# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_sb953_hy
_database_code_depnum_ccdc_archive 'CCDC 1822521'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-1,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H28 O'
_chemical_formula_sum            'C19 H28 O'
_chemical_formula_weight         272.41

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      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                   6.4188(2)
_cell_length_b                   8.9046(3)
_cell_length_c                   26.9419(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1539.91(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      5.2
_cell_measurement_theta_max      71.8

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.527
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8475
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 8+1 runs, 1465 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            13756
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.281
_diffrn_reflns_theta_max         72.051
_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 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3011
_reflns_number_gt                2981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.994

_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)+(0.0321P)²+0.4207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.7565(3) 0.9305(2) 0.37939(8) 0.0305(4) Uani 1 1 d . . . . .
H1A H 0.6679 0.9797 0.4047 0.037 Uiso 1 1 calc R U . . .
H1B H 0.8766 0.8846 0.3967 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8350(3) 1.0474(2) 0.34389(9) 0.0364(5) Uani 1 1 d . . . . .
H2 H 0.8715 1.1437 0.3564 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8551(3) 1.0209(2) 0.29567(10) 0.0468(6) Uani 1 1 d . . . . .
H3 H 0.9020 1.1004 0.2750 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8081(3) 0.8733(2) 0.27223(7) 0.0351(4) Uani 1 1 d . . . . .
H4A H 0.9284 0.8430 0.2515 0.042 Uiso 1 1 calc R U . . .
H4B H 0.6864 0.8851 0.2500 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7619(3) 0.74765(19) 0.30951(6) 0.0243(4) Uani 1 1 d . . . . .
H5 H 0.8989 0.7153 0.3236 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6667(3) 0.6101(2) 0.28441(6) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.7609 0.5746 0.2578 0.032 Uiso 1 1 calc R U . . .
H6B H 0.5323 0.6383 0.2690 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6308(3) 0.48339(18) 0.32174(6) 0.0239(4) Uani 1 1 d . . . . .
H7A H 0.7666 0.4490 0.3349 0.029 Uiso 1 1 calc R U . . .
H7B H 0.5638 0.3974 0.3048 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4929(2) 0.53558(17) 0.36468(5) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.3541 0.5659 0.3511 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5940(2) 0.67350(17) 0.39029(6) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.7362 0.6400 0.4007 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6293(2) 0.80540(18) 0.35359(6) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.4818(3) 0.71991(18) 0.43853(6) 0.0228(3) Uani 1 1 d . . . . .
H11A H 0.5639 0.7993 0.4552 0.027 Uiso 1 1 calc R U . . .
H11B H 0.3440 0.7628 0.4300 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4511(3) 0.58857(19) 0.47450(6) 0.0238(4) Uani 1 1 d . . . . .
H12A H 0.5883 0.5516 0.4860 0.029 Uiso 1 1 calc R U . . .
H12B H 0.3711 0.6226 0.5038 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3343(2) 0.46274(18) 0.44842(6) 0.0187(3) Uani 1 1 d . . . . .
C14 C 0.4605(2) 0.41140(17) 0.40291(6) 0.0175(3) Uani 1 1 d . . . . .
H14 H 0.6021 0.3836 0.4154 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3547(3) 0.26440(18) 0.38738(6) 0.0240(4) Uani 1 1 d . . . . .
H15A H 0.4498 0.2012 0.3674 0.029 Uiso 1 1 calc R U . . .
H15B H 0.2264 0.2841 0.3680 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3033(3) 0.18905(19) 0.43757(6) 0.0265(4) Uani 1 1 d . . . . .
H16A H 0.1636 0.1421 0.4365 0.032 Uiso 1 1 calc R U . . .
H16B H 0.4077 0.1108 0.4456 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3092(2) 0.31450(19) 0.47583(6) 0.0226(3) Uani 1 1 d . . . . .
O17 O 0.29563(19) 0.29829(15) 0.52053(4) 0.0299(3) Uani 1 1 d . . . . .
C18 C 0.4210(3) 0.87146(18) 0.33543(7) 0.0242(4) Uani 1 1 d . . . . .
H18A H 0.3395 0.7927 0.3190 0.036 Uiso 1 1 calc R U . . .
H18B H 0.3427 0.9107 0.3638 0.036 Uiso 1 1 calc R U . . .
H18C H 0.4483 0.9530 0.3119 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1089(2) 0.51008(19) 0.43567(6) 0.0238(4) Uani 1 1 d . . . . .
H19A H 0.0376 0.4270 0.4189 0.036 Uiso 1 1 calc R U . . .
H19B H 0.0343 0.5355 0.4663 0.036 Uiso 1 1 calc R U . . .
H19C H 0.1119 0.5978 0.4137 0.036 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 1.501(3) . ?
C1 C10 1.546(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.327(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.489(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.532(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(2) . ?
C5 C10 1.549(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.525(2) . ?
C8 C9 1.551(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.543(2) . ?
C9 C10 1.552(2) . ?
C9 H9 1.0000 . ?
C10 C18 1.540(2) . ?
C11 C12 1.531(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.520(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.521(2) . ?
C13 C14 1.539(2) . ?
C13 C19 1.546(2) . ?
C14 C15 1.533(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.545(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.520(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.216(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 112.99(16) . . ?
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 122.22(18) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 123.56(18) . . ?
C2 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 113.92(17) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.87(14) . . ?
C6 C5 C10 112.70(13) . . ?
C4 C5 C10 111.51(14) . . ?
C6 C5 H5 106.8 . . ?
C4 C5 H5 106.8 . . ?
C10 C5 H5 106.8 . . ?
C5 C6 C7 111.14(14) . . ?
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 . . ?
C6 C7 C8 111.12(13) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C14 C8 C7 111.67(12) . . ?
C14 C8 C9 109.32(12) . . ?
C7 C8 C9 109.55(13) . . ?
C14 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C11 C9 C8 113.04(13) . . ?
C11 C9 C10 113.72(12) . . ?
C8 C9 C10 112.15(12) . . ?
C11 C9 H9 105.7 . . ?
C8 C9 H9 105.7 . . ?
C10 C9 H9 105.7 . . ?
C18 C10 C1 109.01(14) . . ?
C18 C10 C5 111.12(13) . . ?
C1 C10 C5 107.09(13) . . ?
C18 C10 C9 111.38(13) . . ?
C1 C10 C9 109.63(13) . . ?
C5 C10 C9 108.50(13) . . ?
C12 C11 C9 112.86(13) . . ?
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 109.50(13) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C17 117.86(13) . . ?
C12 C13 C14 109.12(13) . . ?
C17 C13 C14 100.65(12) . . ?
C12 C13 C19 111.31(13) . . ?
C17 C13 C19 104.21(13) . . ?
C14 C13 C19 113.38(13) . . ?
C8 C14 C15 119.68(13) . . ?
C8 C14 C13 113.21(12) . . ?
C15 C14 C13 103.75(12) . . ?
C8 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C13 C14 H14 106.5 . . ?
C14 C15 C16 103.08(13) . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 C15 105.61(13) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
O17 C17 C16 125.62(16) . . ?
O17 C17 C13 126.26(16) . . ?
C16 C17 C13 108.12(13) . . ?
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 . . ?

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 -21.3(3) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C2 C3 C4 C5 -7.7(3) . . . . ?
C3 C4 C5 C6 166.80(16) . . . . ?
C3 C4 C5 C10 39.6(2) . . . . ?
C4 C5 C6 C7 177.40(15) . . . . ?
C10 C5 C6 C7 -56.01(19) . . . . ?
C5 C6 C7 C8 56.8(2) . . . . ?
C6 C7 C8 C14 -178.52(14) . . . . ?
C6 C7 C8 C9 -57.26(18) . . . . ?
C14 C8 C9 C11 -49.18(16) . . . . ?
C7 C8 C9 C11 -171.84(13) . . . . ?
C14 C8 C9 C10 -179.35(12) . . . . ?
C7 C8 C9 C10 57.98(16) . . . . ?
C2 C1 C10 C18 -69.64(19) . . . . ?
C2 C1 C10 C5 50.67(19) . . . . ?
C2 C1 C10 C9 168.20(14) . . . . ?
C6 C5 C10 C18 -68.09(18) . . . . ?
C4 C5 C10 C18 58.69(18) . . . . ?
C6 C5 C10 C1 172.96(14) . . . . ?
C4 C5 C10 C1 -60.26(18) . . . . ?
C6 C5 C10 C9 54.69(17) . . . . ?
C4 C5 C10 C9 -178.53(14) . . . . ?
C11 C9 C10 C18 -63.02(17) . . . . ?
C8 C9 C10 C18 66.80(17) . . . . ?
C11 C9 C10 C1 57.71(17) . . . . ?
C8 C9 C10 C1 -172.46(13) . . . . ?
C11 C9 C10 C5 174.36(13) . . . . ?
C8 C9 C10 C5 -55.82(16) . . . . ?
C8 C9 C11 C12 51.39(17) . . . . ?
C10 C9 C11 C12 -179.23(13) . . . . ?
C9 C11 C12 C13 -55.96(18) . . . . ?
C11 C12 C13 C17 173.20(13) . . . . ?
C11 C12 C13 C14 59.34(16) . . . . ?
C11 C12 C13 C19 -66.53(16) . . . . ?
C7 C8 C14 C15 -60.95(18) . . . . ?
C9 C8 C14 C15 177.66(13) . . . . ?
C7 C8 C14 C13 176.22(13) . . . . ?
C9 C8 C14 C13 54.83(16) . . . . ?
C12 C13 C14 C8 -61.19(16) . . . . ?
C17 C13 C14 C8 174.17(13) . . . . ?
C19 C13 C14 C8 63.48(17) . . . . ?
C12 C13 C14 C15 167.55(13) . . . . ?
C17 C13 C14 C15 42.91(14) . . . . ?
C19 C13 C14 C15 -67.78(16) . . . . ?
C8 C14 C15 C16 -166.43(14) . . . . ?
C13 C14 C15 C16 -39.10(15) . . . . ?
C14 C15 C16 C17 19.51(17) . . . . ?
C15 C16 C17 O17 -172.90(16) . . . . ?
C15 C16 C17 C13 7.27(17) . . . . ?
C12 C13 C17 O17 31.0(2) . . . . ?
C14 C13 C17 O17 149.42(16) . . . . ?
C19 C13 C17 O17 -92.93(19) . . . . ?
C12 C13 C17 C16 -149.20(14) . . . . ?
C14 C13 C17 C16 -30.75(15) . . . . ?
C19 C13 C17 C16 86.90(15) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.032



# start Validation Reply Form

_vrf_PLAT230_sb953_hy            
;
PROBLEM: Hirshfeld Test Diff for    C2     --  C3      ..       18.6 s.u.  
RESPONSE: due to libration of the cyclohexen ring c1, c2, c3, c4, c5, c10
;
####################################################################### 
# 
# 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_sb951_hy
_database_code_depnum_ccdc_archive 'CCDC 1822524'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2S,3S,5S,8R,9S,10S,13S,14S)-2,3-dihydroxy-10,13-
dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H30 O3'
_chemical_formula_sum            'C19 H30 O3'
_chemical_formula_weight         306.43

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

_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, y+1/2, -z'

_cell_length_a                   9.5196(4)
_cell_length_b                   7.7586(3)
_cell_length_c                   11.9999(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.939(3)
_cell_angle_gamma                90
_cell_volume                     822.11(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5872
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      72.0

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 14+1 runs, 1970 frames, 20/40/60 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 Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            9462
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.971
_diffrn_reflns_theta_max         72.166
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3203
_reflns_number_gt                2917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.987

_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)+(0.0841P)²+0.1491P] 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 
;
 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.

 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = 0.00(15) (Platon: Spek, 2009).

 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3203
_refine_ls_number_parameters     205
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.1405(3) 0.5032(4) 0.2931(3) 0.0252(6) Uani 1 1 d . . . . .
H1A H 0.1074 0.6059 0.3257 0.030 Uiso 1 1 calc R U . . .
H1B H 0.2443 0.5262 0.2964 0.030 Uiso 1 1 calc R U . . .
C2 C 0.0360(4) 0.4819(5) 0.1614(3) 0.0311(7) Uani 1 1 d . . . . .
H2 H 0.0516 0.5819 0.1147 0.037 Uiso 1 1 calc R U . . .
O2 O -0.1165(3) 0.4850(4) 0.1552(2) 0.0399(6) Uani 1 1 d D . . . .
H2O H -0.174(5) 0.489(8) 0.084(3) 0.060 Uiso 1 1 d D U . . .
C3 C 0.0685(4) 0.3158(4) 0.1071(3) 0.0298(7) Uani 1 1 d . . . . .
H3 H -0.0122 0.2986 0.0258 0.036 Uiso 1 1 calc R U . . .
O3 O 0.2099(3) 0.3411(3) 0.0943(2) 0.0377(6) Uani 1 1 d D . . . .
H3O H 0.254(5) 0.248(5) 0.094(5) 0.057 Uiso 1 1 d D U . . .
C4 C 0.0704(4) 0.1608(4) 0.1854(3) 0.0276(7) Uani 1 1 d . . . . .
H4A H 0.0992 0.0567 0.1511 0.033 Uiso 1 1 calc R U . . .
H4B H -0.0326 0.1422 0.1851 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1813(3) 0.1853(4) 0.3146(3) 0.0229(6) Uani 1 1 d . . . . .
H5 H 0.2829 0.2050 0.3101 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1968(4) 0.0244(4) 0.3914(3) 0.0275(7) Uani 1 1 d . . . . .
H6A H 0.2219 -0.0754 0.3509 0.033 Uiso 1 1 calc R U . . .
H6B H 0.0988 0.0003 0.3993 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3198(4) 0.0458(4) 0.5164(3) 0.0277(7) Uani 1 1 d . . . . .
H7A H 0.4199 0.0495 0.5091 0.033 Uiso 1 1 calc R U . . .
H7B H 0.3184 -0.0556 0.5660 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2993(3) 0.2094(4) 0.5800(3) 0.0215(6) Uani 1 1 d . . . . .
H8 H 0.2057 0.1967 0.5985 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2805(3) 0.3699(4) 0.4980(3) 0.0209(6) Uani 1 1 d . . . . .
H9 H 0.3745 0.3766 0.4796 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1467(3) 0.3479(4) 0.3755(3) 0.0214(6) Uani 1 1 d . . . . .
C11 C 0.2736(3) 0.5378(4) 0.5633(3) 0.0263(7) Uani 1 1 d . . . . .
H11A H 0.1774 0.5404 0.5772 0.032 Uiso 1 1 calc R U . . .
H11B H 0.2726 0.6364 0.5106 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4060(4) 0.5608(4) 0.6842(3) 0.0269(7) Uani 1 1 d . . . . .
H12A H 0.5016 0.5753 0.6706 0.032 Uiso 1 1 calc R U . . .
H12B H 0.3897 0.6655 0.7250 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4175(3) 0.4042(4) 0.7630(3) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.4331(3) 0.2391(4) 0.6970(3) 0.0246(7) Uani 1 1 d . . . . .
H14 H 0.5236 0.2562 0.6750 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4772(4) 0.1004(4) 0.7961(3) 0.0332(8) Uani 1 1 d . . . . .
H15A H 0.3873 0.0577 0.8102 0.040 Uiso 1 1 calc R U . . .
H15B H 0.5288 0.0019 0.7752 0.040 Uiso 1 1 calc R U . . .
C16 C 0.5853(4) 0.1981(5) 0.9061(3) 0.0377(8) Uani 1 1 d . . . . .
H16A H 0.5621 0.1717 0.9781 0.045 Uiso 1 1 calc R U . . .
H16B H 0.6917 0.1656 0.9224 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5600(3) 0.3886(5) 0.8747(3) 0.0293(7) Uani 1 1 d . . . . .
O17 O 0.6424(2) 0.5060(4) 0.9271(2) 0.0348(6) Uani 1 1 d . . . . .
C18 C -0.0044(3) 0.3332(4) 0.3945(3) 0.0255(6) Uani 1 1 d . . . . .
H18A H -0.0001 0.2346 0.4467 0.038 Uiso 1 1 calc R U . . .
H18B H -0.0218 0.4390 0.4321 0.038 Uiso 1 1 calc R U . . .
H18C H -0.0874 0.3167 0.3167 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2848(4) 0.3973(5) 0.8075(3) 0.0316(7) Uani 1 1 d . . . . .
H19A H 0.1886 0.4068 0.7387 0.047 Uiso 1 1 calc R U . . .
H19B H 0.2877 0.2877 0.8489 0.047 Uiso 1 1 calc R U . . .
H19C H 0.2938 0.4930 0.8631 0.047 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 1.529(4) . ?
C1 C10 1.546(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.426(4) . ?
C2 C3 1.527(5) . ?
C2 H2 1.0000 . ?
O2 H2O 0.83(3) . ?
C3 O3 1.425(4) . ?
C3 C4 1.522(5) . ?
C3 H3 1.0000 . ?
O3 H3O 0.83(3) . ?
C4 C5 1.527(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(4) . ?
C5 C10 1.553(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.520(4) . ?
C8 C9 1.555(4) . ?
C8 H8 1.0000 . ?
C9 C11 1.534(4) . ?
C9 C10 1.554(4) . ?
C9 H9 1.0000 . ?
C10 C18 1.543(4) . ?
C11 C12 1.537(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.514(4) . ?
C13 C14 1.542(4) . ?
C13 C19 1.546(4) . ?
C14 C15 1.541(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.537(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.213(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 115.5(3) . . ?
C2 C1 H1A 108.4 . . ?
C10 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
C10 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
O2 C2 C3 110.9(3) . . ?
O2 C2 C1 108.0(3) . . ?
C3 C2 C1 112.0(3) . . ?
O2 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C2 O2 H2O 109(4) . . ?
O3 C3 C4 112.5(3) . . ?
O3 C3 C2 106.2(3) . . ?
C4 C3 C2 111.2(3) . . ?
O3 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C3 O3 H3O 112(4) . . ?
C3 C4 C5 111.9(2) . . ?
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 112.7(2) . . ?
C6 C5 C10 111.7(2) . . ?
C4 C5 C10 113.0(2) . . ?
C6 C5 H5 106.3 . . ?
C4 C5 H5 106.3 . . ?
C10 C5 H5 106.3 . . ?
C5 C6 C7 111.7(3) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 112.7(3) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 111.5(2) . . ?
C14 C8 C9 108.8(2) . . ?
C7 C8 C9 110.7(2) . . ?
C14 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C11 C9 C10 113.6(2) . . ?
C11 C9 C8 111.9(2) . . ?
C10 C9 C8 111.7(2) . . ?
C11 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
C8 C9 H9 106.3 . . ?
C18 C10 C1 109.7(2) . . ?
C18 C10 C5 112.5(2) . . ?
C1 C10 C5 107.2(2) . . ?
C18 C10 C9 110.4(2) . . ?
C1 C10 C9 110.0(2) . . ?
C5 C10 C9 106.9(2) . . ?
C9 C11 C12 113.8(2) . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 109.8(2) . . ?
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 116.6(3) . . ?
C17 C13 C14 99.3(3) . . ?
C12 C13 C14 110.1(2) . . ?
C17 C13 C19 105.6(2) . . ?
C12 C13 C19 111.4(3) . . ?
C14 C13 C19 113.4(3) . . ?
C8 C14 C15 120.0(3) . . ?
C8 C14 C13 113.1(2) . . ?
C15 C14 C13 103.6(3) . . ?
C8 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C13 C14 H14 106.5 . . ?
C16 C15 C14 102.7(3) . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 C15 105.8(3) . . ?
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 126.2(3) . . ?
O17 C17 C16 126.1(3) . . ?
C13 C17 C16 107.7(3) . . ?
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 . . ?

