#------------------------------------------------------------------------------
#$Date: 2019-10-08 11:07:38 +0300 (Tue, 08 Oct 2019) $
#$Revision: 219160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234469.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_7234469
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            'C82 H102 N6 O2 Si4'
_chemical_formula_weight         1316.06
_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                110.316(3)
_cell_angle_beta                 97.166(3)
_cell_angle_gamma                101.674(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9319(8)
_cell_length_b                   14.4277(12)
_cell_length_c                   18.4216(16)
_cell_measurement_reflns_used    2615
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      23.5010
_cell_measurement_theta_min      2.4129
_cell_volume                     1892.0(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_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  0.1013
_diffrn_reflns_av_sigmaI/netI    0.1350
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30885
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         9032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0611
_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)+(0.0417P)²+0.2694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                4918
_reflns_number_total             9032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9877.cif
_cod_data_source_block           TAND
_cod_database_code               7234469
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
Si1 Si 1.21567(10) 0.97129(5) 0.33964(4) 0.01621(18) Uani 1 1 d . . .
Si2 Si 0.40480(10) 0.58300(5) -0.31678(4) 0.01517(18) Uani 1 1 d . . .
C1 C 0.9077(3) 0.44673(19) -0.08572(14) 0.0162(6) Uani 1 1 d . . .
C2 C 0.9091(3) 0.55524(19) -0.03837(14) 0.0139(6) Uani 1 1 d . . .
C3 C 1.0002(3) 0.60707(19) 0.04321(14) 0.0152(6) Uani 1 1 d . . .
C4 C 0.9224(3) 0.75251(18) 0.04668(13) 0.0138(6) Uani 1 1 d . . .
C5 C 0.9356(3) 0.85697(19) 0.08755(13) 0.0141(6) Uani 1 1 d . . .
C6 C 0.8544(3) 0.91057(18) 0.04816(13) 0.0131(6) Uani 1 1 d . . .
C7 C 0.8723(3) 1.01630(19) 0.08476(14) 0.0151(6) Uani 1 1 d . . .
H7 H 0.9397 1.0524 0.1373 0.018 Uiso 1 1 calc R . .
C8 C 0.7947(3) 1.06947(19) 0.04645(14) 0.0148(6) Uani 1 1 d . . .
C9 C 0.8157(3) 1.17769(19) 0.08254(14) 0.0169(6) Uani 1 1 d . . .
H9 H 0.8863 1.2152 0.1343 0.020 Uiso 1 1 calc R . .
C10 C 0.7365(4) 1.2276(2) 0.04400(14) 0.0193(6) Uani 1 1 d . . .
H10 H 0.7509 1.2992 0.0693 0.023 Uiso 1 1 calc R . .
C11 C 0.6323(3) 1.1734(2) -0.03386(15) 0.0188(6) Uani 1 1 d . . .
H11 H 0.5782 1.2093 -0.0603 0.023 Uiso 1 1 calc R . .
C12 C 0.6090(3) 1.07095(19) -0.07110(14) 0.0169(6) Uani 1 1 d . . .
H12 H 0.5385 1.0360 -0.1231 0.020 Uiso 1 1 calc R . .
C13 C 0.6896(3) 1.01519(19) -0.03271(14) 0.0147(6) Uani 1 1 d . . .
C14 C 0.6706(3) 0.91079(19) -0.06962(14) 0.0154(6) Uani 1 1 d . . .
H14 H 0.6013 0.8751 -0.1218 0.019 Uiso 1 1 calc R . .
C15 C 0.7510(3) 0.85628(19) -0.03188(13) 0.0133(6) Uani 1 1 d . . .
C16 C 0.7351(3) 0.74977(18) -0.07119(13) 0.0135(6) Uani 1 1 d . . .
C17 C 0.8250(3) 0.69910(19) -0.03334(14) 0.0133(6) Uani 1 1 d . . .
C18 C 1.0317(3) 0.90551(18) 0.16802(14) 0.0146(6) Uani 1 1 d . . .
C19 C 1.1089(4) 0.94031(19) 0.23619(14) 0.0179(6) Uani 1 1 d . . .
C20 C 1.4285(4) 0.9332(2) 0.33894(15) 0.0225(7) Uani 1 1 d . . .
H20 H 1.4753 0.9392 0.3938 0.027 Uiso 1 1 calc R . .
