#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233769.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_7233769
loop_
_publ_author_name
'Huawei Sun'
'Yi Zhang'
'Wei Yan'
'Wenxin Chen'
'Qi Lan'
'Siwei Liu'
'Long Jiang'
'Zhenguo Chi'
'Xudong Chen'
'Jiarui Xu'
_publ_section_title
;
 A novel ultrasound-sensitive mechanofluorochromic AIE-compound with
 remarkable blue-shifting and enhanced emission
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5812
_journal_page_last               5817
_journal_paper_doi               10.1039/C4TC00553H
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C33 H30 N4 O2'
_chemical_formula_weight         514.61
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.5266(16)
_cell_angle_beta                 92.1596(16)
_cell_angle_gamma                105.3963(17)
_cell_formula_units_Z            4
_cell_length_a                   13.0465(3)
_cell_length_b                   14.1234(3)
_cell_length_c                   15.2036(3)
_cell_measurement_reflns_used    30911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.8248
_cell_measurement_theta_min      2.9379
_cell_volume                     2669.92(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64083
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_correction_T_min  0.7832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         9446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0482
_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)+(0.0761P)²+1.2436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                8314
_reflns_number_total             9446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-5812.cif
_cod_data_source_block           exp_4931
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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 

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2669.92(9)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C66 H60 N8 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1029.22
_cod_database_code               7233769
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 0.07580(13) 0.31509(12) 0.50598(10) 0.0275(3) Uani 1 1 d . . .
C2 C 0.16703(13) 0.39537(11) 0.52928(10) 0.0271(3) Uani 1 1 d . . .
H2 H 0.1682 0.4434 0.5795 0.033 Uiso 1 1 calc R . .
C3 C 0.25503(12) 0.40516(11) 0.47987(10) 0.0260(3) Uani 1 1 d . . .
H3 H 0.3150 0.4612 0.4958 0.031 Uiso 1 1 calc R . .
C4 C 0.25801(12) 0.33489(11) 0.40723(10) 0.0255(3) Uani 1 1 d . . .
C5 C 0.16586(13) 0.25696(11) 0.38234(10) 0.0281(3) Uani 1 1 d . . .
H5 H 0.1652 0.2089 0.3322 0.034 Uiso 1 1 calc R . .
C6 C 0.07585(13) 0.24830(12) 0.42888(11) 0.0294(3) Uani 1 1 d . . .
H6 H 0.0132 0.1966 0.4086 0.035 Uiso 1 1 calc R . .
C7 C 0.35561(12) 0.32938(11) 0.36178(10) 0.0269(3) Uani 1 1 d . . .
C8 C -0.01882(12) 0.37376(12) 0.63013(11) 0.0286(3) Uani 1 1 d . . .
C9 C -0.03307(14) 0.46477(13) 0.61650(12) 0.0345(4) Uani 1 1 d . . .
H9 H -0.0383 0.4794 0.5575 0.041 Uiso 1 1 calc R . .
C10 C -0.03987(13) 0.53467(12) 0.68723(12) 0.0342(4) Uani 1 1 d . . .
H10 H -0.0472 0.5974 0.6764 0.041 Uiso 1 1 calc R . .
C11 C -0.03598(12) 0.51368(12) 0.77447(11) 0.0297(3) Uani 1 1 d . . .
C12 C -0.02353(13) 0.42120(12) 0.78747(11) 0.0312(4) Uani 1 1 d . . .
H12 H -0.0216 0.4050 0.8461 0.037 Uiso 1 1 calc R . .
C13 C -0.01403(13) 0.35282(12) 0.71673(11) 0.0299(3) Uani 1 1 d . . .
H13 H -0.0041 0.2909 0.7274 0.036 Uiso 1 1 calc R . .
C14 C -0.08492(13) 0.20354(12) 0.55291(10) 0.0290(3) Uani 1 1 d . . .
C15 C -0.04909(13) 0.12023(13) 0.55847(11) 0.0333(4) Uani 1 1 d . . .
H15 H 0.0254 0.1271 0.5649 0.040 Uiso 1 1 calc R . .
C16 C -0.11989(14) 0.02733(13) 0.55485(11) 0.0344(4) Uani 1 1 d . . .
H16 H -0.0932 -0.0288 0.5570 0.041 Uiso 1 1 calc R . .
C17 C -0.22947(13) 0.01449(12) 0.54810(10) 0.0312(4) Uani 1 1 d . . .
C18 C -0.26507(13) 0.09912(13) 0.54621(11) 0.0323(4) Uani 1 1 d . . .
H18 H -0.3394 0.0930 0.5441 0.039 Uiso 1 1 calc R . .
C19 C -0.19395(13) 0.19210(12) 0.54734(11) 0.0314(4) Uani 1 1 d . . .
H19 H -0.2203 0.2483 0.5443 0.038 Uiso 1 1 calc R . .
C20 C 0.41282(12) 0.51100(11) 0.35024(10) 0.0266(3) Uani 1 1 d . . .
