# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Vijaykanth6b
_database_code_depnum_ccdc_archive 'CCDC 2211500'
loop_
_audit_author_name
_audit_author_address
'Natalia Fridman'
;Technion Israel Institute of Technology
Israel
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Vijaykanth6b
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.973(5)
_cell_length_b                   8.157(8)
_cell_length_c                   48.990(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1987(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2519
_cell_measurement_theta_min      1.663
_cell_measurement_theta_max      24.466

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            5908
_diffrn_reflns_av_unetI/netI     0.1963
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         1.663
_diffrn_reflns_theta_max         24.466
_diffrn_reflns_theta_full        24.466
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2519
_reflns_number_gt                1487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0971P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2519
_refine_ls_number_parameters     268
_refine_ls_number_restraints     268
_refine_ls_R_factor_all          0.2009
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT340_Vijaykanth6b        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01557 Ang.  
RESPONSE: Partly disordered phenyl rings in the structure
;
# end Validation Reply Form

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 -0.3777(12) -0.5905(8) -0.63453(13) 0.0495(19) Uani 1 1 d . U . . .
O2 O -0.7578(13) -0.5311(10) -0.65749(13) 0.064(2) Uani 1 1 d . U . . .
O3 O -0.0436(12) -0.5419(9) -0.72166(13) 0.055(2) Uani 1 1 d . U . . .
O4 O -0.3222(12) -0.4065(9) -0.74844(13) 0.053(2) Uani 1 1 d . U . . .
H4 H -0.1950 -0.4155 -0.7596 0.079 Uiso 1 1 calc R U . . .
N1 N -0.3492(18) -0.4954(9) -0.67705(17) 0.038(2) Uani 1 1 d . U . . .
H1 H -0.18(2) -0.525(13) -0.679(2) 0.07(4) Uiso 1 1 d . . . . .
N2 N -0.0187(15) 0.0442(10) -0.71260(15) 0.044(2) Uani 1 1 d . U . . .
C1 C -0.3832(18) -0.5746(13) -0.58489(17) 0.043(2) Uani 1 1 d . U . . .
H1A H -0.2202 -0.6444 -0.5821 0.052 Uiso 1 1 calc R U . . .
C2 C -0.5700(19) -0.5874(14) -0.5606(2) 0.049(3) Uani 1 1 d . U . . .
C3 C -0.708(2) -0.7241(15) -0.5515(2) 0.061(3) Uani 1 1 d . U . . .
H3 H -0.6843 -0.8281 -0.5599 0.073 Uiso 1 1 calc R U . . .
C4 C -0.887(2) -0.7029(17) -0.5289(2) 0.073(3) Uani 1 1 d . U . . .
H4A H -0.9873 -0.7939 -0.5223 0.087 Uiso 1 1 calc R U . . .
C5 C -0.916(3) -0.5553(19) -0.5169(2) 0.078(4) Uani 1 1 d . U . . .
H5 H -1.0392 -0.5429 -0.5022 0.094 Uiso 1 1 calc R U . . .
C6 C -0.773(2) -0.4261(18) -0.5254(2) 0.078(4) Uani 1 1 d . U . . .
H6 H -0.7892 -0.3241 -0.5162 0.093 Uiso 1 1 calc R U . . .
C7 C -0.601(2) -0.4405(15) -0.5479(2) 0.054(3) Uani 1 1 d . U . . .
C8 C -0.433(2) -0.3177(14) -0.5621(2) 0.054(3) Uani 1 1 d . U . . .
C9 C -0.387(3) -0.1547(17) -0.5568(3) 0.081(4) Uani 1 1 d . U . . .
H9 H -0.4714 -0.1023 -0.5418 0.097 Uiso 1 1 calc R U . . .
C10 C -0.216(3) -0.0680(17) -0.5738(3) 0.086(4) Uani 1 1 d . U . . .
H10 H -0.1848 0.0449 -0.5703 0.103 Uiso 1 1 calc R U . . .
C11 C -0.089(3) -0.1396(16) -0.5956(3) 0.075(4) Uani 1 1 d . U . . .
H11 H 0.0296 -0.0777 -0.6068 0.090 Uiso 1 1 calc R U . . .
C12 C -0.137(2) -0.3061(15) -0.6011(2) 0.064(3) Uani 1 1 d . U . . .
H12 H -0.0527 -0.3577 -0.6163 0.077 Uiso 1 1 calc R U . . .
C13 C -0.309(2) -0.3952(13) -0.5841(2) 0.049(3) Uani 1 1 d . U . . .
C14 C -0.535(2) -0.6273(14) -0.61062(19) 0.054(3) Uani 1 1 d . U . . .
H14A H -0.5722 -0.7465 -0.6099 0.065 Uiso 1 1 calc R U . . .
H14B H -0.7094 -0.5689 -0.6116 0.065 Uiso 1 1 calc R U . . .
C15 C -0.511(2) -0.5368(14) -0.6569(2) 0.042(2) Uani 1 1 d . U . . .
C16 C -0.4579(16) -0.4437(12) -0.70317(18) 0.038(2) Uani 1 1 d . U . . .
H16 H -0.6116 -0.5186 -0.7074 0.045 Uiso 1 1 calc R U . A 1
C17 C -0.5718(16) -0.2691(12) -0.7023(2) 0.046(3) Uani 1 1 d . U . . .
H17A H -0.6569 -0.2450 -0.7201 0.056 Uiso 1 1 calc R U . . .
H17B H -0.7145 -0.2648 -0.6882 0.056 Uiso 1 1 calc R U . . .
C18 C -0.2510(19) -0.4682(12) -0.72531(19) 0.033(2) Uani 1 1 d . U . . .
C19 C -0.3681(19) -0.1359(12) -0.6962(2) 0.041(2) Uani 1 1 d . U . . .
C20 C -0.326(2) -0.0708(15) -0.6700(2) 0.056(3) Uani 1 1 d . U . . .
H20 H -0.4249 -0.1141 -0.6551 0.067 Uiso 1 1 calc R U . . .
C21 C -0.144(2) 0.0552(14) -0.6654(2) 0.066(3) Uani 1 1 d . U . . .
H21 H -0.1240 0.1023 -0.6478 0.079 Uiso 1 1 calc R U . . .
C22 C 0.007(2) 0.1102(12) -0.6872(2) 0.052(3) Uani 1 1 d . U . . .
H22 H 0.1330 0.1963 -0.6845 0.062 Uiso 1 1 calc R U . . .
C23 C -0.2068(17) -0.0717(13) -0.71671(19) 0.042(2) Uani 1 1 d . U . . .
H23 H -0.2308 -0.1121 -0.7347 0.051 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
O1 C15 1.352(11) . ?
O1 C14 1.441(10) . ?
O2 C15 1.230(11) . ?
O3 C18 1.207(11) . ?
O4 C18 1.290(10) . ?
O4 H4 0.8400 . ?
N1 C15 1.318(12) . ?
N1 C16 1.452(11) . ?
N1 H1 0.88(11) . ?
N2 C23 1.345(12) . ?
N2 C22 1.360(12) . ?
C1 C13 1.509(15) . ?
C1 C2 1.511(12) . ?
C1 C14 1.531(12) . ?
C1 H1A 1.0000 . ?
C2 C7 1.361(14) . ?
C2 C3 1.384(14) . ?
C3 C4 1.431(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.348(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.337(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.480(15) . ?
C8 C9 1.374(16) . ?
C8 C13 1.393(14) . ?
C9 C10 1.387(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.405(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(14) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C18 1.508(12) . ?
C16 C17 1.533(14) . ?
C16 H16 1.0000 . ?
C17 C19 1.515(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C23 1.388(12) . ?
C19 C20 1.403(13) . ?
C20 C21 1.388(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(14) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 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
C15 O1 C14 117.4(7) . . ?
C18 O4 H4 109.5 . . ?
C15 N1 C16 120.6(8) . . ?
