#------------------------------------------------------------------------------
#$Date: 2023-01-21 10:37:29 +0200 (Sat, 21 Jan 2023) $
#$Revision: 280493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106520.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_8106520
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Baashen, Mohammed'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
_publ_section_title
;
 Crystal structure of
 3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde,
 a rare Z′ = 3 structure, C20H17N5O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              313
_journal_page_last               315
_journal_paper_doi               10.1515/ncrs-2016-0258
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C20 H17 N5 O'
_chemical_formula_sum            'C20 H17 N5 O'
_chemical_formula_weight         343.39
_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                85.958(5)
_cell_angle_beta                 87.407(5)
_cell_angle_gamma                87.619(5)
_cell_formula_units_Z            6
_cell_length_a                   11.5358(7)
_cell_length_b                   13.8746(9)
_cell_length_c                   16.3942(10)
_cell_measurement_reflns_used    6352
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0770
_cell_measurement_theta_min      3.7340
_cell_volume                     2612.8(3)
_computing_cell_refinement       'CrysAlis PRO [11]'
_computing_data_collection       'CrysAlis PRO [11]'
_computing_data_reduction        'CrysAlis PRO [11]'
_computing_molecular_graphics    'ORTEP-3 for Windows [13]'
_computing_publication_material  'WinGX [13] and CHEMDRAW Ultra [14]'
_computing_structure_refinement  'SHELXS2013 [12]'
_computing_structure_solution    'SHELXS2013 [12]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.834
_diffrn_reflns_theta_min         3.404
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         12359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7462
_reflns_number_total             12359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0258_suppl.cif
_cod_data_source_block           bmk1560b
_cod_database_code               8106520
_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   0.962
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_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
C1 C 0.5837(3) 1.2072(2) -0.35853(17) 0.0893(9) Uani 1 1 d . . . . .
H1A H 0.6588 1.1886 -0.3813 0.134 Uiso 1 1 calc R U . . .
H1B H 0.5863 1.2704 -0.3385 0.134 Uiso 1 1 calc R U . . .
H1C H 0.5275 1.2082 -0.4001 0.134 Uiso 1 1 calc R U . . .
C2 C 0.5498(2) 1.13542(16) -0.28889(14) 0.0591(6) Uani 1 1 d . . . . .
C3 C 0.4667(2) 1.15996(15) -0.22981(14) 0.0595(6) Uani 1 1 d . . . . .
H3 H 0.4313 1.2215 -0.2334 0.071 Uiso 1 1 calc R U . . .
C4 C 0.43494(19) 1.09528(14) -0.16536(13) 0.0547(5) Uani 1 1 d . . . . .
H4 H 0.3797 1.1134 -0.1256 0.066 Uiso 1 1 calc R U . . .
C5 C 0.48633(17) 1.00347(13) -0.16085(12) 0.0471(5) Uani 1 1 d . . . . .
C6 C 0.56954(18) 0.97730(15) -0.21870(13) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.6043 0.9156 -0.2154 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6008(2) 1.04366(16) -0.28158(14) 0.0610(6) Uani 1 1 d . . . . .
H7 H 0.6580 1.0261 -0.3202 0.073 Uiso 1 1 calc R U . . .
C8 C 0.34403(17) 0.90783(14) -0.07013(12) 0.0463(4) Uani 1 1 d . . . . .
C9 C 0.36366(16) 0.83480(14) -0.01070(11) 0.0453(4) Uani 1 1 d . . . . .
C10 C 0.23450(18) 0.95040(16) -0.10442(14) 0.0614(6) Uani 1 1 d . . . . .
H10A H 0.2034 0.9999 -0.0707 0.092 Uiso 1 1 calc R U . . .
H10B H 0.1792 0.9008 -0.1058 0.092 Uiso 1 1 calc R U . . .
H10C H 0.2503 0.9780 -0.1589 0.092 Uiso 1 1 calc R U . . .
C11 C 0.28006(17) 0.77584(13) 0.03711(12) 0.0464(5) Uani 1 1 d . . . . .
C12 C 0.29786(17) 0.69943(13) 0.09794(12) 0.0478(5) Uani 1 1 d . . . . .
C13 C 0.18816(18) 0.67041(14) 0.12169(12) 0.0500(5) Uani 1 1 d . . . . .
H13 H 0.1699 0.6212 0.1611 0.060 Uiso 1 1 calc R U . . .
C14 C 0.40469(19) 0.65853(15) 0.13092(14) 0.0606(6) Uani 1 1 d . . . . .
H14 H 0.4741 0.6764 0.1040 0.073 Uiso 1 1 calc R U . . .
C15 C -0.01161(17) 0.72332(14) 0.07813(12) 0.0490(5) Uani 1 1 d . . . . .
C16 C -0.0704(2) 0.65878(17) 0.13051(14) 0.0667(6) Uani 1 1 d . . . . .
H16 H -0.0305 0.6182 0.1682 0.080 Uiso 1 1 calc R U . . .
