# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_KA971_0m
_database_code_depnum_ccdc_archive 'CCDC 2022481'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu '
;Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-08-10 deposited with the CCDC.	2021-01-04 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 H17 N3 O'
_chemical_formula_sum            'C22 H17 N3 O'
_chemical_formula_weight         339.38

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.954(3)
_cell_length_b                   20.606(13)
_cell_length_c                   16.560(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.728(15)
_cell_angle_gamma                90
_cell_volume                     1689.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7473
_cell_measurement_theta_min      2.333
_cell_measurement_theta_max      25.845

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7045
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16855
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3445
_reflns_number_gt                2492
_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, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+0.6759P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3445
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.3233(4) 0.62865(10) 0.31076(13) 0.0427(5) Uani 1 1 d . . . . .
C2 C 0.1284(5) 0.58832(12) 0.27314(15) 0.0583(6) Uani 1 1 d . . . . .
H2 H 0.063589 0.597946 0.221226 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0334(6) 0.53495(13) 0.31246(17) 0.0680(7) Uani 1 1 d . . . . .
H3 H -0.093948 0.508412 0.286524 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1233(6) 0.51973(12) 0.39016(17) 0.0670(7) Uani 1 1 d . . . . .
H4 H 0.055760 0.483502 0.416265 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3130(5) 0.55853(11) 0.42840(15) 0.0577(6) Uani 1 1 d . . . . .
H5 H 0.374027 0.548520 0.480587 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4149(4) 0.61301(10) 0.38921(13) 0.0438(5) Uani 1 1 d . . . . .
C7 C 0.6115(4) 0.65529(10) 0.43026(12) 0.0443(5) Uani 1 1 d . . . . .
C8 C 0.5827(4) 0.72121(9) 0.30770(11) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.6885(4) 0.77808(9) 0.26629(12) 0.0380(5) Uani 1 1 d . . . . .
C10 C 0.5819(4) 0.79744(10) 0.19088(12) 0.0439(5) Uani 1 1 d . . . . .
H10 H 0.432002 0.775987 0.168735 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6952(5) 0.84774(11) 0.14890(14) 0.0527(6) Uani 1 1 d . . . . .
H11 H 0.622718 0.860188 0.098807 0.063 Uiso 1 1 calc R U . . .
C12 C 0.9193(5) 0.87971(12) 0.18223(15) 0.0575(6) Uani 1 1 d . . . . .
H12 H 0.997990 0.913334 0.153799 0.069 Uiso 1 1 calc R U . . .
C13 C 1.0257(4) 0.86223(11) 0.25663(15) 0.0539(6) Uani 1 1 d . . . . .
H13 H 1.174062 0.884498 0.278414 0.065 Uiso 1 1 calc R U . . .
C14 C 0.9129(4) 0.81131(10) 0.29980(12) 0.0417(5) Uani 1 1 d . . . . .
C15 C 0.8335(4) 0.76256(10) 0.43011(12) 0.0407(5) Uani 1 1 d . . . . .
H15 H 0.942493 0.741484 0.472947 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6421(4) 0.81030(9) 0.47049(11) 0.0363(5) Uani 1 1 d . . . . .
C17 C 0.5937(4) 0.87249(9) 0.44157(12) 0.0408(5) Uani 1 1 d . . . . .
H17 H 0.681183 0.886776 0.395958 0.049 Uiso 1 1 calc R U . . .
C18 C 0.4157(4) 0.91389(10) 0.47987(12) 0.0422(5) Uani 1 1 d . . . . .
H18 H 0.383531 0.955088 0.458756 0.051 Uiso 1 1 calc R U . . .
C19 C 0.2856(4) 0.89473(10) 0.54894(12) 0.0410(5) Uani 1 1 d . . . . .
C20 C 0.3356(4) 0.83293(10) 0.57787(13) 0.0476(5) Uani 1 1 d . . . . .
H20 H 0.250502 0.819023 0.624077 0.057 Uiso 1 1 calc R U . . .
C21 C 0.5101(4) 0.79110(10) 0.53952(12) 0.0451(5) Uani 1 1 d . . . . .
H21 H 0.539115 0.749653 0.560255 0.054 Uiso 1 1 calc R U . . .
C22 C 0.0970(5) 0.93957(12) 0.59241(14) 0.0572(6) Uani 1 1 d . . . . .
H22A H 0.141324 0.983816 0.580387 0.086 Uiso 1 1 calc R U . . .
H22B H 0.115889 0.932468 0.649591 0.086 Uiso 1 1 calc R U . . .
H22C H -0.085901 0.930912 0.574851 0.086 Uiso 1 1 calc R U . . .
H3N H 1.138(5) 0.8158(12) 0.3968(16) 0.066(8) Uiso 1 1 d . . . . .
N1 N 0.4176(3) 0.68202(8) 0.26925(10) 0.0430(4) Uani 1 1 d . . . . .
N2 N 0.6750(3) 0.71106(8) 0.38685(9) 0.0384(4) Uani 1 1 d . . . . .
N3 N 1.0160(3) 0.79101(10) 0.37424(11) 0.0478(5) Uani 1 1 d . . . . .
O1 O 0.7093(4) 0.64569(8) 0.49788(10) 0.0625(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 N1 1.385(3) . ?
C1 C6 1.401(3) . ?
C1 C2 1.405(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.459(3) . ?
C7 O1 1.223(3) . ?
C7 N2 1.396(3) . ?
C8 N1 1.302(3) . ?
C8 N2 1.391(2) . ?
C8 C9 1.463(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.406(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.385(3) . ?
C15 N3 1.438(3) . ?
C15 N2 1.491(2) . ?
C15 C16 1.533(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.387(3) . ?
C16 C21 1.392(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 C22 1.512(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N3 H3N 0.87(3) . ?

