# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

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

data_KA781_0m
_database_code_depnum_ccdc_archive 'CCDC 2065302'
loop_
_audit_author_name
_audit_author_address
'NAGENDER THADEM'
;CSIR Indian Institute of Chemical Technology 
India
;
_audit_update_record             
;
2021-02-26 deposited with the CCDC.	2021-09-02 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         'C28 H21 N3 O2'
_chemical_formula_sum            'C28 H21 N3 O2'
_chemical_formula_weight         431.48

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   10.5012(10)
_cell_length_b                   21.4163(19)
_cell_length_c                   10.7561(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.366(3)
_cell_angle_gamma                90
_cell_volume                     2167.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7153
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31296
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6275
_reflns_number_gt                5689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.972

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²+0.3115P] 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 2368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6275
_refine_ls_number_parameters     298
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.016
_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
C1 C 0.3594(3) 0.67025(9) 0.2687(2) 0.0510(5) Uani 1 1 d . . . . .
C2 C 0.4886(3) 0.68201(9) 0.2623(2) 0.0530(5) Uani 1 1 d . . . . .
C3 C 0.4947(5) 0.73260(13) 0.1795(3) 0.0817(10) Uani 1 1 d . . . . .
H3 H 0.578791 0.741336 0.173863 0.098 Uiso 1 1 calc R U . . .
C4 C 0.3768(6) 0.76827(14) 0.1083(4) 0.1017(14) Uani 1 1 d . . . . .
H4 H 0.381388 0.801370 0.054517 0.122 Uiso 1 1 calc R U . . .
C5 C 0.2499(6) 0.75611(15) 0.1147(4) 0.0983(14) Uani 1 1 d . . . . .
H5 H 0.171170 0.781223 0.065478 0.118 Uiso 1 1 calc R U . . .
C6 C 0.2393(4) 0.70762(13) 0.1926(3) 0.0743(9) Uani 1 1 d . . . . .
H6 H 0.153545 0.699441 0.195227 0.089 Uiso 1 1 calc R U . . .
C7 C 0.4606(2) 0.58878(8) 0.41317(17) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.5899(2) 0.59966(9) 0.40378(18) 0.0384(4) Uani 1 1 d . . . . .
C9 C 0.47536(17) 0.53269(8) 0.50586(15) 0.0301(3) Uani 1 1 d . . . . .
C10 C 0.62790(18) 0.51267(9) 0.54544(17) 0.0352(3) Uani 1 1 d . . . . .
C11 C 0.6919(2) 0.55292(10) 0.48644(19) 0.0396(4) Uani 1 1 d . . . . .
C12 C 0.7074(2) 0.46543(11) 0.6342(2) 0.0459(4) Uani 1 1 d . . . . .
H12 H 0.666997 0.439002 0.675498 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8488(2) 0.45838(14) 0.6603(2) 0.0582(6) Uani 1 1 d . . . . .
H13 H 0.903170 0.426720 0.719089 0.070 Uiso 1 1 calc R U . . .
C14 C 0.9097(2) 0.49806(16) 0.5996(3) 0.0634(7) Uani 1 1 d . . . . .
H14 H 1.004282 0.492335 0.618076 0.076 Uiso 1 1 calc R U . . .
C15 C 0.8334(2) 0.54551(14) 0.5128(2) 0.0562(6) Uani 1 1 d . . . . .
H15 H 0.874921 0.571998 0.472786 0.067 Uiso 1 1 calc R U . . .
C16 C 0.23294(19) 0.50624(8) 0.44081(18) 0.0355(3) Uani 1 1 d . . . . .
H16 H 0.169311 0.529861 0.358524 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1613(2) 0.44482(10) 0.4482(3) 0.0490(5) Uani 1 1 d . . . . .
H17A H 0.170711 0.437888 0.541059 0.059 Uiso 1 1 calc R U . . .
H17B H 0.061135 0.445147 0.383363 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2404(3) 0.39477(10) 0.4093(2) 0.0491(5) Uani 1 1 d . . . . .
H18A H 0.237622 0.354757 0.450258 0.059 Uiso 1 1 calc R U . . .
H18B H 0.201834 0.390119 0.309415 0.059 Uiso 1 1 calc R U . . .
C19 C 0.3894(2) 0.42130(8) 0.4710(2) 0.0405(4) Uani 1 1 d . . . . .
H19A H 0.435291 0.417740 0.571332 0.049 Uiso 1 1 calc R U . . .
H19B H 0.447435 0.400653 0.433933 0.049 Uiso 1 1 calc R U . . .
C20 C 0.44701(18) 0.54912(7) 0.63265(16) 0.0305(3) Uani 1 1 d . . . . .
H20 H 0.481600 0.513995 0.697602 0.037 Uiso 1 1 calc R U . . .
C21 C 0.28493(19) 0.54899(8) 0.57123(18) 0.0335(3) Uani 1 1 d . . . . .
H21 H 0.258817 0.528837 0.638453 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2129(2) 0.61197(9) 0.5361(2) 0.0430(4) Uani 1 1 d . . . . .
C23 C 0.4305(3) 0.65928(9) 0.7002(2) 0.0454(4) Uani 1 1 d . . . . .
C24 C 0.5131(2) 0.60709(9) 0.71287(17) 0.0378(4) Uani 1 1 d . . . . .
C25 C 0.4842(3) 0.71161(11) 0.7843(3) 0.0619(7) Uani 1 1 d . . . . .
H25 H 0.426145 0.745828 0.775120 0.074 Uiso 1 1 calc R U . . .
C26 C 0.6235(4) 0.71190(13) 0.8804(3) 0.0747(9) Uani 1 1 d . . . . .
H26 H 0.660700 0.746649 0.936880 0.090 Uiso 1 1 calc R U . . .
C27 C 0.7090(3) 0.66132(15) 0.8943(3) 0.0690(8) Uani 1 1 d . . . . .
H27 H 0.803770 0.662158 0.959763 0.083 Uiso 1 1 calc R U . . .
C28 C 0.6552(3) 0.60898(12) 0.8115(2) 0.0529(5) Uani 1 1 d . . . . .