C17 C -0.1892(2) 0.65501(19) 0.12641(16) 0.0740(7) Uani 1 1 d . . . . .
H17 H -0.2292 0.6110 0.1614 0.089 Uiso 1 1 calc R U . . .
C18 C -0.2495(2) 0.71475(18) 0.07182(15) 0.0672(6) Uani 1 1 d . . . . .
H18 H -0.3294 0.7107 0.0690 0.081 Uiso 1 1 calc R U . . .
C19 C -0.1906(2) 0.78037(18) 0.02151(16) 0.0710(7) Uani 1 1 d . . . . .
H19 H -0.2311 0.8224 -0.0147 0.085 Uiso 1 1 calc R U . . .
C20 C -0.07219(19) 0.78484(16) 0.02390(15) 0.0637(6) Uani 1 1 d . . . . .
H20 H -0.0327 0.8293 -0.0110 0.076 Uiso 1 1 calc R U . . .
C21 C 0.8783(3) -0.01809(19) 0.85670(16) 0.0825(8) Uani 1 1 d . . . . .
H21A H 0.8896 -0.0823 0.8387 0.124 Uiso 1 1 calc R U . . .
H21B H 0.7974 -0.0055 0.8697 0.124 Uiso 1 1 calc R U . . .
H21C H 0.9220 -0.0123 0.9045 0.124 Uiso 1 1 calc R U . . .
C22 C 0.9192(2) 0.05409(15) 0.78943(13) 0.0556(5) Uani 1 1 d . . . . .
C23 C 1.0215(2) 0.03783(16) 0.74434(14) 0.0619(6) Uani 1 1 d . . . . .
H23 H 1.0651 -0.0192 0.7552 0.074 Uiso 1 1 calc R U . . .
C24 C 1.06060(18) 0.10431(15) 0.68356(13) 0.0580(6) Uani 1 1 d . . . . .
H24 H 1.1296 0.0922 0.6538 0.070 Uiso 1 1 calc R U . . .
C25 C 0.99589(17) 0.18890(13) 0.66755(12) 0.0459(5) Uani 1 1 d . . . . .
C26 C 0.89352(18) 0.20651(14) 0.71080(13) 0.0523(5) Uani 1 1 d . . . . .
H26 H 0.8500 0.2635 0.7000 0.063 Uiso 1 1 calc R U . . .
C27 C 0.85592(19) 0.13852(15) 0.77060(13) 0.0571(5) Uani 1 1 d . . . . .
H27 H 0.7857 0.1501 0.7991 0.069 Uiso 1 1 calc R U . . .
C28 C 1.13904(17) 0.29433(13) 0.58506(12) 0.0459(4) Uani 1 1 d . . . . .
C29 C 1.12698(16) 0.34506(13) 0.51064(12) 0.0444(4) Uani 1 1 d . . . . .
C30 C 1.23670(19) 0.28372(16) 0.64173(13) 0.0607(6) Uani 1 1 d . . . . .
H30A H 1.2062 0.2798 0.6973 0.091 Uiso 1 1 calc R U . . .
H30B H 1.2847 0.3387 0.6328 0.091 Uiso 1 1 calc R U . . .
H30C H 1.2821 0.2259 0.6316 0.091 Uiso 1 1 calc R U . . .
C31 C 1.21337(17) 0.39641(13) 0.45809(12) 0.0444(4) Uani 1 1 d . . . . .
C32 C 1.19619(17) 0.46291(13) 0.38921(12) 0.0478(5) Uani 1 1 d . . . . .
C33 C 1.30661(17) 0.48380(13) 0.35982(12) 0.0491(5) Uani 1 1 d . . . . .
H33 H 1.3257 0.5253 0.3146 0.059 Uiso 1 1 calc R U . . .
C34 C 1.08854(19) 0.50342(15) 0.35610(14) 0.0598(6) Uani 1 1 d . . . . .
H34 H 1.0193 0.4865 0.3837 0.072 Uiso 1 1 calc R U . . .
C35 C 1.50596(17) 0.42941(12) 0.40207(12) 0.0451(4) Uani 1 1 d . . . . .
C36 C 1.56754(18) 0.38670(14) 0.46653(13) 0.0534(5) Uani 1 1 d . . . . .
H36 H 1.5283 0.3636 0.5143 0.064 Uiso 1 1 calc R U . . .
C37 C 1.6872(2) 0.37856(16) 0.45981(15) 0.0621(6) Uani 1 1 d . . . . .
H37 H 1.7285 0.3496 0.5030 0.075 Uiso 1 1 calc R U . . .
C38 C 1.7455(2) 0.41297(16) 0.38959(16) 0.0653(6) Uani 1 1 d . . . . .
H38 H 1.8260 0.4066 0.3849 0.078 Uiso 1 1 calc R U . . .
C39 C 1.6842(2) 0.45682(16) 0.32626(15) 0.0658(6) Uani 1 1 d . . . . .
H39 H 1.7239 0.4809 0.2791 0.079 Uiso 1 1 calc R U . . .
