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_1570188
_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, 2.5(C6 F4 I2)'
_chemical_formula_sum            'C33 H12 F10 I5'
_chemical_formula_weight         1232.93
_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_creation_date             2023-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-13 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                94.961(6)
_cell_angle_beta                 93.811(6)
_cell_angle_gamma                97.532(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1683(5)
_cell_length_b                   15.3618(13)
_cell_length_c                   18.5460(13)
_cell_measurement_reflns_used    2904
_cell_measurement_temperature    291.9(4)
_cell_measurement_theta_max      71.7970
_cell_measurement_theta_min      3.8720
_cell_volume                     1730.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -111.00 -74.00   1.00    1.79    --  -41.27-140.00 134.00   37
  2  \w    -59.00 -33.00   1.00    1.79    --  -41.27 140.00-166.00   26
  3  \w    -80.00 -38.00   1.00    1.79    --  -41.27 130.00  19.00   42
  4  \w     65.00  90.00   1.00    1.79    --   41.27-130.00 -52.00   25
  5  \w     46.00  71.00   1.00    1.79    --   41.27-140.00 134.00   25
  6  \w     61.00 124.00   1.00    7.16    --  102.80-140.00 134.00   63
  7  \w     61.00 111.00   1.00    7.16    --  102.80-130.00 -52.00   50
  8  \w     91.00 120.00   1.00    7.16    --  102.80 140.00-166.00   29
  9  \w    110.00 136.00   1.00    7.16    --  102.80 130.00  19.00   26
 10  \w   -120.00   0.00   1.00    1.79    --  -41.27 -19.00  90.00  120
 11  \w   -109.00 -18.00   1.00    1.79    --  -41.27 -38.00   0.00   91
 12  \w     28.00  89.00   1.00    1.79    --   41.27-125.00 -30.00   61
 13  \w     45.00 114.00   1.00    7.16    --  102.80 -45.00 -90.00   69
 14  \w    103.00 163.00   1.00    7.16    --  102.80  77.00  30.00   60
 15  \w    106.00 177.00   1.00    7.16    --  102.80  77.00-120.00   71
 16  \w     39.00  74.00   1.00    7.16    --  102.80-111.00-150.00   35
 17  \w     64.00 103.00   1.00    7.16    --  102.80 -94.00 -30.00   39
 18  \w    116.00 176.00   1.00    7.16    --  102.80 111.00 -30.00   60
 19  \w     81.00 106.00   1.00    7.16    --  102.80-111.00-150.00   25
 20  \w    103.00 136.00   1.00    7.16    --  102.80  77.00   0.00   33
 21  \w    145.00 173.00   1.00    7.16    --  102.80  77.00   0.00   28
 22  \w     40.00  65.00   1.00    7.16    --  102.80 -77.00  30.00   25
 23  \w    104.00 174.00   1.00    7.16    --  102.80 111.00  60.00   70
 24  \w    115.00 167.00   1.00    7.16    --  102.80 111.00 -90.00   52
 25  \w     59.00 108.00   1.00    7.16    --  102.80-111.00 150.00   49
 26  \w     93.00 168.00   1.00    7.16    --  102.80  30.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713471000
_diffrn_orient_matrix_UB_12      -0.0071477000
_diffrn_orient_matrix_UB_13      0.0802252000
_diffrn_orient_matrix_UB_21      0.1458550000
_diffrn_orient_matrix_UB_22      -0.0698352000
_diffrn_orient_matrix_UB_23      -0.0234190000
_diffrn_orient_matrix_UB_31      0.1936506000
_diffrn_orient_matrix_UB_32      0.0734885000
_diffrn_orient_matrix_UB_33      -0.0033208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14023
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.640
_diffrn_reflns_theta_min         3.951
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    36.001
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    2.366
_exptl_crystal_description       lath
_exptl_crystal_F_000             1130
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.130
_refine_diff_density_min         -1.635
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6690
_refine_ls_number_restraints     348
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0750
_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^)+(0.1183P)^2^+2.5413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3422
_reflns_number_total             6690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           benzanthra_14tfib_auto_gaussian
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570188
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.221
_shelx_estimated_absorpt_t_min   0.064
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1A(H1A), C7A(H7A), C14A(H14A), C2A(H2A), C4A(H4A), C5A(H5A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C17A(H17A), C18A(H18A)
3.b Fitted hexagon refined as free rotating group:
 C15A(C6A,C7A,C8A,C13A,C14A)
;
_shelx_res_checksum              44137
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.854
_oxdiff_exptl_absorpt_empirical_full_min 0.570