#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/65/7106519.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_7106519
loop_
_publ_author_name
'Lukas Zophel'
'Dirk Beckmann'
'Volker Enkelmann'
'Dennis Chercka'
'Ralph Rieger'
'Klaus Mullen'
_publ_section_title
;
 Asymmetric pyrene derivatives for organic field-effect transistors
;
_journal_name_full               Chem.Commun.
_journal_page_first              6960
_journal_paper_doi               10.1039/c1cc11827g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C26 H16 O2 S2'
_chemical_formula_sum            'C26 H16 O2 S2'
_chemical_formula_weight         424.54
_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
_audit_creation_date             10-04-28
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 101.0025(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   46.7200(10)
_cell_length_b                   4.29240(10)
_cell_length_c                   18.9060(7)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3721.74(18)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16633
_diffrn_reflns_theta_full        25.112
_diffrn_reflns_theta_max         29.544
_diffrn_reflns_theta_min         0.888
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.000590
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.06 0.708 1.67
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0491
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0464
_reflns_limit_h_max              62
_reflns_limit_h_min              -64
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3476
_reflns_number_total             5130
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            c1cc11827g.txt
_cod_data_source_block           zokond
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               7106519
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.211333(9) 0.08944(12) 0.26560(2) 0.0282 1.0000 Uani . . . . . .
S2 S 0.151619(10) 0.77071(12) 0.48905(2) 0.0285 1.0000 Uani . . . . . .
O29 O 0.04662(3) 0.1211(3) 0.06670(7) 0.0291 1.0000 Uani . . . . . .
O30 O 0.02123(3) 0.5167(3) 0.15681(8) 0.0303 1.0000 Uani . . . . . .
C1 C 0.10958(3) 0.2548(4) 0.21660(8) 0.0199 1.0000 Uani . . . . . .
C2 C 0.13925(3) 0.1659(4) 0.23678(8) 0.0203 1.0000 Uani . . . . . .
C3 C 0.14986(4) -0.0557(4) 0.19370(9) 0.0229 1.0000 Uani . . . . . .
C4 C 0.13289(4) -0.1668(4) 0.13011(9) 0.0251 1.0000 Uani . . . . . .
C5 C 0.10460(4) -0.0636(4) 0.10777(9) 0.0249 1.0000 Uani . . . . . .
C6 C 0.09243(3) 0.1408(4) 0.15132(9) 0.0218 1.0000 Uani . . . . . .
C7 C 0.06250(4) 0.2368(4) 0.13078(9) 0.0239 1.0000 Uani . . . . . .
C8 C 0.05003(3) 0.4233(4) 0.17424(9) 0.0237 1.0000 Uani . . . . . .
C9 C 0.06685(3) 0.5440(4) 0.24029(9) 0.0214 1.0000 Uani . . . . . .
C10 C 0.09674(3) 0.4601(4) 0.26144(8) 0.0197 1.0000 Uani . . . . . .
C11 C 0.11343(3) 0.5735(4) 0.32718(8) 0.0202 1.0000 Uani . . . . . .
C12 C 0.09964(4) 0.7812(4) 0.36729(9) 0.0263 1.0000 Uani . . . . . .
C13 C 0.07048(4) 0.8631(4) 0.34582(10) 0.0279 1.0000 Uani . . . . . .
C14 C 0.05386(4) 0.7440(4) 0.28360(9) 0.0245 1.0000 Uani . . . . . .
C15 C 0.15739(3) 0.3000(4) 0.30162(8) 0.0200 1.0000 Uani . . . . . .
C16 C 0.14425(3) 0.4856(4) 0.34873(8) 0.0198 1.0000 Uani . . . . . .
C17 C 0.16208(3) 0.5841(4) 0.41571(8) 0.0216 1.0000 Uani . . . . . .
C18 C 0.19212(4) 0.5262(4) 0.43269(9) 0.0243 1.0000 Uani . . . . . .
C19 C 0.20569(4) 0.3715(4) 0.38187(9) 0.0242 1.0000 Uani . . . . . .
C20 C 0.18852(3) 0.2578(4) 0.31866(8) 0.0213 1.0000 Uani . . . . . .
C21 C 0.23629(4) 0.3182(5) 0.38706(11) 0.0296 1.0000 Uani . . . . . .
C22 C 0.24223(4) 0.1708(5) 0.32850(11) 0.0320 1.0000 Uani . . . . . .
