Gold-Catalyzed Benzannulation of 5-Hydroxy-3-oxoalk-6-ynoate Esters to o-Phenolic Esters.
Teo, Wan Teng; Rao, Weidong; Ng, Charmaine Jia Huan; Koh, Shaun Wei Yong; Chan, Philip Wai Hong; Organic letters 16 (2014) 1248–1251; doi:10.1021/ol5002363

data_1513437
_publ_section_title
;
 Gold-Catalyzed Benzannulation of 5-Hydroxy-3-oxoalk-6-ynoate Esters to
 o-Phenolic Esters.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1248
_journal_page_last               1251
_journal_paper_doi               10.1021/ol5002363
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C21 H18 O3'
_chemical_formula_weight         318.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                115.1446(11)
_cell_angle_beta                 98.6848(12)
_cell_angle_gamma                96.7865(12)
_cell_formula_units_Z            2
_cell_length_a                   8.9589(3)
_cell_length_b                   9.9488(4)
_cell_length_c                   10.2552(4)
_cell_measurement_reflns_used    6340
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      28.3127
_cell_measurement_theta_min      2.3099
_cell_volume                     800.79(5)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13044
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.2515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                3446
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5002363_si_002.cif
_cod_data_source_block           I
_cod_database_code               1513437
_shelx_res_checksum              32639
_shelx_hkl_checksum              53102