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 O2 70.1(3) . . . . ?
C10 C1 C2 C3 -52.3(4) . . . . ?
O2 C2 C3 O3 167.9(3) . . . . ?
C1 C2 C3 O3 -71.4(3) . . . . ?
O2 C2 C3 C4 -69.4(3) . . . . ?
C1 C2 C3 C4 51.3(4) . . . . ?
O3 C3 C4 C5 64.2(3) . . . . ?
C2 C3 C4 C5 -54.7(3) . . . . ?
C3 C4 C5 C6 -174.2(2) . . . . ?
C3 C4 C5 C10 58.0(3) . . . . ?
C4 C5 C6 C7 174.3(2) . . . . ?
C10 C5 C6 C7 -57.2(3) . . . . ?
C5 C6 C7 C8 52.5(3) . . . . ?
C6 C7 C8 C14 -172.9(2) . . . . ?
C6 C7 C8 C9 -51.7(3) . . . . ?
C14 C8 C9 C11 -52.1(3) . . . . ?
C7 C8 C9 C11 -175.0(2) . . . . ?
C14 C8 C9 C10 179.2(2) . . . . ?
C7 C8 C9 C10 56.3(3) . . . . ?
C2 C1 C10 C18 -70.5(3) . . . . ?
C2 C1 C10 C5 52.0(3) . . . . ?
C2 C1 C10 C9 167.9(2) . . . . ?
C6 C5 C10 C18 -61.8(3) . . . . ?
C4 C5 C10 C18 66.6(3) . . . . ?
C6 C5 C10 C1 177.5(2) . . . . ?
C4 C5 C10 C1 -54.1(3) . . . . ?
C6 C5 C10 C9 59.6(3) . . . . ?
C4 C5 C10 C9 -172.1(2) . . . . ?
C11 C9 C10 C18 -64.3(3) . . . . ?
C8 C9 C10 C18 63.5(3) . . . . ?
C11 C9 C10 C1 56.9(3) . . . . ?
C8 C9 C10 C1 -175.3(2) . . . . ?
C11 C9 C10 C5 173.0(2) . . . . ?
C8 C9 C10 C5 -59.2(3) . . . . ?
C10 C9 C11 C12 -179.7(2) . . . . ?
C8 C9 C11 C12 52.6(3) . . . . ?
C9 C11 C12 C13 -54.0(3) . . . . ?
C11 C12 C13 C17 168.0(3) . . . . ?
C11 C12 C13 C14 55.9(3) . . . . ?
C11 C12 C13 C19 -70.7(3) . . . . ?
C7 C8 C14 C15 -58.0(4) . . . . ?
C9 C8 C14 C15 179.6(3) . . . . ?
C7 C8 C14 C13 179.2(2) . . . . ?
C9 C8 C14 C13 56.8(3) . . . . ?
C17 C13 C14 C8 176.9(2) . . . . ?
C12 C13 C14 C8 -60.2(3) . . . . ?
C19 C13 C14 C8 65.3(3) . . . . ?
C17 C13 C14 C15 45.5(3) . . . . ?
C12 C13 C14 C15 168.4(2) . . . . ?
C19 C13 C14 C15 -66.1(3) . . . . ?
C8 C14 C15 C16 -165.8(3) . . . . ?
C13 C14 C15 C16 -38.6(3) . . . . ?
C14 C15 C16 C17 16.0(4) . . . . ?
C12 C13 C17 O17 23.8(5) . . . . ?
C14 C13 C17 O17 142.0(3) . . . . ?
C19 C13 C17 O17 -100.4(4) . . . . ?
C12 C13 C17 C16 -153.7(3) . . . . ?
C14 C13 C17 C16 -35.6(3) . . . . ?
C19 C13 C17 C16 82.0(3) . . . . ?
C15 C16 C17 O17 -164.9(3) . . . . ?
C15 C16 C17 C13 12.6(4) . . . . ?

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
O2 H2O O17 0.83(3) 2.04(3) 2.845(3) 165(5) 1_454
O3 H3O O17 0.83(3) 2.18(3) 3.012(4) 174(5) 2_646

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.049


####################################################################### 
# 
# 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_sb943_hy
_database_code_depnum_ccdc_archive 'CCDC 1822523'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2S,3R,5S,8R,9S,10S,13S,14S)-2,3-dihydroxy-10,13-dimethyl-
hexadecahydro-17H-cyclopenta[a]phenanthren-17-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H30 O3'
_chemical_formula_sum            'C19 H30 O3'
_chemical_formula_weight         306.43

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                   7.0823(2)
_cell_length_b                   10.2458(3)
_cell_length_c                   12.0686(3)
_cell_angle_alpha                73.204(2)
_cell_angle_beta                 89.279(2)
_cell_angle_gamma                84.178(2)
_cell_volume                     833.93(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9512
_cell_measurement_theta_min      3.8
_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    1.220
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.633
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8477
_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., 20+1 runs, 2962 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            15480
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.826
_diffrn_reflns_theta_max         72.325
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             6149
_reflns_number_gt                5585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.872
_reflns_Friedel_fraction_full    0.902

_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)+(0.0568P)²+0.1931P] 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 
;
 Flack x determined using 2360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6149
_refine_ls_number_parameters     409
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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 0.5823(4) 0.5750(3) 0.6744(2) 0.0202(6) Uani 1 1 d . . . . .
H1A H 0.4535 0.5861 0.6400 0.024 Uiso 1 1 calc R U . . .
H1B H 0.6523 0.4934 0.6591 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5637(4) 0.5469(3) 0.8059(2) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.5181 0.4543 0.8380 0.026 Uiso 1 1 calc R U . . .
O2 O 0.4272(3) 0.6455(2) 0.83141(19) 0.0285(5) Uani 1 1 d D . . . .
H2O H 0.375(6) 0.603(4) 0.893(3) 0.043 Uiso 1 1 d D U . . .
C3 C 0.7547(4) 0.5457(3) 0.8632(2) 0.0227(6) Uani 1 1 d . . . . .
H3 H 0.8386 0.4653 0.8534 0.027 Uiso 1 1 calc R U . . .
O3 O 0.7317(3) 0.5252(2) 0.98497(18) 0.0291(5) Uani 1 1 d D . . . .
H3O H 0.686(6) 0.600(3) 0.991(4) 0.044 Uiso 1 1 d D U . . .
C4 C 0.8509(4) 0.6735(3) 0.8054(2) 0.0216(6) Uani 1 1 d . . . . .
H4A H 0.9765 0.6674 0.8427 0.026 Uiso 1 1 calc R U . . .
H4B H 0.7731 0.7550 0.8154 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8760(4) 0.6892(3) 0.6766(2) 0.0178(6) Uani 1 1 d . . . . .
H5 H 0.9475 0.6019 0.6714 0.021 Uiso 1 1 calc R U . . .
C6 C 0.9978(4) 0.8030(3) 0.6176(2) 0.0211(6) Uani 1 1 d . . . . .
H6A H 1.1208 0.7881 0.6597 0.025 Uiso 1 1 calc R U . . .
H6B H 0.9332 0.8923 0.6203 0.025 Uiso 1 1 calc R U . . .
C7 C 1.0330(4) 0.8064(3) 0.4921(2) 0.0220(6) Uani 1 1 d . . . . .
H7A H 1.1120 0.7217 0.4901 0.026 Uiso 1 1 calc R U . . .
H7B H 1.1047 0.8852 0.4546 0.026 Uiso 1 1 calc R U . . .
C8 C 0.8493(4) 0.8186(3) 0.4237(2) 0.0167(5) Uani 1 1 d . . . . .
H8 H 0.7754 0.9082 0.4202 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7281(4) 0.7013(3) 0.4851(2) 0.0155(5) Uani 1 1 d . . . . .
H9 H 0.8099 0.6139 0.4913 0.019 Uiso 1 1 calc R U . . .
C10 C 0.6835(4) 0.7019(3) 0.6120(2) 0.0149(5) Uani 1 1 d . . . . .
C11 C 0.5506(4) 0.6967(3) 0.4138(2) 0.0220(6) Uani 1 1 d . . . . .
H11A H 0.4911 0.6121 0.4519 0.026 Uiso 1 1 calc R U . . .
H11B H 0.4578 0.7758 0.4139 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5940(4) 0.7004(3) 0.2878(2) 0.0246(6) Uani 1 1 d . . . . .
H12A H 0.6704 0.6145 0.2862 0.030 Uiso 1 1 calc R U . . .
H12B H 0.4737 0.7074 0.2445 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7023(4) 0.8222(3) 0.2306(2) 0.0212(6) Uani 1 1 d . . . . .
C14 C 0.8857(4) 0.8125(3) 0.3005(2) 0.0202(6) Uani 1 1 d . . . . .
H14 H 0.9529 0.7197 0.3077 0.024 Uiso 1 1 calc R U . . .
C15 C 1.0057(5) 0.9159(4) 0.2192(3) 0.0306(7) Uani 1 1 d . . . . .
H15A H 1.1421 0.8952 0.2412 0.037 Uiso 1 1 calc R U . . .
H15B H 0.9630 1.0109 0.2191 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9677(5) 0.8937(4) 0.1008(3) 0.0363(8) Uani 1 1 d . . . . .
H16A H 0.9563 0.9822 0.0392 0.044 Uiso 1 1 calc R U . . .
H16B H 1.0725 0.8327 0.0816 0.044 Uiso 1 1 calc R U . . .
C17 C 0.7829(5) 0.8282(3) 0.1121(3) 0.0291(7) Uani 1 1 d . . . . .
O17 O 0.7120(4) 0.7881(3) 0.03934(19) 0.0409(6) Uani 1 1 d . . . . .
C18 C 0.5594(4) 0.8334(3) 0.6127(2) 0.0185(6) Uani 1 1 d . . . . .
H18A H 0.6250 0.9133 0.5729 0.028 Uiso 1 1 calc R U . . .
H18B H 0.4383 0.8374 0.5728 0.028 Uiso 1 1 calc R U . . .
H18C H 0.5357 0.8336 0.6928 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5760(4) 0.9585(3) 0.2130(2) 0.0240(6) Uani 1 1 d . . . . .
H19A H 0.6494 1.0351 0.1761 0.036 Uiso 1 1 calc R U . . .
H19B H 0.4665 0.9604 0.1635 0.036 Uiso 1 1 calc R U . . .
H19C H 0.5317 0.9666 0.2882 0.036 Uiso 1 1 calc R U . . .
C21 C 0.0873(4) 0.4302(3) 0.3261(2) 0.0207(6) Uani 1 1 d . . . . .
H21A H -0.0383 0.4124 0.3609 0.025 Uiso 1 1 calc R U . . .
H21B H 0.1242 0.5134 0.3427 0.025 Uiso 1 1 calc R U . . .
C22 C 0.0660(4) 0.4605(3) 0.1950(2) 0.0230(6) Uani 1 1 d . . . . .
H22 H -0.0109 0.5512 0.1645 0.028 Uiso 1 1 calc R U . . .
O22 O -0.0333(3) 0.3593(2) 0.16817(18) 0.0277(5) Uani 1 1 d D . . . .
H22O H -0.107(5) 0.400(4) 0.108(3) 0.042 Uiso 1 1 d D U . . .
C23 C 0.2580(4) 0.4691(3) 0.1354(2) 0.0236(6) Uani 1 1 d . . . . .
H23 H 0.3105 0.5530 0.1433 0.028 Uiso 1 1 calc R U . . .
O23 O 0.2333(3) 0.4861(2) 0.01427(18) 0.0297(5) Uani 1 1 d D . . . .
H23O H 0.213(6) 0.410(3) 0.007(4) 0.045 Uiso 1 1 d D U . . .
C24 C 0.3998(4) 0.3469(3) 0.1927(2) 0.0221(6) Uani 1 1 d . . . . .
H24A H 0.5242 0.3592 0.1548 0.026 Uiso 1 1 calc R U . . .
H24B H 0.3552 0.2622 0.1831 0.026 Uiso 1 1 calc R U . . .
C25 C 0.4227(4) 0.3326(3) 0.3219(2) 0.0178(6) Uani 1 1 d . . . . .
H25 H 0.4575 0.4229 0.3270 0.021 Uiso 1 1 calc R U . . .
C26 C 0.5846(4) 0.2266(3) 0.3798(2) 0.0211(6) Uani 1 1 d . . . . .
H26A H 0.7029 0.2481 0.3368 0.025 Uiso 1 1 calc R U . . .
H26B H 0.5563 0.1349 0.3773 0.025 Uiso 1 1 calc R U . . .
C27 C 0.6139(4) 0.2243(3) 0.5052(2) 0.0214(6) Uani 1 1 d . . . . .
H27A H 0.6583 0.3122 0.5072 0.026 Uiso 1 1 calc R U . . .
H27B H 0.7135 0.1499 0.5420 0.026 Uiso 1 1 calc R U . . .
C28 C 0.4307(4) 0.2022(3) 0.5739(2) 0.0163(5) Uani 1 1 d . . . . .
H28 H 0.3942 0.1093 0.5777 0.020 Uiso 1 1 calc R U . . .
C29 C 0.2673(4) 0.3103(3) 0.5136(2) 0.0164(6) Uani 1 1 d . . . . .
H29 H 0.3107 0.4018 0.5082 0.020 Uiso 1 1 calc R U . . .
C30 C 0.2323(4) 0.3086(3) 0.3867(2) 0.0163(6) Uani 1 1 d . . . . .
C31 C 0.0859(4) 0.2997(3) 0.5868(2) 0.0219(6) Uani 1 1 d . . . . .
H31A H -0.0080 0.3782 0.5497 0.026 Uiso 1 1 calc R U . . .
H31B H 0.0304 0.2147 0.5870 0.026 Uiso 1 1 calc R U . . .
C32 C 0.1200(4) 0.2983(3) 0.7128(2) 0.0248(7) Uani 1 1 d . . . . .
H32A H 0.1581 0.3881 0.7144 0.030 Uiso 1 1 calc R U . . .
H32B H 0.0014 0.2825 0.7567 0.030 Uiso 1 1 calc R U . . .
C33 C 0.2756(4) 0.1852(3) 0.7686(2) 0.0213(6) Uani 1 1 d . . . . .
C34 C 0.4564(4) 0.2094(3) 0.6970(2) 0.0199(6) Uani 1 1 d . . . . .
H34 H 0.4809 0.3060 0.6896 0.024 Uiso 1 1 calc R U . . .
C35 C 0.6148(4) 0.1180(3) 0.7770(3) 0.0277(7) Uani 1 1 d . . . . .
H35A H 0.7406 0.1504 0.7543 0.033 Uiso 1 1 calc R U . . .
H35B H 0.6173 0.0214 0.7764 0.033 Uiso 1 1 calc R U . . .
C36 C 0.5582(5) 0.1343(4) 0.8963(3) 0.0345(8) Uani 1 1 d . . . . .
H36A H 0.5799 0.0452 0.9569 0.041 Uiso 1 1 calc R U . . .
H36B H 0.6335 0.2007 0.9164 0.041 Uiso 1 1 calc R U . . .
C37 C 0.3483(5) 0.1862(3) 0.8859(3) 0.0299(7) Uani 1 1 d . . . . .
O37 O 0.2570(4) 0.2223(3) 0.9593(2) 0.0446(7) Uani 1 1 d . . . . .
C38 C 0.1616(4) 0.1725(3) 0.3849(2) 0.0186(6) Uani 1 1 d . . . . .
H38A H 0.2554 0.0965 0.4238 0.028 Uiso 1 1 calc R U . . .
H38B H 0.0406 0.1617 0.4252 0.028 Uiso 1 1 calc R U . . .
H38C H 0.1435 0.1725 0.3045 0.028 Uiso 1 1 calc R U . . .
C39 C 0.2109(5) 0.0414(3) 0.7872(3) 0.0277(7) Uani 1 1 d . . . . .
H39A H 0.1619 0.0339 0.7140 0.042 Uiso 1 1 calc R U . . .
H39B H 0.3190 -0.0280 0.8146 0.042 Uiso 1 1 calc R U . . .
H39C H 0.1108 0.0267 0.8450 0.042 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 1.535(4) . ?
C1 C10 1.543(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.423(3) . ?
C2 C3 1.525(4) . ?
C2 H2 1.0000 . ?
O2 H2O 0.85(2) . ?
C3 O3 1.433(3) . ?
C3 C4 1.518(4) . ?
C3 H3 1.0000 . ?
O3 H3O 0.82(2) . ?
C4 C5 1.526(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.523(4) . ?
C5 C10 1.554(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.523(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.525(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.523(4) . ?
C8 C9 1.552(4) . ?
C8 H8 1.0000 . ?
C9 C11 1.544(4) . ?
C9 C10 1.561(3) . ?
C9 H9 1.0000 . ?
C10 C18 1.535(4) . ?
C11 C12 1.539(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.521(4) . ?
C13 C14 1.537(4) . ?
C13 C19 1.542(4) . ?
C14 C15 1.539(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.541(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.206(4) . ?
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 1.528(4) . ?
C21 C30 1.541(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O22 1.422(4) . ?
C22 C23 1.529(4) . ?
C22 H22 1.0000 . ?
O22 H22O 0.87(2) . ?
C23 O23 1.432(4) . ?
C23 C24 1.522(4) . ?
C23 H23 1.0000 . ?
O23 H23O 0.83(2) . ?
C24 C25 1.532(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.520(4) . ?
C25 C30 1.556(3) . ?
C25 H25 1.0000 . ?
C26 C27 1.523(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.532(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C34 1.523(4) . ?
C28 C29 1.546(3) . ?
C28 H28 1.0000 . ?
C29 C31 1.545(4) . ?
C29 C30 1.559(4) . ?
C29 H29 1.0000 . ?
C30 C38 1.534(4) . ?
C31 C32 1.538(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.523(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C37 1.515(4) . ?
C33 C34 1.536(4) . ?
C33 C39 1.541(4) . ?
C34 C35 1.536(4) . ?
C34 H34 1.0000 . ?
C35 C36 1.540(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.521(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 O37 1.211(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 115.7(2) . . ?
C2 C1 H1A 108.3 . . ?
C10 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
C10 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
O2 C2 C3 110.8(2) . . ?
O2 C2 C1 110.3(2) . . ?
C3 C2 C1 111.2(2) . . ?
O2 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C2 O2 H2O 106(3) . . ?
O3 C3 C4 112.6(3) . . ?
O3 C3 C2 110.0(2) . . ?
C4 C3 C2 111.8(2) . . ?
O3 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C3 O3 H3O 105(3) . . ?
C3 C4 C5 110.6(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 113.0(2) . . ?
C6 C5 C10 112.5(2) . . ?
C4 C5 C10 112.3(2) . . ?
C6 C5 H5 106.1 . . ?
C4 C5 H5 106.1 . . ?
C10 C5 H5 106.1 . . ?
C5 C6 C7 111.0(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 . . ?
C6 C7 C8 112.5(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 112.2(2) . . ?
C14 C8 C9 108.6(2) . . ?
C7 C8 C9 110.1(2) . . ?
C14 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C11 C9 C8 113.1(2) . . ?
C11 C9 C10 113.6(2) . . ?
C8 C9 C10 111.5(2) . . ?
C11 C9 H9 106.0 . . ?
C8 C9 H9 106.0 . . ?
C10 C9 H9 106.0 . . ?
C18 C10 C1 110.2(2) . . ?
C18 C10 C5 111.5(2) . . ?
C1 C10 C5 107.1(2) . . ?
C18 C10 C9 110.4(2) . . ?
C1 C10 C9 110.0(2) . . ?
C5 C10 C9 107.6(2) . . ?
C12 C11 C9 113.5(2) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.0(2) . . ?
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 . . ?
C12 C13 C17 116.5(3) . . ?
C12 C13 C14 109.2(2) . . ?
C17 C13 C14 100.6(2) . . ?
C12 C13 C19 111.3(2) . . ?
C17 C13 C19 105.1(2) . . ?
C14 C13 C19 113.7(2) . . ?
C8 C14 C13 113.1(2) . . ?
C8 C14 C15 120.2(3) . . ?
C13 C14 C15 104.2(2) . . ?
C8 C14 H14 106.1 . . ?
C13 C14 H14 106.1 . . ?
C15 C14 H14 106.1 . . ?
C14 C15 C16 102.2(3) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 106.1(2) . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O17 C17 C16 125.8(3) . . ?
O17 C17 C13 125.9(3) . . ?
C16 C17 C13 108.3(3) . . ?
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 116.1(2) . . ?
C22 C21 H21A 108.3 . . ?
C30 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C30 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
O22 C22 C21 110.2(2) . . ?
O22 C22 C23 110.3(2) . . ?
C21 C22 C23 111.9(2) . . ?
O22 C22 H22 108.1 . . ?
C21 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C22 O22 H22O 108(3) . . ?
O23 C23 C24 112.1(2) . . ?
O23 C23 C22 110.2(2) . . ?
C24 C23 C22 112.1(2) . . ?
O23 C23 H23 107.4 . . ?
C24 C23 H23 107.4 . . ?
C22 C23 H23 107.4 . . ?
C23 O23 H23O 107(3) . . ?
C23 C24 C25 110.5(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 112.9(2) . . ?
C26 C25 C30 112.6(2) . . ?
C24 C25 C30 111.8(2) . . ?
C26 C25 H25 106.4 . . ?
C24 C25 H25 106.4 . . ?
C30 C25 H25 106.4 . . ?
C25 C26 C27 111.3(2) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 C28 111.7(2) . . ?
C26 C27 H27A 109.3 . . ?
C28 C27 H27A 109.3 . . ?
C26 C27 H27B 109.3 . . ?
C28 C27 H27B 109.3 . . ?
H27A C27 H27B 107.9 . . ?
C34 C28 C27 111.7(2) . . ?
C34 C28 C29 108.9(2) . . ?
C27 C28 C29 110.8(2) . . ?
C34 C28 H28 108.5 . . ?
C27 C28 H28 108.5 . . ?
C29 C28 H28 108.5 . . ?
C31 C29 C28 112.0(2) . . ?
C31 C29 C30 113.5(2) . . ?
C28 C29 C30 111.8(2) . . ?
C31 C29 H29 106.3 . . ?
C28 C29 H29 106.3 . . ?
C30 C29 H29 106.3 . . ?
C38 C30 C21 110.6(2) . . ?
C38 C30 C25 111.8(2) . . ?
C21 C30 C25 106.9(2) . . ?
C38 C30 C29 110.7(2) . . ?
C21 C30 C29 109.4(2) . . ?
C25 C30 C29 107.3(2) . . ?
C32 C31 C29 113.8(2) . . ?
C32 C31 H31A 108.8 . . ?
C29 C31 H31A 108.8 . . ?
C32 C31 H31B 108.8 . . ?
C29 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
C33 C32 C31 109.7(2) . . ?
C33 C32 H32A 109.7 . . ?
C31 C32 H32A 109.7 . . ?
C33 C32 H32B 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C37 C33 C32 115.7(3) . . ?
C37 C33 C34 100.7(2) . . ?
C32 C33 C34 108.8(2) . . ?
C37 C33 C39 105.3(2) . . ?
C32 C33 C39 112.0(3) . . ?
C34 C33 C39 113.8(2) . . ?
C28 C34 C35 120.9(2) . . ?
C28 C34 C33 112.8(2) . . ?
C35 C34 C33 104.3(2) . . ?
C28 C34 H34 105.9 . . ?
C35 C34 H34 105.9 . . ?
C33 C34 H34 105.9 . . ?
C34 C35 C36 102.5(2) . . ?
C34 C35 H35A 111.3 . . ?
C36 C35 H35A 111.3 . . ?
C34 C35 H35B 111.3 . . ?
C36 C35 H35B 111.3 . . ?
H35A C35 H35B 109.2 . . ?
C37 C36 C35 106.0(3) . . ?
C37 C36 H36A 110.5 . . ?
C35 C36 H36A 110.5 . . ?
C37 C36 H36B 110.5 . . ?
C35 C36 H36B 110.5 . . ?
H36A C36 H36B 108.7 . . ?
O37 C37 C33 126.5(3) . . ?
O37 C37 C36 125.2(3) . . ?
C33 C37 C36 108.2(3) . . ?
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 O2 72.0(3) . . . . ?
C10 C1 C2 C3 -51.3(3) . . . . ?
O2 C2 C3 O3 54.5(3) . . . . ?
C1 C2 C3 O3 177.5(2) . . . . ?
O2 C2 C3 C4 -71.4(3) . . . . ?
C1 C2 C3 C4 51.7(3) . . . . ?
O3 C3 C4 C5 178.8(2) . . . . ?
C2 C3 C4 C5 -56.8(3) . . . . ?
C3 C4 C5 C6 -171.3(2) . . . . ?
C3 C4 C5 C10 60.1(3) . . . . ?
C4 C5 C6 C7 175.1(2) . . . . ?
C10 C5 C6 C7 -56.5(3) . . . . ?
C5 C6 C7 C8 54.9(3) . . . . ?
C6 C7 C8 C14 -176.2(2) . . . . ?
C6 C7 C8 C9 -55.1(3) . . . . ?
C14 C8 C9 C11 -50.1(3) . . . . ?
C7 C8 C9 C11 -173.4(2) . . . . ?
C14 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C10 57.2(3) . . . . ?
C2 C1 C10 C18 -69.4(3) . . . . ?
C2 C1 C10 C5 52.0(3) . . . . ?
C2 C1 C10 C9 168.7(2) . . . . ?
C6 C5 C10 C18 -64.0(3) . . . . ?
C4 C5 C10 C18 64.9(3) . . . . ?
C6 C5 C10 C1 175.4(2) . . . . ?
C4 C5 C10 C1 -55.7(3) . . . . ?
C6 C5 C10 C9 57.2(3) . . . . ?
C4 C5 C10 C9 -173.9(2) . . . . ?
C11 C9 C10 C18 -64.7(3) . . . . ?
C8 C9 C10 C18 64.5(3) . . . . ?
C11 C9 C10 C1 57.1(3) . . . . ?
C8 C9 C10 C1 -173.8(2) . . . . ?
C11 C9 C10 C5 173.4(2) . . . . ?
C8 C9 C10 C5 -57.4(3) . . . . ?
C8 C9 C11 C12 50.0(3) . . . . ?
C10 C9 C11 C12 178.3(2) . . . . ?
C9 C11 C12 C13 -53.2(3) . . . . ?
C11 C12 C13 C17 170.8(2) . . . . ?
C11 C12 C13 C14 57.7(3) . . . . ?
C11 C12 C13 C19 -68.7(3) . . . . ?
C7 C8 C14 C13 179.1(2) . . . . ?
C9 C8 C14 C13 57.1(3) . . . . ?
C7 C8 C14 C15 -57.1(3) . . . . ?
C9 C8 C14 C15 -179.1(2) . . . . ?
C12 C13 C14 C8 -62.4(3) . . . . ?
C17 C13 C14 C8 174.5(2) . . . . ?
C19 C13 C14 C8 62.6(3) . . . . ?
C12 C13 C14 C15 165.4(2) . . . . ?
C17 C13 C14 C15 42.3(3) . . . . ?
C19 C13 C14 C15 -69.6(3) . . . . ?
C8 C14 C15 C16 -167.8(2) . . . . ?
C13 C14 C15 C16 -39.9(3) . . . . ?
C14 C15 C16 C17 21.4(3) . . . . ?
C15 C16 C17 O17 -175.4(3) . . . . ?
C15 C16 C17 C13 4.7(3) . . . . ?
C12 C13 C17 O17 33.5(4) . . . . ?
C14 C13 C17 O17 151.4(3) . . . . ?
C19 C13 C17 O17 -90.2(4) . . . . ?
C12 C13 C17 C16 -146.6(3) . . . . ?
C14 C13 C17 C16 -28.7(3) . . . . ?
C19 C13 C17 C16 89.7(3) . . . . ?
C30 C21 C22 O22 73.2(3) . . . . ?
C30 C21 C22 C23 -49.9(3) . . . . ?
O22 C22 C23 O23 52.1(3) . . . . ?
C21 C22 C23 O23 175.2(2) . . . . ?
O22 C22 C23 C24 -73.5(3) . . . . ?
C21 C22 C23 C24 49.6(3) . . . . ?
O23 C23 C24 C25 179.8(2) . . . . ?
C22 C23 C24 C25 -55.7(3) . . . . ?
C23 C24 C25 C26 -171.0(2) . . . . ?
C23 C24 C25 C30 60.9(3) . . . . ?
C24 C25 C26 C27 175.0(2) . . . . ?
C30 C25 C26 C27 -57.3(3) . . . . ?
C25 C26 C27 C28 54.8(3) . . . . ?
C26 C27 C28 C34 -176.2(2) . . . . ?
C26 C27 C28 C29 -54.6(3) . . . . ?
C34 C28 C29 C31 -51.1(3) . . . . ?
C27 C28 C29 C31 -174.4(3) . . . . ?
C34 C28 C29 C30 -179.8(2) . . . . ?
C27 C28 C29 C30 56.9(3) . . . . ?
C22 C21 C30 C38 -69.5(3) . . . . ?
C22 C21 C30 C25 52.5(3) . . . . ?
C22 C21 C30 C29 168.4(2) . . . . ?
C26 C25 C30 C38 -64.2(3) . . . . ?
C24 C25 C30 C38 64.0(3) . . . . ?
C26 C25 C30 C21 174.6(2) . . . . ?
C24 C25 C30 C21 -57.2(3) . . . . ?
C26 C25 C30 C29 57.3(3) . . . . ?
C24 C25 C30 C29 -174.4(2) . . . . ?
C31 C29 C30 C38 -62.6(3) . . . . ?
C28 C29 C30 C38 65.3(3) . . . . ?
C31 C29 C30 C21 59.6(3) . . . . ?
C28 C29 C30 C21 -172.5(2) . . . . ?
C31 C29 C30 C25 175.2(2) . . . . ?
C28 C29 C30 C25 -56.9(3) . . . . ?
C28 C29 C31 C32 51.1(3) . . . . ?
C30 C29 C31 C32 178.8(2) . . . . ?
C29 C31 C32 C33 -54.0(3) . . . . ?
C31 C32 C33 C37 170.1(3) . . . . ?
C31 C32 C33 C34 57.7(3) . . . . ?
C31 C32 C33 C39 -69.1(3) . . . . ?
C27 C28 C34 C35 -54.6(3) . . . . ?
C29 C28 C34 C35 -177.3(2) . . . . ?
C27 C28 C34 C33 -179.1(2) . . . . ?
C29 C28 C34 C33 58.3(3) . . . . ?
C37 C33 C34 C28 175.4(2) . . . . ?
C32 C33 C34 C28 -62.6(3) . . . . ?
C39 C33 C34 C28 63.2(3) . . . . ?
C37 C33 C34 C35 42.3(3) . . . . ?
C32 C33 C34 C35 164.4(2) . . . . ?
C39 C33 C34 C35 -69.9(3) . . . . ?
C28 C34 C35 C36 -167.2(3) . . . . ?
C33 C34 C35 C36 -38.9(3) . . . . ?
C34 C35 C36 C37 19.8(3) . . . . ?
C32 C33 C37 O37 32.9(5) . . . . ?
C34 C33 C37 O37 150.0(3) . . . . ?
C39 C33 C37 O37 -91.5(4) . . . . ?
C32 C33 C37 C36 -146.8(3) . . . . ?
C34 C33 C37 C36 -29.7(3) . . . . ?
C39 C33 C37 C36 88.9(3) . . . . ?
C35 C36 C37 O37 -173.3(3) . . . . ?
C35 C36 C37 C33 6.4(4) . . . . ?

