#------------------------------------------------------------------------------
#$Date: 2024-07-19 04:16:12 +0300 (Fri, 19 Jul 2024) $
#$Revision: 293469 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249072.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_7249072
loop_
_publ_author_name
'Khetmalis, Yogesh Mahadu'
'Shobha, Singarapalle'
'Nandikolla, Adinarayana'
'Chandu, Ala'
'Murugesan, Sankaranarayanan'
'Kumar, Muthyala Murali Krishna'
'Chandra Sekhar, Kondapalli Venkata Gowri'
_publ_section_title
;
 Design, synthesis, and anti-mycobacterial evaluation of
 1,8-naphthyridine-3-carbonitrile analogues
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              22676
_journal_page_last               22689
_journal_paper_doi               10.1039/D4RA04262J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 F N6 O'
_chemical_formula_sum            'C21 H19 F N6 O'
_chemical_formula_weight         390.42
_chemical_name_systematic        ANC-5
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-22 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                85.352(2)
_cell_angle_beta                 88.350(2)
_cell_angle_gamma                73.647(2)
_cell_formula_units_Z            2
_cell_length_a                   6.03380(10)
_cell_length_b                   7.3549(2)
_cell_length_c                   20.9236(5)
_cell_measurement_reflns_used    5473
_cell_measurement_temperature    126
_cell_measurement_theta_max      79.3530
_cell_measurement_theta_min      4.2280
_cell_volume                     888.04(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      126
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -19.00   0.50    0.75    --    0.00 -37.00  60.00  116
  2  ω    -57.00 -27.00   0.50    0.75    --    0.00 -37.00 120.00   60
  3  ω    -21.00  14.00   0.50    0.75    --    0.00 -37.00 120.00   70
  4  ω    -18.00  42.00   0.50    0.75    --    0.00  37.00  30.00  120
  5  ω     46.00  87.00   0.50    0.75    --    0.00  37.00  30.00   82
  6  ω      4.00  29.00   0.50    0.75    --    0.00 -77.00-180.00   50
  7  ω     89.00 115.00   0.50    2.50    --  107.20 -82.00 -30.00   52
  8  ω     26.00 139.00   0.50    2.50    --  107.20 -82.00-120.00  226
  9  ω     18.00 113.00   0.50    2.50    --  107.20 -61.00 120.00  190
 10  ω     29.00  55.00   0.50    2.50    --  107.20 -82.00  60.00   52
 11  ω     96.00 136.00   0.50    2.50    --  107.20 -82.00-180.00   80
 12  ω    113.00 194.00   0.50    2.50    --  107.20  30.00 -30.00  162
 13  ω     29.00 119.00   0.50    2.50    --  107.20 -30.00-120.00  180
 14  ω     21.00 111.00   0.50    2.50    --  107.20 -45.00-150.00  180
 15  ω     19.00 118.00   0.50    2.50    --  107.20 -45.00   0.00  198
 16  ω    107.00 134.00   0.50    2.50    --  107.20 -82.00  30.00   54
 17  ω     28.00  95.00   0.50    2.50    --  107.20 -82.00  30.00  134
 18  ω     86.00 137.00   0.50    2.50    --  107.20 -82.00 -90.00  102
 19  ω     80.00 105.00   0.50    2.50    --  107.20 -82.00-150.00   50
 20  ω    108.00 134.00   0.50    2.50    --  107.20 -82.00   0.00   52
 21  ω     23.00 112.00   0.50    2.50    --  107.20 -82.00 120.00  178
 22  ω     85.00 110.00   0.50    2.50    --  107.20 -82.00  60.00   50
 23  ω     56.00 170.00   0.50    2.50    --  107.20   0.00  90.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0740267000
_diffrn_orient_matrix_UB_12      -0.1892595000
_diffrn_orient_matrix_UB_13      0.0416823000
_diffrn_orient_matrix_UB_21      -0.0197998000
_diffrn_orient_matrix_UB_22      0.1100423000
_diffrn_orient_matrix_UB_23      0.0604766000
_diffrn_orient_matrix_UB_31      -0.2548206000
_diffrn_orient_matrix_UB_32      0.0005391000
_diffrn_orient_matrix_UB_33      0.0078926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9099
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.758
_diffrn_reflns_theta_min         4.240
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_preparation       '10% MeOH in DCM'
_exptl_crystal_recrystallization_method Cu
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0461
_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)+(0.0625P)²+0.3180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3350
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra04262j2.cif
_cod_data_source_block           ANC-5
_cod_database_code               7249072
_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   0.959
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C1(H1), C2(H2), C3(H3), C6(H6A), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_submission_original_sample_id NCF
_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 2.095
_oxdiff_exptl_absorpt_empirical_full_min 0.754
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 0.01356(18) 0.84487(15) 0.70886(5) 0.0421(3) Uani 1 1 d . . . . .
