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

data_rad634_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2000542'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_chemical_absolute_configuration ?
_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'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   16.8562(8)
_cell_length_b                   18.0364(8)
_cell_length_c                   11.8855(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.028(2)
_cell_angle_gamma                90
_cell_volume                     3372.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    298.41
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0894 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.8926.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rods
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30279
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         2.833
_diffrn_ambient_temperature      298.41
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6001
_reflns_number_total             8703
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_coef       0.0057(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         8703
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.048
_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)+(0.0419P)²+1.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O2A-H2A = O2-H2
 0.82 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C12(H12), C12A(H12A)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A),
  C9A(H9A), C11A(H11A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A),
 C20A(H20A)
;
_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
O1 O 0.43340(18) 0.17804(13) 0.8988(2) 0.0587(7) Uani 1 1 d . . . . .
O2 O 0.5830(2) 0.21217(15) 0.5623(2) 0.0655(8) Uani 1 1 d D . . . .
O3 O 0.5385(2) 0.25243(14) 0.7060(3) 0.0718(8) Uani 1 1 d . . . . .
N1 N 0.50108(17) 0.11708(16) 0.7589(2) 0.0391(6) Uani 1 1 d . . . . .
H1 H 0.493(3) 0.162(2) 0.796(3) 0.056(11) Uiso 1 1 d . . . . .
C1 C 0.42323(18) 0.04929(18) 0.8602(2) 0.0362(7) Uani 1 1 d . . . . .
C2 C 0.4068(2) 0.11395(19) 0.9171(3) 0.0435(8) Uani 1 1 d . . . . .
C3 C 0.3603(2) 0.1052(2) 0.9962(3) 0.0503(9) Uani 1 1 d . . . . .
H3 H 0.348822 0.146668 1.034287 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3331(2) 0.0385(2) 1.0163(3) 0.0493(9) Uani 1 1 d . . . . .
H4 H 0.302420 0.035189 1.067293 0.059 Uiso 1 1 calc R U . . .
C5 C 0.34927(19) -0.02748(19) 0.9628(3) 0.0406(7) Uani 1 1 d . . . . .
C6 C 0.3204(2) -0.0968(2) 0.9863(3) 0.0523(9) Uani 1 1 d . . . . .
H6 H 0.290144 -0.099657 1.038011 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3359(3) -0.1601(2) 0.9346(4) 0.0615(10) Uani 1 1 d . . . . .
H7 H 0.315967 -0.205540 0.950404 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3817(3) -0.1561(2) 0.8584(4) 0.0571(9) Uani 1 1 d . . . . .
H8 H 0.392821 -0.199141 0.823717 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4107(2) -0.08928(19) 0.8336(3) 0.0459(8) Uani 1 1 d . . . . .
H9 H 0.441331 -0.087978 0.782358 0.055 Uiso 1 1 calc R U . . .
C10 C 0.39515(19) -0.02279(17) 0.8838(3) 0.0357(7) Uani 1 1 d . . . . .
C11 C 0.46756(19) 0.05575(18) 0.7800(3) 0.0358(6) Uani 1 1 d . . . . .
H11 H 0.473315 0.013292 0.739221 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5483(2) 0.12221(17) 0.6776(3) 0.0389(7) Uani 1 1 d . . . . .
H12 H 0.516703 0.096129 0.602551 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5552(2) 0.20329(19) 0.6500(3) 0.0470(8) Uani 1 1 d . . . . .
C14 C 0.6378(2) 0.0879(2) 0.7331(3) 0.0494(8) Uani 1 1 d . . . . .
H14A H 0.668804 0.096640 0.679539 0.059 Uiso 1 1 calc R U . . .
H14B H 0.668432 0.112150 0.809196 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6345(2) 0.0055(2) 0.7540(3) 0.0438(8) Uani 1 1 d . . . . .
C16 C 0.6571(2) -0.0224(2) 0.8694(3) 0.0521(9) Uani 1 1 d . . . . .
H16 H 0.677938 0.009333 0.935127 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6490(3) -0.0969(3) 0.8881(4) 0.0650(11) Uani 1 1 d . . . . .
H17 H 0.665032 -0.114882 0.966430 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6177(3) -0.1447(3) 0.7932(4) 0.0675(11) Uani 1 1 d . . . . .