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
O2 H2O O23 0.85(2) 1.94(3) 2.778(3) 167(4) 1_556
O3 H3O O17 0.82(2) 2.19(3) 2.941(3) 151(4) 1_556
O22 H22O O3 0.87(2) 1.95(3) 2.810(3) 168(4) 1_454
O23 H23O O37 0.83(2) 2.16(3) 2.952(4) 159(4) 1_554
C36 H36A O17 0.99 2.61 3.532(4) 154.8 1_546

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039


####################################################################### 
# 
# 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_sb920_hy
_database_code_depnum_ccdc_archive 'CCDC 1822528'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2S,3R,5S,8R,9S,10S,13S,14S,17S)-2-hydroxy-10,13-dimethyl-
hexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H36 O5'
_chemical_formula_sum            'C23 H36 O5'
_chemical_formula_weight         392.52

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                   7.7219(3)
_cell_length_b                   13.4724(4)
_cell_length_c                   20.1540(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2096.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      72.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.689
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7378
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?


_exptl_special_details           
;
 dx = 40 mm, 1 deg., 9+1 runs, 1637 frames, 4/6/8 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            20103
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.947
_diffrn_reflns_theta_max         72.059
_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             4140
_reflns_number_gt                4106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.997
_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    Shelxtl
_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)+(0.0370P)²+0.5785P] 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       0.0086(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = -0.02(3) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.5754(2) 0.38980(12) 0.45337(8) 0.0150(3) Uani 1 1 d . . . . .
H1A H 0.6788 0.4333 0.4530 0.018 Uiso 1 1 calc R U . . .
H1B H 0.5764 0.3526 0.4957 0.018 Uiso 1 1 calc R U . . .
C2 C 0.5912(2) 0.31520(12) 0.39608(8) 0.0148(3) Uani 1 1 d . . . . .
H2 H 0.6916 0.2702 0.4049 0.018 Uiso 1 1 calc R U . . .
O2 O 0.62051(18) 0.36667(9) 0.33527(6) 0.0196(3) Uani 1 1 d . . . . .
H2O H 0.703(4) 0.3389(19) 0.3161(13) 0.033(7) Uiso 1 1 d . . . . .
C3 C 0.4268(2) 0.25341(12) 0.39196(8) 0.0145(3) Uani 1 1 d . . . . .
H3 H 0.4134 0.2154 0.4343 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2684(2) 0.31886(12) 0.38265(8) 0.0149(3) Uani 1 1 d . . . . .
H4A H 0.1633 0.2773 0.3785 0.018 Uiso 1 1 calc R U . . .
H4B H 0.2806 0.3588 0.3417 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2527(2) 0.38743(12) 0.44315(8) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.2515 0.3430 0.4829 0.016 Uiso 1 1 calc R U . . .
C6 C 0.0824(2) 0.44461(13) 0.44489(9) 0.0181(4) Uani 1 1 d . . . . .
H6A H -0.0156 0.3979 0.4394 0.022 Uiso 1 1 calc R U . . .
H6B H 0.0791 0.4927 0.4078 0.022 Uiso 1 1 calc R U . . .
C7 C 0.0640(2) 0.49984(13) 0.51095(9) 0.0171(3) Uani 1 1 d . . . . .
H7A H -0.0424 0.5408 0.5097 0.021 Uiso 1 1 calc R U . . .
H7B H 0.0510 0.4508 0.5472 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2189(2) 0.56678(11) 0.52613(7) 0.0119(3) Uani 1 1 d . . . . .
H8 H 0.2192 0.6232 0.4939 0.014 Uiso 1 1 calc R U . . .
C9 C 0.3929(2) 0.50993(11) 0.51978(7) 0.0113(3) Uani 1 1 d . . . . .
H9 H 0.3902 0.4566 0.5543 0.014 Uiso 1 1 calc R U . . .
C10 C 0.4117(2) 0.45613(11) 0.45172(8) 0.0122(3) Uani 1 1 d . . . . .
C11 C 0.5461(2) 0.57744(12) 0.53758(8) 0.0144(3) Uani 1 1 d . . . . .
H11A H 0.6549 0.5388 0.5346 0.017 Uiso 1 1 calc R U . . .
H11B H 0.5529 0.6323 0.5050 0.017 Uiso 1 1 calc R U . . .
C12 C 0.5297(2) 0.62124(12) 0.60759(8) 0.0145(3) Uani 1 1 d . . . . .
H12A H 0.5347 0.5671 0.6407 0.017 Uiso 1 1 calc R U . . .
H12B H 0.6279 0.6667 0.6161 0.017 Uiso 1 1 calc R U . . .
C13 C 0.3595(2) 0.67778(11) 0.61520(8) 0.0122(3) Uani 1 1 d . . . . .
C14 C 0.2083(2) 0.60878(12) 0.59633(8) 0.0122(3) Uani 1 1 d . . . . .
H14 H 0.2159 0.5505 0.6269 0.015 Uiso 1 1 calc R U . . .
C15 C 0.0474(2) 0.66725(12) 0.61777(8) 0.0148(3) Uani 1 1 d . . . . .
H15A H -0.0518 0.6223 0.6259 0.018 Uiso 1 1 calc R U . . .
H15B H 0.0143 0.7167 0.5837 0.018 Uiso 1 1 calc R U . . .
C16 C 0.1062(2) 0.71889(12) 0.68291(8) 0.0162(3) Uani 1 1 d . . . . .
H16A H 0.0801 0.7908 0.6815 0.019 Uiso 1 1 calc R U . . .
H16B H 0.0470 0.6894 0.7218 0.019 Uiso 1 1 calc R U . . .
C17 C 0.3039(2) 0.70116(12) 0.68679(8) 0.0147(3) Uani 1 1 d . . . . .
H17 H 0.3283 0.6428 0.7159 0.018 Uiso 1 1 calc R U . . .
O18 O 0.38731(16) 0.78933(9) 0.71392(6) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.5354(2) 0.77718(15) 0.74750(9) 0.0246(4) Uani 1 1 d . . . . .
O19 O 0.5977(2) 0.69684(12) 0.75935(8) 0.0383(4) Uani 1 1 d . . . . .
C19 C 0.6109(3) 0.87421(18) 0.76871(12) 0.0378(5) Uani 1 1 d . . . . .
H19A H 0.5496 0.8983 0.8081 0.057 Uiso 1 1 calc R U . . .
H19B H 0.5989 0.9226 0.7327 0.057 Uiso 1 1 calc R U . . .
H19C H 0.7339 0.8653 0.7792 0.057 Uiso 1 1 calc R U . . .
O20 O 0.45071(15) 0.18294(8) 0.33768(6) 0.0159(3) Uani 1 1 d . . . . .
C20 C 0.3404(2) 0.10568(12) 0.33653(8) 0.0163(3) Uani 1 1 d . . . . .
O21 O 0.22629(18) 0.09415(9) 0.37671(6) 0.0250(3) Uani 1 1 d . . . . .
C21 C 0.3770(3) 0.03645(13) 0.27999(8) 0.0203(4) Uani 1 1 d . . . . .
H21A H 0.3145 -0.0260 0.2869 0.030 Uiso 1 1 calc R U . . .
H21B H 0.5017 0.0232 0.2778 0.030 Uiso 1 1 calc R U . . .
H21C H 0.3389 0.0670 0.2383 0.030 Uiso 1 1 calc R U . . .
C22 C 0.4248(2) 0.53267(12) 0.39503(8) 0.0167(3) Uani 1 1 d . . . . .
H22A H 0.5266 0.5748 0.4020 0.025 Uiso 1 1 calc R U . . .
H22B H 0.4357 0.4979 0.3525 0.025 Uiso 1 1 calc R U . . .
H22C H 0.3203 0.5740 0.3945 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3637(2) 0.77451(12) 0.57450(8) 0.0163(3) Uani 1 1 d . . . . .
H23A H 0.2536 0.8098 0.5799 0.024 Uiso 1 1 calc R U . . .
H23B H 0.4588 0.8166 0.5901 0.024 Uiso 1 1 calc R U . . .
H23C H 0.3812 0.7587 0.5275 0.024 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(2) . ?
C1 C10 1.548(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.426(2) . ?
C2 C3 1.521(2) . ?
C2 H2 1.0000 . ?
O2 H2O 0.83(3) . ?
C3 O20 1.4604(18) . ?
C3 C4 1.519(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.524(2) . ?
C5 C10 1.548(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.532(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.526(2) . ?
C8 C9 1.552(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.535(2) . ?
C9 C10 1.558(2) . ?
C9 H9 1.0000 . ?
C10 C22 1.542(2) . ?
C11 C12 1.535(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.538(2) . ?
C13 C23 1.540(2) . ?
C13 C14 1.540(2) . ?
C14 C15 1.533(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.553(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.547(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.458(2) . ?
C17 H17 1.0000 . ?
O18 C18 1.339(2) . ?
C18 O19 1.209(3) . ?
C18 C19 1.494(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O20 C20 1.345(2) . ?
C20 O21 1.207(2) . ?
C20 C21 1.500(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 115.26(13) . . ?
C2 C1 H1A 108.5 . . ?
C10 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C10 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
O2 C2 C3 110.59(13) . . ?
O2 C2 C1 109.91(13) . . ?
C3 C2 C1 109.44(13) . . ?
O2 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C2 O2 H2O 107.5(17) . . ?
O20 C3 C4 112.75(13) . . ?
O20 C3 C2 106.92(12) . . ?
C4 C3 C2 111.17(13) . . ?
O20 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C3 C4 C5 108.36(13) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C4 113.00(13) . . ?
C6 C5 C10 112.33(13) . . ?
C4 C5 C10 112.69(13) . . ?
C6 C5 H5 106.0 . . ?
C4 C5 H5 106.0 . . ?
C10 C5 H5 106.0 . . ?
C5 C6 C7 110.19(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 . . ?
C8 C7 C6 112.84(14) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 111.23(13) . . ?
C14 C8 C9 107.82(12) . . ?
C7 C8 C9 111.70(12) . . ?
C14 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C11 C9 C8 110.82(12) . . ?
C11 C9 C10 114.18(13) . . ?
C8 C9 C10 112.51(12) . . ?
C11 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C22 C10 C5 111.66(13) . . ?
C22 C10 C1 110.39(13) . . ?
C5 C10 C1 107.76(12) . . ?
C22 C10 C9 110.32(12) . . ?
C5 C10 C9 107.60(12) . . ?
C1 C10 C9 109.02(13) . . ?
C12 C11 C9 112.29(13) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.82(13) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C17 115.90(13) . . ?
C12 C13 C23 110.54(13) . . ?
C17 C13 C23 109.41(12) . . ?
C12 C13 C14 109.06(12) . . ?
C17 C13 C14 98.25(12) . . ?
C23 C13 C14 113.25(13) . . ?
C8 C14 C15 119.70(13) . . ?
C8 C14 C13 114.33(13) . . ?
C15 C14 C13 103.57(13) . . ?
C8 C14 H14 106.1 . . ?
C15 C14 H14 106.1 . . ?
C13 C14 H14 106.1 . . ?
C14 C15 C16 103.40(13) . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C17 C16 C15 105.17(13) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
O18 C17 C13 113.28(13) . . ?
O18 C17 C16 109.21(13) . . ?
C13 C17 C16 105.06(13) . . ?
O18 C17 H17 109.7 . . ?
C13 C17 H17 109.7 . . ?
C16 C17 H17 109.7 . . ?
C18 O18 C17 117.86(14) . . ?
O19 C18 O18 123.36(18) . . ?
O19 C18 C19 124.84(18) . . ?
O18 C18 C19 111.80(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O20 C3 115.82(12) . . ?
O21 C20 O20 123.41(16) . . ?
O21 C20 C21 124.59(16) . . ?
O20 C20 C21 112.01(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 O2 68.27(18) . . . . ?
C10 C1 C2 C3 -53.37(18) . . . . ?
O2 C2 C3 O20 59.83(16) . . . . ?
C1 C2 C3 O20 -178.95(12) . . . . ?
O2 C2 C3 C4 -63.62(16) . . . . ?
C1 C2 C3 C4 57.60(17) . . . . ?
O20 C3 C4 C5 178.31(12) . . . . ?
C2 C3 C4 C5 -61.64(16) . . . . ?
C3 C4 C5 C6 -170.51(13) . . . . ?
C3 C4 C5 C10 60.82(16) . . . . ?
C4 C5 C6 C7 172.00(14) . . . . ?
C10 C5 C6 C7 -59.14(17) . . . . ?
C5 C6 C7 C8 54.18(18) . . . . ?
C6 C7 C8 C14 -171.86(14) . . . . ?
C6 C7 C8 C9 -51.34(18) . . . . ?
C14 C8 C9 C11 -55.51(16) . . . . ?
C7 C8 C9 C11 -178.01(13) . . . . ?
C14 C8 C9 C10 175.29(12) . . . . ?
C7 C8 C9 C10 52.78(16) . . . . ?
C6 C5 C10 C22 -61.92(17) . . . . ?
C4 C5 C10 C22 67.10(17) . . . . ?
C6 C5 C10 C1 176.69(13) . . . . ?
C4 C5 C10 C1 -54.29(16) . . . . ?
C6 C5 C10 C9 59.27(16) . . . . ?
C4 C5 C10 C9 -171.71(13) . . . . ?
C2 C1 C10 C22 -71.19(17) . . . . ?
C2 C1 C10 C5 50.98(17) . . . . ?
C2 C1 C10 C9 167.48(13) . . . . ?
C11 C9 C10 C22 -60.93(17) . . . . ?
C8 C9 C10 C22 66.51(17) . . . . ?
C11 C9 C10 C5 177.04(13) . . . . ?
C8 C9 C10 C5 -55.51(16) . . . . ?
C11 C9 C10 C1 60.44(16) . . . . ?
C8 C9 C10 C1 -172.12(12) . . . . ?
C8 C9 C11 C12 56.93(16) . . . . ?
C10 C9 C11 C12 -174.76(13) . . . . ?
C9 C11 C12 C13 -56.38(17) . . . . ?
C11 C12 C13 C17 164.21(14) . . . . ?
C11 C12 C13 C23 -70.59(16) . . . . ?
C11 C12 C13 C14 54.54(17) . . . . ?
C7 C8 C14 C15 -55.90(18) . . . . ?
C9 C8 C14 C15 -178.69(13) . . . . ?
C7 C8 C14 C13 -179.56(13) . . . . ?
C9 C8 C14 C13 57.65(16) . . . . ?
C12 C13 C14 C8 -57.79(17) . . . . ?
C17 C13 C14 C8 -178.93(13) . . . . ?
C23 C13 C14 C8 65.74(17) . . . . ?
C12 C13 C14 C15 170.26(12) . . . . ?
C17 C13 C14 C15 49.12(14) . . . . ?
C23 C13 C14 C15 -66.20(15) . . . . ?
C8 C14 C15 C16 -165.77(14) . . . . ?
C13 C14 C15 C16 -37.05(15) . . . . ?
C14 C15 C16 C17 9.78(16) . . . . ?
C12 C13 C17 O18 82.45(16) . . . . ?
C23 C13 C17 O18 -43.33(17) . . . . ?
C14 C13 C17 O18 -161.63(13) . . . . ?
C12 C13 C17 C16 -158.42(14) . . . . ?
C23 C13 C17 C16 75.80(16) . . . . ?
C14 C13 C17 C16 -42.50(14) . . . . ?
C15 C16 C17 O18 142.68(13) . . . . ?
C15 C16 C17 C13 20.86(16) . . . . ?
C13 C17 O18 C18 -91.84(17) . . . . ?
C16 C17 O18 C18 151.45(14) . . . . ?
C17 O18 C18 O19 -4.1(3) . . . . ?
C17 O18 C18 C19 176.58(16) . . . . ?
C4 C3 O20 C20 -73.83(16) . . . . ?
C2 C3 O20 C20 163.70(13) . . . . ?
C3 O20 C20 O21 0.9(2) . . . . ?
C3 O20 C20 C21 -178.88(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
O2 H2O O19 0.83(3) 1.98(3) 2.7940(19) 166(2) 2_664
C4 H4A O21 0.99 2.52 3.047(2) 113.4 .
C19 H19A O21 0.98 2.54 3.420(3) 149.2 2_565
C21 H21C O18 0.98 2.65 3.384(2) 131.5 2_564

