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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/82/7108228.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_7108228
loop_
_publ_author_name
'Remi Chauvin'
'Arnaud Rives'
'Iaroslav Baglai'
'Volodymyr Malytskyi'
'Valerie Maraval'
'Nathalie Saffon'
'Zoia Voitenko'
_publ_section_title
;
 Highly pi electron-rich macro-aromatics:
 bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references
;
_journal_name_full               Chem.Commun.
_journal_page_first              8763
_journal_paper_doi               10.1039/c2cc34176j
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C60 H72 N2 Si2'
_chemical_formula_weight         877.38
_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                104.252(5)
_cell_angle_beta                 91.728(4)
_cell_angle_gamma                95.653(4)
_cell_formula_units_Z            1
_cell_length_a                   9.2348(9)
_cell_length_b                   9.3293(9)
_cell_length_c                   15.6051(16)
_cell_measurement_reflns_used    8732
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.70
_cell_volume                     1294.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35105
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0448
_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)+(0.0563P)²+0.3908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                4025
_reflns_number_total             5230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc34176j.txt
_cod_data_source_block           18
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7108228
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
Si1 Si 0.24232(5) 0.79269(5) 0.13440(3) 0.03102(14) Uani 1 1 d .
N1 N 0.28421(17) 0.48668(17) 0.63466(9) 0.0433(4) Uani 1 1 d .
C1 C 0.30894(19) 0.81297(19) 0.24880(11) 0.0375(4) Uani 1 1 d .
C2 C 0.37700(18) 0.82183(18) 0.31719(11) 0.0331(4) Uani 1 1 d .
C3 C 0.46804(18) 0.82551(17) 0.39387(10) 0.0318(4) Uani 1 1 d .
C4 C 0.60236(19) 0.90113(18) 0.39956(11) 0.0350(4) Uani 1 1 d .
C5 C 0.72487(19) 0.96670(18) 0.40025(10) 0.0352(4) Uani 1 1 d .
C6 C 0.86343(18) 1.03302(17) 0.40518(10) 0.0322(4) Uani 1 1 d .
C7 C 0.95970(18) 1.01172(18) 0.47198(10) 0.0340(4) Uani 1 1 d .
C8 C 0.91535(18) 1.12101(17) 0.34283(10) 0.0314(4) Uani 1 1 d .
C9 C 0.8217(2) 1.1386(2) 0.27562(11) 0.0395(4) Uani 1 1 d .
H9 H 0.7233 1.0953 0.2703 0.047 Uiso 1 1 calc R
C10 C 0.8707(2) 1.2186(2) 0.21650(12) 0.0480(5) Uani 1 1 d .
H10 H 0.8061 1.2282 0.1702 0.058 Uiso 1 1 calc R
C11 C 1.0124(2) 1.2845(2) 0.22405(12) 0.0485(5) Uani 1 1 d .
H11 H 1.0453 1.3397 0.1834 0.058 Uiso 1 1 calc R
C12 C 1.1055(2) 1.2697(2) 0.29069(12) 0.0466(5) Uani 1 1 d .
H12 H 1.2028 1.3161 0.2967 0.056 Uiso 1 1 calc R
C13 C 1.05827(19) 1.18719(19) 0.34957(11) 0.0385(4) Uani 1 1 d .
H13 H 1.1242 1.1759 0.3948 0.046 Uiso 1 1 calc R
C14 C 0.41919(17) 0.74145(17) 0.45724(10) 0.0300(3) Uani 1 1 d .
C15 C 0.50530(18) 0.74295(19) 0.53253(11) 0.0354(4) Uani 1 1 d .
H15 H 0.5970 0.8020 0.5434 0.042 Uiso 1 1 calc R
C16 C 0.46173(19) 0.66193(19) 0.59108(11) 0.0371(4) Uani 1 1 d .
H16 H 0.5233 0.6668 0.6418 0.045 Uiso 1 1 calc R
C17 C 0.32723(18) 0.57130(18) 0.57767(10) 0.0331(4) Uani 1 1 d .
C18 C 0.23941(18) 0.57152(18) 0.50257(10) 0.0338(4) Uani 1 1 d .
H18 H 0.1471 0.5136 0.4917 0.041 Uiso 1 1 calc R
C19 C 0.28493(17) 0.65430(18) 0.44457(10) 0.0321(4) Uani 1 1 d .
H19 H 0.2230 0.6520 0.3944 0.039 Uiso 1 1 calc R
C20 C 0.3735(2) 0.4928(2) 0.71366(12) 0.0526(5) Uani 1 1 d .
H20A H 0.4704 0.4653 0.6970 0.079 Uiso 1 1 calc R
H20B H 0.3278 0.4232 0.7453 0.079 Uiso 1 1 calc R
H20C H 0.3827 0.5939 0.7521 0.079 Uiso 1 1 calc R
C21 C 0.1437(2) 0.3986(2) 0.62071(13) 0.0533(5) Uani 1 1 d .
H21A H 0.0664 0.4646 0.6266 0.080 Uiso 1 1 calc R
H21B H 0.1342 0.3401 0.6649 0.080 Uiso 1 1 calc R
H21C H 0.1354 0.3314 0.5612 0.080 Uiso 1 1 calc R
C22 C 0.2333(2) 0.58914(18) 0.07341(11) 0.0379(4) Uani 1 1 d .
H22 H 0.1313 0.5446 0.0768 0.045 Uiso 1 1 calc R
C23 C 0.3330(2) 0.4995(2) 0.11440(15) 0.0549(5) Uani 1 1 d .
H23A H 0.3165 0.3945 0.0820 0.082 Uiso 1 1 calc R
H23B H 0.3115 0.5093 0.1766 0.082 Uiso 1 1 calc R
H23C H 0.4349 0.5372 0.1109 0.082 Uiso 1 1 calc R
C24 C 0.2592(2) 0.5686(2) -0.02543(12) 0.0522(5) Uani 1 1 d .
