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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233705.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_7233705
loop_
_publ_author_name
'S. Uttiya'
'L. Miozzo'
'E. M. Fumagalli'
'S. Bergantin'
'R. Ruffo'
'M. Parravicini'
'A. Papagni'
'M. Moret'
'A. Sassella'
_publ_section_title
;
 Connecting molecule oxidation to single crystal structural and charge
 transport properties in rubrene derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4147
_journal_page_last               4155
_journal_paper_doi               10.1039/C3TC32527J
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C38 H24 S2'
_chemical_formula_weight         544.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 103.954(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5679(5)
_cell_length_b                   7.0143(2)
_cell_length_c                   14.3020(7)
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1320.94(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Curved image plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 37
	           Slice: 20.0000 - 170.0000
	     Image width: 4.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0285
scan:
	Number of images: 19
	           Slice: 94.0000 - 170.0000
	     Image width: 4.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0285
;
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.010133
_diffrn_orient_matrix_UB_12      0.002982
_diffrn_orient_matrix_UB_13      0.075206
_diffrn_orient_matrix_UB_21      -0.139237
_diffrn_orient_matrix_UB_22      0.023461
_diffrn_orient_matrix_UB_23      -0.019691
_diffrn_orient_matrix_UB_31      -0.014092
_diffrn_orient_matrix_UB_32      -0.068230
_diffrn_orient_matrix_UB_33      0.018351
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12413
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.935
_diffrn_source_current           35.0
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.23
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;
_exptl_crystal_colour            Red
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0392P)²+0.9584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             3015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000003.cif
_cod_data_source_block           PCOD1000003
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C38 H24 S2 '
_cod_database_code               7233705
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22060(9) 0.6473(2) 0.62124(11) 0.0284(6) Uani 1 1 d G U . . .
C2 C 0.28999(12) 0.7544(2) 0.58608(10) 0.0315(6) Uani 1 1 d G U . . .
H2 H 0.2686 0.8208 0.5268 0.038 Uiso 1 1 calc R U . . .
C3 C 0.39075(10) 0.7643(3) 0.63771(13) 0.0398(7) Uani 1 1 d G U . . .
H3 H 0.4382 0.8375 0.6137 0.048 Uiso 1 1 calc R U . . .
C4 C 0.42212(9) 0.6671(3) 0.72450(12) 0.0455(8) Uani 1 1 d G U . . .
H4 H 0.4910 0.6738 0.7598 0.055 Uiso 1 1 calc R U . . .
C5 C 0.35273(12) 0.5599(3) 0.75967(10) 0.0438(7) Uani 1 1 d G U . . .
H5 H 0.3742 0.4935 0.8190 0.053 Uiso 1 1 calc R U . . .
C6 C 0.25197(11) 0.5500(2) 0.70804(11) 0.0311(6) Uani 1 1 d G U . . .
H6 H 0.2046 0.4768 0.7321 0.037 Uiso 1 1 calc R U . . .
C11 C 0.10722(17) 0.6512(3) 0.57245(17) 0.0253(5) Uani 1 1 d . U . . .
C12 C 0.05572(17) 0.5009(3) 0.51275(17) 0.0245(5) Uani 1 1 d . U . . .
C13 C 0.10892(17) 0.3539(3) 0.47691(17) 0.0256(5) Uani 1 1 d D U . . .
C14 C 0.05618(18) 0.1986(4) 0.42570(17) 0.0263(5) Uani 1 1 d . U . . .
C15 C 0.10836(19) 0.0441(4) 0.39208(18) 0.0289(6) Uani 1 1 d . U . . .
H15 H 0.1804 0.0456 0.4059 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0574(2) -0.1031(4) 0.34133(18) 0.0324(6) Uani 1 1 d . U . . .
H16 H 0.0941 -0.2043 0.3213 0.039 Uiso 1 1 calc R U . . .
C17 C -0.0496(2) -0.1076(4) 0.31794(18) 0.0330(6) Uani 1 1 d . U . . .
H17 H -0.0847 -0.2120 0.2826 0.040 Uiso 1 1 calc R U . . .
C18 C 0.05252(18) 0.8045(4) 0.59891(17) 0.0269(5) Uani 1 1 d . U . . .
C19 C 0.10295(19) 0.9629(4) 0.65413(18) 0.0303(6) Uani 1 1 d . U . . .
H19 H 0.1751 0.9667 0.6715 0.036 Uiso 1 1 calc R U . . .
