# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2162471'
loop_
_audit_author_name
_audit_author_address
'Prashant Kumar'
;SRM University Delhi NCR Sonepat
India
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   24.354(3)
_cell_length_b                   8.7486(14)
_cell_length_c                   16.091(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3428.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1465
_cell_measurement_theta_min      3.4870
_cell_measurement_theta_max      17.7500

_exptl_crystal_description       'rod shape'
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40622
_diffrn_reflns_av_unetI/netI     0.1518
_diffrn_reflns_av_R_equivalents  0.12
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.346
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6054
_reflns_number_gt                2216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6041
_refine_ls_number_parameters     469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2110
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.1990
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.5001(3) 0.0412(9) 0.6005(5) 0.053(2) Uani 1 1 d . . . . .
N2 N 0.4304(4) 0.2683(9) 0.5408(6) 0.055(2) Uani 1 1 d . . . . .
O3 O 0.2718(3) 0.5082(8) 0.6078(5) 0.078(2) Uani 1 1 d . . . . .
C1 C 0.4190(4) 0.1193(11) 0.5223(6) 0.049(3) Uani 1 1 d . . . . .
N3 N 0.3275(4) 0.6901(10) 0.6633(5) 0.057(2) Uani 1 1 d . . . . .
O1 O 0.4869(3) 0.4485(8) 0.6000(5) 0.073(2) Uani 1 1 d . . . . .
C9 C 0.5596(4) 0.2193(11) 0.6669(7) 0.051(3) Uani 1 1 d . . . . .
C8 C 0.4756(5) 0.3107(13) 0.5881(7) 0.056(3) Uani 1 1 d . . . . .
N4 N 0.2544(4) 0.9128(10) 0.6070(6) 0.064(2) Uani 1 1 d . . . . .
O4 O 0.2837(3) 0.6270(9) 0.4307(6) 0.094(3) Uani 1 1 d . . . . .
C28 C 0.2470(5) 0.7666(13) 0.5883(7) 0.055(3) Uani 1 1 d . . . . .
C6 C 0.4552(4) 0.0094(11) 0.5516(6) 0.051(3) Uani 1 1 d . . . . .
C14 C 0.5621(4) 0.3222(12) 0.7316(7) 0.058(3) Uani 1 1 d . . . . .
O2 O 0.4714(3) 0.3134(9) 0.7793(6) 0.091(3) Uani 1 1 d . . . . .
C2 C 0.3746(4) 0.0766(14) 0.4759(7) 0.067(3) Uani 1 1 d . . . . .
H1 H 0.350081 0.150404 0.457230 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5120(5) 0.3926(13) 0.7679(7) 0.069(3) Uani 1 1 d . . . . .
C11 C 0.6570(5) 0.1725(14) 0.6840(9) 0.083(4) Uani 1 1 d . . . . .
H6 H 0.688803 0.121428 0.668020 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6120(5) 0.3513(13) 0.7706(7) 0.074(3) Uani 1 1 d . . . . .
H8 H 0.614016 0.423387 0.812937 0.089 Uiso 1 1 calc R U . . .
C37 C 0.2414(5) 0.3890(14) 0.4120(8) 0.070(3) Uani 1 1 d . . . . .
C16 C 0.5127(5) 0.5575(13) 0.7941(8) 0.067(3) Uani 1 1 d . . . . .
C44 C 0.3975(5) 0.3890(12) 0.5055(8) 0.082(4) Uani 1 1 d . . . . .
H16 H 0.410838 0.486094 0.524628 0.123 Uiso 1 1 calc R U . . .
H15 H 0.399802 0.384909 0.445978 0.123 Uiso 1 1 calc R U . . .
H14 H 0.359960 0.376406 0.522355 0.123 Uiso 1 1 calc R U . . .
C35 C 0.1927(4) 0.6186(12) 0.4811(7) 0.063(3) Uani 1 1 d . . . . .
C17 C 0.4782(5) 0.6021(15) 0.8591(8) 0.076(4) Uani 1 1 d . . . . .
