#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/80/2108035.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_2108035
loop_
_publ_author_name
'Szell, Patrick M. J.'
'Gabidullin, Bulat'
'Bryce, David L.'
_publ_section_title
;
 1,3,5-Tri(iodoethynyl)-2,4,6-trifluorobenzene: halogen-bonded frameworks
 and NMR spectroscopic analysis
;
_journal_coeditor_code           XM5005
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520617000944
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 P, 2(C12 F3 I3), 2(C2 H3 N), Br'
_chemical_formula_sum            'C52 H26 Br F6 I6 N2 P'
_chemical_formula_weight         1665.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.1095(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5544(3)
_cell_length_b                   16.4031(4)
_cell_length_c                   30.8221(8)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.30
_cell_volume                     5305.8(2)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            24116
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_min         2.304
_exptl_absorpt_coefficient_mu    4.354
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.898
_refine_diff_density_min         -1.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0351P)²+11.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                5916
_reflns_number_total             6501
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xm5005sup1.cif
_cod_data_source_block           1f
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               2108035
_cod_database_fobs_code          2108035
_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.
;
_shelx_estimated_absorpt_t_min   0.397
_shelx_estimated_absorpt_t_max   0.448
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
I I1 0.44671(2) 0.14616(2) 0.65143(2) 0.03741(6) Uani d 1
I I2 0.26141(2) 0.65835(2) 0.44640(2) 0.03483(6) Uani d 1
I I3 0.46543(2) 0.08589(2) 0.31933(2) 0.03593(6) Uani d 1
Br Br1 0.5000 0.06053(2) 0.7500 0.03846(10) Uani d 1
P P1 0.5000 0.38958(6) 0.2500 0.02527(18) Uani d 1
F F1 0.36519(18) 0.39499(11) 0.54407(6) 0.0403(4) Uani d 1
F F2 0.3866(2) 0.37352(11) 0.39377(6) 0.0464(5) Uani d 1
F F3 0.44052(18) 0.14197(10) 0.48199(6) 0.0398(4) Uani d 1
N N1 0.2173(4) -0.1637(2) 0.42132(14) 0.0689(10) Uani d 1
C C1 0.4075(3) 0.26766(16) 0.51525(9) 0.0286(5) Uani d 1
C C2 0.3832(3) 0.35032(16) 0.50901(9) 0.0296(5) Uani d 1
C C3 0.3746(3) 0.38862(17) 0.46848(9) 0.0308(6) Uani d 1
C C4 0.3928(3) 0.33935(17) 0.43306(9) 0.0318(6) Uani d 1
C C5 0.4149(3) 0.25602(17) 0.43598(9) 0.0300(5) Uani d 1
