#------------------------------------------------------------------------------
#$Date: 2023-09-25 11:25:22 +0300 (Mon, 25 Sep 2023) $
#$Revision: 286498 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107529.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_8107529
loop_
_publ_author_name
'Dey, Lucky'
'Rabi, Saswata'
'Palit, Debashis'
'Rahman, Ismail M. M.'
'Tiekink, Edward R. T.'
'Roy, Tapashi Ghosh'
_publ_section_title
;
 Redetermination of the crystal structure of
 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine,
 C32H28N4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              679
_journal_page_last               682
_journal_paper_doi               10.1515/ncrs-2023-0146
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C32 H28 N4'
_chemical_formula_sum            'C32 H28 N4'
_chemical_formula_weight         468.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 113.598(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7218(4)
_cell_length_b                   20.7769(5)
_cell_length_c                   14.9434(3)
_cell_measurement_reflns_used    14297
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      75.6940
_cell_measurement_theta_min      3.4520
_cell_volume                     5042.1(2)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            61154
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.454
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         8987
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0519
_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)+(0.0798P)²+1.5841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7152
_reflns_number_total             8987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0146_suppl_001.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107529
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63057(11) 0.21429(9) 0.97094(12) 0.0515(4) Uani 1 1 d D . . . .
H1N H 0.5858(10) 0.2334(11) 0.9335(15) 0.062 Uiso 1 1 d D U . . .
N2 N 0.53963(10) 0.31781(9) 0.88668(12) 0.0517(4) Uani 1 1 d . . . . .
N3 N 0.45995(11) 0.25619(9) 0.71711(12) 0.0526(4) Uani 1 1 d D . . . .
H3N H 0.4877(14) 0.2318(10) 0.7655(13) 0.063 Uiso 1 1 d D U . . .
N4 N 0.55001(10) 0.15062(8) 0.79833(11) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.69313(13) 0.25547(11) 1.01063(14) 0.0521(5) Uani 1 1 d . . . . .
C2 C 0.68113(14) 0.32139(11) 0.99288(15) 0.0555(5) Uani 1 1 d . . . . .
H2 H 0.725192 0.348257 1.027389 0.067 Uiso 1 1 calc R U . . .
C3 C 0.60834(13) 0.35110(10) 0.92742(14) 0.0503(5) Uani 1 1 d . . . . .
C4 C 0.46386(12) 0.34405(10) 0.82207(14) 0.0459(4) Uani 1 1 d . . . . .
C5 C 0.42139(12) 0.31133(10) 0.73432(14) 0.0463(4) Uani 1 1 d . . . . .
C6 C 0.34326(13) 0.33192(12) 0.67237(16) 0.0587(5) Uani 1 1 d . . . . .
H6 H 0.314576 0.309940 0.614396 0.070 Uiso 1 1 calc R U . . .
C7 C 0.30793(14) 0.38477(12) 0.69627(18) 0.0614(6) Uani 1 1 d . . . . .
H7 H 0.255718 0.398349 0.654253 0.074 Uiso 1 1 calc R U . . .
C8 C 0.34964(14) 0.41736(11) 0.78193(18) 0.0592(6) Uani 1 1 d . . . . .
H8 H 0.325959 0.453294 0.797427 0.071 Uiso 1 1 calc R U . . .
C9 C 0.42695(14) 0.39674(10) 0.84525(17) 0.0543(5) Uani 1 1 d . . . . .
H9 H 0.454413 0.418393 0.903854 0.065 Uiso 1 1 calc R U . . .
C10 C 0.45917(12) 0.23380(10) 0.63292(14) 0.0447(4) Uani 1 1 d . . . . .
C11 C 0.49909(13) 0.17745(10) 0.63006(14) 0.0495(5) Uani 1 1 d . . . . .
H11 H 0.494599 0.163851 0.568840 0.059 Uiso 1 1 calc R U . . .
C12 C 0.54629(12) 0.13794(10) 0.71038(14) 0.0473(4) Uani 1 1 d . . . . .
C13 C 0.59362(11) 0.11363(10) 0.88233(14) 0.0465(4) Uani 1 1 d . . . . .
C14 C 0.63390(12) 0.14656(11) 0.97152(14) 0.0488(5) Uani 1 1 d . . . . .
C15 C 0.67159(15) 0.11160(13) 1.05728(16) 0.0639(6) Uani 1 1 d . . . . .
H15 H 0.696281 0.133264 1.116396 0.077 Uiso 1 1 calc R U . . .
C16 C 0.67291(17) 0.04492(14) 1.05598(19) 0.0736(7) Uani 1 1 d . . . . .
H16 H 0.699779 0.022136 1.113648 0.088 Uiso 1 1 calc R U . . .
C17 C 0.63464(17) 0.01270(13) 0.9697(2) 0.0719(7) Uani 1 1 d . . . . .
