#------------------------------------------------------------------------------
#$Date: 2022-09-20 12:16:34 +0300 (Tue, 20 Sep 2022) $
#$Revision: 278002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105801.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_8105801
loop_
_publ_author_name
'Yerima, Iliya B.'
'Zamisa, Sizwe J.'
'Bala, Muhammad D.'
_publ_section_title
;
 Crystal structure of
 4-tert-butyl-1-(2,6-dimethylphenyl)-1H-1,2,3-triazole, C14H19N3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              625
_journal_page_last               627
_journal_paper_doi               10.1515/ncrs-2018-0574
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C14 H19 N3'
_chemical_formula_sum            'C14 H19 N3'
_chemical_formula_weight         229.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.2821(8)
_cell_length_b                   10.8464(4)
_cell_length_c                   10.8509(4)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.62
_cell_volume                     2622.45(17)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            72736
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.620
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5979
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0551P)²+0.4612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5773
_reflns_number_total             5979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0574_suppl.cif
_cod_data_source_block           tbutyltriazole
_cod_database_code               8105801
_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_max   0.983
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C18(H18), C19(H19), C20(H20), C24(H24)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C1 C 0.70307(7) 0.38396(14) 0.43648(14) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.75697(7) 0.42424(14) 0.38431(15) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.81006(7) 0.37433(16) 0.43103(16) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.847534 0.400505 0.398486 0.026 Uiso 1 1 calc R . . . .
C4 C 0.80877(8) 0.28688(15) 0.52451(16) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.845282 0.253377 0.554884 0.025 Uiso 1 1 calc R . . . .
C5 C 0.75470(7) 0.24828(14) 0.57362(16) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.754479 0.188168 0.637296 0.023 Uiso 1 1 calc R . . . .
C6 C 0.70054(7) 0.29626(15) 0.53110(15) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.64183(8) 0.25353(17) 0.58471(18) 0.0268(4) Uani 1 1 d . . . . .
H7A H 0.649477 0.191681 0.648647 0.040 Uiso 1 1 calc GR . . . .
H7B H 0.617114 0.217135 0.519466 0.040 Uiso 1 1 calc GR . . . .
H7C H 0.620667 0.323962 0.620934 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.75829(8) 0.51641(16) 0.28038(17) 0.0236(3) Uani 1 1 d . . . . .
H8A H 0.799164 0.522335 0.247580 0.035 Uiso 1 1 calc GR . . . .
H8B H 0.745587 0.597269 0.311116 0.035 Uiso 1 1 calc GR . . . .
H8C H 0.730970 0.489565 0.214887 0.035 Uiso 1 1 calc GR . . . .
C9 C 0.60965(7) 0.38343(14) 0.30650(15) 0.0163(3) Uani 1 1 d . . . . .
H9 H 0.610986 0.302391 0.273389 0.020 Uiso 1 1 calc R . . . .
C10 C 0.56838(7) 0.47402(14) 0.28144(14) 0.0143(3) Uani 1 1 d . . . . .
C11 C 0.51467(7) 0.47172(14) 0.19617(15) 0.0157(3) Uani 1 1 d . . . . .
C12 C 0.51446(7) 0.58739(15) 0.11468(16) 0.0208(3) Uani 1 1 d . . . . .
H12A H 0.479566 0.585237 0.059752 0.031 Uiso 1 1 calc R . . . .
H12B H 0.512382 0.661013 0.166865 0.031 Uiso 1 1 calc R . . . .
H12C H 0.551300 0.589776 0.065405 0.031 Uiso 1 1 calc R . . . .
C14 C 0.45680(7) 0.46738(18) 0.27213(17) 0.0256(4) Uani 1 1 d . . . . .
H14A H 0.422132 0.465898 0.216583 0.038 Uiso 1 1 calc R . . . .
H14B H 0.456675 0.392995 0.323397 0.038 Uiso 1 1 calc R . . . .
H14C H 0.454563 0.540467 0.325029 0.038 Uiso 1 1 calc R . . . .
C15 C 0.51814(8) 0.35765(15) 0.11334(17) 0.0220(3) Uani 1 1 d . . . . .
H15A H 0.483362 0.356081 0.058071 0.033 Uiso 1 1 calc R . . . .
H15B H 0.555082 0.360666 0.064420 0.033 Uiso 1 1 calc R . . . .
H15C H 0.518192 0.283194 0.164502 0.033 Uiso 1 1 calc R . . . .
