# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1921283'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Benemerita Universidad Autonoma de Puebla
Mexico
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

# Clave Lab.  :  JC_E006
# Clave IF-UAP:  JC_E006
# Solicitud: 326
# Firma en la Solicitud: Dr. Jesus Sandoval (FCQ-BUAP) 
# Clave datos : ... \BUAP\Sylvain\JC_E006\55mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-05-20

_chemical_name_systematic        (25R)-5α-Spirostan-3β,5-diol
_chemical_name_common            ?
_chemical_melting_point          527
_chemical_formula_moiety         'C27 H44 O4, 0.5(H2 O)'
_chemical_formula_sum            'C27 H45 O4.50'
_chemical_formula_weight         441.63
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~=-63 (c=1, CHCl~3~)'

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.3797(10)
_cell_length_b                   8.0820(4)
_cell_length_c                   28.058(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.811(6)
_cell_angle_gamma                90
_cell_volume                     2542.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    11028
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      22.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.044
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -10 0.0240
-1 3 11 0.0200
5 0 -1 0.1960
-1 0 0 0.1990
0 1 -4 0.2990
0 -1 4 0.3050

_exptl_absorpt_coefficient_mu    0.049
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2935
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1201 frames, 50-70 /frame, 1 deg./frame, detector distance = 55 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            42679
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_av_R_equivalents  0.1544
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         20.499
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.879
_reflns_number_total             9025
_reflns_number_gt                3338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_max     0.725
_reflns_Friedel_fraction_full    0.747

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0085P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ? # -0.7(10)
_refine_ls_number_reflns         9025
_refine_ls_number_parameters     594
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   0.602
_refine_ls_restrained_S_all      0.602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.8587(4) 0.9642(5) 0.40978(15) 0.0494(13) Uani 1 1 d . . . . .
H1AA H 0.791564 1.030149 0.394437 0.059 Uiso 1 1 calc R U . . .
H1AB H 0.827511 0.870999 0.425454 0.059 Uiso 1 1 calc R U . . .
C2A C 0.9370(4) 1.0694(5) 0.44811(15) 0.0516(13) Uani 1 1 d . . . . .
H2AA H 0.960563 1.169409 0.433104 0.062 Uiso 1 1 calc R U . . .
H2AB H 0.890893 1.101751 0.472664 0.062 Uiso 1 1 calc R U . . .
C3A C 1.0479(4) 0.9775(5) 0.47197(15) 0.0439(12) Uani 1 1 d . . . . .
H3AA H 1.024378 0.888825 0.492227 0.053 Uiso 1 1 calc R U . . .
O3A O 1.1280(3) 1.0889(4) 0.50199(10) 0.0548(9) Uani 1 1 d . . . . .
H3A H 1.098(4) 1.141(5) 0.5273(15) 0.082 Uiso 1 1 d . U . . .
C4A C 1.1160(4) 0.9023(5) 0.43491(14) 0.0455(12) Uani 1 1 d . . . . .
H4AA H 1.179773 0.833136 0.451531 0.055 Uiso 1 1 calc R U . . .
H4AB H 1.152040 0.990523 0.418880 0.055 Uiso 1 1 calc R U . . .
C5A C 1.0362(4) 0.7988(5) 0.39692(14) 0.0392(11) Uani 1 1 d . . . . .
C6A C 1.1063(4) 0.7214(5) 0.36063(14) 0.0467(12) Uani 1 1 d . . . . .
H6AA H 1.172197 0.657332 0.377922 0.056 Uiso 1 1 calc R U . . .
H6AB H 1.139218 0.808393 0.343056 0.056 Uiso 1 1 calc R U . . .
O6A O 0.9886(3) 0.6625(3) 0.42231(10) 0.0485(9) Uani 1 1 d . . . . .
H6A H 1.046(4) 0.584(5) 0.4308(16) 0.073 Uiso 1 1 d . U . . .
C7A C 1.0263(4) 0.6081(5) 0.32450(14) 0.0474(12) Uani 1 1 d . . . . .
H7AA H 1.071944 0.566265 0.300889 0.057 Uiso 1 1 calc R U . . .
H7AB H 1.000670 0.514304 0.341699 0.057 Uiso 1 1 calc R U . . .
C8A C 0.9174(4) 0.6997(5) 0.29851(14) 0.0398(11) Uani 1 1 d . . . . .
H8AA H 0.945459 0.786542 0.278804 0.048 Uiso 1 1 calc R U . . .
C9A C 0.8465(4) 0.7855(5) 0.33470(14) 0.0391(11) Uani 1 1 d . . . . .
H9AA H 0.819924 0.696704 0.354147 0.047 Uiso 1 1 calc R U . . .
C10A C 0.9274(4) 0.8991(5) 0.37054(15) 0.0406(12) Uani 1 1 d . . . . .
C11A C 0.7340(4) 0.8702(5) 0.30905(16) 0.0539(14) Uani 1 1 d . . . . .
H11A H 0.756763 0.969266 0.293333 0.065 Uiso 1 1 calc R U . . .
H11B H 0.687051 0.904547 0.333099 0.065 Uiso 1 1 calc R U . . .
C12A C 0.6555(4) 0.7632(5) 0.27110(15) 0.0531(13) Uani 1 1 d . . . . .
H12A H 0.618938 0.676158 0.287396 0.064 Uiso 1 1 calc R U . . .
H12B H 0.592074 0.830964 0.253611 0.064 Uiso 1 1 calc R U . . .
C13A C 0.7260(4) 0.6850(5) 0.23507(15) 0.0440(12) Uani 1 1 d . . . . .
C14A C 0.8315(4) 0.5903(5) 0.26486(14) 0.0418(12) Uani 1 1 d . . . . .
H14A H 0.796003 0.515465 0.285953 0.050 Uiso 1 1 calc R U . . .
C15A C 0.8749(4) 0.4796(5) 0.22715(14) 0.0534(13) Uani 1 1 d . . . . .
H15A H 0.925118 0.390604 0.242292 0.064 Uiso 1 1 calc R U . . .
H15B H 0.918301 0.542563 0.206362 0.064 Uiso 1 1 calc R U . . .
C16A C 0.7567(4) 0.4135(5) 0.19910(15) 0.0491(13) Uani 1 1 d . . . . .
H16A H 0.736372 0.308432 0.213152 0.059 Uiso 1 1 calc R U . . .
O16A O 0.7572(3) 0.3932(4) 0.14848(10) 0.0552(9) Uani 1 1 d . . . . .
C17A C 0.6602(4) 0.5447(5) 0.20361(15) 0.0449(12) Uani 1 1 d . . . . .
H17A H 0.600644 0.495717 0.220820 0.054 Uiso 1 1 calc R U . . .
C18A C 0.7685(4) 0.8216(5) 0.20438(15) 0.0611(14) Uani 1 1 d . . . . .
H18A H 0.700827 0.880542 0.187419 0.092 Uiso 1 1 calc R U . . .
H18B H 0.812249 0.773378 0.181481 0.092 Uiso 1 1 calc R U . . .
H18C H 0.819174 0.896811 0.224972 0.092 Uiso 1 1 calc R U . . .
C19A C 0.9699(4) 1.0496(5) 0.34368(14) 0.0536(13) Uani 1 1 d . . . . .
H19D H 0.999129 1.011911 0.315431 0.080 Uiso 1 1 calc R U . . .
H19E H 1.032525 1.105943 0.364751 0.080 Uiso 1 1 calc R U . . .
H19F H 0.904290 1.123957 0.334245 0.080 Uiso 1 1 calc R U . . .
C20A C 0.6020(4) 0.5796(6) 0.15167(15) 0.0577(14) Uani 1 1 d . . . . .
H20A H 0.640875 0.676832 0.140413 0.069 Uiso 1 1 calc R U . . .
C21A C 0.4677(5) 0.6128(7) 0.14440(18) 0.098(2) Uani 1 1 d . . . . .
H21A H 0.453069 0.711034 0.161713 0.148 Uiso 1 1 calc R U . . .
H21B H 0.428240 0.520569 0.156344 0.148 Uiso 1 1 calc R U . . .
H21C H 0.437669 0.627703 0.110571 0.148 Uiso 1 1 calc R U . . .
C22A C 0.6383(5) 0.4265(6) 0.12460(17) 0.0517(13) Uani 1 1 d . . . . .
C23A C 0.6404(5) 0.4495(6) 0.07128(16) 0.0664(15) Uani 1 1 d . . . . .
H23A H 0.699495 0.532331 0.067138 0.080 Uiso 1 1 calc R U . . .
H23B H 0.563164 0.489157 0.055327 0.080 Uiso 1 1 calc R U . . .
C24A C 0.6698(5) 0.2878(7) 0.04782(16) 0.0748(17) Uani 1 1 d . . . . .
H24A H 0.660974 0.303035 0.013103 0.090 Uiso 1 1 calc R U . . .
H24B H 0.752057 0.258053 0.059849 0.090 Uiso 1 1 calc R U . . .
C25A C 0.5888(5) 0.1492(7) 0.05857(19) 0.0759(17) Uani 1 1 d . . . . .
H25A H 0.507162 0.173374 0.042538 0.091 Uiso 1 1 calc R U . . .
C26A C 0.5914(5) 0.1423(6) 0.1130(2) 0.0792(17) Uani 1 1 d . . . . .
H26A H 0.536648 0.057329 0.120036 0.095 Uiso 1 1 calc R U . . .
H26B H 0.670909 0.111394 0.128838 0.095 Uiso 1 1 calc R U . . .
O26A O 0.5596(3) 0.2966(4) 0.13237(11) 0.0636(9) Uani 1 1 d . . . . .
C27A C 0.6272(6) -0.0188(7) 0.0403(2) 0.121(3) Uani 1 1 d . . . . .
H27A H 0.571610 -0.102709 0.046029 0.182 Uiso 1 1 calc R U . . .
H27B H 0.705353 -0.046574 0.057120 0.182 Uiso 1 1 calc R U . . .
H27C H 0.628633 -0.011739 0.006200 0.182 Uiso 1 1 calc R U . . .
C1B C 0.4448(5) 0.5174(5) 0.37360(15) 0.0569(15) Uani 1 1 d . . . . .
H1BA H 0.444328 0.587618 0.345530 0.068 Uiso 1 1 calc R U . . .
H1BB H 0.365881 0.521673 0.382209 0.068 Uiso 1 1 calc R U . . .
C2B C 0.5352(5) 0.5869(5) 0.41577(15) 0.0593(14) Uani 1 1 d . . . . .
H2BA H 0.612160 0.598677 0.405674 0.071 Uiso 1 1 calc R U . . .
H2BB H 0.509448 0.695833 0.424239 0.071 Uiso 1 1 calc R U . . .
C3B C 0.5480(4) 0.4758(5) 0.45974(15) 0.0455(12) Uani 1 1 d . . . . .
H3BA H 0.470366 0.474211 0.470417 0.055 Uiso 1 1 calc R U . . .
O3B O 0.6325(3) 0.5394(4) 0.49918(12) 0.0551(10) Uani 1 1 d . . . . .
H3B H 0.695(4) 0.553(7) 0.4956(19) 0.083 Uiso 1 1 d . U . . .
C4B C 0.5756(4) 0.2995(4) 0.44750(14) 0.0417(11) Uani 1 1 d . . . . .
H4BA H 0.578215 0.230880 0.476022 0.050 Uiso 1 1 calc R U . . .
H4BB H 0.653596 0.295488 0.437963 0.050 Uiso 1 1 calc R U . . .
C5B C 0.4826(4) 0.2302(5) 0.40659(15) 0.0370(11) Uani 1 1 d . . . . .
C6B C 0.5052(4) 0.0506(4) 0.39564(14) 0.0404(12) Uani 1 1 d . . . . .
H6BA H 0.506502 -0.014434 0.424779 0.048 Uiso 1 1 calc R U . . .
H6BB H 0.582957 0.041061 0.386091 0.048 Uiso 1 1 calc R U . . .
O6B O 0.3680(3) 0.2416(3) 0.42232(10) 0.0468(9) Uani 1 1 d . . . . .
H6B H 0.365(4) 0.172(5) 0.4452(15) 0.070 Uiso 1 1 d . U . . .
C7B C 0.4107(4) -0.0196(4) 0.35550(15) 0.0463(13) Uani 1 1 d . . . . .
H7BA H 0.336263 -0.030334 0.367690 0.056 Uiso 1 1 calc R U . . .
H7BB H 0.435050 -0.129674 0.347378 0.056 Uiso 1 1 calc R U . . .
C8B C 0.3887(4) 0.0855(4) 0.30925(14) 0.0385(11) Uani 1 1 d . . . . .
H8BA H 0.459547 0.080557 0.293745 0.046 Uiso 1 1 calc R U . . .
C9B C 0.3664(4) 0.2675(4) 0.32233(14) 0.0377(11) Uani 1 1 d . . . . .
H9BA H 0.296267 0.266565 0.338334 0.045 Uiso 1 1 calc R U . . .
C10B C 0.4710(4) 0.3382(5) 0.35993(14) 0.0387(11) Uani 1 1 d . . . . .
C11B C 0.3329(4) 0.3746(4) 0.27669(15) 0.0576(15) Uani 1 1 d . . . . .
H11C H 0.400683 0.381218 0.259962 0.069 Uiso 1 1 calc R U . . .
H11D H 0.314476 0.485860 0.286098 0.069 Uiso 1 1 calc R U . . .
C12B C 0.2248(5) 0.3038(5) 0.24198(16) 0.0603(14) Uani 1 1 d . . . . .
H12C H 0.155049 0.306499 0.257612 0.072 Uiso 1 1 calc R U . . .
H12D H 0.208531 0.372202 0.213203 0.072 Uiso 1 1 calc R U . . .
C13B C 0.2477(4) 0.1264(5) 0.22752(14) 0.0409(11) Uani 1 1 d . . . . .
C14B C 0.2824(4) 0.0218(4) 0.27420(14) 0.0380(11) Uani 1 1 d . . . . .
H14B H 0.214551 0.031349 0.291365 0.046 Uiso 1 1 calc R U . . .
C15B C 0.2783(4) -0.1545(5) 0.25548(15) 0.0466(12) Uani 1 1 d . . . . .
H15C H 0.266426 -0.232429 0.280517 0.056 Uiso 1 1 calc R U . . .
H15D H 0.351154 -0.182526 0.243750 0.056 Uiso 1 1 calc R U . . .
C16B C 0.1700(4) -0.1540(5) 0.21367(15) 0.0486(13) Uani 1 1 d . . . . .
H16B H 0.103016 -0.215878 0.222665 0.058 Uiso 1 1 calc R U . . .
O16B O 0.1997(3) -0.2151(3) 0.16943(10) 0.0493(8) Uani 1 1 d . . . . .
C17B C 0.1361(4) 0.0298(5) 0.20342(14) 0.0430(12) Uani 1 1 d . . . . .
H17B H 0.068492 0.058461 0.219266 0.052 Uiso 1 1 calc R U . . .
C18B C 0.3478(4) 0.1214(5) 0.19662(14) 0.0563(13) Uani 1 1 d . . . . .
H18D H 0.422158 0.151734 0.216266 0.084 Uiso 1 1 calc R U . . .
H18E H 0.329481 0.197748 0.170183 0.084 Uiso 1 1 calc R U . . .
H18F H 0.353855 0.011611 0.184204 0.084 Uiso 1 1 calc R U . . .
C19B C 0.5890(4) 0.3350(5) 0.33941(15) 0.0572(14) Uani 1 1 d . . . . .
H19A H 0.610919 0.222398 0.334410 0.086 Uiso 1 1 calc R U . . .
H19B H 0.650933 0.387203 0.361924 0.086 Uiso 1 1 calc R U . . .
H19C H 0.578403 0.393344 0.309178 0.086 Uiso 1 1 calc R U . . .
C20B C 0.0968(4) 0.0356(5) 0.14852(15) 0.0501(13) Uani 1 1 d . . . . .
H20B H 0.151655 0.108460 0.134994 0.060 Uiso 1 1 calc R U . . .
C21B C -0.0299(5) 0.1001(6) 0.13248(16) 0.0747(16) Uani 1 1 d . . . . .
H21D H -0.033516 0.214745 0.141096 0.112 Uiso 1 1 calc R U . . .
H21E H -0.084112 0.037705 0.148198 0.112 Uiso 1 1 calc R U . . .
H21F H -0.051871 0.088445 0.098060 0.112 Uiso 1 1 calc R U . . .
C22B C 0.1157(5) -0.1431(5) 0.13173(15) 0.0496(13) Uani 1 1 d . . . . .
C23B C 0.1649(5) -0.1518(5) 0.08487(15) 0.0587(15) Uani 1 1 d . . . . .
H23C H 0.245212 -0.107240 0.090210 0.070 Uiso 1 1 calc R U . . .
H23D H 0.116308 -0.083212 0.060818 0.070 Uiso 1 1 calc R U . . .
C24B C 0.1674(5) -0.3274(6) 0.06540(17) 0.0709(16) Uani 1 1 d . . . . .
H24C H 0.188836 -0.324335 0.033393 0.085 Uiso 1 1 calc R U . . .
H24D H 0.227731 -0.390934 0.086274 0.085 Uiso 1 1 calc R U . . .
C25B C 0.0475(5) -0.4113(6) 0.06271(16) 0.0635(15) Uani 1 1 d . . . . .
H25B H -0.010529 -0.350662 0.039280 0.076 Uiso 1 1 calc R U . . .
C26B C 0.0096(4) -0.3971(6) 0.11169(16) 0.0600(14) Uani 1 1 d . . . . .
H26C H -0.068309 -0.447559 0.110166 0.072 Uiso 1 1 calc R U . . .
H26D H 0.065542 -0.457597 0.135348 0.072 Uiso 1 1 calc R U . . .
O26B O 0.0043(3) -0.2271(4) 0.12728(10) 0.0551(9) Uani 1 1 d . . . . .
C27B C 0.0495(5) -0.5898(6) 0.04567(18) 0.099(2) Uani 1 1 d . . . . .
H27D H -0.028698 -0.636817 0.043348 0.148 Uiso 1 1 calc R U . . .
H27E H 0.104947 -0.652209 0.068376 0.148 Uiso 1 1 calc R U . . .
H27F H 0.073622 -0.592876 0.014511 0.148 Uiso 1 1 calc R U . . .
O1 O 0.1611(4) 0.4003(5) 0.44457(16) 0.0921(15) Uani 1 1 d . . . . .
H11 H 0.154(6) 0.321(7) 0.460(2) 0.138 Uiso 1 1 d . U . . .
H12 H 0.201(6) 0.364(8) 0.426(2) 0.138 Uiso 1 1 d . U . . .


