#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:04:49 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/07/2020791.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_2020791
loop_
_publ_author_name
'Zarei, Seyed Amir'
'Piltan, Mohammad'
'Mashhun, Asmar'
'Rudbari, Hadi Amiri'
'Bruno, Giuseppe'
_publ_section_title
;
 2,2'-[(Disulfanediyl)bis{5-[(1E)-(2-hydroxybenzylidene)amino]-1,3-thiazole-4,2-diyl}]diphenol:
 synthesis, crystal structure and calculation of molecular
 hyperpolarizability
;
_journal_coeditor_code           UK3134
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229617008257
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C32 H22 N4 O4 S4'
_chemical_formula_moiety         'C32 H22 N4 O4 S4'
_chemical_formula_sum            'C32 H22 N4 O4 S4'
_chemical_formula_weight         654.77
_chemical_name_common
2,2'-(Disulfanediylbis{5-[(1E)-(2-hydroxybenzylidene)amino]-1,3-thiazole-4,2-diyl})diphenol
_chemical_name_systematic
2-[5-[(E)-(2-Hydroxybenzylidene)amino]-4-(2-{5-[(E)-(2-hydroxybenzylidene)amino]-2-(2-hydroxyphenyl)-1,3-thiazol-4-yl}disulfanyl)-1,3-thiazol-2-yl]phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 96.933(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1813(7)
_cell_length_b                   7.2661(4)
_cell_length_c                   15.6283(8)
_cell_measurement_reflns_used    7100
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.6
_cell_volume                     1485.88(14)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
XPW (Siemens, 1996)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46264
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.626
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       irregular
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0712P)²+0.3626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                2127
_reflns_number_total             2918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            uk3134sup1.cif
_cod_data_source_block           I
_cod_database_code               2020791
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_occupancy
S S1 0.51227(4) 0.27182(8) 0.40014(4) 0.0504(2) Uani d 1
S S2 0.45256(5) -0.26435(9) 0.29971(5) 0.0680(3) Uani d 1
O O1 0.20486(15) -0.0275(3) 0.18068(13) 0.0707(5) Uani d 1
C C1 0.60088(16) 0.1073(3) 0.44137(14) 0.0476(5) Uani d 1
C C2 0.68782(17) 0.1542(3) 0.50469(14) 0.0486(5) Uani d 1
C C3 0.71056(19) 0.3356(4) 0.52755(15) 0.0581(6) Uani d 1
H H3 0.670628 0.429445 0.500667 0.070 Uiso calc 1
C C4 0.7905(2) 0.3802(4) 0.58887(17) 0.0695(7) Uani d 1
H H4 0.804961 0.502434 0.603168 0.083 Uiso calc 1
C C5 0.8494(2) 0.2387(5) 0.62913(18) 0.0724(8) Uani d 1
H H5 0.902945 0.266913 0.671441 0.087 Uiso calc 1
C C6 0.82965(19) 0.0594(4) 0.60741(16) 0.0664(7) Uani d 1
H H6 0.869725 -0.033344 0.635078 0.080 Uiso calc 1
C C7 0.75044(18) 0.0143(4) 0.54450(15) 0.0554(6) Uani d 1
O O2 0.73547(15) -0.1661(3) 0.52538(14) 0.0717(6) Uani d 1
N N1 0.58145(14) -0.0592(3) 0.41213(12) 0.0527(5) Uani d 1
C C8 0.49473(18) -0.0641(3) 0.35449(15) 0.0509(6) Uani d 1
C C9 0.44575(16) 0.1005(3) 0.33905(14) 0.0469(5) Uani d 1
N N2 0.35841(14) 0.1230(3) 0.28175(12) 0.0494(5) Uani d 1
C C10 0.31827(17) 0.2798(3) 0.26292(15) 0.0509(6) Uani d 1
H H10 0.349447 0.384448 0.288246 0.061 Uiso calc 1
C C11 0.22652(17) 0.3003(3) 0.20390(15) 0.0506(6) Uani d 1
C C12 0.17275(18) 0.1465(4) 0.16608(15) 0.0551(6) Uani d 1
C C13 0.0829(2) 0.1748(5) 0.11118(17) 0.0744(8) Uani d 1
H H13 0.046400 0.074815 0.086368 0.089 Uiso calc 1
C C14 0.0483(2) 0.3503(6) 0.09371(19) 0.0872(10) Uani d 1
H H14 -0.012374 0.367658 0.057622 0.105 Uiso calc 1
C C15 0.1012(2) 0.5014(5) 0.1283(2) 0.0884(10) Uani d 1
H H15 0.077111 0.619459 0.114700 0.106 Uiso calc 1
C C16 0.1895(2) 0.4769(4) 0.18286(17) 0.0687(7) Uani d 1
H H16 0.225294 0.578972 0.206231 0.082 Uiso calc 1
H H1 0.266(2) -0.023(4) 0.2164(19) 0.096(11) Uiso d 1
H H2 0.688(3) -0.178(5) 0.481(2) 0.112(13) Uiso 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C10 C11 . 122.3(2) y
C9 C8 S2 . 121.82(18) y
N2 C9 S1 . 126.64(17) y
N1 C1 S1 . 114.32(17) y
N1 C1 C2 . 123.9(2) y
C8 S2 S2 2_655 100.33(8) y
C10 N2 C9 . 123.1(2) y
N1 C8 S2 . 122.42(18) y
C9 S1 C1 . 89.02(11) y
C1 N1 C8 . 111.53(19) y
C2 C1 S1 . 121.81(18) y
C12 O1 H1 . 108(2) ?
