Palladium-catalyzed highly efficient synthesis of functionalized indolizines via cross-coupling/cycloisomerization cascade
Liangwei Zhang; Xiangdong Li; Yuanhong Liu; Dayong Zhang; Chem.Commun. 51 (2015) 6633–; doi:10.1039/C5cc01151E

data_7116913
_publ_section_title
;
 Palladium-catalyzed highly efficient synthesis of functionalized
 indolizines via cross-coupling/cycloisomerization cascade
;
_journal_name_full               Chem.Commun.
_journal_page_first              6633
_journal_paper_doi               10.1039/C5cc01151E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C21 H32 N O2, Cl'
_chemical_formula_sum            'C21 H31 Cl N O2'
_chemical_formula_weight         364.92
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-02-05 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                94.479(5)
_cell_angle_beta                 93.887(6)
_cell_angle_gamma                100.786(6)
_cell_formula_units_Z            2
_cell_length_a                   7.085(2)
_cell_length_b                   12.661(4)
_cell_length_c                   12.767(4)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    130
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      2.19
_cell_volume                     1117.6(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.065
_diffrn_reflns_theta_min         1.606
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0789 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7605.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         6966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1135P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4046
_reflns_number_total             6966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01151e2-3.cif
_cod_data_source_block           mo_dm15042_0m
_cod_original_cell_volume        1117.5(5)
_cod_database_code               7116913
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              59810
_shelx_hkl_checksum              55161
_olex2_submission_special_instructions 'No special instructions were received'