#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506200.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506200
loop_
_publ_author_name
'Wong, Ken-Tsung'
'Chao, Teng-Chih'
'Chi, Liang-Chen'
'Chu, Ying-Ying'
'Balaiah, Akula'
'Chiu, Shih-Feng'
'Liu, Yi-Hung'
'Wang, Yu'
_publ_section_title
;
 Syntheses and structures of novel heteroarene-fused coplanar
 pi-conjugated chromophores.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5033
_journal_page_last               5036
_journal_paper_doi               10.1021/ol061791y
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C52 H38 S2'
_chemical_formula_weight         726.94
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.407(2)
_cell_angle_beta                 104.026(2)
_cell_angle_gamma                107.311(2)
_cell_formula_units_Z            1
_cell_length_a                   9.8963(3)
_cell_length_b                   10.7278(5)
_cell_length_c                   10.7354(4)
_cell_measurement_reflns_used    17975
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     940.43(7)
_computing_cell_refinement       'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_data_collection       'COLLECT (Nonius BV)'
_computing_data_reduction        'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7074
_diffrn_reflns_theta_full        27.37
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.026(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0612
_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)+(0.0660P)²+0.3875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                2481
_reflns_number_total             4128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061791ysi20060720_074059.cif
_cod_data_source_block           ic11872
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        940.43(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.44912(9) 0.16769(9) 0.00152(9) 0.0666(3) Uani 1 1 d .
C1 C 0.0426(3) 0.0310(3) -0.1067(3) 0.0574(7) Uani 1 1 d .
H1A H 0.0714 0.0499 -0.1769 0.069 Uiso 1 1 calc R
C2 C 0.1501(3) 0.0452(3) 0.0142(3) 0.0534(6) Uani 1 1 d .
C3 C 0.1076(3) 0.0118(3) 0.1190(3) 0.0538(6) Uani 1 1 d .
C4 C 0.2487(3) 0.0302(3) 0.2371(3) 0.0548(6) Uani 1 1 d .
C5 C 0.3766(3) 0.1017(3) 0.1946(3) 0.0560(7) Uani 1 1 d .
C6 C 0.5422(3) 0.1679(3) 0.2537(3) 0.0621(7) Uani 1 1 d .
C7 C 0.6493(3) 0.1996(4) 0.3846(4) 0.0777(9) Uani 1 1 d .
H7A H 0.6170 0.1805 0.4531 0.093 Uiso 1 1 calc R
C8 C 0.8032(4) 0.2596(5) 0.4114(5) 0.1001(13) Uani 1 1 d .
H8A H 0.8744 0.2801 0.4985 0.120 Uiso 1 1 calc R
C9 C 0.8550(4) 0.2904(5) 0.3120(5) 0.0981(12) Uani 1 1 d .
H9A H 0.9598 0.3292 0.3327 0.118 Uiso 1 1 calc R
C10 C 0.7534(3) 0.2641(4) 0.1831(4) 0.0789(9) Uani 1 1 d .
H10A H 0.7877 0.2847 0.1161 0.095 Uiso 1 1 calc R
C11 C 0.5974(3) 0.2058(3) 0.1560(3) 0.0649(8) Uani 1 1 d .
C12 C 0.3165(3) 0.0995(3) 0.0662(3) 0.0570(7) Uani 1 1 d .
C13 C 0.2607(3) 0.1264(3) 0.3876(3) 0.0547(7) Uani 1 1 d .
C14 C 0.3073(4) 0.2763(4) 0.4363(4) 0.0798(10) Uani 1 1 d .
H14A H 0.3351 0.3180 0.3784 0.096 Uiso 1 1 calc R
C15 C 0.3134(4) 0.3662(4) 0.5699(4) 0.0838(10) Uani 1 1 d .
H15A H 0.3446 0.4662 0.5994 0.101 Uiso 1 1 calc R
C16 C 0.2736(4) 0.3079(4) 0.6586(3) 0.0714(8) Uani 1 1 d .
C17 C 0.2250(4) 0.1587(4) 0.6080(4) 0.0832(10) Uani 1 1 d .
H17A H 0.1953 0.1164 0.6648 0.100 Uiso 1 1 calc R
C18 C 0.2190(4) 0.0697(4) 0.4755(4) 0.0753(9) Uani 1 1 d .
H18A H 0.1860 -0.0305 0.4457 0.090 Uiso 1 1 calc R
C19 C 0.2912(5) 0.4049(4) 0.8095(4) 0.1017(12) Uani 1 1 d .
H19A H 0.2578 0.3449 0.8544 0.153 Uiso 1 1 calc R
H19B H 0.2300 0.4588 0.8036 0.153 Uiso 1 1 calc R
H19C H 0.3970 0.4721 0.8658 0.153 Uiso 1 1 calc R
C20 C 0.2393(3) -0.1220(3) 0.2199(3) 0.0574(7) Uani 1 1 d .
C21 C 0.1048(4) -0.2368(4) 0.1799(5) 0.1079(15) Uani 1 1 d .
H21A H 0.0138 -0.2253 0.1572 0.129 Uiso 1 1 calc R
C22 C 0.0988(4) -0.3702(4) 0.1718(6) 0.1199(17) Uani 1 1 d .
H22A H 0.0044 -0.4451 0.1455 0.144 Uiso 1 1 calc R
C23 C 0.2280(4) -0.3944(4) 0.2016(4) 0.0771(9) Uani 1 1 d .
C24 C 0.3601(4) -0.2815(4) 0.2400(5) 0.0945(12) Uani 1 1 d .