C21 C 0.32096(13) 0.52077(13) 0.30796(11) 0.0326(4) Uani 1 1 d . . .
H21 H 0.2684 0.4637 0.2792 0.039 Uiso 1 1 calc R . .
C22 C 0.30638(14) 0.61459(14) 0.30804(13) 0.0401(4) Uani 1 1 d . . .
H22 H 0.2424 0.6214 0.2810 0.048 Uiso 1 1 calc R . .
C23 C 0.38412(15) 0.69840(13) 0.34708(13) 0.0409(4) Uani 1 1 d . . .
H23 H 0.3741 0.7624 0.3457 0.049 Uiso 1 1 calc R . .
C24 C 0.47612(15) 0.68867(13) 0.38795(13) 0.0382(4) Uani 1 1 d . . .
H24 H 0.5297 0.7461 0.4146 0.046 Uiso 1 1 calc R . .
C25 C 0.49045(13) 0.59529(12) 0.39015(11) 0.0328(4) Uani 1 1 d . . .
H25 H 0.5535 0.5888 0.4190 0.039 Uiso 1 1 calc R . .
C26 C 0.53342(13) 0.40584(12) 0.32198(11) 0.0297(3) Uani 1 1 d . . .
C27 C 0.56564(16) 0.43244(15) 0.24093(13) 0.0440(4) Uani 1 1 d . . .
H27 H 0.5205 0.4556 0.2035 0.053 Uiso 1 1 calc R . .
C28 C 0.66458(18) 0.42515(17) 0.21448(15) 0.0548(5) Uani 1 1 d . . .
H28 H 0.6871 0.4438 0.1590 0.066 Uiso 1 1 calc R . .
C29 C 0.72999(15) 0.39105(14) 0.26835(15) 0.0473(5) Uani 1 1 d . . .
H29 H 0.7975 0.3863 0.2500 0.057 Uiso 1 1 calc R . .
C30 C 0.69737(14) 0.36392(13) 0.34874(14) 0.0398(4) Uani 1 1 d . . .
H30 H 0.7421 0.3395 0.3854 0.048 Uiso 1 1 calc R . .
C31 C 0.59940(13) 0.37207(12) 0.37643(12) 0.0319(4) Uani 1 1 d . . .
H31 H 0.5777 0.3546 0.4324 0.038 Uiso 1 1 calc R . .
C32 C 0.41409(13) 0.14687(12) -0.02418(10) 0.0280(3) Uani 1 1 d . . .
C33 C 0.31398(13) 0.07724(12) -0.04611(10) 0.0286(3) Uani 1 1 d . . .
H33 H 0.3042 0.0278 -0.0968 0.034 Uiso 1 1 calc R . .
C34 C 0.22986(13) 0.08045(12) 0.00573(10) 0.0288(3) Uani 1 1 d . . .
H34 H 0.1634 0.0318 -0.0090 0.035 Uiso 1 1 calc R . .
C35 C 0.24047(13) 0.15357(12) 0.07922(11) 0.0287(3) Uani 1 1 d . . .
C36 C 0.33999(13) 0.22235(12) 0.10083(11) 0.0309(3) Uani 1 1 d . . .
H36 H 0.3488 0.2729 0.1505 0.037 Uiso 1 1 calc R . .
C37 C 0.42540(13) 0.21825(12) 0.05163(11) 0.0312(4) Uani 1 1 d . . .
H37 H 0.4929 0.2643 0.0692 0.037 Uiso 1 1 calc R . .
C38 C 0.15187(13) 0.16748(12) 0.13317(11) 0.0296(3) Uani 1 1 d . . .
C39 C 0.59656(13) 0.22345(13) -0.05634(11) 0.0337(4) Uani 1 1 d . . .
C40 C 0.67676(15) 0.21721(15) 0.00297(13) 0.0414(4) Uani 1 1 d . . .
H40 H 0.6704 0.1583 0.0287 0.050 Uiso 1 1 calc R . .
C41 C 0.76671(15) 0.29724(16) 0.02486(13) 0.0448(5) Uani 1 1 d . . .
H41 H 0.8217 0.2924 0.0654 0.054 Uiso 1 1 calc R . .
C42 C 0.77729(14) 0.38388(15) -0.01161(12) 0.0413(4) Uani 1 1 d . . .
C43 C 0.69947(16) 0.38723(15) -0.07435(13) 0.0468(5) Uani 1 1 d . . .
H43 H 0.7077 0.4444 -0.1030 0.056 Uiso 1 1 calc R . .
C44 C 0.60961(15) 0.30797(14) -0.09578(12) 0.0413(4) Uani 1 1 d . . .
H44 H 0.5561 0.3118 -0.1383 0.050 Uiso 1 1 calc R . .
C45 C 0.48981(12) 0.07559(12) -0.15493(11) 0.0292(3) Uani 1 1 d . . .
C46 C 0.45884(13) 0.09859(12) -0.23610(12) 0.0329(4) Uani 1 1 d . . .
H46 H 0.4412 0.1593 -0.2383 0.039 Uiso 1 1 calc R . .