C C6 0.4213(3) 0.22302(16) 0.47772(9) 0.0296(5) Uani d 1
C C7 0.4166(3) 0.23075(17) 0.55740(9) 0.0311(6) Uani d 1
C C8 0.4255(3) 0.19913(17) 0.59225(10) 0.0340(6) Uani d 1
C C9 0.3427(3) 0.47332(18) 0.46346(10) 0.0337(6) Uani d 1
C C10 0.3114(3) 0.54210(18) 0.45826(10) 0.0352(6) Uani d 1
C C11 0.4278(3) 0.20688(18) 0.39826(10) 0.0348(6) Uani d 1
C C12 0.4396(3) 0.16491(18) 0.36774(10) 0.0369(6) Uani d 1
C C13 0.3642(3) 0.32396(16) 0.24000(9) 0.0275(5) Uani d 1
C C14 0.3273(3) 0.29776(19) 0.19767(10) 0.0363(6) Uani d 1
H H14A 0.3658 0.3199 0.1738 0.044 Uiso calc 1
C C15 0.2331(3) 0.2388(2) 0.19095(11) 0.0446(8) Uani d 1
H H15A 0.2058 0.2209 0.1621 0.054 Uiso calc 1
C C16 0.1790(3) 0.20579(19) 0.22559(12) 0.0429(7) Uani d 1
H H16A 0.1146 0.1654 0.2205 0.052 Uiso calc 1
C C17 0.2173(3) 0.23090(18) 0.26755(11) 0.0403(7) Uani d 1
H H17A 0.1793 0.2079 0.2913 0.048 Uiso calc 1
C C18 0.3112(3) 0.28945(17) 0.27514(10) 0.0327(6) Uani d 1
H H18A 0.3392 0.3060 0.3041 0.039 Uiso calc 1
C C19 0.4891(3) 0.45535(16) 0.29574(8) 0.0270(5) Uani d 1
C C20 0.3717(3) 0.47779(17) 0.30850(9) 0.0312(6) Uani d 1
H H20A 0.2955 0.4540 0.2949 0.037 Uiso calc 1
C C21 0.3671(3) 0.53551(18) 0.34143(10) 0.0351(6) Uani d 1
H H21A 0.2873 0.5502 0.3508 0.042 Uiso calc 1
C C22 0.4780(3) 0.57163(19) 0.36060(10) 0.0383(7) Uani d 1
H H22A 0.4741 0.6109 0.3831 0.046 Uiso calc 1
C C23 0.5942(3) 0.5504(2) 0.34698(10) 0.0403(7) Uani d 1
H H23A 0.6699 0.5759 0.3598 0.048 Uiso calc 1
C C24 0.6008(3) 0.49212(19) 0.31472(10) 0.0374(6) Uani d 1
H H24A 0.6809 0.4773 0.3056 0.045 Uiso calc 1
C C25 0.2778(4) -0.1076(2) 0.42848(12) 0.0481(8) Uani d 1
C C26 0.3575(4) -0.0365(2) 0.43878(15) 0.0590(10) Uani d 1
H H26A 0.3365 -0.0124 0.4662 0.089 Uiso calc 1
H H26B 0.3424 0.0037 0.4153 0.089 Uiso calc 1
H H26C 0.4473 -0.0527 0.4418 0.089 Uiso calc 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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C19 P1 C19 2_655 . 105.80(17)
C19 P1 C13 2_655 2_655 112.36(12)
C19 P1 C13 . 2_655 110.12(12)
C19 P1 C13 2_655 . 110.11(12)
C19 P1 C13 . . 112.36(12)
C13 P1 C13 2_655 . 106.21(18)
C2 C1 C6 . . 115.7(3)
C2 C1 C7 . . 122.2(3)
C6 C1 C7 . . 122.1(3)
F1 C2 C1 . . 117.6(3)
F1 C2 C3 . . 118.5(2)
C1 C2 C3 . . 123.9(3)
C4 C3 C2 . . 116.2(3)
C4 C3 C9 . . 122.0(3)
C2 C3 C9 . . 121.7(3)
F2 C4 C5 . . 117.8(3)
F2 C4 C3 . . 118.3(2)
C5 C4 C3 . . 124.0(3)
C4 C5 C6 . . 115.8(3)
C4 C5 C11 . . 122.1(3)
C6 C5 C11 . . 122.1(3)
F3 C6 C1 . . 117.8(2)
F3 C6 C5 . . 117.8(2)
C1 C6 C5 . . 124.5(3)
C8 C7 C1 . . 178.9(3)
C7 C8 I1 . . 178.2(3)
C10 C9 C3 . . 177.0(3)