C23 C 0.20569(4) 0.6338(5) 0.50251(10) 0.0307 1.0000 Uani . . . . . .
C24 C 0.18656(4) 0.7661(5) 0.53869(10) 0.0335 1.0000 Uani . . . . . .
C25 C 0.04165(5) 0.3474(5) 0.01022(11) 0.0403 1.0000 Uani . . . . . .
C26 C 0.00009(4) 0.2757(5) 0.14632(14) 0.0389 1.0000 Uani . . . . . .
H31 H 0.1691 -0.1331 0.2086 0.0305 1.0000 Uiso R . . . . .
H41 H 0.1409 -0.3132 0.1015 0.0320 1.0000 Uiso R . . . . .
H51 H 0.0934 -0.1317 0.0632 0.0318 1.0000 Uiso R . . . . .
H121 H 0.1106 0.8683 0.4102 0.0341 1.0000 Uiso R . . . . .
H131 H 0.0619 1.0031 0.3746 0.0352 1.0000 Uiso R . . . . .
H141 H 0.0338 0.7964 0.2701 0.0318 1.0000 Uiso R . . . . .
H211 H 0.2507 0.3806 0.4271 0.0378 1.0000 Uiso R . . . . .
H221 H 0.2614 0.1172 0.3226 0.0398 1.0000 Uiso R . . . . .
H231 H 0.2260 0.6144 0.5214 0.0398 1.0000 Uiso R . . . . .
H241 H 0.1918 0.8476 0.5861 0.0423 1.0000 Uiso R . . . . .
H251 H 0.0307 0.2561 -0.0323 0.0535 1.0000 Uiso R . . . . .
H252 H 0.0598 0.4195 0.0010 0.0535 1.0000 Uiso R . . . . .
H253 H 0.0311 0.5176 0.0245 0.0535 1.0000 Uiso R . . . . .
H261 H -0.0189 0.3639 0.1347 0.0501 1.0000 Uiso R . . . . .
H262 H 0.0018 0.1564 0.1892 0.0501 1.0000 Uiso R . . . . .
H263 H 0.0033 0.1450 0.1080 0.0501 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C20 . S1 . C22 . 92.42(9) yes
C17 . S2 . C24 . 92.73(9) yes
C7 . O29 . C25 . 113.15(14) yes
C8 . O30 . C26 . 116.24(14) yes
C2 . C1 . C6 . 120.01(15) yes
C2 . C1 . C10 . 120.33(14) yes
C6 . C1 . C10 . 119.67(14) yes
C1 . C2 . C3 . 117.50(15) yes
C1 . C2 . C15 . 119.86(15) yes
C3 . C2 . C15 . 122.63(15) yes
C2 . C3 . C4 . 121.86(15) yes
C2 . C3 . H31 . 119.0 no
C4 . C3 . H31 . 119.2 no
C3 . C4 . C5 . 120.53(16) yes
C3 . C4 . H41 . 119.9 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . C6 . 119.64(16) yes
C4 . C5 . H51 . 120.5 no
C6 . C5 . H51 . 119.9 no
C1 . C6 . C5 . 120.15(15) yes
C1 . C6 . C7 . 119.52(15) yes
C5 . C6 . C7 . 120.33(15) yes
C6 . C7 . O29 . 117.64(15) yes
C6 . C7 . C8 . 120.91(15) yes
O29 . C7 . C8 . 121.39(15) yes
O30 . C8 . C7 . 122.57(15) yes
O30 . C8 . C9 . 116.63(15) yes
C7 . C8 . C9 . 120.77(14) yes
C8 . C9 . C10 . 119.78(15) yes
C8 . C9 . C14 . 120.10(14) yes
C10 . C9 . C14 . 120.12(15) yes
C1 . C10 . C9 . 119.27(14) yes
C1 . C10 . C11 . 120.45(14) yes
C9 . C10 . C11 . 120.27(14) yes
C10 . C11 . C12 . 117.26(14) yes
C10 . C11 . C16 . 119.99(14) yes
C12 . C11 . C16 . 122.66(14) yes
C11 . C12 . C13 . 121.85(16) yes
C11 . C12 . H121 . 118.9 no
C13 . C12 . H121 . 119.3 no
C12 . C13 . C14 . 121.10(16) yes
C12 . C13 . H131 . 119.4 no
C14 . C13 . H131 . 119.5 no
C9 . C14 . C13 . 119.30(15) yes
C9 . C14 . H141 . 120.2 no
C13 . C14 . H141 . 120.5 no
C2 . C15 . C16 . 119.63(14) yes