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.167
_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_sb947_hy
_database_code_depnum_ccdc_archive 'CCDC 1822526'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2S,3R,5S,8R,9S,10S,13S,14S)-2-hydroxy-10,13-dimethyl-
17-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H32 O4'
_chemical_formula_sum            'C21 H32 O4'
_chemical_formula_weight         348.46

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

_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, y+1/2, -z'

_cell_length_a                   9.8746(3)
_cell_length_b                   7.6958(2)
_cell_length_c                   12.2229(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.870(1)
_cell_angle_gamma                90
_cell_volume                     928.36(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      3.6
_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    1.247
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.673
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8221
_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., 13+1 runs, 2378 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            12308
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.618
_diffrn_reflns_theta_max         72.327
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3655
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.990

_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)+(0.0326P)²+0.2503P] 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 
;
 Flack x determined using 1624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3655
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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 0.33810(18) 0.2377(2) 0.60306(13) 0.0157(3) Uani 1 1 d . . . . .
H1A H 0.2919 0.1252 0.5896 0.019 Uiso 1 1 calc R U . . .
H1B H 0.4275 0.2313 0.5690 0.019 Uiso 1 1 calc R U . . .
C2 C 0.36133(18) 0.2598(2) 0.72694(14) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.4278 0.1701 0.7537 0.021 Uiso 1 1 calc R U . . .
O2 O 0.23625(14) 0.2325(2) 0.77887(10) 0.0245(3) Uani 1 1 d D . . . .
H2O H 0.247(3) 0.247(4) 0.8479(17) 0.037 Uiso 1 1 d D U . . .
C3 C 0.42020(17) 0.4397(2) 0.75072(14) 0.0158(4) Uani 1 1 d . . . . .
H3 H 0.5126 0.4469 0.7199 0.019 Uiso 1 1 calc R U . . .
O31 O 0.43119(12) 0.46975(17) 0.86883(10) 0.0175(3) Uani 1 1 d . . . . .
C31 C 0.53640(18) 0.3913(2) 0.92231(15) 0.0171(4) Uani 1 1 d . . . . .
O32 O 0.61754(14) 0.30179(19) 0.87739(11) 0.0248(3) Uani 1 1 d . . . . .
C32 C 0.5381(2) 0.4266(3) 1.04275(15) 0.0239(4) Uani 1 1 d . . . . .
H32A H 0.5277 0.3170 1.0825 0.036 Uiso 1 1 calc R U . . .
H32B H 0.4633 0.5048 1.0595 0.036 Uiso 1 1 calc R U . . .
H32C H 0.6244 0.4810 1.0651 0.036 Uiso 1 1 calc R U . . .
C4 C 0.33307(19) 0.5834(2) 0.70163(14) 0.0175(4) Uani 1 1 d . . . . .
H4A H 0.3751 0.6975 0.7183 0.021 Uiso 1 1 calc R U . . .
H4B H 0.2425 0.5810 0.7341 0.021 Uiso 1 1 calc R U . . .
C5 C 0.31830(18) 0.5594(2) 0.57747(15) 0.0151(3) Uani 1 1 d . . . . .
H5 H 0.4123 0.5589 0.5493 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2443(2) 0.7111(2) 0.52080(15) 0.0200(4) Uani 1 1 d . . . . .
H6A H 0.2918 0.8208 0.5398 0.024 Uiso 1 1 calc R U . . .
H6B H 0.1512 0.7189 0.5481 0.024 Uiso 1 1 calc R U . . .
C7 C 0.23721(19) 0.6901(2) 0.39609(14) 0.0178(4) Uani 1 1 d . . . . .
H7A H 0.3289 0.7073 0.3675 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1776 0.7817 0.3642 0.021 Uiso 1 1 calc R U . . .
C8 C 0.18362(17) 0.5117(2) 0.35853(14) 0.0144(4) Uani 1 1 d . . . . .
H8 H 0.0865 0.5020 0.3784 0.017 Uiso 1 1 calc R U . . .
C9 C 0.26520(18) 0.3657(2) 0.41838(14) 0.0140(3) Uani 1 1 d . . . . .
H9 H 0.3625 0.3878 0.4028 0.017 Uiso 1 1 calc R U . . .
C10 C 0.25422(17) 0.3819(2) 0.54472(14) 0.0135(3) Uani 1 1 d . . . . .
C11 C 0.2332(2) 0.1829(2) 0.37331(14) 0.0185(4) Uani 1 1 d . . . . .
H11A H 0.2970 0.0985 0.4078 0.022 Uiso 1 1 calc R U . . .
H11B H 0.1404 0.1498 0.3936 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2435(2) 0.1722(2) 0.24830(14) 0.0198(4) Uani 1 1 d . . . . .
H12A H 0.3384 0.1923 0.2278 0.024 Uiso 1 1 calc R U . . .
H12B H 0.2162 0.0549 0.2226 0.024 Uiso 1 1 calc R U . . .
C13 C 0.15191(19) 0.3080(2) 0.19452(13) 0.0172(4) Uani 1 1 d . . . . .
C14 C 0.19243(18) 0.4911(2) 0.23515(15) 0.0152(4) Uani 1 1 d . . . . .
H14 H 0.2900 0.5066 0.2179 0.018 Uiso 1 1 calc R U . . .
C15 C 0.11131(19) 0.6126(3) 0.15751(15) 0.0201(4) Uani 1 1 d . . . . .
H15A H 0.1509 0.7308 0.1571 0.024 Uiso 1 1 calc R U . . .
H15B H 0.0153 0.6200 0.1779 0.024 Uiso 1 1 calc R U . . .
C16 C 0.1256(2) 0.5214(3) 0.04539(16) 0.0230(4) Uani 1 1 d . . . . .
H16A H 0.0388 0.5248 0.0026 0.028 Uiso 1 1 calc R U . . .
H16B H 0.1963 0.5786 0.0025 0.028 Uiso 1 1 calc R U . . .
C17 C 0.16542(18) 0.3349(3) 0.07220(14) 0.0193(4) Uani 1 1 d . . . . .
O17 O 0.20692(14) 0.2275(2) 0.00843(10) 0.0257(3) Uani 1 1 d . . . . .
C18 C 0.10517(18) 0.3678(3) 0.57811(14) 0.0189(4) Uani 1 1 d . . . . .
H18A H 0.0516 0.4590 0.5413 0.028 Uiso 1 1 calc R U . . .
H18B H 0.0691 0.2537 0.5567 0.028 Uiso 1 1 calc R U . . .
H18C H 0.1002 0.3817 0.6576 0.028 Uiso 1 1 calc R U . . .
C19 C 0.00107(19) 0.2650(3) 0.21075(15) 0.0237(4) Uani 1 1 d . . . . .
H19A H -0.0557 0.3545 0.1753 0.036 Uiso 1 1 calc R U . . .
H19B H -0.0202 0.1516 0.1780 0.036 Uiso 1 1 calc R U . . .
H19C H -0.0165 0.2617 0.2892 0.036 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 1.533(2) . ?
C1 C10 1.545(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.423(2) . ?
C2 C3 1.526(2) . ?
C2 H2 1.0000 . ?
O2 H2O 0.85(2) . ?
C3 O31 1.463(2) . ?
C3 C4 1.513(2) . ?
C3 H3 1.0000 . ?
O31 C31 1.352(2) . ?
C31 O32 1.203(2) . ?
C31 C32 1.496(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C4 C5 1.531(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(2) . ?
C5 C10 1.553(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.532(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.536(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.522(2) . ?
C8 C9 1.552(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.540(2) . ?
C9 C10 1.557(2) . ?
C9 H9 1.0000 . ?
C10 C18 1.544(2) . ?
C11 C12 1.537(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.520(2) . ?
C13 C14 1.543(3) . ?
C13 C19 1.545(2) . ?
C14 C15 1.538(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.550(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.521(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.216(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 115.91(14) . . ?
C2 C1 H1A 108.3 . . ?
C10 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
C10 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
O2 C2 C3 112.32(15) . . ?
O2 C2 C1 108.67(14) . . ?
C3 C2 C1 109.41(14) . . ?
O2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C2 O2 H2O 109.7(18) . . ?
O31 C3 C4 107.40(14) . . ?
O31 C3 C2 110.29(14) . . ?
C4 C3 C2 112.29(14) . . ?
O31 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
C31 O31 C3 115.97(13) . . ?
O32 C31 O31 123.24(16) . . ?
O32 C31 C32 124.53(16) . . ?
O31 C31 C32 112.23(15) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C4 C5 109.87(14) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C4 112.68(14) . . ?
C6 C5 C10 111.70(14) . . ?
C4 C5 C10 112.72(14) . . ?
C6 C5 H5 106.4 . . ?
C4 C5 H5 106.4 . . ?
C10 C5 H5 106.4 . . ?
C5 C6 C7 112.06(14) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 113.32(14) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C14 C8 C7 111.05(14) . . ?
C14 C8 C9 110.24(14) . . ?
C7 C8 C9 109.74(14) . . ?
C14 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C11 C9 C8 113.31(14) . . ?
C11 C9 C10 114.06(14) . . ?
C8 C9 C10 110.98(14) . . ?
C11 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C10 C9 H9 105.9 . . ?
C18 C10 C1 109.20(14) . . ?
C18 C10 C5 112.19(14) . . ?
C1 C10 C5 107.76(13) . . ?
C18 C10 C9 110.76(13) . . ?
C1 C10 C9 110.30(13) . . ?
C5 C10 C9 106.56(13) . . ?
C12 C11 C9 112.65(14) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.61(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 . . ?
C12 C13 C17 116.72(15) . . ?
C12 C13 C14 110.18(14) . . ?
C17 C13 C14 99.34(14) . . ?
C12 C13 C19 111.13(16) . . ?
C17 C13 C19 105.75(14) . . ?
C14 C13 C19 113.28(15) . . ?
C8 C14 C15 120.16(15) . . ?
C8 C14 C13 113.07(14) . . ?
C15 C14 C13 103.43(14) . . ?
C8 C14 H14 106.4 . . ?
C15 C14 H14 106.4 . . ?
C13 C14 H14 106.4 . . ?
C14 C15 C16 102.09(15) . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15B 111.4 . . ?
C16 C15 H15B 111.4 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 105.50(15) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
O17 C17 C13 125.47(18) . . ?
O17 C17 C16 126.39(17) . . ?
C13 C17 C16 108.06(15) . . ?
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 . . ?

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 O2 70.23(19) . . . . ?
C10 C1 C2 C3 -52.7(2) . . . . ?
O2 C2 C3 O31 53.89(18) . . . . ?
C1 C2 C3 O31 174.66(13) . . . . ?
O2 C2 C3 C4 -65.85(19) . . . . ?
C1 C2 C3 C4 54.92(19) . . . . ?
C4 C3 O31 C31 -159.89(14) . . . . ?
C2 C3 O31 C31 77.46(17) . . . . ?
C3 O31 C31 O32 0.1(2) . . . . ?
C3 O31 C31 C32 -178.97(15) . . . . ?
O31 C3 C4 C5 179.74(14) . . . . ?
C2 C3 C4 C5 -58.85(18) . . . . ?
C3 C4 C5 C6 -173.71(15) . . . . ?
C3 C4 C5 C10 58.73(18) . . . . ?
C4 C5 C6 C7 176.86(15) . . . . ?
C10 C5 C6 C7 -55.05(19) . . . . ?
C5 C6 C7 C8 50.6(2) . . . . ?
C6 C7 C8 C14 -174.11(14) . . . . ?
C6 C7 C8 C9 -51.98(19) . . . . ?
C14 C8 C9 C11 -48.67(19) . . . . ?
C7 C8 C9 C11 -171.29(14) . . . . ?
C14 C8 C9 C10 -178.51(13) . . . . ?
C7 C8 C9 C10 58.87(17) . . . . ?
C2 C1 C10 C18 -70.49(19) . . . . ?
C2 C1 C10 C5 51.61(19) . . . . ?
C2 C1 C10 C9 167.57(14) . . . . ?
C6 C5 C10 C18 -61.43(19) . . . . ?
C4 C5 C10 C18 66.64(18) . . . . ?
C6 C5 C10 C1 178.34(14) . . . . ?
C4 C5 C10 C1 -53.59(17) . . . . ?
C6 C5 C10 C9 59.95(17) . . . . ?
C4 C5 C10 C9 -171.98(14) . . . . ?
C11 C9 C10 C18 -69.40(19) . . . . ?
C8 C9 C10 C18 60.04(18) . . . . ?
C11 C9 C10 C1 51.62(19) . . . . ?
C8 C9 C10 C1 -178.95(14) . . . . ?
C11 C9 C10 C5 168.32(14) . . . . ?
C8 C9 C10 C5 -62.25(17) . . . . ?
C8 C9 C11 C12 51.1(2) . . . . ?
C10 C9 C11 C12 179.38(15) . . . . ?
C9 C11 C12 C13 -55.6(2) . . . . ?
C11 C12 C13 C17 170.89(15) . . . . ?
C11 C12 C13 C14 58.65(19) . . . . ?
C11 C12 C13 C19 -67.75(19) . . . . ?
C7 C8 C14 C15 -62.6(2) . . . . ?
C9 C8 C14 C15 175.59(15) . . . . ?
C7 C8 C14 C13 174.80(14) . . . . ?
C9 C8 C14 C13 52.95(18) . . . . ?
C12 C13 C14 C8 -59.37(18) . . . . ?
C17 C13 C14 C8 177.54(14) . . . . ?
C19 C13 C14 C8 65.81(19) . . . . ?
C12 C13 C14 C15 169.09(14) . . . . ?
C17 C13 C14 C15 46.00(16) . . . . ?
C19 C13 C14 C15 -65.73(17) . . . . ?
C8 C14 C15 C16 -168.30(15) . . . . ?
C13 C14 C15 C16 -41.10(17) . . . . ?
C14 C15 C16 C17 19.53(18) . . . . ?
C12 C13 C17 O17 24.9(3) . . . . ?
C14 C13 C17 O17 143.22(19) . . . . ?
C19 C13 C17 O17 -99.2(2) . . . . ?
C12 C13 C17 C16 -152.01(16) . . . . ?
C14 C13 C17 C16 -33.70(17) . . . . ?
C19 C13 C17 C16 83.84(18) . . . . ?
C15 C16 C17 O17 -167.71(18) . . . . ?
C15 C16 C17 C13 9.17(19) . . . . ?

