#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234422.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_7234422
loop_
_publ_author_name
'Liang Xu'
'Hai Zhu'
'Guankui Long'
'Jun Zhao'
'Dongsheng Li'
'Rakesh Ganguly'
'Yongxin Li'
'Qing-Hua Xu'
'Qichun Zhang'
_publ_section_title
;
 4-Diphenylamino-phenyl substituted pyrazine: nonlinear optical switching
 by protonation
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9191
_journal_page_last               9196
_journal_paper_doi               10.1039/C5TC01657F
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C44 H32 N4'
_chemical_formula_weight         616.73
_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
_cell_angle_alpha                97.458(3)
_cell_angle_beta                 104.211(3)
_cell_angle_gamma                109.487(3)
_cell_formula_units_Z            4
_cell_length_a                   10.9996(4)
_cell_length_b                   15.5466(7)
_cell_length_c                   20.7794(10)
_cell_measurement_reflns_used    7837
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      28.5751
_cell_measurement_theta_min      2.8051
_cell_volume                     3159.0(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_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2025
_diffrn_reflns_av_unetI/netI     0.2437
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            76801
_diffrn_reflns_theta_full        28.87
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     865
_refine_ls_number_reflns         16434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.2432
_refine_ls_R_factor_gt           0.0780
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0707P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.2041
_reflns_number_gt                5742
_reflns_number_total             16434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-9191.cif
_cod_data_source_block           I
_cod_original_cell_volume        3159.0(2)
_cod_database_code               7234422
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2348(3) 0.0867(2) 0.14824(18) 0.0262(8) Uani d . . . 1 . .
C C2 0.2032(3) 0.0529(2) 0.20341(18) 0.0293(8) Uani d . . . 1 . .
H H2 0.246 0.0916 0.2483 0.035 Uiso calc U . R 1 . .
C C3 0.1087(3) -0.0377(2) 0.1926(2) 0.0330(9) Uani d . . . 1 . .
H H3 0.0889 -0.0615 0.2303 0.04 Uiso calc U . R 1 . .
C C4 0.0440(3) -0.0929(2) 0.1274(2) 0.0364(10) Uani d . . . 1 . .
H H4 -0.0218 -0.1541 0.1199 0.044 Uiso calc U . R 1 . .
C C5 0.0752(3) -0.0588(2) 0.0726(2) 0.0348(9) Uani d . . . 1 . .
H H5 0.0305 -0.097 0.0277 0.042 Uiso calc U . R 1 . .
C C6 0.1705(3) 0.0302(2) 0.08280(18) 0.0304(9) Uani d . . . 1 . .
H H6 0.192 0.0527 0.045 0.036 Uiso calc U . R 1 . .
C C7 0.3126(3) 0.2322(2) 0.10928(17) 0.0239(8) Uani d . . . 1 . .
C C8 0.4174(3) 0.2784(2) 0.08479(17) 0.0291(8) Uani d . . . 1 . .
H H8 0.5038 0.2749 0.1012 0.035 Uiso calc U . R 1 . .
C C9 0.3952(3) 0.3294(2) 0.03650(18) 0.0342(9) Uani d . . . 1 . .
H H9 0.4676 0.3616 0.0204 0.041 Uiso calc U . R 1 . .
C C10 0.2702(3) 0.3346(2) 0.01113(18) 0.0333(9) Uani d . . . 1 . .
H H10 0.256 0.3695 -0.0223 0.04 Uiso calc U . R 1 . .
C C11 0.1665(3) 0.2882(2) 0.03510(17) 0.0297(9) Uani d . . . 1 . .
H H11 0.08 0.2913 0.0181 0.036 Uiso calc U . R 1 . .
C C12 0.1869(3) 0.2369(2) 0.08380(17) 0.0275(8) Uani d . . . 1 . .
H H12 0.1143 0.2049 0.0997 0.033 Uiso calc U . R 1 . .
C C13 0.4588(3) 0.2077(2) 0.21046(17) 0.0241(8) Uani d . . . 1 . .
C C14 0.5159(3) 0.1433(2) 0.22764(18) 0.0302(9) Uani d . . . 1 . .
H H14 0.469 0.0789 0.2052 0.036 Uiso calc U . R 1 . .
C C15 0.6402(3) 0.1721(2) 0.27695(18) 0.0284(8) Uani d . . . 1 . .
H H15 0.6778 0.1268 0.2873 0.034 Uiso calc U . R 1 . .
C C16 0.7121(3) 0.2653(2) 0.31193(16) 0.0222(8) Uani d . . . 1 . .
C C17 0.6527(3) 0.3291(2) 0.29567(16) 0.0237(8) Uani d . . . 1 . .
