#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128344.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_7128344
loop_
_publ_author_name
'Liang, Qiuming'
'Hayashi, Kasumi'
'Zeng, Yimin'
'Jimenez-Santiago, Jose L'
'Song, Datong'
_publ_section_title
;
 Constructing fused N-heterocycles from unprotected mesoionic
 N-heterocyclic olefins and organic azides via diazo transfer.
;
_journal_issue                   50
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6137
_journal_page_last               6140
_journal_paper_doi               10.1039/d1cc02245h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C17 H12 F3 N5'
_chemical_formula_weight         343.32
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                115.153(14)
_cell_angle_beta                 99.218(15)
_cell_angle_gamma                109.557(14)
_cell_formula_units_Z            4
_cell_length_a                   11.812(6)
_cell_length_b                   11.965(6)
_cell_length_c                   13.312(6)
_cell_measurement_reflns_used    32131
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.560
_cell_measurement_theta_min      2.107
_cell_volume                     1500.5(13)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32131
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.107
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0614
_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)+(0.0398P)²+1.5345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4525
_reflns_number_total             6893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl482
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_original_cell_volume        1500.4(12)
_cod_database_code               7128344
_shelx_shelxl_version_number     2016/6
_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   0.964
_shelx_estimated_absorpt_t_max   0.988
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
F1 F -0.02979(15) 0.12755(18) 0.08721(16) 0.0450(5) Uani 1 1 d . . . . .
N1 N 0.32985(19) -0.0123(2) 0.59073(18) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.8039(3) 0.2866(3) 0.7681(2) 0.0342(6) Uani 1 1 d . . . . .
H1 H 0.820479 0.334885 0.726868 0.041 Uiso 1 1 calc R U . . .
F2 F -0.15473(16) -0.08351(17) 0.02469(14) 0.0436(4) Uani 1 1 d . . . . .
N2 N 0.2243(2) -0.0402(2) 0.51277(18) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.9045(3) 0.3105(3) 0.8569(3) 0.0395(7) Uani 1 1 d . . . . .
H2 H 0.989486 0.374738 0.875418 0.047 Uiso 1 1 calc R U . . .
F3 F -0.17278(16) 0.07813(18) 0.16251(15) 0.0428(4) Uani 1 1 d . . . . .
N3 N 0.26412(19) 0.0411(2) 0.46733(18) 0.0238(5) Uani 1 1 d . . . . .
C3 C 0.8830(3) 0.2423(3) 0.9185(3) 0.0374(7) Uani 1 1 d . . . . .
H3 H 0.952326 0.260315 0.979939 0.045 Uiso 1 1 calc R U . . .
F4 F 0.10834(16) 0.58268(17) 0.42730(15) 0.0448(4) Uani 1 1 d . . . . .
N4 N 0.5969(2) 0.2435(2) 0.59144(19) 0.0279(5) Uani 1 1 d . . . . .
C4 C 0.7601(3) 0.1481(3) 0.8901(2) 0.0365(7) Uani 1 1 d . . . . .
H4 H 0.744349 0.100361 0.931928 0.044 Uiso 1 1 calc R U . . .
F5 F 0.12464(19) 0.42415(19) 0.28504(15) 0.0506(5) Uani 1 1 d . . . . .
N5 N 0.48669(19) 0.2128(2) 0.50894(19) 0.0269(5) Uani 1 1 d . . . . .
C5 C 0.6587(3) 0.1221(3) 0.8006(2) 0.0289(6) Uani 1 1 d . . . . .
H5 H 0.574399 0.055459 0.780934 0.035 Uiso 1 1 calc R U . . .
F6 F -0.02168(16) 0.3705(2) 0.35675(17) 0.0552(5) Uani 1 1 d . . . . .
N6 N 0.61939(19) 0.5113(2) 0.85820(18) 0.0260(5) Uani 1 1 d . . . . .
C6 C 0.6787(2) 0.1922(2) 0.7392(2) 0.0245(5) Uani 1 1 d . . . . .