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
O2 H2O O17 0.85(2) 2.02(2) 2.8304(17) 158(3) 1_556
C32 H32B O32 0.98 2.55 3.428(3) 149.3 2_657

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.160
_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_sb903_hy
_database_code_depnum_ccdc_archive 'CCDC 1822529'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(3R,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2-oxohexadecahydro-
1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H34 O5'
_chemical_formula_sum            'C23 H34 O5'
_chemical_formula_weight         390.50

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

_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, y+1/2, -z'

_cell_length_a                   7.1015(3)
_cell_length_b                   25.1361(8)
_cell_length_c                   11.8745(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.269(2)
_cell_angle_gamma                90
_cell_volume                     2117.98(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3609
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      67.7

_exptl_crystal_description       neeldes
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.682
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8707
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   'SADABD (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 0.5 deg., 6+1 runs, 2005 frames, 30/60 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 Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 0.5°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            12893
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.517
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             7180
_reflns_number_gt                5010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.860

_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    Shelxtl
_computing_publication_material  publCIF

_refine_special_details          
;
 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_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.8259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1613 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   0.4(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7180
_refine_ls_number_parameters     510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.022
_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 0.7700(9) 0.3126(3) 0.3122(5) 0.0330(14) Uani 1 1 d . . . . .
H1A H 0.6436 0.3247 0.3336 0.040 Uiso 1 1 calc R U . . .
H1B H 0.8134 0.3368 0.2528 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7551(9) 0.2568(3) 0.2654(5) 0.0357(15) Uani 1 1 d . . . . .
O2 O 0.6079(7) 0.23315(19) 0.2530(4) 0.0482(12) Uani 1 1 d . . . . .
C3 C 0.9427(9) 0.2329(2) 0.2362(5) 0.0343(14) Uani 1 1 d . . . . .
H3 H 0.9951 0.2540 0.1732 0.041 Uiso 1 1 calc R U . . .
C4 C 1.0819(9) 0.2352(3) 0.3371(5) 0.0378(15) Uani 1 1 d . . . . .
H4A H 1.2071 0.2227 0.3144 0.045 Uiso 1 1 calc R U . . .
H4B H 1.0389 0.2114 0.3972 0.045 Uiso 1 1 calc R U . . .
C5 C 1.0983(8) 0.2919(2) 0.3821(5) 0.0309(14) Uani 1 1 d . . . . .
H5 H 1.1409 0.3141 0.3179 0.037 Uiso 1 1 calc R U . . .
C6 C 1.2522(9) 0.2970(2) 0.4751(5) 0.0334(15) Uani 1 1 d . . . . .
H6A H 1.2182 0.2752 0.5406 0.040 Uiso 1 1 calc R U . . .
H6B H 1.3725 0.2833 0.4473 0.040 Uiso 1 1 calc R U . . .
C7 C 1.2778(9) 0.3547(2) 0.5121(5) 0.0323(14) Uani 1 1 d . . . . .
H7A H 1.3694 0.3562 0.5770 0.039 Uiso 1 1 calc R U . . .
H7B H 1.3310 0.3753 0.4497 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0948(8) 0.3806(2) 0.5452(5) 0.0293(13) Uani 1 1 d . . . . .
H8 H 1.0496 0.3618 0.6132 0.035 Uiso 1 1 calc R U . . .
C9 C 0.9420(8) 0.3750(2) 0.4495(5) 0.0287(13) Uani 1 1 d . . . . .
H9 H 0.9953 0.3923 0.3819 0.034 Uiso 1 1 calc R U . . .
C10 C 0.9084(9) 0.3163(2) 0.4167(5) 0.0319(14) Uani 1 1 d . . . . .
C11 C 0.7619(9) 0.4060(3) 0.4734(5) 0.0331(14) Uani 1 1 d . . . . .
H11A H 0.6954 0.3876 0.5338 0.040 Uiso 1 1 calc R U . . .
H11B H 0.6781 0.4056 0.4048 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7963(9) 0.4640(2) 0.5090(5) 0.0339(14) Uani 1 1 d . . . . .
H12A H 0.8455 0.4843 0.4450 0.041 Uiso 1 1 calc R U . . .
H12B H 0.6757 0.4804 0.5296 0.041 Uiso 1 1 calc R U . . .
C13 C 0.9368(9) 0.4668(2) 0.6090(5) 0.0331(14) Uani 1 1 d . . . . .
C14 C 1.1197(8) 0.4392(2) 0.5744(5) 0.0293(13) Uani 1 1 d . . . . .
H14 H 1.1583 0.4572 0.5039 0.035 Uiso 1 1 calc R U . . .
C15 C 1.2652(9) 0.4555(2) 0.6673(5) 0.0347(15) Uani 1 1 d . . . . .
H15A H 1.3933 0.4571 0.6374 0.042 Uiso 1 1 calc R U . . .
H15B H 1.2657 0.4300 0.7308 0.042 Uiso 1 1 calc R U . . .
C16 C 1.2002(9) 0.5113(2) 0.7054(5) 0.0355(15) Uani 1 1 d . . . . .
H16A H 1.1811 0.5118 0.7875 0.043 Uiso 1 1 calc R U . . .
H16B H 1.2946 0.5387 0.6875 0.043 Uiso 1 1 calc R U . . .
C17 C 1.0137(9) 0.5212(2) 0.6390(5) 0.0342(14) Uani 1 1 d . . . . .
H17 H 1.0375 0.5417 0.5688 0.041 Uiso 1 1 calc R U . . .
O18 O 0.8881(6) 0.55107(17) 0.7094(4) 0.0409(11) Uani 1 1 d . . . . .
C18 C 0.7840(10) 0.5907(3) 0.6633(6) 0.0425(16) Uani 1 1 d . . . . .
O19 O 0.7960(8) 0.6055(2) 0.5682(5) 0.0602(15) Uani 1 1 d . . . . .
C19 C 0.6531(11) 0.6123(3) 0.7482(7) 0.058(2) Uani 1 1 d . . . . .
H19A H 0.5841 0.6428 0.7158 0.086 Uiso 1 1 calc R U . . .
H19B H 0.7262 0.6237 0.8157 0.086 Uiso 1 1 calc R U . . .
H19C H 0.5635 0.5846 0.7685 0.086 Uiso 1 1 calc R U . . .
O20 O 0.9201(7) 0.17884(16) 0.2003(3) 0.0407(11) Uani 1 1 d . . . . .
C20 C 0.8613(9) 0.1722(3) 0.0909(5) 0.0386(15) Uani 1 1 d . . . . .
O21 O 0.8425(7) 0.20839(18) 0.0266(4) 0.0432(11) Uani 1 1 d . . . . .
C21 C 0.8333(11) 0.1145(3) 0.0637(6) 0.0494(19) Uani 1 1 d . . . . .
H21A H 0.7983 0.1106 -0.0166 0.074 Uiso 1 1 calc R U . . .
H21B H 0.7326 0.1001 0.1088 0.074 Uiso 1 1 calc R U . . .
H21C H 0.9505 0.0951 0.0809 0.074 Uiso 1 1 calc R U . . .
C22 C 0.8232(9) 0.2836(3) 0.5135(5) 0.0336(14) Uani 1 1 d . . . . .
H22A H 0.8043 0.2467 0.4889 0.050 Uiso 1 1 calc R U . . .
H22B H 0.9096 0.2845 0.5798 0.050 Uiso 1 1 calc R U . . .
H22C H 0.7018 0.2991 0.5326 0.050 Uiso 1 1 calc R U . . .
C23 C 0.8548(9) 0.4410(2) 0.7135(5) 0.0339(14) Uani 1 1 d . . . . .
H23A H 0.8050 0.4058 0.6938 0.051 Uiso 1 1 calc R U . . .
H23B H 0.9540 0.4376 0.7728 0.051 Uiso 1 1 calc R U . . .
H23C H 0.7529 0.4634 0.7407 0.051 Uiso 1 1 calc R U . . .
C101 C 0.2754(9) 0.4348(2) 0.2030(5) 0.0321(14) Uani 1 1 d . . . . .
H10A H 0.1461 0.4221 0.1843 0.039 Uiso 1 1 calc R U . . .
H10B H 0.3315 0.4111 0.2619 0.039 Uiso 1 1 calc R U . . .
C102 C 0.2658(9) 0.4910(3) 0.2491(5) 0.0359(15) Uani 1 1 d . . . . .
O102 O 0.1187(7) 0.5136(2) 0.2632(4) 0.0507(13) Uani 1 1 d . . . . .
C103 C 0.4555(10) 0.5157(3) 0.2732(5) 0.0378(15) Uani 1 1 d . . . . .
H103 H 0.5194 0.4956 0.3365 0.045 Uiso 1 1 calc R U . . .
C104 C 0.5792(9) 0.5128(3) 0.1719(5) 0.0384(15) Uani 1 1 d . . . . .
H10C H 0.7076 0.5254 0.1935 0.046 Uiso 1 1 calc R U . . .
H10D H 0.5271 0.5363 0.1114 0.046 Uiso 1 1 calc R U . . .
C105 C 0.5893(9) 0.4557(2) 0.1280(5) 0.0316(14) Uani 1 1 d . . . . .
H105 H 0.6438 0.4338 0.1916 0.038 Uiso 1 1 calc R U . . .
C106 C 0.7254(9) 0.4511(2) 0.0328(5) 0.0343(15) Uani 1 1 d . . . . .
H10E H 0.8507 0.4647 0.0586 0.041 Uiso 1 1 calc R U . . .
H10F H 0.6797 0.4732 -0.0316 0.041 Uiso 1 1 calc R U . . .
C107 C 0.7441(8) 0.3934(3) -0.0058(5) 0.0319(14) Uani 1 1 d . . . . .
H10G H 0.8242 0.3923 -0.0721 0.038 Uiso 1 1 calc R U . . .
H10H H 0.8080 0.3726 0.0553 0.038 Uiso 1 1 calc R U . . .
C108 C 0.5554(8) 0.3677(2) -0.0366(5) 0.0295(13) Uani 1 1 d . . . . .
H108 H 0.4969 0.3872 -0.1025 0.035 Uiso 1 1 calc R U . . .
C109 C 0.4223(8) 0.3726(2) 0.0635(4) 0.0284(13) Uani 1 1 d . . . . .
H109 H 0.4912 0.3557 0.1293 0.034 Uiso 1 1 calc R U . . .
C110 C 0.3936(9) 0.4316(2) 0.0969(5) 0.0298(13) Uani 1 1 d . . . . .
C111 C 0.2392(8) 0.3403(2) 0.0452(5) 0.0323(14) Uani 1 1 d . . . . .
H11C H 0.1715 0.3399 0.1165 0.039 Uiso 1 1 calc R U . . .
H11D H 0.1575 0.3587 -0.0121 0.039 Uiso 1 1 calc R U . . .
C112 C 0.2694(9) 0.2828(3) 0.0069(5) 0.0346(15) Uani 1 1 d . . . . .
H11E H 0.3345 0.2624 0.0682 0.041 Uiso 1 1 calc R U . . .
H11F H 0.1459 0.2657 -0.0103 0.041 Uiso 1 1 calc R U . . .
C113 C 0.3872(9) 0.2820(2) -0.0976(5) 0.0312(13) Uani 1 1 d . . . . .
C114 C 0.5746(8) 0.3095(2) -0.0686(5) 0.0303(14) Uani 1 1 d . . . . .
H114 H 0.6298 0.2910 -0.0005 0.036 Uiso 1 1 calc R U . . .
C115 C 0.7009(10) 0.2955(3) -0.1664(6) 0.0419(16) Uani 1 1 d . . . . .
H11G H 0.8352 0.2946 -0.1408 0.050 Uiso 1 1 calc R U . . .
H11H H 0.6849 0.3216 -0.2285 0.050 Uiso 1 1 calc R U . . .
C116 C 0.6330(10) 0.2400(3) -0.2045(5) 0.0419(16) Uani 1 1 d . . . . .
H11I H 0.5957 0.2401 -0.2857 0.050 Uiso 1 1 calc R U . . .
H11J H 0.7337 0.2133 -0.1911 0.050 Uiso 1 1 calc R U . . .
C117 C 0.4627(9) 0.2275(2) -0.1331(5) 0.0376(15) Uani 1 1 d . . . . .
H117 H 0.5039 0.2065 -0.0650 0.045 Uiso 1 1 calc R U . . .
O118 O 0.3251(7) 0.19750(18) -0.2008(4) 0.0472(12) Uani 1 1 d . . . . .
C118 C 0.2377(11) 0.1571(3) -0.1552(7) 0.0493(19) Uani 1 1 d . . . . .
O119 O 0.2668(9) 0.1416(2) -0.0592(5) 0.0697(17) Uani 1 1 d . . . . .
C119 C 0.0983(11) 0.1324(3) -0.2380(8) 0.067(2) Uani 1 1 d . . . . .
H11K H 0.0312 0.1035 -0.2011 0.101 Uiso 1 1 calc R U . . .
H11L H 0.1650 0.1180 -0.3020 0.101 Uiso 1 1 calc R U . . .
H11M H 0.0077 0.1594 -0.2649 0.101 Uiso 1 1 calc R U . . .
O120 O 0.4393(7) 0.57052(17) 0.3073(4) 0.0429(12) Uani 1 1 d . . . . .
C120 C 0.3952(10) 0.5785(3) 0.4150(5) 0.0388(16) Uani 1 1 d . . . . .
O121 O 0.3788(7) 0.54276(18) 0.4815(4) 0.0437(11) Uani 1 1 d . . . . .
C121 C 0.3725(12) 0.6362(3) 0.4413(6) 0.0501(19) Uani 1 1 d . . . . .
H12C H 0.2973 0.6401 0.5082 0.075 Uiso 1 1 calc R U . . .
H12D H 0.3085 0.6540 0.3771 0.075 Uiso 1 1 calc R U . . .
H12E H 0.4968 0.6523 0.4557 0.075 Uiso 1 1 calc R U . . .
C122 C 0.2914(9) 0.4634(3) 0.0031(5) 0.0369(15) Uani 1 1 d . . . . .
H12F H 0.3639 0.4619 -0.0653 0.055 Uiso 1 1 calc R U . . .
H12G H 0.1659 0.4482 -0.0124 0.055 Uiso 1 1 calc R U . . .
H12H H 0.2789 0.5005 0.0270 0.055 Uiso 1 1 calc R U . . .
C123 C 0.2780(9) 0.3073(3) -0.1985(5) 0.0365(15) Uani 1 1 d . . . . .
H12I H 0.3559 0.3065 -0.2648 0.055 Uiso 1 1 calc R U . . .
H12J H 0.1615 0.2873 -0.2144 0.055 Uiso 1 1 calc R U . . .
H12K H 0.2470 0.3443 -0.1806 0.055 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 1.512(9) . ?
C1 C10 1.555(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.206(7) . ?
C2 C3 1.514(9) . ?
C3 O20 1.432(7) . ?
C3 C4 1.524(8) . ?
C3 H3 1.0000 . ?
C4 C5 1.525(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(8) . ?
C5 C10 1.551(8) . ?
C5 H5 1.0000 . ?
C6 C7 1.525(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.519(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.521(8) . ?
C8 C9 1.546(8) . ?
C8 H8 1.0000 . ?
C9 C11 1.534(8) . ?
C9 C10 1.542(8) . ?
C9 H9 1.0000 . ?
C10 C22 1.555(8) . ?
C11 C12 1.535(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.510(8) . ?
C13 C23 1.534(8) . ?
C13 C14 1.542(9) . ?
C14 C15 1.537(8) . ?
C14 H14 1.0000 . ?
C15 C16 1.549(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.535(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.455(7) . ?
C17 H17 1.0000 . ?
O18 C18 1.344(8) . ?
C18 O19 1.195(8) . ?
C18 C19 1.500(10) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O20 C20 1.358(7) . ?
C20 O21 1.193(7) . ?
C20 C21 1.496(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C101 C102 1.517(9) . ?
C101 C110 1.544(8) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 O102 1.206(7) . ?
C102 C103 1.501(9) . ?
C103 O120 1.442(7) . ?
C103 C104 1.519(9) . ?
C103 H103 1.0000 . ?
C104 C105 1.529(9) . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C105 C106 1.521(8) . ?
C105 C110 1.548(8) . ?
C105 H105 1.0000 . ?
C106 C107 1.528(9) . ?
C106 H10E 0.9900 . ?
C106 H10F 0.9900 . ?
C107 C108 1.519(8) . ?
C107 H10G 0.9900 . ?
