#------------------------------------------------------------------------------
#$Date: 2019-09-09 10:03:42 +0300 (Mon, 09 Sep 2019) $
#$Revision: 218090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233710.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_7233710
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 H26 S2'
_chemical_formula_weight         546.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.276(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5180(6)
_cell_length_b                   6.0678(3)
_cell_length_c                   20.8427(10)
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1454.29(13)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 40
	           Slice: 50.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 420.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.0074
scan:
	Number of images: 35
	           Slice: 72.0000 - 177.0000
	     Image width: 3.0000
	        Exp time: 420.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0074
;
_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      -0.029364
_diffrn_orient_matrix_UB_12      0.015735
_diffrn_orient_matrix_UB_13      0.080329
_diffrn_orient_matrix_UB_21      -0.155105
_diffrn_orient_matrix_UB_22      -0.013300
_diffrn_orient_matrix_UB_23      -0.054093
_diffrn_orient_matrix_UB_31      -0.000200
_diffrn_orient_matrix_UB_32      -0.046530
_diffrn_orient_matrix_UB_33      0.012015
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14547
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.714
_diffrn_source_current           35.0
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.21
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;
_exptl_crystal_colour            Yellow
_exptl_crystal_description       Needle
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6467
_refine_ls_number_restraints     431
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0480P)²+0.4083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4379
_reflns_number_total             6467
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000008.cif
_cod_data_source_block           PCOD1000008
_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        1454.29(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C38 H26 S2 '
_cod_database_code               7233710
_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'
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
C1A C 0.7037(13) 0.566(4) 0.7152(14) 0.084(3) Uani 0.616(7) 1 d D U P A 1
H1A H 0.7842 0.5733 0.7210 0.101 Uiso 0.616(7) 1 calc R U P A 1
C2A C 0.6500(15) 0.407(4) 0.6812(15) 0.081(3) Uani 0.616(7) 1 d D U P A 1
H2A H 0.6868 0.2896 0.6622 0.097 Uiso 0.616(7) 1 calc R U P A 1
C3A C 0.518(2) 0.447(5) 0.6781(15) 0.0796(18) Uani 0.616(7) 1 d D U P A 1
H3AA H 0.4620 0.3582 0.6568 0.096 Uiso 0.616(7) 1 calc R U P A 1
C4A C 0.4962(17) 0.630(8) 0.711(3) 0.055(2) Uani 0.616(7) 1 d D U P A 1
S1A S 0.6228(4) 0.7391(9) 0.7446(3) 0.0853(13) Uani 0.616(7) 1 d D U P A 1
C2B C 0.6998(19) 0.507(6) 0.708(2) 0.084(3) Uani 0.384(7) 1 d D U P A 2
H2B H 0.7803 0.5025 0.7153 0.101 Uiso 0.384(7) 1 calc R U P A 2
