Helicene quinones: redox-triggered chiroptical switching and chiral recognition of the semiquinone radical anion lithium salt by electron nuclear double resonance spectroscopy.
Schweinfurth, David; Zalibera, Michal; Kathan, Michael; Shen, Chengshuo; Mazzolini, Marcella; Trapp, Nils; Crassous, Jeanne; Gescheidt, Georg; Diederich, François; Journal of the American Chemical Society 136 (2014) 13045–13052; doi:10.1021/ja5069323

data_4122590
_publ_section_title
;
 Helicene quinones: redox-triggered chiroptical switching and chiral
 recognition of the semiquinone radical anion lithium salt by electron
 nuclear double resonance spectroscopy.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13045
_journal_page_last               13052
_journal_paper_doi               10.1021/ja5069323
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C26 H14 O2, C H Cl3'
_chemical_formula_sum            'C27 H15 Cl3 O2'
_chemical_formula_weight         477.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4713)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.708(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1039(3)
_cell_length_b                   19.8611(6)
_cell_length_c                   14.8094(5)
_cell_measurement_reflns_used    5729
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.59
_cell_volume                     2070.31(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12433
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         1.886
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0363 before and 0.0326 after correction.
The Ratio of minimum to maximum transmission is 0.9388.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            'metallic black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0471P)^2^+1.3911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4108
_reflns_number_total             4771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5069323_si_003.cif
_cod_data_source_block           d142313_0m
_cod_depositor_comments
'Adding full bibliography for 4122590--4122591.cif.'
_cod_database_code               4122590
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1L(H1L)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C15(H15), C16(H16),
 C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              19882
_shelx_hkl_checksum              60316