_geom_special_details            ?

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
C1A C2A 1.532(5) . ?
C1A C10A 1.547(5) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A C3A 1.518(5) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3A O3A 1.445(5) . ?
C3A C4A 1.525(5) . ?
C3A H3AA 0.9800 . ?
O3A H3A 0.94(4) . ?
C4A C5A 1.527(5) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5A O6A 1.465(4) . ?
C5A C6A 1.531(5) . ?
C5A C10A 1.557(5) . ?
C6A C7A 1.543(5) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
O6A H6A 0.91(4) . ?
C7A C8A 1.518(5) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A C14A 1.522(5) . ?
C8A C9A 1.563(5) . ?
C8A H8AA 0.9800 . ?
C9A C11A 1.520(5) . ?
C9A C10A 1.545(5) . ?
C9A H9AA 0.9800 . ?
C10A C19A 1.551(5) . ?
C11A C12A 1.535(5) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13A 1.531(5) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C18A 1.528(5) . ?
C13A C14A 1.543(5) . ?
C13A C17A 1.550(5) . ?
C14A C15A 1.531(5) . ?
C14A H14A 0.9800 . ?
C15A C16A 1.535(6) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C16A O16A 1.431(4) . ?
C16A C17A 1.548(5) . ?
C16A H16A 0.9800 . ?
O16A C22A 1.429(5) . ?
C17A C20A 1.520(5) . ?
C17A H17A 0.9800 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A C21A 1.531(6) . ?
C20A C22A 1.544(6) . ?
C20A H20A 0.9800 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A O26A 1.420(5) . ?
C22A C23A 1.512(6) . ?
C23A C24A 1.526(6) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C24A C25A 1.513(6) . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C25A C26A 1.523(6) . ?
C25A C27A 1.542(6) . ?
C25A H25A 0.9800 . ?
C26A O26A 1.432(5) . ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C1B C2B 1.536(6) . ?
C1B C10B 1.540(5) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C3B 1.513(5) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C3B O3B 1.432(5) . ?
C3B C4B 1.511(5) . ?
C3B H3BA 0.9800 . ?
O3B H3B 0.75(5) . ?
C4B C5B 1.529(5) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C5B O6B 1.449(5) . ?
C5B C6B 1.514(5) . ?
C5B C10B 1.561(5) . ?
C6B C7B 1.528(5) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
O6B H6B 0.86(4) . ?
C7B C8B 1.536(5) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B C14B 1.513(5) . ?
C8B C9B 1.548(5) . ?
C8B H8BA 0.9800 . ?
C9B C11B 1.539(5) . ?
C9B C10B 1.559(5) . ?
C9B H9BA 0.9800 . ?
C10B C19B 1.549(5) . ?
C11B C12B 1.544(6) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C13B 1.524(5) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C17B 1.544(6) . ?
C13B C18B 1.545(5) . ?
C13B C14B 1.552(5) . ?
C14B C15B 1.517(5) . ?
C14B H14B 0.9800 . ?
C15B C16B 1.549(6) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C16B O16B 1.429(5) . ?
C16B C17B 1.549(5) . ?
C16B H16B 0.9800 . ?
O16B C22B 1.424(5) . ?
C17B C20B 1.530(5) . ?
C17B H17B 0.9800 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B H19A 0.9600 . ?
C19B H19B 0.9600 . ?
C19B H19C 0.9600 . ?
C20B C21B 1.528(6) . ?
C20B C22B 1.546(6) . ?
C20B H20B 0.9800 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B O26B 1.425(5) . ?
C22B C23B 1.516(5) . ?
C23B C24B 1.523(5) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C24B C25B 1.514(6) . ?
C24B H24C 0.9700 . ?
C24B H24D 0.9700 . ?
C25B C26B 1.513(5) . ?
C25B C27B 1.521(6) . ?
C25B H25B 0.9800 . ?
C26B O26B 1.447(5) . ?
C26B H26C 0.9700 . ?
C26B H26D 0.9700 . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?
O1 H11 0.79(6) . ?
O1 H12 0.80(6) . ?

