Rh-Mediated Enantioselective Synthesis, Crystal Structures, and Photophysical/Chiroptical Properties of Phenanthrenol-Based [9]Helicene-like Molecules.
Yamano, Ryota; Hara, Jun; Murayama, Koichi; Sugiyama, Haruki; Teraoka, Kota; Uekusa, Hidehiro; Kawauchi, Susumu; Shibata, Yu; Tanaka, Ken; Organic letters 19 (2017) 42–45; doi:10.1021/acs.orglett.6b03279

data_1545221
_publ_section_title
;
 Rh-Mediated Enantioselective Synthesis, Crystal Structures, and
 Photophysical/Chiroptical Properties of Phenanthrenol-Based
 [9]Helicene-like Molecules.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              42
_journal_page_last               45
_journal_paper_doi               10.1021/acs.orglett.6b03279
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C40 H26 O6'
_chemical_formula_sum            'C40 H26 O6'
_chemical_formula_weight         602.61
_chemical_name_systematic        1
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.448(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6621(10)
_cell_length_b                   9.8166(11)
_cell_length_c                   19.265(2)
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.05
_cell_measurement_theta_min      4.69
_cell_volume                     1420.2(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9800
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         4.504
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.34(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0930
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1904P)^2^+0.7818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2500
_refine_ls_wR_factor_ref         0.2975
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3138
_reflns_number_total             4572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03279_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1545221
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.897
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              45804
_shelx_hkl_checksum              98761