H H17 0.6983 0.3931 0.3193 0.028 Uiso calc U . R 1 . .
C C18 0.5288(3) 0.3015(2) 0.24582(17) 0.0261(8) Uani d . . . 1 . .
H H18 0.491 0.3467 0.2356 0.031 Uiso calc U . R 1 . .
C C19 0.8457(3) 0.2881(2) 0.36507(17) 0.0233(8) Uani d . . . 1 . .
C C20 0.9541(3) 0.3791(2) 0.38710(16) 0.0207(7) Uani d . . . 1 . .
C C21 1.0886(3) 0.3201(2) 0.45679(16) 0.0230(8) Uani d . . . 1 . .
C C22 1.2159(3) 0.3329(2) 0.50036(16) 0.0247(8) Uani d . . . 1 . .
H H22 1.2888 0.3922 0.5127 0.03 Uiso calc U . R 1 . .
C C23 1.2341(3) 0.2587(2) 0.52511(17) 0.0311(9) Uani d . . . 1 . .
H H23 1.3206 0.2662 0.5538 0.037 Uiso calc U . R 1 . .
C C24 1.1254(4) 0.1719(2) 0.50800(17) 0.0314(9) Uani d . . . 1 . .
H H24 1.1388 0.1216 0.5262 0.038 Uiso calc U . R 1 . .
C C25 1.0009(3) 0.1583(2) 0.46569(17) 0.0265(8) Uani d . . . 1 . .
H H25 0.9279 0.0994 0.4552 0.032 Uiso calc U . R 1 . .
C C26 0.9810(3) 0.2325(2) 0.43758(16) 0.0219(8) Uani d . . . 1 . .
C C27 0.9465(3) 0.4612(2) 0.35971(16) 0.0204(7) Uani d . . . 1 . .
C C28 0.9299(3) 0.5342(2) 0.39804(17) 0.0250(8) Uani d . . . 1 . .
H H28 0.9268 0.5326 0.4432 0.03 Uiso calc U . R 1 . .
C C29 0.9177(3) 0.6093(2) 0.37138(17) 0.0236(8) Uani d . . . 1 . .
H H29 0.9054 0.6584 0.398 0.028 Uiso calc U . R 1 . .
C C30 0.9233(3) 0.6127(2) 0.30545(17) 0.0225(8) Uani d . . . 1 . .
C C31 0.9482(3) 0.5426(2) 0.26811(17) 0.0238(8) Uani d . . . 1 . .
H H31 0.9576 0.5463 0.2242 0.029 Uiso calc U . R 1 . .
C C32 0.9592(3) 0.4678(2) 0.29514(17) 0.0251(8) Uani d . . . 1 . .
H H32 0.9756 0.4201 0.2694 0.03 Uiso calc U . R 1 . .
C C33 0.9717(3) 0.7791(2) 0.31111(17) 0.0255(8) Uani d . . . 1 . .
C C34 0.9124(3) 0.8426(2) 0.32365(18) 0.0311(9) Uani d . . . 1 . .
H H34 0.8164 0.8225 0.3092 0.037 Uiso calc U . R 1 . .
C C35 0.9915(4) 0.9351(2) 0.35707(18) 0.0352(9) Uani d . . . 1 . .
H H35 0.9497 0.9785 0.3639 0.042 Uiso calc U . R 1 . .
C C36 1.1313(4) 0.9647(2) 0.38053(19) 0.0379(10) Uani d . . . 1 . .
H H36 1.1852 1.0281 0.4037 0.045 Uiso calc U . R 1 . .
C C37 1.1922(4) 0.9018(2) 0.37014(18) 0.0325(9) Uani d . . . 1 . .
H H37 1.2881 0.9219 0.3866 0.039 Uiso calc U . R 1 . .
C C38 1.1135(3) 0.8094(2) 0.33567(17) 0.0294(8) Uani d . . . 1 . .
H H38 1.1559 0.7663 0.3286 0.035 Uiso calc U . R 1 . .
C C39 0.7720(3) 0.6562(2) 0.22248(16) 0.0238(8) Uani d . . . 1 . .
C C40 0.7434(3) 0.7173(2) 0.18361(18) 0.0308(9) Uani d . . . 1 . .
H H40 0.8099 0.7783 0.1909 0.037 Uiso calc U . R 1 . .
C C41 0.6186(4) 0.6901(3) 0.13424(19) 0.0412(10) Uani d . . . 1 . .
H H41 0.5994 0.7331 0.1088 0.049 Uiso calc U . R 1 . .
C C42 0.5218(4) 0.6008(3) 0.1218(2) 0.0418(10) Uani d . . . 1 . .
H H42 0.436 0.5828 0.0883 0.05 Uiso calc U . R 1 . .
