546255 0.284972 0.039 Uiso 1 1 calc R U . . .
H53B H 0.338166 0.454089 0.252568 0.039 Uiso 1 1 calc R U . . .
H53C H 0.241208 0.534613 0.249636 0.039 Uiso 1 1 calc R U . . .
C54 C 0.4042(5) 0.2562(3) 0.37908(18) 0.0324(12) Uani 1 1 d . . . . .
H54A H 0.473223 0.289706 0.392040 0.039 Uiso 1 1 calc R U . . .
H54B H 0.341870 0.258564 0.403969 0.039 Uiso 1 1 calc R U . . .
C55 C 0.3206(5) 0.0775(4) 0.64005(18) 0.0361(13) Uani 1 1 d . . . . .
H55A H 0.259115 0.104775 0.660377 0.043 Uiso 1 1 calc R U . . .
H55B H 0.306618 0.010350 0.636303 0.043 Uiso 1 1 calc R U . . .
H55C H 0.396962 0.087487 0.655390 0.043 Uiso 1 1 calc R U . . .
C56 C 0.3773(5) 0.1237(4) 0.25915(18) 0.0352(13) Uani 1 1 d . . . . .
H56A H 0.346286 0.151035 0.229225 0.042 Uiso 1 1 calc R U . . .
H56B H 0.452776 0.152571 0.266873 0.042 Uiso 1 1 calc R U . . .
H56C H 0.387788 0.056263 0.254788 0.042 Uiso 1 1 calc R U . . .
C57 C 0.1764(5) 0.0901(4) 0.2879(2) 0.0397(14) Uani 1 1 d . . . . .
H57A H 0.145349 0.115187 0.257419 0.048 Uiso 1 1 calc R U . . .
H57B H 0.192402 0.023205 0.284050 0.048 Uiso 1 1 calc R U . . .
H57C H 0.118730 0.099174 0.313729 0.048 Uiso 1 1 calc R U . . .
C58 C 0.4661(4) 0.3220(3) 0.29885(19) 0.0329(12) Uani 1 1 d . . . . .
H58A H 0.439994 0.354033 0.269386 0.039 Uiso 1 1 calc R U . . .
H58B H 0.525127 0.360245 0.315308 0.039 Uiso 1 1 calc R U . . .
H58C H 0.500178 0.261377 0.290230 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C6 1.433(5) . ?
O1 H1 0.8400 . ?
O2 C10 1.390(5) . ?
O2 C47 1.429(6) . ?
O3 C16 1.369(5) . ?
O3 C52 1.417(6) . ?
O4 C33 1.431(6) . ?
O4 H4 0.8400 . ?
C5 C8 1.393(6) . ?
C5 C10 1.396(6) . ?
C5 H5 0.9500 . ?
C6 C15 1.508(6) . ?
C6 C17 1.543(6) . ?
C6 H6 1.0000 . ?
C7 C45 1.543(6) . ?
C7 C44 1.545(6) . ?
C7 C19 1.559(6) . ?
C7 C20 1.559(6) . ?
C8 C9 1.389(7) . ?
C8 C17 1.528(6) . ?
C9 C29 1.382(7) . ?
C9 C35 1.501(6) . ?
C10 C43 1.398(6) . ?
C11 C30 1.389(7) . ?
C11 C16 1.393(7) . ?
C11 H11 0.9500 . ?
C12 C55 1.536(7) . ?
C12 C48 1.538(6) . ?
C12 C51 1.540(7) . ?
C12 C18 1.561(6) . ?
C13 C58 1.541(7) . ?
C13 C54 1.549(6) . ?
C13 C39 1.551(6) . ?
C13 C21 1.566(6) . ?
C14 C17 1.549(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C19 1.527(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C42 1.393(7) . ?
C17 C20 1.567(6) . ?
C18 C40 1.526(6) . ?
C18 C31 1.559(6) . ?
C18 H18 1.0000 . ?
C19 C31 1.570(6) . ?
C19 H19 1.0000 . ?
C20 C35 1.555(6) . ?
C20 H20 1.0000 . ?
C21 C22 1.541(6) . ?
C21 C36 1.555(6) . ?
C21 H21 1.0000 . ?
C22 C33 1.519(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C49 1.546(6) . ?
C23 C36 1.568(6) . ?
C23 C34 1.574(7) . ?
C23 H23 1.0000 . ?
C24 C32 1.546(6) . ?
C24 C31 1.546(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C31 1.537(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C38 1.527(6) . ?