H17 H 0.635836 -0.032042 0.968731 0.086 Uiso 1 1 calc R U . . .
C18 C 0.59406(14) 0.04654(11) 0.88376(17) 0.0594(5) Uani 1 1 d . . . . .
H18 H 0.566599 0.024057 0.825942 0.071 Uiso 1 1 calc R U . . .
C19 C 0.77959(14) 0.23247(13) 1.06839(17) 0.0651(6) Uani 1 1 d . . . . .
H19A H 0.815677 0.268865 1.090823 0.098 Uiso 0.5 1 calc R U P . .
H19B H 0.781090 0.207909 1.123496 0.098 Uiso 0.5 1 calc R U P . .
H19C H 0.797174 0.205952 1.027726 0.098 Uiso 0.5 1 calc R U P . .
H19D H 0.780284 0.186286 1.070540 0.098 Uiso 0.5 1 calc R U P . .
H19E H 0.814870 0.247242 1.037867 0.098 Uiso 0.5 1 calc R U P . .
H19F H 0.798787 0.249199 1.133637 0.098 Uiso 0.5 1 calc R U P . .
C20 C 0.61502(13) 0.41936(11) 0.89907(15) 0.0505(5) Uani 1 1 d . . . . .
C21 C 0.60038(14) 0.43395(13) 0.80336(16) 0.0603(6) Uani 1 1 d . . . . .
H21 H 0.585579 0.401381 0.756791 0.072 Uiso 1 1 calc R U . . .
C22 C 0.60753(16) 0.49659(15) 0.7760(2) 0.0728(7) Uani 1 1 d . . . . .
H22 H 0.598641 0.505655 0.711624 0.087 Uiso 1 1 calc R U . . .
C23 C 0.62777(15) 0.54555(14) 0.8439(2) 0.0727(7) Uani 1 1 d . . . . .
H23 H 0.631307 0.587755 0.825198 0.087 Uiso 1 1 calc R U . . .
C24 C 0.64254(17) 0.53162(13) 0.9384(2) 0.0733(7) Uani 1 1 d . . . . .
H24 H 0.655760 0.564557 0.984328 0.088 Uiso 1 1 calc R U . . .
C25 C 0.63804(16) 0.46908(12) 0.96673(17) 0.0646(6) Uani 1 1 d . . . . .
H25 H 0.650630 0.460077 1.032114 0.078 Uiso 1 1 calc R U . . .
C26 C 0.42112(13) 0.27138(10) 0.54026(14) 0.0484(5) Uani 1 1 d . . . . .
C27 C 0.35835(16) 0.24507(13) 0.46017(17) 0.0683(6) Uani 1 1 d . . . . .
H27 H 0.337628 0.204657 0.464771 0.082 Uiso 1 1 calc R U . . .
C28 C 0.3262(2) 0.27863(18) 0.3731(2) 0.0947(10) Uani 1 1 d . . . . .
H28 H 0.283336 0.260832 0.319670 0.114 Uiso 1 1 calc R U . . .
C29 C 0.3567(2) 0.33777(18) 0.3647(2) 0.0915(10) Uani 1 1 d . . . . .
H29 H 0.334418 0.360313 0.306089 0.110 Uiso 1 1 calc R U . . .
C30 C 0.4202(2) 0.36344(14) 0.4432(2) 0.0793(8) Uani 1 1 d . . . . .
H30 H 0.442011 0.403191 0.437417 0.095 Uiso 1 1 calc R U . . .
C31 C 0.45229(16) 0.33075(12) 0.53086(19) 0.0634(6) Uani 1 1 d . . . . .
H31 H 0.495143 0.348807 0.583974 0.076 Uiso 1 1 calc R U . . .
C32 C 0.59283(17) 0.08498(13) 0.68721(19) 0.0698(7) Uani 1 1 d . . . . .
H32A H 0.580331 0.085081 0.618488 0.105 Uiso 0.5 1 calc R U P . .
H32B H 0.650852 0.091519 0.723044 0.105 Uiso 0.5 1 calc R U P . .
H32C H 0.577172 0.044361 0.705241 0.105 Uiso 0.5 1 calc R U P . .
H32D H 0.625239 0.062227 0.746027 0.105 Uiso 0.5 1 calc R U P . .
H32E H 0.554718 0.055788 0.641471 0.105 Uiso 0.5 1 calc R U P . .
H32F H 0.628397 0.102946 0.659275 0.105 Uiso 0.5 1 calc R U P . .
N5 N 0.85358(11) 0.22182(8) 0.83225(13) 0.0510(4) Uani 1 1 d D . . . .
H5N H 0.8979(10) 0.2418(11) 0.8388(17) 0.061 Uiso 1 1 d D U . . .
N6 N 0.94547(10) 0.32469(8) 0.83876(11) 0.0448(4) Uani 1 1 d . . . . .