C C43 0.5503(3) 0.5385(2) 0.15793(18) 0.0338(9) Uani d . . . 1 . .
H H43 0.4852 0.4765 0.1485 0.041 Uiso calc U . R 1 . .
C C44 0.6736(3) 0.5656(2) 0.20811(17) 0.0269(8) Uani d . . . 1 . .
H H44 0.6918 0.522 0.2332 0.032 Uiso calc U . R 1 . .
C C46 -0.2498(3) 0.0845(2) 0.12322(18) 0.0280(8) Uani d . . . 1 . .
C C47 -0.3889(3) 0.0581(2) 0.10172(17) 0.0318(9) Uani d . . . 1 . .
H H47 -0.4272 0.1042 0.1063 0.038 Uiso calc U . R 1 . .
C C48 -0.4730(3) -0.0352(2) 0.07345(18) 0.0343(9) Uani d . . . 1 . .
H H48 -0.5686 -0.0529 0.0594 0.041 Uiso calc U . R 1 . .
C C49 -0.4184(3) -0.1027(2) 0.06558(19) 0.0359(9) Uani d . . . 1 . .
H H49 -0.4759 -0.1666 0.0457 0.043 Uiso calc U . R 1 . .
C C50 -0.2789(3) -0.0762(2) 0.08700(19) 0.0366(10) Uani d . . . 1 . .
H H50 -0.2408 -0.1222 0.082 0.044 Uiso calc U . R 1 . .
C C51 -0.1944(3) 0.0167(2) 0.11567(18) 0.0331(9) Uani d . . . 1 . .
H H51 -0.0988 0.0343 0.1302 0.04 Uiso calc U . R 1 . .
C C52 -0.1957(3) 0.2420(2) 0.10622(18) 0.0248(8) Uani d . . . 1 . .
C C53 -0.2023(3) 0.2234(3) 0.03853(19) 0.0357(9) Uani d . . . 1 . .
H H53 -0.1879 0.1699 0.0198 0.043 Uiso calc U . R 1 . .
C C54 -0.2299(3) 0.2825(3) -0.0022(2) 0.0459(11) Uani d . . . 1 . .
H H54 -0.2358 0.2688 -0.049 0.055 Uiso calc U . R 1 . .
C C55 -0.2489(4) 0.3611(3) 0.0247(2) 0.0494(12) Uani d . . . 1 . .
H H55 -0.2657 0.4024 -0.003 0.059 Uiso calc U . R 1 . .
C C56 -0.2433(3) 0.3793(3) 0.0926(2) 0.0421(11) Uani d . . . 1 . .
H H56 -0.2565 0.4331 0.1116 0.05 Uiso calc U . R 1 . .
C C57 -0.2185(3) 0.3194(2) 0.1327(2) 0.0319(9) Uani d . . . 1 . .
H H57 -0.217 0.3313 0.179 0.038 Uiso calc U . R 1 . .
C C58 -0.0432(3) 0.2143(2) 0.20176(17) 0.0243(8) Uani d . . . 1 . .
C C59 -0.0254(3) 0.1680(2) 0.25387(17) 0.0284(8) Uani d . . . 1 . .
H H59 -0.0987 0.1148 0.2549 0.034 Uiso calc U . R 1 . .
C C60 0.0985(3) 0.1986(2) 0.30451(17) 0.0262(8) Uani d . . . 1 . .
H H60 0.1087 0.1653 0.3394 0.031 Uiso calc U . R 1 . .
C C61 0.2086(3) 0.2770(2) 0.30564(17) 0.0236(8) Uani d . . . 1 . .
C C62 0.1887(3) 0.3240(2) 0.25393(17) 0.0257(8) Uani d . . . 1 . .
H H62 0.2613 0.378 0.2533 0.031 Uiso calc U . R 1 . .
C C63 0.0652(3) 0.2938(2) 0.20319(17) 0.0253(8) Uani d . . . 1 . .
H H63 0.0542 0.3279 0.1689 0.03 Uiso calc U . R 1 . .
C C64 0.3420(3) 0.3003(2) 0.35797(17) 0.0231(8) Uani d . . . 1 . .
C C65 0.4440(3) 0.3939(2) 0.38735(17) 0.0238(8) Uani d . . . 1 . .
C C66 0.5857(3) 0.3322(2) 0.44986(16) 0.0212(7) Uani d . . . 1 . .
C C67 0.7101(3) 0.3449(2) 0.49584(16) 0.0262(8) Uani d . . . 1 . .
H H67 0.7775 0.4062 0.5153 0.031 Uiso calc U . R 1 . .
C C68 0.7343(3) 0.2691(2) 0.51253(17) 0.0282(8) Uani d . . . 1 . .
