# 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 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_DR16_a
_database_code_depnum_ccdc_archive 'CCDC 2016035'
loop_
_audit_author_name
_audit_author_address
'Moorthy Mathivanan'
;bharathiar university
India
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4 O4'
_chemical_formula_weight         380.40

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                   4.9758(2)
_cell_length_b                   13.6254(5)
_cell_length_c                   15.0972(6)
_cell_angle_alpha                63.6610(10)
_cell_angle_beta                 84.3720(10)
_cell_angle_gamma                82.3240(10)
_cell_volume                     908.20(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1007
_cell_measurement_theta_min      1.6701
_cell_measurement_theta_max      22.3702

_exptl_crystal_description       lump
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7129
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            52560
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.700
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4515
_reflns_number_gt                3388
_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       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_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)+(0.1030P)²+0.9518P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4515
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.2509
_refine_ls_wR_factor_gt          0.2355
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.5308(4) 0.57590(15) 0.64770(14) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.2576(5) 0.48682(16) 0.61282(15) 0.0525(6) Uani 1 1 d . . . . .
O3 O 0.4455(5) 0.84115(17) 0.37537(14) 0.0520(6) Uani 1 1 d . . . . .
H3A H 0.345832 0.829214 0.341837 0.078 Uiso 1 1 calc R U . . .
O4 O 0.0499(5) 0.88701(18) 0.15282(16) 0.0582(6) Uani 1 1 d . . . . .
N1 N 0.1306(5) 0.7325(2) 0.33426(17) 0.0429(6) Uani 1 1 d . . . . .
N2 N -0.0369(5) 0.7217(2) 0.27235(17) 0.0449(6) Uani 1 1 d . . . . .
H2A H -0.118671 0.663474 0.291196 0.054 Uiso 1 1 calc R U . . .
N3 N 1.0921(6) 0.7554(2) 0.75346(19) 0.0545(7) Uani 1 1 d . . . . .
N4 N -0.5949(6) 0.7748(3) -0.0123(2) 0.0598(8) Uani 1 1 d . . . . .
C1 C 0.3369(6) 0.6623(2) 0.48688(19) 0.0383(6) Uani 1 1 d . . . . .
C2 C 0.3647(6) 0.5706(2) 0.5828(2) 0.0400(6) Uani 1 1 d . . . . .
C3 C 0.6610(5) 0.6684(2) 0.62373(19) 0.0353(6) Uani 1 1 d . . . . .
C4 C 0.6365(5) 0.7598(2) 0.53200(18) 0.0356(6) Uani 1 1 d . . . . .
C5 C 0.4697(6) 0.7565(2) 0.46082(19) 0.0380(6) Uani 1 1 d . . . . .
C6 C 0.8137(6) 0.6645(2) 0.69656(19) 0.0391(6) Uani 1 1 d . . . . .
H6A H 0.825664 0.601863 0.756659 0.047 Uiso 1 1 calc R U . . .
C7 C 0.9511(6) 0.7544(2) 0.68053(19) 0.0397(6) Uani 1 1 d . . . . .
C8 C 0.9326(6) 0.8465(2) 0.5866(2) 0.0438(7) Uani 1 1 d . . . . .
H8A H 1.026899 0.906490 0.573015 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7781(6) 0.8485(2) 0.51549(19) 0.0427(7) Uani 1 1 d . . . . .
H9A H 0.767305 0.910398 0.454825 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1658(6) 0.6537(2) 0.4208(2) 0.0412(6) Uani 1 1 d . . . . .
H10A H 0.078967 0.590441 0.440696 0.049 Uiso 1 1 calc R U . . .
C11 C -0.0687(6) 0.8057(2) 0.1808(2) 0.0418(6) Uani 1 1 d . . . . .
C12 C -0.2559(6) 0.7901(2) 0.1171(2) 0.0391(6) Uani 1 1 d . . . . .
C13 C -0.3942(7) 0.6982(3) 0.1450(2) 0.0496(7) Uani 1 1 d . . . . .
H13A H -0.376819 0.639972 0.207750 0.060 Uiso 1 1 calc R U . . .
C14 C -0.5578(7) 0.6947(3) 0.0780(3) 0.0566(8) Uani 1 1 d . . . . .
H14A H -0.647892 0.632316 0.097418 0.068 Uiso 1 1 calc R U . . .
C15 C -0.4636(8) 0.8627(3) -0.0377(2) 0.0582(9) Uani 1 1 d . . . . .
H15A H -0.487898 0.920302 -0.100411 0.070 Uiso 1 1 calc R U . . .
C16 C -0.2933(7) 0.8738(3) 0.0233(2) 0.0483(7) Uani 1 1 d . . . . .
H16A H -0.204705 0.936953 0.001554 0.058 Uiso 1 1 calc R U . . .
C17 C 1.0507(8) 0.6742(3) 0.8596(3) 0.0655(10) Uani 1 1 d . . . . .
