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#$Date: 2019-10-08 11:07:38 +0300 (Tue, 08 Oct 2019) $
#$Revision: 219160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234468.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_7234468
loop_
_publ_author_name
'Junbo Li'
'Jianwei Miao'
'Guankui Long'
'Jing Zhang'
'Yongxin Li'
'Rakesh Ganguly'
'Yang Zhao'
'Yi Liu'
'Bin Liu'
'Qichun Zhang'
_publ_section_title
;
 N-Heteroheptacenequinone and N-heterononacenequinone: synthesis, physical
 properties, crystal structures and photoelectrochemical behaviors
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9877
_journal_page_last               9884
_journal_paper_doi               10.1039/C5TC02010G
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C70 H92 N4 O2 Si4'
_chemical_formula_weight         1133.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                84.169(2)
_cell_angle_beta                 88.405(2)
_cell_angle_gamma                63.987(2)
_cell_formula_units_Z            1
_cell_length_a                   10.1577(4)
_cell_length_b                   10.6488(4)
_cell_length_c                   17.1688(6)
_cell_measurement_temperature    103(2)
_cell_volume                     1660.04(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58385
_diffrn_reflns_theta_full        30.12
_diffrn_reflns_theta_max         30.12
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9479
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.058
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         9733
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1013P)²+1.9985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2499
_reflns_number_gt                5186
_reflns_number_total             9733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9877.cif
_cod_data_source_block           TAHD
_cod_database_code               7234468
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3324(3) 0.1053(3) 0.41599(18) 0.0314(7) Uani 1 1 d . . .
H1 H 0.2749 0.0557 0.4275 0.038 Uiso 1 1 calc R . .
C2 C 0.3603(4) 0.1703(4) 0.4731(2) 0.0369(7) Uani 1 1 d . . .
H2 H 0.3231 0.1648 0.5240 0.044 Uiso 1 1 calc R . .
C3 C 0.4450(4) 0.2466(4) 0.45703(19) 0.0372(7) Uani 1 1 d . . .
H3 H 0.4640 0.2915 0.4974 0.045 Uiso 1 1 calc R . .
C4 C 0.4986(3) 0.2556(3) 0.38462(19) 0.0340(7) Uani 1 1 d . . .
H4 H 0.5544 0.3073 0.3749 0.041 Uiso 1 1 calc R . .
C5 C 0.4726(3) 0.1886(3) 0.32250(17) 0.0274(6) Uani 1 1 d . . .
C6 C 0.3879(3) 0.1104(3) 0.33899(17) 0.0280(6) Uani 1 1 d . . .
C7 C 0.3624(3) 0.0408(3) 0.28016(17) 0.0282(6) Uani 1 1 d . . .
C8 C 0.4201(3) 0.0470(3) 0.20487(17) 0.0269(6) Uani 1 1 d . . .
C9 C 0.4426(3) -0.0059(3) 0.07857(17) 0.0266(6) Uani 1 1 d . . .
C10 C 0.5326(3) 0.0663(3) 0.06287(17) 0.0260(6) Uani 1 1 d . . .
C11 C 0.5990(3) 0.0709(3) -0.01601(18) 0.0321(7) Uani 1 1 d . . .
C12 C 0.5053(3) 0.1238(3) 0.18876(17) 0.0261(6) Uani 1 1 d . . .
C13 C 0.5319(3) 0.1935(3) 0.24771(17) 0.0272(6) Uani 1 1 d . . .
C14 C 0.6195(3) 0.2671(3) 0.22994(17) 0.0294(6) Uani 1 1 d . . .
C15 C 0.6936(4) 0.3286(3) 0.21408(18) 0.0333(7) Uani 1 1 d . . .
C16 C 0.6962(4) 0.5753(4) 0.1153(2) 0.0410(8) Uani 1 1 d . . .
H16 H 0.6043 0.6365 0.1414 0.049 Uiso 1 1 calc R . .