N7 N 0.5711(2) 0.5348(2) 0.77624(19) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.5726(2) 0.1704(2) 0.6465(2) 0.0238(5) Uani 1 1 d . . . . .
N8 N 0.44485(19) 0.4461(2) 0.72635(19) 0.0254(5) Uani 1 1 d . . . . .
C8 C 0.4383(2) 0.0853(2) 0.5980(2) 0.0230(5) Uani 1 1 d . . . . .
N9 N 0.3640(2) 0.2423(2) 0.85482(19) 0.0278(5) Uani 1 1 d . . . . .
C9 C 0.3946(2) 0.1189(2) 0.5166(2) 0.0232(5) Uani 1 1 d . . . . .
N10 N 0.3123(2) 0.2667(2) 0.76836(19) 0.0270(5) Uani 1 1 d . . . . .
C10 C 0.1736(2) 0.0395(2) 0.3808(2) 0.0239(5) Uani 1 1 d . . . . .
C11 C 0.0428(2) -0.0349(3) 0.3497(2) 0.0295(6) Uani 1 1 d . . . . .
H11 H 0.010914 -0.086623 0.385408 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0405(3) -0.0327(3) 0.2659(2) 0.0308(6) Uani 1 1 d . . . . .
H12 H -0.130673 -0.083391 0.243338 0.037 Uiso 1 1 calc R U . . .
C13 C 0.0074(2) 0.0433(3) 0.2149(2) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.1380(2) 0.1173(3) 0.2464(2) 0.0280(6) Uani 1 1 d . . . . .
H14 H 0.169705 0.168895 0.210512 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2234(2) 0.1160(3) 0.3311(2) 0.0270(6) Uani 1 1 d . . . . .
H15 H 0.313594 0.166710 0.353930 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0851(2) 0.0425(3) 0.1237(2) 0.0291(6) Uani 1 1 d . . . . .
C17 C 0.3156(3) -0.0888(3) 0.6526(2) 0.0313(6) Uani 1 1 d . . . . .
H17A H 0.225020 -0.154480 0.624306 0.047 Uiso 1 1 calc R U . . .
H17B H 0.344945 -0.023996 0.738155 0.047 Uiso 1 1 calc R U . . .
H17C H 0.367233 -0.139241 0.637046 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4996(3) 0.2090(3) 1.0281(3) 0.0362(7) Uani 1 1 d . . . . .
H18 H 0.410814 0.148148 0.984138 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5646(3) 0.1933(3) 1.1135(3) 0.0435(7) Uani 1 1 d . . . . .
H19 H 0.520085 0.122059 1.127376 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6941(3) 0.2808(3) 1.1789(2) 0.0378(7) Uani 1 1 d . . . . .
H20 H 0.739167 0.270393 1.237558 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7561(3) 0.3836(3) 1.1567(3) 0.0381(7) Uani 1 1 d . . . . .
H21 H 0.845012 0.444034 1.200320 0.046 Uiso 1 1 calc R U . . .
C22 C 0.6911(3) 0.3999(3) 1.0723(2) 0.0340(6) Uani 1 1 d . . . . .
H22 H 0.735540 0.472312 1.059720 0.041 Uiso 1 1 calc R U . . .
C23 C 0.5618(2) 0.3120(3) 1.0055(2) 0.0276(6) Uani 1 1 d . . . . .
C24 C 0.4914(2) 0.3245(2) 0.9133(2) 0.0249(5) Uani 1 1 d . . . . .
C25 C 0.5289(2) 0.4095(2) 0.8639(2) 0.0245(5) Uani 1 1 d . . . . .
C26 C 0.4153(2) 0.3674(2) 0.7786(2) 0.0248(5) Uani 1 1 d . . . . .
C27 C 0.3607(2) 0.4463(2) 0.6373(2) 0.0257(5) Uani 1 1 d . . . . .
C28 C 0.2309(2) 0.3612(3) 0.5989(2) 0.0273(6) Uani 1 1 d . . . . .
H28 H 0.200809 0.301607 0.628437 0.033 Uiso 1 1 calc R U . . .
