# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_dm16283_0m
_database_code_depnum_ccdc_archive 'CCDC 1957856'
loop_
_audit_author_name
_audit_author_address
'Xiao-Long Zhang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2019-10-07 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2016-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            
'tricyclic compounds containing trihydro-quinoline'
_chemical_name_systematic        
'tricyclic compounds containing trihydro-quinoline'
_chemical_formula_moiety         'C28 H18 Cl3 F3 N2 O4'
_chemical_formula_sum            'C28 H18 Cl3 F3 N2 O4'
_chemical_formula_weight         609.79
_chemical_absolute_configuration rmad
_chemical_melting_point          298
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3488(9)
_cell_length_b                   10.4603(11)
_cell_length_c                   29.766(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2599.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4813
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.750
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0664 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.9161.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            23723
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.910
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5545
_reflns_number_total             6831
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 2027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      0.971
_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)+(0.0305P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.07114(9) 0.76771(8) 0.65073(2) 0.02932(17) Uani 1 1 d . . . . .
Cl2 Cl 0.98808(9) 0.40692(7) 0.57302(2) 0.02924(17) Uani 1 1 d . . . . .
Cl3 Cl 0.41467(9) 0.34887(7) 0.80670(2) 0.02757(17) Uani 1 1 d . . . . .
F1 F 0.5361(2) 0.93105(15) 0.58734(5) 0.0284(4) Uani 1 1 d . . . . .
F2 F 0.7680(2) 0.95391(17) 0.55806(7) 0.0374(5) Uani 1 1 d . . . . .
F3 F 0.5677(2) 0.90809(16) 0.51573(5) 0.0349(4) Uani 1 1 d . . . . .
O1 O 0.8085(2) 0.71319(19) 0.54523(6) 0.0225(4) Uani 1 1 d . . . . .
O2 O 0.2619(3) 0.3094(2) 0.64233(7) 0.0326(6) Uani 1 1 d . . . . .
O3 O 0.1451(3) 0.3700(2) 0.70295(8) 0.0372(6) Uani 1 1 d . . . . .
O4 O 0.7322(3) 0.1319(2) 0.72379(7) 0.0310(5) Uani 1 1 d . . . . .
N1 N 0.5742(3) 0.6548(2) 0.57785(7) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.2595(3) 0.3687(2) 0.67769(8) 0.0199(5) Uani 1 1 d . . . . .
C1 C 0.4120(3) 0.6756(2) 0.59231(8) 0.0161(5) Uani 1 1 d . . . . .
C2 C 0.3042(3) 0.7471(3) 0.56748(9) 0.0193(6) Uani 1 1 d . . . . .
H2 H 0.3328 0.7768 0.5391 0.023 Uiso 1 1 calc R . . . .
C3 C 0.1531(3) 0.7747(3) 0.58477(9) 0.0210(6) Uani 1 1 d . . . . .
H3 H 0.0805 0.8233 0.5684 0.025 Uiso 1 1 calc R . . . .
C4 C 0.1129(3) 0.7283(3) 0.62685(9) 0.0198(6) Uani 1 1 d . . . . .
C5 C 0.2153(3) 0.6491(3) 0.65058(9) 0.0186(6) Uani 1 1 d . . . . .
H5 H 0.1837 0.6156 0.6781 0.022 Uiso 1 1 calc R . . . .
C6 C 0.3645(3) 0.6199(2) 0.63331(8) 0.0162(6) Uani 1 1 d . . . . .
C7 C 0.4780(3) 0.5230(2) 0.65376(8) 0.0154(5) Uani 1 1 d . . . . .
H7 H 0.5681 0.5711 0.6664 0.018 Uiso 1 1 calc R . . . .
C8 C 0.4086(3) 0.4425(2) 0.69178(8) 0.0161(5) Uani 1 1 d . . . . .
H8 H 0.3790 0.5002 0.7164 0.019 Uiso 1 1 calc R . . . .
C9 C 0.5332(3) 0.3463(3) 0.70988(8) 0.0170(5) Uani 1 1 d . . . . .
H9 H 0.4749 0.2783 0.7255 0.020 Uiso 1 1 calc R . . . .
C10 C 0.6295(3) 0.2850(3) 0.67267(9) 0.0201(6) Uani 1 1 d . . . . .
C11 C 0.6337(3) 0.3267(3) 0.63036(9) 0.0196(6) Uani 1 1 d . . . . .
