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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/7/12/44/7124400.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_7124400
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 90.628(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5273(4)
_cell_length_b                   5.88431(18)
_cell_length_c                   23.5890(7)
_cell_measurement_reflns_used    6810
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      29.0600
_cell_measurement_theta_min      3.5210
_cell_volume                     1599.95(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 0.998
_diffrn_measured_fraction_theta_max 0.894
_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  0.0258
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12445
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         29.358
_diffrn_reflns_theta_min         3.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79065
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0178P)²+0.3814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3528
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06735c2.cif
_cod_data_source_block           mono_2mdppo_14tfib_123K
_cod_database_code               7124400
_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   0.485
_shelx_estimated_absorpt_t_max   0.745
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1B I 0.80669(2) 0.35904(2) 0.39003(2) 0.02169(5) Uani 1 1 d . .
P1A P 0.57529(4) 0.05867(8) 0.30504(2) 0.01712(11) Uani 1 1 d . .
F1B F 0.82969(10) 0.7940(2) 0.46892(5) 0.0270(3) Uani 1 1 d . .
C7A C 0.49610(17) -0.0235(3) 0.36724(8) 0.0192(4) Uani 1 1 d . .
O1A O 0.62532(12) 0.2920(2) 0.31090(6) 0.0216(3) Uani 1 1 d . .
C8A C 0.5046(2) -0.2350(4) 0.39304(9) 0.0301(5) Uani 1 1 d . .
H8A H 0.554041 -0.348241 0.377820 0.036 Uiso 1 1 calc R U
C12A C 0.4231(2) 0.1387(4) 0.39031(10) 0.0313(5) Uani 1 1 d . .
H12A H 0.416844 0.284043 0.373038 0.038 Uiso 1 1 calc R U
C6A C 0.3999(2) -0.1409(4) 0.23937(10) 0.0302(5) Uani 1 1 d . .
H6A H 0.402176 -0.262826 0.265749 0.036 Uiso 1 1 calc R U
C1A C 0.47287(17) 0.0450(3) 0.24714(8) 0.0191(4) Uani 1 1 d . .
C4A C 0.3197(2) 0.0291(4) 0.15541(10) 0.0351(5) Uani 1 1 d . .
H4A H 0.267414 0.023346 0.124043 0.042 Uiso 1 1 calc R U
C2B C 0.91329(17) 0.6452(3) 0.48379(8) 0.0199(4) Uani 1 1 d . .
C10A C 0.3683(2) -0.1186(4) 0.46360(10) 0.0372(6) Uani 1 1 d . .
H10A H 0.324757 -0.151416 0.496561 0.045 Uiso 1 1 calc R U
C2A C 0.46759(18) 0.2242(4) 0.20831(8) 0.0250(5) Uani 1 1 d . .
H2A H 0.516680 0.352560 0.213195 0.030 Uiso 1 1 calc R U
C9A C 0.4403(2) -0.2802(4) 0.44121(10) 0.0359(6) Uani 1 1 d . .
H9A H 0.446295 -0.424908 0.458877 0.043 Uiso 1 1 calc R U
C13A C 0.68098(19) -0.1568(3) 0.29254(9) 0.0242(5) Uani 1 1 d . .
H13A H 0.736162 -0.161920 0.324412 0.036 Uiso 1 1 calc R U
H13B H 0.722540 -0.122467 0.257546 0.036 Uiso 1 1 calc R U
H13C H 0.642254 -0.304422 0.288791 0.036 Uiso 1 1 calc R U
C1B C 0.92474(17) 0.4427(3) 0.45462(8) 0.0187(4) Uani 1 1 d . .
C5A C 0.3242(2) -0.1498(4) 0.19371(10) 0.0387(6) Uani 1 1 d . .
H5A H 0.275247 -0.278134 0.188500 0.046 Uiso 1 1 calc R U
C3A C 0.3911(2) 0.2151(4) 0.16277(9) 0.0322(5) Uani 1 1 d . .
H3A H 0.387671 0.337390 0.136505 0.039 Uiso 1 1 calc R U
C11A C 0.3594(2) 0.0908(4) 0.43824(10) 0.0410(6) Uani 1 1 d . .
H11A H 0.309446 0.202898 0.453605 0.049 Uiso 1 1 calc R U
F2B F 0.96976(11) 0.89920(19) 0.55545(5) 0.0276(3) Uani 1 1 d . .
C3B C 0.98626(18) 0.7004(3) 0.52833(8) 0.0197(4) 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
O1A P1A C13A 113.85(9) . .
O1A P1A C1A 111.15(9) . .
C13A P1A C1A 106.65(10) . .
O1A P1A C7A 111.67(8) . .
C13A P1A C7A 107.25(9) . .
C1A P1A C7A 105.80(9) . .
C12A C7A C8A 118.99(18) . .
C12A C7A P1A 116.72(15) . .
C8A C7A P1A 124.29(15) . .
C7A C8A C9A 119.7(2) . .
C7A C8A H8A 120.2 . .
C9A C8A H8A 120.2 . .
