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_7061909
_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         '2(C7 H7 Cl N2 O3.014)'
_chemical_formula_sum            'C14 H14 Cl2 N4 O6'
_chemical_formula_weight         405.19
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-28 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                   18.7318(5)
_cell_length_b                   18.7318(5)
_cell_length_c                   5.1839(2)
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    300(1)
_cell_measurement_theta_max      74.0730
_cell_measurement_theta_min      4.7120
_cell_volume                     1818.93(10)
_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    '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      air
_diffrn_ambient_temperature      300(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9778
_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    -77.00  14.00   0.50    2.00    --  -38.50 104.00  28.00  182
  2  \w    104.00 171.00   0.50    8.00    --  102.63 104.00  28.00  134
  3  \w     34.00 107.00   0.50    8.00    --  102.63-104.00 -72.00  146
  4  \w   -101.00 -27.00   0.50    2.00    --  -38.50 -57.00-150.00  148
  5  \w      7.00  88.00   0.50    2.00    --   49.31-104.00 -72.00  162
  6  \w     46.00 116.00   0.50    2.00    --   49.31  38.00 120.00  140
  7  \w     38.00 107.00   0.50    8.00    --  102.63 -45.00 -30.00  138
  8  \w    125.00 168.00   0.50    8.00    --  102.63 125.00 -60.00   86
  9  \w    123.00 148.00   0.50    8.00    --  102.63  77.00-150.00   50
 10  \w     95.00 171.00   0.50    8.00    --  102.63  15.00-150.00  152
;
_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      -0.0746278000
_diffrn_orient_matrix_UB_12      -0.0290093000
_diffrn_orient_matrix_UB_13      0.0702549000
_diffrn_orient_matrix_UB_21      0.0273865000
_diffrn_orient_matrix_UB_22      -0.0769338000
_diffrn_orient_matrix_UB_23      -0.0317331000
_diffrn_orient_matrix_UB_31      0.0210472000
_diffrn_orient_matrix_UB_32      -0.0014366000
_diffrn_orient_matrix_UB_33      0.2870723000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7563
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.310
_diffrn_reflns_theta_min         4.721
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.480
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evapration'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1506
_reflns_number_total             1850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7061906--7061913.cif.'
_cod_original_cell_volume        1818.93(12)
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               7061909
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C56 H56 Cl8 N16 O24 '
_shelx_estimated_absorpt_t_max   0.634
_shelx_estimated_absorpt_t_min   0.445
_diffrn_oxdiff_digest_frames
;
0198e203fe803829c5675960c548fe55030003042ca
;
_diffrn_oxdiff_digest_hkl
;
01d2c7e1d33a59487d4b81091c80f988a6f06e
;
_reflns_odcompleteness_completeness 99.78
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              48800
_olex2_exptl_crystal_mounting_method 'Mounted on the 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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.533