C29 C 0.1453(2) 0.3638(3) 0.5169(2) 0.0288(6) Uani 1 1 d . . . . .
H29 H 0.055726 0.307058 0.490711 0.035 Uiso 1 1 calc R U . . .
C30 C 0.1905(3) 0.4492(3) 0.4732(2) 0.0290(6) Uani 1 1 d . . . . .
C31 C 0.3217(3) 0.5316(3) 0.5101(2) 0.0313(6) Uani 1 1 d . . . . .
H31 H 0.352262 0.588242 0.478113 0.038 Uiso 1 1 calc R U . . .
C32 C 0.4073(3) 0.5309(3) 0.5934(2) 0.0319(6) Uani 1 1 d . . . . .
H32 H 0.496897 0.587907 0.620017 0.038 Uiso 1 1 calc R U . . .
C33 C 0.1003(3) 0.4562(3) 0.3858(3) 0.0346(6) Uani 1 1 d . . . . .
C34 C 0.7567(2) 0.5964(3) 0.9279(2) 0.0325(6) Uani 1 1 d . . . . .
H34A H 0.798164 0.536340 0.921624 0.049 Uiso 1 1 calc R U . . .
H34B H 0.768730 0.654110 1.011219 0.049 Uiso 1 1 calc R U . . .
H34C H 0.795246 0.655660 0.897520 0.049 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
N2 N1 C8 112.6(2) . . ?
N2 N1 C17 117.4(2) . . ?
C8 N1 C17 130.0(2) . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
N1 N2 N3 105.40(19) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
N2 N3 C9 110.8(2) . . ?
N2 N3 C10 120.6(2) . . ?
C9 N3 C10 128.6(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C7 N4 N5 112.5(2) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C9 N5 N4 103.1(2) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N7 N6 C25 112.7(2) . . ?
N7 N6 C34 117.0(2) . . ?
C25 N6 C34 130.3(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 122.4(2) . . ?
C1 C6 C7 119.6(2) . . ?
N6 N7 N8 105.60(19) . . ?
N4 C7 C8 106.6(2) . . ?
N4 C7 C6 120.0(2) . . ?
C8 C7 C6 133.4(2) . . ?
N7 N8 C26 110.1(2) . . ?
N7 N8 C27 121.2(2) . . ?
C26 N8 C27 128.6(2) . . ?
N1 C8 C9 104.7(2) . . ?
N1 C8 C7 151.9(2) . . ?
C9 C8 C7 103.4(2) . . ?
C24 N9 N10 112.9(2) . . ?
N5 C9 N3 139.2(2) . . ?
N5 C9 C8 114.4(2) . . ?
N3 C9 C8 106.5(2) . . ?
C26 N10 N9 102.1(2) . . ?
C15 C10 C11 122.1(2) . . ?
C15 C10 N3 116.7(2) . . ?
C11 C10 N3 121.1(2) . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 C16 120.4(2) . . ?
C12 C13 C16 118.7(2) . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 118.4(2) . . ?
C10 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1 C16 F3 106.4(2) . . ?
F1 C16 F2 105.8(2) . . ?
F3 C16 F2 104.7(2) . . ?
F1 C16 C13 113.9(2) . . ?
F3 C16 C13 112.4(2) . . ?
F2 C16 C13 113.0(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C23 C18 H18 119.4 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 117.8(3) . . ?
C22 C23 C24 122.1(2) . . ?
C18 C23 C24 120.1(2) . . ?
N9 C24 C25 106.3(2) . . ?
N9 C24 C23 120.4(2) . . ?
C25 C24 C23 133.3(2) . . ?
N6 C25 C26 104.9(2) . . ?
N6 C25 C24 151.6(2) . . ?
C26 C25 C24 103.6(2) . . ?
N10 C26 N8 138.1(2) . . ?
N10 C26 C25 115.2(2) . . ?
N8 C26 C25 106.7(2) . . ?
C32 C27 C28 121.6(3) . . ?
C32 C27 N8 120.9(2) . . ?
C28 C27 N8 117.4(2) . . ?
