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#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/26/4112696.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_4112696
loop_
_publ_author_name
'Adriana V. Szeghalmi'
'Marco Erdmann'
'Volker Engel'
'Michael Schmitt'
'Stephan Amthor'
'Volker Kriegisch'
'Gilbert Nöll'
'Rainer Stahl'
'Christoph Lambert'
'Dirk Leusser'
'Dietmar Stalke'
'Manfred Zabel'
'Jürgen Popp'
_publ_contact_author_address
;Prof. Dr. C. Lambert
Am Hubland
97074 Würzburg
Germany
;
_publ_contact_author_email       lambert@chemie.uni-wuerzburg.de
_publ_contact_author_fax         ++49(0)931-8884606
_publ_contact_author_name        'C. Lambert'
_publ_contact_author_phone       ++49(0)931-8885318
_publ_section_title
;
 How Delocalized IsN,N,N',N'-Tetraphenylphenylenediamine Radical Cation?
 An Experimental and Theoretical Study on the Electronic and Molecular
 Structure
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7834
_journal_page_last               7845
_journal_paper_doi               10.1021/ja0395386
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C30 H24 N2'
_chemical_formula_weight         412.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.4957(12)
_cell_angle_beta                 100.0727(12)
_cell_angle_gamma                95.2343(13)
_cell_formula_units_Z            2
_cell_length_a                   8.3524(6)
_cell_length_b                   10.2700(7)
_cell_length_c                   13.8018(10)
_cell_measurement_reflns_used    7384
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      2.2
_cell_volume                     1105.16(14)
_computing_cell_refinement       'SAINT-NT V5/6.0'
_computing_data_collection       'SMART-NT V5.6'
_computing_data_reduction        'SAINT-NT V5/6.0'
_computing_molecular_graphics    'SHELXTL-NT V5.1'
_computing_publication_material  'SHELXTL-NT V5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Smart Apex with D8-Goniometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21476
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.05; Sheldrick'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0110P)²+0.6400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3489
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0395386si20031118_044116.cif
_cod_data_source_block           JA0395386_twin_1
_cod_database_code               4112696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C14 C 0.1553(3) 0.9776(2) 0.98429(17) 0.0333(5) Uani 1 1 d .
H14 H 0.2624 0.9618 0.9743 0.040 Uiso 1 1 calc R
C15 C 0.1145(3) 0.9821(2) 1.07805(16) 0.0315(5) Uani 1 1 d .
H15 H 0.1945 0.9699 1.1316 0.038 Uiso 1 1 calc R
N1 N 0.0814(2) 0.9931(2) 0.80779(14) 0.0370(5) Uani 1 1 d .
C8 C -0.1378(3) 0.8146(3) 0.69141(18) 0.0395(6) Uani 1 1 d .
H8 H -0.1181 0.7592 0.7356 0.047 Uiso 1 1 calc R
C3 C 0.4459(3) 1.0443(3) 0.6962(2) 0.0458(7) Uani 1 1 d .
H3 H 0.4797 1.0092 0.6327 0.055 Uiso 1 1 calc R
C6 C 0.3451(3) 1.1455(2) 0.87897(19) 0.0389(6) Uani 1 1 d .
H6 H 0.3113 1.1825 0.9422 0.047 Uiso 1 1 calc R
C1 C 0.2399(3) 1.0445(2) 0.79883(17) 0.0335(5) Uani 1 1 d .
C29 C 1.0186(3) 0.6225(3) 0.07828(19) 0.0426(6) Uani 1 1 d .
H29 H 1.0318 0.7072 0.1317 0.051 Uiso 1 1 calc R
C2 C 0.2926(3) 0.9932(3) 0.70674(18) 0.0391(6) Uani 1 1 d .
H2 H 0.2231 0.9229 0.6510 0.047 Uiso 1 1 calc R
C17 C 0.9679(3) 0.6002(3) 0.37603(19) 0.0483(7) Uani 1 1 d .