C16 C 0.71746(7) 0.87876(15) 0.20703(15) 0.0160(3) Uani 1 1 d . . . . .
C17 C 0.76986(7) 0.92056(15) 0.26432(16) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.82418(8) 0.87134(16) 0.22288(18) 0.0245(4) Uani 1 1 d . . . . .
H18 H 0.860739 0.898255 0.259025 0.029 Uiso 1 1 calc R . . . .
C19 C 0.82554(8) 0.78391(16) 0.12989(17) 0.0236(4) Uani 1 1 d . . . . .
H19 H 0.862911 0.751458 0.103002 0.028 Uiso 1 1 calc R . . . .
C20 C 0.77282(7) 0.74349(15) 0.07588(16) 0.0204(3) Uani 1 1 d . . . . .
H20 H 0.774318 0.683305 0.012346 0.025 Uiso 1 1 calc R . . . .
C21 C 0.71747(7) 0.79031(14) 0.11387(15) 0.0176(3) Uani 1 1 d . . . . .
C22 C 0.66043(8) 0.74362(18) 0.05665(18) 0.0274(4) Uani 1 1 d . . . . .
H22A H 0.632178 0.812152 0.046687 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.642598 0.680660 0.110074 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.669308 0.707612 -0.024154 0.041 Uiso 1 1 calc GR . . . .
C23 C 0.76827(8) 1.01344(17) 0.36751(18) 0.0265(4) Uani 1 1 d . . . . .
H23A H 0.758927 1.095102 0.333969 0.040 Uiso 1 1 calc GR . . . .
H23B H 0.807464 1.015846 0.408408 0.040 Uiso 1 1 calc GR . . . .
H23C H 0.737372 0.989778 0.427288 0.040 Uiso 1 1 calc GR . . . .
C24 C 0.61704(7) 0.88303(14) 0.31517(15) 0.0170(3) Uani 1 1 d . . . . .
H24 H 0.615105 0.801986 0.348126 0.020 Uiso 1 1 calc R . . . .
C25 C 0.57548(7) 0.97587(14) 0.32809(14) 0.0149(3) Uani 1 1 d . . . . .
C27 C 0.51724(7) 0.97660(14) 0.39987(15) 0.0159(3) Uani 1 1 d . . . . .
C28 C 0.48538(7) 1.10062(16) 0.38487(17) 0.0225(3) Uani 1 1 d . . . . .
H28A H 0.447791 1.099795 0.431762 0.034 Uiso 1 1 calc R . . . .
H28B H 0.511319 1.166726 0.415733 0.034 Uiso 1 1 calc R . . . .
H28C H 0.476612 1.114790 0.297509 0.034 Uiso 1 1 calc R . . . .
C29 C 0.53173(8) 0.95632(16) 0.53691(15) 0.0210(3) Uani 1 1 d . . . . .
H29A H 0.494408 0.956556 0.584708 0.031 Uiso 1 1 calc R . . . .
H29B H 0.552024 0.876839 0.547238 0.031 Uiso 1 1 calc R . . . .
H29C H 0.557979 1.022655 0.566136 0.031 Uiso 1 1 calc R . . . .
C30 C 0.47648(7) 0.87174(16) 0.35522(16) 0.0221(3) Uani 1 1 d . . . . .
H30A H 0.438885 0.872816 0.402090 0.033 Uiso 1 1 calc R . . . .
H30B H 0.467739 0.882880 0.267407 0.033 Uiso 1 1 calc R . . . .
H30C H 0.496764 0.792545 0.367634 0.033 Uiso 1 1 calc R . . . .
N1 N 0.64796(6) 0.43451(12) 0.38848(12) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.63172(6) 0.55171(13) 0.41429(13) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.58322(6) 0.57529(12) 0.34949(13) 0.0181(3) Uani 1 1 d . . . . .
N4 N 0.66117(6) 0.93211(12) 0.24546(13) 0.0166(3) Uani 1 1 d . . . . .
N5 N 0.64846(6) 1.04973(13) 0.21523(15) 0.0232(3) Uani 1 1 d . . . . .
N6 N 0.59617(6) 1.07586(12) 0.26556(15) 0.0210(3) 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'
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 C6 122.94(14) . .
C2 C1 N1 117.80(14) . .
C6 C1 N1 119.25(14) . .
C1 C2 C8 121.81(14) . .
