# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kmd_a
_database_code_depnum_ccdc_archive 'CCDC 2068242'
loop_
_audit_author_name
_audit_author_address
'Nayarassery N. Adarsh'
;Chemistry and Biomolecular Science, Clarkson University, Potsdam New York
India
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 N5 O4'
_chemical_formula_sum            'C27 H21 N5 O4'
_chemical_formula_weight         479.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   26.676(2)
_cell_length_b                   11.1232(8)
_cell_length_c                   8.1112(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.747(4)
_cell_angle_gamma                90
_cell_volume                     2337.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      1.992
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   0.990
_exptl_transmission_factor_min   0.968
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.113
_diffrn_reflns_theta_min         1.992
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Microfocal D8 venture Bruker APEX 3'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2043
_reflns_number_total             2588
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+3.2374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), N2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c :
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.500000 0.9546(3) 0.250000 0.0454(8) Uani 1 2 d S T P . .
H1 H 0.499999 1.038220 0.250001 0.054 Uiso 1 2 calc R U P . .
C2 C 0.52661(8) 0.89164(18) 0.3905(3) 0.0394(5) Uani 1 1 d . . . . .
H2 H 0.545172 0.931911 0.486116 0.047 Uiso 1 1 calc R U . . .
C3 C 0.52504(7) 0.76717(17) 0.3857(2) 0.0303(4) Uani 1 1 d . . . . .
N1 N 0.500000 0.70502(19) 0.250000 0.0292(5) Uani 1 2 d S T P . .
C4 C 0.55275(8) 0.69535(18) 0.5370(2) 0.0349(4) Uani 1 1 d . . . . .
O1 O 0.57090(7) 0.74221(15) 0.67419(19) 0.0576(5) Uani 1 1 d . . . . .
N2 N 0.55505(6) 0.57694(15) 0.5044(2) 0.0354(4) Uani 1 1 d . . . . .
H2A H 0.538976 0.549564 0.406992 0.042 Uiso 1 1 calc R U . . .
N3 N 0.58273(6) 0.49873(15) 0.6243(2) 0.0362(4) Uani 1 1 d . . . . .
C5 C 0.58831(8) 0.39331(18) 0.5688(3) 0.0360(5) Uani 1 1 d . . . . .
H5 H 0.572478 0.374518 0.456815 0.043 Uiso 1 1 calc R U . . .
C6 C 0.61885(7) 0.30158(18) 0.6765(2) 0.0335(4) Uani 1 1 d . . . . .
C7 C 0.64965(8) 0.33037(18) 0.8366(3) 0.0371(5) Uani 1 1 d . . . . .
H7 H 0.649105 0.407981 0.878763 0.045 Uiso 1 1 calc R U . . .
C8 C 0.68060(8) 0.24502(18) 0.9315(3) 0.0381(5) Uani 1 1 d . . . . .
H8 H 0.700887 0.264994 1.037870 0.046 Uiso 1 1 calc R U . . .
C9 C 0.68191(8) 0.12866(18) 0.8700(3) 0.0357(5) Uani 1 1 d . . . . .
C10 C 0.65073(8) 0.09735(19) 0.7142(3) 0.0409(5) Uani 1 1 d . . . . .
H10 H 0.650533 0.018958 0.674212 0.049 Uiso 1 1 calc R U . . .
C11 C 0.61971(8) 0.18466(19) 0.6184(3) 0.0395(5) Uani 1 1 d . . . . .
H11 H 0.599038 0.164221 0.512766 0.047 Uiso 1 1 calc R U . . .
O2 O 0.71616(6) 0.05422(13) 0.97399(18) 0.0471(4) Uani 1 1 d . . . . .
C12 C 0.72771(9) -0.05960(19) 0.9101(3) 0.0453(5) Uani 1 1 d . . . . .
H12A H 0.735134 -0.050125 0.799430 0.054 Uiso 1 1 calc R U . . .
