#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/80/2108089.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_2108089
loop_
_publ_author_name
'Liu, Rui'
'Gao, Yuan Jun'
'Jin, Wei Jun'
_publ_section_title
;
 Color-tunable phosphorescence of 1,10-phenanthrolines by
 4,7-methyl/-diphenyl/-dichloro substituents in cocrystals assembled
 via bifurcated C---I···N halogen bonds using
 1,4-diiodotetrafluorobenzene as a bonding donor
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              247
_journal_page_last               254
_journal_paper_doi               10.1107/S205252061700292X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_sum            'C30 H12 Cl4 F4 I2 N4'
_chemical_formula_weight         900.04
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.149(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5713(10)
_cell_length_b                   21.091(2)
_cell_length_c                   7.1214(7)
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.25
_cell_volume                     1508.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8418
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    2.493
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_refine_diff_density_max         0.852
_refine_diff_density_min         -1.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.6889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                2899
_reflns_number_total             3404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao5026sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2019-10-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C15 H6 Cl2 F2 I N2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     450.02
_cod_database_code               2108089
_cod_database_fobs_code          2108089
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I I1 0.27436(2) 0.398258(11) 0.16527(3) 0.05797(11) Uani d . 1 1
Cl Cl1 0.52755(13) 0.05800(4) 0.33875(19) 0.0847(3) Uani d . 1 1
Cl Cl2 1.00409(9) 0.32697(6) 0.72108(19) 0.0875(3) Uani d . 1 1
F F1 0.0283(2) 0.42786(13) 0.3243(4) 0.0872(8) Uani d . 1 1
F F2 -0.1796(2) 0.50480(13) 0.1982(4) 0.0871(8) Uani d . 1 1
N N2 0.5753(3) 0.35926(12) 0.3659(4) 0.0500(6) Uani d . 1 1
N N1 0.4044(2) 0.26266(13) 0.2260(4) 0.0497(6) Uani d . 1 1
C C7 0.5306(3) 0.24772(13) 0.3336(4) 0.0392(6) Uani d . 1 1
C C8 0.6219(3) 0.29911(13) 0.4076(4) 0.0390(6) Uani d . 1 1
C C12 0.7560(3) 0.28519(14) 0.5181(4) 0.0416(6) Uani d . 1 1
C C1 0.1113(3) 0.45930(13) 0.0667(4) 0.0445(6) Uani d . 1 1
C C15 0.5765(3) 0.18467(13) 0.3742(4) 0.0425(6) Uani d . 1 1
C C2 0.0157(3) 0.46304(15) 0.1622(5) 0.0500(7) Uani d . 1 1
C C14 0.7117(3) 0.17305(14) 0.4867(5) 0.0497(7) Uani d . 1 1
H H14 0.7412 0.1315 0.5132 0.060 Uiso calc R 1 1
C C3 -0.0921(3) 0.50290(16) 0.0971(5) 0.0517(7) Uani d . 1 1
C C4 0.4814(4) 0.13679(15) 0.2981(5) 0.0537(8) Uani d . 1 1
C C13 0.7974(3) 0.22100(15) 0.5552(5) 0.0494(7) Uani d . 1 1
H H13 0.8852 0.2121 0.6279 0.059 Uiso calc R 1 1
C C11 0.8394(3) 0.33799(17) 0.5827(5) 0.0548(8) Uani d . 1 1
C C5 0.3537(4) 0.15177(18) 0.1925(5) 0.0625(9) Uani d . 1 1
H H5 0.2904 0.1203 0.1437 0.075 Uiso calc R 1 1
C C6 0.3208(3) 0.21569(19) 0.1598(5) 0.0615(9) Uani d . 1 1
H H6 0.2338 0.2258 0.0862 0.074 Uiso calc R 1 1
C C10 0.7919(4) 0.39821(16) 0.5393(7) 0.0673(10) Uani d . 1 1
H H10 0.8472 0.4331 0.5816 0.081 Uiso calc R 1 1
C C9 0.6589(4) 0.40598(16) 0.4305(7) 0.0651(10) Uani d . 1 1
H H9 0.6271 0.4471 0.4017 0.078 Uiso calc R 1 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C1 I1 N1 . . 152.39(9)
C1 I1 N2 . . 156.94(9)
