TADDOL-Derived Cationic Phosphonites: Toward an Effective Enantioselective Synthesis of [6]Helicenes via Au-Catalyzed Alkyne Hydroarylation
Nicholls, Leo D. M.; Marx, Maximilian; Hartung, Thierry; González-Fernández, Elisa; Golz, Christopher; Alcarazo, Manuel; ACS Catalysis 8 (2018) 6079–; doi:10.1021/acscatal.8b01374

data_4515685
_publ_section_title
;
 TADDOL-Derived Cationic Phosphonites: Toward an Effective
 Enantioselective Synthesis of [6]Helicenes via Au-Catalyzed Alkyne
 Hydroarylation
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6079
_journal_paper_doi               10.1021/acscatal.8b01374
_journal_volume                  8
_journal_year                    2018
_chemical_compound_source        chloroform
_chemical_formula_moiety         'C40 H28'
_chemical_formula_sum            'C40 H28'
_chemical_formula_weight         508.62
_chemical_name_systematic
;
 7-(4-methylphenyl)methylene)-fluoreneo[c:c]fluorene-
 7-(bis(4-methylphenyl)methylene)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GON-GC-485-01_100K_9622
_audit_creation_date             2018-04-07
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 107.002(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6931(12)
_cell_length_b                   9.8945(5)
_cell_length_c                   11.3008(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.2204
_cell_measurement_theta_min      3.7437
_cell_volume                     2640.4(2)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30429
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.386
_diffrn_reflns_theta_max         67.386
_diffrn_reflns_theta_min         3.744
_diffrn_source                   'Nonius FR-591 Cu rotating anode'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.94245
_exptl_absorpt_correction_T_min  0.88133
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0345P)^2^+3.3379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2276
_reflns_number_total             2358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01374_si_013.cif
_cod_data_source_block           15ba
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4515685
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.937
_shelx_res_checksum              42838
_shelx_hkl_checksum              45069