H H68 0.8181 0.2779 0.5445 0.034 Uiso calc U . R 1 . .
C C69 0.6365(3) 0.1775(2) 0.48301(18) 0.0318(9) Uani d . . . 1 . .
H H69 0.6558 0.1252 0.4943 0.038 Uiso calc U . R 1 . .
C C70 0.5140(3) 0.1638(2) 0.43811(17) 0.0291(8) Uani d . . . 1 . .
H H70 0.448 0.102 0.4185 0.035 Uiso calc U . R 1 . .
C C71 0.4860(3) 0.2410(2) 0.42121(16) 0.0231(8) Uani d . . . 1 . .
C C72 0.4281(3) 0.4788(2) 0.36745(16) 0.0223(8) Uani d . . . 1 . .
C C73 0.5248(3) 0.5354(2) 0.34227(17) 0.0277(8) Uani d . . . 1 . .
H H73 0.6049 0.524 0.3438 0.033 Uiso calc U . R 1 . .
C C74 0.5050(3) 0.6081(2) 0.31516(17) 0.0266(8) Uani d . . . 1 . .
H H74 0.571 0.6461 0.2978 0.032 Uiso calc U . R 1 . .
C C75 0.3884(3) 0.6255(2) 0.31328(17) 0.0237(8) Uani d . . . 1 . .
C C76 0.2987(3) 0.5744(2) 0.34355(17) 0.0263(8) Uani d . . . 1 . .
H H76 0.2229 0.5898 0.3459 0.032 Uiso calc U . R 1 . .
C C77 0.3175(3) 0.5015(2) 0.37040(17) 0.0263(8) Uani d . . . 1 . .
H H77 0.2548 0.4668 0.3909 0.032 Uiso calc U . R 1 . .
C C78 0.2506(3) 0.6561(2) 0.21494(17) 0.0255(8) Uani d . . . 1 . .
C C79 0.1802(3) 0.7110(2) 0.19034(18) 0.0293(9) Uani d . . . 1 . .
H H79 0.2077 0.7741 0.2142 0.035 Uiso calc U . R 1 . .
C C80 0.0699(3) 0.6738(3) 0.13103(18) 0.0335(9) Uani d . . . 1 . .
H H80 0.0221 0.7115 0.115 0.04 Uiso calc U . R 1 . .
C C81 0.0297(4) 0.5828(2) 0.09549(19) 0.0357(9) Uani d . . . 1 . .
H H81 -0.0458 0.5577 0.0551 0.043 Uiso calc U . R 1 . .
C C82 0.0995(3) 0.5282(2) 0.11881(18) 0.0321(9) Uani d . . . 1 . .
H H82 0.0723 0.4655 0.0942 0.039 Uiso calc U . R 1 . .
C C83 0.2092(3) 0.5644(2) 0.17801(18) 0.0289(8) Uani d . . . 1 . .
H H83 0.2567 0.5262 0.1935 0.035 Uiso calc U . R 1 . .
C C84 0.4539(3) 0.7852(2) 0.29714(19) 0.0298(9) Uani d . . . 1 . .
C C85 0.4973(3) 0.8328(2) 0.24960(19) 0.0347(9) Uani d . . . 1 . .
H H85 0.4613 0.8031 0.2024 0.042 Uiso calc U . R 1 . .
C C86 0.5926(4) 0.9233(2) 0.2712(2) 0.0453(11) Uani d . . . 1 . .
H H86 0.6207 0.9563 0.2386 0.054 Uiso calc U . R 1 . .
C C87 0.6476(4) 0.9662(3) 0.3399(2) 0.0569(13) Uani d . . . 1 . .
H H87 0.7141 1.0283 0.3546 0.068 Uiso calc U . R 1 . .
C C88 0.6056(4) 0.9188(3) 0.3870(2) 0.0459(11) Uani d . . . 1 . .
H H88 0.6432 0.9485 0.4342 0.055 Uiso calc U . R 1 . .
C C89 0.5098(3) 0.8287(2) 0.36644(19) 0.0334(9) Uani d . . . 1 . .
H H89 0.4819 0.7962 0.3993 0.04 Uiso calc U . R 1 . .
N N1 0.3323(3) 0.17864(18) 0.15898(14) 0.0255(7) Uani d . . . 1 . .
N N2 0.8595(3) 0.21720(18) 0.39132(13) 0.0240(7) Uani d . . . 1 . .
N N3 1.0713(2) 0.39427(17) 0.43218(13) 0.0222(6) Uani d . . . 1 . .
N N4 0.8964(3) 0.68415(17) 0.27497(14) 0.0254(7) Uani d . . . 1 . .
