#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/66/2236632.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_2236632
loop_
_publ_author_name
'Kargar, Hadi'
'Kia, Reza'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 4-Bromo-2-[(E)-(2-{2-[(2-{[(E)-5-bromo-2-hydroxybenzylidene]amino}phenyl)sulfanyl]ethylsulfanyl}phenyl)iminomethyl]phenol
;
_journal_coeditor_code           SU2486
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2635
_journal_paper_doi               10.1107/S1600536812034071
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C28 H22 Br2 N2 O2 S2'
_chemical_formula_moiety         'C28 H22 Br2 N2 O2 S2'
_chemical_formula_sum            'C28 H22 Br2 N2 O2 S2'
_chemical_formula_weight         642.42
_chemical_name_systematic
4-Bromo-2-[(E)-(2-{2-[(2-{[(E)-5-bromo-2-hydroxybenzylidene]amino}phenyl)sulfanyl]ethylsulfanyl}phenyl)iminomethyl]phenol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.444(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.9124(18)
_cell_length_b                   5.4112(7)
_cell_length_c                   17.409(2)
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      2.47
_cell_volume                     1309.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0930
_diffrn_reflns_av_sigmaI/netI    0.1255
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10754
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.284
_exptl_absorpt_correction_T_max  0.6940
_exptl_absorpt_correction_T_min  0.3927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0524
_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)+(0.0347P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                1277
_reflns_number_total             2879
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2486.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236632
_cod_database_fobs_code          2236632
loop_
_symmetry_equiv_pos_as_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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.55873(4) 1.84843(11) 0.63714(3) 0.0707(3) Uani d . 1 1
S S1 0.08346(11) 0.7463(2) 0.57293(8) 0.0622(4) Uani d . 1 1
O O1 0.2265(3) 1.2258(6) 0.51696(19) 0.0684(11) Uani d . 1 1
H H1 0.2092 1.1303 0.5566 0.103 Uiso d R 1 1
N N1 0.2327(3) 0.9977(8) 0.6512(2) 0.0479(10) Uani d . 1 1
C C1 0.2994(4) 1.3675(9) 0.5463(3) 0.0502(13) Uani d . 1 1
C C2 0.3336(4) 1.5574(10) 0.5026(3) 0.0633(16) Uani d . 1 1
H H2 0.3048 1.5889 0.4544 0.076 Uiso calc R 1 1
C C3 0.4094(4) 1.7013(9) 0.5286(3) 0.0577(15) Uani d . 1 1
H H3 0.4322 1.8277 0.4981 0.069 Uiso calc R 1 1
C C4 0.4522(3) 1.6562(9) 0.6015(3) 0.0492(13) Uani d . 1 1
C C5 0.4185(3) 1.4704(9) 0.6453(3) 0.0483(13) Uani d . 1 1
H H5 0.4480 1.4404 0.6934 0.058 Uiso calc R 1 1
