Structural flexibility of favipiravir and its structural analogues in solutions: experimental and computational insight.
Gerasimova, Tatiana P.; Zagidullin, Almaz A.; Nikolaeva, Anastasiia N.; Fayzullin, Robert R.; Saitova, Aliya M.; Miluykov, Vasili A.; Grimme, Stefan; Katsyuba, Sergey A.; Organic & biomolecular chemistry 22 (2024) 3668–3683; doi:10.1039/d4ob00404c

data_7159893
_publ_section_title
;
 Structural flexibility of favipiravir and its structural analogues in
 solutions: experimental and computational insight.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3668
_journal_page_last               3683
_journal_paper_doi               10.1039/d4ob00404c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C5 H5 N3 O2, 0.59(H2 O)'
_chemical_formula_sum            'C5 H6.18 N3 O2.59'
_chemical_formula_weight         149.75
_chemical_melting_point          538
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-08-23 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9049(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.62939(6)
_cell_length_b                   17.4327(3)
_cell_length_c                   10.06875(17)
_cell_measurement_reflns_used    6388
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      76.5090
_cell_measurement_theta_min      2.4150
_cell_volume                     627.555(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'XtaLAB Synergy, single source at home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.564
_diffrn_reflns_theta_min         5.074
_diffrn_source                   'microfocus sealed X-ray tube'
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_exptl_absorpt_correction_T_max  1.000
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_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020).
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model. Empirical absorption correction using
spherical harmonics, frame scaling and detector area scaling,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method 'from a water solution'
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1286
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0644P)^2^+0.2760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1278
_reflns_number_total             1286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00404c2.cif
_cod_data_source_block           mil317
_cod_depositor_comments
'Adding full bibliography for 7159893--7159895.cif.'
_cod_original_cell_volume        627.555(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159893
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.675
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              50464
_shelx_hkl_checksum              35483