H9 H 0.455532 0.530847 0.884888 0.092 Uiso 1 1 calc R U . . .
C24 C 0.3835(5) 0.8854(14) 0.7241(8) 0.074(4) Uani 1 1 d . . . . .
H17 H 0.408925 0.812207 0.740552 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3659(5) -0.0758(14) 0.4565(7) 0.074(3) Uani 1 1 d . . . . .
H2 H 0.335681 -0.103733 0.424578 0.089 Uiso 1 1 calc R U . . .
C10 C 0.6072(4) 0.1434(13) 0.6423(7) 0.071(3) Uani 1 1 d . . . . .
H5 H 0.606098 0.073979 0.598520 0.086 Uiso 1 1 calc R U . . .
C39 C 0.2126(7) 0.128(2) 0.4250(12) 0.111(6) Uani 1 1 d . . . . .
H28 H 0.193296 0.052266 0.453364 0.133 Uiso 1 1 calc R U . . .
C18 C 0.4778(7) 0.754(2) 0.8850(10) 0.099(5) Uani 1 1 d . . . . .
H10 H 0.456712 0.784220 0.930394 0.119 Uiso 1 1 calc R U . . .
C30 C 0.1960(5) 0.7298(12) 0.5442(8) 0.063(3) Uani 1 1 d . . . . .
C29 C 0.2822(5) 0.6444(14) 0.6185(7) 0.060(3) Uani 1 1 d . . . . .
C38 C 0.2097(6) 0.2798(17) 0.4529(11) 0.097(5) Uani 1 1 d . . . . .
H29 H 0.187251 0.306736 0.497366 0.116 Uiso 1 1 calc R U . . .
C43 C 0.3650(5) 0.5739(12) 0.6985(8) 0.090(4) Uani 1 1 d . . . . .
H32 H 0.353606 0.474073 0.680743 0.134 Uiso 1 1 calc R U . . .
H31 H 0.401729 0.593059 0.679488 0.134 Uiso 1 1 calc R U . . .
H30 H 0.363986 0.579228 0.758047 0.134 Uiso 1 1 calc R U . . .
C25 C 0.3917(5) 1.0334(18) 0.7416(8) 0.085(4) Uani 1 1 d . . . . .
H18 H 0.422884 1.060861 0.771306 0.102 Uiso 1 1 calc R U . . .
C34 C 0.1418(6) 0.5937(14) 0.4421(8) 0.084(4) Uani 1 1 d . . . . .
H24 H 0.138888 0.521248 0.400005 0.101 Uiso 1 1 calc R U . . .
C4 C 0.4021(6) -0.1869(14) 0.4847(7) 0.078(4) Uani 1 1 d . . . . .
H3 H 0.396221 -0.289085 0.471525 0.094 Uiso 1 1 calc R U . . .
C27 C 0.3086(5) 1.1057(14) 0.6725(8) 0.082(4) Uani 1 1 d . . . . .
H20 H 0.283549 1.179731 0.655714 0.099 Uiso 1 1 calc R U . . .
C12 C 0.6589(5) 0.2727(14) 0.7462(9) 0.082(4) Uani 1 1 d . . . . .
H7 H 0.691865 0.290216 0.773622 0.098 Uiso 1 1 calc R U . . .
C5 C 0.4457(4) -0.1469(12) 0.5310(7) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.469921 -0.221669 0.549677 0.078 Uiso 1 1 calc R U . . .
C42 C 0.2730(5) 0.3441(16) 0.3444(8) 0.076(4) Uani 1 1 d . . . . .
H25 H 0.294279 0.416346 0.316910 0.091 Uiso 1 1 calc R U . . .
C31 C 0.1485(5) 0.8100(14) 0.5661(8) 0.079(4) Uani 1 1 d . . . . .
H21 H 0.150375 0.883793 0.607615 0.094 Uiso 1 1 calc R U . . .
