Helically Chiral 1-Sulfur-Functionalized [6]Helicene: Synthesis, Optical Resolution, and Functionalization.
Tsujihara, Tetsuya; Zhou, Da-Yang; Suzuki, Takeyuki; Tamura, Satoru; Kawano, Tomikazu; Organic letters 19 (2017) 3311–3314; doi:10.1021/acs.orglett.7b01470

data_1546466
_publ_section_title
;
 Helically Chiral 1-Sulfur-Functionalized [6]Helicene: Synthesis, Optical
 Resolution, and Functionalization.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3311
_journal_page_last               3314
_journal_paper_doi               10.1021/acs.orglett.7b01470
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C40 H29 N O3 S'
_chemical_formula_sum            'C40 H29 N O3 S'
_chemical_formula_weight         603.73
_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_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.4224(17)
_cell_length_b                   16.987(3)
_cell_length_c                   18.800(4)
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.06
_cell_volume                     3009.1(10)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24114
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.061
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264.00
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0390P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4342
_reflns_number_total             6852
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b01470_si_004.cif
_cod_data_source_block           20170313-4
_cod_original_cell_volume        3009.2(10)
_cod_database_code               1546466
_shelxl_version_number           2014/6
_shelx_res_checksum              57045
_shelx_hkl_checksum              90004