data_cu_szw_1218_a
_audit_creation_date               2025-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety          
 'C H2 Cl, C0.551 H1.102 Cl0.774, C26 H12 F6 N4, C0.449 H0.898 Cl0.226'
_chemical_formula_sum              'C28 H16 Cl2 F6 N4'
_chemical_formula_weight           593.35
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
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'
 'Cl' 'Cl' 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             18
_space_group_name_H-M_alt          'P 21 21 2'
_space_group_name_Hall             'P 2 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x+1/2, y+1/2, -z'
 '-x, -y, z'

_cell_length_a                     12.9156(9)
_cell_length_b                     20.0304(13)
_cell_length_c                     9.9686(6)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2578.9(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9085
_cell_measurement_temperature      200(2)
_cell_measurement_theta_max        70.159
_cell_measurement_theta_min        4.415
_shelx_estimated_absorpt_T_max     0.497
_shelx_estimated_absorpt_T_min     0.398
_exptl_absorpt_coefficient_mu      2.899
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.4655
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0871 after correction.
The Ratio of minimum to maximum transmission is 0.6179.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellowish yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     yellowish
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.528
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1200
_exptl_crystal_size_max            0.39
_exptl_crystal_size_mid            0.34
_exptl_crystal_size_min            0.28
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0549
_diffrn_reflns_av_unetI/netI       0.0491
_diffrn_reflns_Laue_measured_fraction_full  0.983
_diffrn_reflns_Laue_measured_fraction_max  0.980
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         24
_diffrn_reflns_limit_k_min         -20
_diffrn_reflns_limit_l_max         8
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              13766
_diffrn_reflns_point_group_measured_fraction_full  0.957
_diffrn_reflns_point_group_measured_fraction_max  0.950
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           70.197
_diffrn_reflns_theta_min           4.073
_diffrn_ambient_temperature        200.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.983
_diffrn_measured_fraction_theta_max  0.980
_diffrn_measurement_device_type    'Bruker APEX-IICCD'
_diffrn_measurement_method         ?
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.1
_diffrn_source_power               0.055
_diffrn_source_voltage             50.0
_reflns_Friedel_coverage           0.708
_reflns_Friedel_fraction_full      0.922
_reflns_Friedel_fraction_max       0.911
_reflns_number_gt                  4533
_reflns_number_total               4666
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.41 (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.390
_refine_diff_density_min           -0.520
_refine_diff_density_rms           0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.132(7)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       381
_refine_ls_number_reflns           4666
_refine_ls_number_restraints       18
_refine_ls_R_factor_all            0.0494
_refine_ls_R_factor_gt             0.0476
_refine_ls_restrained_S_all        1.070
_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)+(0.0671P)²+1.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1188
_refine_ls_wR_factor_ref           0.1195
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 Cl00, Cl
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Cl \\sim Cl00: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 1.7A
Uanis(Cl) \\sim Ueq, Uanis(Cl00) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(Cl)=1-FVAR(1)
 Sof(Cl00)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=1-FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C2A(H2AA,H2AB)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C13(H13), C14(H14), C17(H17), C18(H18), C20(H20), C21(H21),
 C23(H23), C24(H24), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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 0.06474(8) 0.42994(4) -0.04658(9) 0.0409(3) Uani 1 1 d . . . . .
 Cl00 Cl 0.3342(2) 0.4913(2) 0.1501(8) 0.1066(16) Uani 0.774(14) 1 d . U P A
 1
 F1 F 0.4935(3) 0.74300(18) 0.0948(3) 0.0745(10) Uani 1 1 d . . . . .
 F2 F 0.3945(2) 0.66701(16) 0.1694(3) 0.0594(8) Uani 1 1 d . . . . .
 F3 F 0.5500(2) 0.67410(16) 0.2382(3) 0.0615(8) Uani 1 1 d . . . . .
 N1 N 0.18246(19) 0.65200(13) 0.4898(3) 0.0206(5) Uani 1 1 d . . . . .
 N2 N 0.29907(19) 0.75900(13) 0.6453(3) 0.0208(5) Uani 1 1 d . . . . .
 N3 N 0.1298(2) 0.60867(15) 0.2909(3) 0.0315(6) Uani 1 1 d . . . . .