C22 C 0.3001(5) 0.9508(14) 0.6533(7) 0.070(3) Uani 1 1 d . . . . .
C36 C 0.2421(5) 0.5483(14) 0.4422(7) 0.068(3) Uani 1 1 d . . . . .
C40 C 0.2434(7) 0.0886(17) 0.3565(13) 0.100(5) Uani 1 1 d . . . . .
H27 H 0.243821 -0.011511 0.337003 0.120 Uiso 1 1 calc R U . . .
C7 C 0.5093(4) 0.1856(12) 0.6180(7) 0.050(3) Uani 1 1 d . . . . .
C26 C 0.3558(7) 1.1465(15) 0.7174(8) 0.084(4) Uani 1 1 d . . . . .
H19 H 0.362666 1.248169 0.730545 0.101 Uiso 1 1 calc R U . . .
C33 C 0.0964(6) 0.675(2) 0.4657(11) 0.106(5) Uani 1 1 d . . . . .
H23 H 0.063136 0.657938 0.438824 0.127 Uiso 1 1 calc R U . . .
C19 C 0.5086(8) 0.8588(18) 0.8434(13) 0.115(6) Uani 1 1 d . . . . .
H11 H 0.507036 0.960953 0.859282 0.138 Uiso 1 1 calc R U . . .
C32 C 0.0986(5) 0.7819(16) 0.5275(10) 0.093(4) Uani 1 1 d . . . . .
H22 H 0.067229 0.834836 0.543479 0.112 Uiso 1 1 calc R U . . .
C21 C 0.5436(5) 0.6656(16) 0.7562(9) 0.082(4) Uani 1 1 d . . . . .
H13 H 0.566867 0.636308 0.713211 0.098 Uiso 1 1 calc R U . . .
C23 C 0.3366(5) 0.8430(13) 0.6812(7) 0.054(3) Uani 1 1 d . . . . .
C41 C 0.2733(7) 0.1992(19) 0.3179(10) 0.097(5) Uani 1 1 d . . . . .
H26 H 0.294545 0.173348 0.272007 0.117 Uiso 1 1 calc R U . . .
C20 C 0.5419(7) 0.8175(18) 0.7789(12) 0.098(5) Uani 1 1 d . . . . .
H12 H 0.562894 0.890019 0.751038 0.117 Uiso 1 1 calc R U . . .


_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
N1 C7 1.314(11) . ?
N1 C6 1.376(12) . ?
N2 C1 1.365(11) . ?
N2 C8 1.387(13) . ?
N2 C44 1.443(12) . ?
O3 C29 1.230(11) . ?
C1 C2 1.364(13) . ?
C1 C6 1.388(12) . ?
N3 C23 1.385(12) . ?
N3 C29 1.378(13) . ?
N3 C43 1.479(13) . ?
O1 C8 1.251(12) . ?
C9 C14 1.377(13) . ?
C9 C10 1.393(13) . ?
C9 C7 1.487(13) . ?
C8 C7 1.451(13) . ?
N4 C28 1.327(12) . ?
N4 C22 1.379(13) . ?
O4 C36 1.239(12) . ?
C28 C29 1.453(15) . ?
C28 C30 1.466(15) . ?
C6 C5 1.426(12) . ?
C14 C13 1.391(13) . ?
C14 C15 1.487(14) . ?
O2 C15 1.220(11) . ?
C2 C3 1.386(13) . ?
C2 H1 0.9300 . ?
C15 C16 1.503(14) . ?
C11 C12 1.330(16) . ?
C11 C10 1.411(13) . ?
C11 H6 0.9300 . ?
C13 C12 1.389(14) . ?
C13 H8 0.9300 . ?
C37 C42 1.389(16) . ?
C37 C38 1.394(17) . ?
C37 C36 1.476(15) . ?
C16 C21 1.354(15) . ?
C16 C17 1.398(16) . ?
C44 H16 0.9600 . ?
C44 H15 0.9600 . ?
C44 H14 0.9600 . ?
C35 C30 1.409(15) . ?