C3 C2 C1 117.37(14) . .
C3 C2 C8 120.82(15) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.82(15) . .
C4 C3 H3 119.6 . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.42(15) . .
C5 C4 H4 119.8 . .
C4 C5 H5 119.5 . .
C4 C5 C6 120.95(15) . .
C6 C5 H5 119.5 . .
C1 C6 C7 121.83(14) . .
C5 C6 C1 117.49(14) . .
C5 C6 C7 120.67(15) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C2 C8 H8A 109.5 . .
C2 C8 H8B 109.5 . .
C2 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 H9 127.5 . .
N1 C9 H9 127.5 . .
N1 C9 C10 105.07(13) . .
C9 C10 C11 129.72(14) . .
N3 C10 C9 107.87(13) . .
N3 C10 C11 122.41(13) . .
C10 C11 C12 109.95(13) . .
C10 C11 C14 109.73(13) . .
C10 C11 C15 109.41(13) . .
C14 C11 C12 109.43(14) . .
C14 C11 C15 109.49(14) . .
C15 C11 C12 108.81(14) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 C15 H15A 109.5 . .
C11 C15 H15B 109.5 . .
C11 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N4 117.86(14) . .
C21 C16 C17 123.06(14) . .
C21 C16 N4 119.08(14) . .
C16 C17 C23 121.84(15) . .
C18 C17 C16 117.16(15) . .
C18 C17 C23 121.00(15) . .
C17 C18 H18 119.5 . .
C19 C18 C17 120.99(16) . .
C19 C18 H18 119.5 . .
C18 C19 H19 119.8 . .
C20 C19 C18 120.46(15) . .
C20 C19 H19 119.8 . .
C19 C20 H20 119.7 . .
C19 C20 C21 120.63(16) . .
C21 C20 H20 119.7 . .
C16 C21 C20 117.70(15) . .
C16 C21 C22 122.11(14) . .
C20 C21 C22 120.18(15) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C17 C23 H23A 109.5 . .
C17 C23 H23B 109.5 . .
C17 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C25 C24 H24 127.5 . .
N4 C24 H24 127.5 . .
N4 C24 C25 105.00(13) . .
C24 C25 C27 129.32(14) . .
N6 C25 C24 107.76(14) . .
N6 C25 C27 122.90(13) . .
C25 C27 C28 110.35(13) . .
C25 C27 C29 108.48(12) . .
C25 C27 C30 109.95(13) . .
C28 C27 C29 109.03(13) . .
C28 C27 C30 110.10(13) . .
C30 C27 C29 108.89(13) . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C27 C29 H29A 109.5 . .
C27 C29 H29B 109.5 . .
C27 C29 H29C 109.5 . .
H29A C29 H29B 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C27 C30 H30A 109.5 . .
C27 C30 H30B 109.5 . .
C27 C30 H30C 109.5 . .
H30A C30 H30B 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C9 N1 C1 128.29(13) . .
N2 N1 C1 120.72(12) . .
N2 N1 C9 110.67(13) . .
N3 N2 N1 107.00(12) . .
N2 N3 C10 109.39(13) . .
C24 N4 C16 129.57(13) . .
N5 N4 C16 119.48(13) . .
N5 N4 C24 110.89(13) . .
N6 N5 N4 106.78(13) . .
N5 N6 C25 109.57(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.398(2) .
C1 C6 1.401(2) .
C1 N1 1.4422(19) .
C2 C3 1.396(2) .
C2 C8 1.507(2) .
C3 H3 0.9500 .
C3 C4 1.389(2) .
C4 H4 0.9500 .
C4 C5 1.382(2) .
C5 H5 0.9500 .
C5 C6 1.393(2) .
C6 C7 1.505(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9 0.9500 .
C9 C10 1.373(2) .
C9 N1 1.352(2) .
C10 C11 1.513(2) .
C10 N3 1.364(2) .
C11 C12 1.535(2) .
C11 C14 1.531(2) .
C11 C15 1.531(2) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.398(2) .
C16 C21 1.394(2) .
C16 N4 1.4428(19) .
C17 C18 1.397(2) .
C17 C23 1.507(2) .
C18 H18 0.9500 .
C18 C19 1.385(3) .
C19 H19 0.9500 .
C19 C20 1.384(2) .
C20 H20 0.9500 .
C20 C21 1.396(2) .
C21 C22 1.502(2) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24 0.9500 .