C21 C 1.5666(4) 1.0048(2) 0.31847(17) 0.0344(8) Uani 1 1 d . . .
H21A H 1.6721 0.9794 0.3146 0.052 Uiso 1 1 calc R . .
H21B H 1.5974 1.0737 0.3600 0.052 Uiso 1 1 calc R . .
H21C H 1.5191 1.0072 0.2676 0.052 Uiso 1 1 calc R . .
C22 C 1.4021(4) 0.8211(2) 0.28329(18) 0.0391(8) Uani 1 1 d . . .
H22A H 1.3551 0.8122 0.2288 0.059 Uiso 1 1 calc R . .
H22B H 1.3190 0.7758 0.2995 0.059 Uiso 1 1 calc R . .
H22C H 1.5153 0.8037 0.2861 0.059 Uiso 1 1 calc R . .
C23 C 1.0586(4) 0.8962(2) 0.38174(15) 0.0208(6) Uani 1 1 d . . .
H23 H 0.9846 0.9415 0.4071 0.025 Uiso 1 1 calc R . .
C24 C 1.1570(4) 0.8717(2) 0.44721(16) 0.0310(8) Uani 1 1 d . . .
H24A H 1.0716 0.8365 0.4695 0.046 Uiso 1 1 calc R . .
H24B H 1.2306 0.9355 0.4891 0.046 Uiso 1 1 calc R . .
H24C H 1.2316 0.8274 0.4248 0.046 Uiso 1 1 calc R . .
C25 C 0.9315(4) 0.7977(2) 0.31894(16) 0.0291(7) Uani 1 1 d . . .
H25A H 0.9988 0.7504 0.2934 0.044 Uiso 1 1 calc R . .
H25B H 0.8646 0.8146 0.2791 0.044 Uiso 1 1 calc R . .
H25C H 0.8500 0.7653 0.3443 0.044 Uiso 1 1 calc R . .
C26 C 1.2514(4) 1.11299(19) 0.39496(14) 0.0196(6) Uani 1 1 d . . .
H26 H 1.3404 1.1487 0.3728 0.023 Uiso 1 1 calc R . .
C27 C 1.3271(4) 1.1490(2) 0.48401(15) 0.0297(7) Uani 1 1 d . . .
H27A H 1.3488 1.2235 0.5090 0.045 Uiso 1 1 calc R . .
H27B H 1.4381 1.1302 0.4918 0.045 Uiso 1 1 calc R . .
H27C H 1.2428 1.1161 0.5081 0.045 Uiso 1 1 calc R . .
C28 C 1.0826(4) 1.1459(2) 0.38040(16) 0.0265(7) Uani 1 1 d . . .
H28A H 0.9895 1.1090 0.3983 0.040 Uiso 1 1 calc R . .
H28B H 1.0453 1.1300 0.3237 0.040 Uiso 1 1 calc R . .
H28C H 1.1051 1.2198 0.4099 0.040 Uiso 1 1 calc R . .
C29 C 0.6304(3) 0.69380(18) -0.14991(14) 0.0146(6) Uani 1 1 d . . .
C30 C 0.5397(3) 0.64760(19) -0.21544(14) 0.0158(6) Uani 1 1 d . . .
C31 C 0.3554(4) 0.69040(19) -0.34413(14) 0.0189(6) Uani 1 1 d . . .
H31 H 0.4720 0.7403 -0.3336 0.023 Uiso 1 1 calc R . .
C32 C 0.2475(4) 0.7496(2) -0.29106(16) 0.0282(7) Uani 1 1 d . . .
H32A H 0.2445 0.8117 -0.3010 0.042 Uiso 1 1 calc R . .
H32B H 0.3018 0.7684 -0.2354 0.042 Uiso 1 1 calc R . .
H32C H 0.1271 0.7064 -0.3028 0.042 Uiso 1 1 calc R . .
C33 C 0.2733(4) 0.6600(2) -0.43191(15) 0.0315(8) Uani 1 1 d . . .
H33A H 0.1535 0.6159 -0.4445 0.047 Uiso 1 1 calc R . .
H33B H 0.3447 0.6230 -0.4650 0.047 Uiso 1 1 calc R . .
H33C H 0.2694 0.7218 -0.4422 0.047 Uiso 1 1 calc R . .
