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_7061906
_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         'C7 H7 F N2 O3'
_chemical_formula_sum            'C7 H7 F N2 O3'
_chemical_formula_weight         186.15
_chemical_name_systematic        Ethyl-6-fluoro-3-hydroxypyrazine-2-carboxylate
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 90.480(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2620(5)
_cell_length_b                   4.72480(10)
_cell_length_c                   16.6253(4)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6600
_cell_measurement_theta_min      6.8580
_cell_volume                     1591.55(6)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_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    -73.00 -25.00   0.50    0.50    --  -38.50  96.00 106.00   96
  2  \w    -22.00  19.00   0.50    0.50    --  -38.50  96.00 106.00   82
  3  \w      7.00  42.00   0.50    0.50    --   48.56 -96.00  -3.00   70
  4  \w    139.00 169.00   0.50    0.75    --  106.21  96.00 106.00   60
  5  \w   -101.00 -50.00   0.50    0.50    --  -38.50 -57.00  30.00  102
  6  \w    -11.00  20.00   0.50    0.50    --   48.56 -57.00-120.00   62
  7  \w     87.00 112.00   0.50    0.50    --   48.56  57.00-180.00   50
  8  \w     28.00  59.00   0.50    0.50    --   48.56 -57.00-120.00   62
  9  \w    104.00 169.00   0.50    0.75    --  106.21  77.00 -60.00  130
 10  \w     94.00 168.00   0.50    0.75    --  106.21  61.00   0.00  148
 11  \w    103.00 157.00   0.50    0.75    --  106.21  15.00-180.00  108
 12  \w     37.00 104.00   0.50    0.75    --  106.21-111.00 150.00  134
 13  \w     40.00  93.00   0.50    0.75    --  106.21 -94.00 -90.00  106
 14  \w     57.00 109.00   0.50    0.75    --  106.21-111.00-120.00  104
 15  \w     38.00  63.00   0.50    0.75    --  106.21 -94.00-120.00   50
 16  \w     42.00  81.00   0.50    0.75    --  106.21 -45.00 120.00   78
 17  \w    109.00 134.00   0.50    0.75    --  106.21  77.00-150.00   50
 18  \w     71.00 100.00   0.50    0.75    --  106.21 -94.00 -60.00   58
 19  \w     79.00 104.00   0.50    0.75    --  106.21 -96.00  -3.00   50
;
_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      0.0441189000
_diffrn_orient_matrix_UB_12      -0.1280093000
_diffrn_orient_matrix_UB_13      0.0665637000
_diffrn_orient_matrix_UB_21      0.0556861000
_diffrn_orient_matrix_UB_22      0.2070286000
_diffrn_orient_matrix_UB_23      -0.0223087000
_diffrn_orient_matrix_UB_31      -0.0270401000
_diffrn_orient_matrix_UB_32      0.2170699000
_diffrn_orient_matrix_UB_33      0.0604848000
_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  0.0227
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.482
_diffrn_reflns_theta_min         5.321
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51138
_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    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_preparation       'AS PER 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         0.248
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0543P)^2^+1.0509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1477
_reflns_number_total             1614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7061906--7061913.cif.'
_cod_database_code               7061906
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C48 H32 F16 N24 O16 '
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.585
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C3(H3)
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              7557
_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 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.444