N7 N 1.01554(11) 0.26686(9) 0.73130(12) 0.0506(4) Uani 1 1 d D . . . .
H7N H 0.9880(13) 0.2453(10) 0.7569(16) 0.061 Uiso 1 1 d D U . . .
N8 N 0.93210(10) 0.15837(8) 0.73492(12) 0.0472(4) Uani 1 1 d . . . . .
C33 C 0.79168(13) 0.26388(11) 0.81390(14) 0.0497(5) Uani 1 1 d . . . . .
C34 C 0.80484(12) 0.32959(10) 0.81409(14) 0.0459(4) Uani 1 1 d . . . . .
H34 H 0.761638 0.356465 0.810072 0.055 Uiso 1 1 calc R U . . .
C35 C 0.87906(11) 0.35946(10) 0.81993(12) 0.0418(4) Uani 1 1 d . . . . .
C36 C 1.02174(11) 0.34914(9) 0.84551(13) 0.0401(4) Uani 1 1 d . . . . .
C37 C 1.05892(11) 0.31840(9) 0.78982(13) 0.0420(4) Uani 1 1 d . . . . .
C38 C 1.13667(12) 0.33829(11) 0.79888(15) 0.0501(5) Uani 1 1 d . . . . .
H38 H 1.161355 0.318764 0.761440 0.060 Uiso 1 1 calc R U . . .
C39 C 1.17731(13) 0.38686(11) 0.86318(15) 0.0543(5) Uani 1 1 d . . . . .
H39 H 1.229049 0.400005 0.868318 0.065 Uiso 1 1 calc R U . . .
C40 C 1.14216(13) 0.41601(10) 0.91969(15) 0.0522(5) Uani 1 1 d . . . . .
H40 H 1.170388 0.448221 0.963535 0.063 Uiso 1 1 calc R U . . .
C41 C 1.06453(12) 0.39726(10) 0.91112(14) 0.0469(4) Uani 1 1 d . . . . .
H41 H 1.040814 0.416939 0.949458 0.056 Uiso 1 1 calc R U . . .
C42 C 1.01915(12) 0.24155(10) 0.65022(14) 0.0461(4) Uani 1 1 d . . . . .
C43 C 0.98189(14) 0.18351(10) 0.61373(15) 0.0513(5) Uani 1 1 d . . . . .
H43 H 0.986371 0.168880 0.557238 0.062 Uiso 1 1 calc R U . . .
C44 C 0.93749(13) 0.14359(10) 0.65261(15) 0.0484(5) Uani 1 1 d . . . . .
C45 C 0.89150(12) 0.12105(10) 0.78052(14) 0.0476(5) Uani 1 1 d . . . . .
C46 C 0.85081(13) 0.15404(10) 0.83057(15) 0.0503(5) Uani 1 1 d . . . . .
C47 C 0.81487(17) 0.11901(13) 0.88226(19) 0.0697(7) Uani 1 1 d . . . . .
H47 H 0.787946 0.140584 0.915489 0.084 Uiso 1 1 calc R U . . .
C48 C 0.81851(19) 0.05206(14) 0.8851(2) 0.0783(8) Uani 1 1 d . . . . .
H48 H 0.793666 0.029282 0.919594 0.094 Uiso 1 1 calc R U . . .
C49 C 0.85843(17) 0.01985(12) 0.8375(2) 0.0701(7) Uani 1 1 d . . . . .
H49 H 0.860548 -0.024882 0.839079 0.084 Uiso 1 1 calc R U . . .
C50 C 0.89547(14) 0.05356(11) 0.78708(17) 0.0599(6) Uani 1 1 d . . . . .
H50 H 0.923946 0.031159 0.756481 0.072 Uiso 1 1 calc R U . . .
C51 C 0.70504(15) 0.24006(13) 0.7823(2) 0.0664(6) Uani 1 1 d . . . . .
H51A H 0.667922 0.276015 0.765134 0.100 Uiso 1 1 calc R U . . .
H51B H 0.699751 0.216552 0.834778 0.100 Uiso 1 1 calc R U . . .
H51C H 0.691937 0.212340 0.726669 0.100 Uiso 1 1 calc R U . . .
C52 C 0.87404(12) 0.42957(10) 0.79436(13) 0.0439(4) Uani 1 1 d . . . . .
C53 C 0.90029(14) 0.45110(12) 0.72398(17) 0.0607(6) Uani 1 1 d . . . . .
H53 H 0.921874 0.422078 0.693061 0.073 Uiso 1 1 calc R U . . .
C54 C 0.89453(17) 0.51588(14) 0.6993(2) 0.0786(8) Uani 1 1 d . . . . .
H54 H 0.912919 0.529947 0.652475 0.094 Uiso 1 1 calc R U . . .