C15 N1 H1 127(7) . . ?
C16 N1 H1 109(7) . . ?
C23 N2 C22 118.7(9) . . ?
C13 C1 C2 101.4(8) . . ?
C13 C1 C14 114.3(8) . . ?
C2 C1 C14 108.9(8) . . ?
C13 C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
C14 C1 H1A 110.6 . . ?
C7 C2 C3 120.3(10) . . ?
C7 C2 C1 111.8(10) . . ?
C3 C2 C1 127.9(10) . . ?
C2 C3 C4 117.5(12) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 120.8(13) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C6 C5 C4 120.7(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.3(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.3(11) . . ?
C2 C7 C8 108.3(10) . . ?
C6 C7 C8 131.3(12) . . ?
C9 C8 C13 120.8(12) . . ?
C9 C8 C7 131.2(12) . . ?
C13 C8 C7 107.9(10) . . ?
C8 C9 C10 118.8(13) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 122.3(14) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 119.0(14) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 119.5(12) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 C12 119.7(11) . . ?
C8 C13 C1 110.6(9) . . ?
C12 C13 C1 129.7(10) . . ?
O1 C14 C1 110.1(7) . . ?
O1 C14 H14A 109.7 . . ?
C1 C14 H14A 109.7 . . ?
O1 C14 H14B 109.6 . . ?
C1 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O2 C15 N1 125.5(10) . . ?
O2 C15 O1 121.4(9) . . ?
N1 C15 O1 113.1(8) . . ?
N1 C16 C18 110.0(7) . . ?
N1 C16 C17 112.5(8) . . ?
C18 C16 C17 113.3(8) . . ?
N1 C16 H16 106.9 . . ?
C18 C16 H16 106.9 . . ?
C17 C16 H16 106.9 . . ?
C19 C17 C16 115.2(7) . . ?
C19 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C19 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
O3 C18 O4 124.0(9) . . ?
O3 C18 C16 122.9(9) . . ?
O4 C18 C16 113.1(8) . . ?
C23 C19 C20 115.6(10) . . ?
C23 C19 C17 120.9(10) . . ?
C20 C19 C17 123.4(10) . . ?
C21 C20 C19 121.8(10) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 117.9(10) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
N2 C22 C21 121.8(11) . . ?
N2 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
N2 C23 C19 123.9(9) . . ?
N2 C23 H23 118.0 . . ?
C19 C23 H23 118.0 . . ?

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
C13 C1 C2 C7 0.1(10) . . . . ?
C14 C1 C2 C7 -120.8(10) . . . . ?
C13 C1 C2 C3 178.2(10) . . . . ?
C14 C1 C2 C3 57.3(13) . . . . ?
C7 C2 C3 C4 1.8(14) . . . . ?
C1 C2 C3 C4 -176.1(9) . . . . ?
C2 C3 C4 C5 -1.0(16) . . . . ?
C3 C4 C5 C6 -1.4(19) . . . . ?
C4 C5 C6 C7 3.1(19) . . . . ?
C3 C2 C7 C6 -0.2(15) . . . . ?
C1 C2 C7 C6 178.0(9) . . . . ?
C3 C2 C7 C8 -179.5(9) . . . . ?
C1 C2 C7 C8 -1.3(11) . . . . ?
C5 C6 C7 C2 -2.3(16) . . . . ?
C5 C6 C7 C8 176.8(11) . . . . ?
C2 C7 C8 C9 -177.7(12) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
C2 C7 C8 C13 2.1(11) . . . . ?
C6 C7 C8 C13 -177.1(10) . . . . ?
C13 C8 C9 C10 0.0(17) . . . . ?
C7 C8 C9 C10 179.8(10) . . . . ?
C8 C9 C10 C11 -0.5(19) . . . . ?
C9 C10 C11 C12 0.8(19) . . . . ?
C10 C11 C12 C13 -0.8(18) . . . . ?
C9 C8 C13 C12 0.0(15) . . . . ?
C7 C8 C13 C12 -179.8(9) . . . . ?
C9 C8 C13 C1 177.8(10) . . . . ?
C7 C8 C13 C1 -2.0(11) . . . . ?
C11 C12 C13 C8 0.4(15) . . . . ?
C11 C12 C13 C1 -176.9(11) . . . . ?
C2 C1 C13 C8 1.2(10) . . . . ?
C14 C1 C13 C8 118.2(9) . . . . ?
C2 C1 C13 C12 178.7(9) . . . . ?
C14 C1 C13 C12 -64.3(14) . . . . ?
C15 O1 C14 C1 -142.2(9) . . . . ?
C13 C1 C14 O1 57.8(11) . . . . ?
C2 C1 C14 O1 170.4(8) . . . . ?
C16 N1 C15 O2 -2.6(16) . . . . ?
C16 N1 C15 O1 176.5(8) . . . . ?
C14 O1 C15 O2 -5.3(15) . . . . ?
C14 O1 C15 N1 175.5(8) . . . . ?
C15 N1 C16 C18 -157.5(9) . . . . ?
C15 N1 C16 C17 75.2(11) . . . . ?
N1 C16 C17 C19 63.2(11) . . . . ?
C18 C16 C17 C19 -62.2(12) . . . . ?
N1 C16 C18 O3 9.7(13) . . . . ?
C17 C16 C18 O3 136.4(9) . . . . ?
N1 C16 C18 O4 -172.1(8) . . . . ?
C17 C16 C18 O4 -45.3(11) . . . . ?
C16 C17 C19 C23 82.4(12) . . . . ?
C16 C17 C19 C20 -96.7(12) . . . . ?
C23 C19 C20 C21 3.0(15) . . . . ?
C17 C19 C20 C21 -177.8(9) . . . . ?
C19 C20 C21 C22 -3.3(15) . . . . ?
C23 N2 C22 C21 3.4(14) . . . . ?
C20 C21 C22 N2 0.0(15) . . . . ?
C22 N2 C23 C19 -3.8(13) . . . . ?
C20 C19 C23 N2 0.6(13) . . . . ?
C17 C19 C23 N2 -178.6(8) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_Vijaykanth7b
_database_code_depnum_ccdc_archive 'CCDC 2211502'
loop_
_audit_author_name
_audit_author_address
'Natalia Fridman'
;Technion Israel Institute of Technology
Israel
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Vijaykanth7b
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.917(11)
_cell_length_b                   4.929(2)
_cell_length_c                   15.665(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.334(10)
_cell_angle_gamma                90
_cell_volume                     1984.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2155
_cell_measurement_theta_min      1.584
_cell_measurement_theta_max      24.415

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            10556
_diffrn_reflns_av_unetI/netI     0.1218
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.584
_diffrn_reflns_theta_max         24.415
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2155
_reflns_number_gt                1309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0597P)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_number_reflns         2155
_refine_ls_number_parameters     263
_refine_ls_number_restraints     268
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.869
_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
O1 O 0.26063(10) 0.6915(5) 0.52153(18) 0.0493(8) Uani 1 1 d . U . . .
O2 O 0.21486(10) 0.3018(5) 0.5041(2) 0.0717(10) Uani 1 1 d . U . . .
O3 O 0.09940(11) 1.0027(5) 0.40079(19) 0.0645(10) Uani 1 1 d . U . . .
O4 O 0.04182(10) 0.6716(5) 0.4035(2) 0.0542(8) Uani 1 1 d . U . . .
H4 H 0.0230 0.7750 0.3701 0.081 Uiso 1 1 calc R U . . .
N1 N 0.17502(12) 0.7098(6) 0.4926(2) 0.0431(9) Uani 1 1 d . U . . .
H1 H 0.1787 0.8872 0.4945 0.052 Uiso 1 1 calc R U . . .
N2 N 0.03445(12) 1.0304(6) 0.6671(2) 0.0462(9) Uani 1 1 d . U . . .
C1 C 0.34536(15) 0.6592(8) 0.6022(3) 0.0510(11) Uani 1 1 d . U . . .