N N5 -0.1670(3) 0.18161(18) 0.14842(14) 0.0299(7) Uani d . . . 1 . .
N N6 0.3645(3) 0.22644(18) 0.37520(13) 0.0245(7) Uani d . . . 1 . .
N N7 0.5627(3) 0.40854(18) 0.43185(13) 0.0246(7) Uani d . . . 1 . .
N N8 0.3569(3) 0.69203(18) 0.27744(14) 0.0283(7) Uani d . . . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C2 . . 119.6(3)
C6 C1 N1 . . 120.2(3)
C2 C1 N1 . . 120.2(3)
C1 C2 C3 . . 119.9(3)
C1 C2 H2 . . 120.1
C3 C2 H2 . . 120.1
C4 C3 C2 . . 120.1(3)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C3 C4 C5 . . 119.9(3)
C3 C4 H4 . . 120.1
C5 C4 H4 . . 120.1
C6 C5 C4 . . 120.6(4)
C6 C5 H5 . . 119.7
C4 C5 H5 . . 119.7
C5 C6 C1 . . 120.0(3)
C5 C6 H6 . . 120.0
C1 C6 H6 . . 120.0
C12 C7 C8 . . 119.1(3)
C12 C7 N1 . . 119.9(3)
C8 C7 N1 . . 120.9(3)
C9 C8 C7 . . 119.7(3)
C9 C8 H8 . . 120.2
C7 C8 H8 . . 120.2
C10 C9 C8 . . 121.3(3)
C10 C9 H9 . . 119.3
C8 C9 H9 . . 119.3
C11 C10 C9 . . 118.8(3)
C11 C10 H10 . . 120.6
C9 C10 H10 . . 120.6
C10 C11 C12 . . 120.7(3)
C10 C11 H11 . . 119.6
C12 C11 H11 . . 119.6
C7 C12 C11 . . 120.3(3)
C7 C12 H12 . . 119.8
C11 C12 H12 . . 119.8
C14 C13 C18 . . 118.1(3)
C14 C13 N1 . . 120.7(3)
C18 C13 N1 . . 121.2(3)
C15 C14 C13 . . 120.6(3)
C15 C14 H14 . . 119.7
C13 C14 H14 . . 119.7
C14 C15 C16 . . 122.0(3)
C14 C15 H15 . . 119.0
C16 C15 H15 . . 119.0
C15 C16 C17 . . 117.1(3)
C15 C16 C19 . . 117.2(3)
C17 C16 C19 . . 125.6(3)
C18 C17 C16 . . 121.6(3)
C18 C17 H17 . . 119.2
C16 C17 H17 . . 119.2
C17 C18 C13 . . 120.6(3)
C17 C18 H18 . . 119.7
C13 C18 H18 . . 119.7
N2 C19 C20 . . 120.6(3)
N2 C19 C16 . . 115.3(3)
C20 C19 C16 . . 124.1(3)
N3 C20 C19 . . 121.5(3)
N3 C20 C27 . . 114.8(3)
C19 C20 C27 . . 123.7(3)
N3 C21 C22 . . 119.0(3)
N3 C21 C26 . . 120.3(3)
C22 C21 C26 . . 120.7(3)
C23 C22 C21 . . 119.3(3)
C23 C22 H22 . . 120.4
C21 C22 H22 . . 120.4
C22 C23 C24 . . 120.1(3)
C22 C23 H23 . . 119.9
C24 C23 H23 . . 119.9
C25 C24 C23 . . 121.3(3)
C25 C24 H24 . . 119.3
C23 C24 H24 . . 119.3
C24 C25 C26 . . 119.6(3)
C24 C25 H25 . . 120.2
C26 C25 H25 . . 120.2
N2 C26 C21 . . 121.3(3)
N2 C26 C25 . . 119.8(3)
C21 C26 C25 . . 118.9(3)
C28 C27 C32 . . 118.5(3)
C28 C27 C20 . . 121.0(3)
C32 C27 C20 . . 120.4(3)
C29 C28 C27 . . 121.0(3)
C29 C28 H28 . . 119.5
C27 C28 H28 . . 119.5
C28 C29 C30 . . 119.9(3)
C28 C29 H29 . . 120.1
C30 C29 H29 . . 120.1
C29 C30 C31 . . 119.5(3)
C29 C30 N4 . . 120.2(3)
C31 C30 N4 . . 120.2(3)
C32 C31 C30 . . 119.9(3)
C32 C31 H31 . . 120.1
C30 C31 H31 . . 120.1
C31 C32 C27 . . 121.0(3)
C31 C32 H32 . . 119.5