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
C2A C1A C10A 112.6(4) . . ?
C2A C1A H1AA 109.1 . . ?
C10A C1A H1AA 109.1 . . ?
C2A C1A H1AB 109.1 . . ?
C10A C1A H1AB 109.1 . . ?
H1AA C1A H1AB 107.8 . . ?
C3A C2A C1A 112.2(3) . . ?
C3A C2A H2AA 109.2 . . ?
C1A C2A H2AA 109.2 . . ?
C3A C2A H2AB 109.2 . . ?
C1A C2A H2AB 109.2 . . ?
H2AA C2A H2AB 107.9 . . ?
O3A C3A C2A 110.3(3) . . ?
O3A C3A C4A 107.6(4) . . ?
C2A C3A C4A 112.1(4) . . ?
O3A C3A H3AA 109.0 . . ?
C2A C3A H3AA 109.0 . . ?
C4A C3A H3AA 109.0 . . ?
C3A O3A H3A 116(3) . . ?
C3A C4A C5A 112.5(4) . . ?
C3A C4A H4AA 109.1 . . ?
C5A C4A H4AA 109.1 . . ?
C3A C4A H4AB 109.1 . . ?
C5A C4A H4AB 109.1 . . ?
H4AA C4A H4AB 107.8 . . ?
O6A C5A C4A 107.3(3) . . ?
O6A C5A C6A 107.1(3) . . ?
C4A C5A C6A 111.9(4) . . ?
O6A C5A C10A 107.0(3) . . ?
C4A C5A C10A 112.2(3) . . ?
C6A C5A C10A 111.0(3) . . ?
C5A C6A C7A 111.3(4) . . ?
C5A C6A H6AA 109.4 . . ?
C7A C6A H6AA 109.4 . . ?
C5A C6A H6AB 109.4 . . ?
C7A C6A H6AB 109.4 . . ?
H6AA C6A H6AB 108.0 . . ?
C5A O6A H6A 110(3) . . ?
C8A C7A C6A 111.6(3) . . ?
C8A C7A H7AA 109.3 . . ?
C6A C7A H7AA 109.3 . . ?
C8A C7A H7AB 109.3 . . ?
C6A C7A H7AB 109.3 . . ?
H7AA C7A H7AB 108.0 . . ?
C7A C8A C14A 113.6(3) . . ?
C7A C8A C9A 111.9(3) . . ?
C14A C8A C9A 108.2(3) . . ?
C7A C8A H8AA 107.6 . . ?
C14A C8A H8AA 107.6 . . ?
C9A C8A H8AA 107.6 . . ?
C11A C9A C10A 113.6(3) . . ?
C11A C9A C8A 112.3(3) . . ?
C10A C9A C8A 111.7(3) . . ?
C11A C9A H9AA 106.2 . . ?
C10A C9A H9AA 106.2 . . ?
C8A C9A H9AA 106.2 . . ?
C9A C10A C1A 110.4(4) . . ?
C9A C10A C19A 110.5(3) . . ?
C1A C10A C19A 108.4(3) . . ?
C9A C10A C5A 109.7(3) . . ?
C1A C10A C5A 107.2(3) . . ?
C19A C10A C5A 110.5(4) . . ?
C9A C11A C12A 114.7(3) . . ?
C9A C11A H11A 108.6 . . ?
C12A C11A H11A 108.6 . . ?
C9A C11A H11B 108.6 . . ?
C12A C11A H11B 108.6 . . ?
H11A C11A H11B 107.6 . . ?
C13A C12A C11A 112.4(4) . . ?
C13A C12A H12A 109.1 . . ?
C11A C12A H12A 109.1 . . ?
C13A C12A H12B 109.1 . . ?
C11A C12A H12B 109.1 . . ?
H12A C12A H12B 107.8 . . ?
C18A C13A C12A 109.0(3) . . ?
C18A C13A C14A 111.8(4) . . ?
C12A C13A C14A 107.1(3) . . ?
C18A C13A C17A 112.1(3) . . ?
C12A C13A C17A 114.9(4) . . ?
C14A C13A C17A 101.6(3) . . ?
C8A C14A C15A 121.3(4) . . ?
C8A C14A C13A 114.0(3) . . ?
C15A C14A C13A 103.2(3) . . ?
C8A C14A H14A 105.7 . . ?
C15A C14A H14A 105.7 . . ?
C13A C14A H14A 105.7 . . ?
C14A C15A C16A 101.5(4) . . ?
C14A C15A H15A 111.5 . . ?
C16A C15A H15A 111.5 . . ?
C14A C15A H15B 111.5 . . ?
C16A C15A H15B 111.5 . . ?
H15A C15A H15B 109.3 . . ?
O16A C16A C15A 113.4(4) . . ?
O16A C16A C17A 106.4(3) . . ?
C15A C16A C17A 107.0(3) . . ?
O16A C16A H16A 110.0 . . ?
C15A C16A H16A 110.0 . . ?
C17A C16A H16A 110.0 . . ?
C22A O16A C16A 106.3(3) . . ?
C20A C17A C16A 104.3(3) . . ?
C20A C17A C13A 120.0(4) . . ?
C16A C17A C13A 105.5(3) . . ?
C20A C17A H17A 108.8 . . ?
C16A C17A H17A 108.8 . . ?
C13A C17A H17A 108.8 . . ?
C13A C18A H18A 109.5 . . ?
C13A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C13A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C10A C19A H19D 109.5 . . ?
C10A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C10A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C17A C20A C21A 114.9(4) . . ?
C17A C20A C22A 102.4(4) . . ?
C21A C20A C22A 114.8(4) . . ?
C17A C20A H20A 108.1 . . ?
C21A C20A H20A 108.1 . . ?
C22A C20A H20A 108.1 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
O26A C22A O16A 111.1(4) . . ?
O26A C22A C23A 111.1(4) . . ?
O16A C22A C23A 108.3(4) . . ?
O26A C22A C20A 106.8(4) . . ?
O16A C22A C20A 103.4(4) . . ?
C23A C22A C20A 116.0(4) . . ?
C22A C23A C24A 111.3(4) . . ?
C22A C23A H23A 109.4 . . ?
C24A C23A H23A 109.4 . . ?
C22A C23A H23B 109.4 . . ?
C24A C23A H23B 109.4 . . ?
H23A C23A H23B 108.0 . . ?
C25A C24A C23A 111.2(4) . . ?
C25A C24A H24A 109.4 . . ?
C23A C24A H24A 109.4 . . ?
C25A C24A H24B 109.4 . . ?
C23A C24A H24B 109.4 . . ?
H24A C24A H24B 108.0 . . ?
C24A C25A C26A 108.6(4) . . ?
C24A C25A C27A 111.6(5) . . ?
C26A C25A C27A 110.1(5) . . ?
C24A C25A H25A 108.8 . . ?
C26A C25A H25A 108.8 . . ?
C27A C25A H25A 108.8 . . ?
O26A C26A C25A 112.7(4) . . ?
O26A C26A H26A 109.1 . . ?
C25A C26A H26A 109.1 . . ?
O26A C26A H26B 109.1 . . ?
C25A C26A H26B 109.1 . . ?
H26A C26A H26B 107.8 . . ?
C22A O26A C26A 112.3(4) . . ?
C25A C27A H27A 109.5 . . ?
C25A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C25A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C2B C1B C10B 113.8(4) . . ?
C2B C1B H1BA 108.8 . . ?
C10B C1B H1BA 108.8 . . ?
C2B C1B H1BB 108.8 . . ?
C10B C1B H1BB 108.8 . . ?
H1BA C1B H1BB 107.7 . . ?
C3B C2B C1B 111.7(4) . . ?
C3B C2B H2BA 109.3 . . ?
C1B C2B H2BA 109.3 . . ?
C3B C2B H2BB 109.3 . . ?
C1B C2B H2BB 109.3 . . ?
H2BA C2B H2BB 107.9 . . ?
O3B C3B C4B 112.1(4) . . ?
O3B C3B C2B 112.1(3) . . ?
C4B C3B C2B 111.7(3) . . ?
O3B C3B H3BA 106.9 . . ?
C4B C3B H3BA 106.9 . . ?
C2B C3B H3BA 106.9 . . ?
C3B O3B H3B 119(4) . . ?
C3B C4B C5B 111.8(3) . . ?
C3B C4B H4BA 109.2 . . ?
C5B C4B H4BA 109.2 . . ?
C3B C4B H4BB 109.2 . . ?
C5B C4B H4BB 109.2 . . ?
H4BA C4B H4BB 107.9 . . ?
O6B C5B C6B 108.4(3) . . ?
O6B C5B C4B 107.0(3) . . ?
C6B C5B C4B 112.5(3) . . ?
O6B C5B C10B 105.6(3) . . ?
C6B C5B C10B 111.0(3) . . ?
C4B C5B C10B 111.9(3) . . ?
C5B C6B C7B 112.5(3) . . ?
C5B C6B H6BA 109.1 . . ?
C7B C6B H6BA 109.1 . . ?
C5B C6B H6BB 109.1 . . ?
C7B C6B H6BB 109.1 . . ?
H6BA C6B H6BB 107.8 . . ?
C5B O6B H6B 110(3) . . ?
C6B C7B C8B 114.2(3) . . ?
C6B C7B H7BA 108.7 . . ?
C8B C7B H7BA 108.7 . . ?
C6B C7B H7BB 108.7 . . ?
C8B C7B H7BB 108.7 . . ?
H7BA C7B H7BB 107.6 . . ?
C14B C8B C7B 111.0(3) . . ?
C14B C8B C9B 109.4(3) . . ?
C7B C8B C9B 109.6(3) . . ?
C14B C8B H8BA 108.9 . . ?
C7B C8B H8BA 108.9 . . ?
C9B C8B H8BA 108.9 . . ?
C11B C9B C8B 111.4(3) . . ?
C11B C9B C10B 114.1(3) . . ?
C8B C9B C10B 111.8(3) . . ?
C11B C9B H9BA 106.3 . . ?
C8B C9B H9BA 106.3 . . ?
C10B C9B H9BA 106.3 . . ?
C1B C10B C19B 109.0(4) . . ?
C1B C10B C9B 110.8(4) . . ?
C19B C10B C9B 110.7(3) . . ?
C1B C10B C5B 108.0(3) . . ?
C19B C10B C5B 110.4(3) . . ?
C9B C10B C5B 107.9(3) . . ?
C9B C11B C12B 112.0(3) . . ?
C9B C11B H11C 109.2 . . ?
C12B C11B H11C 109.2 . . ?
C9B C11B H11D 109.2 . . ?
C12B C11B H11D 109.2 . . ?
H11C C11B H11D 107.9 . . ?
C13B C12B C11B 111.3(4) . . ?
C13B C12B H12C 109.4 . . ?
C11B C12B H12C 109.4 . . ?
C13B C12B H12D 109.4 . . ?
C11B C12B H12D 109.4 . . ?
H12C C12B H12D 108.0 . . ?
C12B C13B C17B 115.3(4) . . ?
C12B C13B C18B 110.5(4) . . ?
C17B C13B C18B 111.7(3) . . ?
C12B C13B C14B 108.5(3) . . ?
C17B C13B C14B 99.6(3) . . ?
C18B C13B C14B 110.7(4) . . ?
C8B C14B C15B 121.2(4) . . ?
C8B C14B C13B 115.1(3) . . ?
C15B C14B C13B 103.3(3) . . ?
C8B C14B H14B 105.3 . . ?
C15B C14B H14B 105.3 . . ?
C13B C14B H14B 105.3 . . ?
C14B C15B C16B 103.5(3) . . ?
C14B C15B H15C 111.1 . . ?
C16B C15B H15C 111.1 . . ?
C14B C15B H15D 111.1 . . ?
C16B C15B H15D 111.1 . . ?
H15C C15B H15D 109.0 . . ?
O16B C16B C15B 112.4(4) . . ?
O16B C16B C17B 105.0(3) . . ?
C15B C16B C17B 106.5(3) . . ?
O16B C16B H16B 110.9 . . ?
C15B C16B H16B 110.9 . . ?
C17B C16B H16B 110.9 . . ?
C22B O16B C16B 106.0(3) . . ?
C20B C17B C13B 120.2(4) . . ?
C20B C17B C16B 103.7(3) . . ?
C13B C17B C16B 104.1(3) . . ?
C20B C17B H17B 109.4 . . ?
C13B C17B H17B 109.4 . . ?
C16B C17B H17B 109.4 . . ?
C13B C18B H18D 109.5 . . ?
C13B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C13B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C10B C19B H19A 109.5 . . ?
C10B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
C10B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C21B C20B C17B 114.0(4) . . ?
C21B C20B C22B 113.7(4) . . ?
C17B C20B C22B 104.3(3) . . ?
C21B C20B H20B 108.2 . . ?
C17B C20B H20B 108.2 . . ?
C22B C20B H20B 108.2 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O16B C22B O26B 110.2(3) . . ?
O16B C22B C23B 109.0(4) . . ?
O26B C22B C23B 110.9(4) . . ?
O16B C22B C20B 105.4(3) . . ?
O26B C22B C20B 107.7(4) . . ?
C23B C22B C20B 113.5(4) . . ?
C22B C23B C24B 112.8(4) . . ?
C22B C23B H23C 109.0 . . ?
C24B C23B H23C 109.0 . . ?
C22B C23B H23D 109.0 . . ?
C24B C23B H23D 109.0 . . ?
H23C C23B H23D 107.8 . . ?
C25B C24B C23B 111.3(4) . . ?
C25B C24B H24C 109.4 . . ?
C23B C24B H24C 109.4 . . ?
C25B C24B H24D 109.4 . . ?
C23B C24B H24D 109.4 . . ?
H24C C24B H24D 108.0 . . ?
C26B C25B C24B 108.4(4) . . ?
C26B C25B C27B 112.3(4) . . ?
C24B C25B C27B 112.2(5) . . ?
C26B C25B H25B 107.9 . . ?
C24B C25B H25B 107.9 . . ?
C27B C25B H25B 107.9 . . ?
O26B C26B C25B 112.3(4) . . ?
O26B C26B H26C 109.1 . . ?
C25B C26B H26C 109.1 . . ?
O26B C26B H26D 109.1 . . ?
C25B C26B H26D 109.1 . . ?
H26C C26B H26D 107.9 . . ?
C22B O26B C26B 113.4(4) . . ?
C25B C27B H27D 109.5 . . ?
C25B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C25B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
H11 O1 H12 100(6) . . ?