H1A H 0.3536 0.8520 0.5894 0.061 Uiso 1 1 calc R U . . .
C2 C 0.04559(15) 0.8295(7) 0.6153(3) 0.0442(11) Uani 1 1 d . U . . .
H2 H 0.0186 0.7677 0.5731 0.053 Uiso 1 1 calc R U . . .
C3 C 0.42768(18) 0.4358(10) 0.5536(4) 0.0831(16) Uani 1 1 d . U . . .
H3 H 0.4235 0.5254 0.4995 0.100 Uiso 1 1 calc R U . . .
C4 C 0.4683(2) 0.2527(12) 0.5746(5) 0.113(2) Uani 1 1 d . U . . .
H4A H 0.4926 0.2190 0.5353 0.136 Uiso 1 1 calc R U . . .
C5 C 0.4728(3) 0.1198(13) 0.6535(5) 0.115(3) Uani 1 1 d . U . . .
H5 H 0.5004 -0.0059 0.6672 0.138 Uiso 1 1 calc R U . . .
C6 C 0.4388(2) 0.1642(10) 0.7119(4) 0.104(2) Uani 1 1 d . U . . .
H6 H 0.4426 0.0701 0.7652 0.124 Uiso 1 1 calc R U . . .
C7 C 0.39853(19) 0.3501(9) 0.6917(4) 0.0683(14) Uani 1 1 d . U . . .
C8 C 0.3579(2) 0.4451(9) 0.7394(4) 0.0726(14) Uani 1 1 d . U . . .
C9 C 0.3457(3) 0.3769(11) 0.8218(4) 0.101(2) Uani 1 1 d . U . . .
H9 H 0.3660 0.2493 0.8570 0.121 Uiso 1 1 calc R U . . .
C10 C 0.3037(3) 0.4998(12) 0.8496(4) 0.115(2) Uani 1 1 d . U . . .
H10 H 0.2946 0.4529 0.9046 0.138 Uiso 1 1 calc R U . . .
C11 C 0.2745(2) 0.6871(12) 0.8016(4) 0.0967(18) Uani 1 1 d . U . . .
H11 H 0.2461 0.7715 0.8240 0.116 Uiso 1 1 calc R U . . .
C12 C 0.2858(2) 0.7562(10) 0.7196(3) 0.0778(15) Uani 1 1 d . U . . .
H12 H 0.2653 0.8854 0.6855 0.093 Uiso 1 1 calc R U . . .
C13 C 0.32747(18) 0.6325(8) 0.6895(3) 0.0587(12) Uani 1 1 d . U . . .
C14 C 0.30754(14) 0.5372(8) 0.5311(3) 0.0508(12) Uani 1 1 d . U . . .
H14A H 0.3230 0.5384 0.4765 0.061 Uiso 1 1 calc R U . . .
H14B H 0.3000 0.3468 0.5453 0.061 Uiso 1 1 calc R U . . .
C15 C 0.21627(16) 0.5470(8) 0.5059(3) 0.0441(11) Uani 1 1 d . U . . .
C16 C 0.12414(14) 0.5889(7) 0.4750(3) 0.0388(10) Uani 1 1 d . U . . .
H16 H 0.1278 0.4266 0.4379 0.047 Uiso 1 1 calc R U . . .
C17 C 0.10313(15) 0.4871(7) 0.5558(3) 0.0462(11) Uani 1 1 d . U . . .
H17A H 0.0701 0.3892 0.5384 0.055 Uiso 1 1 calc R U . . .
H17B H 0.1282 0.3554 0.5852 0.055 Uiso 1 1 calc R U . . .
C18 C 0.08770(15) 0.7813(8) 0.4230(3) 0.0380(10) Uani 1 1 d . U . . .
C19 C 0.09342(15) 0.7054(7) 0.6188(3) 0.0402(10) Uani 1 1 d . U . . .
C20 C 0.13137(16) 0.7951(8) 0.6811(3) 0.0506(11) Uani 1 1 d . U . . .
H20 H 0.1651 0.7161 0.6863 0.061 Uiso 1 1 calc R U . . .
C21 C 0.12085(17) 1.0003(8) 0.7365(3) 0.0530(12) Uani 1 1 d . U . . .
H21 H 0.1471 1.0627 0.7799 0.064 Uiso 1 1 calc R U . . .
C22 C 0.07186(17) 1.1133(8) 0.7278(3) 0.0497(11) Uani 1 1 d . U . . .
H22 H 0.0645 1.2536 0.7661 0.060 Uiso 1 1 calc R U . . .
C23 C 0.39409(17) 0.4840(9) 0.6122(4) 0.0609(12) Uani 1 1 d . 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
O1 C15 1.348(4) . ?
O1 C14 1.425(4) . ?
O2 C15 1.210(4) . ?
O3 C18 1.196(4) . ?
O4 C18 1.306(4) . ?
O4 H4 0.8400 . ?
N1 C15 1.332(4) . ?
N1 C16 1.441(4) . ?
N1 H1 0.8800 . ?
N2 C22 1.333(5) . ?
N2 C2 1.334(4) . ?
C1 C13 1.505(6) . ?
C1 C14 1.511(5) . ?
C1 C23 1.521(5) . ?
C1 H1A 1.0000 . ?
C2 C19 1.377(5) . ?
C2 H2 0.9500 . ?
C3 C23 1.364(6) . ?
C3 C4 1.394(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.367(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(6) . ?
C6 H6 0.9500 . ?
C7 C23 1.402(6) . ?
C7 C8 1.444(7) . ?
C8 C13 1.389(6) . ?
C8 C9 1.410(7) . ?
C9 C10 1.363(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.359(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C18 1.503(5) . ?
C16 C17 1.525(5) . ?
C16 H16 1.0000 . ?
C17 C19 1.502(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C20 1.368(5) . ?
C20 C21 1.382(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(5) . ?
C21 H21 0.9500 . ?
C22 H22 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
C15 O1 C14 115.7(3) . . ?
C18 O4 H4 109.5 . . ?
C15 N1 C16 118.5(3) . . ?
C15 N1 H1 120.7 . . ?
C16 N1 H1 120.7 . . ?
C22 N2 C2 117.9(4) . . ?
C13 C1 C14 112.9(3) . . ?
C13 C1 C23 101.8(4) . . ?
C14 C1 C23 107.6(3) . . ?
C13 C1 H1A 111.4 . . ?
C14 C1 H1A 111.4 . . ?
C23 C1 H1A 111.4 . . ?
N2 C2 C19 124.7(4) . . ?
N2 C2 H2 117.7 . . ?
C19 C2 H2 117.7 . . ?
C23 C3 C4 118.8(6) . . ?
C23 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.4(7) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C6 C5 C4 122.1(7) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 118.8(7) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C23 119.0(6) . . ?
C6 C7 C8 132.1(6) . . ?
C23 C7 C8 108.9(4) . . ?
C13 C8 C9 119.7(5) . . ?
C13 C8 C7 108.9(5) . . ?
C9 C8 C7 131.4(5) . . ?
C10 C9 C8 117.9(6) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 122.5(6) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.3(5) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C8 121.1(5) . . ?
C12 C13 C1 128.3(4) . . ?
C8 C13 C1 110.5(4) . . ?
O1 C14 C1 109.2(3) . . ?
O1 C14 H14A 109.8 . . ?
C1 C14 H14A 109.8 . . ?
O1 C14 H14B 109.8 . . ?
C1 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O2 C15 N1 125.2(4) . . ?
O2 C15 O1 123.7(4) . . ?
N1 C15 O1 111.1(3) . . ?
N1 C16 C18 109.8(3) . . ?
N1 C16 C17 113.1(3) . . ?
C18 C16 C17 113.0(3) . . ?
N1 C16 H16 106.8 . . ?
C18 C16 H16 106.8 . . ?
C17 C16 H16 106.8 . . ?