H11 H 0.6946 0.2813 0.6096 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5452(3) 0.4429(2) 0.61452(8) 0.0167(6) Uani 1 1 d . . . . .
H12 H 0.4545 0.4141 0.5962 0.020 Uiso 1 1 calc R . . . .
C13 C 0.6525(3) 0.5271(2) 0.58479(9) 0.0165(5) Uani 1 1 d . . . . .
H13 H 0.7536 0.5412 0.6008 0.020 Uiso 1 1 calc R . . . .
C14 C 0.6910(3) 0.4639(3) 0.54033(9) 0.0173(6) Uani 1 1 d . . . . .
C15 C 0.8387(3) 0.4059(3) 0.53215(9) 0.0205(6) Uani 1 1 d . . . . .
C16 C 0.8725(4) 0.3486(3) 0.49113(9) 0.0249(6) Uani 1 1 d . . . . .
H16 H 0.9714 0.3100 0.4863 0.030 Uiso 1 1 calc R . . . .
C17 C 0.7588(4) 0.3492(3) 0.45752(10) 0.0261(7) Uani 1 1 d . . . . .
H17 H 0.7812 0.3111 0.4300 0.031 Uiso 1 1 calc R . . . .
C18 C 0.6109(4) 0.4064(3) 0.46464(9) 0.0254(7) Uani 1 1 d . . . . .
H18 H 0.5344 0.4071 0.4419 0.030 Uiso 1 1 calc R . . . .
C19 C 0.5779(4) 0.4624(3) 0.50583(9) 0.0202(6) Uani 1 1 d . . . . .
H19 H 0.4783 0.4998 0.5106 0.024 Uiso 1 1 calc R . . . .
C20 C 0.6768(3) 0.7420(3) 0.55957(8) 0.0172(6) Uani 1 1 d . . . . .
C21 C 0.6336(3) 0.8849(3) 0.55570(9) 0.0215(6) Uani 1 1 d . . . . .
C22 C 0.6389(3) 0.4137(3) 0.74422(8) 0.0182(6) Uani 1 1 d . . . . .
C23 C 0.5927(3) 0.4222(3) 0.78913(9) 0.0205(6) Uani 1 1 d . . . . .
C24 C 0.6836(4) 0.4873(3) 0.82088(10) 0.0264(7) Uani 1 1 d . . . . .
H24 H 0.6497 0.4917 0.8506 0.032 Uiso 1 1 calc R . . . .
C25 C 0.8249(4) 0.5455(3) 0.80778(11) 0.0294(7) Uani 1 1 d . . . . .
H25 H 0.8863 0.5897 0.8287 0.035 Uiso 1 1 calc R . . . .
C26 C 0.8746(4) 0.5378(3) 0.76365(10) 0.0300(7) Uani 1 1 d . . . . .
H26 H 0.9699 0.5765 0.7548 0.036 Uiso 1 1 calc R . . . .
C27 C 0.7821(4) 0.4721(3) 0.73237(10) 0.0245(7) Uani 1 1 d . . . . .
H27 H 0.8170 0.4673 0.7028 0.029 Uiso 1 1 calc R . . . .
C28 C 0.7257(4) 0.1727(3) 0.68571(10) 0.0274(7) Uani 1 1 d . . . . .
H28 H 0.7845 0.1310 0.6636 0.033 Uiso 1 1 calc R . . . .


_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 C4 1.743(3) . ?
Cl2 C15 1.742(3) . ?
Cl3 C23 1.753(3) . ?
F1 C21 1.335(3) . ?
F2 C21 1.336(3) . ?
F3 C21 1.333(3) . ?
O1 C20 1.217(3) . ?
O2 N2 1.222(3) . ?
O3 N2 1.216(3) . ?
O4 C28 1.212(3) . ?
N1 C1 1.438(3) . ?
N1 C13 1.501(3) . ?
N1 C20 1.364(3) . ?
N2 C8 1.524(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.409(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.515(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.525(3) . ?
C7 C12 1.543(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.544(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.511(4) . ?
C9 C22 1.523(4) . ?
C10 C11 1.333(4) . ?
C10 C28 1.475(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.498(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.537(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.514(4) . ?
C14 C15 1.395(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.542(4) . ?
C22 C23 1.394(3) . ?
C22 C27 1.388(4) . ?