O1 O 0.97843(17) 0.63425(16) 0.41891(5) 0.0321(3) Uani 1 1 d . . . . .
N1 N 0.2455(2) 0.36013(19) 0.16705(6) 0.0315(3) Uani 1 1 d . . . . .
N2 N 0.4461(2) 0.57626(18) 0.18093(6) 0.0263(3) Uani 1 1 d . . . . .
N3 N 1.0280(3) 0.8013(2) 0.06308(7) 0.0409(3) Uani 1 1 d . . . . .
N4 N 0.6389(2) 0.79866(18) 0.20033(6) 0.0258(3) Uani 1 1 d . . . . .
N5 N 0.72816(19) 0.72812(18) 0.33562(6) 0.0254(3) Uani 1 1 d . . . . .
N6 N 0.6493(2) 0.7145(2) 0.51026(6) 0.0313(3) Uani 1 1 d . . . . .
H6 H 0.797617 0.680222 0.519223 0.038 Uiso 1 1 calc R U . . .
C1 C 0.2146(3) 0.2205(2) 0.13534(8) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.095191 0.166116 0.149922 0.042 Uiso 1 1 calc R U . . .
C2 C 0.3446(3) 0.1468(2) 0.08190(8) 0.0400(4) Uani 1 1 d . . . . .
H2 H 0.314615 0.045270 0.061617 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5162(3) 0.2249(2) 0.05964(8) 0.0386(4) Uani 1 1 d . . . . .
H3 H 0.607175 0.179094 0.023422 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5543(3) 0.3745(2) 0.09172(7) 0.0307(3) Uani 1 1 d . . . . .
C5 C 0.4150(2) 0.4372(2) 0.14574(7) 0.0273(3) Uani 1 1 d . . . . .
C6 C 0.7200(3) 0.4701(2) 0.07237(7) 0.0316(3) Uani 1 1 d . . . . .
H6A H 0.811896 0.436606 0.035193 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7484(2) 0.6119(2) 0.10740(7) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.6100(2) 0.6580(2) 0.16443(7) 0.0251(3) Uani 1 1 d . . . . .
C9 C 0.9036(3) 0.7185(2) 0.08376(7) 0.0316(3) Uani 1 1 d . . . . .
C10 C 0.8681(2) 0.7859(2) 0.22568(7) 0.0272(3) Uani 1 1 d . . . . .
H10A H 0.877952 0.914877 0.232662 0.033 Uiso 1 1 calc R U . . .
H10B H 0.988271 0.731035 0.193949 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4595(2) 0.8760(2) 0.24726(7) 0.0261(3) Uani 1 1 d . . . . .
H11A H 0.307089 0.880168 0.229874 0.031 Uiso 1 1 calc R U . . .
H11B H 0.458842 1.008068 0.253645 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9126(2) 0.6624(2) 0.28869(7) 0.0273(3) Uani 1 1 d . . . . .
H12A H 0.924133 0.529368 0.280505 0.033 Uiso 1 1 calc R U . . .
H12B H 1.061740 0.665157 0.306530 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4924(2) 0.7611(2) 0.31176(7) 0.0260(3) Uani 1 1 d . . . . .
H13A H 0.380323 0.830033 0.343118 0.031 Uiso 1 1 calc R U . . .
H13B H 0.461545 0.637441 0.307354 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7790(2) 0.6957(2) 0.39908(7) 0.0251(3) Uani 1 1 d . . . . .
C15 C 0.5744(2) 0.7414(2) 0.44493(7) 0.0263(3) Uani 1 1 d . . . . .
H15A H 0.481837 0.874806 0.435558 0.032 Uiso 1 1 calc R U . . .
H15B H 0.474746 0.658181 0.438460 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4866(2) 0.7429(2) 0.55916(7) 0.0259(3) Uani 1 1 d . . . . .
C17 C 0.5594(3) 0.7061(2) 0.62318(7) 0.0283(3) Uani 1 1 d . . . . .
