Gold-Catalyzed Intramolecular Indole/Alkyne Cyclization Cascades through a Heterolytic Fragmentation: 1,5-Indole Migration and Allenylation
Guijie Li; Yuanhong Liu; Journal of Organic Chemistry 75 (2010) 3526–3528; doi:10.1021/jo1005125

data_4025434
_publ_section_title
;
 Gold-Catalyzed Intramolecular Indole/Alkyne Cyclization Cascades through
 a Heterolytic Fragmentation: 1,5-Indole Migration and Allenylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3526
_journal_page_last               3528
_journal_paper_doi               10.1021/jo1005125
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C35 H29 N O2'
_chemical_formula_weight         495.59
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.799(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7594(10)
_cell_length_b                   18.7562(19)
_cell_length_c                   15.1482(16)
_cell_measurement_reflns_used    1288
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.721
_cell_measurement_theta_min      5.151
_cell_volume                     2692.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0734
_diffrn_reflns_av_sigmaI/netI    0.1147
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14123
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7778
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.169
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(3.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0221P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2187
_reflns_number_total             5004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1005125_si_003.cif
_cod_data_source_block           cd29308
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025434