Metal-free, visible-light-mediated phototransformations of <i>ortho</i>-biaryl appended chalcones: access to oxathia[5]helicenes and 1,2,3,4-tetrasubstituted cyclobutanes.
Zakharov, A. V.; Evsikova, E. E.; Grebennikova, P. D.; Krylova, M. A.; Fakhrutdinov, A. N.; Shirinian, V. Z.; Organic & biomolecular chemistry 23 (2025) 5182–5190; doi:10.1039/d5ob00490j

data_7160521
_publ_section_title
;
 Metal-free, visible-light-mediated phototransformations of
 <i>ortho</i>-biaryl appended chalcones: access to oxathia[5]helicenes and
 1,2,3,4-tetrasubstituted cyclobutanes.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5182
_journal_page_last               5190
_journal_paper_doi               10.1039/d5ob00490j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H16 O3 S'
_chemical_formula_sum            'C26 H16 O3 S'
_chemical_formula_weight         408.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-01-14
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-03-17 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3152(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.74314(5)
_cell_length_b                   7.47998(5)
_cell_length_c                   31.73273(18)
_cell_measurement_reflns_used    17329
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      79.4740
_cell_measurement_theta_min      5.5900
_cell_volume                     1832.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     34.00  96.00   0.50    0.17    --   42.08-125.00 -90.00  124
  2  \w     45.00 111.00   0.50    0.68    --  117.50-125.00  60.00  132
  3  \w     46.00 111.00   0.50    0.68    --  117.50-125.00 -60.00  130
  4  \w     69.00  95.00   0.50    0.68    --  117.50-105.00-120.32   52
  5  \w     51.00 105.00   0.50    0.68    --  117.50 -95.00-150.00  108
  6  \w     52.00 102.00   0.50    0.68    --  117.50 -95.00-180.00  100
  7  \w     76.00 101.00   0.50    0.68    --  117.50 -95.00  30.00   50
  8  \w     43.00 154.00   0.50    0.68    --  117.50 -88.00 -68.70  222
  9  \w     43.00 154.00   0.50    0.68    --  117.50 -88.00 -68.70  222
 10  \w     44.00 110.00   0.50    0.68    --  117.50 -78.00 -72.43  132
 11  \w     44.00  85.00   0.50    0.68    --  117.50 -77.00 -30.00   82
 12  \w     46.00 109.00   0.50    0.68    --  117.50 -78.00  40.95  126
 13  \w     44.00  98.00   0.50    0.68    --  117.50 -75.00  70.00  108
 14  \w     50.00  80.00   0.50    0.68    --  117.50 -77.00 120.00   60
 15  \w     44.00 105.00   0.50    0.68    --  117.50 -77.00 150.00  122
 16  \w     44.00  71.00   0.50    0.68    --  117.50 -61.00  90.00   54
 17  \w     44.00  70.00   0.50    0.68    --  117.50 -61.00  30.00   52
 18  \w    -31.00  72.00   0.50    0.17    --   42.08 -75.00  70.00  206
 19  \w    -39.00  27.00   0.50    0.17    --   42.08 -19.00 -60.00  132
 20  \w     45.00  71.00   0.50    0.68    --  117.50 -61.00-180.00   52
 21  \w    149.00 178.00   0.50    0.68    --  117.50   0.00 -60.00   58
 22  \w     88.00 178.00   0.50    0.68    --  117.50  75.00-161.00  180
 23  \w     87.00 146.00   0.50    0.68    --  117.50  77.00 -60.00  118
 24  \w     96.00 122.00   0.50    0.68    --  117.50  61.00 -60.00   52
 25  \w    103.00 128.00   0.50    0.68    --  117.50  45.00-120.00   50
 26  \w     98.00 177.00   0.50    0.68    --  117.50  30.00-180.00  158
 27  \w    152.00 177.00   0.50    0.68    --  117.50  61.00 -90.00   50
 28  \w     98.00 177.00   0.50    0.68    --  117.50  30.00-180.00  158
 29  \w    133.00 176.00   0.50    0.68    --  117.50  77.00 -30.00   86
 30  \w     36.00 178.00   0.50    0.68    --  117.50   0.00 -60.00  284
 31  \w    133.00 159.00   0.50    0.68    --  117.50  30.00   0.00   52
 32  \w    116.00 142.00   0.50    0.68    --  117.50  45.00 120.00   52
 33  \w    128.00 178.00   0.50    0.68    --  117.50  77.00 120.00  100
 34  \w     96.00 163.00   0.50    0.68    --  117.50 125.00 150.00  134
 35  \w    130.00 167.00   0.50    0.68    --  117.50 125.00 120.00   74
 36  \w    102.00 144.00   0.50    0.68    --  117.50 125.00-180.00   84
 37  \w   -116.00 -12.00   0.50    0.17    --  -42.08 -75.00  70.00  208
 38  \w   -171.00 -66.00   0.50    0.68    --  -96.00 -75.00  70.00  210
 39  \w    -51.00 -19.00   0.50    0.68    --  -96.00  45.00 -30.00   64
 40  \w    -71.00 -21.00   0.50    0.68    --  -96.00  61.00  30.00  100
 41  \w    -72.00  33.00   0.50    0.17    --  -42.08  75.00-161.00  210
 42  \w    -98.00 -21.00   0.50    0.68    --  -96.00  75.00-161.00  154
 43  \w    -98.00 -21.00   0.50    0.68    --  -96.00  75.00-161.00  154
;
_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      0.1074809000
_diffrn_orient_matrix_UB_12      -0.1188934000
_diffrn_orient_matrix_UB_13      0.0317602000
_diffrn_orient_matrix_UB_21      -0.0501982000
_diffrn_orient_matrix_UB_22      0.1204518000
_diffrn_orient_matrix_UB_23      0.0365128000
_diffrn_orient_matrix_UB_31      -0.1604540000
_diffrn_orient_matrix_UB_32      -0.1173563000
_diffrn_orient_matrix_UB_33      0.0052987000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            25432
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.671
_diffrn_reflns_theta_min         2.793
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.9609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3855
_reflns_number_total             3976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00490j2.cif
_cod_data_source_block           GDP41
_cod_depositor_comments
'Adding full bibliography for 7160521--7160522.cif.'
_cod_original_cell_volume        1832.703(19)
_cod_database_code               7160521
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C26H16ClO3
_chemical_oxdiff_usercomment     GPD41
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.606
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19),
 C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              85000
_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.869