H18 H 0.611472 -0.194806 0.806562 0.081 Uiso 1 1 calc R U . . .
C19 C 0.5957(3) -0.1177(2) 0.6778(4) 0.0656(11) Uani 1 1 d . . . . .
H19 H 0.574838 -0.149783 0.612458 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6043(2) -0.0433(2) 0.6586(3) 0.0547(9) Uani 1 1 d . . . . .
H20 H 0.589610 -0.025629 0.580192 0.066 Uiso 1 1 calc R U . . .
O1A O 0.0681(2) -0.16294(14) 0.4656(2) 0.0627(7) Uani 1 1 d . . . . .
O2A O -0.0829(2) -0.19764(15) -0.0183(2) 0.0626(7) Uani 1 1 d D . . . .
O3A O -0.0337(2) -0.23764(14) 0.1719(2) 0.0690(8) Uani 1 1 d . . . . .
N1A N -0.00203(17) -0.10112(16) 0.2597(2) 0.0395(6) Uani 1 1 d . . . . .
H1A H 0.010(3) -0.143(2) 0.309(4) 0.057(11) Uiso 1 1 d . . . . .
C1A C 0.0764(2) -0.03367(18) 0.4399(3) 0.0367(7) Uani 1 1 d . . . . .
C2A C 0.0943(2) -0.0991(2) 0.5119(3) 0.0454(8) Uani 1 1 d . . . . .
C3A C 0.1414(2) -0.0918(2) 0.6382(3) 0.0539(9) Uani 1 1 d . . . . .
H3A H 0.153606 -0.133850 0.686742 0.065 Uiso 1 1 calc R U . . .
C4A C 0.1683(2) -0.0254(2) 0.6876(3) 0.0516(9) Uani 1 1 d . . . . .
H4A H 0.199148 -0.022812 0.769948 0.062 Uiso 1 1 calc R U . . .
C5A C 0.1516(2) 0.0414(2) 0.6195(3) 0.0430(8) Uani 1 1 d . . . . .
C6A C 0.1796(2) 0.1102(2) 0.6753(3) 0.0547(10) Uani 1 1 d . . . . .
H6A H 0.210342 0.112014 0.757694 0.066 Uiso 1 1 calc R U . . .
C7A C 0.1623(3) 0.1743(2) 0.6102(4) 0.0619(10) Uani 1 1 d . . . . .
H7A H 0.180738 0.219551 0.648019 0.074 Uiso 1 1 calc R U . . .
C8A C 0.1171(3) 0.1715(2) 0.4874(4) 0.0589(10) Uani 1 1 d . . . . .
H8A H 0.105558 0.215196 0.442855 0.071 Uiso 1 1 calc R U . . .
C9A C 0.0889(2) 0.10505(19) 0.4303(3) 0.0469(8) Uani 1 1 d . . . . .
H9A H 0.058338 0.104629 0.347756 0.056 Uiso 1 1 calc R U . . .
C10A C 0.10528(19) 0.03805(18) 0.4939(3) 0.0373(7) Uani 1 1 d . . . . .
C11A C 0.03016(19) -0.03940(18) 0.3154(3) 0.0362(7) Uani 1 1 d . . . . .
H11A H 0.021899 0.003636 0.269468 0.043 Uiso 1 1 calc R U . . .
C12A C -0.0494(2) -0.10732(18) 0.1310(3) 0.0390(7) Uani 1 1 d . . . . .
H12A H -0.018908 -0.080434 0.087316 0.047 Uiso 1 1 calc R U . . .
C13A C -0.0533(2) -0.18861(19) 0.0980(3) 0.0458(8) Uani 1 1 d . . . . .
C14A C -0.1396(2) -0.0762(2) 0.0944(3) 0.0513(9) Uani 1 1 d . . . . .
H14C H -0.170192 -0.087581 0.010127 0.062 Uiso 1 1 calc R U . . .
H14D H -0.168588 -0.101001 0.141100 0.062 Uiso 1 1 calc R U . . .
C15A C -0.1430(2) 0.0057(2) 0.1122(3) 0.0466(8) Uani 1 1 d . . . . .
C16A C -0.1707(2) 0.0350(2) 0.1991(4) 0.0584(10) Uani 1 1 d . . . . .
