Copper-catalyzed cascade cyclization reaction of 3-aminocyclobutenones with electron-deficient internal alkynes: synthesis of fully substituted indoles.
Yu, Yang; Wang, Xin-Yu; Peng, Ju-Yin; Liu, Tao; Zhao, Yu-Long; Chemical communications (Cambridge, England) 56 (2020) 9815–9818; doi:10.1039/d0cc00512f

data_7126951
_publ_section_title
;
 Copper-catalyzed cascade cyclization reaction of 3-aminocyclobutenones
 with electron-deficient internal alkynes: synthesis of fully substituted
 indoles.
;
_journal_issue                   68
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9815
_journal_page_last               9818
_journal_paper_doi               10.1039/d0cc00512f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C25 H25 N O8'
_chemical_formula_weight         467.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-11-26 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   11.712(2)
_cell_length_b                   11.717(2)
_cell_length_c                   17.423(3)
_cell_measurement_reflns_used    9041
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      63.63
_cell_measurement_theta_min      3.77
_cell_volume                     2390.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12417
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.797
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_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.929
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
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_refine_ls_abs_structure_details
;
 Flack x determined using 1459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_coef       0.0082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3806
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0368P)^2^+0.2351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3391
_reflns_number_total             3806
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           zhaoyl191120_1_0m
_cod_depositor_comments          'Adding full bibliography for 7126951.cif.'
_cod_original_cell_volume        2390.9(8)
_cod_database_code               7126951
_shelxl_version_number           2014-3
_shelx_res_checksum              80078
_shelx_hkl_checksum              23361