Gold-Catalyzed Cycloisomerization of 1,7-Diyne Benzoates to Indeno[1,2-c]azepines and Azabicyclo[4.2.0]octa-1(8),5-dines
Weidong Rao; Ming Joo Koh; Prasath Kothandaraman; Philip Wai Hong Chan; Journal of the American Chemical Society 134 (2012) 10811–10814; doi:10.1021/ja304964s

data_4118211
_publ_section_title
;
 Gold-Catalyzed Cycloisomerization of 1,7-Diyne Benzoates to
 Indeno[1,2-c]azepines and Azabicyclo[4.2.0]octa-1(8),5-dines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10811
_journal_page_last               10814
_journal_paper_doi               10.1021/ja304964s
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H33.5 N O4.25 S'
_chemical_formula_weight         628.24
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8294(5)
_cell_length_b                   14.2973(5)
_cell_length_c                   19.0353(7)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.48
_cell_volume                     3219.4(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40900
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9468
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1322
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.222
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         10234
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0997P)^2^+0.2280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                8903
_reflns_number_total             10234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja304964s_si_009.cif
_cod_data_source_block           chan208
_cod_original_formula_sum        'C40 H33.50 N O4.25 S'
_cod_database_code               4118211