Two polymorphs of remdesivir: crystal structure, solubility, and pharmacokinetic study
Yu, Kaxi; Chen, Shuai; Amgoth, Chander; Tang, Guping; Bai, Hongzhen; Hu, Xiurong; CrystEngComm 23 (2021) 2923–2927; doi:10.1039/D1CE00175B

data_7242581
_publ_section_title
;
 Two polymorphs of remdesivir: crystal structure, solubility, and
 pharmacokinetic study
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2923
_journal_page_last               2927
_journal_paper_doi               10.1039/D1CE00175B
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H35 N6 O8 P'
_chemical_formula_sum            'C27 H35 N6 O8 P'
_chemical_formula_weight         602.58
_chemical_name_common            remdesivir
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-07 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                96.105(4)
_cell_angle_beta                 99.219(4)
_cell_angle_gamma                94.937(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5565(11)
_cell_length_b                   10.5456(16)
_cell_length_c                   17.147(2)
_cell_measurement_reflns_used    783
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      40.07
_cell_measurement_theta_min      7.47
_cell_volume                     1510.2(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1329
_diffrn_reflns_av_unetI/netI     0.2058
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24237
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.319
_diffrn_reflns_theta_min         4.097
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5372
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(5)
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         11093
_refine_ls_number_restraints     552
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.2598
_refine_ls_R_factor_gt           0.1215
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2953
_refine_ls_wR_factor_ref         0.3938
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                4142
_reflns_number_total             11093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00175b2.cif
_cod_data_source_block           rdvformi
_cod_depositor_comments
'Adding full bibliography for 7242581--7242582.cif.'
_cod_original_cell_volume        1510.1(4)
_cod_database_code               7242581
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C23A-C22A = C26A-C23A = C26A-C27A
 1.53 with sigma of 0.02
 C23A-C24A
 1.53 with sigma of 0.02
 C24A-C25A
 1.53 with sigma of 0.02
 C24B-C23B = C24B-C25B
 1.53 with sigma of 0.02
 C26B-C23B
 1.53 with sigma of 0.02
 C26B-C27B
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
O8B \\sim C22B \\sim C23B \\sim C24B \\sim C25B \\sim C27B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
O8A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C22B \\sim C23B \\sim C26B \\sim C27B: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Riding coordinates:
 N6A(H6A), N6B(H6B)
4.b Rotating group:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB)
4.c Ternary CH refined with riding coordinates:
 C8A(H8A), C9A(H9A), C10A(H10A), C19A(H19A), C23A(H23A), C8B(H8B), C9B(H9B),
 C10B(H10B), C19B(H19B), C23B(H23B)
4.d Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C22A(H22A,H22B), C24A(H24A,H24B), C26A(H26A,H26B), C12B(H12C,
 H12D), C22B(H22C,H22D), C24B(H24C,H24D), C26B(H26C,H26D)
4.e Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C4A(H4A), C2A(H2AA), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A),
  C18A(H18A), C5B(H5B), C4B(H4B), C2B(H2BA), C14B(H14B), C15B(H15B), C16B(H16B),
  C17B(H17B), C18B(H18B)
4.f Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C25A(H25A,H25B,H25C), C27A(H27A,H27B,H27C), C20B(H20D,
 H20E,H20F), C25B(H25D,H25E,H25F), C27B(H27D,H27E,H27F)
4.g Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O2A(H2A), O3B(H3B), O2B(H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'