C27 C32 H32 . . 119.5
C34 C33 C38 . . 118.6(3)
C34 C33 N4 . . 123.4(3)
C38 C33 N4 . . 118.0(3)
C33 C34 C35 . . 120.6(3)
C33 C34 H34 . . 119.7
C35 C34 H34 . . 119.7
C36 C35 C34 . . 120.4(3)
C36 C35 H35 . . 119.8
C34 C35 H35 . . 119.8
C37 C36 C35 . . 119.8(3)
C37 C36 H36 . . 120.1
C35 C36 H36 . . 120.1
C36 C37 C38 . . 120.1(3)
C36 C37 H37 . . 120.0
C38 C37 H37 . . 120.0
C37 C38 C33 . . 120.4(3)
C37 C38 H38 . . 119.8
C33 C38 H38 . . 119.8
C40 C39 C44 . . 117.9(3)
C40 C39 N4 . . 121.3(3)
C44 C39 N4 . . 120.8(3)
C41 C40 C39 . . 120.6(3)
C41 C40 H40 . . 119.7
C39 C40 H40 . . 119.7
C42 C41 C40 . . 120.6(4)
C42 C41 H41 . . 119.7
C40 C41 H41 . . 119.7
C43 C42 C41 . . 119.6(4)
C43 C42 H42 . . 120.2
C41 C42 H42 . . 120.2
C42 C43 C44 . . 120.3(3)
C42 C43 H43 . . 119.9
C44 C43 H43 . . 119.9
C43 C44 C39 . . 121.0(3)
C43 C44 H44 . . 119.5
C39 C44 H44 . . 119.5
C47 C46 C51 . . 119.5(3)
C47 C46 N5 . . 118.5(3)
C51 C46 N5 . . 121.9(3)
C46 C47 C48 . . 120.3(3)
C46 C47 H47 . . 119.8
C48 C47 H47 . . 119.8
C49 C48 C47 . . 120.3(3)
C49 C48 H48 . . 119.8
C47 C48 H48 . . 119.8
C48 C49 C50 . . 119.2(3)
C48 C49 H49 . . 120.4
C50 C49 H49 . . 120.4
C51 C50 C49 . . 120.7(3)
C51 C50 H50 . . 119.6
C49 C50 H50 . . 119.6
C50 C51 C46 . . 119.8(3)
C50 C51 H51 . . 120.1
C46 C51 H51 . . 120.1
C53 C52 C57 . . 119.4(3)
C53 C52 N5 . . 120.4(3)
C57 C52 N5 . . 120.2(3)
C52 C53 C54 . . 120.1(4)
C52 C53 H53 . . 120.0
C54 C53 H53 . . 120.0
C55 C54 C53 . . 120.5(4)
C55 C54 H54 . . 119.8
C53 C54 H54 . . 119.8
C54 C55 C56 . . 119.3(4)
C54 C55 H55 . . 120.4
C56 C55 H55 . . 120.4
C57 C56 C55 . . 120.1(4)
C57 C56 H56 . . 119.9
C55 C56 H56 . . 119.9
C56 C57 C52 . . 120.5(4)
C56 C57 H57 . . 119.7
C52 C57 H57 . . 119.7
C59 C58 C63 . . 118.1(3)
C59 C58 N5 . . 121.1(3)
C63 C58 N5 . . 120.8(3)
C58 C59 C60 . . 120.6(3)
C58 C59 H59 . . 119.7
C60 C59 H59 . . 119.7
C59 C60 C61 . . 121.8(3)
C59 C60 H60 . . 119.1
C61 C60 H60 . . 119.1
C62 C61 C60 . . 117.1(3)
C62 C61 C64 . . 124.1(3)
C60 C61 C64 . . 118.6(3)
C63 C62 C61 . . 121.4(3)
C63 C62 H62 . . 119.3
C61 C62 H62 . . 119.3
C62 C63 C58 . . 121.0(3)
C62 C63 H63 . . 119.5
C58 C63 H63 . . 119.5
N6 C64 C65 . . 120.6(3)
N6 C64 C61 . . 114.4(3)
C65 C64 C61 . . 124.9(3)
N7 C65 C64 . . 121.2(3)
N7 C65 C72 . . 115.4(3)
C64 C65 C72 . . 123.2(3)
N7 C66 C67 . . 119.6(3)
N7 C66 C71 . . 120.5(3)
C67 C66 C71 . . 119.9(3)
C68 C67 C66 . . 119.6(3)
C68 C67 H67 . . 120.2
C66 C67 H67 . . 120.2
C67 C68 C69 . . 120.9(3)
C67 C68 H68 . . 119.6
C69 C68 H68 . . 119.6