C47 C 0.45351(13) 0.03374(12) -0.31376(11) 0.0327(4) Uani 1 1 d . . .
H47 H 0.4333 0.0506 -0.3691 0.039 Uiso 1 1 calc R . .
C48 C 0.47770(12) -0.05597(12) -0.31105(11) 0.0289(3) Uani 1 1 d . . .
C49 C 0.50805(13) -0.07940(13) -0.22979(11) 0.0331(4) Uani 1 1 d . . .
H49 H 0.5245 -0.1407 -0.2273 0.040 Uiso 1 1 calc R . .
C50 C 0.51433(14) -0.01357(13) -0.15242(11) 0.0347(4) Uani 1 1 d . . .
H50 H 0.5357 -0.0298 -0.0972 0.042 Uiso 1 1 calc R . .
C51 C -0.01730(12) 0.09078(12) 0.19300(11) 0.0292(3) Uani 1 1 d . . .
C52 C -0.07719(14) 0.14960(13) 0.16295(12) 0.0368(4) Uani 1 1 d . . .
H52 H -0.0573 0.1829 0.1133 0.044 Uiso 1 1 calc R . .
C53 C -0.16651(15) 0.15929(14) 0.20623(14) 0.0445(5) Uani 1 1 d . . .
H53 H -0.2070 0.2003 0.1865 0.053 Uiso 1 1 calc R . .
C54 C -0.19710(14) 0.11005(15) 0.27756(14) 0.0444(5) Uani 1 1 d . . .
H54 H -0.2576 0.1182 0.3074 0.053 Uiso 1 1 calc R . .
C55 C -0.13960(14) 0.04902(15) 0.30535(12) 0.0418(4) Uani 1 1 d . . .
H55 H -0.1617 0.0135 0.3534 0.050 Uiso 1 1 calc R . .
C56 C -0.04936(14) 0.03921(13) 0.26342(11) 0.0356(4) Uani 1 1 d . . .
H56 H -0.0097 -0.0027 0.2829 0.043 Uiso 1 1 calc R . .
C57 C 0.10897(13) -0.00735(12) 0.15579(10) 0.0287(3) Uani 1 1 d . . .
C58 C 0.19914(13) -0.00436(13) 0.20859(11) 0.0319(4) Uani 1 1 d . . .
H58 H 0.2405 0.0567 0.2414 0.038 Uiso 1 1 calc R . .
C59 C 0.22845(14) -0.09140(14) 0.21314(12) 0.0358(4) Uani 1 1 d . . .
H59 H 0.2907 -0.0897 0.2485 0.043 Uiso 1 1 calc R . .
C60 C 0.16758(15) -0.18020(14) 0.16665(13) 0.0387(4) Uani 1 1 d . . .
H60 H 0.1883 -0.2394 0.1697 0.046 Uiso 1 1 calc R . .
C61 C 0.07603(15) -0.18341(13) 0.11531(13) 0.0402(4) Uani 1 1 d . . .
H61 H 0.0336 -0.2449 0.0841 0.048 Uiso 1 1 calc R . .
C62 C 0.04664(14) -0.09684(13) 0.10953(12) 0.0342(4) Uani 1 1 d . . .
H62 H -0.0157 -0.0987 0.0742 0.041 Uiso 1 1 calc R . .
C63 C 0.7135(2) 0.65262(19) 0.0945(2) 0.0720(7) Uani 1 1 d . . .
C64 C 0.6195(3) 0.5846(2) 0.0387(3) 0.1031(12) Uani 1 1 d . . .
H64A H 0.6334 0.5834 -0.0243 0.155 Uiso 1 1 calc R . .
H64B H 0.5564 0.6083 0.0495 0.155 Uiso 1 1 calc R . .
H64C H 0.6072 0.5175 0.0543 0.155 Uiso 1 1 calc R . .
C65 C 0.7737(2) 0.7828(2) 0.2125(2) 0.0832(8) Uani 1 1 d . . .
H65A H 0.8438 0.7817 0.1902 0.100 Uiso 1 1 calc R . .
H65B H 0.7662 0.8510 0.2146 0.100 Uiso 1 1 calc R . .
C66 C 0.7664(3) 0.7535(3) 0.2996(3) 0.1126(14) Uani 1 1 d . . .
H66A H 0.7037 0.7678 0.3260 0.169 Uiso 1 1 calc R . .
H66B H 0.8308 0.7905 0.3374 0.169 Uiso 1 1 calc R . .
H66C H 0.7597 0.6822 0.2949 0.169 Uiso 1 1 calc R . .
N1 N -0.01224(11) 0.30067(10) 0.55668(9) 0.0324(3) Uani 1 1 d . . .
N2 N 0.43207(10) 0.41566(10) 0.35088(9) 0.0279(3) Uani 1 1 d . . .
N3 N -0.04228(12) 0.58266(11) 0.84730(10) 0.0389(3) Uani 1 1 d . . .
H3B H -0.0816 0.5505 0.8881 0.058 Uiso 1 1 d R . .
