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_1569828
_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         'C84 H72 O12, 2(C3 H6 O)'
_chemical_formula_sum            'C90 H84 O14'
_chemical_formula_weight         1389.57
_chemical_name_common            dodecamethoxy[12]cycloparaphenylene
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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             2023-04-18T14:43:42-00:00
_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                 104.097(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.514(3)
_cell_length_b                   9.4966(13)
_cell_length_c                   39.416(6)
_cell_measurement_reflns_used    9311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.59
_cell_measurement_wavelength     0.7288
_cell_volume                     7447.5(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            25207
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        25.709
_diffrn_reflns_theta_max         25.709
_diffrn_reflns_theta_min         2.456
_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    0.086
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             2944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone/MeOH'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0276(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     969
_refine_ls_number_reflns         13026
_refine_ls_number_restraints     639
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1274
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2752
_refine_ls_wR_factor_ref         0.282
_reflns_Friedel_coverage         0
_reflns_number_gt                10055
_reflns_number_total             13026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03561a2.cif
_cod_data_source_block           aak_4101_acetone_sync
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569828--1569831.cif.
;
_cod_original_cell_volume        7447.4(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569828
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.991
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              22437