# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1858311'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Wael_111Hw_02_0817
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H25 Cl N4 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         585.04

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5696(6)
_cell_length_b                   19.6736(7)
_cell_length_c                   9.4182(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.241(3)
_cell_angle_gamma                90
_cell_volume                     2872.83(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5666
_cell_measurement_theta_min      3.6297
_cell_measurement_theta_max      65.5781
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216

_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
__diffrn_source_type             'Incoatec Cu-ImS'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'

_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24182
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_theta_min         5.22
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_full        66.51
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             4927
_reflns_number_gt                3560
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1520
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         4927
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+1.2275P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.548
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.11763(7) 0.63672(7) 1.07956(11) 0.1049(5) Uani d . 1 . .
O O2 0.38191(13) 0.79931(11) 0.38506(18) 0.0567(6) Uani d . 1 . .
O O3 0.26729(13) 0.89178(9) 0.6624(2) 0.0537(5) Uani d . 1 . .
O O1 0.45869(12) 0.65282(11) 0.39789(18) 0.0525(5) Uani d . 1 . .
N N1 0.48087(12) 0.68290(11) 0.6310(2) 0.0349(5) Uani d . 1 . .
H H1 0.4543 0.6936 0.704 0.042 Uiso calc R 1 . .
N N4 0.43802(13) 0.84825(11) 0.5908(2) 0.0393(5) Uani d . 1 . .
H H4 0.4331 0.8503 0.6809 0.047 Uiso calc R 1 . .
N N2 0.21799(13) 0.58570(10) 0.5462(2) 0.0373(5) Uani d . 1 . .
N N3 0.17598(12) 0.63022(10) 0.6238(2) 0.0351(5) Uani d . 1 . .
C C3 0.7495(2) 0.68690(19) 0.7054(4) 0.0716(10) Uani d . 1 . .
H H3 0.8092 0.6883 0.7233 0.086 Uiso calc R 1 . .
C C4 0.71260(18) 0.65530(17) 0.5866(3) 0.0566(8) Uani d . 1 . .
H H4A 0.7475 0.6343 0.5246 0.068 Uiso calc R 1 . .
C C5 0.62408(17) 0.65396(15) 0.5566(3) 0.0447(6) Uani d . 1 . .
H H5 0.5995 0.6324 0.475 0.054 Uiso calc R 1 . .
C C6 0.57233(15) 0.68520(13) 0.6498(3) 0.0362(6) Uani d . 1 . .
C C7 0.43126(15) 0.66596(13) 0.5125(2) 0.0339(5) Uani d . 1 . .
C C8 0.33691(15) 0.65919(13) 0.5354(2) 0.0324(5) Uani d . 1 . .
C C12 0.28825(14) 0.71354(12) 0.5893(2) 0.0304(5) Uani d . 1 . .
C C13 0.30867(15) 0.78188(12) 0.5925(2) 0.0312(5) Uani d . 1 . .
C C18 0.37967(16) 0.81063(13) 0.5127(2) 0.0353(6) Uani d . 1 . .
C C19 0.50743(17) 0.88518(14) 0.5392(3) 0.0433(6) Uani d . 1 . .
C C24 0.5844(2) 0.88728(19) 0.6224(4) 0.0677(9) Uani d . 1 . .
H H24 0.5913 0.8635 0.7081 0.081 Uiso calc R 1 . .
C C23 0.6522(2) 0.9255(2) 0.5770(6) 0.0943(14) Uani d . 1 . .
H H23 0.7044 0.9274 0.6334 0.113 Uiso calc R 1 . .
C C22 0.6430(3) 0.9600(2) 0.4507(6) 0.0972(15) Uani d . 1 . .
H H22 0.6885 0.9853 0.4211 0.117 Uiso calc R 1 . .
C C34 0.06384(19) 0.41832(16) 0.4170(4) 0.0602(8) Uani d . 1 . .
H H34 0.0285 0.3819 0.3878 0.072 Uiso calc R 1 . .
C C33 0.0765(2) 0.43443(15) 0.5582(4) 0.0598(8) Uani d . 1 . .
H H33 0.0499 0.4088 0.6246 0.072 Uiso calc R 1 . .
C C32 0.12878(18) 0.48892(14) 0.6034(3) 0.0491(7) Uani d . 1 . .
H H32 0.1376 0.5 0.6996 0.059 Uiso calc R 1 . .
C C31 0.16725(16) 0.52618(12) 0.5029(3) 0.0381(6) Uani d . 1 . .
