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_1559081
_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 H44 O4, 0.5(H2 O)'
_chemical_formula_sum            'C27 H45 O4.5'
_chemical_formula_weight         441.63
_chemical_melting_point          527
_chemical_name_systematic        (25R)-5\a-Spirostan-3\b,5-diol
_chemical_optical_rotation       '[\a]^25^~D~=-63 (c=1, CHCl~3~)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-20
_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                 99.811(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3797(10)
_cell_length_b                   8.0820(4)
_cell_length_c                   28.058(2)
_cell_measurement_reflns_used    11028
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      2.30
_cell_volume                     2542.8(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
1201 frames, 50-70 /frame, 1 deg./frame, detector distance = 55 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  0.1544
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42679
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.499
_diffrn_reflns_theta_min         2.303
_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    0.049
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2935
_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    1.154
_exptl_crystal_description       plate
_exptl_crystal_F_000             972
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/CH2Cl2'
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.602
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     594
_refine_ls_number_reflns         9025
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.602
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0085P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                3338
_reflns_number_total             9025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01701a3.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 1559081--1559084.cif.'
_cod_original_cell_volume        2542.7(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C27 H45 O4.50'
_cod_database_code               1559081
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              44136