H3A H -0.0741 0.6274 0.8288 0.058 Uiso 1 1 d R . .
N4 N -0.30114(13) -0.07924(11) 0.54085(11) 0.0413(4) Uani 1 1 d . . .
H4B H -0.3631 -0.0735 0.5635 0.062 Uiso 1 1 d R . .
H4A H -0.2729 -0.1183 0.5720 0.062 Uiso 1 1 d R . .
N5 N 0.49971(11) 0.14424(11) -0.07434(9) 0.0351(3) Uani 1 1 d . . .
N6 N 0.07748(11) 0.08238(10) 0.15089(9) 0.0296(3) Uani 1 1 d . . .
N7 N 0.86745(13) 0.46649(14) 0.01100(11) 0.0545(5) Uani 1 1 d . . .
H7A H 0.9087 0.4547 0.0557 0.082 Uiso 1 1 d R . .
H7B H 0.8456 0.5214 0.0295 0.082 Uiso 1 1 d R . .
N8 N 0.47504(12) -0.12124(11) -0.39047(10) 0.0377(3) Uani 1 1 d . . .
H8A H 0.4130 -0.1292 -0.4236 0.057 Uiso 1 1 d R . .
H8B H 0.4789 -0.1811 -0.3768 0.057 Uiso 1 1 d R . .
O1 O 0.37068(9) 0.24824(8) 0.33705(8) 0.0354(3) Uani 1 1 d . . .
O2 O 0.14425(10) 0.25069(9) 0.15995(9) 0.0391(3) Uani 1 1 d . . .
O3 O 0.8051(2) 0.65157(18) 0.0804(2) 0.1154(9) Uani 1 1 d . . .
O4 O 0.68897(15) 0.71340(15) 0.15456(15) 0.0836(6) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1 C1 C2 122.09(14) . .
N1 C1 C6 120.28(14) . .
C2 C1 C6 117.63(14) . .
C3 C2 C1 120.71(14) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 121.60(14) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C3 C4 C5 117.52(14) . .
C3 C4 C7 124.68(14) . .
C5 C4 C7 117.31(13) . .
C6 C5 C4 121.50(14) . .
C6 C5 H5 119.2 . .
C4 C5 H5 119.2 . .
C5 C6 C1 120.78(14) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
O1 C7 N2 119.85(14) . .
O1 C7 C4 119.79(14) . .
N2 C7 C4 120.30(13) . .
C9 C8 C13 118.54(15) . .
C9 C8 N1 121.35(15) . .
C13 C8 N1 120.08(14) . .
C10 C9 C8 121.20(16) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C9 C10 C11 120.48(15) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
N3 C11 C12 120.17(15) . .
N3 C11 C10 121.91(15) . .
C12 C11 C10 117.91(15) . .
C13 C12 C11 121.25(15) . .
C13 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C12 C13 C8 120.57(15) . .
C12 C13 H13 119.7 . .
C8 C13 H13 119.7 . .
C19 C14 C15 118.28(15) . .
C19 C14 N1 119.91(15) . .
C15 C14 N1 121.75(14) . .
C16 C15 C14 121.12(15) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C15 C16 C17 121.21(16) . .
C15 C16 H16 119.4 . .
C17 C16 H16 119.4 . .
C16 C17 N4 121.50(16) . .
C16 C17 C18 117.42(15) . .
N4 C17 C18 121.06(16) . .
C19 C18 C17 121.34(15) . .
C19 C18 H18 119.3 . .
C17 C18 H18 119.3 . .
C14 C19 C18 120.54(15) . .
C14 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C21 C20 C25 119.74(15) . .
C21 C20 N2 121.45(14) . .
C25 C20 N2 118.76(14) . .
C20 C21 C22 119.45(16) . .
C20 C21 H21 120.3 . .
C22 C21 H21 120.3 . .
C23 C22 C21 120.69(17) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C24 C23 C22 119.78(16) . .
C24 C23 H23 120.1 . .
C22 C23 H23 120.1 . .
C23 C24 C25 120.05(16) . .
C23 C24 H24 120.0 . .
C25 C24 H24 120.0 . .
C24 C25 C20 120.26(16) . .
C24 C25 H25 119.9 . .
C20 C25 H25 119.9 . .
C27 C26 C31 120.08(16) . .
C27 C26 N2 119.92(15) . .
C31 C26 N2 119.98(15) . .
C26 C27 C28 119.63(18) . .
C26 C27 H27 120.2 . .
C28 C27 H27 120.2 . .
C29 C28 C27 120.34(19) . .
C29 C28 H28 119.8 . .
C27 C28 H28 119.8 . .
C30 C29 C28 119.92(17) . .
C30 C29 H29 120.0 . .
C28 C29 H29 120.0 . .
C29 C30 C31 120.31(18) . .
C29 C30 H30 119.8 . .
C31 C30 H30 119.8 . .
C26 C31 C30 119.72(17) . .
C26 C31 H31 120.1 . .
C30 C31 H31 120.1 . .
N5 C32 C37 120.58(15) . .