C55 C 0.86205(18) 0.55944(13) 0.7433(2) 0.0771(7) Uani 1 1 d . . . . .
H55 H 0.858818 0.602803 0.726703 0.093 Uiso 1 1 calc R U . . .
C56 C 0.83443(18) 0.53852(12) 0.81182(18) 0.0706(7) Uani 1 1 d . . . . .
H56 H 0.812592 0.567794 0.842117 0.085 Uiso 1 1 calc R U . . .
C57 C 0.83897(15) 0.47399(11) 0.83599(15) 0.0578(5) Uani 1 1 d . . . . .
H57 H 0.818240 0.460048 0.880828 0.069 Uiso 1 1 calc R U . . .
C58 C 1.05683(13) 0.27752(10) 0.59236(14) 0.0496(5) Uani 1 1 d . . . . .
C59 C 1.11143(15) 0.24678(13) 0.56110(17) 0.0635(6) Uani 1 1 d . . . . .
H59 H 1.127636 0.204675 0.580478 0.076 Uiso 1 1 calc R U . . .
C60 C 1.14202(18) 0.27870(18) 0.5009(2) 0.0813(9) Uani 1 1 d . . . . .
H60 H 1.178443 0.257886 0.479838 0.098 Uiso 1 1 calc R U . . .
C61 C 1.1186(2) 0.34059(19) 0.47263(19) 0.0916(10) Uani 1 1 d . . . . .
H61 H 1.139330 0.361902 0.432608 0.110 Uiso 1 1 calc R U . . .
C62 C 1.0648(2) 0.37138(16) 0.50287(19) 0.0831(9) Uani 1 1 d . . . . .
H62 H 1.048891 0.413458 0.482996 0.100 Uiso 1 1 calc R U . . .
C63 C 1.03398(16) 0.34053(12) 0.56257(16) 0.0636(6) Uani 1 1 d . . . . .
H63 H 0.997649 0.361973 0.583081 0.076 Uiso 1 1 calc R U . . .
C64 C 0.89527(18) 0.08669(12) 0.58934(19) 0.0705(7) Uani 1 1 d . . . . .
H64A H 0.908291 0.085711 0.532875 0.106 Uiso 0.5 1 calc R U P . .
H64B H 0.913944 0.047643 0.625927 0.106 Uiso 0.5 1 calc R U P . .
H64C H 0.836771 0.090570 0.569054 0.106 Uiso 0.5 1 calc R U P . .
H64D H 0.864380 0.063571 0.619029 0.106 Uiso 0.5 1 calc R U P . .
H64E H 0.858727 0.101640 0.525978 0.106 Uiso 0.5 1 calc R U P . .
H64F H 0.935900 0.058713 0.582850 0.106 Uiso 0.5 1 calc R U P . .
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'
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
C1 N1 C14 127.70(19) . .
C1 N1 H1N 112.1(17) . .
C14 N1 H1N 119.3(17) . .
C3 N2 C4 124.25(18) . .
C10 N3 C5 129.18(18) . .
C10 N3 H3N 112.0(17) . .
C5 N3 H3N 118.8(17) . .
C12 N4 C13 124.80(17) . .
N1 C1 C2 120.5(2) . .
N1 C1 C19 121.6(2) . .
C2 C1 C19 117.6(2) . .
C1 C2 C3 126.06(19) . .
C1 C2 H2 117.0 . .
C3 C2 H2 117.0 . .
N2 C3 C2 120.6(2) . .
N2 C3 C20 121.93(19) . .
C2 C3 C20 117.14(18) . .
C9 C4 C5 119.12(19) . .
C9 C4 N2 123.21(18) . .
C5 C4 N2 117.43(18) . .
C6 C5 C4 119.56(19) . .
C6 C5 N3 123.73(19) . .
C4 C5 N3 116.60(17) . .
C7 C6 C5 120.5(2) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C8 C7 C6 120.2(2) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C9 120.0(2) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C8 C9 C4 120.6(2) . .
C8 C9 H9 119.7 . .
C4 C9 H9 119.7 . .
N3 C10 C11 120.88(18) . .
N3 C10 C26 121.41(18) . .
C11 C10 C26 117.52(17) . .
C10 C11 C12 127.02(18) . .
C10 C11 H11 116.5 . .
C12 C11 H11 116.5 . .
N4 C12 C11 120.42(18) . .
N4 C12 C32 124.50(19) . .
C11 C12 C32 115.01(18) . .
C18 C13 N4 123.82(18) . .
C18 C13 C14 118.20(19) . .
N4 C13 C14 117.80(18) . .
C15 C14 N1 122.1(2) . .
C15 C14 C13 119.5(2) . .
N1 C14 C13 118.32(17) . .
C16 C15 C14 120.9(2) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C17 C16 C15 119.9(2) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C16 C17 C18 120.2(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C13 121.3(2) . .