C40 C 1.56400(19) 0.46557(15) 0.33182(13) 0.0553(5) Uani 1 1 d . . . . .
H40 H 1.5231 0.4954 0.2888 0.066 Uiso 1 1 calc R U . . .
C41 C 0.8478(2) -0.11266(18) 0.59993(15) 0.0736(7) Uani 1 1 d . . . . .
H41A H 0.8055 -0.1709 0.6011 0.110 Uiso 0.5 1 calc R U P . .
H41B H 0.8357 -0.0840 0.6514 0.110 Uiso 0.5 1 calc R U P . .
H41C H 0.9290 -0.1276 0.5905 0.110 Uiso 0.5 1 calc R U P . .
H41D H 0.9080 -0.0841 0.6275 0.110 Uiso 0.5 1 calc R U P . .
H41E H 0.8778 -0.1710 0.5772 0.110 Uiso 0.5 1 calc R U P . .
H41F H 0.7844 -0.1274 0.6382 0.110 Uiso 0.5 1 calc R U P . .
C42 C 0.80536(18) -0.04255(15) 0.53197(12) 0.0531(5) Uani 1 1 d . . . . .
C43 C 0.8520(2) 0.04740(16) 0.51683(14) 0.0636(6) Uani 1 1 d . . . . .
H43 H 0.9099 0.0653 0.5497 0.076 Uiso 1 1 calc R U . . .
C44 C 0.81505(18) 0.11137(15) 0.45443(14) 0.0574(5) Uani 1 1 d . . . . .
H44 H 0.8476 0.1716 0.4455 0.069 Uiso 1 1 calc R U . . .
C45 C 0.72963(16) 0.08518(13) 0.40557(12) 0.0450(4) Uani 1 1 d . . . . .
C46 C 0.68009(17) -0.00362(14) 0.41920(13) 0.0513(5) Uani 1 1 d . . . . .
H46 H 0.6217 -0.0209 0.3864 0.062 Uiso 1 1 calc R U . . .
C47 C 0.71846(18) -0.06680(14) 0.48248(13) 0.0526(5) Uani 1 1 d . . . . .
H47 H 0.6852 -0.1267 0.4919 0.063 Uiso 1 1 calc R U . . .
C48 C 0.58588(16) 0.18712(13) 0.32257(12) 0.0429(4) Uani 1 1 d . . . . .
C49 C 0.60166(16) 0.23997(13) 0.24931(12) 0.0448(4) Uani 1 1 d . . . . .
C50 C 0.48398(17) 0.17299(14) 0.38008(12) 0.0514(5) Uani 1 1 d . . . . .
H50A H 0.4495 0.1130 0.3712 0.077 Uiso 1 1 calc R U . . .
H50B H 0.4280 0.2254 0.3709 0.077 Uiso 1 1 calc R U . . .
H50C H 0.5085 0.1714 0.4354 0.077 Uiso 1 1 calc R U . . .
C51 C 0.51597(17) 0.29574(13) 0.20050(12) 0.0453(4) Uani 1 1 d . . . . .
C52 C 0.53391(18) 0.36505(14) 0.13362(12) 0.0487(5) Uani 1 1 d . . . . .
C53 C 0.42401(19) 0.39389(14) 0.11154(13) 0.0525(5) Uani 1 1 d . . . . .
H53 H 0.4052 0.4390 0.0690 0.063 Uiso 1 1 calc R U . . .
C54 C 0.6414(2) 0.40189(16) 0.09763(14) 0.0646(6) Uani 1 1 d . . . . .
H54 H 0.7103 0.3749 0.1180 0.078 Uiso 1 1 calc R U . . .
C55 C 0.22398(18) 0.35042(14) 0.16356(13) 0.0515(5) Uani 1 1 d . . . . .
C56 C 0.1655(2) 0.40945(16) 0.10694(14) 0.0631(6) Uani 1 1 d . . . . .
H56 H 0.2061 0.4479 0.0676 0.076 Uiso 1 1 calc R U . . .
C57 C 0.0459(2) 0.4108(2) 0.10937(17) 0.0781(7) Uani 1 1 d . . . . .
H57 H 0.0059 0.4502 0.0710 0.094 Uiso 1 1 calc R U . . .
C58 C -0.0146(2) 0.3555(2) 0.16704(19) 0.0864(8) Uani 1 1 d . . . . .
H58 H -0.0953 0.3571 0.1679 0.104 Uiso 1 1 calc R U . . .
C59 C 0.0438(2) 0.2976(2) 0.2237(2) 0.0946(10) Uani 1 1 d . . . . .
H59 H 0.0028 0.2598 0.2633 0.114 Uiso 1 1 calc R U . . .
C60 C 0.1629(2) 0.29523(18) 0.22220(17) 0.0786(8) Uani 1 1 d . . . . .
H60 H 0.2025 0.2561 0.2610 0.094 Uiso 1 1 calc R U . . .
N1 N 0.45217(13) 0.93438(11) -0.09626(9) 0.0467(4) Uani 1 1 d . . . . .