N5 C32 C33 121.36(14) . .
C37 C32 C33 118.04(14) . .
C34 C33 C32 120.36(15) . .
C34 C33 H33 119.8 . .
C32 C33 H33 119.8 . .
C33 C34 C35 121.38(15) . .
C33 C34 H34 119.3 . .
C35 C34 H34 119.3 . .
C34 C35 C36 118.03(14) . .
C34 C35 C38 124.60(15) . .
C36 C35 C38 117.26(14) . .
C37 C36 C35 121.30(15) . .
C37 C36 H36 119.4 . .
C35 C36 H36 119.4 . .
C36 C37 C32 120.82(15) . .
C36 C37 H37 119.6 . .
C32 C37 H37 119.6 . .
O2 C38 N6 121.71(15) . .
O2 C38 C35 120.84(15) . .
N6 C38 C35 117.44(14) . .
C44 C39 C40 119.02(17) . .
C44 C39 N5 120.55(16) . .
C40 C39 N5 120.40(17) . .
C39 C40 C41 119.91(19) . .
C39 C40 H40 120.0 . .
C41 C40 H40 120.0 . .
C42 C41 C40 120.92(18) . .
C42 C41 H41 119.5 . .
C40 C41 H41 119.5 . .
C43 C42 C41 118.58(17) . .
C43 C42 N7 119.73(19) . .
C41 C42 N7 121.64(18) . .
C42 C43 C44 120.48(19) . .
C42 C43 H43 119.8 . .
C44 C43 H43 119.8 . .
C39 C44 C43 120.92(18) . .
C39 C44 H44 119.5 . .
C43 C44 H44 119.5 . .
C50 C45 C46 119.20(15) . .
C50 C45 N5 119.82(15) . .
C46 C45 N5 120.95(15) . .
C47 C46 C45 120.54(15) . .
C47 C46 H46 119.7 . .
C45 C46 H46 119.7 . .
C46 C47 C48 120.17(15) . .
C46 C47 H47 119.9 . .
C48 C47 H47 119.9 . .
C47 C48 C49 119.37(15) . .
C47 C48 N8 120.33(15) . .
C49 C48 N8 120.26(15) . .
C50 C49 C48 120.11(15) . .
C50 C49 H49 119.9 . .
C48 C49 H49 119.9 . .
C45 C50 C49 120.60(15) . .
C45 C50 H50 119.7 . .
C49 C50 H50 119.7 . .
C52 C51 C56 119.94(16) . .
C52 C51 N6 120.20(15) . .
C56 C51 N6 119.86(15) . .
C51 C52 C53 119.36(18) . .
C51 C52 H52 120.3 . .
C53 C52 H52 120.3 . .
C54 C53 C52 120.80(18) . .
C54 C53 H53 119.6 . .
C52 C53 H53 119.6 . .
C55 C54 C53 119.71(17) . .
C55 C54 H54 120.1 . .
C53 C54 H54 120.1 . .
C54 C55 C56 120.27(18) . .
C54 C55 H55 119.9 . .
C56 C55 H55 119.9 . .
C51 C56 C55 119.86(17) . .
C51 C56 H56 120.1 . .
C55 C56 H56 120.1 . .
C58 C57 C62 120.49(15) . .
C58 C57 N6 119.93(15) . .
C62 C57 N6 119.55(15) . .
C57 C58 C59 119.43(16) . .
C57 C58 H58 120.3 . .
C59 C58 H58 120.3 . .
C60 C59 C58 120.32(16) . .
C60 C59 H59 119.8 . .
C58 C59 H59 119.8 . .
C59 C60 C61 120.17(16) . .
C59 C60 H60 119.9 . .
C61 C60 H60 119.9 . .
C62 C61 C60 120.00(17) . .
C62 C61 H61 120.0 . .
C60 C61 H61 120.0 . .
C61 C62 C57 119.57(16) . .
C61 C62 H62 120.2 . .
C57 C62 H62 120.2 . .
O3 C63 O4 124.3(3) . .
O3 C63 C64 122.0(3) . .
O4 C63 C64 113.7(3) . .
C63 C64 H64A 109.5 . .
C63 C64 H64B 109.5 . .
H64A C64 H64B 109.5 . .
C63 C64 H64C 109.5 . .
H64A C64 H64C 109.5 . .
H64B C64 H64C 109.5 . .
C66 C65 O4 107.6(3) . .
C66 C65 H65A 110.2 . .
O4 C65 H65A 110.2 . .
C66 C65 H65B 110.2 . .
O4 C65 H65B 110.2 . .
H65A C65 H65B 108.5 . .
C65 C66 H66A 109.5 . .
C65 C66 H66B 109.5 . .
H66A C66 H66B 109.5 . .
C65 C66 H66C 109.5 . .
H66A C66 H66C 109.5 . .
H66B C66 H66C 109.5 . .
C1 N1 C14 120.52(13) . .
C1 N1 C8 121.11(13) . .
C14 N1 C8 116.44(12) . .
C7 N2 C20 125.12(13) . .
