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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/62/7226290.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_7226290
loop_
_publ_author_name
'Nemec, Vinko'
'Cinčić, Dominik'
_publ_section_title
;
 Uncommon halogen bond motifs in cocrystals of aromatic amines and
 1,4-diiodotetrafluorobenzene
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              7425
_journal_paper_doi               10.1039/C6CE01703G
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         ' C6 F4 I2, C7 H6 N2 '
_chemical_formula_sum            'C13 H6 F4 I2 N2'
_chemical_formula_weight         520.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                100.565(11)
_cell_angle_beta                 107.57
_cell_angle_gamma                105.95
_cell_formula_units_Z            2
_cell_length_a                   8.4368(10)
_cell_length_b                   8.4962(2)
_cell_length_c                   11.8803(10)
_cell_measurement_reflns_used    3215
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      3.8
_cell_volume                     746.94(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7773
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.246
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0299P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2285
_reflns_number_total             3215
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01703g2.cif
_cod_data_source_block           3abn_tfib
_cod_depositor_comments
'Adding full bibliography for 7226290--7226295.cif.'
_cod_original_cell_volume        746.97(11)
_cod_database_code               7226290
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C10 C 0.6546(5) 0.5639(5) 0.5998(3) 0.0509(9) Uani 1 1 d . .
C3 C 0.6838(5) 0.2446(4) 0.0442(3) 0.0430(8) Uani 1 1 d . .
C7 C 1.0872(6) 0.2225(5) -0.0083(4) 0.0579(10) Uani 1 1 d . .
C12 C 0.9114(5) 0.8317(4) 0.4220(3) 0.0449(9) Uani 1 1 d . .
C11 C 1.0375(5) 0.8672(5) 0.5368(3) 0.0484(9) Uani 1 1 d . .
C13 C 0.8767(5) 0.9683(5) 0.3876(3) 0.0497(9) Uani 1 1 d . .
N1 N 1.2162(6) 0.1997(5) 0.0050(4) 0.0804(12) Uani 1 1 d . .
N2 N 0.6043(5) 0.2209(5) 0.1302(3) 0.0559(9) Uani 1 1 d . .
F1 F 1.0773(4) 0.7428(3) 0.5785(2) 0.0737(7) Uani 1 1 d . .
F2 F 0.7566(4) 0.9411(3) 0.2750(2) 0.0774(8) Uani 1 1 d . .
F3 F 0.3154(4) 0.7027(3) 0.4323(2) 0.0768(7) Uani 1 1 d . .
F4 F 0.8060(3) 0.6219(3) 0.6977(2) 0.0798(8) Uani 1 1 d . .
H1N H 0.621(8) 0.149(7) 0.160(5) 0.120 Uiso 1 1 d . U
H2N H 0.489(8) 0.201(7) 0.094(5) 0.120 Uiso 1 1 d . U
C8 C 0.4089(6) 0.6043(5) 0.4673(3) 0.0516(10) Uani 1 1 d . .
C9 C 0.5650(5) 0.6723(4) 0.5690(3) 0.0498(9) Uani 1 1 d . .
C2 C 0.8402(5) 0.2171(4) 0.0561(3) 0.0435(9) Uani 1 1 d . .
H2 H 0.8917 0.1759 0.1197 0.052 Uiso 1 1 calc R U
C1 C 0.9209(4) 0.2507(4) -0.0266(3) 0.0420(8) Uani 1 1 d . .
C6 C 0.8495(5) 0.3143(4) -0.1206(3) 0.0498(9) Uani 1 1 d . .
H6 H 0.9061 0.3393 -0.1747 0.060 Uiso 1 1 calc R U
C5 C 0.6930(5) 0.3395(5) -0.1320(3) 0.0531(10) Uani 1 1 d . .
H5 H 0.6417 0.3807 -0.1957 0.064 Uiso 1 1 calc R U
C4 C 0.6107(5) 0.3059(5) -0.0525(3) 0.0484(9) Uani 1 1 d . .
H4 H 0.5040 0.3240 -0.0627 0.058 Uiso 1 1 calc R U
I1 I 0.78271(4) 0.58196(3) 0.30642(2) 0.05193(10) Uani 1 1 d . .
I2 I 0.65880(5) 0.92445(3) 0.67279(3) 0.07468(12) 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 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'
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
F4 C10 C8 118.5(4) . 2_666
F4 C10 C9 120.0(3) . .
C8 C10 C9 121.5(4) 2_666 .
C2 C3 C4 118.3(3) . .
C2 C3 N2 121.2(3) . .
C4 C3 N2 120.4(3) . .
N1 C7 C1 179.5(5) . .
C11 C12 C13 116.8(3) . .
C11 C12 I1 120.9(3) . .
C13 C12 I1 122.3(3) . .
F1 C11 C13 118.3(3) . 2_776
F1 C11 C12 120.9(3) . .
C13 C11 C12 120.8(3) 2_776 .
F2 C13 C11 118.3(3) . 2_776
F2 C13 C12 119.3(3) . .
C11 C13 C12 122.4(3) 2_776 .
F3 C8 C10 118.5(4) . 2_666
F3 C8 C9 120.2(3) . .
C10 C8 C9 121.4(4) 2_666 .
C10 C9 C8 117.1(3) . .
C10 C9 I2 121.3(3) . .
C8 C9 I2 121.6(3) . .
C3 C2 C1 119.9(3) . .
C6 C1 C2 121.5(3) . .
C6 C1 C7 120.9(4) . .
C2 C1 C7 117.5(3) . .
C5 C6 C1 118.0(4) . .
C4 C5 C6 121.5(3) . .
C5 C4 C3 120.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C10 F4 1.332(4) .
C10 C8 1.367(5) 2_666
C10 C9 1.375(5) .
C3 C2 1.372(5) .
C3 C4 1.392(5) .
C3 N2 1.396(5) .
C7 N1 1.127(5) .
C7 C1 1.447(6) .
C12 C11 1.371(5) .
C12 C13 1.374(5) .
C12 I1 2.081(3) .
C11 F1 1.328(4) .
C11 C13 1.369(5) 2_776
C13 F2 1.345(4) .
C13 C11 1.369(5) 2_776
F3 C8 1.337(4) .
C8 C10 1.367(5) 2_666
C8 C9 1.376(5) .
C9 I2 2.061(3) .
C2 C1 1.382(5) .
C1 C6 1.376(5) .
C6 C5 1.366(5) .
C5 C4 1.358(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202620
