#------------------------------------------------------------------------------
#$Date: 2022-11-07 06:40:33 +0100 (Mon 07 de Nov de 2022) $
#$Revision: 279014 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/19/7061910.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061910
loop_
_publ_author_name
'Ghosh, Priyanka'
'Panda, Subhra Jyoti'
'Purohit, Chandra Shekhar'
_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 Br N3 O2'
_chemical_formula_sum            'C5 H4 Br N3 O2'
_chemical_formula_weight         218.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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                 93.394(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.26356(16)
_cell_length_b                   5.3334(2)
_cell_length_c                   15.8471(6)
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    157(30)
_cell_measurement_theta_max      74.4320
_cell_measurement_theta_min      5.5830
_cell_volume                     359.72(2)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      157(30)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9687
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  28.00   0.50    0.30    --  -38.50  82.00 -18.00  186
  2  ω    -17.00  76.00   0.50    0.30    --   49.31 -82.00-140.00  186
  3  ω     37.00 129.00   0.50    1.11    --  102.63 -82.00-140.00  184
  4  ω    103.00 169.00   0.50    1.11    --  102.63  82.00 -18.00  132
  5  ω    -44.00  31.00   0.50    0.30    --  -38.50  19.00-120.00  150
  6  ω    -50.00  24.00   0.50    0.30    --  -38.50  57.00 120.00  148
  7  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 -30.00  148
  8  ω     38.00 112.00   0.50    0.30    --   49.31  57.00  30.00  148
  9  ω     90.00 165.00   0.50    1.11    --  102.63  61.00 -30.00  150
 10  ω     90.00 165.00   0.50    1.11    --  102.63  61.00 -60.00  150
 11  ω     95.00 171.00   0.50    1.11    --  102.63  15.00-150.00  152
 12  ω     38.00 112.00   0.50    1.11    --  102.63-125.00  30.00  148
 13  ω     99.00 171.00   0.50    1.11    --  102.63  30.00 -60.00  144
 14  ω     40.00 116.00   0.50    1.11    --  102.63 -61.00  90.00  152
 15  ω     99.00 171.00   0.50    1.11    --  102.63  30.00  60.00  144
 16  ω     98.00 167.00   0.50    1.11    --  102.63  45.00  30.00  138
 17  ω     98.00 167.00   0.50    1.11    --  102.63  45.00 120.00  138
 18  ω     90.00 165.00   0.50    1.11    --  102.63  61.00   0.00  150
 19  ω     38.00 112.00   0.50    1.11    --  102.63-125.00  60.00  148
 20  ω     35.00 106.00   0.50    1.11    --  102.63 -30.00   0.00  142
 21  ω     38.00 112.00   0.50    1.11    --  102.63-125.00-180.00  148
 22  ω     38.00 107.00   0.50    1.11    --  102.63 -45.00 120.00  138
 23  ω     98.00 167.00   0.50    1.11    --  102.63  45.00   0.00  138
 24  ω     98.00 167.00   0.50    1.11    --  102.63  47.00   1.01  138
 25  ω     95.00 171.00   0.50    1.11    --  102.63  15.00 -60.00  152
 26  ω     38.00 107.00   0.50    1.11    --  102.63 -45.00   0.00  138
 27  ω   -102.00 -19.00   0.50    0.30    --  -38.50 -72.00-118.00  166
 28  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 -90.00  148
 29  ω     38.00 112.00   0.50    0.30    --   49.31  57.00-180.00  148
 30  ω     38.00 112.00   0.50    0.30    --   49.31  57.00  60.00  148
 31  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 120.00  148
 32  ω     38.00 112.00   0.50    0.30    --   49.31  57.00-150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2523452000
_diffrn_orient_matrix_UB_12      -0.1988902000
_diffrn_orient_matrix_UB_13      -0.0156040000
_diffrn_orient_matrix_UB_21      0.1801767000
_diffrn_orient_matrix_UB_22      0.0753954000
_diffrn_orient_matrix_UB_23      0.0832668000
_diffrn_orient_matrix_UB_31      -0.1870168000
_diffrn_orient_matrix_UB_32      -0.1954637000
_diffrn_orient_matrix_UB_33      0.0479464000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5212
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.106
_diffrn_reflns_theta_min         5.593
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38759
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0573
_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/[σ²(Fo²)+(0.1150P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1390
_reflns_number_total             1447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02996k2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7061906--7061913.cif.'
