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_7242582
_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_systematic        Remdesivir
_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
_audit_creation_date             2020-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-10 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.022(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5286(17)
_cell_length_b                   12.809(2)
_cell_length_c                   11.1106(19)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.45
_cell_volume                     1475.5(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28620
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.275
_diffrn_reflns_theta_min         2.448
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.0877 after correction.
The Ratio of minimum to maximum transmission is 0.6437.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 2533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6455
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0817P)^2^+0.9910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                5990
_reflns_number_total             6455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00175b2.cif
_cod_data_source_block           200424_rdv_tri_3_2nd_0m
_cod_depositor_comments
'Adding full bibliography for 7242581--7242582.cif.'
_cod_original_cell_volume        1475.6(4)
_cod_database_code               7242582
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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
 N6-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C19(H19), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C24(H24A,H24B), C26(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              21330
_shelx_hkl_checksum              82028
_olex2_submission_special_instructions 'No special instructions were received'