#------------------------------------------------------------------------------
#$Date: 2022-04-04 02:12:35 +0300 (Mon, 04 Apr 2022) $
#$Revision: 274288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566735.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_1566735
loop_
_publ_author_name
'Sun, Susu'
'Chen, Lai'
'Huo, Jingqian'
'Wang, Ying'
'Kou, Song'
'Yuan, Shitao'
'Fu, Yining'
'Zhang, Jinlin'
_publ_section_title
;
 Discovery of Novel Pyrazole Amides as Potent Fungicide Candidates and
 Evaluation of Their Mode of Action.
;
_journal_issue                   11
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              3447
_journal_page_last               3457
_journal_paper_doi               10.1021/acs.jafc.2c00092
_journal_volume                  70
_journal_year                    2022
_chemical_formula_moiety         'C22 H22 Cl F3 N4 O'
_chemical_formula_sum            'C22 H22 Cl F3 N4 O'
_chemical_formula_weight         450.88
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4942(5)
_cell_length_b                   8.0752(2)
_cell_length_c                   27.7657(6)
_cell_measurement_reflns_used    14750
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.1220
_cell_measurement_theta_min      3.6900
_cell_volume                     4261.09(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      113.15
_diffrn_detector                 pilatus
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     69.00  94.00   0.50    6.00    --    5.00  45.00   0.00   50
  2  ω    -13.00  28.00   0.50    6.00    --  -13.60  45.00  30.00   82
  3  ω   -102.00  75.00   0.50    6.00    --  -13.60  45.00 120.00  354
  4  ω      7.00  75.00   0.50    6.00    --  -13.60  45.00   0.00  136
  5  ω    -61.00 -34.00   0.50    6.00    --  -13.60  45.00  60.00   54
  6  ω      2.00  65.00   0.50    6.00    --  -13.60  45.00  60.00  126
  7  ω    -56.00 -31.00   0.50    6.00    --  -13.60  45.00  30.00   50
  8  ω    -38.00 -12.00   0.50    6.00    --  -13.60  45.00  90.00   52
  9  ω   -103.00  75.00   0.50    6.00    --  -13.60  45.00 169.21  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku 007hf'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0040065000
_diffrn_orient_matrix_UB_12      -0.0802309000
_diffrn_orient_matrix_UB_13      0.0094020000
_diffrn_orient_matrix_UB_21      -0.0066614000
_diffrn_orient_matrix_UB_22      -0.0325604000
_diffrn_orient_matrix_UB_23      -0.0243164000
_diffrn_orient_matrix_UB_31      0.0365204000
_diffrn_orient_matrix_UB_32      -0.0146993000
_diffrn_orient_matrix_UB_33      0.0025594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            27323
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.051
_diffrn_reflns_theta_min         3.396
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_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     284
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0353
_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)+(0.0418P)²+5.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             5003
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jf2c00092_si_002.cif
_cod_data_source_block           m20210315a
_cod_database_code               1566735
_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   0.967
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N4(H4)
2.b Ternary CH refined with riding coordinates:
 C22(H22)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.843
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
Cl1 Cl 0.56221(2) 0.89514(4) 0.37960(2) 0.02425(9) Uani 1 1 d . . . . .
F1 F 0.49178(5) 1.22294(11) 0.38753(4) 0.0365(2) Uani 1 1 d . . . . .
F2 F 0.38010(5) 1.16736(12) 0.37473(4) 0.0411(2) Uani 1 1 d . . . . .
F3 F 0.13462(4) 0.92544(11) 0.61623(3) 0.0292(2) Uani 1 1 d . . . . .
O1 O 0.35732(5) 1.11915(11) 0.48588(4) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.50279(6) 0.74403(13) 0.44429(4) 0.0182(2) Uani 1 1 d . . . . .
N2 N 0.45570(6) 0.75735(13) 0.47307(4) 0.0177(2) Uani 1 1 d . . . . .
