# 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_nks_mkg_454b
_database_code_depnum_ccdc_archive 'CCDC 2098113'
loop_
_audit_author_name
_audit_author_address
'Nagendra K. Sharma'
;SCS, National Institute of Science Education and Research (NISER), Bhubaneswar, Odisha
India
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.9566(4)
_cell_length_b                   13.9478(11)
_cell_length_c                   8.1538(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.607(3)
_cell_angle_gamma                90
_cell_volume                     1309.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10426
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.839
_diffrn_reflns_theta_max         75.317
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2602
_reflns_number_gt                2307
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0628P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2602
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
O14 O 0.01434(8) 0.70312(8) 0.22241(11) 0.0550(3) Uani 1 1 d . . . . .
O12 O -0.06107(8) 0.61926(7) -0.01553(12) 0.0553(3) Uani 1 1 d . . . . .
N1 N 0.23898(9) 0.67668(7) 0.18235(13) 0.0430(3) Uani 1 1 d . . . . .
O17 O 0.13167(9) 0.98314(7) -0.02113(13) 0.0581(3) Uani 1 1 d . . . . .
C15 C 0.19554(11) 0.84053(9) 0.10724(15) 0.0437(3) Uani 1 1 d . . . . .
H15 H 0.1323 0.8166 0.0243 0.052 Uiso 1 1 calc R U . . .
O20 O 0.32458(9) 0.53214(7) 0.28150(14) 0.0614(3) Uani 1 1 d . . . . .
C8 C 0.37430(10) 0.77938(9) 0.34351(15) 0.0415(3) Uani 1 1 d . . . . .
O19 O 0.27091(13) 0.99248(8) 0.22073(18) 0.0902(5) Uani 1 1 d . . . . .
C9 C 0.26443(10) 0.77463(9) 0.20598(14) 0.0396(3) Uani 1 1 d . . . . .
C3 C 0.41058(10) 0.68595(9) 0.38757(15) 0.0440(3) Uani 1 1 d . . . . .
C2 C 0.32474(10) 0.61892(9) 0.28350(16) 0.0446(3) Uani 1 1 d . . . . .
C11 C 0.02609(11) 0.65776(8) 0.10345(14) 0.0415(3) Uani 1 1 d . . . . .
C16 C 0.20751(12) 0.94442(10) 0.11392(17) 0.0486(3) Uani 1 1 d . . . . .
C10 C 0.13883(11) 0.63686(10) 0.06121(16) 0.0468(3) Uani 1 1 d . . . . .
H10A H 0.1484 0.5679 0.0564 0.056 Uiso 1 1 calc R U . . .
H10B H 0.1349 0.6625 -0.0508 0.056 Uiso 1 1 calc R U . . .
C4 C 0.51198(12) 0.66439(11) 0.51066(17) 0.0549(4) Uani 1 1 d . . . . .
H4 H 0.5349 0.6013 0.5376 0.066 Uiso 1 1 calc R U . . .
C6 C 0.54282(13) 0.83376(12) 0.55099(19) 0.0607(4) Uani 1 1 d . . . . .
H6 H 0.5884 0.8837 0.6086 0.073 Uiso 1 1 calc R U . . .
C7 C 0.44146(12) 0.85512(10) 0.42614(17) 0.0523(3) Uani 1 1 d . . . . .
H7 H 0.4193 0.9183 0.3988 0.063 Uiso 1 1 calc R U . . .
C5 C 0.57764(12) 0.74052(13) 0.59172(19) 0.0617(4) Uani 1 1 d . . . . .
H5 H 0.6464 0.7288 0.6751 0.074 Uiso 1 1 calc R U . . .
C13 C -0.17638(12) 0.63832(12) 0.0010(2) 0.0641(4) Uani 1 1 d . . . . .
H13A H -0.2326 0.6068 -0.0893 0.096 Uiso 1 1 calc R U . . .
H13B H -0.1904 0.7062 -0.0054 0.096 Uiso 1 1 calc R U . . .
H13C H -0.1826 0.6147 0.1088 0.096 Uiso 1 1 calc R U . . .
C18 C 0.13375(16) 1.08554(11) -0.0355(2) 0.0699(5) Uani 1 1 d . . . . .
H18A H 0.0805 1.1050 -0.1407 0.105 Uiso 1 1 calc R U . . .
H18B H 0.2107 1.1061 -0.0335 0.105 Uiso 1 1 calc R U . . .
H18C H 0.1115 1.1141 0.0581 0.105 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
O14 C11 1.1976(15) . ?
