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_1569831
_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_absolute_configuration unk
_chemical_formula_moiety         'C76 H56 O4, C2 H Cl3 [+ solvent]'
_chemical_formula_sum            'C78 H57 Cl3 O4'
_chemical_formula_weight         1164.58
_chemical_name_common            tetramethoxy[12]cycloparaphenylene
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      43
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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             2023-04-17T15:09:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   57.683(4)
_cell_length_b                   12.1111(8)
_cell_length_c                   50.915(3)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.47
_cell_measurement_wavelength     0.71073
_cell_volume                     35569(4)
_computing_cell_refinement       'SAINT V8.38A 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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.08256
_diffrn_orient_matrix_UB_12      -0.00011
_diffrn_orient_matrix_UB_13      -0.000232
_diffrn_orient_matrix_UB_21      0.001018
_diffrn_orient_matrix_UB_22      -0.003096
_diffrn_orient_matrix_UB_23      0.017118
_diffrn_orient_matrix_UB_31      -0.000632
_diffrn_orient_matrix_UB_32      -0.019395
_diffrn_orient_matrix_UB_33      -0.002731
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_unetI/netI     0.09
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       68
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            101139
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.027
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.87
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             9728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: trichloroethylene/n-heptane'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     786
_refine_ls_number_reflns         15535
_refine_ls_number_restraints     1003
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.18
_refine_ls_R_factor_gt           0.1202
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1793P)^2^+212.6177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3064
_refine_ls_wR_factor_ref         0.3545
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                9099
_reflns_number_total             15535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03561a2.cif
_cod_data_source_block           AAK_4245_4_TCE_hept
_cod_depositor_comments
'Adding full bibliography for 1569828--1569831.cif.'
_cod_database_code               1569831
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.988
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              23477
_shelx_fab_checksum              40176