H16A H -0.188967 0.003419 0.246688 0.070 Uiso 1 1 calc R U . . .
C17A C -0.1714(3) 0.1107(3) 0.2162(5) 0.0774(14) Uani 1 1 d . . . . .
H17A H -0.190931 0.129673 0.274297 0.093 Uiso 1 1 calc R U . . .
C18A C -0.1436(3) 0.1577(3) 0.1484(5) 0.0880(16) Uani 1 1 d . . . . .
H18A H -0.143532 0.208663 0.160786 0.106 Uiso 1 1 calc R U . . .
C19A C -0.1163(4) 0.1300(3) 0.0631(5) 0.0823(14) Uani 1 1 d . . . . .
H19A H -0.097297 0.162032 0.016835 0.099 Uiso 1 1 calc R U . . .
C20A C -0.1164(3) 0.0545(2) 0.0440(4) 0.0624(10) Uani 1 1 d . . . . .
H20A H -0.098139 0.036287 -0.015843 0.075 Uiso 1 1 calc R U . . .
H2A H -0.079(3) -0.2430(16) -0.041(4) 0.084(15) Uiso 1 1 d D . . . .
H2 H 0.580(3) 0.2573(15) 0.537(4) 0.074(14) Uiso 1 1 d 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
O1 C2 1.286(4) . ?
O2 C13 1.297(4) . ?
O2 H2 0.86(3) . ?
O3 C13 1.200(4) . ?
N1 H1 0.96(4) . ?
N1 C11 1.307(4) . ?
N1 C12 1.459(4) . ?
C1 C2 1.424(4) . ?
C1 C10 1.445(4) . ?
C1 C11 1.411(4) . ?
C2 C3 1.432(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.340(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.420(5) . ?
C5 C6 1.406(5) . ?
C5 C10 1.418(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9800 . ?
C12 C13 1.512(5) . ?
C12 C14 1.543(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.511(5) . ?
C15 C16 1.381(5) . ?
C15 C20 1.380(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(6) . ?
C20 H20 0.9300 . ?
O1A C2A 1.285(4) . ?
O2A C13A 1.300(4) . ?
O2A H2A 0.87(3) . ?
O3A C13A 1.206(4) . ?
N1A H1A 0.93(4) . ?
N1A C11A 1.309(4) . ?
N1A C12A 1.454(4) . ?
C1A C2A 1.424(4) . ?
C1A C10A 1.448(4) . ?
C1A C11A 1.408(4) . ?
C2A C3A 1.431(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.340(5) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.422(5) . ?
C5A C6A 1.407(5) . ?
C5A C10A 1.416(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.363(6) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.384(6) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.375(5) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.399(5) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9800 . ?
C12A C13A 1.513(5) . ?
C12A C14A 1.530(5) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A C15A 1.496(5) . ?
C15A C16A 1.382(5) . ?
C15A C20A 1.376(5) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.380(6) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.364(7) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.351(7) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.381(6) . ?
C20A H20A 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
C13 O2 H2 114(3) . . ?
C11 N1 H1 119(2) . . ?
C11 N1 C12 123.9(3) . . ?
C12 N1 H1 117(2) . . ?
C2 C1 C10 120.8(3) . . ?
C11 C1 C2 119.5(3) . . ?
C11 C1 C10 119.6(3) . . ?
O1 C2 C1 121.2(3) . . ?
O1 C2 C3 121.0(3) . . ?
C1 C2 C3 117.8(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 118.7 . . ?
C3 C4 C5 122.7(3) . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 C10 119.7(3) . . ?
C10 C5 C4 119.0(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 C1 118.5(3) . . ?
C9 C10 C1 124.2(3) . . ?
C9 C10 C5 117.3(3) . . ?
N1 C11 C1 124.7(3) . . ?
N1 C11 H11 117.6 . . ?
C1 C11 H11 117.6 . . ?
N1 C12 H12 109.0 . . ?
N1 C12 C13 107.9(3) . . ?
N1 C12 C14 112.0(3) . . ?
C13 C12 H12 109.0 . . ?
C13 C12 C14 110.0(3) . . ?
C14 C12 H12 109.0 . . ?
O2 C13 C12 111.8(3) . . ?
O3 C13 O2 125.3(3) . . ?
O3 C13 C12 122.8(3) . . ?
