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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/7/12/43/7124397.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_7124397
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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.72260(10)
_cell_length_b                   16.3731(3)
_cell_length_c                   32.1528(7)
_cell_measurement_reflns_used    3900
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     3012.61(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            15206
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.987
_diffrn_reflns_theta_min         2.567
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: nitromethane'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.701
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.306
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0419
_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)+13.4079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3352
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06735c2.cif
_cod_data_source_block           ortho_2mdppo_14tfib_123K
_cod_database_code               7124397
_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   0.626
_shelx_estimated_absorpt_t_max   0.744
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
C1A C 0.4172(7) 0.7388(2) 0.12549(12) 0.0203(8) Uani 1 1 d . .
C2A C 0.2601(8) 0.7809(3) 0.10103(14) 0.0247(8) Uani 1 1 d . .
H2A H 0.114973 0.798266 0.112328 0.030 Uiso 1 1 calc R U
C3A C 0.3153(8) 0.7982(3) 0.05941(14) 0.0273(9) Uani 1 1 d . .
H3A H 0.209069 0.828339 0.042680 0.033 Uiso 1 1 calc R U
C4A C 0.5240(8) 0.7713(3) 0.04279(13) 0.0267(9) Uani 1 1 d . .
H4A H 0.558898 0.781785 0.014407 0.032 Uiso 1 1 calc R U
C5A C 0.6830(8) 0.7290(3) 0.06719(14) 0.0275(9) Uani 1 1 d . .
H5A H 0.826710 0.710912 0.055639 0.033 Uiso 1 1 calc R U
C6A C 0.6308(8) 0.7133(3) 0.10874(13) 0.0244(9) Uani 1 1 d . .
H6A H 0.740371 0.685296 0.125733 0.029 Uiso 1 1 calc R U
C7A C 0.4065(7) 0.6087(3) 0.18555(12) 0.0207(8) Uani 1 1 d . .
C8A C 0.6086(8) 0.5804(3) 0.20510(13) 0.0257(9) Uani 1 1 d . .
H8A H 0.719094 0.618216 0.215907 0.031 Uiso 1 1 calc R U
C9A C 0.6485(8) 0.4964(3) 0.20879(14) 0.0268(9) Uani 1 1 d . .
H9A H 0.785387 0.477181 0.222346 0.032 Uiso 1 1 calc R U
C10A C 0.4888(8) 0.4412(3) 0.19270(13) 0.0279(9) Uani 1 1 d . .
H10A H 0.516940 0.384247 0.195284 0.033 Uiso 1 1 calc R U
C11A C 0.2883(8) 0.4684(3) 0.17286(14) 0.0254(9) Uani 1 1 d . .
H11A H 0.180188 0.430435 0.161525 0.031 Uiso 1 1 calc R U
C12A C 0.2465(8) 0.5524(3) 0.16967(13) 0.0233(8) Uani 1 1 d . .
H12A H 0.107845 0.571252 0.156570 0.028 Uiso 1 1 calc R U
C13A C 0.5346(8) 0.7714(3) 0.21092(13) 0.0239(8) Uani 1 1 d . .
H13A H 0.497282 0.829703 0.209330 0.036 Uiso 1 1 calc R U
H13B H 0.695107 0.762424 0.201337 0.036 Uiso 1 1 calc R U
H13C H 0.519504 0.752746 0.239759 0.036 Uiso 1 1 calc R U
O1A O 0.0848(5) 0.73268(19) 0.18630(9) 0.0240(6) Uani 1 1 d . .
P1A P 0.33734(18) 0.71529(6) 0.17870(3) 0.0187(2) Uani 1 1 d . .
C1B C 0.8728(8) 0.4907(3) 0.03707(13) 0.0222(8) Uani 1 1 d . .
C2B C 0.8021(7) 0.4532(3) 0.00068(14) 0.0226(8) Uani 1 1 d . .
C3B C 0.9282(8) 0.4614(2) -0.03552(13) 0.0225(8) Uani 1 1 d . .
F1B F 0.6070(5) 0.40729(17) 0.00012(8) 0.0312(6) Uani 1 1 d . .
F2B F 0.8531(5) 0.42218(17) -0.06986(8) 0.0301(6) Uani 1 1 d . .
I1B I 0.68972(5) 0.47469(2) 0.09239(2) 0.02887(14) 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
C2A C1A C6A 119.9(4) . .
C2A C1A P1A 118.7(3) . .
C6A C1A P1A 121.4(3) . .
C1A C2A C3A 119.9(4) . .
C1A C2A H2A 120.1 . .
C3A C2A H2A 120.1 . .
C4A C3A C2A 120.0(4) . .
C4A C3A H3A 120.0 . .
C2A C3A H3A 120.0 . .
C3A C4A C5A 120.5(4) . .
C3A C4A H4A 119.7 . .
C5A C4A H4A 119.7 . .
C4A C5A C6A 119.6(4) . .
C4A C5A H5A 120.2 . .
