Cu(I)-Catalyzed Chemoselective and Stereoselective [3 + 3] Cycloaddition of Azomethine Ylides with 2-Indolylnitroethylenes: Facile Access to Highly Substituted Tetrahydro-γ-Carbolines
Yang, Wu-Lin; Li, Chun-Yan; Qin, Wen-Jing; Tang, Fei-Fei; Yu, Xingxin; Deng, Wei-Ping; ACS Catalysis 6 (2016) 5685–; doi:10.1021/acscatal.6b01596

data_4513926
_publ_section_title
;
 Cu(I)-Catalyzed Chemoselective and Stereoselective [3 + 3] Cycloaddition
 of Azomethine Ylides with 2-Indolylnitroethylenes: Facile Access to
 Highly Substituted Tetrahydro-\g-Carbolines
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              5685
_journal_paper_doi               10.1021/acscatal.6b01596
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H20 Cl N3 O4'
_chemical_formula_weight         413.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.770(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.480(4)
_cell_length_b                   5.679(2)
_cell_length_c                   19.061(7)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.636
_cell_measurement_theta_min      5.236
_cell_volume                     1008.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5532
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.175
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
; 
 Flack x determined using 691 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.15(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0855
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+1.4965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2099
_refine_ls_wR_factor_ref         0.2354
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                2305
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01596_si_002.cif
_cod_data_source_block           cd16418
_cod_depositor_comments
'Adding full bibliography for 4513926--4513927.cif.'
_cod_database_code               4513926
_shelxl_version_number           2013-4
_shelx_res_checksum              40077
_shelx_hkl_checksum              85697