Cortisone and cortisol break hydrogen-bonding rules to make a drug‒prodrug solid solution
Verma, Vivek; Bordignon, Simone; Chierotti, Michele R.; Lestari, Monica; Lyons, Kieran; Padrela, Luis; Ryan, Kevin M.; Lusi, Matteo; IUCrJ 7 (2020) –; doi:10.1107/S2052252520013263

data_1559401
_publ_section_title
;
 Cortisone and cortisol break hydrogen-bonding rules to make a
 drug--prodrug solid solution
;
_journal_issue                   6
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252520013263
_journal_volume                  7
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C21 H29.48 O5'
_chemical_formula_weight         361.92
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6953(9)
_cell_length_b                   10.1268(11)
_cell_length_c                   23.619(3)
_cell_measurement_reflns_used    72
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     1840.6(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'bruker d8 quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15740
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_min         2.650
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             782
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.1038
_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^)+(0.1970P)^2^+1.1973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3033
_refine_ls_wR_factor_ref         0.3150
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4255
_reflns_number_total             5534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5036.cif
_cod_data_source_block           KL5
_cod_database_code               1559401
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              31187
_shelx_hkl_checksum              25325