# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_sb991_hy
_database_code_depnum_ccdc_archive 'CCDC 2207135'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3S,5S,8R,9S,10S,13S,14R)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,10,11,12,13,14-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one
_chemical_name_common            
;
3β-hydroxy-5α,14β-androst-15-en-17-one
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H28 O2'
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.1269(3)
_cell_length_b                   6.8473(3)
_cell_length_c                   20.2325(9)
_cell_angle_alpha                98.233(2)
_cell_angle_beta                 95.708(2)
_cell_angle_gamma                101.625(2)
_cell_volume                     815.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8795
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.572
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7765
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 14+1 runs, 1917 frames, 20/30/40 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            9963
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.455
_diffrn_reflns_theta_max         72.138
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.851
_reflns_number_total             5361
_reflns_number_gt                5197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.675
_reflns_Friedel_fraction_full    0.707

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    .
_computing_publication_material  publCIF

_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)+(0.0782P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5361
_refine_ls_number_parameters     385
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.4472(4) 0.1297(4) -0.04969(12) 0.0224(5) Uani 1 1 d . . . . .
H1A H 0.5206 0.2750 -0.0381 0.027 Uiso 1 1 calc R U . . .
H1B H 0.5663 0.0515 -0.0467 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3291(5) 0.0864(4) -0.12226(13) 0.0240(5) Uani 1 1 d . . . . .
H2A H 0.2212 0.1750 -0.1267 0.029 Uiso 1 1 calc R U . . .
H2B H 0.4420 0.1180 -0.1532 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2052(4) -0.1326(4) -0.14223(13) 0.0215(5) Uani 1 1 d . . . . .
H3 H 0.3176 -0.2201 -0.1416 0.026 Uiso 1 1 calc R U . . .
O3 O 0.0964(3) -0.1571(3) -0.20945(9) 0.0251(4) Uani 1 1 d D . . . .
H3O H 0.051(6) -0.281(4) -0.2250(19) 0.038 Uiso 1 1 d D U . . .
C4 C 0.0408(4) -0.1913(4) -0.09280(13) 0.0222(5) Uani 1 1 d . . . . .
H4A H -0.0309 -0.3370 -0.1052 0.027 Uiso 1 1 calc R U . . .
H4B H -0.0789 -0.1138 -0.0957 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1610(4) -0.1488(4) -0.02036(13) 0.0192(5) Uani 1 1 d . . . . .
H5 H 0.2798 -0.2297 -0.0204 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0087(4) -0.2226(4) 0.03051(13) 0.0242(5) Uani 1 1 d . . . . .
H6A H -0.1053 -0.1395 0.0355 0.029 Uiso 1 1 calc R U . . .
H6B H -0.0710 -0.3647 0.0139 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1468(4) -0.2081(4) 0.09860(13) 0.0235(5) Uani 1 1 d . . . . .
H7A H 0.2485 -0.3034 0.0944 0.028 Uiso 1 1 calc R U . . .
H7B H 0.0447 -0.2484 0.1316 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2867(4) 0.0065(4) 0.12472(12) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.1777 0.0948 0.1338 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4264(4) 0.0931(4) 0.07215(12) 0.0173(5) Uani 1 1 d . . . . .
H9 H 0.5431 0.0116 0.0653 0.021 Uiso 1 1 calc R U . . .
C10 C 0.2861(4) 0.0754(4) 0.00221(13) 0.0182(5) Uani 1 1 d . . . . .
C11 C 0.5508(4) 0.3098(4) 0.10261(12) 0.0206(5) Uani 1 1 d . . . . .
H11A H 0.6330 0.3724 0.0685 0.025 Uiso 1 1 calc R U . . .
H11B H 0.4407 0.3911 0.1158 0.025 Uiso 1 1 calc R U . . .
C12 C 0.7166(4) 0.3104(4) 0.16439(12) 0.0200(5) Uani 1 1 d . . . . .
H12A H 0.7975 0.4513 0.1823 0.024 Uiso 1 1 calc R U . . .
H12B H 0.8291 0.2328 0.1504 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6012(4) 0.2180(4) 0.22126(12) 0.0181(5) Uani 1 1 d . . . . .
C14 C 0.4309(4) 0.0157(4) 0.19278(12) 0.0188(5) Uani 1 1 d . . . . .
H14 H 0.3234 -0.0055 0.2265 0.023 Uiso 1 1 calc R U . . .
C15 C 0.5740(5) -0.1387(4) 0.19726(13) 0.0232(5) Uani 1 1 d . . . . .
H15 H 0.5299 -0.2737 0.1737 0.028 Uiso 1 1 calc R U . . .
C16 C 0.7673(5) -0.0674(4) 0.23732(13) 0.0240(5) Uani 1 1 d . . . . .
H16 H 0.8739 -0.1444 0.2488 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7900(4) 0.1487(4) 0.26093(12) 0.0214(5) Uani 1 1 d . . . . .
O17 O 0.9365(3) 0.2581(3) 0.30316(10) 0.0301(5) Uani 1 1 d . . . . .
C18 C 0.1228(5) 0.2197(4) 0.00566(13) 0.0244(5) Uani 1 1 d . . . . .
H18A H 0.0202 0.1858 0.0385 0.037 Uiso 1 1 calc R U . . .
H18B H 0.2085 0.3594 0.0194 0.037 Uiso 1 1 calc R U . . .
H18C H 0.0360 0.2057 -0.0388 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5038(5) 0.3721(4) 0.26445(13) 0.0239(5) Uani 1 1 d . . . . .
H19A H 0.3844 0.4111 0.2368 0.036 Uiso 1 1 calc R U . . .
H19B H 0.4417 0.3123 0.3016 0.036 Uiso 1 1 calc R U . . .
H19C H 0.6228 0.4921 0.2827 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4725(4) 1.0417(4) 0.44486(13) 0.0243(5) Uani 1 1 d . . . . .
H21A H 0.5634 1.1788 0.4450 0.029 Uiso 1 1 calc R U . . .
H21B H 0.5758 0.9582 0.4602 0.029 Uiso 1 1 calc R U . . .
C22 C 0.3636(4) 0.9497(4) 0.37254(13) 0.0243(5) Uani 1 1 d . . . . .
H22A H 0.2734 1.0405 0.3550 0.029 Uiso 1 1 calc R U . . .
H22B H 0.4826 0.9380 0.3434 0.029 Uiso 1 1 calc R U . . .
C23 C 0.2138(4) 0.7430(4) 0.36958(13) 0.0218(5) Uani 1 1 d . . . . .
H23 H 0.3085 0.6495 0.3839 0.026 Uiso 1 1 calc R U . . .
O23 O 0.1152(3) 0.6701(3) 0.30106(9) 0.0251(4) Uani 1 1 d D . . . .
H23O H 0.056(6) 0.546(4) 0.299(2) 0.038 Uiso 1 1 d D U . . .
C24 C 0.0372(4) 0.7542(4) 0.41679(13) 0.0241(5) Uani 1 1 d . . . . .
H24A H -0.0551 0.6170 0.4157 0.029 Uiso 1 1 calc R U . . .
H24B H -0.0634 0.8399 0.4015 0.029 Uiso 1 1 calc R U . . .
C25 C 0.1483(4) 0.8428(4) 0.48908(12) 0.0201(5) Uani 1 1 d . . . . .
H25 H 0.2504 0.7529 0.5013 0.024 Uiso 1 1 calc R U . . .
C26 C -0.0190(5) 0.8348(4) 0.54021(13) 0.0262(6) Uani 1 1 d . . . . .
H26A H -0.1213 0.9260 0.5317 0.031 Uiso 1 1 calc R U . . .
H26B H -0.1109 0.6956 0.5350 0.031 Uiso 1 1 calc R U . . .
C27 C 0.1041(4) 0.8986(4) 0.61181(13) 0.0232(5) Uani 1 1 d . . . . .
H27A H 0.1920 0.7974 0.6220 0.028 Uiso 1 1 calc R U . . .
H27B H -0.0073 0.9015 0.6440 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2625(4) 1.1071(4) 0.62134(12) 0.0174(5) Uani 1 1 d . . . . .
H28 H 0.1686 1.2080 0.6144 0.021 Uiso 1 1 calc R U . . .
C29 C 0.4266(4) 1.1142(4) 0.56838(12) 0.0190(5) Uani 1 1 d . . . . .
H29 H 0.5127 1.0073 0.5747 0.023 Uiso 1 1 calc R U . . .
C30 C 0.3008(4) 1.0562(4) 0.49508(12) 0.0183(5) Uani 1 1 d . . . . .
C31 C 0.6025(5) 1.3181(4) 0.58135(14) 0.0296(6) Uani 1 1 d . . . . .
H31A H 0.7547 1.2900 0.5882 0.036 Uiso 1 1 calc R U . . .
H31B H 0.5922 1.3827 0.5407 0.036 Uiso 1 1 calc R U . . .
C32 C 0.5740(5) 1.4669(4) 0.64218(14) 0.0264(5) Uani 1 1 d . . . . .
H32A H 0.4342 1.5149 0.6323 0.032 Uiso 1 1 calc R U . . .
H32B H 0.7017 1.5856 0.6501 0.032 Uiso 1 1 calc R U . . .
C33 C 0.5632(4) 1.3711(4) 0.70600(12) 0.0193(5) Uani 1 1 d . . . . .
C34 C 0.3886(4) 1.1671(4) 0.69391(12) 0.0182(5) Uani 1 1 d . . . . .
H34 H 0.2752 1.1778 0.7258 0.022 Uiso 1 1 calc R U . . .
C35 C 0.5222(4) 1.0190(4) 0.71401(12) 0.0216(5) Uani 1 1 d . . . . .
H35 H 0.4572 0.8804 0.7134 0.026 Uiso 1 1 calc R U . . .
C36 C 0.7407(5) 1.0995(4) 0.73283(13) 0.0248(5) Uani 1 1 d . . . . .
H36 H 0.8499 1.0287 0.7474 0.030 Uiso 1 1 calc R U . . .
C37 C 0.7847(4) 1.3133(4) 0.72745(14) 0.0247(5) Uani 1 1 d . . . . .
O37 O 0.9674(3) 1.4324(3) 0.73954(14) 0.0414(6) Uani 1 1 d . . . . .
C38 C 0.1649(5) 1.2145(4) 0.47892(14) 0.0265(6) Uani 1 1 d . . . . .
H38A H 0.0557 1.2236 0.5109 0.040 Uiso 1 1 calc R U . . .
H38B H 0.2674 1.3466 0.4827 0.040 Uiso 1 1 calc R U . . .
H38C H 0.0853 1.1736 0.4330 0.040 Uiso 1 1 calc R U . . .
C39 C 0.5202(4) 1.5196(4) 0.76509(13) 0.0226(5) Uani 1 1 d . . . . .
H39A H 0.3790 1.5604 0.7532 0.034 Uiso 1 1 calc R U . . .
H39B H 0.5101 1.4540 0.8050 0.034 Uiso 1 1 calc R U . . .
H39C H 0.6442 1.6393 0.7748 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.531(3) . ?
C1 C10 1.545(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.514(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.425(3) . ?
C3 C4 1.526(4) . ?
C3 H3 1.0000 . ?
O3 H3O 0.84(2) . ?
C4 C5 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(3) . ?
C5 C10 1.552(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.540(3) . ?
C8 C14 1.546(3) . ?
C8 H8 1.0000 . ?
C9 C11 1.534(3) . ?
C9 C10 1.556(3) . ?
C9 H9 1.0000 . ?
C10 C18 1.541(3) . ?
C11 C12 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.554(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C19 1.526(3) . ?
C13 C17 1.534(3) . ?
C13 C14 1.552(3) . ?
C14 C15 1.510(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.327(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.462(4) . ?
C16 H16 0.9500 . ?
C17 O17 1.221(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.535(3) . ?
