Gold-catalyzed oxidative cycloalkenations of alkynes with quinoline N-oxides
Wagh, Sachin Bhausaheb; Sharma, Pankaj; Patil, Manoj D.; Liu, Rai-Shung; Organic Chemistry Frontiers 6 (2019) 226–; doi:10.1039/C8QO01175C

data_1554533
_publ_section_title
;
 Gold-catalyzed oxidative cycloalkenations of alkynes with quinoline
 N-oxides
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              226
_journal_paper_doi               10.1039/C8QO01175C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-13 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.222(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.0827(15)
_cell_length_b                   8.2829(6)
_cell_length_c                   8.2169(4)
_cell_measurement_reflns_used    6280
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.599
_cell_measurement_theta_min      2.645
_cell_volume                     1428.93(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16223
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_extinction_coef       0.052(5)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4764
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0399P)^2^+0.2051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                3974
_reflns_number_total             4764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo01175c2.cif
_cod_data_source_block           d19251
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               1554533