C9 C10 I2 . . 177.1(3)
C12 C11 C5 . . 178.5(3)
C11 C12 I3 . . 175.1(3)
C14 C13 C18 . . 120.6(3)
C14 C13 P1 . . 119.1(2)
C18 C13 P1 . . 119.4(2)
C15 C14 C13 . . 118.7(3)
C16 C15 C14 . . 120.6(3)
C15 C16 C17 . . 120.5(3)
C16 C17 C18 . . 120.1(3)
C17 C18 C13 . . 119.4(3)
C20 C19 C24 . . 120.4(3)
C20 C19 P1 . . 121.1(2)
C24 C19 P1 . . 117.9(2)
C19 C20 C21 . . 119.2(3)
C22 C21 C20 . . 120.5(3)
C23 C22 C21 . . 119.9(3)
C22 C23 C24 . . 120.4(3)
C23 C24 C19 . . 119.6(3)
N1 C25 C26 . . 178.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C8 . 2.011(3)
I2 C10 . 2.002(3)
I3 C12 . 2.017(3)
P1 C19 2_655 1.789(3)
P1 C19 . 1.789(3)
P1 C13 2_655 1.793(3)
P1 C13 . 1.793(3)
F1 C2 . 1.336(3)
F2 C4 . 1.330(3)
F3 C6 . 1.349(3)
N1 C25 . 1.128(5)
C1 C2 . 1.390(4)
C1 C6 . 1.390(4)
C1 C7 . 1.427(4)
C2 C3 . 1.393(4)
C3 C4 . 1.388(4)
C3 C9 . 1.434(4)
C4 C5 . 1.388(4)
C5 C6 . 1.391(4)
C5 C11 . 1.433(4)
C7 C8 . 1.188(4)
C9 C10 . 1.182(4)
C11 C12 . 1.183(4)
C13 C14 . 1.389(4)
C13 C18 . 1.391(4)
C14 C15 . 1.387(5)
C15 C16 . 1.374(5)
C16 C17 . 1.376(5)
C17 C18 . 1.381(4)
C19 C20 . 1.389(4)
C19 C24 . 1.396(4)
C20 C21 . 1.393(4)
C21 C22 . 1.387(5)
C22 C23 . 1.383(5)
C23 C24 . 1.386(4)
C25 C26 . 1.454(6)
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
C6 C1 C2 F1 . 177.9(2)
C7 C1 C2 F1 . -1.6(4)
C6 C1 C2 C3 . -1.0(4)
C7 C1 C2 C3 . 179.5(3)
F1 C2 C3 C4 . -179.3(3)
C1 C2 C3 C4 . -0.4(4)
F1 C2 C3 C9 . -2.3(4)
C1 C2 C3 C9 . 176.6(3)
C2 C3 C4 F2 . -179.4(3)
C9 C3 C4 F2 . 3.6(4)
C2 C3 C4 C5 . 1.7(5)
C9 C3 C4 C5 . -175.3(3)
F2 C4 C5 C6 . 179.6(3)
C3 C4 C5 C6 . -1.5(4)
F2 C4 C5 C11 . -1.6(4)
C3 C4 C5 C11 . 177.3(3)
C2 C1 C6 F3 . -177.7(2)
C7 C1 C6 F3 . 1.8(4)
C2 C1 C6 C5 . 1.3(4)
C7 C1 C6 C5 . -179.2(3)
C4 C5 C6 F3 . 178.9(3)
C11 C5 C6 F3 . 0.1(4)
C4 C5 C6 C1 . -0.1(4)
C11 C5 C6 C1 . -178.9(3)
C19 P1 C13 C14 2_655 33.3(3)
C19 P1 C13 C14 . 151.0(2)
C13 P1 C13 C14 2_655 -88.6(2)
C19 P1 C13 C18 2_655 -157.4(2)
C19 P1 C13 C18 . -39.7(3)
C13 P1 C13 C18 2_655 80.7(2)
C18 C13 C14 C15 . 2.4(4)
P1 C13 C14 C15 . 171.6(2)
C13 C14 C15 C16 . -1.1(5)
C14 C15 C16 C17 . 0.0(5)
C15 C16 C17 C18 . -0.2(5)
C16 C17 C18 C13 . 1.4(5)
C14 C13 C18 C17 . -2.6(4)
P1 C13 C18 C17 . -171.7(2)
C19 P1 C19 C20 2_655 93.9(2)
C13 P1 C19 C20 2_655 -144.4(2)
C13 P1 C19 C20 . -26.2(3)
C19 P1 C19 C24 2_655 -77.8(2)
C13 P1 C19 C24 2_655 43.9(3)
C13 P1 C19 C24 . 162.0(2)
C24 C19 C20 C21 . -2.0(4)
P1 C19 C20 C21 . -173.5(2)
C19 C20 C21 C22 . 1.5(4)
C20 C21 C22 C23 . 0.1(5)
C21 C22 C23 C24 . -1.1(5)
C22 C23 C24 C19 . 0.5(5)
C20 C19 C24 C23 . 1.0(4)
P1 C19 C24 C23 . 172.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064611