C29 C28 C27 119.1(2) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 C33 121.2(2) . . ?
C31 C30 C33 118.4(2) . . ?
C32 C31 C30 119.9(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C27 C32 C31 119.0(2) . . ?
C27 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
F6 C33 F4 106.9(2) . . ?
F6 C33 F5 107.2(2) . . ?
F4 C33 F5 105.5(2) . . ?
F6 C33 C30 112.0(2) . . ?
F4 C33 C30 112.4(2) . . ?
F5 C33 C30 112.3(2) . . ?
N6 C34 H34A 109.5 . . ?
N6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.332(3) . ?
N1 N2 1.325(3) . ?
N1 C8 1.370(3) . ?
N1 C17 1.459(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.393(4) . ?
C1 H1 0.9500 . ?
F2 C16 1.349(3) . ?
N2 N3 1.348(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
F3 C16 1.342(3) . ?
N3 C9 1.367(3) . ?
N3 C10 1.429(3) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
F4 C33 1.335(3) . ?
N4 C7 1.351(3) . ?
N4 N5 1.384(3) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
F5 C33 1.338(3) . ?
N5 C9 1.330(3) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
F6 C33 1.331(3) . ?
N6 N7 1.328(3) . ?
N6 C25 1.365(3) . ?
N6 C34 1.462(3) . ?
C6 C7 1.475(3) . ?
N7 N8 1.347(3) . ?
C7 C8 1.414(3) . ?
N8 C26 1.381(3) . ?
N8 C27 1.421(3) . ?
C8 C9 1.391(3) . ?
N9 C24 1.350(3) . ?
N9 N10 1.401(3) . ?
N10 C26 1.333(3) . ?
C10 C15 1.379(3) . ?
C10 C11 1.383(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(4) . ?
C13 C16 1.493(4) . ?
C14 C15 1.396(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.383(4) . ?
C18 C23 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.461(4) . ?
C24 C25 1.423(4) . ?
C25 C26 1.385(4) . ?
C27 C32 1.379(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.382(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(4) . ?
C30 C33 1.496(4) . ?
C31 C32 1.380(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
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
_geom_torsion_publ_flag
C8 N1 N2 N3 0.0(3) . . . . ?
C17 N1 N2 N3 -178.7(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 N2 N3 C9 0.4(3) . . . . ?
N1 N2 N3 C10 -178.79(19) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C7 N4 N5 C9 0.3(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -177.9(2) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 C6 C7 178.7(2) . . . . ?
C25 N6 N7 N8 0.2(3) . . . . ?
C34 N6 N7 N8 -179.2(2) . . . . ?
N5 N4 C7 C8 0.2(3) . . . . ?
N5 N4 C7 C6 -178.7(2) . . . . ?
C5 C6 C7 N4 178.5(2) . . . . ?
C1 C6 C7 N4 -1.0(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C1 C6 C7 C8 -179.5(3) . . . . ?
N6 N7 N8 C26 0.1(3) . . . . ?
N6 N7 N8 C27 177.3(2) . . . . ?
N2 N1 C8 C9 -0.4(3) . . . . ?
C17 N1 C8 C9 178.1(2) . . . . ?
N2 N1 C8 C7 179.0(4) . . . . ?
C17 N1 C8 C7 -2.5(6) . . . . ?
N4 C7 C8 N1 180.0(4) . . . . ?
C6 C7 C8 N1 -1.4(7) . . . . ?
N4 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 178.0(2) . . . . ?
N4 N5 C9 N3 179.3(3) . . . . ?
N4 N5 C9 C8 -0.7(3) . . . . ?
N2 N3 C9 N5 179.4(3) . . . . ?
C10 N3 C9 N5 -1.5(5) . . . . ?
N2 N3 C9 C8 -0.6(3) . . . . ?
C10 N3 C9 C8 178.5(2) . . . . ?
N1 C8 C9 N5 -179.4(2) . . . . ?
C7 C8 C9 N5 0.9(3) . . . . ?
N1 C8 C9 N3 0.6(2) . . . . ?
