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_4122591
_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 H16 O2'
_chemical_formula_sum            'C26 H16 O2'
_chemical_formula_weight         360.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8979(12)
_cell_length_b                   16.1975(17)
_cell_length_c                   21.268(2)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.71
_cell_measurement_theta_min      4.16
_cell_volume                     3409.7(6)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1436
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12948
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.733
_diffrn_reflns_theta_min         4.157
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Three non-related domains treated during integration and absorption
correction, in agreement with very poor crystal quality (stacked
platelets).
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
For component 1:
 wR2(int) was 0.0940 before and 0.0586 after correction.
For component 2:
 wR2(int) was 0.1142 before and 0.0380 after correction.
For component 3:
 wR2(int) was 0.1305 before and 0.0590 after correction.
Final HKLF 4 output contains 18634 reflections, Rint = 0.2380
 (7924 with I > 3sig(I), Rint = 0.2071)
;
_exptl_crystal_colour            'dull brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   0.8642
_exptl_transmission_factor_min   0.5076
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0850
_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^)+(0.1271P)^2^+4.9197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2329
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2452
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5069323_si_002.cif
_cod_data_source_block           cu_d261113twinn
_cod_depositor_comments
'Adding full bibliography for 4122590--4122591.cif.'
_cod_original_cell_volume        3409.8(6)
_cod_database_code               4122591
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18), C19(H19),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;