Copper(I) Catalyzed Synthesis of Functionalized Indolizinones from Substituted Pyridine Homologated Ynones.
Sahoo, Sushree Ranjan; Sarkar, Debayan; Henkel, Felix; Reuter, Hans; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02853

data_4037755
_publ_section_title
;
 Copper(I) Catalyzed Synthesis of Functionalized Indolizinones from
 Substituted Pyridine Homologated Ynones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02853
_journal_year                    2019
_chemical_formula_sum            'C31 H20 Cl N O Se2'
_chemical_formula_weight         615.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.726(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9756(5)
_cell_length_b                   11.2230(4)
_cell_length_c                   16.6743(6)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.25
_cell_volume                     2584.89(16)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            190895
_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         28.000
_diffrn_reflns_theta_min         2.338
_exptl_absorpt_coefficient_mu    2.990
_exptl_absorpt_correction_T_max  0.684
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       bloc
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+1.4332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5430
_reflns_number_total             6243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02853_si_002.cif
_cod_data_source_block           HF2019_7_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037755
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.324
_shelx_estimated_absorpt_t_max   0.750
_shelx_res_checksum              82398
_shelx_hkl_checksum              10517