Selective [5 + 1] and [5 + 2] Cycloaddition of Ynamides or Propargyl Esters with Benzo[ d]isoxazoles via Gold Catalysis.
Xu, Wei; Zhao, Jidong; Li, Xiangdong; Liu, Yuanhong; The Journal of organic chemistry 83 (2018) 15470–15485; doi:10.1021/acs.joc.8b02935

data_4034749
_publ_section_title
;
 Selective [5 + 1] and [5 + 2] Cycloaddition of Ynamides or Propargyl
 Esters with Benzo[ d]isoxazoles via Gold Catalysis.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15470
_journal_page_last               15485
_journal_paper_doi               10.1021/acs.joc.8b02935
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H26 N2 O3 S'
_chemical_formula_weight         494.59
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                71.037(6)
_cell_angle_beta                 72.442(6)
_cell_angle_gamma                68.706(6)
_cell_formula_units_Z            1
_cell_length_a                   7.5699(15)
_cell_length_b                   8.2998(15)
_cell_length_c                   11.079(2)
_cell_measurement_reflns_used    3484
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      53.583
_cell_measurement_theta_min      5.430
_cell_volume                     599.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9431
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.715
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
; 
 Flack x determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(7)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1111P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1900
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                3357
_reflns_number_total             4210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02935_si_006.cif
_cod_data_source_block           mo_d8v18466_0m
_cod_database_code               4034749
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
_shelx_res_checksum              1189
_shelx_hkl_checksum              54606