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_1545223
_publ_section_title
;
 Synthesis of \d- and \a-Carbolines via Nickel-Catalyzed [2 + 2 + 2]
 Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes.
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_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_formula_sum            'C32 H30 N2 O2 S'
_chemical_formula_weight         506.64
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
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_symmetry_space_group_name_Hall  '-P 2yn'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_max 0.998
_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  0.0603
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_point_group_measured_fraction_full 0.998
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_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7456
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_description       prismatic
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_number_reflns         5119
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0959
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_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1049P)^2^+0.6882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             5119
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_original_cell_volume        2760.3(6)
_cod_database_code               1545223
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
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