C19 C17 C16 114.6(3) . . ?
C19 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C19 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O3 C18 O4 124.5(4) . . ?
O3 C18 C16 124.6(4) . . ?
O4 C18 C16 110.9(3) . . ?
C20 C19 C2 116.5(4) . . ?
C20 C19 C17 122.3(4) . . ?
C2 C19 C17 121.2(4) . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
N2 C22 C21 121.6(4) . . ?
N2 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C3 C23 C7 121.9(5) . . ?
C3 C23 C1 128.5(5) . . ?
C7 C23 C1 109.4(4) . . ?

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
C22 N2 C2 C19 -1.6(6) . . . . ?
C23 C3 C4 C5 1.4(9) . . . . ?
C3 C4 C5 C6 -0.5(10) . . . . ?
C4 C5 C6 C7 -0.4(10) . . . . ?
C5 C6 C7 C23 0.3(8) . . . . ?
C5 C6 C7 C8 -178.2(5) . . . . ?
C6 C7 C8 C13 -180.0(5) . . . . ?
C23 C7 C8 C13 1.3(5) . . . . ?
C6 C7 C8 C9 -0.9(9) . . . . ?
C23 C7 C8 C9 -179.6(5) . . . . ?
C13 C8 C9 C10 0.0(8) . . . . ?
C7 C8 C9 C10 -179.0(5) . . . . ?
C8 C9 C10 C11 -1.3(9) . . . . ?
C9 C10 C11 C12 1.7(10) . . . . ?
C10 C11 C12 C13 -0.7(8) . . . . ?
C11 C12 C13 C8 -0.5(7) . . . . ?
C11 C12 C13 C1 175.8(5) . . . . ?
C9 C8 C13 C12 0.9(7) . . . . ?
C7 C8 C13 C12 -179.9(4) . . . . ?
C9 C8 C13 C1 -176.1(4) . . . . ?
C7 C8 C13 C1 3.2(5) . . . . ?
C14 C1 C13 C12 -67.6(6) . . . . ?
C23 C1 C13 C12 177.4(4) . . . . ?
C14 C1 C13 C8 109.1(4) . . . . ?
C23 C1 C13 C8 -5.9(5) . . . . ?
C15 O1 C14 C1 -140.7(4) . . . . ?
C13 C1 C14 O1 66.7(4) . . . . ?
C23 C1 C14 O1 178.3(3) . . . . ?
C16 N1 C15 O2 0.4(6) . . . . ?
C16 N1 C15 O1 -179.9(3) . . . . ?
C14 O1 C15 O2 3.6(6) . . . . ?
C14 O1 C15 N1 -176.0(3) . . . . ?
C15 N1 C16 C18 -153.5(3) . . . . ?
C15 N1 C16 C17 79.2(4) . . . . ?
N1 C16 C17 C19 64.6(4) . . . . ?
C18 C16 C17 C19 -61.0(4) . . . . ?
N1 C16 C18 O3 -0.9(5) . . . . ?
C17 C16 C18 O3 126.4(4) . . . . ?
N1 C16 C18 O4 177.6(3) . . . . ?
C17 C16 C18 O4 -55.1(4) . . . . ?
N2 C2 C19 C20 1.1(6) . . . . ?
N2 C2 C19 C17 -177.8(3) . . . . ?
C16 C17 C19 C20 -87.2(5) . . . . ?
C16 C17 C19 C2 91.5(4) . . . . ?
C2 C19 C20 C21 -0.1(6) . . . . ?
C17 C19 C20 C21 178.7(3) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C2 N2 C22 C21 1.2(6) . . . . ?
C20 C21 C22 N2 -0.4(6) . . . . ?
C4 C3 C23 C7 -1.6(7) . . . . ?
C4 C3 C23 C1 -175.8(4) . . . . ?
C6 C7 C23 C3 0.7(7) . . . . ?
C8 C7 C23 C3 179.5(4) . . . . ?
C6 C7 C23 C1 175.9(4) . . . . ?
C8 C7 C23 C1 -5.2(5) . . . . ?
C13 C1 C23 C3 -178.5(4) . . . . ?
C14 C1 C23 C3 62.6(6) . . . . ?
C13 C1 C23 C7 6.7(5) . . . . ?
C14 C1 C23 C7 -112.2(4) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_Vijayakanth11b
_database_code_depnum_ccdc_archive 'CCDC 2211503'
loop_
_audit_author_name
_audit_author_address
'Natalia Fridman'
;Technion Israel Institute of Technology
Israel
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Vijayakanth11b
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O4 [+ solvent]'
_chemical_formula_sum            'C23 H20 N2 O4 [+ solvent]'
_chemical_formula_weight         388.41

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.510(3)
_cell_length_b                   29.996(7)
_cell_length_c                   5.7849(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.787(7)
_cell_angle_gamma                90
_cell_volume                     2150.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3518
_cell_measurement_theta_min      1.643
_cell_measurement_theta_max      24.579

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            8168
_diffrn_reflns_av_unetI/netI     0.1153
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.643
_diffrn_reflns_theta_max         24.579
_diffrn_reflns_theta_full        24.579
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3518
_reflns_number_gt                1486
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.1094P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3518
_refine_ls_number_parameters     382
_refine_ls_number_restraints     737
_refine_ls_R_factor_all          0.1831
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.1873
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.916
_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
O1 O 0.4110(3) 0.42139(10) 0.7592(5) 0.0568(9) Uani 1 1 d . U . . .
O2 O 0.4790(3) 0.42927(12) 0.4200(5) 0.0672(11) Uani 1 1 d . U . . .
O3 O 0.0949(3) 0.42359(15) 0.2360(7) 0.0982(15) Uani 1 1 d . U . . .
O4 O 0.1372(3) 0.43423(14) -0.1210(6) 0.0775(12) Uani 1 1 d . U . . .
H4 H 0.0709 0.4302 -0.1623 0.116 Uiso 1 1 calc R U . . .
N1 N 0.2993(3) 0.43597(13) 0.4365(6) 0.0579(11) Uani 1 1 d . U . . .
H1 H 0.2480 0.4352 0.5267 0.070 Uiso 1 1 calc R U . . .
N2 N 0.0651(3) 0.56505(15) 0.2751(7) 0.0685(13) Uani 1 1 d . U . . .