N2 N 0.53532(14) 0.88023(12) -0.05527(10) 0.0543(4) Uani 1 1 d . . . . .
N3 N 0.48085(14) 0.82014(12) -0.00338(10) 0.0541(4) Uani 1 1 d . . . . .
N4 N 0.16724(14) 0.79213(12) 0.02524(10) 0.0511(4) Uani 1 1 d . . . . .
N5 N 0.11219(14) 0.72591(11) 0.07767(10) 0.0487(4) Uani 1 1 d . . . . .
N6 N 1.03332(14) 0.25626(11) 0.60200(10) 0.0463(4) Uani 1 1 d . . . . .
N7 N 0.95884(14) 0.28316(12) 0.54184(11) 0.0545(4) Uani 1 1 d . . . . .
N8 N 1.01618(15) 0.33728(12) 0.48647(11) 0.0535(4) Uani 1 1 d . . . . .
N9 N 1.32598(14) 0.37813(11) 0.46925(10) 0.0466(4) Uani 1 1 d . . . . .
N10 N 1.38207(14) 0.43328(11) 0.40828(9) 0.0451(4) Uani 1 1 d . . . . .
N11 N 0.69354(13) 0.14981(11) 0.33874(10) 0.0464(4) Uani 1 1 d . . . . .
N12 N 0.77293(15) 0.17919(13) 0.27893(11) 0.0582(5) Uani 1 1 d . . . . .
N13 N 0.71603(15) 0.23375(12) 0.22477(11) 0.0572(5) Uani 1 1 d . . . . .
N14 N 0.40405(14) 0.28389(11) 0.21795(10) 0.0497(4) Uani 1 1 d . . . . .
N15 N 0.34801(14) 0.34560(11) 0.16206(10) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.41041(14) 0.60292(12) 0.19079(11) 0.0797(5) Uani 1 1 d . . . . .
O2 O 1.08280(14) 0.55765(11) 0.29511(10) 0.0737(5) Uani 1 1 d . . . . .
O3 O 0.64867(16) 0.46490(13) 0.04334(11) 0.0873(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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C7 C2 C3 117.71(19) . .
C7 C2 C1 121.5(2) . .
C3 C2 C1 120.8(2) . .
C2 C3 C4 121.6(2) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C5 C4 C3 119.1(2) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
C6 C5 C4 120.46(18) . .
C6 C5 N1 119.45(17) . .
C4 C5 N1 120.08(18) . .
C5 C6 C7 119.25(19) . .
C5 C6 H6 120.4 . .
C7 C6 H6 120.4 . .
C6 C7 C2 121.9(2) . .
C6 C7 H7 119.1 . .
C2 C7 H7 119.1 . .
N1 C8 C9 103.98(16) . .
N1 C8 C10 124.55(17) . .
C9 C8 C10 131.44(19) . .
N3 C9 C8 108.89(17) . .
N3 C9 C11 122.03(16) . .
C8 C9 C11 129.03(18) . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N4 C11 C12 110.83(17) . .
N4 C11 C9 118.94(16) . .
C12 C11 C9 130.23(18) . .
C13 C12 C11 104.75(17) . .
C13 C12 C14 125.38(17) . .
C11 C12 C14 129.86(19) . .
N5 C13 C12 107.63(16) . .
N5 C13 H13 126.2 . .
C12 C13 H13 126.2 . .
O1 C14 C12 124.8(2) . .
O1 C14 H14 117.6 . .
C12 C14 H14 117.6 . .
C16 C15 C20 119.8(2) . .
C16 C15 N5 120.68(18) . .
C20 C15 N5 119.46(18) . .
C15 C16 C17 119.1(2) . .
C15 C16 H16 120.5 . .
C17 C16 H16 120.5 . .
C18 C17 C16 121.3(2) . .
C18 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
C19 C18 C17 119.2(2) . .
C19 C18 H18 120.4 . .
C17 C18 H18 120.4 . .
C18 C19 C20 120.6(2) . .
C18 C19 H19 119.7 . .
C20 C19 H19 119.7 . .
C19 C20 C15 120.0(2) . .
C19 C20 H20 120.0 . .
C15 C20 H20 120.0 . .
C22 C21 H21A 109.5 . .
C22 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C22 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C27 C22 C23 117.54(19) . .
C27 C22 C21 121.3(2) . .
C23 C22 C21 121.2(2) . .
C24 C23 C22 121.6(2) . .
C24 C23 H23 119.2 . .
C22 C23 H23 119.2 . .
C25 C24 C23 119.2(2) . .
C25 C24 H24 120.4 . .
C23 C24 H24 120.4 . .
C26 C25 C24 120.50(18) . .
C26 C25 N6 120.00(17) . .
C24 C25 N6 119.40(17) . .
C25 C26 C27 119.15(19) . .
C25 C26 H26 120.4 . .
C27 C26 H26 120.4 . .
C22 C27 C26 122.0(2) . .
C22 C27 H27 119.0 . .
C26 C27 H27 119.0 . .
N6 C28 C29 103.91(16) . .
