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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/7/22/62/7226294.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_7226294
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, 2(C6 H6 N2 O2)'
_chemical_formula_sum            'C18 H12 F4 I2 N4 O4'
_chemical_formula_weight         678.12
_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                96.727(2)
_cell_angle_beta                 112.766(4)
_cell_angle_gamma                103.570(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4529(6)
_cell_length_b                   10.6844(8)
_cell_length_c                   12.1719(17)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    295
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.7
_cell_volume                     1071.87(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0907
_diffrn_reflns_av_unetI/netI     0.1402
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11446
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.667
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.002
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0727P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1750
_reflns_number_total             3771
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01703g2.cif
_cod_data_source_block           4noa2_tfib
_cod_depositor_comments
'Adding full bibliography for 7226290--7226295.cif.'
_cod_original_cell_volume        1071.86(19)
_cod_database_code               7226294
_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
C1 C 0.1356(12) 0.1572(12) 0.8497(10) 0.054(3) Uani 1 1 d D .
C2 C 0.0466(13) 0.1825(12) 0.9138(11) 0.055(3) Uani 1 1 d . .
H2 H 0.0282 0.1289 0.9648 0.066 Uiso 1 1 calc R U
C3 C -0.0113(13) 0.2848(12) 0.9005(11) 0.054(3) Uani 1 1 d . .
H3 H -0.0722 0.3016 0.9417 0.064 Uiso 1 1 calc R U
C4 C 0.0181(12) 0.3683(12) 0.8247(11) 0.052(3) Uani 1 1 d D .
C5 C 0.1065(13) 0.3402(13) 0.7621(11) 0.056(3) Uani 1 1 d . .
H5 H 0.1262 0.3938 0.7114 0.067 Uiso 1 1 calc R U
C6 C 0.1621(12) 0.2396(12) 0.7738(10) 0.055(3) Uani 1 1 d D .
H6 H 0.2207 0.2222 0.7308 0.066 Uiso 1 1 calc R U
C7 C 0.8422(12) 0.8527(11) 0.6406(10) 0.048(3) Uani 1 1 d . .
C8 C 0.8061(13) 0.9572(12) 0.5845(11) 0.057(3) Uani 1 1 d . .
H8 H 0.8472 0.9808 0.5292 0.069 Uiso 1 1 calc R U
C9 C 0.7124(13) 1.0231(11) 0.6103(11) 0.053(3) Uani 1 1 d . .
H9 H 0.6914 1.0923 0.5735 0.063 Uiso 1 1 calc R U
C10 C 0.6469(13) 0.9882(11) 0.6915(10) 0.046(3) Uani 1 1 d . .
C11 C 0.6867(13) 0.8854(12) 0.7489(10) 0.053(3) Uani 1 1 d . .
H11 H 0.6469 0.8633 0.8052 0.063 Uiso 1 1 calc R U
C12 C 0.7821(13) 0.8169(11) 0.7247(10) 0.053(3) Uani 1 1 d . .
H12 H 0.8057 0.7492 0.7630 0.064 Uiso 1 1 calc R U
C13 C 0.5379(13) 0.5682(12) 0.9183(10) 0.047(3) Uani 1 1 d . .
C14 C 0.4487(12) 0.6094(11) 0.9752(11) 0.049(3) Uani 1 1 d . .
C15 C 0.5855(12) 0.4618(12) 0.9434(11) 0.054(3) Uani 1 1 d . .
C16 C 0.3906(11) 0.5546(12) 0.5207(10) 0.046(3) Uani 1 1 d . .
C17 C 0.4280(12) 0.4520(11) 0.5728(10) 0.044(3) Uani 1 1 d . .
C18 C 0.5333(12) 0.3976(10) 0.5506(10) 0.044(3) Uani 1 1 d . .
N1 N 0.1993(12) 0.0414(11) 0.8612(12) 0.065(3) Uani 1 1 d . .
N2 N -0.0410(12) 0.4735(11) 0.8146(10) 0.074(3) Uani 1 1 d D .
H1N H -0.145(4) 0.455(4) 0.765(9) 0.111 Uiso 1 1 d D U
H2N H 0.016(8) 0.543(5) 0.800(11) 0.111 Uiso 1 1 d D U
N3 N 0.9431(11) 0.7820(11) 0.6129(11) 0.060(3) Uani 1 1 d . .
N4 N 0.5506(14) 1.0487(13) 0.7167(12) 0.075(3) Uani 1 1 d D .
H3N H 0.497(14) 1.015(13) 0.758(11) 0.113 Uiso 1 1 d D U
H4N H 0.519(15) 1.107(11) 0.677(12) 0.113 Uiso 1 1 d D U
O1 O 0.1807(12) -0.0224(11) 0.9366(10) 0.091(3) Uani 1 1 d . .
O2 O 0.2685(11) 0.0150(11) 0.7987(10) 0.096(3) Uani 1 1 d . .
