Cleavage of a carbon-carbon triple bond via gold-catalyzed cascade cyclization/oxidative cleavage reactions of (Z)-enynols with molecular oxygen.
Liu, Yuanhong; Song, Feijie; Guo, Shenghai; Journal of the American Chemical Society 128 (2006) 11332–11333; doi:10.1021/ja062610q

data_4101571
_publ_section_title
;
 Cleavage of a carbon-carbon triple bond via gold-catalyzed cascade
 cyclization/oxidative cleavage reactions of (Z)-enynols with molecular
 oxygen.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11332
_journal_page_last               11333
_journal_paper_doi               10.1021/ja062610q
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C23 H17 Cl O2'
_chemical_formula_weight         360.82
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.28(3)
_cell_angle_beta                 96.25(4)
_cell_angle_gamma                91.27(4)
_cell_formula_units_Z            4
_cell_length_a                   10.232(19)
_cell_length_b                   14.05(3)
_cell_length_c                   14.11(3)
_cell_measurement_reflns_used    1576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.085
_cell_measurement_theta_min      4.728
_cell_volume                     1932(6)
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.1495
_diffrn_reflns_av_sigmaI/netI    0.1928
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11296
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74317
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.235
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0063(13)
_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   0.764
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         8063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.764
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                3038
_reflns_number_total             8063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062610qsi20060414_010437.cif
_cod_data_source_block           cd25347
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4101571