#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/86/7218667.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_7218667
loop_
_publ_author_name
'Syssa-Magalé, Jean-Laurent'
'Boubekeur, Kamal'
'Leroy, Jacques'
'Chamoreau, Lise-Marie'
'Fave, Claire'
'Schöllhorn, Bernd'
_publ_section_title
;
 Directed synthesis of a halogen-bonded open porphyrin network
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              10380
_journal_paper_doi               10.1039/C4CE01704H
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C10 H8 N2, C6 F3 I3)'
_chemical_formula_sum            'C16 H8 F3 I3 N2'
_chemical_formula_weight         665.94
_chemical_name_systematic
;
1,3,5-Trifluoro-2,4,6-tri-iodobenzene 4,4'-bipyridine
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                 91.621(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.1140(8)
_cell_length_b                   9.0710(9)
_cell_length_c                   24.104(5)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      4.5
_cell_volume                     899.2(3)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7515
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.243
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'exposing equimolar solutions of the respective XB donor and acceptor molecules in chloroform to a saturated atmosphere of n-pentane at room temperature. '
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.851
_refine_diff_density_min         -2.286
_refine_diff_density_rms         0.282
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.26(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0566
_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)+(0.0868P)²+0.2042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                3868
_reflns_number_total             4736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01704h2.cif
_cod_data_source_block           smjl259sb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7218667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.26096(14) 0.58102(9) 0.38837(3) 0.04130(18) Uani 1 1 d .
I2 I 0.88582(12) 0.53645(8) 0.16744(3) 0.04037(18) Uani 1 1 d .
I3 I 0.7529(2) 1.13389(8) 0.27649(4) 0.0560(2) Uani 1 1 d .
F1 F 0.5198(19) 0.4627(7) 0.2773(3) 0.0453(17) Uani 1 1 d .
F2 F 0.9220(19) 0.8845(8) 0.1908(3) 0.0509(17) Uani 1 1 d .
F3 F 0.425(2) 0.9221(8) 0.3626(3) 0.0525(18) Uani 1 1 d .
C1 C 0.469(3) 0.6901(11) 0.3208(4) 0.033(2) Uani 1 1 d .
C2 C 0.574(3) 0.6095(10) 0.2774(5) 0.0331(19) Uani 1 1 d .
C3 C 0.727(2) 0.6694(11) 0.2324(4) 0.0315(19) Uani 1 1 d .
C4 C 0.770(2) 0.8199(12) 0.2332(4) 0.033(2) Uani 1 1 d .
C5 C 0.673(2) 0.9074(10) 0.2765(4) 0.033(2) Uani 1 1 d .
C6 C 0.525(3) 0.8397(12) 0.3200(4) 0.036(2) Uani 1 1 d .
N1 N 0.552(3) 0.6397(13) -0.0311(5) 0.053(3) Uani 1 1 d .
N2 N 0.102(3) 1.3176(13) 0.0919(4) 0.044(2) Uani 1 1 d .
C7 C 0.452(4) 0.6477(13) 0.0213(6) 0.053(3) Uani 1 1 d .
H7 H 0.4407 0.5615 0.0421 0.064 Uiso 1 1 calc R
C8 C 0.366(4) 0.7794(13) 0.0455(5) 0.059(4) Uani 1 1 d .
H8 H 0.2943 0.7788 0.0818 0.071 Uiso 1 1 calc R
C9 C 0.382(3) 0.9089(13) 0.0184(4) 0.036(2) Uani 1 1 d .
C10 C 0.289(3) 1.0505(13) 0.0442(5) 0.041(3) Uani 1 1 d .
C11 C 0.347(4) 1.0781(13) 0.0988(5) 0.047(3) Uani 1 1 d .
H11 H 0.4463 1.0063 0.1210 0.057 Uiso 1 1 calc R
C12 C 0.261(4) 1.2109(15) 0.1218(5) 0.054(3) Uani 1 1 d .
H12 H 0.3131 1.2284 0.1591 0.065 Uiso 1 1 calc R
C13 C 0.047(3) 1.2927(14) 0.0385(4) 0.048(3) Uani 1 1 d .
H13 H -0.0566 1.3645 0.0169 0.058 Uiso 1 1 calc R
C14 C 0.140(4) 1.1628(14) 0.0141(5) 0.054(3) Uani 1 1 d .
H14 H 0.1006 1.1501 -0.0238 0.064 Uiso 1 1 calc R
C15 C 0.481(4) 0.9032(16) -0.0345(5) 0.055(3) Uani 1 1 d .
H15 H 0.4977 0.9897 -0.0550 0.066 Uiso 1 1 calc R
C16 C 0.560(5) 0.7658(18) -0.0590(6) 0.073(5) Uani 1 1 d .
H16 H 0.6192 0.7642 -0.0959 0.088 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 117.5(9)
C2 C1 I1 119.3(7)
C6 C1 I1 123.0(8)
F1 C2 C1 118.4(9)
F1 C2 C3 117.8(10)
C1 C2 C3 123.8(9)
C4 C3 C2 116.2(9)
C4 C3 I2 122.5(7)
C2 C3 I2 121.3(8)
F2 C4 C3 119.0(9)
F2 C4 C5 118.3(9)
C3 C4 C5 122.7(9)
C6 C5 C4 117.7(9)
C6 C5 I3 121.0(8)
C4 C5 I3 121.3(7)
F3 C6 C5 119.2(10)
F3 C6 C1 118.8(10)
C5 C6 C1 122.0(10)
C16 N1 C7 116.2(11)
C13 N2 C12 117.5(11)
N1 C7 C8 122.3(12)
N1 C7 H7 118.9
C8 C7 H7 118.9
C9 C8 C7 122.2(11)
C9 C8 H8 118.9
C7 C8 H8 118.9
C8 C9 C15 116.5(11)
C8 C9 C10 122.4(9)
C15 C9 C10 121.2(11)
C11 C10 C14 115.8(11)
C11 C10 C9 121.8(11)
C14 C10 C9 122.3(11)
C10 C11 C12 120.9(12)
C10 C11 H11 119.5
C12 C11 H11 119.5
N2 C12 C11 122.1(12)
N2 C12 H12 118.9
C11 C12 H12 118.9
N2 C13 C14 121.4(11)
N2 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C10 122.1(11)
C13 C14 H14 118.9
C10 C14 H14 118.9
C9 C15 C16 120.3(13)
C9 C15 H15 119.9
C16 C15 H15 119.9
N1 C16 C15 122.5(12)
N1 C16 H16 118.8
C15 C16 H16 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.108(10)
I2 C3 2.097(10)
I3 C5 2.081(9)
F1 C2 1.350(11)
F2 C4 1.347(12)
F3 C6 1.344(13)
C1 C2 1.357(15)
C1 C6 1.378(15)
C2 C3 1.378(14)
C3 C4 1.377(15)
C4 C5 1.379(15)
C5 C6 1.372(14)
N1 C16 1.328(19)
N1 C7 1.342(18)
N2 C13 1.320(14)
N2 C12 1.363(18)
C7 C8 1.381(16)
C7 H7 0.9300
C8 C9 1.347(16)
C8 H8 0.9300
C9 C15 1.349(17)
C9 C10 1.482(14)
C10 C11 1.354(17)
C10 C14 1.384(18)
C11 C12 1.378(18)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.375(18)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.421(19)
C15 H15 0.9300
C16 H16 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199441