H17 H 0.719535 0.657844 0.632289 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2487(3) 0.8131(2) 0.54713(7) 0.0292(3) Uani 1 1 d . . . . .
H18 H 0.195099 0.836403 0.504166 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0910(3) 0.8487(2) 0.59746(8) 0.0318(3) Uani 1 1 d . . . . .
H19 H -0.069579 0.898099 0.589143 0.038 Uiso 1 1 calc R U . . .
C20 C 0.4020(3) 0.7389(2) 0.67322(7) 0.0307(3) Uani 1 1 d . . . . .
H20 H 0.452655 0.711848 0.716422 0.037 Uiso 1 1 calc R U . . .
C21 C 0.1700(3) 0.8117(2) 0.65936(7) 0.0312(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 0.0181 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'
O O 0.0492 0.0322 '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
C1 N1 C5 117.02(14) . . ?
C8 N2 C5 119.60(12) . . ?
C8 N4 C10 119.95(12) . . ?
C8 N4 C11 118.01(11) . . ?
C11 N4 C10 110.12(11) . . ?
C12 N5 C13 115.18(11) . . ?
C14 N5 C12 118.93(11) . . ?
C14 N5 C13 122.22(11) . . ?
C15 N6 H6 120.3 . . ?
C16 N6 H6 120.3 . . ?
C16 N6 C15 119.49(12) . . ?
N1 C1 H1 117.5 . . ?
N1 C1 C2 125.06(15) . . ?
C2 C1 H1 117.5 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.39(15) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.50(16) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 118.71(15) . . ?
C6 C4 C3 123.89(15) . . ?
C6 C4 C5 117.38(14) . . ?
N1 C5 N2 115.17(13) . . ?
N1 C5 C4 122.33(14) . . ?
N2 C5 C4 122.49(13) . . ?
C4 C6 H6A 120.1 . . ?
C7 C6 C4 119.82(14) . . ?
C7 C6 H6A 120.1 . . ?
C6 C7 C8 119.14(13) . . ?
C6 C7 C9 118.81(13) . . ?
C9 C7 C8 121.91(14) . . ?
N2 C8 N4 118.96(12) . . ?
N2 C8 C7 121.32(13) . . ?
N4 C8 C7 119.59(13) . . ?
N3 C9 C7 177.89(16) . . ?
N4 C10 H10A 109.4 . . ?
N4 C10 H10B 109.4 . . ?
N4 C10 C12 110.99(11) . . ?
H10A C10 H10B 108.0 . . ?
C12 C10 H10A 109.4 . . ?
C12 C10 H10B 109.4 . . ?
N4 C11 H11A 108.9 . . ?
N4 C11 H11B 108.9 . . ?
N4 C11 C13 113.21(11) . . ?
H11A C11 H11B 107.7 . . ?
C13 C11 H11A 108.9 . . ?
C13 C11 H11B 108.9 . . ?
N5 C12 C10 111.62(11) . . ?
N5 C12 H12A 109.3 . . ?
N5 C12 H12B 109.3 . . ?
C10 C12 H12A 109.3 . . ?
C10 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N5 C13 C11 111.17(11) . . ?
N5 C13 H13A 109.4 . . ?
N5 C13 H13B 109.4 . . ?
C11 C13 H13A 109.4 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O1 C14 N5 122.60(13) . . ?
O1 C14 C15 121.35(13) . . ?
N5 C14 C15 116.05(12) . . ?
N6 C15 C14 111.13(12) . . ?
N6 C15 H15A 109.4 . . ?
N6 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N6 C16 C17 119.58(13) . . ?
N6 C16 C18 122.20(13) . . ?
C17 C16 C18 118.19(13) . . ?
C16 C17 H17 119.4 . . ?
C20 C17 C16 121.11(14) . . ?
C20 C17 H17 119.4 . . ?
C16 C18 H18 119.7 . . ?
C19 C18 C16 120.62(14) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.4 . . ?
C21 C19 C18 119.22(14) . . ?
C21 C19 H19 120.4 . . ?
C17 C20 H20 120.6 . . ?
C21 C20 C17 118.89(14) . . ?
C21 C20 H20 120.6 . . ?
F1 C21 C19 119.01(14) . . ?
F1 C21 C20 119.04(14) . . ?
C19 C21 C20 121.94(14) . . ?
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 C21 1.3704(17) . ?