O12 C11 1.3310(14) . ?
O12 C13 1.4456(18) . ?
N1 C2 1.3877(15) . ?
N1 C9 1.4016(15) . ?
N1 C10 1.4428(15) . ?
O17 C16 1.3376(16) . ?
O17 C18 1.4338(18) . ?
C15 C9 1.3471(17) . ?
C15 C16 1.4556(18) . ?
C15 H15 0.9300 . ?
O20 C2 1.2105(16) . ?
C8 C7 1.3870(18) . ?
C8 C3 1.3898(18) . ?
C8 C9 1.4816(16) . ?
O19 C16 1.1947(18) . ?
C3 C4 1.3831(17) . ?
C3 C2 1.4762(17) . ?
C11 C10 1.5068(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C6 C5 1.379(2) . ?
C6 C7 1.3892(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
C11 O12 C13 115.93(11) . . ?
C2 N1 C9 112.70(10) . . ?
C2 N1 C10 121.86(10) . . ?
C9 N1 C10 125.37(10) . . ?
C16 O17 C18 116.53(12) . . ?
C9 C15 C16 128.23(12) . . ?
C9 C15 H15 115.9 . . ?
C16 C15 H15 115.9 . . ?
C7 C8 C3 119.27(11) . . ?
C7 C8 C9 132.95(12) . . ?
C3 C8 C9 107.77(11) . . ?
C15 C9 N1 120.51(11) . . ?
C15 C9 C8 134.17(11) . . ?
N1 C9 C8 105.26(10) . . ?
C4 C3 C8 122.90(12) . . ?
C4 C3 C2 128.14(12) . . ?
C8 C3 C2 108.96(10) . . ?
O20 C2 N1 125.05(12) . . ?
O20 C2 C3 129.75(12) . . ?
N1 C2 C3 105.20(11) . . ?
O14 C11 O12 124.33(12) . . ?
O14 C11 C10 126.47(11) . . ?
O12 C11 C10 109.18(10) . . ?
O19 C16 O17 122.02(13) . . ?
O19 C16 C15 128.50(13) . . ?
O17 C16 C15 109.46(11) . . ?
N1 C10 C11 113.44(10) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C5 C4 C3 117.08(14) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C5 C6 C7 121.75(14) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 118.00(14) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C6 C5 C4 120.99(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O17 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
C16 C15 C9 N1 179.45(12) . . . . ?
C16 C15 C9 C8 -3.6(2) . . . . ?
C2 N1 C9 C15 174.16(11) . . . . ?
C10 N1 C9 C15 -2.71(18) . . . . ?
C2 N1 C9 C8 -3.55(13) . . . . ?
C10 N1 C9 C8 179.59(11) . . . . ?
C7 C8 C9 C15 4.6(2) . . . . ?
C3 C8 C9 C15 -174.41(13) . . . . ?
C7 C8 C9 N1 -178.14(13) . . . . ?
C3 C8 C9 N1 2.83(13) . . . . ?
C7 C8 C3 C4 -0.37(19) . . . . ?
C9 C8 C3 C4 178.81(12) . . . . ?
C7 C8 C3 C2 179.59(11) . . . . ?
C9 C8 C3 C2 -1.22(13) . . . . ?
C9 N1 C2 O20 -177.24(12) . . . . ?
C10 N1 C2 O20 -0.3(2) . . . . ?
C9 N1 C2 C3 2.82(13) . . . . ?
C10 N1 C2 C3 179.81(11) . . . . ?
C4 C3 C2 O20 -0.8(2) . . . . ?
C8 C3 C2 O20 179.19(14) . . . . ?
C4 C3 C2 N1 179.09(13) . . . . ?
C8 C3 C2 N1 -0.87(13) . . . . ?
C13 O12 C11 O14 2.50(19) . . . . ?
C13 O12 C11 C10 -176.20(12) . . . . ?
C18 O17 C16 O19 2.7(2) . . . . ?
C18 O17 C16 C15 -178.86(12) . . . . ?
C9 C15 C16 O19 -10.7(3) . . . . ?
C9 C15 C16 O17 170.93(12) . . . . ?
C2 N1 C10 C11 115.04(13) . . . . ?
C9 N1 C10 C11 -68.37(15) . . . . ?
O14 C11 C10 N1 0.72(19) . . . . ?
O12 C11 C10 N1 179.38(10) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C5 -179.50(13) . . . . ?
C3 C8 C7 C6 -0.25(19) . . . . ?
C9 C8 C7 C6 -179.18(13) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C7 C6 C5 C4 -0.7(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035