N6 C28 C30 123.97(17) . .
C29 C28 C30 132.01(18) . .
N8 C29 C28 109.00(17) . .
N8 C29 C31 121.15(17) . .
C28 C29 C31 129.76(18) . .
C28 C30 H30A 109.5 . .
C28 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C28 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
N9 C31 C32 111.11(17) . .
N9 C31 C29 119.76(16) . .
C32 C31 C29 129.00(18) . .
C33 C32 C31 104.50(17) . .
C33 C32 C34 126.04(17) . .
C31 C32 C34 129.45(19) . .
N10 C33 C32 107.69(16) . .
N10 C33 H33 126.2 . .
C32 C33 H33 126.2 . .
O2 C34 C32 124.5(2) . .
O2 C34 H34 117.7 . .
C32 C34 H34 117.7 . .
C40 C35 C36 120.17(19) . .
C40 C35 N10 120.48(17) . .
C36 C35 N10 119.33(17) . .
C37 C36 C35 119.9(2) . .
C37 C36 H36 120.1 . .
C35 C36 H36 120.1 . .
C38 C37 C36 120.3(2) . .
C38 C37 H37 119.9 . .
C36 C37 H37 119.9 . .
C37 C38 C39 119.7(2) . .
C37 C38 H38 120.2 . .
C39 C38 H38 120.2 . .
C38 C39 C40 120.9(2) . .
C38 C39 H39 119.6 . .
C40 C39 H39 119.6 . .
C35 C40 C39 119.1(2) . .
C35 C40 H40 120.5 . .
C39 C40 H40 120.5 . .
C42 C41 H41A 109.5 . .
C42 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C42 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C42 C41 H41D 109.5 . .
H41A C41 H41D 141.1 . .
H41B C41 H41D 56.3 . .
H41C C41 H41D 56.3 . .
C42 C41 H41E 109.5 . .
H41A C41 H41E 56.3 . .
H41B C41 H41E 141.1 . .
H41C C41 H41E 56.3 . .
H41D C41 H41E 109.5 . .
C42 C41 H41F 109.5 . .
H41A C41 H41F 56.3 . .
H41B C41 H41F 56.3 . .
H41C C41 H41F 141.1 . .
H41D C41 H41F 109.5 . .
H41E C41 H41F 109.5 . .
C43 C42 C47 117.77(18) . .
C43 C42 C41 121.4(2) . .
C47 C42 C41 120.8(2) . .
C44 C43 C42 121.9(2) . .
C44 C43 H43 119.1 . .
C42 C43 H43 119.1 . .
C45 C44 C43 119.24(19) . .
C45 C44 H44 120.4 . .
C43 C44 H44 120.4 . .
C44 C45 C46 120.63(18) . .
C44 C45 N11 119.66(17) . .
C46 C45 N11 119.69(18) . .
C45 C46 C47 119.1(2) . .
C45 C46 H46 120.4 . .
C47 C46 H46 120.4 . .
C42 C47 C46 121.34(19) . .
C42 C47 H47 119.3 . .
C46 C47 H47 119.3 . .
N11 C48 C49 103.88(16) . .
N11 C48 C50 122.89(16) . .
C49 C48 C50 133.11(17) . .
N13 C49 C48 109.09(16) . .
N13 C49 C51 121.80(17) . .
C48 C49 C51 129.11(17) . .
C48 C50 H50A 109.5 . .
C48 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
C48 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
N14 C51 C52 111.63(17) . .
N14 C51 C49 119.19(16) . .
C52 C51 C49 129.18(18) . .
C53 C52 C51 104.16(17) . .
C53 C52 C54 126.43(18) . .
C51 C52 C54 129.36(19) . .
N15 C53 C52 108.08(17) . .
N15 C53 H53 126.0 . .
C52 C53 H53 126.0 . .
O3 C54 C52 125.1(2) . .
O3 C54 H54 117.5 . .
C52 C54 H54 117.5 . .
C60 C55 C56 119.9(2) . .
C60 C55 N15 119.42(18) . .
C56 C55 N15 120.70(18) . .
C55 C56 C57 119.0(2) . .
C55 C56 H56 120.5 . .
C57 C56 H56 120.5 . .
C58 C57 C56 121.1(2) . .
C58 C57 H57 119.5 . .
C56 C57 H57 119.5 . .
C57 C58 C59 119.7(2) . .
C57 C58 H58 120.2 . .
C59 C58 H58 120.2 . .
C58 C59 C60 120.0(3) . .
C58 C59 H59 120.0 . .
C60 C59 H59 120.0 . .
C59 C60 C55 120.2(2) . .
C59 C60 H60 119.9 . .
C55 C60 H60 119.9 . .
C8 N1 N2 111.10(14) . .
C8 N1 C5 129.31(16) . .
N2 N1 C5 119.46(15) . .
N3 N2 N1 106.77(15) . .
N2 N3 C9 109.26(15) . .
C11 N4 N5 105.14(15) . .
C13 N5 N4 111.64(16) . .