O1 C14 1.2315(18) . ?
N1 C1 1.324(2) . ?
N1 C5 1.351(2) . ?
N2 C5 1.3642(19) . ?
N2 C8 1.3191(19) . ?
N3 C9 1.148(2) . ?
N4 C8 1.3785(19) . ?
N4 C10 1.4707(17) . ?
N4 C11 1.4639(18) . ?
N5 C12 1.4654(18) . ?
N5 C13 1.4694(17) . ?
N5 C14 1.3582(18) . ?
N6 H6 0.8800 . ?
N6 C15 1.4328(18) . ?
N6 C16 1.3841(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(2) . ?
C4 C5 1.417(2) . ?
C4 C6 1.409(2) . ?
C6 H6A 0.9500 . ?
C6 C7 1.373(2) . ?
C7 C8 1.444(2) . ?
C7 C9 1.435(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C13 1.520(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5190(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.403(2) . ?
C16 C18 1.405(2) . ?
C17 H17 0.9500 . ?
C17 C20 1.382(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C21 1.373(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(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
_geom_torsion_publ_flag
O1 C14 C15 N6 3.6(2) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
N4 C10 C12 N5 -54.17(16) . . . . ?
N4 C11 C13 N5 50.83(16) . . . . ?
N5 C14 C15 N6 -175.93(12) . . . . ?
N6 C16 C17 C20 177.82(13) . . . . ?
N6 C16 C18 C19 -176.78(14) . . . . ?
C1 N1 C5 N2 -177.97(12) . . . . ?
C1 N1 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 C6 -177.96(15) . . . . ?
C3 C4 C5 N1 -0.8(2) . . . . ?
C3 C4 C5 N2 177.52(13) . . . . ?
C3 C4 C6 C7 -178.68(14) . . . . ?
C4 C6 C7 C8 1.2(2) . . . . ?
C4 C6 C7 C9 -174.64(13) . . . . ?
C5 N1 C1 C2 0.3(2) . . . . ?
C5 N2 C8 N4 179.82(12) . . . . ?
C5 N2 C8 C7 4.0(2) . . . . ?
C5 C4 C6 C7 3.0(2) . . . . ?
C6 C4 C5 N1 177.63(13) . . . . ?
C6 C4 C5 N2 -4.1(2) . . . . ?
C6 C7 C8 N2 -4.9(2) . . . . ?
C6 C7 C8 N4 179.27(13) . . . . ?
C8 N2 C5 N1 178.96(12) . . . . ?
C8 N2 C5 C4 0.5(2) . . . . ?
C8 N4 C10 C12 -84.04(16) . . . . ?
C8 N4 C11 C13 85.78(15) . . . . ?
C9 C7 C8 N2 170.80(13) . . . . ?
C9 C7 C8 N4 -5.0(2) . . . . ?
C10 N4 C8 N2 127.55(14) . . . . ?
C10 N4 C8 C7 -56.52(18) . . . . ?
C10 N4 C11 C13 -57.07(15) . . . . ?
C11 N4 C8 N2 -11.57(19) . . . . ?
C11 N4 C8 C7 164.36(12) . . . . ?
C11 N4 C10 C12 57.99(15) . . . . ?
C12 N5 C13 C11 -47.18(16) . . . . ?
C12 N5 C14 O1 9.1(2) . . . . ?
C12 N5 C14 C15 -171.42(12) . . . . ?
C13 N5 C12 C10 49.46(16) . . . . ?
C13 N5 C14 O1 166.40(14) . . . . ?
C13 N5 C14 C15 -14.1(2) . . . . ?
C14 N5 C12 C10 -151.66(13) . . . . ?
C14 N5 C13 C11 154.70(13) . . . . ?
C15 N6 C16 C17 176.35(13) . . . . ?
C15 N6 C16 C18 -5.5(2) . . . . ?
C16 N6 C15 C14 -177.76(12) . . . . ?
C16 C17 C20 C21 -0.9(2) . . . . ?
C16 C18 C19 C21 -1.0(2) . . . . ?
C17 C16 C18 C19 1.4(2) . . . . ?
C17 C20 C21 F1 -179.82(13) . . . . ?
C17 C20 C21 C19 1.3(2) . . . . ?
C18 C16 C17 C20 -0.4(2) . . . . ?
C18 C19 C21 F1 -179.22(13) . . . . ?
C18 C19 C21 C20 -0.3(2) . . . . ?