H24A H 0.4506 -0.2941 0.2596 0.113 Uiso 1 1 calc R
C25 C 0.3671(4) -0.1476(4) 0.2516(4) 0.0883(11) Uani 1 1 d .
H25A H 0.4625 -0.0719 0.2822 0.106 Uiso 1 1 calc R
C26 C 0.2233(5) -0.5395(4) 0.1954(5) 0.1092(14) Uani 1 1 d .
H26A H 0.3253 -0.5348 0.2197 0.164 Uiso 1 1 calc R
H26B H 0.1591 -0.6169 0.0998 0.164 Uiso 1 1 calc R
H26C H 0.1825 -0.5585 0.2627 0.164 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
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'
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
_geom_angle_site_symmetry_1
C12 S1 C11 89.82(14) .
C3 C1 C2 117.8(2) 2
C3 C1 H1A 121.1 2
C2 C1 H1A 121.1 .
C1 C2 C3 121.8(2) .
C1 C2 C12 131.8(3) .
C3 C2 C12 106.3(2) .
C1 C3 C2 120.4(2) 2
C1 C3 C4 129.0(2) 2
C2 C3 C4 110.7(2) .
C5 C4 C13 114.1(2) .
C5 C4 C20 110.0(2) .
C13 C4 C20 111.8(2) .
C5 C4 C3 99.8(2) .
C13 C4 C3 110.4(2) .
C20 C4 C3 110.1(2) .
C12 C5 C6 112.4(2) .
C12 C5 C4 110.5(2) .
C6 C5 C4 137.0(2) .
C7 C6 C11 118.1(3) .
C7 C6 C5 131.6(3) .
C11 C6 C5 110.2(3) .
C8 C7 C6 119.3(3) .
C8 C7 H7A 120.4 .
C6 C7 H7A 120.4 .
C7 C8 C9 121.7(3) .
C7 C8 H8A 119.1 .
C9 C8 H8A 119.1 .
C10 C9 C8 120.9(3) .
C10 C9 H9A 119.6 .
C8 C9 H9A 119.6 .
C9 C10 C11 117.8(3) .
C9 C10 H10A 121.1 .
C11 C10 H10A 121.1 .
C10 C11 C6 122.1(3) .
C10 C11 S1 125.5(3) .
C6 C11 S1 112.5(2) .
C5 C12 C2 111.8(2) .
C5 C12 S1 114.9(2) .
C2 C12 S1 133.1(2) .
C18 C13 C14 117.1(3) .
C18 C13 C4 122.6(3) .
C14 C13 C4 120.2(2) .
C13 C14 C15 121.7(3) .
C13 C14 H14A 119.1 .
C15 C14 H14A 119.1 .
C16 C15 C14 120.5(3) .
C16 C15 H15A 119.7 .
C14 C15 H15A 119.7 .
C17 C16 C15 117.2(3) .
C17 C16 C19 121.1(3) .
C15 C16 C19 121.6(3) .
C16 C17 C18 122.2(3) .
C16 C17 H17A 118.9 .
C18 C17 H17A 118.9 .
C13 C18 C17 121.2(3) .
C13 C18 H18A 119.4 .
C17 C18 H18A 119.4 .
C16 C19 H19A 109.5 .
C16 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C16 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C21 C20 C25 115.3(3) .
C21 C20 C4 122.7(3) .
C25 C20 C4 121.9(3) .
C20 C21 C22 122.1(3) .
C20 C21 H21A 118.9 .
C22 C21 H21A 118.9 .
C23 C22 C21 121.6(4) .
C23 C22 H22A 119.2 .
C21 C22 H22A 119.2 .
C24 C23 C22 116.1(3) .
C24 C23 C26 121.8(3) .
C22 C23 C26 122.1(3) .
C23 C24 C25 122.5(3) .
C23 C24 H24A 118.7 .
C25 C24 H24A 118.7 .
C20 C25 C24 122.3(3) .
C20 C25 H25A 118.9 .
C24 C25 H25A 118.9 .
C23 C26 H26A 109.5 .
C23 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C23 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C12 1.721(3) .
S1 C11 1.750(3) .
C1 C3 1.377(4) 2
C1 C2 1.392(3) .
C1 H1A 0.9300 .
C2 C3 1.410(4) .
C2 C12 1.456(4) .
C3 C1 1.377(4) 2
C3 C4 1.550(3) .
C4 C5 1.533(4) .
C4 C13 1.536(4) .
C4 C20 1.549(4) .
C5 C12 1.351(4) .
C5 C6 1.442(4) .
C6 C7 1.395(4) .
C6 C11 1.416(4) .
C7 C8 1.376(5) .
C7 H7A 0.9300 .
C8 C9 1.385(5) .
C8 H8A 0.9300 .
C9 C10 1.375(5) .
C9 H9A 0.9300 .
C10 C11 1.392(4) .
C10 H10A 0.9300 .
C13 C18 1.369(4) .
C13 C14 1.388(4) .
C14 C15 1.396(5) .
C14 H14A 0.9300 .
C15 C16 1.380(5) .
C15 H15A 0.9300 .
C16 C17 1.377(5) .
C16 C19 1.523(5) .
C17 C18 1.385(5) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 C21 1.361(4) .
C20 C25 1.361(4) .
C21 C22 1.386(5) .
C21 H21A 0.9300 .
C22 C23 1.364(5) .
C22 H22A 0.9300 .
C23 C24 1.339(5) .
C23 C26 1.521(5) .
C24 C25 1.378(5) .
C24 H24A 0.9300 .
C25 H25A 0.9300 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101421354
