#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/93/1559398.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1559398
loop_
_publ_author_name
'Verma, Vivek'
'Bordignon, Simone'
'Chierotti, Michele R.'
'Lestari, Monica'
'Lyons, Kieran'
'Padrela, Luis'
'Ryan, Kevin M.'
'Lusi, Matteo'
_publ_section_title
;
 Cortisone and cortisol break hydrogen-bonding rules to make a
 drug--prodrug solid solution
;
_journal_coeditor_code           LQ5036SUP1
_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 H28 O5'
_chemical_formula_weight         360.43
_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                   7.7819(4)
_cell_length_b                   10.0468(5)
_cell_length_c                   23.6401(13)
_cell_measurement_reflns_used    623
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     1848.26(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'bruker d8 quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20384
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.542
_diffrn_reflns_theta_min         2.661
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0504
_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/[σ²(Fo²)+(0.0687P)²+0.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3995
_reflns_number_total             5481
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5036.cif
_cod_data_source_block           C_KL1_C
_cod_database_code               1559398
_shelx_shelxl_version_number     2014/7
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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 0.0474(3) 0.3213(3) 0.86522(10) 0.0509(7) Uani 1 1 d . . . . .
H1A H -0.0535 0.3719 0.8544 0.061 Uiso 1 1 calc R U . . .
H1B H 0.0427 0.2367 0.8456 0.061 Uiso 1 1 calc R U . . .
C2 C 0.0402(4) 0.2953(3) 0.92885(11) 0.0518(7) Uani 1 1 d . . . . .
H2A H 0.0330 0.3793 0.9490 0.062 Uiso 1 1 calc R U . . .
H2B H -0.0615 0.2436 0.9378 0.062 Uiso 1 1 calc R U . . .
O3 O 0.1910(4) 0.1308(2) 0.98169(10) 0.0756(7) Uani 1 1 d . . . . .
C3 C 0.1951(4) 0.2222(3) 0.94707(10) 0.0472(6) Uani 1 1 d . . . . .
C4 C 0.3567(3) 0.2643(2) 0.92148(10) 0.0387(5) Uani 1 1 d . . . . .
H4 H 0.4587 0.2326 0.9369 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3661(3) 0.3461(2) 0.87698(9) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.5358(3) 0.3933(2) 0.85490(10) 0.0380(5) Uani 1 1 d . . . . .
H6A H 0.6273 0.3500 0.8758 0.046 Uiso 1 1 calc R U . . .
H6B H 0.5455 0.4884 0.8611 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5577(3) 0.3640(3) 0.79205(10) 0.0386(5) Uani 1 1 d . . . . .
H7A H 0.6632 0.4051 0.7789 0.046 Uiso 1 1 calc R U . . .
H7B H 0.5685 0.2687 0.7867 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4085(3) 0.4149(2) 0.75649(9) 0.0278(4) Uani 1 1 d . . . . .
H8 H 0.4086 0.5124 0.7568 0.033 Uiso 1 1 calc R U . . .
C9 C 0.2369(3) 0.3634(2) 0.78192(9) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.2442 0.2661 0.7802 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2084(3) 0.3971(2) 0.84553(9) 0.0320(5) Uani 1 1 d . . . . .
O11 O -0.0314(2) 0.4699(2) 0.75665(8) 0.0642(6) Uani 1 1 d . . . . .
C11 C 0.0887(3) 0.4010(3) 0.74278(10) 0.0408(5) Uani 1 1 d . . . . .
C12 C 0.1055(3) 0.3482(3) 0.68288(10) 0.0430(6) Uani 1 1 d . . . . .
H12A H 0.0072 0.3752 0.6604 0.052 Uiso 1 1 calc R U . . .
H12B H 0.1109 0.2518 0.6832 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2712(3) 0.40623(19) 0.65785(8) 0.0289(4) Uani 1 1 d . . . . .
C14 C 0.4222(3) 0.3658(2) 0.69566(9) 0.0288(4) Uani 1 1 d . . . . .
H14 H 0.4219 0.2683 0.6973 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5793(3) 0.4057(3) 0.66075(10) 0.0417(5) Uani 1 1 d . . . . .
H15A H 0.6783 0.3521 0.6708 0.050 Uiso 1 1 calc R U . . .
H15B H 0.6071 0.4989 0.6665 0.050 Uiso 1 1 calc R U . . .
C16 C 0.5244(3) 0.3797(3) 0.59909(11) 0.0421(6) Uani 1 1 d . . . . .
H16A H 0.5891 0.3059 0.5834 0.051 Uiso 1 1 calc R U . . .
H16B H 0.5454 0.4580 0.5761 0.051 Uiso 1 1 calc R U . . .
O17 O 0.2993(3) 0.20737(14) 0.60257(7) 0.0431(4) Uani 1 1 d . . . . .
H17 H 0.3448 0.1707 0.5754 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3309(3) 0.3466(2) 0.59999(9) 0.0322(5) Uani 1 1 d . . . . .
C18 C 0.2529(4) 0.5579(2) 0.65260(11) 0.0457(6) Uani 1 1 d . . . . .