 N4 N 0.3554(2) 0.86609(14) 0.6503(3) 0.0302(6) Uani 1 1 d . . . . .
 C1 C 0.0507(3) 0.48264(18) 0.0983(3) 0.0326(8) Uani 1 1 d . . . . .
 H1A H 0.0569 0.4552 0.1806 0.039 Uiso 1 1 calc R U . . .
 H1B H 0.1070 0.5161 0.0993 0.039 Uiso 1 1 calc R U . . .
 F4 F -0.0362(3) 0.89781(16) 0.3592(7) 0.119(2) Uani 1 1 d . . . . .
 C3 C 0.0610(3) 0.88246(18) 0.3648(4) 0.0384(8) Uani 1 1 d . . . . .
 C4 C 0.0815(3) 0.81006(17) 0.3423(3) 0.0279(7) Uani 1 1 d . . . . .
 C5 C 0.1263(2) 0.77210(15) 0.4434(3) 0.0222(6) Uani 1 1 d . . . . .
 H5 H 0.1437 0.7908 0.5280 0.027 Uiso 1 1 calc R U . . .
 C6 C 0.1442(2) 0.70545(16) 0.4144(3) 0.0210(6) Uani 1 1 d . . . . .
 C7 C 0.2171(2) 0.64748(16) 0.6233(3) 0.0205(6) Uani 1 1 d . . . . .
 C8 C 0.2551(2) 0.70110(16) 0.6995(3) 0.0218(6) Uani 1 1 d . . . . .
 C9 C 0.3499(2) 0.76955(15) 0.5246(3) 0.0209(6) Uani 1 1 d . . . . .
 C10 C 0.3771(2) 0.72773(16) 0.4206(3) 0.0227(6) Uani 1 1 d . . . . .
 H10 H 0.3583 0.6819 0.4205 0.027 Uiso 1 1 calc R U . . .
 C11 C 0.4333(2) 0.75582(17) 0.3154(3) 0.0263(7) Uani 1 1 d . . . . .
 C12 C 0.4669(3) 0.7108(2) 0.2053(3) 0.0338(8) Uani 1 1 d . . . . .
 C13 C 0.0536(3) 0.7824(2) 0.2169(4) 0.0361(8) Uani 1 1 d . . . . .
 H13 H 0.0242 0.8101 0.1496 0.043 Uiso 1 1 calc R U . . .
 C14 C 0.0687(3) 0.71576(19) 0.1917(3) 0.0354(8) Uani 1 1 d . . . . .
 H14 H 0.0489 0.6967 0.1082 0.043 Uiso 1 1 calc R U . . .
 C15 C 0.1140(3) 0.67651(17) 0.2916(3) 0.0271(7) Uani 1 1 d . . . . .
 C16 C 0.1675(3) 0.59505(16) 0.4101(3) 0.0264(7) Uani 1 1 d . . . . .
 C17 C 0.1808(3) 0.53062(17) 0.4701(4) 0.0354(8) Uani 1 1 d . . . . .
 H17 H 0.1794 0.4915 0.4163 0.042 Uiso 1 1 calc R U . . .
 C18 C 0.1953(3) 0.52613(17) 0.6033(4) 0.0349(8) Uani 1 1 d . . . . .
 H18 H 0.1957 0.4833 0.6443 0.042 Uiso 1 1 calc R U . . .
 C19 C 0.2104(3) 0.58436(17) 0.6853(4) 0.0294(7) Uani 1 1 d . . . . .
 C20 C 0.2200(3) 0.57943(19) 0.8256(4) 0.0356(8) Uani 1 1 d . . . . .
 H20 H 0.2180 0.5368 0.8672 0.043 Uiso 1 1 calc R U . . .
 C21 C 0.2322(3) 0.6353(2) 0.9024(4) 0.0350(8) Uani 1 1 d . . . . .
 H21 H 0.2280 0.6321 0.9974 0.042 Uiso 1 1 calc R U . . .
 C22 C 0.2509(3) 0.69766(18) 0.8418(3) 0.0277(7) Uani 1 1 d . . . . .
 C23 C 0.2638(3) 0.7582(2) 0.9173(3) 0.0330(8) Uani 1 1 d . . . . .
