#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:59:26 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/64/7156480.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7156480
loop_
_publ_author_name
'Saito, Rei'
'Uemura, Naohiro'
'Ishikawa, Hiroki'
'Magara, Akina'
'Yoshida, Yasushi'
'Mino, Takashi'
'Kasashima, Yoshio'
'Sakamoto, Masami'
_publ_section_title
;
 Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of
 DBU.
;
_journal_issue                   42
_journal_name_full               'Organic & 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/[σ²(Fo²)+(0.0952P)²+0.1574P] where P=(Fo²+2Fc²)/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 > 2σ(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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.30702(17) 0.3667(4) 0.62829(9) 0.0265(5) Uani d . . 1
C C2 0.28377(18) 0.4694(4) 0.73682(10) 0.0275(5) Uani d . . 1
H H2 0.3426 0.3518 0.7529 0.033 Uiso calc U R 1
C C3 0.3313(2) 0.7165(5) 0.72503(10) 0.0324(5) Uani d . . 1
H H3A 0.2732 0.8289 0.7069 0.039 Uiso calc U R 1
H H3B 0.3655 0.7942 0.7607 0.039 Uiso calc U R 1
C C4 0.41182(18) 0.6971(4) 0.68872(10) 0.0294(5) Uani d . . 1
C C5 0.20684(19) 0.0766(5) 0.56827(11) 0.0339(6) Uani d . . 1
H H5A 0.1402 0.167 0.5697 0.041 Uiso calc U R 1
H H5B 0.2149 -0.0608 0.5958 0.041 Uiso calc U R 1
C C6 0.1993(2) -0.0325(6) 0.51114(11) 0.0419(6) Uani d . . 1
H H6A 0.27 -0.0966 0.5078 0.05 Uiso calc U R 1
H H6B 0.1792 0.1016 0.4832 0.05 Uiso calc U R 1
C C7 0.1184(2) -0.2437(5) 0.49873(13) 0.0447(7) Uani d . . 1
H H7A 0.1384 -0.3782 0.5259 0.067 Uiso calc U R 1
H H7B 0.1169 -0.3087 0.4614 0.067 Uiso calc U R 1
H H7C 0.0478 -0.1801 0.5009 0.067 Uiso calc U R 1
C C8 0.47934(17) 0.5169(4) 0.61277(9) 0.0268(5) Uani d . . 1
C C9 0.55035(19) 0.3216(5) 0.61986(10) 0.0300(5) Uani d . . 1
H H9 0.5438 0.1883 0.6445 0.036 Uiso calc U R 1
C C10 0.63216(19) 0.3221(5) 0.59038(11) 0.0330(5) Uani d . . 1
H H10 0.6829 0.1903 0.5955 0.04 Uiso calc U R 1
C C11 0.63962(19) 0.5141(5) 0.55370(10) 0.0331(5) Uani d . . 1
H H11 0.6947 0.5125 0.5332 0.04 Uiso calc U R 1
C C12 0.5673(2) 0.7078(5) 0.54689(10) 0.0321(5) Uani d . . 1
H H12 0.5728 0.8393 0.5216 0.039 Uiso calc U R 1
C C13 0.48635(19) 0.7119(4) 0.57680(10) 0.0297(5) Uani d . . 1
H H13 0.4369 0.8462 0.5726 0.036 Uiso calc U R 1
C C14 0.20644(18) 0.4833(5) 0.77554(9) 0.0279(5) Uani d . . 1
C C15 0.2112(2) 0.3037(5) 0.81660(10) 0.0346(6) Uani d . . 1
H H15 0.2642 0.1771 0.8208 0.042 Uiso calc U R 1
C C16 0.1392(2) 0.3081(6) 0.85152(11) 0.0422(6) Uani d . . 1
H H16 0.1425 0.1835 0.8794 0.051 Uiso calc U R 1
C C17 0.0628(2) 0.4921(6) 0.84603(12) 0.0449(7) Uani d . . 1
H H17 0.0133 0.494 0.8699 0.054 Uiso calc U R 1
C C18 0.0581(2) 0.6733(6) 0.80591(13) 0.0445(7) Uani d . . 1
H H18 0.0061 0.8019 0.8026 0.053 Uiso calc U R 1
C C19 0.1291(2) 0.6688(5) 0.77030(11) 0.0369(6) Uani d . . 1
H H19 0.1249 0.7928 0.7423 0.044 Uiso calc U R 1
N N1 0.39654(15) 0.5240(4) 0.64566(8) 0.0278(4) Uani d . . 1
N N2 0.29671(15) 0.2486(4) 0.58298(8) 0.0306(5) Uani d . . 1
O O1 0.48952(14) 0.8331(4) 0.69661(7) 0.0399(5) Uani d . . 1
