#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233706.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_7233706
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 H25 Cl S2'
_chemical_formula_weight         581.19
_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                 105.5490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5166(2)
_cell_length_b                   17.9901(4)
_cell_length_c                   15.6600(4)
_cell_measurement_reflns_used    13126
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     2854.36(11)
_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      253(2)
_diffrn_detector                 'Curved image plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
	Number of images: 44
	           Slice: 24.0000 - 156.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0434
;
_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      0.064552
_diffrn_orient_matrix_UB_12      0.012905
_diffrn_orient_matrix_UB_13      -0.073541
_diffrn_orient_matrix_UB_21      -0.036888
_diffrn_orient_matrix_UB_22      0.031793
_diffrn_orient_matrix_UB_23      -0.026800
_diffrn_orient_matrix_UB_31      0.034809
_diffrn_orient_matrix_UB_32      0.054034
_diffrn_orient_matrix_UB_33      0.016189
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16313
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.264
_diffrn_source_current           35.0
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.31
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.851
_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             1208
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         6499
_refine_ls_number_restraints     407
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0459
_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)+(0.0434P)²+1.4729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5783
_reflns_number_total             6500
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000004.cif
_cod_data_source_block           PCOD1000004
_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_cell_volume        2854.35(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C38 H25 Cl1 S2 '
_cod_database_code               7233706
_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 0.26123(17) 0.03236(10) 0.38676(12) 0.0339(4) Uani 1 1 d . U . . .
C2 C 0.22629(19) -0.00248(10) 0.45666(14) 0.0410(4) Uani 1 1 d . U . . .
H2 H 0.2793 0.0033 0.5142 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1132(2) -0.04574(12) 0.44121(17) 0.0528(5) Uani 1 1 d . U . . .
H3 H 0.0902 -0.0683 0.4884 0.063 Uiso 1 1 calc R U . . .
C4 C 0.0347(2) -0.05527(13) 0.35573(19) 0.0597(6) Uani 1 1 d . U . . .
H4 H -0.0419 -0.0836 0.3455 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0698(2) -0.02292(13) 0.28576(17) 0.0560(6) Uani 1 1 d . U . . .
H5 H 0.0177 -0.0303 0.2283 0.067 Uiso 1 1 calc R U . . .
C6 C 0.18260(19) 0.02073(11) 0.30031(14) 0.0436(4) Uani 1 1 d . U . . .
H6 H 0.2059 0.0422 0.2526 0.052 Uiso 1 1 calc R U . . .
C7 C 0.64539(16) 0.27376(9) 0.60038(11) 0.0305(3) Uani 1 1 d . U . . .
C8 C 0.70572(18) 0.34258(10) 0.59972(12) 0.0364(4) Uani 1 1 d . U . . .
H8 H 0.6587 0.3813 0.5662 0.044 Uiso 1 1 calc R U . . .
C9 C 0.83572(19) 0.35401(12) 0.64878(14) 0.0451(5) Uani 1 1 d . U . . .
H9 H 0.8751 0.4000 0.6465 0.054 Uiso 1 1 calc R U . . .
C10 C 0.90672(18) 0.29849(13) 0.70040(13) 0.0463(5) Uani 1 1 d . U . . .
H10 H 0.9926 0.3071 0.7343 0.056 Uiso 1 1 calc R U . . .
C11 C 0.84924(19) 0.22993(13) 0.70137(13) 0.0453(5) Uani 1 1 d . U . . .
H11 H 0.8969 0.1918 0.7357 0.054 Uiso 1 1 calc R U . . .
C12 C 0.72076(17) 0.21725(11) 0.65155(12) 0.0379(4) Uani 1 1 d . U . . .
H12 H 0.6839 0.1703 0.6521 0.045 Uiso 1 1 calc R U . . .
C13 C 0.42044(16) 0.32711(9) 0.50939(12) 0.0329(4) Uani 1 1 d . U . . .