C1B C 0.635(2) 0.368(8) 0.673(3) 0.081(3) Uani 0.384(7) 1 d D U P A 2
H1B H 0.6675 0.2532 0.6509 0.097 Uiso 0.384(7) 1 calc R U P A 2
S1B S 0.5048(10) 0.4041(18) 0.6699(6) 0.0796(18) Uani 0.384(7) 1 d D U P A 2
C4B C 0.503(3) 0.644(13) 0.714(5) 0.055(2) Uani 0.384(7) 1 d D U P A 2
C3B C 0.615(2) 0.682(6) 0.7361(19) 0.0853(13) Uani 0.384(7) 1 d D U P A 2
H3BA H 0.6379 0.7959 0.7637 0.102 Uiso 0.384(7) 1 calc R U P A 2
C7C C 0.3305(17) 0.925(7) 0.6113(7) 0.054(4) Uani 0.698(7) 1 d D U P B 1
C8C C 0.2516(19) 0.998(7) 0.5662(10) 0.087(2) Uani 0.698(7) 1 d D U P B 1
H8CA H 0.1738 1.0256 0.5729 0.104 Uiso 0.698(7) 1 calc R U P B 1
C9C C 0.3062(13) 1.027(4) 0.5051(7) 0.085(3) Uani 0.698(7) 1 d D U P B 1
H9C H 0.2652 1.0702 0.4675 0.102 Uiso 0.698(7) 1 calc R U P B 1
C10C C 0.4194(14) 0.985(4) 0.5080(6) 0.079(3) Uani 0.698(7) 1 d D U P B 1
H10C H 0.4656 0.9932 0.4729 0.094 Uiso 0.698(7) 1 calc R U P B 1
S2C S 0.4700(3) 0.9146(10) 0.58351(15) 0.0779(10) Uani 0.698(7) 1 d D U P B 1
C7D C 0.341(4) 0.951(19) 0.6153(17) 0.054(4) Uani 0.302(7) 1 d D U P B 2
S2D S 0.2353(11) 1.002(4) 0.5548(5) 0.087(2) Uani 0.302(7) 1 d D U P B 2
C10D C 0.330(3) 1.026(11) 0.4955(15) 0.085(3) Uani 0.302(7) 1 d D U P B 2
H10D H 0.3095 1.0517 0.4523 0.102 Uiso 0.302(7) 1 calc R U P B 2
C9D C 0.439(3) 1.001(11) 0.5218(16) 0.079(3) Uani 0.302(7) 1 d D U P B 2
H9D H 0.5046 1.0243 0.4986 0.094 Uiso 0.302(7) 1 calc R U P B 2
C8D C 0.448(3) 0.932(10) 0.5911(15) 0.0779(10) Uani 0.302(7) 1 d D U P B 2
H8DA H 0.5152 0.8841 0.6138 0.094 Uiso 0.302(7) 1 calc R U P B 2
C5 C 0.3865(4) 0.7443(9) 0.7199(2) 0.0516(11) Uani 1 1 d D U . . .
C6 C 0.3164(4) 0.8678(9) 0.67886(19) 0.0500(11) Uani 1 1 d D U . . .
C11 C 0.2246(4) 0.8910(9) 0.72719(19) 0.0474(11) Uani 1 1 d . U . . .
C12 C 0.1139(4) 0.9636(8) 0.7240(2) 0.0478(11) Uani 1 1 d . U . . .
C13 C 0.07176(18) 1.1133(3) 0.67089(9) 0.0519(12) Uani 1 1 d G U . . .
C14 C 0.1288(2) 1.3113(4) 0.66108(11) 0.0691(15) Uani 1 1 d G U . . .
H14 H 0.1949 1.3478 0.6865 0.083 Uiso 1 1 calc R U . . .
C15 C 0.0869(3) 1.4549(4) 0.61320(12) 0.091(2) Uani 1 1 d G U . . .
H15 H 0.1250 1.5874 0.6066 0.109 Uiso 1 1 calc R U . . .
C16 C -0.0120(3) 1.4005(5) 0.57514(11) 0.092(2) Uani 1 1 d G U . . .
H16 H -0.0400 1.4965 0.5431 0.110 Uiso 1 1 calc R U . . .
C17 C -0.0690(3) 1.2024(6) 0.58495(9) 0.0821(18) Uani 1 1 d G U . . .
H17 H -0.1351 1.1660 0.5595 0.099 Uiso 1 1 calc R U . . .
C18 C -0.0271(2) 1.0589(4) 0.63282(7) 0.0683(15) Uani 1 1 d G U . . .
H18 H -0.0653 0.9264 0.6394 0.082 Uiso 1 1 calc R U . . .
C19 C 0.02676(16) 0.9051(4) 0.77119(8) 0.0487(11) Uani 1 1 d G U . . .
C20 C -0.05668(19) 1.0608(4) 0.78508(8) 0.0592(13) Uani 1 1 d G U . . .
H20 H -0.0553 1.1997 0.7663 0.071 Uiso 1 1 calc R U . . .
C21 C -0.1421(2) 1.0090(5) 0.82707(10) 0.0694(15) Uani 1 1 d G U . . .
H21 H -0.1980 1.1132 0.8364 0.083 Uiso 1 1 calc R U . . .
C22 C -0.1441(2) 0.8014(6) 0.85518(10) 0.0687(15) Uani 1 1 d G U . . .
H22 H -0.2013 0.7667 0.8833 0.082 Uiso 1 1 calc R U . . .
C23 C -0.0607(2) 0.6456(5) 0.84130(11) 0.0609(13) Uani 1 1 d G U . . .
H23 H -0.0620 0.5067 0.8601 0.073 Uiso 1 1 calc R U . . .
