Synthesis of thiazolidines via regioselective addition of unsymmetric thioureas to maleic acid derivatives
Pankova, Alena S.; Samartsev, Mikhail A.; Shulgin, Igor A.; Golubev, Pavel R.; Avdontceva, Margarita S.; Kuznetsov, Mikhail A.; RSC Adv. 4 (2014) 51780–; doi:10.1039/C4RA07840C

data_7218532
_publ_section_title
;
 Synthesis of thiazolidines via regioselective addition of unsymmetric
 thioureas to maleic acid derivatives
;
_journal_issue                   93
_journal_name_full               'RSC Adv.'
_journal_page_first              51780
_journal_paper_doi               10.1039/C4RA07840C
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C20 H20 N4 O5 S'
_chemical_formula_sum            'C20 H20 N4 O5 S'
_chemical_formula_weight         428.46
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1594(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7923(2)
_cell_length_b                   7.50518(16)
_cell_length_c                   24.2322(4)
_cell_measurement_reflns_used    6055
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.4170
_cell_measurement_theta_min      3.1920
_cell_volume                     1961.37(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -91.00   52.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777    0.0000 -150.0000 143

  2 omega  -87.00  -35.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  120.0000 52

  3 omega  -14.00   12.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  150.0000 26

  4 omega  -45.00   48.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   19.0000   60.0000 93

  5 omega    7.00   86.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  150.0000 79
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0232445000
_diffrn_orient_matrix_UB_12      0.0673893000
_diffrn_orient_matrix_UB_13      0.0181276000
_diffrn_orient_matrix_UB_21      0.0574292000
_diffrn_orient_matrix_UB_22      -0.0456873000
_diffrn_orient_matrix_UB_23      0.0027186000
_diffrn_orient_matrix_UB_31      0.0220621000
_diffrn_orient_matrix_UB_32      0.0480018000
_diffrn_orient_matrix_UB_33      -0.0228481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15190
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+1.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                3734
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra07840c2.cif
_cod_data_source_block           pg_ap
_cod_original_cell_volume        1961.36(7)
_cod_database_code               7218532
_chemical_oxdiff_formula         'C25 H25 S O5 N5'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'