Enantiomer-enriched π-extended helicenes with a perylene core from binaphthol: axial-to-helical chirality transfer with a stepwise Scholl reaction mechanism
Li, Zhi-Ao; Zhu, Ke-Lin; Yao, Nai-Te; Liang, Jiaqi; Shang, Yi-Ling; Zhang, Ye; Gong, Han-Yuan; Chemical Science 16 (2025) 9978–9987; doi:10.1039/D5SC01498K

data_1574541
_publ_section_title
;
 Enantiomer-enriched \p-extended helicenes with a perylene core from
 binaphthol: axial-to-helical chirality transfer with a stepwise Scholl
 reaction mechanism
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9978
_journal_page_last               9987
_journal_paper_doi               10.1039/D5SC01498K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C135.75 H143 Cl1.5 O4.75'
_chemical_formula_weight         1903.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-18 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.1480(4)
_cell_length_b                   30.1006(4)
_cell_length_c                   11.7950(2)
_cell_measurement_reflns_used    19834
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      62.500
_cell_measurement_theta_min      1.932
_cell_volume                     12478.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            70643
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.500
_diffrn_reflns_theta_max         62.500
_diffrn_reflns_theta_min         1.932
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62598
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.013
_exptl_crystal_description       plate
_exptl_crystal_F_000             4084
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 7052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(15)
_refine_ls_extinction_coef       0.00073(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1511
_refine_ls_number_reflns         19834
_refine_ls_number_restraints     678
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0735
_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^)+(0.1299P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.2053
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                17826
_reflns_number_total             19834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01498k4.cif
_cod_data_source_block           A_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1574540--1574544.cif.'
_cod_original_formula_sum        'C135.75 H143 Cl1.50 O4.75'
_cod_database_code               1574541
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              20811