N1 I1 N2 . . 50.67(6)
C9 N2 C8 . . 117.8(3)
C9 N2 I1 . . 115.9(2)
C8 N2 I1 . . 125.91(19)
C6 N1 C7 . . 117.6(3)
C6 N1 I1 . . 114.8(2)
C7 N1 I1 . . 126.99(19)
N1 C7 C15 . . 123.4(3)
N1 C7 C8 . . 117.6(2)
C15 C7 C8 . . 119.0(3)
N2 C8 C12 . . 123.0(3)
N2 C8 C7 . . 117.8(2)
C12 C8 C7 . . 119.2(2)
C11 C12 C8 . . 115.7(3)
C11 C12 C13 . . 124.6(3)
C8 C12 C13 . . 119.7(3)
C3 C1 C2 3_565 . 116.5(3)
C3 C1 I1 3_565 . 122.0(2)
C2 C1 I1 . . 121.5(2)
C4 C15 C7 . . 115.9(3)
C4 C15 C14 . . 124.3(3)
C7 C15 C14 . . 119.8(3)
F1 C2 C3 . . 118.5(3)
F1 C2 C1 . . 119.9(3)
C3 C2 C1 . . 121.6(3)
C13 C14 C15 . . 121.3(3)
C13 C14 H14 . . 119.4
C15 C14 H14 . . 119.4
F2 C3 C1 . 3_565 119.7(3)
F2 C3 C2 . . 118.4(3)
C1 C3 C2 3_565 . 121.9(3)
C5 C4 C15 . . 120.8(3)
C5 C4 Cl1 . . 119.6(3)
C15 C4 Cl1 . . 119.6(3)
C14 C13 C12 . . 121.0(3)
C14 C13 H13 . . 119.5
C12 C13 H13 . . 119.5
C10 C11 C12 . . 120.9(3)
C10 C11 Cl2 . . 119.2(3)
C12 C11 Cl2 . . 119.9(3)
C4 C5 C6 . . 118.0(3)
C4 C5 H5 . . 121.0
C6 C5 H5 . . 121.0
N1 C6 C5 . . 124.4(3)
N1 C6 H6 . . 117.8
C5 C6 H6 . . 117.8
C11 C10 C9 . . 118.3(3)
C11 C10 H10 . . 120.9
C9 C10 H10 . . 120.9
N2 C9 C10 . . 124.3(3)
N2 C9 H9 . . 117.9
C10 C9 H9 . . 117.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C1 . 2.090(3)
I1 N1 . 3.144(3)
I1 N2 . 3.163(3)
Cl1 C4 . 1.731(4)
Cl2 C11 . 1.728(3)
F1 C2 . 1.343(4)
F2 C3 . 1.339(4)
N2 C9 . 1.308(4)
N2 C8 . 1.360(3)
N1 C6 . 1.314(4)
N1 C7 . 1.352(4)
C7 C15 . 1.414(4)
C7 C8 . 1.438(4)
C8 C12 . 1.421(4)
C12 C11 . 1.406(4)
C12 C13 . 1.422(4)
C1 C3 3_565 1.375(4)
C1 C2 . 1.384(4)
C15 C4 . 1.409(4)
C15 C14 . 1.426(4)
C2 C3 . 1.375(4)
C14 C13 . 1.344(5)
C14 H14 . 0.9300
C3 C1 3_565 1.375(4)
C4 C5 . 1.362(5)
C13 H13 . 0.9300
C11 C10 . 1.365(5)
C5 C6 . 1.394(6)
C5 H5 . 0.9300
C6 H6 . 0.9300
C10 C9 . 1.388(6)
C10 H10 . 0.9300
C9 H9 . 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C1 I1 N2 C9 . . -2.0(4)
N1 I1 N2 C9 . . 178.7(3)
C1 I1 N2 C8 . . 171.1(3)
N1 I1 N2 C8 . . -8.2(2)
C1 I1 N1 C6 . . -0.1(3)
N2 I1 N1 C6 . . 179.3(3)
C1 I1 N1 C7 . . -170.8(2)
N2 I1 N1 C7 . . 8.6(2)
C6 N1 C7 C15 . . 1.2(4)
I1 N1 C7 C15 . . 171.65(19)
C6 N1 C7 C8 . . -179.5(3)
I1 N1 C7 C8 . . -9.1(4)
C9 N2 C8 C12 . . 0.4(5)
I1 N2 C8 C12 . . -172.58(19)
C9 N2 C8 C7 . . -179.0(3)
I1 N2 C8 C7 . . 8.1(4)
N1 C7 C8 N2 . . 0.5(4)
C15 C7 C8 N2 . . 179.8(3)
N1 C7 C8 C12 . . -178.8(3)
C15 C7 C8 C12 . . 0.5(4)
N2 C8 C12 C11 . . -0.2(4)
C7 C8 C12 C11 . . 179.1(3)
N2 C8 C12 C13 . . -179.8(3)
C7 C8 C12 C13 . . -0.5(4)
N1 I1 C1 C3 . 3_565 -107.3(3)
N2 I1 C1 C3 . 3_565 73.9(4)
N1 I1 C1 C2 . . 71.8(3)
N2 I1 C1 C2 . . -107.0(3)
N1 C7 C15 C4 . . -1.1(4)
C8 C7 C15 C4 . . 179.6(3)
N1 C7 C15 C14 . . 179.2(3)
C8 C7 C15 C14 . . -0.1(4)
C3 C1 C2 F1 3_565 . -179.5(3)
I1 C1 C2 F1 . . 1.4(4)
C3 C1 C2 C3 3_565 . -0.5(5)
I1 C1 C2 C3 . . -179.6(3)
C4 C15 C14 C13 . . -179.9(3)
C7 C15 C14 C13 . . -0.2(5)
F1 C2 C3 F2 . . 0.0(5)
C1 C2 C3 F2 . . -179.0(3)
F1 C2 C3 C1 . 3_565 179.5(3)
C1 C2 C3 C1 . 3_565 0.6(6)
C7 C15 C4 C5 . . 0.0(4)
C14 C15 C4 C5 . . 179.7(3)
C7 C15 C4 Cl1 . . 179.8(2)
C14 C15 C4 Cl1 . . -0.5(4)
C15 C14 C13 C12 . . 0.1(5)
C11 C12 C13 C14 . . -179.4(3)
C8 C12 C13 C14 . . 0.2(5)
C8 C12 C11 C10 . . -0.1(5)
C13 C12 C11 C10 . . 179.5(3)
C8 C12 C11 Cl2 . . 179.2(2)
C13 C12 C11 Cl2 . . -1.2(4)
C15 C4 C5 C6 . . 0.9(5)
Cl1 C4 C5 C6 . . -178.9(3)
C7 N1 C6 C5 . . -0.2(5)
I1 N1 C6 C5 . . -171.8(3)
C4 C5 C6 N1 . . -0.8(6)
C12 C11 C10 C9 . . 0.3(6)
Cl2 C11 C10 C9 . . -179.1(3)
C8 N2 C9 C10 . . -0.2(6)
I1 N2 C9 C10 . . 173.4(3)
C11 C10 C9 N2 . . -0.1(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064623