H18A H 0.2335 0.5957 0.6894 0.069 Uiso 1 1 calc R U . . .
H18B H 0.1576 0.5785 0.6284 0.069 Uiso 1 1 calc R U . . .
H18C H 0.3563 0.5945 0.6368 0.069 Uiso 1 1 calc R U . . .
C19 C 0.1923(4) 0.5468(2) 0.85717(12) 0.0531(7) Uani 1 1 d . . . . .
H19A H 0.1989 0.5624 0.8972 0.080 Uiso 1 1 calc R U . . .
H19B H 0.0840 0.5783 0.8431 0.080 Uiso 1 1 calc R U . . .
H19C H 0.2840 0.5932 0.8385 0.080 Uiso 1 1 calc R U . . .
O20 O 0.2765(3) 0.5048(2) 0.52600(9) 0.0681(6) Uani 1 1 d . . . . .
C20 C 0.2317(3) 0.4050(2) 0.54990(10) 0.0395(5) Uani 1 1 d . . . . .
O21 O -0.0163(3) 0.3992(2) 0.48742(9) 0.0665(7) Uani 1 1 d . . . . .
H21 H -0.0494 0.4728 0.4978 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0681(4) 0.3356(3) 0.53215(12) 0.0558(7) Uani 1 1 d . . . . .
H21A H 0.0953 0.2451 0.5210 0.067 Uiso 1 1 calc R U . . .
H21B H -0.0090 0.3310 0.5644 0.067 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 114.4(2) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 110.0(2) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O3 C3 C4 121.0(3) . . ?
O3 C3 C2 123.0(3) . . ?
C4 C3 C2 116.0(2) . . ?
C5 C4 C3 123.5(2) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 C10 123.2(2) . . ?
C6 C5 C10 115.71(18) . . ?
C5 C6 C7 112.21(18) . . ?
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 . . ?
C8 C7 C6 112.83(19) . . ?
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 111.03(18) . . ?
C7 C8 C9 109.31(18) . . ?
C14 C8 C9 108.53(17) . . ?
C7 C8 H8 109.3 . . ?
C14 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C11 C9 C8 109.42(18) . . ?
C11 C9 C10 115.09(18) . . ?
C8 C9 C10 115.06(17) . . ?
C11 C9 H9 105.4 . . ?
C8 C9 H9 105.4 . . ?
C10 C9 H9 105.4 . . ?
C5 C10 C19 107.9(2) . . ?
C5 C10 C1 109.98(19) . . ?
C19 C10 C1 111.4(2) . . ?
C5 C10 C9 106.45(17) . . ?
C19 C10 C9 113.48(19) . . ?
C1 C10 C9 107.48(17) . . ?
O11 C11 C12 121.3(2) . . ?
O11 C11 C9 124.2(2) . . ?
C12 C11 C9 114.5(2) . . ?
C11 C12 C13 107.44(18) . . ?
C11 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 C12 108.61(17) . . ?
C14 C13 C18 112.42(19) . . ?
C12 C13 C18 109.3(2) . . ?
C14 C13 C17 100.41(17) . . ?
C12 C13 C17 116.23(17) . . ?
C18 C13 C17 109.70(18) . . ?
C8 C14 C15 118.73(19) . . ?
C8 C14 C13 114.27(17) . . ?
C15 C14 C13 103.23(17) . . ?
C8 C14 H14 106.6 . . ?
C15 C14 H14 106.6 . . ?
C13 C14 H14 106.6 . . ?
C14 C15 C16 104.17(19) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C17 107.09(19) . . ?
C15 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C17 O17 H17 109.5 . . ?
O17 C17 C20 108.84(19) . . ?
O17 C17 C16 112.46(19) . . ?
C20 C17 C16 113.5(2) . . ?
O17 C17 C13 106.73(17) . . ?
C20 C17 C13 112.31(18) . . ?
C16 C17 C13 102.69(18) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O20 C20 C21 119.9(2) . . ?
O20 C20 C17 122.5(2) . . ?
C21 C20 C17 117.6(2) . . ?
C21 O21 H21 109.5 . . ?
O21 C21 C20 113.2(2) . . ?
O21 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
O21 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
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 1.528(3) . ?
C1 C10 1.538(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.476(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C3 1.230(3) . ?
C3 C4 1.458(4) . ?
C4 C5 1.337(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.497(3) . ?
C5 C10 1.524(3) . ?
C6 C7 1.524(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.522(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.524(3) . ?
C8 C9 1.553(3) . ?
C8 H8 0.9800 . ?
C9 C11 1.526(3) . ?
C9 C10 1.557(3) . ?
C9 H9 0.9800 . ?
C10 C19 1.533(3) . ?
O11 C11 1.208(3) . ?
C11 C12 1.518(3) . ?
C12 C13 1.534(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.531(3) . ?
C13 C18 1.536(3) . ?
C13 C17 1.564(3) . ?
C14 C15 1.528(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.541(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.542(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O17 C17 1.422(2) . ?
O17 H17 0.8200 . ?
C17 C20 1.531(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O20 C20 1.203(3) . ?
C20 C21 1.511(4) . ?
O21 C21 1.399(3) . ?
O21 H21 0.8200 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 222786
