#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:53:12 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284322 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159343.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_7159343
loop_
_publ_author_name
'Guo, Honghong'
'Lin, Jianying'
'Liu, Qiang'
'Li, Xing'
_publ_section_title
;
 Construction of 1,2-dihydro-1,3,5-triazines via reactions
 involving amidines.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4269
_journal_page_last               4275
_journal_paper_doi               10.1039/d3ob00283g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C27 H19 F2 N3'
_chemical_formula_sum            'C27 H19 F2 N3'
_chemical_formula_weight         423.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.307(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1865(2)
_cell_length_b                   11.3004(2)
_cell_length_c                   19.1635(4)
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0480
_cell_measurement_theta_min      4.5520
_cell_volume                     2146.71(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -13.00   1.00    1.00    --  -35.62 147.00  11.00   89
  2  ω    -69.00 -44.00   1.00    1.00    --  -35.62 124.00-153.00   25
  3  ω     31.00  56.00   1.00    1.00    --   35.62-124.00 127.00   25
  4  ω    103.00 128.00   1.00    1.24    --  107.12 147.00  11.00   25
  5  ω     42.00 115.00   1.00    1.24    --  107.12-124.00 127.00   73
  6  ω    111.00 136.00   1.00    1.24    --  107.12 124.00-153.00   25
  7  ω     86.00 113.00   1.00    1.24    --  107.12-147.00 -37.00   27
  8  ω    -93.00 -40.00   1.00    1.00    --  -35.62 178.00-120.00   53
  9  ω   -102.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   82
 10  ω     20.00  99.00   1.00    1.00    --   35.62  57.00  30.00   79
 11  ω     24.00  72.00   1.00    1.00    --   35.62 -99.00 -60.00   48
 12  ω     81.00 106.00   1.00    1.24    --  107.12 -95.00   0.00   25
 13  ω     49.00  80.00   1.00    1.24    --  107.12 -95.00 -30.00   31
 14  ω    119.00 174.00   1.00    1.24    --  107.12  45.00-150.00   55
 15  ω     90.00 176.00   1.00    1.24    --  107.12  45.00   0.00   86
 16  ω     48.00 110.00   1.00    1.24    --  107.12 -95.00 150.00   62
 17  ω    100.00 175.00   1.00    1.24    --  107.12 111.00  30.00   75
 18  ω    102.00 167.00   1.00    1.24    --  107.12 111.00 150.00   65
 19  ω    133.00 169.00   1.00    1.24    --  107.12 111.00  60.00   36
 20  ω    103.00 128.00   1.00    1.24    --  107.12  61.00 -60.00   25
 21  ω     37.00 120.00   1.00    1.24    --  107.12 -30.00  60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315789000
_diffrn_orient_matrix_UB_12      -0.1329409000
_diffrn_orient_matrix_UB_13      -0.0117631000
_diffrn_orient_matrix_UB_21      -0.1040308000
_diffrn_orient_matrix_UB_22      0.0286884000
_diffrn_orient_matrix_UB_23      -0.0699740000
_diffrn_orient_matrix_UB_31      0.1109060000
_diffrn_orient_matrix_UB_32      -0.0108180000
_diffrn_orient_matrix_UB_33      -0.0423053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_min         4.544
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             880
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0803P)²+0.4810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3534
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00283g2.cif
_cod_data_source_block           yhb-2-20221012
_cod_depositor_comments
'Adding full bibliography for 7159343--7159344.cif.'
_cod_database_code               7159343
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 F1 N1 O1'
_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.
;
_diffrn_oxdiff_digest_frames
;
01473b9dfc98ce9f966b3a0889676fd31800030107c
;
_diffrn_oxdiff_digest_hkl
;
01a56ec8086894cece25038b96f5cc11f59884
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C25(H25), C12(H12), C21(H21), C23(H23), C32(H32), C18(H18),
 C28(H28), C22(H22), C16(H16), C17(H17), C11(H11), C9(H9), C10(H10), C31(H31),
 C29(H29), C30(H30)
;
_olex2_date_sample_data_collection 2022-10-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.493
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
F19 F 0.07484(13) 0.12754(12) 0.04601(8) 0.0709(4) Uani 1 1 d . . . . .