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
C10A C1A C2A C3A -55.7(5) . . . . ?
C1A C2A C3A O3A 170.8(3) . . . . ?
C1A C2A C3A C4A 51.0(5) . . . . ?
O3A C3A C4A C5A -172.7(3) . . . . ?
C2A C3A C4A C5A -51.4(5) . . . . ?
C3A C4A C5A O6A -61.6(4) . . . . ?
C3A C4A C5A C6A -178.8(3) . . . . ?
C3A C4A C5A C10A 55.6(5) . . . . ?
O6A C5A C6A C7A 59.0(4) . . . . ?
C4A C5A C6A C7A 176.3(4) . . . . ?
C10A C5A C6A C7A -57.5(4) . . . . ?
C5A C6A C7A C8A 55.6(5) . . . . ?
C6A C7A C8A C14A -176.2(4) . . . . ?
C6A C7A C8A C9A -53.3(5) . . . . ?
C7A C8A C9A C11A -177.2(4) . . . . ?
C14A C8A C9A C11A -51.2(4) . . . . ?
C7A C8A C9A C10A 53.9(4) . . . . ?
C14A C8A C9A C10A 179.8(3) . . . . ?
C11A C9A C10A C1A 59.0(5) . . . . ?
C8A C9A C10A C1A -172.8(3) . . . . ?
C11A C9A C10A C19A -60.9(5) . . . . ?
C8A C9A C10A C19A 67.3(4) . . . . ?
C11A C9A C10A C5A 176.9(4) . . . . ?
C8A C9A C10A C5A -54.8(4) . . . . ?
C2A C1A C10A C9A 176.6(3) . . . . ?
C2A C1A C10A C19A -62.3(5) . . . . ?
C2A C1A C10A C5A 57.1(4) . . . . ?
O6A C5A C10A C9A -59.4(4) . . . . ?
C4A C5A C10A C9A -176.9(3) . . . . ?
C6A C5A C10A C9A 57.2(4) . . . . ?
O6A C5A C10A C1A 60.5(4) . . . . ?
C4A C5A C10A C1A -57.0(4) . . . . ?
C6A C5A C10A C1A 177.0(3) . . . . ?
O6A C5A C10A C19A 178.5(3) . . . . ?
C4A C5A C10A C19A 61.0(4) . . . . ?
C6A C5A C10A C19A -65.0(4) . . . . ?
C10A C9A C11A C12A 176.7(4) . . . . ?
C8A C9A C11A C12A 48.7(5) . . . . ?
C9A C11A C12A C13A -51.1(5) . . . . ?
C11A C12A C13A C18A -66.8(5) . . . . ?
C11A C12A C13A C14A 54.3(4) . . . . ?
C11A C12A C13A C17A 166.4(4) . . . . ?
C7A C8A C14A C15A -50.9(5) . . . . ?
C9A C8A C14A C15A -175.8(3) . . . . ?
C7A C8A C14A C13A -175.1(4) . . . . ?
C9A C8A C14A C13A 59.9(4) . . . . ?
C18A C13A C14A C8A 57.7(5) . . . . ?
C12A C13A C14A C8A -61.7(5) . . . . ?
C17A C13A C14A C8A 177.5(4) . . . . ?
C18A C13A C14A C15A -75.7(4) . . . . ?
C12A C13A C14A C15A 164.9(3) . . . . ?
C17A C13A C14A C15A 44.0(4) . . . . ?
C8A C14A C15A C16A -173.3(4) . . . . ?
C13A C14A C15A C16A -44.2(4) . . . . ?
C14A C15A C16A O16A 144.3(3) . . . . ?
C14A C15A C16A C17A 27.3(4) . . . . ?
C15A C16A O16A C22A -147.2(4) . . . . ?
C17A C16A O16A C22A -29.9(4) . . . . ?
O16A C16A C17A C20A 5.2(5) . . . . ?
C15A C16A C17A C20A 126.8(4) . . . . ?
O16A C16A C17A C13A -122.0(3) . . . . ?
C15A C16A C17A C13A -0.5(5) . . . . ?
C18A C13A C17A C20A -23.8(6) . . . . ?
C12A C13A C17A C20A 101.4(5) . . . . ?
C14A C13A C17A C20A -143.4(4) . . . . ?
C18A C13A C17A C16A 93.3(4) . . . . ?
C12A C13A C17A C16A -141.5(4) . . . . ?
C14A C13A C17A C16A -26.3(4) . . . . ?
C16A C17A C20A C21A 144.1(4) . . . . ?
C13A C17A C20A C21A -98.2(5) . . . . ?
C16A C17A C20A C22A 18.9(5) . . . . ?
C13A C17A C20A C22A 136.7(4) . . . . ?
C16A O16A C22A O26A -71.9(4) . . . . ?
C16A O16A C22A C23A 165.9(4) . . . . ?
C16A O16A C22A C20A 42.3(4) . . . . ?
C17A C20A C22A O26A 80.0(4) . . . . ?
C21A C20A C22A O26A -45.3(5) . . . . ?
C17A C20A C22A O16A -37.3(5) . . . . ?
C21A C20A C22A O16A -162.5(4) . . . . ?
C17A C20A C22A C23A -155.7(4) . . . . ?
C21A C20A C22A C23A 79.1(6) . . . . ?
O26A C22A C23A C24A -54.3(6) . . . . ?
O16A C22A C23A C24A 67.9(5) . . . . ?
C20A C22A C23A C24A -176.5(5) . . . . ?
C22A C23A C24A C25A 52.2(6) . . . . ?
C23A C24A C25A C26A -51.7(6) . . . . ?
C23A C24A C25A C27A -173.2(4) . . . . ?
C24A C25A C26A O26A 55.9(6) . . . . ?
C27A C25A C26A O26A 178.4(5) . . . . ?
O16A C22A O26A C26A -62.2(5) . . . . ?
C23A C22A O26A C26A 58.4(5) . . . . ?
C20A C22A O26A C26A -174.2(4) . . . . ?
C25A C26A O26A C22A -60.4(6) . . . . ?
C10B C1B C2B C3B -54.0(5) . . . . ?
C1B C2B C3B O3B 179.7(4) . . . . ?
C1B C2B C3B C4B 53.1(5) . . . . ?
O3B C3B C4B C5B 177.9(3) . . . . ?
C2B C3B C4B C5B -55.4(5) . . . . ?
C3B C4B C5B O6B -58.0(4) . . . . ?
C3B C4B C5B C6B -176.9(4) . . . . ?
C3B C4B C5B C10B 57.2(5) . . . . ?
O6B C5B C6B C7B 60.6(4) . . . . ?
C4B C5B C6B C7B 178.8(3) . . . . ?
C10B C5B C6B C7B -54.9(5) . . . . ?
C5B C6B C7B C8B 51.5(5) . . . . ?
C6B C7B C8B C14B -171.8(4) . . . . ?
C6B C7B C8B C9B -50.9(5) . . . . ?
C14B C8B C9B C11B -53.1(5) . . . . ?
C7B C8B C9B C11B -175.0(4) . . . . ?
C14B C8B C9B C10B 177.9(3) . . . . ?
C7B C8B C9B C10B 56.0(4) . . . . ?
C2B C1B C10B C19B -66.3(5) . . . . ?
C2B C1B C10B C9B 171.7(4) . . . . ?
C2B C1B C10B C5B 53.6(5) . . . . ?
C11B C9B C10B C1B 54.3(5) . . . . ?
C8B C9B C10B C1B -178.1(3) . . . . ?
C11B C9B C10B C19B -66.8(4) . . . . ?
C8B C9B C10B C19B 60.8(4) . . . . ?
C11B C9B C10B C5B 172.4(3) . . . . ?
C8B C9B C10B C5B -60.0(4) . . . . ?
O6B C5B C10B C1B 61.2(4) . . . . ?
C6B C5B C10B C1B 178.5(4) . . . . ?
C4B C5B C10B C1B -54.8(5) . . . . ?
O6B C5B C10B C19B -179.7(3) . . . . ?
C6B C5B C10B C19B -62.4(4) . . . . ?
C4B C5B C10B C19B 64.3(4) . . . . ?
O6B C5B C10B C9B -58.7(4) . . . . ?
C6B C5B C10B C9B 58.6(4) . . . . ?
C4B C5B C10B C9B -174.7(3) . . . . ?
C8B C9B C11B C12B 55.2(5) . . . . ?
C10B C9B C11B C12B -177.0(4) . . . . ?
C9B C11B C12B C13B -56.9(5) . . . . ?
C11B C12B C13B C17B 165.6(4) . . . . ?
C11B C12B C13B C18B -66.5(5) . . . . ?
C11B C12B C13B C14B 55.0(5) . . . . ?
C7B C8B C14B C15B -58.1(5) . . . . ?
C9B C8B C14B C15B -179.1(3) . . . . ?
C7B C8B C14B C13B 176.4(3) . . . . ?
C9B C8B C14B C13B 55.3(4) . . . . ?
C12B C13B C14B C8B -56.6(5) . . . . ?
C17B C13B C14B C8B -177.4(4) . . . . ?
C18B C13B C14B C8B 64.8(4) . . . . ?
C12B C13B C14B C15B 169.1(4) . . . . ?
C17B C13B C14B C15B 48.2(4) . . . . ?
C18B C13B C14B C15B -69.5(4) . . . . ?
C8B C14B C15B C16B -168.4(4) . . . . ?
C13B C14B C15B C16B -37.6(4) . . . . ?
C14B C15B C16B O16B 126.8(4) . . . . ?
C14B C15B C16B C17B 12.4(5) . . . . ?
C15B C16B O16B C22B -154.9(3) . . . . ?
C17B C16B O16B C22B -39.6(4) . . . . ?
C12B C13B C17B C20B 89.3(5) . . . . ?
C18B C13B C17B C20B -37.9(5) . . . . ?
C14B C13B C17B C20B -154.8(4) . . . . ?
C12B C13B C17B C16B -155.3(4) . . . . ?
C18B C13B C17B C16B 77.5(4) . . . . ?
C14B C13B C17B C16B -39.4(4) . . . . ?
O16B C16B C17B C20B 24.6(5) . . . . ?
C15B C16B C17B C20B 144.0(4) . . . . ?
O16B C16B C17B C13B -101.9(4) . . . . ?
C15B C16B C17B C13B 17.5(5) . . . . ?
C13B C17B C20B C21B -121.8(4) . . . . ?
C16B C17B C20B C21B 122.6(4) . . . . ?
C13B C17B C20B C22B 113.6(4) . . . . ?
C16B C17B C20B C22B -2.0(5) . . . . ?
C16B O16B C22B O26B -77.6(4) . . . . ?
C16B O16B C22B C23B 160.5(3) . . . . ?
C16B O16B C22B C20B 38.3(4) . . . . ?
C21B C20B C22B O16B -146.0(4) . . . . ?
C17B C20B C22B O16B -21.3(5) . . . . ?
C21B C20B C22B O26B -28.4(5) . . . . ?
C17B C20B C22B O26B 96.3(4) . . . . ?
C21B C20B C22B C23B 94.7(5) . . . . ?
C17B C20B C22B C23B -140.5(4) . . . . ?
O16B C22B C23B C24B 70.5(5) . . . . ?
O26B C22B C23B C24B -51.0(6) . . . . ?
C20B C22B C23B C24B -172.4(4) . . . . ?
C22B C23B C24B C25B 51.1(6) . . . . ?
C23B C24B C25B C26B -52.6(5) . . . . ?
C23B C24B C25B C27B -177.2(4) . . . . ?
C24B C25B C26B O26B 57.1(5) . . . . ?
C27B C25B C26B O26B -178.3(4) . . . . ?
O16B C22B O26B C26B -65.5(4) . . . . ?
C23B C22B O26B C26B 55.3(5) . . . . ?
C20B C22B O26B C26B -180.0(3) . . . . ?
C25B C26B O26B C22B -60.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3A H3A O6A 0.94(4) 1.86(4) 2.754(4) 158(4) 2_756 yes
O6A H6A O1 0.91(4) 1.98(4) 2.884(5) 175(4) 1_655 yes
O3B H3B O3A 0.75(5) 2.02(5) 2.760(4) 171(6) 2_746 yes
O6B H6B O3B 0.86(4) 1.89(4) 2.744(4) 173(4) 2_646 yes
O1 H11 O3A 0.79(6) 2.26(6) 3.046(5) 177(7) 1_445 yes
O1 H12 O6B 0.80(6) 2.16(7) 2.842(5) 143(7) . yes

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1921286'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Benemerita Universidad Autonoma de Puebla
Mexico
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

# Clave Lab.  :  JC_E005
# Clave IF-UAP:  JC_E005
# Solicitud: 325
# Firma en la Solicitud: Dr. Jesus Sandoval (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\JC_E005\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-05-20

_chemical_name_systematic        5α-Cholestane-3β,6β-diol
_chemical_name_common            ?
_chemical_melting_point          465
_chemical_formula_moiety         'C27 H48 O2'
_chemical_formula_sum            'C27 H48 O2'
_chemical_formula_weight         404.65
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~=+623.5 (c=2 x 10^-4^, CHCl~3~)'

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       ?

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'

_cell_length_a                   8.3599(3)
_cell_length_b                   10.7489(4)
_cell_length_c                   28.4769(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2558.93(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    18957
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.69

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.092
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 4 0 0.0560
-6 -8 -1 0.0360
-1 1 3 0.3150
1 -1 -3 0.2780
0 -1 5 0.0790
0 1 -5 0.0720

_exptl_absorpt_coefficient_mu    0.042
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4766
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.550
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1280 frames, 50-60 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            55190
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         21.499
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5952
_reflns_number_gt                2864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ? # -0.9(10)
_refine_ls_number_reflns         5952
_refine_ls_number_parameters     312
_refine_ls_number_restraints     158
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   0.767
_refine_ls_restrained_S_all      0.789
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1494(3) 0.6600(3) 0.14659(10) 0.0550(8) Uani 1 1 d . . . . .
H1A H 0.147954 0.583602 0.164705 0.066 Uiso 1 1 calc R U . . .
H1B H 0.112982 0.726543 0.166974 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0312(3) 0.6471(3) 0.10562(10) 0.0608(8) Uani 1 1 d . . . . .
H2A H 0.057842 0.573746 0.087384 0.073 Uiso 1 1 calc R U . . .
H2B H -0.076192 0.636400 0.117896 0.073 Uiso 1 1 calc R U . . .
C3 C 0.0358(3) 0.7597(3) 0.07444(9) 0.0564(8) Uani 1 1 d . . . . .
H3A H 0.002244 0.832393 0.092723 0.068 Uiso 1 1 calc R U . . .
O3 O -0.0688(2) 0.7469(3) 0.03456(7) 0.0768(7) Uani 1 1 d . . . . .
H3 H -0.166(4) 0.742(4) 0.0412(12) 0.115 Uiso 1 1 d . U . . .
C4 C 0.2037(3) 0.7816(3) 0.05652(9) 0.0539(7) Uani 1 1 d . . . . .
H4A H 0.205500 0.855109 0.036758 0.065 Uiso 1 1 calc R U . . .
H4B H 0.237835 0.711126 0.037771 0.065 Uiso 1 1 calc R U . . .
C5 C 0.3181(3) 0.7992(3) 0.09793(9) 0.0453(7) Uani 1 1 d . . . . .
H5A H 0.269871 0.866325 0.116432 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4820(3) 0.8498(3) 0.08377(9) 0.0506(7) Uani 1 1 d . . . . .
H6A H 0.465200 0.926817 0.066017 0.061 Uiso 1 1 calc R U . . .
O6 O 0.5750(2) 0.7672(2) 0.05519(7) 0.0626(6) Uani 1 1 d . . . . .
H6 H 0.523(4) 0.749(3) 0.0299(11) 0.094 Uiso 1 1 d . U . . .
C7 C 0.5794(3) 0.8813(3) 0.12714(9) 0.0488(7) Uani 1 1 d . . . . .
H7A H 0.533152 0.954109 0.142033 0.059 Uiso 1 1 calc R U . . .
H7B H 0.687291 0.902581 0.117554 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5874(3) 0.7760(2) 0.16310(8) 0.0407(6) Uani 1 1 d . . . . .
H8A H 0.648233 0.707009 0.149399 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4192(3) 0.7283(2) 0.17587(8) 0.0413(6) Uani 1 1 d . . . . .
H9A H 0.362022 0.800351 0.188669 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3224(3) 0.6873(2) 0.13174(9) 0.0435(7) Uani 1 1 d . . . . .
C11 C 0.4242(3) 0.6327(3) 0.21549(10) 0.0558(8) Uani 1 1 d . . . . .
H11A H 0.469516 0.555988 0.203408 0.067 Uiso 1 1 calc R U . . .
H11B H 0.315576 0.615032 0.225413 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5222(3) 0.6741(3) 0.25871(9) 0.0521(7) Uani 1 1 d . . . . .
H12A H 0.468314 0.743039 0.273956 0.063 Uiso 1 1 calc R U . . .
H12B H 0.528227 0.605937 0.280972 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6919(3) 0.7140(2) 0.24482(9) 0.0424(6) Uani 1 1 d . . . . .
C14 C 0.6708(3) 0.8171(2) 0.20810(9) 0.0406(6) Uani 1 1 d . . . . .
H14A H 0.600934 0.879540 0.222520 0.049 Uiso 1 1 calc R U . . .
C15 C 0.8350(3) 0.8777(3) 0.20370(10) 0.0526(7) Uani 1 1 d . . . . .
H15A H 0.825296 0.964836 0.195248 0.063 Uiso 1 1 calc R U . . .
H15B H 0.899483 0.835721 0.180243 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9089(3) 0.8632(3) 0.25307(10) 0.0567(8) Uani 1 1 d . . . . .
H16A H 0.923804 0.944096 0.267496 0.068 Uiso 1 1 calc R U . . .
H16B H 1.012165 0.822355 0.250972 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7917(3) 0.7835(2) 0.28267(9) 0.0479(7) Uani 1 1 d . . . . .
H17A H 0.719237 0.840965 0.298844 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7854(3) 0.6026(2) 0.22587(11) 0.0581(8) Uani 1 1 d . . . . .
H18A H 0.790194 0.538889 0.249435 0.087 Uiso 1 1 calc R U . . .
H18B H 0.891948 0.628336 0.217838 0.087 Uiso 1 1 calc R U . . .
H18C H 0.732872 0.570745 0.198417 0.087 Uiso 1 1 calc R U . . .
C19 C 0.3947(3) 0.5697(3) 0.10954(10) 0.0568(7) Uani 1 1 d . . . . .
H19A H 0.342774 0.553148 0.080143 0.085 Uiso 1 1 calc R U . . .
H19B H 0.379618 0.500371 0.130310 0.085 Uiso 1 1 calc R U . . .
H19C H 0.507043 0.582262 0.104314 0.085 Uiso 1 1 calc R U . . .
C20 C 0.8803(3) 0.7087(3) 0.32058(11) 0.0641(8) Uani 1 1 d . . . . .
H20A H 0.954844 0.652823 0.304426 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7693(5) 0.6280(4) 0.35013(15) 0.1210(17) Uani 1 1 d . . . . .
H21A H 0.830543 0.585028 0.373599 0.182 Uiso 1 1 calc R U . . .
H21B H 0.716727 0.568445 0.330298 0.182 Uiso 1 1 calc R U . . .
H21C H 0.690708 0.679572 0.365123 0.182 Uiso 1 1 calc R U . . .
C22 C 0.9793(4) 0.7918(3) 0.35297(11) 0.0737(9) Uani 1 1 d . . . . .
H22A H 1.031559 0.854337 0.333790 0.088 Uiso 1 1 calc R U . . .
H22B H 0.906333 0.835001 0.373840 0.088 Uiso 1 1 calc R U . . .
C23 C 1.1035(6) 0.7303(4) 0.38219(17) 0.139(2) Uani 1 1 d D . . . .
H23A H 1.049926 0.676900 0.404714 0.167 Uiso 0.705(8) 1 calc R U P A 1
H23B H 1.167004 0.677191 0.361935 0.167 Uiso 0.705(8) 1 calc R U P A 1
H23C H 1.195078 0.710156 0.362726 0.167 Uiso 0.295(8) 1 calc R U P A 2
H23D H 1.060991 0.653152 0.394724 0.167 Uiso 0.295(8) 1 calc R U P A 2
C24A C 1.2136(14) 0.8131(11) 0.4083(4) 0.171(5) Uani 0.705(8) 1 d D U P A 1
H24A H 1.310608 0.821385 0.389822 0.206 Uiso 0.705(8) 1 calc R U P A 1
H24B H 1.164624 0.894827 0.409747 0.206 Uiso 0.705(8) 1 calc R U P A 1
C25A C 1.2562(16) 0.7813(11) 0.4519(4) 0.154(4) Uani 0.705(8) 1 d D U P A 1
H25A H 1.151334 0.767477 0.466335 0.185 Uiso 0.705(8) 1 calc R U P A 1
C26A C 1.3312(18) 0.6629(11) 0.4598(6) 0.255(10) Uani 0.705(8) 1 d D U P A 1
H26A H 1.255494 0.597554 0.453855 0.382 Uiso 0.705(8) 1 calc R U P A 1
H26B H 1.367246 0.658019 0.491715 0.382 Uiso 0.705(8) 1 calc R U P A 1
H26C H 1.420864 0.653920 0.438986 0.382 Uiso 0.705(8) 1 calc R U P A 1
C27A C 1.3288(9) 0.8796(6) 0.4859(2) 0.142(3) Uani 0.705(8) 1 d D U P A 1
H27A H 1.294222 0.961175 0.476643 0.213 Uiso 0.705(8) 1 calc R U P A 1
H27B H 1.443390 0.875331 0.484581 0.213 Uiso 0.705(8) 1 calc R U P A 1
H27C H 1.293456 0.862869 0.517308 0.213 Uiso 0.705(8) 1 calc R U P A 1
C24B C 1.1593(16) 0.8171(16) 0.4244(5) 0.053(3) Uani 0.295(8) 1 d D U P A 2
H24C H 1.188610 0.897235 0.411307 0.064 Uiso 0.295(8) 1 calc R U P A 2
H24D H 1.067582 0.830665 0.444620 0.064 Uiso 0.295(8) 1 calc R U P A 2
C25B C 1.301(3) 0.772(3) 0.4559(9) 0.133(7) Uani 0.295(8) 1 d D U P A 2
H25B H 1.326155 0.832972 0.480343 0.160 Uiso 0.295(8) 1 calc R U P A 2
C26B C 1.246(3) 0.648(3) 0.4773(10) 0.160(11) Uani 0.295(8) 1 d D U P A 2
H26D H 1.332535 0.611061 0.494225 0.240 Uiso 0.295(8) 1 calc R U P A 2
H26E H 1.211509 0.593357 0.452709 0.240 Uiso 0.295(8) 1 calc R U P A 2
H26F H 1.158084 0.663420 0.498373 0.240 Uiso 0.295(8) 1 calc R U P A 2
C27B C 1.4429(16) 0.7424(17) 0.4274(7) 0.144(8) Uani 0.295(8) 1 d D U P A 2
H27D H 1.528062 0.715396 0.447614 0.216 Uiso 0.295(8) 1 calc R U P A 2
H27E H 1.476049 0.815284 0.410521 0.216 Uiso 0.295(8) 1 calc R U P A 2
H27F H 1.417251 0.677413 0.405581 0.216 Uiso 0.295(8) 1 calc R U P A 2