O3 O 0.9700(11) 0.6942(9) 0.6665(10) 0.088(3) Uani 1 1 d . .
O4 O 0.9988(12) 0.8192(11) 0.5418(10) 0.089(3) Uani 1 1 d . .
F1 F 0.5767(8) 0.6299(7) 0.8419(6) 0.0655(19) Uani 1 1 d . .
F2 F 0.6723(8) 0.4246(7) 0.8866(6) 0.070(2) Uani 1 1 d . .
F3 F 0.3555(8) 0.4008(7) 0.6401(6) 0.0667(19) Uani 1 1 d . .
F4 F 0.5637(8) 0.2947(7) 0.6006(6) 0.069(2) Uani 1 1 d . .
I1 I 0.36227(9) 0.77119(8) 0.93807(8) 0.0588(3) Uani 1 1 d . .
I2 I 0.23042(8) 0.64358(8) 0.55358(7) 0.0584(3) 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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.5(11) . .
C2 C1 N1 119.9(12) . .
C6 C1 N1 120.6(12) . .
C3 C2 C1 118.9(12) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 121.1(11) . .
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 . .
N2 C4 C5 121.8(12) . .
N2 C4 C3 119.6(12) . .
C5 C4 C3 118.7(12) . .
C6 C5 C4 120.6(12) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C1 121.4(11) . .
C5 C6 H6 119.3 . .
C1 C6 H6 119.3 . .
C12 C7 C8 120.1(11) . .
C12 C7 N3 119.0(11) . .
C8 C7 N3 120.9(12) . .
C9 C8 C7 120.9(11) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.7(11) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
N4 C10 C9 122.4(11) . .
N4 C10 C11 119.9(12) . .
C9 C10 C11 117.8(10) . .
C12 C11 C10 122.8(11) . .
C12 C11 H11 118.6 . .
C10 C11 H11 118.6 . .
C11 C12 C7 117.7(11) . .
C11 C12 H12 121.1 . .
C7 C12 H12 121.1 . .
F1 C13 C15 119.5(11) . .
F1 C13 C14 122.3(11) . .
C15 C13 C14 118.2(12) . .
C13 C14 C15 118.3(11) . 2_667
C13 C14 I1 121.2(9) . .
C15 C14 I1 120.5(9) 2_667 .
C13 C15 F2 116.6(11) . .
C13 C15 C14 123.5(11) . 2_667
F2 C15 C14 119.9(11) . 2_667
C17 C16 C18 118.6(9) . 2_666
C17 C16 I2 121.1(9) . .
C18 C16 I2 120.3(9) 2_666 .
F3 C17 C18 119.6(10) . .
F3 C17 C16 120.8(9) . .
C18 C17 C16 119.6(11) . .
F4 C18 C17 117.8(10) . .
F4 C18 C16 120.3(10) . 2_666
C17 C18 C16 121.8(10) . 2_666
O2 N1 O1 123.4(13) . .
O2 N1 C1 119.5(13) . .
O1 N1 C1 117.2(12) . .
C4 N2 H1N 116(3) . .
C4 N2 H2N 116(3) . .
H1N N2 H2N 110(5) . .
O3 N3 O4 125.9(11) . .
O3 N3 C7 116.7(12) . .
O4 N3 C7 117.4(12) . .
C10 N4 H3N 120(9) . .
C10 N4 H4N 120(9) . .
H3N N4 H4N 118(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.398(16) .
C1 C6 1.399(9) .
C1 N1 1.496(15) .
C2 C3 1.332(15) .
C2 H2 0.9300 .
C3 C4 1.413(16) .
C3 H3 0.9300 .
C4 N2 1.365(15) .
C4 C5 1.388(16) .
C5 C6 1.302(16) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C12 1.399(15) .
C7 C8 1.416(16) .
C7 N3 1.456(14) .
C8 C9 1.354(15) .
C8 H8 0.9300 .
C9 C10 1.397(15) .
C9 H9 0.9300 .
C10 N4 1.337(14) .
C10 C11 1.415(15) .
C11 C12 1.378(15) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 F1 1.315(12) .
C13 C15 1.343(15) .
C13 C14 1.392(16) .
C14 C15 1.404(16) 2_667
C14 I1 2.103(11) .
C15 F2 1.356(13) .
C15 C14 1.404(16) 2_667
C16 C17 1.379(15) .
C16 C18 1.396(15) 2_666
C16 I2 2.100(10) .
C17 F3 1.343(12) .
C17 C18 1.358(14) .
C18 F4 1.354(12) .
C18 C16 1.396(15) 2_666
N1 O2 1.228(14) .
N1 O1 1.246(14) .
N2 H1N 0.89(2) .
N2 H2N 0.89(2) .
N3 O3 1.223(13) .
N3 O4 1.233(13) .
N4 H3N 0.89(2) .
N4 H4N 0.88(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202624
