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_4515691
_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_formula_moiety
'C55 H49 Au Cl F12 N3 O4 P, F6 Sb, C H2 Cl2, C7 H8'
_chemical_formula_sum            'C63 H59 Au Cl3 F18 N3 O4 P Sb'
_chemical_formula_weight         1720.16
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.008(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5608(6)
_cell_length_b                   22.3675(9)
_cell_length_c                   14.1582(8)
_cell_measurement_reflns_used    7024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.37
_cell_volume                     3647.1(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            55246
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.324
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.602
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4069
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1247 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.4069.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             1696
_refine_diff_density_max         2.218
_refine_diff_density_min         -1.485
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details
;
 Flack x determined using 9454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     839
_refine_ls_number_reflns         22149
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+6.0724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                21171
_reflns_number_total             22149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01374_si_008.cif
_cod_data_source_block           mo_0149_cg_0m
_cod_database_code               4515691
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F10 \\sim F11 \\sim F12 \\sim C27: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
3.a Everything fixed:
 C29, C30
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.c Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17),
 C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33),
  C39(H39), C41(H41), C49(H49), C51(H51), C59(H59), C60(H60), C61(H61),
 C62(H62), C63(H63)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C43(H43A,H43B,H43C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C53(H53A,H53B,H53C), C54(H54A,
 H54B,H54C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C)
;
_shelx_res_checksum              98947
_shelx_hkl_checksum              19232
_olex2_submission_special_instructions 'No special instructions were received'