C14 C 0.4185(2) 0.38961(11) 0.56206(15) 0.0459(5) Uani 1 1 d . U . . .
H14 H 0.4719 0.3909 0.6200 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3381(3) 0.44959(13) 0.5290(2) 0.0691(7) Uani 1 1 d . U . . .
H15 H 0.3386 0.4910 0.5647 0.083 Uiso 1 1 calc R U . . .
C16 C 0.2576(3) 0.44872(15) 0.4442(2) 0.0790(8) Uani 1 1 d . U . . .
H16 H 0.2024 0.4888 0.4230 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2586(2) 0.38818(14) 0.39029(19) 0.0641(6) Uani 1 1 d . U . . .
H17 H 0.2052 0.3877 0.3324 0.077 Uiso 1 1 calc R U . . .
C18 C 0.33969(18) 0.32794(11) 0.42281(14) 0.0420(4) Uani 1 1 d . U . . .
H18 H 0.3401 0.2874 0.3861 0.050 Uiso 1 1 calc R U . . .
C19 C 0.58661(15) 0.18849(9) 0.42938(10) 0.0283(3) Uani 1 1 d . U . . .
C20 C 0.58605(16) 0.12262(9) 0.37635(11) 0.0300(3) Uani 1 1 d . U . . .
C21 C 0.68684(18) 0.10832(10) 0.33328(12) 0.0366(4) Uani 1 1 d . U . . .
H21 H 0.7515 0.1440 0.3351 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6899(2) 0.04281(11) 0.28924(14) 0.0448(5) Uani 1 1 d . U . . .
H22 H 0.7573 0.0343 0.2623 0.054 Uiso 1 1 calc R U . . .
C23 C 0.5930(2) -0.01123(11) 0.28439(14) 0.0466(5) Uani 1 1 d . U . . .
H23 H 0.5975 -0.0561 0.2558 0.056 Uiso 1 1 calc R U . . .
C24 C 0.49122(19) 0.00177(10) 0.32162(13) 0.0404(4) Uani 1 1 d . U . . .
H24 H 0.4258 -0.0340 0.3168 0.049 Uiso 1 1 calc R U . . .
C25 C 0.48419(17) 0.06918(9) 0.36749(11) 0.0316(3) Uani 1 1 d . U . . .
C26 C 0.37598(16) 0.08430(9) 0.40432(11) 0.0302(3) Uani 1 1 d . U . . .
C27 C 0.38004(15) 0.14713(9) 0.45651(11) 0.0282(3) Uani 1 1 d . U . . .
C28 C 0.26802(15) 0.16879(9) 0.49162(11) 0.0306(3) Uani 1 1 d . U . . .
C29 C 0.29192(16) 0.20315(9) 0.56940(11) 0.0313(3) Uani 1 1 d . U . . .
C30 C 0.43218(16) 0.22163(9) 0.61712(11) 0.0304(3) Uani 1 1 d . U . . .
H30 H 0.4783 0.1753 0.6391 0.036 Uiso 1 1 calc R U . . .
C31 C 0.50067(15) 0.25764(9) 0.54842(11) 0.0275(3) Uani 1 1 d . U . . .
C32 C 0.49279(15) 0.19670(9) 0.47638(10) 0.0265(3) Uani 1 1 d . U . . .
C33 C 0.42519(19) 0.26824(11) 0.69557(12) 0.0399(4) Uani 1 1 d . U . . .
H33 H 0.4999 0.2880 0.7350 0.048 Uiso 1 1 calc R U . . .
C34 C 0.3046(2) 0.27904(12) 0.70427(13) 0.0451(5) Uani 1 1 d . U . . .
H34 H 0.2889 0.3057 0.7513 0.054 Uiso 1 1 calc R U . . .
S2 S 0.17624(5) 0.23924(3) 0.62045(3) 0.04500(14) Uani 1 1 d . U . . .