C17 C18 H18 119.4 . .
C13 C18 H18 119.4 . .
C1 C19 H19A 109.5 . .
C1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
H19D C19 H19E 109.5 . .
H19D C19 H19F 109.5 . .
H19E C19 H19F 109.5 . .
C21 C20 C25 118.0(2) . .
C21 C20 C3 119.82(19) . .
C25 C20 C3 122.15(19) . .
C20 C21 C22 120.7(2) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C23 C22 C21 120.3(2) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C24 C23 C22 119.5(2) . .
C24 C23 H23 120.3 . .
C22 C23 H23 120.3 . .
C23 C24 C25 120.5(3) . .
C23 C24 H24 119.7 . .
C25 C24 H24 119.7 . .
C24 C25 C20 121.0(2) . .
C24 C25 H25 119.5 . .
C20 C25 H25 119.5 . .
C27 C26 C31 118.8(2) . .
C27 C26 C10 120.3(2) . .
C31 C26 C10 120.68(19) . .
C26 C27 C28 120.2(3) . .
C26 C27 H27 119.9 . .
C28 C27 H27 119.9 . .
C29 C28 C27 120.7(3) . .
C29 C28 H28 119.7 . .
C27 C28 H28 119.7 . .
C28 C29 C30 119.4(3) . .
C28 C29 H29 120.3 . .
C30 C29 H29 120.3 . .
C29 C30 C31 120.5(3) . .
C29 C30 H30 119.8 . .
C31 C30 H30 119.8 . .
C30 C31 C26 120.4(3) . .
C30 C31 H31 119.8 . .
C26 C31 H31 119.8 . .
C12 C32 H32A 109.5 . .
C12 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C12 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
H32D C32 H32E 109.5 . .
H32D C32 H32F 109.5 . .
H32E C32 H32F 109.5 . .
C33 N5 C46 128.85(18) . .
C33 N5 H5N 110.2(17) . .
C46 N5 H5N 120.5(17) . .
C35 N6 C36 124.70(17) . .
C42 N7 C37 130.42(17) . .
C42 N7 H7N 116.0(17) . .
C37 N7 H7N 112.9(17) . .
C44 N8 C45 124.80(17) . .
N5 C33 C34 121.21(18) . .
N5 C33 C51 120.0(2) . .
C34 C33 C51 118.5(2) . .
C33 C34 C35 125.45(19) . .
C33 C34 H34 117.3 . .
C35 C34 H34 117.3 . .
N6 C35 C34 120.01(18) . .
N6 C35 C52 123.11(17) . .
C34 C35 C52 116.63(17) . .
C41 C36 C37 119.40(17) . .
C41 C36 N6 123.05(17) . .
C37 C36 N6 117.23(16) . .
C38 C37 N7 124.19(18) . .
C38 C37 C36 119.21(18) . .
N7 C37 C36 116.53(16) . .
C39 C38 C37 120.32(19) . .
C39 C38 H38 119.8 . .
C37 C38 H38 119.8 . .
C40 C39 C38 120.75(19) . .
C40 C39 H39 119.6 . .
C38 C39 H39 119.6 . .
C39 C40 C41 119.78(19) . .
C39 C40 H40 120.1 . .
C41 C40 H40 120.1 . .
C40 C41 C36 120.50(19) . .
C40 C41 H41 119.8 . .
C36 C41 H41 119.8 . .
N7 C42 C43 120.69(18) . .
N7 C42 C58 121.40(18) . .
C43 C42 C58 117.70(17) . .
C42 C43 C44 127.32(18) . .
C42 C43 H43 116.3 . .
C44 C43 H43 116.3 . .
N8 C44 C43 120.63(18) . .
N8 C44 C64 124.6(2) . .
C43 C44 C64 114.71(19) . .
N8 C45 C50 124.27(19) . .
N8 C45 C46 117.35(18) . .
C50 C45 C46 118.10(19) . .
C47 C46 C45 119.2(2) . .
C47 C46 N5 122.3(2) . .
C45 C46 N5 118.34(17) . .
C46 C47 C48 121.0(2) . .
C46 C47 H47 119.5 . .
C48 C47 H47 119.5 . .
C49 C48 C47 120.1(2) . .
C49 C48 H48 119.9 . .
C47 C48 H48 119.9 . .
C48 C49 C50 119.9(2) . .
C48 C49 H49 120.1 . .
C50 C49 H49 120.1 . .
C49 C50 C45 121.7(2) . .
C49 C50 H50 119.1 . .
C45 C50 H50 119.1 . .
C33 C51 H51A 109.5 . .
C33 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C33 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C53 C52 C57 118.2(2) . .
C53 C52 C35 120.27(19) . .
C57 C52 C35 121.48(17) . .
C52 C53 C54 120.2(2) . .
