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_4035558
_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            'C19 H15 Br Cl N O2'
_chemical_formula_weight         404.68
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 116.170(8)
_cell_angle_gamma                90
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_cell_length_b                   6.319(2)
_cell_length_c                   19.015(6)
_cell_measurement_reflns_used    1940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.83
_cell_volume                     3377.2(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.996
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
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_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
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_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.100
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_refine_ls_extinction_method     none
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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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2110
_reflns_number_total             3150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01120_si_004.cif
_cod_data_source_block           4i
_cod_original_cell_volume        3377(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035558
_shelx_estimated_absorpt_t_min   0.745
_shelx_estimated_absorpt_t_max   0.781
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_shelx_res_checksum              2232
_shelx_hkl_checksum              15588