C24 C 0.0247(2) 0.6975(4) 0.79930(11) 0.0529(12) Uani 1 1 d G U . . .
H24 H 0.0806 0.5933 0.7900 0.064 Uiso 1 1 calc R U . . .
C25 C 0.3067(4) 0.7642(8) 0.7735(2) 0.0483(11) Uani 1 1 d . U . . .
C26 C 0.3201(4) 0.7133(8) 0.8369(2) 0.0471(11) Uani 1 1 d . U . . .
C27 C 0.24477(15) 0.7999(3) 0.88730(8) 0.0447(10) Uani 1 1 d G U . . .
C28 C 0.1980(2) 1.0111(3) 0.88605(11) 0.0533(12) Uani 1 1 d G U . . .
H28 H 0.2118 1.1056 0.8522 0.064 Uiso 1 1 calc R U . . .
C29 C 0.1306(2) 1.0811(4) 0.93541(12) 0.0613(13) Uani 1 1 d G U . . .
H29 H 0.0993 1.2224 0.9346 0.074 Uiso 1 1 calc R U . . .
C30 C 0.11007(19) 0.9399(5) 0.98603(11) 0.0659(14) Uani 1 1 d G U . . .
H30 H 0.0650 0.9867 1.0191 0.079 Uiso 1 1 calc R U . . .
C31 C 0.15685(18) 0.7287(4) 0.98729(10) 0.0618(14) Uani 1 1 d G U . . .
H31 H 0.1431 0.6342 1.0212 0.074 Uiso 1 1 calc R U . . .
C32 C 0.22420(14) 0.6587(3) 0.93793(9) 0.0535(12) Uani 1 1 d G U . . .
H32 H 0.2555 0.5173 0.9388 0.064 Uiso 1 1 calc R U . . .
C33 C 0.41698(16) 0.5603(3) 0.86016(8) 0.0499(11) Uani 1 1 d G U . . .
C34 C 0.4302(2) 0.3560(4) 0.83131(10) 0.0578(13) Uani 1 1 d G U . . .
H34 H 0.3811 0.3150 0.7964 0.069 Uiso 1 1 calc R U . . .
C35 C 0.5170(2) 0.2130(4) 0.85464(13) 0.0679(15) Uani 1 1 d G U . . .
H35 H 0.5258 0.0763 0.8353 0.081 Uiso 1 1 calc R U . . .
C36 C 0.5904(2) 0.2743(5) 0.90681(12) 0.0727(16) Uani 1 1 d G U . . .
H36 H 0.6485 0.1786 0.9224 0.087 Uiso 1 1 calc R U . . .
C37 C 0.57721(16) 0.4786(5) 0.93567(11) 0.0664(15) Uani 1 1 d G U . . .
H37 H 0.6264 0.5196 0.9706 0.080 Uiso 1 1 calc R U . . .
C38 C 0.49047(13) 0.6216(4) 0.91234(10) 0.0570(13) Uani 1 1 d G U . . .
H38 H 0.4816 0.7583 0.9316 0.068 Uiso 1 1 calc R 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
C2A C1A S1A 115.4(14) . .
C1A C2A C3A 109.8(17) . .
C4A C3A C2A 109(2) . .
C3A C4A C5 130(2) . .
C3A C4A S1A 110.6(13) . .
C5 C4A S1A 119.1(19) . .
C1A S1A C4A 95.4(9) . .
C1B C2B C3B 107(2) . .
C2B C1B S1B 118(2) . .
C1B S1B C4B 98.0(17) . .
C3B C4B C5 138(4) . .
C3B C4B S1B 106.4(17) . .
C5 C4B S1B 115(3) . .
C4B C3B C2B 111(2) . .
C8C C7C C6 129.8(17) . .
C8C C7C S2C 112.4(10) . .
C6 C7C S2C 117.7(13) . .
C7C C8C C9C 109.9(16) . .
C10C C9C C8C 114.1(14) . .
C9C C10C S2C 111.9(13) . .
C10C S2C C7C 91.4(7) . .
C8D C7D C6 122(4) . .
C8D C7D S2D 111.0(19) . .
C6 C7D S2D 124(3) . .
C10D S2D C7D 95.4(15) . .
C9D C10D S2D 108(3) . .
C10D C9D C8D 115(3) . .
C7D C8D C9D 109(2) . .