C21 C30 1.541(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.513(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O23 1.432(3) . ?
C23 C24 1.519(4) . ?
C23 H23 1.0000 . ?
O23 H23O 0.85(2) . ?
C24 C25 1.534(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.526(4) . ?
C25 C30 1.549(3) . ?
C25 H25 1.0000 . ?
C26 C27 1.526(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.531(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.540(3) . ?
C28 C34 1.547(3) . ?
C28 H28 1.0000 . ?
C29 C31 1.553(4) . ?
C29 C30 1.559(3) . ?
C29 H29 1.0000 . ?
C30 C38 1.544(3) . ?
C31 C32 1.529(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.531(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C37 1.528(3) . ?
C33 C39 1.535(3) . ?
C33 C34 1.550(3) . ?
C34 C35 1.500(3) . ?
C34 H34 1.0000 . ?
C35 C36 1.335(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.456(4) . ?
C36 H36 0.9500 . ?
C37 O37 1.224(4) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 113.2(2) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.5(2) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O3 C3 C2 107.51(19) . . ?
O3 C3 C4 112.5(2) . . ?
C2 C3 C4 110.9(2) . . ?
O3 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C3 O3 H3O 110(3) . . ?
C3 C4 C5 111.1(2) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 113.3(2) . . ?
C6 C5 C10 111.9(2) . . ?
C4 C5 C10 112.80(19) . . ?
C6 C5 H5 106.0 . . ?
C4 C5 H5 106.0 . . ?
C10 C5 H5 106.0 . . ?
C7 C6 C5 110.3(2) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 112.0(2) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.7(2) . . ?
C7 C8 C14 110.92(19) . . ?
C9 C8 C14 112.70(19) . . ?
C7 C8 H8 106.7 . . ?
C9 C8 H8 106.7 . . ?
C14 C8 H8 106.7 . . ?
C11 C9 C8 108.03(19) . . ?
C11 C9 C10 113.71(18) . . ?
C8 C9 C10 113.41(19) . . ?
C11 C9 H9 107.1 . . ?
C8 C9 H9 107.1 . . ?
C10 C9 H9 107.1 . . ?
C18 C10 C1 109.2(2) . . ?
C18 C10 C5 112.1(2) . . ?
C1 C10 C5 107.64(19) . . ?
C18 C10 C9 110.9(2) . . ?
C1 C10 C9 109.10(19) . . ?
C5 C10 C9 107.86(17) . . ?
C12 C11 C9 110.5(2) . . ?
C12 C11 H11A 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C19 C13 C17 112.8(2) . . ?
C19 C13 C14 114.2(2) . . ?
C17 C13 C14 102.62(19) . . ?
C19 C13 C12 111.5(2) . . ?
C17 C13 C12 103.61(19) . . ?
C14 C13 C12 111.29(19) . . ?
C15 C14 C8 117.8(2) . . ?
C15 C14 C13 102.57(19) . . ?
C8 C14 C13 116.51(19) . . ?
C15 C14 H14 106.4 . . ?
C8 C14 H14 106.4 . . ?
C13 C14 H14 106.4 . . ?
C16 C15 C14 113.4(2) . . ?
C16 C15 H15 123.3 . . ?
C14 C15 H15 123.3 . . ?
C15 C16 C17 109.1(2) . . ?
C15 C16 H16 125.4 . . ?
C17 C16 H16 125.4 . . ?
O17 C17 C16 126.7(2) . . ?
O17 C17 C13 125.3(2) . . ?
C16 C17 C13 108.0(2) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C30 113.4(2) . . ?
C22 C21 H21A 108.9 . . ?
C30 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C30 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 111.3(2) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
O23 C23 C22 107.9(2) . . ?
O23 C23 C24 112.1(2) . . ?
C22 C23 C24 110.6(2) . . ?
O23 C23 H23 108.8 . . ?
C22 C23 H23 108.8 . . ?
C24 C23 H23 108.8 . . ?
C23 O23 H23O 106(3) . . ?
C23 C24 C25 110.7(2) . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C26 C25 C24 113.0(2) . . ?
C26 C25 C30 112.4(2) . . ?
C24 C25 C30 112.91(19) . . ?
C26 C25 H25 105.9 . . ?
C24 C25 H25 105.9 . . ?
C30 C25 H25 105.9 . . ?
C27 C26 C25 110.5(2) . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 C28 111.9(2) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 C29 110.91(19) . . ?
C27 C28 C34 110.98(19) . . ?
C29 C28 C34 111.67(19) . . ?
C27 C28 H28 107.7 . . ?
C29 C28 H28 107.7 . . ?
C34 C28 H28 107.7 . . ?
C28 C29 C31 111.5(2) . . ?
C28 C29 C30 111.98(18) . . ?
C31 C29 C30 113.89(19) . . ?
C28 C29 H29 106.3 . . ?
C31 C29 H29 106.3 . . ?
C30 C29 H29 106.3 . . ?
C21 C30 C38 109.5(2) . . ?
C21 C30 C25 107.5(2) . . ?
C38 C30 C25 112.0(2) . . ?
C21 C30 C29 109.50(19) . . ?
C38 C30 C29 111.0(2) . . ?
C25 C30 C29 107.20(18) . . ?
C32 C31 C29 114.2(2) . . ?
C32 C31 H31A 108.7 . . ?
C29 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C29 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 112.1(2) . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C37 C33 C32 111.2(2) . . ?
C37 C33 C39 107.0(2) . . ?
C32 C33 C39 110.9(2) . . ?
C37 C33 C34 103.6(2) . . ?
C32 C33 C34 111.8(2) . . ?
C39 C33 C34 112.0(2) . . ?
C35 C34 C28 113.9(2) . . ?
C35 C34 C33 104.0(2) . . ?
C28 C34 C33 113.84(19) . . ?
C35 C34 H34 108.3 . . ?
C28 C34 H34 108.3 . . ?
C33 C34 H34 108.3 . . ?
C36 C35 C34 114.0(2) . . ?
C36 C35 H35 123.0 . . ?
C34 C35 H35 123.0 . . ?
C35 C36 C37 109.0(2) . . ?
C35 C36 H36 125.5 . . ?
C37 C36 H36 125.5 . . ?
O37 C37 C36 126.6(3) . . ?
O37 C37 C33 124.2(2) . . ?
C36 C37 C33 109.3(2) . . ?
C30 C38 H38A 109.5 . . ?
C30 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C30 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33 C39 H39A 109.5 . . ?
C33 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C33 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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 -56.3(3) . . . . ?
C1 C2 C3 O3 178.5(2) . . . . ?
C1 C2 C3 C4 55.1(3) . . . . ?
O3 C3 C4 C5 -175.9(2) . . . . ?
C2 C3 C4 C5 -55.5(3) . . . . ?
C3 C4 C5 C6 -174.7(2) . . . . ?
C3 C4 C5 C10 56.9(3) . . . . ?
C4 C5 C6 C7 170.4(2) . . . . ?
C10 C5 C6 C7 -60.7(3) . . . . ?
C5 C6 C7 C8 55.4(3) . . . . ?
C6 C7 C8 C9 -50.8(3) . . . . ?
C6 C7 C8 C14 -178.2(2) . . . . ?
C7 C8 C9 C11 177.70(19) . . . . ?
C14 C8 C9 C11 -55.8(2) . . . . ?
C7 C8 C9 C10 50.7(3) . . . . ?
C14 C8 C9 C10 177.16(19) . . . . ?
C2 C1 C10 C18 -67.4(3) . . . . ?
C2 C1 C10 C5 54.5(3) . . . . ?
C2 C1 C10 C9 171.3(2) . . . . ?
C6 C5 C10 C18 -64.0(3) . . . . ?
C4 C5 C10 C18 65.2(3) . . . . ?
C6 C5 C10 C1 175.91(19) . . . . ?
C4 C5 C10 C1 -54.9(3) . . . . ?
C6 C5 C10 C9 58.3(2) . . . . ?
C4 C5 C10 C9 -172.50(19) . . . . ?
C11 C9 C10 C18 -54.0(3) . . . . ?
C8 C9 C10 C18 69.9(3) . . . . ?
C11 C9 C10 C1 66.2(3) . . . . ?
C8 C9 C10 C1 -169.8(2) . . . . ?
C11 C9 C10 C5 -177.10(19) . . . . ?
C8 C9 C10 C5 -53.1(3) . . . . ?
C8 C9 C11 C12 63.4(2) . . . . ?
C10 C9 C11 C12 -169.8(2) . . . . ?
C9 C11 C12 C13 -60.2(3) . . . . ?
C11 C12 C13 C19 -82.4(3) . . . . ?
C11 C12 C13 C17 156.0(2) . . . . ?
C11 C12 C13 C14 46.4(3) . . . . ?
C7 C8 C14 C15 50.8(3) . . . . ?
C9 C8 C14 C15 -76.6(3) . . . . ?
C7 C8 C14 C13 173.3(2) . . . . ?
C9 C8 C14 C13 45.9(3) . . . . ?
C19 C13 C14 C15 -142.2(2) . . . . ?
C17 C13 C14 C15 -19.8(2) . . . . ?
C12 C13 C14 C15 90.5(2) . . . . ?
C19 C13 C14 C8 87.6(3) . . . . ?
C17 C13 C14 C8 -150.0(2) . . . . ?
C12 C13 C14 C8 -39.7(3) . . . . ?
C8 C14 C15 C16 145.6(2) . . . . ?
C13 C14 C15 C16 16.2(3) . . . . ?
C14 C15 C16 C17 -4.7(3) . . . . ?
C15 C16 C17 O17 172.8(3) . . . . ?
C15 C16 C17 C13 -9.3(3) . . . . ?
C19 C13 C17 O17 -40.3(4) . . . . ?
C14 C13 C17 O17 -163.7(2) . . . . ?
C12 C13 C17 O17 80.4(3) . . . . ?
C19 C13 C17 C16 141.8(2) . . . . ?
C14 C13 C17 C16 18.4(3) . . . . ?
C12 C13 C17 C16 -97.5(2) . . . . ?
C30 C21 C22 C23 -56.1(3) . . . . ?
C21 C22 C23 O23 178.7(2) . . . . ?
C21 C22 C23 C24 55.9(3) . . . . ?
O23 C23 C24 C25 -177.2(2) . . . . ?
C22 C23 C24 C25 -56.8(3) . . . . ?
C23 C24 C25 C26 -173.2(2) . . . . ?
C23 C24 C25 C30 57.9(3) . . . . ?
C24 C25 C26 C27 172.5(2) . . . . ?
C30 C25 C26 C27 -58.3(3) . . . . ?
C25 C26 C27 C28 55.0(3) . . . . ?
C26 C27 C28 C29 -54.3(3) . . . . ?
C26 C27 C28 C34 -179.0(2) . . . . ?
C27 C28 C29 C31 -174.8(2) . . . . ?
C34 C28 C29 C31 -50.4(3) . . . . ?
C27 C28 C29 C30 56.3(2) . . . . ?
C34 C28 C29 C30 -179.38(19) . . . . ?
C22 C21 C30 C38 -68.2(3) . . . . ?
C22 C21 C30 C25 53.8(3) . . . . ?
C22 C21 C30 C29 169.9(2) . . . . ?
C26 C25 C30 C21 175.9(2) . . . . ?
C24 C25 C30 C21 -54.8(2) . . . . ?
C26 C25 C30 C38 -63.7(3) . . . . ?
C24 C25 C30 C38 65.6(3) . . . . ?
C26 C25 C30 C29 58.3(3) . . . . ?
C24 C25 C30 C29 -172.5(2) . . . . ?
C28 C29 C30 C21 -173.4(2) . . . . ?
C31 C29 C30 C21 58.9(3) . . . . ?
C28 C29 C30 C38 65.6(3) . . . . ?
C31 C29 C30 C38 -62.1(3) . . . . ?
C28 C29 C30 C25 -57.0(2) . . . . ?
C31 C29 C30 C25 175.3(2) . . . . ?
C28 C29 C31 C32 -0.8(3) . . . . ?
C30 C29 C31 C32 127.1(2) . . . . ?
C29 C31 C32 C33 52.5(3) . . . . ?
C31 C32 C33 C37 64.5(3) . . . . ?
C31 C32 C33 C39 -176.6(2) . . . . ?
C31 C32 C33 C34 -50.8(3) . . . . ?
C27 C28 C34 C35 57.4(3) . . . . ?
C29 C28 C34 C35 -66.9(3) . . . . ?
C27 C28 C34 C33 176.41(19) . . . . ?
C29 C28 C34 C33 52.1(3) . . . . ?
C37 C33 C34 C35 3.8(2) . . . . ?
C32 C33 C34 C35 123.7(2) . . . . ?
C39 C33 C34 C35 -111.1(2) . . . . ?
C37 C33 C34 C28 -120.7(2) . . . . ?
C32 C33 C34 C28 -0.8(3) . . . . ?
C39 C33 C34 C28 124.3(2) . . . . ?
C28 C34 C35 C36 122.2(2) . . . . ?
C33 C34 C35 C36 -2.3(3) . . . . ?
C34 C35 C36 C37 -0.5(3) . . . . ?
C35 C36 C37 O37 -178.6(3) . . . . ?
C35 C36 C37 C33 3.1(3) . . . . ?
C32 C33 C37 O37 57.1(3) . . . . ?
C39 C33 C37 O37 -64.2(3) . . . . ?
C34 C33 C37 O37 177.4(3) . . . . ?
C32 C33 C37 C36 -124.6(2) . . . . ?
C39 C33 C37 C36 114.1(2) . . . . ?
C34 C33 C37 C36 -4.3(3) . . . . ?

