#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:08:58 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299121 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160344.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_7160344
loop_
_publ_author_name
'Guo, Xiaoshuang'
'Zhao, Peng'
'Jiang, Chengjun'
'Ma, Yongmin'
'Miao, Maozhong'
_publ_section_title
;
 Atmospheric oxygen mediated oxidation coupling of primary and secondary
 alcohols: synthesis of pyrazolo[1,5-a]pyrimidines.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2092
_journal_page_last               2095
_journal_paper_doi               10.1039/d4ob02045f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H14 F3 N3'
_chemical_formula_sum            'C16 H14 F3 N3'
_chemical_formula_weight         305.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2024-12-04 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.81(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.52(5)
_cell_length_b                   17.03(3)
_cell_length_c                   15.65(4)
_cell_measurement_reflns_used    220
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.456
_cell_measurement_theta_min      2.995
_cell_volume                     5803(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_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  0.0541
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.398
_diffrn_reflns_theta_min         1.518
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         8229
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0513
_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)+(0.0592P)²+2.3117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4743
_reflns_number_total             8229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob02045f2.cif
_cod_data_source_block           mo230825a
_cod_depositor_comments          'Adding full bibliography for 7160344.cif.'
_cod_original_cell_volume        5803(21)
_cod_database_code               7160344
_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_max   0.987
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F7-C32 \\sim F9-C32
 with sigma of 0.02
 F5-C32 \\sim F8-C32
 with sigma of 0.02
 F4-C32 \\sim F00F-C32
 with sigma of 0.02
3. Others
 Sof(F00F)=Sof(F8)=Sof(F9)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F7)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C13(H13a,H13b), C14(H14a,H14b)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C1(H1),
 C2(H2), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
4.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C15(H15a,H15b,H15c)
;
_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
F00F F 0.2051(3) 0.8994(5) 0.0015(7) 0.113(2) Uani 0.499(17) 1 d D . P A 2
F4 F 0.2681(4) 0.8462(5) 0.1202(5) 0.098(2) Uani 0.501(17) 1 d D . P A 1
F5 F 0.2777(6) 0.8329(4) 0.0010(11) 0.116(2) Uani 0.501(17) 1 d D . P A 1
F7 F 0.2022(2) 0.8950(4) -0.0238(7) 0.121(3) Uani 0.501(17) 1 d D . P A 1
F8 F 0.2812(5) 0.8320(6) 0.1033(10) 0.191(5) Uani 0.499(17) 1 d D . P A 2
F9 F 0.2563(6) 0.8591(9) -0.0528(11) 0.138(3) Uani 0.499(17) 1 d D . P A 2
N4 N 0.61883(6) 1.04560(8) 0.58234(11) 0.0544(4) Uani 1 1 d . . . . .
N5 N 0.56477(5) 1.03138(7) 0.48843(10) 0.0437(3) Uani 1 1 d . . . . .
N6 N 0.47657(6) 1.09796(7) 0.34525(10) 0.0475(3) Uani 1 1 d . . . . .
C17 C 0.61893(8) 1.12423(11) 0.58987(15) 0.0619(5) Uani 1 1 d . . . . .
H17 H 0.650691 1.151853 0.646591 0.074 Uiso 1 1 calc R U . . .
C18 C 0.56763(8) 1.16061(10) 0.50584(14) 0.0590(5) Uani 1 1 d . . . . .
H18 H 0.558971 1.214071 0.496254 0.071 Uiso 1 1 calc R U . . .
C19 C 0.53185(7) 1.09959(9) 0.43882(13) 0.0468(4) Uani 1 1 d . . . . .
C20 C 0.45471(7) 1.02819(8) 0.30210(12) 0.0428(3) Uani 1 1 d . . . . .
C21 C 0.39334(7) 1.02615(9) 0.20023(12) 0.0440(3) Uani 1 1 d . . . . .
C22 C 0.37025(8) 1.09272(10) 0.13639(13) 0.0560(4) Uani 1 1 d . . . . .
H22 H 0.393831 1.138191 0.156848 0.067 Uiso 1 1 calc R U . . .
C23 C 0.31251(9) 1.09161(11) 0.04287(14) 0.0661(5) Uani 1 1 d . . . . .
H23 H 0.297998 1.136368 0.001417 0.079 Uiso 1 1 calc R U . . .
