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_4125733
_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         'C68 H60 Au Cl N2 O4 P, F6 Sb, 1.5(C H2 Cl2)'
_chemical_formula_sum            'C69.5 H63 Au Cl4 F6 N2 O4 P Sb'
_chemical_formula_weight         1595.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GON-GC-351-02
_audit_creation_date             2014-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.750(4)
_cell_length_b                   24.403(14)
_cell_length_c                   25.635(6)
_cell_measurement_reflns_used    133626
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.9999
_cell_measurement_theta_min      2.6043
_cell_volume                     6725(5)
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            112554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.104
_diffrn_reflns_theta_min         2.610
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_T_max  0.94783
_exptl_absorpt_correction_T_min  0.77513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       plate
_exptl_crystal_F_000             3172
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.272
_refine_diff_density_min         -2.379
_refine_diff_density_rms         0.196
_refine_ls_abs_structure_details
;
 Flack x determined using 6240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     816
_refine_ls_number_reflns         23459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0847P)^2^+24.8537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                16974
_reflns_number_total             23459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12443_si_002.cif
_cod_data_source_block           9178sadabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'ORTHORHOMBIC' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_Hall     'p 2ac 2ab'
_cod_original_formula_sum        'C69.50 H63 Au Cl4 F6 N2 O4 P Sb'
_cod_database_code               4125733
_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: F1A(0.5) F1B(0.5) F4A(0.5) F4B(0.5) F5A(0.5) F5B(0.5) Cl4(0.5)
 Cl5(0.5) C99(0.5) H99A(0.5) H99B(0.5)
3.a Ternary CH refined with riding coordinates:
 C64(H64), C65(H65)
3.b Secondary CH2 refined with riding coordinates:
 C98(H98A,H98B), C99(H99A,H99B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C24(H24), C25(H25),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C34(H34), C36(H36), C37(H37),
  C38(H38), C39(H39), C41(H41), C42(H42), C45(H45), C46(H46), C48(H48),
 C49(H49), C50(H50), C51(H51), C53(H53), C55(H55), C56(H56), C58(H58), C59(H59),
  C60(H60), C61(H61), C63(H63)
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), C67(H67A,H67B,H67C), C68(H68A,
 H68B,H68C)
;
_shelx_res_checksum              18359
_shelx_hkl_checksum              12826
_olex2_submission_special_instructions 'No special instructions were received'
_shelxl_version_number           2014-3