#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/80/2108034.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_2108034
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         'C21 H20 O P, 2(C12 F3 I3), 2(C2 H3 N), Br'
_chemical_formula_sum            'C49 H26 Br F6 I6 N2 O P'
_chemical_formula_weight         1645.00
_chemical_melting_point          415
_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                 95.6557(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5098(5)
_cell_length_b                   16.2789(7)
_cell_length_c                   30.9417(15)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.31
_cell_volume                     5268.0(4)
_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 0.975
_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  0.0388
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            35395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.534
_diffrn_reflns_theta_min         1.323
_exptl_absorpt_coefficient_mu    4.385
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3056
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.345
_refine_diff_density_min         -1.781
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6513
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0297P)²+174.9186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                6031
_reflns_number_total             6513
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xm5005sup1.cif
_cod_data_source_block           1e
_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               2108034
_cod_database_fobs_code          2108034
_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   0.559
_shelx_estimated_absorpt_t_max   0.668
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.03499(6) 0.91655(4) 0.17890(2) 0.04371(16) Uani d 1 . .
I I2 0.04897(6) 0.84508(4) -0.15360(2) 0.04458(16) Uani d 1 . .
I I3 0.24286(6) 0.33895(4) 0.05260(2) 0.04930(18) Uani d 1 . .
Br Br1 0.0000 1.06383(8) 0.2500 0.0454(3) Uani d 1 . .
P P1 -0.5000 1.0970(3) 0.2500 0.0789(16) Uani d 1 . .
F F1 0.0599(6) 0.8584(3) 0.01623(18) 0.0460(13) Uani d 1 . .
F F2 0.1342(6) 0.6019(3) -0.04406(16) 0.0462(13) Uani d 1 . .
F F3 0.1207(7) 0.6282(3) 0.10592(17) 0.0538(15) Uani d 1 . .
C C1 0.0863(8) 0.7449(5) 0.0629(3) 0.0367(18) Uani d 1 . .
C C2 0.0807(8) 0.7769(5) 0.0215(3) 0.0342(17) Uani d 1 . .
C C3 0.0912(8) 0.7310(5) -0.0161(3) 0.0344(17) Uani d 1 . .
C C4 0.1172(8) 0.6476(5) -0.0092(3) 0.0349(17) Uani d 1 . .
C C5 0.1286(9) 0.6106(6) 0.0315(3) 0.0390(18) Uani d 1 . .
C C6 0.1115(8) 0.6616(6) 0.0665(3) 0.0374(18) Uani d 1 . .
C C7 0.0759(9) 0.7952(6) 0.1006(3) 0.042(2) Uani d 1 . .
C C8 0.0626(10) 0.8383(6) 0.1304(3) 0.044(2) Uani d 1 . .
C C9 0.0814(8) 0.7670(5) -0.0585(3) 0.0368(18) Uani d 1 . .
C C10 0.0721(10) 0.7952(6) -0.0937(3) 0.043(2) Uani d 1 . .
C C11 0.1617(9) 0.5253(6) 0.0368(3) 0.042(2) Uani d 1 . .
C C12 0.1919(9) 0.4560(6) 0.0417(3) 0.0413(19) Uani d 1 . .
C C13 -0.4851(12) 1.0309(6) 0.2044(3) 0.054(3) Uani d 1 . .
C C14 -0.3678(12) 1.0134(7) 0.1900(4) 0.059(3) Uani d 1 . .
H H14A -0.2927 1.0402 0.2025 0.070 Uiso calc 1 . .
C C15 -0.3614(12) 0.9563(8) 0.1573(4) 0.062(3) Uani d 1 . .
H H15A -0.2814 0.9451 0.1466 0.075 Uiso calc 1 . .
C C16 -0.4696(13) 0.9155(8) 0.1398(4) 0.063(3) Uani d 1 . .
H H16A -0.4635 0.8746 0.1183 0.076 Uiso calc 1 . .
C C17 -0.5861(14) 0.9343(9) 0.1539(4) 0.075(4) Uani d 1 . .
H H17A -0.6608 0.9074 0.1412 0.090 Uiso calc 1 . .
C C18 -0.5963(15) 0.9922(10) 0.1864(5) 0.083(4) Uani d 1 . .
H H18A -0.6770 1.0050 0.1961 0.099 Uiso calc 1 . .