C107 H10H 0.9900 . ?
C108 C114 1.518(8) . ?
C108 C109 1.552(8) . ?
C108 H108 1.0000 . ?
C109 C111 1.541(8) . ?
C109 C110 1.550(8) . ?
C109 H109 1.0000 . ?
C110 C122 1.531(8) . ?
C111 C112 1.533(8) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C112 C113 1.524(8) . ?
C112 H11E 0.9900 . ?
C112 H11F 0.9900 . ?
C113 C114 1.527(8) . ?
C113 C117 1.537(8) . ?
C113 C123 1.539(8) . ?
C114 C115 1.537(8) . ?
C114 H114 1.0000 . ?
C115 C116 1.537(9) . ?
C115 H11G 0.9900 . ?
C115 H11H 0.9900 . ?
C116 C117 1.536(9) . ?
C116 H11I 0.9900 . ?
C116 H11J 0.9900 . ?
C117 O118 1.452(7) . ?
C117 H117 1.0000 . ?
O118 C118 1.317(8) . ?
C118 O119 1.215(9) . ?
C118 C119 1.503(10) . ?
C119 H11K 0.9800 . ?
C119 H11L 0.9800 . ?
C119 H11M 0.9800 . ?
O120 C120 1.344(7) . ?
C120 O121 1.205(8) . ?
C120 C121 1.492(9) . ?
C121 H12C 0.9800 . ?
C121 H12D 0.9800 . ?
C121 H12E 0.9800 . ?
C122 H12F 0.9800 . ?
C122 H12G 0.9800 . ?
C122 H12H 0.9800 . ?
C123 H12I 0.9800 . ?
C123 H12J 0.9800 . ?
C123 H12K 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 112.4(5) . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
O2 C2 C1 123.3(6) . . ?
O2 C2 C3 122.9(6) . . ?
C1 C2 C3 113.7(5) . . ?
O20 C3 C2 110.8(5) . . ?
O20 C3 C4 109.4(5) . . ?
C2 C3 C4 110.8(5) . . ?
O20 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C3 C4 C5 110.4(5) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 111.9(5) . . ?
C4 C5 C10 114.0(5) . . ?
C6 C5 C10 112.3(5) . . ?
C4 C5 H5 105.9 . . ?
C6 C5 H5 105.9 . . ?
C10 C5 H5 105.9 . . ?
C7 C6 C5 111.2(5) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 112.9(5) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C14 112.4(5) . . ?
C7 C8 C9 110.7(5) . . ?
C14 C8 C9 109.2(5) . . ?
C7 C8 H8 108.2 . . ?
C14 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C11 C9 C10 114.3(5) . . ?
C11 C9 C8 112.6(5) . . ?
C10 C9 C8 111.7(5) . . ?
C11 C9 H9 105.8 . . ?
C10 C9 H9 105.8 . . ?
C8 C9 H9 105.8 . . ?
C9 C10 C5 108.5(5) . . ?
C9 C10 C1 110.2(5) . . ?
C5 C10 C1 107.1(5) . . ?
C9 C10 C22 112.3(5) . . ?
C5 C10 C22 110.8(5) . . ?
C1 C10 C22 107.8(5) . . ?
C9 C11 C12 114.2(5) . . ?
C9 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 110.5(5) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C17 C13 C12 116.4(5) . . ?
C17 C13 C23 109.7(5) . . ?
C12 C13 C23 110.7(5) . . ?
C17 C13 C14 99.8(5) . . ?
C12 C13 C14 107.7(5) . . ?
C23 C13 C14 112.1(5) . . ?
C8 C14 C15 119.4(5) . . ?
C8 C14 C13 113.9(5) . . ?
C15 C14 C13 103.8(5) . . ?
C8 C14 H14 106.3 . . ?
C15 C14 H14 106.3 . . ?
C13 C14 H14 106.3 . . ?
C14 C15 C16 104.5(5) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 105.0(5) . . ?
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 . . ?
O18 C17 C13 112.2(5) . . ?
O18 C17 C16 109.0(5) . . ?
C13 C17 C16 105.7(5) . . ?
O18 C17 H17 110.0 . . ?
C13 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
C18 O18 C17 119.2(5) . . ?
O19 C18 O18 123.9(7) . . ?
O19 C18 C19 126.2(7) . . ?
O18 C18 C19 109.9(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O20 C3 115.4(5) . . ?
O21 C20 O20 122.7(6) . . ?
O21 C20 C21 126.1(6) . . ?
O20 C20 C21 111.1(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C102 C101 C110 112.2(5) . . ?
C102 C101 H10A 109.2 . . ?
C110 C101 H10A 109.2 . . ?
C102 C101 H10B 109.2 . . ?
C110 C101 H10B 109.2 . . ?
H10A C101 H10B 107.9 . . ?
O102 C102 C103 123.8(6) . . ?
O102 C102 C101 122.6(6) . . ?
C103 C102 C101 113.6(5) . . ?
O120 C103 C102 111.5(5) . . ?
O120 C103 C104 108.9(5) . . ?
C102 C103 C104 111.8(5) . . ?
O120 C103 H103 108.2 . . ?
C102 C103 H103 108.2 . . ?
C104 C103 H103 108.2 . . ?
C103 C104 C105 110.6(5) . . ?
C103 C104 H10C 109.5 . . ?
C105 C104 H10C 109.5 . . ?
C103 C104 H10D 109.5 . . ?
C105 C104 H10D 109.5 . . ?
H10C C104 H10D 108.1 . . ?
C106 C105 C104 111.4(5) . . ?
C106 C105 C110 112.5(5) . . ?
C104 C105 C110 113.3(5) . . ?
C106 C105 H105 106.3 . . ?
C104 C105 H105 106.3 . . ?
C110 C105 H105 106.3 . . ?
C105 C106 C107 111.1(5) . . ?
C105 C106 H10E 109.4 . . ?
C107 C106 H10E 109.4 . . ?
C105 C106 H10F 109.4 . . ?
C107 C106 H10F 109.4 . . ?
H10E C106 H10F 108.0 . . ?
C108 C107 C106 112.9(5) . . ?
C108 C107 H10G 109.0 . . ?
C106 C107 H10G 109.0 . . ?
C108 C107 H10H 109.0 . . ?
C106 C107 H10H 109.0 . . ?
H10G C107 H10H 107.8 . . ?
C114 C108 C107 112.5(5) . . ?
C114 C108 C109 109.3(5) . . ?
C107 C108 C109 109.9(5) . . ?
C114 C108 H108 108.4 . . ?
C107 C108 H108 108.4 . . ?
C109 C108 H108 108.4 . . ?
C111 C109 C110 114.8(5) . . ?
C111 C109 C108 112.7(5) . . ?
C110 C109 C108 111.2(5) . . ?
C111 C109 H109 105.8 . . ?
C110 C109 H109 105.8 . . ?
C108 C109 H109 105.8 . . ?
C122 C110 C101 108.0(5) . . ?
C122 C110 C105 111.3(5) . . ?
C101 C110 C105 107.2(5) . . ?
C122 C110 C109 112.2(5) . . ?
C101 C110 C109 109.9(5) . . ?
C105 C110 C109 108.1(5) . . ?
C112 C111 C109 114.2(5) . . ?
C112 C111 H11C 108.7 . . ?
C109 C111 H11C 108.7 . . ?
C112 C111 H11D 108.7 . . ?
C109 C111 H11D 108.7 . . ?
H11C C111 H11D 107.6 . . ?
C113 C112 C111 109.9(5) . . ?
C113 C112 H11E 109.7 . . ?
C111 C112 H11E 109.7 . . ?
C113 C112 H11F 109.7 . . ?
C111 C112 H11F 109.7 . . ?
H11E C112 H11F 108.2 . . ?
C112 C113 C114 108.2(5) . . ?
C112 C113 C117 116.3(5) . . ?
C114 C113 C117 98.9(5) . . ?
C112 C113 C123 110.7(5) . . ?
C114 C113 C123 113.4(5) . . ?
C117 C113 C123 109.0(5) . . ?
C108 C114 C113 114.0(5) . . ?
C108 C114 C115 118.1(5) . . ?
C113 C114 C115 104.8(5) . . ?
C108 C114 H114 106.4 . . ?
C113 C114 H114 106.4 . . ?
C115 C114 H114 106.4 . . ?
C114 C115 C116 104.2(5) . . ?
C114 C115 H11G 110.9 . . ?
C116 C115 H11G 110.9 . . ?
C114 C115 H11H 110.9 . . ?
C116 C115 H11H 110.9 . . ?
H11G C115 H11H 108.9 . . ?
C117 C116 C115 105.6(5) . . ?
C117 C116 H11I 110.6 . . ?
C115 C116 H11I 110.6 . . ?
C117 C116 H11J 110.6 . . ?
C115 C116 H11J 110.6 . . ?
H11I C116 H11J 108.8 . . ?
O118 C117 C116 109.2(5) . . ?
O118 C117 C113 112.4(5) . . ?
C116 C117 C113 105.0(5) . . ?
O118 C117 H117 110.0 . . ?
C116 C117 H117 110.0 . . ?
C113 C117 H117 110.0 . . ?
C118 O118 C117 119.4(6) . . ?
O119 C118 O118 124.6(7) . . ?
O119 C118 C119 124.4(7) . . ?
O118 C118 C119 111.0(7) . . ?
C118 C119 H11K 109.5 . . ?
C118 C119 H11L 109.5 . . ?
H11K C119 H11L 109.5 . . ?
C118 C119 H11M 109.5 . . ?
H11K C119 H11M 109.5 . . ?
H11L C119 H11M 109.5 . . ?
C120 O120 C103 115.7(5) . . ?
O121 C120 O120 123.0(6) . . ?
O121 C120 C121 125.0(6) . . ?
O120 C120 C121 112.0(6) . . ?
C120 C121 H12C 109.5 . . ?
C120 C121 H12D 109.5 . . ?
H12C C121 H12D 109.5 . . ?
C120 C121 H12E 109.5 . . ?
H12C C121 H12E 109.5 . . ?
H12D C121 H12E 109.5 . . ?
C110 C122 H12F 109.5 . . ?
C110 C122 H12G 109.5 . . ?
H12F C122 H12G 109.5 . . ?
C110 C122 H12H 109.5 . . ?
H12F C122 H12H 109.5 . . ?
H12G C122 H12H 109.5 . . ?
C113 C123 H12I 109.5 . . ?
C113 C123 H12J 109.5 . . ?
H12I C123 H12J 109.5 . . ?
C113 C123 H12K 109.5 . . ?
H12I C123 H12K 109.5 . . ?
H12J C123 H12K 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 O2 124.3(7) . . . . ?
C10 C1 C2 C3 -55.3(7) . . . . ?
O2 C2 C3 O20 -3.8(8) . . . . ?
C1 C2 C3 O20 175.8(5) . . . . ?
O2 C2 C3 C4 -125.4(6) . . . . ?
C1 C2 C3 C4 54.3(7) . . . . ?
O20 C3 C4 C5 -176.1(5) . . . . ?
C2 C3 C4 C5 -53.7(7) . . . . ?
C3 C4 C5 C6 -173.8(5) . . . . ?
C3 C4 C5 C10 57.3(7) . . . . ?
C4 C5 C6 C7 175.2(5) . . . . ?
C10 C5 C6 C7 -55.0(7) . . . . ?
C5 C6 C7 C8 53.4(7) . . . . ?
C6 C7 C8 C14 -176.2(5) . . . . ?
C6 C7 C8 C9 -53.9(6) . . . . ?
C7 C8 C9 C11 -173.4(5) . . . . ?
C14 C8 C9 C11 -49.2(6) . . . . ?
C7 C8 C9 C10 56.4(6) . . . . ?
C14 C8 C9 C10 -179.4(5) . . . . ?
C11 C9 C10 C5 173.6(5) . . . . ?
C8 C9 C10 C5 -57.1(6) . . . . ?
C11 C9 C10 C1 56.7(6) . . . . ?
C8 C9 C10 C1 -174.0(5) . . . . ?
C11 C9 C10 C22 -63.5(7) . . . . ?
C8 C9 C10 C22 65.8(6) . . . . ?
C4 C5 C10 C9 -174.7(5) . . . . ?
C6 C5 C10 C9 56.7(6) . . . . ?
C4 C5 C10 C1 -55.8(6) . . . . ?
C6 C5 C10 C1 175.6(5) . . . . ?
C4 C5 C10 C22 61.6(6) . . . . ?
C6 C5 C10 C22 -67.1(6) . . . . ?
C2 C1 C10 C9 171.2(5) . . . . ?
C2 C1 C10 C5 53.4(6) . . . . ?
C2 C1 C10 C22 -65.9(7) . . . . ?
C10 C9 C11 C12 178.5(5) . . . . ?
C8 C9 C11 C12 49.6(7) . . . . ?
C9 C11 C12 C13 -54.1(7) . . . . ?
C11 C12 C13 C17 168.3(5) . . . . ?
C11 C12 C13 C23 -65.5(7) . . . . ?
C11 C12 C13 C14 57.4(6) . . . . ?
C7 C8 C14 C15 -56.5(7) . . . . ?
C9 C8 C14 C15 -179.7(5) . . . . ?
C7 C8 C14 C13 -179.7(5) . . . . ?
C9 C8 C14 C13 57.1(6) . . . . ?
C17 C13 C14 C8 176.3(5) . . . . ?
C12 C13 C14 C8 -61.7(6) . . . . ?
C23 C13 C14 C8 60.2(7) . . . . ?
C17 C13 C14 C15 44.9(6) . . . . ?
C12 C13 C14 C15 166.9(5) . . . . ?
C23 C13 C14 C15 -71.1(6) . . . . ?
C8 C14 C15 C16 -158.7(5) . . . . ?
C13 C14 C15 C16 -30.7(6) . . . . ?
C14 C15 C16 C17 4.5(6) . . . . ?
C12 C13 C17 O18 83.5(7) . . . . ?
C23 C13 C17 O18 -43.2(7) . . . . ?
C14 C13 C17 O18 -161.0(5) . . . . ?
C12 C13 C17 C16 -157.9(5) . . . . ?
C23 C13 C17 C16 75.5(6) . . . . ?
C14 C13 C17 C16 -42.4(6) . . . . ?
C15 C16 C17 O18 144.9(5) . . . . ?
C15 C16 C17 C13 24.1(6) . . . . ?
C13 C17 O18 C18 -104.5(6) . . . . ?
C16 C17 O18 C18 138.8(6) . . . . ?
C17 O18 C18 O19 -4.8(10) . . . . ?
C17 O18 C18 C19 174.8(5) . . . . ?
C2 C3 O20 C20 81.5(6) . . . . ?
C4 C3 O20 C20 -156.1(5) . . . . ?
C3 O20 C20 O21 5.2(9) . . . . ?
C3 O20 C20 C21 -177.2(6) . . . . ?
C110 C101 C102 O102 124.1(7) . . . . ?
C110 C101 C102 C103 -55.0(7) . . . . ?
O102 C102 C103 O120 -4.2(9) . . . . ?
C101 C102 C103 O120 174.9(5) . . . . ?
O102 C102 C103 C104 -126.4(7) . . . . ?
C101 C102 C103 C104 52.7(7) . . . . ?
O120 C103 C104 C105 -176.2(5) . . . . ?
C102 C103 C104 C105 -52.5(7) . . . . ?
C103 C104 C105 C106 -175.3(5) . . . . ?
C103 C104 C105 C110 56.7(7) . . . . ?
C104 C105 C106 C107 176.5(5) . . . . ?
C110 C105 C106 C107 -55.0(7) . . . . ?
C105 C106 C107 C108 53.6(7) . . . . ?
C106 C107 C108 C114 -176.8(5) . . . . ?
C106 C107 C108 C109 -54.8(7) . . . . ?
C114 C108 C109 C111 -47.7(7) . . . . ?
C107 C108 C109 C111 -171.6(5) . . . . ?
C114 C108 C109 C110 -178.3(5) . . . . ?
C107 C108 C109 C110 57.8(6) . . . . ?
C102 C101 C110 C122 -65.3(7) . . . . ?
C102 C101 C110 C105 54.8(6) . . . . ?
C102 C101 C110 C109 172.0(5) . . . . ?
C106 C105 C110 C122 -66.5(7) . . . . ?
C104 C105 C110 C122 61.0(7) . . . . ?
C106 C105 C110 C101 175.6(5) . . . . ?
C104 C105 C110 C101 -56.9(6) . . . . ?
C106 C105 C110 C109 57.2(6) . . . . ?
C104 C105 C110 C109 -175.3(5) . . . . ?
C111 C109 C110 C122 -64.6(6) . . . . ?
C108 C109 C110 C122 64.8(6) . . . . ?
C111 C109 C110 C101 55.5(6) . . . . ?
C108 C109 C110 C101 -175.0(5) . . . . ?
C111 C109 C110 C105 172.2(5) . . . . ?
C108 C109 C110 C105 -58.3(6) . . . . ?
C110 C109 C111 C112 177.3(5) . . . . ?
C108 C109 C111 C112 48.6(7) . . . . ?
C109 C111 C112 C113 -53.8(7) . . . . ?
C111 C112 C113 C114 58.3(7) . . . . ?
C111 C112 C113 C117 168.5(5) . . . . ?
C111 C112 C113 C123 -66.5(7) . . . . ?
C107 C108 C114 C113 178.7(5) . . . . ?
C109 C108 C114 C113 56.4(6) . . . . ?
C107 C108 C114 C115 -57.6(7) . . . . ?
C109 C108 C114 C115 -180.0(5) . . . . ?
C112 C113 C114 C108 -62.5(6) . . . . ?
C117 C113 C114 C108 175.9(5) . . . . ?
C123 C113 C114 C108 60.6(7) . . . . ?
C112 C113 C114 C115 166.9(5) . . . . ?
C117 C113 C114 C115 45.2(6) . . . . ?
C123 C113 C114 C115 -70.0(6) . . . . ?
C108 C114 C115 C116 -159.6(5) . . . . ?
C113 C114 C115 C116 -31.4(7) . . . . ?
C114 C115 C116 C117 4.4(7) . . . . ?
C115 C116 C117 O118 144.7(5) . . . . ?
C115 C116 C117 C113 23.9(7) . . . . ?
C112 C113 C117 O118 83.7(7) . . . . ?
C114 C113 C117 O118 -160.8(5) . . . . ?
C123 C113 C117 O118 -42.2(7) . . . . ?
C112 C113 C117 C116 -157.7(5) . . . . ?
C114 C113 C117 C116 -42.2(6) . . . . ?
C123 C113 C117 C116 76.4(6) . . . . ?
C116 C117 O118 C118 138.6(6) . . . . ?
C113 C117 O118 C118 -105.3(7) . . . . ?
C117 O118 C118 O119 -1.9(11) . . . . ?
C117 O118 C118 C119 178.6(6) . . . . ?
C102 C103 O120 C120 79.2(7) . . . . ?
C104 C103 O120 C120 -156.9(5) . . . . ?
C103 O120 C120 O121 3.4(10) . . . . ?
C103 O120 C120 C121 -177.3(6) . . . . ?