C7 C8 C9 N3 -179.14(19) . . . . ?
C24 N9 N10 C26 -0.1(3) . . . . ?
N2 N3 C10 C15 -174.2(2) . . . . ?
C9 N3 C10 C15 6.8(4) . . . . ?
N2 N3 C10 C11 6.1(3) . . . . ?
C9 N3 C10 C11 -172.9(2) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
N3 C10 C11 C12 179.8(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C11 C12 C13 C16 179.4(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C16 C13 C14 C15 -179.4(2) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
N3 C10 C15 C14 -179.9(2) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C14 C13 C16 F1 -5.9(3) . . . . ?
C12 C13 C16 F1 174.8(2) . . . . ?
C14 C13 C16 F3 -127.0(3) . . . . ?
C12 C13 C16 F3 53.7(3) . . . . ?
C14 C13 C16 F2 114.8(3) . . . . ?
C12 C13 C16 F2 -64.4(3) . . . . ?
C23 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -1.1(4) . . . . ?
C21 C22 C23 C18 1.2(4) . . . . ?
C21 C22 C23 C24 -178.3(2) . . . . ?
C19 C18 C23 C22 -0.7(4) . . . . ?
C19 C18 C23 C24 178.8(3) . . . . ?
N10 N9 C24 C25 -0.1(3) . . . . ?
N10 N9 C24 C23 -179.1(2) . . . . ?
C22 C23 C24 N9 -176.2(2) . . . . ?
C18 C23 C24 N9 4.3(4) . . . . ?
C22 C23 C24 C25 5.2(4) . . . . ?
C18 C23 C24 C25 -174.3(3) . . . . ?
N7 N6 C25 C26 -0.4(3) . . . . ?
C34 N6 C25 C26 178.9(2) . . . . ?
N7 N6 C25 C24 -179.8(4) . . . . ?
C34 N6 C25 C24 -0.6(6) . . . . ?
N9 C24 C25 N6 179.7(4) . . . . ?
C23 C24 C25 N6 -1.5(7) . . . . ?
N9 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 C26 179.1(3) . . . . ?
N9 N10 C26 N8 179.6(3) . . . . ?
N9 N10 C26 C25 0.3(3) . . . . ?
N7 N8 C26 N10 -179.7(3) . . . . ?
C27 N8 C26 N10 3.4(5) . . . . ?
N7 N8 C26 C25 -0.3(3) . . . . ?
C27 N8 C26 C25 -177.2(2) . . . . ?
N6 C25 C26 N10 179.9(2) . . . . ?
C24 C25 C26 N10 -0.4(3) . . . . ?
N6 C25 C26 N8 0.4(3) . . . . ?
C24 C25 C26 N8 -179.9(2) . . . . ?
N7 N8 C27 C32 4.4(3) . . . . ?
C26 N8 C27 C32 -178.9(2) . . . . ?
N7 N8 C27 C28 -174.0(2) . . . . ?
C26 N8 C27 C28 2.6(4) . . . . ?
C32 C27 C28 C29 -1.8(4) . . . . ?
N8 C27 C28 C29 176.6(2) . . . . ?
C27 C28 C29 C30 1.1(4) . . . . ?
C28 C29 C30 C31 0.7(4) . . . . ?
C28 C29 C30 C33 -179.0(2) . . . . ?
C29 C30 C31 C32 -1.7(4) . . . . ?
C33 C30 C31 C32 178.0(2) . . . . ?
C28 C27 C32 C31 0.8(4) . . . . ?
N8 C27 C32 C31 -177.6(2) . . . . ?
C30 C31 C32 C27 0.9(4) . . . . ?
C29 C30 C33 F6 -1.4(4) . . . . ?
C31 C30 C33 F6 178.9(2) . . . . ?
C29 C30 C33 F4 119.0(3) . . . . ?
C31 C30 C33 F4 -60.7(3) . . . . ?
C29 C30 C33 F5 -122.2(3) . . . . ?
C31 C30 C33 F5 58.1(3) . . . . ?