C35 C34 1.408(14) . ?
C35 C36 1.488(14) . ?
C17 C18 1.397(17) . ?
C17 H9 0.9300 . ?
C24 C25 1.340(15) . ?
C24 C23 1.386(14) . ?
C24 H17 0.9300 . ?
C3 C4 1.390(14) . ?
C3 H2 0.9300 . ?
C10 H5 0.9300 . ?
C39 C40 1.38(2) . ?
C39 C38 1.405(18) . ?
C39 H28 0.9300 . ?
C18 C19 1.36(2) . ?
C18 H10 0.9300 . ?
C30 C31 1.399(15) . ?
C38 H29 0.9300 . ?
C43 H32 0.9600 . ?
C43 H31 0.9600 . ?
C43 H30 0.9600 . ?
C25 C26 1.376(16) . ?
C25 H18 0.9300 . ?
C34 C33 1.371(16) . ?
C34 H24 0.9300 . ?
C4 C5 1.343(14) . ?
C4 H3 0.9300 . ?
C27 C22 1.406(14) . ?
C27 C26 1.402(16) . ?
C27 H20 0.9300 . ?
C12 H7 0.9300 . ?
C5 H4 0.9300 . ?
C42 C41 1.337(15) . ?
C42 H25 0.9300 . ?
C31 C32 1.386(15) . ?
C31 H21 0.9300 . ?
C22 C23 1.371(14) . ?
C40 C41 1.36(2) . ?
C40 H27 0.9300 . ?
C26 H19 0.9300 . ?
C33 C32 1.364(19) . ?
C33 H23 0.9300 . ?
C19 C20 1.37(2) . ?
C19 H11 0.9300 . ?
C32 H22 0.9300 . ?
C21 C20 1.379(16) . ?
C21 H13 0.9300 . ?
C41 H26 0.9300 . ?
C20 H12 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
C7 N1 C6 116.9(9) . . ?
C1 N2 C8 122.5(9) . . ?
C1 N2 C44 119.9(9) . . ?
C8 N2 C44 117.4(9) . . ?
C2 C1 N2 122.8(10) . . ?
C2 C1 C6 120.0(10) . . ?
N2 C1 C6 117.2(9) . . ?
C23 N3 C29 121.1(10) . . ?
C23 N3 C43 119.1(9) . . ?
C29 N3 C43 119.7(9) . . ?
C14 C9 C10 119.4(10) . . ?
C14 C9 C7 124.5(10) . . ?
C10 C9 C7 116.1(9) . . ?
O1 C8 N2 121.1(10) . . ?
O1 C8 C7 123.4(11) . . ?
N2 C8 C7 115.4(10) . . ?
C28 N4 C22 117.7(9) . . ?
N4 C28 C29 123.6(11) . . ?
N4 C28 C30 115.9(10) . . ?
C29 C28 C30 120.0(10) . . ?
N1 C6 C1 124.0(9) . . ?
N1 C6 C5 117.1(10) . . ?
C1 C6 C5 118.8(10) . . ?
C9 C14 C13 119.9(10) . . ?
C9 C14 C15 122.1(10) . . ?
C13 C14 C15 117.7(10) . . ?
C1 C2 C3 120.6(11) . . ?
C1 C2 H1 119.7 . . ?
C3 C2 H1 119.7 . . ?
O2 C15 C14 119.3(10) . . ?
O2 C15 C16 120.8(11) . . ?
C14 C15 C16 119.8(10) . . ?
C12 C11 C10 120.4(12) . . ?
C12 C11 H6 119.8 . . ?
C10 C11 H6 119.8 . . ?
C12 C13 C14 120.0(11) . . ?
C12 C13 H8 120.0 . . ?
C14 C13 H8 120.0 . . ?
C42 C37 C38 118.9(12) . . ?
C42 C37 C36 121.3(12) . . ?
C38 C37 C36 119.8(13) . . ?
C21 C16 C17 118.4(12) . . ?
C21 C16 C15 123.4(12) . . ?