C52 C53 H53 119.9 . .
C54 C53 H53 119.9 . .
C55 C54 C53 120.8(2) . .
C55 C54 H54 119.6 . .
C53 C54 H54 119.6 . .
C56 C55 C54 119.5(2) . .
C56 C55 H55 120.3 . .
C54 C55 H55 120.3 . .
C55 C56 C57 120.1(2) . .
C55 C56 H56 119.9 . .
C57 C56 H56 119.9 . .
C56 C57 C52 121.1(2) . .
C56 C57 H57 119.5 . .
C52 C57 H57 119.5 . .
C59 C58 C63 118.6(2) . .
C59 C58 C42 120.0(2) . .
C63 C58 C42 121.2(2) . .
C58 C59 C60 120.2(3) . .
C58 C59 H59 119.9 . .
C60 C59 H59 119.9 . .
C61 C60 C59 120.0(3) . .
C61 C60 H60 120.0 . .
C59 C60 H60 120.0 . .
C60 C61 C62 120.3(3) . .
C60 C61 H61 119.8 . .
C62 C61 H61 119.8 . .
C61 C62 C63 120.4(3) . .
C61 C62 H62 119.8 . .
C63 C62 H62 119.8 . .
C62 C63 C58 120.4(3) . .
C62 C63 H63 119.8 . .
C58 C63 H63 119.8 . .
C44 C64 H64A 109.5 . .
C44 C64 H64B 109.5 . .
H64A C64 H64B 109.5 . .
C44 C64 H64C 109.5 . .
H64A C64 H64C 109.5 . .
H64B C64 H64C 109.5 . .
H64D C64 H64E 109.5 . .
H64D C64 H64F 109.5 . .
H64E C64 H64F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.337(3) .
N1 C14 1.408(3) .
N1 H1N 0.862(10) .
N2 C3 1.318(3) .
N2 C4 1.412(3) .
N3 C10 1.336(3) .
N3 C5 1.409(3) .
N3 H3N 0.858(10) .
N4 C12 1.316(2) .
N4 C13 1.410(3) .
C1 C2 1.395(3) .
C1 C19 1.504(3) .
C2 C3 1.411(3) .
C2 H2 0.9300 .
C3 C20 1.498(3) .
C4 C9 1.388(3) .
C4 C5 1.399(3) .
C5 C6 1.390(3) .
C6 C7 1.380(3) .
C6 H6 0.9300 .
C7 C8 1.373(3) .
C7 H7 0.9300 .
C8 C9 1.385(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C11 1.377(3) .
C10 C26 1.495(3) .
C11 C12 1.418(3) .
C11 H11 0.9300 .
C12 C32 1.497(3) .
C13 C18 1.394(3) .
C13 C14 1.412(3) .
C14 C15 1.389(3) .
C15 C16 1.386(4) .
C15 H15 0.9300 .
C16 C17 1.367(4) .
C16 H16 0.9300 .
C17 C18 1.387(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C19 H19D 0.9600 .
C19 H19E 0.9600 .
C19 H19F 0.9600 .
C20 C21 1.381(3) .
C20 C25 1.388(3) .
C21 C22 1.385(4) .
C21 H21 0.9300 .
C22 C23 1.379(4) .
C22 H22 0.9300 .
C23 C24 1.361(4) .
C23 H23 0.9300 .
C24 C25 1.379(4) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C26 C27 1.379(3) .
C26 C31 1.381(3) .
C27 C28 1.382(4) .
C27 H27 0.9300 .
C28 C29 1.368(5) .
C28 H28 0.9300 .
C29 C30 1.368(5) .
C29 H29 0.9300 .
C30 C31 1.380(4) .
C30 H30 0.9300 .
C31 H31 0.9300 .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
C32 H32D 0.9600 .
C32 H32E 0.9600 .
C32 H32F 0.9600 .
N5 C33 1.342(3) .
N5 C46 1.409(3) .
N5 H5N 0.858(10) .
N6 C35 1.312(3) .
N6 C36 1.409(2) .
N7 C42 1.346(2) .
N7 C37 1.401(3) .
N7 H7N 0.857(10) .
N8 C44 1.308(3) .
N8 C45 1.406(3) .
C33 C34 1.385(3) .
C33 C51 1.498(3) .
C34 C35 1.425(3) .
C34 H34 0.9300 .
C35 C52 1.500(3) .
C36 C41 1.393(3) .
C36 C37 1.405(3) .
C37 C38 1.392(3) .
C38 C39 1.381(3) .
C38 H38 0.9300 .
C39 C40 1.374(3) .
C39 H39 0.9300 .
C40 C41 1.386(3) .
C40 H40 0.9300 .
C41 H41 0.9300 .
C42 C43 1.378(3) .
C42 C58 1.488(3) .
C43 C44 1.418(3) .
C43 H43 0.9300 .