C C6 0.3408(3) 1.3230(8) 0.6206(2) 0.0439(12) Uani d . 1 1
C C7 0.3043(4) 1.1325(9) 0.6696(3) 0.0510(13) Uani d . 1 1
H H7 0.3352 1.1076 0.7174 0.061 Uiso calc R 1 1
C C8 0.1967(3) 0.8149(9) 0.7006(3) 0.0436(12) Uani d . 1 1
C C9 0.2299(4) 0.7718(10) 0.7752(3) 0.0672(16) Uani d . 1 1
H H9 0.2797 0.8671 0.7968 0.081 Uiso calc R 1 1
C C10 0.1892(4) 0.5876(10) 0.8175(3) 0.0692(17) Uani d . 1 1
H H10 0.2109 0.5615 0.8681 0.083 Uiso calc R 1 1
C C11 0.1171(4) 0.4423(10) 0.7861(3) 0.0616(15) Uani d . 1 1
H H11 0.0911 0.3157 0.8148 0.074 Uiso calc R 1 1
C C12 0.0836(4) 0.4857(10) 0.7114(3) 0.0595(15) Uani d . 1 1
H H12 0.0338 0.3893 0.6903 0.071 Uiso calc R 1 1
C C13 0.1228(3) 0.6697(9) 0.6678(3) 0.0447(12) Uani d . 1 1
C C14 0.0071(4) 0.4938(9) 0.5431(2) 0.0567(14) Uani d . 1 1
H H14A 0.0368 0.3379 0.5582 0.068 Uiso calc R 1 1
H H14B -0.0543 0.5063 0.5671 0.068 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'
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'
Br Br -0.2901 2.4595 '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
C13 S1 C14 . 104.3(2)
C1 O1 H1 . 104.8
C7 N1 C8 . 123.0(4)
O1 C1 C2 . 119.0(4)
O1 C1 C6 . 121.3(5)
C2 C1 C6 . 119.7(5)
C3 C2 C1 . 121.3(5)
C3 C2 H2 . 119.3
C1 C2 H2 . 119.3
C2 C3 C4 . 119.4(5)
C2 C3 H3 . 120.3
C4 C3 H3 . 120.3
C5 C4 C3 . 119.7(5)
C5 C4 Br1 . 120.4(4)
C3 C4 Br1 . 119.9(4)
C4 C5 C6 . 122.0(4)
C4 C5 H5 . 119.0
C6 C5 H5 . 119.0
C5 C6 C1 . 117.7(4)
C5 C6 C7 . 120.8(4)
C1 C6 C7 . 121.5(4)
N1 C7 C6 . 123.7(5)
N1 C7 H7 . 118.1
C6 C7 H7 . 118.1
C9 C8 C13 . 120.1(5)
C9 C8 N1 . 125.2(5)
C13 C8 N1 . 114.7(4)
C10 C9 C8 . 119.8(5)
C10 C9 H9 . 120.1
C8 C9 H9 . 120.1
C11 C10 C9 . 120.9(5)
C11 C10 H10 . 119.5
C9 C10 H10 . 119.5
C10 C11 C12 . 119.3(5)
C10 C11 H11 . 120.3
C12 C11 H11 . 120.3
C13 C12 C11 . 121.0(5)
C13 C12 H12 . 119.5
C11 C12 H12 . 119.5
C12 C13 C8 . 118.8(4)
C12 C13 S1 . 124.8(4)
C8 C13 S1 . 116.3(4)
C14 C14 S1 3_566 107.8(4)
C14 C14 H14A 3_566 110.2
S1 C14 H14A . 110.2
C14 C14 H14B 3_566 110.2
S1 C14 H14B . 110.2
H14A C14 H14B . 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.894(5)
S1 C13 . 1.766(5)
S1 C14 . 1.793(5)
O1 C1 . 1.354(5)
O1 H1 . 0.9026
N1 C7 . 1.265(5)
N1 C8 . 1.416(5)
C1 C2 . 1.377(6)
C1 C6 . 1.413(6)
C2 C3 . 1.373(6)
C2 H2 . 0.9300
C3 C4 . 1.399(6)
C3 H3 . 0.9300
C4 C5 . 1.358(6)
C5 C6 . 1.396(6)
C5 H5 . 0.9300
C6 C7 . 1.444(6)
C7 H7 . 0.9300
C8 C9 . 1.379(6)
C8 C13 . 1.397(6)
C9 C10 . 1.376(6)
C9 H9 . 0.9300
C10 C11 . 1.369(7)
C10 H10 . 0.9300
C11 C12 . 1.383(6)
C11 H11 . 0.9300
C12 C13 . 1.379(6)
C12 H12 . 0.9300
C14 C14 3_566 1.508(8)
C14 H14A . 0.9700
C14 H14B . 0.9700
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
O1 H1 N1 0.90 1.81 2.641(5) 151 y
O1 H1 S1 0.90 2.74 3.436(4) 135 y