C26 C39 1.535(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C42 1.389(7) . ?
C27 C28 1.391(7) . ?
C27 H27 0.9500 . ?
C28 C30 1.396(7) . ?
C28 C49 1.505(6) . ?
C29 C43 1.389(7) . ?
C29 H29 0.9500 . ?
C30 C34 1.527(7) . ?
C32 C48 1.515(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.540(7) . ?
C33 H33 1.0000 . ?
C34 C41 1.546(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C53 1.532(7) . ?
C36 C38 1.542(6) . ?
C37 C50 1.535(6) . ?
C37 C57 1.541(7) . ?
C37 C56 1.544(7) . ?
C37 C39 1.555(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39 1.0000 . ?
C40 C45 1.531(6) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C50 1.512(7) . ?
C46 C54 1.534(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?

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
C6 O1 H1 109.5 . . ?
C10 O2 C47 116.6(4) . . ?
C16 O3 C52 117.4(4) . . ?
C33 O4 H4 109.5 . . ?
C8 C5 C10 118.4(4) . . ?
C8 C5 H5 120.8 . . ?
C10 C5 H5 120.8 . . ?
O1 C6 C15 109.0(4) . . ?
O1 C6 C17 112.9(4) . . ?
C15 C6 C17 114.7(4) . . ?
O1 C6 H6 106.6 . . ?
C15 C6 H6 106.6 . . ?
C17 C6 H6 106.6 . . ?
C45 C7 C44 108.5(4) . . ?
C45 C7 C19 109.2(4) . . ?
C44 C7 C19 113.4(4) . . ?
C45 C7 C20 107.3(4) . . ?
C44 C7 C20 112.5(4) . . ?
C19 C7 C20 105.8(4) . . ?
C9 C8 C5 120.5(4) . . ?
C9 C8 C17 108.9(4) . . ?
C5 C8 C17 130.2(4) . . ?
C29 C9 C8 120.7(5) . . ?
C29 C9 C35 128.5(5) . . ?
C8 C9 C35 110.8(4) . . ?
O2 C10 C5 123.4(4) . . ?
O2 C10 C43 115.5(4) . . ?
C5 C10 C43 121.1(4) . . ?
C30 C11 C16 119.0(5) . . ?
C30 C11 H11 120.5 . . ?
C16 C11 H11 120.5 . . ?
C55 C12 C48 107.9(4) . . ?
C55 C12 C51 106.6(4) . . ?
C48 C12 C51 110.4(4) . . ?
C55 C12 C18 109.8(4) . . ?
C48 C12 C18 107.7(4) . . ?
C51 C12 C18 114.2(4) . . ?
C58 C13 C54 108.5(4) . . ?
C58 C13 C39 114.2(4) . . ?
C54 C13 C39 107.1(4) . . ?
C58 C13 C21 111.7(4) . . ?
C54 C13 C21 107.4(4) . . ?
C39 C13 C21 107.6(4) . . ?
C17 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C17 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C15 C19 109.9(4) . . ?
C6 C15 H15A 109.7 . . ?
C19 C15 H15A 109.7 . . ?
C6 C15 H15B 109.7 . . ?
C19 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O3 C16 C42 115.0(4) . . ?
O3 C16 C11 124.4(5) . . ?
C42 C16 C11 120.6(5) . . ?
C8 C17 C6 118.7(4) . . ?
C8 C17 C14 107.2(4) . . ?
C6 C17 C14 106.9(4) . . ?
C8 C17 C20 101.7(4) . . ?
C6 C17 C20 112.9(4) . . ?
C14 C17 C20 109.1(4) . . ?
C40 C18 C31 111.0(4) . . ?
C40 C18 C12 114.9(4) . . ?
C31 C18 C12 116.6(4) . . ?
C40 C18 H18 104.2 . . ?
C31 C18 H18 104.2 . . ?
C12 C18 H18 104.2 . . ?
C15 C19 C7 109.1(4) . . ?
C15 C19 C31 114.7(4) . . ?
C7 C19 C31 117.6(4) . . ?
C15 C19 H19 104.6 . . ?
C7 C19 H19 104.6 . . ?
C31 C19 H19 104.6 . . ?
C35 C20 C7 114.0(4) . . ?
C35 C20 C17 101.7(4) . . ?
C7 C20 C17 116.5(4) . . ?
C35 C20 H20 108.1 . . ?
C7 C20 H20 108.1 . . ?
C17 C20 H20 108.1 . . ?
C22 C21 C36 108.2(4) . . ?
