Synthesis of Oxazocenones via Gold(I)-Catalyzed 8-Endo-Dig Hydroalkoxylation of Alkynamides.
Scully, Stephen S.; Zheng, Shao-Liang; Wagner, Bridget K.; Schreiber, Stuart L.; Organic letters 17 (2015) 418–421; doi:10.1021/ol503273v

data_1518568
_publ_section_title
;
 Synthesis of Oxazocenones via Gold(I)-Catalyzed 8-Endo-Dig
 Hydroalkoxylation of Alkynamides.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              418
_journal_page_last               421
_journal_paper_doi               10.1021/ol503273v
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H37 N5 O8 S'
_chemical_formula_weight         639.71
_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   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 100.907(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9519(5)
_cell_length_b                   18.6953(7)
_cell_length_c                   14.8640(6)
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      3.02
_cell_volume                     2988.4(2)
_computing_cell_refinement       'SAINT 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9443
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.755
_diffrn_reflns_theta_min         3.028
_exptl_absorpt_coefficient_mu    1.483
_exptl_absorpt_correction_T_max  0.752819
_exptl_absorpt_correction_T_min  0.442811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 3038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         9443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+2.5520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.774
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                8410
_reflns_number_total             9443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503273v_si_004.cif
_cod_data_source_block           SSS-1-73c
_cod_depositor_comments
'Adding full bibliography for 1518568--1518572.cif.'
_cod_database_code               1518568
_shelx_estimated_absorpt_t_min   0.648
_shelx_estimated_absorpt_t_max   0.916
_shelxl_version_number           2014-3
_shelx_res_checksum              64518
_shelx_hkl_checksum              25084