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_1570181
_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         '3(C6 F4 I2), C48 H20'
_chemical_formula_sum            'C66 H20 F12 I6'
_chemical_formula_weight         1802.22
_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
_audit_creation_date             2023-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-29 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                72.718(3)
_cell_angle_beta                 87.214(3)
_cell_angle_gamma                81.882(3)
_cell_formula_units_Z            1
_cell_length_a                   5.1812(2)
_cell_length_b                   15.4603(5)
_cell_length_c                   17.4682(6)
_cell_measurement_reflns_used    4702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.6880
_cell_measurement_theta_min      1.5040
_cell_volume                     1322.66(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_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_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f      0.00 180.00   0.20    0.20   0.00   0.00   0.00    --   900
  2  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00   0.00  850
  3  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 120.00  850
  4  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 240.00  850
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0229264000
_diffrn_orient_matrix_UB_12      -0.0327513000
_diffrn_orient_matrix_UB_13      0.0364424000
_diffrn_orient_matrix_UB_21      -0.0413199000
_diffrn_orient_matrix_UB_22      0.0323407000
_diffrn_orient_matrix_UB_23      0.0194313000
_diffrn_orient_matrix_UB_31      -0.1257239000
_diffrn_orient_matrix_UB_32      -0.0099153000
_diffrn_orient_matrix_UB_33      0.0005702000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15312
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.513
_diffrn_reflns_theta_min         1.511
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    3.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.114a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.263
_exptl_crystal_density_meas      ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             842
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.441
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     443
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0700P)^2^+4.8563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3602
_reflns_number_total             4751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           2021ncs0398_ljm1a
_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_database_code               1570181
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C66 H20 I6 F12'
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.52
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F4B, C6B, C1A, I1A, C1A, I2A, C1B, I1B, C1B, I2B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4B, I3B, C4B, I4B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. 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
4. Others
 Fixed Sof: C5B(0.7) C6B(0.7) I1A(0.9) F2B(0.7) I2B(0.7) F3B(0.49) I3B(0.7)
 F4B(0.49) C5(0.3) C6(0.3) I2A(0.1) I1B(0.3) I4B(0.3) F5B(0.3) F6B(0.51)
 F7B(0.51)
5.a Aromatic/amide H refined with riding coordinates:
 C4C(H4C), C5C(H5C), C7C(H7C), C8C(H8C), C12C(H12C), C13C(H13C), C15C(H15C),
 C16C(H16C), C20C(H20C), C24C(H24C)
;
_shelx_res_checksum              90001
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.069
_oxdiff_exptl_absorpt_empirical_full_min 0.409