C22 C21 C13 115.0(4) . . ?
C36 C21 C13 117.7(4) . . ?
C22 C21 H21 104.8 . . ?
C36 C21 H21 104.8 . . ?
C13 C21 H21 104.8 . . ?
C33 C22 C21 110.5(4) . . ?
C33 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
C33 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C49 C23 C36 113.6(4) . . ?
C49 C23 C34 102.5(4) . . ?
C36 C23 C34 115.7(4) . . ?
C49 C23 H23 108.2 . . ?
C36 C23 H23 108.2 . . ?
C34 C23 H23 108.2 . . ?
C32 C24 C31 113.3(4) . . ?
C32 C24 H24A 108.9 . . ?
C31 C24 H24A 108.9 . . ?
C32 C24 H24B 108.9 . . ?
C31 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C31 C25 H25A 109.5 . . ?
C31 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C31 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C38 C26 C39 109.1(4) . . ?
C38 C26 H26A 109.9 . . ?
C39 C26 H26A 109.9 . . ?
C38 C26 H26B 109.9 . . ?
C39 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C42 C27 C28 119.3(5) . . ?
C42 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C30 120.4(5) . . ?
C27 C28 C49 128.8(5) . . ?
C30 C28 C49 110.7(4) . . ?
C9 C29 C43 119.7(5) . . ?
C9 C29 H29 120.1 . . ?
C43 C29 H29 120.1 . . ?
C11 C30 C28 120.4(5) . . ?
C11 C30 C34 130.4(5) . . ?
C28 C30 C34 109.1(4) . . ?
C25 C31 C24 108.5(4) . . ?
C25 C31 C18 114.4(4) . . ?
C24 C31 C18 107.5(4) . . ?
C25 C31 C19 111.4(4) . . ?
C24 C31 C19 107.8(4) . . ?
C18 C31 C19 107.0(4) . . ?
C48 C32 C24 111.3(4) . . ?
C48 C32 H32A 109.4 . . ?
C24 C32 H32A 109.4 . . ?
C48 C32 H32B 109.4 . . ?
C24 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
O4 C33 C22 111.0(4) . . ?
O4 C33 C34 109.0(4) . . ?
C22 C33 C34 115.5(4) . . ?
O4 C33 H33 107.0 . . ?
C22 C33 H33 107.0 . . ?
C34 C33 H33 107.0 . . ?
C30 C34 C33 119.5(4) . . ?
C30 C34 C41 107.9(4) . . ?
C33 C34 C41 106.5(4) . . ?
C30 C34 C23 101.0(4) . . ?
C33 C34 C23 112.6(4) . . ?
C41 C34 C23 109.0(4) . . ?
C9 C35 C20 103.3(4) . . ?
C9 C35 H35A 111.1 . . ?
C20 C35 H35A 111.1 . . ?
C9 C35 H35B 111.1 . . ?
C20 C35 H35B 111.1 . . ?
H35A C35 H35B 109.1 . . ?
C53 C36 C38 108.3(4) . . ?
C53 C36 C21 113.8(4) . . ?
C38 C36 C21 109.1(4) . . ?
C53 C36 C23 112.4(4) . . ?
C38 C36 C23 106.9(4) . . ?
C21 C36 C23 106.1(4) . . ?
C50 C37 C57 107.5(4) . . ?
C50 C37 C56 111.3(4) . . ?
C57 C37 C56 106.7(4) . . ?
C50 C37 C39 107.1(4) . . ?
C57 C37 C39 108.8(4) . . ?
C56 C37 C39 115.1(4) . . ?
C26 C38 C36 112.9(4) . . ?
C26 C38 H38A 109.0 . . ?
C36 C38 H38A 109.0 . . ?
C26 C38 H38B 109.0 . . ?
C36 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C26 C39 C13 111.3(4) . . ?
C26 C39 C37 115.2(4) . . ?
C13 C39 C37 117.0(4) . . ?
C26 C39 H39 103.8 . . ?
C13 C39 H39 103.8 . . ?
C37 C39 H39 103.8 . . ?
C18 C40 C45 110.5(4) . . ?
C18 C40 H40A 109.6 . . ?
C45 C40 H40A 109.6 . . ?
C18 C40 H40B 109.6 . . ?
C45 C40 H40B 109.6 . . ?
H40A C40 H40B 108.1 . . ?
C34 C41 H41A 109.5 . . ?
C34 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C34 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C27 C42 C16 120.3(5) . . ?
C27 C42 H42 119.9 . . ?