_cod_database_code               7061910
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 I2 N10 O6 '
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.422
_shelx_estimated_absorpt_t_min   0.214
_diffrn_oxdiff_digest_frames
;
0188be171ad84768efa723952c0e3c353f000717079
;
_diffrn_oxdiff_digest_hkl
;
01656af49ff726057aaddf0a18f9926ea748c9
;
_reflns_odcompleteness_completeness 99.86
_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:
 C4(H4)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.529
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1205(2) 0.0423(3) 0.57600(5) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.621(2) 0.6891(16) 0.8530(6) 0.066(2) Uani 1 1 d . . . . .
H1 H 0.564029 0.636916 0.898359 0.098 Uiso 1 1 calc R U . . .
O2 O 0.3035(17) 0.4233(13) 0.9524(5) 0.0517(15) Uani 1 1 d . . . . .
N1 N 0.590(2) 0.5922(16) 0.7130(6) 0.058(2) Uani 1 1 d . . . . .
N2 N 0.1913(17) 0.1934(14) 0.7431(5) 0.0423(15) Uani 1 1 d . . . . .
N3 N 0.011(2) 0.0989(13) 0.9004(5) 0.050(2) Uani 1 1 d . . . . .
H3A H -0.053194 0.061803 0.949243 0.060 Uiso 1 1 calc R U . . .
H3B H -0.050552 0.011952 0.856801 0.060 Uiso 1 1 calc R U . . .
C1 C 0.5021(18) 0.542(2) 0.7903(5) 0.0460(16) Uani 1 1 d . . . . .
C2 C 0.3008(18) 0.3415(15) 0.8055(6) 0.0378(15) Uani 1 1 d . . . . .
C3 C 0.280(2) 0.2483(17) 0.6668(5) 0.0446(18) Uani 1 1 d . . . . .
C4 C 0.474(3) 0.447(2) 0.6514(7) 0.058(2) Uani 1 1 d . . . . .
H4 H 0.524623 0.479359 0.596139 0.070 Uiso 1 1 calc R U . . .
C5 C 0.204(2) 0.2892(17) 0.8922(6) 0.0411(16) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C4 N1 C1 116.7(9) . . ?
C3 N2 C2 116.2(8) . . ?
H3A N3 H3B 120.0 . . ?
C5 N3 H3A 120.0 . . ?
C5 N3 H3B 120.0 . . ?
O1 C1 C2 121.8(8) . . ?
N1 C1 O1 116.8(9) . . ?
N1 C1 C2 121.4(9) . . ?
N2 C2 C1 121.2(8) . . ?
N2 C2 C5 118.2(7) . . ?
C1 C2 C5 120.6(8) . . ?
N2 C3 Br1 117.1(7) . . ?
N2 C3 C4 122.8(9) . . ?
C4 C3 Br1 120.1(7) . . ?
N1 C4 C3 121.6(9) . . ?
N1 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
O2 C5 N3 123.6(8) . . ?
O2 C5 C2 120.0(8) . . ?
N3 C5 C2 116.4(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.904(10) . ?
O1 H1 0.8200 . ?
O1 C1 1.341(13) . ?
O2 C5 1.245(11) . ?
N1 C1 1.330(12) . ?
N1 C4 1.321(16) . ?
N2 C2 1.329(11) . ?
N2 C3 1.321(11) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C5 1.318(11) . ?
C1 C2 1.401(12) . ?
C2 C5 1.484(12) . ?
C3 C4 1.374(15) . ?
C4 H4 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 N1 -179.6(8) . . . . ?
O1 C1 C2 N2 -178.3(10) . . . . ?
O1 C1 C2 C5 1.7(15) . . . . ?
N1 C1 C2 N2 0.2(14) . . . . ?
N1 C1 C2 C5 -179.8(9) . . . . ?
N2 C2 C5 O2 179.7(8) . . . . ?
N2 C2 C5 N3 -0.9(13) . . . . ?
N2 C3 C4 N1 1.6(16) . . . . ?
C1 N1 C4 C3 -2.1(15) . . . . ?
C1 C2 C5 O2 -0.3(14) . . . . ?
C1 C2 C5 N3 179.1(9) . . . . ?
C2 N2 C3 Br1 -179.0(6) . . . . ?
C2 N2 C3 C4 -0.1(13) . . . . ?
C3 N2 C2 C1 -0.8(12) . . . . ?
C3 N2 C2 C5 179.2(8) . . . . ?
C4 N1 C1 O1 179.8(10) . . . . ?
C4 N1 C1 C2 1.2(15) . . . . ?