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 122.57(18) . . ?
N1 C1 C2 119.1(2) . . ?
C6 C1 C2 118.3(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 119.17(19) . . ?
O1 C7 N2 121.0(2) . . ?
O1 C7 C6 124.8(2) . . ?
N2 C7 C6 114.16(18) . . ?
N1 C8 N2 123.47(19) . . ?
N1 C8 C9 119.75(18) . . ?
N2 C8 C9 116.74(16) . . ?
C10 C9 C14 119.08(19) . . ?
C10 C9 C8 121.07(18) . . ?
C14 C9 C8 119.70(18) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
N3 C14 C13 122.72(19) . . ?
N3 C14 C9 118.0(2) . . ?
C13 C14 C9 119.2(2) . . ?
N3 C15 N2 108.25(16) . . ?
N3 C15 C16 115.34(18) . . ?
N2 C15 C16 110.06(15) . . ?
N3 C15 H15 107.6 . . ?
N2 C15 H15 107.6 . . ?
C16 C15 H15 107.6 . . ?
C17 C16 C21 117.76(18) . . ?
C17 C16 C15 123.04(18) . . ?
C21 C16 C15 119.20(18) . . ?
C16 C17 C18 120.93(19) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 121.15(19) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 117.77(19) . . ?
C20 C19 C22 120.4(2) . . ?
C18 C19 C22 121.9(2) . . ?
C19 C20 C21 121.5(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C1 117.76(18) . . ?
C8 N2 C7 122.41(16) . . ?
C8 N2 C15 119.95(17) . . ?
C7 N2 C15 117.53(16) . . ?
C14 N3 C15 118.30(16) . . ?
C14 N3 H3N 116.0(17) . . ?
C15 N3 H3N 114.0(17) . . ?

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 C3 179.4(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
N1 C1 C6 C5 -179.98(19) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N1 C1 C6 C7 1.8(3) . . . . ?
C2 C1 C6 C7 -178.25(19) . . . . ?
C5 C6 C7 O1 3.4(3) . . . . ?
C1 C6 C7 O1 -178.4(2) . . . . ?
C5 C6 C7 N2 -174.06(18) . . . . ?
C1 C6 C7 N2 4.1(3) . . . . ?
N1 C8 C9 C10 10.9(3) . . . . ?
N2 C8 C9 C10 -171.34(17) . . . . ?
N1 C8 C9 C14 -164.62(18) . . . . ?
N2 C8 C9 C14 13.2(3) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C8 C9 C10 C11 -174.72(18) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 N3 178.7(2) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 N3 -179.59(17) . . . . ?
C8 C9 C14 N3 -4.0(3) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C8 C9 C14 C13 174.85(18) . . . . ?
N3 C15 C16 C17 16.4(2) . . . . ?
N2 C15 C16 C17 -106.4(2) . . . . ?
N3 C15 C16 C21 -163.39(17) . . . . ?
N2 C15 C16 C21 73.8(2) . . . . ?
C21 C16 C17 C18 -0.9(3) . . . . ?
C15 C16 C17 C18 179.30(17) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C17 C18 C19 C22 178.52(19) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C22 C19 C20 C21 -179.3(2) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C15 C16 C21 C20 179.92(18) . . . . ?
N2 C8 N1 C1 2.1(3) . . . . ?
C9 C8 N1 C1 179.76(16) . . . . ?
C6 C1 N1 C8 -5.1(3) . . . . ?
C2 C1 N1 C8 174.96(19) . . . . ?
N1 C8 N2 C7 4.3(3) . . . . ?
C9 C8 N2 C7 -173.39(16) . . . . ?
N1 C8 N2 C15 -171.73(17) . . . . ?
C9 C8 N2 C15 10.6(2) . . . . ?
O1 C7 N2 C8 175.30(19) . . . . ?
C6 C7 N2 C8 -7.2(3) . . . . ?
O1 C7 N2 C15 -8.6(3) . . . . ?
C6 C7 N2 C15 168.96(16) . . . . ?
N3 C15 N2 C8 -40.2(2) . . . . ?
C16 C15 N2 C8 86.7(2) . . . . ?
N3 C15 N2 C7 143.61(17) . . . . ?
C16 C15 N2 C7 -89.5(2) . . . . ?
C13 C14 N3 C15 151.2(2) . . . . ?
C9 C14 N3 C15 -30.0(3) . . . . ?
N2 C15 N3 C14 50.1(2) . . . . ?
C16 C15 N3 C14 -73.6(2) . . . . ?

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046