C17 C16 C15 118.1(12) . . ?
N2 C44 H16 109.5 . . ?
N2 C44 H15 109.5 . . ?
H16 C44 H15 109.5 . . ?
N2 C44 H14 109.5 . . ?
H16 C44 H14 109.5 . . ?
H15 C44 H14 109.5 . . ?
C30 C35 C34 118.6(11) . . ?
C30 C35 C36 122.8(11) . . ?
C34 C35 C36 117.5(11) . . ?
C16 C17 C18 119.6(14) . . ?
C16 C17 H9 120.2 . . ?
C18 C17 H9 120.2 . . ?
C25 C24 C23 119.1(12) . . ?
C25 C24 H17 120.4 . . ?
C23 C24 H17 120.4 . . ?
C2 C3 C4 120.1(11) . . ?
C2 C3 H2 119.9 . . ?
C4 C3 H2 119.9 . . ?
C9 C10 C11 119.6(10) . . ?
C9 C10 H5 120.2 . . ?
C11 C10 H5 120.2 . . ?
C40 C39 C38 121.3(15) . . ?
C40 C39 H28 119.4 . . ?
C38 C39 H28 119.4 . . ?
C19 C18 C17 119.4(16) . . ?
C19 C18 H10 120.3 . . ?
C17 C18 H10 120.3 . . ?
C31 C30 C35 118.8(11) . . ?
C31 C30 C28 118.0(11) . . ?
C35 C30 C28 123.3(11) . . ?
O3 C29 N3 121.3(11) . . ?
O3 C29 C28 123.0(11) . . ?
N3 C29 C28 115.7(10) . . ?
C37 C38 C39 118.0(15) . . ?
C37 C38 H29 121.0 . . ?
C39 C38 H29 121.0 . . ?
N3 C43 H32 109.5 . . ?
N3 C43 H31 109.5 . . ?
H32 C43 H31 109.5 . . ?
N3 C43 H30 109.5 . . ?
H32 C43 H30 109.5 . . ?
H31 C43 H30 109.5 . . ?
C24 C25 C26 122.7(13) . . ?
C24 C25 H18 118.6 . . ?
C26 C25 H18 118.6 . . ?
C33 C34 C35 120.5(13) . . ?
C33 C34 H24 119.8 . . ?
C35 C34 H24 119.8 . . ?
C5 C4 C3 120.1(11) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C22 C27 C26 118.6(12) . . ?
C22 C27 H20 120.7 . . ?
C26 C27 H20 120.7 . . ?
C11 C12 C13 120.7(12) . . ?
C11 C12 H7 119.6 . . ?
C13 C12 H7 119.6 . . ?
C4 C5 C6 120.4(11) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C41 C42 C37 121.4(14) . . ?
C41 C42 H25 119.3 . . ?
C37 C42 H25 119.3 . . ?
C32 C31 C30 121.5(12) . . ?
C32 C31 H21 119.2 . . ?
C30 C31 H21 119.2 . . ?
C23 C22 N4 122.3(11) . . ?
C23 C22 C27 119.7(12) . . ?
N4 C22 C27 118.0(12) . . ?
O4 C36 C37 119.0(11) . . ?
O4 C36 C35 119.5(11) . . ?
C37 C36 C35 121.3(11) . . ?
C41 C40 C39 118.6(16) . . ?
C41 C40 H27 120.7 . . ?
C39 C40 H27 120.7 . . ?
N1 C7 C8 123.9(10) . . ?
N1 C7 C9 116.4(9) . . ?
C8 C7 C9 119.6(9) . . ?
C25 C26 C27 118.9(12) . . ?
C25 C26 H19 120.6 . . ?
C27 C26 H19 120.6 . . ?
C32 C33 C34 121.7(14) . . ?
C32 C33 H23 119.1 . . ?
C34 C33 H23 119.1 . . ?
C18 C19 C20 121.7(16) . . ?
C18 C19 H11 119.2 . . ?
C20 C19 H11 119.2 . . ?