H12B H 0.698685 -0.113966 0.899420 0.054 Uiso 1 1 calc R U . . .
C13 C 0.77283(9) -0.10676(19) 1.0319(3) 0.0428(5) Uani 1 1 d . . . . .
C14 C 0.81007(9) -0.1403(2) 1.1287(3) 0.0505(6) Uani 1 1 d . . . . .
H14 H 0.839634 -0.167000 1.205602 0.061 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
C1 H1 0.9300 . ?
C1 C2 1.382(2) 2_655 ?
C1 C2 1.382(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 N1 1.337(2) . ?
C3 C4 1.503(3) . ?
C4 O1 1.220(2) . ?
C4 N2 1.348(3) . ?
N2 H2A 0.8600 . ?
N2 N3 1.381(2) . ?
N3 C5 1.277(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.459(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(3) . ?
C9 C10 1.382(3) . ?
C9 O2 1.366(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
O2 C12 1.429(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.461(3) . ?
C13 C14 1.171(3) . ?
C14 H14 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 H1 120.5 2_655 . ?
C2 C1 H1 120.5 . . ?
C2 C1 C2 119.1(3) . 2_655 ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.18(17) . . ?
N1 C3 C2 123.07(18) . . ?
N1 C3 C4 116.75(17) . . ?
C3 N1 C3 117.7(2) . 2_655 ?
O1 C4 C3 121.94(18) . . ?
O1 C4 N2 124.76(18) . . ?
N2 C4 C3 113.30(16) . . ?
C4 N2 H2A 119.4 . . ?
C4 N2 N3 121.26(16) . . ?
N3 N2 H2A 119.4 . . ?
C5 N3 N2 114.68(16) . . ?
N3 C5 H5 119.1 . . ?
N3 C5 C6 121.74(18) . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 121.11(18) . . ?
C11 C6 C5 120.31(18) . . ?
C11 C6 C7 118.51(18) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.40(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.48(19) . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.09(18) . . ?
O2 C9 C8 114.40(18) . . ?
O2 C9 C10 125.50(18) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.01(19) . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 121.47(19) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C9 O2 C12 118.92(16) . . ?
O2 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
O2 C12 C13 106.67(18) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C14 C13 C12 177.2(2) . . ?
C13 C14 H14 180.0 . . ?

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
C1 C2 C3 N1 1.7(3) . . . . ?
C1 C2 C3 C4 -178.98(16) . . . . ?
C2 C1 C2 C3 -0.79(14) 2_655 . . . ?
C2 C3 N1 C3 -0.86(15) . . . 2_655 ?
C2 C3 C4 O1 10.5(3) . . . . ?
C2 C3 C4 N2 -169.54(19) . . . . ?
C3 C4 N2 N3 174.55(16) . . . . ?
N1 C3 C4 O1 -170.10(18) . . . . ?
N1 C3 C4 N2 9.8(2) . . . . ?
C4 C3 N1 C3 179.79(19) . . . 2_655 ?
C4 N2 N3 C5 -169.73(19) . . . . ?
O1 C4 N2 N3 -5.5(3) . . . . ?
N2 N3 C5 C6 176.68(17) . . . . ?
N3 C5 C6 C7 -9.8(3) . . . . ?
N3 C5 C6 C11 173.1(2) . . . . ?
C5 C6 C7 C8 -175.82(19) . . . . ?
C5 C6 C11 C10 176.2(2) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C6 C11 C10 -0.9(3) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C7 C8 C9 O2 177.09(19) . . . . ?
C8 C9 C10 C11 2.3(3) . . . . ?
C8 C9 O2 C12 -168.42(19) . . . . ?
C9 C10 C11 C6 -0.9(3) . . . . ?
C9 O2 C12 C13 167.66(18) . . . . ?
C10 C9 O2 C12 10.5(3) . . . . ?
C11 C6 C7 C8 1.2(3) . . . . ?
O2 C9 C10 C11 -176.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
