Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes.
Wang, Gaonan; You, Xu; Gan, Yi; Liu, Yuanhong; Organic letters 19 (2017) 110–113; doi:10.1021/acs.orglett.6b03385

data_1545222
_publ_section_title
;
 Synthesis of \d- and \a-Carbolines via Nickel-Catalyzed [2 + 2 + 2]
 Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              110
_journal_page_last               113
_journal_paper_doi               10.1021/acs.orglett.6b03385
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H26 N2 O2 S'
_chemical_formula_weight         454.57
_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   geom
_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                   10.818(3)
_cell_length_b                   14.183(4)
_cell_length_c                   15.569(4)
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.517
_cell_measurement_theta_min      4.585
_cell_volume                     2388.8(11)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13806
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.942
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3747
_reflns_number_total             4445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03385_si_005.cif
_cod_data_source_block           cd16724
_cod_original_cell_volume        2388.6(12)
_cod_database_code               1545222
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
_shelx_res_checksum              50083
_shelx_hkl_checksum              1464