 H23 H 0.2573 0.7567 1.0122 0.040 Uiso 1 1 calc R U . . .
 C24 C 0.2847(3) 0.81665(19) 0.8577(4) 0.0340(8) Uani 1 1 d . . . . .
 H24 H 0.2825 0.8569 0.9080 0.041 Uiso 1 1 calc R U . . .
 C25 C 0.3100(2) 0.81803(16) 0.7193(4) 0.0269(7) Uani 1 1 d . . . . .
 C26 C 0.3811(2) 0.83715(15) 0.5295(4) 0.0250(6) Uani 1 1 d . . . . .
 C27 C 0.4379(3) 0.86410(17) 0.4221(4) 0.0306(7) Uani 1 1 d . . . . .
 H27 H 0.4588 0.9096 0.4227 0.037 Uiso 1 1 calc R U . . .
 C28 C 0.4624(3) 0.82334(18) 0.3166(4) 0.0312(7) Uani 1 1 d . . . . .
 H28 H 0.4997 0.8411 0.2427 0.037 Uiso 1 1 calc R U . . .
 F29 F 0.0960(4) 0.90456(15) 0.4797(4) 0.1090(18) Uani 1 1 d . . . . .
 F30 F 0.1064(4) 0.92047(15) 0.2752(5) 0.1023(15) Uani 1 1 d . . . . .
 C2 C 0.4627(12) 0.4976(11) 0.088(5) 0.122(12) Uani 0.55(4) 1 d . . P A 1
 H2A H 0.4605 0.4568 0.0324 0.146 Uiso 0.55(4) 1 calc R U P A 1
 H2B H 0.4488 0.5339 0.0233 0.146 Uiso 0.55(4) 1 calc R U P A 1
 Cl Cl 0.3512(11) 0.4724(10) 0.068(3) 0.119(5) Uani 0.226(14) 1 d . U P A 2
 C2A C 0.4666(13) 0.4965(11) 0.198(5) 0.090(9) Uani 0.45(4) 1 d . . P A 2
 H2AA H 0.4397 0.5378 0.2401 0.108 Uiso 0.45(4) 1 calc R U P A 2
 H2AB H 0.4591 0.4617 0.2681 0.108 Uiso 0.45(4) 1 calc R U P A 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.798(3) . ?
 Cl00 C2 1.77(3) . ?
 F1 C12 1.322(4) . ?
 F2 C12 1.332(4) . ?
 F3 C12 1.341(5) . ?
 N1 C6 1.398(4) . ?
 N1 C7 1.407(4) . ?
 N1 C16 1.404(4) . ?
 N2 C8 1.400(4) . ?
 N2 C9 1.387(4) . ?
 N2 C25 1.401(4) . ?
 N3 C15 1.374(5) . ?
 N3 C16 1.313(5) . ?
 N4 C25 1.320(5) . ?
 N4 C26 1.377(5) . ?
 C1 C1 1.483(7) 4_565 ?
 C1 H1A 0.9900 . ?
 C1 H1B 0.9900 . ?
 F4 C3 1.293(5) . ?
 C3 C4 1.491(5) . ?
 C3 F29 1.308(5) . ?
 C3 F30 1.311(5) . ?
 C4 C5 1.389(4) . ?
 C4 C13 1.414(5) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.386(4) . ?
 C6 C15 1.409(4) . ?
 C7 C8 1.404(4) . ?
 C7 C19 1.410(4) . ?
 C8 C22 1.421(4) . ?
 C9 C10 1.378(5) . ?
 C9 C26 1.413(4) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.394(4) . ?
 C11 C12 1.485(5) . ?
 C11 C28 1.403(5) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.371(6) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.397(5) . ?
 C16 C17 1.433(5) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.344(6) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.437(5) . ?
 C19 C20 1.408(5) . ?
 C20 H20 0.9500 . ?
 C20 C21 1.366(6) . ?
 C21 H21 0.9500 . ?
 C21 C22 1.408(5) . ?
 C22 C23 1.436(5) . ?
 C23 H23 0.9500 . ?
 C23 C24 1.341(6) . ?
 C24 H24 0.9500 . ?
 C24 C25 1.419(5) . ?
 C26 C27 1.406(5) . ?