C7 N2 C26 117.43(12) . .
C20 N2 C26 116.45(12) . .
C11 N3 H3B 109.3 . .
C11 N3 H3A 109.4 . .
H3B N3 H3A 109.5 . .
C17 N4 H4B 109.2 . .
C17 N4 H4A 109.3 . .
H4B N4 H4A 109.5 . .
C32 N5 C39 119.56(13) . .
C32 N5 C45 122.15(13) . .
C39 N5 C45 117.22(13) . .
C38 N6 C51 119.85(13) . .
C38 N6 C57 119.96(13) . .
C51 N6 C57 116.97(13) . .
C42 N7 H7A 109.3 . .
C42 N7 H7B 109.3 . .
H7A N7 H7B 109.5 . .
C48 N8 H8A 109.3 . .
C48 N8 H8B 109.3 . .
H8A N8 H8B 109.5 . .
C63 O4 C65 118.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.392(2) .
C1 C2 1.405(2) .
C1 C6 1.405(2) .
C2 C3 1.382(2) .
C2 H2 0.9500 .
C3 C4 1.394(2) .
C3 H3 0.9500 .
C4 C5 1.398(2) .
C4 C7 1.486(2) .
C5 C6 1.380(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.2270(19) .
C7 N2 1.388(2) .
C8 C9 1.387(2) .
C8 C13 1.389(2) .
C8 N1 1.440(2) .
C9 C10 1.384(2) .
C9 H9 0.9500 .
C10 C11 1.398(2) .
C10 H10 0.9500 .
C11 N3 1.396(2) .
C11 C12 1.396(2) .
C12 C13 1.381(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C19 1.386(2) .
C14 C15 1.388(2) .
C14 N1 1.438(2) .
C15 C16 1.383(2) .
C15 H15 0.9500 .
C16 C17 1.391(2) .
C16 H16 0.9500 .
C17 N4 1.391(2) .
C17 C18 1.396(2) .
C18 C19 1.390(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.386(2) .
C20 C25 1.391(2) .
C20 N2 1.435(2) .
C21 C22 1.388(2) .
C21 H21 0.9500 .
C22 C23 1.384(3) .
C22 H22 0.9500 .
C23 C24 1.378(3) .
C23 H23 0.9500 .
C24 C25 1.385(2) .
C24 H24 0.9500 .
C25 H25 0.9500 .
C26 C27 1.383(3) .
C26 C31 1.386(2) .
C26 N2 1.444(2) .
C27 C28 1.392(3) .
C27 H27 0.9500 .
C28 C29 1.378(3) .
C28 H28 0.9500 .
C29 C30 1.377(3) .
C29 H29 0.9500 .
C30 C31 1.389(2) .
C30 H30 0.9500 .
C31 H31 0.9500 .
C32 N5 1.382(2) .
C32 C37 1.404(2) .
C32 C33 1.408(2) .
C33 C34 1.382(2) .
C33 H33 0.9500 .
C34 C35 1.394(2) .
C34 H34 0.9500 .
C35 C36 1.397(2) .
C35 C38 1.482(2) .
C36 C37 1.375(2) .
C36 H36 0.9500 .
C37 H37 0.9500 .
C38 O2 1.223(2) .
C38 N6 1.394(2) .
C39 C44 1.379(3) .
C39 C40 1.384(3) .
C39 N5 1.437(2) .
C40 C41 1.390(3) .
C40 H40 0.9500 .
C41 C42 1.385(3) .
C41 H41 0.9500 .
C42 C43 1.381(3) .
C42 N7 1.414(2) .
C43 C44 1.383(3) .
C43 H43 0.9500 .
C44 H44 0.9500 .
C45 C50 1.384(2) .
C45 C46 1.389(2) .
C45 N5 1.438(2) .
C46 C47 1.384(2) .
C46 H46 0.9500 .
C47 C48 1.390(2) .
C47 H47 0.9500 .
C48 C49 1.390(2) .
C48 N8 1.413(2) .
C49 C50 1.386(2) .
C49 H49 0.9500 .
C50 H50 0.9500 .
C51 C52 1.388(2) .
C51 C56 1.389(2) .
C51 N6 1.439(2) .
C52 C53 1.389(3) .
C52 H52 0.9500 .
C53 C54 1.379(3) .
C53 H53 0.9500 .
C54 C55 1.378(3) .
C54 H54 0.9500 .
C55 C56 1.390(3) .
C55 H55 0.9500 .
C56 H56 0.9500 .
C57 C58 1.387(2) .
C57 C62 1.390(2) .
C57 N6 1.442(2) .
C58 C59 1.390(2) .
C58 H58 0.9500 .
C59 C60 1.378(3) .
C59 H59 0.9500 .
C60 C61 1.389(3) .
C60 H60 0.9500 .
C61 C62 1.387(3) .
C61 H61 0.9500 .
C62 H62 0.9500 .
C63 O3 1.226(3) .
C63 O4 1.279(4) .
C63 C64 1.493(4) .
C64 H64A 0.9800 .