C13 N5 C15 129.53(16) . .
N4 N5 C15 118.82(15) . .
C28 N6 N7 111.08(15) . .
C28 N6 C25 129.91(16) . .
N7 N6 C25 118.77(15) . .
N8 N7 N6 106.99(15) . .
N7 N8 C29 109.02(15) . .
C31 N9 N10 105.00(14) . .
C33 N10 N9 111.70(16) . .
C33 N10 C35 128.89(16) . .
N9 N10 C35 119.39(14) . .
C48 N11 N12 111.15(15) . .
C48 N11 C45 129.19(16) . .
N12 N11 C45 119.63(15) . .
N13 N12 N11 106.63(15) . .
N12 N13 C49 109.26(16) . .
C51 N14 N15 104.75(15) . .
C53 N15 N14 111.38(16) . .
C53 N15 C55 129.24(16) . .
N14 N15 C55 119.37(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.510(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.380(3) .
C2 C3 1.381(3) .
C3 C4 1.384(3) .
C3 H3 0.9300 .
C4 C5 1.381(3) .
C4 H4 0.9300 .
C5 C6 1.375(3) .
C5 N1 1.430(2) .
C6 C7 1.379(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 N1 1.358(2) .
C8 C9 1.374(2) .
C8 C10 1.489(3) .
C9 N3 1.368(2) .
C9 C11 1.456(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N4 1.332(2) .
C11 C12 1.418(3) .
C12 C13 1.375(3) .
C12 C14 1.446(3) .
C13 N5 1.343(2) .
C13 H13 0.9300 .
C14 O1 1.208(2) .
C14 H14 0.9300 .
C15 C16 1.374(3) .
C15 C20 1.381(3) .
C15 N5 1.430(3) .
C16 C17 1.379(3) .
C16 H16 0.9300 .
C17 C18 1.369(3) .
C17 H17 0.9300 .
C18 C19 1.366(3) .
C18 H18 0.9300 .
C19 C20 1.372(3) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C22 1.509(3) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C27 1.378(3) .
C22 C23 1.383(3) .
C23 C24 1.382(3) .
C23 H23 0.9300 .
C24 C25 1.380(3) .
C24 H24 0.9300 .
C25 C26 1.372(3) .
C25 N6 1.437(2) .
C26 C27 1.380(3) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C28 N6 1.359(2) .
C28 C29 1.375(3) .
C28 C30 1.489(3) .
C29 N8 1.366(2) .
C29 C31 1.462(3) .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
C31 N9 1.332(2) .
C31 C32 1.423(3) .
C32 C33 1.376(3) .
C32 C34 1.453(3) .
C33 N10 1.347(2) .
C33 H33 0.9300 .
C34 O2 1.211(2) .
C34 H34 0.9300 .
C35 C40 1.379(3) .
C35 C36 1.385(3) .
C35 N10 1.427(2) .
C36 C37 1.380(3) .
C36 H36 0.9300 .
C37 C38 1.373(3) .
C37 H37 0.9300 .
C38 C39 1.375(3) .
C38 H38 0.9300 .
C39 C40 1.386(3) .
C39 H39 0.9300 .
C40 H40 0.9300 .
C41 C42 1.511(3) .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
C41 H41D 0.9600 .
C41 H41E 0.9600 .
C41 H41F 0.9600 .
C42 C43 1.381(3) .
C42 C47 1.384(3) .
C43 C44 1.377(3) .
C43 H43 0.9300 .
C44 C45 1.374(3) .
C44 H44 0.9300 .
C45 C46 1.379(3) .
C45 N11 1.432(2) .
C46 C47 1.386(3) .
C46 H46 0.9300 .
C47 H47 0.9300 .
C48 N11 1.356(2) .
C48 C49 1.371(2) .
C48 C50 1.484(3) .
C49 N13 1.363(2) .
C49 C51 1.462(3) .
C50 H50A 0.9600 .
C50 H50B 0.9600 .
C50 H50C 0.9600 .
C51 N14 1.324(2) .
C51 C52 1.420(2) .
C52 C53 1.370(3) .
C52 C54 1.446(3) .
C53 N15 1.345(2) .
C53 H53 0.9300 .
C54 O3 1.205(2) .
C54 H54 0.9300 .
C55 C60 1.373(3) .
C55 C56 1.375(3) .
C55 N15 1.429(3) .
C56 C57 1.378(3) .
C56 H56 0.9300 .
C57 C58 1.362(4) .
C57 H57 0.9300 .
C58 C59 1.367(4) .
C58 H58 0.9300 .
C59 C60 1.373(3) .
C59 H59 0.9300 .
C60 H60 0.9300 .
N1 N2 1.365(2) .
N2 N3 1.307(2) .
N4 N5 1.369(2) .
N6 N7 1.360(2) .
N7 N8 1.310(2) .
N9 N10 1.370(2) .
N11 N12 1.364(2) .
N12 N13 1.307(2) .
N14 N15 1.374(2) .
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
C7 C2 C3 C4 -0.1(3) . . . .