C24 C 0.27642(8) 1.02531(11) 0.01056(13) 0.0618(5) Uani 1 1 d . . . . .
H24 H 0.237590 1.025163 -0.051751 0.074 Uiso 1 1 calc R U . . .
C25 C 0.29904(7) 0.95864(10) 0.07270(13) 0.0531(4) Uani 1 1 d . . . . .
C26 C 0.35704(7) 0.95907(9) 0.16660(12) 0.0493(4) Uani 1 1 d . . . . .
H26 H 0.371599 0.913894 0.207227 0.059 Uiso 1 1 calc R U . . .
C27 C 0.48838(7) 0.95759(8) 0.35021(12) 0.0433(3) Uani 1 1 d . . . . .
H27 H 0.471872 0.909844 0.316788 0.052 Uiso 1 1 calc R U . . .
C28 C 0.54410(7) 0.95844(8) 0.44387(12) 0.0417(3) Uani 1 1 d . . . . .
C29 C 0.58455(7) 0.88975(9) 0.50204(12) 0.0477(4) Uani 1 1 d . . . . .
H29A H 0.588954 0.885211 0.567784 0.057 Uiso 1 1 calc R U . . .
H29B H 0.624967 0.899989 0.517591 0.057 Uiso 1 1 calc R U . . .
C30 C 0.56173(8) 0.81197(10) 0.44523(14) 0.0610(5) Uani 1 1 d . . . . .
H30A H 0.558442 0.815462 0.380355 0.073 Uiso 1 1 calc R U . . .
H30B H 0.521043 0.801628 0.428464 0.073 Uiso 1 1 calc R U . . .
C31 C 0.60409(9) 0.74386(11) 0.50937(16) 0.0727(6) Uani 1 1 d . . . . .
H31A H 0.590218 0.696982 0.467868 0.109 Uiso 1 1 calc R U . . .
H31B H 0.603522 0.735998 0.569568 0.109 Uiso 1 1 calc R U . . .
H31C H 0.645179 0.755727 0.531039 0.109 Uiso 1 1 calc R U . . .
C32 C 0.26140(9) 0.88425(13) 0.03745(16) 0.0711(6) Uani 1 1 d D . . . .
F1 F 0.25852(6) 0.72713(9) 0.39535(12) 0.1177(6) Uani 1 1 d . . . . .
F2 F 0.18726(5) 0.67466(8) 0.25385(10) 0.0879(4) Uani 1 1 d . . . . .
F3 F 0.25697(7) 0.73899(9) 0.25847(15) 0.1262(6) Uani 1 1 d . . . . .
N1 N 0.62098(6) 0.58331(8) 0.80649(11) 0.0568(4) Uani 1 1 d . . . . .
N2 N 0.56374(5) 0.56571(7) 0.72142(10) 0.0460(3) Uani 1 1 d . . . . .
N3 N 0.47081(6) 0.62771(7) 0.58271(10) 0.0501(3) Uani 1 1 d . . . . .
C1 C 0.62122(8) 0.66185(11) 0.80631(15) 0.0643(5) Uani 1 1 d . . . . .
H1 H 0.654859 0.691363 0.856427 0.077 Uiso 1 1 calc R U . . .
C2 C 0.56708(8) 0.69554(10) 0.72513(14) 0.0627(5) Uani 1 1 d . . . . .
H2 H 0.558229 0.748725 0.711147 0.075 Uiso 1 1 calc R U . . .
C3 C 0.52912(7) 0.63279(9) 0.66945(12) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.44774(7) 0.55661(9) 0.54878(12) 0.0444(3) Uani 1 1 d . . . . .
C5 C 0.38312(7) 0.55215(9) 0.45512(12) 0.0458(4) Uani 1 1 d . . . . .
C6 C 0.34577(7) 0.61802(9) 0.42643(12) 0.0491(4) Uani 1 1 d . . . . .
H6 H 0.361441 0.663886 0.465354 0.059 Uiso 1 1 calc R U . . .
C7 C 0.28507(7) 0.61578(10) 0.33984(13) 0.0521(4) Uani 1 1 d . . . . .
C8 C 0.26076(8) 0.54816(11) 0.27984(13) 0.0601(5) Uani 1 1 d . . . . .
H8 H 0.220165 0.546862 0.222147 0.072 Uiso 1 1 calc R U . . .