H28 H 0.714106 0.574967 0.821771 0.063 Uiso 1 1 calc R U . . .
O1 O 0.28728(17) 0.66280(7) 0.60552(17) 0.0503(4) Uani 1 1 d . . . . .
O2 O 0.09054(18) 0.61978(9) 0.4570(2) 0.0615(5) Uani 1 1 d . . . . .
N1 N 0.3459(2) 0.62219(8) 0.34806(17) 0.0432(4) Uani 1 1 d . . . . .
N2 N 0.6071(2) 0.64524(9) 0.33081(18) 0.0513(5) Uani 1 1 d . . . . .
N3 N 0.36317(16) 0.48714(7) 0.42663(14) 0.0325(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.384(2) . ?
C1 C6 1.408(4) . ?
C1 C2 1.412(4) . ?
C2 N2 1.378(3) . ?
C2 C3 1.422(3) . ?
C3 C4 1.365(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.306(3) . ?
C7 C8 1.424(3) . ?
C7 C9 1.524(2) . ?
C8 N2 1.314(2) . ?
C8 C11 1.447(3) . ?
C9 N3 1.475(2) . ?
C9 C10 1.525(2) . ?
C9 C20 1.560(2) . ?
C10 C12 1.387(3) . ?
C10 C11 1.406(3) . ?
C11 C15 1.392(3) . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.499(2) . ?
C16 C17 1.535(3) . ?
C16 C21 1.557(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.514(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.475(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C24 1.495(2) . ?
C20 C21 1.528(2) . ?
C20 H20 0.9800 . ?
C21 C22 1.510(3) . ?
C21 H21 0.9800 . ?
C22 O2 1.196(3) . ?
C22 O1 1.355(3) . ?
C23 C24 1.384(3) . ?
C23 C25 1.392(3) . ?
C23 O1 1.395(3) . ?
C24 C28 1.396(3) . ?
C25 C26 1.366(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9300 . ?
C28 H28 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
N1 C1 C6 118.1(2) . . ?
N1 C1 C2 121.8(2) . . ?
C6 C1 C2 120.1(2) . . ?
N2 C2 C1 122.10(17) . . ?
N2 C2 C3 119.3(3) . . ?
C1 C2 C3 118.6(3) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 123.63(17) . . ?
N1 C7 C9 125.74(16) . . ?
C8 C7 C9 110.62(16) . . ?
N2 C8 C7 123.5(2) . . ?
N2 C8 C11 128.3(2) . . ?
C7 C8 C11 108.20(15) . . ?
N3 C9 C7 108.68(13) . . ?
N3 C9 C10 116.48(14) . . ?
C7 C9 C10 101.14(14) . . ?
N3 C9 C20 103.93(13) . . ?
C7 C9 C20 113.00(13) . . ?
C10 C9 C20 113.83(13) . . ?
C12 C10 C11 119.71(18) . . ?
C12 C10 C9 129.33(17) . . ?
C11 C10 C9 110.80(15) . . ?
C15 C11 C10 121.3(2) . . ?
C15 C11 C8 129.5(2) . . ?
C10 C11 C8 109.22(16) . . ?
C10 C12 C13 118.7(2) . . ?
C10 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C11 118.2(2) . . ?
C14 C15 H15 120.9 . . ?
C11 C15 H15 120.9 . . ?
N3 C16 C17 105.19(15) . . ?
N3 C16 C21 106.35(14) . . ?
C17 C16 C21 116.16(16) . . ?
N3 C16 H16 109.6 . . ?
C17 C16 H16 109.6 . . ?
C21 C16 H16 109.6 . . ?
C18 C17 C16 104.39(17) . . ?
C18 C17 H17A 110.9 . . ?
C16 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C19 C18 C17 101.48(16) . . ?
C19 C18 H18A 111.5 . . ?
C17 C18 H18A 111.5 . . ?
C19 C18 H18B 111.5 . . ?
C17 C18 H18B 111.5 . . ?
H18A C18 H18B 109.3 . . ?
N3 C19 C18 102.04(17) . . ?
N3 C19 H19A 111.4 . . ?
C18 C19 H19A 111.4 . . ?
N3 C19 H19B 111.4 . . ?
C18 C19 H19B 111.4 . . ?
H19A C19 H19B 109.2 . . ?
C24 C20 C21 113.16(15) . . ?
C24 C20 C9 118.16(14) . . ?
C21 C20 C9 103.30(13) . . ?
C24 C20 H20 107.2 . . ?
C21 C20 H20 107.2 . . ?
C9 C20 H20 107.2 . . ?
C22 C21 C20 116.40(15) . . ?
C22 C21 C16 111.31(15) . . ?
C20 C21 C16 105.56(14) . . ?
C22 C21 H21 107.7 . . ?
C20 C21 H21 107.7 . . ?
C16 C21 H21 107.7 . . ?
O2 C22 O1 116.99(19) . . ?
O2 C22 C21 124.3(2) . . ?
O1 C22 C21 118.53(17) . . ?
C24 C23 C25 122.1(2) . . ?
C24 C23 O1 122.75(18) . . ?
C25 C23 O1 115.2(2) . . ?
C23 C24 C28 117.6(2) . . ?
C23 C24 C20 120.27(17) . . ?
C28 C24 C20 121.89(19) . . ?
C26 C25 C23 118.9(3) . . ?
C26 C25 H25 120.5 . . ?
C23 C25 H25 120.5 . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C24 120.3(3) . . ?
C27 C28 H28 119.8 . . ?
C24 C28 H28 119.8 . . ?
C22 O1 C23 122.01(15) . . ?
C7 N1 C1 114.55(19) . . ?
C8 N2 C2 114.4(2) . . ?
C9 N3 C19 117.32(14) . . ?
C9 N3 C16 106.95(13) . . ?
C19 N3 C16 106.02(14) . . ?

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
N1 C1 C2 N2 2.1(3) . . . . ?
C6 C1 C2 N2 -177.6(2) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
N2 C2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
N1 C1 C6 C5 179.0(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
N1 C7 C8 N2 1.4(3) . . . . ?
C9 C7 C8 N2 -179.81(16) . . . . ?
