#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:40:33 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279014 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061909.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_7061909
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  14.00   0.50    2.00    --  -38.50 104.00  28.00  182
  2  ω    104.00 171.00   0.50    8.00    --  102.63 104.00  28.00  134
  3  ω     34.00 107.00   0.50    8.00    --  102.63-104.00 -72.00  146
  4  ω   -101.00 -27.00   0.50    2.00    --  -38.50 -57.00-150.00  148
  5  ω      7.00  88.00   0.50    2.00    --   49.31-104.00 -72.00  162
  6  ω     46.00 116.00   0.50    2.00    --   49.31  38.00 120.00  140
  7  ω     38.00 107.00   0.50    8.00    --  102.63 -45.00 -30.00  138
  8  ω    125.00 168.00   0.50    8.00    --  102.63 125.00 -60.00   86
  9  ω    123.00 148.00   0.50    8.00    --  102.63  77.00-150.00   50
 10  ω     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       'ω 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/[σ²(Fo²)+(0.0558P)²+0.3289P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.634
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'
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
Cl1 Cl 0.68039(4) 0.82365(3) 1.03549(12) 0.0866(3) Uani 1 1 d . . . . .
O1 O 0.60123(9) 1.02721(8) 0.2692(3) 0.0812(5) Uani 1 1 d . . . . .
H1 H 0.566445 1.014035 0.185781 0.122 Uiso 1 1 calc R U . . .
O3 O 0.48129(8) 0.84087(7) 0.3913(3) 0.0731(4) Uani 1 1 d . . . . .
N1 N 0.67582(10) 0.99211(10) 0.5816(4) 0.0772(5) Uani 1 1 d . . . . .
N2 N 0.59717(8) 0.86861(8) 0.6687(3) 0.0548(4) Uani 1 1 d . . . . .
C1 C 0.61762(11) 0.97769(10) 0.4451(4) 0.0607(5) Uani 1 1 d . . . . .
C2 C 0.57791(10) 0.91583(9) 0.4875(3) 0.0526(4) Uani 1 1 d . . . . .
C3 C 0.65470(10) 0.88388(11) 0.7999(4) 0.0610(5) Uani 1 1 d . . . . .
C4 C 0.69445(12) 0.94497(12) 0.7585(5) 0.0756(6) Uani 1 1 d . . . . .
H4 H 0.735109 0.953031 0.857262 0.091 Uiso 1 1 calc R U . . .
C5 C 0.51330(10) 0.90058(10) 0.3322(4) 0.0593(5) Uani 1 1 d . . . . .
C6 C 0.41552(14) 0.82467(14) 0.2518(6) 0.0986(9) Uani 1 1 d . . . . .
H6A H 0.386870 0.867509 0.233460 0.118 Uiso 1 1 calc R U . . .
H6B H 0.426622 0.806726 0.080881 0.118 Uiso 1 1 calc R U . . .
C7 C 0.37633(17) 0.7709(2) 0.3982(9) 0.1287(13) Uani 1 1 d . . . . .
H7A H 0.331124 0.762133 0.316841 0.193 Uiso 1 1 calc R U . . .
H7B H 0.368638 0.787746 0.570833 0.193 Uiso 1 1 calc R U . . .
H7C H 0.403435 0.727420 0.403124 0.193 Uiso 1 1 calc R U . . .
O5 O 0.4997(17) 0.9366(14) 0.142(5) 0.070(3) Uani 0.47(7) 1 d . . . A 1
O4 O 0.4875(11) 0.9458(13) 0.189(5) 0.069(3) Uani 0.54(7) 1 d . . . A -1
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'
Cl Cl 0.3639 0.7018 '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 . . ?
C5 O3 C6 116.69(16) . . ?
C4 N1 C1 116.84(18) . . ?
C3 N2 C2 116.28(16) . . ?
O1 C1 C2 124.18(18) . . ?
N1 C1 O1 114.29(18) . . ?
N1 C1 C2 121.53(17) . . ?
N2 C2 C1 121.03(17) . . ?
N2 C2 C5 118.29(16) . . ?
C1 C2 C5 120.68(16) . . ?
N2 C3 Cl1 117.00(15) . . ?
N2 C3 C4 123.04(18) . . ?
C4 C3 Cl1 119.96(15) . . ?
N1 C4 C3 121.28(19) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
O3 C5 C2 114.38(15) . . ?
O5 C5 O3 124.5(12) . . ?
O5 C5 C2 120.2(13) . . ?
O5 C5 O4 17.7(14) . . ?
O4 C5 O3 123.6(10) . . ?
O4 C5 C2 121.1(11) . . ?
O3 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C7 C6 O3 108.1(2) . . ?
C7 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
Cl1 C3 1.7310(19) . ?
O1 H1 0.8200 . ?
O1 C1 1.336(2) . ?
O3 C5 1.306(2) . ?
O3 C6 1.460(3) . ?
N1 C1 1.328(3) . ?
N1 C4 1.320(3) . ?
N2 C2 1.340(2) . ?
N2 C3 1.306(2) . ?
C1 C2 1.395(3) . ?
C2 C5 1.481(2) . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C5 O5 1.22(2) . ?
C5 O4 1.22(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.459(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
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
Cl1 C3 C4 N1 -179.46(18) . . . . ?
O1 C1 C2 N2 -179.51(18) . . . . ?
O1 C1 C2 C5 0.7(3) . . . . ?
N1 C1 C2 N2 0.1(3) . . . . ?
N1 C1 C2 C5 -179.72(19) . . . . ?
N2 C2 C5 O3 0.0(3) . . . . ?
N2 C2 C5 O5 -169.5(18) . . . . ?
N2 C2 C5 O4 169.9(16) . . . . ?
N2 C3 C4 N1 0.3(4) . . . . ?
C1 N1 C4 C3 -0.5(3) . . . . ?
C1 C2 C5 O3 179.83(18) . . . . ?
C1 C2 C5 O5 10.3(18) . . . . ?
C1 C2 C5 O4 -10.3(16) . . . . ?
C2 N2 C3 Cl1 179.85(13) . . . . ?
C2 N2 C3 C4 0.1(3) . . . . ?
C3 N2 C2 C1 -0.3(3) . . . . ?
C3 N2 C2 C5 179.52(17) . . . . ?
C4 N1 C1 O1 179.9(2) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
C5 O3 C6 C7 -161.4(3) . . . . ?
C6 O3 C5 C2 177.4(2) . . . . ?
C6 O3 C5 O5 -14(2) . . . . ?
C6 O3 C5 O4 7.9(17) . . . . ?
