Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of DBU.
Saito, Rei; Uemura, Naohiro; Ishikawa, Hiroki; Magara, Akina; Yoshida, Yasushi; Mino, Takashi; Kasashima, Yoshio; Sakamoto, Masami; Organic & biomolecular chemistry 16 (2018) 7910–7919; doi:10.1039/c8ob02066c

data_7156480
_publ_section_title
;
 Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of
 DBU.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7910
_journal_page_last               7919
_journal_paper_doi               10.1039/c8ob02066c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_weight         324.43
_chemical_melting_point          164.5(5)
_chemical_name_common            2h
_chemical_name_systematic
N-Phenyl-N'-propyl-6-phenyl-2-iminotetrahydro-1,3-thiazin-4-one
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.767(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8458(5)
_cell_length_b                   5.3427(2)
_cell_length_c                   24.6144(10)
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.1837
_cell_measurement_theta_min      3.5145
_cell_volume                     1653.82(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10898
_diffrn_reflns_theta_full        68.34
_diffrn_reflns_theta_max         68.34
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3 and Hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0952P)^2^+0.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2264
_reflns_number_total             3012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02066c2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '164-165' was changed to '164.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156480--7156486.cif.
;
_cod_database_code               7156480
_shelx_res_checksum              44486