N1 C7 C8 C11 -178.61(16) . . . . ?
C9 C7 C8 C11 0.14(19) . . . . ?
N1 C7 C9 N3 54.7(2) . . . . ?
C8 C7 C9 N3 -124.05(15) . . . . ?
N1 C7 C9 C10 177.78(17) . . . . ?
C8 C7 C9 C10 -0.94(17) . . . . ?
N1 C7 C9 C20 -60.2(2) . . . . ?
C8 C7 C9 C20 121.13(15) . . . . ?
N3 C9 C10 C12 -65.7(2) . . . . ?
C7 C9 C10 C12 176.75(19) . . . . ?
C20 C9 C10 C12 55.3(3) . . . . ?
N3 C9 C10 C11 119.02(16) . . . . ?
C7 C9 C10 C11 1.45(18) . . . . ?
C20 C9 C10 C11 -120.04(16) . . . . ?
C12 C10 C11 C15 1.5(3) . . . . ?
C9 C10 C11 C15 177.28(18) . . . . ?
C12 C10 C11 C8 -177.28(17) . . . . ?
C9 C10 C11 C8 -1.5(2) . . . . ?
N2 C8 C11 C15 2.2(3) . . . . ?
C7 C8 C11 C15 -177.8(2) . . . . ?
N2 C8 C11 C10 -179.23(18) . . . . ?
C7 C8 C11 C10 0.82(19) . . . . ?
C11 C10 C12 C13 -1.3(3) . . . . ?
C9 C10 C12 C13 -176.27(19) . . . . ?
C10 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C11 -0.2(4) . . . . ?
C10 C11 C15 C14 -0.7(3) . . . . ?
C8 C11 C15 C14 177.8(2) . . . . ?
N3 C16 C17 C18 -10.8(2) . . . . ?
C21 C16 C17 C18 -128.04(18) . . . . ?
C16 C17 C18 C19 34.3(2) . . . . ?
C17 C18 C19 N3 -45.54(19) . . . . ?
N3 C9 C20 C24 -162.52(14) . . . . ?
C7 C9 C20 C24 -44.9(2) . . . . ?
C10 C9 C20 C24 69.76(19) . . . . ?
N3 C9 C20 C21 -36.72(15) . . . . ?
C7 C9 C20 C21 80.92(16) . . . . ?
C10 C9 C20 C21 -164.44(14) . . . . ?
C24 C20 C21 C22 29.1(2) . . . . ?
C9 C20 C21 C22 -99.85(17) . . . . ?
C24 C20 C21 C16 153.11(13) . . . . ?
C9 C20 C21 C16 24.16(16) . . . . ?
N3 C16 C21 C22 123.57(15) . . . . ?
C17 C16 C21 C22 -119.79(18) . . . . ?
N3 C16 C21 C20 -3.59(17) . . . . ?
C17 C16 C21 C20 113.05(17) . . . . ?
C20 C21 C22 O2 159.9(2) . . . . ?
C16 C21 C22 O2 38.9(3) . . . . ?
C20 C21 C22 O1 -25.3(2) . . . . ?
C16 C21 C22 O1 -146.36(17) . . . . ?
C25 C23 C24 C28 -1.6(3) . . . . ?
O1 C23 C24 C28 -179.94(19) . . . . ?
C25 C23 C24 C20 172.61(19) . . . . ?
O1 C23 C24 C20 -5.7(3) . . . . ?
C21 C20 C24 C23 -14.6(2) . . . . ?
C9 C20 C24 C23 106.25(19) . . . . ?
C21 C20 C24 C28 159.38(17) . . . . ?
C9 C20 C24 C28 -79.8(2) . . . . ?
C24 C23 C25 C26 1.3(3) . . . . ?
O1 C23 C25 C26 179.7(2) . . . . ?
C23 C25 C26 C27 -0.3(4) . . . . ?
C25 C26 C27 C28 -0.3(5) . . . . ?
C26 C27 C28 C24 0.0(4) . . . . ?
C23 C24 C28 C27 1.0(3) . . . . ?
C20 C24 C28 C27 -173.1(2) . . . . ?
O2 C22 O1 C23 180.0(2) . . . . ?
C21 C22 O1 C23 4.9(3) . . . . ?
C24 C23 O1 C22 11.5(3) . . . . ?
C25 C23 O1 C22 -166.93(19) . . . . ?
C8 C7 N1 C1 -0.6(3) . . . . ?
C9 C7 N1 C1 -179.14(16) . . . . ?
C6 C1 N1 C7 178.6(2) . . . . ?
C2 C1 N1 C7 -1.1(3) . . . . ?
C7 C8 N2 C2 -0.4(3) . . . . ?
C11 C8 N2 C2 179.62(17) . . . . ?
C1 C2 N2 C8 -1.2(3) . . . . ?
C3 C2 N2 C8 -179.7(2) . . . . ?
C7 C9 N3 C19 155.86(15) . . . . ?
C10 C9 N3 C19 42.5(2) . . . . ?
C20 C9 N3 C19 -83.55(17) . . . . ?
C7 C9 N3 C16 -85.31(16) . . . . ?
C10 C9 N3 C16 161.34(13) . . . . ?
C20 C9 N3 C16 35.28(16) . . . . ?
C18 C19 N3 C9 159.04(15) . . . . ?
C18 C19 N3 C16 39.71(18) . . . . ?
C17 C16 N3 C9 -143.79(15) . . . . ?
C21 C16 N3 C9 -20.03(17) . . . . ?
C17 C16 N3 C19 -17.87(19) . . . . ?
C21 C16 N3 C19 105.90(15) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_KA802_0m
_database_code_depnum_ccdc_archive 'CCDC 2065303'
loop_
_audit_author_name
_audit_author_address
'NAGENDER THADEM'
;CSIR Indian Institute of Chemical Technology 
India
;
_audit_update_record             
;
2021-02-26 deposited with the CCDC.	2021-09-02 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         'C25 H25 N3 O3'
_chemical_formula_sum            'C25 H25 N3 O3'
_chemical_formula_weight         415.48

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                   10.5361(2)
_cell_length_b                   20.5984(4)
_cell_length_c                   9.9179(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2152.45(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5100
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15870
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             5861
_reflns_number_gt                3152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.774
_reflns_Friedel_fraction_full    0.815

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)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 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5861
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.0316(3) 0.44785(15) 0.7805(4) 0.0467(9) Uani 1 1 d . . . . .