C24 C25 1.375(2) .
C24 N4 1.350(2) .
C25 C27 1.514(2) .
C25 N6 1.360(2) .
C27 C28 1.530(2) .
C27 C29 1.537(2) .
C27 C30 1.534(2) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
N1 N2 1.3511(19) .
N2 N3 1.3146(19) .
N4 N5 1.3474(19) .
N5 N6 1.318(2) .
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
C24 H24 N3 0.95 2.56 3.442(2) 154.6 .
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
C1 C2 C3 C4 0.9(2) . . . .
C1 N1 N2 N3 174.21(13) . . . .
C2 C1 C6 C5 0.0(2) . . . .
C2 C1 C6 C7 -179.35(16) . . . .
C2 C1 N1 C9 99.55(19) . . . .
C2 C1 N1 N2 -73.31(19) . . . .
C2 C3 C4 C5 -0.5(3) . . . .
C3 C4 C5 C6 -0.2(3) . . . .
C4 C5 C6 C1 0.5(2) . . . .
C4 C5 C6 C7 179.81(16) . . . .
C6 C1 C2 C3 -0.6(2) . . . .
C6 C1 C2 C8 178.45(15) . . . .
C6 C1 N1 C9 -79.6(2) . . . .
C6 C1 N1 N2 107.59(17) . . . .
C8 C2 C3 C4 -178.23(15) . . . .
C9 C10 C11 C12 -131.93(17) . . . .
C9 C10 C11 C14 107.66(19) . . . .
C9 C10 C11 C15 -12.5(2) . . . .
C9 C10 N3 N2 0.47(18) . . . .
C9 N1 N2 N3 0.19(18) . . . .
C10 C9 N1 C1 -173.35(15) . . . .
C10 C9 N1 N2 0.09(18) . . . .
C11 C10 N3 N2 -179.68(14) . . . .
C16 C17 C18 C19 -0.7(3) . . . .
C16 N4 N5 N6 -177.49(14) . . . .
C17 C16 C21 C20 -0.9(2) . . . .
C17 C16 C21 C22 177.86(16) . . . .
C17 C16 N4 C24 -106.13(19) . . . .
C17 C16 N4 N5 70.8(2) . . . .
C17 C18 C19 C20 0.1(3) . . . .
C18 C19 C20 C21 0.2(3) . . . .
C19 C20 C21 C16 0.2(2) . . . .
C19 C20 C21 C22 -178.58(16) . . . .
C21 C16 C17 C18 1.2(2) . . . .
C21 C16 C17 C23 -178.08(15) . . . .
C21 C16 N4 C24 75.0(2) . . . .
C21 C16 N4 N5 -108.07(18) . . . .
C23 C17 C18 C19 178.54(16) . . . .
C24 C25 C27 C28 -178.96(17) . . . .
C24 C25 C27 C29 61.7(2) . . . .
C24 C25 C27 C30 -57.3(2) . . . .
C24 C25 N6 N5 -0.30(19) . . . .
C24 N4 N5 N6 -0.03(19) . . . .
C25 C24 N4 C16 176.99(15) . . . .
C25 C24 N4 N5 -0.15(19) . . . .
C27 C25 N6 N5 178.08(14) . . . .
N1 C1 C2 C3 -179.71(14) . . . .
N1 C1 C2 C8 -0.6(2) . . . .
N1 C1 C6 C5 179.04(14) . . . .
N1 C1 C6 C7 -0.3(2) . . . .
N1 C9 C10 C11 179.83(15) . . . .
N1 C9 C10 N3 -0.33(17) . . . .
N1 N2 N3 C10 -0.40(18) . . . .
N3 C10 C11 C12 48.3(2) . . . .
N3 C10 C11 C14 -72.15(19) . . . .
N3 C10 C11 C15 167.70(15) . . . .
N4 C16 C17 C18 -177.67(15) . . . .
N4 C16 C17 C23 3.1(2) . . . .
N4 C16 C21 C20 177.89(14) . . . .
N4 C16 C21 C22 -3.3(2) . . . .
N4 C24 C25 C27 -177.97(15) . . . .
N4 C24 C25 N6 0.27(18) . . . .
N4 N5 N6 C25 0.20(19) . . . .
N6 C25 C27 C28 3.0(2) . . . .
N6 C25 C27 C29 -116.34(17) . . . .
N6 C25 C27 C30 124.68(17) . . . .
