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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/43/7124398.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_7124398
loop_
_publ_author_name
'Topić, Filip'
'Lisac, Katarina'
'Arhangelskis, Mihails'
'Rissanen, Kari'
'Cinčić, Dominik'
'Friščić, Tomislav'
_publ_section_title
;
 Cocrystal trimorphism as a consequence of orthogonality of halogen- and
 hydrogen-bonds synthons
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06735C
_journal_year                    2019
_chemical_formula_moiety         '2(C13 H13 O P), C6 F4 I2'
_chemical_formula_sum            'C32 H26 F4 I2 O2 P2'
_chemical_formula_weight         834.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-03-23 deposited with the CCDC.    2019-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                113.430(5)
_cell_angle_beta                 100.733(5)
_cell_angle_gamma                97.582(5)
_cell_formula_units_Z            1
_cell_length_a                   6.0447(4)
_cell_length_b                   11.5656(6)
_cell_length_c                   12.5757(7)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      29.2260
_cell_measurement_theta_min      3.5190
_cell_volume                     771.60(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5563
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         29.455
_diffrn_reflns_theta_min         3.219
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.195
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             406
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.138
_refine_diff_density_max         1.072
_refine_diff_density_min         -1.884
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0295
_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)+(0.0401P)²+0.2956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3289
_reflns_number_total             3547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06735c2.cif
_cod_data_source_block           tric_2mdppo_14tfib_123K
_cod_original_cell_volume        771.60(8)
_cod_database_code               7124398
_shelx_shelxl_version_number     2017/1
_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   0.528
_shelx_estimated_absorpt_t_max   0.752
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1B C 0.5135(5) 0.1276(3) 0.0844(3) 0.0185(6) Uani 1 1 d . .
C2B C 0.6980(5) 0.0690(3) 0.0900(3) 0.0219(6) Uani 1 1 d . .
C3B C 0.6838(5) -0.0551(3) 0.0084(3) 0.0220(6) Uani 1 1 d . .
F1B F 0.8940(3) 0.13368(17) 0.17659(17) 0.0304(4) Uani 1 1 d . .
F2B F 0.8701(3) -0.10667(17) 0.01926(18) 0.0304(4) Uani 1 1 d . .
I1B I 0.53710(3) 0.31551(2) 0.20959(2) 0.01911(8) Uani 1 1 d . .
C1A C 0.4409(5) 0.7851(3) 0.5067(3) 0.0183(6) Uani 1 1 d . .
C2A C 0.6582(5) 0.8373(3) 0.5859(3) 0.0262(7) Uani 1 1 d . .
H2A H 0.777397 0.791342 0.573433 0.031 Uiso 1 1 calc R U
C3A C 0.7021(6) 0.9564(3) 0.6835(3) 0.0308(7) Uani 1 1 d . .
H3A H 0.850993 0.991166 0.738566 0.037 Uiso 1 1 calc R U
C4A C 0.5331(6) 1.0250(3) 0.7018(3) 0.0300(7) Uani 1 1 d . .
H4A H 0.565658 1.107608 0.768017 0.036 Uiso 1 1 calc R U
C5A C 0.3178(6) 0.9735(4) 0.6239(4) 0.0422(10) Uani 1 1 d . .
H5A H 0.199906 1.020284 0.637076 0.051 Uiso 1 1 calc R U
C6A C 0.2693(6) 0.8546(4) 0.5264(3) 0.0396(9) Uani 1 1 d . .
H6A H 0.118920 0.820066 0.472747 0.048 Uiso 1 1 calc R U
C7A C 0.2659(5) 0.6395(2) 0.2474(2) 0.0164(5) Uani 1 1 d . .
C8A C 0.0507(5) 0.6702(3) 0.2229(3) 0.0211(6) Uani 1 1 d . .
H8A H -0.043200 0.680665 0.277359 0.025 Uiso 1 1 calc R U
C9A C -0.0244(5) 0.6851(3) 0.1191(3) 0.0239(6) Uani 1 1 d . .
H9A H -0.167783 0.708593 0.104064 0.029 Uiso 1 1 calc R U
C10A C 0.1071(5) 0.6661(3) 0.0367(3) 0.0213(6) Uani 1 1 d . .
H10A H 0.054730 0.676942 -0.034076 0.026 Uiso 1 1 calc R U
C11A C 0.3164(5) 0.6311(3) 0.0587(3) 0.0214(6) Uani 1 1 d . .
H11A H 0.405382 0.615554 0.001691 0.026 Uiso 1 1 calc R U
C12A C 0.3954(5) 0.6187(3) 0.1636(3) 0.0182(6) Uani 1 1 d . .
H12A H 0.539460 0.595854 0.178465 0.022 Uiso 1 1 calc R U
C13A C 0.1647(5) 0.5264(3) 0.4049(3) 0.0232(6) Uani 1 1 d . .
H13A H 0.222626 0.518143 0.479132 0.035 Uiso 1 1 calc R U
H13B H 0.119353 0.440494 0.336694 0.035 Uiso 1 1 calc R U
H13C H 0.030398 0.565348 0.410531 0.035 Uiso 1 1 calc R U
O1A O 0.6026(3) 0.57700(19) 0.37724(19) 0.0196(4) Uani 1 1 d . .
P1A P 0.38636(12) 0.62659(7) 0.38376(7) 0.01550(15) 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'
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'
O O 0.0106 0.0060 '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'
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
C2B C1B C3B 116.6(3) . 2_655
C2B C1B I1B 120.8(2) . .
C3B C1B I1B 122.7(2) 2_655 .
F1B C2B C3B 119.1(3) . .
