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_7160522
_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         'C28 H19 Cl O3'
_chemical_formula_sum            'C28 H19 Cl O3'
_chemical_formula_weight         438.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-17 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                   4.43650(10)
_cell_length_b                   11.7816(2)
_cell_length_c                   40.0556(6)
_cell_measurement_reflns_used    7109
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6030
_cell_measurement_theta_min      2.2150
_cell_volume                     2093.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.134a 64-bit (release 09-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_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    -25.00  35.00   0.50    7.00    --  -44.13  16.00 -82.00  120
  2  \w   -110.00 -17.00   0.50    7.00    --  -44.13 -16.00 108.00  186
  3  \w    -82.00  -1.00   0.50    7.00    --  -44.13 110.00  68.00  162
  4  \w    -97.00 -22.00   0.50   28.00    --  -96.00 139.00 140.00  150
  5  \w     45.00 122.00   0.50   28.00    --  117.50-139.00  80.00  154
  6  \w     89.00 178.00   0.50   28.00    --  117.50  16.00 -82.00  178
  7  \w    103.00 178.00   0.50   28.00    --  117.50 110.00  68.00  150
  8  \w   -110.00 -17.00   0.50    7.00    --  -44.13 -16.00 108.00  186
  9  \w    -25.00  32.00   0.50    7.00    --  -44.13  19.00-150.00  114
 10  \w     99.00 132.00   0.50   28.00    --  117.50  61.00 -30.00   66
 11  \w     59.00  85.00   0.50   28.00    --  117.50 -95.00 -90.00   52
 12  \w     99.00 124.00   0.50   28.00    --  117.50  27.00 -17.10   50
 13  \w    142.00 173.00   0.50   28.00    --  117.50  27.00 -17.10   62
 14  \w    130.00 156.00   0.50   28.00    --  117.50  61.00  60.00   52
 15  \w     99.00 127.00   0.50   28.00    --  117.50  45.00  90.00   56
 16  \w     47.00  75.00   0.50   28.00    --  117.50 -95.00 -60.00   56
 17  \w     80.00 105.00   0.50   28.00    --  117.50 -95.00 -60.00   50
 18  \w     87.00 128.00   0.50   28.00    --  117.50  15.00 -90.00   82
 19  \w     45.00  70.00   0.50   28.00    --  117.50 -61.00  30.00   50
 20  \w     45.00  70.00   0.50   28.00    --  117.50 -61.00  60.00   50
 21  \w     45.00  70.00   0.50   28.00    --  117.50 -61.00 150.00   50
 22  \w     47.00  78.00   0.50   28.00    --  117.50 -77.00 -30.00   62
 23  \w    148.00 178.00   0.50   28.00    --  117.50  61.00 -30.00   60
 24  \w    153.00 178.00   0.50   28.00    --  117.50  45.00  90.00   50
 25  \w     97.00 145.00   0.50   28.00    --  117.50  61.00   0.00   96
 26  \w     88.00 114.00   0.50   28.00    --  117.50 -83.00  27.62   52
 27  \w     53.00 104.00   0.50   28.00    --  117.50 -77.00   0.00  102
 28  \w    126.00 162.00   0.50   28.00    --  117.50  30.00 -30.00   72
 29  \w     45.00  71.00   0.50   28.00    --  117.50 -61.00  90.00   52
;
_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      0.0705163000
_diffrn_orient_matrix_UB_12      0.1194704000
_diffrn_orient_matrix_UB_13      -0.0134910000
_diffrn_orient_matrix_UB_21      0.0168385000
_diffrn_orient_matrix_UB_22      0.0456431000
_diffrn_orient_matrix_UB_23      0.0359476000
_diffrn_orient_matrix_UB_31      0.3406260000
_diffrn_orient_matrix_UB_32      -0.0269298000
_diffrn_orient_matrix_UB_33      0.0010339000
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            8900
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.761
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.134a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         8900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0880P)^2^+0.6317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                8349
_reflns_number_total             8900
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 176.4797\% 
around [-0.00 0.00 1.00] (reciprocal) or [0.01 0.00 1.00] (direct)
;
_cod_data_source_file            d5ob00490j2.cif
_cod_data_source_block           1265-cl
_cod_depositor_comments
'Adding full bibliography for 7160521--7160522.cif.'
_cod_database_code               7160522
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H23N2O3Cl
_chemical_oxdiff_usercomment     1265-Cl
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7288(13)
 0.2712(13)
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:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              8884
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2