#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233704.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_7233704
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            'C44 H26 N2'
_chemical_formula_weight         582.70
_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                 98.099(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.9125(6)
_cell_length_b                   7.1151(2)
_cell_length_c                   14.4263(4)
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     1515.42(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
	Number of images: 24
	           Slice: 50.0000 - 170.0000
	     Image width: 5.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.0386
scan:
	Number of images: 21
	           Slice: 72.0000 - 177.0000
	     Image width: 5.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0386
;
_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      -0.042459
_diffrn_orient_matrix_UB_12      0.054924
_diffrn_orient_matrix_UB_13      -0.009102
_diffrn_orient_matrix_UB_21      0.111404
_diffrn_orient_matrix_UB_22      0.085638
_diffrn_orient_matrix_UB_23      -0.002912
_diffrn_orient_matrix_UB_31      -0.001565
_diffrn_orient_matrix_UB_32      -0.000267
_diffrn_orient_matrix_UB_33      -0.067715
_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  0.1059
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14179
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         3.178
_diffrn_source_current           35.0
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_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             608
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.033(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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     171
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0665
_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)+(0.0408P)²+0.4282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2336
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_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        'C44 H26 N2 '
_cod_database_code               7233704
_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
N N 0.53603(13) 0.6012(3) 0.78506(14) 0.0476(6) Uani 1 1 d . U . . .
C1 C 0.19763(5) 0.36233(14) 0.46089(6) 0.0313(5) Uani 1 1 d G U . . .
C2 C 0.26292(7) 0.26398(10) 0.52005(6) 0.0352(5) Uani 1 1 d G U . . .
H2 H 0.2458 0.1913 0.5700 0.042 Uiso 1 1 calc R U . . .
C3 C 0.35321(7) 0.27196(13) 0.50618(6) 0.0409(6) Uani 1 1 d G U . . .
H3 H 0.3978 0.2047 0.5466 0.049 Uiso 1 1 calc R U . . .
C4 C 0.37821(6) 0.37828(18) 0.43315(6) 0.0453(6) Uani 1 1 d G U . . .
H4 H 0.4399 0.3837 0.4237 0.054 Uiso 1 1 calc R U . . .
C5 C 0.31292(7) 0.47663(17) 0.37398(5) 0.0415(6) Uani 1 1 d G U . . .
H5 H 0.3300 0.5493 0.3241 0.050 Uiso 1 1 calc R U . . .
C6 C 0.22263(7) 0.46866(16) 0.38785(5) 0.0354(5) Uani 1 1 d G U . . .
H6 H 0.1780 0.5359 0.3474 0.042 Uiso 1 1 calc R U . . .
C7 C 0.19459(5) 0.62948(14) 0.60653(6) 0.0312(5) Uani 1 1 d G U . . .
C8 C 0.21545(7) 0.51868(16) 0.68599(5) 0.0346(5) Uani 1 1 d G U . . .
H8 H 0.1693 0.4479 0.7090 0.042 Uiso 1 1 calc R U . . .
C9 C 0.30387(7) 0.51147(16) 0.73178(4) 0.0369(5) Uani 1 1 d G U . . .
H9 H 0.3181 0.4357 0.7861 0.044 Uiso 1 1 calc R U . . .
C10 C 0.37142(6) 0.61508(16) 0.69811(6) 0.0341(5) Uani 1 1 d G U . . .
C11 C 0.35056(7) 0.72589(12) 0.61865(6) 0.0353(5) Uani 1 1 d G U . . .
H11 H 0.3967 0.7967 0.5956 0.042 Uiso 1 1 calc R U . . .
C12 C 0.26214(7) 0.73309(10) 0.57286(6) 0.0336(5) Uani 1 1 d G U . . .
H12 H 0.2479 0.8088 0.5185 0.040 Uiso 1 1 calc R U . . .
C13 C 0.09717(13) 0.3523(3) 0.46884(13) 0.0293(5) Uani 1 1 d . U . . .
C14 C 0.04965(13) 0.4988(3) 0.50865(13) 0.0288(5) Uani 1 1 d . U . . .
C15 C 0.09566(13) 0.6437(3) 0.56464(13) 0.0295(5) Uani 1 1 d . U . . .
C16 C 0.04778(14) 0.7966(3) 0.59454(13) 0.0300(5) Uani 1 1 d . U . . .
C17 C 0.09275(15) 0.9483(3) 0.64913(14) 0.0349(5) Uani 1 1 d . U . . .
H17 H 0.1570 0.9483 0.6624 0.042 Uiso 1 1 calc R U . . .
C18 C 0.04552(15) 1.0906(3) 0.68191(14) 0.0360(5) Uani 1 1 d . U . . .
H18 H 0.0770 1.1885 0.7176 0.043 Uiso 1 1 calc R U . . .
C19 C -0.05015(15) 1.0946(3) 0.66346(14) 0.0359(5) Uani 1 1 d . U . . .
H19 H -0.0826 1.1959 0.6859 0.043 Uiso 1 1 calc R U . . .
C20 C -0.09562(15) 0.9540(3) 0.61375(14) 0.0340(5) Uani 1 1 d . U . . .
H20 H -0.1599 0.9578 0.6029 0.041 Uiso 1 1 calc R U . . .
C21 C -0.04969(14) 0.7999(3) 0.57710(13) 0.0297(5) Uani 1 1 d . U . . .
C22 C 0.46299(15) 0.6077(3) 0.74632(15) 0.0389(6) 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'
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 122.85(9) . .
C6 C1 C13 117.08(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 117.30(10) . .
C12 C7 C15 122.51(10) . .
C9 C8 C7 120.0 . .
C10 C9 C8 120.0 . .
C11 C10 C9 120.0 . .
C11 C10 C22 120.30(12) . .
C9 C10 C22 119.70(12) . .
C10 C11 C12 120.0 . .
C11 C12 C7 120.0 . .
C21 C13 C14 120.42(18) 3_566 .
C21 C13 C1 115.88(17) 3_566 .
C14 C13 C1 123.16(17) . .
C15 C14 C13 122.04(18) . .
C15 C14 C14 118.8(2) . 3_566
C13 C14 C14 119.2(2) . 3_566
C16 C15 C14 120.70(18) . .
C16 C15 C7 115.98(16) . .
C14 C15 C7 122.75(17) . .
C15 C16 C21 120.25(18) . .
C15 C16 C17 122.01(19) . .
C21 C16 C17 117.59(19) . .
C18 C17 C16 121.6(2) . .
C17 C18 C19 120.6(2) . .
C20 C19 C18 120.1(2) . .
C19 C20 C21 122.0(2) . .
C13 C21 C20 121.84(19) 3_566 .
C13 C21 C16 119.91(19) 3_566 .
C20 C21 C16 118.09(19) . .
N C22 C10 179.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C22 1.153(3) .
C1 C2 1.3900 .
C1 C6 1.3900 .
C1 C13 1.520(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 1.517(2) .
C8 C9 1.3900 .
C9 C10 1.3900 .
C10 C11 1.3900 .
C10 C22 1.443(2) .
C11 C12 1.3900 .
C13 C21 1.407(3) 3_566
C13 C14 1.426(3) .
C14 C15 1.425(3) .
C14 C14 1.467(4) 3_566
C15 C16 1.402(3) .
C16 C21 1.440(3) .
C16 C17 1.444(3) .
C17 C18 1.356(3) .
C18 C19 1.414(3) .
C19 C20 1.355(3) .
C20 C21 1.433(3) .
C21 C13 1.407(3) 3_566
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102135096