C70 C69 C68 . . 120.2(3)
C70 C69 H69 . . 119.9
C68 C69 H69 . . 119.9
C69 C70 C71 . . 119.8(3)
C69 C70 H70 . . 120.1
C71 C70 H70 . . 120.1
N6 C71 C70 . . 119.4(3)
N6 C71 C66 . . 121.1(3)
C70 C71 C66 . . 119.5(3)
C77 C72 C73 . . 118.9(3)
C77 C72 C65 . . 122.2(3)
C73 C72 C65 . . 118.8(3)
C74 C73 C72 . . 120.6(3)
C74 C73 H73 . . 119.7
C72 C73 H73 . . 119.7
C73 C74 C75 . . 119.9(3)
C73 C74 H74 . . 120.1
C75 C74 H74 . . 120.1
C76 C75 C74 . . 119.2(3)
C76 C75 N8 . . 119.8(3)
C74 C75 N8 . . 120.8(3)
C77 C76 C75 . . 121.0(3)
C77 C76 H76 . . 119.5
C75 C76 H76 . . 119.5
C76 C77 C72 . . 119.9(3)
C76 C77 H77 . . 120.0
C72 C77 H77 . . 120.0
C83 C78 C79 . . 118.3(3)
C83 C78 N8 . . 121.3(3)
C79 C78 N8 . . 120.3(3)
C80 C79 C78 . . 120.4(3)
C80 C79 H79 . . 119.8
C78 C79 H79 . . 119.8
C81 C80 C79 . . 120.5(3)
C81 C80 H80 . . 119.7
C79 C80 H80 . . 119.7
C80 C81 C82 . . 119.7(3)
C80 C81 H81 . . 120.2
C82 C81 H81 . . 120.2
C81 C82 C83 . . 120.3(3)
C81 C82 H82 . . 119.8
C83 C82 H82 . . 119.8
C82 C83 C78 . . 120.7(3)
C82 C83 H83 . . 119.6
C78 C83 H83 . . 119.6
C85 C84 C89 . . 119.6(3)
C85 C84 N8 . . 121.9(3)
C89 C84 N8 . . 118.5(3)
C86 C85 C84 . . 119.9(4)
C86 C85 H85 . . 120.1
C84 C85 H85 . . 120.1
C85 C86 C87 . . 120.3(4)
C85 C86 H86 . . 119.8
C87 C86 H86 . . 119.8
C88 C87 C86 . . 119.9(4)
C88 C87 H87 . . 120.1
C86 C87 H87 . . 120.1
C89 C88 C87 . . 120.7(4)
C89 C88 H88 . . 119.7
C87 C88 H88 . . 119.7
C88 C89 C84 . . 119.7(4)
C88 C89 H89 . . 120.2
C84 C89 H89 . . 120.2
C13 N1 C1 . . 119.2(3)
C13 N1 C7 . . 120.6(3)
C1 N1 C7 . . 119.0(3)
C19 N2 C26 . . 118.0(3)
C20 N3 C21 . . 118.1(3)
C39 N4 C33 . . 122.3(3)
C39 N4 C30 . . 116.7(3)
C33 N4 C30 . . 118.1(3)
C58 N5 C52 . . 119.7(3)
C58 N5 C46 . . 122.3(3)
C52 N5 C46 . . 116.1(3)
C64 N6 C71 . . 118.4(3)
C65 N7 C66 . . 118.1(3)
C78 N8 C84 . . 123.1(3)
C78 N8 C75 . . 117.3(3)
C84 N8 C75 . . 117.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.387(4)
C1 C2 . 1.394(4)
C1 N1 . 1.421(4)
C2 C3 . 1.394(4)
C2 H2 . 0.95
C3 C4 . 1.377(5)
C3 H3 . 0.95
C4 C5 . 1.385(5)
C4 H4 . 0.95
C5 C6 . 1.380(4)
C5 H5 . 0.95
C6 H6 . 0.95
C7 C12 . 1.383(4)
C7 C8 . 1.391(4)
C7 N1 . 1.429(4)
C8 C9 . 1.382(5)
C8 H8 . 0.95
C9 C10 . 1.380(5)
C9 H9 . 0.95
C10 C11 . 1.376(5)
C10 H10 . 0.95
C11 C12 . 1.388(4)
C11 H11 . 0.95
C12 H12 . 0.95
C13 C14 . 1.388(4)
C13 C18 . 1.398(4)
C13 N1 . 1.417(4)
C14 C15 . 1.380(4)
C14 H14 . 0.95
C15 C16 . 1.391(4)
C15 H15 . 0.95
C16 C17 . 1.391(4)
C16 C19 . 1.502(4)
C17 C18 . 1.384(4)
C17 H17 . 0.95