C C11 0.21108(14) 0.69008(12) 0.6510(2) 0.0309(5) Uani d . 1 . .
C C21 0.5660(3) 0.95699(18) 0.3684(4) 0.0813(13) Uani d . 1 . .
H H21 0.5598 0.98 0.2818 0.098 Uiso calc R 1 . .
C C20 0.4974(2) 0.92030(15) 0.4115(3) 0.0578(8) Uani d . 1 . .
H H20 0.4451 0.9192 0.3553 0.069 Uiso calc R 1 . .
C C14 0.25702(16) 0.82931(13) 0.6654(2) 0.0366(6) Uani d . 1 . .
C C15 0.18917(16) 0.80086(13) 0.7454(3) 0.0361(6) Uani d . 1 . .
H H15 0.1605 0.8301 0.8026 0.043 Uiso calc R 1 . .
C C16 0.16580(14) 0.73505(13) 0.7411(2) 0.0323(5) Uani d . 1 . .
C C25 0.09575(15) 0.70932(13) 0.8241(2) 0.0362(6) Uani d . 1 . .
C C30 0.10367(18) 0.64805(15) 0.8976(3) 0.0459(7) Uani d . 1 . .
H H30 0.1528 0.6216 0.8929 0.055 Uiso calc R 1 . .
C C29 0.0383(2) 0.62606(18) 0.9783(3) 0.0589(8) Uani d . 1 . .
H H29 0.0435 0.585 1.0274 0.071 Uiso calc R 1 . .
C C28 -0.0339(2) 0.6657(2) 0.9847(3) 0.0612(9) Uani d . 1 . .
C C27 -0.04246(19) 0.7264(2) 0.9162(3) 0.0613(9) Uani d . 1 . .
H H27 -0.0913 0.7529 0.9234 0.074 Uiso calc R 1 . .
C C26 0.02205(17) 0.74860(16) 0.8355(3) 0.0485(7) Uani d . 1 . .
H H26 0.0162 0.7901 0.7885 0.058 Uiso calc R 1 . .
C C9 0.30164(15) 0.59564(13) 0.5146(3) 0.0357(6) Uani d . 1 . .
C C10 0.34962(19) 0.53458(15) 0.4691(3) 0.0532(7) Uani d . 1 . .
H H10A 0.3424 0.5308 0.3671 0.08 Uiso calc R 1 . .
H H10B 0.3274 0.4945 0.5109 0.08 Uiso calc R 1 . .
H H10C 0.4098 0.5393 0.5 0.08 Uiso calc R 1 . .
C C2 0.6981(2) 0.71677(19) 0.7991(4) 0.0745(11) Uani d . 1 . .
H H2 0.7232 0.7374 0.8815 0.089 Uiso calc R 1 . .
C C1 0.60938(18) 0.71625(16) 0.7716(3) 0.0534(7) Uani d . 1 . .
H H1A 0.5749 0.7367 0.8349 0.064 Uiso calc R 1 . .
C C36 0.15506(18) 0.51011(14) 0.3602(3) 0.0476(7) Uani d . 1 . .
H H36 0.1815 0.5355 0.2932 0.057 Uiso calc R 1 . .
C C35 0.1028(2) 0.45544(16) 0.3181(4) 0.0588(8) Uani d . 1 . .
