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_4513927
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1807(16)
_cell_length_b                   13.199(3)
_cell_length_c                   19.659(4)
_cell_measurement_reflns_used    3851
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      54.190
_cell_measurement_theta_min      5.163
_cell_volume                     1863.2(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0573
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.072
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0404P)^2^+0.3876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3328
_reflns_number_total             3656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01596_si_003.cif
_cod_data_source_block           mo_dm15302_0m
_cod_depositor_comments
'Adding full bibliography for 4513926--4513927.cif.'
_cod_original_cell_volume        1863.1(7)
_cod_database_code               4513927
_shelxl_version_number           2013-4
_shelx_res_checksum              9940
_shelx_hkl_checksum              46098