C64 H64B 0.9800 .
C64 H64C 0.9800 .
C65 C66 1.439(5) .
C65 O4 1.444(3) .
C65 H65A 0.9900 .
C65 H65B 0.9900 .
C66 H66A 0.9800 .
C66 H66B 0.9800 .
C66 H66C 0.9800 .
N3 H3B 0.9100 .
N3 H3A 0.9100 .
N4 H4B 0.9100 .
N4 H4A 0.9100 .
N7 H7A 0.9100 .
N7 H7B 0.9100 .
N8 H8A 0.9100 .
N8 H8B 0.9100 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B N7 0.91 2.37 3.246(2) 162.7 1_456
N3 H3A O2 0.91 2.14 3.0068(19) 157.7 2_566
N4 H4B N8 0.91 2.21 3.073(2) 158.2 1_456
N4 H4A O1 0.91 2.54 3.1787(19) 127.5 2_556
N7 H7A N3 0.91 2.45 3.345(3) 168.7 2_666
N7 H7B O3 0.91 2.11 3.013(3) 175.4 .
N8 H8B O1 0.91 2.48 3.179(2) 133.5 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 177.03(14) . . . .
C6 C1 C2 C3 -2.8(2) . . . .
C1 C2 C3 C4 -1.9(2) . . . .
C2 C3 C4 C5 4.0(2) . . . .
C2 C3 C4 C7 -167.68(14) . . . .
C3 C4 C5 C6 -1.4(2) . . . .
C7 C4 C5 C6 170.92(15) . . . .
C4 C5 C6 C1 -3.3(2) . . . .
N1 C1 C6 C5 -174.46(15) . . . .
C2 C1 C6 C5 5.3(2) . . . .
C3 C4 C7 O1 139.96(16) . . . .
C5 C4 C7 O1 -31.8(2) . . . .
C3 C4 C7 N2 -37.1(2) . . . .
C5 C4 C7 N2 151.23(15) . . . .
C13 C8 C9 C10 1.5(2) . . . .
N1 C8 C9 C10 179.69(15) . . . .
C8 C9 C10 C11 -2.1(3) . . . .
C9 C10 C11 N3 179.79(16) . . . .
C9 C10 C11 C12 0.9(2) . . . .
N3 C11 C12 C13 -178.12(15) . . . .
C10 C11 C12 C13 0.8(2) . . . .
C11 C12 C13 C8 -1.3(2) . . . .
C9 C8 C13 C12 0.2(2) . . . .
N1 C8 C13 C12 -178.01(14) . . . .
C19 C14 C15 C16 2.7(2) . . . .
N1 C14 C15 C16 179.93(15) . . . .
C14 C15 C16 C17 -1.9(3) . . . .
C15 C16 C17 N4 177.40(16) . . . .
C15 C16 C17 C18 -0.8(2) . . . .
C16 C17 C18 C19 2.6(2) . . . .
N4 C17 C18 C19 -175.58(15) . . . .
C15 C14 C19 C18 -0.8(2) . . . .
N1 C14 C19 C18 -178.15(15) . . . .
C17 C18 C19 C14 -1.8(2) . . . .
C25 C20 C21 C22 -1.7(2) . . . .
N2 C20 C21 C22 -179.14(15) . . . .
C20 C21 C22 C23 2.3(3) . . . .
C21 C22 C23 C24 -1.3(3) . . . .
C22 C23 C24 C25 -0.2(3) . . . .
C23 C24 C25 C20 0.8(3) . . . .
C21 C20 C25 C24 0.2(2) . . . .
N2 C20 C25 C24 177.68(15) . . . .
C31 C26 C27 C28 0.0(3) . . . .
N2 C26 C27 C28 178.39(18) . . . .
C26 C27 C28 C29 0.4(3) . . . .
C27 C28 C29 C30 0.1(3) . . . .
C28 C29 C30 C31 -0.9(3) . . . .
C27 C26 C31 C30 -0.8(2) . . . .
N2 C26 C31 C30 -179.22(14) . . . .
C29 C30 C31 C26 1.3(3) . . . .
N5 C32 C33 C34 179.10(15) . . . .
C37 C32 C33 C34 0.5(2) . . . .
C32 C33 C34 C35 1.7(2) . . . .
C33 C34 C35 C36 -1.8(2) . . . .
C33 C34 C35 C38 174.29(15) . . . .
C34 C35 C36 C37 -0.3(2) . . . .
C38 C35 C36 C37 -176.69(15) . . . .
C35 C36 C37 C32 2.5(3) . . . .
N5 C32 C37 C36 178.80(15) . . . .
C33 C32 C37 C36 -2.6(2) . . . .
C34 C35 C38 O2 -139.54(17) . . . .
C36 C35 C38 O2 36.6(2) . . . .
C34 C35 C38 N6 39.6(2) . . . .
C36 C35 C38 N6 -144.24(15) . . . .
C44 C39 C40 C41 2.8(3) . . . .
N5 C39 C40 C41 -175.28(16) . . . .
