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_7061913
_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         'C6 H5 F N2 O3'
_chemical_formula_sum            'C6 H5 F N2 O3'
_chemical_formula_weight         172.12
_chemical_name_systematic        Methyl-6-fluoro-3-hydroxypyrazine-2-carboxylate
_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   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                67.238(5)
_cell_angle_beta                 82.602(5)
_cell_angle_gamma                81.791(4)
_cell_formula_units_Z            4
_cell_length_a                   4.1240(2)
_cell_length_b                   12.7162(6)
_cell_length_c                   14.3351(9)
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2610
_cell_measurement_theta_min      3.9580
_cell_volume                     683.88(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 n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.944
_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    -50.00  20.00   0.50    0.50    --  -38.50  79.00  29.00  140
  2  \w     -5.00  52.00   0.50    0.50    --   48.56 -79.00 -94.00  114
  3  \w    129.00 156.00   0.50    2.00    --  106.21  79.00  29.00   54
  4  \w     87.00 129.00   0.50    2.00    --  106.21 -79.00 -94.00   84
  5  \w    -66.00 -36.00   0.50    0.50    --  -38.50 -37.00 -60.00   60
  6  \w   -105.00 -79.00   0.50    0.50    --  -38.50 -37.00 -60.00   52
  7  \w    -84.00 -18.00   0.50    0.50    --  -38.50 125.00 150.00  132
  8  \w     81.00 112.00   0.50    0.50    --   48.56  57.00 120.00   62
  9  \w    -13.00  51.00   0.50    0.50    --   48.56 -19.00 -30.00  128
 10  \w     59.00 103.00   0.50    0.50    --   48.56  37.00 -60.00   88
 11  \w     47.00  75.00   0.50    0.50    --   48.56  57.00 120.00   56
 12  \w    109.00 169.00   0.50    2.00    --  106.21  45.00   0.00  120
 13  \w    118.00 170.00   0.50    2.00    --  106.21  77.00  90.00  104
 14  \w     39.00  67.00   0.50    2.00    --  106.21 -94.00-180.00   56
 15  \w     44.00  75.00   0.50    2.00    --  106.21 -61.00-180.00   62
 16  \w     50.00  87.00   0.50    2.00    --  106.21 -94.00  30.00   74
 17  \w    103.00 174.00   0.50    2.00    --  106.21  30.00  60.00  142
 18  \w     53.00  95.00   0.50    2.00    --  106.21 -94.00 120.00   84
 19  \w     42.00 109.00   0.50    2.00    --  106.21 -45.00 -30.00  134
 20  \w     80.00 108.00   0.50    2.00    --  106.21-111.00 -30.00   56
 21  \w     38.00  75.00   0.50    2.00    --  106.21-111.00 -30.00   74
 22  \w     77.00 109.00   0.50    2.00    --  106.21-111.00-150.00   64
 23  \w     47.00  80.00   0.50    2.00    --  106.21 -15.00  30.00   66
 24  \w     84.00 113.00   0.50    2.00    --  106.21 -15.00  30.00   58
 25  \w     38.00  74.00   0.50    2.00    --  106.21-111.00-150.00   72
 26  \w     81.00 106.00   0.50    2.00    --  106.21 -94.00-180.00   50
 27  \w    104.00 134.00   0.50    2.00    --  106.21 111.00   0.00   60
 28  \w    139.00 164.00   0.50    2.00    --  106.21 111.00   0.00   50
 29  \w     55.00 100.00   0.50    2.00    --  106.21 -94.00  60.00   90
 30  \w    106.00 169.00   0.50    2.00    --  106.21  61.00 -30.00  126
 31  \w    131.00 171.00   0.50    2.00    --  106.21  77.00 120.00   80
 32  \w     54.00 106.00   0.50    2.00    --  106.21 -94.00 -90.00  104
 33  \w     42.00 107.00   0.50    2.00    --  106.21 -30.00  30.00  130
;
_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      -0.0326846000
_diffrn_orient_matrix_UB_12      0.0489254000
_diffrn_orient_matrix_UB_13      0.0841041000
_diffrn_orient_matrix_UB_21      0.2884128000
_diffrn_orient_matrix_UB_22      0.0717806000
_diffrn_orient_matrix_UB_23      -0.0540013000
_diffrn_orient_matrix_UB_31      -0.2431616000
_diffrn_orient_matrix_UB_32      0.0994761000
_diffrn_orient_matrix_UB_33      -0.0606782000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6244
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.412
_diffrn_reflns_theta_min         3.789
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83504
_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    1.672
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'AS MENTIONED IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0519
_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^)+(0.1044P)^2^+0.0850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2393
_reflns_number_total             2744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
Adding full bibliography for 7061906--7061913.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H10 F2 N4 O6'
_cod_original_formula_weight         344.24
_cod_original_formula_moiety         '2(C6 H5 F N2 O3)'
_cod_original_formula_units_Z            2
_cod_database_code               7061913
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H14 F8 N10 O8 '
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.553
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              4441
_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 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.681