# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DNMH
_database_code_depnum_ccdc_archive 'CCDC 2019887'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2022-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 N4 O4'
_chemical_formula_weight         336.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.787(2)
_cell_length_b                   12.178(5)
_cell_length_c                   17.714(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.997(11)
_cell_angle_gamma                90
_cell_volume                     1446.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2112
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   .981
_exptl_transmission_factor_max   .986
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10216
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2539
_reflns_number_gt                1613
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0364P)²+4.8771P] 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         2539
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
O001 O 0.2909(6) 0.1754(3) 0.4827(2) 0.0346(10) Uani 1 1 d . . . . .
O002 O 0.3250(6) 0.0576(3) 0.5756(2) 0.0391(11) Uani 1 1 d . . . . .
O1 O 0.4166(6) 0.3310(4) 0.8667(2) 0.0447(11) Uani 1 1 d . . . . .
O004 O 0.4328(6) 0.1600(4) 0.8352(2) 0.0434(11) Uani 1 1 d . . . . .
N005 N 0.2641(6) 0.3870(3) 0.5107(2) 0.0236(10) Uani 1 1 d . . . . .
H005 H 0.250703 0.339471 0.472795 0.028 Uiso 1 1 calc R U . . .
N1 N 0.3132(6) 0.1521(4) 0.5517(2) 0.0244(10) Uani 1 1 d . . . . .
N007 N 0.2488(6) 0.4984(4) 0.4970(2) 0.0260(11) Uani 1 1 d . . . . .
N2 N 0.4102(6) 0.2586(4) 0.8186(2) 0.0298(11) Uani 1 1 d . . . . .
C009 C 0.3249(7) 0.2409(4) 0.6072(3) 0.0179(11) Uani 1 1 d . . . . .
C00A C 0.3005(7) 0.3533(4) 0.5843(3) 0.0186(11) Uani 1 1 d . . . . .
C00B C 0.3610(7) 0.2115(4) 0.6831(3) 0.0205(12) Uani 1 1 d . . . . .
H00B H 0.376786 0.136243 0.696836 0.025 Uiso 1 1 calc R U . . .
C00C C 0.2069(8) 0.7215(4) 0.4638(3) 0.0254(13) Uani 1 1 d . . . . .
H00C H 0.229807 0.697485 0.515429 0.030 Uiso 1 1 calc R U . . .
C00D C 0.3744(8) 0.2907(5) 0.7392(3) 0.0251(12) Uani 1 1 d . . . . .
C00E C 0.1532(7) 0.6790(4) 0.3298(3) 0.0236(12) Uani 1 1 d . . . . .
C00F C 0.1898(7) 0.6443(4) 0.4074(3) 0.0214(12) Uani 1 1 d . . . . .
C00G C 0.3493(7) 0.4005(4) 0.7193(3) 0.0230(12) Uani 1 1 d . . . . .
H00G H 0.355781 0.455009 0.758017 0.028 Uiso 1 1 calc R U . . .
C00H C 0.2104(7) 0.5264(5) 0.4270(3) 0.0276(13) Uani 1 1 d . . . . .
H00H H 0.195237 0.472267 0.387842 0.033 Uiso 1 1 calc R U . . .
C00I C 0.3153(7) 0.4303(4) 0.6444(3) 0.0231(12) Uani 1 1 d . . . . .
H00I H 0.300982 0.506089 0.632041 0.028 Uiso 1 1 calc R U . . .
C00J C 0.0859(8) 0.6419(4) 0.1924(3) 0.0266(13) Uani 1 1 d . . . . .
H00J H 0.066885 0.590948 0.151279 0.032 Uiso 1 1 calc R U . . .
C00K C 0.1372(7) 0.7929(4) 0.3128(3) 0.0214(12) Uani 1 1 d . . . . .
C00L C 0.1250(7) 0.6048(5) 0.2655(3) 0.0262(13) Uani 1 1 d . . . . .
H00L H 0.133944 0.527985 0.274565 0.031 Uiso 1 1 calc R U . . .
C00M C 0.1922(8) 0.8346(4) 0.4492(3) 0.0260(12) Uani 1 1 d . . . . .
H00M H 0.205196 0.885855 0.490153 0.031 Uiso 1 1 calc R U . . .
C00N C 0.1581(7) 0.8705(4) 0.3737(3) 0.0299(13) Uani 1 1 d . . . . .
H00N H 0.148847 0.946863 0.362769 0.036 Uiso 1 1 calc R U . . .
C00O C 0.0733(8) 0.7563(5) 0.1771(3) 0.0318(14) Uani 1 1 d . . . . .
