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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/7/22/62/7226292.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_7226292
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(C8 H9 N O)'
_chemical_formula_sum            'C22 H18 F4 I2 N2 O2'
_chemical_formula_weight         672.20
_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                113.014(5)
_cell_angle_beta                 96.686(4)
_cell_angle_gamma                104.202(5)
_cell_formula_units_Z            1
_cell_length_a                   6.1553(3)
_cell_length_b                   9.6907(6)
_cell_length_c                   10.8382(5)
_cell_measurement_reflns_used    2381
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      4.0
_cell_volume                     560.28(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7170
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         4.038
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.862
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_description       plate
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0199
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0335P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2168
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01703g2.cif
_cod_data_source_block           4aap2_tfib
_cod_depositor_comments
'Adding full bibliography for 7226290--7226295.cif.'
_cod_database_code               7226292
_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
F2 F -0.2507(3) 0.45916(19) 0.17966(17) 0.0558(4) Uani 1 1 d . .
F1 F 0.3145(3) 0.34962(18) -0.06777(17) 0.0557(4) Uani 1 1 d . .
C11 C -0.1238(4) 0.4781(2) 0.0908(2) 0.0359(4) Uani 1 1 d . .
C10 C 0.0366(4) 0.4005(2) 0.0608(2) 0.0342(4) Uani 1 1 d . .
C9 C 0.1587(4) 0.4237(2) -0.0326(2) 0.0360(4) Uani 1 1 d . .
N1 N 0.3067(6) 0.6077(3) 0.5599(3) 0.0610(6) Uani 1 1 d . .
O1 O 0.1475(4) 1.0309(3) 0.2583(2) 0.0641(5) Uani 1 1 d . .
C7 C 0.2905(4) 0.9633(3) 0.2527(2) 0.0422(5) Uani 1 1 d . .
C8 C 0.4663(5) 0.9798(3) 0.1706(3) 0.0538(6) Uani 1 1 d . .
H8A H 0.4473 1.0517 0.1326 0.081 Uiso 1 1 calc R U
H8B H 0.4461 0.8784 0.0971 0.081 Uiso 1 1 calc R U
H8C H 0.6183 1.0200 0.2294 0.081 Uiso 1 1 calc R U
H1N H 0.202(6) 0.620(4) 0.611(3) 0.062(9) Uiso 1 1 d . .
H2N H 0.446(8) 0.626(6) 0.604(5) 0.120(18) Uiso 1 1 d . .
I1 I 0.08904(3) 0.24901(2) 0.14626(2) 0.04367(7) Uani 1 1 d . .
C1 C 0.2941(4) 0.8641(2) 0.3268(2) 0.0341(4) Uani 1 1 d . .
C6 C 0.4638(4) 0.7952(3) 0.3331(2) 0.0401(5) Uani 1 1 d . .
H6 H 0.5772 0.8061 0.2847 0.048 Uiso 1 1 calc R U
C2 C 0.1242(4) 0.8444(3) 0.3995(2) 0.0421(5) Uani 1 1 d . .
H2 H 0.0075 0.8892 0.3961 0.051 Uiso 1 1 calc R U
C4 C 0.3024(4) 0.6934(3) 0.4836(2) 0.0414(5) Uani 1 1 d . .
C3 C 0.1274(4) 0.7596(3) 0.4761(3) 0.0447(5) Uani 1 1 d . .
H3 H 0.0123 0.7467 0.5229 0.054 Uiso 1 1 calc R U
C5 C 0.4684(4) 0.7107(3) 0.4094(3) 0.0465(5) Uani 1 1 d . .
H5 H 0.5839 0.6647 0.4115 0.056 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 '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
F2 C11 C10 120.03(19) . .
F2 C11 C9 118.30(19) . 2_565
C10 C11 C9 121.67(19) . 2_565
C11 C10 C9 116.94(19) . .
C11 C10 I1 122.17(15) . .
C9 C10 I1 120.86(15) . .
F1 C9 C11 118.80(19) . 2_565
F1 C9 C10 119.82(19) . .
C11 C9 C10 121.38(19) 2_565 .
O1 C7 C1 120.7(2) . .
O1 C7 C8 120.3(2) . .
C1 C7 C8 119.1(2) . .
C6 C1 C2 118.1(2) . .
C6 C1 C7 123.0(2) . .
C2 C1 C7 118.9(2) . .
C5 C6 C1 121.2(2) . .
C3 C2 C1 121.0(2) . .
N1 C4 C5 120.7(2) . .
N1 C4 C3 120.6(2) . .
C5 C4 C3 118.7(2) . .
C2 C3 C4 120.2(2) . .
C6 C5 C4 120.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F2 C11 1.347(2) .
F1 C9 1.337(2) .
C11 C10 1.376(3) .
C11 C9 1.374(3) 2_565
C10 C9 1.383(3) .
C10 I1 2.084(2) .
C9 C11 1.374(3) 2_565
N1 C4 1.384(3) .
O1 C7 1.213(3) .
C7 C1 1.475(3) .
C7 C8 1.497(3) .
C1 C6 1.380(3) .
C1 C2 1.401(3) .
C6 C5 1.376(3) .
C2 C3 1.379(3) .
C4 C5 1.390(3) .
C4 C3 1.392(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202622
