#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/21/2222125.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_2222125
loop_
_publ_author_name
'Zhang, Gang'
'Wang, Yan-lun'
'Long, Sheng-ru'
'Yang, Jie'
_publ_section_title
;
 Bis[4-(4-aminophenylsulfanyl)phenyl] ketone
;
_journal_coeditor_code           RZ2311
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1251
_journal_paper_doi               10.1107/S1600536809016948
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H20 N2 O S2'
_chemical_formula_moiety         'C25 H20 N2 O S2'
_chemical_formula_sum            'C25 H20 N2 O S2'
_chemical_formula_weight         428.55
_chemical_name_common            4,4'-bis(4-aminophenylthio)benzophenone
_chemical_name_systematic
;
Bis[4-(4-aminophenylsulfanyl)phenyl) ketone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.64(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.945(3)
_cell_length_b                   6.025(2)
_cell_length_c                   20.793(5)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      9.36
_cell_measurement_theta_min      4.31
_cell_volume                     2221.0(11)
_computing_cell_refinement       'DIFRAC (Gabe et al., 1993)'
_computing_data_collection       'DIFRAC (Gabe et al., 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.0100
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2261
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        2.361
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.8992
_exptl_absorpt_correction_T_min  0.8773
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '(WinGX; Farrugia, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0979P)²+0.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                1441
_reflns_number_total             1990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz2311.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2221.1(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222125
_cod_database_fobs_code          2222125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, 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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.59611(4) 0.88028(12) 0.52196(3) 0.0591(3) Uani d . 1 . .
O O1 0.5000 0.1894(4) 0.2500 0.0638(7) Uani d S 1 . .
N N1 0.8241(2) 0.3345(7) 0.73370(17) 0.0954(11) Uani d . 1 . .
H HN1 0.811(2) 0.224(7) 0.7515(19) 0.096(13) Uiso d . 1 . .
H HN2 0.8651(18) 0.371(5) 0.7407(16) 0.071(11) Uiso d . 1 . .
C C1 0.5000 0.3937(5) 0.2500 0.0397(7) Uani d S 1 . .
C C2 0.52388(11) 0.5146(3) 0.31641(10) 0.0364(5) Uani d . 1 . .
C C3 0.57458(12) 0.4134(4) 0.37505(11) 0.0427(5) Uani d . 1 . .
H H3 0.5933 0.2731 0.3714 0.051 Uiso calc R 1 . .
C C4 0.59739(12) 0.5168(4) 0.43805(11) 0.0437(5) Uani d . 1 . .
H H4 0.6312 0.4466 0.4764 0.052 Uiso calc R 1 . .
C C5 0.56977(12) 0.7271(4) 0.44448(11) 0.0409(5) Uani d . 1 . .
C C6 0.51783(12) 0.8281(4) 0.38664(10) 0.0396(5) Uani d . 1 . .
H H6 0.4979 0.9662 0.3907 0.048 Uiso calc R 1 . .
C C7 0.49596(11) 0.7241(3) 0.32367(10) 0.0371(5) Uani d . 1 . .
H H7 0.4621 0.7944 0.2854 0.045 Uiso calc R 1 . .
C C8 0.66367(12) 0.7082(4) 0.58244(11) 0.0484(6) Uani d . 1 . .
C C9 0.73981(14) 0.7565(5) 0.60170(13) 0.0606(7) Uani d . 1 . .
H H9 0.7555 0.8750 0.5814 0.073 Uiso calc R 1 . .
C C10 0.79254(14) 0.6301(5) 0.65085(14) 0.0650(8) Uani d . 1 . .
H H10 0.8435 0.6644 0.6631 0.078 Uiso calc R 1 . .
C C11 0.77125(14) 0.4541(5) 0.68221(12) 0.0580(7) Uani d . 1 . .
C C12 0.69484(15) 0.4026(5) 0.66200(13) 0.0634(7) Uani d . 1 . .
