Synthesis of 2-iminothiazolidin-4-ones via copper-catalyzed [2 + 1 + 2] tandem annulation
Zhao, Mingming; Guo, Yiming; Wang, Qi; Liu, Lanqi; Zhang, Shujie; Guo, Wei; Wu, Lin-Ping; Qiu, Fayang G.; RSC Advances 13 (2023) 2220–2224; doi:10.1039/D2RA07872D

data_7246126
_publ_section_title
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 Synthesis of 2-iminothiazolidin-4-ones via copper-catalyzed [2 + 1 + 2]
 tandem annulation
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2220
_journal_page_last               2224
_journal_paper_doi               10.1039/D2RA07872D
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.33
_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
_audit_creation_date             2022-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.935(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5249(3)
_cell_length_b                   5.74470(10)
_cell_length_c                   12.9917(2)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.1130
_cell_measurement_theta_min      5.0390
_cell_volume                     1307.76(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_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    -56.00 -31.00   0.50    0.50    --    0.90 -36.00  21.00   50
  2  \w     10.00  35.00   0.50    0.50    --    0.90  36.00 178.00   50
  3  \w     48.00  73.00   0.50    0.50    --  105.10 -36.00  21.00   50
  4  \w    138.00 182.00   0.50    0.50    --  105.10  36.00 178.00   88
  5  \w    -39.00  13.00   0.50    0.50    --   -0.90 -82.00 120.00  104
  6  \w    -37.00  26.00   0.50    0.50    --   -0.90 -82.00  30.00  126
  7  \w    -47.00 -13.00   0.50    0.50    --   -0.90 -77.00-180.00   68
  8  \w     82.00 127.00   0.50    0.50    --  105.10  82.00 120.00   90
  9  \w    150.00 191.00   0.50    0.50    --  105.10  38.00 -60.00   82
 10  \w     82.00 194.00   0.50    0.50    --  105.10  82.00  90.00  224
 11  \w     75.00 119.00   0.50    0.50    --  105.10 -77.00 150.00   88
 12  \w    110.00 136.00   0.50    0.50    --  105.10  38.00 -60.00   52
 13  \w     98.00 123.00   0.50    0.50    --  105.10  38.00  60.00   50
 14  \w    161.00 187.00   0.50    0.50    --  105.10  38.00  60.00   52
 15  \w     73.00 194.00   0.50    0.50    --  105.10  19.00-120.00  242
 16  \w     19.00 106.00   0.50    0.50    --  105.10 -38.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003178000
_diffrn_orient_matrix_UB_12      -0.0250901000
_diffrn_orient_matrix_UB_13      -0.1179187000
_diffrn_orient_matrix_UB_21      0.0779208000
_diffrn_orient_matrix_UB_22      0.1236714000
_diffrn_orient_matrix_UB_23      0.0312654000
_diffrn_orient_matrix_UB_31      0.0407478000
_diffrn_orient_matrix_UB_32      -0.2365693000
_diffrn_orient_matrix_UB_33      0.0288409000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6834
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.734
_diffrn_reflns_theta_min         5.048
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    8.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             722
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0622P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2488
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07872d2.cif
_cod_data_source_block           lj-0704
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H N O S'
_cod_original_formula_weight         75.09
_cod_original_formula_moiety         '0.211(C13 H14 N2 O3 S)'
_cod_original_formula_units_Z            19
_cod_database_code               7246126
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C N O H S '
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              80541
_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 2.309
_oxdiff_exptl_absorpt_empirical_full_min 0.535