trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism
Hilario-Martínez, J. Ciciolil; Murillo, Fernando; García-Méndez, Jair; Dzib, Eugenia; Sandoval-Ramírez, Jesús; Muñoz-Hernández, Miguel Ángel; Bernès, Sylvain; Kürti, László; Duarte, Fernanda; Merino, Gabriel; Fernández-Herrera, María A.; Chemical Science 11 (2020) 12764–12768; doi:10.1039/D0SC01701A

data_1559083
_publ_section_title
;
 trans-Hydroboration--oxidation products in \D5-steroids via a
 hydroboration-retro-hydroboration mechanism
;
_journal_issue                   47
_journal_name_full               'Chemical Science'
_journal_page_first              12764
_journal_page_last               12768
_journal_paper_doi               10.1039/D0SC01701A
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H47 D O2'
_chemical_formula_sum            'C27 H47 D O2'
_chemical_formula_weight         405.66
_chemical_melting_point          467
_chemical_name_systematic        5\b-Cholestane-3\b,6\b-diol
_chemical_optical_rotation       '[\a]^25^~D~=+607 (c= 2 x 10^-4^, CHCl~3~)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-06
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1858(3)
_cell_length_b                   10.4115(6)
_cell_length_c                   30.9258(12)
_cell_measurement_reflns_used    24243
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.03
_cell_volume                     2635.7(2)
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_data_reduction        'X-AREA 1.86'
_computing_molecular_graphics
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
1398 frames, 45-55 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            45768
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         22.499
_diffrn_reflns_theta_min         2.031
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.041
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.022
_exptl_crystal_description       Prism
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/CH2Cl2'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.811
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3034
_reflns_number_total             6932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01701a3.cif
_cod_data_source_block           1c
_cod_depositor_comments
'Adding full bibliography for 1559081--1559084.cif.'
_cod_database_code               1559083
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              4786