C1 C2 C3 C4 -179.7(2) . . . .
C2 C3 C4 C5 -1.0(3) . . . .
C3 C4 C5 C6 1.3(3) . . . .
C3 C4 C5 N1 -177.99(19) . . . .
C4 C5 C6 C7 -0.3(3) . . . .
N1 C5 C6 C7 178.96(19) . . . .
C5 C6 C7 C2 -0.9(3) . . . .
C3 C2 C7 C6 1.1(3) . . . .
C1 C2 C7 C6 -179.3(2) . . . .
N1 C8 C9 N3 -0.1(2) . . . .
C10 C8 C9 N3 177.7(2) . . . .
N1 C8 C9 C11 -177.50(19) . . . .
C10 C8 C9 C11 0.3(4) . . . .
N3 C9 C11 N4 -178.05(19) . . . .
C8 C9 C11 N4 -0.9(3) . . . .
N3 C9 C11 C12 2.0(3) . . . .
C8 C9 C11 C12 179.1(2) . . . .
N4 C11 C12 C13 0.3(2) . . . .
C9 C11 C12 C13 -179.8(2) . . . .
N4 C11 C12 C14 -179.1(2) . . . .
C9 C11 C12 C14 0.8(4) . . . .
C11 C12 C13 N5 0.1(2) . . . .
C14 C12 C13 N5 179.5(2) . . . .
C13 C12 C14 O1 -10.5(4) . . . .
C11 C12 C14 O1 168.8(2) . . . .
C20 C15 C16 C17 1.7(4) . . . .
N5 C15 C16 C17 -176.8(2) . . . .
C15 C16 C17 C18 -0.6(4) . . . .
C16 C17 C18 C19 -1.1(4) . . . .
C17 C18 C19 C20 1.7(4) . . . .
C18 C19 C20 C15 -0.7(4) . . . .
C16 C15 C20 C19 -1.0(4) . . . .
N5 C15 C20 C19 177.4(2) . . . .
C27 C22 C23 C24 1.2(3) . . . .
C21 C22 C23 C24 -178.9(2) . . . .
C22 C23 C24 C25 0.0(4) . . . .
C23 C24 C25 C26 -0.6(3) . . . .
C23 C24 C25 N6 -177.19(19) . . . .
C24 C25 C26 C27 0.0(3) . . . .
N6 C25 C26 C27 176.55(18) . . . .
C23 C22 C27 C26 -1.8(3) . . . .
C21 C22 C27 C26 178.2(2) . . . .
C25 C26 C27 C22 1.3(3) . . . .
N6 C28 C29 N8 1.0(2) . . . .
C30 C28 C29 N8 -175.2(2) . . . .
N6 C28 C29 C31 -175.44(19) . . . .
C30 C28 C29 C31 8.4(4) . . . .
N8 C29 C31 N9 -158.72(18) . . . .
C28 C29 C31 N9 17.3(3) . . . .
N8 C29 C31 C32 16.8(3) . . . .
C28 C29 C31 C32 -167.2(2) . . . .
N9 C31 C32 C33 -0.3(2) . . . .
C29 C31 C32 C33 -176.08(19) . . . .
N9 C31 C32 C34 -179.0(2) . . . .
C29 C31 C32 C34 5.2(4) . . . .
C31 C32 C33 N10 -0.1(2) . . . .
C34 C32 C33 N10 178.6(2) . . . .
C33 C32 C34 O2 4.0(4) . . . .
C31 C32 C34 O2 -177.5(2) . . . .
C40 C35 C36 C37 -1.3(3) . . . .
N10 C35 C36 C37 177.05(18) . . . .
C35 C36 C37 C38 0.3(3) . . . .
C36 C37 C38 C39 0.8(4) . . . .
C37 C38 C39 C40 -0.9(4) . . . .
C36 C35 C40 C39 1.2(3) . . . .
N10 C35 C40 C39 -177.12(19) . . . .
C38 C39 C40 C35 -0.1(3) . . . .
C47 C42 C43 C44 -0.6(3) . . . .
C41 C42 C43 C44 179.2(2) . . . .
C42 C43 C44 C45 -0.2(3) . . . .
C43 C44 C45 C46 0.8(3) . . . .
C43 C44 C45 N11 -177.81(19) . . . .
C44 C45 C46 C47 -0.7(3) . . . .
N11 C45 C46 C47 177.93(17) . . . .
C43 C42 C47 C46 0.7(3) . . . .
C41 C42 C47 C46 -179.0(2) . . . .
C45 C46 C47 C42 -0.1(3) . . . .
N11 C48 C49 N13 -0.6(2) . . . .
C50 C48 C49 N13 175.2(2) . . . .
N11 C48 C49 C51 179.02(19) . . . .
C50 C48 C49 C51 -5.2(4) . . . .
N13 C49 C51 N14 166.39(18) . . . .
C48 C49 C51 N14 -13.2(3) . . . .
N13 C49 C51 C52 -13.9(3) . . . .
C48 C49 C51 C52 166.4(2) . . . .
