# 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 2022

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2089344'
loop_
_audit_author_name
_audit_author_address
'Yue Huang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H30 Cl N4 O4'
_chemical_formula_sum            'C35 H30 Cl N4 O4'
_chemical_formula_weight         606.08
_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 0.0033 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'
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                   6.4132(4)
_cell_length_b                   10.9919(7)
_cell_length_c                   40.683(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2867.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8872
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.351
_cell_measurement_theta_min      2.385
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.8560.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            20912
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.385
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4754
_reflns_number_total             5813
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.048
_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)+(0.0443P)²+0.4124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C34(H34), C32(H32), C31(H31), C24(H24), C30(H30), C22(H22), C15(H15),
 C23(H23), C11(H11), C14(H14), C5(H5), C1(H1A), C21(H21), C12(H12), C13(H13),
 C2(H2), C4(H4A), C3(H3)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.26559(15) 0.46882(8) 0.53699(2) 0.0334(2) Uani 1 1 d . . . . .
O2 O 0.6405(3) 0.66044(18) 0.35775(5) 0.0225(5) Uani 1 1 d . . . . .
O1 O 0.7289(4) 0.4236(2) 0.42668(5) 0.0264(5) Uani 1 1 d . . . . .
O4 O 0.0001(3) 0.4784(2) 0.34656(5) 0.0299(6) Uani 1 1 d . . . . .
O3 O 0.4096(4) 0.5998(2) 0.31962(6) 0.0355(6) Uani 1 1 d . . . . .
N3 N 0.1584(4) 0.3702(2) 0.30438(6) 0.0210(6) Uani 1 1 d . . . . .
N4 N 0.3301(4) 0.2930(2) 0.30143(6) 0.0237(6) Uani 1 1 d . . . . .
H4 H 0.364135 0.252223 0.283603 0.028 Uiso 1 1 calc R U . . .
N1 N 0.2804(4) 0.3095(2) 0.38476(6) 0.0202(6) Uani 1 1 d . . . . .
N2 N 0.6025(4) 0.6113(2) 0.44179(6) 0.0224(6) Uani 1 1 d . . . . .
C25 C 0.5010(5) 0.5838(3) 0.34489(8) 0.0203(7) Uani 1 1 d . . . . .
C29 C 0.2625(5) 0.3453(3) 0.44461(7) 0.0176(6) Uani 1 1 d . . . . .
C34 C 0.2540(5) 0.4209(3) 0.47190(7) 0.0195(7) Uani 1 1 d . . . . .
H34 H 0.239168 0.506313 0.469161 0.023 Uiso 1 1 calc R U . . .
C20 C 0.4341(5) 0.6860(3) 0.43301(7) 0.0207(7) Uani 1 1 d . . . . .
C19 C 0.3132(5) 0.6288(3) 0.40916(7) 0.0186(7) Uani 1 1 d . . . . .
C16 C 0.4801(5) 0.4744(3) 0.36677(7) 0.0163(7) Uani 1 1 d . . . . .
H16 H 0.622365 0.437908 0.368806 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3340(5) 0.3726(3) 0.35429(7) 0.0175(7) Uani 1 1 d . . . . .
C28 C 0.2451(5) 0.4005(3) 0.41048(7) 0.0182(7) Uani 1 1 d . . . . .
H28 H 0.101040 0.433894 0.407776 0.022 Uiso 1 1 calc R U . . .
C32 C 0.2809(5) 0.2479(3) 0.50811(8) 0.0234(7) Uani 1 1 d . . . . .
H32 H 0.286899 0.215008 0.529677 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4302(5) 0.2904(3) 0.32857(8) 0.0189(7) Uani 1 1 d . . . . .
C7 C 0.1424(5) 0.4184(3) 0.33554(8) 0.0207(7) Uani 1 1 d . . . . .
C31 C 0.2855(5) 0.1740(3) 0.48113(8) 0.0244(7) Uani 1 1 d . . . . .
H31 H 0.293751 0.088440 0.484121 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1354(5) 0.6844(3) 0.39783(8) 0.0247(8) Uani 1 1 d . . . . .
H24 H 0.048996 0.645135 0.382103 0.030 Uiso 1 1 calc R U . . .
C18 C 0.5984(5) 0.5038(3) 0.42477(7) 0.0195(7) Uani 1 1 d . . . . .
C17 C 0.4041(5) 0.5037(3) 0.40251(7) 0.0165(7) Uani 1 1 d . . . . .
C10 C 0.6165(5) 0.2129(3) 0.33277(8) 0.0220(7) Uani 1 1 d . . . . .