H H35 0.0941 0.4439 0.2221 0.071 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0709(6) 0.1720(13) 0.0757(6) -0.0523(7) 0.0284(5) 0.0051(6)
O2 0.0653(13) 0.0746(15) 0.0313(10) -0.0263(11) 0.0098(9) -0.0065(9)
O3 0.0582(12) 0.0299(11) 0.0752(13) -0.0054(9) 0.0186(10) -0.0032(9)
O1 0.0378(10) 0.0848(16) 0.0352(10) -0.0023(10) 0.0050(8) -0.0110(9)
N1 0.0284(10) 0.0428(13) 0.0334(10) 0.0005(9) 0.0017(8) -0.0034(9)
N4 0.0419(12) 0.0423(13) 0.0344(10) -0.0145(10) 0.0081(9) -0.0005(9)
N2 0.0331(11) 0.0329(11) 0.0461(11) -0.0055(9) 0.0042(9) -0.0060(10)
N3 0.0325(11) 0.0313(11) 0.0416(11) -0.0023(9) 0.0041(9) -0.0052(9)
C3 0.0341(16) 0.073(2) 0.104(3) 0.0038(15) -0.0100(17) -0.017(2)
C4 0.0360(15) 0.063(2) 0.0707(19) 0.0118(14) 0.0043(14) -0.0025(17)
C5 0.0379(14) 0.0482(16) 0.0476(15) 0.0049(12) 0.0011(11) -0.0033(13)
C6 0.0315(13) 0.0334(13) 0.0424(13) -0.0002(10) -0.0030(10) 0.0030(11)
C7 0.0305(12) 0.0367(14) 0.0342(12) -0.0013(10) 0.0006(10) -0.0011(11)
C8 0.0293(12) 0.0345(14) 0.0330(12) -0.0010(10) 0.0002(9) -0.0029(10)
C12 0.0282(11) 0.0345(13) 0.0276(11) -0.0031(10) -0.0016(9) -0.0017(10)
C13 0.0318(12) 0.0321(13) 0.0293(11) -0.0035(10) 0.0008(9) -0.0016(10)
C18 0.0395(14) 0.0349(14) 0.0315(13) -0.0050(11) 0.0037(10) 0.0023(11)
C19 0.0451(15) 0.0322(15) 0.0549(16) -0.0081(11) 0.0166(13) -0.0035(12)
C24 0.0463(18) 0.069(2) 0.088(2) -0.0145(16) 0.0051(16) 0.0071(19)
C23 0.049(2) 0.084(3) 0.152(4) -0.0220(19) 0.019(2) -0.001(3)
C22 0.089(3) 0.067(3) 0.145(4) -0.030(2) 0.065(3) -0.003(3)
C34 0.0455(17) 0.0377(17) 0.095(2) -0.0094(13) -0.0056(17) -0.0097(17)
C33 0.0514(18) 0.0386(17) 0.090(2) -0.0109(13) 0.0104(16) 0.0063(16)
C32 0.0483(16) 0.0412(16) 0.0580(16) -0.0058(13) 0.0051(13) 0.0009(13)
C31 0.0334(13) 0.0259(13) 0.0546(15) -0.0032(10) 0.0020(11) -0.0031(11)
C11 0.0288(12) 0.0306(13) 0.0327(12) -0.0024(10) -0.0001(9) -0.0002(10)
C21 0.119(4) 0.049(2) 0.085(3) -0.024(2) 0.056(3) -0.0010(18)
C20 0.084(2) 0.0383(17) 0.0548(17) -0.0108(15) 0.0264(16) -0.0024(14)
C14 0.0381(14) 0.0331(15) 0.0379(13) -0.0045(11) -0.0005(10) -0.0019(11)
C15 0.0343(13) 0.0351(14) 0.0391(13) -0.0005(10) 0.0046(10) -0.0060(11)
C16 0.0289(12) 0.0351(14) 0.0325(12) -0.0035(10) 0.0000(9) -0.0038(10)
C25 0.0328(13) 0.0424(15) 0.0331(12) -0.0083(11) 0.0025(10) -0.0052(11)
C30 0.0439(15) 0.0533(18) 0.0402(14) -0.0097(13) 0.0015(12) 0.0010(13)
C29 0.065(2) 0.068(2) 0.0426(15) -0.0233(17) 0.0005(14) 0.0090(14)
C28 0.0458(18) 0.097(3) 0.0416(15) -0.0273(18) 0.0084(13) -0.0068(17)
C27 0.0385(16) 0.091(3) 0.0555(18) -0.0055(16) 0.0117(13) -0.0141(18)
C26 0.0390(15) 0.0561(18) 0.0508(15) -0.0019(13) 0.0065(12) -0.0041(13)
C9 0.0311(13) 0.0354(14) 0.0404(13) -0.0001(10) 0.0026(10) -0.0029(11)
C10 0.0426(16) 0.0408(16) 0.077(2) 0.0017(12) 0.0095(14) -0.0115(15)
C2 0.0483(18) 0.076(2) 0.094(2) 0.0042(17) -0.0230(17) -0.035(2)
C1 0.0401(15) 0.0551(19) 0.0627(18) 0.0023(13) -0.0068(13) -0.0169(15)
C36 0.0494(16) 0.0380(15) 0.0547(16) -0.0051(12) 0.0007(13) -0.0063(13)
C35 0.0602(19) 0.0448(18) 0.0688(19) -0.0088(15) -0.0081(16) -0.0146(15)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C28 . 1.742(3) ?
O2 C18 . 1.226(3) ?
O3 C14 . 1.240(3) ?
O1 C7 . 1.225(3) ?
N1 C7 . 1.340(3) ?
N1 C6 . 1.419(3) ?