C16 C42 H42 119.9 . . ?
C29 C43 C10 119.5(5) . . ?
C29 C43 H43 120.3 . . ?
C10 C43 H43 120.3 . . ?
C7 C44 H44A 109.5 . . ?
C7 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C7 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C40 C45 C7 113.5(4) . . ?
C40 C45 H45A 108.9 . . ?
C7 C45 H45A 108.9 . . ?
C40 C45 H45B 108.9 . . ?
C7 C45 H45B 108.9 . . ?
H45A C45 H45B 107.7 . . ?
C50 C46 C54 111.2(4) . . ?
C50 C46 H46A 109.4 . . ?
C54 C46 H46A 109.4 . . ?
C50 C46 H46B 109.4 . . ?
C54 C46 H46B 109.4 . . ?
H46A C46 H46B 108.0 . . ?
O2 C47 H47A 109.5 . . ?
O2 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O2 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C32 C48 C12 113.8(4) . . ?
C32 C48 H48A 108.8 . . ?
C12 C48 H48A 108.8 . . ?
C32 C48 H48B 108.8 . . ?
C12 C48 H48B 108.8 . . ?
H48A C48 H48B 107.7 . . ?
C28 C49 C23 103.0(4) . . ?
C28 C49 H49A 111.2 . . ?
C23 C49 H49A 111.2 . . ?
C28 C49 H49B 111.2 . . ?
C23 C49 H49B 111.2 . . ?
H49A C49 H49B 109.1 . . ?
C46 C50 C37 112.8(4) . . ?
C46 C50 H50A 109.0 . . ?
C37 C50 H50A 109.0 . . ?
C46 C50 H50B 109.0 . . ?
C37 C50 H50B 109.0 . . ?
H50A C50 H50B 107.8 . . ?
C12 C51 H51A 109.5 . . ?
C12 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C12 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O3 C52 H52A 109.5 . . ?
O3 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O3 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C36 C53 H53A 109.5 . . ?
C36 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C36 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C46 C54 C13 112.8(4) . . ?
C46 C54 H54A 109.0 . . ?
C13 C54 H54A 109.0 . . ?
C46 C54 H54B 109.0 . . ?
C13 C54 H54B 109.0 . . ?
H54A C54 H54B 107.8 . . ?
C12 C55 H55A 109.5 . . ?
C12 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C12 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C37 C56 H56A 109.5 . . ?
C37 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C37 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C37 C57 H57A 109.5 . . ?
C37 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C37 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C13 C58 H58A 109.5 . . ?
C13 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C13 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?

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
C10 C5 C8 C9 -1.3(7) . . . . ?
C10 C5 C8 C17 -173.6(4) . . . . ?
C5 C8 C9 C29 -0.6(7) . . . . ?
C17 C8 C9 C29 173.2(4) . . . . ?
C5 C8 C9 C35 -179.7(4) . . . . ?
C17 C8 C9 C35 -5.9(5) . . . . ?
C47 O2 C10 C5 -14.3(6) . . . . ?
C47 O2 C10 C43 165.1(4) . . . . ?
C8 C5 C10 O2 -178.9(4) . . . . ?
C8 C5 C10 C43 1.6(7) . . . . ?
O1 C6 C15 C19 178.5(3) . . . . ?
C17 C6 C15 C19 -53.8(5) . . . . ?
C52 O3 C16 C42 -175.9(4) . . . . ?
C52 O3 C16 C11 5.2(7) . . . . ?
C30 C11 C16 O3 179.6(4) . . . . ?
C30 C11 C16 C42 0.8(7) . . . . ?
C9 C8 C17 C6 151.1(4) . . . . ?
C5 C8 C17 C6 -35.9(7) . . . . ?
C9 C8 C17 C14 -87.9(5) . . . . ?
C5 C8 C17 C14 85.2(6) . . . . ?
C9 C8 C17 C20 26.6(5) . . . . ?
C5 C8 C17 C20 -160.3(5) . . . . ?
O1 C6 C17 C8 46.0(5) . . . . ?
C15 C6 C17 C8 -79.7(5) . . . . ?
O1 C6 C17 C14 -75.2(5) . . . . ?
C15 C6 C17 C14 159.1(4) . . . . ?
O1 C6 C17 C20 164.8(4) . . . . ?
C15 C6 C17 C20 39.1(5) . . . . ?
C55 C12 C18 C40 -56.9(5) . . . . ?
C48 C12 C18 C40 -174.1(4) . . . . ?
C51 C12 C18 C40 62.8(5) . . . . ?