C39 C40 C41 C42 0.3(3) . . . .
C40 C41 C42 C43 -3.8(3) . . . .
C40 C41 C42 N7 178.98(17) . . . .
C41 C42 C43 C44 4.2(3) . . . .
N7 C42 C43 C44 -178.52(18) . . . .
C40 C39 C44 C43 -2.4(3) . . . .
N5 C39 C44 C43 175.68(17) . . . .
C42 C43 C44 C39 -1.1(3) . . . .
C50 C45 C46 C47 -0.6(2) . . . .
N5 C45 C46 C47 177.50(15) . . . .
C45 C46 C47 C48 0.9(2) . . . .
C46 C47 C48 C49 -0.5(2) . . . .
C46 C47 C48 N8 -178.35(15) . . . .
C47 C48 C49 C50 -0.2(2) . . . .
N8 C48 C49 C50 177.64(15) . . . .
C46 C45 C50 C49 -0.1(2) . . . .
N5 C45 C50 C49 -178.23(15) . . . .
C48 C49 C50 C45 0.5(3) . . . .
C56 C51 C52 C53 2.6(3) . . . .
N6 C51 C52 C53 -177.97(15) . . . .
C51 C52 C53 C54 -1.0(3) . . . .
C52 C53 C54 C55 -1.2(3) . . . .
C53 C54 C55 C56 1.8(3) . . . .
C52 C51 C56 C55 -1.9(2) . . . .
N6 C51 C56 C55 178.60(15) . . . .
C54 C55 C56 C51 -0.3(3) . . . .
C62 C57 C58 C59 1.7(2) . . . .
N6 C57 C58 C59 179.70(14) . . . .
C57 C58 C59 C60 -1.0(2) . . . .
C58 C59 C60 C61 -0.4(3) . . . .
C59 C60 C61 C62 1.1(3) . . . .
C60 C61 C62 C57 -0.4(3) . . . .
C58 C57 C62 C61 -1.0(2) . . . .
N6 C57 C62 C61 -179.03(15) . . . .
C2 C1 N1 C14 -156.52(15) . . . .
C6 C1 N1 C14 23.3(2) . . . .
C2 C1 N1 C8 7.1(2) . . . .
C6 C1 N1 C8 -173.11(15) . . . .
C19 C14 N1 C1 -136.08(16) . . . .
C15 C14 N1 C1 46.7(2) . . . .
C19 C14 N1 C8 59.6(2) . . . .
C15 C14 N1 C8 -117.66(17) . . . .
C9 C8 N1 C1 69.9(2) . . . .
C13 C8 N1 C1 -111.94(18) . . . .
C9 C8 N1 C14 -125.81(17) . . . .
C13 C8 N1 C14 52.3(2) . . . .
O1 C7 N2 C20 159.50(15) . . . .
C4 C7 N2 C20 -23.5(2) . . . .
O1 C7 N2 C26 -8.6(2) . . . .
C4 C7 N2 C26 168.42(14) . . . .
C21 C20 N2 C7 -40.3(2) . . . .
C25 C20 N2 C7 142.28(16) . . . .
C21 C20 N2 C26 127.94(16) . . . .
C25 C20 N2 C26 -49.5(2) . . . .
C27 C26 N2 C7 116.48(18) . . . .
C31 C26 N2 C7 -65.1(2) . . . .
C27 C26 N2 C20 -52.7(2) . . . .
C31 C26 N2 C20 125.77(16) . . . .
C37 C32 N5 C39 -8.9(2) . . . .
C33 C32 N5 C39 172.49(15) . . . .
C37 C32 N5 C45 -176.71(15) . . . .
C33 C32 N5 C45 4.7(2) . . . .
C44 C39 N5 C32 -86.8(2) . . . .
C40 C39 N5 C32 91.3(2) . . . .
C44 C39 N5 C45 81.6(2) . . . .
C40 C39 N5 C45 -100.37(19) . . . .
C50 C45 N5 C32 -95.2(2) . . . .
C46 C45 N5 C32 86.7(2) . . . .
C50 C45 N5 C39 96.73(19) . . . .
C46 C45 N5 C39 -81.4(2) . . . .
O2 C38 N6 C51 7.1(2) . . . .
C35 C38 N6 C51 -172.09(14) . . . .
O2 C38 N6 C57 -152.04(16) . . . .
C35 C38 N6 C57 28.8(2) . . . .
C52 C51 N6 C38 46.8(2) . . . .
C56 C51 N6 C38 -133.71(16) . . . .
C52 C51 N6 C57 -153.48(15) . . . .
C56 C51 N6 C57 26.0(2) . . . .
C58 C57 N6 C38 50.2(2) . . . .
C62 C57 N6 C38 -131.76(16) . . . .
C58 C57 N6 C51 -109.49(17) . . . .
C62 C57 N6 C51 68.55(19) . . . .
O3 C63 O4 C65 -2.8(4) . . . .
C64 C63 O4 C65 -179.9(3) . . . .
C66 C65 O4 C63 -110.0(3) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338786