C12 C14 H14A 109.2 . . ?
C12 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C12 112.1(3) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 120.6(3) . . ?
C20 C15 C14 121.1(3) . . ?
C20 C15 C16 118.2(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(4) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C13A O2A H2A 114(3) . . ?
C11A N1A H1A 114(2) . . ?
C11A N1A C12A 124.7(3) . . ?
C12A N1A H1A 121(2) . . ?
C2A C1A C10A 120.6(3) . . ?
C11A C1A C2A 119.3(3) . . ?
C11A C1A C10A 120.2(3) . . ?
O1A C2A C1A 121.3(3) . . ?
O1A C2A C3A 120.5(3) . . ?
C1A C2A C3A 118.2(3) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A C2A 121.0(3) . . ?
C4A C3A H3A 119.5 . . ?
C3A C4A H4A 118.6 . . ?
C3A C4A C5A 122.8(3) . . ?
C5A C4A H4A 118.6 . . ?
C6A C5A C4A 121.0(3) . . ?
C6A C5A C10A 120.0(3) . . ?
C10A C5A C4A 119.1(3) . . ?
C5A C6A H6A 119.6 . . ?
C7A C6A C5A 120.9(3) . . ?
C7A C6A H6A 119.6 . . ?
C6A C7A H7A 120.2 . . ?
C6A C7A C8A 119.5(4) . . ?
C8A C7A H7A 120.2 . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A C7A 120.9(4) . . ?
C9A C8A H8A 119.5 . . ?
C8A C9A H9A 119.3 . . ?
C8A C9A C10A 121.3(3) . . ?
C10A C9A H9A 119.3 . . ?
C5A C10A C1A 118.4(3) . . ?
C9A C10A C1A 124.2(3) . . ?
C9A C10A C5A 117.4(3) . . ?
N1A C11A C1A 124.5(3) . . ?
N1A C11A H11A 117.7 . . ?
C1A C11A H11A 117.7 . . ?
N1A C12A H12A 109.0 . . ?
N1A C12A C13A 107.7(3) . . ?
N1A C12A C14A 112.7(3) . . ?
C13A C12A H12A 109.0 . . ?
C13A C12A C14A 109.6(3) . . ?
C14A C12A H12A 109.0 . . ?
O2A C13A C12A 111.2(3) . . ?
O3A C13A O2A 125.6(3) . . ?
O3A C13A C12A 123.1(3) . . ?
C12A C14A H14C 108.8 . . ?
C12A C14A H14D 108.8 . . ?
H14C C14A H14D 107.7 . . ?
C15A C14A C12A 114.0(3) . . ?
C15A C14A H14C 108.8 . . ?
C15A C14A H14D 108.8 . . ?
C16A C15A C14A 121.6(3) . . ?
C20A C15A C14A 120.7(3) . . ?
C20A C15A C16A 117.7(4) . . ?
C15A C16A H16A 119.6 . . ?
C17A C16A C15A 120.8(4) . . ?
C17A C16A H16A 119.6 . . ?
C16A C17A H17A 119.8 . . ?
C18A C17A C16A 120.3(4) . . ?
C18A C17A H17A 119.8 . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.7(5) . . ?
C19A C18A H18A 120.2 . . ?
C18A C19A H19A 119.7 . . ?
C18A C19A C20A 120.5(5) . . ?
C20A C19A H19A 119.7 . . ?
C15A C20A C19A 121.0(4) . . ?
C15A C20A H20A 119.5 . . ?
C19A C20A H20A 119.5 . . ?

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
O1 C2 C3 C4 -179.4(3) . . . . ?
N1 C12 C13 O2 -168.7(3) . . . . ?
N1 C12 C13 O3 13.0(5) . . . . ?
N1 C12 C14 C15 64.2(4) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C1 C10 C5 1.3(4) . . . . ?
C2 C1 C10 C9 -178.4(3) . . . . ?
C2 C1 C11 N1 5.1(4) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C3 C4 C5 C10 -0.8(5) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C4 C5 C10 C1 -0.4(4) . . . . ?
C4 C5 C10 C9 179.3(3) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C5 C10 C1 179.3(3) . . . . ?
C6 C5 C10 C9 -1.0(4) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C1 -179.4(3) . . . . ?