F26 F 0.79983(16) 0.40688(14) 0.46585(7) 0.0757(4) Uani 1 1 d . . . . .
N1 N 0.63667(13) 0.53561(13) 0.15531(8) 0.0348(3) Uani 1 1 d . . . . .
N3 N 0.49684(14) 0.44797(13) 0.22139(8) 0.0370(3) Uani 1 1 d . . . . .
N5 N 0.43068(14) 0.44090(12) 0.09332(8) 0.0366(3) Uani 1 1 d . . . . .
C7 C 0.76898(16) 0.53455(15) 0.14171(9) 0.0346(4) Uani 1 1 d . . . . .
C4 C 0.42144(15) 0.40570(15) 0.15582(9) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.60866(16) 0.50145(14) 0.21870(9) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.51847(16) 0.54303(14) 0.09424(9) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.551618 0.540901 0.050139 0.041 Uiso 1 1 calc R . . . .
C13 C 0.32679(16) 0.30776(15) 0.16184(10) 0.0360(4) Uani 1 1 d . . . . .
C27 C 0.43770(17) 0.65626(16) 0.09318(10) 0.0393(4) Uani 1 1 d . . . . .
C20 C 0.70540(16) 0.52821(15) 0.28748(9) 0.0355(4) Uani 1 1 d . . . . .
C14 C 0.24415(17) 0.26144(16) 0.09981(10) 0.0405(4) Uani 1 1 d . . . . .
H14 H 0.247818 0.290506 0.054902 0.049 Uiso 1 1 calc R . . . .
C8 C 0.80593(19) 0.62243(18) 0.09992(11) 0.0460(4) Uani 1 1 d . . . . .
H8 H 0.746067 0.683113 0.081842 0.055 Uiso 1 1 calc R . . . .
C25 C 0.70848(18) 0.45450(16) 0.34552(10) 0.0411(4) Uani 1 1 d . . . . .
H25 H 0.653302 0.388037 0.340892 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8578(2) 0.44411(18) 0.16838(11) 0.0474(5) Uani 1 1 d . . . . .
H12 H 0.832591 0.384296 0.195978 0.057 Uiso 1 1 calc R . . . .
C15 C 0.15678(18) 0.17146(17) 0.10658(12) 0.0473(5) Uani 1 1 d . . . . .
C21 C 0.7883(2) 0.62828(17) 0.29596(11) 0.0457(4) Uani 1 1 d . . . . .
H21 H 0.787638 0.677978 0.257199 0.055 Uiso 1 1 calc R . . . .
C24 C 0.7942(2) 0.48106(18) 0.40998(10) 0.0473(5) Uani 1 1 d . . . . .
C23 C 0.8761(2) 0.57948(19) 0.42009(11) 0.0516(5) Uani 1 1 d . . . . .
H23 H 0.932650 0.595754 0.464513 0.062 Uiso 1 1 calc R . . . .
C32 C 0.3158(2) 0.6646(2) 0.04242(13) 0.0553(5) Uani 1 1 d . . . . .
H32 H 0.286737 0.602160 0.011057 0.066 Uiso 1 1 calc R . . . .
C18 C 0.3194(2) 0.26165(19) 0.22814(11) 0.0496(5) Uani 1 1 d . . . . .
H18 H 0.374609 0.291875 0.269868 0.060 Uiso 1 1 calc R . . . .
C28 C 0.4795(3) 0.75027(18) 0.13875(13) 0.0577(5) Uani 1 1 d . . . . .
H28 H 0.561352 0.745963 0.172369 0.069 Uiso 1 1 calc R . . . .
C22 C 0.8714(2) 0.6530(2) 0.36231(12) 0.0541(5) Uani 1 1 d . . . . .
H22 H 0.925022 0.720557 0.367960 0.065 Uiso 1 1 calc R . . . .
C16 C 0.1475(2) 0.12437(19) 0.17108(13) 0.0556(5) Uani 1 1 d . . . . .
H16 H 0.087515 0.063285 0.173568 0.067 Uiso 1 1 calc R . . . .
C17 C 0.2300(2) 0.1707(2) 0.23217(13) 0.0596(6) Uani 1 1 d . . . . .
H17 H 0.225693 0.140490 0.276746 0.071 Uiso 1 1 calc R . . . .