C35A C 0.6880(7) 0.2486(6) 0.4274(12) 0.0301(6) Uani 0.751(3) 1 d D U P A 1
C36A C 0.8220(9) 0.2464(7) 0.4625(9) 0.0412(9) Uani 0.751(3) 1 d D U P A 1
H36A H 0.8666 0.2064 0.4945 0.049 Uiso 0.751(3) 1 calc R U P A 1
C37A C 0.8859(6) 0.3128(3) 0.4444(5) 0.0414(8) Uani 0.751(3) 1 d D U P A 1
H37A H 0.9764 0.3210 0.4633 0.050 Uiso 0.751(3) 1 calc R U P A 1
C38A C 0.7971(3) 0.3625(2) 0.3959(3) 0.0418(8) Uani 0.751(3) 1 d D U P A 1
H38A H 0.8203 0.4086 0.3778 0.050 Uiso 0.751(3) 1 calc R U P A 1
S1A S 0.63749(8) 0.32996(4) 0.37204(6) 0.0384(2) Uani 0.751(3) 1 d D U P A 1
C35B C 0.677(2) 0.244(2) 0.428(4) 0.0301(6) Uani 0.249(3) 1 d D U P A 2
S1B S 0.8454(6) 0.2389(5) 0.4690(7) 0.0412(9) Uani 0.249(3) 1 d D U P A 2
C38B C 0.870(2) 0.3251(11) 0.4297(17) 0.0414(8) Uani 0.249(3) 1 d D U P A 2
H38B H 0.9521 0.3472 0.4387 0.050 Uiso 0.249(3) 1 calc R U P A 2
C37B C 0.7558(11) 0.3576(9) 0.3840(11) 0.0418(8) Uani 0.249(3) 1 d D U P A 2
H37B H 0.7488 0.4040 0.3571 0.050 Uiso 0.249(3) 1 calc R U P A 2
C36B C 0.6496(13) 0.3099(6) 0.3837(9) 0.0384(2) Uani 0.249(3) 1 d D U P A 2
H36B H 0.5634 0.3228 0.3542 0.046 Uiso 0.249(3) 1 calc R U P A 2
Cl Cl 0.10641(4) 0.16318(3) 0.42514(3) 0.04508(13) 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'
Cl Cl 0.1484 0.1585 '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 118.73(17) . .
C2 C1 C26 120.49(16) . .
C6 C1 C26 120.70(17) . .
C3 C2 C1 120.6(2) . .
C4 C3 C2 120.0(2) . .
C5 C4 C3 120.0(2) . .
C4 C5 C6 120.5(2) . .
C5 C6 C1 120.0(2) . .
C8 C7 C12 117.41(16) . .
C8 C7 C31 123.24(15) . .
C12 C7 C31 119.35(15) . .
C9 C8 C7 120.61(18) . .
C10 C9 C8 121.07(19) . .
C9 C10 C11 119.18(18) . .
C10 C11 C12 120.42(19) . .
C11 C12 C7 121.27(18) . .
C18 C13 C14 117.65(17) . .
C18 C13 C31 121.40(16) . .
C14 C13 C31 120.78(16) . .
C15 C14 C13 120.7(2) . .
C16 C15 C14 120.7(2) . .
C15 C16 C17 119.9(2) . .
C16 C17 C18 119.8(2) . .
C17 C18 C13 121.3(2) . .
C35B C19 C32 121(3) . .
C35B C19 C20 119(3) . .
C32 C19 C20 119.85(15) . .
C32 C19 C35A 122.4(8) . .
C20 C19 C35A 117.7(8) . .
C25 C20 C21 118.02(15) . .
C25 C20 C19 119.89(14) . .
C21 C20 C19 122.08(15) . .
C22 C21 C20 120.97(17) . .
C21 C22 C23 120.75(17) . .
C24 C23 C22 120.03(18) . .
C23 C24 C25 120.90(18) . .
C20 C25 C24 119.18(15) . .
