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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/7/22/62/7226295.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_7226295
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 H8 N2 O)'
_chemical_formula_sum            'C18 H16 F4 I2 N4 O2'
_chemical_formula_weight         650.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 93.507(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0259(3)
_cell_length_b                   8.6495(4)
_cell_length_c                   20.3527(13)
_cell_measurement_reflns_used    2077
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.8
_cell_volume                     1058.82(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6366
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.822
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.027
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.425
_refine_ls_extinction_coef       0.0169(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0531P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1433
_reflns_number_total             2077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01703g2.cif
_cod_data_source_block           5a2mp2_tfib
_cod_depositor_comments
'Adding full bibliography for 7226290--7226295.cif.'
_cod_database_code               7226295
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
C6 C 0.7291(8) 0.4912(6) 0.4330(3) 0.0664(14) Uani 1 1 d . .
H1C H 0.7209 0.4405 0.4748 0.100 Uiso 1 1 calc R U
H2C H 0.6035 0.5586 0.4257 0.100 Uiso 1 1 calc R U
H3C H 0.7283 0.4152 0.3987 0.100 Uiso 1 1 calc R U
I1 I 0.28097(5) 0.74331(3) 0.11745(2) 0.05904(19) Uani 1 1 d . .
C2 C 1.1709(8) 0.7367(5) 0.3786(2) 0.0515(12) Uani 1 1 d . .
H2 H 1.2737 0.7271 0.4144 0.062 Uiso 1 1 calc R U
N1 N 0.8205(6) 0.6637(5) 0.3274(2) 0.0544(9) Uani 1 1 d . .
C5 C 0.8677(9) 0.7561(5) 0.2759(2) 0.0572(12) Uani 1 1 d . .
H5 H 0.7653 0.7598 0.2398 0.069 Uiso 1 1 calc R U
F2 F 0.1008(4) 0.6366(3) -0.02726(14) 0.0681(8) Uani 1 1 d . .
C1 C 0.9691(7) 0.6599(5) 0.3773(2) 0.0461(10) Uani 1 1 d . .
F1 F 0.7344(4) 0.5506(4) 0.11556(15) 0.0713(9) Uani 1 1 d . .
C8 C 0.4132(7) 0.5996(4) 0.0467(2) 0.0474(11) Uani 1 1 d . .
N2 N 1.0935(8) 0.9397(5) 0.2199(2) 0.0636(12) Uani 1 1 d . .
H1N H 1.187(10) 1.016(6) 0.229(3) 0.095 Uiso 1 1 d . U
H2N H 0.970(9) 0.994(6) 0.208(3) 0.095 Uiso 1 1 d . U
C3 C 1.2153(7) 0.8282(5) 0.3254(2) 0.0534(12) Uani 1 1 d . .
H3 H 1.3511 0.8788 0.3242 0.064 Uiso 1 1 calc R U
C4 C 1.0568(7) 0.8439(5) 0.2739(2) 0.0494(11) Uani 1 1 d . .
O1 O 0.9292(5) 0.5794(4) 0.43306(16) 0.0591(8) Uani 1 1 d . .
C7 C 0.6161(7) 0.5268(5) 0.0583(2) 0.0507(11) Uani 1 1 d . .
C9 C 0.3010(7) 0.5696(5) -0.0125(3) 0.0503(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'
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
C3 C2 C1 118.1(4) . .
C1 N1 C5 116.5(4) . .
N1 C5 C4 124.1(4) . .
N1 C1 O1 120.6(4) . .
N1 C1 C2 124.0(4) . .
O1 C1 C2 115.3(4) . .
C9 C8 C7 116.5(4) . .
C9 C8 I1 121.9(3) . .
C7 C8 I1 121.5(4) . .
C2 C3 C4 119.6(4) . .
C5 C4 C3 117.4(4) . .
C5 C4 N2 121.4(5) . .
C3 C4 N2 121.2(4) . .
C1 O1 C6 117.7(4) . .
F1 C7 C9 119.2(4) . 3_665
F1 C7 C8 119.6(4) . .
C9 C7 C8 121.2(4) 3_665 .
F2 C9 C7 117.8(4) . 3_665
F2 C9 C8 119.9(4) . .
C7 C9 C8 122.3(4) 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 O1 1.427(6) .
I1 C8 2.096(4) .
C2 C3 1.381(7) .
C2 C1 1.385(6) .
N1 C1 1.313(5) .
N1 C5 1.362(6) .
C5 C4 1.372(6) .
F2 C9 1.356(5) .
C1 O1 1.365(5) .
F1 C7 1.345(5) .
C8 C9 1.370(6) .
C8 C7 1.383(6) .
N2 C4 1.404(6) .
C3 C4 1.381(6) .
C7 C9 1.368(7) 3_665
C9 C7 1.367(7) 3_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202625
