#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/83/4508358.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_4508358
loop_
_publ_author_name
'Mamada, Masashi'
'Katagiri, Hiroshi'
'Mizukami, Makoto'
'Honda, Kota'
'Minamiki, Tsukuru'
'Teraoka, Ryo'
'Uemura, Taisuke'
'Tokito, Shizuo'
_publ_section_title
;
 syn-/anti-Anthradithiophene Derivative Isomer Effects on Semiconducting
 Properties.
;
_journal_issue                   19
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              9670
_journal_page_last               9677
_journal_paper_doi               10.1021/am4027136
_journal_volume                  5
_journal_year                    2013
_chemical_formula_moiety         'C18 H10 S2'
_chemical_formula_sum            'C18 H10 S2'
_chemical_formula_weight         290.38
_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                86.589(10)
_cell_angle_beta                 78.271(8)
_cell_angle_gamma                86.424(9)
_cell_formula_units_Z            2
_cell_length_a                   5.9155(16)
_cell_length_b                   7.772(2)
_cell_length_c                   13.991(4)
_cell_measurement_reflns_used    2060
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.4623
_cell_measurement_theta_min      3.0830
_cell_volume                     627.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10207
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_diffrn_standards_number         2858
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     200
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²+0.1176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2539
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am4027136_si_002.cif
_cod_data_source_block           anti-4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        627.8(3)
_cod_database_code               4508358
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1332(2) 0.55959(15) 0.24428(8) 0.0159(2) Uani 1 1 d DU . .
C2 C -0.0919(2) 0.64650(16) 0.25355(8) 0.0159(2) Uani 1 1 d DU A .
S1A S -0.18260(12) 0.72700(12) 0.36938(4) 0.01881(18) Uani 0.6775(15) 1 d PDU A
1
C3A C 0.0738(3) 0.6484(3) 0.40417(13) 0.0190(3) Uani 0.6775(15) 1 d PDU A 1
H3A H 0.1069 0.6639 0.4667 0.026(6) Uiso 0.6775(15) 1 calc PR A 1
C4A C 0.2206(8) 0.5632(7) 0.3331(3) 0.0178(4) Uani 0.6775(15) 1 d PDU A 1
H4A H 0.3658 0.5112 0.3410 0.021 Uiso 0.6775(15) 1 calc PR A 1
S1B S 0.2389(3) 0.5717(3) 0.35081(12) 0.0191(3) Uani 0.3225(15) 1 d PDU A 2
C3B C -0.0096(5) 0.6901(5) 0.40602(18) 0.0189(4) Uani 0.3225(15) 1 d PDU A 2
H3B H -0.0333 0.7283 0.4707 0.023 Uiso 0.3225(15) 1 calc PR A 2
C4B C -0.1651(11) 0.7220(12) 0.3473(4) 0.0183(4) Uani 0.3225(15) 1 d PDU A 2
H4B H -0.3071 0.7870 0.3659 0.022 Uiso 0.3225(15) 1 calc PR A 2
C7 C 0.6394(2) 0.13922(15) 0.23077(8) 0.0153(2) Uani 1 1 d DU . .
C8 C 0.4164(2) 0.06916(16) 0.26559(8) 0.0155(2) Uani 1 1 d DU B .
S2A S 0.32680(6) 0.08520(5) 0.39180(3) 0.01833(13) Uani 0.9005(15) 1 d PDU B 1
C5A C 0.5797(3) 0.18577(19) 0.39766(10) 0.0188(3) Uani 0.9005(15) 1 d PDU B 1
H5A H 0.6119 0.2230 0.4567 0.023 Uiso 0.9005(15) 1 calc PR B 1
C6A C 0.7263(4) 0.2057(3) 0.30928(15) 0.0174(3) Uani 0.9005(15) 1 d PDU B 1
H6A H 0.8705 0.2580 0.3006 0.021 Uiso 0.9005(15) 1 calc PR B 1
S2B S 0.7495(7) 0.2161(7) 0.3259(3) 0.0183(5) Uani 0.0995(15) 1 d PDU B 2
C5B C 0.5032(10) 0.1561(10) 0.41050(18) 0.0182(4) Uani 0.0995(15) 1 d PDU B 2
H5B H 0.4816 0.1736 0.4784 0.022 Uiso 0.0995(15) 1 calc PR B 2
C6B C 0.3448(9) 0.0816(7) 0.3696(2) 0.0174(4) Uani 0.0995(15) 1 d PDU B 2
H6B H 0.2024 0.0422 0.4061 0.021 Uiso 0.0995(15) 1 calc PR B 2
C9 C 0.2967(2) 0.00145(16) 0.20339(9) 0.0147(2) Uani 1 1 d U . .
