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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/7/12/44/7124401.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_7124401
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_compound_source        isobutanol
_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                116.0359(6)
_cell_angle_beta                 100.5276(7)
_cell_angle_gamma                94.7799(7)
_cell_formula_units_Z            1
_cell_length_a                   6.04730(10)
_cell_length_b                   12.0007(2)
_cell_length_c                   12.56410(10)
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    253.0(1)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      0.407
_cell_volume                     791.56(2)
_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      253.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19024
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         3.237
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             406
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0040(10)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0202
_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)+(0.0178P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3360
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06735c2.cif
_cod_data_source_block           tric_2mdppo_14tfib_253K
_cod_database_code               7124401
_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   0.566
_shelx_estimated_absorpt_t_max   0.815
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 0.5096(4) 0.12761(19) 0.08242(19) 0.0416(4) Uani 1 1 d . .
C2B C 0.6936(4) 0.0687(2) 0.0888(2) 0.0471(5) Uani 1 1 d . .
C3B C 0.6835(4) -0.0557(2) 0.0090(2) 0.0482(5) Uani 1 1 d . .
F1B F 0.8875(3) 0.13326(14) 0.17580(15) 0.0760(5) Uani 1 1 d . .
F2B F 0.8703(3) -0.10729(14) 0.02138(16) 0.0762(5) Uani 1 1 d . .
I1B I 0.52804(2) 0.31644(2) 0.20621(2) 0.04339(7) Uani 1 1 d . .
C1A C 0.4274(3) 0.79034(19) 0.51198(18) 0.0390(4) Uani 1 1 d . .
C2A C 0.6404(4) 0.8380(2) 0.5901(2) 0.0587(6) Uani 1 1 d . .
H2A H 0.754186 0.789349 0.577370 0.070 Uiso 1 1 calc R U
C3A C 0.6878(6) 0.9581(3) 0.6882(3) 0.0776(9) Uani 1 1 d . .
H3A H 0.832522 0.988798 0.741406 0.093 Uiso 1 1 calc R U
C4A C 0.5261(6) 1.0312(2) 0.7074(2) 0.0705(8) Uani 1 1 d . .
H4A H 0.560017 1.112211 0.772625 0.085 Uiso 1 1 calc R U
C5A C 0.3154(6) 0.9858(3) 0.6312(3) 0.0951(12) Uani 1 1 d . .
H5A H 0.203887 1.035959 0.643981 0.114 Uiso 1 1 calc R U
C6A C 0.2635(5) 0.8649(3) 0.5339(3) 0.0850(11) Uani 1 1 d . .
H6A H 0.116527 0.834005 0.483137 0.102 Uiso 1 1 calc R U
C7A C 0.2496(3) 0.64208(17) 0.25008(17) 0.0351(4) Uani 1 1 d . .
C8A C 0.0369(4) 0.6753(2) 0.2273(2) 0.0461(5) Uani 1 1 d . .
H8A H -0.053930 0.689481 0.282644 0.055 Uiso 1 1 calc R U
C9A C -0.0393(4) 0.6874(2) 0.1228(2) 0.0519(5) Uani 1 1 d . .
H9A H -0.179577 0.711601 0.109191 0.062 Uiso 1 1 calc R U
C10A C 0.0916(4) 0.6636(2) 0.0385(2) 0.0479(5) Uani 1 1 d . .
H10A H 0.039975 0.672146 -0.031439 0.058 Uiso 1 1 calc R U
C11A C 0.2992(4) 0.6273(2) 0.05860(19) 0.0454(5) Uani 1 1 d . .
H11A H 0.386102 0.609526 0.001165 0.054 Uiso 1 1 calc R U
C12A C 0.3787(4) 0.61710(18) 0.16423(18) 0.0395(4) Uani 1 1 d . .
H12A H 0.519604 0.593368 0.177565 0.047 Uiso 1 1 calc R U
C13A C 0.1523(4) 0.5425(2) 0.4117(2) 0.0481(5) Uani 1 1 d . .
H13A H 0.210376 0.535455 0.484431 0.072 Uiso 1 1 calc R U
H13B H 0.106215 0.459744 0.343017 0.072 Uiso 1 1 calc R U
H13C H 0.022947 0.584077 0.420580 0.072 Uiso 1 1 calc R U
O1A O 0.5839(2) 0.57775(14) 0.37759(13) 0.0433(3) Uani 1 1 d . .
P1A P 0.37084(8) 0.63217(5) 0.38737(4) 0.03362(11) 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 116.49(19) . 2_655
C2B C1B I1B 120.79(15) . .
C3B C1B I1B 122.72(15) 2_655 .
F1B C2B C3B 118.82(19) . .
F1B C2B C1B 119.64(19) . .
C3B C2B C1B 121.53(19) . .
F2B C3B C2B 118.16(19) . .
F2B C3B C1B 119.86(19) . 2_655
C2B C3B C1B 121.98(19) . 2_655
C2A C1A C6A 118.1(2) . .