H17A H 1.069344 0.708984 0.902203 0.079 Uiso 1 1 calc R U . . .
H17B H 0.868218 0.652192 0.870359 0.079 Uiso 1 1 calc R U . . .
C18 C 1.2452(9) 0.5775(4) 0.8856(4) 0.0898(15) Uani 1 1 d . . . . .
H18A H 1.213702 0.527304 0.953636 0.135 Uiso 1 1 calc R U . . .
H18B H 1.224901 0.542275 0.844258 0.135 Uiso 1 1 calc R U . . .
H18C H 1.425815 0.599007 0.876069 0.135 Uiso 1 1 calc R U . . .
C19 C 1.2530(7) 0.8459(3) 0.7354(2) 0.0504(7) Uani 1 1 d . . . . .
H19A H 1.329677 0.873945 0.668165 0.060 Uiso 1 1 calc R U . . .
H19B H 1.402040 0.817781 0.779847 0.060 Uiso 1 1 calc R U . . .
C20 C 1.0876(9) 0.9382(3) 0.7502(3) 0.0651(10) Uani 1 1 d . . . . .
H20A H 1.200764 0.995177 0.737654 0.098 Uiso 1 1 calc R U . . .
H20B H 0.941918 0.967287 0.705432 0.098 Uiso 1 1 calc R U . . .
H20C H 1.014266 0.911136 0.817089 0.098 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 C2 1.373(3) . ?
O1 C3 1.381(3) . ?
O2 C2 1.204(3) . ?
O3 C5 1.297(3) . ?
O3 H3A 0.8200 . ?
O4 C11 1.210(3) . ?
N1 C10 1.281(4) . ?
N1 N2 1.378(3) . ?
N2 C11 1.355(4) . ?
N2 H2A 0.8600 . ?
N3 C7 1.369(3) . ?
N3 C19 1.468(4) . ?
N3 C17 1.503(4) . ?
N4 C14 1.327(4) . ?
N4 C15 1.327(5) . ?
C1 C5 1.403(4) . ?
C1 C10 1.425(3) . ?
C1 C2 1.437(4) . ?
C3 C6 1.375(3) . ?
C3 C4 1.395(3) . ?
C4 C9 1.395(3) . ?
C4 C5 1.440(3) . ?
C6 C7 1.398(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.418(4) . ?
C8 C9 1.369(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.501(4) . ?
C12 C16 1.379(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.379(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.449(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.499(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 O1 C3 121.3(2) . . ?
C5 O3 H3A 109.5 . . ?
C10 N1 N2 119.0(2) . . ?
C11 N2 N1 117.9(2) . . ?
C11 N2 H2A 121.0 . . ?
N1 N2 H2A 121.0 . . ?
C7 N3 C19 122.0(2) . . ?
C7 N3 C17 120.9(2) . . ?
C19 N3 C17 116.3(2) . . ?
C14 N4 C15 116.4(3) . . ?
C5 C1 C10 121.9(2) . . ?
C5 C1 C2 121.0(2) . . ?
C10 C1 C2 117.1(2) . . ?
O2 C2 O1 115.3(2) . . ?
O2 C2 C1 126.2(2) . . ?
O1 C2 C1 118.5(2) . . ?
C6 C3 O1 115.5(2) . . ?
C6 C3 C4 122.5(2) . . ?
O1 C3 C4 122.0(2) . . ?
C9 C4 C3 117.2(2) . . ?
C9 C4 C5 124.4(2) . . ?
C3 C4 C5 118.4(2) . . ?
O3 C5 C1 122.4(2) . . ?
O3 C5 C4 118.9(2) . . ?
C1 C5 C4 118.7(2) . . ?
C3 C6 C7 120.2(2) . . ?
C3 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
N3 C7 C6 121.5(2) . . ?
N3 C7 C8 120.8(2) . . ?
C6 C7 C8 117.6(2) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C4 121.5(2) . . ?
C8 C9 H9A 119.3 . . ?
C4 C9 H9A 119.3 . . ?
N1 C10 C1 120.5(2) . . ?
N1 C10 H10A 119.7 . . ?
C1 C10 H10A 119.7 . . ?
O4 C11 N2 121.6(2) . . ?
O4 C11 C12 122.8(3) . . ?
N2 C11 C12 115.6(2) . . ?
C16 C12 C13 117.5(3) . . ?
C16 C12 C11 117.3(3) . . ?
C13 C12 C11 125.2(2) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
N4 C14 C13 124.2(3) . . ?
N4 C14 H14A 117.9 . . ?
C13 C14 H14A 117.9 . . ?
N4 C15 C16 124.0(3) . . ?
N4 C15 H15A 118.0 . . ?
C16 C15 H15A 118.0 . . ?
C12 C16 C15 119.2(3) . . ?
C12 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C18 C17 N3 111.4(4) . . ?
C18 C17 H17A 109.3 . . ?
N3 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N3 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.4(3) . . ?
N3 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.061