C6 C 0.0151(5) 0.3791(3) 0.27802(7) 0.0224(7) Uani 1 1 d . . . . .
C33 C 0.2672(5) 0.3716(3) 0.50310(7) 0.0217(7) Uani 1 1 d . . . . .
C30 C 0.2784(5) 0.2208(3) 0.44942(8) 0.0229(7) Uani 1 1 d . . . . .
H30 H 0.284452 0.167570 0.431061 0.028 Uiso 1 1 calc R U . . .
C22 C 0.2079(6) 0.8555(3) 0.43306(9) 0.0326(9) Uani 1 1 d . . . . .
H22 H 0.171402 0.934269 0.440800 0.039 Uiso 1 1 calc R U . . .
C26 C 0.6708(5) 0.7754(3) 0.34065(8) 0.0263(8) Uani 1 1 d . . . . .
H26A H 0.648563 0.763652 0.316781 0.032 Uiso 1 1 calc R U . . .
H26B H 0.815571 0.804133 0.344002 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7041(5) 0.1906(3) 0.36364(9) 0.0270(8) Uani 1 1 d . . . . .
H15 H 0.645202 0.227029 0.382668 0.032 Uiso 1 1 calc R U . . .
C23 C 0.0836(6) 0.7998(3) 0.40983(9) 0.0299(8) Uani 1 1 d . . . . .
H23 H -0.037759 0.839879 0.401953 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7074(6) 0.1585(3) 0.30522(9) 0.0295(8) Uani 1 1 d . . . . .
H11 H 0.649447 0.172469 0.284064 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8769(6) 0.1154(3) 0.36657(10) 0.0336(9) Uani 1 1 d . . . . .
H14 H 0.934397 0.099683 0.387668 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0322(6) 0.2988(3) 0.25161(8) 0.0309(8) Uani 1 1 d . . . . .
H5 H 0.144982 0.242929 0.250325 0.037 Uiso 1 1 calc R U . . .
C1 C -0.1468(5) 0.4622(3) 0.27941(8) 0.0305(8) Uani 1 1 d . . . . .
H1A H -0.155667 0.518293 0.297123 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3843(6) 0.7993(3) 0.44531(8) 0.0291(8) Uani 1 1 d . . . . .
H21 H 0.468217 0.837207 0.461598 0.035 Uiso 1 1 calc R U . . .
C35 C 0.7525(6) 0.6387(3) 0.46730(8) 0.0345(9) Uani 1 1 d . . . . .
H35A H 0.817963 0.717524 0.462760 0.052 Uiso 1 1 calc R U . . .
H35B H 0.859740 0.575212 0.467816 0.052 Uiso 1 1 calc R U . . .
H35C H 0.681539 0.642001 0.488615 0.052 Uiso 1 1 calc R U . . .
C12 C 0.8796(6) 0.0851(3) 0.30841(10) 0.0369(9) Uani 1 1 d . . . . .
H12 H 0.940144 0.049132 0.289446 0.044 Uiso 1 1 calc R U . . .
C27 C 0.5202(6) 0.8688(3) 0.35347(9) 0.0344(9) Uani 1 1 d . . . . .
H27A H 0.549090 0.947546 0.343149 0.052 Uiso 1 1 calc R U . . .
H27B H 0.536017 0.876043 0.377352 0.052 Uiso 1 1 calc R U . . .
H27C H 0.377367 0.843632 0.348280 0.052 Uiso 1 1 calc R U . . .
C13 C 0.9658(6) 0.0632(3) 0.33908(10) 0.0388(10) Uani 1 1 d . . . . .
H13 H 1.085185 0.012637 0.341173 0.047 Uiso 1 1 calc R U . . .
C2 C -0.2953(6) 0.4630(4) 0.25487(9) 0.0435(10) Uani 1 1 d . . . . .
H2 H -0.407255 0.519504 0.255808 0.052 Uiso 1 1 calc R U . . .
C4 C -0.1199(7) 0.3022(4) 0.22713(9) 0.0440(11) Uani 1 1 d . . . . .
H4A H -0.110940 0.248334 0.208933 0.053 Uiso 1 1 calc R U . . .
C3 C -0.2824(7) 0.3830(4) 0.22918(9) 0.0473(11) Uani 1 1 d . . . . .
H3 H -0.386925 0.383437 0.212629 0.057 Uiso 1 1 calc R U . . .
H1 H 0.167(6) 0.265(3) 0.3830(8) 0.021(9) Uiso 1 1 d . . . . .