C17 C 0.6474(8) 0.5291(6) 0.0442(3) 0.104(2) Uani 1 1 d . . .
H17A H 0.5732 0.6116 0.0138 0.157 Uiso 1 1 calc R . .
H17B H 0.6057 0.4640 0.0620 0.157 Uiso 1 1 calc R . .
H17C H 0.7319 0.4821 0.0113 0.157 Uiso 1 1 calc R . .
C18 C 0.7726(4) 0.6680(4) 0.0900(2) 0.0497(10) Uani 1 1 d . . .
H18A H 0.8604 0.6148 0.0606 0.075 Uiso 1 1 calc R . .
H18B H 0.8007 0.6977 0.1364 0.075 Uiso 1 1 calc R . .
H18C H 0.7058 0.7509 0.0567 0.075 Uiso 1 1 calc R . .
C19 C 0.9887(4) 0.2987(4) 0.1575(2) 0.0457(9) Uani 1 1 d . . .
H19 H 1.0264 0.2174 0.1989 0.055 Uiso 1 1 calc R . .
C20 C 0.9823(6) 0.2377(6) 0.0803(3) 0.0841(17) Uani 1 1 d . . .
H20A H 0.9653 0.3091 0.0361 0.126 Uiso 1 1 calc R . .
H20B H 0.9022 0.2097 0.0825 0.126 Uiso 1 1 calc R . .
H20C H 1.0753 0.1555 0.0736 0.126 Uiso 1 1 calc R . .
C21 C 1.1013(4) 0.3593(4) 0.1528(3) 0.0537(11) Uani 1 1 d . . .
H21A H 1.1941 0.2905 0.1336 0.081 Uiso 1 1 calc R . .
H21B H 1.1171 0.3806 0.2050 0.081 Uiso 1 1 calc R . .
H21C H 1.0644 0.4456 0.1168 0.081 Uiso 1 1 calc R . .
C22 C 0.8221(5) 0.4903(5) 0.2859(2) 0.0540(11) Uani 1 1 d . . .
H22 H 0.8797 0.5459 0.2757 0.065 Uiso 1 1 calc R . .
C23 C 0.9093(7) 0.3657(6) 0.3467(2) 0.0850(19) Uani 1 1 d . . .
H23A H 0.9146 0.4009 0.3965 0.127 Uiso 1 1 calc R . .
H23B H 1.0086 0.3126 0.3278 0.127 Uiso 1 1 calc R . .
H23C H 0.8601 0.3042 0.3544 0.127 Uiso 1 1 calc R . .
C24 C 0.6725(6) 0.5884(6) 0.3166(3) 0.090(2) Uani 1 1 d . . .
H24A H 0.6130 0.5370 0.3268 0.135 Uiso 1 1 calc R . .
H24B H 0.6225 0.6685 0.2774 0.135 Uiso 1 1 calc R . .
H24C H 0.6864 0.6223 0.3653 0.135 Uiso 1 1 calc R . .
C25 C 0.2792(3) -0.0381(3) 0.29392(17) 0.0303(6) Uani 1 1 d . . .
C26 C 0.2099(3) -0.1057(3) 0.30236(18) 0.0322(7) Uani 1 1 d . . .
C27 C 0.1096(4) -0.2748(5) 0.2104(2) 0.0551(11) Uani 1 1 d . . .
H27 H 0.0534 -0.3323 0.2142 0.066 Uiso 1 1 calc R . .
C28 C 0.0339(6) -0.1522(6) 0.1470(2) 0.0789(17) Uani 1 1 d . . .
H28A H 0.0842 -0.0916 0.1432 0.118 Uiso 1 1 calc R . .
H28B H -0.0685 -0.0977 0.1608 0.118 Uiso 1 1 calc R . .
H28C H 0.0377 -0.1890 0.0965 0.118 Uiso 1 1 calc R . .
C29 C 0.2649(6) -0.3691(6) 0.1862(4) 0.093(2) Uani 1 1 d . . .
