Synthesis and metalation of polycatechol nanohoops derived from fluorocycloparaphenylenes.
Kamin, Ashlyn A.; Clayton, Tara D.; Otteson, Claire E.; Gannon, Paige M.; Krajewski, Sebastian; Kaminsky, Werner; Jasti, Ramesh; Xiao, Dianne J.; Chemical science 14 (2023) 9724–9732; doi:10.1039/d3sc03561a

data_1569830
_publ_section_title
;
 Synthesis and metalation of polycatechol nanohoops derived from
 fluorocycloparaphenylenes.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              9724
_journal_page_last               9732
_journal_paper_doi               10.1039/d3sc03561a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C72 H44 F4 [+solvent]'
_chemical_formula_sum            'C72 H44 F4'
_chemical_formula_weight         985.07
_chemical_name_systematic        tetrafluoro[12]cycloparaphenylene
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-07-06T15:54:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-07-07 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.289(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.7037(19)
_cell_length_b                   8.3789(8)
_cell_length_c                   21.004(2)
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.66
_cell_measurement_wavelength     0.7288
_cell_volume                     3292.5(5)
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6324
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         27.106
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'ALS-U Lawrence Berkeley National Laboratory'
_diffrn_source_type              'ALS-U Beamline 12.2.1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.994
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: trichloroethylene/n-heptane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6324
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1591P)^2^+1.1411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.224
_reflns_Friedel_coverage         0
_reflns_number_gt                5358
_reflns_number_total             6324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03561a2.cif
_cod_data_source_block           TC_252_TCE_hept_synchrotron_data
_cod_depositor_comments
'Adding full bibliography for 1569828--1569831.cif.'
_cod_original_cell_volume        3292.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1569830
_shelx_estimated_absorpt_t_min   0.98
_shelx_estimated_absorpt_t_max   0.997
_shelx_shelxl_version_number     2019/3
_shelx_fab_checksum              55344
_shelx_res_checksum              82946