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
O3 H3O O37 0.84(2) 1.94(2) 2.775(3) 176(4) 1_434
C16 H16 O23 0.95 2.40 3.332(3) 167.7 1_645
O23 H23O O17 0.85(2) 1.97(2) 2.821(3) 175(4) 1_455
C36 H36 O3 0.95 2.34 3.290(3) 174.5 1_666

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_sb1125_hy
_database_code_depnum_ccdc_archive 'CCDC 2207136'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(benzyloxy)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,10,11,12,13,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one

_chemical_name_common            
;
3β-benzyloxy-5α-androst-14-en-17-one
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H34 O2'
_chemical_formula_sum            'C26 H34 O2'
_chemical_formula_weight         378.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   9.4289(2)
_cell_length_b                   12.1170(2)
_cell_length_c                   17.9189(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2047.23(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 7+1 runs, 1382 frames, 8/14/20 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19971
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.405
_diffrn_reflns_theta_max         72.104
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4009
_reflns_number_gt                3782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  publCIF

_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)+(0.0356P)²+0.5614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 The absolute configuration has not been established by 
 anomalous dispersion effects in diffraction measurement
 on the crystal. The enantiomer has been assigned by
 reference to an unchanging chiral centre in the synthetic
 procedure.
;
_refine_ls_abs_structure_Flack   0.12(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4009
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.4306(2) 0.57087(16) 0.33544(10) 0.0250(4) Uani 1 1 d . . . . .
H1A H 0.4448 0.4901 0.3395 0.030 Uiso 1 1 calc R U . . .
H1B H 0.3370 0.5885 0.3574 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4295(2) 0.60330(16) 0.25255(10) 0.0257(4) Uani 1 1 d . . . . .
H2A H 0.5186 0.5781 0.2288 0.031 Uiso 1 1 calc R U . . .
H2B H 0.3495 0.5659 0.2272 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4150(2) 0.72742(16) 0.24275(10) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.3206 0.7512 0.2624 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5306(2) 0.78753(16) 0.28528(11) 0.0257(4) Uani 1 1 d . . . . .
H4A H 0.5166 0.8682 0.2804 0.031 Uiso 1 1 calc R U . . .
H4B H 0.6242 0.7689 0.2636 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5284(2) 0.75547(16) 0.36795(10) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.4315 0.7744 0.3866 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6321(2) 0.82389(17) 0.41452(11) 0.0274(4) Uani 1 1 d . . . . .
H6A H 0.7308 0.8038 0.4014 0.033 Uiso 1 1 calc R U . . .
H6B H 0.6187 0.9033 0.4037 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6062(2) 0.80207(17) 0.49736(11) 0.0270(4) Uani 1 1 d . . . . .
H7A H 0.6764 0.8439 0.5271 0.032 Uiso 1 1 calc R U . . .
H7B H 0.5106 0.8291 0.5110 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6175(2) 0.68019(17) 0.51671(10) 0.0243(4) Uani 1 1 d . . . . .
H8 H 0.7184 0.6573 0.5094 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5236(2) 0.60708(16) 0.46549(10) 0.0226(4) Uani 1 1 d . . . . .
H9 H 0.4231 0.6278 0.4765 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5468(2) 0.62987(16) 0.38079(10) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.5391(2) 0.48563(17) 0.48790(10) 0.0273(4) Uani 1 1 d . . . . .
H11A H 0.4830 0.4392 0.4533 0.033 Uiso 1 1 calc R U . . .
H11B H 0.6399 0.4635 0.4834 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4888(2) 0.46557(18) 0.56805(11) 0.0289(4) Uani 1 1 d . . . . .
H12A H 0.5025 0.3869 0.5811 0.035 Uiso 1 1 calc R U . . .
H12B H 0.3863 0.4824 0.5718 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5716(2) 0.53833(18) 0.62318(11) 0.0282(4) Uani 1 1 d . . . . .
C14 C 0.5781(2) 0.65685(17) 0.59680(10) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.5376(2) 0.72765(19) 0.64950(11) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.5378 0.8055 0.6433 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4916(2) 0.6707(2) 0.71991(11) 0.0352(5) Uani 1 1 d . . . . .
H16A H 0.3946 0.6933 0.7345 0.042 Uiso 1 1 calc R U . . .
H16B H 0.5576 0.6868 0.7615 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4963(2) 0.5493(2) 0.69857(11) 0.0340(5) Uani 1 1 d . . . . .
O17 O 0.4486(2) 0.47337(16) 0.73421(9) 0.0506(5) Uani 1 1 d . . . . .
C18 C 0.6939(2) 0.58846(18) 0.35583(11) 0.0289(4) Uani 1 1 d . . . . .
H18A H 0.7677 0.6261 0.3848 0.043 Uiso 1 1 calc R U . . .
H18B H 0.7005 0.5087 0.3642 0.043 Uiso 1 1 calc R U . . .
H18C H 0.7072 0.6042 0.3026 0.043 Uiso 1 1 calc R U . . .
C19 C 0.7208(3) 0.4920(2) 0.63807(12) 0.0367(5) Uani 1 1 d . . . . .
H19A H 0.7133 0.4154 0.6550 0.055 Uiso 1 1 calc R U . . .
H19B H 0.7768 0.4949 0.5920 0.055 Uiso 1 1 calc R U . . .
H19C H 0.7675 0.5364 0.6767 0.055 Uiso 1 1 calc R U . . .
O3 O 0.42589(16) 0.75944(12) 0.16575(7) 0.0299(3) Uani 1 1 d . . . . .
C20 C 0.3025(2) 0.73820(18) 0.12252(11) 0.0286(4) Uani 1 1 d . . . . .
H20A H 0.2494 0.8078 0.1150 0.034 Uiso 1 1 calc R U . . .
H20B H 0.2402 0.6860 0.1496 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3417(2) 0.68990(17) 0.04762(11) 0.0262(4) Uani 1 1 d . . . . .
C22 C 0.4547(2) 0.61837(18) 0.04072(12) 0.0325(5) Uani 1 1 d . . . . .
H22 H 0.5114 0.6019 0.0831 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4860(3) 0.5703(2) -0.02729(13) 0.0408(6) Uani 1 1 d . . . . .
H23 H 0.5646 0.5216 -0.0312 0.049 Uiso 1 1 calc R U . . .
C24 C 0.4048(3) 0.5923(2) -0.08931(13) 0.0431(6) Uani 1 1 d . . . . .
H24 H 0.4264 0.5587 -0.1358 0.052 Uiso 1 1 calc R U . . .
C25 C 0.2917(3) 0.6637(2) -0.08322(13) 0.0443(6) Uani 1 1 d . . . . .
H25 H 0.2349 0.6792 -0.1257 0.053 Uiso 1 1 calc R U . . .
C26 C 0.2602(3) 0.71310(19) -0.01522(12) 0.0361(5) Uani 1 1 d . . . . .
H26 H 0.1827 0.7629 -0.0116 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.536(3) . ?
C1 C10 1.540(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.437(2) . ?
C3 C4 1.516(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.532(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(3) . ?
C5 C10 1.549(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.509(3) . ?
C8 C9 1.553(3) . ?
C8 H8 1.0000 . ?
C9 C11 1.532(3) . ?
C9 C10 1.558(2) . ?
C9 H9 1.0000 . ?
C10 C18 1.542(3) . ?
C11 C12 1.532(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.537(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.513(3) . ?
C13 C17 1.532(3) . ?
C13 C19 1.539(3) . ?
C14 C15 1.332(3) . ?
C15 C16 1.502(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.521(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.207(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O3 C20 1.421(2) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.378(3) . ?
C21 C26 1.392(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 113.33(16) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.43(15) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O3 C3 C4 107.56(16) . . ?
O3 C3 C2 111.81(15) . . ?
C4 C3 C2 110.64(16) . . ?
O3 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
C3 C4 C5 110.76(16) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 112.43(16) . . ?
C6 C5 C10 112.35(16) . . ?
C4 C5 C10 113.04(15) . . ?
C6 C5 H5 106.1 . . ?
C4 C5 H5 106.1 . . ?
C10 C5 H5 106.1 . . ?
C7 C6 C5 109.53(16) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 112.24(17) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C14 C8 C7 112.44(17) . . ?
C14 C8 C9 108.36(16) . . ?
C7 C8 C9 112.32(16) . . ?
C14 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C11 C9 C8 109.80(16) . . ?
C11 C9 C10 114.34(15) . . ?
C8 C9 C10 113.26(15) . . ?
C11 C9 H9 106.3 . . ?
C8 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
C1 C10 C18 109.64(16) . . ?
C1 C10 C5 107.37(15) . . ?
C18 C10 C5 112.15(16) . . ?
C1 C10 C9 109.40(15) . . ?
C18 C10 C9 110.54(16) . . ?
C5 C10 C9 107.65(15) . . ?
C12 C11 C9 111.61(16) . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.73(17) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C17 102.24(18) . . ?
C14 C13 C12 111.36(16) . . ?
C17 C13 C12 112.41(18) . . ?
C14 C13 C19 111.30(18) . . ?
C17 C13 C19 107.60(17) . . ?
C12 C13 C19 111.53(18) . . ?
C15 C14 C8 128.6(2) . . ?
C15 C14 C13 112.23(18) . . ?
C8 C14 C13 119.00(17) . . ?
C14 C15 C16 112.5(2) . . ?
C14 C15 H15 123.8 . . ?
C16 C15 H15 123.8 . . ?
C15 C16 C17 102.98(17) . . ?
C15 C16 H16A 111.2 . . ?
C17 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C17 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
O17 C17 C16 126.4(2) . . ?
O17 C17 C13 125.0(2) . . ?
C16 C17 C13 108.61(18) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O3 C3 114.59(15) . . ?
O3 C20 C21 110.74(16) . . ?
O3 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C20 120.83(18) . . ?
C26 C21 C20 120.35(19) . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.3(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.3(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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 -55.9(2) . . . . ?
C1 C2 C3 O3 175.12(16) . . . . ?
C1 C2 C3 C4 55.2(2) . . . . ?
O3 C3 C4 C5 -178.61(16) . . . . ?
C2 C3 C4 C5 -56.2(2) . . . . ?
C3 C4 C5 C6 -173.48(17) . . . . ?
C3 C4 C5 C10 58.0(2) . . . . ?
C4 C5 C6 C7 170.21(17) . . . . ?
C10 C5 C6 C7 -60.9(2) . . . . ?
C5 C6 C7 C8 56.3(2) . . . . ?
C6 C7 C8 C14 -174.43(16) . . . . ?
C6 C7 C8 C9 -51.9(2) . . . . ?
C14 C8 C9 C11 -55.0(2) . . . . ?
C7 C8 C9 C11 -179.81(16) . . . . ?
C14 C8 C9 C10 175.85(16) . . . . ?
C7 C8 C9 C10 51.0(2) . . . . ?
C2 C1 C10 C18 -68.0(2) . . . . ?
C2 C1 C10 C5 54.1(2) . . . . ?
C2 C1 C10 C9 170.65(16) . . . . ?
C6 C5 C10 C1 176.14(15) . . . . ?
C4 C5 C10 C1 -55.3(2) . . . . ?
C6 C5 C10 C18 -63.4(2) . . . . ?
C4 C5 C10 C18 65.2(2) . . . . ?
C6 C5 C10 C9 58.4(2) . . . . ?
C4 C5 C10 C9 -173.01(15) . . . . ?
C11 C9 C10 C1 64.0(2) . . . . ?
C8 C9 C10 C1 -169.18(16) . . . . ?
C11 C9 C10 C18 -56.8(2) . . . . ?
C8 C9 C10 C18 70.0(2) . . . . ?
C11 C9 C10 C5 -179.62(16) . . . . ?
C8 C9 C10 C5 -52.8(2) . . . . ?
C8 C9 C11 C12 61.9(2) . . . . ?
C10 C9 C11 C12 -169.50(16) . . . . ?
C9 C11 C12 C13 -57.7(2) . . . . ?
C11 C12 C13 C14 47.8(2) . . . . ?
C11 C12 C13 C17 161.87(18) . . . . ?
C11 C12 C13 C19 -77.2(2) . . . . ?
C7 C8 C14 C15 -0.4(3) . . . . ?
C9 C8 C14 C15 -125.1(2) . . . . ?
C7 C8 C14 C13 174.81(18) . . . . ?
C9 C8 C14 C13 50.1(2) . . . . ?
C17 C13 C14 C15 8.7(2) . . . . ?
C12 C13 C14 C15 128.93(19) . . . . ?
C19 C13 C14 C15 -105.9(2) . . . . ?
C17 C13 C14 C8 -167.27(16) . . . . ?
C12 C13 C14 C8 -47.0(2) . . . . ?
C19 C13 C14 C8 78.1(2) . . . . ?
C8 C14 C15 C16 173.48(18) . . . . ?
C13 C14 C15 C16 -2.0(3) . . . . ?
C14 C15 C16 C17 -5.7(2) . . . . ?
C15 C16 C17 O17 -168.6(2) . . . . ?
C15 C16 C17 C13 11.0(2) . . . . ?
C14 C13 C17 O17 167.7(2) . . . . ?
C12 C13 C17 O17 48.2(3) . . . . ?
C19 C13 C17 O17 -75.0(3) . . . . ?
C14 C13 C17 C16 -11.9(2) . . . . ?
C12 C13 C17 C16 -131.45(19) . . . . ?
C19 C13 C17 C16 105.4(2) . . . . ?
C4 C3 O3 C20 -161.85(16) . . . . ?
C2 C3 O3 C20 76.5(2) . . . . ?
C3 O3 C20 C21 -136.70(17) . . . . ?
O3 C20 C21 C22 35.8(3) . . . . ?
O3 C20 C21 C26 -147.08(19) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C20 C21 C22 C23 176.9(2) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
C20 C21 C26 C25 -176.4(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.031


####################################################################### 
# 
# 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 
# 
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# Please retain this information to preserve the provenance of 
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data_sb983_hy
_database_code_depnum_ccdc_archive 'CCDC 2207139'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-((3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one

_chemical_name_common            
;
3β-hydroxy-5α,14α-card-(20,22)-endolide
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H34 O3'
_chemical_formula_sum            'C23 H34 O3'
_chemical_formula_weight         358.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   7.3887(2)
_cell_length_b                   13.9158(5)
_cell_length_c                   18.7736(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1930.30(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      72.1

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9160
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 10+1 runs, 2067 frames, 20/30/40 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            23035
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.954
_diffrn_reflns_theta_max         72.138
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3799
_reflns_number_gt                3724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    .
_computing_publication_material  publCIF

