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#$Date: 2023-05-06 13:43:34 +0300 (Sat, 06 May 2023) $
#$Revision: 283573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312035
loop_
_publ_author_name
'Mosquera, Marta E. G.'
'Dortez, Silvia'
'Fernández-Palacio, Francisco'
'Gómez-Sal, Pilar'
_publ_section_title
;
 Pyridine-4-thiol as halogen-bond (HaB) acceptor: influence of the
 noncovalent interaction in its reactivity.
;
_journal_coeditor_code           QZ3003
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              112
_journal_page_last               117
_journal_paper_doi               10.1107/S205322962300205X
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C6 F4 I2, 2C5 H5 N S'
_chemical_formula_moiety         'C6 F4 I2, 2(C5 H5 N S)'
_chemical_formula_sum            'C16 H10 F4 I2 N2 S2'
_chemical_formula_weight         624.18
_chemical_name_systematic
;
1,2,4,5-Tetrafluoro-3,6-diiodobenzene bis(pyridin-1-ium-4-ylsulfanide)
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.77(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.288(8)
_cell_length_b                   5.790(4)
_cell_length_c                   10.546(9)
_cell_measurement_reflns_used    215
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      16.12
_cell_measurement_theta_min      3.16
_cell_volume                     961.7(12)
_computing_cell_refinement
;
DIRAX/LSQ (Duisenberg et al.,  2003)
;
_computing_data_collection
;
COLLECT (Nonius, 2004)
;
_computing_data_reduction
;
EvalCCD (Duisenberg et al.,  2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.749
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.527
_exptl_absorpt_correction_T_max  0.426
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.991
_refine_diff_density_min         -1.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0226P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                1458
_reflns_number_total             2181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qz3003sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2312035--2312036.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8563(3) 0.0026(8) 0.2712(4) 0.0330(10) Uani d 1 . .
C C2 0.7891(3) -0.1543(8) 0.2540(5) 0.0350(11) Uani d 1 . .
H H2 0.74811 -0.136116 0.303246 0.042 Uiso calc 1 . .
C C3 0.7815(3) -0.3326(8) 0.1679(5) 0.0397(11) Uani d 1 . .
H H3 0.735913 -0.439004 0.158066 0.048 Uiso calc 1 . .
C C4 0.9026(3) -0.2109(9) 0.1069(5) 0.0400(12) Uani d 1 . .
H H4 0.94134 -0.231938 0.054024 0.048 Uiso calc 1 . .
C C5 0.9132(3) -0.0325(9) 0.1917(4) 0.0387(11) Uani d 1 . .
H H5 0.959431 0.070832 0.198036 0.046 Uiso calc 1 . .
C C6 0.5758(3) 0.4353(8) 0.4694(4) 0.0312(10) Uani d 1 . .
C C7 0.5349(3) 0.6360(8) 0.4217(5) 0.0365(11) Uani d 1 . .
C C8 0.4605(3) 0.7008(8) 0.4527(5) 0.0354(11) Uani d 1 . .
F F1 0.56773(17) 0.7763(5) 0.3454(3) 0.0503(8) Uani d 1 . .
F F2 0.42425(16) 0.8996(4) 0.4053(3) 0.0434(7) Uani d 1 . .
I I1 0.69103(2) 0.34216(5) 0.42717(3) 0.03545(12) Uani d 1 . .
N N1 0.8384(3) -0.3580(7) 0.0967(4) 0.0380(9) Uani d 1 . .
S S1 0.87081(7) 0.2220(2) 0.38297(12) 0.0365(3) Uani d 1 . .
H H1 0.831(3) -0.461(8) 0.043(4) 0.032(14) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 116.1(4) ?
C2 C1 S1 . . 122.6(3) ?
C5 C1 S1 . . 121.3(3) ?
C3 C2 C1 . . 121.0(4) ?
N1 C3 C2 . . 120.0(4) ?
N1 C4 C5 . . 120.6(4) ?
C4 C5 C1 . . 120.7(4) ?
C7 C6 C8 . 3_666 117.6(4) ?
C7 C6 I1 . . 121.0(3) ?
C8 C6 I1 3_666 . 121.4(3) ?
F1 C7 C6 . . 120.1(4) ?
F1 C7 C8 . . 118.8(4) ?
C6 C7 C8 . . 121.1(4) ?
F2 C8 C6 . 3_666 120.1(4) ?
F2 C8 C7 . . 118.5(4) ?
C6 C8 C7 3_666 . 121.4(4) ?
C4 N1 C3 . . 121.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.398(6) ?
C1 C5 . 1.415(5) ?
C1 S1 . 1.708(5) ?
C2 C3 . 1.360(6) ?
C3 N1 . 1.341(6) ?
C4 N1 . 1.332(6) ?
C4 C5 . 1.348(6) ?
C6 C7 . 1.370(6) ?
C6 C8 3_666 1.376(6) ?
C6 I1 . 2.107(4) ?
C7 F1 . 1.346(5) ?
C7 C8 . 1.385(6) ?
C8 F2 . 1.332(5) ?