F1B C2B C1B 119.7(3) . .
C3B C2B C1B 121.2(3) . .
F2B C3B C2B 118.2(3) . .
F2B C3B C1B 119.6(3) . 2_655
C2B C3B C1B 122.2(3) . 2_655
C2A C1A C6A 119.0(3) . .
C2A C1A P1A 118.8(2) . .
C6A C1A P1A 122.2(2) . .
C1A C2A C3A 119.9(3) . .
C1A C2A H2A 120.0 . .
C3A C2A H2A 120.0 . .
C4A C3A C2A 120.8(3) . .
C4A C3A H3A 119.6 . .
C2A C3A H3A 119.6 . .
C5A C4A C3A 119.5(3) . .
C5A C4A H4A 120.3 . .
C3A C4A H4A 120.3 . .
C4A C5A C6A 120.9(3) . .
C4A C5A H5A 119.6 . .
C6A C5A H5A 119.6 . .
C5A C6A C1A 119.9(3) . .
C5A C6A H6A 120.0 . .
C1A C6A H6A 120.0 . .
C12A C7A C8A 119.0(3) . .
C12A C7A P1A 117.7(2) . .
C8A C7A P1A 123.3(2) . .
C9A C8A C7A 119.9(3) . .
C9A C8A H8A 120.1 . .
C7A C8A H8A 120.1 . .
C8A C9A C10A 120.8(3) . .
C8A C9A H9A 119.6 . .
C10A C9A H9A 119.6 . .
C9A C10A C11A 119.4(3) . .
C9A C10A H10A 120.3 . .
C11A C10A H10A 120.3 . .
C12A C11A C10A 120.2(3) . .
C12A C11A H11A 119.9 . .
C10A C11A H11A 119.9 . .
C11A C12A C7A 120.7(3) . .
C11A C12A H12A 119.6 . .
C7A C12A H12A 119.6 . .
P1A C13A H13A 109.5 . .
P1A C13A H13B 109.5 . .
H13A C13A H13B 109.5 . .
P1A C13A H13C 109.5 . .
H13A C13A H13C 109.5 . .
H13B C13A H13C 109.5 . .
O1A P1A C13A 113.66(13) . .
O1A P1A C1A 111.65(13) . .
C13A P1A C1A 106.13(14) . .
O1A P1A C7A 110.73(13) . .
C13A P1A C7A 106.90(14) . .
C1A P1A C7A 107.40(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1B C2B 1.385(4) .
C1B C3B 1.388(4) 2_655
C1B I1B 2.082(3) .
C2B F1B 1.336(3) .
C2B C3B 1.372(4) .
C3B F2B 1.352(3) .
C1A C2A 1.381(4) .
C1A C6A 1.393(4) .
C1A P1A 1.805(3) .
C2A C3A 1.383(5) .
C2A H2A 0.9500 .
C3A C4A 1.371(5) .
C3A H3A 0.9500 .
C4A C5A 1.366(5) .
C4A H4A 0.9500 .
C5A C6A 1.378(5) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A C12A 1.392(4) .
C7A C8A 1.405(4) .
C7A P1A 1.805(3) .
C8A C9A 1.386(4) .
C8A H8A 0.9500 .
C9A C10A 1.387(4) .
C9A H9A 0.9500 .
C10A C11A 1.391(4) .
C10A H10A 0.9500 .
C11A C12A 1.387(4) .
C11A H11A 0.9500 .
C12A H12A 0.9500 .
C13A P1A 1.782(3) .
C13A H13A 0.9800 .
C13A H13B 0.9800 .
C13A H13C 0.9800 .
O1A P1A 1.4980(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3B C1B C2B F1B 179.5(3) 2_655 .
I1B C1B C2B F1B -0.2(4) . .
C3B C1B C2B C3B -0.8(5) 2_655 .
I1B C1B C2B C3B 179.6(2) . .
F1B C2B C3B F2B -0.1(4) . .
C1B C2B C3B F2B -179.8(3) . .
F1B C2B C3B C1B -179.4(3) . 2_655
C1B C2B C3B C1B 0.8(5) . 2_655
C6A C1A C2A C3A 0.4(5) . .
P1A C1A C2A C3A -177.5(3) . .
C1A C2A C3A C4A -1.1(5) . .
C2A C3A C4A C5A 1.4(5) . .
C3A C4A C5A C6A -1.0(6) . .
C4A C5A C6A C1A 0.3(7) . .
C2A C1A C6A C5A 0.0(6) . .
P1A C1A C6A C5A 177.9(3) . .
C12A C7A C8A C9A -2.9(4) . .
P1A C7A C8A C9A 176.5(2) . .
C7A C8A C9A C10A 2.0(5) . .
C8A C9A C10A C11A 0.3(4) . .
C9A C10A C11A C12A -1.7(4) . .
C10A C11A C12A C7A 0.8(4) . .
C8A C7A C12A C11A 1.5(4) . .
P1A C7A C12A C11A -178.0(2) . .
C2A C1A P1A O1A -6.2(3) . .
C6A C1A P1A O1A 175.9(3) . .
C2A C1A P1A C13A 118.1(3) . .
C6A C1A P1A C13A -59.7(3) . .
C2A C1A P1A C7A -127.8(2) . .
C6A C1A P1A C7A 54.4(3) . .
C12A C7A P1A O1A -7.5(3) . .
C8A C7A P1A O1A 173.1(2) . .
C12A C7A P1A C13A -131.8(2) . .
C8A C7A P1A C13A 48.7(3) . .
C12A C7A P1A C1A 114.7(2) . .
C8A C7A P1A C1A -64.8(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196574