_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)+(0.0459P)²+0.3438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3799
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.6839(2) 0.88730(11) 0.40141(10) 0.0231(3) Uani 1 1 d . . . . .
H1A H 0.5534 0.8725 0.3964 0.028 Uiso 1 1 calc R U . . .
H1B H 0.7160 0.8804 0.4524 0.028 Uiso 1 1 calc R U . . .
C2 C 0.7165(2) 0.99219(11) 0.37857(10) 0.0248(4) Uani 1 1 d . . . . .
H2A H 0.6720 1.0015 0.3293 0.030 Uiso 1 1 calc R U . . .
H2B H 0.6475 1.0357 0.4102 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9157(2) 1.01768(11) 0.38197(9) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.9551 1.0157 0.4329 0.025 Uiso 1 1 calc R U . . .
O3 O 0.93700(17) 1.11385(8) 0.35636(7) 0.0254(3) Uani 1 1 d D . . . .
H3O H 1.045(3) 1.1266(17) 0.3517(13) 0.038 Uiso 1 1 d D U . . .
C4 C 1.0298(2) 0.94681(11) 0.34010(9) 0.0202(3) Uani 1 1 d . . . . .
H4A H 1.1594 0.9624 0.3468 0.024 Uiso 1 1 calc R U . . .
H4B H 1.0017 0.9533 0.2888 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9958(2) 0.84297(10) 0.36334(8) 0.0166(3) Uani 1 1 d . . . . .
H5 H 1.0277 0.8398 0.4151 0.020 Uiso 1 1 calc R U . . .
C6 C 1.1212(2) 0.77216(11) 0.32545(9) 0.0219(3) Uani 1 1 d . . . . .
H6A H 1.2481 0.7940 0.3301 0.026 Uiso 1 1 calc R U . . .
H6B H 1.0907 0.7700 0.2741 0.026 Uiso 1 1 calc R U . . .
C7 C 1.1018(2) 0.67175(11) 0.35755(10) 0.0213(3) Uani 1 1 d . . . . .
H7A H 1.1462 0.6726 0.4073 0.026 Uiso 1 1 calc R U . . .
H7B H 1.1776 0.6261 0.3303 0.026 Uiso 1 1 calc R U . . .
C8 C 0.9044(2) 0.63734(10) 0.35650(8) 0.0158(3) Uani 1 1 d . . . . .
H8 H 0.8666 0.6279 0.3058 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7761(2) 0.71154(10) 0.39139(8) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.8153 0.7177 0.4422 0.019 Uiso 1 1 calc R U . . .
C10 C 0.7936(2) 0.81357(11) 0.35774(8) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.5802(2) 0.67321(11) 0.39298(9) 0.0205(3) Uani 1 1 d . . . . .
H11A H 0.5033 0.7191 0.4196 0.025 Uiso 1 1 calc R U . . .
H11B H 0.5337 0.6696 0.3436 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5646(2) 0.57323(10) 0.42779(9) 0.0196(3) Uani 1 1 d . . . . .
H12A H 0.5956 0.5782 0.4790 0.024 Uiso 1 1 calc R U . . .
H12B H 0.4381 0.5504 0.4241 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6903(2) 0.50063(10) 0.39217(8) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.8835(2) 0.54196(10) 0.39595(8) 0.0159(3) Uani 1 1 d . . . . .
H14 H 0.9080 0.5557 0.4473 0.019 Uiso 1 1 calc R U . . .
C15 C 1.0050(2) 0.45779(11) 0.37554(9) 0.0217(3) Uani 1 1 d . . . . .
H15A H 1.1292 0.4668 0.3942 0.026 Uiso 1 1 calc R U . . .
H15B H 1.0108 0.4500 0.3232 0.026 Uiso 1 1 calc R U . . .
C16 C 0.9122(2) 0.37027(11) 0.41088(10) 0.0237(4) Uani 1 1 d . . . . .
H16A H 0.9824 0.3485 0.4528 0.028 Uiso 1 1 calc R U . . .
H16B H 0.9032 0.3163 0.3767 0.028 Uiso 1 1 calc R U . . .
C17 C 0.7204(2) 0.40402(11) 0.43397(9) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.7260 0.4200 0.4858 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5753(2) 0.32996(11) 0.42424(8) 0.0176(3) Uani 1 1 d . . . . .
C19 C 0.5665(2) 0.25350(11) 0.38122(9) 0.0225(3) Uani 1 1 d . . . . .
H19 H 0.6604 0.2322 0.3504 0.027 Uiso 1 1 calc R U . . .
C20 C 0.3892(2) 0.20797(11) 0.38920(9) 0.0213(3) Uani 1 1 d . . . . .
O20 O 0.32390(17) 0.13954(9) 0.35892(7) 0.0296(3) Uani 1 1 d . . . . .
O21 O 0.29385(15) 0.25632(8) 0.43987(6) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.4028(2) 0.33452(11) 0.46619(9) 0.0207(3) Uani 1 1 d . . . . .
H22A H 0.4272 0.3267 0.5177 0.025 Uiso 1 1 calc R U . . .
H22B H 0.3409 0.3968 0.4585 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7266(2) 0.81375(12) 0.28028(9) 0.0239(4) Uani 1 1 d . . . . .
H23A H 0.7963 0.7669 0.2525 0.036 Uiso 1 1 calc R U . . .
H23B H 0.5981 0.7965 0.2791 0.036 Uiso 1 1 calc R U . . .
H23C H 0.7429 0.8780 0.2598 0.036 Uiso 1 1 calc R U . . .
C24 C 0.6280(2) 0.47884(12) 0.31581(9) 0.0214(3) Uani 1 1 d . . . . .
H24A H 0.7105 0.4322 0.2941 0.032 Uiso 1 1 calc R U . . .
H24B H 0.5052 0.4522 0.3169 0.032 Uiso 1 1 calc R U . . .
H24C H 0.6284 0.5383 0.2878 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.540(2) . ?
C1 C10 1.543(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.515(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.4307(18) . ?
C3 C4 1.517(2) . ?
C3 H3 1.0000 . ?
O3 H3O 0.82(2) . ?
C4 C5 1.530(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(2) . ?
C5 C10 1.5531(19) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.535(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.528(2) . ?
C8 C9 1.547(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.542(2) . ?
C9 C10 1.5593(19) . ?
C9 H9 1.0000 . ?
C10 C23 1.536(2) . ?
C11 C12 1.541(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.526(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C24 1.536(2) . ?
C13 C14 1.541(2) . ?
C13 C17 1.5725(19) . ?
C14 C15 1.525(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.547(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.554(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.499(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.337(2) . ?
C18 C22 1.500(2) . ?
C19 C20 1.463(2) . ?
C19 H19 0.9500 . ?
C20 O20 1.209(2) . ?
C20 O21 1.361(2) . ?
O21 C22 1.4408(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 113.57(13) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.24(13) . . ?
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 108.15(13) . . ?
O3 C3 C4 111.91(13) . . ?
C2 C3 C4 111.44(13) . . ?
O3 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C3 O3 H3O 110.1(17) . . ?
C3 C4 C5 112.03(13) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 112.14(13) . . ?
C6 C5 C10 112.45(12) . . ?
C4 C5 C10 112.78(12) . . ?
C6 C5 H5 106.3 . . ?
C4 C5 H5 106.3 . . ?
C10 C5 H5 106.3 . . ?
C5 C6 C7 110.44(13) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.66(13) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C14 C8 C7 111.15(12) . . ?
C14 C8 C9 108.22(12) . . ?
C7 C8 C9 111.63(12) . . ?
C14 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C11 C9 C8 110.63(12) . . ?
C11 C9 C10 113.61(12) . . ?
C8 C9 C10 112.66(12) . . ?
C11 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C23 C10 C1 109.44(13) . . ?
C23 C10 C5 111.93(13) . . ?
C1 C10 C5 107.12(12) . . ?
C23 C10 C9 111.00(12) . . ?
C1 C10 C9 110.28(12) . . ?
C5 C10 C9 106.99(12) . . ?
C12 C11 C9 112.99(12) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.47(12) . . ?
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 . . ?
C12 C13 C24 110.93(13) . . ?
C12 C13 C14 107.24(12) . . ?
C24 C13 C14 113.23(13) . . ?
C12 C13 C17 115.69(12) . . ?
C24 C13 C17 109.84(12) . . ?
C14 C13 C17 99.48(11) . . ?
C15 C14 C8 119.08(13) . . ?
C15 C14 C13 104.32(12) . . ?
C8 C14 C13 113.30(12) . . ?
C15 C14 H14 106.5 . . ?
C8 C14 H14 106.5 . . ?
C13 C14 H14 106.5 . . ?
C14 C15 C16 103.63(12) . . ?
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 106.61(12) . . ?
C15 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C18 C17 C16 114.24(12) . . ?
C18 C17 C13 115.19(12) . . ?
C16 C17 C13 104.39(12) . . ?
C18 C17 H17 107.5 . . ?
C16 C17 H17 107.5 . . ?
C13 C17 H17 107.5 . . ?
C19 C18 C17 130.93(15) . . ?
C19 C18 C22 108.05(14) . . ?
C17 C18 C22 121.02(14) . . ?
C18 C19 C20 109.01(14) . . ?
C18 C19 H19 125.5 . . ?
C20 C19 H19 125.5 . . ?
O20 C20 O21 120.75(15) . . ?
O20 C20 C19 130.53(16) . . ?
O21 C20 C19 108.72(13) . . ?
C20 O21 C22 108.90(12) . . ?
O21 C22 C18 105.23(12) . . ?
O21 C22 H22A 110.7 . . ?
C18 C22 H22A 110.7 . . ?
O21 C22 H22B 110.7 . . ?
C18 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 -56.06(19) . . . . ?
C1 C2 C3 O3 176.80(13) . . . . ?
C1 C2 C3 C4 53.40(19) . . . . ?
O3 C3 C4 C5 -175.37(13) . . . . ?
C2 C3 C4 C5 -54.14(18) . . . . ?
C3 C4 C5 C6 -175.48(13) . . . . ?
C3 C4 C5 C10 56.35(17) . . . . ?
C4 C5 C6 C7 172.00(13) . . . . ?
C10 C5 C6 C7 -59.65(17) . . . . ?
C5 C6 C7 C8 55.16(18) . . . . ?
C6 C7 C8 C14 -173.77(13) . . . . ?
C6 C7 C8 C9 -52.84(18) . . . . ?
C14 C8 C9 C11 -54.62(16) . . . . ?
C7 C8 C9 C11 -177.24(13) . . . . ?
C14 C8 C9 C10 177.00(12) . . . . ?
C7 C8 C9 C10 54.37(17) . . . . ?
C2 C1 C10 C23 -66.28(18) . . . . ?
C2 C1 C10 C5 55.26(17) . . . . ?
C2 C1 C10 C9 171.35(14) . . . . ?
C6 C5 C10 C23 -63.15(17) . . . . ?
C4 C5 C10 C23 64.86(17) . . . . ?
C6 C5 C10 C1 176.90(13) . . . . ?
C4 C5 C10 C1 -55.09(17) . . . . ?
C6 C5 C10 C9 58.65(16) . . . . ?
C4 C5 C10 C9 -173.34(12) . . . . ?
C11 C9 C10 C23 -60.09(17) . . . . ?
C8 C9 C10 C23 66.73(16) . . . . ?
C11 C9 C10 C1 61.37(17) . . . . ?
C8 C9 C10 C1 -171.82(12) . . . . ?
C11 C9 C10 C5 177.54(12) . . . . ?
C8 C9 C10 C5 -55.65(16) . . . . ?
C8 C9 C11 C12 53.33(18) . . . . ?
C10 C9 C11 C12 -178.80(13) . . . . ?
C9 C11 C12 C13 -54.85(18) . . . . ?
C11 C12 C13 C24 -67.98(16) . . . . ?
C11 C12 C13 C14 56.14(17) . . . . ?
C11 C12 C13 C17 166.06(13) . . . . ?
C7 C8 C14 C15 -52.88(18) . . . . ?
C9 C8 C14 C15 -175.79(13) . . . . ?
C7 C8 C14 C13 -176.09(13) . . . . ?
C9 C8 C14 C13 61.00(16) . . . . ?
C12 C13 C14 C15 167.49(12) . . . . ?
C24 C13 C14 C15 -69.81(15) . . . . ?
C17 C13 C14 C15 46.69(14) . . . . ?
C12 C13 C14 C8 -61.51(16) . . . . ?
C24 C13 C14 C8 61.19(16) . . . . ?
C17 C13 C14 C8 177.69(12) . . . . ?
C8 C14 C15 C16 -165.41(13) . . . . ?
C13 C14 C15 C16 -37.88(16) . . . . ?
C14 C15 C16 C17 13.27(17) . . . . ?
C15 C16 C17 C18 142.05(14) . . . . ?
C15 C16 C17 C13 15.36(16) . . . . ?
C12 C13 C17 C18 82.15(16) . . . . ?
C24 C13 C17 C18 -44.37(18) . . . . ?
C14 C13 C17 C18 -163.41(13) . . . . ?
C12 C13 C17 C16 -151.75(13) . . . . ?
C24 C13 C17 C16 81.73(15) . . . . ?
C14 C13 C17 C16 -37.31(14) . . . . ?
C16 C17 C18 C19 -23.0(2) . . . . ?
C13 C17 C18 C19 97.8(2) . . . . ?
C16 C17 C18 C22 157.59(14) . . . . ?
C13 C17 C18 C22 -81.54(18) . . . . ?
C17 C18 C19 C20 -176.33(15) . . . . ?
C22 C18 C19 C20 3.10(18) . . . . ?
C18 C19 C20 O20 177.44(17) . . . . ?
C18 C19 C20 O21 -2.31(18) . . . . ?
O20 C20 O21 C22 -179.34(14) . . . . ?
C19 C20 O21 C22 0.43(17) . . . . ?
C20 O21 C22 C18 1.35(16) . . . . ?
C19 C18 C22 O21 -2.80(17) . . . . ?
C17 C18 C22 O21 176.70(13) . . . . ?