C1 C 0.5074(13) 0.3544(4) 0.866(3) 0.063(4) Uani 0.534(18) 1 d D U P A 1
H1A H 0.4965 0.3433 0.7018 0.075 Uiso 0.534(18) 1 calc R U P A 1
C1A C 0.5300(14) 0.3549(4) 0.866(3) 0.056(4) Uani 0.466(18) 1 d D U P A 2
H1AA H 0.5165 0.3436 0.7018 0.068 Uiso 0.466(18) 1 calc R U P A 2
C2 C 0.4186(13) 0.3361(7) 0.999(3) 0.063(3) Uani 0.534(18) 1 d D U P A 1
C2A C 0.4557(15) 0.3311(8) 1.015(4) 0.069(4) Uani 0.466(18) 1 d D U P A 2
C3 C 0.3083(13) 0.3405(9) 0.947(4) 0.084(4) Uani 0.534(18) 1 d D U P A 1
H3 H 0.2773 0.3571 0.8144 0.101 Uiso 0.534(18) 1 calc R U P A 1
C3A C 0.3451(16) 0.3318(10) 0.994(4) 0.078(5) Uani 0.466(18) 1 d D U P A 2
H3A H 0.3038 0.3461 0.8650 0.094 Uiso 0.466(18) 1 calc R U P A 2
C4 C 0.2416(17) 0.3196(7) 1.098(3) 0.101(5) Uani 0.534(18) 1 d D U P A 1
H4A H 0.1651 0.3206 1.0655 0.122 Uiso 0.534(18) 1 calc R U P A 1
C4A C 0.2931(19) 0.3106(9) 1.171(4) 0.098(5) Uani 0.466(18) 1 d D U P A 2
H4AA H 0.2172 0.3123 1.1701 0.117 Uiso 0.466(18) 1 calc R U P A 2
C5 C 0.2946(18) 0.2974(6) 1.298(4) 0.102(5) Uani 0.534(18) 1 d D U P A 1
H5 H 0.2518 0.2861 1.4082 0.123 Uiso 0.534(18) 1 calc R U P A 1
C5A C 0.359(2) 0.2874(12) 1.346(5) 0.094(6) Uani 0.466(18) 1 d D U P A 2
H5A H 0.3255 0.2705 1.4558 0.113 Uiso 0.466(18) 1 calc R U P A 2
C6 C 0.4058(19) 0.2913(9) 1.341(4) 0.093(5) Uani 0.534(18) 1 d D U P A 1
H6 H 0.4385 0.2736 1.4677 0.112 Uiso 0.534(18) 1 calc R U P A 1
C6A C 0.4723(19) 0.2882(7) 1.367(3) 0.092(5) Uani 0.466(18) 1 d D U P A 2
H6A H 0.5151 0.2740 1.4938 0.110 Uiso 0.466(18) 1 calc R U P A 2
C7 C 0.4657(16) 0.3122(7) 1.191(3) 0.073(4) Uani 0.534(18) 1 d D U P A 1
C7A C 0.5197(17) 0.3100(9) 1.198(4) 0.069(4) Uani 0.466(18) 1 d D U P A 2
C8 C 0.5804(16) 0.3103(7) 1.188(3) 0.076(4) Uani 0.534(18) 1 d D U P A 1
C8A C 0.6335(17) 0.3158(7) 1.179(3) 0.074(4) Uani 0.466(18) 1 d D U P A 2
C9 C 0.6593(17) 0.2916(6) 1.343(3) 0.091(4) Uani 0.534(18) 1 d D U P A 1
H9 H 0.6421 0.2760 1.4763 0.109 Uiso 0.534(18) 1 calc R U P A 1
C9A C 0.7203(19) 0.2980(12) 1.308(5) 0.097(6) Uani 0.466(18) 1 d D U P A 2
H9A H 0.7142 0.2803 1.4417 0.116 Uiso 0.466(18) 1 calc R U P A 2
C10 C 0.7674(17) 0.2961(10) 1.301(4) 0.098(5) Uani 0.534(18) 1 d D U P A 1
H10 H 0.8237 0.2836 1.4080 0.117 Uiso 0.534(18) 1 calc R U P A 1
C10A C 0.8214(18) 0.3069(8) 1.233(4) 0.100(6) Uani 0.466(18) 1 d D U P A 2
H10A H 0.8851 0.2954 1.3208 0.120 Uiso 0.466(18) 1 calc R U P A 2
C11 C 0.7931(16) 0.3189(7) 1.101(3) 0.095(5) Uani 0.534(18) 1 d D U P A 1
H11 H 0.8660 0.3207 1.0724 0.114 Uiso 0.534(18) 1 calc R U P A 1
C11A C 0.8299(16) 0.3328(8) 1.030(4) 0.098(5) Uani 0.466(18) 1 d D U P A 2
H11A H 0.8986 0.3376 0.9813 0.118 Uiso 0.466(18) 1 calc R U P A 2
C12 C 0.7123(14) 0.3385(8) 0.948(4) 0.078(5) Uani 0.534(18) 1 d D U P A 1
H12 H 0.7283 0.3541 0.8141 0.094 Uiso 0.534(18) 1 calc R U P A 1
C12A C 0.7386(14) 0.3508(10) 0.902(4) 0.080(5) Uani 0.466(18) 1 d D U P A 2
H12A H 0.7430 0.3689 0.7694 0.096 Uiso 0.466(18) 1 calc R U P A 2
C13 C 0.6082(14) 0.3346(7) 0.996(4) 0.065(4) Uani 0.534(18) 1 d D U P A 1
C13A C 0.6408(15) 0.3413(9) 0.977(4) 0.064(4) Uani 0.466(18) 1 d D U P A 2
C14 C 0.5149(4) 0.40539(15) 0.8685(7) 0.0547(13) Uani 1 1 d D U . . .
H14A H 0.5304 0.4166 1.0306 0.066 Uiso 1 1 calc R U . A 1
H14B H 0.5729 0.4155 0.7804 0.066 Uiso 1 1 calc R U . A 1
C15 C 0.4013(4) 0.42890(15) 0.5250(8) 0.0489(12) Uani 1 1 d . U . . .
C16 C 0.2733(4) 0.44493(17) 0.1890(7) 0.0537(13) Uani 1 1 d . U . . .
H16 H 0.3207 0.4258 0.1044 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2943(4) 0.49393(16) 0.1293(7) 0.0589(14) Uani 1 1 d . U . . .
H17A H 0.3722 0.5003 0.1696 0.071 Uiso 1 1 calc R U . . .
H17B H 0.2753 0.4983 -0.0409 0.071 Uiso 1 1 calc R U . . .
C18 C 0.1581(4) 0.4322(2) 0.1080(9) 0.0685(15) Uani 1 1 d . U . . .
C19 C 0.2315(4) 0.52641(16) 0.2546(7) 0.0531(12) Uani 1 1 d . U . . .
C20 C 0.2716(4) 0.54391(18) 0.4715(8) 0.0620(14) Uani 1 1 d . U . . .
H20 H 0.3425 0.5364 0.5411 0.074 Uiso 1 1 calc R U . . .
C21 C 0.2097(5) 0.57212(19) 0.5869(9) 0.0720(15) Uani 1 1 d . U . . .
H21 H 0.2379 0.5850 0.7325 0.086 Uiso 1 1 calc R U . . .
C22 C 0.1045(5) 0.58128(18) 0.4838(9) 0.0728(16) Uani 1 1 d . U . . .
H22 H 0.0598 0.5996 0.5647 0.087 Uiso 1 1 calc R U . . .
C23 C 0.1282(4) 0.53828(18) 0.1653(8) 0.0623(14) Uani 1 1 d . U . . .
H23 H 0.0994 0.5269 0.0166 0.075 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
O1 C15 1.362(5) . ?
O1 C14 1.448(5) . ?
O2 C15 1.215(5) . ?
O3 C18 1.183(6) . ?
O4 C18 1.317(6) . ?
O4 H4 0.8400 . ?
N1 C15 1.326(6) . ?
N1 C16 1.450(5) . ?
N1 H1 0.8800 . ?
N2 C22 1.333(6) . ?
N2 C23 1.344(6) . ?
C1 C13 1.499(12) . ?
C1 C14 1.532(12) . ?
C1 C2 1.533(12) . ?
C1 H1A 1.0000 . ?
C1A C13A 1.503(13) . ?
C1A C14 1.526(12) . ?
C1A C2A 1.528(13) . ?
C1A H1AA 1.0000 . ?
C2 C3 1.379(13) . ?
C2 C7 1.387(13) . ?
C2A C3A 1.373(14) . ?
C2A C7A 1.391(15) . ?
C3 C4 1.432(13) . ?
C3 H3 0.9500 . ?
C3A C4A 1.436(15) . ?
C3A H3A 0.9500 . ?
C4 C5 1.419(18) . ?
C4 H4A 0.9500 . ?
C4A C5A 1.40(2) . ?
C4A H4AA 0.9500 . ?
C5 C6 1.39(2) . ?
C5 H5 0.9500 . ?
C5A C6A 1.41(2) . ?
C5A H5A 0.9500 . ?
C6 C7 1.373(16) . ?
C6 H6 0.9500 . ?
C6A C7A 1.373(16) . ?
C6A H6A 0.9500 . ?
C7 C8 1.437(16) . ?
C7A C8A 1.453(17) . ?
C8 C9 1.361(15) . ?
C8 C13 1.414(14) . ?
C8A C9A 1.342(17) . ?
