Gold-catalyzed cyclization of 1,6-diynyl dithioacetals via 1,7-carbene transfer and aromatic C-H functionalization.
Xu, Wei; Chen, Ming; Sun, Ning; Liu, Yuanhong; Chemical communications (Cambridge, England) 52 (2016) 11000–11003; doi:10.1039/c6cc05302e

data_7124881
_publ_section_title
;
 Gold-catalyzed cyclization of 1,6-diynyl dithioacetals via 1,7-carbene
 transfer and aromatic C-H functionalization.
;
_journal_issue                   73
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11000
_journal_page_last               11003
_journal_paper_doi               10.1039/c6cc05302e
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C52 H40 O2 S4'
_chemical_formula_weight         825.08
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-05-23 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.501(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.601(2)
_cell_length_b                   19.272(4)
_cell_length_c                   11.193(2)
_cell_measurement_reflns_used    2376
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.682
_cell_measurement_theta_min      4.380
_cell_volume                     2028.4(7)
_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 0.974
_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  0.0783
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10876
_diffrn_reflns_point_group_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.051
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
; 
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.26(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     552
_refine_ls_number_reflns         5962
_refine_ls_number_restraints     475
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0938
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1163P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2244
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.637
_reflns_Friedel_fraction_max     0.654
_reflns_number_gt                3694
_reflns_number_total             5962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05302e2.cif
_cod_data_source_block           cd15255
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7124881
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-4
_shelx_res_checksum              51483