C44 C64 1.512(3) .
C45 C50 1.405(3) .
C45 C46 1.407(3) .
C46 C47 1.388(3) .
C47 C48 1.392(4) .
C47 H47 0.9300 .
C48 C49 1.364(4) .
C48 H48 0.9300 .
C49 C50 1.373(3) .
C49 H49 0.9300 .
C50 H50 0.9300 .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
C52 C53 1.384(3) .
C52 C57 1.391(3) .
C53 C54 1.388(4) .
C53 H53 0.9300 .
C54 C55 1.373(4) .
C54 H54 0.9300 .
C55 C56 1.371(4) .
C55 H55 0.9300 .
C56 C57 1.383(3) .
C56 H56 0.9300 .
C57 H57 0.9300 .
C58 C59 1.387(3) .
C58 C63 1.390(3) .
C59 C60 1.391(4) .
C59 H59 0.9300 .
C60 C61 1.365(5) .
C60 H60 0.9300 .
C61 C62 1.366(5) .
C61 H61 0.9300 .
C62 C63 1.377(4) .
C62 H62 0.9300 .
C63 H63 0.9300 .
C64 H64A 0.9600 .
C64 H64B 0.9600 .
C64 H64C 0.9600 .
C64 H64D 0.9600 .
C64 H64E 0.9600 .
C64 H64F 0.9600 .
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
C14 N1 C1 C2 171.7(2) . . . .
C14 N1 C1 C19 -3.1(3) . . . .
N1 C1 C2 C3 -6.3(3) . . . .
C19 C1 C2 C3 168.7(2) . . . .
C4 N2 C3 C2 178.67(19) . . . .
C4 N2 C3 C20 -7.7(3) . . . .
C1 C2 C3 N2 10.0(3) . . . .
C1 C2 C3 C20 -163.9(2) . . . .
C3 N2 C4 C9 -55.0(3) . . . .
C3 N2 C4 C5 130.8(2) . . . .
C9 C4 C5 C6 -0.2(3) . . . .
N2 C4 C5 C6 174.26(19) . . . .
C9 C4 C5 N3 -176.68(19) . . . .
N2 C4 C5 N3 -2.2(3) . . . .
C10 N3 C5 C6 38.7(3) . . . .
C10 N3 C5 C4 -145.0(2) . . . .
C4 C5 C6 C7 0.8(3) . . . .
N3 C5 C6 C7 177.0(2) . . . .
C5 C6 C7 C8 -0.3(4) . . . .
C6 C7 C8 C9 -0.8(4) . . . .
C7 C8 C9 C4 1.5(3) . . . .
C5 C4 C9 C8 -0.9(3) . . . .
N2 C4 C9 C8 -175.1(2) . . . .
C5 N3 C10 C11 -178.1(2) . . . .
C5 N3 C10 C26 6.9(3) . . . .
N3 C10 C11 C12 -2.0(3) . . . .
C26 C10 C11 C12 173.1(2) . . . .
C13 N4 C12 C11 178.58(18) . . . .
C13 N4 C12 C32 -4.7(3) . . . .
C10 C11 C12 N4 5.8(3) . . . .
C10 C11 C12 C32 -171.2(2) . . . .
C12 N4 C13 C18 -42.3(3) . . . .
C12 N4 C13 C14 142.7(2) . . . .
C1 N1 C14 C15 52.6(3) . . . .
C1 N1 C14 C13 -130.8(2) . . . .
C18 C13 C14 C15 -0.7(3) . . . .
N4 C13 C14 C15 174.56(19) . . . .
C18 C13 C14 N1 -177.34(19) . . . .
N4 C13 C14 N1 -2.1(3) . . . .
N1 C14 C15 C16 179.0(2) . . . .
C13 C14 C15 C16 2.5(3) . . . .
C14 C15 C16 C17 -1.9(4) . . . .
C15 C16 C17 C18 -0.5(4) . . . .
C16 C17 C18 C13 2.3(4) . . . .
N4 C13 C18 C17 -176.6(2) . . . .
C14 C13 C18 C17 -1.7(3) . . . .
N2 C3 C20 C21 -58.8(3) . . . .
C2 C3 C20 C21 115.1(2) . . . .
N2 C3 C20 C25 123.2(2) . . . .
C2 C3 C20 C25 -62.9(3) . . . .
C25 C20 C21 C22 -0.8(3) . . . .
C3 C20 C21 C22 -179.0(2) . . . .
C20 C21 C22 C23 -1.3(4) . . . .
C21 C22 C23 C24 1.5(4) . . . .
C22 C23 C24 C25 0.5(4) . . . .
C23 C24 C25 C20 -2.8(4) . . . .
C21 C20 C25 C24 2.9(4) . . . .
C3 C20 C25 C24 -179.0(2) . . . .