 C27 H27 0.9500 . ?
 C27 C28 1.368(6) . ?
 C28 H28 0.9500 . ?
 C2 C2 0.97(3) 4_665 ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 Cl C2A 2.03(4) . ?
 C2A C2A 0.87(4) 4_665 ?
 C2A H2AA 0.9900 . ?
 C2A H2AB 0.9900 . ?

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
 C6 N1 C7 132.1(3) . . ?
 C6 N1 C16 105.6(3) . . ?
 C16 N1 C7 121.8(3) . . ?
 C8 N2 C25 122.5(3) . . ?
 C9 N2 C8 130.8(3) . . ?
 C9 N2 C25 106.3(2) . . ?
 C16 N3 C15 104.8(3) . . ?
 C25 N4 C26 104.8(3) . . ?
 Cl1 C1 H1A 109.4 . . ?
 Cl1 C1 H1B 109.4 . . ?
 C1 C1 Cl1 111.4(2) 4_565 . ?
 C1 C1 H1A 109.4 4_565 . ?
 C1 C1 H1B 109.4 4_565 . ?
 H1A C1 H1B 108.0 . . ?
 F4 C3 C4 113.4(3) . . ?
 F4 C3 F29 107.0(5) . . ?
 F4 C3 F30 105.4(4) . . ?
 F29 C3 C4 113.6(3) . . ?
 F29 C3 F30 104.2(4) . . ?
 F30 C3 C4 112.5(4) . . ?
 C5 C4 C3 119.8(3) . . ?
 C5 C4 C13 122.2(3) . . ?
 C13 C4 C3 118.0(3) . . ?
 C4 C5 H5 121.8 . . ?
 C6 C5 C4 116.4(3) . . ?
 C6 C5 H5 121.8 . . ?
 N1 C6 C15 104.5(3) . . ?
 C5 C6 N1 133.2(3) . . ?
 C5 C6 C15 122.1(3) . . ?
 N1 C7 C19 116.9(3) . . ?
 C8 C7 N1 125.0(3) . . ?
 C8 C7 C19 118.1(3) . . ?
 N2 C8 C7 124.6(3) . . ?
 N2 C8 C22 116.1(3) . . ?
 C7 C8 C22 119.3(3) . . ?
 N2 C9 C26 104.5(3) . . ?
 C10 C9 N2 132.9(3) . . ?
 C10 C9 C26 122.4(3) . . ?
 C9 C10 H10 121.5 . . ?
 C9 C10 C11 116.9(3) . . ?
 C11 C10 H10 121.5 . . ?
 C10 C11 C12 117.6(3) . . ?
 C10 C11 C28 121.4(3) . . ?
 C28 C11 C12 120.9(3) . . ?
 F1 C12 F2 106.3(3) . . ?
 F1 C12 F3 105.3(3) . . ?
 F1 C12 C11 113.3(3) . . ?
 F2 C12 F3 105.5(3) . . ?
 F2 C12 C11 113.1(3) . . ?
 F3 C12 C11 112.7(3) . . ?
 C4 C13 H13 119.8 . . ?
 C14 C13 C4 120.5(3) . . ?
 C14 C13 H13 119.8 . . ?
 C13 C14 H14 120.8 . . ?
 C13 C14 C15 118.4(3) . . ?
 C15 C14 H14 120.8 . . ?
 N3 C15 C6 111.7(3) . . ?
 N3 C15 C14 127.9(3) . . ?
 C14 C15 C6 120.2(3) . . ?
 N1 C16 C17 118.6(3) . . ?
 N3 C16 N1 113.3(3) . . ?
 N3 C16 C17 127.5(3) . . ?
 C16 C17 H17 120.3 . . ?
 C18 C17 C16 119.3(3) . . ?
 C18 C17 H17 120.3 . . ?
 C17 C18 H18 119.1 . . ?
 C17 C18 C19 121.7(3) . . ?
 C19 C18 H18 119.1 . . ?
 C7 C19 C18 119.2(3) . . ?
 C20 C19 C7 119.5(3) . . ?
 C20 C19 C18 121.3(3) . . ?
 C19 C20 H20 119.7 . . ?
 C21 C20 C19 120.7(3) . . ?
