#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233711.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_7233711
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            'C42 H26 N2 O4'
_chemical_formula_weight         622.68
_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                 100.6160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0983(3)
_cell_length_b                   7.1706(2)
_cell_length_c                   14.2489(5)
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.4
_cell_volume                     1516.24(7)
_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      153(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 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 50
	           Slice: 20.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0234
scan:
	Number of images: 25
	           Slice: 95.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0234
;
_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      0.066123
_diffrn_orient_matrix_UB_12      -0.011485
_diffrn_orient_matrix_UB_13      0.024378
_diffrn_orient_matrix_UB_21      0.010597
_diffrn_orient_matrix_UB_22      0.134657
_diffrn_orient_matrix_UB_23      0.034698
_diffrn_orient_matrix_UB_31      -0.012988
_diffrn_orient_matrix_UB_32      -0.015539
_diffrn_orient_matrix_UB_33      0.064271
_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  0.0759
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14425
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.909
_diffrn_source_current           35.0
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.984
_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             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.025(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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0673
_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)+(0.0374P)²+1.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000009.cif
_cod_data_source_block           PCOD1000009
_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        'C42 H26 N2 O4 '
_cod_database_code               7233711
_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 0.19529(5) 1.14297(13) 0.97104(6) 0.0262(4) Uani 1 1 d G U . . .
C2 C 0.25861(7) 1.24832(10) 1.03195(6) 0.0325(5) Uani 1 1 d G U . . .
H2 H 0.2404 1.3229 1.0801 0.039 Uiso 1 1 calc R U . . .
C3 C 0.34855(6) 1.24458(13) 1.02233(7) 0.0405(6) Uani 1 1 d G U . . .
H3 H 0.3918 1.3166 1.0640 0.049 Uiso 1 1 calc R U . . .
C4 C 0.37518(6) 1.13549(17) 0.95181(7) 0.0432(6) Uani 1 1 d G U . . .
H4 H 0.4366 1.1329 0.9452 0.052 Uiso 1 1 calc R U . . .
C5 C 0.31186(7) 1.03014(17) 0.89090(5) 0.0402(6) Uani 1 1 d G U . . .
H5 H 0.3301 0.9556 0.8427 0.048 Uiso 1 1 calc R U . . .
C6 C 0.22192(6) 1.03388(15) 0.90052(5) 0.0320(5) Uani 1 1 d G U . . .
H6 H 0.1786 0.9619 0.8589 0.038 Uiso 1 1 calc R U . . .
C7 C 0.19385(5) 0.87770(13) 1.11751(6) 0.0248(4) Uani 1 1 d G U . . .
C8 C 0.21080(6) 0.98589(15) 1.19981(5) 0.0299(5) Uani 1 1 d G U . . .
H8 H 0.1629 1.0508 1.2202 0.036 Uiso 1 1 calc R U . . .
C9 C 0.29784(7) 0.99904(16) 1.25222(5) 0.0329(5) Uani 1 1 d G U . . .
H9 H 0.3094 1.0730 1.3085 0.040 Uiso 1 1 calc R U . . .
C10 C 0.36794(6) 0.90400(16) 1.22232(6) 0.0314(5) Uani 1 1 d G U . . .
C11 C 0.35099(6) 0.79580(12) 1.14002(7) 0.0328(5) Uani 1 1 d G U . . .
H11 H 0.3989 0.7308 1.1196 0.039 Uiso 1 1 calc R U . . .
C12 C 0.26395(6) 0.78265(9) 1.08761(6) 0.0295(5) Uani 1 1 d G U . . .
H12 H 0.2524 0.7087 1.0314 0.035 Uiso 1 1 calc R U . . .
C13 C 0.09515(12) 1.1510(3) 0.97373(14) 0.0241(4) Uani 1 1 d . U . . .
C14 C 0.04961(12) 1.0027(3) 1.01090(14) 0.0234(4) Uani 1 1 d . U . . .
C15 C 0.09629(12) 0.8587(3) 1.06942(14) 0.0244(4) Uani 1 1 d . U . . .