N3 C10 C26 C27 -122.2(2) . . . .
C11 C10 C26 C27 62.7(3) . . . .
N3 C10 C26 C31 62.8(3) . . . .
C11 C10 C26 C31 -112.3(2) . . . .
C31 C26 C27 C28 -1.6(4) . . . .
C10 C26 C27 C28 -176.7(3) . . . .
C26 C27 C28 C29 0.9(5) . . . .
C27 C28 C29 C30 0.7(5) . . . .
C28 C29 C30 C31 -1.4(5) . . . .
C29 C30 C31 C26 0.6(4) . . . .
C27 C26 C31 C30 0.9(4) . . . .
C10 C26 C31 C30 175.9(2) . . . .
C46 N5 C33 C34 -176.69(19) . . . .
C46 N5 C33 C51 -3.2(3) . . . .
N5 C33 C34 C35 8.8(3) . . . .
C51 C33 C34 C35 -164.74(19) . . . .
C36 N6 C35 C34 179.55(17) . . . .
C36 N6 C35 C52 5.5(3) . . . .
C33 C34 C35 N6 -9.1(3) . . . .
C33 C34 C35 C52 165.31(18) . . . .
C35 N6 C36 C41 57.9(3) . . . .
C35 N6 C36 C37 -128.60(19) . . . .
C42 N7 C37 C38 -26.7(3) . . . .
C42 N7 C37 C36 156.4(2) . . . .
C41 C36 C37 C38 -2.3(3) . . . .
N6 C36 C37 C38 -175.98(17) . . . .
C41 C36 C37 N7 174.84(17) . . . .
N6 C36 C37 N7 1.1(3) . . . .
N7 C37 C38 C39 -175.7(2) . . . .
C36 C37 C38 C39 1.2(3) . . . .
C37 C38 C39 C40 0.5(3) . . . .
C38 C39 C40 C41 -1.0(3) . . . .
C39 C40 C41 C36 -0.1(3) . . . .
C37 C36 C41 C40 1.8(3) . . . .
N6 C36 C41 C40 175.09(18) . . . .
C37 N7 C42 C43 168.2(2) . . . .
C37 N7 C42 C58 -17.2(3) . . . .
N7 C42 C43 C44 -0.4(3) . . . .
C58 C42 C43 C44 -175.3(2) . . . .
C45 N8 C44 C43 -178.18(19) . . . .
C45 N8 C44 C64 5.0(3) . . . .
C42 C43 C44 N8 -4.0(3) . . . .
C42 C43 C44 C64 173.1(2) . . . .
C44 N8 C45 C50 41.2(3) . . . .
C44 N8 C45 C46 -145.0(2) . . . .
N8 C45 C46 C47 -175.6(2) . . . .
C50 C45 C46 C47 -1.4(3) . . . .
N8 C45 C46 N5 -0.3(3) . . . .
C50 C45 C46 N5 173.86(19) . . . .
C33 N5 C46 C47 -52.6(3) . . . .
C33 N5 C46 C45 132.3(2) . . . .
C45 C46 C47 C48 0.0(4) . . . .
N5 C46 C47 C48 -175.1(2) . . . .
C46 C47 C48 C49 0.6(4) . . . .
C47 C48 C49 C50 0.4(4) . . . .
C48 C49 C50 C45 -1.9(4) . . . .
N8 C45 C50 C49 176.1(2) . . . .
C46 C45 C50 C49 2.4(3) . . . .
N6 C35 C52 C53 48.4(3) . . . .
C34 C35 C52 C53 -125.8(2) . . . .
N6 C35 C52 C57 -135.3(2) . . . .
C34 C35 C52 C57 50.5(3) . . . .
C57 C52 C53 C54 2.6(3) . . . .
C35 C52 C53 C54 179.1(2) . . . .
C52 C53 C54 C55 -0.7(4) . . . .
C53 C54 C55 C56 -0.5(4) . . . .
C54 C55 C56 C57 -0.3(4) . . . .
C55 C56 C57 C52 2.3(4) . . . .
C53 C52 C57 C56 -3.5(3) . . . .
C35 C52 C57 C56 -179.8(2) . . . .
N7 C42 C58 C59 134.0(2) . . . .
C43 C42 C58 C59 -51.2(3) . . . .
N7 C42 C58 C63 -50.7(3) . . . .
C43 C42 C58 C63 124.1(2) . . . .
C63 C58 C59 C60 -0.3(3) . . . .
C42 C58 C59 C60 175.2(2) . . . .
C58 C59 C60 C61 0.3(4) . . . .
C59 C60 C61 C62 -0.3(4) . . . .
C60 C61 C62 C63 0.4(4) . . . .
C61 C62 C63 C58 -0.4(4) . . . .
C59 C58 C63 C62 0.3(3) . . . .
C42 C58 C63 C62 -175.0(2) . . . .