H17 H 0.8536 0.5978 0.3751 0.058 Uiso 1 1 calc R
C12 C -0.0773(3) 1.0237(3) 0.65154(18) 0.0413(6) Uani 1 1 d .
H12 H -0.0166 1.1129 0.6690 0.050 Uiso 1 1 calc R
C30 C 1.0614(3) 0.6203(3) -0.01480(18) 0.0423(6) Uani 1 1 d .
H30 H 1.1037 0.7037 -0.0245 0.051 Uiso 1 1 calc R
C7 C -0.0459(3) 0.9434(2) 0.71668(16) 0.0341(5) Uani 1 1 d .
C25 C 0.4251(3) 0.3189(3) 0.15738(19) 0.0468(7) Uani 1 1 d .
H25 H 0.3152 0.2772 0.1490 0.056 Uiso 1 1 calc R
C13 C 0.0418(3) 0.9960(2) 0.90461(16) 0.0314(5) Uani 1 1 d .
C23 C 0.6157(3) 0.4858(3) 0.13053(19) 0.0449(6) Uani 1 1 d .
H23 H 0.6360 0.5601 0.1040 0.054 Uiso 1 1 calc R
C4 C 0.5491(3) 1.1439(3) 0.7754(2) 0.0463(7) Uani 1 1 d .
H4 H 0.6535 1.1789 0.7673 0.056 Uiso 1 1 calc R
C5 C 0.4990(3) 1.1931(3) 0.8678(2) 0.0458(6) Uani 1 1 d .
H5 H 0.5713 1.2604 0.9243 0.055 Uiso 1 1 calc R
C21 C 1.1898(3) 0.5627(3) 0.2884(2) 0.0447(6) Uani 1 1 d .
H21 H 1.2291 0.5339 0.2263 0.054 Uiso 1 1 calc R
C9 C -0.2582(3) 0.7667(3) 0.60196(19) 0.0468(7) Uani 1 1 d .
H9 H -0.3218 0.6788 0.5852 0.056 Uiso 1 1 calc R
C11 C -0.1956(3) 0.9745(3) 0.56221(19) 0.0491(7) Uani 1 1 d .
H11 H -0.2152 1.0292 0.5175 0.059 Uiso 1 1 calc R
C22 C 0.7456(3) 0.4400(2) 0.18089(17) 0.0373(6) Uani 1 1 d .
N2 N 0.9092(3) 0.5021(2) 0.18852(15) 0.0479(6) Uani 1 1 d .
C16 C 1.0215(3) 0.5546(2) 0.28368(18) 0.0382(6) Uani 1 1 d .
C27 C 0.7140(3) 0.3332(3) 0.2207(2) 0.0465(7) Uani 1 1 d .
H27 H 0.8022 0.3008 0.2561 0.056 Uiso 1 1 calc R
C24 C 0.4567(3) 0.4249(3) 0.1183(2) 0.0493(7) Uani 1 1 d .
H24 H 0.3682 0.4565 0.0825 0.059 Uiso 1 1 calc R
C20 C 1.3005(3) 0.6117(3) 0.3817(2) 0.0536(7) Uani 1 1 d .
H20 H 1.4151 0.6158 0.3833 0.064 Uiso 1 1 calc R
C26 C 0.5530(3) 0.2735(3) 0.2086(2) 0.0504(7) Uani 1 1 d .
H26 H 0.5314 0.2004 0.2361 0.060 Uiso 1 1 calc R
C18 C 1.0803(4) 0.6487(3) 0.4688(2) 0.0565(8) Uani 1 1 d .
H18 H 1.0421 0.6784 0.5312 0.068 Uiso 1 1 calc R
C28 C 0.9568(3) 0.5020(3) 0.09366(18) 0.0405(6) Uani 1 1 d .
C10 C -0.2863(3) 0.8459(3) 0.5370(2) 0.0525(7) Uani 1 1 d .