C23 C24 1.390(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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 C13 120.3(2) . . ?
C20 N1 C1 127.5(2) . . ?
C20 N1 C13 112.1(2) . . ?
O2 N2 C8 118.7(2) . . ?
O3 N2 O2 123.5(2) . . ?
O3 N2 C8 117.8(2) . . ?
C2 C1 N1 122.3(2) . . ?
C2 C1 C6 120.2(3) . . ?
C6 C1 N1 117.5(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl1 120.0(2) . . ?
C5 C4 Cl1 118.5(2) . . ?
C5 C4 C3 121.5(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 116.7(2) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 124.2(2) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 115.5(2) . . ?
C6 C7 C12 106.7(2) . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C12 113.6(2) . . ?
C12 C7 H7 106.9 . . ?
N2 C8 C7 112.7(2) . . ?
N2 C8 H8 108.1 . . ?
N2 C8 C9 108.4(2) . . ?
C7 C8 H8 108.1 . . ?
C7 C8 C9 111.3(2) . . ?
C9 C8 H8 108.1 . . ?
C8 C9 H9 107.7 . . ?
C10 C9 C8 112.3(2) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C22 112.3(2) . . ?
C22 C9 C8 108.8(2) . . ?
C22 C9 H9 107.7 . . ?
C11 C10 C9 124.6(3) . . ?
C11 C10 C28 119.6(3) . . ?
C28 C10 C9 115.8(2) . . ?
C10 C11 H11 118.3 . . ?
C10 C11 C12 123.3(3) . . ?
C12 C11 H11 118.3 . . ?
C7 C12 H12 107.8 . . ?
C11 C12 C7 112.4(2) . . ?
C11 C12 H12 107.8 . . ?
C11 C12 C13 111.0(2) . . ?
C13 C12 C7 109.7(2) . . ?
C13 C12 H12 107.8 . . ?
N1 C13 C12 109.6(2) . . ?
N1 C13 H13 107.9 . . ?
N1 C13 C14 111.2(2) . . ?
C12 C13 H13 107.9 . . ?
C14 C13 C12 112.1(2) . . ?
C14 C13 H13 107.9 . . ?
C15 C14 C13 122.0(2) . . ?
C19 C14 C13 120.3(2) . . ?
C19 C14 C15 117.7(2) . . ?
C14 C15 Cl2 120.5(2) . . ?
C16 C15 Cl2 118.1(2) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.3 . . ?
C18 C19 C14 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
O1 C20 N1 122.8(3) . . ?
O1 C20 C21 115.1(2) . . ?
N1 C20 C21 122.1(2) . . ?
F1 C21 F2 106.2(2) . . ?
F1 C21 C20 116.1(2) . . ?
F2 C21 C20 108.9(2) . . ?
F3 C21 F1 108.2(2) . . ?
F3 C21 F2 107.2(2) . . ?
F3 C21 C20 109.9(2) . . ?
C23 C22 C9 120.9(2) . . ?
C27 C22 C9 122.1(2) . . ?
C27 C22 C23 117.0(3) . . ?
C22 C23 Cl3 119.5(2) . . ?
C24 C23 Cl3 118.3(2) . . ?
C24 C23 C22 122.2(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 121.7(3) . . ?
C22 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
O4 C28 C10 123.4(3) . . ?
O4 C28 H28 118.3 . . ?
C10 C28 H28 118.3 . . ?

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 C4 C5 C6 -177.6(2) . . . . ?
Cl2 C15 C16 C17 -178.1(2) . . . . ?
Cl3 C23 C24 C25 179.8(2) . . . . ?
O1 C20 C21 F1 -149.5(2) . . . . ?
O1 C20 C21 F2 -29.7(3) . . . . ?
O1 C20 C21 F3 87.4(3) . . . . ?
O2 N2 C8 C7 47.0(3) . . . . ?
O2 N2 C8 C9 -76.6(3) . . . . ?
O3 N2 C8 C7 -134.4(2) . . . . ?
O3 N2 C8 C9 102.0(3) . . . . ?
N1 C1 C2 C3 -174.0(2) . . . . ?
N1 C1 C6 C5 173.2(2) . . . . ?
N1 C1 C6 C7 -11.4(3) . . . . ?
N1 C13 C14 C15 134.7(3) . . . . ?
N1 C13 C14 C19 -45.1(3) . . . . ?
