Gold(I)-Catalyzed Cascade Hydroarylation/Cycloaromatization to Indolizines via Pyridine Ring Construction.
Li, Xiangdong; Xie, Xin; Liu, Yuanhong; The Journal of organic chemistry 81 (2016) 3688–3699; doi:10.1021/acs.joc.6b00346

data_4036713
_publ_section_title
;
 Gold(I)-Catalyzed Cascade Hydroarylation/Cycloaromatization to
 Indolizines via Pyridine Ring Construction.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3688
_journal_page_last               3699
_journal_paper_doi               10.1021/acs.joc.6b00346
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C35 H29 N O3'
_chemical_formula_sum            'C35 H29 N O3'
_chemical_formula_weight         511.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                64.763(3)
_cell_angle_beta                 84.332(3)
_cell_angle_gamma                62.918(2)
_cell_formula_units_Z            2
_cell_length_a                   11.2211(14)
_cell_length_b                   12.2573(16)
_cell_length_c                   12.3317(17)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.443
_cell_measurement_theta_min      2.37
_cell_volume                     1356.4(3)
_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      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.609
_diffrn_reflns_theta_min         1.839
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0505 before and 0.0338 after correction.
The Ratio of minimum to maximum transmission is 0.8995.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0563P)^2^+0.1549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3625
_reflns_number_total             6246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00346_si_005.cif
_cod_data_source_block           mo_dm15942_0m
_cod_database_code               4036713
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              35320
_shelx_hkl_checksum              9834
_olex2_submission_special_instructions 'No special instructions were received'