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_1576969
_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_formula_moiety         'C28 H16 S'
_chemical_formula_sum            'C28 H16 S'
_chemical_formula_weight         384.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_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                   18.3772(6)
_cell_length_b                   8.0425(3)
_cell_length_c                   24.7367(8)
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8170
_cell_measurement_theta_min      4.2870
_cell_volume                     3656.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega -103.00  -36.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 134

  2 omega  -45.00  -15.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   90.0000 60

  3 omega   20.00   76.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 112

  4 omega   58.00   85.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 54

  5 omega   78.00  107.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 58

  6 omega   15.00   73.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 116

  7 omega   57.00   88.00   0.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 62

  8 omega   60.00  101.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 82

  9 omega   50.00   91.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 82

 10 omega   97.00  176.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 158

 11 omega   37.00   81.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 88

 12 omega   56.00  104.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 96

 13 omega  134.00  177.00   0.5000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0750631000
_diffrn_orient_matrix_UB_12      0.0515773000
_diffrn_orient_matrix_UB_13      0.0220329000
_diffrn_orient_matrix_UB_21      0.0316692000
_diffrn_orient_matrix_UB_22      0.0079782000
_diffrn_orient_matrix_UB_23      0.0575955000
_diffrn_orient_matrix_UB_31      0.0196772000
_diffrn_orient_matrix_UB_32      0.1843580000
_diffrn_orient_matrix_UB_33      -0.0086859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8481
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.927
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.8894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2782
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc01717g2.cif
_cod_data_source_block           201709162
_cod_depositor_comments
'Adding full bibliography for 1576969--1576975.cif.'
_cod_database_code               1576969
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H41N2S2
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.803
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'