Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio- and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through Cyclodimerization of 1-Ethynyl-2-propenyl Esters.
Zhao, Jidong; Yang, Shuang; Xie, Xin; Li, Xiangdong; Liu, Yuanhong; The Journal of organic chemistry 83 (2018) 1287–1297; doi:10.1021/acs.joc.7b02816

data_4033380
_publ_section_title
;
 Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio-
 and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through
 Cyclodimerization of 1-Ethynyl-2-propenyl Esters.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1287
_journal_page_last               1297
_journal_paper_doi               10.1021/acs.joc.7b02816
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H28 O4 S2'
_chemical_formula_weight         564.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 106.361(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9992(18)
_cell_length_b                   7.6753(11)
_cell_length_c                   14.812(2)
_cell_measurement_reflns_used    1661
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.241
_cell_measurement_theta_min      5.733
_cell_volume                     1418.0(3)
_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 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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8235
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.844
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1041 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.618
_reflns_Friedel_fraction_full    0.731
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                3511
_reflns_number_total             4614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02816_si_003.cif
_cod_data_source_block           cd16761
_cod_depositor_comments
'Adding full bibliography for 4033380--4033384.cif.'
_cod_database_code               4033380
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              48149
_shelx_hkl_checksum              30028