Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring Expansion of Alkynyl Quinols.
Zhao, Jidong; Liu, Jun; Xie, Xin; Li, Shi; Liu, Yuanhong; Organic letters 17 (2015) 5926–5929; doi:10.1021/acs.orglett.5b03160

data_1555465
_publ_section_title
;
 Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring
 Expansion of Alkynyl Quinols.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5926
_journal_page_last               5929
_journal_paper_doi               10.1021/acs.orglett.5b03160
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H14 O4'
_chemical_formula_weight         330.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2786(15)
_cell_length_b                   23.641(4)
_cell_length_c                   7.5289(11)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.022
_cell_measurement_theta_min      4.716
_cell_volume                     1651.5(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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9514
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.723
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
; 
 Flack x determined using 762 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0498P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2173
_reflns_number_total             3146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03160_si_004.cif
_cod_data_source_block           cd15149
_cod_original_cell_volume        1651.5(4)
_cod_database_code               1555465
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              34084
_shelx_hkl_checksum              55779