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
O3 H3O O20 0.82(2) 2.07(2) 2.8813(18) 168(2) 1_665
C19 H19 O3 0.95 2.63 3.389(2) 137.5 1_545
C22 H22A O3 0.99 2.51 3.417(2) 152.9 4_466
O3 H3O O20 0.82(2) 2.07(2) 2.8813(18) 168(2) 1_665
C19 H19 O3 0.95 2.63 3.389(2) 137.5 1_545
C22 H22A O3 0.99 2.51 3.417(2) 152.9 4_466

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.034




#==============================================================================

####################################################################### 
# 
# 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_sb1119_hy
_database_code_depnum_ccdc_archive 'CCDC 2207137'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3S,5S,8R,9R,10S,13S,14S)-3-(benzyloxy)-14-hydroxy-8,10,13-trimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

_chemical_name_common            
;
3β-benzyloxy-14β-hydroxy-5α-androst-17-one
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H36 O3'
_chemical_formula_sum            'C26 H36 O3'
_chemical_formula_weight         396.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   6.4304(2)
_cell_length_b                   10.3893(3)
_cell_length_c                   31.1434(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2080.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8164
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      72.2

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.629
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8064
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 7+1 runs, 1396 frames, 20/60 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18135
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         72.244
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4089
_reflns_number_gt                3793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  publCIF
_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)+(0.0537P)²+0.5598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The absolute configuration has not been established by 
 anomalous dispersion effects in diffraction measurement
 on the crystal. The enantiomer has been assigned by
 reference to an unchanging chiral centre in the synthetic
 procedure.
;
_refine_ls_abs_structure_Flack   -0.08(15)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4089
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.4402(4) 0.2353(2) 0.35544(8) 0.0193(5) Uani 1 1 d . . . . .
H1A H 0.4074 0.1541 0.3403 0.023 Uiso 1 1 calc R U . . .
H1B H 0.3501 0.2402 0.3812 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3903(4) 0.3493(2) 0.32573(8) 0.0207(6) Uani 1 1 d . . . . .
H2A H 0.4680 0.3393 0.2985 0.025 Uiso 1 1 calc R U . . .
H2B H 0.2399 0.3488 0.3189 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4471(4) 0.4770(2) 0.34621(8) 0.0194(5) Uani 1 1 d . . . . .
H3 H 0.3558 0.4906 0.3718 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6718(4) 0.4785(2) 0.36092(8) 0.0192(5) Uani 1 1 d . . . . .
H4A H 0.7010 0.5603 0.3761 0.023 Uiso 1 1 calc R U . . .
H4B H 0.7646 0.4736 0.3356 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7166(4) 0.3644(2) 0.39111(8) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.6181 0.3730 0.4158 0.021 Uiso 1 1 calc R U . . .
C6 C 0.9347(4) 0.3702(2) 0.41005(8) 0.0205(5) Uani 1 1 d . . . . .
H6A H 0.9556 0.4545 0.4242 0.025 Uiso 1 1 calc R U . . .
H6B H 1.0384 0.3623 0.3867 0.025 Uiso 1 1 calc R U . . .
C7 C 0.9689(4) 0.2619(2) 0.44291(9) 0.0220(6) Uani 1 1 d . . . . .
H7A H 1.1154 0.2634 0.4527 0.026 Uiso 1 1 calc R U . . .
H7B H 0.8792 0.2773 0.4682 0.026 Uiso 1 1 calc R U . . .
C8 C 0.9194(4) 0.1287(2) 0.42411(8) 0.0165(5) Uani 1 1 d . . . . .
H8 H 1.0190 0.1141 0.3999 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6988(4) 0.1260(2) 0.40464(8) 0.0160(5) Uani 1 1 d . . . . .
H9 H 0.5996 0.1460 0.4285 0.019 Uiso 1 1 calc R U . . .
C10 C 0.6691(4) 0.2323(2) 0.36981(8) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.6455(4) -0.0096(2) 0.38857(8) 0.0183(5) Uani 1 1 d . . . . .
H11A H 0.5009 -0.0107 0.3777 0.022 Uiso 1 1 calc R U . . .
H11B H 0.7390 -0.0324 0.3645 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6682(4) -0.1092(2) 0.42421(8) 0.0193(5) Uani 1 1 d . . . . .
H12A H 0.6312 -0.1952 0.4128 0.023 Uiso 1 1 calc R U . . .
H12B H 0.5701 -0.0884 0.4477 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8928(4) -0.1134(2) 0.44245(8) 0.0176(5) Uani 1 1 d . . . . .
C14 C 0.9604(4) 0.0228(2) 0.45748(8) 0.0180(5) Uani 1 1 d . . . . .
O14 O 1.1813(3) 0.02696(17) 0.46494(6) 0.0222(4) Uani 1 1 d D . . . .
H14 H 1.219(6) -0.034(3) 0.4811(10) 0.033 Uiso 1 1 d D U . . .
C15 C 0.8461(5) 0.0396(2) 0.50053(8) 0.0203(5) Uani 1 1 d . . . . .
H15A H 0.7004 0.0670 0.4958 0.024 Uiso 1 1 calc R U . . .
H15B H 0.9169 0.1044 0.5187 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8546(5) -0.0947(2) 0.52155(8) 0.0214(5) Uani 1 1 d . . . . .
H16A H 0.9778 -0.1025 0.5404 0.026 Uiso 1 1 calc R U . . .
H16B H 0.7279 -0.1108 0.5388 0.026 Uiso 1 1 calc R U . . .
C17 C 0.8683(4) -0.1878(2) 0.48446(8) 0.0178(5) Uani 1 1 d . . . . .
O17 O 0.8527(3) -0.30445(17) 0.48689(6) 0.0227(4) Uani 1 1 d . . . . .
C18 C 0.8083(4) 0.2064(2) 0.33048(8) 0.0205(5) Uani 1 1 d . . . . .
H18A H 0.9543 0.2044 0.3395 0.031 Uiso 1 1 calc R U . . .
H18B H 0.7708 0.1234 0.3177 0.031 Uiso 1 1 calc R U . . .
H18C H 0.7884 0.2750 0.3093 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0409(5) -0.1782(2) 0.41110(8) 0.0221(6) Uani 1 1 d . . . . .
H19A H 1.0507 -0.1265 0.3848 0.033 Uiso 1 1 calc R U . . .
H19B H 1.1789 -0.1855 0.4242 0.033 Uiso 1 1 calc R U . . .
H19C H 0.9886 -0.2642 0.4040 0.033 Uiso 1 1 calc R U . . .
O3 O 0.4003(3) 0.57445(16) 0.31497(6) 0.0218(4) Uani 1 1 d . . . . .
C20 C 0.4101(5) 0.7020(2) 0.33113(8) 0.0218(6) Uani 1 1 d . . . . .
H20A H 0.5547 0.7344 0.3294 0.026 Uiso 1 1 calc R U . . .
H20B H 0.3667 0.7032 0.3616 0.026 Uiso 1 1 calc R U . . .
C21 C 0.2678(4) 0.7870(2) 0.30491(8) 0.0202(5) Uani 1 1 d . . . . .
C22 C 0.3352(5) 0.9043(2) 0.28854(8) 0.0232(6) Uani 1 1 d . . . . .
H22 H 0.4753 0.9305 0.2927 0.028 Uiso 1 1 calc R U . . .
C23 C 0.1986(5) 0.9836(3) 0.26604(9) 0.0272(6) Uani 1 1 d . . . . .
H23 H 0.2453 1.0642 0.2553 0.033 Uiso 1 1 calc R U . . .
C24 C -0.0042(5) 0.9456(3) 0.25931(8) 0.0260(6) Uani 1 1 d . . . . .
