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_7061908
_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 H6 N2 O3, 2.5(H2 O)'
_chemical_formula_sum            'C6 H11 N2 O5.5'
_chemical_formula_weight         199.16
_chemical_name_systematic        Methyl-3-oxo-4-hydropyrazine-2-carboxylate
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_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            16
_cell_length_a                   11.35633(17)
_cell_length_b                   12.7400(3)
_cell_length_c                   24.1766(5)
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.5820
_cell_measurement_theta_min      5.5150
_cell_volume                     3497.86(12)
_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      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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    -54.00 -22.00   0.50    6.00    --  -38.50 108.00-105.00   64
  2  \w     28.00  53.00   0.50    6.00    --   48.56-108.00 156.00   50
  3  \w     42.00 108.00   0.50   10.00    --  106.21-108.00 156.00  132
  4  \w    113.00 142.00   0.50   10.00    --  106.21 108.00-105.00   58
  5  \w   -104.00 -37.00   0.50    6.00    --  -38.50 -37.00 150.00  134
  6  \w    -25.00  25.00   0.50    6.00    --  -38.50  37.00  90.00  100
  7  \w    -50.00   8.00   0.50    6.00    --  -38.50  57.00   0.00  116
  8  \w     61.00  86.00   0.50    6.00    --   48.56  37.00 -30.00   50
  9  \w    119.00 170.00   0.50   10.00    --  106.21  30.00-150.00  102
 10  \w     49.00 109.00   0.50   10.00    --  106.21 -45.00   0.00  120
 11  \w    106.00 142.00   0.50   10.00    --  106.21  77.00  60.00   72
 12  \w     44.00 103.00   0.50   10.00    --  106.21-111.00-120.00  118
 13  \w     38.00 106.00   0.50   10.00    --  106.21 -94.00 -30.00  136
 14  \w     48.00 110.00   0.50   10.00    --  106.21 -30.00 -90.00  124
;
_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      -0.0640319000
_diffrn_orient_matrix_UB_12      0.0077895000
_diffrn_orient_matrix_UB_13      -0.0560227000
_diffrn_orient_matrix_UB_21      0.1118654000
_diffrn_orient_matrix_UB_22      0.0466182000
_diffrn_orient_matrix_UB_23      -0.0263980000
_diffrn_orient_matrix_UB_31      0.0422619000
_diffrn_orient_matrix_UB_32      -0.1113429000
_diffrn_orient_matrix_UB_33      -0.0149384000
_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  0.0520
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.777
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64118
_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    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_preparation       'AS PER METHOD 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         0.379
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.00016(5)
_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   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0573P)^2^+2.5388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2937
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
Adding full bibliography for 7061906--7061913.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H22 N4 O11'
_cod_original_formula_weight         398.33
_cod_original_formula_moiety         '2(C6 H6 N2 O3), 5(H2 O)'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        3497.87(12)
_cod_database_code               7061908
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88 H184 N40 O88 '
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.592
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B
 0.85 with sigma of 0.02
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O10-H10A = O10-H10B
 0.85 with sigma of 0.02
 O11-H11A = O11-H11B
 0.85 with sigma of 0.02
 H10A-H10B
 1.34 with sigma of 0.04
 H7A-H7B
 1.34 with sigma of 0.04
 H8A-H8B
 1.34 with sigma of 0.04
 H9A-H9B
 1.34 with sigma of 0.04
 H11A-H11B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), N4(H4A), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              93158
_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 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.542