Gold-Catalyzed Benzannulation of 3-Alkoxy-1,5-enynes: Access to Functionalized Benzenes
Guijie Li; Yuanhong Liu; Journal of Organic Chemistry 75 (2010) 2903–2909; doi:10.1021/jo100137j

data_4025388
_publ_section_title
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 Gold-Catalyzed Benzannulation of 3-Alkoxy-1,5-enynes: Access to
 Functionalized Benzenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2903
_journal_page_last               2909
_journal_paper_doi               10.1021/jo100137j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C22 H27 O'
_chemical_formula_weight         307.44
_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                 93.435(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.292(3)
_cell_length_b                   6.2213(14)
_cell_length_c                   18.490(4)
_cell_measurement_reflns_used    849
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.174
_cell_measurement_theta_min      5.337
_cell_volume                     1755.9(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0904
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8763
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68268
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0051(18)
_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   0.780
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                1294
_reflns_number_total             3254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100137j_si_002.cif
_cod_data_source_block           cd29532
_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_original_cell_volume        1755.9(7)
_cod_database_code               4025388