#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:59:26 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/64/7156484.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_7156484
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_name_common            3i
_chemical_name_systematic
5-Benzyl-3-isopropyl-1-phenyl-2-thioxoimidazolidin-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                 106.841(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4130(15)
_cell_length_b                   17.816(2)
_cell_length_c                   7.9085(10)
_cell_measurement_reflns_used    912
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.4646
_cell_measurement_theta_min      2.2863
_cell_volume                     1674.0(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0561
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9554
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3 and Hexane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0512
_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)+(0.0697P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                2379
_reflns_number_total             3838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob02066c2.cif
_cod_data_source_block           I_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7156480--7156486.cif.'
_cod_original_cell_volume        1674.0(4)
_cod_database_code               7156484
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 -0.0972(2) 0.29187(15) 0.5692(4) 0.0368(6) Uani d . . 1
H H1A -0.0617 0.2489 0.5294 0.055 Uiso calc U R 1
H H1B -0.1754 0.2964 0.4955 0.055 Uiso calc U R 1
H H1C -0.0957 0.2844 0.6927 0.055 Uiso calc U R 1
C C2 -0.03325(19) 0.36312(13) 0.5538(3) 0.0285(6) Uani d . . 1
H H2 -0.0397 0.3705 0.4259 0.034 Uiso calc U R 1
C C3 -0.0818(2) 0.43260(15) 0.6166(4) 0.0450(7) Uani d . . 1
H H3A -0.0858 0.4244 0.7372 0.067 Uiso calc U R 1
H H3B -0.1575 0.4422 0.538 0.067 Uiso calc U R 1
H H3C -0.0334 0.4759 0.6151 0.067 Uiso calc U R 1
C C4 0.17208(19) 0.35261(12) 0.5660(3) 0.0239(5) Uani d . . 1
C C5 0.1287(2) 0.34262(13) 0.8279(3) 0.0275(6) Uani d . . 1
C C6 0.25515(19) 0.33471(13) 0.8700(3) 0.0273(5) Uani d . . 1
H H6 0.2775 0.2826 0.9135 0.033 Uiso calc U R 1
C C7 0.3193(2) 0.39135(13) 1.0095(3) 0.0294(6) Uani d . . 1
H H7A 0.3021 0.3811 1.122 0.035 Uiso calc U R 1
H H7B 0.4011 0.3837 1.0303 0.035 Uiso calc U R 1
C C8 0.29113(19) 0.47217(13) 0.9588(3) 0.0275(5) Uani d . . 1
C C9 0.1985(2) 0.50715(15) 0.9907(3) 0.0367(6) Uani d . . 1
H H9 0.1525 0.4797 1.046 0.044 Uiso calc U R 1
C C10 0.1727(2) 0.58093(15) 0.9432(4) 0.0401(7) Uani d . . 1
H H10 0.1084 0.6036 0.964 0.048 Uiso calc U R 1
C C11 0.2400(2) 0.62181(15) 0.8654(3) 0.0399(7) Uani d . . 1
H H11 0.2227 0.6728 0.8339 0.048 Uiso calc U R 1
C C12 0.3324(2) 0.58842(14) 0.8334(3) 0.0378(6) Uani d . . 1
H H12 0.379 0.6164 0.7801 0.045 Uiso calc U R 1
C C13 0.3572(2) 0.51418(14) 0.8789(3) 0.0322(6) Uani d . . 1
H H13 0.4206 0.4915 0.8552 0.039 Uiso calc U R 1
C C14 0.38121(19) 0.34143(13) 0.6711(3) 0.0271(5) Uani d . . 1
C C15 0.4125(2) 0.39336(14) 0.5636(3) 0.0345(6) Uani d . . 1
H H15 0.3596 0.4289 0.4981 0.041 Uiso calc U R 1
C C16 0.5220(2) 0.39279(16) 0.5529(4) 0.0463(8) Uani d . . 1
H H16 0.5438 0.4279 0.4786 0.056 Uiso calc U R 1
C C17 0.5995(2) 0.34213(18) 0.6484(4) 0.0502(8) Uani d . . 1
H H17 0.6746 0.3426 0.6412 0.06 Uiso calc U R 1
C C18 0.5673(2) 0.29053(17) 0.7549(4) 0.0457(7) Uani d . . 1
H H18 0.6207 0.2555 0.8213 0.055 Uiso calc U R 1
