Gold-Catalyzed Cyclization of 3-(2'-Azidoaryl)-1-arylpropargyl Carbonates or 3-Aryl-1-(2'-azidoaryl)propargyl Carbonates to Produce Quinolines
Shugao Zhu; Luling Wu; Xian Huang; Journal of Organic Chemistry 78 (2013) 9120–9126; doi:10.1021/jo401324k

data_4028598
_publ_section_title
;
 Gold-Catalyzed Cyclization of 3-(2'-Azidoaryl)-1-arylpropargyl Carbonates
 or 3-Aryl-1-(2'-azidoaryl)propargyl Carbonates to Produce Quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9120
_journal_page_last               9126
_journal_paper_doi               10.1021/jo401324k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H10 F N O'
_chemical_formula_weight         239.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.215(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7400(5)
_cell_length_b                   7.1758(3)
_cell_length_c                   13.2748(7)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5226
_cell_measurement_theta_min      2.8329
_cell_volume                     1117.49(9)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4857
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.031(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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.2338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1738
_reflns_number_total             2047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401324k_si_003.cif
_cod_data_source_block           110712_zsg_110630
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028598