C11A C12A C7A 120.7(2) . .
C11A C12A H12A 119.7 . .
C7A C12A H12A 119.7 . .
C5A C6A C1A 120.6(2) . .
C5A C6A H6A 119.7 . .
C1A C6A H6A 119.7 . .
C6A C1A C2A 119.02(19) . .
C6A C1A P1A 121.78(16) . .
C2A C1A P1A 119.19(16) . .
C3A C4A C5A 120.1(2) . .
C3A C4A H4A 119.9 . .
C5A C4A H4A 119.9 . .
F1B C2B C3B 118.34(17) . .
F1B C2B C1B 120.20(18) . .
C3B C2B C1B 121.46(18) . .
C9A C10A C11A 119.8(2) . .
C9A C10A H10A 120.1 . .
C11A C10A H10A 120.1 . .
C3A C2A C1A 120.2(2) . .
C3A C2A H2A 119.9 . .
C1A C2A H2A 119.9 . .
C10A C9A C8A 120.8(2) . .
C10A C9A H9A 119.6 . .
C8A C9A H9A 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 . .
C2B C1B C3B 117.01(18) . 3_766
C2B C1B I1B 120.04(15) . .
C3B C1B I1B 122.91(14) 3_766 .
C6A C5A C4A 119.9(2) . .
C6A C5A H5A 120.1 . .
C4A C5A H5A 120.1 . .
C4A C3A C2A 120.2(2) . .
C4A C3A H3A 119.9 . .
C2A C3A H3A 119.9 . .
C10A C11A C12A 120.0(2) . .
C10A C11A H11A 120.0 . .
C12A C11A H11A 120.0 . .
F2B C3B C2B 118.60(17) . .
F2B C3B C1B 119.89(18) . 3_766
C2B C3B C1B 121.52(17) . 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1B C1B 2.091(2) .
P1A O1A 1.4952(14) .
P1A C13A 1.785(2) .
P1A C1A 1.797(2) .
P1A C7A 1.8025(19) .
F1B C2B 1.346(2) .
C7A C12A 1.387(3) .
C7A C8A 1.389(3) .
C8A C9A 1.389(3) .
C8A H8A 0.9500 .
C12A C11A 1.384(3) .
C12A H12A 0.9500 .
C6A C5A 1.380(3) .
C6A C1A 1.391(3) .
C6A H6A 0.9500 .
C1A C2A 1.398(3) .
C4A C3A 1.379(3) .
C4A C5A 1.388(3) .
C4A H4A 0.9500 .
C2B C3B 1.378(3) .
C2B C1B 1.383(3) .
C10A C9A 1.372(3) .
C10A C11A 1.373(3) .
C10A H10A 0.9500 .
C2A C3A 1.383(3) .
C2A H2A 0.9500 .
C9A H9A 0.9500 .
C13A H13A 0.9800 .
C13A H13B 0.9800 .
C13A H13C 0.9800 .
C1B C3B 1.384(3) 3_766
C5A H5A 0.9500 .
C3A H3A 0.9500 .
C11A H11A 0.9500 .
F2B C3B 1.348(2) .
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_4
O1A P1A C7A C12A 43.8(2) .
C13A P1A C7A C12A 169.19(17) .
C1A P1A C7A C12A -77.26(18) .
O1A P1A C7A C8A -135.71(18) .
C13A P1A C7A C8A -10.3(2) .
C1A P1A C7A C8A 103.23(19) .
C12A C7A C8A C9A -0.1(3) .
P1A C7A C8A C9A 179.45(18) .
C8A C7A C12A C11A -0.1(4) .
P1A C7A C12A C11A -179.7(2) .
C5A C6A C1A C2A 0.7(3) .
C5A C6A C1A P1A -178.26(18) .
O1A P1A C1A C6A -168.38(16) .
C13A P1A C1A C6A 66.99(19) .
C7A P1A C1A C6A -46.98(19) .
O1A P1A C1A C2A 12.67(18) .
C13A P1A C1A C2A -111.96(17) .
C7A P1A C1A C2A 134.07(16) .
C6A C1A C2A C3A -0.3(3) .
P1A C1A C2A C3A 178.68(16) .
C11A C10A C9A C8A 0.0(4) .
C7A C8A C9A C10A 0.1(4) .
F1B C2B C1B C3B 179.00(16) 3_766
C3B C2B C1B C3B -0.9(3) 3_766
F1B C2B C1B I1B -3.3(2) .
C3B C2B C1B I1B 176.88(14) .
C1A C6A C5A C4A -0.7(4) .
C3A C4A C5A C6A 0.3(4) .
C5A C4A C3A C2A 0.1(4) .
C1A C2A C3A C4A -0.1(3) .
C9A C10A C11A C12A -0.2(4) .
C7A C12A C11A C10A 0.3(4) .
F1B C2B C3B F2B 0.9(3) .
C1B C2B C3B F2B -179.26(17) .
F1B C2B C3B C1B -178.97(17) 3_766
C1B C2B C3B C1B 0.9(3) 3_766
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196574