N1 H1 . 0.86 ?
N4 C18 . 1.339(3) ?
N4 C19 . 1.424(3) ?
N4 H4 . 0.86 ?
N2 N3 . 1.348(3) ?
N2 C9 . 1.376(3) ?
N2 C31 . 1.450(3) ?
N3 C11 . 1.314(3) ?
C3 C4 . 1.361(5) ?
C3 C2 . 1.376(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(4) ?
C4 H4A . 0.93 ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.93 ?
C6 C1 . 1.379(4) ?
C7 C8 . 1.510(3) ?
C8 C9 . 1.372(3) ?
C8 C12 . 1.430(3) ?
C12 C13 . 1.381(3) ?
C12 C11 . 1.457(3) ?
C13 C14 . 1.446(3) ?
C13 C18 . 1.503(3) ?
C19 C24 . 1.372(4) ?
C19 C20 . 1.384(4) ?
C24 C23 . 1.394(5) ?
C24 H24 . 0.93 ?
C23 C22 . 1.366(7) ?
C23 H23 . 0.93 ?
C22 C21 . 1.368(7) ?
C22 H22 . 0.93 ?
C34 C33 . 1.363(5) ?
C34 C35 . 1.368(5) ?
C34 H34 . 0.93 ?
C33 C32 . 1.389(4) ?
C33 H33 . 0.93 ?
C32 C31 . 1.377(4) ?
C32 H32 . 0.93 ?
C31 C36 . 1.377(4) ?
C11 C16 . 1.452(3) ?
C21 C20 . 1.380(5) ?
C21 H21 . 0.93 ?
C20 H20 . 0.93 ?
C14 C15 . 1.464(3) ?
C15 C16 . 1.344(3) ?
C15 H15 . 0.93 ?
C16 C25 . 1.487(3) ?
C25 C30 . 1.390(4) ?
C25 C26 . 1.396(4) ?
C30 C29 . 1.393(4) ?
C30 H30 . 0.93 ?
C29 C28 . 1.375(5) ?
C29 H29 . 0.93 ?
C28 C27 . 1.358(5) ?
C27 C26 . 1.384(4) ?
C27 H27 . 0.93 ?
C26 H26 . 0.93 ?
C9 C10 . 1.498(4) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C2 C1 . 1.382(4) ?
C2 H2 . 0.93 ?
C1 H1A . 0.93 ?
C36 C35 . 1.385(4) ?
C36 H36 . 0.93 ?
C35 H35 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C6 . . 127.4(2) ?
C7 N1 H1 . . 116.3 ?
C6 N1 H1 . . 116.3 ?
C18 N4 C19 . . 126.3(2) ?
C18 N4 H4 . . 116.8 ?
C19 N4 H4 . . 116.8 ?
N3 N2 C9 . . 122.7(2) ?
N3 N2 C31 . . 113.48(19) ?
C9 N2 C31 . . 123.8(2) ?
C11 N3 N2 . . 118.33(19) ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 121.0(3) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
C4 C5 C6 . . 119.2(3) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C1 C6 C5 . . 119.9(2) ?
C1 C6 N1 . . 117.1(2) ?
C5 C6 N1 . . 122.8(2) ?
O1 C7 N1 . . 124.5(2) ?
O1 C7 C8 . . 121.9(2) ?
N1 C7 C8 . . 113.4(2) ?
C9 C8 C12 . . 120.9(2) ?
C9 C8 C7 . . 116.2(2) ?
C12 C8 C7 . . 122.6(2) ?
C13 C12 C8 . . 127.4(2) ?
C13 C12 C11 . . 119.8(2) ?
C8 C12 C11 . . 112.8(2) ?
C12 C13 C14 . . 120.1(2) ?
C12 C13 C18 . . 122.3(2) ?
C14 C13 C18 . . 117.5(2) ?
O2 C18 N4 . . 124.1(2) ?
O2 C18 C13 . . 120.7(2) ?
N4 C18 C13 . . 115.24(19) ?
C24 C19 C20 . . 120.3(3) ?
C24 C19 N4 . . 118.1(3) ?
C20 C19 N4 . . 121.5(3) ?
C19 C24 C23 . . 119.2(4) ?
C19 C24 H24 . . 120.4 ?
C23 C24 H24 . . 120.4 ?
C22 C23 C24 . . 120.9(4) ?
C22 C23 H23 . . 119.6 ?
C24 C23 H23 . . 119.6 ?
C23 C22 C21 . . 119.3(4) ?
