Iodine promoted cyclization of N,N'-diphenylthiocarbamides with enaminones：a protocol for the synthesis of poly-substituted 2-iminothiazolines
Dong, Zhi-Bing; Xu, Xiao-Hu; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01477G

data_7158927
_publ_section_title
;
 Iodine promoted cyclization of N,N'-diphenylthiocarbamides with
 enaminones&#xFF1A;a protocol for the synthesis of poly-substituted
 2-iminothiazolines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01477G
_journal_year                    2022
_chemical_formula_moiety         'C22 H16 N2 O S'
_chemical_formula_sum            'C22 H16 N2 O S'
_chemical_formula_weight         356.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bks90
_audit_creation_date             2022-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.110(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8239(14)
_cell_length_b                   15.770(4)
_cell_length_c                   9.954(3)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.44
_cell_volume                     905.1(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.437
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                2037
_reflns_number_total             2760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01477g2.cif
_cod_data_source_block           0324dzb_0m
_cod_original_cell_volume        905.0(4)
_cod_database_code               7158927
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_shelx_res_checksum              15296
_olex2_submission_special_instructions 'No special instructions were received'