H9 H 0.1495 -0.0438 0.2279 0.018 Uiso 1 1 calc R B .
C10 C 0.7391(2) 0.13894(16) 0.13270(9) 0.0145(2) Uani 1 1 d U B .
H10 H 0.8863 0.1853 0.1098 0.017 Uiso 1 1 calc R . .
C11 C 0.6215(2) 0.06920(15) 0.06563(9) 0.0136(2) Uani 1 1 d U . .
C12 C 0.7183(2) 0.06766(15) -0.03478(9) 0.0137(2) Uani 1 1 d U B .
H12 H 0.8654 0.1137 -0.0582 0.016 Uiso 1 1 calc R . .
C13 C 0.6035(2) 0.00002(15) -0.10133(9) 0.0136(2) Uani 1 1 d U . .
C14 C -0.2087(2) 0.65651(16) 0.17786(9) 0.0154(2) Uani 1 1 d U . .
H14 H -0.3567 0.7148 0.1850 0.019 Uiso 1 1 calc R A .
C15 C 0.2360(2) 0.48289(16) 0.15903(9) 0.0150(2) Uani 1 1 d U A .
H15 H 0.3839 0.4249 0.1536 0.018 Uiso 1 1 calc R . .
C16 C 0.1199(2) 0.49078(15) 0.07895(9) 0.0141(2) Uani 1 1 d U . .
C17 C 0.2192(2) 0.41398(15) -0.00937(9) 0.0143(2) Uani 1 1 d U A .
H17 H 0.3669 0.3555 -0.0156 0.017 Uiso 1 1 calc R . .
C18 C 0.1061(2) 0.42128(15) -0.08845(9) 0.0139(2) Uani 1 1 d U . .
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
_geom_angle_site_symmetry_3
C15 C1 C2 120.50(9) . .
C15 C1 C4A 128.0(2) . .
C2 C1 C4A 111.5(2) . .
C15 C1 S1B 128.85(11) . .
C2 C1 S1B 110.65(7) . .
C4A C1 S1B 2.0(3) . .
C14 C2 C1 121.26(9) . .
C14 C2 C4B 127.0(2) . .
C1 C2 C4B 111.7(2) . .
C14 C2 S1A 127.94(10) . .
C1 C2 S1A 110.79(6) . .
C4B C2 S1A 2.9(4) . .
C2 S1A C3A 91.47(8) . .
C4A C3A S1A 113.32(18) . .
C4A C3A H3A 123.3 . .
S1A C3A H3A 123.3 . .
C3A C4A C1 112.9(3) . .
C3A C4A H4A 123.5 . .
C1 C4A H4A 123.5 . .
C1 S1B C3B 91.60(9) . .
C4B C3B S1B 113.28(19) . .
C4B C3B H3B 123.4 . .
S1B C3B H3B 123.4 . .
C3B C4B C2 112.8(3) . .
C3B C4B H4B 123.6 . .
C2 C4B H4B 123.6 . .
C10 C7 C6A 128.73(14) . .
C10 C7 C8 120.06(10) . .
C6A C7 C8 111.20(14) . .
C10 C7 S2B 128.33(16) . .
C6A C7 S2B 1.3(3) . .
C8 C7 S2B 111.61(10) . .
C9 C8 C6B 127.2(2) . .
C9 C8 C7 121.75(10) . .