C2 C 0.0969(4) 0.4078(2) 0.8665(5) 0.0769(13) Uani 1 1 d . . . . .
H2 H 0.184943 0.405931 0.861792 0.092 Uiso 1 1 calc R U . . .
C3 C 0.0331(5) 0.3704(3) 0.9600(5) 0.0983(18) Uani 1 1 d . . . . .
H3 H 0.078913 0.343966 1.018487 0.118 Uiso 1 1 calc R U . . .
C4 C -0.0951(5) 0.3716(2) 0.9676(5) 0.0808(14) Uani 1 1 d . . . . .
H4 H -0.137339 0.345790 1.030119 0.097 Uiso 1 1 calc R U . . .
C5 C -0.1611(4) 0.4106(2) 0.8838(5) 0.0717(12) Uani 1 1 d . . . . .
H5 H -0.249169 0.411662 0.888903 0.086 Uiso 1 1 calc R U . . .
C6 C -0.0992(4) 0.44903(18) 0.7904(4) 0.0581(10) Uani 1 1 d . . . . .
H6 H -0.145932 0.475882 0.733662 0.070 Uiso 1 1 calc R U . . .
C7 C 0.0994(3) 0.48893(15) 0.6785(4) 0.0538(9) Uani 1 1 d . . . . .
H7A H 0.037156 0.512338 0.625279 0.065 Uiso 1 1 calc R U . . .
H7B H 0.151193 0.520674 0.725281 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1343(3) 0.40605(15) 0.4931(3) 0.0427(8) Uani 1 1 d . . . . .
C9 C 0.2348(3) 0.37452(14) 0.4314(3) 0.0377(7) Uani 1 1 d . . . . .
C10 C 0.3576(3) 0.40309(14) 0.4822(3) 0.0389(7) Uani 1 1 d . . . . .
C11 C 0.3091(3) 0.44942(15) 0.5937(4) 0.0436(8) Uani 1 1 d . . . . .
C12 C 0.0101(3) 0.39070(18) 0.4620(4) 0.0583(10) Uani 1 1 d . . . . .
H12 H -0.057519 0.412621 0.501547 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0098(4) 0.3414(2) 0.3696(4) 0.0648(11) Uani 1 1 d . . . . .
H13 H -0.092429 0.330694 0.345313 0.078 Uiso 1 1 calc R U . . .
C14 C 0.0890(4) 0.30788(19) 0.3129(4) 0.0603(10) Uani 1 1 d . . . . .
H14 H 0.072527 0.273925 0.253639 0.072 Uiso 1 1 calc R U . . .
C15 C 0.2134(3) 0.32430(16) 0.3434(3) 0.0458(8) Uani 1 1 d . . . . .
H15 H 0.280874 0.301763 0.305058 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5745(3) 0.38384(16) 0.5308(3) 0.0417(7) Uani 1 1 d . . . . .
H16 H 0.576331 0.414965 0.605490 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6564(4) 0.32580(18) 0.5669(4) 0.0549(9) Uani 1 1 d . . . . .
H17A H 0.732838 0.339166 0.613698 0.066 Uiso 1 1 calc R U . . .
H17B H 0.679689 0.301301 0.487101 0.066 Uiso 1 1 calc R U . . .
C18 C 0.5694(4) 0.2861(2) 0.6593(4) 0.0656(11) Uani 1 1 d . . . . .
H18A H 0.596367 0.290105 0.752433 0.079 Uiso 1 1 calc R U . . .
H18B H 0.571510 0.240576 0.634244 0.079 Uiso 1 1 calc R U . . .
C19 C 0.4350(4) 0.31380(18) 0.6411(4) 0.0585(10) Uani 1 1 d . . . . .
H19A H 0.373654 0.279537 0.625352 0.070 Uiso 1 1 calc R U . . .
H19B H 0.409173 0.338881 0.719162 0.070 Uiso 1 1 calc R U . . .
C20 C 0.4392(3) 0.44442(14) 0.3799(3) 0.0407(8) Uani 1 1 d . . . . .
H20 H 0.431713 0.490962 0.398782 0.049 Uiso 1 1 calc R U . . .
C21 C 0.4096(3) 0.42990(15) 0.2337(3) 0.0420(8) Uani 1 1 d . . . . .
C22 C 0.6022(3) 0.38103(17) 0.2742(3) 0.0461(9) Uani 1 1 d . . . . .
C23 C 0.5779(3) 0.42071(15) 0.3985(3) 0.0436(8) Uani 1 1 d . . . . .
H23 H 0.636638 0.457532 0.403747 0.052 Uiso 1 1 calc R U . . .
C24 C 0.4991(4) 0.36168(18) 0.0493(4) 0.0595(10) Uani 1 1 d . . . . .
H24A H 0.583505 0.346538 0.026082 0.071 Uiso 1 1 calc R U . . .
H24B H 0.477431 0.396597 -0.012139 0.071 Uiso 1 1 calc R U . . .
C25 C 0.4073(4) 0.30747(19) 0.0307(4) 0.0707(12) Uani 1 1 d . . . . .
H25A H 0.412840 0.291509 -0.060059 0.106 Uiso 1 1 calc R U . . .
H25B H 0.322755 0.322867 0.047574 0.106 Uiso 1 1 calc R U . . .
H25C H 0.427012 0.273075 0.092559 0.106 Uiso 1 1 calc R U . . .
O1 O 0.3743(2) 0.47999(12) 0.6734(3) 0.0656(7) Uani 1 1 d . . . . .
O2 O 0.3234(2) 0.45007(12) 0.1667(3) 0.0618(7) Uani 1 1 d . . . . .
O3 O 0.6958(3) 0.34930(14) 0.2480(3) 0.0680(8) Uani 1 1 d . . . . .
N1 N 0.1800(3) 0.45105(12) 0.5884(3) 0.0444(7) Uani 1 1 d . . . . .
