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_7127507
_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         '2(C12 F8 I2 N2), 3(C10 H8)'
_chemical_formula_sum            'C54 H24 F16 I4 N4'
_chemical_formula_weight         1540.37
_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                71.556(4)
_cell_angle_beta                 89.199(3)
_cell_angle_gamma                83.434(4)
_cell_formula_units_Z            1
_cell_length_a                   6.0053(3)
_cell_length_b                   11.9473(5)
_cell_length_c                   18.8788(7)
_cell_measurement_reflns_used    4721
_cell_measurement_temperature    253.0(1)
_cell_measurement_theta_max      77.5740
_cell_measurement_theta_min      2.4560
_cell_volume                     1276.14(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253.0(1)
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15831
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         79.776
_diffrn_reflns_theta_min         2.468
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_exptl_absorpt_coefficient_mu    20.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.180
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     2126
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0604P)^2^+1.6616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3616
_reflns_number_total             5150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04758a2.cif
_cod_data_source_block           azu_ofiab_3-2_253K
_cod_database_code               7127507
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.129
_shelx_estimated_absorpt_t_max   0.584
_shelx_res_checksum              779