H29A H 0.2610 -0.4094 0.1380 0.139 Uiso 1 1 calc R . .
H29B H 0.3131 -0.4448 0.2280 0.139 Uiso 1 1 calc R . .
H29C H 0.3203 -0.3135 0.1771 0.139 Uiso 1 1 calc R . .
C30 C 0.1988(4) -0.3594(4) 0.3865(3) 0.0503(10) Uani 1 1 d . . .
H30 H 0.2834 -0.4281 0.3586 0.060 Uiso 1 1 calc R . .
C31 C 0.1117(4) -0.4416(4) 0.4140(2) 0.0485(9) Uani 1 1 d . . .
H31A H 0.1716 -0.5215 0.4513 0.073 Uiso 1 1 calc R . .
H31B H 0.0854 -0.4759 0.3688 0.073 Uiso 1 1 calc R . .
H31C H 0.0224 -0.3800 0.4395 0.073 Uiso 1 1 calc R . .
C32 C 0.2693(6) -0.3297(6) 0.4530(2) 0.0702(14) Uani 1 1 d . . .
H32A H 0.1933 -0.2692 0.4867 0.105 Uiso 1 1 calc R . .
H32B H 0.3284 -0.2822 0.4324 0.105 Uiso 1 1 calc R . .
H32C H 0.3323 -0.4181 0.4834 0.105 Uiso 1 1 calc R . .
C33 C -0.0879(3) -0.0858(3) 0.33156(19) 0.0321(7) Uani 1 1 d . . .
H33 H -0.1166 -0.0017 0.2923 0.038 Uiso 1 1 calc R . .
C34 C -0.1965(3) -0.1483(3) 0.3204(2) 0.0358(7) Uani 1 1 d . . .
H34A H -0.1691 -0.2343 0.3560 0.054 Uiso 1 1 calc R . .
H34B H -0.1936 -0.1703 0.2662 0.054 Uiso 1 1 calc R . .
H34C H -0.2957 -0.0800 0.3321 0.054 Uiso 1 1 calc R . .
C35 C -0.1032(4) -0.0328(4) 0.4129(2) 0.0514(10) Uani 1 1 d . . .
H35A H -0.2039 0.0380 0.4192 0.077 Uiso 1 1 calc R . .
H35B H -0.0354 0.0090 0.4180 0.077 Uiso 1 1 calc R . .
H35C H -0.0800 -0.1117 0.4534 0.077 Uiso 1 1 calc R . .
N1 N 0.3898(3) -0.0167(3) 0.14799(14) 0.0283(5) Uani 1 1 d . . .
N2 N 0.5630(3) 0.1295(3) 0.11650(14) 0.0281(5) Uani 1 1 d . . .
O1 O 0.6767(4) 0.1286(4) -0.02902(16) 0.0737(10) Uani 1 1 d U . .
Si1 Si 0.80380(10) 0.42615(10) 0.19096(5) 0.0324(2) Uani 1 1 d . . .
Si2 Si 0.10474(9) -0.21010(9) 0.30961(5) 0.0306(2) Uani 1 1 d . . .
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'
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
_geom_angle_site_symmetry_3
C2 C1 C6 121.1(3) . .
C1 C2 C3 120.5(3) . .
C4 C3 C2 120.5(3) . .
C3 C4 C5 121.2(3) . .
C13 C5 C4 121.6(2) . .
C13 C5 C6 120.1(3) . .
C4 C5 C6 118.2(3) . .
C7 C6 C1 121.5(2) . .
C7 C6 C5 120.1(3) . .
C1 C6 C5 118.4(3) . .
C6 C7 C8 120.0(2) . .
C6 C7 C25 122.0(3) . .
C8 C7 C25 118.1(3) . .
N1 C8 C7 119.1(2) . .
N1 C8 C12 121.0(2) . .
C7 C8 C12 119.9(3) . .
N1 C9 C10 122.1(3) . .