H00O H 0.047889 0.781684 0.125791 0.038 Uiso 1 1 calc R U . . .
C00P C 0.0973(8) 0.8293(5) 0.2354(3) 0.0328(14) Uani 1 1 d . . . . .
H00P H 0.087452 0.905686 0.224592 0.039 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 N1 1.240(5) . ?
O002 N1 1.224(5) . ?
O1 N2 1.222(6) . ?
O004 N2 1.239(6) . ?
N005 C00A 1.352(6) . ?
N005 N007 1.379(6) . ?
N005 H005 0.8800 . ?
N1 C009 1.456(6) . ?
N007 C00H 1.274(6) . ?
N2 C00D 1.444(6) . ?
C009 C00B 1.375(7) . ?
C009 C00A 1.430(7) . ?
C00A C00I 1.411(7) . ?
C00B C00D 1.379(7) . ?
C00B H00B 0.9500 . ?
C00C C00F 1.363(7) . ?
C00C C00M 1.403(7) . ?
C00C H00C 0.9500 . ?
C00D C00G 1.387(7) . ?
C00E C00K 1.419(7) . ?
C00E C00F 1.423(7) . ?
C00E C00L 1.443(7) . ?
C00F C00H 1.479(7) . ?
C00G C00I 1.360(7) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J C00L 1.358(7) . ?
C00J C00O 1.420(7) . ?
C00J H00J 0.9500 . ?
C00K C00N 1.425(7) . ?
C00K C00P 1.427(7) . ?
C00L H00L 0.9500 . ?
C00M C00N 1.392(7) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00O C00P 1.352(7) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?

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
C00A N005 N007 117.7(4) . . ?
C00A N005 H005 121.1 . . ?
N007 N005 H005 121.1 . . ?
O002 N1 O001 123.2(4) . . ?
O002 N1 C009 118.1(4) . . ?
O001 N1 C009 118.7(4) . . ?
C00H N007 N005 115.6(5) . . ?
O1 N2 O004 123.0(5) . . ?
O1 N2 C00D 117.7(5) . . ?
O004 N2 C00D 119.3(5) . . ?
C00B C009 C00A 121.5(4) . . ?
C00B C009 N1 116.7(4) . . ?
C00A C009 N1 121.8(4) . . ?
N005 C00A C00I 120.4(5) . . ?
N005 C00A C009 124.1(5) . . ?
C00I C00A C009 115.5(4) . . ?
C009 C00B C00D 120.3(5) . . ?
C009 C00B H00B 119.9 . . ?
C00D C00B H00B 119.9 . . ?
C00F C00C C00M 123.2(5) . . ?
C00F C00C H00C 118.4 . . ?
C00M C00C H00C 118.4 . . ?
C00B C00D C00G 120.0(5) . . ?
C00B C00D N2 119.7(5) . . ?
C00G C00D N2 120.3(5) . . ?
C00K C00E C00F 119.4(5) . . ?
C00K C00E C00L 116.6(5) . . ?
C00F C00E C00L 124.0(5) . . ?
C00C C00F C00E 119.0(5) . . ?
C00C C00F C00H 120.3(5) . . ?
C00E C00F C00H 120.7(5) . . ?
C00I C00G C00D 120.0(5) . . ?
C00I C00G H00G 120.0 . . ?
C00D C00G H00G 120.0 . . ?
N007 C00H C00F 119.0(5) . . ?
N007 C00H H00H 120.5 . . ?
C00F C00H H00H 120.5 . . ?
C00G C00I C00A 122.7(5) . . ?
C00G C00I H00I 118.6 . . ?
C00A C00I H00I 118.6 . . ?
C00L C00J C00O 120.3(5) . . ?
C00L C00J H00J 119.8 . . ?
C00O C00J H00J 119.8 . . ?
C00E C00K C00N 119.5(5) . . ?
C00E C00K C00P 120.3(5) . . ?
C00N C00K C00P 120.2(5) . . ?
C00J C00L C00E 121.8(5) . . ?
C00J C00L H00L 119.1 . . ?
C00E C00L H00L 119.1 . . ?
C00N C00M C00C 118.8(5) . . ?
C00N C00M H00M 120.6 . . ?
C00C C00M H00M 120.6 . . ?
C00M C00N C00K 120.1(5) . . ?
C00M C00N H00N 119.9 . . ?
C00K C00N H00N 119.9 . . ?
C00P C00O C00J 120.2(5) . . ?
C00P C00O H00O 119.9 . . ?
C00J C00O H00O 119.9 . . ?
C00O C00P C00K 120.8(5) . . ?
C00O C00P H00P 119.6 . . ?
C00K C00P H00P 119.6 . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.075

