Halogen bonding with carbon: directional assembly of non-derivatised aromatic carbon systems into robust supramolecular ladder architectures.
Vainauskas, Jogirdas; Borchers, Tristan H.; Arhangelskis, Mihails; McCormick McPherson, Laura J; Spilfogel, Toni S.; Hamzehpoor, Ehsan; Topić, Filip; Coles, Simon J.; Perepichka, Dmytro F.; Barrett, Christopher J.; Friščić, Tomislav; Chemical science 14 (2023) 13031–13041; doi:10.1039/d3sc04191c

data_1570186
_publ_section_title
;
 Halogen bonding with carbon: directional assembly of non-derivatised
 aromatic carbon systems into robust supramolecular ladder architectures.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13031
_journal_page_last               13041
_journal_paper_doi               10.1039/d3sc04191c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C18 H12, C6 F4 I2'
_chemical_formula_sum            'C24 H12 F4 I2'
_chemical_formula_weight         630.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.617(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.1824(19)
_cell_length_b                   5.9202(7)
_cell_length_c                   8.9814(9)
_cell_measurement_reflns_used    5318
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.32
_cell_measurement_theta_min      2.30
_cell_volume                     1019.90(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.539
_diffrn_reflns_theta_min         2.303
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    24.621
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1577 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.8273.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_density_meas      ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             596
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2,4-trichlorobenzene'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.730
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.00090(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0131P)^2^+6.4952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1621
_reflns_number_total             2020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           sfulldata_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570178--1570188.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570186
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.110
_shelx_estimated_absorpt_t_max   0.417
_shelx_res_checksum              11268