N1 C9 C11 115.9(2) . 2_655
C10 C9 C11 122.0(2) . 2_655
N2 C10 C9 122.1(2) . .
N2 C10 C11 116.6(2) . .
C9 C10 C11 121.3(2) . .
O1 C11 C9 121.7(3) . 2_655
O1 C11 C10 121.6(3) . .
C9 C11 C10 116.6(2) 2_655 .
N2 C12 C13 119.0(2) . .
N2 C12 C8 120.5(2) . .
C13 C12 C8 120.4(3) . .
C5 C13 C12 119.5(2) . .
C5 C13 C14 121.6(3) . .
C12 C13 C14 118.9(2) . .
C15 C14 C13 179.2(3) . .
C14 C15 Si1 178.7(3) . .
C18 C16 C17 111.1(4) . .
C18 C16 Si1 113.3(2) . .
C17 C16 Si1 113.7(3) . .
C21 C19 C20 111.1(3) . .
C21 C19 Si1 112.7(3) . .
C20 C19 Si1 113.7(3) . .
C24 C22 C23 111.9(4) . .
C24 C22 Si1 111.7(3) . .
C23 C22 Si1 110.6(3) . .
C26 C25 C7 177.3(3) . .
C25 C26 Si2 176.9(3) . .
C29 C27 C28 110.3(4) . .
C29 C27 Si2 112.5(3) . .
C28 C27 Si2 111.4(3) . .
C32 C30 C31 112.4(3) . .
C32 C30 Si2 116.2(3) . .
C31 C30 Si2 115.0(2) . .
C35 C33 C34 110.9(3) . .
C35 C33 Si2 113.2(2) . .
C34 C33 Si2 112.0(2) . .
C9 N1 C8 117.2(2) . .
C10 N2 C12 117.1(2) . .
C15 Si1 C22 104.84(14) . .
C15 Si1 C16 106.65(14) . .
C22 Si1 C16 111.93(18) . .
C15 Si1 C19 107.84(15) . .
C22 Si1 C19 110.59(19) . .
C16 Si1 C19 114.39(17) . .
C26 Si2 C30 106.63(15) . .
C26 Si2 C33 106.08(14) . .
C30 Si2 C33 115.41(17) . .
C26 Si2 C27 107.25(14) . .
C30 Si2 C27 111.4(2) . .
C33 Si2 C27 109.64(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.358(4) .
C1 C6 1.428(4) .
C2 C3 1.425(4) .
C3 C4 1.355(4) .
C4 C5 1.432(4) .
C5 C13 1.409(4) .
C5 C6 1.442(3) .
C6 C7 1.404(4) .
C7 C8 1.412(4) .
C7 C25 1.430(4) .
C8 N1 1.358(4) .
C8 C12 1.434(3) .
C9 N1 1.309(4) .
C9 C10 1.435(3) .
C9 C11 1.499(4) 2_655
C10 N2 1.311(4) .
C10 C11 1.502(4) .
C11 O1 1.198(3) .
C11 C9 1.499(4) 2_655
C12 N2 1.364(4) .
C12 C13 1.412(4) .
C13 C14 1.430(4) .
C14 C15 1.206(4) .
C15 Si1 1.844(3) .
C16 C18 1.527(4) .
C16 C17 1.532(6) .
C16 Si1 1.882(4) .
C19 C21 1.537(4) .
C19 C20 1.549(6) .
C19 Si1 1.887(4) .
C22 C24 1.534(7) .
C22 C23 1.541(7) .
C22 Si1 1.874(3) .
C25 C26 1.206(4) .
C26 Si2 1.843(3) .
C27 C29 1.525(6) .
C27 C28 1.535(7) .
C27 Si2 1.894(4) .
C30 C32 1.495(5) .
C30 C31 1.530(4) .
C30 Si2 1.869(4) .
C33 C35 1.538(5) .
C33 C34 1.541(4) .
C33 Si2 1.874(3) .
