Copper-catalysed perarylation of cyclopentadiene: synthesis of hexaarylcyclopentadienes.
Gisbert, Yohan; Simón Marqués, Pablo; Baccini, Caterina; Abid, Seifallah; Saffon-Merceron, Nathalie; Rapenne, Gwénaël; Kammerer, Claire; Chemical science 15 (2024) 9127–9137; doi:10.1039/d4sc02458c

data_1571638
_publ_section_title
;
 Copper-catalysed perarylation of cyclopentadiene: synthesis of
 hexaarylcyclopentadienes.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              9127
_journal_page_last               9137
_journal_paper_doi               10.1039/d4sc02458c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C65 H78'
_chemical_formula_weight         859.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-13 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.818(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   13.3024(8)
_cell_length_c                   21.865(2)
_cell_measurement_reflns_used    9182
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      3.01
_cell_volume                     5574.3(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8-Venture Photon III-C14 detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            152698
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.558
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.024
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.260
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_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         8531
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_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0865P)^2^+2.5811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6367
_reflns_number_total             8531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02458c2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 1571637--1571645.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1571638
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.988
_exptl_absorpt_special_details
;
SADABS-2016/2 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_shelx_res_checksum              82651