N3 N 0.34893(6) 0.85932(13) 0.51692(4) 0.0168(2) Uani 1 1 d . . . . .
H3 H 0.367805 0.759867 0.518841 0.020 Uiso 1 1 calc R . . . .
N4 N 0.34804(6) 0.66247(14) 0.59630(4) 0.0216(2) Uani 1 1 d . . . . .
H4 H 0.387942 0.712720 0.602558 0.026 Uiso 1 1 d R . . . .
C1 C 0.54278(8) 0.59254(17) 0.44303(6) 0.0264(3) Uani 1 1 d . . . . .
H1A H 0.536934 0.519521 0.470022 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.592696 0.619723 0.446866 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.525625 0.536345 0.411349 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.50500(7) 0.88268(16) 0.41761(4) 0.0169(2) Uani 1 1 d . . . . .
C3 C 0.45745(6) 0.99440(15) 0.42889(4) 0.0159(2) Uani 1 1 d . . . . .
C4 C 0.42827(6) 0.90874(15) 0.46390(4) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.37467(6) 0.97295(15) 0.48972(4) 0.0155(2) Uani 1 1 d . . . . .
C6 C 0.29460(6) 0.88466(15) 0.54261(4) 0.0154(2) Uani 1 1 d . . . . .
C7 C 0.24336(7) 1.00594(16) 0.52908(5) 0.0183(2) Uani 1 1 d . . . . .
H7 H 0.245310 1.079069 0.502616 0.022 Uiso 1 1 calc R . . . .
C8 C 0.18921(7) 1.02093(16) 0.55404(5) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.154339 1.104451 0.545315 0.025 Uiso 1 1 calc R . . . .
C9 C 0.18758(7) 0.91153(16) 0.59169(5) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.23742(7) 0.79000(16) 0.60655(5) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.234165 0.716353 0.632628 0.023 Uiso 1 1 calc R . . . .
C11 C 0.29282(7) 0.77762(15) 0.58237(4) 0.0166(2) Uani 1 1 d . . . . .
C12 C 0.34643(7) 0.53995(16) 0.63308(5) 0.0191(3) Uani 1 1 d . . . . .
C13 C 0.29603(7) 0.41549(17) 0.62459(5) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.261104 0.414276 0.594650 0.026 Uiso 1 1 calc R . . . .
C14 C 0.29649(7) 0.29279(17) 0.65968(5) 0.0214(3) Uani 1 1 d . . . . .
H14 H 0.261424 0.208991 0.653323 0.026 Uiso 1 1 calc R . . . .
C15 C 0.34711(7) 0.28908(16) 0.70415(5) 0.0195(3) Uani 1 1 d . . . . .
C16 C 0.39740(7) 0.41415(18) 0.71176(5) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.432808 0.414837 0.741449 0.029 Uiso 1 1 calc R . . . .
C17 C 0.39716(7) 0.53859(17) 0.67691(5) 0.0234(3) Uani 1 1 d . . . . .
H17 H 0.431970 0.622974 0.683224 0.028 Uiso 1 1 calc R . . . .
C18 C 0.34618(8) 0.15018(17) 0.74183(5) 0.0249(3) Uani 1 1 d . . . . .
C19 C 0.27338(10) 0.1366(2) 0.75320(8) 0.0464(5) Uani 1 1 d . . . . .
H19A H 0.260492 0.243163 0.765618 0.070 Uiso 1 1 calc GR . . . .
H19B H 0.273984 0.050938 0.778280 0.070 Uiso 1 1 calc GR . . . .
H19C H 0.238884 0.107149 0.723016 0.070 Uiso 1 1 calc GR . . . .
C20 C 0.40003(12) 0.1815(3) 0.79032(6) 0.0519(5) Uani 1 1 d . . . . .
H20A H 0.447423 0.185253 0.783860 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.397447 0.091989 0.813678 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.389659 0.287380 0.804436 0.078 Uiso 1 1 calc GR . . . .
