Two-Component Domino Reactions Initiated from Ketenes: Serendipitous Synthesis of Quinolizidinones Analogous to Chelated Lobeline's Conformation.
Drège, Emmanuelle; Venot, Pierre-Etienne; Le Bideau, Franck; Retailleau, Pascal; Joseph, Delphine; The Journal of organic chemistry 80 (2015) 10119–10126; doi:10.1021/acs.joc.5b01727

data_4036363
_publ_section_title
;
 Two-Component Domino Reactions Initiated from Ketenes: Serendipitous
 Synthesis of Quinolizidinones Analogous to Chelated Lobeline's
 Conformation.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10119
_journal_page_last               10126
_journal_paper_doi               10.1021/acs.joc.5b01727
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C23 H24 Cl N O3'
_chemical_formula_sum            'C23 H24 Cl N O3'
_chemical_formula_weight         397.88
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.242(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.926(2)
_cell_length_b                   11.464(1)
_cell_length_c                   11.398(1)
_cell_measurement_reflns_used    4067
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      0.407
_cell_volume                     2017.0(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2012)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.008
_diffrn_reflns_theta_min         3.082
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'from a mixture of dcm and diethylether solution'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.4121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2931
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01727_si_001.cif
_cod_data_source_block           Compound_6f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036363
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              17990
_shelx_hkl_checksum              11260