N2 N 0.4492(2) 0.35458(11) 0.5238(3) 0.0384(6) Uani 1 1 d . . . . .
N3 N 0.5009(3) 0.38711(12) 0.1873(3) 0.0431(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(5) . ?
C1 C6 1.381(5) . ?
C1 C7 1.500(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.459(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C12 1.381(5) . ?
C8 C9 1.385(4) . ?
C8 N1 1.409(4) . ?
C9 C15 1.372(4) . ?
C9 C10 1.508(4) . ?
C10 N2 1.449(4) . ?
C10 C11 1.547(5) . ?
C10 C20 1.579(4) . ?
C11 O1 1.222(4) . ?
C11 N1 1.362(4) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.453(4) . ?
C16 C23 1.516(5) . ?
C16 C17 1.517(5) . ?
C16 H16 0.9800 . ?
C17 C18 1.532(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.538(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N2 1.443(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.513(5) . ?
C20 C23 1.552(4) . ?
C20 H20 0.9800 . ?
C21 O2 1.200(4) . ?
C21 N3 1.384(4) . ?
C22 O3 1.211(4) . ?
C22 N3 1.377(4) . ?
C22 C23 1.502(5) . ?
C23 H23 0.9800 . ?
C24 N3 1.466(5) . ?
C24 C25 1.489(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C2 C1 C6 117.9(4) . . ?
C2 C1 C7 121.3(3) . . ?
C6 C1 C7 120.8(3) . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.5(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C1 112.9(2) . . ?
N1 C7 H7A 109.0 . . ?
C1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C12 C8 C9 121.2(3) . . ?
C12 C8 N1 128.6(3) . . ?
C9 C8 N1 110.1(3) . . ?
C15 C9 C8 120.6(3) . . ?
C15 C9 C10 130.4(3) . . ?
C8 C9 C10 109.0(3) . . ?
N2 C10 C9 113.4(2) . . ?
N2 C10 C11 116.2(3) . . ?
C9 C10 C11 101.3(2) . . ?
N2 C10 C20 101.1(2) . . ?
C9 C10 C20 117.5(3) . . ?
C11 C10 C20 107.9(2) . . ?
O1 C11 N1 125.0(3) . . ?
O1 C11 C10 126.5(3) . . ?
N1 C11 C10 108.5(3) . . ?
C8 C12 C13 117.3(4) . . ?
C8 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C9 C15 C14 118.5(3) . . ?
C9 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N2 C16 C23 100.9(2) . . ?
N2 C16 C17 101.6(3) . . ?
C23 C16 C17 125.8(3) . . ?
N2 C16 H16 109.0 . . ?
C23 C16 H16 109.0 . . ?
C17 C16 H16 109.0 . . ?
C16 C17 C18 102.8(3) . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C17 C18 C19 106.4(3) . . ?
C17 C18 H18A 110.5 . . ?
C19 C18 H18A 110.5 . . ?
C17 C18 H18B 110.5 . . ?
C19 C18 H18B 110.5 . . ?
H18A C18 H18B 108.6 . . ?
N2 C19 C18 102.5(3) . . ?
N2 C19 H19A 111.3 . . ?
C18 C19 H19A 111.3 . . ?
N2 C19 H19B 111.3 . . ?
C18 C19 H19B 111.3 . . ?
H19A C19 H19B 109.2 . . ?
C21 C20 C23 104.3(3) . . ?
C21 C20 C10 113.4(2) . . ?
C23 C20 C10 105.4(2) . . ?
C21 C20 H20 111.1 . . ?
C23 C20 H20 111.1 . . ?
C10 C20 H20 111.1 . . ?
O2 C21 N3 124.3(3) . . ?
O2 C21 C20 128.2(3) . . ?
N3 C21 C20 107.5(3) . . ?
O3 C22 N3 123.1(3) . . ?
O3 C22 C23 127.5(3) . . ?
N3 C22 C23 109.4(3) . . ?
C22 C23 C16 116.2(2) . . ?
C22 C23 C20 103.5(3) . . ?
C16 C23 C20 103.8(3) . . ?
C22 C23 H23 110.9 . . ?
C16 C23 H23 110.9 . . ?
C20 C23 H23 110.9 . . ?
N3 C24 C25 113.1(3) . . ?
N3 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
N3 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 N1 C8 110.6(3) . . ?
C11 N1 C7 124.8(3) . . ?
C8 N1 C7 124.3(3) . . ?
C19 N2 C10 124.2(3) . . ?
C19 N2 C16 107.3(3) . . ?
C10 N2 C16 109.4(2) . . ?
C22 N3 C21 112.9(3) . . ?
C22 N3 C24 124.2(3) . . ?
C21 N3 C24 121.9(3) . . ?

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
C6 C1 C2 C3 -0.3(6) . . . . ?
C7 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C7 C1 C6 C5 179.4(3) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C2 C1 C7 N1 56.5(5) . . . . ?
C6 C1 C7 N1 -123.3(3) . . . . ?
C12 C8 C9 C15 -4.0(5) . . . . ?
N1 C8 C9 C15 174.1(3) . . . . ?
C12 C8 C9 C10 178.2(3) . . . . ?
N1 C8 C9 C10 -3.7(3) . . . . ?
C15 C9 C10 N2 -45.9(4) . . . . ?
C8 C9 C10 N2 131.7(3) . . . . ?
C15 C9 C10 C11 -171.1(3) . . . . ?
C8 C9 C10 C11 6.5(3) . . . . ?
C15 C9 C10 C20 71.7(4) . . . . ?
C8 C9 C10 C20 -110.7(3) . . . . ?
N2 C10 C11 O1 49.8(4) . . . . ?
C9 C10 C11 O1 173.2(3) . . . . ?
C20 C10 C11 O1 -62.8(4) . . . . ?
N2 C10 C11 N1 -130.5(3) . . . . ?
C9 C10 C11 N1 -7.2(3) . . . . ?
C20 C10 C11 N1 116.9(3) . . . . ?
C9 C8 C12 C13 1.7(5) . . . . ?
N1 C8 C12 C13 -176.0(3) . . . . ?