C8 C9 C10 C5 0.9(5) . . . . ?
C10 C1 C2 O1 178.3(3) . . . . ?
C10 C1 C2 C3 -1.2(4) . . . . ?
C10 C1 C11 N1 -174.8(3) . . . . ?
C10 C5 C6 C7 0.2(5) . . . . ?
C11 N1 C12 C13 164.4(3) . . . . ?
C11 N1 C12 C14 -74.5(4) . . . . ?
C11 C1 C2 O1 -1.6(5) . . . . ?
C11 C1 C2 C3 178.9(3) . . . . ?
C11 C1 C10 C5 -178.7(3) . . . . ?
C11 C1 C10 C9 1.6(4) . . . . ?
C12 N1 C11 C1 178.6(3) . . . . ?
C12 C14 C15 C16 -108.9(4) . . . . ?
C12 C14 C15 C20 67.4(4) . . . . ?
C13 C12 C14 C15 -175.8(3) . . . . ?
C14 C12 C13 O2 68.9(4) . . . . ?
C14 C12 C13 O3 -109.4(4) . . . . ?
C14 C15 C16 C17 176.0(3) . . . . ?
C14 C15 C20 C19 -175.4(3) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C15 C20 C19 1.0(5) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C18 C19 C20 C15 -0.5(6) . . . . ?
C20 C15 C16 C17 -0.5(5) . . . . ?
O1A C2A C3A C4A -179.3(4) . . . . ?
N1A C12A C13A O2A -169.9(3) . . . . ?
N1A C12A C13A O3A 12.3(5) . . . . ?
N1A C12A C14A C15A 65.7(4) . . . . ?
C1A C2A C3A C4A -0.2(5) . . . . ?
C2A C1A C10A C5A 0.0(4) . . . . ?
C2A C1A C10A C9A -178.5(3) . . . . ?
C2A C1A C11A N1A 3.4(5) . . . . ?
C2A C3A C4A C5A 0.5(6) . . . . ?
C3A C4A C5A C6A 178.8(3) . . . . ?
C3A C4A C5A C10A -0.6(5) . . . . ?
C4A C5A C6A C7A -178.9(3) . . . . ?
C4A C5A C10A C1A 0.3(4) . . . . ?
C4A C5A C10A C9A 179.0(3) . . . . ?
C5A C6A C7A C8A -0.5(6) . . . . ?
C6A C5A C10A C1A -179.1(3) . . . . ?
C6A C5A C10A C9A -0.4(4) . . . . ?
C6A C7A C8A C9A 0.4(6) . . . . ?
C7A C8A C9A C10A -0.4(6) . . . . ?
C8A C9A C10A C1A 179.0(3) . . . . ?
C8A C9A C10A C5A 0.4(5) . . . . ?
C10A C1A C2A O1A 179.0(3) . . . . ?
C10A C1A C2A C3A -0.1(5) . . . . ?
C10A C1A C11A N1A -176.5(3) . . . . ?
C10A C5A C6A C7A 0.5(5) . . . . ?
C11A N1A C12A C13A 164.2(3) . . . . ?
C11A N1A C12A C14A -74.9(4) . . . . ?
C11A C1A C2A O1A -0.9(5) . . . . ?
C11A C1A C2A C3A 180.0(3) . . . . ?
C11A C1A C10A C5A 180.0(3) . . . . ?
C11A C1A C10A C9A 1.4(4) . . . . ?
C12A N1A C11A C1A -179.6(3) . . . . ?
C12A C14A C15A C16A -111.3(4) . . . . ?
C12A C14A C15A C20A 67.0(4) . . . . ?
C13A C12A C14A C15A -174.4(3) . . . . ?
C14A C12A C13A O2A 67.2(4) . . . . ?
C14A C12A C13A O3A -110.6(4) . . . . ?
C14A C15A C16A C17A 178.4(4) . . . . ?
C14A C15A C20A C19A -177.5(4) . . . . ?
C15A C16A C17A C18A -0.9(7) . . . . ?
C16A C15A C20A C19A 0.8(6) . . . . ?
C16A C17A C18A C19A 0.8(8) . . . . ?
C17A C18A C19A C20A 0.1(8) . . . . ?
C18A C19A C20A C15A -0.9(8) . . . . ?
C20A C15A C16A C17A 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
