#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/87/4508701.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508701
loop_
_publ_author_name
'Fridman, N.'
'Speiser, S.'
'Kaftory, M.'
_publ_section_title
;
 Structures and Chromogenic Properties of Bisimidazole Derivatives
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1653
_journal_paper_doi               10.1021/cg060107j
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C36 H28 N4 S'
_chemical_formula_sum            'C36 H28 N4 S'
_chemical_formula_weight         548.68
_chemical_name_systematic
;
 1H-Imidazole, 2,2'-(2,5-thiophenediyl)bis[1-methyl-4,5-diphenyl]
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.43(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.728(5)
_cell_length_b                   9.962(2)
_cell_length_c                   12.387(2)
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      1.018
_cell_volume                     2835.6(10)
_computing_cell_refinement       'Denzo SMN (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'Denzo SMN (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi scan'
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0891
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3407
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1796
_reflns_number_total             2486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060107jsup5.cif
_cod_data_source_block           natalia69
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2835.6(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4508701
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.5000 0.13229(8) -0.2500 0.0519(3) Uani 1 2 d S
N1 N 0.55862(7) 0.18704(18) -0.01067(15) 0.0509(5) Uani 1 1 d .
N2 N 0.60267(8) -0.00909(17) 0.03366(15) 0.0517(5) Uani 1 1 d .
C1 C 0.67158(9) 0.0316(2) 0.21799(19) 0.0516(6) Uani 1 1 d .
C2 C 0.66026(10) -0.0698(2) 0.2864(2) 0.0595(6) Uani 1 1 d .
H2 H 0.6237 -0.1099 0.2695 0.066(7) Uiso 1 1 calc R
C3 C 0.70168(13) -0.1125(3) 0.3787(2) 0.0761(8) Uani 1 1 d .
H3 H 0.6929 -0.1797 0.4240 0.110(11) Uiso 1 1 calc R
C4 C 0.75542(13) -0.0561(3) 0.4031(3) 0.0896(10) Uani 1 1 d .
H4 H 0.7837 -0.0852 0.4650 0.097(9) Uiso 1 1 calc R
C5 C 0.76809(12) 0.0434(3) 0.3369(3) 0.0949(10) Uani 1 1 d .
H5 H 0.8050 0.0819 0.3545 0.116(11) Uiso 1 1 calc R
C6 C 0.72668(11) 0.0877(3) 0.2438(3) 0.0753(8) Uani 1 1 d .
H6 H 0.7359 0.1548 0.1989 0.060(7) Uiso 1 1 calc R
C7 C 0.62613(9) 0.0778(2) 0.12048(19) 0.0498(6) Uani 1 1 d .
C8 C 0.59777(9) 0.1988(2) 0.0920(2) 0.0505(6) Uani 1 1 d .
C9 C 0.59931(9) 0.3241(2) 0.1567(2) 0.0523(6) Uani 1 1 d .
C10 C 0.62951(12) 0.3365(2) 0.2672(2) 0.0705(7) Uani 1 1 d .
H10 H 0.6531 0.2662 0.3013 0.095(9) Uiso 1 1 calc R
C11 C 0.62557(13) 0.4505(3) 0.3280(3) 0.0849(9) Uani 1 1 d .
H11 H 0.6459 0.4552 0.4025 0.105(10) Uiso 1 1 calc R
C12 C 0.59202(12) 0.5568(3) 0.2801(3) 0.0785(8) Uani 1 1 d .
H12 H 0.5892 0.6335 0.3211 0.091(9) Uiso 1 1 calc R
C13 C 0.56270(12) 0.5472(3) 0.1699(3) 0.0797(9) Uani 1 1 d .
H13 H 0.5402 0.6192 0.1357 0.098(10) Uiso 1 1 calc R
C14 C 0.56595(10) 0.4330(2) 0.1091(2) 0.0677(7) Uani 1 1 d .
H14 H 0.5454 0.4289 0.0347 0.075(8) Uiso 1 1 calc R
C15 C 0.56238(9) 0.0615(2) -0.04326(19) 0.0487(6) Uani 1 1 d .
C16 C 0.52892(9) 0.0121(2) -0.15133(18) 0.0480(6) Uani 1 1 d .
C17 C 0.51624(10) -0.1142(2) -0.19416(19) 0.0565(6) Uani 1 1 d .
H17 H 0.5279 -0.1921 -0.1534 0.074(8) Uiso 1 1 calc R
C18 C 0.62272(14) -0.1452(3) 0.0214(3) 0.0795(9) Uani 1 1 d .
H18A H 0.6605 -0.1579 0.0708 0.124(12) Uiso 1 1 calc R
H18B H 0.6249 -0.1591 -0.0541 0.101(11) Uiso 1 1 calc R
H18C H 0.5959 -0.2084 0.0395 0.121(13) Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 S1 C16 92.19(15) 2_654 .
C15 N1 C8 106.28(17) . .
C15 N2 C7 107.23(18) . .
C15 N2 C18 126.6(2) . .
C7 N2 C18 125.74(19) . .
C6 C1 C2 117.9(2) . .
C6 C1 C7 121.2(2) . .
C2 C1 C7 120.9(2) . .