C8A C13A 1.411(14) . ?
C9 C10 1.414(19) . ?
C9 H9 0.9500 . ?
C9A C10A 1.42(2) . ?
C9A H9A 0.9500 . ?
C10 C11 1.417(18) . ?
C10 H10 0.9500 . ?
C10A C11A 1.425(18) . ?
C10A H10A 0.9500 . ?
C11 C12 1.382(13) . ?
C11 H11 0.9500 . ?
C11A C12A 1.383(14) . ?
C11A H11A 0.9500 . ?
C12 C13 1.372(14) . ?
C12 H12 0.9500 . ?
C12A C13A 1.381(15) . ?
C12A H12A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C18 1.503(7) . ?
C16 C17 1.541(6) . ?
C16 H16 1.0000 . ?
C17 C19 1.498(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C23 1.373(6) . ?
C19 C20 1.390(6) . ?
C20 C21 1.379(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 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
C15 O1 C14 116.3(4) . . ?
C18 O4 H4 109.5 . . ?
C15 N1 C16 119.1(4) . . ?
C15 N1 H1 120.5 . . ?
C16 N1 H1 120.5 . . ?
C22 N2 C23 118.5(4) . . ?
C13 C1 C14 110.1(13) . . ?
C13 C1 C2 103.1(9) . . ?
C14 C1 C2 113.7(12) . . ?
C13 C1 H1A 109.9 . . ?
C14 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C13A C1A C14 111.9(14) . . ?
C13A C1A C2A 103.2(10) . . ?
C14 C1A C2A 111.8(14) . . ?
C13A C1A H1AA 109.9 . . ?
C14 C1A H1AA 109.9 . . ?
C2A C1A H1AA 109.9 . . ?
C3 C2 C7 121.9(11) . . ?
C3 C2 C1 128.9(10) . . ?
C7 C2 C1 109.2(11) . . ?
C3A C2A C7A 122.9(13) . . ?
C3A C2A C1A 128.7(12) . . ?
C7A C2A C1A 108.2(12) . . ?
C2 C3 C4 118.3(13) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C2A C3A C4A 118.6(15) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A H3A 120.7 . . ?
C5 C4 C3 117.1(14) . . ?
C5 C4 H4A 121.4 . . ?
C3 C4 H4A 121.4 . . ?
C5A C4A C3A 117.3(17) . . ?
C5A C4A H4AA 121.3 . . ?
C3A C4A H4AA 121.3 . . ?
C6 C5 C4 123.7(15) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C4A C5A C6A 122.5(16) . . ?
C4A C5A H5A 118.8 . . ?
C6A C5A H5A 118.8 . . ?
C7 C6 C5 116.3(17) . . ?
C7 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
C7A C6A C5A 118.5(16) . . ?
C7A C6A H6A 120.8 . . ?
C5A C6A H6A 120.8 . . ?
C6 C7 C2 122.3(14) . . ?
C6 C7 C8 128.3(14) . . ?
C2 C7 C8 109.1(11) . . ?
C6A C7A C2A 119.9(15) . . ?
C6A C7A C8A 129.3(14) . . ?
C2A C7A C8A 110.8(12) . . ?
C9 C8 C13 119.8(14) . . ?
C9 C8 C7 130.2(14) . . ?
C13 C8 C7 109.9(11) . . ?
C9A C8A C13A 122.5(16) . . ?
C9A C8A C7A 129.6(15) . . ?
C13A C8A C7A 107.6(11) . . ?
C8 C9 C10 118.2(14) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C8A C9A C10A 116.3(18) . . ?
C8A C9A H9A 121.8 . . ?
C10A C9A H9A 121.8 . . ?
C9 C10 C11 121.1(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C9A C10A C11A 121.7(15) . . ?
C9A C10A H10A 119.2 . . ?
C11A C10A H10A 119.2 . . ?
C12 C11 C10 120.0(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12A C11A C10A 120.2(15) . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C13 C12 C11 117.9(13) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C13A C12A C11A 117.2(14) . . ?
C13A C12A H12A 121.4 . . ?
C11A C12A H12A 121.4 . . ?
C12 C13 C8 122.9(12) . . ?
C12 C13 C1 128.6(11) . . ?
C8 C13 C1 108.5(11) . . ?
C12A C13A C8A 122.0(12) . . ?
C12A C13A C1A 128.0(11) . . ?
C8A C13A C1A 110.0(12) . . ?
O1 C14 C1A 115.4(7) . . ?
O1 C14 C1 106.1(7) . . ?
O1 C14 H14A 110.5 . . ?
C1 C14 H14A 110.5 . . ?
O1 C14 H14B 110.5 . . ?
C1 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O2 C15 N1 126.8(4) . . ?
O2 C15 O1 121.9(4) . . ?
N1 C15 O1 111.2(4) . . ?
N1 C16 C18 109.7(4) . . ?
N1 C16 C17 112.1(4) . . ?
C18 C16 C17 110.9(4) . . ?
N1 C16 H16 108.0 . . ?
C18 C16 H16 108.0 . . ?
C17 C16 H16 108.0 . . ?
C19 C17 C16 113.3(4) . . ?
C19 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C19 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O3 C18 O4 125.5(5) . . ?
O3 C18 C16 123.7(5) . . ?
O4 C18 C16 110.7(5) . . ?
C23 C19 C20 116.6(5) . . ?
C23 C19 C17 121.0(4) . . ?
C20 C19 C17 122.2(5) . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 118.2(5) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
N2 C22 C21 121.8(5) . . ?
N2 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
N2 C23 C19 124.1(4) . . ?
N2 C23 H23 117.9 . . ?
C19 C23 H23 117.9 . . ?

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
C13 C1 C2 C3 -175(3) . . . . ?
C14 C1 C2 C3 66(3) . . . . ?
C13 C1 C2 C7 5(2) . . . . ?
C14 C1 C2 C7 -114.4(17) . . . . ?
C13A C1A C2A C3A 180(3) . . . . ?
C14 C1A C2A C3A 59(3) . . . . ?
C13A C1A C2A C7A 4(3) . . . . ?
C14 C1A C2A C7A -116(2) . . . . ?
C7 C2 C3 C4 0(4) . . . . ?
C1 C2 C3 C4 179(2) . . . . ?
C7A C2A C3A C4A 1(5) . . . . ?
C1A C2A C3A C4A -173(3) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C2A C3A C4A C5A -5(4) . . . . ?
C3 C4 C5 C6 -7(3) . . . . ?
C3A C4A C5A C6A 7(5) . . . . ?
C4 C5 C6 C7 7(4) . . . . ?
C4A C5A C6A C7A -5(5) . . . . ?
C5 C6 C7 C2 -4(4) . . . . ?
C5 C6 C7 C8 -177(2) . . . . ?
C3 C2 C7 C6 0(4) . . . . ?
C1 C2 C7 C6 -179(2) . . . . ?
C3 C2 C7 C8 175(2) . . . . ?
C1 C2 C7 C8 -4(3) . . . . ?
C5A C6A C7A C2A 1(4) . . . . ?
C5A C6A C7A C8A 180(3) . . . . ?
C3A C2A C7A C6A 1(4) . . . . ?
C1A C2A C7A C6A 176(2) . . . . ?
C3A C2A C7A C8A -178(3) . . . . ?
C1A C2A C7A C8A -3(3) . . . . ?
C6 C7 C8 C9 -8(5) . . . . ?
C2 C7 C8 C9 178(2) . . . . ?
C6 C7 C8 C13 176(3) . . . . ?
C2 C7 C8 C13 2(3) . . . . ?
C6A C7A C8A C9A 7(5) . . . . ?
C2A C7A C8A C9A -174(3) . . . . ?
C6A C7A C8A C13A -179(3) . . . . ?
C2A C7A C8A C13A 0(3) . . . . ?
C13 C8 C9 C10 -2(3) . . . . ?
C7 C8 C9 C10 -178(3) . . . . ?
