# 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_KA924_0m
_database_code_depnum_ccdc_archive 'CCDC 2033884'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2021-04-08 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         'C17 H14 N2 O3, C H4 O'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.755(3)
_cell_length_b                   9.844(3)
_cell_length_c                   10.982(4)
_cell_angle_alpha                111.200(12)
_cell_angle_beta                 98.323(12)
_cell_angle_gamma                105.109(11)
_cell_volume                     821.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.398
_cell_measurement_theta_max      30.4735

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_T_max  0.7461
_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            14740
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2893
_reflns_number_gt                2287
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.0578P)²+0.3424P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2893
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.0102(2) 0.28785(18) 0.6468(2) 0.0858(7) Uani 1 1 d . . . . .
N1 N 0.2990(2) 0.81195(17) 0.89589(17) 0.0459(4) Uani 1 1 d . . . . .
C1 C 0.4060(2) 0.7388(2) 0.89774(18) 0.0402(4) Uani 1 1 d . . . . .
O2 O -0.08230(17) 0.46772(16) 0.62064(14) 0.0520(4) Uani 1 1 d . . . . .
N2 N 0.1579(2) 0.69829(18) 0.81382(17) 0.0445(4) Uani 1 1 d . . . . .
C2 C 0.3371(2) 0.57830(19) 0.81973(17) 0.0363(4) Uani 1 1 d . . . . .
H2N H 0.063(3) 0.725(3) 0.797(3) 0.074(7) Uiso 1 1 d . . . . .
O3 O 0.68900(18) 0.89385(16) 0.92746(16) 0.0556(4) Uani 1 1 d . . . . .
C3 C 0.1737(2) 0.5547(2) 0.76555(18) 0.0392(4) Uani 1 1 d . . . . .
H3O H 0.698(3) 0.990(3) 0.984(3) 0.077(8) Uiso 1 1 d . . . . .
O4 O 0.9228(3) 0.8354(3) 0.7893(2) 0.0896(7) Uani 1 1 d . . . . .
C4 C 0.0292(2) 0.4211(2) 0.6722(2) 0.0448(5) Uani 1 1 d . . . . .
H4O H 0.850(4) 0.849(4) 0.840(3) 0.107(11) Uiso 1 1 d . . . . .
C5 C -0.2321(2) 0.3489(2) 0.5263(2) 0.0527(5) Uani 1 1 d . . . . .
H5A H -0.273321 0.272819 0.560964 0.063 Uiso 1 1 calc R U . . .
H5AB H -0.212305 0.296567 0.439654 0.063 Uiso 1 1 calc R U . . .
C6 C -0.3527(3) 0.4274(3) 0.5106(3) 0.0645(6) Uani 1 1 d . . . . .
H6A H -0.309602 0.503602 0.477809 0.097 Uiso 1 1 calc R U . . .
H6B H -0.372688 0.477077 0.596682 0.097 Uiso 1 1 calc R U . . .
H6C H -0.453618 0.352270 0.447178 0.097 Uiso 1 1 calc R U . . .
C7 C 0.5838(2) 0.7898(2) 0.9662(2) 0.0419(5) Uani 1 1 d . . . . .
H7 H 0.602010 0.834173 1.064838 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6104(2) 0.6349(2) 0.91730(18) 0.0391(4) Uani 1 1 d . . . . .
C9 C 0.4696(2) 0.51238(19) 0.83242(17) 0.0349(4) Uani 1 1 d . . . . .
C10 C 0.7592(2) 0.6127(2) 0.9524(2) 0.0475(5) Uani 1 1 d . . . . .
H10 H 0.852525 0.696412 1.009157 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7651(2) 0.4658(2) 0.9018(2) 0.0478(5) Uani 1 1 d . . . . .
H11 H 0.863618 0.450376 0.924883 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6261(2) 0.3377(2) 0.81580(18) 0.0404(4) Uani 1 1 d . . . . .
C13 C 0.4739(2) 0.3587(2) 0.77759(17) 0.0370(4) Uani 1 1 d . . . . .
C14 C 0.3387(2) 0.2273(2) 0.6874(2) 0.0466(5) Uani 1 1 d . . . . .
H14 H 0.238817 0.238891 0.660855 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3521(3) 0.0833(2) 0.6386(2) 0.0575(6) Uani 1 1 d . . . . .
H15 H 0.261817 -0.001437 0.578168 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5002(3) 0.0617(2) 0.6783(2) 0.0574(6) Uani 1 1 d . . . . .
H16 H 0.507343 -0.037127 0.645786 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6325(3) 0.1850(2) 0.7641(2) 0.0512(5) Uani 1 1 d . . . . .
H17 H 0.730304 0.169572 0.789845 0.061 Uiso 1 1 calc R U . . .
C18 C 0.9232(5) 0.9112(5) 0.7085(5) 0.1248(15) Uani 1 1 d . . . . .
H18A H 0.961933 1.020786 0.763322 0.187 Uiso 1 1 calc R U . . .
H18B H 0.813784 0.880047 0.653544 0.187 Uiso 1 1 calc R U . . .
H18C H 0.994143 0.886636 0.651227 0.187 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 C4 1.198(2) . ?
N1 C1 1.324(2) . ?
N1 N2 1.349(2) . ?
C1 C2 1.403(3) . ?
C1 C7 1.490(3) . ?
O2 C4 1.321(2) . ?
O2 C5 1.446(2) . ?
N2 C3 1.371(2) . ?
N2 H2N 0.94(3) . ?
C2 C3 1.391(3) . ?
C2 C9 1.483(2) . ?