C9 C 0.29788(8) 0.48308(11) 0.30734(15) 0.0655(5) Uani 1 1 d . . . . .
H9 H 0.282254 0.437691 0.267336 0.079 Uiso 1 1 calc R U . . .
C10 C 0.35832(8) 0.48444(10) 0.39404(13) 0.0560(4) Uani 1 1 d . . . . .
H10 H 0.382606 0.439837 0.411723 0.067 Uiso 1 1 calc R U . . .
C11 C 0.48269(7) 0.48742(9) 0.59950(12) 0.0469(4) Uani 1 1 d . . . . .
H11 H 0.465059 0.438478 0.572785 0.056 Uiso 1 1 calc R U . . .
C12 C 0.54139(7) 0.49157(9) 0.68627(12) 0.0447(3) Uani 1 1 d . . . . .
C13 C 0.58377(7) 0.42464(9) 0.74616(13) 0.0510(4) Uani 1 1 d . . . . .
H13A H 0.592367 0.424203 0.815303 0.061 Uiso 1 1 calc R U . . .
H13B H 0.622296 0.433656 0.753913 0.061 Uiso 1 1 calc R U . . .
C14 C 0.55935(8) 0.34419(9) 0.69691(14) 0.0570(4) Uani 1 1 d . . . . .
H14A H 0.523065 0.332207 0.695307 0.068 Uiso 1 1 calc R U . . .
H14B H 0.547535 0.345154 0.625717 0.068 Uiso 1 1 calc R U . . .
C15 C 0.60712(9) 0.28056(10) 0.75693(16) 0.0693(5) Uani 1 1 d . . . . .
H15A H 0.590217 0.230591 0.724687 0.104 Uiso 1 1 calc R U . . .
H15B H 0.618799 0.279422 0.827376 0.104 Uiso 1 1 calc R U . . .
H15C H 0.642562 0.291428 0.756709 0.104 Uiso 1 1 calc R U . . .
C16 C 0.24674(8) 0.68909(12) 0.31096(16) 0.0662(5) 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C17 N4 N5 102.66(14) . . ?
N4 N5 C19 112.98(15) . . ?
N4 N5 C28 125.08(13) . . ?
C28 N5 C19 121.92(18) . . ?
C20 N6 C19 117.18(14) . . ?
N4 C17 H17 122.9 . . ?
N4 C17 C18 114.23(17) . . ?
C18 C17 H17 122.9 . . ?
C17 C18 H18 127.5 . . ?
C17 C18 C19 105.0(2) . . ?
C19 C18 H18 127.5 . . ?
N5 C19 C18 105.2(2) . . ?
N6 C19 N5 122.10(15) . . ?
N6 C19 C18 132.74(17) . . ?
N6 C20 C21 117.26(14) . . ?
N6 C20 C27 121.72(19) . . ?
C27 C20 C21 121.02(14) . . ?
C22 C21 C20 120.61(17) . . ?
C26 C21 C20 121.39(15) . . ?
C26 C21 C22 117.98(19) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.74(19) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.03(18) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.8(2) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 C26 120.61(18) . . ?
C24 C25 C32 119.95(19) . . ?
C26 C25 C32 119.42(17) . . ?
C21 C26 C25 120.83(16) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C20 C27 H27 119.2 . . ?
C28 C27 C20 121.67(15) . . ?
C28 C27 H27 119.2 . . ?
N5 C28 C29 117.27(18) . . ?
C27 C28 N5 115.35(14) . . ?
C27 C28 C29 127.37(15) . . ?
C28 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
C28 C29 C30 114.81(19) . . ?
H29A C29 H29B 107.5 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
C29 C30 C31 112.4(2) . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
F00F C32 F9 101.6(5) . . ?
F00F C32 C25 110.6(4) . . ?
F4 C32 C25 110.6(4) . . ?
F5 C32 F4 102.1(6) . . ?
F5 C32 F7 110.4(6) . . ?
F5 C32 C25 115.2(4) . . ?
F7 C32 F4 102.3(5) . . ?
F7 C32 C25 114.8(4) . . ?
F8 C32 F00F 110.2(8) . . ?
F8 C32 F9 111.8(7) . . ?
F8 C32 C25 115.1(4) . . ?
F9 C32 C25 106.7(5) . . ?