C20 C25 C26 119.50(15) . .
C24 C25 C26 121.32(16) . .
C27 C26 C25 119.27(15) . .
C27 C26 C1 120.92(14) . .
C25 C26 C1 119.81(15) . .
C26 C27 C32 121.43(14) . .
C26 C27 C28 122.07(15) . .
C32 C27 C28 116.44(14) . .
C29 C28 C27 119.30(15) . .
C29 C28 Cl 119.30(13) . .
C27 C28 Cl 120.61(12) . .
C28 C29 C30 118.59(14) . .
C28 C29 S2 127.42(13) . .
C30 C29 S2 113.65(12) . .
C29 C30 C33 105.85(14) . .
C29 C30 C31 108.50(13) . .
C33 C30 C31 117.18(14) . .
C13 C31 C7 114.41(13) . .
C13 C31 C32 111.49(13) . .
C7 C31 C32 111.47(12) . .
C13 C31 C30 107.51(13) . .
C7 C31 C30 106.34(13) . .
C32 C31 C30 104.95(12) . .
C19 C32 C27 118.53(14) . .
C19 C32 C31 123.44(14) . .
C27 C32 C31 118.02(13) . .
C34 C33 C30 115.02(17) . .
C33 C34 S2 115.26(15) . .
C29 S2 C34 90.19(9) . .
C36A C35A C19 128.4(8) . .
C36A C35A S1A 112.0(6) . .
C19 C35A S1A 119.6(5) . .
C35A C36A C37A 112.5(9) . .
C38A C37A C36A 111.6(6) . .
C37A C38A S1A 112.3(4) . .
C35A S1A C38A 91.6(3) . .
C36B C35B C19 125.3(19) . .
C36B C35B S1B 106.8(13) . .
C19 C35B S1B 127.4(19) . .
C38B S1B C35B 93.4(12) . .
C37B C38B S1B 112.7(15) . .
C38B C37B C36B 109.2(15) . .
C35B C36B C37B 117.9(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.393(3) .
C1 C6 1.400(3) .
C1 C26 1.492(2) .
C2 C3 1.387(3) .
C3 C4 1.382(4) .
C4 C5 1.376(4) .
C5 C6 1.389(3) .
C7 C8 1.392(2) .
C7 C12 1.401(3) .
C7 C31 1.549(2) .
C8 C9 1.392(3) .
C9 C10 1.373(3) .
C10 C11 1.376(3) .
C11 C12 1.386(3) .
C13 C18 1.394(3) .
C13 C14 1.398(3) .
C13 C31 1.540(2) .
C14 C15 1.383(3) .
C15 C16 1.370(4) .
C16 C17 1.380(4) .
C17 C18 1.389(3) .
C19 C35B 1.38(2) .
C19 C32 1.388(2) .
C19 C20 1.446(2) .
C19 C35A 1.525(6) .
C20 C25 1.418(2) .
C20 C21 1.424(2) .
C21 C22 1.370(3) .
C22 C23 1.396(3) .
C23 C24 1.369(3) .
C24 C25 1.422(2) .
C25 C26 1.433(2) .
C26 C27 1.389(2) .
C27 C32 1.449(2) .
C27 C28 1.480(2) .
C28 C29 1.328(2) .
C28 Cl 1.7417(17) .
C29 C30 1.501(2) .
C29 S2 1.7498(16) .
C30 C33 1.505(2) .
C30 C31 1.585(2) .
C31 C32 1.559(2) .
C33 C34 1.325(3) .
C34 S2 1.763(2) .
C35A C36A 1.369(12) .
C35A S1A 1.711(9) .
C36A C37A 1.435(12) .
C37A C38A 1.366(5) .
C38A S1A 1.722(3) .
C35B C36B 1.37(2) .
C35B S1B 1.71(2) .
S1B C38B 1.712(16) .
C38B C37B 1.350(14) .
C37B C36B 1.407(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338766