C21 C 0.36526(10) -0.01482(19) 0.72078(6) 0.0363(4) Uani 1 1 d . . . . .
H21A H 0.332155 -0.037377 0.689348 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.362669 -0.104097 0.744212 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.413157 -0.008406 0.715319 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.44048(7) 1.16507(16) 0.40969(5) 0.0200(3) Uani 1 1 d . . . . .
H22 H 0.436095 1.240236 0.437475 0.024 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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 C1 121.34(11) . . ?
C2 N1 N2 111.62(10) . . ?
C2 N1 C1 127.01(11) . . ?
C4 N2 N1 104.84(10) . . ?
C5 N3 H3 116.8 . . ?
C5 N3 C6 126.46(11) . . ?
C6 N3 H3 116.8 . . ?
C11 N4 H4 110.2 . . ?
C11 N4 C12 121.08(10) . . ?
C12 N4 H4 110.2 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 Cl1 119.71(9) . . ?
N1 C2 C3 108.24(11) . . ?
C3 C2 Cl1 132.02(10) . . ?
C2 C3 C4 103.31(11) . . ?
C2 C3 C22 129.18(11) . . ?
C4 C3 C22 127.51(11) . . ?
N2 C4 C3 111.98(11) . . ?
N2 C4 C5 121.45(11) . . ?
C3 C4 C5 126.56(11) . . ?
O1 C5 N3 124.87(11) . . ?
O1 C5 C4 120.26(11) . . ?
N3 C5 C4 114.86(11) . . ?
C7 C6 N3 122.58(11) . . ?
C7 C6 C11 120.17(11) . . ?
C11 C6 N3 117.22(11) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.41(11) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.15(12) . . ?
C9 C8 H8 120.9 . . ?
F3 C9 C8 118.41(11) . . ?
F3 C9 C10 118.12(11) . . ?
C8 C9 C10 123.46(12) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.44(11) . . ?
C11 C10 H10 120.8 . . ?
C6 C11 N4 117.97(11) . . ?
C10 C11 N4 122.71(11) . . ?
C10 C11 C6 119.31(11) . . ?
C13 C12 N4 120.52(12) . . ?
C17 C12 N4 120.55(12) . . ?
C17 C12 C13 118.86(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.25(12) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.85(13) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C18 120.23(12) . . ?
C16 C15 C14 116.98(12) . . ?
C16 C15 C18 122.79(12) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.64(12) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 C16 120.41(13) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C15 110.24(12) . . ?
C19 C18 C20 108.47(15) . . ?
C19 C18 C21 109.42(14) . . ?
C20 C18 C15 111.59(13) . . ?
C20 C18 C21 107.54(14) . . ?
C21 C18 C15 109.51(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 C22 C3 110.55(10) . . ?
F1 C22 H22 109.6 . . ?
F2 C22 F1 106.24(11) . . ?
F2 C22 C3 111.06(11) . . ?
F2 C22 H22 109.6 . . ?
C3 C22 H22 109.6 . . ?
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
Cl1 C2 1.7003(12) . ?
F1 C22 1.3679(15) . ?
F2 C22 1.3488(16) . ?
F3 C9 1.3623(14) . ?
O1 C5 1.2262(15) . ?
N1 N2 1.3490(14) . ?
N1 C1 1.4551(16) . ?
N1 C2 1.3485(16) . ?
N2 C4 1.3360(16) . ?
N3 H3 0.8800 . ?
N3 C5 1.3539(16) . ?
N3 C6 1.4173(15) . ?
N4 H4 0.8600 . ?
N4 C11 1.4098(16) . ?
N4 C12 1.4273(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3787(17) . ?
C3 C4 1.4116(16) . ?
C3 C22 1.4881(17) . ?
C4 C5 1.4861(16) . ?
C6 C7 1.3896(17) . ?
