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_4035557
_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            'C24 H17 Br2 N O2'
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
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_cell_angle_alpha                90
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_cell_length_b                   15.224(2)
_cell_length_c                   10.0932(15)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.49
_cell_volume                     1995.9(5)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
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_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
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_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.592
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_exptl_absorpt_coefficient_mu    4.082
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
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_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.101
_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     262
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
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_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^)+(0.0911P)^2^+1.6833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1709
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_reflns_number_gt                2982
_reflns_number_total             4533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01120_si_002.cif
_cod_data_source_block           180108a
_cod_original_cell_volume        1996.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035557
_shelx_estimated_absorpt_t_min   0.496
_shelx_estimated_absorpt_t_max   0.580
_shelxl_version_number           2014-3
_shelx_res_checksum              7823
_shelx_hkl_checksum              22635