C8 C12 C13 C14 1.4(5) . . . . ?
C12 C13 C14 C15 -2.4(6) . . . . ?
C8 C9 C15 C14 3.0(5) . . . . ?
C10 C9 C15 C14 -179.7(3) . . . . ?
C13 C14 C15 C9 0.1(5) . . . . ?
N2 C16 C17 C18 -35.2(3) . . . . ?
C23 C16 C17 C18 -147.9(3) . . . . ?
C16 C17 C18 C19 14.3(4) . . . . ?
C17 C18 C19 N2 12.2(4) . . . . ?
N2 C10 C20 C21 102.6(3) . . . . ?
C9 C10 C20 C21 -21.3(4) . . . . ?
C11 C10 C20 C21 -134.9(3) . . . . ?
N2 C10 C20 C23 -10.8(3) . . . . ?
C9 C10 C20 C23 -134.8(3) . . . . ?
C11 C10 C20 C23 111.6(3) . . . . ?
C23 C20 C21 O2 -165.0(3) . . . . ?
C10 C20 C21 O2 80.8(4) . . . . ?
C23 C20 C21 N3 15.7(3) . . . . ?
C10 C20 C21 N3 -98.5(3) . . . . ?
O3 C22 C23 C16 -62.0(5) . . . . ?
N3 C22 C23 C16 119.8(3) . . . . ?
O3 C22 C23 C20 -175.1(3) . . . . ?
N3 C22 C23 C20 6.8(3) . . . . ?
N2 C16 C23 C22 -77.3(3) . . . . ?
C17 C16 C23 C22 35.7(4) . . . . ?
N2 C16 C23 C20 35.6(3) . . . . ?
C17 C16 C23 C20 148.6(3) . . . . ?
C21 C20 C23 C22 -13.3(3) . . . . ?
C10 C20 C23 C22 106.4(3) . . . . ?
C21 C20 C23 C16 -135.1(2) . . . . ?
C10 C20 C23 C16 -15.4(3) . . . . ?
O1 C11 N1 C8 -174.9(3) . . . . ?
C10 C11 N1 C8 5.5(3) . . . . ?
O1 C11 N1 C7 -0.9(5) . . . . ?
C10 C11 N1 C7 179.4(3) . . . . ?
C12 C8 N1 C11 176.7(3) . . . . ?
C9 C8 N1 C11 -1.2(4) . . . . ?
C12 C8 N1 C7 2.8(5) . . . . ?
C9 C8 N1 C7 -175.2(3) . . . . ?
C1 C7 N1 C11 -106.4(4) . . . . ?
C1 C7 N1 C8 66.7(4) . . . . ?
C18 C19 N2 C10 -165.4(3) . . . . ?
C18 C19 N2 C16 -36.2(3) . . . . ?
C9 C10 N2 C19 -69.2(4) . . . . ?
C11 C10 N2 C19 47.6(4) . . . . ?
C20 C10 N2 C19 164.1(3) . . . . ?
C9 C10 N2 C16 162.5(2) . . . . ?
C11 C10 N2 C16 -80.7(3) . . . . ?
C20 C10 N2 C16 35.7(3) . . . . ?
C23 C16 N2 C19 176.3(3) . . . . ?
C17 C16 N2 C19 46.0(3) . . . . ?
C23 C16 N2 C10 -46.4(3) . . . . ?
C17 C16 N2 C10 -176.8(3) . . . . ?
O3 C22 N3 C21 -175.0(3) . . . . ?
C23 C22 N3 C21 3.3(3) . . . . ?
O3 C22 N3 C24 -6.2(5) . . . . ?
C23 C22 N3 C24 172.0(3) . . . . ?
O2 C21 N3 C22 168.4(3) . . . . ?
C20 C21 N3 C22 -12.3(3) . . . . ?
O2 C21 N3 C24 -0.7(5) . . . . ?
C20 C21 N3 C24 178.7(3) . . . . ?
C25 C24 N3 C22 112.6(4) . . . . ?
C25 C24 N3 C21 -79.6(4) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_KA807_0m
_database_code_depnum_ccdc_archive 'CCDC 2065304'
loop_
_audit_author_name
_audit_author_address
'NAGENDER THADEM'
;CSIR Indian Institute of Chemical Technology 
India
;
_audit_update_record             
;
2021-02-26 deposited with the CCDC.	2021-09-02 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 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

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                   14.0372(2)
_cell_length_b                   9.4978(2)
_cell_length_c                   14.4733(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.2323(10)
_cell_angle_gamma                90
_cell_volume                     1773.15(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5642
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.97

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25150
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.635
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3571
_reflns_number_gt                2484
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.1569P] 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         3571
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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
C1 C 0.32160(18) 0.5415(3) 0.50361(17) 0.0330(6) Uani 1 1 d . . . . .
C2 C 0.2914(2) 0.5011(3) 0.4044(2) 0.0462(7) Uani 1 1 d . . . . .
H2 H 0.238131 0.547779 0.353378 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3434(3) 0.3876(3) 0.3826(2) 0.0586(8) Uani 1 1 d . . . . .
H3 H 0.324462 0.358558 0.316342 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4220(3) 0.3191(3) 0.4584(3) 0.0591(8) Uani 1 1 d . . . . .
H4 H 0.456873 0.246188 0.442091 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4506(2) 0.3556(3) 0.5580(2) 0.0518(7) Uani 1 1 d . . . . .
H5 H 0.502902 0.307545 0.609043 0.062 Uiso 1 1 calc R U . . .
C6 C 0.39878(18) 0.4659(3) 0.57882(19) 0.0371(6) Uani 1 1 d . . . . .
C7 C 0.34522(17) 0.6279(3) 0.66508(17) 0.0316(5) Uani 1 1 d . . . . .
C8 C 0.28251(16) 0.6559(2) 0.55227(16) 0.0283(5) Uani 1 1 d . . . . .
C9 C 0.4839(3) 0.4646(4) 0.7693(2) 0.0738(11) Uani 1 1 d . . . . .
H9A H 0.471867 0.365459 0.772005 0.111 Uiso 1 1 calc R U . . .