S1A S 0.25983(10) 0.4734(2) 0.39012(8) 0.0348(3) Uani 0.784(3) 1 d D U P A 1
C7A C 0.2200(4) 0.3572(16) 0.4795(8) 0.0271(15) Uani 0.784(3) 1 d D U P A 1
C8A C 0.2988(9) 0.270(2) 0.5424(11) 0.0413(12) Uani 0.784(3) 1 d D U P A 1
H8A H 0.2911 0.2010 0.5974 0.050 Uiso 0.784(3) 1 calc R U P A 1
C9A C 0.3937(5) 0.2918(10) 0.5175(4) 0.0359(10) Uani 0.784(3) 1 d D U P A 1
H9A H 0.4557 0.2381 0.5530 0.043 Uiso 0.784(3) 1 calc R U P A 1
C10A C 0.3842(3) 0.4008(9) 0.4357(4) 0.0377(10) Uani 0.784(3) 1 d D U P A 1
H10A H 0.4390 0.4322 0.4077 0.045 Uiso 0.784(3) 1 calc R U P A 1
C7B C 0.2187(12) 0.381(7) 0.485(3) 0.0271(15) Uani 0.216(3) 1 d D U P A 2
C8B C 0.2545(16) 0.447(4) 0.4111(16) 0.0348(3) Uani 0.216(3) 1 d D U P A 2
H8B H 0.2100 0.5040 0.3569 0.042 Uiso 0.216(3) 1 calc R U P A 2
C9B C 0.3610(14) 0.428(4) 0.4155(17) 0.0377(10) Uani 0.216(3) 1 d D U P A 2
H9B H 0.3971 0.4830 0.3729 0.045 Uiso 0.216(3) 1 calc R U P A 2
C10B C 0.3996(18) 0.316(4) 0.4939(17) 0.0359(10) Uani 0.216(3) 1 d D U P A 2
H10B H 0.4688 0.2774 0.5121 0.043 Uiso 0.216(3) 1 calc R U P A 2
S1B S 0.3116(9) 0.250(2) 0.5563(10) 0.0413(12) Uani 0.216(3) 1 d D U P A 2
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
C2 C1 C6 120.0 . .
C2 C1 C11 121.32(13) . .
C6 C1 C11 118.32(13) . .
C3 C2 C1 120.0 . .
C2 C3 C4 120.0 . .
C5 C4 C3 120.0 . .
C4 C5 C6 120.0 . .
C5 C6 C1 120.0 . .
C18 C11 C12 120.7(2) . .
C18 C11 C1 115.37(19) . .
C12 C11 C1 123.6(2) . .
C13 C12 C11 122.2(2) . .
C13 C12 C12 119.1(3) . 3_566
C11 C12 C12 118.8(3) . 3_566
C14 C13 C12 120.6(2) . .
C14 C13 C7B 121(2) . .
C12 C13 C7B 118(2) . .
C14 C13 C7A 114.0(6) . .
C12 C13 C7A 125.0(5) . .
C13 C14 C18 120.3(2) . 3_566
C13 C14 C15 121.8(2) . .
C18 C14 C15 117.9(2) 3_566 .
C16 C15 C14 121.7(2) . .
C15 C16 C17 120.5(2) . .
C19 C17 C16 120.2(2) 3_566 .
C11 C18 C14 120.0(2) . 3_566
C11 C18 C19 121.7(2) . .
C14 C18 C19 118.2(2) 3_566 .
C17 C19 C18 121.4(2) 3_566 .
C7A S1A C10A 92.0(3) . .
C8A C7A C13 129.2(9) . .
C8A C7A S1A 111.6(7) . .
C13 C7A S1A 119.1(5) . .
C7A C8A C9A 113.5(11) . .
C10A C9A C8A 111.6(7) . .
C9A C10A S1A 111.4(5) . .
C8B C7B C13 122(2) . .
C8B C7B S1B 107.6(16) . .
C13 C7B S1B 124.8(19) . .
C7B C8B C9B 119(2) . .
C10B C9B C8B 106(2) . .
C9B C10B S1B 114(2) . .
C7B S1B C10B 93.0(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3900 .
C1 C6 1.3900 .
C1 C11 1.529(2) .
C2 C3 1.3900 .
C3 C4 1.3900 .
C4 C5 1.3900 .
C5 C6 1.3900 .
C11 C18 1.409(3) .
C11 C12 1.429(3) .
C12 C13 1.423(3) .
C12 C12 1.467(4) 3_566
C13 C14 1.408(3) .
C13 C7B 1.478(16) .
C13 C7A 1.498(5) .
C14 C18 1.431(3) 3_566
C14 C15 1.439(3) .
C15 C16 1.352(4) .
C16 C17 1.411(4) .
C17 C19 1.361(4) 3_566
C18 C14 1.431(3) 3_566
C18 C19 1.437(3) .
C19 C17 1.361(4) 3_566
S1A C7A 1.710(8) .
S1A C10A 1.733(4) .
C7A C8A 1.365(12) .
C8A C9A 1.424(13) .
C9A C10A 1.378(6) .
C7B C8B 1.35(2) .
C7B S1B 1.69(2) .
C8B C9B 1.44(2) .
C9B C10B 1.368(16) .
C10B S1B 1.718(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 54762566