C3 C2 C1 121.7(2) . .
C3 C2 H2 119.1 . .
C1 C2 H2 119.1 . .
C4 C3 C2 119.6(3) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 120.1(3) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C4 C5 C6 120.9(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C1 C6 C5 119.7(3) . .
C1 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C8 C7 N2 105.71(19) . .
C8 C7 C1 133.6(2) . .
N2 C7 C1 120.68(18) . .
N1 C8 C7 109.52(19) . .
N1 C8 C9 119.43(19) . .
C7 C8 C9 130.7(2) . .
C10 C9 C14 116.8(2) . .
C10 C9 C8 123.3(2) . .
C14 C9 C8 119.7(2) . .
C11 C10 C9 121.7(2) . .
C11 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C12 C11 C10 120.7(3) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 118.3(3) . .
C11 C12 H12 120.8 . .
C13 C12 H12 120.8 . .
C12 C13 C14 121.2(3) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C13 C14 C9 121.2(2) . .
C13 C14 H14 119.4 . .
C9 C14 H14 119.4 . .
N1 C15 N2 111.26(19) . .
N1 C15 C16 122.34(19) . .
N2 C15 C16 126.3(2) . .
C17 C16 C15 132.9(2) . .
C17 C16 S1 110.65(16) . .
C15 C16 S1 116.40(16) . .
C16 C17 C17 113.25(13) . 2_654
C16 C17 H17 123.4 . .
C17 C17 H17 123.4 2_654 .
N2 C18 H18A 109.5 . .
N2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C16 1.726(2) 2_654
S1 C16 1.726(2) .
N1 C15 1.324(3) .
N1 C8 1.380(3) .
N2 C15 1.365(3) .
N2 C7 1.385(3) .
N2 C18 1.458(3) .
C1 C6 1.384(3) .
C1 C2 1.387(3) .
C1 C7 1.478(3) .
C2 C3 1.376(3) .
C2 H2 0.9300 .
C3 C4 1.357(4) .
C3 H3 0.9300 .
C4 C5 1.367(4) .
C4 H4 0.9300 .
C5 C6 1.388(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.383(3) .
C8 C9 1.479(3) .
C9 C10 1.383(3) .
C9 C14 1.385(3) .
C10 C11 1.379(4) .
C10 H10 0.9300 .
C11 C12 1.368(4) .
C11 H11 0.9300 .
C12 C13 1.372(4) .
C12 H12 0.9300 .
C13 C14 1.378(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.461(3) .
C16 C17 1.369(3) .
C17 C17 1.406(5) 2_654
C17 H17 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.3(4) . .
C7 C1 C2 C3 -178.8(2) . .
C1 C2 C3 C4 -1.0(4) . .
C2 C3 C4 C5 0.6(5) . .
C3 C4 C5 C6 -0.4(5) . .
C2 C1 C6 C5 -1.1(4) . .
C7 C1 C6 C5 179.0(3) . .
C4 C5 C6 C1 0.7(5) . .
C15 N2 C7 C8 0.8(2) . .
C18 N2 C7 C8 173.9(2) . .
C15 N2 C7 C1 -179.9(2) . .
C18 N2 C7 C1 -6.7(4) . .
C6 C1 C7 C8 -63.2(4) . .
C2 C1 C7 C8 116.9(3) . .
C6 C1 C7 N2 117.6(3) . .
C2 C1 C7 N2 -62.2(3) . .
C15 N1 C8 C7 0.8(2) . .
C15 N1 C8 C9 -173.3(2) . .
N2 C7 C8 N1 -1.0(3) . .
C1 C7 C8 N1 179.8(2) . .
N2 C7 C8 C9 172.2(2) . .
C1 C7 C8 C9 -7.0(4) . .
N1 C8 C9 C10 168.5(2) . .
C7 C8 C9 C10 -4.2(4) . .
N1 C8 C9 C14 -6.7(3) . .
C7 C8 C9 C14 -179.4(2) . .
C14 C9 C10 C11 1.5(4) . .
C8 C9 C10 C11 -173.7(3) . .
C9 C10 C11 C12 -1.0(5) . .
C10 C11 C12 C13 -0.3(5) . .
C11 C12 C13 C14 1.1(4) . .
C12 C13 C14 C9 -0.5(4) . .
C10 C9 C14 C13 -0.8(4) . .
C8 C9 C14 C13 174.7(2) . .
C8 N1 C15 N2 -0.4(2) . .
C8 N1 C15 C16 -177.3(2) . .
C7 N2 C15 N1 -0.3(3) . .
C18 N2 C15 N1 -173.4(2) . .
C7 N2 C15 C16 176.6(2) . .
C18 N2 C15 C16 3.5(4) . .
N1 C15 C16 C17 -164.7(2) . .
N2 C15 C16 C17 18.8(4) . .
N1 C15 C16 S1 17.4(3) . .
N2 C15 C16 S1 -159.08(19) . .
C16 S1 C16 C17 -0.13(12) 2_654 .
C16 S1 C16 C15 178.2(2) 2_654 .
C15 C16 C17 C17 -177.6(2) . 2_654
S1 C16 C17 C17 0.4(3) . 2_654
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102256802
