Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts
Yang, Beining; Wang, Yatang; Yang, Xiaojuan; Li, Yinyin; Zhang, Zhiying; Hua, Xiaofeng; Ouyang, Lu; Zheng, Lvyin; Guo, Wei; Green Chemistry 26 (2024) 4477–4483; doi:10.1039/D4GC00375F

data_7248335
_publ_section_title
;
 Visible-light-driven three-component annulation for the synthesis of
 highly functionalized 2-iminothiazolidin-4-ones without photocatalysts
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              4477
_journal_page_last               4483
_journal_paper_doi               10.1039/D4GC00375F
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H17 Cl N2 O S'
_chemical_formula_sum            'C22 H17 Cl N2 O S'
_chemical_formula_weight         392.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-01-27
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-01-28 deposited with the CCDC.	2024-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7375(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.71587(8)
_cell_length_b                   16.8188(3)
_cell_length_c                   20.0111(3)
_cell_measurement_reflns_used    10288
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      76.2600
_cell_measurement_theta_min      2.1920
_cell_volume                     1923.59(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_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     -5.00  80.00   0.50    0.20    --   48.13-100.00  81.00  170
  2  \w     35.00  76.00   0.50    0.40    --  104.75-100.00  81.00   82
  3  \w     81.00 106.00   0.50    0.40    --  104.75 -99.00 -30.00   50
  4  \w     39.00  64.00   0.50    0.40    --  104.75 -99.00 -30.00   50
  5  \w     33.00  62.00   0.50    0.40    --  104.75 -57.00 -90.00   58
  6  \w     38.00  63.00   0.50    0.40    --  104.75 -57.00-150.00   50
  7  \w     34.00  67.00   0.50    0.40    --  104.75 -57.00-120.00   66
  8  \w     40.00  66.00   0.50    0.40    --  104.75 -57.00 -60.00   52
  9  \w     33.00  68.00   0.50    0.40    --  104.75 -57.00  60.00   70
 10  \w    112.00 138.00   0.50    0.40    --  104.75 100.00-172.00   52
 11  \w     97.00 167.00   0.50    0.40    --  104.75  38.00-150.00  140
 12  \w    141.00 178.00   0.50    0.40    --  104.75  19.00-180.00   74
 13  \w     96.00 122.00   0.50    0.40    --  104.75  19.00-180.00   52
 14  \w    -17.00   9.00   0.50    0.20    --  -48.13  19.00-180.00   52
 15  \w    -25.00  11.00   0.50    0.20    --  -48.13  19.00-150.00   72
 16  \w    -20.00  24.00   0.50    0.20    --  -48.13  19.00 150.00   88
 17  \w    -25.00  25.00   0.50    0.20    --  -48.13  19.00 -60.00  100
 18  \w    -38.00  21.00   0.50    0.20    --  -48.13 100.00-172.00  118
 19  \w    -60.00 -34.00   0.50    0.40    -- -104.00 100.00-172.00   52
 20  \w    -99.00 -64.00   0.50    0.40    -- -104.00 100.00-172.00   70
 21  \w   -103.00 -35.00   0.50    0.40    -- -104.00  77.00-180.00  136
 22  \w    -64.00 -39.00   0.50    0.40    -- -104.00  57.00-180.00   50
 23  \w    -63.00 -33.00   0.50    0.40    -- -104.00  57.00 -60.00   60
 24  \w   -102.00 -32.00   0.50    0.40    -- -104.00  77.00  30.00  140
 25  \w    -62.00 -32.00   0.50    0.40    -- -104.00  57.00  30.00   60
 26  \w   -154.00-129.00   0.50    0.40    -- -104.00-100.00  81.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0409451000
_diffrn_orient_matrix_UB_12      -0.0603613000
_diffrn_orient_matrix_UB_13      0.0568946000
_diffrn_orient_matrix_UB_21      -0.0794791000
_diffrn_orient_matrix_UB_22      0.0623984000
_diffrn_orient_matrix_UB_23      0.0512105000
_diffrn_orient_matrix_UB_31      -0.2544157000
_diffrn_orient_matrix_UB_32      -0.0292299000
_diffrn_orient_matrix_UB_33      -0.0078665000
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13250
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.608
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.880
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.058
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1044P)^2^+1.7985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.1876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3643
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00375f2.cif
_cod_data_source_block           gw01-hcg
_cod_depositor_comments          'Adding full bibliography for 7248335.cif.'
_cod_database_code               7248335
_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
2. Rigid bond restraints
 Cl1, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim C22: within 2A with sigma of 0.0004 and sigma for terminal atoms of
0.0008 within 2A
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              90499
_shelx_hkl_checksum              56531
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.665