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_7159895
_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         'C8 H10 K N5 O5'
_chemical_formula_sum            'C8 H10 K N5 O5'
_chemical_formula_weight         295.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-02-18 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                86.9918(11)
_cell_angle_beta                 85.9992(11)
_cell_angle_gamma                68.7003(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1404(3)
_cell_length_b                   8.4811(4)
_cell_length_c                   9.2843(4)
_cell_measurement_reflns_used    31722
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      37.66
_cell_measurement_theta_min      2.20
_cell_volume                     595.49(4)
_computing_cell_refinement       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_collection       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_reduction        'APEX4 v2021.10-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      162(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            70459
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.780
_diffrn_reflns_theta_min         2.200
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.8806
_exptl_absorpt_correction_T_min  0.7348
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group -1 for scaling and error model
 Mean and maximum errors in direction cosine check function =   0.001   0.003
 Restraint esd for equal adjacent scale factors =  0.0090
 Maximum odd and even orders for spherical harmonics =   1   4
 wR2(int) =  0.1614 (selected reflections only, before parameter refinement)
 wR2(int) =  0.0532 (selected reflections only, after parameter refinement)

   70839 total and   5676 unique reflections assuming Friedel's law
 plus   2776 total and  1529 unique reflections in fast scans
 Reflections rejected for which |I-<I>|/su >   3.00
 where:  su^2 = sigma(I)^2 + (  0.04000 <I>)^2  (sigma(I) from SAINT)

   70457 total and   5676 unique reflections left after |I-<I>|/su test
 plus   2692 total and  1520 unique reflections in fast scans
 su^2 = [K*sigma(I)]^2 + [g<I>]^2  where sigma(I) is from SAINT

 Error model 5: refine all K and overall g
 Run 2theta R(int) Incid. factors Diffr. factors    K      g   I/s(lim) Total I>2sig(I)
   1  21.9  0.0409  0.152 - 0.377  0.991 - 1.040  0.918  0.0262  38.2    4169    3080
   2  21.9  0.0348  0.078 - 0.221  0.987 - 1.039  0.911  0.0262  38.2    4140    3301
   3  21.9  0.0344  0.103 - 0.142  0.987 - 1.025  0.921  0.0262  38.2    4073    3292
   4  21.9  0.0415  0.119 - 0.350  0.987 - 1.035  0.889  0.0262  38.2    4140    3165
   5  21.9  0.0404  0.144 - 0.280  0.991 - 1.036  0.943  0.0262  38.2    4164    3145
   6  21.9  0.0405  0.099 - 0.336  0.987 - 1.037  0.934  0.0262  38.2    4206    3166
   7  21.9  0.0435  0.142 - 0.384  0.987 - 1.038  0.960  0.0262  38.2    4201    3119
   8  21.9  0.0359  0.128 - 0.189  0.987 - 1.027  0.933  0.0262  38.2    4114    3234
   9  21.9  0.0418  0.148 - 0.349  0.987 - 1.029  0.908  0.0262  38.2    4170    3144
  10  21.9  0.0324  0.082 - 0.146  0.987 - 1.035  0.933  0.0262  38.2    4115    3409
  11  21.9  0.0424  0.127 - 0.366  0.987 - 1.031  0.923  0.0262  38.2    4135    3117
  12  21.9  0.0384  0.102 - 0.313  0.988 - 1.040  0.959  0.0262  38.2    6218    4971
  13  21.9  0.0411  0.120 - 0.312  0.987 - 1.040  1.022  0.0262  38.2    6873    5368
  14 -21.9  0.0371  0.081 - 0.275  0.987 - 1.040  0.933  0.0262  38.2    4081    3189
  15  34.9  0.0288  0.141 - 0.311  0.994 - 1.040  0.891  0.0262  38.2    4493    3782
  16   0.0  0.0351  0.189 - 0.268  0.991 - 1.040  1.061  0.0262  38.2    1761    1492
  17   0.0  0.0320  0.154 - 0.256  0.987 - 1.026  1.014  0.0262  38.2    1404    1216
  18f  0.0  0.0980  1.137 - 2.997  0.989 - 1.034  1.084  0.0262  38.2    2692    1689

       2 Overloads replaced by fast scan measurements
   70459 Corrected reflections written to file hkl
 Estimated minimum and maximum transmission:  0.7348  0.8806
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.0800
 3lambda correction factor = 0.00150
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.591
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0356P)^2^+0.1456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4715
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00404c2.cif
_cod_data_source_block           zagid009
_cod_depositor_comments
'Adding full bibliography for 7159893--7159895.cif.'
_cod_database_code               7159895
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.767
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              19385
_shelx_hkl_checksum              74909