H10 H -0.3679 0.8120 0.4750 0.063 Uiso 1 1 calc R
C19 C 1.2464(4) 0.6550(3) 0.4728(2) 0.0580(8) Uani 1 1 d .
H19 H 1.3226 0.6886 0.5372 0.070 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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'
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
C15 C14 C13 120.9(2) . .
C14 C15 C13 121.2(2) . 2_577
C1 N1 C13 122.66(19) . .
C1 N1 C7 118.60(18) . .
C13 N1 C7 118.65(18) . .
C9 C8 C7 120.0(2) . .
C4 C3 C2 121.1(2) . .
C1 C6 C5 120.5(2) . .
C6 C1 C2 118.3(2) . .
C6 C1 N1 122.0(2) . .
C2 C1 N1 119.7(2) . .
C28 C29 C30 120.3(2) . .
C3 C2 C1 120.3(2) . .
C18 C17 C16 120.1(3) . .
C11 C12 C7 120.2(2) . .
C28 C30 C29 120.7(2) 2_765 .
C8 C7 C12 119.3(2) . .
C8 C7 N1 120.7(2) . .
C12 C7 N1 120.0(2) . .
C26 C25 C24 119.5(2) . .
C14 C13 C15 117.88(19) . 2_577
C14 C13 N1 121.9(2) . .
C15 C13 N1 120.2(2) 2_577 .
C24 C23 C22 120.6(2) . .
C3 C4 C5 118.8(2) . .
C4 C5 C6 120.8(2) . .
C20 C21 C16 121.0(2) . .
C10 C9 C8 120.3(2) . .
C12 C11 C10 120.3(2) . .
C23 C22 C27 119.1(2) . .
C23 C22 N2 119.0(2) . .
C27 C22 N2 121.9(2) . .
C16 N2 C22 121.82(19) . .
C16 N2 C28 121.2(2) . .
C22 N2 C28 116.87(19) . .
C21 C16 C17 118.1(2) . .
C21 C16 N2 120.8(2) . .
C17 C16 N2 121.2(2) . .
C22 C27 C26 119.7(2) . .
C25 C24 C23 120.4(3) . .
C19 C20 C21 120.5(3) . .
C25 C26 C27 120.7(2) . .
C19 C18 C17 121.4(3) . .
C29 C28 C30 118.9(2) . 2_765
C29 C28 N2 121.3(2) . .
C30 C28 N2 119.7(2) 2_765 .
C9 C10 C11 119.9(2) . .
C18 C19 C20 118.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C14 C15 1.384(3) .
C14 C13 1.389(3) .
C15 C13 1.394(3) 2_577
N1 C1 1.419(3) .
N1 C13 1.425(3) .
N1 C7 1.429(3) .
C8 C9 1.381(3) .
C8 C7 1.386(3) .
C3 C4 1.363(4) .
C3 C2 1.387(3) .
C6 C1 1.383(3) .
C6 C5 1.383(3) .
C1 C2 1.395(3) .
C29 C28 1.383(3) .
C29 C30 1.387(3) .
C17 C18 1.379(4) .
C17 C16 1.394(3) .
C12 C11 1.371(3) .
C12 C7 1.391(3) .
C30 C28 1.385(3) 2_765
C25 C26 1.368(4) .
C25 C24 1.370(4) .
C13 C15 1.394(3) 2_577
C23 C24 1.376(3) .
C23 C22 1.377(3) .
C4 C5 1.385(4) .
C21 C20 1.378(4) .
C21 C16 1.390(3) .
C9 C10 1.377(4) .
C11 C10 1.380(4) .
C22 C27 1.383(3) .
C22 N2 1.428(3) .
N2 C16 1.403(3) .
N2 C28 1.433(3) .
C27 C26 1.388(3) .
C20 C19 1.378(4) .
C18 C19 1.373(4) .
C28 C30 1.385(3) 2_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139119150