C33 C32 C31 118.9(13) . . ?
C33 C32 H22 120.5 . . ?
C31 C32 H22 120.5 . . ?
C16 C21 C20 122.5(14) . . ?
C16 C21 H13 118.8 . . ?
C20 C21 H13 118.8 . . ?
C22 C23 C24 120.9(11) . . ?
C22 C23 N3 119.5(11) . . ?
C24 C23 N3 119.6(11) . . ?
C42 C41 C40 121.7(16) . . ?
C42 C41 H26 119.1 . . ?
C40 C41 H26 119.1 . . ?
C19 C20 C21 118.3(16) . . ?
C19 C20 H12 120.8 . . ?
C21 C20 H12 120.8 . . ?

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
C8 N2 C1 C2 179.9(10) . . . . ?
C44 N2 C1 C2 -5.1(15) . . . . ?
C8 N2 C1 C6 -1.1(14) . . . . ?
C44 N2 C1 C6 173.9(9) . . . . ?
C1 N2 C8 O1 175.7(9) . . . . ?
C44 N2 C8 O1 0.6(15) . . . . ?
C1 N2 C8 C7 -1.3(14) . . . . ?
C44 N2 C8 C7 -176.4(9) . . . . ?
C22 N4 C28 C29 4.3(15) . . . . ?
C22 N4 C28 C30 175.8(10) . . . . ?
C7 N1 C6 C1 -1.8(14) . . . . ?
C7 N1 C6 C5 178.7(9) . . . . ?
C2 C1 C6 N1 -178.2(9) . . . . ?
N2 C1 C6 N1 2.7(14) . . . . ?
C2 C1 C6 C5 1.2(14) . . . . ?
N2 C1 C6 C5 -177.8(9) . . . . ?
C10 C9 C14 C13 1.1(16) . . . . ?
C7 C9 C14 C13 -176.6(10) . . . . ?
C10 C9 C14 C15 -172.3(10) . . . . ?
C7 C9 C14 C15 10.0(17) . . . . ?
N2 C1 C2 C3 177.8(10) . . . . ?
C6 C1 C2 C3 -1.1(16) . . . . ?
C9 C14 C15 O2 41.7(16) . . . . ?
C13 C14 C15 O2 -131.9(12) . . . . ?
C9 C14 C15 C16 -141.6(11) . . . . ?
C13 C14 C15 C16 44.9(14) . . . . ?
C9 C14 C13 C12 -2.3(17) . . . . ?
C15 C14 C13 C12 171.4(11) . . . . ?
O2 C15 C16 C21 -151.9(12) . . . . ?
C14 C15 C16 C21 31.4(16) . . . . ?
O2 C15 C16 C17 25.7(16) . . . . ?
C14 C15 C16 C17 -151.0(11) . . . . ?
C21 C16 C17 C18 -2.2(17) . . . . ?
C15 C16 C17 C18 180.0(10) . . . . ?
C1 C2 C3 C4 0.4(18) . . . . ?
C14 C9 C10 C11 0.3(17) . . . . ?
C7 C9 C10 C11 178.2(10) . . . . ?
C12 C11 C10 C9 -1(2) . . . . ?
C16 C17 C18 C19 4(2) . . . . ?
C34 C35 C30 C31 0.6(16) . . . . ?
C36 C35 C30 C31 168.2(10) . . . . ?
C34 C35 C30 C28 -179.2(10) . . . . ?
C36 C35 C30 C28 -11.7(17) . . . . ?
N4 C28 C30 C31 -37.2(15) . . . . ?
C29 C28 C30 C31 134.6(11) . . . . ?
N4 C28 C30 C35 142.7(11) . . . . ?
C29 C28 C30 C35 -45.6(16) . . . . ?
C23 N3 C29 O3 -174.6(9) . . . . ?
C43 N3 C29 O3 0.6(15) . . . . ?
C23 N3 C29 C28 3.3(13) . . . . ?
C43 N3 C29 C28 178.5(9) . . . . ?