H9B H 0.472888 0.511319 0.823085 0.111 Uiso 1 1 calc R U . . .
H9C H 0.553922 0.479862 0.776046 0.111 Uiso 1 1 calc R U . . .
C10 C 0.2886(2) 0.8381(3) 0.42907(19) 0.0441(7) Uani 1 1 d . . . . .
H10A H 0.222242 0.802507 0.382455 0.053 Uiso 1 1 calc R U . . .
H10B H 0.343113 0.802521 0.410099 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2893(2) 0.9962(3) 0.4333(2) 0.0550(8) Uani 1 1 d . . . . .
H11A H 0.255612 1.036329 0.366548 0.066 Uiso 1 1 calc R U . . .
H11B H 0.359606 1.032123 0.463922 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2288(2) 1.0291(3) 0.4980(3) 0.0585(8) Uani 1 1 d . . . . .
H12A H 0.156621 1.048312 0.456365 0.070 Uiso 1 1 calc R U . . .
H12B H 0.258103 1.109869 0.540805 0.070 Uiso 1 1 calc R U . . .
C13 C 0.23930(18) 0.8946(3) 0.56155(18) 0.0354(6) Uani 1 1 d . . . . .
H13 H 0.272645 0.918233 0.633150 0.042 Uiso 1 1 calc R U . . .
C14 C 0.16325(16) 0.6546(2) 0.52605(16) 0.0295(5) Uani 1 1 d . . . . .
H14 H 0.127788 0.632702 0.454363 0.035 Uiso 1 1 calc R U . . .
C15 C 0.13803(17) 0.8089(2) 0.54167(17) 0.0325(5) Uani 1 1 d . . . . .
H15 H 0.085456 0.842045 0.477791 0.039 Uiso 1 1 calc R U . . .
C16 C 0.0981(2) 0.8378(3) 0.6215(2) 0.0443(7) Uani 1 1 d . . . . .
C17 C 0.08682(18) 0.5890(3) 0.65038(18) 0.0377(6) Uani 1 1 d . . . . .
C18 C 0.12998(16) 0.5481(3) 0.58376(17) 0.0321(5) Uani 1 1 d . . . . .
C19 C 0.0561(2) 0.4933(3) 0.7051(2) 0.0485(7) Uani 1 1 d . . . . .
H19 H 0.025467 0.524206 0.747873 0.058 Uiso 1 1 calc R U . . .
C20 C 0.0713(2) 0.3514(3) 0.6956(2) 0.0555(8) Uani 1 1 d . . . . .
H20 H 0.052121 0.286145 0.733079 0.067 Uiso 1 1 calc R U . . .
C21 C 0.1150(2) 0.3064(3) 0.6302(2) 0.0530(8) Uani 1 1 d . . . . .
H21 H 0.125786 0.210902 0.623999 0.064 Uiso 1 1 calc R U . . .
C22 C 0.14255(19) 0.4035(3) 0.5743(2) 0.0448(7) Uani 1 1 d . . . . .
H22 H 0.170183 0.372007 0.529277 0.054 Uiso 1 1 calc R U . . .
O1 O 0.33787(13) 0.6926(2) 0.73462(12) 0.0449(5) Uani 1 1 d . . . . .
O2 O 0.07146(15) 0.7302(2) 0.66801(14) 0.0512(5) Uani 1 1 d . . . . .
O3 O 0.0876(2) 0.9538(2) 0.6476(2) 0.0812(8) Uani 1 1 d . . . . .
N1 N 0.41271(15) 0.5207(2) 0.67363(15) 0.0407(5) Uani 1 1 d . . . . .
N2 N 0.30752(14) 0.8008(2) 0.53401(13) 0.0315(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(3) . ?
C1 C6 1.395(3) . ?
C1 C8 1.511(3) . ?
C2 C3 1.406(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.408(3) . ?
C7 O1 1.218(3) . ?
C7 N1 1.362(3) . ?
C7 C8 1.542(3) . ?
C8 N2 1.470(3) . ?
C8 C14 1.564(3) . ?
C9 N1 1.452(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.478(3) . ?
C10 C11 1.503(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.525(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.547(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.474(3) . ?
C13 C15 1.564(3) . ?
C13 H13 0.9800 . ?
C14 C18 1.499(3) . ?
C14 C15 1.544(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.495(3) . ?
C15 H15 0.9800 . ?
C16 O3 1.192(3) . ?
C16 O2 1.355(3) . ?
C17 C19 1.381(4) . ?
C17 C18 1.381(3) . ?
C17 O2 1.398(3) . ?
C18 C22 1.399(3) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
C2 C1 C6 119.6(2) . . ?
C2 C1 C8 131.7(2) . . ?
C6 C1 C8 108.7(2) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C1 122.5(2) . . ?
C5 C6 N1 127.9(2) . . ?
C1 C6 N1 109.7(2) . . ?
O1 C7 N1 125.8(2) . . ?
O1 C7 C8 126.1(2) . . ?
N1 C7 C8 108.14(19) . . ?
N2 C8 C1 115.67(18) . . ?
N2 C8 C7 105.98(17) . . ?
C1 C8 C7 102.04(18) . . ?
N2 C8 C14 105.81(17) . . ?
C1 C8 C14 115.61(18) . . ?
C7 C8 C14 111.40(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 101.7(2) . . ?
N2 C10 H10A 111.4 . . ?
C11 C10 H10A 111.4 . . ?
N2 C10 H10B 111.4 . . ?
C11 C10 H10B 111.4 . . ?
H10A C10 H10B 109.3 . . ?
C10 C11 C12 103.5(2) . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.0 . . ?
C11 C12 C13 104.5(2) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
N2 C13 C12 104.95(19) . . ?
N2 C13 C15 106.01(19) . . ?
C12 C13 C15 117.0(2) . . ?
N2 C13 H13 109.5 . . ?
C12 C13 H13 109.5 . . ?
C15 C13 H13 109.5 . . ?
C18 C14 C15 114.75(19) . . ?
C18 C14 C8 114.15(18) . . ?
C15 C14 C8 104.03(18) . . ?
C18 C14 H14 107.9 . . ?