C13A C8A C9A C10A 1(5) . . . . ?
C7A C8A C9A C10A 175(3) . . . . ?
C8 C9 C10 C11 -1(4) . . . . ?
C8A C9A C10A C11A -1(5) . . . . ?
C9 C10 C11 C12 2(4) . . . . ?
C9A C10A C11A C12A 2(4) . . . . ?
C10 C11 C12 C13 -1(3) . . . . ?
C10A C11A C12A C13A -2(4) . . . . ?
C11 C12 C13 C8 -2(4) . . . . ?
C11 C12 C13 C1 177(2) . . . . ?
C9 C8 C13 C12 4(4) . . . . ?
C7 C8 C13 C12 -180(2) . . . . ?
C9 C8 C13 C1 -175(2) . . . . ?
C7 C8 C13 C1 1(3) . . . . ?
C14 C1 C13 C12 -61(3) . . . . ?
C2 C1 C13 C12 177(2) . . . . ?
C14 C1 C13 C8 118.2(18) . . . . ?
C2 C1 C13 C8 -3(2) . . . . ?
C11A C12A C13A C8A 2(4) . . . . ?
C11A C12A C13A C1A -177(3) . . . . ?
C9A C8A C13A C12A -2(4) . . . . ?
C7A C8A C13A C12A -177(3) . . . . ?
C9A C8A C13A C1A 178(3) . . . . ?
C7A C8A C13A C1A 3(3) . . . . ?
C14 C1A C13A C12A -64(3) . . . . ?
C2A C1A C13A C12A 175(3) . . . . ?
C14 C1A C13A C8A 116(2) . . . . ?
C2A C1A C13A C8A -5(3) . . . . ?
C15 O1 C14 C1A -87.0(9) . . . . ?
C15 O1 C14 C1 -92.4(8) . . . . ?
C13A C1A C14 O1 178.4(10) . . . . ?
C2A C1A C14 O1 -66.3(13) . . . . ?
C13 C1 C14 O1 -174.9(9) . . . . ?
C2 C1 C14 O1 -59.9(12) . . . . ?
C16 N1 C15 O2 0.5(8) . . . . ?
C16 N1 C15 O1 179.5(4) . . . . ?
C14 O1 C15 O2 -11.6(6) . . . . ?
C14 O1 C15 N1 169.3(4) . . . . ?
C15 N1 C16 C18 155.3(4) . . . . ?
C15 N1 C16 C17 -80.9(5) . . . . ?
N1 C16 C17 C19 -58.5(5) . . . . ?
C18 C16 C17 C19 64.5(5) . . . . ?
N1 C16 C18 O3 11.7(8) . . . . ?
C17 C16 C18 O3 -112.7(6) . . . . ?
N1 C16 C18 O4 -171.3(4) . . . . ?
C17 C16 C18 O4 64.3(5) . . . . ?
C16 C17 C19 C23 -86.2(5) . . . . ?
C16 C17 C19 C20 89.9(5) . . . . ?
C23 C19 C20 C21 -0.7(7) . . . . ?
C17 C19 C20 C21 -177.0(5) . . . . ?
C19 C20 C21 C22 2.3(8) . . . . ?
C23 N2 C22 C21 1.7(8) . . . . ?
C20 C21 C22 N2 -2.9(8) . . . . ?
C22 N2 C23 C19 0.0(8) . . . . ?
C20 C19 C23 N2 -0.5(8) . . . . ?
C17 C19 C23 N2 175.8(5) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.053




####################################################################### 
# 
# 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_Vijaykanth5b
_database_code_depnum_ccdc_archive 'CCDC 2211501'
loop_
_audit_author_name
_audit_author_address
'Natalia Fridman'
;Technion Israel Institute of Technology
Israel
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Vijaykanth5b
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9371(9)
_cell_length_b                   8.0769(15)
_cell_length_c                   48.489(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1933.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3194
_cell_measurement_theta_min      1.680
_cell_measurement_theta_max      24.492

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            17376
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         1.680
_diffrn_reflns_theta_max         24.492
_diffrn_reflns_theta_full        24.492
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3194
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.651
_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0366P)²+0.6827P] 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 829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
O1 O 0.3804(5) 0.5927(3) 0.63415(5) 0.0340(7) Uani 1 1 d . . . . .
O2 O 0.7647(5) 0.5318(4) 0.65725(5) 0.0419(8) Uani 1 1 d . . . . .
O3 O 0.0439(5) 0.5463(4) 0.72162(5) 0.0377(7) Uani 1 1 d . . . . .
O4 O 0.3236(5) 0.4041(4) 0.74886(5) 0.0370(7) Uani 1 1 d . . . . .
H4 H 0.2023 0.4204 0.7607 0.055 Uiso 1 1 calc R U . . .
N1 N 0.3507(6) 0.4960(4) 0.67678(6) 0.0285(8) Uani 1 1 d . . . . .
H1 H 0.1743 0.4986 0.6742 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0189(7) -0.0435(4) 0.71244(6) 0.0306(8) Uani 1 1 d . . . . .
C1 C 0.3923(8) 0.5762(5) 0.58459(7) 0.0315(9) Uani 1 1 d . . . . .
H1A H 0.2285 0.6473 0.5819 0.038 Uiso 1 1 calc R U . . .
C2 C 0.5809(8) 0.5910(5) 0.55998(8) 0.0350(10) Uani 1 1 d . . . . .
C3 C 0.7232(9) 0.7273(6) 0.55090(9) 0.0422(11) Uani 1 1 d . . . . .
H3 H 0.6990 0.8322 0.5594 0.051 Uiso 1 1 calc R U . . .
C4 C 0.9033(10) 0.7083(7) 0.52895(9) 0.0489(13) Uani 1 1 d . . . . .
H4A H 1.0037 0.8008 0.5225 0.059 Uiso 1 1 calc R U . . .
C5 C 0.9358(10) 0.5568(7) 0.51673(9) 0.0570(14) Uani 1 1 d . . . . .
H5 H 1.0599 0.5456 0.5019 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7933(10) 0.4206(7) 0.52546(9) 0.0526(13) Uani 1 1 d . . . . .
H6 H 0.8162 0.3165 0.5166 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6143(9) 0.4376(5) 0.54751(8) 0.0382(10) Uani 1 1 d . . . . .
C8 C 0.4458(9) 0.3171(5) 0.56183(9) 0.0386(11) Uani 1 1 d . . . . .
C9 C 0.3992(12) 0.1523(6) 0.55644(10) 0.0557(14) Uani 1 1 d . . . . .
H9 H 0.4866 0.0992 0.5414 0.067 Uiso 1 1 calc R U . . .
C10 C 0.2236(11) 0.0649(6) 0.57319(11) 0.0605(14) Uani 1 1 d . . . . .
H10 H 0.1909 -0.0490 0.5696 0.073 Uiso 1 1 calc R U . . .
C11 C 0.0954(11) 0.1413(6) 0.59500(11) 0.0530(13) Uani 1 1 d . . . . .
H11 H -0.0252 0.0795 0.6063 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1404(10) 0.3080(6) 0.60071(9) 0.0442(12) Uani 1 1 d . . . . .
H12 H 0.0535 0.3607 0.6158 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3149(8) 0.3944(5) 0.58377(8) 0.0342(10) Uani 1 1 d . . . . .
C14 C 0.5441(9) 0.6284(5) 0.61032(8) 0.0378(11) Uani 1 1 d . . . . .
H14A H 0.7179 0.5677 0.6115 0.045 Uiso 1 1 calc R U . . .
H14B H 0.5842 0.7484 0.6095 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5181(8) 0.5391(5) 0.65656(8) 0.0299(9) Uani 1 1 d . . . . .
C16 C 0.4612(7) 0.4445(5) 0.70320(7) 0.0271(9) Uani 1 1 d . . . . .
