# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1861614'
loop_
_audit_author_name
_audit_author_address
'Geeta Hundal'
;Jawaharlal Nehru University
India
;
_audit_update_record             
;
2018-08-12 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          190
_chemical_formula_moiety         'C18 H20 N4 O4'
_chemical_formula_sum            'C18 H20 N4 O4'
_chemical_formula_weight         356.38

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.189(5)
_cell_length_b                   7.915(4)
_cell_length_c                   10.643(3)
_cell_angle_alpha                80.745(13)
_cell_angle_beta                 82.34(4)
_cell_angle_gamma                88.94(5)
_cell_volume                     427.6(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1571
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.98

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5093
_exptl_absorpt_correction_T_max  0.74580
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction  
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6013
_diffrn_reflns_av_R_equivalents  0.1161
_diffrn_reflns_av_sigmaI/netI    0.2561
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2601
_reflns_number_gt                1873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration unk
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         2601
_refine_ls_number_parameters     236
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0365(8) 0.0950(6) 0.2735(4) 0.0328(11) Uani 1 1 d . . .
O2 O 0.5910(9) 0.2854(6) 0.4953(4) 0.0351(12) Uani 1 1 d . . .
O3 O -0.2740(11) 0.6216(7) -0.2426(4) 0.0481(15) Uani 1 1 d . . .
O4 O 0.0512(13) 0.7896(8) -0.2685(5) 0.0597(17) Uani 1 1 d . . .
N1 N 0.4492(11) 0.0518(6) 0.3131(4) 0.0242(12) Uani 1 1 d . . .
H1 H 0.6123 0.0399 0.2806 0.029 Uiso 1 1 d R . .
N2 N 0.1580(10) 0.2885(7) 0.5085(4) 0.0284(13) Uani 1 1 d . . .
H2A H 0.0166 0.2287 0.5088 0.034 Uiso 1 1 d R . .
N3 N -0.0787(13) 0.5485(7) 0.3348(5) 0.0375(15) Uani 1 1 d . . .
H3A H -0.2116 0.4907 0.3807 0.045 Uiso 1 1 d R . .
N4 N -0.1076(14) 0.6928(8) -0.1979(5) 0.0406(17) Uani 1 1 d . . .
C1 C 0.3612(13) 0.1205(8) 0.0906(5) 0.0281(15) Uani 1 1 d . . .
C2 C 0.2120(11) 0.2229(8) 0.0104(5) 0.0251(15) Uani 1 1 d . . .
H2 H 0.0554 0.2710 0.0462 0.030 Uiso 1 1 calc R . .
C3 C 0.2867(15) 0.2565(9) -0.1208(6) 0.0363(17) Uani 1 1 d . . .
H3 H 0.1795 0.3263 -0.1736 0.044 Uiso 1 1 calc R . .
C4 C 0.5117(13) 0.1915(9) -0.1761(6) 0.0301(15) Uani 1 1 d . . .
H4 H 0.5634 0.2165 -0.2662 0.036 Uiso 1 1 calc R . .
C5 C 0.6645(14) 0.0862(9) -0.0958(6) 0.0325(16) Uani 1 1 d . . .
H5 H 0.8215 0.0392 -0.1321 0.039 Uiso 1 1 calc R . .
C6 C 0.5883(11) 0.0502(8) 0.0362(5) 0.0238(14) Uani 1 1 d . . .
H6 H 0.6918 -0.0225 0.0892 0.029 Uiso 1 1 calc R . .
C7 C 0.2705(10) 0.0886(7) 0.2317(5) 0.0171(12) Uani 1 1 d . . .
C8 C 0.3809(12) 0.0300(8) 0.4544(5) 0.0216(13) Uani 1 1 d . . .
H8 H 0.2022 -0.0197 0.4794 0.026 Uiso 1 1 calc R . .
C9 C 0.3856(13) 0.2114(8) 0.4890(5) 0.0246(14) Uani 1 1 d . . .
C10 C 0.1239(13) 0.4672(8) 0.5288(6) 0.0316(16) Uani 1 1 d . . .
H10A H 0.2698 0.5003 0.5710 0.038 Uiso 1 1 calc R . .
H10B H -0.0390 0.4768 0.5872 0.038 Uiso 1 1 calc R . .
C11 C 0.1129(13) 0.5916(9) 0.4032(6) 0.0303(16) Uani 1 1 d . . .
H11A H 0.0799 0.7086 0.4232 0.036 Uiso 1 1 calc R . .
H11B H 0.2837 0.5925 0.3491 0.036 Uiso 1 1 calc R . .
C12 C -0.0922(13) 0.5894(8) 0.2050(6) 0.0263(15) Uani 1 1 d . . .
C13 C -0.2693(17) 0.5142(8) 0.1484(6) 0.040(2) Uani 1 1 d . . .
H13 H -0.3884 0.4344 0.2010 0.048 Uiso 1 1 calc R . .
C14 C -0.2851(15) 0.5486(9) 0.0170(6) 0.0352(17) Uani 1 1 d . . .
H14 H -0.4187 0.4995 -0.0186 0.042 Uiso 1 1 calc R . .
C15 C -0.0958(17) 0.6589(9) -0.0620(6) 0.039(2) Uani 1 1 d . . .
C16 C 0.0927(15) 0.7311(8) -0.0078(6) 0.0345(18) Uani 1 1 d . . .
H16 H 0.2207 0.8038 -0.0611 0.041 Uiso 1 1 calc R . .
C17 C 0.0973(15) 0.6993(8) 0.1216(6) 0.0341(17) Uani 1 1 d . . .
H17 H 0.2285 0.7507 0.1573 0.041 Uiso 1 1 calc R . .
C18 C 0.5758(13) -0.0859(8) 0.5213(6) 0.0284(14) Uani 1 1 d . . .
H18A H 0.7484 -0.0324 0.5017 0.043 Uiso 1 1 calc R . .
H18B H 0.5822 -0.1966 0.4910 0.043 Uiso 1 1 calc R . .
H18C H 0.5224 -0.1032 0.6143 0.043 Uiso 1 1 calc R . .