_geom_special_details            ?

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
C1 C2 1.535(3) . ?
C1 C10 1.535(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.440(3) . ?
C3 C4 1.512(3) . ?
C3 H3A 0.9800 . ?
O3 H3 0.84(4) . ?
C4 C5 1.530(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.529(3) . ?
C5 C10 1.541(4) . ?
C5 H5A 0.9800 . ?
C6 O6 1.433(3) . ?
C6 C7 1.518(3) . ?
C6 H6A 0.9800 . ?
O6 H6 0.86(3) . ?
C7 C8 1.528(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.524(3) . ?
C8 C9 1.540(3) . ?
C8 H8A 0.9800 . ?
C9 C11 1.527(3) . ?
C9 C10 1.558(3) . ?
C9 H9A 0.9800 . ?
C10 C19 1.537(4) . ?
C11 C12 1.544(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.534(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.528(3) . ?
C13 C14 1.534(3) . ?
C13 C17 1.554(3) . ?
C14 C15 1.525(3) . ?
C14 H14A 0.9800 . ?
C15 C16 1.543(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.551(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.537(4) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.524(5) . ?
C20 C22 1.528(4) . ?
C20 H20A 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.486(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24A 1.480(10) . ?
C23 C24B 1.591(16) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C24A C25A 1.337(12) . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C25A C26A 1.436(14) . ?
C25A C27A 1.556(12) . ?
C25A H25A 0.9800 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C24B C25B 1.563(18) . ?
C24B H24C 0.9700 . ?
C24B H24D 0.9700 . ?
C25B C27B 1.47(2) . ?
C25B C26B 1.53(2) . ?
C25B H25B 0.9800 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?

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
C2 C1 C10 114.5(2) . . ?
C2 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C10 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 111.1(2) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O3 C3 C2 112.0(2) . . ?
O3 C3 C4 108.2(2) . . ?
C2 C3 C4 110.4(2) . . ?
O3 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C3 O3 H3 115(2) . . ?
C3 C4 C5 109.8(2) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C4 113.6(2) . . ?
C6 C5 C10 114.92(19) . . ?
C4 C5 C10 113.6(2) . . ?
C6 C5 H5A 104.4 . . ?
C4 C5 H5A 104.4 . . ?
C10 C5 H5A 104.4 . . ?
O6 C6 C7 108.0(2) . . ?
O6 C6 C5 114.6(2) . . ?
C7 C6 C5 110.2(2) . . ?
O6 C6 H6A 107.9 . . ?
C7 C6 H6A 107.9 . . ?
C5 C6 H6A 107.9 . . ?
C6 O6 H6 110(2) . . ?
C6 C7 C8 113.8(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C14 C8 C7 111.6(2) . . ?
C14 C8 C9 108.40(18) . . ?
C7 C8 C9 111.37(18) . . ?
C14 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C11 C9 C8 111.90(19) . . ?
C11 C9 C10 114.8(2) . . ?
C8 C9 C10 112.20(19) . . ?
C11 C9 H9A 105.7 . . ?
C8 C9 H9A 105.7 . . ?
C10 C9 H9A 105.7 . . ?
C1 C10 C19 109.1(2) . . ?
C1 C10 C5 107.4(2) . . ?
C19 C10 C5 113.2(2) . . ?
C1 C10 C9 108.7(2) . . ?
C19 C10 C9 111.1(2) . . ?
C5 C10 C9 107.2(2) . . ?
C9 C11 C12 114.2(2) . . ?
C9 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 111.5(2) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 112.6(2) . . ?
C18 C13 C12 110.2(2) . . ?
C14 C13 C12 105.72(19) . . ?
C18 C13 C17 110.3(2) . . ?
C14 C13 C17 100.78(19) . . ?
C12 C13 C17 116.9(2) . . ?
C8 C14 C15 117.8(2) . . ?
C8 C14 C13 114.6(2) . . ?
C15 C14 C13 105.14(19) . . ?
C8 C14 H14A 106.1 . . ?
C15 C14 H14A 106.1 . . ?
C13 C14 H14A 106.1 . . ?
C14 C15 C16 104.0(2) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 107.3(2) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C20 C17 C16 111.5(2) . . ?
C20 C17 C13 119.6(2) . . ?
C16 C17 C13 103.2(2) . . ?
C20 C17 H17A 107.3 . . ?
C16 C17 H17A 107.3 . . ?
C13 C17 H17A 107.3 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 109.2(3) . . ?
C21 C20 C17 113.1(2) . . ?
C22 C20 C17 112.3(2) . . ?
C21 C20 H20A 107.3 . . ?
C22 C20 H20A 107.3 . . ?
C17 C20 H20A 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 117.2(3) . . ?
C23 C22 H22A 108.0 . . ?
C20 C22 H22A 108.0 . . ?
C23 C22 H22B 108.0 . . ?
C20 C22 H22B 108.0 . . ?
H22A C22 H22B 107.3 . . ?
C24A C23 C22 116.6(5) . . ?
C22 C23 C24B 111.5(6) . . ?
C24A C23 H23A 108.1 . . ?
C22 C23 H23A 108.1 . . ?
C24A C23 H23B 108.1 . . ?
C22 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C22 C23 H23C 109.3 . . ?
C24B C23 H23C 109.3 . . ?
C22 C23 H23D 109.3 . . ?
C24B C23 H23D 109.3 . . ?
H23C C23 H23D 108.0 . . ?
C25A C24A C23 118.5(10) . . ?
C25A C24A H24A 107.7 . . ?
C23 C24A H24A 107.7 . . ?
C25A C24A H24B 107.7 . . ?
C23 C24A H24B 107.7 . . ?
H24A C24A H24B 107.1 . . ?
C24A C25A C26A 119.2(12) . . ?
C24A C25A C27A 120.5(10) . . ?
C26A C25A C27A 109.6(10) . . ?
C24A C25A H25A 101.0 . . ?
C26A C25A H25A 101.0 . . ?
C27A C25A H25A 101.0 . . ?
C25A C26A H26A 109.5 . . ?
C25A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C25A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C25A C27A H27A 109.5 . . ?
C25A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C25A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C25B C24B C23 118.2(16) . . ?
C25B C24B H24C 107.7 . . ?
C23 C24B H24C 107.7 . . ?
C25B C24B H24D 107.7 . . ?
C23 C24B H24D 107.7 . . ?
H24C C24B H24D 107.1 . . ?
C27B C25B C26B 106(2) . . ?
C27B C25B C24B 111.2(17) . . ?
C26B C25B C24B 105.6(17) . . ?
C27B C25B H25B 111.2 . . ?
C26B C25B H25B 111.2 . . ?
C24B C25B H25B 111.2 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C25B C27B H27D 109.5 . . ?
C25B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C25B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 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 C1 C2 C3 -54.7(3) . . . . ?
C1 C2 C3 O3 177.3(2) . . . . ?
C1 C2 C3 C4 56.6(3) . . . . ?
O3 C3 C4 C5 178.5(2) . . . . ?
C2 C3 C4 C5 -58.7(3) . . . . ?
C3 C4 C5 C6 -167.3(3) . . . . ?
C3 C4 C5 C10 58.8(3) . . . . ?
C4 C5 C6 O6 -65.8(3) . . . . ?
C10 C5 C6 O6 67.4(3) . . . . ?
C4 C5 C6 C7 172.2(2) . . . . ?
C10 C5 C6 C7 -54.6(3) . . . . ?
O6 C6 C7 C8 -74.9(3) . . . . ?
C5 C6 C7 C8 51.0(3) . . . . ?
C6 C7 C8 C14 -173.8(2) . . . . ?
C6 C7 C8 C9 -52.5(3) . . . . ?
C14 C8 C9 C11 -50.8(3) . . . . ?
C7 C8 C9 C11 -174.0(2) . . . . ?
C14 C8 C9 C10 178.5(2) . . . . ?
C7 C8 C9 C10 55.3(3) . . . . ?
C2 C1 C10 C19 -71.8(3) . . . . ?
C2 C1 C10 C5 51.3(3) . . . . ?
C2 C1 C10 C9 166.9(2) . . . . ?
C6 C5 C10 C1 173.2(2) . . . . ?
C4 C5 C10 C1 -53.6(3) . . . . ?
C6 C5 C10 C19 -66.3(3) . . . . ?
C4 C5 C10 C19 66.9(3) . . . . ?
C6 C5 C10 C9 56.5(3) . . . . ?
C4 C5 C10 C9 -170.22(19) . . . . ?
C11 C9 C10 C1 59.2(3) . . . . ?
C8 C9 C10 C1 -171.6(2) . . . . ?
C11 C9 C10 C19 -60.9(3) . . . . ?
C8 C9 C10 C19 68.3(3) . . . . ?
C11 C9 C10 C5 174.9(2) . . . . ?
C8 C9 C10 C5 -55.8(3) . . . . ?
C8 C9 C11 C12 49.9(3) . . . . ?
C10 C9 C11 C12 179.3(2) . . . . ?
C9 C11 C12 C13 -53.7(3) . . . . ?
C11 C12 C13 C18 -65.5(3) . . . . ?
C11 C12 C13 C14 56.4(3) . . . . ?
C11 C12 C13 C17 167.6(2) . . . . ?
C7 C8 C14 C15 -52.2(3) . . . . ?
C9 C8 C14 C15 -175.2(2) . . . . ?
C7 C8 C14 C13 -176.7(2) . . . . ?
C9 C8 C14 C13 60.3(3) . . . . ?
C18 C13 C14 C8 57.6(3) . . . . ?
C12 C13 C14 C8 -62.8(3) . . . . ?
C17 C13 C14 C8 175.12(19) . . . . ?
C18 C13 C14 C15 -73.4(3) . . . . ?
C12 C13 C14 C15 166.2(2) . . . . ?
C17 C13 C14 C15 44.1(2) . . . . ?
C8 C14 C15 C16 -160.0(2) . . . . ?
C13 C14 C15 C16 -30.9(3) . . . . ?
C14 C15 C16 C17 5.4(3) . . . . ?
C15 C16 C17 C20 151.0(2) . . . . ?
C15 C16 C17 C13 21.4(3) . . . . ?
C18 C13 C17 C20 -44.6(3) . . . . ?
C14 C13 C17 C20 -163.8(2) . . . . ?
C12 C13 C17 C20 82.3(3) . . . . ?
C18 C13 C17 C16 79.8(2) . . . . ?
C14 C13 C17 C16 -39.4(2) . . . . ?
C12 C13 C17 C16 -153.3(2) . . . . ?
C16 C17 C20 C21 -179.4(3) . . . . ?
C13 C17 C20 C21 -59.0(4) . . . . ?
C16 C17 C20 C22 56.4(3) . . . . ?
C13 C17 C20 C22 176.8(2) . . . . ?
C21 C20 C22 C23 70.0(5) . . . . ?
C17 C20 C22 C23 -163.7(3) . . . . ?
C20 C22 C23 C24A 171.6(7) . . . . ?
C20 C22 C23 C24B -162.7(6) . . . . ?
C22 C23 C24A C25A 140.6(12) . . . . ?
C23 C24A C25A C26A 57(2) . . . . ?
C23 C24A C25A C27A -162.1(9) . . . . ?
C22 C23 C24B C25B -174.3(13) . . . . ?
C23 C24B C25B C27B 55(2) . . . . ?
C23 C24B C25B C26B -60(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O6 0.84(4) 2.22(4) 3.043(2) 169(4) 1_455 yes
O6 H6 O3 0.86(3) 1.99(3) 2.828(3) 164(3) 4_565 yes

