Photochemical Skeletal Editing: One-Step Transformation of Diaryl Dithiophenes into Regiodefined Helicenes
Shi, Xiaoli; Mei, Ling; Dong, Chenxi; Zhao, Chunmei; Chen, Chen; Xu, Yimin; Xu, Wan; Li, Chunli; Wang, Guangxia; Ma, Zhiying; Wang, Hua; Chemical Science  (2026) –; doi:10.1039/D6SC01717G

data_1576972
_publ_section_title
;
 Photochemical skeletal editing: one-step transformation of diaryl
 dithiophenes into regiodefined helicenes.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              10082
_journal_page_last               10091
_journal_paper_doi               10.1039/d6sc01717g
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H16 S'
_chemical_formula_sum            'C25 H16 S'
_chemical_formula_weight         348.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-08 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3336(16)
_cell_length_b                   28.904(3)
_cell_length_c                   7.6135(8)
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.82
_cell_volume                     3374.3(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297.11
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         2.657
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1024 before and 0.0777 after correction. The Ratio of minimum to maximum transmission is 0.8737. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.19(19)
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0433P)^2^+1.7432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2282
_reflns_number_total             3769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc01717g2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1576969--1576975.cif.'
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               1576972
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.81(19)
 0.19(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24)
3.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              42245
_olex2_submission_special_instructions 'No special instructions were received'