_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 C7 1.239(7) . ?
O2 C9 1.240(8) . ?
O3 N4 1.226(8) . ?
O4 N4 1.226(9) . ?
N1 C7 1.349(7) . ?
N1 C8 1.481(7) . ?
N1 H1 0.8795 . ?
N2 C9 1.326(8) . ?
N2 C10 1.469(8) . ?
N2 H2A 0.8801 . ?
N3 C12 1.378(8) . ?
N3 C11 1.386(9) . ?
N3 H3A 0.8793 . ?
N4 C15 1.438(8) . ?
C1 C2 1.384(9) . ?
C1 C6 1.389(9) . ?
C1 C7 1.495(7) . ?
C2 C3 1.382(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C18 1.523(9) . ?
C8 C9 1.540(8) . ?
C8 H8 1.0000 . ?
C10 C11 1.535(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.358(10) . ?
C12 C17 1.436(9) . ?
C13 C14 1.395(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(11) . ?
C16 C17 1.363(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C7 N1 C8 122.5(5) . . ?
C7 N1 H1 118.4 . . ?
C8 N1 H1 119.1 . . ?
C9 N2 C10 124.9(5) . . ?
C9 N2 H2A 117.8 . . ?
C10 N2 H2A 117.3 . . ?
C12 N3 C11 128.4(5) . . ?
C12 N3 H3A 115.8 . . ?
C11 N3 H3A 115.7 . . ?
O4 N4 O3 120.5(6) . . ?
O4 N4 C15 120.0(7) . . ?
O3 N4 C15 119.5(7) . . ?
C2 C1 C6 118.5(5) . . ?
C2 C1 C7 118.8(5) . . ?
C6 C1 C7 122.7(6) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.1(6) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 120.1(6) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 N1 120.4(5) . . ?
O1 C7 C1 121.1(5) . . ?
N1 C7 C1 118.5(5) . . ?
N1 C8 C18 110.8(5) . . ?
N1 C8 C9 105.6(4) . . ?
C18 C8 C9 111.0(5) . . ?
N1 C8 H8 109.8 . . ?
C18 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
O2 C9 N2 120.9(6) . . ?
O2 C9 C8 122.4(6) . . ?
N2 C9 C8 116.7(6) . . ?
N2 C10 C11 112.7(5) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N3 C11 C10 112.6(5) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 N3 121.4(6) . . ?
C13 C12 C17 116.9(6) . . ?
N3 C12 C17 121.4(7) . . ?
C12 C13 C14 123.2(7) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 118.1(7) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 119.9(6) . . ?
C16 C15 N4 121.6(7) . . ?
C14 C15 N4 118.5(7) . . ?
C17 C16 C15 120.6(7) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 121.3(7) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 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
C6 C1 C2 C3 -0.5(9) . . . . ?
C7 C1 C2 C3 -180.0(6) . . . . ?
C1 C2 C3 C4 -0.7(9) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C2 C1 C6 C5 1.4(9) . . . . ?
C7 C1 C6 C5 -179.2(6) . . . . ?
C4 C5 C6 C1 -1.0(10) . . . . ?
C8 N1 C7 O1 -4.6(8) . . . . ?
C8 N1 C7 C1 175.7(5) . . . . ?
C2 C1 C7 O1 26.6(8) . . . . ?
C6 C1 C7 O1 -152.8(6) . . . . ?
C2 C1 C7 N1 -153.7(5) . . . . ?
C6 C1 C7 N1 26.9(8) . . . . ?
C7 N1 C8 C18 153.8(5) . . . . ?
C7 N1 C8 C9 -85.9(6) . . . . ?
C10 N2 C9 O2 4.9(8) . . . . ?
C10 N2 C9 C8 -173.2(5) . . . . ?
N1 C8 C9 O2 -78.4(6) . . . . ?
C18 C8 C9 O2 41.7(7) . . . . ?
N1 C8 C9 N2 99.7(6) . . . . ?
C18 C8 C9 N2 -140.2(5) . . . . ?
C9 N2 C10 C11 91.1(7) . . . . ?
C12 N3 C11 C10 -156.1(6) . . . . ?
N2 C10 C11 N3 55.6(8) . . . . ?
C11 N3 C12 C13 168.8(6) . . . . ?
C11 N3 C12 C17 -4.5(10) . . . . ?
N3 C12 C13 C14 -178.2(6) . . . . ?
C17 C12 C13 C14 -4.7(10) . . . . ?
C12 C13 C14 C15 4.2(10) . . . . ?
C13 C14 C15 C16 -1.3(9) . . . . ?
C13 C14 C15 N4 179.0(6) . . . . ?
O4 N4 C15 C16 -0.7(9) . . . . ?
O3 N4 C15 C16 177.8(6) . . . . ?
O4 N4 C15 C14 179.0(6) . . . . ?
O3 N4 C15 C14 -2.5(9) . . . . ?
C14 C15 C16 C17 -0.8(10) . . . . ?
N4 C15 C16 C17 178.9(6) . . . . ?
C15 C16 C17 C12 0.3(10) . . . . ?
C13 C12 C17 C16 2.4(9) . . . . ?
N3 C12 C17 C16 175.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.109