C18 H18 . 0.95
C19 N2 . 1.328(4)
C19 C20 . 1.439(4)
C20 N3 . 1.320(4)
C20 C27 . 1.482(4)
C21 N3 . 1.370(4)
C21 C22 . 1.401(4)
C21 C26 . 1.403(4)
C22 C23 . 1.377(4)
C22 H22 . 0.95
C23 C24 . 1.402(5)
C23 H23 . 0.95
C24 C25 . 1.365(4)
C24 H24 . 0.95
C25 C26 . 1.413(4)
C25 H25 . 0.95
C26 N2 . 1.366(4)
C27 C28 . 1.389(4)
C27 C32 . 1.396(4)
C28 C29 . 1.388(4)
C28 H28 . 0.95
C29 C30 . 1.393(4)
C29 H29 . 0.95
C30 C31 . 1.395(4)
C30 N4 . 1.426(4)
C31 C32 . 1.383(4)
C31 H31 . 0.95
C32 H32 . 0.95
C33 C34 . 1.383(4)
C33 C38 . 1.405(4)
C33 N4 . 1.421(4)
C34 C35 . 1.384(4)
C34 H34 . 0.95
C35 C36 . 1.384(5)
C35 H35 . 0.95
C36 C37 . 1.379(5)
C36 H36 . 0.95
C37 C38 . 1.388(4)
C37 H37 . 0.95
C38 H38 . 0.95
C39 C40 . 1.388(4)
C39 C44 . 1.400(4)
C39 N4 . 1.413(4)
C40 C41 . 1.388(5)
C40 H40 . 0.95
C41 C42 . 1.382(5)
C41 H41 . 0.95
C42 C43 . 1.370(5)
C42 H42 . 0.95
C43 C44 . 1.384(4)
C43 H43 . 0.95
C44 H44 . 0.95
C46 C47 . 1.381(4)
C46 C51 . 1.391(4)
C46 N5 . 1.424(4)
C47 C48 . 1.386(4)
C47 H47 . 0.95
C48 C49 . 1.383(5)
C48 H48 . 0.95
C49 C50 . 1.384(5)
C49 H49 . 0.95
C50 C51 . 1.383(4)
C50 H50 . 0.95
C51 H51 . 0.95
C52 C53 . 1.377(5)
C52 C57 . 1.382(4)
C52 N5 . 1.423(4)
C53 C54 . 1.383(5)
C53 H53 . 0.95
C54 C55 . 1.379(5)
C54 H54 . 0.95
C55 C56 . 1.383(6)
C55 H55 . 0.95
C56 C57 . 1.377(5)
C56 H56 . 0.95
C57 H57 . 0.95
C58 C59 . 1.387(4)
C58 C63 . 1.393(4)
C58 N5 . 1.411(4)
C59 C60 . 1.387(4)
C59 H59 . 0.95
C60 C61 . 1.396(4)
C60 H60 . 0.95
C61 C62 . 1.390(4)
C61 C64 . 1.492(4)
C62 C63 . 1.386(4)
C62 H62 . 0.95
C63 H63 . 0.95
C64 N6 . 1.327(4)
C64 C65 . 1.447(4)
C65 N7 . 1.329(4)
C65 C72 . 1.484(4)
C66 N7 . 1.373(4)
C66 C67 . 1.397(4)
C66 C71 . 1.411(4)
C67 C68 . 1.360(4)
C67 H67 . 0.95
C68 C69 . 1.409(4)
C68 H68 . 0.95
C69 C70 . 1.368(4)
C69 H69 . 0.95
C70 C71 . 1.400(4)
C70 H70 . 0.95
C71 N6 . 1.365(4)
C72 C77 . 1.388(4)
C72 C73 . 1.396(4)
C73 C74 . 1.382(4)
C73 H73 . 0.95
C74 C75 . 1.389(4)
C74 H74 . 0.95
C75 C76 . 1.383(4)
C75 N8 . 1.434(4)
C76 C77 . 1.380(4)
C76 H76 . 0.95
C77 H77 . 0.95
C78 C83 . 1.393(4)
C78 C79 . 1.396(4)
C78 N8 . 1.413(4)
C79 C80 . 1.392(5)
C79 H79 . 0.95
C80 C81 . 1.375(5)
C80 H80 . 0.95
C81 C82 . 1.380(5)
C81 H81 . 0.95
C82 C83 . 1.387(4)
C82 H82 . 0.95
C83 H83 . 0.95
C84 C85 . 1.392(5)
C84 C89 . 1.394(5)
C84 N8 . 1.415(4)
C85 C86 . 1.379(5)
C85 H85 . 0.95
C86 C87 . 1.382(5)
C86 H86 . 0.95
C87 C88 . 1.378(5)
C87 H87 . 0.95
C88 C89 . 1.376(5)
C88 H88 . 0.95
C89 H89 . 0.95
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338980