S S1 0.21156(4) 0.34229(12) 0.67082(3) 0.0323(2) Uani d . . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 N1 119.6(2)
N2 C1 S1 121.58(17)
N1 C1 S1 118.80(16)
C3 C2 C14 114.96(19)
C3 C2 S1 107.82(16)
C14 C2 S1 107.38(15)
C3 C2 H2 108.8
C14 C2 H2 108.8
S1 C2 H2 108.8
C4 C3 C2 114.2(2)
C4 C3 H3A 108.7
C2 C3 H3A 108.7
C4 C3 H3B 108.7
C2 C3 H3B 108.7
H3A C3 H3B 107.6
O1 C4 N1 120.2(2)
O1 C4 C3 120.4(2)
N1 C4 C3 119.5(2)
N2 C5 C6 111.8(2)
N2 C5 H5A 109.3
C6 C5 H5A 109.3
N2 C5 H5B 109.3
C6 C5 H5B 109.3
H5A C5 H5B 107.9
C5 C6 C7 112.7(2)
C5 C6 H6A 109.1
C7 C6 H6A 109.1
C5 C6 H6B 109.1
C7 C6 H6B 109.1
H6A C6 H6B 107.8
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 121.7(2)
C9 C8 N1 119.2(2)
C13 C8 N1 119.0(2)
C8 C9 C10 119.0(2)
C8 C9 H9 120.5
C10 C9 H9 120.5
C11 C10 C9 120.1(2)
C11 C10 H10 120.0
C9 C10 H10 120.0
C12 C11 C10 120.1(2)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.4(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C8 C13 C12 118.7(2)
C8 C13 H13 120.6
C12 C13 H13 120.6
C15 C14 C19 119.1(2)
C15 C14 C2 119.2(2)
C19 C14 C2 121.7(2)
C14 C15 C16 120.3(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C17 C16 C15 120.3(3)
C17 C16 H16 119.9
C15 C16 H16 119.9
C18 C17 C16 119.9(2)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 120.2(3)
C17 C18 H18 119.9
C19 C18 H18 119.9
C18 C19 C14 120.2(2)
C18 C19 H19 119.9
C14 C19 H19 119.9
C4 N1 C1 127.16(19)
C4 N1 C8 115.70(18)
C1 N1 C8 117.01(18)
C1 N2 C5 117.86(19)
C1 S1 C2 102.16(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.265(3)
C1 N1 1.418(3)
C1 S1 1.772(2)
C2 C3 1.507(3)
C2 C14 1.512(3)
C2 S1 1.829(2)
C2 H2 1.0
C3 C4 1.503(3)
C3 H3A 0.99
C3 H3B 0.99
C4 O1 1.218(3)
C4 N1 1.390(3)
C5 N2 1.462(3)
C5 C6 1.507(3)
C5 H5A 0.99
C5 H5B 0.99
C6 C7 1.522(4)
C6 H6A 0.99
C6 H6B 0.99
C7 H7A 0.98
C7 H7B 0.98
C7 H7C 0.98
C8 C9 1.373(3)
C8 C13 1.382(3)
C8 N1 1.463(3)
C9 C10 1.394(3)
C9 H9 0.95
C10 C11 1.383(4)
C10 H10 0.95
C11 C12 1.378(4)
C11 H11 0.95
C12 C13 1.392(3)
C12 H12 0.95
C13 H13 0.95
C14 C15 1.386(3)
C14 C19 1.391(3)
C15 C16 1.386(3)
C15 H15 0.95
C16 C17 1.376(4)
C16 H16 0.95
C17 C18 1.375(4)
C17 H17 0.95
C18 C19 1.388(4)
C18 H18 0.95
C19 H19 0.95
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C14 C2 C3 C4 177.19(19)
S1 C2 C3 C4 -63.1(2)
C2 C3 C4 O1 -143.9(2)
C2 C3 C4 N1 36.7(3)
N2 C5 C6 C7 170.4(2)
C13 C8 C9 C10 0.7(4)
N1 C8 C9 C10 -176.9(2)
C8 C9 C10 C11 -1.4(4)
C9 C10 C11 C12 1.1(4)
C10 C11 C12 C13 0.0(4)
C9 C8 C13 C12 0.4(4)
N1 C8 C13 C12 178.1(2)
C11 C12 C13 C8 -0.8(4)
C3 C2 C14 C15 -137.3(2)
S1 C2 C14 C15 102.8(2)
C3 C2 C14 C19 44.1(3)
S1 C2 C14 C19 -75.9(3)
C19 C14 C15 C16 0.6(4)
C2 C14 C15 C16 -178.0(2)
C14 C15 C16 C17 -0.6(4)
C15 C16 C17 C18 -0.3(4)
C16 C17 C18 C19 1.1(5)
C17 C18 C19 C14 -1.0(4)
C15 C14 C19 C18 0.1(4)
C2 C14 C19 C18 178.8(2)
O1 C4 N1 C1 -174.7(2)
C3 C4 N1 C1 4.8(4)
O1 C4 N1 C8 1.0(3)
C3 C4 N1 C8 -179.5(2)
N2 C1 N1 C4 168.5(2)
S1 C1 N1 C4 -11.2(3)
N2 C1 N1 C8 -7.2(3)
S1 C1 N1 C8 173.18(16)
C9 C8 N1 C4 105.5(2)
C13 C8 N1 C4 -72.2(3)
C9 C8 N1 C1 -78.4(3)
C13 C8 N1 C1 104.0(3)
N1 C1 N2 C5 176.3(2)
S1 C1 N2 C5 -4.1(3)
C6 C5 N2 C1 174.9(2)
N2 C1 S1 C2 164.1(2)
N1 C1 S1 C2 -16.2(2)
C3 C2 S1 C1 49.95(18)
C14 C2 S1 C1 174.36(16)