C55 C12 C18 C31 170.6(4) . . . . ?
C48 C12 C18 C31 53.4(5) . . . . ?
C51 C12 C18 C31 -69.7(5) . . . . ?
C6 C15 C19 C7 67.7(5) . . . . ?
C6 C15 C19 C31 -157.9(4) . . . . ?
C45 C7 C19 C15 -179.6(4) . . . . ?
C44 C7 C19 C15 59.4(5) . . . . ?
C20 C7 C19 C15 -64.4(5) . . . . ?
C45 C7 C19 C31 47.5(5) . . . . ?
C44 C7 C19 C31 -73.5(5) . . . . ?
C20 C7 C19 C31 162.7(4) . . . . ?
C45 C7 C20 C35 -74.3(5) . . . . ?
C44 C7 C20 C35 44.9(5) . . . . ?
C19 C7 C20 C35 169.3(4) . . . . ?
C45 C7 C20 C17 167.7(4) . . . . ?
C44 C7 C20 C17 -73.1(5) . . . . ?
C19 C7 C20 C17 51.3(5) . . . . ?
C8 C17 C20 C35 -35.7(4) . . . . ?
C6 C17 C20 C35 -163.9(4) . . . . ?
C14 C17 C20 C35 77.4(4) . . . . ?
C8 C17 C20 C7 88.9(4) . . . . ?
C6 C17 C20 C7 -39.4(5) . . . . ?
C14 C17 C20 C7 -158.1(4) . . . . ?
C58 C13 C21 C22 -52.8(5) . . . . ?
C54 C13 C21 C22 66.1(5) . . . . ?
C39 C13 C21 C22 -178.9(4) . . . . ?
C58 C13 C21 C36 76.6(5) . . . . ?
C54 C13 C21 C36 -164.5(4) . . . . ?
C39 C13 C21 C36 -49.5(5) . . . . ?
C36 C21 C22 C33 66.2(5) . . . . ?
C13 C21 C22 C33 -159.9(4) . . . . ?
C42 C27 C28 C30 0.8(7) . . . . ?
C42 C27 C28 C49 -177.4(5) . . . . ?
C8 C9 C29 C43 2.2(8) . . . . ?
C35 C9 C29 C43 -178.9(5) . . . . ?
C16 C11 C30 C28 0.1(7) . . . . ?
C16 C11 C30 C34 -174.8(5) . . . . ?
C27 C28 C30 C11 -0.9(7) . . . . ?
C49 C28 C30 C11 177.6(4) . . . . ?
C27 C28 C30 C34 175.0(4) . . . . ?
C49 C28 C30 C34 -6.5(5) . . . . ?
C32 C24 C31 C25 -71.7(5) . . . . ?
C32 C24 C31 C18 52.5(5) . . . . ?
C32 C24 C31 C19 167.5(4) . . . . ?
C40 C18 C31 C25 -66.9(5) . . . . ?
C12 C18 C31 C25 67.4(5) . . . . ?
C40 C18 C31 C24 172.5(4) . . . . ?
C12 C18 C31 C24 -53.2(5) . . . . ?
C40 C18 C31 C19 57.0(5) . . . . ?
C12 C18 C31 C19 -168.7(4) . . . . ?
C15 C19 C31 C25 -56.1(5) . . . . ?
C7 C19 C31 C25 74.3(5) . . . . ?
C15 C19 C31 C24 62.8(5) . . . . ?
C7 C19 C31 C24 -166.8(4) . . . . ?
C15 C19 C31 C18 178.2(4) . . . . ?
C7 C19 C31 C18 -51.4(5) . . . . ?
C31 C24 C32 C48 -56.0(6) . . . . ?
C21 C22 C33 O4 -176.7(4) . . . . ?
C21 C22 C33 C34 -52.0(6) . . . . ?
C11 C30 C34 C33 -33.8(7) . . . . ?
C28 C30 C34 C33 150.9(4) . . . . ?
C11 C30 C34 C41 88.0(6) . . . . ?
C28 C30 C34 C41 -87.4(5) . . . . ?
C11 C30 C34 C23 -157.7(5) . . . . ?
C28 C30 C34 C23 26.9(5) . . . . ?
O4 C33 C34 C30 46.0(6) . . . . ?
C22 C33 C34 C30 -79.8(6) . . . . ?
O4 C33 C34 C41 -76.4(5) . . . . ?
C22 C33 C34 C41 157.8(4) . . . . ?
O4 C33 C34 C23 164.2(4) . . . . ?