C23 C22 H22 . . 120.4 ?
C21 C22 H22 . . 120.4 ?
C33 C34 C35 . . 120.4(3) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C34 C33 C32 . . 120.5(3) ?
C34 C33 H33 . . 119.8 ?
C32 C33 H33 . . 119.8 ?
C31 C32 C33 . . 118.7(3) ?
C31 C32 H32 . . 120.7 ?
C33 C32 H32 . . 120.7 ?
C32 C31 C36 . . 121.3(2) ?
C32 C31 N2 . . 119.8(2) ?
C36 C31 N2 . . 118.9(2) ?
N3 C11 C16 . . 116.4(2) ?
N3 C11 C12 . . 123.4(2) ?
C16 C11 C12 . . 120.1(2) ?
C22 C21 C20 . . 121.1(4) ?
C22 C21 H21 . . 119.4 ?
C20 C21 H21 . . 119.4 ?
C21 C20 C19 . . 119.2(4) ?
C21 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
O3 C14 C13 . . 123.4(2) ?
O3 C14 C15 . . 119.4(2) ?
C13 C14 C15 . . 117.2(2) ?
C16 C15 C14 . . 124.0(2) ?
C16 C15 H15 . . 118.0 ?
C14 C15 H15 . . 118.0 ?
C15 C16 C11 . . 117.4(2) ?
C15 C16 C25 . . 121.4(2) ?
C11 C16 C25 . . 121.2(2) ?
C30 C25 C26 . . 118.5(2) ?
C30 C25 C16 . . 121.4(2) ?
C26 C25 C16 . . 120.0(2) ?
C25 C30 C29 . . 120.3(3) ?
C25 C30 H30 . . 119.8 ?
C29 C30 H30 . . 119.8 ?
C28 C29 C30 . . 119.3(3) ?
C28 C29 H29 . . 120.4 ?
C30 C29 H29 . . 120.4 ?
C27 C28 C29 . . 121.5(3) ?
C27 C28 Cl1 . . 119.1(3) ?
C29 C28 Cl1 . . 119.3(3) ?
C28 C27 C26 . . 119.6(3) ?
C28 C27 H27 . . 120.2 ?
C26 C27 H27 . . 120.2 ?
C27 C26 C25 . . 120.7(3) ?
C27 C26 H26 . . 119.6 ?
C25 C26 H26 . . 119.6 ?
C8 C9 N2 . . 118.2(2) ?
C8 C9 C10 . . 124.6(2) ?
N2 C9 C10 . . 117.0(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C6 C1 C2 . . 119.6(3) ?
C6 C1 H1A . . 120.2 ?
C2 C1 H1A . . 120.2 ?
C31 C36 C35 . . 118.9(3) ?
C31 C36 H36 . . 120.6 ?
C35 C36 H36 . . 120.6 ?
C34 C35 C36 . . 120.4(3) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N2 N3 C11 . . . . 11.0(3) ?
C31 N2 N3 C11 . . . . -170.4(2) ?
C2 C3 C4 C5 . . . . 1.4(6) ?
C3 C4 C5 C6 . . . . -0.2(5) ?
C4 C5 C6 C1 . . . . -0.9(4) ?
C4 C5 C6 N1 . . . . -176.4(3) ?
C7 N1 C6 C1 . . . . 168.0(3) ?
C7 N1 C6 C5 . . . . -16.4(4) ?
C6 N1 C7 O1 . . . . -3.8(4) ?
C6 N1 C7 C8 . . . . 171.8(2) ?
O1 C7 C8 C9 . . . . 59.7(3) ?
N1 C7 C8 C9 . . . . -116.1(2) ?
O1 C7 C8 C12 . . . . -126.5(3) ?
N1 C7 C8 C12 . . . . 57.8(3) ?
C9 C8 C12 C13 . . . . -167.8(2) ?
C7 C8 C12 C13 . . . . 18.6(4) ?
C9 C8 C12 C11 . . . . 14.7(3) ?
C7 C8 C12 C11 . . . . -158.9(2) ?
C8 C12 C13 C14 . . . . -173.1(2) ?
C11 C12 C13 C14 . . . . 4.3(3) ?
C8 C12 C13 C18 . . . . 11.7(4) ?
C11 C12 C13 C18 . . . . -171.0(2) ?
C19 N4 C18 O2 . . . . 5.1(4) ?
C19 N4 C18 C13 . . . . -175.0(2) ?
C12 C13 C18 O2 . . . . 52.4(4) ?
