Cocrystal trimorphism as a consequence of orthogonality of halogen- and hydrogen-bonds synthons
Topić, Filip; Lisac, Katarina; Arhangelskis, Mihails; Rissanen, Kari; Cinčić, Dominik; Friščić, Tomislav; Chemical Communications  (2019) –; doi:10.1039/C9CC06735C

data_7124401
_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 \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f scans + \w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0178P)^2^+0.4440P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.566
_shelx_estimated_absorpt_t_max   0.815
_shelx_res_checksum              47006