# 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 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2004227'
loop_
_audit_author_name
_audit_author_address
'Pallavi Rungta'
;University of Delhi
India
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-12-09 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            'C11 H14 N6 O5'
_chemical_formula_weight         310.28

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.820(2)
_cell_length_b                   6.612(3)
_cell_length_c                   14.279(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.88(4)
_cell_angle_gamma                90
_cell_volume                     643.4(5)
_cell_formula_units_Z            2
_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    1.601
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.129
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7538
_diffrn_reflns_av_unetI/netI     0.1606
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2249
_reflns_number_gt                995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0605P)²] 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       0.033(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   4.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2249
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1788
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
C1 C 0.9346(14) 0.3549(16) 0.4387(6) 0.044(3) Uani 1 1 d . . . . .
C2 C 1.0091(14) 0.3635(18) 0.5327(7) 0.047(3) Uani 1 1 d . . . . .
H2 H 1.1420 0.3813 0.5470 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8787(13) 0.3447(16) 0.5991(7) 0.044(3) Uani 1 1 d . . . . .
H3 H 0.9227 0.3415 0.6614 0.053 Uiso 1 1 calc R U . . .
C4 C 0.6139(13) 0.3315(18) 0.4858(7) 0.045(3) Uani 1 1 d . . . . .
C5 C 0.5463(13) 0.3188(18) 0.6542(6) 0.044(3) Uani 1 1 d . . . . .
H5 H 0.4152 0.2929 0.6267 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5331(16) 0.4977(18) 0.7194(9) 0.060(3) Uani 1 1 d . . . . .
H6 H 0.6118 0.6107 0.6969 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6112(15) 0.4261(19) 0.8133(9) 0.058(3) Uani 1 1 d . . . . .
H7 H 0.5472 0.4920 0.8657 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5674(18) 0.199(2) 0.8074(9) 0.059(3) Uani 1 1 d . . . . .
C9 C 0.688(2) 0.053(3) 0.8730(10) 0.095(6) Uani 1 1 d . . . . .
H9A H 0.7879 -0.0146 0.8377 0.114 Uiso 1 1 calc R U . . .
H9B H 0.7523 0.1291 0.9232 0.114 Uiso 1 1 calc R U . . .
C10 C 0.389(3) 0.005(3) 0.9119(11) 0.127(8) Uani 1 1 d . . . . .
H10A H 0.3771 0.0764 0.9707 0.153 Uiso 1 1 calc R U . . .
H10B H 0.2915 -0.1023 0.9093 0.153 Uiso 1 1 calc R U . . .
C11 C 0.3545(17) 0.145(2) 0.8329(8) 0.063(3) Uani 1 1 d . . . . .
H11 H 0.2880 0.2668 0.8550 0.076 Uiso 1 1 calc R U . . .
N1 N 1.0613(11) 0.3658(14) 0.3684(6) 0.056(3) Uani 1 1 d . . . . .
H1A H 1.0181 0.3655 0.3112 0.067 Uiso 1 1 calc R U . . .
H1B H 1.1854 0.3731 0.3808 0.067 Uiso 1 1 calc R U . . .
N2 N 0.7456(10) 0.3440(16) 0.4176(5) 0.046(2) Uani 1 1 d . . . . .
N3 N 0.6828(10) 0.3298(13) 0.5791(5) 0.039(2) Uani 1 1 d . . . . .
N4 N 0.8270(15) 0.448(2) 0.8184(8) 0.101(5) Uani 1 1 d . . . . .
N5 N 0.9009(17) 0.548(2) 0.8739(9) 0.079(3) Uani 1 1 d . . . . .
N6 N 0.986(2) 0.640(4) 0.9264(13) 0.167(8) Uani 1 1 d . . . . .
O1 O 0.3369(11) 0.5577(13) 0.7294(5) 0.079(3) Uani 1 1 d . . . . .
H1 H 0.2920 0.5990 0.6790 0.118 Uiso 1 1 calc R U . . .
O2 O 0.4367(9) 0.3216(15) 0.4690(5) 0.060(2) Uani 1 1 d . . . . .
O3 O 0.6022(9) 0.1471(13) 0.7126(5) 0.053(2) Uani 1 1 d . . . . .
O4 O 0.2442(11) 0.057(2) 0.7634(6) 0.121(5) Uani 1 1 d . . . . .
H4 H 0.2773 0.1015 0.7126 0.181 Uiso 1 1 calc R U . . .
O5 O 0.574(2) -0.077(2) 0.9070(13) 0.178(7) Uani 1 1 d . . . . .