_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 C33 1.745(3) . ?
O2 C25 1.335(4) . ?
O2 C26 1.455(3) . ?
O1 C18 1.217(4) . ?
O4 C7 1.212(4) . ?
O3 C25 1.196(4) . ?
N3 N4 1.395(4) . ?
N3 C7 1.378(4) . ?
N3 C6 1.416(4) . ?
N4 H4 0.8800 . ?
N4 C9 1.278(4) . ?
N1 C8 1.461(4) . ?
N1 C28 1.465(4) . ?
N1 H1 0.88(3) . ?
N2 C20 1.403(4) . ?
N2 C18 1.370(4) . ?
N2 C35 1.447(4) . ?
C25 C16 1.502(4) . ?
C29 C34 1.388(4) . ?
C29 C28 1.520(4) . ?
C29 C30 1.386(4) . ?
C34 H34 0.9500 . ?
C34 C33 1.383(4) . ?
C20 C19 1.392(4) . ?
C20 C21 1.379(5) . ?
C19 C24 1.373(4) . ?
C19 C17 1.517(4) . ?
C16 H16 1.0000 . ?
C16 C8 1.546(4) . ?
C16 C17 1.567(4) . ?
C8 C9 1.513(4) . ?
C8 C7 1.531(4) . ?
C28 H28 1.0000 . ?
C28 C17 1.559(4) . ?
C32 H32 0.9500 . ?
C32 C31 1.366(4) . ?
C32 C33 1.377(4) . ?
C9 C10 1.478(4) . ?
C31 H31 0.9500 . ?
C31 C30 1.390(4) . ?
C24 H24 0.9500 . ?
C24 C23 1.399(4) . ?
C18 C17 1.541(4) . ?
C10 C15 1.397(5) . ?
C10 C11 1.397(5) . ?
C6 C5 1.395(5) . ?
C6 C1 1.385(5) . ?
C30 H30 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.380(5) . ?
C22 C21 1.383(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.503(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(5) . ?
C23 H23 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.374(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.395(5) . ?
C1 H1A 0.9500 . ?
C1 C2 1.380(5) . ?
C21 H21 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.386(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C13 H13 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.368(6) . ?
C4 H4A 0.9500 . ?
C4 C3 1.372(6) . ?
C3 H3 0.9500 . ?

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
C25 O2 C26 116.7(2) . . ?
N4 N3 C6 119.3(2) . . ?
C7 N3 N4 111.8(2) . . ?
C7 N3 C6 128.5(3) . . ?
N3 N4 H4 125.2 . . ?
C9 N4 N3 109.6(2) . . ?
C9 N4 H4 125.2 . . ?
C8 N1 C28 108.6(2) . . ?
C8 N1 H1 113(2) . . ?
C28 N1 H1 108(2) . . ?
C20 N2 C35 124.9(3) . . ?
C18 N2 C20 111.2(3) . . ?
C18 N2 C35 123.7(3) . . ?
O2 C25 C16 109.4(3) . . ?
O3 C25 O2 124.9(3) . . ?
O3 C25 C16 125.7(3) . . ?
C34 C29 C28 119.3(3) . . ?
C30 C29 C34 118.7(3) . . ?
C30 C29 C28 121.9(3) . . ?
C29 C34 H34 120.1 . . ?
C33 C34 C29 119.8(3) . . ?
C33 C34 H34 120.1 . . ?
C19 C20 N2 110.0(3) . . ?
C21 C20 N2 127.9(3) . . ?
C21 C20 C19 122.1(3) . . ?
C20 C19 C17 108.6(3) . . ?
C24 C19 C20 119.7(3) . . ?
C24 C19 C17 131.5(3) . . ?
C25 C16 H16 106.8 . . ?
C25 C16 C8 116.1(2) . . ?
C25 C16 C17 114.4(2) . . ?
C8 C16 H16 106.8 . . ?
C8 C16 C17 105.4(2) . . ?
C17 C16 H16 106.8 . . ?
N1 C8 C16 102.0(2) . . ?
N1 C8 C9 113.5(2) . . ?
N1 C8 C7 112.9(2) . . ?
C9 C8 C16 114.3(2) . . ?
C9 C8 C7 100.3(2) . . ?
C7 C8 C16 114.3(2) . . ?
N1 C28 C29 111.6(2) . . ?
N1 C28 H28 108.3 . . ?
N1 C28 C17 104.3(2) . . ?
C29 C28 H28 108.3 . . ?
C29 C28 C17 115.6(2) . . ?
