Copper-Catalyzed Ring Expansion of Cyclopropyl Ketones/Formation of N-acyliminium/Hetero-[4 + 2]-Cycloaddition: A Route to Substituted Pentacyclic Isoindolin-1-one.
Li, Jian; Bai, Shuhua; Li, Yang; Wang, Zhengbing; Huo, Xiaoyu; Liu, Li; The Journal of organic chemistry 83 (2018) 8780–8785; doi:10.1021/acs.joc.8b01120

data_4035556
_publ_section_title
;
 Copper-Catalyzed Ring Expansion of Cyclopropyl Ketones/Formation of
 N-acyliminium/Hetero-[4 + 2]-Cycloaddition: A Route to Substituted
 Pentacyclic Isoindolin-1-one.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8780
_journal_page_last               8785
_journal_paper_doi               10.1021/acs.joc.8b01120
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C25 H20 Br N O2'
_chemical_formula_weight         446.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.845(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.333(2)
_cell_length_b                   15.334(2)
_cell_length_c                   10.1707(15)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.21
_cell_measurement_theta_min      2.47
_cell_volume                     2000.4(5)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13061
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.296
_diffrn_reflns_theta_min         1.588
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2968
_reflns_number_total             4446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01120_si_003.cif
_cod_data_source_block           180120a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035556
_shelx_estimated_absorpt_t_min   0.682
_shelx_estimated_absorpt_t_max   0.746
_shelxl_version_number           2014-3
_shelx_res_checksum              36724
_shelx_hkl_checksum              30707