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
C16 H16B O121 0.99 2.54 3.093(8) 115.0 1_655
C117 H117 O21 1.00 2.60 3.270(8) 124.4 .
C119 H11K O102 0.98 2.59 3.368(9) 136.0 2_545

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.044




#==============================================================================
#_eof # End of Crystallographic Information File

####################################################################### 
# 
# 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_sb959_hy
_database_code_depnum_ccdc_archive 'CCDC 1822525'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2R,3R,5S,8R,9S,10S,13S,14S)-10,13-dimethylhexadecahydrospiro-
[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolane]-2,3-diol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H34 O4'
_chemical_formula_sum            'C21 H34 O4'
_chemical_formula_weight         350.48

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

_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, y+1/2, -z'

_cell_length_a                   11.0162(3)
_cell_length_b                   6.7430(2)
_cell_length_c                   12.6811(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.877(2)
_cell_angle_gamma                90
_cell_volume                     914.49(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8712
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      71.8

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.684
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7919
_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., 16+1 runs, 2520 frames, 20/30/40/50 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            14546
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.590
_diffrn_reflns_theta_max         71.823
_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 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3541
_reflns_number_gt                3243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.984

_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          
;
absolute configuration determined by mixture of ad/syn
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.4510P] 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 
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = 0.01(14) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   0.14(18)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     232
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.3369(3) 0.8775(5) 0.7713(2) 0.0193(6) Uani 1 1 d . . . . .
H1A H 0.3970 0.9683 0.7493 0.023 Uiso 1 1 calc R U . . .
H1B H 0.2567 0.9493 0.7625 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3863(3) 0.8227(5) 0.8908(2) 0.0222(7) Uani 1 1 d . . . . .
H2 H 0.4703 0.7595 0.9006 0.027 Uiso 1 1 calc R U . . .
O2 O 0.3979(2) 0.9952(4) 0.95774(17) 0.0310(6) Uani 1 1 d D . . . .
H2O H 0.467(3) 1.054(6) 0.957(3) 0.047 Uiso 1 1 d D U . . .
C3 C 0.2993(3) 0.6793(5) 0.9280(2) 0.0215(6) Uani 1 1 d . . . . .
H3 H 0.2188 0.7491 0.9264 0.026 Uiso 1 1 calc R U . . .
O3 O 0.3522(2) 0.6151(4) 1.03666(17) 0.0276(5) Uani 1 1 d D . . . .
H3O H 0.345(4) 0.710(5) 1.081(3) 0.041 Uiso 1 1 d D U . . .
C4 C 0.2714(3) 0.4987(5) 0.8545(2) 0.0207(6) Uani 1 1 d . . . . .
H4A H 0.2079 0.4156 0.8769 0.025 Uiso 1 1 calc R U . . .
H4B H 0.3484 0.4186 0.8628 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2234(3) 0.5570(4) 0.7351(2) 0.0173(6) Uani 1 1 d . . . . .
H5 H 0.1456 0.6363 0.7305 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1856(3) 0.3785(5) 0.6615(2) 0.0194(6) Uani 1 1 d . . . . .
H6A H 0.1261 0.2957 0.6896 0.023 Uiso 1 1 calc R U . . .
H6B H 0.2604 0.2972 0.6615 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1247(3) 0.4437(5) 0.5455(2) 0.0197(6) Uani 1 1 d . . . . .
H7A H 0.0461 0.5154 0.5446 0.024 Uiso 1 1 calc R U . . .
H7B H 0.1037 0.3253 0.4985 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2121(3) 0.5785(5) 0.5005(2) 0.0159(6) Uani 1 1 d . . . . .
H8 H 0.2880 0.5001 0.4968 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2548(2) 0.7588(4) 0.5766(2) 0.0152(6) Uani 1 1 d . . . . .
H9 H 0.1770 0.8331 0.5795 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3163(3) 0.6953(5) 0.6954(2) 0.0162(6) Uani 1 1 d . . . . .
C11 C 0.3363(3) 0.9037(5) 0.5292(2) 0.0184(6) Uani 1 1 d . . . . .
H11A H 0.3514 1.0243 0.5750 0.022 Uiso 1 1 calc R U . . .
H11B H 0.4183 0.8409 0.5325 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2776(3) 0.9648(5) 0.4114(2) 0.0189(6) Uani 1 1 d . . . . .
H12A H 0.2019 1.0456 0.4087 0.023 Uiso 1 1 calc R U . . .
H12B H 0.3378 1.0466 0.3835 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2427(3) 0.7809(5) 0.3401(2) 0.0173(6) Uani 1 1 d . . . . .
C14 C 0.1521(3) 0.6543(4) 0.3869(2) 0.0170(6) Uani 1 1 d . . . . .
H14 H 0.0815 0.7429 0.3935 0.020 Uiso 1 1 calc R U . . .
C15 C 0.0988(3) 0.5043(5) 0.2961(2) 0.0205(6) Uani 1 1 d . . . . .
H15A H 0.0129 0.4642 0.2980 0.025 Uiso 1 1 calc R U . . .
H15B H 0.1521 0.3845 0.3033 0.025 Uiso 1 1 calc R U . . .
C16 C 0.0989(3) 0.6171(5) 0.1893(2) 0.0241(7) Uani 1 1 d . . . . .
H16A H 0.1459 0.5415 0.1451 0.029 Uiso 1 1 calc R U . . .
H16B H 0.0123 0.6373 0.1458 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1624(3) 0.8171(5) 0.2241(2) 0.0204(7) Uani 1 1 d . . . . .
O18 O 0.07250(19) 0.9687(4) 0.22502(15) 0.0224(5) Uani 1 1 d . . . . .
C19 C 0.0575(3) 1.0741(5) 0.1253(2) 0.0247(7) Uani 1 1 d . . . . .
H19A H 0.0257 1.2100 0.1309 0.030 Uiso 1 1 calc R U . . .
H19B H 0.0004 1.0036 0.0648 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1896(3) 1.0770(5) 0.1110(3) 0.0266(7) Uani 1 1 d . . . . .
H20A H 0.1910 1.0952 0.0338 0.032 Uiso 1 1 calc R U . . .
H20B H 0.2397 1.1830 0.1551 0.032 Uiso 1 1 calc R U . . .
O21 O 0.2336(2) 0.8851(4) 0.14937(17) 0.0258(5) Uani 1 1 d . . . . .
C22 C 0.4425(3) 0.5937(5) 0.7012(2) 0.0222(6) Uani 1 1 d . . . . .
H22A H 0.4298 0.4779 0.6531 0.033 Uiso 1 1 calc R U . . .
H22B H 0.4992 0.6872 0.6781 0.033 Uiso 1 1 calc R U . . .
H22C H 0.4791 0.5513 0.7760 0.033 Uiso 1 1 calc R U . . .
C23 C 0.3591(3) 0.6646(5) 0.3292(2) 0.0209(6) Uani 1 1 d . . . . .
H23A H 0.3332 0.5481 0.2831 0.031 Uiso 1 1 calc R U . . .
H23B H 0.4120 0.7498 0.2963 0.031 Uiso 1 1 calc R U . . .
H23C H 0.4062 0.6218 0.4012 0.031 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 1.527(4) . ?
C1 C10 1.543(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.428(4) . ?
C2 C3 1.515(4) . ?
C2 H2 1.0000 . ?
O2 H2O 0.86(2) . ?
C3 O3 1.429(4) . ?
C3 C4 1.519(4) . ?
C3 H3 1.0000 . ?
O3 H3O 0.87(2) . ?
C4 C5 1.530(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(4) . ?
C5 C10 1.554(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.530(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.522(4) . ?
C8 C9 1.553(4) . ?
C8 H8 1.0000 . ?
C9 C11 1.543(4) . ?
C9 C10 1.557(4) . ?
C9 H9 1.0000 . ?
C10 C22 1.536(4) . ?
C11 C12 1.535(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.529(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.537(4) . ?
C13 C23 1.537(4) . ?
C13 C17 1.543(4) . ?
C14 C15 1.539(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.553(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.535(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.425(4) . ?
C17 O21 1.442(3) . ?
O18 C19 1.425(4) . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O21 1.426(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 112.9(3) . . ?
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 . . ?
O2 C2 C3 108.0(2) . . ?
O2 C2 C1 110.7(3) . . ?
C3 C2 C1 111.2(2) . . ?
O2 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C2 O2 H2O 109(3) . . ?
O3 C3 C2 110.6(2) . . ?
O3 C3 C4 108.9(3) . . ?
C2 C3 C4 111.7(2) . . ?
O3 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C3 O3 H3O 109(3) . . ?
C3 C4 C5 111.8(3) . . ?
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 112.5(2) . . ?
C6 C5 C10 112.4(2) . . ?
C4 C5 C10 112.1(2) . . ?
C6 C5 H5 106.4 . . ?
C4 C5 H5 106.4 . . ?
C10 C5 H5 106.4 . . ?
C5 C6 C7 110.9(3) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.1(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C14 C8 C7 112.5(2) . . ?
C14 C8 C9 108.9(2) . . ?
C7 C8 C9 111.0(2) . . ?
C14 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C11 C9 C8 111.8(2) . . ?
C11 C9 C10 113.1(2) . . ?
C8 C9 C10 112.5(2) . . ?
C11 C9 H9 106.3 . . ?
C8 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
C22 C10 C1 109.2(2) . . ?
C22 C10 C5 112.1(3) . . ?
C1 C10 C5 106.6(2) . . ?
C22 C10 C9 110.3(2) . . ?
C1 C10 C9 110.4(2) . . ?
C5 C10 C9 108.1(2) . . ?
C12 C11 C9 113.6(2) . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.2(3) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 108.5(2) . . ?
C12 C13 C23 111.7(2) . . ?
C14 C13 C23 112.6(3) . . ?
C12 C13 C17 116.2(2) . . ?
C14 C13 C17 100.3(2) . . ?
C23 C13 C17 107.2(2) . . ?
C8 C14 C13 112.2(2) . . ?
C8 C14 C15 119.3(2) . . ?
C13 C14 C15 104.0(2) . . ?
C8 C14 H14 106.9 . . ?
C13 C14 H14 106.9 . . ?
C15 C14 H14 106.9 . . ?
C14 C15 C16 104.5(2) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 105.9(2) . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O18 C17 O21 105.4(2) . . ?
O18 C17 C16 111.3(2) . . ?
O21 C17 C16 111.8(2) . . ?
O18 C17 C13 110.3(2) . . ?
O21 C17 C13 113.5(2) . . ?
C16 C17 C13 104.7(2) . . ?
C17 O18 C19 106.5(2) . . ?
O18 C19 C20 101.7(2) . . ?
O18 C19 H19A 111.4 . . ?
C20 C19 H19A 111.4 . . ?
O18 C19 H19B 111.4 . . ?
C20 C19 H19B 111.4 . . ?
H19A C19 H19B 109.3 . . ?
O21 C20 C19 101.9(3) . . ?
O21 C20 H20A 111.4 . . ?
C19 C20 H20A 111.4 . . ?
O21 C20 H20B 111.4 . . ?
C19 C20 H20B 111.4 . . ?
H20A C20 H20B 109.3 . . ?
C20 O21 C17 108.6(2) . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 O2 -177.2(2) . . . . ?
C10 C1 C2 C3 -57.2(3) . . . . ?
O2 C2 C3 O3 -63.8(3) . . . . ?
C1 C2 C3 O3 174.6(3) . . . . ?
O2 C2 C3 C4 174.6(2) . . . . ?
C1 C2 C3 C4 53.0(3) . . . . ?
O3 C3 C4 C5 -175.7(2) . . . . ?
C2 C3 C4 C5 -53.2(3) . . . . ?
C3 C4 C5 C6 -175.6(2) . . . . ?
C3 C4 C5 C10 56.6(3) . . . . ?
C4 C5 C6 C7 173.6(2) . . . . ?
C10 C5 C6 C7 -58.7(3) . . . . ?
C5 C6 C7 C8 57.1(3) . . . . ?
C6 C7 C8 C14 -177.3(2) . . . . ?
C6 C7 C8 C9 -55.1(3) . . . . ?
C14 C8 C9 C11 -52.1(3) . . . . ?
C7 C8 C9 C11 -176.4(2) . . . . ?
C14 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C9 C10 55.1(3) . . . . ?
C2 C1 C10 C22 -63.6(3) . . . . ?
C2 C1 C10 C5 57.7(3) . . . . ?
C2 C1 C10 C9 174.9(2) . . . . ?
C6 C5 C10 C22 -65.5(3) . . . . ?
C4 C5 C10 C22 62.5(3) . . . . ?
C6 C5 C10 C1 175.1(2) . . . . ?
C4 C5 C10 C1 -57.0(3) . . . . ?
C6 C5 C10 C9 56.4(3) . . . . ?
C4 C5 C10 C9 -175.7(2) . . . . ?
C11 C9 C10 C22 -59.3(3) . . . . ?
C8 C9 C10 C22 68.6(3) . . . . ?
C11 C9 C10 C1 61.5(3) . . . . ?
C8 C9 C10 C1 -170.6(2) . . . . ?
C11 C9 C10 C5 177.8(2) . . . . ?
C8 C9 C10 C5 -54.3(3) . . . . ?
C8 C9 C11 C12 50.8(3) . . . . ?
C10 C9 C11 C12 179.0(2) . . . . ?
C9 C11 C12 C13 -53.7(3) . . . . ?
C11 C12 C13 C14 57.8(3) . . . . ?
C11 C12 C13 C23 -66.8(3) . . . . ?
C11 C12 C13 C17 169.8(2) . . . . ?
C7 C8 C14 C13 -177.1(2) . . . . ?
C9 C8 C14 C13 59.5(3) . . . . ?
C7 C8 C14 C15 -55.2(3) . . . . ?
C9 C8 C14 C15 -178.6(2) . . . . ?
C12 C13 C14 C8 -63.0(3) . . . . ?
C23 C13 C14 C8 61.1(3) . . . . ?
C17 C13 C14 C8 174.7(2) . . . . ?
C12 C13 C14 C15 166.7(2) . . . . ?
C23 C13 C14 C15 -69.1(3) . . . . ?
C17 C13 C14 C15 44.5(3) . . . . ?
C8 C14 C15 C16 -156.8(2) . . . . ?
C13 C14 C15 C16 -30.9(3) . . . . ?
C14 C15 C16 C17 4.9(3) . . . . ?
C15 C16 C17 O18 -96.3(3) . . . . ?
C15 C16 C17 O21 146.0(2) . . . . ?
C15 C16 C17 C13 22.8(3) . . . . ?
C12 C13 C17 O18 -38.1(3) . . . . ?
C14 C13 C17 O18 78.5(3) . . . . ?
C23 C13 C17 O18 -163.8(2) . . . . ?
C12 C13 C17 O21 79.9(3) . . . . ?
C14 C13 C17 O21 -163.5(2) . . . . ?
C23 C13 C17 O21 -45.8(3) . . . . ?
C12 C13 C17 C16 -157.9(2) . . . . ?
C14 C13 C17 C16 -41.2(3) . . . . ?
C23 C13 C17 C16 76.5(3) . . . . ?
O21 C17 O18 C19 23.0(3) . . . . ?
C16 C17 O18 C19 -98.5(3) . . . . ?
C13 C17 O18 C19 145.8(2) . . . . ?
C17 O18 C19 C20 -37.9(3) . . . . ?
O18 C19 C20 O21 38.0(3) . . . . ?
C19 C20 O21 C17 -25.0(3) . . . . ?
O18 C17 O21 C20 2.5(3) . . . . ?
C16 C17 O21 C20 123.6(3) . . . . ?
C13 C17 O21 C20 -118.3(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
O2 H2O O3 0.86(2) 2.02(3) 2.854(3) 164(4) 2_657
O3 H3O O21 0.87(2) 2.04(3) 2.821(3) 149(4) 1_556

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042


####################################################################### 
# 
# 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_sb958_hy
_database_code_depnum_ccdc_archive 'CCDC 1822522'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2R,3S,5S,8R,9S,10S,13S,14S)-2,3-dihydroxy-10,13-dimethylhexadecahydro-
17H-cyclopenta[a]phenanthren-17-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H30 O3'
_chemical_formula_sum            'C19 H30 O3'
_chemical_formula_weight         306.43

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

_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, y+1/2, -z'

_cell_length_a                   6.0976(2)
_cell_length_b                   22.7525(7)
_cell_length_c                   6.2997(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.857(3)
_cell_angle_gamma                90
_cell_volume                     827.08(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4131
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      71.7

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 12+1 runs, 1733 frames, 20/40/60 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 Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            8766
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.886
_diffrn_reflns_theta_max         71.926
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3222
_reflns_number_gt                2741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.995

_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          
;
probably disorder of OH at C3 and C4 in approx. ration 80:20, 
possible disorder of O2, disorder not solved.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²+0.5930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 
 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = -0.09(19) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3222
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.8583(10) 0.47672(19) 0.5214(9) 0.0305(11) Uani 1 1 d . . . . .
H1A H 1.0020 0.4860 0.6453 0.037 Uiso 1 1 calc R U . . .
H1B H 0.7260 0.4819 0.5783 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8673(12) 0.4124(2) 0.4514(10) 0.0398(14) Uani 1 1 d . . . . .
H2 H 1.0067 0.4080 0.4021 0.048 Uiso 1 1 calc R U . . .
O2 O 0.9032(14) 0.3760(2) 0.6462(9) 0.087(2) Uani 1 1 d . . . . .
H2O H 0.7924 0.3804 0.6965 0.130 Uiso 1 1 calc R U . . .
C3 C 0.6593(11) 0.3957(2) 0.2559(11) 0.0420(14) Uani 1 1 d . . . . .
H3 H 0.6781 0.3546 0.2080 0.050 Uiso 1 1 calc R U . . .
O3 O 0.4642(10) 0.39860(17) 0.3322(11) 0.0761(19) Uani 1 1 d . . . . .
H3O H 0.3440 0.3895 0.2269 0.114 Uiso 1 1 calc R U . . .
C4 C 0.6302(10) 0.4378(2) 0.0590(10) 0.0333(12) Uani 1 1 d . . . . .
H4A H 0.4874 0.4276 -0.0647 0.040 Uiso 1 1 calc R U . . .
H4B H 0.7633 0.4334 0.0028 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6153(8) 0.50172(18) 0.1308(8) 0.0226(10) Uani 1 1 d . . . . .
H5 H 0.4813 0.5037 0.1893 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5623(9) 0.5443(2) -0.0643(8) 0.0272(11) Uani 1 1 d . . . . .
H6A H 0.4238 0.5306 -0.1862 0.033 Uiso 1 1 calc R U . . .
H6B H 0.6944 0.5453 -0.1232 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5184(8) 0.60600(19) 0.0088(8) 0.0229(10) Uani 1 1 d . . . . .
H7A H 0.4903 0.6333 -0.1197 0.027 Uiso 1 1 calc R U . . .
H7B H 0.3777 0.6055 0.0547 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7234(7) 0.62805(17) 0.2034(7) 0.0159(8) Uani 1 1 d . . . . .
H8 H 0.8604 0.6328 0.1505 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7853(8) 0.58317(17) 0.4004(7) 0.0168(8) Uani 1 1 d . . . . .
H9 H 0.6441 0.5798 0.4475 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8325(8) 0.52037(18) 0.3265(8) 0.0186(9) Uani 1 1 d . . . . .
C11 C 0.9776(8) 0.60688(17) 0.6044(7) 0.0211(9) Uani 1 1 d . . . . .
H11A H 1.1235 0.6089 0.5676 0.025 Uiso 1 1 calc R U . . .
H11B H 1.0020 0.5789 0.7303 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9265(8) 0.66790(19) 0.6814(8) 0.0228(10) Uani 1 1 d . . . . .
H12A H 0.7931 0.6654 0.7381 0.027 Uiso 1 1 calc R U . . .
H12B H 1.0626 0.6819 0.8052 0.027 Uiso 1 1 calc R U . . .
C13 C 0.8719(8) 0.71116(17) 0.4869(8) 0.0198(9) Uani 1 1 d . . . . .
C14 C 0.6703(7) 0.68708(17) 0.2910(7) 0.0179(9) Uani 1 1 d . . . . .
H14 H 0.5412 0.6795 0.3530 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5925(9) 0.73998(18) 0.1313(9) 0.0273(10) Uani 1 1 d . . . . .
H15A H 0.6960 0.7458 0.0401 0.033 Uiso 1 1 calc R U . . .
H15B H 0.4312 0.7350 0.0302 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6119(9) 0.7914(2) 0.2950(9) 0.0297(11) Uani 1 1 d . . . . .
H16A H 0.6778 0.8265 0.2451 0.036 Uiso 1 1 calc R U . . .
H16B H 0.4576 0.8016 0.3047 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7708(8) 0.77015(18) 0.5199(9) 0.0239(10) Uani 1 1 d . . . . .
O17 O 0.8025(7) 0.79480(15) 0.6976(6) 0.0337(9) Uani 1 1 d . . . . .
C18 C 1.0540(8) 0.5197(2) 0.2600(8) 0.0241(10) Uani 1 1 d . . . . .
H18A H 1.0370 0.5474 0.1366 0.036 Uiso 1 1 calc R U . . .
H18B H 1.1866 0.5313 0.3892 0.036 Uiso 1 1 calc R U . . .
H18C H 1.0794 0.4801 0.2119 0.036 Uiso 1 1 calc R U . . .
C19 C 1.0891(8) 0.7255(2) 0.4221(9) 0.0287(11) Uani 1 1 d . . . . .
H19A H 1.1624 0.6889 0.3984 0.043 Uiso 1 1 calc R U . . .
H19B H 1.0442 0.7487 0.2837 0.043 Uiso 1 1 calc R U . . .
H19C H 1.1987 0.7480 0.5430 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 1.535(6) . ?
C1 C10 1.547(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.437(7) . ?
C2 C3 1.503(9) . ?
C2 H2 1.0000 . ?
O2 H2O 0.8400 . ?
C3 O3 1.422(7) . ?
C3 C4 1.531(8) . ?
C3 H3 1.0000 . ?
O3 H3O 0.8400 . ?
C4 C5 1.535(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(7) . ?
C5 C10 1.549(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.526(5) . ?
C8 C9 1.556(5) . ?
C8 H8 1.0000 . ?
C9 C11 1.531(6) . ?
C9 C10 1.558(5) . ?
C9 H9 1.0000 . ?
C10 C18 1.538(6) . ?
C11 C12 1.535(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.519(6) . ?
C13 C14 1.534(6) . ?
C13 C19 1.542(6) . ?
C14 C15 1.542(6) . ?
C14 H14 1.0000 . ?
C15 C16 1.538(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.211(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 112.8(4) . . ?
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 . . ?
O2 C2 C3 114.2(5) . . ?
O2 C2 C1 108.3(4) . . ?
C3 C2 C1 112.2(5) . . ?
O2 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C2 O2 H2O 109.5 . . ?
O3 C3 C2 106.7(5) . . ?
O3 C3 C4 110.7(5) . . ?
C2 C3 C4 110.6(4) . . ?
O3 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C3 O3 H3O 109.5 . . ?
C3 C4 C5 110.9(4) . . ?
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 112.6(4) . . ?
C6 C5 C10 112.0(3) . . ?
C4 C5 C10 112.2(4) . . ?
C6 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C10 C5 H5 106.5 . . ?
C5 C6 C7 110.8(4) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 111.5(4) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C14 111.4(3) . . ?
C7 C8 C9 110.5(3) . . ?
C14 C8 C9 108.3(3) . . ?
C7 C8 H8 108.9 . . ?
C14 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C11 C9 C8 111.1(3) . . ?
C11 C9 C10 114.1(3) . . ?
C8 C9 C10 112.6(3) . . ?
C11 C9 H9 106.1 . . ?
C8 C9 H9 106.1 . . ?
C10 C9 H9 106.1 . . ?
C18 C10 C1 109.7(4) . . ?
C18 C10 C5 112.4(4) . . ?
C1 C10 C5 107.3(4) . . ?
C18 C10 C9 110.7(4) . . ?
C1 C10 C9 109.4(3) . . ?
C5 C10 C9 107.2(3) . . ?
C9 C11 C12 113.9(3) . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 110.2(4) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C17 C13 C12 117.0(4) . . ?
C17 C13 C14 99.8(4) . . ?
C12 C13 C14 109.1(3) . . ?
C17 C13 C19 105.7(4) . . ?
C12 C13 C19 111.5(4) . . ?
C14 C13 C19 113.3(4) . . ?
C8 C14 C13 113.4(3) . . ?
C8 C14 C15 120.5(4) . . ?
C13 C14 C15 104.1(3) . . ?
C8 C14 H14 105.9 . . ?
C13 C14 H14 105.9 . . ?
C15 C14 H14 105.9 . . ?
C16 C15 C14 102.4(4) . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 105.8(4) . . ?
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 C16 125.5(4) . . ?
O17 C17 C13 125.8(4) . . ?
C16 C17 C13 108.6(4) . . ?
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 . . ?