C1 N1 N2 102.82(13) . . ?
N1 N2 C3 112.55(16) . . ?
N1 N2 C12 125.47(13) . . ?
C12 N2 C3 121.96(17) . . ?
C4 N3 C3 117.46(14) . . ?
N1 C1 H1 122.8 . . ?
N1 C1 C2 114.34(16) . . ?
C2 C1 H1 122.8 . . ?
C1 C2 H2 127.5 . . ?
C3 C2 C1 105.0(2) . . ?
C3 C2 H2 127.5 . . ?
N3 C3 N2 121.60(15) . . ?
N3 C3 C2 133.06(16) . . ?
C2 C3 N2 105.3(2) . . ?
N3 C4 C5 116.73(14) . . ?
N3 C4 C11 121.83(18) . . ?
C11 C4 C5 121.45(15) . . ?
C6 C5 C4 118.92(16) . . ?
C6 C5 C10 118.29(19) . . ?
C10 C5 C4 122.80(16) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.46(17) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C16 118.45(17) . . ?
C8 C7 C6 120.84(17) . . ?
C8 C7 C16 120.69(19) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.83(19) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.81(19) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.76(18) . . ?
C9 C10 H10 119.6 . . ?
C4 C11 H11 119.3 . . ?
C12 C11 C4 121.38(16) . . ?
C12 C11 H11 119.3 . . ?
N2 C12 C13 116.91(18) . . ?
C11 C12 N2 115.74(14) . . ?
C11 C12 C13 127.35(16) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.70(19) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.44(19) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 C7 111.57(18) . . ?
F2 C16 F1 105.9(2) . . ?
F2 C16 C7 112.96(19) . . ?
F3 C16 F1 106.8(2) . . ?
F3 C16 F2 106.9(2) . . ?
F3 C16 C7 112.3(2) . . ?
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
F00F C32 1.287(7) . ?
F4 C32 1.366(7) . ?
F5 C32 1.249(7) . ?
F7 C32 1.304(6) . ?
F8 C32 1.229(7) . ?
F9 C32 1.407(9) . ?
N4 N5 1.367(3) . ?
N4 C17 1.344(3) . ?
N5 C19 1.393(3) . ?
N5 C28 1.376(3) . ?
N6 C19 1.358(3) . ?
N6 C20 1.325(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(3) . ?
C20 C21 1.493(3) . ?
C20 C27 1.429(3) . ?
C21 C22 1.400(3) . ?
C21 C26 1.389(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(3) . ?
C25 C26 1.394(3) . ?
C25 C32 1.509(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.363(3) . ?
C28 C29 1.494(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.515(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.526(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
F1 C16 1.338(4) . ?
F2 C16 1.318(3) . ?
F3 C16 1.313(3) . ?
N1 N2 1.363(3) . ?
N1 C1 1.337(3) . ?
N2 C3 1.399(3) . ?
N2 C12 1.370(3) . ?
N3 C3 1.358(3) . ?
N3 C4 1.323(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C4 C5 1.491(3) . ?
C4 C11 1.428(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.399(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(3) . ?
C7 C8 1.390(3) . ?
C7 C16 1.507(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.363(3) . ?
C12 C13 1.496(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.523(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.517(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
_geom_torsion_publ_flag
N4 N5 C19 N6 -179.20(14) . . . . ?
N4 N5 C19 C18 0.14(18) . . . . ?
N4 N5 C28 C27 179.13(14) . . . . ?
N4 N5 C28 C29 -1.2(2) . . . . ?
N4 C17 C18 C19 -0.2(2) . . . . ?
N5 N4 C17 C18 0.3(2) . . . . ?
N5 C28 C29 C30 -175.37(15) . . . . ?
N6 C20 C21 C22 21.9(2) . . . . ?
N6 C20 C21 C26 -156.98(16) . . . . ?
N6 C20 C27 C28 1.3(2) . . . . ?
C17 N4 N5 C19 -0.24(18) . . . . ?
C17 N4 N5 C28 178.37(15) . . . . ?
C17 C18 C19 N5 0.02(19) . . . . ?
C17 C18 C19 N6 179.26(18) . . . . ?
C19 N5 C28 C27 -2.4(2) . . . . ?
C19 N5 C28 C29 177.35(14) . . . . ?