C16 C 0.05024(13) 0.7055(3) 1.09680(13) 0.0242(4) Uani 1 1 d . U . . .
C17 C 0.09599(14) 0.5576(3) 1.15502(14) 0.0287(5) Uani 1 1 d . U . . .
H17 H 0.1598 0.5615 1.1730 0.034 Uiso 1 1 calc R U . . .
C18 C 0.05029(14) 0.4128(3) 1.18485(15) 0.0314(5) Uani 1 1 d . U . . .
H18 H 0.0824 0.3169 1.2226 0.038 Uiso 1 1 calc R U . . .
C19 C -0.04490(15) 0.4037(3) 1.16015(15) 0.0315(5) Uani 1 1 d . U . . .
H19 H -0.0762 0.3006 1.1804 0.038 Uiso 1 1 calc R U . . .
C20 C -0.09152(14) 0.5422(3) 1.10753(14) 0.0287(5) Uani 1 1 d . U . . .
H20 H -0.1554 0.5351 1.0925 0.034 Uiso 1 1 calc R U . . .
C21 C -0.04691(13) 0.6988(3) 1.07414(14) 0.0249(4) Uani 1 1 d . U . . .
N N 0.45827(12) 0.9208(3) 1.27714(15) 0.0402(5) Uani 1 1 d . U . . .
O O 0.46717(11) 0.9789(3) 1.35921(13) 0.0516(5) Uani 1 1 d . U . . .
O1 O 0.52149(11) 0.8755(4) 1.23951(15) 0.0633(7) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 C13 122.43(9) . .
C6 C1 C13 117.45(9) . .
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 . .
C8 C7 C12 120.0 . .
C8 C7 C15 116.43(9) . .
C12 C7 C15 123.39(9) . .
C7 C8 C9 120.0 . .
C10 C9 C8 120.0 . .
C9 C10 C11 120.0 . .
C9 C10 N 119.28(11) . .
C11 C10 N 120.72(11) . .
C12 C11 C10 120.0 . .
C11 C12 C7 120.0 . .
C21 C13 C14 120.77(17) 3_577 .
C21 C13 C1 116.49(16) 3_577 .
C14 C13 C1 122.19(16) . .
C13 C14 C15 122.54(17) . .
C13 C14 C14 119.0(2) . 3_577
C15 C14 C14 118.5(2) . 3_577
C16 C15 C14 121.01(17) . .
C16 C15 C7 116.01(15) . .
C14 C15 C7 122.29(16) . .
C15 C16 C17 122.02(18) . .
C15 C16 C21 120.15(17) . .
C17 C16 C21 117.61(18) . .
C18 C17 C16 121.69(19) . .
C17 C18 C19 120.58(19) . .
C20 C19 C18 120.1(2) . .
C19 C20 C21 121.83(19) . .
C13 C21 C20 121.86(18) 3_577 .
C13 C21 C16 119.86(18) 3_577 .
C20 C21 C16 118.14(18) . .
O1 N O 123.51(19) . .
O1 N C10 118.43(18) . .
O N C10 118.06(18) . .
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 C13 1.521(2) .
C2 C3 1.3900 .
C3 C4 1.3900 .
C4 C5 1.3900 .
C5 C6 1.3900 .
C7 C8 1.3900 .
C7 C12 1.3900 .
C7 C15 1.5120(19) .
C8 C9 1.3900 .
C9 C10 1.3900 .
C10 C11 1.3900 .
C10 N 1.4464(19) .
C11 C12 1.3900 .
C13 C21 1.404(3) 3_577
C13 C14 1.421(3) .
C14 C15 1.429(3) .
C14 C14 1.473(4) 3_577
C15 C16 1.394(3) .
C16 C17 1.442(3) .
C16 C21 1.443(3) .
C17 C18 1.357(3) .
C18 C19 1.417(3) .
C19 C20 1.360(3) .
C20 C21 1.435(3) .
C21 C13 1.404(3) 3_577
N O1 1.222(3) .
N O 1.225(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102135095