C11 C 0.9844(2) 0.4435(2) 0.15363(13) 0.0632(6) Uani 1 1 d . . . . .
H11 H 1.045075 0.383543 0.172120 0.076 Uiso 1 1 calc R . . . .
C9 C 0.9323(2) 0.6196(2) 0.08517(13) 0.0623(6) Uani 1 1 d . . . . .
H9 H 0.957339 0.678434 0.056882 0.075 Uiso 1 1 calc R . . . .
C10 C 1.0215(2) 0.5304(3) 0.11198(13) 0.0671(7) Uani 1 1 d . . . . .
H10 H 1.106525 0.528914 0.101930 0.080 Uiso 1 1 calc R . . . .
C31 C 0.2379(2) 0.7656(3) 0.03860(17) 0.0759(8) Uani 1 1 d . . . . .
H31 H 0.156943 0.771036 0.004349 0.091 Uiso 1 1 calc R . . . .
C29 C 0.4008(4) 0.8511(2) 0.13491(18) 0.0799(8) Uani 1 1 d . . . . .
H29 H 0.429723 0.914135 0.165851 0.096 Uiso 1 1 calc R . . . .
C30 C 0.2791(3) 0.8579(2) 0.08500(19) 0.0851(10) Uani 1 1 d . . . . .
H30 H 0.225262 0.924874 0.082879 0.102 Uiso 1 1 calc R . . . .
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'
F F 0.0727 0.0534 '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
_geom_angle_publ_flag
C7 N1 C6 119.15(13) . . ?
C2 N1 C7 123.93(14) . . ?
C2 N1 C6 114.96(13) . . ?
C2 N3 C4 115.35(14) . . ?
C4 N5 C6 114.19(14) . . ?
C8 C7 N1 119.57(15) . . ?
C8 C7 C12 120.23(16) . . ?
C12 C7 N1 120.17(16) . . ?
N3 C4 C13 114.57(14) . . ?
N5 C4 N3 126.08(15) . . ?
N5 C4 C13 119.30(15) . . ?
N1 C2 C20 120.02(14) . . ?
N3 C2 N1 122.04(15) . . ?
N3 C2 C20 117.91(15) . . ?
N1 C6 H6 107.6 . . ?
N1 C6 C27 113.52(14) . . ?
N5 C6 N1 110.55(13) . . ?
N5 C6 H6 107.6 . . ?
N5 C6 C27 109.75(13) . . ?
C27 C6 H6 107.6 . . ?
C14 C13 C4 119.25(16) . . ?
C14 C13 C18 119.36(16) . . ?
C18 C13 C4 121.39(16) . . ?
C32 C27 C6 117.36(17) . . ?
C28 C27 C6 123.58(17) . . ?
C28 C27 C32 119.06(19) . . ?
C25 C20 C2 118.60(15) . . ?
C25 C20 C21 119.47(16) . . ?
C21 C20 C2 121.87(16) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.34(18) . . ?
C15 C14 H14 120.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.56(19) . . ?
C9 C8 H8 120.2 . . ?
C20 C25 H25 120.5 . . ?
C24 C25 C20 118.93(17) . . ?
C24 C25 H25 120.5 . . ?
C7 C12 H12 120.3 . . ?
C7 C12 C11 119.35(19) . . ?
C11 C12 H12 120.3 . . ?
F19 C15 C14 118.22(19) . . ?
F19 C15 C16 118.22(18) . . ?
C16 C15 C14 123.56(19) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.70(18) . . ?
C22 C21 H21 120.1 . . ?
F26 C24 C25 118.68(18) . . ?
F26 C24 C23 118.44(18) . . ?
C25 C24 C23 122.88(18) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 C24 117.84(19) . . ?
C22 C23 H23 121.1 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.1(2) . . ?
C31 C32 H32 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.16(18) . . ?
C23 C22 H22 119.4 . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.65(19) . . ?
C17 C16 H16 121.2 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.72(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.5(3) . . ?
C30 C31 H31 119.8 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.9(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
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
F19 C15 1.358(2) . ?
F26 C24 1.351(2) . ?
N1 C7 1.430(2) . ?
N1 C2 1.366(2) . ?
N1 C6 1.476(2) . ?
N3 C4 1.397(2) . ?
N3 C2 1.301(2) . ?
