Synthesis of Racemic, Diastereopure, and Enantiopure Carba- or Oxa[5]-, [6]-, [7]-, and -[19]helicene (Di)thiol Derivatives.
Nejedlý, Jindřich; Šámal, Michal; Rybáček, Jiří; Sánchez, Isabel Gay; Houska, Václav; Warzecha, Tomáš; Vacek, Jaroslav; Sieger, Ladislav; Buděšínský, Miloš; Bednárová, Lucie; Fiedler, Pavel; Císařová, Ivana; Starý, Ivo; Stará, Irena G; The Journal of organic chemistry 85 (2020) 248–276; doi:10.1021/acs.joc.9b02965

data_4037717
_publ_section_title
;
 Synthesis of Racemic, Diastereopure, and Enantiopure Carba- or Oxa[5]-,
 [6]-, [7]-, and -[19]helicene (Di)thiol Derivatives.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              248
_journal_page_last               276
_journal_paper_doi               10.1021/acs.joc.9b02965
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C143 H121 Cl2 O13'
_chemical_formula_sum            'C143 H121 Cl2 O13'
_chemical_formula_weight         2118.29
_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_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90.607(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5750(7)
_cell_length_b                   20.2391(11)
_cell_length_c                   20.8569(11)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.5771
_cell_measurement_theta_min      3.2558
_cell_volume                     5730.0(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            81409
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.847
_diffrn_reflns_theta_min         2.118
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       prism
_exptl_crystal_F_000             2234
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.305
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 9039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1442
_refine_ls_number_reflns         22024
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0837P)^2^+1.1412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                21056
_reflns_number_total             22024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02965_si_003.cif
_cod_data_source_block           cu_jin377_stary
_cod_depositor_comments
'Adding full bibliography for 4037717--4037718.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037717
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.590
_shelx_estimated_absorpt_t_max   0.745
_shelx_res_checksum              69539
_shelx_hkl_checksum              77553