H24A H 0.3569 0.6146 -0.0321 0.078 Uiso 1 1 calc R
H24B H 0.1862 0.6160 -0.0525 0.078 Uiso 1 1 calc R
H24C H 0.2509 0.4622 -0.0548 0.078 Uiso 1 1 calc R
C25 C 0.05431(19) 0.85399(19) 0.13434(11) 0.0383(4) Uani 1 1 d .
H25 H 0.0641 0.9639 0.1606 0.046 Uiso 1 1 calc R
C26 C -0.0427(2) 0.7810(2) 0.19351(13) 0.0481(5) Uani 1 1 d .
H26A H -0.1398 0.8148 0.1930 0.072 Uiso 1 1 calc R
H26B H 0.0006 0.8092 0.2542 0.072 Uiso 1 1 calc R
H26C H -0.0507 0.6726 0.1711 0.072 Uiso 1 1 calc R
C27 C -0.0169(2) 0.8248(2) 0.04101(13) 0.0524(5) Uani 1 1 d .
H27A H -0.0339 0.7173 0.0148 0.079 Uiso 1 1 calc R
H27B H 0.0476 0.8711 0.0043 0.079 Uiso 1 1 calc R
H27C H -0.1101 0.8673 0.0441 0.079 Uiso 1 1 calc R
C28 C 0.3809(2) 0.91266(19) 0.08883(11) 0.0380(4) Uani 1 1 d .
H28 H 0.3541 0.8983 0.0245 0.046 Uiso 1 1 calc R
C29 C 0.5351(2) 0.8675(2) 0.09695(13) 0.0495(5) Uani 1 1 d .
H29A H 0.6046 0.9352 0.0754 0.074 Uiso 1 1 calc R
H29B H 0.5382 0.7655 0.0615 0.074 Uiso 1 1 calc R
H29C H 0.5611 0.8732 0.1591 0.074 Uiso 1 1 calc R
C30 C 0.3795(2) 1.0781(2) 0.13443(14) 0.0553(5) Uani 1 1 d .
H30A H 0.4011 1.0944 0.1982 0.083 Uiso 1 1 calc R
H30B H 0.2831 1.1085 0.1243 0.083 Uiso 1 1 calc R
H30C H 0.4534 1.1372 0.1099 0.083 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'
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'
Si Si 0.0817 0.0704 '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
C1 Si1 C25 109.03(8) .
C1 Si1 C28 104.71(8) .
C25 Si1 C28 113.22(8) .
C1 Si1 C22 108.36(8) .
C25 Si1 C22 109.28(8) .
C28 Si1 C22 112.03(8) .
C17 N1 C21 120.56(15) .
C17 N1 C20 120.60(16) .
C21 N1 C20 118.67(15) .
C2 C1 Si1 167.88(16) .
C1 C2 C3 174.74(18) .
C4 C3 C2 116.14(15) .
C4 C3 C14 123.36(15) .
C2 C3 C14 120.33(14) .
C5 C4 C3 176.78(18) .
C4 C5 C6 175.70(18) .
C5 C6 C7 116.92(15) .
C5 C6 C8 122.61(15) .
C7 C6 C8 120.45(14) .
C7 C7 C6 177.7(2) 2_776
C9 C8 C13 118.41(16) .
C9 C8 C6 120.45(15) .
C13 C8 C6 121.14(15) .
C10 C9 C8 120.48(17) .
C11 C10 C9 120.66(18) .
C12 C11 C10 119.50(18) .
C11 C12 C13 120.38(18) .
C8 C13 C12 120.55(17) .
C19 C14 C15 116.89(15) .
C19 C14 C3 121.46(14) .
C15 C14 C3 121.65(15) .
C16 C15 C14 121.98(16) .
C15 C16 C17 121.36(15) .
N1 C17 C18 121.47(16) .
N1 C17 C16 121.85(15) .
C18 C17 C16 116.68(15) .
C19 C18 C17 121.09(15) .
C18 C19 C14 121.98(15) .
C23 C22 C24 110.42(16) .
C23 C22 Si1 114.45(13) .
C24 C22 Si1 112.02(12) .
C27 C25 C26 111.01(16) .
C27 C25 Si1 112.62(13) .
C26 C25 Si1 110.63(12) .
C30 C28 C29 109.87(16) .
C30 C28 Si1 111.44(12) .
C29 C28 Si1 111.79(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C1 1.8292(17) .
Si1 C25 1.8808(18) .
Si1 C28 1.8870(18) .
Si1 C22 1.8956(17) .
N1 C17 1.370(2) .
N1 C21 1.446(3) .
N1 C20 1.448(2) .
C1 C2 1.203(2) .
C2 C3 1.433(2) .
C3 C4 1.354(2) .
C3 C14 1.461(2) .
C4 C5 1.230(2) .
C5 C6 1.357(2) .
C6 C7 1.413(2) .
C6 C8 1.481(2) .
C7 C7 1.206(3) 2_776
C8 C9 1.390(2) .
C8 C13 1.390(2) .
C9 C10 1.382(3) .
C10 C11 1.379(3) .
C11 C12 1.371(3) .
C12 C13 1.391(3) .
C14 C19 1.395(2) .
C14 C15 1.395(2) .
C15 C16 1.368(2) .
C16 C17 1.411(2) .
C17 C18 1.405(2) .
C18 C19 1.377(2) .
C22 C23 1.529(2) .
C22 C24 1.536(2) .
C25 C27 1.530(2) .
C25 C26 1.535(3) .
C28 C30 1.534(3) .
C28 C29 1.535(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102335534