N4 C28 C29 O3 172.4(10) . . . . ?
C30 C28 C29 O3 1.4(16) . . . . ?
N4 C28 C29 N3 -5.4(15) . . . . ?
C30 C28 C29 N3 -176.4(10) . . . . ?
C42 C37 C38 C39 2.0(19) . . . . ?
C36 C37 C38 C39 -176.5(12) . . . . ?
C40 C39 C38 C37 -4(2) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C30 C35 C34 C33 -0.5(17) . . . . ?
C36 C35 C34 C33 -168.7(12) . . . . ?
C2 C3 C4 C5 0.1(19) . . . . ?
C10 C11 C12 C13 -1(2) . . . . ?
C14 C13 C12 C11 2(2) . . . . ?
C3 C4 C5 C6 0.0(18) . . . . ?
N1 C6 C5 C4 178.8(10) . . . . ?
C1 C6 C5 C4 -0.7(15) . . . . ?
C38 C37 C42 C41 0.1(18) . . . . ?
C36 C37 C42 C41 178.6(11) . . . . ?
C35 C30 C31 C32 0.2(18) . . . . ?
C28 C30 C31 C32 -179.9(11) . . . . ?
C28 N4 C22 C23 -1.3(16) . . . . ?
C28 N4 C22 C27 179.1(10) . . . . ?
C26 C27 C22 C23 2.3(17) . . . . ?
C26 C27 C22 N4 -178.1(11) . . . . ?
C42 C37 C36 O4 -27.4(17) . . . . ?
C38 C37 C36 O4 151.0(13) . . . . ?
C42 C37 C36 C35 148.6(11) . . . . ?
C38 C37 C36 C35 -33.0(17) . . . . ?
C30 C35 C36 O4 -36.1(17) . . . . ?
C34 C35 C36 O4 131.6(12) . . . . ?
C30 C35 C36 C37 148.0(11) . . . . ?
C34 C35 C36 C37 -44.3(15) . . . . ?
C38 C39 C40 C41 3(2) . . . . ?
C6 N1 C7 C8 -0.9(14) . . . . ?
C6 N1 C7 C9 -176.7(9) . . . . ?
O1 C8 C7 N1 -174.5(10) . . . . ?
N2 C8 C7 N1 2.3(14) . . . . ?
O1 C8 C7 C9 1.2(15) . . . . ?
N2 C8 C7 C9 178.1(9) . . . . ?
C14 C9 C7 N1 -137.8(10) . . . . ?
C10 C9 C7 N1 44.4(13) . . . . ?
C14 C9 C7 C8 46.2(15) . . . . ?
C10 C9 C7 C8 -131.6(10) . . . . ?
C24 C25 C26 C27 0(2) . . . . ?
C22 C27 C26 C25 -0.5(18) . . . . ?
C35 C34 C33 C32 -1(2) . . . . ?
C17 C18 C19 C20 -3(2) . . . . ?
C34 C33 C32 C31 1(2) . . . . ?
C30 C31 C32 C33 -1(2) . . . . ?
C17 C16 C21 C20 -0.5(19) . . . . ?
C15 C16 C21 C20 177.2(12) . . . . ?
N4 C22 C23 C24 176.8(10) . . . . ?
C27 C22 C23 C24 -3.6(17) . . . . ?
N4 C22 C23 N3 -0.6(16) . . . . ?
C27 C22 C23 N3 179.0(10) . . . . ?
C25 C24 C23 C22 3.0(17) . . . . ?
C25 C24 C23 N3 -179.6(10) . . . . ?
C29 N3 C23 C22 -0.6(14) . . . . ?
C43 N3 C23 C22 -175.8(10) . . . . ?
C29 N3 C23 C24 -178.0(10) . . . . ?
C43 N3 C23 C24 6.7(14) . . . . ?
C37 C42 C41 C40 -1(2) . . . . ?
C39 C40 C41 C42 -1(2) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C16 C21 C20 C19 2(2) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.042