C17 C28 H28 108.3 . . ?
C31 C32 H32 121.0 . . ?
C31 C32 C33 118.0(3) . . ?
C33 C32 H32 121.0 . . ?
N4 C9 C8 112.3(3) . . ?
N4 C9 C10 121.3(3) . . ?
C10 C9 C8 126.4(3) . . ?
O4 C7 N3 127.3(3) . . ?
O4 C7 C8 126.8(3) . . ?
N3 C7 C8 105.8(3) . . ?
C32 C31 H31 119.2 . . ?
C32 C31 C30 121.7(3) . . ?
C30 C31 H31 119.2 . . ?
C19 C24 H24 120.5 . . ?
C19 C24 C23 118.9(3) . . ?
C23 C24 H24 120.5 . . ?
O1 C18 N2 125.4(3) . . ?
O1 C18 C17 126.4(3) . . ?
N2 C18 C17 108.2(3) . . ?
C19 C17 C16 118.1(2) . . ?
C19 C17 C28 111.8(2) . . ?
C19 C17 C18 101.9(2) . . ?
C28 C17 C16 104.3(2) . . ?
C18 C17 C16 107.1(2) . . ?
C18 C17 C28 114.0(2) . . ?
C15 C10 C9 122.0(3) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 C15 118.6(3) . . ?
C5 C6 N3 119.2(3) . . ?
C1 C6 N3 120.1(3) . . ?
C1 C6 C5 120.5(3) . . ?
C34 C33 Cl1 119.0(2) . . ?
C32 C33 Cl1 119.2(2) . . ?
C32 C33 C34 121.8(3) . . ?
C29 C30 C31 120.0(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C23 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
O2 C26 H26A 109.7 . . ?
O2 C26 H26B 109.7 . . ?
O2 C26 C27 109.9(3) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.8 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.7 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C1 H1A 120.3 . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 H1A 120.3 . . ?
C20 C21 C22 117.5(3) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
N2 C35 H35A 109.5 . . ?
N2 C35 H35B 109.5 . . ?
N2 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4A 119.8 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?

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
O2 C25 C16 C8 -176.4(2) . . . . ?
O2 C25 C16 C17 60.6(3) . . . . ?
O1 C18 C17 C19 -176.2(3) . . . . ?
O1 C18 C17 C16 -51.6(4) . . . . ?
O1 C18 C17 C28 63.2(4) . . . . ?
O3 C25 C16 C8 2.7(5) . . . . ?
O3 C25 C16 C17 -120.3(3) . . . . ?
N3 N4 C9 C8 -1.2(3) . . . . ?
N3 N4 C9 C10 178.2(3) . . . . ?
N3 C6 C5 C4 174.9(3) . . . . ?
N3 C6 C1 C2 -174.6(3) . . . . ?
N4 N3 C7 O4 -172.2(3) . . . . ?
N4 N3 C7 C8 3.7(3) . . . . ?
N4 N3 C6 C5 8.7(4) . . . . ?
N4 N3 C6 C1 -174.9(3) . . . . ?
N4 C9 C10 C15 -167.4(3) . . . . ?
N4 C9 C10 C11 11.7(4) . . . . ?
N1 C8 C9 N4 123.9(3) . . . . ?
N1 C8 C9 C10 -55.4(4) . . . . ?
N1 C8 C7 O4 50.8(4) . . . . ?
N1 C8 C7 N3 -125.1(3) . . . . ?
N1 C28 C17 C19 142.4(2) . . . . ?
N1 C28 C17 C16 13.8(3) . . . . ?
N1 C28 C17 C18 -102.7(3) . . . . ?
N2 C20 C19 C24 177.7(3) . . . . ?
N2 C20 C19 C17 2.3(3) . . . . ?
N2 C20 C21 C22 -179.3(3) . . . . ?
N2 C18 C17 C19 2.5(3) . . . . ?
N2 C18 C17 C16 127.2(2) . . . . ?
N2 C18 C17 C28 -118.1(3) . . . . ?
C25 O2 C26 C27 88.8(3) . . . . ?
C25 C16 C8 N1 -157.5(2) . . . . ?
C25 C16 C8 C9 79.5(3) . . . . ?
C25 C16 C8 C7 -35.3(4) . . . . ?
C25 C16 C17 C19 13.9(4) . . . . ?
C25 C16 C17 C28 138.6(3) . . . . ?
C25 C16 C17 C18 -100.3(3) . . . . ?
C29 C34 C33 Cl1 177.7(2) . . . . ?
C29 C34 C33 C32 -2.5(5) . . . . ?
