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_1570185
_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         'C6 F4 I2, C6 H6'
_chemical_formula_sum            'C12 H6 F4 I2'
_chemical_formula_weight         479.97
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f63h8
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.233(7)
_cell_angle_beta                 90.118(7)
_cell_angle_gamma                100.763(8)
_cell_formula_units_Z            1
_cell_length_a                   5.6444(7)
_cell_length_b                   5.6487(7)
_cell_length_c                   10.5675(13)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.34
_cell_measurement_theta_min      4.18
_cell_volume                     331.00(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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      180
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3945
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.519
_diffrn_reflns_theta_min         4.183
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    37.606
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             219
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_refine_diff_density_max         4.273
_refine_diff_density_min         -2.400
_refine_diff_density_rms         0.519
_refine_ls_extinction_coef       0.029(5)
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1273
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0910
_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^)+(0.1847P)^2^+0.5300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1151
_reflns_number_total             1273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           s7_a
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570185
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C3B(H3B), C2B(H2B)
;
_shelx_res_checksum              38658
_olex2_submission_special_instructions 'No special instructions were received'