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_4125731
_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
_chemical_formula_moiety         'C52.50 H55.50 Au Cl4 F6 N2 O4 P Sb'
_chemical_formula_sum            'C52.5 H55.5 Au Cl4 F6 N2 O4 P Sb'
_chemical_formula_weight         1383.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GON-GC-378-01
_audit_creation_date             2015-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.868(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.420(3)
_cell_length_b                   10.5690(15)
_cell_length_c                   22.221(3)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.1867
_cell_measurement_theta_min      2.5692
_cell_volume                     5497.4(13)
_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, 1997-2012)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            93213
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.205
_diffrn_reflns_theta_min         2.781
_diffrn_source                   1\mS
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.446
_exptl_absorpt_correction_T_max  0.87791
_exptl_absorpt_correction_T_min  0.65419
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       plate
_exptl_crystal_F_000             2734
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.916
_refine_diff_density_min         -1.295
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Flack x determined using 8744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0083(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         20974
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+11.5148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                19613
_reflns_number_total             20974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12443_si_003.cif
_cod_data_source_block           9222sadabs
_cod_original_sg_symbol_Hall     'c 2y'
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C52.50 H55.50 Au Cl4 F6 N2 O4 P Sb'
_cod_database_code               4125731
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.540
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl4A(0.25) Cl4B(0.25) C98(0.25) H98A(0.25) H98B(0.25) Cl5A(0.25)
 Cl5B(0.25) C99(0.25) H99A(0.25) H99B(0.25) H99C(0.25) H99D(0.25)
3.a Ternary CH refined with riding coordinates:
 C23(H23), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C97(H97A,H97B), C98(H98A,H98B), C99(H99A,H99B), C99(H99C,H99D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
  C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
 C49(H49), C50(H50), C51(H51)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_res_checksum              52075
_shelx_hkl_checksum              26987
_olex2_submission_special_instructions 'No special instructions were received'
_shelxl_version_number           2014-3