Reversible single-crystal-to-single-crystal phase transition of nirmatrelvir
Shi, Dier; Liu, Jiyong; Liu, Shuna; Wang, Yu; Yu, Kaxi; Hu, Xiurong; CrystEngComm 27 (2025) 6009–6018; doi:10.1039/D5CE00705D

data_1575371
_publ_section_title
;
 Reversible single-crystal-to-single-crystal phase transition of
 nirmatrelvir
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              6009
_journal_page_last               6018
_journal_paper_doi               10.1039/D5CE00705D
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2453(5)
_cell_length_b                   15.1879(8)
_cell_length_c                   18.1544(8)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    268.0
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.47
_cell_volume                     2549.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      268.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27731
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.244
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.9028.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0369P)^2^+1.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3622
_reflns_number_total             5830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00705d2.cif
_cod_data_source_block           nmtw_1_268k_0m
_cod_depositor_comments
'Adding full bibliography for 1575370--1575374.cif.'
_cod_database_code               1575371
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C6(H6), C17(H17), C3(H3A), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C12(H12A,H12B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C19(H19A,H19B,
 H19C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              22658
_olex2_submission_special_instructions 'No special instructions were received'