C29 C28 C17 C19 -94.6(3) . . . . ?
C29 C28 C17 C16 136.7(3) . . . . ?
C29 C28 C17 C18 20.3(4) . . . . ?
C34 C29 C28 N1 173.7(3) . . . . ?
C34 C29 C28 C17 54.6(4) . . . . ?
C34 C29 C30 C31 0.0(5) . . . . ?
C20 N2 C18 O1 177.5(3) . . . . ?
C20 N2 C18 C17 -1.3(3) . . . . ?
C20 C19 C24 C23 2.1(4) . . . . ?
C20 C19 C17 C16 -119.8(3) . . . . ?
C20 C19 C17 C28 119.2(3) . . . . ?
C20 C19 C17 C18 -2.9(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C19 C24 C23 C22 -1.0(5) . . . . ?
C16 C8 C9 N4 -119.6(3) . . . . ?
C16 C8 C9 C10 61.0(4) . . . . ?
C16 C8 C7 O4 -65.2(4) . . . . ?
C16 C8 C7 N3 118.9(3) . . . . ?
C8 N1 C28 C29 -160.4(3) . . . . ?
C8 N1 C28 C17 -34.8(3) . . . . ?
C8 C16 C17 C19 -114.8(3) . . . . ?
C8 C16 C17 C28 9.9(3) . . . . ?
C8 C16 C17 C18 131.1(2) . . . . ?
C8 C9 C10 C15 11.9(5) . . . . ?
C8 C9 C10 C11 -169.0(3) . . . . ?
C28 N1 C8 C16 40.8(3) . . . . ?
C28 N1 C8 C9 164.3(3) . . . . ?
C28 N1 C8 C7 -82.3(3) . . . . ?
C28 C29 C34 C33 179.3(3) . . . . ?
C28 C29 C30 C31 -177.4(3) . . . . ?
C32 C31 C30 C29 -1.2(5) . . . . ?
C9 C8 C7 O4 172.0(3) . . . . ?
C9 C8 C7 N3 -3.9(3) . . . . ?
C9 C10 C15 C14 178.8(3) . . . . ?
C9 C10 C11 C12 -179.4(3) . . . . ?
C7 N3 N4 C9 -1.7(3) . . . . ?
C7 N3 C6 C5 -163.2(3) . . . . ?
C7 N3 C6 C1 13.2(5) . . . . ?
C7 C8 C9 N4 3.2(3) . . . . ?
C7 C8 C9 C10 -176.2(3) . . . . ?
C31 C32 C33 Cl1 -178.9(2) . . . . ?
C31 C32 C33 C34 1.3(5) . . . . ?
C24 C19 C17 C16 65.6(4) . . . . ?
C24 C19 C17 C28 -55.4(4) . . . . ?
C24 C19 C17 C18 -177.5(3) . . . . ?
C18 N2 C20 C19 -0.7(3) . . . . ?
C18 N2 C20 C21 178.6(3) . . . . ?
C17 C19 C24 C23 176.2(3) . . . . ?
C17 C16 C8 N1 -29.9(3) . . . . ?
C17 C16 C8 C9 -152.8(2) . . . . ?
C17 C16 C8 C7 92.3(3) . . . . ?
C10 C15 C14 C13 0.9(5) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C6 N3 N4 C9 -174.9(3) . . . . ?
C6 N3 C7 O4 0.2(5) . . . . ?
C6 N3 C7 C8 176.1(3) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C33 C32 C31 C30 0.5(5) . . . . ?
C30 C29 C34 C33 1.7(5) . . . . ?
C30 C29 C28 N1 -8.9(4) . . . . ?
C30 C29 C28 C17 -128.0(3) . . . . ?
C26 O2 C25 O3 4.5(4) . . . . ?
C26 O2 C25 C16 -176.4(2) . . . . ?
C15 C10 C11 C12 -0.2(5) . . . . ?
C15 C14 C13 C12 -0.8(5) . . . . ?
C23 C22 C21 C20 1.2(5) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C5 C6 C1 C2 1.8(5) . . . . ?
C5 C4 C3 C2 1.4(6) . . . . ?
C1 C6 C5 C4 -1.5(5) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C21 C20 C19 C24 -1.6(5) . . . . ?
C21 C20 C19 C17 -177.0(3) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C35 N2 C20 C19 -176.0(3) . . . . ?
C35 N2 C20 C21 3.3(5) . . . . ?
C35 N2 C18 O1 -7.1(5) . . . . ?
C35 N2 C18 C17 174.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