H H12 0.6794 0.2819 0.6816 0.076 Uiso calc R 1 . .
C C13 0.64197(13) 0.5290(5) 0.61320(12) 0.0567(7) Uani d . 1 . .
H H13 0.5911 0.4940 0.6007 0.068 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C8 . . 103.99(12) ?
C11 N1 HN1 . . 121(2) ?
C11 N1 HN2 . . 114(2) ?
HN1 N1 HN2 . . 125(3) ?
O1 C1 C2 . . 119.39(12) ?
O1 C1 C2 . 6_656 119.39(12) ?
C2 C1 C2 . 6_656 121.2(2) ?
C7 C2 C3 . . 118.00(18) ?
C7 C2 C1 . . 122.75(18) ?
C3 C2 C1 . . 119.21(19) ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 120.0(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 119.15(19) ?
C4 C5 S1 . . 124.48(16) ?
C6 C5 S1 . . 116.37(17) ?
C7 C6 C5 . . 120.3(2) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C2 . . 121.02(19) ?
C6 C7 H7 . . 119.5 ?
C2 C7 H7 . . 119.5 ?
C9 C8 C13 . . 118.5(2) ?
C9 C8 S1 . . 119.9(2) ?
C13 C8 S1 . . 121.52(17) ?
C10 C9 C8 . . 120.4(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 N1 . . 120.9(3) ?
C10 C11 C12 . . 118.4(2) ?
N1 C11 C12 . . 120.7(3) ?
C13 C12 C11 . . 120.5(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.8(2) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 . 1.769(2) ?
S1 C8 . 1.777(3) ?
O1 C1 . 1.231(3) ?
N1 C11 . 1.383(4) ?
N1 HN1 . 0.84(4) ?
N1 HN2 . 0.77(3) ?
C1 C2 . 1.484(2) ?
C1 C2 6_656 1.484(2) ?
C2 C7 . 1.397(3) ?
C2 C3 . 1.398(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.395(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.397(3) ?
C6 C7 . 1.377(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.385(3) ?
C8 C13 . 1.389(4) ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.377(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.393(4) ?
C12 C13 . 1.377(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 HN2 O1 7_656 0.77(3) 2.52(3) 3.231(4) 154(3)
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C7 . . . . -150.51(15) ?
C2 C1 C2 C7 6_656 . . . 29.49(15) ?
O1 C1 C2 C3 . . . . 27.3(2) ?
C2 C1 C2 C3 6_656 . . . -152.7(2) ?
C7 C2 C3 C4 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . -178.80(18) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C3 C4 C5 C6 . . . . 1.3(3) ?
C3 C4 C5 S1 . . . . -178.56(17) ?
C8 S1 C5 C4 . . . . 1.7(2) ?
C8 S1 C5 C6 . . . . -178.18(16) ?
C4 C5 C6 C7 . . . . -2.0(3) ?
S1 C5 C6 C7 . . . . 177.89(16) ?
C5 C6 C7 C2 . . . . 1.3(3) ?
C3 C2 C7 C6 . . . . 0.2(3) ?
C1 C2 C7 C6 . . . . 178.04(18) ?
C5 S1 C8 C9 . . . . 102.6(2) ?
C5 S1 C8 C13 . . . . -79.8(2) ?
C13 C8 C9 C10 . . . . -0.6(4) ?
S1 C8 C9 C10 . . . . 177.1(2) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C9 C10 C11 N1 . . . . -177.0(3) ?
C9 C10 C11 C12 . . . . 1.5(4) ?
C10 C11 C12 C13 . . . . -1.8(4) ?
N1 C11 C12 C13 . . . . 176.7(3) ?
C11 C12 C13 C8 . . . . 0.9(4) ?
C9 C8 C13 C12 . . . . 0.3(4) ?
S1 C8 C13 C12 . . . . -177.4(2) ?