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.030


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1921284'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Benemerita Universidad Autonoma de Puebla
Mexico
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

# Clave Lab.  :  JC-E002
# Clave IF-UAP:  JC_E002b
# Solicitud: 317b
# Firma en la Solicitud: Dr. Jesus Sandoval (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\JC_E002b\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-05-06

_chemical_name_systematic        5β-Cholestane-3β,6β-diol
_chemical_name_common            ?
_chemical_melting_point          467
_chemical_formula_moiety         'C27 H47 D O2'
_chemical_formula_sum            'C27 H47 D O2'
_chemical_formula_weight         405.66
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~=+607 (c= 2 x 10^-4^, CHCl~3~)'

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       ?

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'

_cell_length_a                   8.1858(3)
_cell_length_b                   10.4115(6)
_cell_length_c                   30.9258(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2635.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    24243
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      26.60

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.022
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.125
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 -7 0.0680
2 1 7 0.0570
1 -5 6 0.1800
0 3 -4 0.1530
3 0 -10 0.4630
-2 0 7 0.3940

_exptl_absorpt_coefficient_mu    0.041
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3630
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1398 frames, 45-55 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            45768
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         22.499
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6932
_reflns_number_gt                3034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         6932
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_restrained_S_all      0.811
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C -0.7681(4) -0.6036(4) -0.09433(11) 0.0803(10) Uani 1 1 d . . . . .
H1A H -0.793931 -0.573758 -0.065422 0.096 Uiso 1 1 calc R U . . .
H1B H -0.774363 -0.530251 -0.113595 0.096 Uiso 1 1 calc R U . . .
C2 C -0.8947(3) -0.7001(4) -0.10782(11) 0.0879(11) Uani 1 1 d . . . . .
H2A H -0.874089 -0.726400 -0.137413 0.105 Uiso 1 1 calc R U . . .
H2B H -1.001880 -0.660470 -0.106804 0.105 Uiso 1 1 calc R U . . .
C3 C -0.8935(3) -0.8171(4) -0.07891(9) 0.0684(9) Uani 1 1 d . . . . .
H3A H -0.963776 -0.882742 -0.091917 0.082 Uiso 1 1 calc R U . . .
O3 O -0.9537(2) -0.7892(3) -0.03667(7) 0.0843(8) Uani 1 1 d . . . . .
H3 H -1.046(5) -0.790(4) -0.0350(15) 0.126 Uiso 1 1 d . U . . .
C4 C -0.7228(3) -0.8712(3) -0.07502(10) 0.0615(7) Uani 1 1 d . . . . .
H4A H -0.695328 -0.913239 -0.102050 0.074 Uiso 1 1 calc R U . . .
H4B H -0.723305 -0.936490 -0.052653 0.074 Uiso 1 1 calc R U . . .
C5 C -0.5892(2) -0.7750(3) -0.06459(9) 0.0554(7) Uani 1 1 d . . . . .
D5A D -0.609006 -0.744542 -0.035067 0.066 Uiso 1 1 calc R U . . .
C6 C -0.4240(3) -0.8454(3) -0.06420(9) 0.0602(8) Uani 1 1 d . . . . .
H6A H -0.438855 -0.927505 -0.049195 0.072 Uiso 1 1 calc R U . . .
O6 O -0.3003(2) -0.7747(3) -0.04204(7) 0.0829(8) Uani 1 1 d . . . . .
H6 H -0.331(5) -0.757(4) -0.0164(13) 0.124 Uiso 1 1 d . U . . .
C7 C -0.3637(3) -0.8735(3) -0.10944(9) 0.0560(7) Uani 1 1 d . . . . .
H7A H -0.430643 -0.941237 -0.121672 0.067 Uiso 1 1 calc R U . . .
H7B H -0.252754 -0.905720 -0.107555 0.067 Uiso 1 1 calc R U . . .
C8 C -0.3656(3) -0.7601(3) -0.14008(8) 0.0484(6) Uani 1 1 d . . . . .
H8A H -0.284809 -0.697590 -0.129881 0.058 Uiso 1 1 calc R U . . .
C9 C -0.5340(3) -0.6937(3) -0.14061(9) 0.0548(7) Uani 1 1 d . . . . .
H9A H -0.611948 -0.758306 -0.150840 0.066 Uiso 1 1 calc R U . . .
C10 C -0.5914(3) -0.6548(3) -0.09454(9) 0.0590(8) Uani 1 1 d . . . . .
C11 C -0.5386(4) -0.5848(3) -0.17358(11) 0.0792(10) Uani 1 1 d . . . . .
H11A H -0.649799 -0.553133 -0.175675 0.095 Uiso 1 1 calc R U . . .
H11B H -0.470951 -0.514900 -0.163149 0.095 Uiso 1 1 calc R U . . .
C12 C -0.4805(4) -0.6230(3) -0.21851(11) 0.0789(10) Uani 1 1 d . . . . .
H12A H -0.477987 -0.547320 -0.236804 0.095 Uiso 1 1 calc R U . . .
H12B H -0.557806 -0.683126 -0.230966 0.095 Uiso 1 1 calc R U . . .
C13 C -0.3111(3) -0.6843(3) -0.21786(9) 0.0562(7) Uani 1 1 d . . . . .
C14 C -0.3217(3) -0.7967(3) -0.18632(8) 0.0478(6) Uani 1 1 d . . . . .
H14A H -0.411616 -0.850716 -0.196686 0.057 Uiso 1 1 calc R U . . .
C15 C -0.1654(3) -0.8739(3) -0.19435(10) 0.0653(8) Uani 1 1 d . . . . .
H15A H -0.180636 -0.963623 -0.186871 0.078 Uiso 1 1 calc R U . . .
H15B H -0.074874 -0.839658 -0.177729 0.078 Uiso 1 1 calc R U . . .
C16 C -0.1357(4) -0.8579(3) -0.24312(10) 0.0733(9) Uani 1 1 d . . . . .
H16A H -0.153612 -0.938778 -0.257948 0.088 Uiso 1 1 calc R U . . .
H16B H -0.024103 -0.830647 -0.248382 0.088 Uiso 1 1 calc R U . . .
C17 C -0.2563(3) -0.7556(3) -0.25972(9) 0.0623(7) Uani 1 1 d . . . . .
H17A H -0.352124 -0.801413 -0.270834 0.075 Uiso 1 1 calc R U . . .
C18 C -0.1800(4) -0.5870(3) -0.20445(12) 0.0808(10) Uani 1 1 d . . . . .
H18A H -0.204294 -0.554674 -0.176102 0.121 Uiso 1 1 calc R U . . .
H18B H -0.178391 -0.517156 -0.224714 0.121 Uiso 1 1 calc R U . . .
H18C H -0.075063 -0.628233 -0.204143 0.121 Uiso 1 1 calc R U . . .
C19 C -0.4857(4) -0.5472(3) -0.07607(13) 0.0883(11) Uani 1 1 d . . . . .
H19A H -0.372424 -0.568424 -0.079780 0.132 Uiso 1 1 calc R U . . .
H19B H -0.508928 -0.536960 -0.045840 0.132 Uiso 1 1 calc R U . . .
H19C H -0.509219 -0.468433 -0.090977 0.132 Uiso 1 1 calc R U . . .
C20 C -0.1846(5) -0.6780(3) -0.29766(11) 0.0828(10) Uani 1 1 d . . . . .
H20A H -0.083263 -0.639093 -0.286995 0.099 Uiso 1 1 calc R U . . .
C21 C -0.2928(7) -0.5679(5) -0.31252(15) 0.153(2) Uani 1 1 d . . . . .
H21A H -0.311271 -0.510110 -0.288827 0.230 Uiso 1 1 calc R U . . .
H21B H -0.395483 -0.601323 -0.322440 0.230 Uiso 1 1 calc R U . . .
H21C H -0.240050 -0.522660 -0.335693 0.230 Uiso 1 1 calc R U . . .
C22 C -0.1363(5) -0.7649(4) -0.33550(11) 0.0887(11) Uani 1 1 d . . . . .
H22A H -0.077986 -0.838260 -0.323834 0.106 Uiso 1 1 calc R U . . .
H22B H -0.235819 -0.797246 -0.348610 0.106 Uiso 1 1 calc R U . . .
C23 C -0.0345(6) -0.7078(4) -0.37022(14) 0.1190(15) Uani 1 1 d . . . . .
H23A H 0.066499 -0.677759 -0.357328 0.143 Uiso 1 1 calc R U . . .
H23B H -0.091364 -0.633211 -0.381451 0.143 Uiso 1 1 calc R U . . .
C24 C 0.0077(6) -0.7929(4) -0.40737(13) 0.1172(15) Uani 1 1 d . . . . .
H24A H 0.069783 -0.863965 -0.395472 0.141 Uiso 1 1 calc R U . . .
H24B H -0.094543 -0.828798 -0.417675 0.141 Uiso 1 1 calc R U . . .
C25 C 0.0935(9) -0.7510(6) -0.44434(19) 0.160(3) Uani 1 1 d . . . . .
H25A H 0.036040 -0.677959 -0.457323 0.192 Uiso 0.458(17) 1 calc R U P A 1
H25B H 0.202925 -0.757180 -0.431668 0.192 Uiso 0.542(17) 1 calc R U P A 2
C26 C 0.1176(8) -0.8562(7) -0.47854(19) 0.171(2) Uani 1 1 d . . . . .
H26A H 0.223949 -0.847549 -0.491324 0.256 Uiso 1 1 calc R U . . .
H26B H 0.035637 -0.847828 -0.500551 0.256 Uiso 1 1 calc R U . . .
H26C H 0.108467 -0.939061 -0.465130 0.256 Uiso 1 1 calc R U . . .
C27A C 0.271(2) -0.7047(19) -0.4274(8) 0.211(15) Uani 0.458(17) 1 d . . P A 1
H27A H 0.262146 -0.673648 -0.398227 0.317 Uiso 0.458(17) 1 calc R U P A 1
H27B H 0.311466 -0.637236 -0.445650 0.317 Uiso 0.458(17) 1 calc R U P A 1
H27C H 0.345897 -0.775894 -0.428116 0.317 Uiso 0.458(17) 1 calc R U P A 1
C27B C 0.110(2) -0.6407(10) -0.4592(4) 0.151(7) Uani 0.542(17) 1 d . . P A 2
H27D H 0.004451 -0.606852 -0.466787 0.226 Uiso 0.542(17) 1 calc R U P A 2
H27E H 0.177785 -0.643580 -0.484444 0.226 Uiso 0.542(17) 1 calc R U P A 2
H27F H 0.159386 -0.586501 -0.437789 0.226 Uiso 0.542(17) 1 calc R U P A 2


_geom_special_details            ?

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
C1 C2 1.503(5) . ?
C1 C10 1.541(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.511(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.426(3) . ?
C3 C4 1.511(4) . ?
C3 H3A 0.9800 . ?
O3 H3 0.76(4) . ?
C4 C5 1.518(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.538(3) . ?
C5 C10 1.557(4) . ?
C5 D5A 0.9800 . ?
C6 O6 1.427(3) . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9800 . ?
O6 H6 0.85(4) . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.523(3) . ?
C8 C9 1.542(3) . ?
C8 H8A 0.9800 . ?
C9 C11 1.525(4) . ?
C9 C10 1.554(4) . ?
C9 H9A 0.9800 . ?
C10 C19 1.527(4) . ?
C11 C12 1.521(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.527(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.526(4) . ?
C13 C18 1.533(4) . ?
C13 C17 1.558(4) . ?
C14 C15 1.531(4) . ?
C14 H14A 0.9800 . ?
C15 C16 1.537(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.541(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.541(4) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.520(5) . ?
C20 C22 1.531(5) . ?
C20 H20A 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.483(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.491(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.411(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27B 1.244(10) . ?
C25 C26 1.536(7) . ?
C25 C27A 1.62(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?

