#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/41/2234197.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234197
loop_
_publ_author_name
'Umar, M. Naveed'
'Tahir, M. Nawaz'
'Shoaib, Mohammad'
'Ali, Akbar'
'Khan, Imran'
_publ_section_title
;
 1,3-Bis(1-phenylethyl)imidazolidine-2-thione
;
_journal_coeditor_code           GK2471
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1188
_journal_paper_doi               10.1107/S160053681201224X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H22 N2 S'
_chemical_formula_moiety         'C19 H22 N2 S'
_chemical_formula_sum            'C19 H22 N2 S'
_chemical_formula_weight         310.45
_chemical_name_systematic
;
1,3-Bis(1-phenylethyl)imidazolidine-2-thione
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8692(5)
_cell_length_b                   5.8692(5)
_cell_length_c                   50.637(5)
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      3.22
_cell_volume                     1744.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.80
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            18956
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.166
_refine_ls_abs_structure_details 'Flack (1983), 569 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0459P)²+1.2139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                1150
_reflns_number_total             1717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2471.cif
_cod_data_source_block           I
_cod_database_code               2234197
_cod_database_fobs_code          2234197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+1/4'
'-y+1/2, x+1/2, z+3/4'
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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 1.12952(18) 1.12952(18) 0.0000 0.0805(6) Uani d S 1 2
N N1 0.8146(6) 0.8492(6) 0.02136(5) 0.0692(10) Uani d . 1 1
C C1 0.9276(6) 0.9276(6) 0.0000 0.0598(14) Uani d S 1 2
C C2 0.6343(8) 0.6919(7) 0.01411(7) 0.0723(12) Uani d . 1 1
H H2A 0.4858 0.7636 0.0154 0.087 Uiso calc R 1 1
H H2B 0.6367 0.5571 0.0252 0.087 Uiso calc R 1 1
C C3 0.8267(8) 0.9498(8) 0.04762(8) 0.0687(12) Uani d . 1 1
H H3 0.962(7) 1.038(7) 0.0469(8) 0.082 Uiso d . 1 1
C C4 0.6154(10) 1.0894(8) 0.05338(9) 0.1018(18) Uani d . 1 1
H H4A 0.5884 1.1932 0.0391 0.153 Uiso calc R 1 1
H H4B 0.6372 1.1738 0.0694 0.153 Uiso calc R 1 1
H H4C 0.4868 0.9897 0.0553 0.153 Uiso calc R 1 1
C C5 0.8783(7) 0.7647(7) 0.06798(7) 0.0579(10) Uani d . 1 1
C C6 1.0569(8) 0.6131(9) 0.06414(9) 0.0843(14) Uani d . 1 1
H H6 1.1454 0.6219 0.0489 0.101 Uiso calc R 1 1
C C7 1.1034(9) 0.4468(9) 0.08326(11) 0.0963(17) Uani d . 1 1
H H7 1.2213 0.3437 0.0805 0.116 Uiso calc R 1 1
C C8 0.9810(11) 0.4343(9) 0.10538(10) 0.1002(19) Uani d . 1 1
H H8 1.0161 0.3253 0.1181 0.120 Uiso calc R 1 1
C C9 0.8049(10) 0.5808(9) 0.10942(9) 0.0949(17) Uani d . 1 1
H H9 0.7157 0.5700 0.1246 0.114 Uiso calc R 1 1
C C10 0.7614(8) 0.7429(8) 0.09100(7) 0.0764(12) Uani d . 1 1
H H10 0.6442 0.8456 0.0943 0.092 Uiso calc R 1 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 C2 . . 111.9(3)
C1 N1 C3 . . 124.7(3)
C2 N1 C3 . . 121.6(3)
N1 C1 N1 6 . 107.9(4)
N1 C1 S1 6 . 126.1(2)
N1 C1 S1 . . 126.1(2)
N1 C2 C2 . 6 102.7(2)
N1 C2 H2A . . 111.2
C2 C2 H2A 6 . 111.2
N1 C2 H2B . . 111.2
C2 C2 H2B 6 . 111.2
H2A C2 H2B . . 109.1
N1 C3 C4 . . 110.8(4)
N1 C3 C5 . . 109.7(3)
C4 C3 C5 . . 114.6(4)
N1 C3 H3 . . 103(2)
C4 C3 H3 . . 113(3)
C5 C3 H3 . . 104(3)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C10 C5 C6 . . 116.2(4)
C10 C5 C3 . . 123.1(4)
C6 C5 C3 . . 120.7(4)
C5 C6 C7 . . 119.8(4)
C5 C6 H6 . . 120.1
C7 C6 H6 . . 120.1
C8 C7 C6 . . 120.9(5)
C8 C7 H7 . . 119.5
C6 C7 H7 . . 119.5
C7 C8 C9 . . 120.1(5)
C7 C8 H8 . . 120.0
C9 C8 H8 . . 120.0
C10 C9 C8 . . 118.9(5)
C10 C9 H9 . . 120.6
C8 C9 H9 . . 120.6
C9 C10 C5 . . 124.1(5)
C9 C10 H10 . . 117.9
C5 C10 H10 . . 117.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.676(5)
N1 C1 . 1.350(4)
N1 C2 . 1.451(5)
N1 C3 . 1.456(5)
C1 N1 6 1.350(4)
C2 C2 6 1.507(7)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 C4 . 1.515(6)
C3 C5 . 1.528(6)
C3 H3 . 0.95(4)
C4 H4A . 0.9600
C4 H4B . 0.9600
C4 H4C . 0.9600
C5 C10 . 1.359(5)
C5 C6 . 1.388(6)
C6 C7 . 1.402(7)
C6 H6 . 0.9300
C7 C8 . 1.333(7)
C7 H7 . 0.9300
C8 C9 . 1.360(7)
C8 H8 . 0.9300
C9 C10 . 1.357(6)
C9 H9 . 0.9300
C10 H10 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 S1 0.95(4) 2.63(4) 3.176(4) 117(3) no
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_site_symmetry_4
_geom_torsion
C2 N1 C1 N1 6 -6.1(2)
C3 N1 C1 N1 6 -171.0(5)
C2 N1 C1 S1 . 173.9(2)
C3 N1 C1 S1 . 9.0(5)
C1 N1 C2 C2 6 14.8(5)
C3 N1 C2 C2 6 -179.8(4)
C1 N1 C3 C4 . 102.8(5)
C2 N1 C3 C4 . -60.7(5)
C1 N1 C3 C5 . -129.6(4)
C2 N1 C3 C5 . 66.9(5)
N1 C3 C5 C10 . -132.8(4)
C4 C3 C5 C10 . -7.4(6)
N1 C3 C5 C6 . 49.8(5)
C4 C3 C5 C6 . 175.2(4)
C10 C5 C6 C7 . 1.4(7)
C3 C5 C6 C7 . 179.1(4)
C5 C6 C7 C8 . -1.2(8)
C6 C7 C8 C9 . 1.5(8)
C7 C8 C9 C10 . -2.0(8)
C8 C9 C10 C5 . 2.4(8)
C6 C5 C10 C9 . -2.1(7)
C3 C5 C10 C9 . -179.7(4)
