Enantioselective Synthesis of [6]Carbohelicenes.
González-Fernández, Elisa; Nicholls, Leo D. M.; Schaaf, Lukas D.; Farès, Christophe; Lehmann, Christian W.; Alcarazo, Manuel; Journal of the American Chemical Society 139 (2017) 1428–1431; doi:10.1021/jacs.6b12443

data_4125734
_publ_section_title
;
 Enantioselective Synthesis of [6]Carbohelicenes.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1428
_journal_page_last               1431
_journal_paper_doi               10.1021/jacs.6b12443
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_compound_source        dichloromethane,pentane
_chemical_formula_moiety
'C55 H48 Au Cl F12 N2 O4 P, F6 Sb, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C55.5 H49 Au Cl2 F18 N2 O4 P Sb'
_chemical_formula_weight         1570.55
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                9794
_audit_creation_date             2015-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                66.668(2)
_cell_angle_beta                 83.965(2)
_cell_angle_gamma                88.252(2)
_cell_formula_units_Z            1
_cell_length_a                   10.9830(12)
_cell_length_b                   11.4243(12)
_cell_length_c                   13.3626(14)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.3493
_cell_measurement_theta_min      2.6323
_cell_volume                     1530.9(3)
_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_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         1\mS
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44170
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.446
_diffrn_reflns_theta_min         2.676
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.047
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       prism
_exptl_crystal_F_000             769
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.062
_refine_diff_density_max         4.005
_refine_diff_density_min         -2.354
_refine_diff_density_rms         0.154
_refine_ls_abs_structure_details
;
 Flack x determined using 7285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         21832
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0558P)^2^+2.1989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                19047
_reflns_number_total             21832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12443_si_004.cif
_cod_data_source_block           9794sadabs
_cod_original_sg_symbol_Hall     'p 1'
_cod_original_sg_symbol_H-M      'p 1'
_cod_original_formula_sum        'C55.50 H49 Au Cl2 F18 N2 O4 P Sb'
_cod_database_code               4125734
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.734
_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. Others
 Fixed Sof: F17B(0.5) F13A(0.5) F14B(0.5) F15B(0.5) F18A(0.5) F16B(0.5)
 F1C(0.33333) C11B(0.5) H11A(0.5) H11B(0.5) H11C(0.5) F10A(0.5) F11A(0.5)
 F12A(0.5) C55B(0.5) F3B(0.33333) F2C(0.33333) C20A(0.5) H20A(0.5) H20B(0.5)
 H20C(0.5) Cl2(0.5) Cl3(0.5) C56(0.5) H56A(0.5) H56B(0.5) F2A(0.33333)
 F1A(0.33333) F1B(0.33333) F3C(0.33333) F2B(0.33333) F3A(0.33333) F10B(0.5)
 F12B(0.5) F11B(0.5) C55A(0.5) F16A(0.5) F18B(0.5) F15A(0.5) F14A(0.5)
 F17A(0.5) F13B(0.5) C11A(0.5) H11D(0.5) H11E(0.5) H11F(0.5) C20B(0.5)
 H20D(0.5) H20E(0.5) H20F(0.5)
3.a Ternary CH refined with riding coordinates:
 C23(H23), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B)
3.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C43(H43), C38(H38), C34(H34), C50(H50), C44(H44), C47(H47), C2(H2),
 C31(H31), C35(H35), C46(H46), C3(H3), C28(H28), C51(H51), C27(H27), C6(H6),
 C54(H54), C30(H30), C8(H8), C53(H53), C17(H17), C15(H15)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C40(H40A,H40B,H40C), C19(H19A,H19B,
 H19C), C41(H41A,H41B,H41C), C21(H21A,H21B,H21C), C11B(H11A,H11B,H11C),
 C20A(H20A,H20B,H20C), C11A(H11D,H11E,H11F), C20B(H20D,H20E,H20F)
;
_shelx_res_checksum              48576
_shelx_hkl_checksum              70118
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'