 C21 C20 H20 119.7 . . ?
 C20 C21 H21 119.8 . . ?
 C20 C21 C22 120.4(3) . . ?
 C22 C21 H21 119.8 . . ?
 C8 C22 C23 118.6(3) . . ?
 C21 C22 C8 118.6(3) . . ?
 C21 C22 C23 122.9(3) . . ?
 C22 C23 H23 119.1 . . ?
 C24 C23 C22 121.9(3) . . ?
 C24 C23 H23 119.1 . . ?
 C23 C24 H24 120.2 . . ?
 C23 C24 C25 119.6(3) . . ?
 C25 C24 H24 120.2 . . ?
 N2 C25 C24 118.2(3) . . ?
 N4 C25 N2 112.7(3) . . ?
 N4 C25 C24 128.6(3) . . ?
 N4 C26 C9 111.4(3) . . ?
 N4 C26 C27 129.1(3) . . ?
 C27 C26 C9 119.3(3) . . ?
 C26 C27 H27 120.8 . . ?
 C28 C27 C26 118.5(3) . . ?
 C28 C27 H27 120.8 . . ?
 C11 C28 H28 119.3 . . ?
 C27 C28 C11 121.4(3) . . ?
 C27 C28 H28 119.3 . . ?
 Cl00 C2 H2A 96.3 . . ?
 Cl00 C2 H2B 96.3 . . ?
 C2 C2 Cl00 159.7(16) 4_665 . ?
 C2 C2 H2A 96.3 4_665 . ?
 C2 C2 H2B 96.3 4_665 . ?
 H2A C2 H2B 103.4 . . ?
 Cl C2A H2AA 102.2 . . ?
 Cl C2A H2AB 102.2 . . ?
 C2A C2A Cl 139.6(14) 4_665 . ?
 C2A C2A H2AA 102.2 4_665 . ?
 C2A C2A H2AB 102.2 4_665 . ?
 H2AA C2A H2AB 104.8 . . ?

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
 N1 C6 C15 N3 1.4(4) . . . . ?
 N1 C6 C15 C14 178.1(3) . . . . ?
 N1 C7 C8 N2 -24.4(5) . . . . ?
 N1 C7 C8 C22 156.4(3) . . . . ?
 N1 C7 C19 C18 15.9(4) . . . . ?
 N1 C7 C19 C20 -165.0(3) . . . . ?
 N1 C16 C17 C18 7.6(5) . . . . ?
 N2 C8 C22 C21 -164.4(3) . . . . ?
 N2 C8 C22 C23 16.9(4) . . . . ?
 N2 C9 C10 C11 -177.0(3) . . . . ?
 N2 C9 C26 N4 3.0(3) . . . . ?
 N2 C9 C26 C27 178.4(3) . . . . ?
 N3 C16 C17 C18 -163.1(4) . . . . ?
 N4 C26 C27 C28 173.7(3) . . . . ?
 F4 C3 C4 C5 -117.6(5) . . . . ?
 F4 C3 C4 C13 62.2(6) . . . . ?
 C3 C4 C5 C6 -179.1(3) . . . . ?
 C3 C4 C13 C14 -178.7(4) . . . . ?
 C4 C5 C6 N1 -176.6(3) . . . . ?
 C4 C5 C6 C15 -3.2(4) . . . . ?
 C4 C13 C14 C15 -1.2(6) . . . . ?
 C5 C4 C13 C14 1.1(5) . . . . ?
 C5 C6 C15 N3 -173.6(3) . . . . ?
 C5 C6 C15 C14 3.1(5) . . . . ?
 C6 N1 C7 C8 -23.9(5) . . . . ?
 C6 N1 C7 C19 154.5(3) . . . . ?
 C6 N1 C16 N3 3.8(4) . . . . ?
 C6 N1 C16 C17 -168.2(3) . . . . ?
 C7 N1 C6 C5 -0.5(5) . . . . ?
 C7 N1 C6 C15 -174.7(3) . . . . ?
 C7 N1 C16 N3 176.6(3) . . . . ?
 C7 N1 C16 C17 4.6(5) . . . . ?
 C7 C8 C22 C21 14.9(5) . . . . ?
 C7 C8 C22 C23 -163.8(3) . . . . ?