C34 C 0.2111(4) 0.48433(19) -0.31563(14) 0.0192(6) Uani 1 1 d . . .
H34 H 0.2613 0.4329 -0.3018 0.023 Uiso 1 1 calc R . .
C35 C 0.1050(4) 0.5238(2) -0.25260(15) 0.0265(7) Uani 1 1 d . . .
H35A H 0.0404 0.5684 -0.2668 0.040 Uiso 1 1 calc R . .
H35B H 0.1855 0.5627 -0.2010 0.040 Uiso 1 1 calc R . .
H35C H 0.0214 0.4656 -0.2498 0.040 Uiso 1 1 calc R . .
C36 C 0.0892(4) 0.4249(2) -0.39775(15) 0.0275(7) Uani 1 1 d . . .
H36A H -0.0022 0.3696 -0.3955 0.041 Uiso 1 1 calc R . .
H36B H 0.1582 0.3958 -0.4362 0.041 Uiso 1 1 calc R . .
H36C H 0.0338 0.4715 -0.4140 0.041 Uiso 1 1 calc R . .
C37 C 0.5459(4) 0.5165(2) -0.38066(14) 0.0196(6) Uani 1 1 d . . .
H37 H 0.4731 0.4789 -0.4357 0.023 Uiso 1 1 calc R . .
C38 C 0.7058(4) 0.5943(2) -0.38392(16) 0.0281(7) Uani 1 1 d . . .
H38A H 0.7767 0.6344 -0.3303 0.042 Uiso 1 1 calc R . .
H38B H 0.6651 0.6403 -0.4064 0.042 Uiso 1 1 calc R . .
H38C H 0.7775 0.5577 -0.4172 0.042 Uiso 1 1 calc R . .
C39 C 0.6053(4) 0.4372(2) -0.35202(16) 0.0272(7) Uani 1 1 d . . .
H39A H 0.6808 0.4051 -0.3856 0.041 Uiso 1 1 calc R . .
H39B H 0.5015 0.3845 -0.3553 0.041 Uiso 1 1 calc R . .
H39C H 0.6712 0.4716 -0.2970 0.041 Uiso 1 1 calc R . .
C40 C 0.6150(4) 0.5033(2) 0.08409(17) 0.0259(7) Uani 1 1 d . . .
C41 C 0.5714(4) 0.5853(2) 0.14517(16) 0.0353(8) Uani 1 1 d . . .
H41A H 0.5315 0.6310 0.1221 0.053 Uiso 1 1 calc R . .
H41B H 0.6760 0.6244 0.1876 0.053 Uiso 1 1 calc R . .
H41C H 0.4775 0.5559 0.1669 0.053 Uiso 1 1 calc R . .
N1 N 0.8204(3) 0.59943(15) -0.07496(11) 0.0141(5) Uani 1 1 d . . .
N2 N 1.0067(3) 0.70261(15) 0.08472(11) 0.0142(5) Uani 1 1 d . . .
N3 N 0.6488(4) 0.44002(19) 0.03563(15) 0.0320(6) Uani 1 1 d . . .
O1 O 0.8373(3) 0.40498(13) -0.15528(10) 0.0233(5) 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'
Si Si 0.0817 0.0704 '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
C19 Si1 C20 107.93(12) . .
C19 Si1 C26 107.33(11) . .
C20 Si1 C26 112.19(12) . .
C19 Si1 C23 107.40(12) . .
C20 Si1 C23 111.53(12) . .
C26 Si1 C23 110.23(12) . .
C30 Si2 C34 107.89(11) . .
C30 Si2 C37 106.75(12) . .
C34 Si2 C37 109.12(12) . .
C30 Si2 C31 104.36(11) . .
C34 Si2 C31 116.90(13) . .
C37 Si2 C31 111.21(12) . .
O1 C1 C2 121.4(2) . .
O1 C1 C3 121.6(2) . 2_765
C2 C1 C3 117.0(2) . 2_765
N1 C2 C3 121.9(2) . .
N1 C2 C1 116.4(2) . .
C3 C2 C1 121.7(2) . .
N2 C3 C2 122.4(2) . .
N2 C3 C1 116.3(2) . 2_765
C2 C3 C1 121.2(2) . 2_765
N2 C4 C5 118.7(2) . .