N14 C51 C52 C53 -0.4(2) . . . .
C49 C51 C52 C53 179.9(2) . . . .
N14 C51 C52 C54 177.1(2) . . . .
C49 C51 C52 C54 -2.6(4) . . . .
C51 C52 C53 N15 0.4(2) . . . .
C54 C52 C53 N15 -177.2(2) . . . .
C53 C52 C54 O3 1.2(4) . . . .
C51 C52 C54 O3 -175.8(2) . . . .
C60 C55 C56 C57 -1.1(4) . . . .
N15 C55 C56 C57 178.8(2) . . . .
C55 C56 C57 C58 0.5(4) . . . .
C56 C57 C58 C59 0.1(5) . . . .
C57 C58 C59 C60 -0.2(5) . . . .
C58 C59 C60 C55 -0.4(5) . . . .
C56 C55 C60 C59 1.0(4) . . . .
N15 C55 C60 C59 -178.8(3) . . . .
C9 C8 N1 N2 0.2(2) . . . .
C10 C8 N1 N2 -177.80(19) . . . .
C9 C8 N1 C5 176.03(18) . . . .
C10 C8 N1 C5 -2.0(3) . . . .
C6 C5 N1 C8 -129.4(2) . . . .
C4 C5 N1 C8 49.8(3) . . . .
C6 C5 N1 N2 46.1(3) . . . .
C4 C5 N1 N2 -134.7(2) . . . .
C8 N1 N2 N3 -0.3(2) . . . .
C5 N1 N2 N3 -176.55(17) . . . .
N1 N2 N3 C9 0.2(2) . . . .
C8 C9 N3 N2 -0.1(2) . . . .
C11 C9 N3 N2 177.56(18) . . . .
C12 C11 N4 N5 -0.5(2) . . . .
C9 C11 N4 N5 179.53(17) . . . .
C12 C13 N5 N4 -0.4(2) . . . .
C12 C13 N5 C15 178.58(19) . . . .
C11 N4 N5 C13 0.6(2) . . . .
C11 N4 N5 C15 -178.53(17) . . . .
C16 C15 N5 C13 1.8(3) . . . .
C20 C15 N5 C13 -176.6(2) . . . .
C16 C15 N5 N4 -179.20(19) . . . .
C20 C15 N5 N4 2.4(3) . . . .
C29 C28 N6 N7 -0.9(2) . . . .
C30 C28 N6 N7 175.65(19) . . . .
C29 C28 N6 C25 173.38(18) . . . .
C30 C28 N6 C25 -10.1(3) . . . .
C26 C25 N6 C28 133.2(2) . . . .
C24 C25 N6 C28 -50.2(3) . . . .
C26 C25 N6 N7 -52.8(3) . . . .
C24 C25 N6 N7 123.8(2) . . . .
C28 N6 N7 N8 0.5(2) . . . .
C25 N6 N7 N8 -174.50(16) . . . .
N6 N7 N8 C29 0.1(2) . . . .
C28 C29 N8 N7 -0.7(2) . . . .
C31 C29 N8 N7 176.06(17) . . . .
C32 C31 N9 N10 0.6(2) . . . .
C29 C31 N9 N10 176.81(16) . . . .
C32 C33 N10 N9 0.5(2) . . . .
C32 C33 N10 C35 178.84(18) . . . .
C31 N9 N10 C33 -0.7(2) . . . .
C31 N9 N10 C35 -179.18(16) . . . .
C40 C35 N10 C33 -13.2(3) . . . .
C36 C35 N10 C33 168.39(19) . . . .
C40 C35 N10 N9 164.97(17) . . . .
C36 C35 N10 N9 -13.4(3) . . . .
C49 C48 N11 N12 0.8(2) . . . .
C50 C48 N11 N12 -175.52(18) . . . .
C49 C48 N11 C45 -177.10(18) . . . .
C50 C48 N11 C45 6.5(3) . . . .
C44 C45 N11 C48 -123.8(2) . . . .
C46 C45 N11 C48 57.6(3) . . . .
C44 C45 N11 N12 58.4(3) . . . .
C46 C45 N11 N12 -120.2(2) . . . .
C48 N11 N12 N13 -0.7(2) . . . .
C45 N11 N12 N13 177.44(17) . . . .
N11 N12 N13 C49 0.3(2) . . . .
C48 C49 N13 N12 0.2(2) . . . .
C51 C49 N13 N12 -179.45(18) . . . .
C52 C51 N14 N15 0.2(2) . . . .
C49 C51 N14 N15 179.89(17) . . . .
C52 C53 N15 N14 -0.3(2) . . . .
C52 C53 N15 C55 -179.82(19) . . . .
C51 N14 N15 C53 0.1(2) . . . .
C51 N14 N15 C55 179.65(17) . . . .
C60 C55 N15 C53 -178.8(2) . . . .
C56 C55 N15 C53 1.3(3) . . . .
C60 C55 N15 N14 1.7(3) . . . .
C56 C55 N15 N14 -178.14(19) . . . .