C6A C5A H5A 120.2 . .
C5A C6A C1A 120.1(4) . .
C5A C6A H6A 119.9 . .
C1A C6A H6A 119.9 . .
C8A C7A C12A 119.3(4) . .
C8A C7A P1A 123.9(3) . .
C12A C7A P1A 116.8(3) . .
C7A C8A C9A 119.9(4) . .
C7A C8A H8A 120.0 . .
C9A C8A H8A 120.0 . .
C10A C9A C8A 120.1(4) . .
C10A C9A H9A 119.9 . .
C8A C9A H9A 119.9 . .
C9A C10A C11A 120.5(4) . .
C9A C10A H10A 119.7 . .
C11A C10A H10A 119.7 . .
C10A C11A C12A 119.4(4) . .
C10A C11A H11A 120.3 . .
C12A C11A H11A 120.3 . .
C7A C12A C11A 120.7(4) . .
C7A C12A H12A 119.7 . .
C11A C12A H12A 119.7 . .
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 114.75(19) . .
O1A P1A C7A 112.15(19) . .
C13A P1A C7A 106.7(2) . .
O1A P1A C1A 110.98(18) . .
C13A P1A C1A 106.21(19) . .
C7A P1A C1A 105.40(18) . .
C2B C1B C3B 117.5(4) . 5_765
C2B C1B I1B 121.4(3) . .
C3B C1B I1B 121.1(3) 5_765 .
F1B C2B C3B 118.6(4) . .
F1B C2B C1B 120.1(4) . .
C3B C2B C1B 121.3(4) . .
F2B C3B C2B 118.6(4) . .
F2B C3B C1B 120.2(4) . 5_765
C2B C3B C1B 121.1(4) . 5_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C2A 1.379(6) .
C1A C6A 1.399(6) .
C1A P1A 1.812(4) .
C2A C3A 1.404(6) .
C2A H2A 0.9500 .
C3A C4A 1.380(7) .
C3A H3A 0.9500 .
C4A C5A 1.386(6) .
C4A H4A 0.9500 .
C5A C6A 1.393(6) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A C8A 1.396(6) .
C7A C12A 1.396(6) .
C7A P1A 1.803(4) .
C8A C9A 1.400(6) .
C8A H8A 0.9500 .
C9A C10A 1.385(7) .
C9A H9A 0.9500 .
C10A C11A 1.387(7) .
C10A H10A 0.9500 .
C11A C12A 1.398(6) .
C11A H11A 0.9500 .
C12A H12A 0.9500 .
C13A P1A 1.786(4) .
C13A H13A 0.9800 .
C13A H13B 0.9800 .
C13A H13C 0.9800 .
O1A P1A 1.493(3) .
C1B C2B 1.382(6) .
C1B C3B 1.383(6) 5_765
C1B I1B 2.081(4) .
C2B F1B 1.347(5) .
C2B C3B 1.376(6) .
C3B F2B 1.348(5) .
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
C6A C1A C2A C3A 0.0(6) . .
P1A C1A C2A C3A -178.4(3) . .
C1A C2A C3A C4A 1.5(7) . .
C2A C3A C4A C5A -1.7(7) . .
C3A C4A C5A C6A 0.3(7) . .
C4A C5A C6A C1A 1.2(7) . .
C2A C1A C6A C5A -1.3(6) . .
P1A C1A C6A C5A 177.1(3) . .
C12A C7A C8A C9A -0.3(6) . .
P1A C7A C8A C9A -179.6(3) . .
C7A C8A C9A C10A 0.6(7) . .
C8A C9A C10A C11A 0.0(7) . .
C9A C10A C11A C12A -0.9(7) . .
C8A C7A C12A C11A -0.6(6) . .
P1A C7A C12A C11A 178.7(3) . .
C10A C11A C12A C7A 1.2(6) . .
C8A C7A P1A O1A -139.2(3) . .
C12A C7A P1A O1A 41.5(4) . .
C8A C7A P1A C13A -12.7(4) . .
C12A C7A P1A C13A 168.0(3) . .
C8A C7A P1A C1A 100.0(4) . .
C12A C7A P1A C1A -79.3(3) . .
C2A C1A P1A O1A 10.7(4) . .
C6A C1A P1A O1A -167.7(3) . .
C2A C1A P1A C13A -114.6(3) . .
C6A C1A P1A C13A 67.0(4) . .
C2A C1A P1A C7A 132.3(3) . .
C6A C1A P1A C7A -46.1(4) . .
C3B C1B C2B F1B -178.6(4) 5_765 .
I1B C1B C2B F1B 2.2(6) . .
C3B C1B C2B C3B 1.7(7) 5_765 .
I1B C1B C2B C3B -177.6(3) . .
F1B C2B C3B F2B -1.0(6) . .
C1B C2B C3B F2B 178.8(4) . .
F1B C2B C3B C1B 178.5(4) . 5_765
C1B C2B C3B C1B -1.7(7) . 5_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196574
