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_7250281
_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         'C22.634 H19.634 N O3 S1.878'
_chemical_formula_sum            'C23 H20 N O3 S2'
_chemical_formula_weight         422.52
_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
_audit_creation_date             2023-07-26
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0229(2)
_cell_length_b                   16.8862(3)
_cell_length_c                   21.3037(3)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4680
_cell_measurement_theta_min      3.9650
_cell_volume                     3965.36(12)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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    -63.00  19.00   1.00    1.00    --  -40.73  38.00 120.00   82
  2  \w     24.00  60.00   1.00    1.00    --   40.73 -57.00 150.00   36
  3  \w     28.00  69.00   1.00    1.00    --  106.95 -95.00 120.00   41
  4  \w     90.00 139.00   1.00    1.00    --  106.95 -77.00  60.00   49
  5  \w     32.00  59.00   1.00    1.00    --  106.95 -77.00  60.00   27
  6  \w      5.00  58.00   1.00    1.00    --   40.73 -99.00 -60.00   53
  7  \w     92.00 177.00   1.00    1.00    --  106.95  61.00-180.00   85
  8  \w     99.00 126.00   1.00    1.00    --  106.95 125.00  60.00   27
  9  \w    144.00 173.00   1.00    1.00    --  106.95 125.00  60.00   29
 10  \w     94.00 142.00   1.00    1.00    --  106.95 125.00  90.00   48
;
_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      -0.0901290000
_diffrn_orient_matrix_UB_12      0.0669133000
_diffrn_orient_matrix_UB_13      0.0153849000
_diffrn_orient_matrix_UB_21      -0.0191100000
_diffrn_orient_matrix_UB_22      -0.0351115000
_diffrn_orient_matrix_UB_23      0.0660343000
_diffrn_orient_matrix_UB_31      0.1051073000
_diffrn_orient_matrix_UB_32      0.0510759000
_diffrn_orient_matrix_UB_33      0.0251812000
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10428
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.622
_diffrn_reflns_theta_min         4.150
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63274
_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    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         4.520
_refine_diff_density_min         -1.514
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.964
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.1082
_refine_ls_shift/su_max          15.000
_refine_ls_shift/su_mean         0.523
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0913P)^2^+3.7758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3020
_refine_ls_wR_factor_ref         0.3144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3255
_reflns_number_total             3921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01102g2.cif
_cod_data_source_block           3-164k
_cod_depositor_comments
'Adding full bibliography for 7250280--7250281.cif.'
_cod_database_code               7250281
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.0007 and sigma for terminal atoms of
0.0014
Uanis(C23) = Uanis(C24)
3. Rigid body (RIGU) restrains
 C6, S01, C24, O2, O3, C8, S02, C23, C7, H8, C9, C21, C22, H23, C1, H7, C11,
 H9, C10, H21, H22, C2, C12, C15, H2, C3, C5, H6, H12, C13, C14, C16, H3, C4,
 H5, H13, N1, H16, C17, O1, C18, H17, C19, H18A, H18B, H18C, H19A, H19B, H19C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
4. Others
 Sof(S02)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              95345
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.650