C3 C2 C7 . 118.4(2) ?
C3 C2 C1 . 121.5(2) ?
C7 C2 C1 . 120.1(2) ?
C4 C3 C2 . 121.8(3) ?
C4 C3 H3 . 119.1 ?
C2 C3 H3 . 119.1 ?
C3 C4 C5 . 118.7(3) ?
C3 C4 H4 . 120.7 ?
C5 C4 H4 . 120.7 ?
C6 C5 C4 . 120.9(3) ?
C6 C5 H5 . 119.5 ?
C4 C5 H5 . 119.5 ?
C5 C6 C7 . 120.5(3) ?
C5 C6 H6 . 119.7 ?
C7 C6 H6 . 119.7 ?
O2 C7 C6 . 117.6(2) ?
O2 C7 C2 . 122.7(2) ?
C6 C7 C2 . 119.7(3) ?
C7 O2 H2 . 110(3) ?
C9 C8 N1 . 115.7(2) ?
C8 C9 N2 . 123.9(2) ?
C8 C9 S1 . 109.45(17) ?
N2 C10 H10 . 118.9 ?
C11 C10 H10 . 118.9 ?
C16 C11 C12 . 118.9(2) ?
C16 C11 C10 . 119.3(2) ?
C12 C11 C10 . 121.8(2) ?
O1 C12 C13 . 118.1(3) ?
O1 C12 C11 . 122.7(2) ?
C13 C12 C11 . 119.2(3) ?
C14 C13 C12 . 119.9(3) ?
C14 C13 H13 . 120.1 ?
C12 C13 H13 . 120.1 ?
C13 C14 C15 . 121.6(3) ?
C13 C14 H14 . 119.2 ?
C15 C14 H14 . 119.2 ?
C16 C15 C14 . 119.5(3) ?
C16 C15 H15 . 120.2 ?
C14 C15 H15 . 120.2 ?
C15 C16 C11 . 120.8(3) ?
C15 C16 H16 . 119.6 ?
C11 C16 H16 . 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
N2 C10 . 1.275(3) y
C1 N1 . 1.307(3) y
C8 C9 . 1.366(3) y
C10 C11 . 1.437(3) y
S1 C1 . 1.740(2) y
S2 S2 2_655 2.1089(16) y
C9 N2 . 1.380(3) y
N1 C8 . 1.368(3) y
C1 C2 . 1.461(3) y
S1 C9 . 1.740(2) y
S2 C8 . 1.745(2) y
O1 C12 . 1.344(3) ?
O1 H1 . 0.92(3) ?
C2 C3 . 1.389(4) ?
C2 C7 . 1.406(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.364(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9300 ?
C7 O2 . 1.354(3) ?
O2 H2 . 0.88(4) ?
C10 H10 . 0.9300 ?
C11 C16 . 1.398(4) ?
C11 C12 . 1.414(3) ?
C12 C13 . 1.391(3) ?
C13 C14 . 1.371(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.376(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.369(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 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
O1 H1 N2 . 0.92(3) 1.83(3) 2.649(3) 146(3)
O2 H2 N1 . 0.88(4) 1.87(4) 2.644(3) 145(4)
C10 H10 S2 1_565 0.93 2.89 3.767(3) 158.4
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
_geom_torsion_publ_flag
S2 S2 C8 C9 2_655 95.8(2) yes
C1 C2 C7 O2 . 1.6(3) yes
C8 N1 C1 S1 . 0.4(2) yes
C9 N2 C10 C11 . -179.2(2) yes
S2 S2 C8 N1 2_655 -80.7(2) yes
C8 N1 C1 C2 . 179.2(2) yes
C10 N2 C9 C8 . -174.2(2) yes

_cod_database_fobs_code 2020791