C14 C13 C18 O2 . . . . -122.9(3) ?
C12 C13 C18 N4 . . . . -127.5(3) ?
C14 C13 C18 N4 . . . . 57.2(3) ?
C18 N4 C19 C24 . . . . -142.7(3) ?
C18 N4 C19 C20 . . . . 39.7(4) ?
C20 C19 C24 C23 . . . . 0.3(5) ?
N4 C19 C24 C23 . . . . -177.3(3) ?
C19 C24 C23 C22 . . . . -0.6(6) ?
C24 C23 C22 C21 . . . . 0.1(7) ?
C35 C34 C33 C32 . . . . 0.3(5) ?
C34 C33 C32 C31 . . . . 0.1(5) ?
C33 C32 C31 C36 . . . . -0.3(4) ?
C33 C32 C31 N2 . . . . 176.4(3) ?
N3 N2 C31 C32 . . . . -52.2(3) ?
C9 N2 C31 C32 . . . . 126.4(3) ?
N3 N2 C31 C36 . . . . 124.6(3) ?
C9 N2 C31 C36 . . . . -56.8(4) ?
N2 N3 C11 C16 . . . . -176.9(2) ?
N2 N3 C11 C12 . . . . 6.7(3) ?
C13 C12 C11 N3 . . . . 163.4(2) ?
C8 C12 C11 N3 . . . . -18.9(3) ?
C13 C12 C11 C16 . . . . -12.9(3) ?
C8 C12 C11 C16 . . . . 164.9(2) ?
C23 C22 C21 C20 . . . . 0.7(6) ?
C22 C21 C20 C19 . . . . -1.0(5) ?
C24 C19 C20 C21 . . . . 0.5(5) ?
N4 C19 C20 C21 . . . . 178.0(3) ?
C12 C13 C14 O3 . . . . -173.8(2) ?
C18 C13 C14 O3 . . . . 1.6(3) ?
C12 C13 C14 C15 . . . . 5.8(3) ?
C18 C13 C14 C15 . . . . -178.8(2) ?
O3 C14 C15 C16 . . . . 171.5(2) ?
C13 C14 C15 C16 . . . . -8.1(4) ?
C14 C15 C16 C11 . . . . -0.1(4) ?
C14 C15 C16 C25 . . . . -179.5(2) ?
N3 C11 C16 C15 . . . . -165.9(2) ?
C12 C11 C16 C15 . . . . 10.6(3) ?
N3 C11 C16 C25 . . . . 13.5(3) ?
C12 C11 C16 C25 . . . . -170.0(2) ?
C15 C16 C25 C30 . . . . -137.5(3) ?
C11 C16 C25 C30 . . . . 43.1(3) ?
C15 C16 C25 C26 . . . . 39.1(3) ?
C11 C16 C25 C26 . . . . -140.3(2) ?
C26 C25 C30 C29 . . . . 1.3(4) ?
C16 C25 C30 C29 . . . . 177.9(2) ?
C25 C30 C29 C28 . . . . -0.2(4) ?
C30 C29 C28 C27 . . . . -1.2(5) ?
C30 C29 C28 Cl1 . . . . 177.4(2) ?
C29 C28 C27 C26 . . . . 1.3(5) ?
Cl1 C28 C27 C26 . . . . -177.3(2) ?
C28 C27 C26 C25 . . . . -0.1(4) ?
C30 C25 C26 C27 . . . . -1.2(4) ?
C16 C25 C26 C27 . . . . -177.9(2) ?
C12 C8 C9 N2 . . . . 0.4(3) ?
C7 C8 C9 N2 . . . . 174.4(2) ?
C12 C8 C9 C10 . . . . -175.2(2) ?
C7 C8 C9 C10 . . . . -1.2(4) ?
N3 N2 C9 C8 . . . . -14.6(4) ?
C31 N2 C9 C8 . . . . 166.9(2) ?
N3 N2 C9 C10 . . . . 161.4(2) ?
C31 N2 C9 C10 . . . . -17.1(4) ?
C4 C3 C2 C1 . . . . -1.5(6) ?
C5 C6 C1 C2 . . . . 0.8(5) ?
N1 C6 C1 C2 . . . . 176.6(3) ?
C3 C2 C1 C6 . . . . 0.4(6) ?
C32 C31 C36 C35 . . . . 0.2(4) ?
N2 C31 C36 C35 . . . . -176.5(3) ?
C33 C34 C35 C36 . . . . -0.4(5) ?
C31 C36 C35 C34 . . . . 0.2(5) ?