C C19 -0.4007(12) 1.1721(8) 0.2597(4) 0.045(3) Uani d 0.5 A -1
C C20 -0.3447(15) 1.2052(9) 0.2248(3) 0.054(5) Uani d 0.5 A -1
H H20A -0.3719 1.1877 0.1960 0.065 Uiso calc 0.5 A -1
C C21 -0.2488(15) 1.2639(9) 0.2318(4) 0.051(4) Uani d 0.5 A -1
H H21A -0.2106 1.2865 0.2079 0.061 Uiso calc 0.5 A -1
C C22 -0.2089(14) 1.2895(9) 0.2738(5) 0.048(5) Uani d 0.5 A -1
H H22A -0.1434 1.3296 0.2786 0.058 Uiso calc 0.5 A -1
C C23 -0.2649(14) 1.2564(10) 0.3088(4) 0.056(4) Uani d 0.5 A -1
H H23A -0.2377 1.2739 0.3375 0.067 Uiso calc 0.5 A -1
C C24 -0.3608(13) 1.1977(9) 0.3017(4) 0.052(4) Uani d 0.5 A -1
H H24A -0.3990 1.1751 0.3256 0.062 Uiso calc 0.5 A -1
O O1 -0.660(3) 1.2121(16) 0.2952(8) 0.103(8) Uani d 0.5 A -1
C C25 -0.668(4) 1.1538(19) 0.2310(12) 0.097(7) Uani d 0.5 A -1
H H25A -0.6631 1.1776 0.2018 0.116 Uiso calc 0.5 A -1
H H25B -0.7371 1.1122 0.2286 0.116 Uiso calc 0.5 A -1
C C26 -0.699(4) 1.2125(18) 0.2575(11) 0.081(6) Uani d 0.5 A -1
C C27 -0.797(4) 1.2767(19) 0.2383(12) 0.082(9) Uani d 0.5 A -1
H H27A -0.8114 1.3177 0.2605 0.124 Uiso calc 0.5 A -1
H H27B -0.8782 1.2491 0.2289 0.124 Uiso calc 0.5 A -1
H H27C -0.7646 1.3038 0.2134 0.124 Uiso calc 0.5 A -1
N N1 0.2885(15) 1.1613(8) 0.0787(6) 0.108(5) Uani d 1 . .
C C28 0.2256(14) 1.1050(8) 0.0728(5) 0.073(3) Uani d 1 . .
C C29 0.1431(14) 1.0364(8) 0.0630(5) 0.079(4) Uani d 1 . .
H H29A 0.0638 1.0440 0.0767 0.118 Uiso calc 1 . .
H H29B 0.1857 0.9860 0.0740 0.118 Uiso calc 1 . .
H H29C 0.1231 1.0321 0.0314 0.118 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'
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'
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 C13 . 2_455 114.3(6)
C19 P1 C13 . . 119.7(6)
C13 P1 C13 2_455 . 106.3(7)
C19 P1 C25 . . 103.7(12)
C13 P1 C25 2_455 . 111.1(11)
C13 P1 C25 . . 100.8(11)
C2 C1 C6 . . 115.8(8)
C2 C1 C7 . . 122.7(8)
C6 C1 C7 . . 121.4(8)
F1 C2 C1 . . 118.3(7)
F1 C2 C3 . . 116.7(8)
C1 C2 C3 . . 125.0(8)
C2 C3 C4 . . 114.9(7)
C2 C3 C9 . . 122.7(8)
C4 C3 C9 . . 122.3(8)
F2 C4 C5 . . 119.0(7)
F2 C4 C3 . . 117.1(7)
C5 C4 C3 . . 123.9(8)
C4 C5 C6 . . 116.2(8)
C4 C5 C11 . . 121.4(8)
C6 C5 C11 . . 122.4(8)
F3 C6 C1 . . 118.1(8)
F3 C6 C5 . . 117.8(8)
C1 C6 C5 . . 124.1(8)
C8 C7 C1 . . 176.7(10)
C7 C8 I1 . . 176.8(9)
C10 C9 C3 . . 178.6(10)
C9 C10 I2 . . 177.7(9)
C12 C11 C5 . . 178.2(11)
C11 C12 I3 . . 177.7(9)
C14 C13 C18 . . 121.2(11)
C14 C13 P1 . . 121.8(9)
C18 C13 P1 . . 116.8(10)
C13 C14 C15 . . 119.0(11)
C16 C15 C14 . . 120.8(12)
C17 C16 C15 . . 119.7(11)
C16 C17 C18 . . 121.0(13)