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
C2 C1 C10 114.5(3) . . ?
C2 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C10 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 111.7(3) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O3 C3 C2 112.1(3) . . ?
O3 C3 C4 108.8(2) . . ?
C2 C3 C4 110.7(2) . . ?
O3 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C3 O3 H3 114(4) . . ?
C3 C4 C5 115.9(3) . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 C6 108.7(2) . . ?
C4 C5 C10 113.3(2) . . ?
C6 C5 C10 113.4(2) . . ?
C4 C5 D5A 107.0 . . ?
C6 C5 D5A 107.0 . . ?
C10 C5 D5A 107.0 . . ?
O6 C6 C7 108.2(2) . . ?
O6 C6 C5 112.4(2) . . ?
C7 C6 C5 111.8(2) . . ?
O6 C6 H6A 108.1 . . ?
C7 C6 H6A 108.1 . . ?
C5 C6 H6A 108.1 . . ?
C6 O6 H6 110(3) . . ?
C6 C7 C8 115.2(2) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C14 112.9(2) . . ?
C7 C8 C9 111.44(19) . . ?
C14 C8 C9 108.28(19) . . ?
C7 C8 H8A 108.0 . . ?
C14 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C11 C9 C8 111.3(2) . . ?
C11 C9 C10 114.3(2) . . ?
C8 C9 C10 112.2(2) . . ?
C11 C9 H9A 106.1 . . ?
C8 C9 H9A 106.1 . . ?
C10 C9 H9A 106.1 . . ?
C19 C10 C1 106.0(3) . . ?
C19 C10 C9 111.3(2) . . ?
C1 C10 C9 112.2(2) . . ?
C19 C10 C5 111.2(2) . . ?
C1 C10 C5 106.6(2) . . ?
C9 C10 C5 109.4(2) . . ?
C12 C11 C9 114.1(3) . . ?
C12 C11 H11A 108.7 . . ?
C9 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C9 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 112.4(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 106.1(2) . . ?
C14 C13 C18 112.0(2) . . ?
C12 C13 C18 111.3(2) . . ?
C14 C13 C17 100.5(2) . . ?
C12 C13 C17 116.7(2) . . ?
C18 C13 C17 109.8(2) . . ?
C8 C14 C13 114.9(2) . . ?
C8 C14 C15 118.8(2) . . ?
C13 C14 C15 104.6(2) . . ?
C8 C14 H14A 105.9 . . ?
C13 C14 H14A 105.9 . . ?
C15 C14 H14A 105.9 . . ?
C14 C15 C16 103.6(2) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 107.5(2) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 C20 111.8(2) . . ?
C16 C17 C13 103.7(2) . . ?
C20 C17 C13 119.5(2) . . ?
C16 C17 H17A 107.1 . . ?
C20 C17 H17A 107.1 . . ?
C13 C17 H17A 107.1 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 111.4(3) . . ?
C21 C20 C17 113.8(3) . . ?
C22 C20 C17 111.7(3) . . ?
C21 C20 H20A 106.5 . . ?
C22 C20 H20A 106.5 . . ?
C17 C20 H20A 106.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 117.5(3) . . ?
C23 C22 H22A 107.9 . . ?
C20 C22 H22A 107.9 . . ?
C23 C22 H22B 107.9 . . ?
C20 C22 H22B 107.9 . . ?
H22A C22 H22B 107.2 . . ?
C22 C23 C24 116.7(3) . . ?
C22 C23 H23A 108.1 . . ?
C24 C23 H23A 108.1 . . ?
C22 C23 H23B 108.1 . . ?
C24 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C25 C24 C23 123.8(4) . . ?
C25 C24 H24A 106.4 . . ?
C23 C24 H24A 106.4 . . ?
C25 C24 H24B 106.4 . . ?
C23 C24 H24B 106.4 . . ?
H24A C24 H24B 106.5 . . ?
C27B C25 C24 129.6(7) . . ?
C27B C25 C26 113.0(7) . . ?
C24 C25 C26 113.7(5) . . ?
C24 C25 C27A 106.1(10) . . ?
C26 C25 C27A 108.6(7) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C27A C25 H25A 109.5 . . ?
C27B C25 H25B 96.4 . . ?
C24 C25 H25B 96.4 . . ?
C26 C25 H25B 96.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27A H27A 109.5 . . ?
C25 C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C25 C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C25 C27B H27D 109.5 . . ?
C25 C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C25 C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 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 C1 C2 C3 58.9(4) . . . . ?
C1 C2 C3 O3 70.2(3) . . . . ?
C1 C2 C3 C4 -51.5(3) . . . . ?
O3 C3 C4 C5 -74.9(3) . . . . ?
C2 C3 C4 C5 48.6(3) . . . . ?
C3 C4 C5 C6 -177.1(2) . . . . ?
C3 C4 C5 C10 -50.1(3) . . . . ?
C4 C5 C6 O6 -161.7(2) . . . . ?
C10 C5 C6 O6 71.3(3) . . . . ?
C4 C5 C6 C7 76.3(3) . . . . ?
C10 C5 C6 C7 -50.7(3) . . . . ?
O6 C6 C7 C8 -74.7(3) . . . . ?
C5 C6 C7 C8 49.7(3) . . . . ?
C6 C7 C8 C14 -173.7(2) . . . . ?
C6 C7 C8 C9 -51.5(3) . . . . ?
C7 C8 C9 C11 -176.4(3) . . . . ?
C14 C8 C9 C11 -51.6(3) . . . . ?
C7 C8 C9 C10 54.1(3) . . . . ?
C14 C8 C9 C10 178.9(2) . . . . ?
C2 C1 C10 C19 -174.9(3) . . . . ?
C2 C1 C10 C9 63.4(4) . . . . ?
C2 C1 C10 C5 -56.3(3) . . . . ?
C11 C9 C10 C19 -59.5(3) . . . . ?
C8 C9 C10 C19 68.3(3) . . . . ?
C11 C9 C10 C1 59.1(3) . . . . ?
C8 C9 C10 C1 -173.0(2) . . . . ?
C11 C9 C10 C5 177.2(2) . . . . ?
C8 C9 C10 C5 -54.9(3) . . . . ?
C4 C5 C10 C19 165.6(2) . . . . ?
C6 C5 C10 C19 -69.9(3) . . . . ?
C4 C5 C10 C1 50.5(3) . . . . ?
C6 C5 C10 C1 175.0(2) . . . . ?
C4 C5 C10 C9 -71.1(3) . . . . ?
C6 C5 C10 C9 53.5(3) . . . . ?
C8 C9 C11 C12 51.0(4) . . . . ?
C10 C9 C11 C12 179.4(3) . . . . ?
C9 C11 C12 C13 -53.8(4) . . . . ?
C11 C12 C13 C14 55.2(3) . . . . ?
C11 C12 C13 C18 -66.8(3) . . . . ?
C11 C12 C13 C17 166.1(3) . . . . ?
C7 C8 C14 C13 -176.2(2) . . . . ?
C9 C8 C14 C13 59.9(3) . . . . ?
C7 C8 C14 C15 -51.4(3) . . . . ?
C9 C8 C14 C15 -175.3(2) . . . . ?
C12 C13 C14 C8 -60.9(3) . . . . ?
C18 C13 C14 C8 60.7(3) . . . . ?
C17 C13 C14 C8 177.16(19) . . . . ?
C12 C13 C14 C15 167.1(2) . . . . ?
C18 C13 C14 C15 -71.3(3) . . . . ?
C17 C13 C14 C15 45.2(3) . . . . ?
C8 C14 C15 C16 -163.9(2) . . . . ?
C13 C14 C15 C16 -34.2(3) . . . . ?
C14 C15 C16 C17 9.3(3) . . . . ?
C15 C16 C17 C20 148.2(3) . . . . ?
C15 C16 C17 C13 18.2(3) . . . . ?
C14 C13 C17 C16 -38.3(3) . . . . ?
C12 C13 C17 C16 -152.4(3) . . . . ?
C18 C13 C17 C16 79.8(3) . . . . ?
C14 C13 C17 C20 -163.6(3) . . . . ?
C12 C13 C17 C20 82.3(3) . . . . ?
C18 C13 C17 C20 -45.5(3) . . . . ?
C16 C17 C20 C21 -174.8(4) . . . . ?
C13 C17 C20 C21 -53.5(4) . . . . ?
C16 C17 C20 C22 58.0(4) . . . . ?
C13 C17 C20 C22 179.3(3) . . . . ?
C21 C20 C22 C23 64.0(5) . . . . ?
C17 C20 C22 C23 -167.5(4) . . . . ?
C20 C22 C23 C24 -178.5(4) . . . . ?
C22 C23 C24 C25 175.4(6) . . . . ?
C23 C24 C25 C27B -22.0(17) . . . . ?
C23 C24 C25 C26 -178.5(6) . . . . ?
C23 C24 C25 C27A 62.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O6 0.76(4) 2.10(4) 2.846(2) 169(5) 1_455 yes
O6 H6 O3 0.85(4) 1.98(4) 2.819(3) 167(4) 4_535 yes

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1921285'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Benemerita Universidad Autonoma de Puebla
Mexico
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

# Clave Lab.  :  JC-E004
# Clave IF-UAP:  JC_E004
# Solicitud: 319
# Firma en la Solicitud: Dr. Jesus Sandoval (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\JC_E004\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-05-06

_chemical_name_systematic        (25R)-5β-Spirostan-3β,6β-diol
_chemical_name_common            ?
_chemical_melting_point          555
_chemical_formula_moiety         'C27 H44 O4'
_chemical_formula_sum            'C27 H44 O4'
_chemical_formula_weight         432.62
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~=+60 (c= 2 x 10^-4^, CHCl~3~)'

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       ?

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'

_cell_length_a                   8.2099(2)
_cell_length_b                   9.1989(3)
_cell_length_c                   32.4182(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2448.29(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    29404
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      23.75

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -4 0.0890
0 -1 5 0.1130
1 1 -2 0.1580
-3 -1 -7 0.1600
-1 -1 0 0.1630
3 2 6 0.1580
1 -1 -3 0.0820
-1 1 3 0.0730
-1 -6 -5 0.1410