C6B C8 C7 111.10(17) . .
C9 C8 S2A 126.78(10) . .
C6B C8 S2A 0.6(2) . .
C7 C8 S2A 111.47(8) . .
C8 S2A C5A 90.86(6) . .
C6A C5A S2A 113.60(13) . .
C6A C5A H5A 123.2 . .
S2A C5A H5A 123.2 . .
C5A C6A C7 112.86(19) . .
C5A C6A H6A 123.6 . .
C7 C6A H6A 123.6 . .
C7 S2B C5B 90.80(9) . .
C6B C5B S2B 113.62(16) . .
C6B C5B H5B 123.2 . .
S2B C5B H5B 123.2 . .
C5B C6B C8 112.9(2) . .
C5B C6B H6B 123.6 . .
C8 C6B H6B 123.6 . .
C8 C9 C13 119.20(11) . 2_655
C8 C9 H9 120.4 . .
C13 C9 H9 120.4 2_655 .
C7 C10 C11 120.08(11) . .
C7 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C12 C11 C10 121.39(11) . .
C12 C11 C13 119.17(11) . 2_655
C10 C11 C13 119.44(11) . 2_655
C13 C12 C11 121.80(11) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C12 C13 C9 121.49(11) . 2_655
C12 C13 C11 119.03(11) . 2_655
C9 C13 C11 119.48(11) 2_655 2_655
C2 C14 C18 119.49(12) . 2_565
C2 C14 H14 120.3 . .
C18 C14 H14 120.3 2_565 .
C1 C15 C16 119.78(12) . .
C1 C15 H15 120.1 . .
C16 C15 H15 120.1 . .
C17 C16 C15 121.48(11) . .
C17 C16 C18 118.96(11) . 2_565
C15 C16 C18 119.56(12) . 2_565
C18 C17 C16 121.81(11) . .
C18 C17 H17 119.1 . .
C16 C17 H17 119.1 . .
C17 C18 C14 121.36(11) . 2_565
C17 C18 C16 119.23(12) . 2_565
C14 C18 C16 119.41(12) 2_565 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C15 1.3755(16) .
C1 C2 1.4402(18) .
C1 C4A 1.442(4) .
C1 S1B 1.7388(14) .
C2 C14 1.3734(16) .
C2 C4B 1.442(4) .
C2 S1A 1.7409(12) .
S1A C3A 1.7493(19) .
C3A C4A 1.355(5) .
C3A H3A 0.9500 .
C4A H4A 0.9500 .
S1B C3B 1.749(2) .
C3B C4B 1.355(5) .
C3B H3B 0.9500 .
C4B H4B 0.9500 .
C7 C10 1.3789(16) .
C7 C6A 1.438(2) .
C7 C8 1.4390(18) .
C7 S2B 1.7456(15) .
C8 C9 1.3738(17) .
C8 C6B 1.438(3) .
C8 S2A 1.7470(13) .
S2A C5A 1.7489(16) .
C5A C6A 1.365(3) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
S2B C5B 1.7492(18) .
C5B C6B 1.365(3) .
C5B H5B 0.9500 .
C6B H6B 0.9500 .
C9 C13 1.4303(17) 2_655
C9 H9 0.9500 .
C10 C11 1.4250(17) .
C10 H10 0.9500 .
C11 C12 1.4056(17) .
C11 C13 1.4485(17) 2_655
C12 C13 1.4011(17) .
C12 H12 0.9500 .
C13 C9 1.4303(17) 2_655
C13 C11 1.4485(17) 2_655
C14 C18 1.4263(18) 2_565
C14 H14 0.9500 .
C15 C16 1.4249(17) .
C15 H15 0.9500 .
C16 C17 1.4061(17) .
C16 C18 1.4477(18) 2_565
C17 C18 1.4013(17) .
C17 H17 0.9500 .
C18 C14 1.4263(18) 2_565
C18 C16 1.4477(18) 2_565
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
C15 C1 C2 C14 -0.55(19) . .
C4A C1 C2 C14 -179.1(3) . .
