A remarkably strained cyclopyrenylene trimer that undergoes metal-free direct oxygen insertion into the biaryl C‒C σ-bond
Kurosaki, Ryo; Hayashi, Hironobu; Suzuki, Mitsuhara; Jiang, Julong; Hatanaka, Miho; Aratani, Naoki; Yamada, Hiroko; Chemical Science  (2019) –; doi:10.1039/C9SC01777A

data_1551383
_publ_section_title
;
 A remarkably strained cyclopyrenylene trimer that undergoes metal-free
 direct oxygen insertion into the biaryl C--C \s-bond
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01777A
_journal_year                    2019
_chemical_formula_moiety         'C66 H60 O7, 0.51(C O), 0.39(C H2 Cl2)'
_chemical_formula_sum            'C66.91 H60.78 Cl0.78 O7.51'
_chemical_formula_weight         1012.83
_chemical_name_systematic        CP3O
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-02 deposited with the CCDC.    2019-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                109.8071(19)
_cell_angle_beta                 114.3435(19)
_cell_angle_gamma                91.189(2)
_cell_formula_units_Z            4
_cell_length_a                   17.7176(19)
_cell_length_b                   18.088(2)
_cell_length_c                   18.855(2)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    90
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      2.28
_cell_volume                     5088.1(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26337
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.462
_diffrn_reflns_theta_max         24.462
_diffrn_reflns_theta_min         1.392
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prism
_exptl_crystal_F_000             2143
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1514
_refine_ls_number_reflns         16673
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1777
_refine_ls_R_factor_gt           0.0829
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1223P)^2^+3.2125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7875
_reflns_number_total             16673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01777a2.cif
_cod_data_source_block           90215RK_0m
_cod_original_cell_volume        5088.2(10)
_cod_database_code               1551383
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              67903