C6 C5 C4A 132(3) . .
C6 C5 C4B 133(5) . .
C6 C5 C25 93.2(4) . .
C4A C5 C25 135(3) . .
C4B C5 C25 134(5) . .
C5 C6 C7C 129.5(13) . .
C5 C6 C7D 128(3) . .
C5 C6 C11 92.6(4) . .
C7C C6 C11 137.6(12) . .
C7D C6 C11 139(3) . .
C12 C11 C6 134.1(4) . .
C12 C11 C25 138.5(4) . .
C6 C11 C25 86.7(3) . .
C11 C12 C19 124.2(4) . .
C11 C12 C13 120.2(4) . .
C19 C12 C13 115.6(3) . .
C14 C13 C18 120.0 . .
C14 C13 C12 119.9(2) . .
C18 C13 C12 120.0(2) . .
C13 C14 C15 120.0 . .
C16 C15 C14 120.0 . .
C15 C16 C17 120.0 . .
C18 C17 C16 120.0 . .
C17 C18 C13 120.0 . .
C20 C19 C24 120.0 . .
C20 C19 C12 118.4(2) . .
C24 C19 C12 121.5(2) . .
C21 C20 C19 120.0 . .
C20 C21 C22 120.0 . .
C23 C22 C21 120.0 . .
C24 C23 C22 120.0 . .
C23 C24 C19 120.0 . .
C26 C25 C5 132.1(4) . .
C26 C25 C11 139.9(4) . .
C5 C25 C11 87.3(3) . .
C25 C26 C27 124.5(4) . .
C25 C26 C33 119.6(4) . .
C27 C26 C33 115.9(3) . .
C28 C27 C32 120.0 . .
C28 C27 C26 123.4(2) . .
C32 C27 C26 116.6(2) . .
C27 C28 C29 120.0 . .
C28 C29 C30 120.0 . .
C31 C30 C29 120.0 . .
C32 C31 C30 120.0 . .
C31 C32 C27 120.0 . .
C34 C33 C38 120.0 . .
C34 C33 C26 120.4(2) . .
C38 C33 C26 119.5(2) . .
C35 C34 C33 120.0 . .
C34 C35 C36 120.0 . .
C37 C36 C35 120.0 . .
C38 C37 C36 120.0 . .
C37 C38 C33 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C2A 1.328(13) .
C1A S1A 1.552(13) .
C2A C3A 1.54(3) .
C3A C4A 1.34(4) .
C4A C5 1.461(11) .
C4A S1A 1.71(3) .
C2B C1B 1.324(18) .
C2B C3B 1.58(3) .
C1B S1B 1.51(2) .
S1B C4B 1.73(5) .
C4B C3B 1.36(4) .
C4B C5 1.486(16) .
C7C C8C 1.34(3) .
C7C C6 1.469(9) .
C7C S2C 1.74(2) .
C8C C9C 1.46(2) .
C9C C10C 1.325(13) .
C10C S2C 1.702(12) .
C7D C8D 1.36(4) .
C7D C6 1.46(2) .
C7D S2D 1.73(4) .
S2D C10D 1.70(2) .
C10D C9D 1.36(2) .
C9D C8D 1.50(3) .
C5 C6 1.366(7) .
C5 C25 1.493(6) .
C6 C11 1.508(6) .
C11 C12 1.347(6) .
C11 C25 1.521(6) .
C12 C19 1.488(5) .
C12 C13 1.492(5) .
C13 C14 1.3900 .
C13 C18 1.3900 .
C14 C15 1.3900 .
C15 C16 1.3900 .
C16 C17 1.3900 .
C17 C18 1.3900 .
C19 C20 1.3900 .
C19 C24 1.3900 .
C20 C21 1.3900 .
C21 C22 1.3900 .
C22 C23 1.3900 .
C23 C24 1.3900 .
C25 C26 1.356(6) .
C26 C27 1.496(5) .
C26 C33 1.510(5) .
C27 C28 1.3900 .
C27 C32 1.3900 .
C28 C29 1.3900 .
C29 C30 1.3900 .
C30 C31 1.3900 .
C31 C32 1.3900 .
C33 C34 1.3900 .
C33 C38 1.3900 .
C34 C35 1.3900 .
C35 C36 1.3900 .
C36 C37 1.3900 .
C37 C38 1.3900 .