O3 C7 1.420(2) . ?
O3 H3O 0.90(3) . ?
C3 C4 1.471(3) . ?
O4 C18 1.349(4) . ?
O4 H4O 0.91(3) . ?
C5 C6 1.487(3) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.516(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.386(3) . ?
C8 C10 1.399(3) . ?
C9 C13 1.424(2) . ?
C10 C11 1.367(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.421(3) . ?
C12 C13 1.428(3) . ?
C13 C14 1.411(3) . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.352(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C1 N1 N2 103.93(15) . . ?
N1 C1 C2 113.25(17) . . ?
N1 C1 C7 133.86(17) . . ?
C2 C1 C7 112.89(16) . . ?
C4 O2 C5 117.03(16) . . ?
N1 N2 C3 112.96(15) . . ?
N1 N2 H2N 118.5(16) . . ?
C3 N2 H2N 128.6(16) . . ?
C3 C2 C1 104.02(15) . . ?
C3 C2 C9 148.76(16) . . ?
C1 C2 C9 107.21(16) . . ?
C7 O3 H3O 106.6(16) . . ?
N2 C3 C2 105.83(16) . . ?
N2 C3 C4 118.29(16) . . ?
C2 C3 C4 135.84(16) . . ?
C18 O4 H4O 112(2) . . ?
O1 C4 O2 123.38(19) . . ?
O1 C4 C3 126.08(18) . . ?
O2 C4 C3 110.53(16) . . ?
O2 C5 C6 106.96(18) . . ?
O2 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O2 C5 H5AB 110.3 . . ?
C6 C5 H5AB 110.3 . . ?
H5A C5 H5AB 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C1 114.74(16) . . ?
O3 C7 C8 110.80(15) . . ?
C1 C7 C8 99.92(14) . . ?
O3 C7 H7 110.3 . . ?
C1 C7 H7 110.3 . . ?
C8 C7 H7 110.3 . . ?
C9 C8 C10 121.85(17) . . ?
C9 C8 C7 113.06(16) . . ?
C10 C8 C7 125.09(17) . . ?
C8 C9 C13 120.09(16) . . ?
C8 C9 C2 106.92(15) . . ?
C13 C9 C2 132.98(17) . . ?
C11 C10 C8 118.81(18) . . ?
C11 C10 H10 120.6 . . ?
C8 C10 H10 120.6 . . ?
C10 C11 C12 121.67(18) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C17 121.45(18) . . ?
C11 C12 C13 120.17(17) . . ?
C17 C12 C13 118.39(18) . . ?
C14 C13 C9 124.34(17) . . ?
C14 C13 C12 118.25(16) . . ?
C9 C13 C12 117.40(17) . . ?
C15 C14 C13 121.07(18) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.75(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 121.68(19) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N2 N1 C1 C2 -0.9(2) . . . . ?
N2 N1 C1 C7 -179.96(19) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C7 C1 C2 C3 179.89(15) . . . . ?
N1 C1 C2 C9 -179.45(15) . . . . ?
C7 C1 C2 C9 -0.2(2) . . . . ?
N1 N2 C3 C2 -0.5(2) . . . . ?
N1 N2 C3 C4 -178.60(15) . . . . ?
C1 C2 C3 N2 -0.06(19) . . . . ?
C9 C2 C3 N2 -179.9(3) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C9 C2 C3 C4 -2.3(4) . . . . ?
C5 O2 C4 O1 -1.6(3) . . . . ?
C5 O2 C4 C3 179.89(15) . . . . ?
N2 C3 C4 O1 -161.1(2) . . . . ?
C2 C3 C4 O1 21.5(4) . . . . ?
N2 C3 C4 O2 17.4(2) . . . . ?
C2 C3 C4 O2 -160.0(2) . . . . ?
C4 O2 C5 C6 165.62(17) . . . . ?
N1 C1 C7 O3 -62.5(3) . . . . ?
C2 C1 C7 O3 118.43(17) . . . . ?
N1 C1 C7 C8 179.0(2) . . . . ?
C2 C1 C7 C8 -0.09(19) . . . . ?
O3 C7 C8 C9 -121.05(17) . . . . ?
C1 C7 C8 C9 0.35(19) . . . . ?
O3 C7 C8 C10 59.3(2) . . . . ?
C1 C7 C8 C10 -179.26(17) . . . . ?
C10 C8 C9 C13 -0.4(3) . . . . ?
C7 C8 C9 C13 -179.99(15) . . . . ?
C10 C8 C9 C2 179.16(16) . . . . ?
C7 C8 C9 C2 -0.5(2) . . . . ?
C3 C2 C9 C8 -179.7(3) . . . . ?
C1 C2 C9 C8 0.39(19) . . . . ?
C3 C2 C9 C13 -0.3(4) . . . . ?
C1 C2 C9 C13 179.82(18) . . . . ?
C9 C8 C10 C11 -0.3(3) . . . . ?
C7 C8 C10 C11 179.28(18) . . . . ?
C8 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C17 -179.63(19) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C8 C9 C13 C14 -178.10(17) . . . . ?
C2 C9 C13 C14 2.5(3) . . . . ?
C8 C9 C13 C12 1.2(2) . . . . ?
C2 C9 C13 C12 -178.20(17) . . . . ?
C11 C12 C13 C14 177.95(17) . . . . ?
C17 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 C13 C9 -1.4(3) . . . . ?
C17 C12 C13 C9 179.01(16) . . . . ?
C9 C13 C14 C15 179.78(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C11 C12 C17 C16 -178.18(19) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and Methanol'