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 O2 177.1(5) . . . . ?
C10 C1 C2 C3 -56.0(6) . . . . ?
O2 C2 C3 O3 57.7(6) . . . . ?
C1 C2 C3 O3 -65.9(5) . . . . ?
O2 C2 C3 C4 178.3(4) . . . . ?
C1 C2 C3 C4 54.6(6) . . . . ?
O3 C3 C4 C5 62.4(6) . . . . ?
C2 C3 C4 C5 -55.8(6) . . . . ?
C3 C4 C5 C6 -174.3(4) . . . . ?
C3 C4 C5 C10 58.4(5) . . . . ?
C4 C5 C6 C7 172.7(4) . . . . ?
C10 C5 C6 C7 -59.8(5) . . . . ?
C5 C6 C7 C8 56.8(5) . . . . ?
C6 C7 C8 C14 -174.5(4) . . . . ?
C6 C7 C8 C9 -54.0(5) . . . . ?
C7 C8 C9 C11 -175.3(4) . . . . ?
C14 C8 C9 C11 -53.0(4) . . . . ?
C7 C8 C9 C10 55.2(5) . . . . ?
C14 C8 C9 C10 177.5(3) . . . . ?
C2 C1 C10 C18 -67.4(6) . . . . ?
C2 C1 C10 C5 55.0(6) . . . . ?
C2 C1 C10 C9 171.0(5) . . . . ?
C6 C5 C10 C18 -63.6(5) . . . . ?
C4 C5 C10 C18 64.1(5) . . . . ?
C6 C5 C10 C1 175.8(4) . . . . ?
C4 C5 C10 C1 -56.5(5) . . . . ?
C6 C5 C10 C9 58.3(4) . . . . ?
C4 C5 C10 C9 -174.0(4) . . . . ?
C11 C9 C10 C18 -61.0(5) . . . . ?
C8 C9 C10 C18 66.9(5) . . . . ?
C11 C9 C10 C1 60.0(5) . . . . ?
C8 C9 C10 C1 -172.1(4) . . . . ?
C11 C9 C10 C5 176.1(4) . . . . ?
C8 C9 C10 C5 -56.0(4) . . . . ?
C8 C9 C11 C12 53.3(5) . . . . ?
C10 C9 C11 C12 -178.1(4) . . . . ?
C9 C11 C12 C13 -54.6(5) . . . . ?
C11 C12 C13 C17 168.1(4) . . . . ?
C11 C12 C13 C14 55.9(5) . . . . ?
C11 C12 C13 C19 -70.1(5) . . . . ?
C7 C8 C14 C13 -179.9(4) . . . . ?
C9 C8 C14 C13 58.4(4) . . . . ?
C7 C8 C14 C15 -55.6(5) . . . . ?
C9 C8 C14 C15 -177.3(4) . . . . ?
C17 C13 C14 C8 176.1(3) . . . . ?
C12 C13 C14 C8 -60.7(5) . . . . ?
C19 C13 C14 C8 64.2(5) . . . . ?
C17 C13 C14 C15 43.3(4) . . . . ?
C12 C13 C14 C15 166.6(4) . . . . ?
C19 C13 C14 C15 -68.6(4) . . . . ?
C8 C14 C15 C16 -168.0(4) . . . . ?
C13 C14 C15 C16 -39.5(5) . . . . ?
C14 C15 C16 C17 19.3(5) . . . . ?
C15 C16 C17 O17 -168.9(5) . . . . ?
C15 C16 C17 C13 7.7(5) . . . . ?
C12 C13 C17 O17 27.8(6) . . . . ?
C14 C13 C17 O17 145.2(5) . . . . ?
C19 C13 C17 O17 -97.0(5) . . . . ?
C12 C13 C17 C16 -148.8(4) . . . . ?
C14 C13 C17 C16 -31.3(4) . . . . ?
C19 C13 C17 C16 86.5(4) . . . . ?

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
O2 H2O O3 0.84 2.54 2.815(10) 100.0 .
O3 H3O O17 0.84 2.44 2.839(5) 110.2 2_646

_refine_diff_density_max         1.003
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.059



# start Validation Reply Form
_vrf_PLAT097_sb958_hy            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.00 eA-3  
RESPONSE: probably disorder of OH at C3 and C4 in approx. ration 80:20
;
####################################################################### 
# 
# 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_sb1028_hy
_database_code_depnum_ccdc_archive 'CCDC 1822527'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger' 'University of Helsinki'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(2R,3S,5aR,5bS,7aS,8S,10aS,10bR,12aS)-8-(benzyloxy)-7a-
methyltetradecahydro-1H,5H-3,5a-methanocyclopenta[5,6]-
naphtho[1,2-c]oxepin-2-yl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H38 O4'
_chemical_formula_sum            'C28 H38 O4'
_chemical_formula_weight         438.58

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

_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, y+1/2, -z'

_cell_length_a                   9.6663(3)
_cell_length_b                   7.5343(2)
_cell_length_c                   16.3096(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.857(2)
_cell_angle_gamma                90
_cell_volume                     1179.31(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      2.7
_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    1.235
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8822
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 17+1 runs, 2511 frames, 16/24/32 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            17473
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.607
_diffrn_reflns_theta_max         72.150
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4591
_reflns_number_gt                4482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.990

_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)+(0.0530P)²+0.1545P] 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 2008 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   0.13(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4591
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.18236(19) 0.4059(3) 0.22494(12) 0.0292(4) Uani 1 1 d . . . . .
H1A H 0.1704 0.2940 0.2551 0.035 Uiso 1 1 calc R U . . .
H1B H 0.0904 0.4487 0.1994 0.035 Uiso 1 1 calc R U . . .
C2 C 0.28441(19) 0.3843(3) 0.16147(12) 0.0301(4) Uani 1 1 d . . . . .
H2 H 0.2667 0.2711 0.1299 0.036 Uiso 1 1 calc R U . . .
O2 O 0.41897(14) 0.3808(2) 0.21031(8) 0.0332(3) Uani 1 1 d . . . . .
C3 C 0.27303(18) 0.5426(3) 0.10370(11) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.1762 0.5511 0.0746 0.034 Uiso 1 1 calc R U . . .
O31 O 0.37070(13) 0.51171(19) 0.04423(8) 0.0312(3) Uani 1 1 d . . . . .
C31 C 0.3541(2) 0.6117(3) -0.02459(12) 0.0304(4) Uani 1 1 d . . . . .
O32 O 0.26215(16) 0.7193(2) -0.03912(9) 0.0358(3) Uani 1 1 d . . . . .
C32 C 0.4632(2) 0.5700(3) -0.07931(13) 0.0403(5) Uani 1 1 d . . . . .
H32A H 0.4577 0.6560 -0.1247 0.060 Uiso 1 1 calc R U . . .
H32B H 0.4480 0.4501 -0.1019 0.060 Uiso 1 1 calc R U . . .
H32C H 0.5555 0.5766 -0.0473 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3102(2) 0.7129(3) 0.15140(11) 0.0287(4) Uani 1 1 d . . . . .
H4A H 0.2784 0.8155 0.1162 0.034 Uiso 1 1 calc R U . . .
H4B H 0.4129 0.7208 0.1636 0.034 Uiso 1 1 calc R U . . .
C5 C 0.24566(19) 0.7252(3) 0.23277(11) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.1441 0.7506 0.2187 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3104(2) 0.8817(3) 0.28343(12) 0.0300(4) Uani 1 1 d . . . . .
H6A H 0.4129 0.8671 0.2919 0.036 Uiso 1 1 calc R U . . .
H6B H 0.2893 0.9929 0.2521 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2565(2) 0.8969(2) 0.36701(12) 0.0285(4) Uani 1 1 d . . . . .
H7A H 0.1562 0.9273 0.3588 0.034 Uiso 1 1 calc R U . . .
H7B H 0.3064 0.9941 0.3990 0.034 Uiso 1 1 calc R U . . .
C8 C 0.27689(18) 0.7240(2) 0.41595(11) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.3789 0.6977 0.4266 0.027 Uiso 1 1 calc R U . . .
C9 C 0.20367(18) 0.5697(2) 0.36556(11) 0.0238(4) Uani 1 1 d . . . . .
H9 H 0.1039 0.6059 0.3528 0.029 Uiso 1 1 calc R U . . .
C10 C 0.25936(17) 0.5478(2) 0.28128(11) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.2027(2) 0.3963(3) 0.41567(12) 0.0306(4) Uani 1 1 d . . . . .
H11A H 0.1436 0.3078 0.3831 0.037 Uiso 1 1 calc R U . . .
H11B H 0.2986 0.3483 0.4250 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1481(2) 0.4227(2) 0.49908(12) 0.0305(4) Uani 1 1 d . . . . .
H12A H 0.0484 0.4563 0.4900 0.037 Uiso 1 1 calc R U . . .
H12B H 0.1558 0.3097 0.5303 0.037 Uiso 1 1 calc R U . . .
C13 C 0.23010(18) 0.5666(2) 0.54930(11) 0.0248(4) Uani 1 1 d . . . . .
C14 C 0.21847(18) 0.7383(2) 0.49844(11) 0.0239(4) Uani 1 1 d . . . . .
H14 H 0.1165 0.7616 0.4848 0.029 Uiso 1 1 calc R U . . .
C15 C 0.2733(2) 0.8829(3) 0.56038(12) 0.0310(4) Uani 1 1 d . . . . .
H15A H 0.2309 0.9994 0.5446 0.037 Uiso 1 1 calc R U . . .
H15B H 0.3759 0.8933 0.5638 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2282(2) 0.8174(3) 0.64383(12) 0.0336(4) Uani 1 1 d . . . . .
H16A H 0.3093 0.8121 0.6870 0.040 Uiso 1 1 calc R U . . .
H16B H 0.1574 0.8979 0.6627 0.040 Uiso 1 1 calc R U . . .
C17 C 0.16637(19) 0.6296(3) 0.62578(12) 0.0274(4) Uani 1 1 d . . . . .
H17 H 0.0633 0.6407 0.6113 0.033 Uiso 1 1 calc R U . . .
O17 O 0.19313(13) 0.50570(19) 0.69123(8) 0.0308(3) Uani 1 1 d . . . . .
C18 C 0.1236(2) 0.5465(3) 0.76025(12) 0.0302(4) Uani 1 1 d . . . . .
H18A H 0.0244 0.5723 0.7418 0.036 Uiso 1 1 calc R U . . .
H18B H 0.1658 0.6534 0.7883 0.036 Uiso 1 1 calc R U . . .
C19 C 0.13423(18) 0.3929(3) 0.81959(11) 0.0274(4) Uani 1 1 d . . . . .
C20 C 0.2135(2) 0.2427(3) 0.80809(13) 0.0347(4) Uani 1 1 d . . . . .
H20 H 0.2618 0.2342 0.7608 0.042 Uiso 1 1 calc R U . . .
C21 C 0.2224(2) 0.1050(3) 0.86526(14) 0.0398(5) Uani 1 1 d . . . . .
H21 H 0.2770 0.0032 0.8571 0.048 Uiso 1 1 calc R U . . .
C22 C 0.1515(2) 0.1161(3) 0.93427(13) 0.0357(4) Uani 1 1 d . . . . .
H22 H 0.1580 0.0223 0.9735 0.043 Uiso 1 1 calc R U . . .
C23 C 0.0713(2) 0.2643(3) 0.94584(12) 0.0323(4) Uani 1 1 d . . . . .
H23 H 0.0219 0.2717 0.9927 0.039 Uiso 1 1 calc R U . . .
C24 C 0.06324(19) 0.4021(3) 0.88901(11) 0.0294(4) Uani 1 1 d . . . . .
H24 H 0.0087 0.5039 0.8975 0.035 Uiso 1 1 calc R U . . .
C25 C 0.40891(19) 0.4764(3) 0.28584(12) 0.0282(4) Uani 1 1 d . . . . .
H25A H 0.4765 0.5756 0.2916 0.034 Uiso 1 1 calc R U . . .
H25B H 0.4291 0.3965 0.3340 0.034 Uiso 1 1 calc R U . . .
C26 C 0.38110(19) 0.5088(3) 0.57486(12) 0.0315(4) Uani 1 1 d . . . . .
H26A H 0.4314 0.6036 0.6070 0.047 Uiso 1 1 calc R U . . .
H26B H 0.3821 0.4010 0.6086 0.047 Uiso 1 1 calc R U . . .
H26C H 0.4264 0.4848 0.5254 0.047 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 1.522(3) . ?
C1 C10 1.542(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.442(2) . ?
C2 C3 1.516(3) . ?
C2 H2 1.0000 . ?
O2 C25 1.440(2) . ?
C3 O31 1.451(2) . ?
C3 C4 1.521(3) . ?
C3 H3 1.0000 . ?
O31 C31 1.345(2) . ?
C31 O32 1.206(3) . ?
C31 C32 1.494(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C4 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(3) . ?
C5 C10 1.550(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.521(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.524(2) . ?
C8 C9 1.546(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.542(2) . ?
C9 C10 1.544(2) . ?
C9 H9 1.0000 . ?
C10 C25 1.536(2) . ?
C11 C12 1.530(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.531(3) . ?
C13 C26 1.533(2) . ?
C13 C14 1.533(2) . ?
C14 C15 1.536(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.558(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.550(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O17 1.419(2) . ?
C17 H17 1.0000 . ?
O17 C18 1.412(2) . ?
C18 C19 1.504(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.392(3) . ?
C19 C24 1.394(3) . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 100.00(14) . . ?
C2 C1 H1A 111.8 . . ?
C10 C1 H1A 111.8 . . ?
C2 C1 H1B 111.8 . . ?
C10 C1 H1B 111.8 . . ?
H1A C1 H1B 109.5 . . ?
O2 C2 C3 110.57(15) . . ?
O2 C2 C1 103.97(14) . . ?
C3 C2 C1 109.50(16) . . ?
O2 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C25 O2 C2 108.35(13) . . ?
O31 C3 C2 106.53(15) . . ?
O31 C3 C4 110.14(15) . . ?
C2 C3 C4 110.53(14) . . ?
O31 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C31 O31 C3 116.46(15) . . ?
O32 C31 O31 123.53(18) . . ?
O32 C31 C32 125.47(19) . . ?
O31 C31 C32 110.99(17) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C4 C5 113.40(15) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 109.32(15) . . ?
C6 C5 C10 112.59(14) . . ?
C4 C5 C10 111.74(15) . . ?
C6 C5 H5 107.7 . . ?
C4 C5 H5 107.7 . . ?
C10 C5 H5 107.7 . . ?
C7 C6 C5 112.37(15) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.55(15) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C14 C8 C7 111.27(14) . . ?
C14 C8 C9 109.16(14) . . ?
C7 C8 C9 109.96(14) . . ?
C14 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
C9 C8 H8 108.8 . . ?
C11 C9 C10 113.98(15) . . ?
C11 C9 C8 112.77(14) . . ?
C10 C9 C8 111.57(13) . . ?
C11 C9 H9 105.9 . . ?
C10 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C25 C10 C1 99.82(15) . . ?
C25 C10 C9 114.86(14) . . ?
C1 C10 C9 114.20(14) . . ?
C25 C10 C5 110.44(14) . . ?
C1 C10 C5 106.72(14) . . ?
C9 C10 C5 110.16(14) . . ?
C12 C11 C9 112.71(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 110.98(15) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C17 115.12(15) . . ?
C12 C13 C26 111.19(16) . . ?
C17 C13 C26 109.22(14) . . ?
C12 C13 C14 108.06(14) . . ?
C17 C13 C14 99.71(14) . . ?
C26 C13 C14 113.14(15) . . ?
C8 C14 C13 114.02(14) . . ?
C8 C14 C15 119.72(15) . . ?
C13 C14 C15 104.19(14) . . ?
C8 C14 H14 106.0 . . ?
C13 C14 H14 106.0 . . ?
C15 C14 H14 106.0 . . ?
C14 C15 C16 103.85(15) . . ?
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 . . ?
C17 C16 C15 105.36(16) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
O17 C17 C13 110.73(15) . . ?
O17 C17 C16 115.24(16) . . ?
C13 C17 C16 104.72(15) . . ?
O17 C17 H17 108.6 . . ?
C13 C17 H17 108.6 . . ?
C16 C17 H17 108.6 . . ?
C18 O17 C17 113.27(14) . . ?
O17 C18 C19 110.06(15) . . ?
O17 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
O17 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C24 118.84(18) . . ?
C20 C19 C18 122.36(16) . . ?
C24 C19 C18 118.80(17) . . ?
C21 C20 C19 120.49(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.84(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.00(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.74(18) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O2 C25 C10 107.04(14) . . ?
O2 C25 H25A 110.3 . . ?
C10 C25 H25A 110.3 . . ?
O2 C25 H25B 110.3 . . ?
C10 C25 H25B 110.3 . . ?
H25A C25 H25B 108.6 . . ?
C13 C26 H26A 109.5 . . ?
C13 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C13 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 O2 43.10(17) . . . . ?
C10 C1 C2 C3 -75.07(17) . . . . ?
C3 C2 O2 C25 91.31(18) . . . . ?
C1 C2 O2 C25 -26.13(19) . . . . ?
O2 C2 C3 O31 67.07(18) . . . . ?
C1 C2 C3 O31 -178.95(14) . . . . ?
O2 C2 C3 C4 -52.57(19) . . . . ?
C1 C2 C3 C4 61.41(18) . . . . ?
C2 C3 O31 C31 163.98(15) . . . . ?
C4 C3 O31 C31 -76.13(19) . . . . ?
C3 O31 C31 O32 -1.8(3) . . . . ?
C3 O31 C31 C32 178.53(16) . . . . ?
O31 C3 C4 C5 -161.06(15) . . . . ?
C2 C3 C4 C5 -43.6(2) . . . . ?
C3 C4 C5 C6 169.39(15) . . . . ?
C3 C4 C5 C10 44.07(19) . . . . ?
C4 C5 C6 C7 -177.22(15) . . . . ?
C10 C5 C6 C7 -52.4(2) . . . . ?
C5 C6 C7 C8 54.8(2) . . . . ?
C6 C7 C8 C14 -178.17(14) . . . . ?
C6 C7 C8 C9 -57.10(19) . . . . ?
C14 C8 C9 C11 -49.85(19) . . . . ?
C7 C8 C9 C11 -172.17(14) . . . . ?
C14 C8 C9 C10 -179.63(13) . . . . ?
C7 C8 C9 C10 58.04(18) . . . . ?
C2 C1 C10 C25 -42.36(17) . . . . ?
C2 C1 C10 C9 -165.42(14) . . . . ?
C2 C1 C10 C5 72.60(17) . . . . ?
C11 C9 C10 C25 -58.9(2) . . . . ?
C8 C9 C10 C25 70.24(19) . . . . ?
C11 C9 C10 C1 55.55(19) . . . . ?
C8 C9 C10 C1 -175.29(14) . . . . ?
C11 C9 C10 C5 175.62(14) . . . . ?
C8 C9 C10 C5 -55.22(17) . . . . ?
C6 C5 C10 C25 -75.80(19) . . . . ?
C4 C5 C10 C25 47.69(19) . . . . ?
C6 C5 C10 C1 176.62(15) . . . . ?
C4 C5 C10 C1 -59.89(18) . . . . ?
C6 C5 C10 C9 52.14(18) . . . . ?
C4 C5 C10 C9 175.62(14) . . . . ?
C10 C9 C11 C12 179.54(14) . . . . ?
C8 C9 C11 C12 51.0(2) . . . . ?
C9 C11 C12 C13 -55.1(2) . . . . ?
C11 C12 C13 C17 168.31(15) . . . . ?
C11 C12 C13 C26 -66.82(19) . . . . ?
C11 C12 C13 C14 57.91(19) . . . . ?
C7 C8 C14 C13 177.64(14) . . . . ?
C9 C8 C14 C13 56.11(18) . . . . ?
C7 C8 C14 C15 -58.1(2) . . . . ?
C9 C8 C14 C15 -179.60(15) . . . . ?
C12 C13 C14 C8 -60.53(18) . . . . ?
C17 C13 C14 C8 178.89(14) . . . . ?
C26 C13 C14 C8 63.0(2) . . . . ?
C12 C13 C14 C15 167.21(14) . . . . ?
C17 C13 C14 C15 46.63(16) . . . . ?
C26 C13 C14 C15 -69.24(18) . . . . ?
C8 C14 C15 C16 -162.01(15) . . . . ?
C13 C14 C15 C16 -33.12(18) . . . . ?
C14 C15 C16 C17 6.50(19) . . . . ?
C12 C13 C17 O17 77.86(18) . . . . ?
C26 C13 C17 O17 -48.0(2) . . . . ?
C14 C13 C17 O17 -166.83(14) . . . . ?
C12 C13 C17 C16 -157.33(15) . . . . ?
C26 C13 C17 C16 76.78(18) . . . . ?
C14 C13 C17 C16 -42.02(16) . . . . ?
C15 C16 C17 O17 144.26(16) . . . . ?
C15 C16 C17 C13 22.36(18) . . . . ?
C13 C17 O17 C18 -173.24(15) . . . . ?
C16 C17 O17 C18 68.2(2) . . . . ?
C17 O17 C18 C19 169.10(14) . . . . ?
O17 C18 C19 C20 5.3(2) . . . . ?
O17 C18 C19 C24 -175.33(15) . . . . ?
C24 C19 C20 C21 -0.5(3) . . . . ?
C18 C19 C20 C21 178.87(19) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
C20 C19 C24 C23 0.1(3) . . . . ?
C18 C19 C24 C23 -179.30(17) . . . . ?
C2 O2 C25 C10 -1.92(19) . . . . ?
C1 C10 C25 O2 28.34(18) . . . . ?
C9 C10 C25 O2 150.93(15) . . . . ?
C5 C10 C25 O2 -83.76(17) . . . . ?

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
C32 H32A O2 0.98 2.58 3.453(3) 148.9 2_655

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035