C17 C18 C13 . . 118.3(13)
C20 C19 C24 . . 120.0
C20 C19 P1 . . 117.6(9)
C24 C19 P1 . . 122.1(8)
C19 C20 C21 . . 120.0
C22 C21 C20 . . 120.0
C21 C22 C23 . . 120.0
C22 C23 C24 . . 120.0
C23 C24 C19 . . 120.0
C26 C25 P1 . . 114(3)
O1 C26 C25 . . 121(3)
O1 C26 C27 . . 122(3)
C25 C26 C27 . . 116(3)
N1 C28 C29 . . 176.6(18)
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(9)
I2 C10 . 2.016(9)
I3 C12 . 1.999(9)
P1 C19 . 1.616(11)
P1 C13 2_455 1.794(11)
P1 C13 . 1.795(11)
P1 C25 . 2.03(4)
F1 C2 . 1.352(9)
F2 C4 . 1.337(9)
F3 C6 . 1.330(10)
C1 C2 . 1.379(12)
C1 C6 . 1.384(12)
C1 C7 . 1.439(12)
C2 C3 . 1.397(11)
C3 C4 . 1.397(12)
C3 C9 . 1.430(12)
C4 C5 . 1.389(12)
C5 C6 . 1.390(12)
C5 C11 . 1.437(13)
C7 C8 . 1.177(13)
C9 C10 . 1.177(12)
C11 C12 . 1.178(13)
C13 C14 . 1.381(17)
C13 C18 . 1.395(18)
C14 C15 . 1.381(16)
C15 C16 . 1.380(17)
C16 C17 . 1.374(18)
C17 C18 . 1.390(19)
C19 C20 . 1.3900
C19 C24 . 1.3900
C20 C21 . 1.3900
C21 C22 . 1.3900
C22 C23 . 1.3900
C23 C24 . 1.3900
O1 C26 . 1.20(4)
C25 C26 . 1.32(4)
C26 C27 . 1.55(4)
N1 C28 . 1.135(19)
C28 C29 . 1.429(19)
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 . -178.2(8)
C7 C1 C2 F1 . -2.4(13)
C6 C1 C2 C3 . 3.8(13)
C7 C1 C2 C3 . 179.5(9)
F1 C2 C3 C4 . 177.7(7)
C1 C2 C3 C4 . -4.1(13)
F1 C2 C3 C9 . 0.3(12)
C1 C2 C3 C9 . 178.4(8)
C2 C3 C4 F2 . -176.9(7)
C9 C3 C4 F2 . 0.6(13)
C2 C3 C4 C5 . 1.9(13)
C9 C3 C4 C5 . 179.4(8)
F2 C4 C5 C6 . 179.2(8)
C3 C4 C5 C6 . 0.4(14)
F2 C4 C5 C11 . 1.8(13)
C3 C4 C5 C11 . -176.9(9)
C2 C1 C6 F3 . 178.6(8)
C7 C1 C6 F3 . 2.7(13)
C2 C1 C6 C5 . -1.1(14)
C7 C1 C6 C5 . -176.9(9)
C4 C5 C6 F3 . 179.5(8)
C11 C5 C6 F3 . -3.2(14)
C4 C5 C6 C1 . -0.9(14)
C11 C5 C6 C1 . 176.4(9)
C19 P1 C13 C14 . 32.0(12)
C13 P1 C13 C14 2_455 -99.3(10)
C25 P1 C13 C14 . 144.8(13)
C19 P1 C13 C18 . -153.4(11)
C13 P1 C13 C18 2_455 75.3(10)
C25 P1 C13 C18 . -40.7(15)
C18 C13 C14 C15 . -0.1(17)
P1 C13 C14 C15 . 174.2(9)
C13 C14 C15 C16 . -1.8(17)
C14 C15 C16 C17 . 2.9(19)
C15 C16 C17 C18 . -2(2)
C16 C17 C18 C13 . 0(2)
C14 C13 C18 C17 . 1(2)
P1 C13 C18 C17 . -173.7(11)
C13 P1 C19 C20 2_455 154.7(7)
C13 P1 C19 C20 . 27.0(10)
C25 P1 C19 C20 . -84.1(13)
C13 P1 C19 C24 2_455 -18.4(11)
C13 P1 C19 C24 . -146.1(8)
C25 P1 C19 C24 . 102.7(13)
C24 C19 C20 C21 . 0.0
P1 C19 C20 C21 . -173.3(11)
C19 C20 C21 C22 . 0.0
C20 C21 C22 C23 . 0.0
C21 C22 C23 C24 . 0.0
C22 C23 C24 C19 . 0.0
C20 C19 C24 C23 . 0.0
P1 C19 C24 C23 . 173.0(12)
P1 C25 C26 O1 . -26(5)
P1 C25 C26 C27 . 160(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064610