C6 C11 1.4087(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3910(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3744(18) . ?
C9 C10 1.3779(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3964(17) . ?
C12 C13 1.3885(19) . ?
C12 C17 1.3867(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3884(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3987(18) . ?
C15 C16 1.3905(19) . ?
C15 C18 1.5367(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3944(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.525(2) . ?
C18 C20 1.533(2) . ?
C18 C21 1.534(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
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
Cl1 C2 C3 C4 -178.27(11) . . . . ?
Cl1 C2 C3 C22 1.2(2) . . . . ?
F3 C9 C10 C11 -178.45(11) . . . . ?
N1 N2 C4 C3 0.15(14) . . . . ?
N1 N2 C4 C5 -178.57(11) . . . . ?
N1 C2 C3 C4 0.03(13) . . . . ?
N1 C2 C3 C22 179.54(12) . . . . ?
N2 N1 C2 Cl1 178.60(9) . . . . ?
N2 N1 C2 C3 0.06(14) . . . . ?
N2 C4 C5 O1 170.01(12) . . . . ?
N2 C4 C5 N3 -9.35(17) . . . . ?
N3 C6 C7 C8 177.01(12) . . . . ?
N3 C6 C11 N4 5.04(17) . . . . ?
N3 C6 C11 C10 -175.45(11) . . . . ?
N4 C12 C13 C14 177.37(12) . . . . ?
N4 C12 C17 C16 -176.95(12) . . . . ?
C1 N1 N2 C4 -178.37(12) . . . . ?
C1 N1 C2 Cl1 -3.28(18) . . . . ?
C1 N1 C2 C3 178.18(12) . . . . ?
C2 N1 N2 C4 -0.13(14) . . . . ?
C2 C3 C4 N2 -0.11(14) . . . . ?
C2 C3 C4 C5 178.53(12) . . . . ?
C2 C3 C22 F1 -16.39(19) . . . . ?
C2 C3 C22 F2 101.27(15) . . . . ?
C3 C4 C5 O1 -8.51(19) . . . . ?
C3 C4 C5 N3 172.13(12) . . . . ?
C4 C3 C22 F1 163.02(12) . . . . ?
C4 C3 C22 F2 -79.32(16) . . . . ?
C5 N3 C6 C7 24.84(19) . . . . ?
C5 N3 C6 C11 -156.96(12) . . . . ?
C6 N3 C5 O1 4.8(2) . . . . ?
C6 N3 C5 C4 -175.86(11) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C7 C6 C11 N4 -176.71(12) . . . . ?
C7 C6 C11 C10 2.80(19) . . . . ?
C7 C8 C9 F3 -179.90(12) . . . . ?
C7 C8 C9 C10 1.2(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 N4 177.07(12) . . . . ?
C9 C10 C11 C6 -2.42(19) . . . . ?
C11 N4 C12 C13 66.05(17) . . . . ?
C11 N4 C12 C17 -117.04(14) . . . . ?
C11 C6 C7 C8 -1.14(19) . . . . ?
C12 N4 C11 C6 -174.05(12) . . . . ?
C12 N4 C11 C10 6.45(19) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C13 C14 C15 C18 -179.44(12) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C14 C15 C18 C19 -52.26(18) . . . . ?
C14 C15 C18 C20 -172.86(14) . . . . ?
C14 C15 C18 C21 68.19(17) . . . . ?
C15 C16 C17 C12 -0.5(2) . . . . ?
C16 C15 C18 C19 128.44(16) . . . . ?
C16 C15 C18 C20 7.8(2) . . . . ?
C16 C15 C18 C21 -111.12(16) . . . . ?
C17 C12 C13 C14 0.4(2) . . . . ?
C18 C15 C16 C17 179.85(13) . . . . ?
C22 C3 C4 N2 -179.64(12) . . . . ?
C22 C3 C4 C5 -1.0(2) . . . . ?
