# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_na-10r_auto
_database_code_depnum_ccdc_archive 'CCDC 2300460'
loop_
_audit_author_name
_audit_author_address
'Ram Kumar Tittal'
;NIT Kurukshetra
India
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-10-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13.75 H10.75 N O4'
_chemical_formula_sum            'C13.75 H10.75 N O4'
_chemical_formula_weight         253.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     07-10-2023
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
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                   4.7711(6)
_cell_length_b                   13.430(5)
_cell_length_c                   19.544(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.722(10)
_cell_angle_gamma                90
_cell_volume                     1248.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    794
_cell_measurement_temperature    216(50)
_cell_measurement_theta_max      27.9910
_cell_measurement_theta_min      3.4850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.512
_diffrn_reflns_Laue_measured_fraction_max 0.512
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            1719
_diffrn_reflns_point_group_measured_fraction_full 0.512
_diffrn_reflns_point_group_measured_fraction_max 0.512
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         3.485
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      216(50)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.512
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00   8.00   0.50    4.00    --   -4.91 -38.00  60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0352649000
_diffrn_orient_matrix_UB_12      0.0453836000
_diffrn_orient_matrix_UB_13      -0.0157416000
_diffrn_orient_matrix_UB_21      0.0179425000
_diffrn_orient_matrix_UB_22      0.0231573000
_diffrn_orient_matrix_UB_23      0.0326851000
_diffrn_orient_matrix_UB_31      0.1438228000
_diffrn_orient_matrix_UB_32      -0.0140406000
_diffrn_orient_matrix_UB_33      0.0028530000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                807
_reflns_number_total             1094
_reflns_odcompleteness_completeness 81.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.32
_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       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1073P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1805
_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,H) groups
2. Others
 Fixed Sof: C00I(0.75) H00I(0.75)
3.a Rotating group:
 N005(H00A,H00B)
3.b Secondary CH2 refined with riding coordinates:
 C00E(H00E,H00F), C00F(H00G,H00H)
3.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00C), C00C(H00D)
3.d :
 C00I(H00I), C00J(H00J)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O001 O -0.3861(5) -0.5772(3) -0.37859(11) 0.0475(12) Uani 1 1 d . . . . .
O002 O -0.4491(5) -0.2248(3) -0.39333(11) 0.0499(13) Uani 1 1 d . . . . .
O003 O -0.7548(7) -0.1373(4) -0.33694(12) 0.0591(15) Uani 1 1 d . . . . .
O004 O -0.6509(6) -0.6673(4) -0.31212(13) 0.0562(15) Uani 1 1 d . . . . .
N005 N -1.1667(6) -0.4014(4) -0.18371(12) 0.0492(15) Uani 1 1 d . . . . .
H00A H -1.272332 -0.348193 -0.187620 0.059 Uiso 1 1 d R U . . .
H00B H -1.072423 -0.400798 -0.143516 0.059 Uiso 1 1 d R U . . .
C006 C -0.6812(7) -0.4904(4) -0.30901(14) 0.0385(15) Uani 1 1 d . . . . .
C007 C -0.7167(7) -0.3127(4) -0.31748(14) 0.0382(15) Uani 1 1 d . . . . .
C008 C -0.5769(7) -0.5864(4) -0.33170(16) 0.0409(17) Uani 1 1 d . . . . .
C009 C -0.8699(7) -0.4903(4) -0.25758(13) 0.0388(15) Uani 1 1 d . . . . .
H009 H -0.919855 -0.550617 -0.237454 0.047 Uiso 1 1 calc R U . . .
C00A C -0.9070(7) -0.3113(4) -0.26672(13) 0.0412(15) Uani 1 1 d . . . . .
H00C H -0.983249 -0.250619 -0.253061 0.049 Uiso 1 1 calc R U . . .
C00B C -0.6495(8) -0.2159(5) -0.34847(15) 0.0426(17) Uani 1 1 d . . . . .
C00C C -0.6052(7) -0.4009(4) -0.33863(14) 0.0372(16) Uani 1 1 d . . . . .
H00D H -0.478285 -0.400924 -0.372947 0.045 Uiso 1 1 calc R U . . .
C00D C -0.9835(7) -0.4009(4) -0.23624(14) 0.0379(15) Uani 1 1 d . . . . .
C00E C -0.2906(8) -0.6701(5) -0.40645(18) 0.0522(18) Uani 1 1 d . . . . .
H00E H -0.450857 -0.709213 -0.426125 0.063 Uiso 1 1 calc R U . . .
H00F H -0.187655 -0.709523 -0.370453 0.063 Uiso 1 1 calc R U . . .
C00F C -0.3846(8) -0.1376(5) -0.43020(17) 0.058(2) Uani 1 1 d . . . . .
H00G H -0.199546 -0.145298 -0.447903 0.070 Uiso 1 1 calc R U . . .
H00H H -0.375655 -0.080371 -0.398973 0.070 Uiso 1 1 calc R U . . .
C00G C -0.5969(9) -0.1184(5) -0.48787(18) 0.0548(19) Uani 1 1 d . . . . .
C00H C -0.1065(8) -0.6429(5) -0.45961(17) 0.0551(19) Uani 1 1 d . . . . .
C00I C -0.7685(11) -0.1041(6) -0.5335(2) 0.046(2) Uani 0.75 1 d . . P . .
H00I H -0.905758 -0.092773 -0.570013 0.056 Uiso 0.75 1 calc R U P . .
C00J C 0.0404(12) -0.6244(7) -0.5022(2) 0.083(3) Uani 1 1 d . . . . .
