A new short synthesis route for favipiravir and its analogue: Their tautomerization behaviour
Ghosh, Priyanka; Panda, Subhra Jyoti; Purohit, Chandra Shekhar; New Journal of Chemistry 46 (2022) 18824–18831; doi:10.1039/D2NJ02996K

data_7061907
_publ_section_title
;
 A new short synthesis route for favipiravir and its analogue: Their
 tautomerization behaviour
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18824
_journal_page_last               18831
_journal_paper_doi               10.1039/D2NJ02996K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C5 H4 F N3 O2'
_chemical_formula_sum            'C5 H4 F N3 O2'
_chemical_formula_weight         157.11
_chemical_name_systematic        FAVIPIRAVIR
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-07
_audit_creation_method
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0668(5)
_cell_length_b                   14.8508(10)
_cell_length_c                   4.5755(3)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5690
_cell_measurement_theta_min      5.9020
_cell_volume                     616.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -78.00  11.00   0.50    0.57    --  -38.50 105.00-130.00  178
  2  \w     11.00  88.00   0.50    0.57    --   48.56-105.00 128.00  154
  3  \w     33.00 108.00   0.50    0.57    --  101.38-105.00 128.00  150
  4  \w    -50.00  24.00   0.50    0.57    --  -38.50  57.00  30.00  148
  5  \w     45.00 115.00   0.50    0.57    --   48.56  37.00 -30.00  140
  6  \w     33.00 107.00   0.50    0.57    --  101.38 -94.00 -60.00  148
  7  \w    103.00 166.00   0.50    0.57    --  101.38  77.00 120.00  126
  8  \w    104.00 171.00   0.50    0.57    --  101.38 111.00 -30.00  134
  9  \w     37.00 106.00   0.50    0.57    --  101.38 -45.00  90.00  138
 10  \w     33.00 105.00   0.50    0.57    --  101.38 -30.00-180.00  144
 11  \w     97.00 166.00   0.50    0.57    --  101.38  45.00 -30.00  138
 12  \w    103.00 166.00   0.50    0.57    --  101.38  77.00 -90.00  126
 13  \w    104.00 170.00   0.50    0.57    --  101.38 105.00-130.00  132
 14  \w     37.00 112.00   0.50    0.57    --   48.56  57.00  90.00  150
 15  \w     37.00 112.00   0.50    0.57    --   48.56  57.00 150.00  150
 16  \w     37.00 112.00   0.50    0.57    --   48.56  57.00  30.00  150
 17  \w     37.00 112.00   0.50    0.57    --   48.56  57.00-120.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356047000
_diffrn_orient_matrix_UB_12      0.1001304000
_diffrn_orient_matrix_UB_13      -0.0515197000
_diffrn_orient_matrix_UB_21      -0.1092335000
_diffrn_orient_matrix_UB_22      -0.0018497000
_diffrn_orient_matrix_UB_23      0.2579474000
_diffrn_orient_matrix_UB_31      0.1251357000
_diffrn_orient_matrix_UB_32      0.0268534000
_diffrn_orient_matrix_UB_33      0.2105568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4149
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.177
_diffrn_reflns_theta_min         5.717
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_preparation       'AS PER PROCEDURE IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1027
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0586
_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^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.787
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                881
_reflns_number_total             1027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7061906--7061913.cif.'
_cod_database_code               7061907
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H16 F4 N8 O8 '
_shelx_estimated_absorpt_t_max   0.774
_shelx_estimated_absorpt_t_min   0.680
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              34433
_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.070
_oxdiff_exptl_absorpt_empirical_full_min 0.617