C15 C14 H14 107.9 . . ?
C8 C14 H14 107.9 . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 C13 110.6(2) . . ?
C14 C15 C13 106.07(18) . . ?
C16 C15 H15 107.3 . . ?
C14 C15 H15 107.3 . . ?
C13 C15 H15 107.3 . . ?
O3 C16 O2 116.5(2) . . ?
O3 C16 C15 123.1(2) . . ?
O2 C16 C15 120.4(2) . . ?
C19 C17 C18 122.5(3) . . ?
C19 C17 O2 114.9(2) . . ?
C18 C17 O2 122.6(2) . . ?
C17 C18 C22 116.8(2) . . ?
C17 C18 C14 121.2(2) . . ?
C22 C18 C14 122.0(2) . . ?
C20 C19 C17 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C17 C19 H19 120.3 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C18 121.6(3) . . ?
C21 C22 H22 119.2 . . ?
C18 C22 H22 119.2 . . ?
C16 O2 C17 122.71(19) . . ?
C7 N1 C6 111.34(19) . . ?
C7 N1 C9 123.6(2) . . ?
C6 N1 C9 124.9(2) . . ?
C8 N2 C13 106.91(17) . . ?
C8 N2 C10 116.75(19) . . ?
C13 N2 C10 105.11(18) . . ?

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
C6 C1 C2 C3 -2.7(4) . . . . ?
C8 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C5 C6 N1 178.9(2) . . . . ?
C2 C1 C6 C5 3.4(4) . . . . ?
C8 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 N1 -176.8(2) . . . . ?
C8 C1 C6 N1 0.7(3) . . . . ?
C2 C1 C8 N2 -71.1(3) . . . . ?
C6 C1 C8 N2 111.8(2) . . . . ?
C2 C1 C8 C7 174.4(3) . . . . ?
C6 C1 C8 C7 -2.7(2) . . . . ?
C2 C1 C8 C14 53.3(3) . . . . ?
C6 C1 C8 C14 -123.8(2) . . . . ?
O1 C7 C8 N2 60.6(3) . . . . ?
N1 C7 C8 N2 -117.6(2) . . . . ?
O1 C7 C8 C1 -178.0(2) . . . . ?
N1 C7 C8 C1 3.9(2) . . . . ?
O1 C7 C8 C14 -54.0(3) . . . . ?
N1 C7 C8 C14 127.8(2) . . . . ?
N2 C10 C11 C12 -41.7(3) . . . . ?
C10 C11 C12 C13 23.7(3) . . . . ?
C11 C12 C13 N2 3.0(3) . . . . ?
C11 C12 C13 C15 -114.2(3) . . . . ?
N2 C8 C14 C18 -151.24(18) . . . . ?
C1 C8 C14 C18 79.3(2) . . . . ?
C7 C8 C14 C18 -36.5(3) . . . . ?
N2 C8 C14 C15 -25.4(2) . . . . ?
C1 C8 C14 C15 -154.85(19) . . . . ?
C7 C8 C14 C15 89.3(2) . . . . ?
C18 C14 C15 C16 8.4(3) . . . . ?
C8 C14 C15 C16 -117.0(2) . . . . ?
C18 C14 C15 C13 132.87(19) . . . . ?
C8 C14 C15 C13 7.5(2) . . . . ?
N2 C13 C15 C16 141.6(2) . . . . ?
C12 C13 C15 C16 -101.8(3) . . . . ?
N2 C13 C15 C14 12.8(2) . . . . ?
C12 C13 C15 C14 129.4(2) . . . . ?
C14 C15 C16 O3 171.1(3) . . . . ?
C13 C15 C16 O3 49.0(4) . . . . ?
C14 C15 C16 O2 -9.1(3) . . . . ?
C13 C15 C16 O2 -131.3(2) . . . . ?
C19 C17 C18 C22 -0.6(4) . . . . ?
O2 C17 C18 C22 179.0(2) . . . . ?
C19 C17 C18 C14 -179.6(2) . . . . ?
O2 C17 C18 C14 0.1(3) . . . . ?
C15 C14 C18 C17 -4.2(3) . . . . ?
C8 C14 C18 C17 115.7(2) . . . . ?
C15 C14 C18 C22 176.9(2) . . . . ?
C8 C14 C18 C22 -63.2(3) . . . . ?
C18 C17 C19 C20 1.8(4) . . . . ?
O2 C17 C19 C20 -177.8(2) . . . . ?
C17 C19 C20 C21 -1.3(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C18 1.7(4) . . . . ?
C17 C18 C22 C21 -1.2(4) . . . . ?
C14 C18 C22 C21 177.8(2) . . . . ?
O3 C16 O2 C17 -175.2(3) . . . . ?
C15 C16 O2 C17 5.1(4) . . . . ?
C19 C17 O2 C16 179.3(2) . . . . ?
C18 C17 O2 C16 -0.3(4) . . . . ?
O1 C7 N1 C6 178.1(2) . . . . ?
C8 C7 N1 C6 -3.7(3) . . . . ?
O1 C7 N1 C9 2.5(4) . . . . ?
C8 C7 N1 C9 -179.3(2) . . . . ?
C5 C6 N1 C7 -178.3(2) . . . . ?
C1 C6 N1 C7 2.0(3) . . . . ?
C5 C6 N1 C9 -2.7(4) . . . . ?
C1 C6 N1 C9 177.5(3) . . . . ?
C1 C8 N2 C13 164.11(18) . . . . ?
C7 C8 N2 C13 -83.7(2) . . . . ?
C14 C8 N2 C13 34.7(2) . . . . ?
C1 C8 N2 C10 46.8(3) . . . . ?
C7 C8 N2 C10 159.06(19) . . . . ?
C14 C8 N2 C10 -82.6(2) . . . . ?
C12 C13 N2 C8 -154.1(2) . . . . ?
C15 C13 N2 C8 -29.6(2) . . . . ?
C12 C13 N2 C10 -29.4(3) . . . . ?
C15 C13 N2 C10 95.1(2) . . . . ?
C11 C10 N2 C8 162.9(2) . . . . ?
C11 C10 N2 C13 44.6(2) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049