N5 C4 1.286(2) . ?
N5 C6 1.458(2) . ?
C7 C8 1.381(2) . ?
C7 C12 1.382(2) . ?
C4 C13 1.490(2) . ?
C2 C20 1.484(2) . ?
C6 H6 0.9800 . ?
C6 C27 1.519(2) . ?
C13 C14 1.391(2) . ?
C13 C18 1.391(3) . ?
C27 C32 1.394(3) . ?
C27 C28 1.379(3) . ?
C20 C25 1.384(2) . ?
C20 C21 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.383(3) . ?
C15 C16 1.369(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C24 C23 1.377(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.377(3) . ?
C32 H32 0.9300 . ?
C32 C31 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(3) . ?
C22 H22 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C31 H31 0.9300 . ?
C31 C30 1.372(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(5) . ?
C30 H30 0.9300 . ?
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
F19 C15 C16 C17 -179.25(19) . . . . ?
F26 C24 C23 C22 178.7(2) . . . . ?
N1 C7 C8 C9 -178.22(19) . . . . ?
N1 C7 C12 C11 178.88(19) . . . . ?
N1 C2 C20 C25 -152.53(16) . . . . ?
N1 C2 C20 C21 30.5(2) . . . . ?
N1 C6 C27 C32 -172.58(15) . . . . ?
N1 C6 C27 C28 8.3(2) . . . . ?
N3 C4 C13 C14 178.21(14) . . . . ?
N3 C4 C13 C18 -1.9(2) . . . . ?
N3 C2 C20 C25 29.2(2) . . . . ?
N3 C2 C20 C21 -147.77(17) . . . . ?
N5 C4 C13 C14 -4.0(2) . . . . ?
N5 C4 C13 C18 175.91(16) . . . . ?
N5 C6 C27 C32 -48.3(2) . . . . ?
N5 C6 C27 C28 132.54(18) . . . . ?
C7 N1 C2 N3 -145.19(17) . . . . ?
C7 N1 C2 C20 36.6(2) . . . . ?
C7 N1 C6 N5 121.01(15) . . . . ?
C7 N1 C6 C27 -115.16(16) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C7 C12 C11 C10 -1.1(4) . . . . ?
C4 N3 C2 N1 13.1(2) . . . . ?
C4 N3 C2 C20 -168.71(14) . . . . ?
C4 N5 C6 N1 37.38(19) . . . . ?
C4 N5 C6 C27 -88.60(17) . . . . ?
C4 C13 C14 C15 -179.60(15) . . . . ?
C4 C13 C18 C17 179.79(18) . . . . ?
C2 N1 C7 C8 -144.02(18) . . . . ?
C2 N1 C7 C12 38.0(3) . . . . ?
C2 N1 C6 N5 -43.65(19) . . . . ?
C2 N1 C6 C27 80.18(18) . . . . ?
C2 N3 C4 N5 -20.2(2) . . . . ?
C2 N3 C4 C13 157.33(14) . . . . ?
C2 C20 C25 C24 -177.70(16) . . . . ?
C2 C20 C21 C22 176.34(17) . . . . ?
C6 N1 C7 C8 52.8(2) . . . . ?
C6 N1 C7 C12 -125.22(18) . . . . ?
C6 N1 C2 N3 18.6(2) . . . . ?
C6 N1 C2 C20 -159.56(14) . . . . ?
C6 N5 C4 N3 -7.1(2) . . . . ?
C6 N5 C4 C13 175.45(13) . . . . ?
C6 C27 C32 C31 -179.78(18) . . . . ?
C6 C27 C28 C29 -180.0(2) . . . . ?
C13 C14 C15 F19 179.07(16) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C13 C18 C17 C16 0.1(3) . . . . ?
C27 C32 C31 C30 -0.6(4) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C20 C25 C24 F26 -178.00(18) . . . . ?
C20 C25 C24 C23 1.3(3) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
C25 C24 C23 C22 -0.6(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C24 C23 C22 C21 -0.7(3) . . . . ?
C32 C27 C28 C29 0.9(3) . . . . ?
C32 C31 C30 C29 1.4(4) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C28 C27 C32 C31 -0.6(3) . . . . ?
C28 C29 C30 C31 -1.2(4) . . . . ?