H00J H 0.159534 -0.609273 -0.536739 0.100 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
O001 C008 1.350(5) . ?
O001 C00E 1.449(7) . ?
O002 C00B 1.354(4) . ?
O002 C00F 1.422(7) . ?
O003 C00B 1.199(7) . ?
O004 C008 1.214(7) . ?
N005 H00A 0.8737 . ?
N005 H00B 0.8725 . ?
N005 C00D 1.402(4) . ?
C006 C008 1.464(7) . ?
C006 C009 1.404(5) . ?
C006 C00C 1.394(7) . ?
C007 C00A 1.399(5) . ?
C007 C00B 1.480(8) . ?
C007 C00C 1.377(7) . ?
C009 H009 0.9400 . ?
C009 C00D 1.395(7) . ?
C00A H00C 0.9400 . ?
C00A C00D 1.404(7) . ?
C00C H00D 0.9400 . ?
C00E H00E 0.9800 . ?
C00E H00F 0.9800 . ?
C00E C00H 1.461(6) . ?
C00F H00G 0.9800 . ?
C00F H00H 0.9800 . ?
C00F C00G 1.475(6) . ?
C00G C00I 1.176(6) . ?
C00H C00J 1.158(6) . ?
C00I H00I 0.9400 . ?
C00J H00J 0.9400 . ?

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
C008 O001 C00E 115.2(4) . . ?
C00B O002 C00F 116.7(5) . . ?
H00A N005 H00B 108.8 . . ?
C00D N005 H00A 108.8 . . ?
C00D N005 H00B 110.7 . . ?
C009 C006 C008 118.1(5) . . ?
C00C C006 C008 121.8(4) . . ?
C00C C006 C009 120.0(5) . . ?
C00A C007 C00B 117.0(5) . . ?
C00C C007 C00A 120.9(5) . . ?
C00C C007 C00B 122.1(4) . . ?
O001 C008 C006 112.9(5) . . ?
O004 C008 O001 121.8(5) . . ?
O004 C008 C006 125.3(4) . . ?
C006 C009 H009 119.9 . . ?
C00D C009 C006 120.2(5) . . ?
C00D C009 H009 119.9 . . ?
C007 C00A H00C 120.1 . . ?
C007 C00A C00D 119.7(5) . . ?
C00D C00A H00C 120.1 . . ?
O002 C00B C007 112.1(5) . . ?
O003 C00B O002 121.9(5) . . ?
O003 C00B C007 126.0(4) . . ?
C006 C00C H00D 120.1 . . ?
C007 C00C C006 119.8(4) . . ?
C007 C00C H00D 120.1 . . ?
N005 C00D C00A 121.0(5) . . ?
C009 C00D N005 119.7(5) . . ?
C009 C00D C00A 119.3(4) . . ?
O001 C00E H00E 110.5 . . ?
O001 C00E H00F 110.5 . . ?
O001 C00E C00H 106.2(5) . . ?
H00E C00E H00F 108.7 . . ?
C00H C00E H00E 110.5 . . ?
C00H C00E H00F 110.5 . . ?
O002 C00F H00G 109.3 . . ?
O002 C00F H00H 109.3 . . ?
O002 C00F C00G 111.6(4) . . ?
H00G C00F H00H 108.0 . . ?
C00G C00F H00G 109.3 . . ?
C00G C00F H00H 109.3 . . ?
C00I C00G C00F 179.0(6) . . ?
C00J C00H C00E 178.0(7) . . ?
C00G C00I H00I 180.0 . . ?
C00H C00J H00J 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
C006 C009 C00D N005 -178.5(2) . . . . ?
C006 C009 C00D C00A 0.0(4) . . . . ?
C007 C00A C00D N005 177.9(2) . . . . ?
C007 C00A C00D C009 -0.5(4) . . . . ?
C008 O001 C00E C00H 175.3(2) . . . . ?
C008 C006 C009 C00D -177.5(3) . . . . ?
C008 C006 C00C C007 177.6(3) . . . . ?
C009 C006 C008 O001 -176.7(2) . . . . ?
C009 C006 C008 O004 3.9(5) . . . . ?
C009 C006 C00C C007 -0.3(5) . . . . ?
C00A C007 C00B O002 175.7(2) . . . . ?
C00A C007 C00B O003 -4.5(5) . . . . ?
C00A C007 C00C C006 -0.3(5) . . . . ?
C00B O002 C00F C00G -78.7(5) . . . . ?
C00B C007 C00A C00D 178.8(3) . . . . ?
C00B C007 C00C C006 -178.3(3) . . . . ?
C00C C006 C008 O001 5.4(4) . . . . ?
C00C C006 C008 O004 -173.9(3) . . . . ?
C00C C006 C009 C00D 0.4(4) . . . . ?
C00C C007 C00A C00D 0.7(4) . . . . ?
C00C C007 C00B O002 -6.3(4) . . . . ?
C00C C007 C00B O003 173.5(3) . . . . ?
C00E O001 C008 O004 3.6(4) . . . . ?
C00E O001 C008 C006 -175.8(3) . . . . ?
C00F O002 C00B O003 -4.7(5) . . . . ?
C00F O002 C00B C007 175.1(3) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.932
# start Validation Reply Form
_vrf_PLAT088_na-10r_auto         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.32 Note  
RESPONSE: Crystal quality was sub-optimal; we were able to make only a single collection. Data were processed after some time: when we realized that completeness was low, crystals were no more available
;
_vrf_PLAT911_na-10r_auto         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.588        821 Report
RESPONSE: This is most probably related to low completness
;
# end Validation Reply Form
