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_7116910
_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_absolute_configuration unk
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-02-05 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.273(3)
_cell_length_b                   18.584(5)
_cell_length_c                   7.3811(18)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.692
_cell_measurement_theta_min      4.383
_cell_volume                     1820.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0851
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9074
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         1.885
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0566P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                2839
_reflns_number_total             3298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01151e2-3.cif
_cod_data_source_block           cd214722
_cod_database_code               7116910
_shelxl_version_number           2013-4
_shelx_res_checksum              29682
_shelx_hkl_checksum              95903