N2 C4 C17 120.4(2) . .
C5 C4 C17 121.0(2) . .
C4 C5 C6 119.4(2) . .
C4 C5 C18 118.3(2) . .
C6 C5 C18 122.3(2) . .
C7 C6 C5 121.6(2) . .
C7 C6 C15 118.5(2) . .
C5 C6 C15 119.9(2) . .
C8 C7 C6 122.0(2) . .
C7 C8 C9 122.4(2) . .
C7 C8 C13 119.5(2) . .
C9 C8 C13 118.1(2) . .
C10 C9 C8 121.2(2) . .
C9 C10 C11 120.4(2) . .
C12 C11 C10 120.9(2) . .
C11 C12 C13 120.6(2) . .
C14 C13 C12 122.0(2) . .
C14 C13 C8 119.2(2) . .
C12 C13 C8 118.8(2) . .
C13 C14 C15 121.9(2) . .
C14 C15 C16 121.4(2) . .
C14 C15 C6 119.0(2) . .
C16 C15 C6 119.6(2) . .
C17 C16 C15 119.9(2) . .
C17 C16 C29 119.5(2) . .
C15 C16 C29 120.7(2) . .
N1 C17 C16 118.6(2) . .
N1 C17 C4 121.3(2) . .
C16 C17 C4 120.1(2) . .
C19 C18 C5 175.7(3) . .
C18 C19 Si1 170.4(2) . .
C21 C20 C22 110.6(2) . .
C21 C20 Si1 111.9(2) . .
C22 C20 Si1 112.16(19) . .
C25 C23 C24 110.1(2) . .
C25 C23 Si1 113.94(18) . .
C24 C23 Si1 111.89(19) . .
C28 C26 C27 111.0(2) . .
C28 C26 Si1 111.28(18) . .
C27 C26 Si1 113.28(18) . .
C30 C29 C16 178.6(3) . .
C29 C30 Si2 177.0(2) . .
C32 C31 C33 110.6(2) . .
C32 C31 Si2 112.85(18) . .
C33 C31 Si2 115.23(18) . .
C36 C34 C35 110.9(2) . .
C36 C34 Si2 112.39(17) . .
C35 C34 Si2 115.34(18) . .
C38 C37 C39 110.8(2) . .
C38 C37 Si2 111.06(18) . .
C39 C37 Si2 111.38(17) . .
N3 C40 C41 178.9(3) . .
C2 N1 C17 117.0(2) . .
C3 N2 C4 116.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C19 1.844(3) .
Si1 C20 1.878(3) .
Si1 C26 1.883(3) .
Si1 C23 1.899(3) .
Si2 C30 1.841(3) .
Si2 C34 1.879(3) .
Si2 C37 1.881(3) .
Si2 C31 1.883(3) .
C1 O1 1.211(3) .
C1 C2 1.501(3) .
C1 C3 1.503(3) 2_765
C2 N1 1.310(3) .
C2 C3 1.439(3) .
C3 N2 1.310(3) .
C3 C1 1.503(3) 2_765
C4 N2 1.373(3) .
C4 C5 1.406(3) .
C4 C17 1.432(3) .
C5 C6 1.419(3) .
C5 C18 1.432(3) .
C6 C7 1.406(3) .
C6 C15 1.448(3) .
C7 C8 1.387(3) .
C8 C9 1.433(3) .
C8 C13 1.440(3) .
C9 C10 1.357(3) .
C10 C11 1.420(3) .
C11 C12 1.358(3) .
C12 C13 1.431(3) .
C13 C14 1.387(3) .
C14 C15 1.408(3) .
C15 C16 1.424(3) .
C16 C17 1.403(3) .
C16 C29 1.435(3) .
C17 N1 1.365(3) .
C18 C19 1.204(3) .
C20 C21 1.525(4) .
C20 C22 1.539(4) .
C23 C25 1.537(3) .
C23 C24 1.537(4) .
C26 C28 1.532(4) .
C26 C27 1.536(3) .
C29 C30 1.204(3) .
C31 C32 1.530(4) .
C31 C33 1.536(3) .
C34 C36 1.535(3) .
C34 C35 1.536(4) .
C37 C38 1.536(3) .
C37 C39 1.544(4) .
C40 N3 1.138(4) .
C40 C41 1.458(4) .