C19 N6 C20 C21 178.78(13) . . . . ?
C19 N6 C20 C27 -1.6(2) . . . . ?
C20 N6 C19 N5 0.0(2) . . . . ?
C20 N6 C19 C18 -179.14(18) . . . . ?
C20 C21 C22 C23 -178.32(16) . . . . ?
C20 C21 C26 C25 178.12(15) . . . . ?
C20 C27 C28 N5 0.7(2) . . . . ?
C20 C27 C28 C29 -178.96(15) . . . . ?
C21 C20 C27 C28 -179.11(14) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C21 C26 C25 -0.8(2) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C23 C24 C25 C32 -177.88(19) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C24 C25 C32 F00F -44.8(5) . . . . ?
C24 C25 C32 F4 -142.9(4) . . . . ?
C24 C25 C32 F5 102.1(8) . . . . ?
C24 C25 C32 F7 -27.8(6) . . . . ?
C24 C25 C32 F8 -170.5(13) . . . . ?
C24 C25 C32 F9 64.9(8) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C26 C25 C32 F00F 136.7(5) . . . . ?
C26 C25 C32 F4 38.6(4) . . . . ?
C26 C25 C32 F5 -76.4(8) . . . . ?
C26 C25 C32 F7 153.7(6) . . . . ?
C26 C25 C32 F8 11.0(13) . . . . ?
C26 C25 C32 F9 -113.6(8) . . . . ?
C27 C20 C21 C22 -157.65(16) . . . . ?
C27 C20 C21 C26 23.4(2) . . . . ?
C27 C28 C29 C30 4.3(2) . . . . ?
C28 N5 C19 N6 2.1(2) . . . . ?
C28 N5 C19 C18 -178.52(14) . . . . ?
C28 C29 C30 C31 -178.68(16) . . . . ?
C32 C25 C26 C21 178.70(17) . . . . ?
N1 N2 C3 N3 -179.99(15) . . . . ?
N1 N2 C3 C2 0.26(19) . . . . ?
N1 N2 C12 C11 179.95(15) . . . . ?
N1 N2 C12 C13 -0.5(2) . . . . ?
N1 C1 C2 C3 0.4(2) . . . . ?
N2 N1 C1 C2 -0.3(2) . . . . ?
N2 C12 C13 C14 -173.35(15) . . . . ?
N3 C4 C5 C6 -17.7(2) . . . . ?
N3 C4 C5 C10 161.93(17) . . . . ?
N3 C4 C11 C12 0.8(3) . . . . ?
C1 N1 N2 C3 -0.01(19) . . . . ?
C1 N1 N2 C12 178.20(16) . . . . ?
C1 C2 C3 N2 -0.4(2) . . . . ?
C1 C2 C3 N3 179.91(19) . . . . ?
C3 N2 C12 C11 -2.0(2) . . . . ?
C3 N2 C12 C13 177.55(15) . . . . ?
C3 N3 C4 C5 178.44(14) . . . . ?
C3 N3 C4 C11 -1.2(2) . . . . ?
C4 N3 C3 N2 -0.1(2) . . . . ?
C4 N3 C3 C2 179.61(19) . . . . ?
C4 C5 C6 C7 -179.55(15) . . . . ?
C4 C5 C10 C9 -179.89(16) . . . . ?
C4 C11 C12 N2 0.8(2) . . . . ?
C4 C11 C12 C13 -178.71(16) . . . . ?
C5 C4 C11 C12 -178.76(15) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C7 C16 -179.05(16) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C16 F1 -38.8(2) . . . . ?
C6 C7 C16 F2 -157.94(18) . . . . ?
C6 C7 C16 F3 81.1(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C7 C16 F1 142.81(19) . . . . ?
C8 C7 C16 F2 23.6(3) . . . . ?
C8 C7 C16 F3 -97.4(3) . . . . ?
C8 C9 C10 C5 -0.5(3) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C11 C4 C5 C6 161.95(16) . . . . ?
C11 C4 C5 C10 -18.5(2) . . . . ?
C11 C12 C13 C14 6.1(3) . . . . ?
C12 N2 C3 N3 1.7(2) . . . . ?
C12 N2 C3 C2 -178.02(16) . . . . ?
C12 C13 C14 C15 174.86(16) . . . . ?
C16 C7 C8 C9 178.24(18) . . . . ?
