Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines.
Dong, Shanliang; Huang, Jingjing; Sha, Hongkai; Qiu, Lihua; Hu, Wenhao; Xu, Xinfang; Organic & biomolecular chemistry 18 (2020) 1926–1932; doi:10.1039/d0ob00222d

data_7157357
_publ_section_title
;
 Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered
 diazoacetates and pyridines: access to polycyclic indolizines.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1926
_journal_page_last               1932
_journal_paper_doi               10.1039/d0ob00222d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-09 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.097(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4156(5)
_cell_length_b                   14.0062(6)
_cell_length_c                   11.1540(6)
_cell_measurement_reflns_used    6771
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.38
_cell_volume                     1426.66(12)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23104
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.663
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0237P)^2^+0.9819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2589
_reflns_number_total             3268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00222d2.cif
_cod_data_source_block           DSL190107C
_cod_depositor_comments
'Adding full bibliography for 7157357--7157358.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157357
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              8238