 C7 C19 C20 C21 2.3(6) . . . . ?
 C8 N2 C9 C10 -2.3(5) . . . . ?
 C8 N2 C9 C26 -177.1(3) . . . . ?
 C8 N2 C25 N4 178.6(3) . . . . ?
 C8 N2 C25 C24 6.2(4) . . . . ?
 C8 C7 C19 C18 -165.6(3) . . . . ?
 C8 C7 C19 C20 13.5(5) . . . . ?
 C8 C22 C23 C24 -3.4(5) . . . . ?
 C9 N2 C8 C7 -26.7(5) . . . . ?
 C9 N2 C8 C22 152.6(3) . . . . ?
 C9 N2 C25 N4 5.5(3) . . . . ?
 C9 N2 C25 C24 -166.8(3) . . . . ?
 C9 C10 C11 C12 177.5(3) . . . . ?
 C9 C10 C11 C28 1.0(4) . . . . ?
 C9 C26 C27 C28 -0.9(5) . . . . ?
 C10 C9 C26 N4 -172.5(3) . . . . ?
 C10 C9 C26 C27 2.9(5) . . . . ?
 C10 C11 C12 F1 162.4(3) . . . . ?
 C10 C11 C12 F2 41.3(4) . . . . ?
 C10 C11 C12 F3 -78.2(4) . . . . ?
 C10 C11 C28 C27 1.0(5) . . . . ?
 C12 C11 C28 C27 -175.4(3) . . . . ?
 C13 C4 C5 C6 1.1(5) . . . . ?
 C13 C14 C15 N3 175.3(4) . . . . ?
 C13 C14 C15 C6 -0.7(5) . . . . ?
 C15 N3 C16 N1 -2.8(4) . . . . ?
 C15 N3 C16 C17 168.3(4) . . . . ?
 C16 N1 C6 C5 171.3(3) . . . . ?
 C16 N1 C6 C15 -2.9(3) . . . . ?
 C16 N1 C7 C8 165.4(3) . . . . ?
 C16 N1 C7 C19 -16.2(4) . . . . ?
 C16 N3 C15 C6 0.8(4) . . . . ?
 C16 N3 C15 C14 -175.6(4) . . . . ?
 C16 C17 C18 C19 -7.6(6) . . . . ?
 C17 C18 C19 C7 -4.4(5) . . . . ?
 C17 C18 C19 C20 176.6(4) . . . . ?
 C18 C19 C20 C21 -178.7(3) . . . . ?
 C19 C7 C8 N2 157.2(3) . . . . ?
 C19 C7 C8 C22 -22.0(5) . . . . ?
 C19 C20 C21 C22 -9.6(6) . . . . ?
 C20 C21 C22 C8 1.0(5) . . . . ?
 C20 C21 C22 C23 179.7(3) . . . . ?
 C21 C22 C23 C24 177.9(3) . . . . ?
 C22 C23 C24 C25 -9.6(5) . . . . ?
 C23 C24 C25 N2 8.3(5) . . . . ?
 C23 C24 C25 N4 -162.7(4) . . . . ?
 C25 N2 C8 C7 162.2(3) . . . . ?
 C25 N2 C8 C22 -18.6(4) . . . . ?
 C25 N2 C9 C10 170.0(3) . . . . ?
 C25 N2 C9 C26 -4.8(3) . . . . ?
 C25 N4 C26 C9 0.3(4) . . . . ?
 C25 N4 C26 C27 -174.6(3) . . . . ?
 C26 N4 C25 N2 -3.6(4) . . . . ?
 C26 N4 C25 C24 167.8(3) . . . . ?
 C26 C9 C10 C11 -2.9(4) . . . . ?
 C26 C27 C28 C11 -1.0(5) . . . . ?
 C28 C11 C12 F1 -21.1(5) . . . . ?
 C28 C11 C12 F2 -142.1(3) . . . . ?
 C28 C11 C12 F3 98.3(4) . . . . ?
 F29 C3 C4 C5 4.8(6) . . . . ?
 F29 C3 C4 C13 -175.4(4) . . . . ?
 F30 C3 C4 C5 122.9(4) . . . . ?
 F30 C3 C4 C13 -57.3(5) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