S1B C1 C2 C14 178.93(14) . .
C15 C1 C2 C4B -178.4(4) . .
C4A C1 C2 C4B 3.1(5) . .
S1B C1 C2 C4B 1.1(5) . .
C15 C1 C2 S1A 178.64(10) . .
C4A C1 C2 S1A 0.1(3) . .
S1B C1 C2 S1A -1.88(16) . .
C14 C2 S1A C3A 179.57(14) . .
C1 C2 S1A C3A 0.45(12) . .
C4B C2 S1A C3A -107(5) . .
C2 S1A C3A C4A -0.9(3) . .
S1A C3A C4A C1 1.1(5) . .
C15 C1 C4A C3A -179.2(2) . .
C2 C1 C4A C3A -0.7(5) . .
S1B C1 C4A C3A 64(7) . .
C15 C1 S1B C3B 179.20(19) . .
C2 C1 S1B C3B -0.2(2) . .
C4A C1 S1B C3B -116(7) . .
C1 S1B C3B C4B -0.8(6) . .
S1B C3B C4B C2 1.6(9) . .
C14 C2 C4B C3B -179.4(4) . .
C1 C2 C4B C3B -1.7(8) . .
S1A C2 C4B C3B 71(5) . .
C10 C7 C8 C9 -0.29(19) . .
C6A C7 C8 C9 178.57(14) . .
S2B C7 C8 C9 179.9(2) . .
C10 C7 C8 C6B 179.8(3) . .
C6A C7 C8 C6B -1.3(3) . .
S2B C7 C8 C6B 0.000(19) . .
C10 C7 C8 S2A -179.70(9) . .
C6A C7 C8 S2A -0.85(17) . .
S2B C7 C8 S2A 0.5(2) . .
C9 C8 S2A C5A -178.66(12) . .
C6B C8 S2A C5A 50(23) . .
C7 C8 S2A C5A 0.72(10) . .
C8 S2A C5A C6A -0.42(14) . .
S2A C5A C6A C7 0.0(2) . .
C10 C7 C6A C5A 179.27(13) . .
C8 C7 C6A C5A 0.5(2) . .
S2B C7 C6A C5A -108(10) . .
C10 C7 S2B C5B -179.8(3) . .
C6A C7 S2B C5B 72(10) . .
C8 C7 S2B C5B 0.00(3) . .
C7 S2B C5B C6B 0.00(4) . .
S2B C5B C6B C8 0.00(4) . .
C9 C8 C6B C5B -179.9(2) . .
C7 C8 C6B C5B 0.00(3) . .
S2A C8 C6B C5B -130(23) . .
C6B C8 C9 C13 -179.9(3) . 2_655
C7 C8 C9 C13 0.20(19) . 2_655
S2A C8 C9 C13 179.52(9) . 2_655
C6A C7 C10 C11 -178.67(16) . .
C8 C7 C10 C11 -0.04(18) . .
S2B C7 C10 C11 179.8(3) . .
C7 C10 C11 C12 179.77(11) . .
C7 C10 C11 C13 0.43(18) . 2_655
C10 C11 C12 C13 -179.73(11) . .
C13 C11 C12 C13 -0.4(2) 2_655 .
C11 C12 C13 C9 -179.86(11) . 2_655
C11 C12 C13 C11 0.4(2) . 2_655
C1 C2 C14 C18 0.32(19) . 2_565
C4B C2 C14 C18 177.8(5) . 2_565
S1A C2 C14 C18 -178.72(10) . 2_565
C2 C1 C15 C16 0.57(19) . .
C4A C1 C15 C16 178.9(3) . .
S1B C1 C15 C16 -178.80(15) . .
C1 C15 C16 C17 -179.98(11) . .
C1 C15 C16 C18 -0.38(18) . 2_565
C15 C16 C17 C18 -179.97(11) . .
C18 C16 C17 C18 0.4(2) 2_565 .
C16 C17 C18 C14 179.76(11) . 2_565
C16 C17 C18 C16 -0.4(2) . 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146668
