Photoinduced tunable fluoroalkylation or sulfonylation/cyclization of methindolylstyrenes via electron donor–acceptor complexes
Wang, Min; Jian, Yu-Rui; Fu, Xin-Yu; Xiang, Wei; Zha, Xiao; Zheng, Hong-Yu; Cui, Bao-Dong; Zhang, Yun; Mou, Xue-Qing; Chen, Yong-Zheng; Green Chemistry 27 (2025) 5433–5441; doi:10.1039/D5GC01102G

data_7250280
_publ_section_title
;
 Photoinduced tunable fluoroalkylation or sulfonylation/cyclization of
 methindolylstyrenes via electron donor--acceptor complexes
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              5433
_journal_page_last               5441
_journal_paper_doi               10.1039/D5GC01102G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C26 H22 N2 O3 S'
_chemical_formula_sum            'C26 H22 N2 O3 S'
_chemical_formula_weight         442.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-05
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-08-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                65.104(4)
_cell_angle_beta                 82.811(4)
_cell_angle_gamma                84.903(4)
_cell_formula_units_Z            4
_cell_length_a                   8.8126(4)
_cell_length_b                   16.8927(7)
_cell_length_c                   19.2951(8)
_cell_measurement_reflns_used    5300
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9640
_cell_measurement_theta_min      2.5430
_cell_volume                     2582.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -54.00  23.00   1.00    1.07    --  -40.73  38.00  90.00   77
  2  \w    -81.00  41.00   1.00    1.07    --  -40.73   0.00  30.00  122
  3  \w     29.00  85.00   1.00    1.07    --   40.73-125.00   0.00   56
  4  \w     38.00 136.00   1.00    1.20    --  106.95 -61.00  30.00   98
  5  \w     79.00 146.00   1.00    1.20    --  106.95  30.00   0.00   67
  6  \w    139.00 166.00   1.00    1.20    --  106.95  35.00 -52.00   27
  7  \w     82.00 125.00   1.00    1.20    --  106.95  35.00 -52.00   43
  8  \w     39.00 135.00   1.00    1.20    --  106.95 -61.00 -90.00   96
  9  \w     77.00 115.00   1.00    1.20    --  106.95-125.00-180.00   38
 10  \w     72.00 118.00   1.00    1.20    --  106.95-125.00 -30.00   46
 11  \w     71.00 109.00   1.00    1.20    --  106.95 -95.00   0.00   38
 12  \w     43.00 140.00   1.00    1.20    --  106.95 -77.00 150.00   97
 13  \w     32.00 135.00   1.00    1.20    --  106.95 -30.00 120.00  103
 14  \w     25.00 153.00   1.00    1.20    --  106.95 -15.00 -30.00  128
 15  \w     31.00  88.00   1.00    1.07    --   40.73-125.00-180.00   57
 16  \w    -51.00  -6.00   1.00    1.07    --  -40.73 125.00-180.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0528637000
_diffrn_orient_matrix_UB_12      -0.0936715000
_diffrn_orient_matrix_UB_13      0.0264024000
_diffrn_orient_matrix_UB_21      0.1569825000
_diffrn_orient_matrix_UB_22      -0.0367096000
_diffrn_orient_matrix_UB_23      0.0296857000
_diffrn_orient_matrix_UB_31      -0.0604805000
_diffrn_orient_matrix_UB_32      -0.0016176000
_diffrn_orient_matrix_UB_33      0.0790141000
_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  0.0820
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16282
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         2.537
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.321
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9103
_refine_ls_number_restraints     524
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.1100
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1583P)^2^+17.5778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3322
_refine_ls_wR_factor_ref         0.3525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6225
_reflns_number_total             9103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01102g2.cif
_cod_data_source_block           3-164h
_cod_depositor_comments
'Adding full bibliography for 7250280--7250281.cif.'
_cod_database_code               7250280
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C48, S2, O4, O5, C35, C45, C34, H35, C36, C46, C49, C25, H34, C43, H36A, H36B,
  C37, H46, C47, H49, C50, C27, C31, C42, C44, C38, H47, H50, H27, C28, C30,
 H31, C41, N3, H44, H38, C39, C51, H28, C29, H30, C40, C01W, H39, N4, O6, H40,
 H01A, H01B, H01C, C32, H32A, H32B, H32C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
 O3, S1, O1, O2, C1, C8, C2, C6, H8, C9, C17, H2, C3, C5, H6, H9, C10, C19,
 C12, H17A, H17B, H3, C4, H5, C11, C26, C20, C24, C13, C7, C16, N2, H26, H20,
 C21, C23, H24, H13, C14, N1, C15, C18, H21, C22, H23, H14, H15, H18A, H18B,
 H18C, C33, H33A, H33B, H33C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C34(H34), C35(H35)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C36(H36A,H36B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31),
  C38(H38), C39(H39), C40(H40), C44(H44), C46(H46), C47(H47), C49(H49), C50(H50)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C33(H33A,H33B,H33C), C01W(H01A,H01B,H01C), C32(H32A,H32B,
 H32C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              51987
_shelx_fab_checksum              85501
_olex2_date_sample_data_collection 2023-07-05
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.899
_oxdiff_exptl_absorpt_empirical_full_min 0.482