H16 H 0.6154 0.5206 0.7075 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2505(8) 0.4696(5) 0.72545(8) 0.0258(9) Uani 1 1 d . . . . .
C18 C 0.5763(7) 0.2682(5) 0.70249(9) 0.0334(10) Uani 1 1 d . . . . .
H18A H 0.7217 0.2635 0.6885 0.040 Uiso 1 1 calc R U . . .
H18B H 0.6593 0.2436 0.7206 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3717(8) 0.1363(5) 0.69612(8) 0.0294(9) Uani 1 1 d . . . . .
C20 C 0.3374(9) 0.0709(5) 0.67005(8) 0.0400(11) Uani 1 1 d . . . . .
H20 H 0.4434 0.1111 0.6551 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1492(10) -0.0533(6) 0.66558(9) 0.0493(12) Uani 1 1 d . . . . .
H21 H 0.1275 -0.0999 0.6477 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0056(9) -0.1084(5) 0.68720(8) 0.0389(11) Uani 1 1 d . . . . .
H22 H -0.1330 -0.1947 0.6842 0.047 Uiso 1 1 calc R U . . .
C23 C 0.2066(7) 0.0731(5) 0.71668(8) 0.0288(9) Uani 1 1 d . . . . .
H23 H 0.2280 0.1150 0.7349 0.035 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
O1 C15 1.353(5) . ?
O1 C14 1.439(4) . ?
O2 C15 1.219(5) . ?
O3 C17 1.207(5) . ?
O4 C17 1.304(4) . ?
O4 H4 0.8400 . ?
N1 C15 1.329(5) . ?
N1 C16 1.453(5) . ?
N1 H1 0.8800 . ?
N2 C23 1.337(5) . ?
N2 C22 1.337(5) . ?
C1 C14 1.515(5) . ?
C1 C13 1.518(6) . ?
C1 C2 1.518(5) . ?
C1 H1A 1.0000 . ?
C2 C3 1.378(6) . ?
C2 C7 1.388(6) . ?
C3 C4 1.396(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.373(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.456(6) . ?
C8 C9 1.376(6) . ?
C8 C13 1.393(6) . ?
C9 C10 1.381(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(6) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C17 1.512(5) . ?
C16 C18 1.534(5) . ?
C16 H16 1.0000 . ?
C18 C19 1.500(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.381(5) . ?
C19 C23 1.385(5) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 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
C15 O1 C14 115.3(3) . . ?
C17 O4 H4 109.5 . . ?
C15 N1 C16 119.4(3) . . ?
C15 N1 H1 120.3 . . ?
C16 N1 H1 120.3 . . ?
C23 N2 C22 118.7(4) . . ?
C14 C1 C13 114.5(3) . . ?
C14 C1 C2 108.8(3) . . ?
C13 C1 C2 102.1(3) . . ?
C14 C1 H1A 110.4 . . ?
C13 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
C3 C2 C7 120.9(4) . . ?
C3 C2 C1 128.8(4) . . ?
C7 C2 C1 110.2(4) . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 118.8(5) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 119.8(4) . . ?
C2 C7 C8 108.7(4) . . ?
C6 C7 C8 131.4(4) . . ?
C9 C8 C13 120.1(5) . . ?
C9 C8 C7 130.7(5) . . ?
C13 C8 C7 109.2(4) . . ?
C8 C9 C10 119.2(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 118.1(5) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C8 121.2(4) . . ?
C12 C13 C1 129.1(4) . . ?
C8 C13 C1 109.7(4) . . ?
O1 C14 C1 109.1(3) . . ?
O1 C14 H14A 109.9 . . ?
C1 C14 H14A 109.9 . . ?
O1 C14 H14B 109.9 . . ?
C1 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O2 C15 N1 126.0(4) . . ?
O2 C15 O1 122.6(4) . . ?
N1 C15 O1 111.3(3) . . ?
N1 C16 C17 109.4(3) . . ?
N1 C16 C18 112.7(3) . . ?
C17 C16 C18 113.3(3) . . ?
N1 C16 H16 107.0 . . ?
C17 C16 H16 107.0 . . ?
C18 C16 H16 107.0 . . ?
O3 C17 O4 125.2(4) . . ?
O3 C17 C16 122.7(3) . . ?
O4 C17 C16 112.1(3) . . ?
C19 C18 C16 114.5(3) . . ?
C19 C18 H18A 108.6 . . ?
C16 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C16 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C23 116.5(4) . . ?
C20 C19 C18 122.9(4) . . ?
C23 C19 C18 120.6(4) . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
N2 C22 C21 121.5(4) . . ?
N2 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
N2 C23 C19 123.8(4) . . ?
N2 C23 H23 118.1 . . ?
C19 C23 H23 118.1 . . ?

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
C14 C1 C2 C3 -56.0(5) . . . . ?
C13 C1 C2 C3 -177.4(4) . . . . ?
C14 C1 C2 C7 119.5(4) . . . . ?
C13 C1 C2 C7 -2.0(4) . . . . ?
C7 C2 C3 C4 -0.3(6) . . . . ?
C1 C2 C3 C4 174.7(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C1 C2 C7 C6 -176.0(4) . . . . ?
C3 C2 C7 C8 178.3(4) . . . . ?
C1 C2 C7 C8 2.5(5) . . . . ?
C5 C6 C7 C2 0.7(6) . . . . ?
C5 C6 C7 C8 -177.4(4) . . . . ?
C2 C7 C8 C9 176.3(5) . . . . ?
C6 C7 C8 C9 -5.4(8) . . . . ?
C2 C7 C8 C13 -2.0(5) . . . . ?
C6 C7 C8 C13 176.3(4) . . . . ?
C13 C8 C9 C10 -0.6(7) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C11 C12 C13 0.6(7) . . . . ?
C11 C12 C13 C8 -0.9(6) . . . . ?
C11 C12 C13 C1 177.6(4) . . . . ?
C9 C8 C13 C12 1.0(6) . . . . ?
C7 C8 C13 C12 179.5(4) . . . . ?
C9 C8 C13 C1 -177.9(4) . . . . ?
C7 C8 C13 C1 0.7(5) . . . . ?
C14 C1 C13 C12 64.6(6) . . . . ?
C2 C1 C13 C12 -178.0(4) . . . . ?
C14 C1 C13 C8 -116.7(4) . . . . ?
C2 C1 C13 C8 0.7(4) . . . . ?
C15 O1 C14 C1 142.9(3) . . . . ?
C13 C1 C14 O1 -58.4(5) . . . . ?
C2 C1 C14 O1 -171.9(3) . . . . ?
C16 N1 C15 O2 4.2(6) . . . . ?
C16 N1 C15 O1 -176.3(3) . . . . ?
C14 O1 C15 O2 4.7(6) . . . . ?
C14 O1 C15 N1 -174.8(3) . . . . ?
C15 N1 C16 C17 156.9(3) . . . . ?
C15 N1 C16 C18 -76.1(4) . . . . ?
N1 C16 C17 O3 -11.1(5) . . . . ?
C18 C16 C17 O3 -137.7(4) . . . . ?
N1 C16 C17 O4 170.9(3) . . . . ?
C18 C16 C17 O4 44.3(4) . . . . ?
N1 C16 C18 C19 -62.3(4) . . . . ?
C17 C16 C18 C19 62.6(5) . . . . ?
C16 C18 C19 C20 98.0(5) . . . . ?
C16 C18 C19 C23 -82.4(5) . . . . ?
C23 C19 C20 C21 -1.1(6) . . . . ?
C18 C19 C20 C21 178.6(4) . . . . ?
C19 C20 C21 C22 1.1(6) . . . . ?
C23 N2 C22 C21 -2.7(6) . . . . ?
C20 C21 C22 N2 0.8(6) . . . . ?
C22 N2 C23 C19 2.8(5) . . . . ?
C20 C19 C23 N2 -0.9(6) . . . . ?
C18 C19 C23 N2 179.5(3) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043