H24 H -0.0971 0.9996 0.2439 0.031 Uiso 1 1 calc R U . . .
C25 C -0.0718(5) 0.8282(3) 0.27509(8) 0.0250(6) Uani 1 1 d . . . . .
H25 H -0.2110 0.8013 0.2702 0.030 Uiso 1 1 calc R U . . .
C26 C 0.0621(5) 0.7499(2) 0.29796(8) 0.0217(5) Uani 1 1 d . . . . .
H26 H 0.0136 0.6702 0.3090 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.537(3) . ?
C1 C10 1.539(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.436(3) . ?
C3 C4 1.516(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.523(4) . ?
C5 C10 1.554(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.537(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.536(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.536(3) . ?
C8 C9 1.543(3) . ?
C8 H8 1.0000 . ?
C9 C11 1.534(3) . ?
C9 C10 1.560(3) . ?
C9 H9 1.0000 . ?
C10 C18 1.541(3) . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.552(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C19 1.521(4) . ?
C13 C17 1.528(3) . ?
C13 C14 1.553(3) . ?
C14 O14 1.440(3) . ?
C14 C15 1.539(4) . ?
O14 H14 0.84(2) . ?
C15 C16 1.542(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.218(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O3 C20 1.419(3) . ?
C20 C21 1.512(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.391(4) . ?
C21 C26 1.394(4) . ?
C22 C23 1.393(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 113.0(2) . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C10 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 111.8(2) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O3 C3 C4 113.4(2) . . ?
O3 C3 C2 106.33(19) . . ?
C4 C3 C2 111.5(2) . . ?
O3 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C3 C4 C5 110.8(2) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 112.2(2) . . ?
C6 C5 C10 112.4(2) . . ?
C4 C5 C10 112.47(19) . . ?
C6 C5 H5 106.4 . . ?
C4 C5 H5 106.4 . . ?
C10 C5 H5 106.4 . . ?
C5 C6 C7 111.2(2) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 112.1(2) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C14 110.58(19) . . ?
C7 C8 C9 110.93(19) . . ?
C14 C8 C9 114.2(2) . . ?
C7 C8 H8 106.9 . . ?
C14 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
C11 C9 C8 110.5(2) . . ?
C11 C9 C10 113.35(19) . . ?
C8 C9 C10 111.9(2) . . ?
C11 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C1 C10 C18 109.2(2) . . ?
C1 C10 C5 107.1(2) . . ?
C18 C10 C5 112.3(2) . . ?
C1 C10 C9 109.5(2) . . ?
C18 C10 C9 111.0(2) . . ?
C5 C10 C9 107.71(19) . . ?
C12 C11 C9 111.38(19) . . ?
C12 C11 H11A 109.4 . . ?
C9 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C9 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 112.0(2) . . ?
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 . . ?
C19 C13 C17 113.0(2) . . ?
C19 C13 C12 111.1(2) . . ?
C17 C13 C12 103.4(2) . . ?
C19 C13 C14 114.9(2) . . ?
C17 C13 C14 103.42(19) . . ?
C12 C13 C14 110.2(2) . . ?
O14 C14 C8 104.9(2) . . ?
O14 C14 C15 109.1(2) . . ?
C8 C14 C15 115.2(2) . . ?
O14 C14 C13 110.6(2) . . ?
C8 C14 C13 113.63(19) . . ?
C15 C14 C13 103.4(2) . . ?
C14 O14 H14 111(3) . . ?
C14 C15 C16 104.5(2) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 104.91(19) . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16B 110.8 . . ?
C15 C16 H16B 110.8 . . ?
H16A C16 H16B 108.8 . . ?
O17 C17 C16 125.8(2) . . ?
O17 C17 C13 124.4(2) . . ?
C16 C17 C13 109.7(2) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O3 C3 114.11(18) . . ?
O3 C20 C21 109.1(2) . . ?
O3 C20 H20A 109.9 . . ?
C21 C20 H20A 109.9 . . ?
O3 C20 H20B 109.9 . . ?
C21 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C20 121.4(3) . . ?
C26 C21 C20 119.8(2) . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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 -55.8(3) . . . . ?
C1 C2 C3 O3 178.0(2) . . . . ?
C1 C2 C3 C4 53.9(3) . . . . ?
O3 C3 C4 C5 -174.77(19) . . . . ?
C2 C3 C4 C5 -54.8(3) . . . . ?
C3 C4 C5 C6 -174.3(2) . . . . ?
C3 C4 C5 C10 57.7(3) . . . . ?
C4 C5 C6 C7 175.2(2) . . . . ?
C10 C5 C6 C7 -56.8(3) . . . . ?
C5 C6 C7 C8 53.8(3) . . . . ?
C6 C7 C8 C14 178.6(2) . . . . ?
C6 C7 C8 C9 -53.6(3) . . . . ?
C7 C8 C9 C11 -176.4(2) . . . . ?
C14 C8 C9 C11 -50.6(3) . . . . ?
C7 C8 C9 C10 56.3(3) . . . . ?
C14 C8 C9 C10 -177.9(2) . . . . ?
C2 C1 C10 C18 -66.2(3) . . . . ?
C2 C1 C10 C5 55.6(3) . . . . ?
C2 C1 C10 C9 172.1(2) . . . . ?
C6 C5 C10 C1 175.4(2) . . . . ?
C4 C5 C10 C1 -56.7(3) . . . . ?
C6 C5 C10 C18 -64.8(3) . . . . ?
C4 C5 C10 C18 63.1(3) . . . . ?
C6 C5 C10 C9 57.7(3) . . . . ?
C4 C5 C10 C9 -174.4(2) . . . . ?
C11 C9 C10 C1 60.8(3) . . . . ?
C8 C9 C10 C1 -173.42(19) . . . . ?
C11 C9 C10 C18 -59.8(3) . . . . ?
C8 C9 C10 C18 66.0(3) . . . . ?
C11 C9 C10 C5 177.0(2) . . . . ?
C8 C9 C10 C5 -57.2(3) . . . . ?
C8 C9 C11 C12 55.9(3) . . . . ?
C10 C9 C11 C12 -177.6(2) . . . . ?
C9 C11 C12 C13 -59.5(3) . . . . ?
C11 C12 C13 C19 -73.7(3) . . . . ?
C11 C12 C13 C17 164.8(2) . . . . ?
C11 C12 C13 C14 54.8(3) . . . . ?
C7 C8 C14 O14 -64.9(3) . . . . ?
C9 C8 C14 O14 169.11(19) . . . . ?
C7 C8 C14 C15 55.0(3) . . . . ?
C9 C8 C14 C15 -70.9(3) . . . . ?
C7 C8 C14 C13 174.2(2) . . . . ?
C9 C8 C14 C13 48.2(3) . . . . ?
C19 C13 C14 O14 -40.1(3) . . . . ?
C17 C13 C14 O14 83.5(2) . . . . ?
C12 C13 C14 O14 -166.54(19) . . . . ?
C19 C13 C14 C8 77.6(3) . . . . ?
C17 C13 C14 C8 -158.8(2) . . . . ?
C12 C13 C14 C8 -48.9(3) . . . . ?
C19 C13 C14 C15 -156.8(2) . . . . ?
C17 C13 C14 C15 -33.2(2) . . . . ?
C12 C13 C14 C15 76.8(2) . . . . ?
O14 C14 C15 C16 -80.0(2) . . . . ?
C8 C14 C15 C16 162.3(2) . . . . ?
C13 C14 C15 C16 37.7(3) . . . . ?
C14 C15 C16 C17 -27.2(3) . . . . ?
C15 C16 C17 O17 -170.5(3) . . . . ?
C15 C16 C17 C13 6.3(3) . . . . ?
C19 C13 C17 O17 -41.4(4) . . . . ?
C12 C13 C17 O17 78.8(3) . . . . ?
C14 C13 C17 O17 -166.3(3) . . . . ?
C19 C13 C17 C16 141.7(2) . . . . ?
C12 C13 C17 C16 -98.1(2) . . . . ?
C14 C13 C17 C16 16.8(3) . . . . ?
C4 C3 O3 C20 -67.4(3) . . . . ?
C2 C3 O3 C20 169.7(2) . . . . ?
C3 O3 C20 C21 -153.4(2) . . . . ?
O3 C20 C21 C22 -131.3(2) . . . . ?
O3 C20 C21 C26 50.9(3) . . . . ?
C26 C21 C22 C23 0.7(4) . . . . ?
C20 C21 C22 C23 -177.2(2) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C22 C21 C26 C25 0.3(4) . . . . ?
C20 C21 C26 C25 178.2(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
O14 H14 O17 0.84(2) 2.14(2) 2.968(3) 170(3) 4_546