N1 C20 C21 F1 30.4(4) . . . . ?
N1 C20 C21 F2 150.2(2) . . . . ?
N1 C20 C21 F3 -92.7(3) . . . . ?
N2 C8 C9 C10 83.3(3) . . . . ?
N2 C8 C9 C22 -151.7(2) . . . . ?
C1 N1 C13 C12 -9.1(3) . . . . ?
C1 N1 C13 C14 115.4(2) . . . . ?
C1 N1 C20 O1 -174.4(2) . . . . ?
C1 N1 C20 C21 5.7(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C7 C8 -166.6(2) . . . . ?
C1 C6 C7 C12 -39.4(3) . . . . ?
C2 C1 C6 C5 -6.9(4) . . . . ?
C2 C1 C6 C7 168.5(2) . . . . ?
C2 C3 C4 Cl1 176.7(2) . . . . ?
C2 C3 C4 C5 -4.1(4) . . . . ?
C3 C4 C5 C6 3.2(4) . . . . ?
C4 C5 C6 C1 2.3(4) . . . . ?
C4 C5 C6 C7 -172.8(3) . . . . ?
C5 C6 C7 C8 8.6(4) . . . . ?
C5 C6 C7 C12 135.8(3) . . . . ?
C6 C1 C2 C3 6.1(4) . . . . ?
C6 C7 C8 N2 57.4(3) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C12 C11 -168.6(2) . . . . ?
C6 C7 C12 C13 67.4(3) . . . . ?
C7 C8 C9 C10 -41.2(3) . . . . ?
C7 C8 C9 C22 83.8(3) . . . . ?
C7 C12 C13 N1 -42.9(3) . . . . ?
C7 C12 C13 C14 -166.8(2) . . . . ?
C8 C7 C12 C11 -40.2(3) . . . . ?
C8 C7 C12 C13 -164.3(2) . . . . ?
C8 C9 C10 C11 13.7(4) . . . . ?
C8 C9 C10 C28 -167.3(2) . . . . ?
C8 C9 C22 C23 85.9(3) . . . . ?
C8 C9 C22 C27 -92.3(3) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C9 C10 C28 O4 -1.6(4) . . . . ?
C9 C22 C23 Cl3 2.5(4) . . . . ?
C9 C22 C23 C24 -177.4(3) . . . . ?
C9 C22 C27 C26 177.4(3) . . . . ?
C10 C9 C22 C23 -149.1(3) . . . . ?
C10 C9 C22 C27 32.7(4) . . . . ?
C10 C11 C12 C7 11.5(4) . . . . ?
C10 C11 C12 C13 134.8(3) . . . . ?
C11 C10 C28 O4 177.4(3) . . . . ?
C11 C12 C13 N1 -167.7(2) . . . . ?
C11 C12 C13 C14 68.3(3) . . . . ?
C12 C7 C8 N2 -66.2(3) . . . . ?
C12 C7 C8 C9 55.8(3) . . . . ?
C12 C13 C14 C15 -102.2(3) . . . . ?
C12 C13 C14 C19 77.9(3) . . . . ?
C13 N1 C1 C2 -141.1(3) . . . . ?
C13 N1 C1 C6 38.8(3) . . . . ?
C13 N1 C20 O1 9.2(3) . . . . ?
C13 N1 C20 C21 -170.7(2) . . . . ?
C13 C14 C15 Cl2 -1.4(4) . . . . ?
C13 C14 C15 C16 -179.8(3) . . . . ?
C13 C14 C19 C18 179.3(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C14 C19 C18 -0.6(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C14 0.7(4) . . . . ?
C19 C14 C15 Cl2 178.5(2) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
C20 N1 C1 C2 42.8(4) . . . . ?
C20 N1 C1 C6 -137.3(3) . . . . ?
C20 N1 C13 C12 167.6(2) . . . . ?
C20 N1 C13 C14 -67.9(3) . . . . ?
C22 C9 C10 C11 -109.3(3) . . . . ?
C22 C9 C10 C28 69.7(3) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C22 C27 C26 -0.9(4) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C26 C27 C22 0.3(5) . . . . ?
C27 C22 C23 Cl3 -179.2(2) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C28 C10 C11 C12 -177.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_chemical_compound_source        'organic synthesis'
_chemical_properties_physical    Oxygen-sensitive
_exptl_crystal_preparation       'Magnetic properties'