C2 . C15 . C20 . 122.34(14) yes
C16 . C15 . C20 . 118.01(14) yes
C11 . C16 . C15 . 119.25(14) yes
C11 . C16 . C17 . 122.72(14) yes
C15 . C16 . C17 . 118.03(14) yes
C16 . C17 . S2 . 128.98(12) yes
C16 . C17 . C18 . 122.38(15) yes
S2 . C17 . C18 . 108.59(12) yes
C17 . C18 . C19 . 119.16(15) yes
C17 . C18 . C23 . 113.78(16) yes
C19 . C18 . C23 . 127.06(16) yes
C18 . C19 . C20 . 119.16(15) yes
C18 . C19 . C21 . 126.85(16) yes
C20 . C19 . C21 . 113.99(16) yes
C15 . C20 . S1 . 128.49(12) yes
C15 . C20 . C19 . 122.65(15) yes
S1 . C20 . C19 . 108.74(12) yes
C19 . C21 . C22 . 112.17(16) yes
C19 . C21 . H211 . 123.7 no
C22 . C21 . H211 . 124.1 no
S1 . C22 . C21 . 112.68(14) yes
S1 . C22 . H221 . 123.6 no
C21 . C22 . H221 . 123.7 no
C18 . C23 . C24 . 112.61(16) yes
C18 . C23 . H231 . 123.7 no
C24 . C23 . H231 . 123.7 no
S2 . C24 . C23 . 112.29(14) yes
S2 . C24 . H241 . 123.7 no
C23 . C24 . H241 . 124.0 no
O29 . C25 . H251 . 109.6 no
O29 . C25 . H252 . 109.6 no
H251 . C25 . H252 . 109.5 no
O29 . C25 . H253 . 109.2 no
H251 . C25 . H253 . 109.5 no
H252 . C25 . H253 . 109.5 no
O30 . C26 . H261 . 109.6 no
O30 . C26 . H262 . 109.4 no
H261 . C26 . H262 . 109.5 no
O30 . C26 . H263 . 109.4 no
H261 . C26 . H263 . 109.5 no
H262 . C26 . H263 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C20 . 1.7532(16) yes
S1 . C22 . 1.7217(19) yes
S2 . C17 . 1.7499(17) yes
S2 . C24 . 1.7207(19) yes
O29 . C7 . 1.386(2) yes
O29 . C25 . 1.429(2) yes
O30 . C8 . 1.3819(19) yes
O30 . C26 . 1.418(2) yes
C1 . C2 . 1.418(2) yes
C1 . C6 . 1.424(2) yes
C1 . C10 . 1.432(2) yes
C2 . C3 . 1.403(2) yes
C2 . C15 . 1.468(2) yes
C3 . C4 . 1.392(2) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.382(2) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.396(2) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.438(2) yes
C7 . C8 . 1.356(2) yes
C8 . C9 . 1.439(2) yes
C9 . C10 . 1.423(2) yes
C9 . C14 . 1.402(2) yes
C10 . C11 . 1.421(2) yes
C11 . C12 . 1.404(2) yes
C11 . C16 . 1.469(2) yes
C12 . C13 . 1.390(2) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.378(3) yes
C13 . H131 . 0.950 no
C14 . H141 . 0.950 no
C15 . C16 . 1.419(2) yes
C15 . C20 . 1.440(2) yes
C16 . C17 . 1.440(2) yes
C17 . C18 . 1.401(2) yes
C18 . C19 . 1.414(2) yes
C18 . C23 . 1.428(2) yes
C19 . C20 . 1.394(2) yes
C19 . C21 . 1.433(2) yes
C21 . C22 . 1.349(3) yes
C21 . H211 . 0.950 no
C22 . H221 . 0.950 no
C23 . C24 . 1.350(3) yes
C23 . H231 . 0.950 no
C24 . H241 . 0.950 no
C25 . H251 . 0.950 no
C25 . H252 . 0.950 no
C25 . H253 . 0.950 no
C26 . H261 . 0.950 no
C26 . H262 . 0.950 no
C26 . H263 . 0.950 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653298
2 PubChem 53473331