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045


####################################################################### 
# 
# 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_sb1120_hy
_database_code_depnum_ccdc_archive 'CCDC 2207138'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3S,5S,8R,9R,10S,13S,14R)-3-(benzyloxy)-14-hydroxy-8,10,13-trimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

_chemical_name_common            
;
3β-benzyloxy-14α-hydroxy-5α-androst-17-one
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H36 O3'
_chemical_formula_sum            'C26 H36 O3'
_chemical_formula_weight         396.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   6.11120(10)
_cell_length_b                   10.7555(2)
_cell_length_c                   32.6186(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2143.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.611
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7555
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 8+1 runs, 1160 frames, 4/12 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16677
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         72.110
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4202
_reflns_number_gt                4125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  publCIF

_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)+(0.0621P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.8243(4) 0.6550(2) 0.55555(6) 0.0292(4) Uani 1 1 d . . . . .
H1A H 0.8877 0.7391 0.5522 0.035 Uiso 1 1 calc R U . . .
H1B H 0.9450 0.5974 0.5625 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7221(4) 0.6145(2) 0.51504(6) 0.0329(5) Uani 1 1 d . . . . .
H2A H 0.6115 0.6768 0.5066 0.039 Uiso 1 1 calc R U . . .
H2B H 0.8370 0.6120 0.4937 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6143(4) 0.4880(2) 0.51789(6) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.7295 0.4231 0.5219 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4522(4) 0.4826(2) 0.55361(6) 0.0292(4) Uani 1 1 d . . . . .
H4A H 0.3983 0.3963 0.5567 0.035 Uiso 1 1 calc R U . . .
H4B H 0.3251 0.5364 0.5474 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5572(3) 0.52512(17) 0.59398(6) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.6808 0.4666 0.5996 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3989(3) 0.51343(19) 0.63001(6) 0.0268(4) Uani 1 1 d . . . . .
H6A H 0.2763 0.5726 0.6263 0.032 Uiso 1 1 calc R U . . .
H6B H 0.3374 0.4283 0.6307 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5148(3) 0.54050(18) 0.67046(6) 0.0247(4) Uani 1 1 d . . . . .
H7A H 0.6234 0.4742 0.6759 0.030 Uiso 1 1 calc R U . . .
H7B H 0.4063 0.5393 0.6930 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6313(3) 0.66675(16) 0.67011(6) 0.0203(4) Uani 1 1 d . . . . .
H8 H 0.5168 0.7331 0.6691 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7814(3) 0.68288(16) 0.63215(5) 0.0198(4) Uani 1 1 d . . . . .
H9 H 0.8986 0.6184 0.6344 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6582(3) 0.65736(17) 0.59136(6) 0.0222(4) Uani 1 1 d . . . . .
C11 C 0.8974(3) 0.81075(19) 0.63293(6) 0.0263(4) Uani 1 1 d . . . . .
H11A H 0.9995 0.8159 0.6094 0.032 Uiso 1 1 calc R U . . .
H11B H 0.7865 0.8771 0.6295 0.032 Uiso 1 1 calc R U . . .
C12 C 1.0251(3) 0.83383(18) 0.67277(6) 0.0258(4) Uani 1 1 d . . . . .
H12A H 1.1486 0.7746 0.6747 0.031 Uiso 1 1 calc R U . . .
H12B H 1.0858 0.9192 0.6727 0.031 Uiso 1 1 calc R U . . .
C13 C 0.8743(3) 0.81741(16) 0.70960(6) 0.0219(4) Uani 1 1 d . . . . .
C14 C 0.7680(3) 0.68726(16) 0.70869(6) 0.0194(4) Uani 1 1 d . . . . .
O14 O 0.9549(2) 0.60476(12) 0.70918(4) 0.0239(3) Uani 1 1 d D . . . .
H14 H 0.904(4) 0.534(2) 0.7149(8) 0.036 Uiso 1 1 d D U . . .
C15 C 0.6578(3) 0.67646(19) 0.75098(6) 0.0263(4) Uani 1 1 d . . . . .
H15A H 0.6339 0.5884 0.7586 0.032 Uiso 1 1 calc R U . . .
H15B H 0.5159 0.7209 0.7515 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8264(3) 0.73912(19) 0.77969(6) 0.0287(4) Uani 1 1 d . . . . .
H16A H 0.7523 0.7955 0.7992 0.034 Uiso 1 1 calc R U . . .
H16B H 0.9088 0.6758 0.7954 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9788(3) 0.81165(17) 0.75175(6) 0.0261(4) Uani 1 1 d . . . . .
O17 O 1.1514(2) 0.85885(14) 0.76209(5) 0.0327(3) Uani 1 1 d . . . . .
C18 C 0.4843(4) 0.75753(19) 0.58332(6) 0.0305(4) Uani 1 1 d . . . . .
H18A H 0.3794 0.7588 0.6060 0.046 Uiso 1 1 calc R U . . .
H18B H 0.5553 0.8390 0.5811 0.046 Uiso 1 1 calc R U . . .
H18C H 0.4073 0.7387 0.5577 0.046 Uiso 1 1 calc R U . . .
C19 C 0.7060(4) 0.92405(18) 0.71236(7) 0.0296(4) Uani 1 1 d . . . . .
H19A H 0.6314 0.9332 0.6859 0.044 Uiso 1 1 calc R U . . .
H19B H 0.5982 0.9049 0.7337 0.044 Uiso 1 1 calc R U . . .
H19C H 0.7814 1.0017 0.7192 0.044 Uiso 1 1 calc R U . . .
O3 O 0.5098(3) 0.46850(14) 0.47914(4) 0.0370(4) Uani 1 1 d . . . . .
C20 C 0.4539(5) 0.3435(2) 0.47055(7) 0.0422(6) Uani 1 1 d . . . . .
H20A H 0.3863 0.3045 0.4950 0.051 Uiso 1 1 calc R U . . .
H20B H 0.5866 0.2956 0.4632 0.051 Uiso 1 1 calc R U . . .
C21 C 0.2943(4) 0.3433(2) 0.43520(7) 0.0334(5) Uani 1 1 d . . . . .
C22 C 0.0893(4) 0.3981(2) 0.44027(8) 0.0423(6) Uani 1 1 d . . . . .
H22 H 0.0511 0.4318 0.4662 0.051 Uiso 1 1 calc R U . . .
C23 C -0.0568(5) 0.4045(2) 0.40906(10) 0.0501(6) Uani 1 1 d . . . . .
H23 H -0.1952 0.4427 0.4132 0.060 Uiso 1 1 calc R U . . .
C24 C -0.0049(5) 0.3560(2) 0.37181(8) 0.0496(7) Uani 1 1 d . . . . .
H24 H -0.1084 0.3611 0.3501 0.060 Uiso 1 1 calc R U . . .
C25 C 0.1954(5) 0.2991(2) 0.36466(8) 0.0485(7) Uani 1 1 d . . . . .
H25 H 0.2293 0.2648 0.3386 0.058 Uiso 1 1 calc R U . . .
C26 C 0.3484(5) 0.2937(2) 0.39739(8) 0.0436(6) Uani 1 1 d . . . . .
H26 H 0.4875 0.2561 0.3933 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.525(3) . ?
C1 C10 1.548(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.431(2) . ?
C3 C4 1.530(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.535(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(3) . ?