_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
C1 N2 1.316(11) . ?
C1 N1 1.348(11) . ?
C1 C2 1.421(12) . ?
C2 C3 1.326(12) . ?
C2 H2 0.9300 . ?
C3 N3 1.360(11) . ?
C3 H3 0.9300 . ?
C4 O2 1.226(9) . ?
C4 N2 1.349(10) . ?
C4 N3 1.398(10) . ?
C5 N3 1.445(10) . ?
C5 O3 1.452(12) . ?
C5 C6 1.509(15) . ?
C5 H5 0.9800 . ?
C6 O1 1.408(12) . ?
C6 C7 1.503(15) . ?
C6 H6 0.9800 . ?
C7 N4 1.478(14) . ?
C7 C8 1.532(16) . ?
C7 H7 0.9800 . ?
C8 O3 1.424(13) . ?
C8 C11 1.550(15) . ?
C8 C9 1.561(17) . ?
C9 O5 1.267(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O5 1.37(2) . ?
C10 C11 1.474(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O4 1.357(13) . ?
C11 H11 0.9800 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N4 N5 1.140(15) . ?
N5 N6 1.115(16) . ?
O1 H1 0.8200 . ?
O4 H4 0.8200 . ?

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
N2 C1 N1 118.6(8) . . ?
N2 C1 C2 122.4(8) . . ?
N1 C1 C2 118.9(8) . . ?
C3 C2 C1 116.4(9) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 N3 122.2(9) . . ?
C2 C3 H3 118.9 . . ?
N3 C3 H3 118.9 . . ?
O2 C4 N2 122.5(9) . . ?
O2 C4 N3 119.0(8) . . ?
N2 C4 N3 118.5(8) . . ?
N3 C5 O3 107.6(8) . . ?
N3 C5 C6 118.1(10) . . ?
O3 C5 C6 106.2(7) . . ?
N3 C5 H5 108.2 . . ?
O3 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
O1 C6 C7 107.9(9) . . ?
O1 C6 C5 111.1(9) . . ?
C7 C6 C5 106.1(9) . . ?
O1 C6 H6 110.5 . . ?
C7 C6 H6 110.5 . . ?
C5 C6 H6 110.5 . . ?
N4 C7 C6 109.7(10) . . ?
N4 C7 C8 106.8(11) . . ?
C6 C7 C8 101.3(10) . . ?
N4 C7 H7 112.8 . . ?
C6 C7 H7 112.8 . . ?
C8 C7 H7 112.8 . . ?
O3 C8 C7 104.5(11) . . ?
O3 C8 C11 110.8(10) . . ?
C7 C8 C11 113.2(11) . . ?
O3 C8 C9 108.7(10) . . ?
C7 C8 C9 118.4(12) . . ?
C11 C8 C9 101.2(11) . . ?
O5 C9 C8 109.4(12) . . ?
O5 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
O5 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O5 C10 C11 109.4(14) . . ?
O5 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
O5 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
O4 C11 C10 111.2(13) . . ?
O4 C11 C8 115.3(9) . . ?
C10 C11 C8 101.4(11) . . ?
O4 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C8 C11 H11 109.6 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C4 120.5(8) . . ?
C3 N3 C4 119.8(7) . . ?
C3 N3 C5 120.0(7) . . ?
C4 N3 C5 120.2(7) . . ?
N5 N4 C7 120.5(12) . . ?
N6 N5 N4 174.7(17) . . ?
C6 O1 H1 109.5 . . ?
C8 O3 C5 107.9(8) . . ?
C11 O4 H4 109.5 . . ?
C9 O5 C10 109.2(15) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057