C C19 0.4584(2) 0.28950(14) 0.7656(3) 0.0345(6) Uani d . . 1
H H19 0.4365 0.2533 0.8374 0.041 Uiso calc U R 1
N N1 0.08723(15) 0.35427(10) 0.6486(2) 0.0249(4) Uani d . . 1
N N2 0.27145(15) 0.34395(10) 0.6949(2) 0.0240(4) Uani d . . 1
O O1 0.07381(14) 0.33990(10) 0.9321(2) 0.0357(4) Uani d . . 1
S S1 0.15065(5) 0.35760(3) 0.34985(8) 0.03093(19) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C1 110.23(19)
N1 C2 C3 111.1(2)
C1 C2 C3 112.8(2)
N1 C2 H2 107.5
C1 C2 H2 107.5
C3 C2 H2 107.5
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N2 C4 N1 107.19(19)
N2 C4 S1 128.23(17)
N1 C4 S1 124.55(18)
O1 C5 N1 126.1(2)
O1 C5 C6 126.7(2)
N1 C5 C6 107.18(19)
N2 C6 C5 101.53(18)
N2 C6 C7 114.84(19)
C5 C6 C7 112.66(19)
N2 C6 H6 109.2
C5 C6 H6 109.2
C7 C6 H6 109.2
C8 C7 C6 113.84(19)
C8 C7 H7A 108.8
C6 C7 H7A 108.8
C8 C7 H7B 108.8
C6 C7 H7B 108.8
H7A C7 H7B 107.7
C13 C8 C9 117.9(2)
C13 C8 C7 120.9(2)
C9 C8 C7 121.2(2)
C10 C9 C8 121.1(2)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C11 120.1(2)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 119.8(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.0(2)
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C8 121.1(2)
C12 C13 H13 119.4
C8 C13 H13 119.4
C19 C14 C15 120.2(2)
C19 C14 N2 119.2(2)
C15 C14 N2 120.5(2)
C14 C15 C16 119.1(3)
C14 C15 H15 120.4
C16 C15 H15 120.4
C17 C16 C15 120.9(3)
C17 C16 H16 119.5
C15 C16 H16 119.5
C16 C17 C18 119.5(3)
C16 C17 H17 120.3
C18 C17 H17 120.3
C19 C18 C17 120.5(3)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C14 119.7(3)
C18 C19 H19 120.1
C14 C19 H19 120.1
C5 N1 C4 111.85(19)
C5 N1 C2 124.18(19)
C4 N1 C2 123.88(19)
C4 N2 C14 126.58(19)
C4 N2 C6 112.13(18)
C14 N2 C6 121.26(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.521(3)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C2 N1 1.475(3)
C2 C3 1.522(3)
C2 H2 1.0
C3 H3A 0.98
C3 H3B 0.98
C3 H3C 0.98
C4 N2 1.362(3)
C4 N1 1.391(3)
C4 S1 1.655(2)
C5 O1 1.213(3)
C5 N1 1.377(3)
C5 C6 1.513(3)
C6 N2 1.466(3)
C6 C7 1.536(3)
C6 H6 1.0
C7 C8 1.508(3)
C7 H7A 0.99
C7 H7B 0.99
C8 C13 1.390(3)
C8 C9 1.393(3)
C9 C10 1.379(4)
C9 H9 0.95
C10 C11 1.380(4)
C10 H10 0.95
C11 C12 1.379(4)
C11 H11 0.95
C12 C13 1.382(3)
C12 H12 0.95
C13 H13 0.95
C14 C19 1.385(3)
C14 C15 1.386(3)
C14 N2 1.429(3)
C15 C16 1.386(3)
C15 H15 0.95
C16 C17 1.374(4)
C16 H16 0.95
C17 C18 1.382(4)
C17 H17 0.95
C18 C19 1.378(3)
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
O1 C5 C6 N2 -179.2(2)
N1 C5 C6 N2 0.3(2)
O1 C5 C6 C7 -55.8(3)
N1 C5 C6 C7 123.6(2)
N2 C6 C7 C8 57.7(3)
C5 C6 C7 C8 -57.9(3)
C6 C7 C8 C13 -95.2(3)
C6 C7 C8 C9 85.0(3)
C13 C8 C9 C10 0.5(4)
C7 C8 C9 C10 -179.6(2)
C8 C9 C10 C11 -1.1(4)
C9 C10 C11 C12 0.8(4)
C10 C11 C12 C13 0.1(4)
C11 C12 C13 C8 -0.7(4)
C9 C8 C13 C12 0.4(4)
C7 C8 C13 C12 -179.5(2)
C19 C14 C15 C16 -0.3(4)
N2 C14 C15 C16 175.5(2)
C14 C15 C16 C17 -0.6(4)
C15 C16 C17 C18 0.7(4)
C16 C17 C18 C19 0.1(4)
C17 C18 C19 C14 -1.1(4)
C15 C14 C19 C18 1.2(4)
N2 C14 C19 C18 -174.7(2)
O1 C5 N1 C4 -178.7(2)
C6 C5 N1 C4 1.9(3)
O1 C5 N1 C2 -1.9(4)
C6 C5 N1 C2 178.61(19)
N2 C4 N1 C5 -3.4(2)
S1 C4 N1 C5 174.74(17)
N2 C4 N1 C2 179.85(19)
S1 C4 N1 C2 -2.0(3)
C1 C2 N1 C5 -62.8(3)
C3 C2 N1 C5 63.0(3)
C1 C2 N1 C4 113.5(2)
C3 C2 N1 C4 -120.7(2)
N1 C4 N2 C14 -178.14(19)
S1 C4 N2 C14 3.8(3)
N1 C4 N2 C6 3.6(2)
S1 C4 N2 C6 -174.46(17)
C19 C14 N2 C4 -138.4(2)
C15 C14 N2 C4 45.7(3)
C19 C14 N2 C6 39.7(3)
C15 C14 N2 C6 -136.1(2)
C5 C6 N2 C4 -2.4(2)
C7 C6 N2 C4 -124.2(2)
C5 C6 N2 C14 179.24(18)
C7 C6 N2 C14 57.4(3)