C2A C1A P1A 119.13(17) . .
C6A C1A P1A 122.79(18) . .
C1A C2A C3A 120.5(3) . .
C1A C2A H2A 119.7 . .
C3A C2A H2A 119.7 . .
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 120.2 . .
C3A C4A H4A 120.2 . .
C4A C5A C6A 120.5(3) . .
C4A C5A H5A 119.7 . .
C6A C5A H5A 119.7 . .
C1A C6A C5A 120.6(3) . .
C1A C6A H6A 119.7 . .
C5A C6A H6A 119.7 . .
C12A C7A C8A 118.89(19) . .
C12A C7A P1A 117.52(15) . .
C8A C7A P1A 123.59(15) . .
C9A C8A C7A 120.2(2) . .
C9A C8A H8A 119.9 . .
C7A C8A H8A 119.9 . .
C10A C9A C8A 120.4(2) . .
C10A C9A H9A 119.8 . .
C8A C9A H9A 119.8 . .
C11A C10A C9A 119.7(2) . .
C11A C10A H10A 120.1 . .
C9A C10A H10A 120.1 . .
C10A C11A C12A 120.2(2) . .
C10A C11A H11A 119.9 . .
C12A C11A H11A 119.9 . .
C7A C12A C11A 120.47(19) . .
C7A C12A H12A 119.8 . .
C11A C12A H12A 119.8 . .
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 113.53(10) . .
O1A P1A C1A 111.46(9) . .
C13A P1A C1A 106.81(11) . .
O1A P1A C7A 110.89(9) . .
C13A P1A C7A 107.02(10) . .
C1A P1A C7A 106.76(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1B C2B 1.375(3) .
C1B C3B 1.378(3) 2_655
C1B I1B 2.090(2) .
C2B F1B 1.344(2) .
C2B C3B 1.374(3) .
C3B F2B 1.349(2) .
C1A C2A 1.368(3) .
C1A C6A 1.375(3) .
C1A P1A 1.805(2) .
C2A C3A 1.386(4) .
C2A H2A 0.9300 .
C3A C4A 1.351(4) .
C3A H3A 0.9300 .
C4A C5A 1.348(5) .
C4A H4A 0.9300 .
C5A C6A 1.387(4) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
C7A C12A 1.388(3) .
C7A C8A 1.395(3) .
C7A P1A 1.8054(19) .
C8A C9A 1.384(3) .
C8A H8A 0.9300 .
C9A C10A 1.381(3) .
C9A H9A 0.9300 .
C10A C11A 1.379(3) .
C10A H10A 0.9300 .
C11A C12A 1.388(3) .
C11A H11A 0.9300 .
C12A H12A 0.9300 .
C13A P1A 1.788(2) .
C13A H13A 0.9600 .
C13A H13B 0.9600 .
C13A H13C 0.9600 .
O1A P1A 1.4932(14) .
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 -179.9(2) 2_655 .
I1B C1B C2B F1B 0.1(3) . .
C3B C1B C2B C3B -0.8(4) 2_655 .
I1B C1B C2B C3B 179.27(19) . .
F1B C2B C3B F2B -0.4(4) . .
C1B C2B C3B F2B -179.5(2) . .
F1B C2B C3B C1B 180.0(2) . 2_655
C1B C2B C3B C1B 0.9(4) . 2_655
C6A C1A C2A C3A -0.1(4) . .
P1A C1A C2A C3A -178.6(2) . .
C1A C2A C3A C4A -1.1(5) . .
C2A C3A C4A C5A 1.0(5) . .
C3A C4A C5A C6A 0.2(6) . .
C2A C1A C6A C5A 1.3(5) . .
P1A C1A C6A C5A 179.8(3) . .
C4A C5A C6A C1A -1.4(6) . .
C12A C7A C8A C9A -2.2(3) . .
P1A C7A C8A C9A 176.59(18) . .
C7A C8A C9A C10A 1.6(4) . .
C8A C9A C10A C11A 0.2(4) . .
C9A C10A C11A C12A -1.4(3) . .
C8A C7A C12A C11A 1.1(3) . .
P1A C7A C12A C11A -177.77(16) . .
C10A C11A C12A C7A 0.7(3) . .
C2A C1A P1A O1A -7.1(2) . .
C6A C1A P1A O1A 174.4(2) . .
C2A C1A P1A C13A 117.4(2) . .
C6A C1A P1A C13A -61.0(3) . .
C2A C1A P1A C7A -128.4(2) . .
C6A C1A P1A C7A 53.2(3) . .
C12A C7A P1A O1A -8.84(18) . .
C8A C7A P1A O1A 172.30(17) . .
C12A C7A P1A C13A -133.16(16) . .
C8A C7A P1A C13A 48.0(2) . .
C12A C7A P1A C1A 112.76(16) . .
C8A C7A P1A C1A -66.10(19) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196574
