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_1576973
_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         'C28 H16 S'
_chemical_formula_sum            'C28 H16 S'
_chemical_formula_weight         384.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-08 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7281(2)
_cell_length_b                   8.24130(10)
_cell_length_c                   16.4447(2)
_cell_measurement_reflns_used    11237
_cell_measurement_temperature    295.1(3)
_cell_measurement_theta_max      75.4540
_cell_measurement_theta_min      2.6790
_cell_volume                     1860.01(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.1(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    107.00 133.00   0.50    1.60    --  109.26  45.00-180.00   52
  2  \w    135.00 165.00   0.50    1.60    --  109.26  45.00-180.00   60
  3  \w     68.00  93.00   0.50    0.40    --   43.30 174.00  30.00   50
  4  \w    -27.00  35.00   0.50    0.40    --  -43.30  19.00 -90.00  124
  5  \w    -72.00 -43.00   0.50    0.40    --  -43.30  77.00 -30.00   58
  6  \w    -39.00  30.00   0.50    0.40    --  -43.30  77.00 -30.00  138
  7  \w     36.00  62.00   0.50    1.60    --  109.26 -94.00 -30.00   52
  8  \w     49.00 101.00   0.50    1.60    --  109.26 -94.00 -90.00  104
  9  \w     79.00 104.00   0.50    1.60    --  109.26-174.00  22.00   50
 10  \w     70.00  96.00   0.50    1.60    --  109.26-114.00 160.00   52
 11  \w     55.00  82.00   0.50    0.40    --   43.30-114.00 160.00   54
 12  \w     67.00  92.00   0.50    0.40    --   43.30-174.00  22.00   50
 13  \w     76.00 105.00   0.50    1.60    --  109.26 -94.00 -30.00   58
 14  \w     45.00  88.00   0.50    1.60    --  109.26 -77.00 -30.00   86
 15  \w     74.00 100.00   0.50    1.60    --  109.26 -77.00-180.00   52
 16  \w     36.00  67.00   0.50    1.60    --  109.26 -77.00-180.00   62
 17  \w     38.00  64.00   0.50    1.60    --  109.26 -61.00-180.00   52
 18  \w     37.00  65.00   0.50    1.60    --  109.26 -61.00-150.00   56
 19  \w     35.00  71.00   0.50    1.60    --  109.26 -61.00 120.00   72
 20  \w     39.00  70.00   0.50    1.60    --  109.26 -61.00 -30.00   62
 21  \w     97.00 131.00   0.50    1.60    --  109.26 125.00 -60.00   68
 22  \w    149.00 178.00   0.50    1.60    --  109.26 125.00 -60.00   58
 23  \w     65.00 112.00   0.50    1.60    --  109.26 174.00  30.00   94
 24  \w     98.00 128.00   0.50    1.60    --  109.26 125.00 150.00   60
 25  \w    147.00 178.00   0.50    1.60    --  109.26 125.00 150.00   62
 26  \w    113.00 158.00   0.50    1.60    --  109.26 114.00-107.00   90
 27  \w    -67.00 -41.00   0.50    1.60    --  -90.25 114.00-107.00   52
 28  \w   -107.00 -39.00   0.50    0.40    --  -43.30 174.00  30.00  136
 29  \w    -73.00  -7.00   0.50    0.40    --  -43.30 114.00-107.00  132
 30  \w    -39.00 -14.00   0.50    1.60    --  -90.25  45.00-120.00   50
 31  \w    -49.00 -14.00   0.50    1.60    --  -90.25  45.00 -90.00   70
 32  \w    -47.00 -22.00   0.50    1.60    --  -90.25  45.00 -60.00   50
 33  \w    -43.00 -17.00   0.50    1.60    --  -90.25  45.00  60.00   52
 34  \w    -50.00 -18.00   0.50    1.60    --  -90.25  45.00  90.00   64
 35  \w    -42.00 -16.00   0.50    1.60    --  -90.25  45.00 120.00   52
 36  \w   -105.00 -80.00   0.50    1.60    --  -90.25-114.00 160.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282125000
_diffrn_orient_matrix_UB_12      0.0801467000
_diffrn_orient_matrix_UB_13      -0.0817633000
_diffrn_orient_matrix_UB_21      0.0820150000
_diffrn_orient_matrix_UB_22      -0.0942364000
_diffrn_orient_matrix_UB_23      -0.0416520000
_diffrn_orient_matrix_UB_31      -0.0712913000
_diffrn_orient_matrix_UB_32      -0.1401403000
_diffrn_orient_matrix_UB_33      -0.0188991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13572
_diffrn_reflns_point_group_measured_fraction_full 0.759
_diffrn_reflns_point_group_measured_fraction_max 0.714
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.733
_diffrn_reflns_theta_min         2.688
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.051(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         5535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0678P)^2^+0.0147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.399
_reflns_Friedel_fraction_full    0.487
_reflns_Friedel_fraction_max     0.439
_reflns_number_gt                5282
_reflns_number_total             5535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc01717g2.cif
_cod_data_source_block           sxl-tm2_2
_cod_depositor_comments
'Adding full bibliography for 1576969--1576975.cif.'
_cod_database_code               1576973
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C112 H64 Cl4 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30), C31(H31), C32(H32), C33(H33), C37(H37), C38(H38), C45(H45),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C53(H53), C54(H54), C55(H55),
  C56(H56)
;
_shelx_res_checksum              92305
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.025
_oxdiff_exptl_absorpt_empirical_full_min 0.626