C5 C10 1.553(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.526(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.533(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.526(2) . ?
C8 C9 1.551(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.547(3) . ?
C9 C10 1.553(2) . ?
C9 H9 1.0000 . ?
C10 C18 1.536(3) . ?
C11 C12 1.536(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.517(3) . ?
C13 C19 1.543(3) . ?
C13 C14 1.543(2) . ?
C14 O14 1.447(2) . ?
C14 C15 1.539(2) . ?
O14 H14 0.84(2) . ?
C15 C16 1.547(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.218(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O3 C20 1.415(3) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.384(3) . ?
C21 C22 1.394(4) . ?
C22 C23 1.356(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.360(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.420(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 112.97(17) . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C10 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 112.43(17) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O3 C3 C2 105.75(16) . . ?
O3 C3 C4 112.24(18) . . ?
C2 C3 C4 111.24(17) . . ?
O3 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C3 C4 C5 111.82(17) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 111.77(15) . . ?
C6 C5 C10 111.69(15) . . ?
C4 C5 C10 113.07(15) . . ?
C6 C5 H5 106.6 . . ?
C4 C5 H5 106.6 . . ?
C10 C5 H5 106.6 . . ?
C7 C6 C5 110.81(15) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 112.23(15) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C14 C8 C7 112.09(14) . . ?
C14 C8 C9 108.57(14) . . ?
C7 C8 C9 112.31(15) . . ?
C14 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C11 C9 C8 110.93(14) . . ?
C11 C9 C10 113.15(14) . . ?
C8 C9 C10 112.18(14) . . ?
C11 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C18 C10 C1 109.64(16) . . ?
C18 C10 C5 112.14(15) . . ?
C1 C10 C5 106.70(15) . . ?
C18 C10 C9 110.96(15) . . ?
C1 C10 C9 109.37(14) . . ?
C5 C10 C9 107.90(14) . . ?
C12 C11 C9 112.97(15) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.91(15) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C17 C13 C12 117.66(16) . . ?
C17 C13 C19 104.96(15) . . ?
C12 C13 C19 111.28(16) . . ?
C17 C13 C14 99.07(14) . . ?
C12 C13 C14 110.13(14) . . ?
C19 C13 C14 113.25(15) . . ?
O14 C14 C8 110.65(14) . . ?
O14 C14 C15 106.80(14) . . ?
C8 C14 C15 119.24(15) . . ?
O14 C14 C13 102.94(13) . . ?
C8 C14 C13 112.17(14) . . ?
C15 C14 C13 103.60(14) . . ?
C14 O14 H14 105.3(19) . . ?
C14 C15 C16 102.60(15) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 105.61(16) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
O17 C17 C13 126.75(19) . . ?
O17 C17 C16 125.38(19) . . ?
C13 C17 C16 107.85(17) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O3 C3 114.95(16) . . ?
O3 C20 C21 107.95(18) . . ?
O3 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O3 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C26 C21 C22 118.9(2) . . ?
C26 C21 C20 121.8(2) . . ?
C22 C21 C20 119.3(2) . . ?
C23 C22 C21 121.6(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 121.6(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 118.2(2) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C21 C26 C25 119.8(3) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?

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 -56.8(2) . . . . ?
C1 C2 C3 O3 174.79(18) . . . . ?
C1 C2 C3 C4 52.7(2) . . . . ?
O3 C3 C4 C5 -170.36(16) . . . . ?
C2 C3 C4 C5 -52.1(2) . . . . ?
C3 C4 C5 C6 -177.10(17) . . . . ?
C3 C4 C5 C10 55.8(2) . . . . ?
C4 C5 C6 C7 172.87(16) . . . . ?
C10 C5 C6 C7 -59.3(2) . . . . ?
C5 C6 C7 C8 54.1(2) . . . . ?
C6 C7 C8 C14 -173.63(15) . . . . ?
C6 C7 C8 C9 -51.1(2) . . . . ?
C14 C8 C9 C11 -55.12(18) . . . . ?
C7 C8 C9 C11 -179.63(15) . . . . ?
C14 C8 C9 C10 177.27(14) . . . . ?
C7 C8 C9 C10 52.75(19) . . . . ?
C2 C1 C10 C18 -65.3(2) . . . . ?
C2 C1 C10 C5 56.3(2) . . . . ?
C2 C1 C10 C9 172.81(16) . . . . ?
C6 C5 C10 C18 -63.2(2) . . . . ?
C4 C5 C10 C18 63.9(2) . . . . ?
C6 C5 C10 C1 176.77(15) . . . . ?
C4 C5 C10 C1 -56.1(2) . . . . ?
C6 C5 C10 C9 59.33(18) . . . . ?
C4 C5 C10 C9 -173.56(15) . . . . ?
C11 C9 C10 C18 -58.8(2) . . . . ?
C8 C9 C10 C18 67.61(19) . . . . ?
C11 C9 C10 C1 62.26(19) . . . . ?
C8 C9 C10 C1 -171.32(15) . . . . ?
C11 C9 C10 C5 177.96(15) . . . . ?
C8 C9 C10 C5 -55.62(18) . . . . ?
C8 C9 C11 C12 54.8(2) . . . . ?
C10 C9 C11 C12 -178.15(15) . . . . ?
C9 C11 C12 C13 -54.7(2) . . . . ?
C11 C12 C13 C17 168.41(16) . . . . ?
C11 C12 C13 C19 -70.5(2) . . . . ?
C11 C12 C13 C14 56.0(2) . . . . ?
C7 C8 C14 O14 69.09(18) . . . . ?
C9 C8 C14 O14 -55.55(18) . . . . ?
C7 C8 C14 C15 -55.3(2) . . . . ?
C9 C8 C14 C15 -179.95(15) . . . . ?
C7 C8 C14 C13 -176.58(15) . . . . ?
C9 C8 C14 C13 58.78(18) . . . . ?
C17 C13 C14 O14 -65.25(16) . . . . ?
C12 C13 C14 O14 58.75(17) . . . . ?
C19 C13 C14 O14 -175.93(16) . . . . ?
C17 C13 C14 C8 175.78(15) . . . . ?
C12 C13 C14 C8 -60.22(19) . . . . ?
C19 C13 C14 C8 65.10(19) . . . . ?
C17 C13 C14 C15 45.90(16) . . . . ?
C12 C13 C14 C15 169.90(15) . . . . ?
C19 C13 C14 C15 -64.78(19) . . . . ?
O14 C14 C15 C16 69.41(18) . . . . ?
C8 C14 C15 C16 -164.35(16) . . . . ?
C13 C14 C15 C16 -38.88(18) . . . . ?
C14 C15 C16 C17 16.0(2) . . . . ?
C12 C13 C17 O17 27.2(3) . . . . ?
C19 C13 C17 O17 -97.2(2) . . . . ?
C14 C13 C17 O17 145.66(19) . . . . ?
C12 C13 C17 C16 -154.48(16) . . . . ?
C19 C13 C17 C16 81.18(18) . . . . ?
C14 C13 C17 C16 -35.98(18) . . . . ?
C15 C16 C17 O17 -168.72(19) . . . . ?
C15 C16 C17 C13 12.9(2) . . . . ?
C2 C3 O3 C20 162.4(2) . . . . ?
C4 C3 O3 C20 -76.1(2) . . . . ?
C3 O3 C20 C21 164.78(19) . . . . ?
O3 C20 C21 C26 113.5(2) . . . . ?
O3 C20 C21 C22 -64.4(3) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
C20 C21 C22 C23 177.6(2) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C20 C21 C26 C25 -178.0(2) . . . . ?
C24 C25 C26 C21 0.6(3) . . . . ?

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
O14 H14 O17 0.84(2) 2.06(2) 2.880(2) 166(3) 3_746

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040