C22 C33 C34 C23 38.4(6) . . . . ?
C49 C23 C34 C30 -36.1(4) . . . . ?
C36 C23 C34 C30 88.0(5) . . . . ?
C49 C23 C34 C33 -164.7(4) . . . . ?
C36 C23 C34 C33 -40.5(6) . . . . ?
C49 C23 C34 C41 77.4(5) . . . . ?
C36 C23 C34 C41 -158.5(4) . . . . ?
C29 C9 C35 C20 163.3(5) . . . . ?
C8 C9 C35 C20 -17.7(5) . . . . ?
C7 C20 C35 C9 -93.4(5) . . . . ?
C17 C20 C35 C9 32.8(5) . . . . ?
C22 C21 C36 C53 58.5(5) . . . . ?
C13 C21 C36 C53 -74.0(5) . . . . ?
C22 C21 C36 C38 179.6(4) . . . . ?
C13 C21 C36 C38 47.1(5) . . . . ?
C22 C21 C36 C23 -65.5(5) . . . . ?
C13 C21 C36 C23 161.9(4) . . . . ?
C49 C23 C36 C53 47.2(5) . . . . ?
C34 C23 C36 C53 -70.9(5) . . . . ?
C49 C23 C36 C38 -71.5(5) . . . . ?
C34 C23 C36 C38 170.4(4) . . . . ?
C49 C23 C36 C21 172.2(4) . . . . ?
C34 C23 C36 C21 54.1(5) . . . . ?
C39 C26 C38 C36 61.0(5) . . . . ?
C53 C36 C38 C26 73.0(5) . . . . ?
C21 C36 C38 C26 -51.3(5) . . . . ?
C23 C36 C38 C26 -165.7(4) . . . . ?
C38 C26 C39 C13 -63.5(5) . . . . ?
C38 C26 C39 C37 160.3(4) . . . . ?
C58 C13 C39 C26 -68.5(5) . . . . ?
C54 C13 C39 C26 171.3(4) . . . . ?
C21 C13 C39 C26 56.1(5) . . . . ?
C58 C13 C39 C37 66.7(6) . . . . ?
C54 C13 C39 C37 -53.4(5) . . . . ?
C21 C13 C39 C37 -168.7(4) . . . . ?
C50 C37 C39 C26 -172.1(4) . . . . ?
C57 C37 C39 C26 -56.2(5) . . . . ?
C56 C37 C39 C26 63.5(6) . . . . ?
C50 C37 C39 C13 54.3(5) . . . . ?
C57 C37 C39 C13 170.2(4) . . . . ?
C56 C37 C39 C13 -70.1(6) . . . . ?
C31 C18 C40 C45 -62.7(5) . . . . ?
C12 C18 C40 C45 162.2(4) . . . . ?
C28 C27 C42 C16 0.1(7) . . . . ?
O3 C16 C42 C27 -179.8(4) . . . . ?
C11 C16 C42 C27 -0.9(7) . . . . ?
C9 C29 C43 C10 -1.8(8) . . . . ?
O2 C10 C43 C29 -179.6(4) . . . . ?
C5 C10 C43 C29 -0.1(7) . . . . ?
C18 C40 C45 C7 58.5(6) . . . . ?
C44 C7 C45 C40 75.0(5) . . . . ?
C19 C7 C45 C40 -49.0(5) . . . . ?
C20 C7 C45 C40 -163.3(4) . . . . ?
C24 C32 C48 C12 56.4(6) . . . . ?
C55 C12 C48 C32 -171.8(4) . . . . ?
C51 C12 C48 C32 72.0(5) . . . . ?
C18 C12 C48 C32 -53.4(5) . . . . ?
C27 C28 C49 C23 161.0(5) . . . . ?
C30 C28 C49 C23 -17.4(5) . . . . ?
C36 C23 C49 C28 -92.6(5) . . . . ?
C34 C23 C49 C28 32.9(5) . . . . ?
C54 C46 C50 C37 58.5(6) . . . . ?
C57 C37 C50 C46 -171.4(4) . . . . ?
C56 C37 C50 C46 72.0(5) . . . . ?
C39 C37 C50 C46 -54.6(5) . . . . ?
C50 C46 C54 C13 -57.4(6) . . . . ?
C58 C13 C54 C46 -71.1(5) . . . . ?
C39 C13 C54 C46 52.7(5) . . . . ?
C21 C13 C54 C46 168.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O4 . . . 2.856(5) 0.840 2.171 138.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


