Halogen bonding to the azulene π-system: cocrystal design of pleochroism.
Vainauskas, Jogirdas; Topić, Filip; Bushuyev, Oleksandr S.; Barrett, Christoper J.; Friščić, Tomislav; Chemical communications (Cambridge, England) 56 (2020) 15145–15148; doi:10.1039/d0cc04758a

data_7127504
_publ_section_title
;
 Halogen bonding to the azulene \p-system: cocrystal design of
 pleochroism.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15145
_journal_page_last               15148
_journal_paper_doi               10.1039/d0cc04758a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '3(C6 F4 I2), 2(C10 H8)'
_chemical_formula_sum            'C38 H16 F12 I6'
_chemical_formula_weight         1461.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-03 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                73.9545(12)
_cell_angle_beta                 80.1893(13)
_cell_angle_gamma                84.8797(12)
_cell_formula_units_Z            1
_cell_length_a                   5.9321(6)
_cell_length_b                   11.9878(13)
_cell_length_c                   14.8586(16)
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.56
_cell_volume                     999.63(18)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 CCD
_diffrn_detector_type            APEX-II
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-DUO, Dual, APEX-II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9931
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.861
_diffrn_reflns_theta_min         1.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_exptl_absorpt_coefficient_mu    4.746
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.2839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    2.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             670
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol/chlorofom'
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.894
_refine_diff_density_min         -1.083
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0283P)^2^+0.4982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3970
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04758a2.cif
_cod_data_source_block           azu_14tfib_2-3_150K
_cod_database_code               7127504
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.186
_shelx_estimated_absorpt_t_max   0.797
_shelx_res_checksum              95006