Synthesis of Functionalized Indolizines via Gold(I)-Catalyzed Intramolecular Hydroarylation/aromatization of Pyrrole-Ynes
Li, Xiangdong; Zhao, JiDong; Xie, Xin; Liu, Yuanhong; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02102J

data_7155865
_publ_section_title
;
 Synthesis of Functionalized Indolizines via Gold(I)-Catalyzed
 Intramolecular Hydroarylation/aromatization of Pyrrole-Ynes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02102J
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C31 H25 N O3'
_chemical_formula_weight         459.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-08-23 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.213(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.427(3)
_cell_length_b                   7.3463(11)
_cell_length_c                   18.485(3)
_cell_measurement_reflns_used    1550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.014
_cell_measurement_theta_min      4.425
_cell_volume                     2356.7(7)
_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 0.972
_diffrn_measured_fraction_theta_max 0.999
_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  0.0512
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13092
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.684
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
; 
 Flack x determined using 1595 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -5.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         8095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.1221
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1818P)^2^+0.4412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2902
_refine_ls_wR_factor_ref         0.3208
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                5581
_reflns_number_total             8095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02102j2.cif
_cod_data_source_block           cd17353
_cod_original_cell_volume        2356.8(6)
_cod_database_code               7155865
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
_shelx_res_checksum              26353