_exptl_absorpt_coefficient_mu    0.049
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5416
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1440 frames, 40-60 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            37982
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         21.498
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5592
_reflns_number_gt                3643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         5592
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 1.0654(2) 0.5667(3) 0.53044(9) 0.0502(7) Uani 1 1 d . . . . .
H1A H 1.090716 0.514513 0.505244 0.060 Uiso 1 1 calc R U . . .
H1B H 1.076444 0.669715 0.524751 0.060 Uiso 1 1 calc R U . . .
C2 C 1.1871(2) 0.5249(3) 0.56293(9) 0.0569(8) Uani 1 1 d . . . . .
H2A H 1.166957 0.581387 0.587670 0.068 Uiso 1 1 calc R U . . .
H2B H 1.295833 0.547942 0.553231 0.068 Uiso 1 1 calc R U . . .
C3 C 1.1783(2) 0.3648(3) 0.57332(9) 0.0526(7) Uani 1 1 d . . . . .
H3A H 1.247390 0.346184 0.597395 0.063 Uiso 1 1 calc R U . . .
O3 O 1.23596(19) 0.2783(2) 0.53950(6) 0.0593(5) Uani 1 1 d . . . . .
H3 H 1.342(4) 0.291(3) 0.5403(10) 0.089 Uiso 1 1 d . U . . .
C4 C 1.0052(2) 0.3192(3) 0.58353(9) 0.0469(6) Uani 1 1 d . . . . .
H4A H 0.977376 0.356634 0.610598 0.056 Uiso 1 1 calc R U . . .
H4B H 1.001134 0.213906 0.585016 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8755(2) 0.3712(2) 0.55243(7) 0.0377(6) Uani 1 1 d . . . . .
H5A H 0.894905 0.318517 0.526620 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7070(2) 0.3237(3) 0.56843(8) 0.0407(6) Uani 1 1 d . . . . .
H6A H 0.717014 0.224442 0.579114 0.049 Uiso 1 1 calc R U . . .
O6 O 0.58477(17) 0.3230(2) 0.53662(7) 0.0565(5) Uani 1 1 d . . . . .
H6 H 0.628(4) 0.292(3) 0.5132(11) 0.085 Uiso 1 1 d . U . . .
C7 C 0.6479(2) 0.4203(2) 0.60341(8) 0.0406(6) Uani 1 1 d . . . . .
H7A H 0.711694 0.399052 0.627850 0.049 Uiso 1 1 calc R U . . .
H7B H 0.535473 0.395821 0.609459 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6583(2) 0.5830(2) 0.59472(7) 0.0349(5) Uani 1 1 d . . . . .
H8A H 0.581717 0.606807 0.572533 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8322(2) 0.6253(2) 0.58066(7) 0.0367(5) Uani 1 1 d . . . . .
H9A H 0.905271 0.597167 0.603204 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8863(2) 0.5349(2) 0.54238(8) 0.0385(5) Uani 1 1 d . . . . .
C11 C 0.8524(3) 0.7906(3) 0.57530(9) 0.0515(7) Uani 1 1 d . . . . .
H11A H 0.965842 0.812184 0.569575 0.062 Uiso 1 1 calc R U . . .
H11B H 0.788671 0.822235 0.551753 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7986(3) 0.8759(3) 0.61351(9) 0.0493(7) Uani 1 1 d . . . . .
H12A H 0.806651 0.979235 0.607843 0.059 Uiso 1 1 calc R U . . .
H12B H 0.871288 0.853801 0.636237 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6234(2) 0.8396(2) 0.62613(7) 0.0374(5) Uani 1 1 d . . . . .
C14 C 0.6150(2) 0.6738(2) 0.63263(7) 0.0350(5) Uani 1 1 d . . . . .
H14A H 0.698978 0.651517 0.653161 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4520(2) 0.6523(2) 0.65486(8) 0.0431(6) Uani 1 1 d . . . . .
H15A H 0.361559 0.656347 0.635644 0.052 Uiso 1 1 calc R U . . .
H15B H 0.449260 0.560215 0.669408 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4476(2) 0.7804(2) 0.68495(8) 0.0396(5) Uani 1 1 d . . . . .
H16A H 0.475771 0.748493 0.712899 0.047 Uiso 1 1 calc R U . . .
O16 O 0.29281(16) 0.85398(17) 0.68474(6) 0.0464(4) Uani 1 1 d . . . . .
C17 C 0.5716(2) 0.8948(2) 0.66914(7) 0.0380(5) Uani 1 1 d . . . . .
H17A H 0.666792 0.895302 0.687385 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5044(3) 0.8892(3) 0.59219(8) 0.0501(6) Uani 1 1 d . . . . .
H18A H 0.394462 0.878398 0.601820 0.075 Uiso 1 1 calc R U . . .
H18B H 0.519946 0.830662 0.567980 0.075 Uiso 1 1 calc R U . . .
H18C H 0.524550 0.989301 0.585609 0.075 Uiso 1 1 calc R U . . .
C19 C 0.7835(3) 0.5742(3) 0.50446(8) 0.0530(7) Uani 1 1 d . . . . .
H19A H 0.811190 0.670291 0.495323 0.080 Uiso 1 1 calc R U . . .
H19B H 0.670039 0.570878 0.511599 0.080 Uiso 1 1 calc R U . . .
H19C H 0.804803 0.505846 0.482734 0.080 Uiso 1 1 calc R U . . .
C20 C 0.4811(3) 1.0410(2) 0.67325(8) 0.0439(6) Uani 1 1 d . . . . .
H20A H 0.451084 1.073341 0.645471 0.053 Uiso 1 1 calc R U . . .
C21 C 0.5798(3) 1.1620(3) 0.69346(10) 0.0633(8) Uani 1 1 d . . . . .
H21A H 0.511312 1.245181 0.697798 0.095 Uiso 1 1 calc R U . . .
H21B H 0.669008 1.188341 0.675811 0.095 Uiso 1 1 calc R U . . .
H21C H 0.621363 1.128744 0.719480 0.095 Uiso 1 1 calc R U . . .
C22 C 0.3246(2) 1.0011(3) 0.69611(8) 0.0433(6) Uani 1 1 d . . . . .
C23 C 0.1779(3) 1.0928(3) 0.68527(9) 0.0567(7) Uani 1 1 d . . . . .
H23A H 0.146844 1.073246 0.656939 0.068 Uiso 1 1 calc R U . . .
H23B H 0.207145 1.194685 0.687232 0.068 Uiso 1 1 calc R U . . .
C24 C 0.0331(3) 1.0635(3) 0.71321(10) 0.0657(8) Uani 1 1 d . . . . .
H24A H -0.010764 0.967902 0.707170 0.079 Uiso 1 1 calc R U . . .
H24B H -0.051437 1.134567 0.707714 0.079 Uiso 1 1 calc R U . . .
C25 C 0.0806(3) 1.0709(3) 0.75842(10) 0.0577(7) Uani 1 1 d . . . . .
H25A H 0.115314 1.170472 0.764566 0.069 Uiso 1 1 calc R U . . .
C26 C 0.2244(3) 0.9713(3) 0.76460(9) 0.0517(6) Uani 1 1 d . . . . .
H26A H 0.257876 0.975112 0.793280 0.062 Uiso 1 1 calc R U . . .
H26B H 0.191725 0.872224 0.758552 0.062 Uiso 1 1 calc R U . . .
O26 O 0.35923(17) 1.00907(18) 0.73912(5) 0.0463(4) Uani 1 1 d . . . . .
C27 C -0.0579(4) 1.0316(4) 0.78759(12) 0.0872(11) Uani 1 1 d . . . . .
H27A H -0.144162 1.101368 0.784786 0.131 Uiso 1 1 calc R U . . .
H27B H -0.018672 1.032133 0.815487 0.131 Uiso 1 1 calc R U . . .
H27C H -0.098233 0.936521 0.780897 0.131 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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
C1 C2 1.502(4) . ?
C1 C10 1.548(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.512(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.435(3) . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9800 . ?
O3 H3 0.88(3) . ?
C4 C5 1.542(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.541(3) . ?
C5 C10 1.544(3) . ?
C5 H5A 0.9800 . ?
C6 O6 1.439(3) . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9800 . ?
O6 H6 0.88(3) . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.528(3) . ?
C8 C9 1.549(3) . ?
C8 H8A 0.9800 . ?
C9 C11 1.540(3) . ?
C9 C10 1.558(3) . ?
C9 H9A 0.9800 . ?
C10 C19 1.535(3) . ?
C11 C12 1.532(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.532(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.541(3) . ?
C13 C14 1.541(3) . ?
C13 C17 1.543(3) . ?
C14 C15 1.532(3) . ?
C14 H14A 0.9800 . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O16 1.440(2) . ?
C16 C17 1.551(3) . ?
C16 H16A 0.9800 . ?
O16 C22 1.427(3) . ?
C17 C20 1.542(3) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.525(3) . ?
C20 C22 1.528(3) . ?
C20 H20A 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O26 1.425(3) . ?
C22 C23 1.512(3) . ?
C23 C24 1.519(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.518(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.508(3) . ?
C25 C27 1.522(4) . ?
C25 H25A 0.9800 . ?
C26 O26 1.424(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C2 C1 C10 114.1(2) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O3 C3 C2 110.7(2) . . ?
O3 C3 C4 108.8(2) . . ?
C2 C3 C4 111.27(19) . . ?
O3 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C3 O3 H3 103(2) . . ?
C3 C4 C5 114.7(2) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 108.16(19) . . ?
C6 C5 C10 113.53(17) . . ?
C4 C5 C10 113.66(18) . . ?
C6 C5 H5A 107.0 . . ?
C4 C5 H5A 107.0 . . ?
C10 C5 H5A 107.0 . . ?
O6 C6 C7 108.31(17) . . ?
O6 C6 C5 112.7(2) . . ?
C7 C6 C5 111.83(18) . . ?
O6 C6 H6A 107.9 . . ?
C7 C6 H6A 107.9 . . ?
C5 C6 H6A 107.9 . . ?
C6 O6 H6 110(2) . . ?
C6 C7 C8 114.7(2) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C14 112.03(19) . . ?
C7 C8 C9 110.62(17) . . ?
C14 C8 C9 108.29(17) . . ?
C7 C8 H8A 108.6 . . ?
C14 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C11 C9 C8 112.37(18) . . ?
C11 C9 C10 113.96(19) . . ?
C8 C9 C10 111.31(17) . . ?
C11 C9 H9A 106.2 . . ?
C8 C9 H9A 106.2 . . ?
C10 C9 H9A 106.2 . . ?
C19 C10 C5 111.53(19) . . ?
C19 C10 C1 106.1(2) . . ?
C5 C10 C1 106.95(17) . . ?
C19 C10 C9 110.83(18) . . ?
C5 C10 C9 109.62(18) . . ?
C1 C10 C9 111.68(18) . . ?
C12 C11 C9 112.6(2) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.02(19) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C18 109.9(2) . . ?
C12 C13 C14 107.16(17) . . ?
C18 C13 C14 111.23(18) . . ?
C12 C13 C17 115.34(19) . . ?
C18 C13 C17 111.89(18) . . ?
C14 C13 C17 100.93(18) . . ?
C8 C14 C15 120.71(18) . . ?
C8 C14 C13 114.87(19) . . ?
C15 C14 C13 103.37(17) . . ?
C8 C14 H14A 105.6 . . ?
C15 C14 H14A 105.6 . . ?
C13 C14 H14A 105.6 . . ?
C16 C15 C14 102.79(17) . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
O16 C16 C15 112.34(18) . . ?
O16 C16 C17 105.00(17) . . ?
C15 C16 C17 107.20(18) . . ?
O16 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
C22 O16 C16 106.46(15) . . ?
C20 C17 C13 119.85(19) . . ?
C20 C17 C16 104.29(16) . . ?
C13 C17 C16 104.85(17) . . ?
C20 C17 H17A 109.1 . . ?
C13 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 114.4(2) . . ?
C21 C20 C17 114.71(19) . . ?
C22 C20 C17 103.75(18) . . ?
C21 C20 H20A 107.9 . . ?
C22 C20 H20A 107.9 . . ?
C17 C20 H20A 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O26 C22 O16 109.75(19) . . ?
O26 C22 C23 110.97(19) . . ?
O16 C22 C23 108.84(19) . . ?
O26 C22 C20 107.14(18) . . ?
O16 C22 C20 104.84(18) . . ?
C23 C22 C20 115.1(2) . . ?
C22 C23 C24 112.7(2) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 111.5(2) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 107.6(2) . . ?
C26 C25 C27 111.0(2) . . ?
C24 C25 C27 113.4(3) . . ?
C26 C25 H25A 108.2 . . ?
C24 C25 H25A 108.2 . . ?
C27 C25 H25A 108.2 . . ?
O26 C26 C25 112.5(2) . . ?
O26 C26 H26A 109.1 . . ?
C25 C26 H26A 109.1 . . ?
O26 C26 H26B 109.1 . . ?
C25 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C26 O26 C22 113.59(17) . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C1 C2 C3 58.9(3) . . . . ?
C1 C2 C3 O3 69.3(2) . . . . ?
C1 C2 C3 C4 -51.8(3) . . . . ?
O3 C3 C4 C5 -74.2(3) . . . . ?
C2 C3 C4 C5 48.0(3) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
C3 C4 C5 C10 -49.8(3) . . . . ?
C4 C5 C6 O6 -160.89(19) . . . . ?
C10 C5 C6 O6 72.0(3) . . . . ?
C4 C5 C6 C7 76.8(2) . . . . ?
C10 C5 C6 C7 -50.3(3) . . . . ?
O6 C6 C7 C8 -75.2(2) . . . . ?
C5 C6 C7 C8 49.6(3) . . . . ?
C6 C7 C8 C14 -173.69(16) . . . . ?
C6 C7 C8 C9 -52.8(3) . . . . ?
C7 C8 C9 C11 -174.9(2) . . . . ?
C14 C8 C9 C11 -51.8(3) . . . . ?
C7 C8 C9 C10 55.9(2) . . . . ?
C14 C8 C9 C10 179.06(19) . . . . ?
C6 C5 C10 C19 -69.1(2) . . . . ?
C4 C5 C10 C19 166.7(2) . . . . ?
C6 C5 C10 C1 175.3(2) . . . . ?
C4 C5 C10 C1 51.1(3) . . . . ?
C6 C5 C10 C9 54.1(2) . . . . ?
C4 C5 C10 C9 -70.1(2) . . . . ?
C2 C1 C10 C19 -175.9(2) . . . . ?
C2 C1 C10 C5 -56.8(3) . . . . ?
C2 C1 C10 C9 63.2(3) . . . . ?
C11 C9 C10 C19 -61.5(2) . . . . ?
C8 C9 C10 C19 66.9(2) . . . . ?
C11 C9 C10 C5 174.99(18) . . . . ?
C8 C9 C10 C5 -56.7(2) . . . . ?
C11 C9 C10 C1 56.6(3) . . . . ?
C8 C9 C10 C1 -175.01(19) . . . . ?
C8 C9 C11 C12 52.4(3) . . . . ?
C10 C9 C11 C12 -179.84(19) . . . . ?
C9 C11 C12 C13 -55.0(3) . . . . ?
C11 C12 C13 C18 -64.9(3) . . . . ?
C11 C12 C13 C14 56.1(3) . . . . ?
C11 C12 C13 C17 167.6(2) . . . . ?
C7 C8 C14 C15 -55.3(3) . . . . ?
C9 C8 C14 C15 -177.58(19) . . . . ?
C7 C8 C14 C13 179.82(17) . . . . ?
C9 C8 C14 C13 57.6(2) . . . . ?
C12 C13 C14 C8 -59.7(2) . . . . ?
C18 C13 C14 C8 60.4(2) . . . . ?
C17 C13 C14 C8 179.27(16) . . . . ?
C12 C13 C14 C15 166.8(2) . . . . ?
C18 C13 C14 C15 -73.1(2) . . . . ?
C17 C13 C14 C15 45.7(2) . . . . ?
C8 C14 C15 C16 -170.3(2) . . . . ?
C13 C14 C15 C16 -40.2(2) . . . . ?
C14 C15 C16 O16 133.73(19) . . . . ?
C14 C15 C16 C17 18.9(2) . . . . ?
C15 C16 O16 C22 -152.0(2) . . . . ?
C17 C16 O16 C22 -35.8(2) . . . . ?
C12 C13 C17 C20 95.2(2) . . . . ?
C18 C13 C17 C20 -31.3(3) . . . . ?
C14 C13 C17 C20 -149.68(18) . . . . ?
C12 C13 C17 C16 -148.25(19) . . . . ?
C18 C13 C17 C16 85.2(2) . . . . ?
C14 C13 C17 C16 -33.17(19) . . . . ?
O16 C16 C17 C20 16.3(2) . . . . ?
C15 C16 C17 C20 135.9(2) . . . . ?
O16 C16 C17 C13 -110.52(18) . . . . ?
C15 C16 C17 C13 9.1(2) . . . . ?
C13 C17 C20 C21 -110.3(3) . . . . ?
C16 C17 C20 C21 132.9(2) . . . . ?
C13 C17 C20 C22 124.1(2) . . . . ?
C16 C17 C20 C22 7.3(2) . . . . ?
C16 O16 C22 O26 -73.8(2) . . . . ?
C16 O16 C22 C23 164.6(2) . . . . ?
C16 O16 C22 C20 41.0(2) . . . . ?
C21 C20 C22 O26 -38.0(3) . . . . ?
C17 C20 C22 O26 87.7(2) . . . . ?
C21 C20 C22 O16 -154.6(2) . . . . ?
C17 C20 C22 O16 -28.9(2) . . . . ?
C21 C20 C22 C23 85.9(3) . . . . ?
C17 C20 C22 C23 -148.4(2) . . . . ?
O26 C22 C23 C24 -49.7(3) . . . . ?
O16 C22 C23 C24 71.1(3) . . . . ?
C20 C22 C23 C24 -171.6(2) . . . . ?
C22 C23 C24 C25 50.5(3) . . . . ?
C23 C24 C25 C26 -52.7(3) . . . . ?
C23 C24 C25 C27 -175.9(2) . . . . ?
C24 C25 C26 O26 58.1(3) . . . . ?
C27 C25 C26 O26 -177.3(2) . . . . ?
C25 C26 O26 C22 -61.1(3) . . . . ?
O16 C22 O26 C26 -65.4(2) . . . . ?
C23 C22 O26 C26 54.9(2) . . . . ?
C20 C22 O26 C26 -178.69(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O6 0.88(3) 2.02(3) 2.895(2) 175(3) 1_655 yes
O6 H6 O3 0.88(3) 2.03(3) 2.915(3) 178(3) 4_456 yes

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.028

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
