# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_vsp-c1
_database_code_depnum_ccdc_archive 'CCDC 2476735'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-03-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 N7 O10'
_chemical_formula_sum            'C9 H5 N7 O10'
_chemical_formula_weight         371.20
_chemical_melting_point          ?
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 1 21/c 1'
_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                   12.7945(4)
_cell_length_b                   8.7209(3)
_cell_length_c                   12.6951(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.9810(10)
_cell_angle_gamma                90
_cell_volume                     1339.49(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1102 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.9370. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29401
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.887
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             3028
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.5609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H00K(0.045) H00L(0.044) H00P(0.048) H00A(0.046) H00B(0.046)
 Fixed X: H00K(0.121865) H00L(0.117737) H00P(0.362214) H00A(0.145083)
 H00B(0.157228)
 Fixed Y: H00K(0.561335) H00L(0.309887) H00P(0.672426) H00A(0.847517)
 H00B(0.821543)
 Fixed Z: H00K(0.317242) H00L(0.582619) H00P(0.426391) H00A(0.51537)
 H00B(0.3975)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.20348(10) 0.73475(13) 0.69699(9) 0.0491(3) Uani 1 1 d . . . . .
N002 N 0.30281(10) 0.81492(14) 0.52185(9) 0.0358(3) Uani 1 1 d . . . . .
N003 N 0.15800(9) 0.62600(13) 0.48028(9) 0.0341(3) Uani 1 1 d . . . . .
O004 O 0.17334(12) 0.51076(14) 0.75241(9) 0.0565(3) Uani 1 1 d . . . . .
O005 O 0.05009(11) 0.28557(16) 0.24999(10) 0.0615(4) Uani 1 1 d . . . . .
O006 O 0.35988(12) 1.01757(16) 0.77149(10) 0.0607(4) Uani 1 1 d . . . . .
O007 O 0.66152(11) 0.82822(18) 0.56794(12) 0.0655(4) Uani 1 1 d . . . . .
O008 O 0.21620(11) 1.05097(15) 0.62483(12) 0.0644(4) Uani 1 1 d . . . . .
N009 N 0.17952(10) 0.59820(14) 0.68004(9) 0.0365(3) Uani 1 1 d . . . . .
O00A O 0.58384(12) 0.62154(17) 0.48395(12) 0.0665(4) Uani 1 1 d . . . . .
N00B N 0.30702(12) 0.99836(14) 0.67300(11) 0.0436(3) Uani 1 1 d . . . . .
O00C O 0.04326(13) 0.14564(16) 0.38873(12) 0.0701(4) Uani 1 1 d . . . . .
O00D O 0.62500(12) 0.8819(2) 0.78031(11) 0.0767(5) Uani 1 1 d . . . . .
N00E N 0.06517(11) 0.26452(16) 0.34943(12) 0.0463(3) Uani 1 1 d . . . . .
C00F C 0.15604(11) 0.53805(16) 0.57072(11) 0.0331(3) Uani 1 1 d . . . . .
N00G N 0.58295(12) 0.74087(17) 0.53289(11) 0.0466(3) Uani 1 1 d . . . . .
C00H C 0.35920(12) 0.90549(16) 0.61075(11) 0.0360(3) Uani 1 1 d . . . . .
N00I N 0.55775(12) 0.96424(19) 0.71621(11) 0.0511(4) Uani 1 1 d . . . . .
O00J O 0.55795(14) 1.10403(18) 0.71675(14) 0.0803(5) Uani 1 1 d . . . . .
C00K C 0.12774(11) 0.53320(18) 0.38961(11) 0.0379(3) Uani 1 1 d . . . . .
H00K H 0.121865 0.561335 0.317242 0.045 Uiso 1 1 calc R . . . .
C00L C 0.12522(11) 0.39136(17) 0.53835(12) 0.0370(3) Uani 1 1 d . . . . .
H00L H 0.117737 0.309887 0.582619 0.044 Uiso 1 1 calc R . . . .
C00M C 0.10738(11) 0.39065(17) 0.42378(12) 0.0369(3) Uani 1 1 d . . . . .
C00N C 0.46956(12) 0.88967(17) 0.62948(11) 0.0375(3) Uani 1 1 d . . . . .
C00O C 0.48144(12) 0.78550(17) 0.55038(12) 0.0387(3) Uani 1 1 d . . . . .
C00P C 0.37821(13) 0.74127(18) 0.48547(12) 0.0403(3) Uani 1 1 d . . . . .
H00P H 0.362214 0.672426 0.426391 0.048 Uiso 1 1 calc R . . . .
C00Q C 0.18323(12) 0.78801(17) 0.47453(12) 0.0380(3) Uani 1 1 d . . . . .
H00A H 0.145083 0.847517 0.515370 0.046 Uiso 1 1 calc R . . . .
H00B H 0.157228 0.821543 0.397500 0.046 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
O001 N009 1.2311(16) . ?
N002 C00H 1.3742(18) . ?
N002 C00P 1.3588(19) . ?
N002 C00Q 1.4694(18) . ?
N003 C00F 1.3878(17) . ?
N003 C00K 1.3564(18) . ?
N003 C00Q 1.4564(18) . ?
O004 N009 1.2162(16) . ?
O005 N00E 1.2273(19) . ?
O006 N00B 1.2242(17) . ?
O007 N00G 1.2239(19) . ?
O008 N00B 1.2135(19) . ?
N009 C00F 1.4214(17) . ?
O00A N00G 1.2140(19) . ?
N00B C00H 1.4386(19) . ?
O00C N00E 1.2220(19) . ?
O00D N00I 1.210(2) . ?
N00E C00M 1.4356(19) . ?
C00F C00L 1.362(2) . ?
N00G C00O 1.441(2) . ?
C00H C00N 1.360(2) . ?
N00I O00J 1.219(2) . ?
N00I C00N 1.4492(19) . ?
C00K C00M 1.369(2) . ?
C00L C00M 1.397(2) . ?
C00N C00O 1.399(2) . ?
C00O C00P 1.365(2) . ?

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
C00H N002 C00Q 128.78(12) . . ?
C00P N002 C00H 108.05(12) . . ?
C00P N002 C00Q 123.06(12) . . ?
C00F N003 C00Q 129.91(11) . . ?
C00K N003 C00F 107.18(12) . . ?
C00K N003 C00Q 122.89(12) . . ?
O001 N009 C00F 119.29(12) . . ?
O004 N009 O001 123.24(12) . . ?
O004 N009 C00F 117.46(12) . . ?
O006 N00B C00H 115.92(13) . . ?
O008 N00B O006 125.69(14) . . ?
O008 N00B C00H 118.39(13) . . ?
O005 N00E C00M 117.48(14) . . ?
O00C N00E O005 124.51(14) . . ?
O00C N00E C00M 117.96(14) . . ?
N003 C00F N009 123.29(12) . . ?
C00L C00F N003 110.53(12) . . ?
C00L C00F N009 126.14(13) . . ?
O007 N00G C00O 116.80(14) . . ?
O00A N00G O007 125.19(15) . . ?
O00A N00G C00O 118.00(14) . . ?
N002 C00H N00B 124.14(13) . . ?
C00N C00H N002 108.85(12) . . ?
C00N C00H N00B 127.00(13) . . ?
O00D N00I O00J 126.18(16) . . ?
O00D N00I C00N 116.89(15) . . ?
O00J N00I C00N 116.91(16) . . ?
N003 C00K C00M 107.70(12) . . ?
C00F C00L C00M 104.57(13) . . ?
C00K C00M N00E 123.84(13) . . ?
C00K C00M C00L 110.02(13) . . ?
C00L C00M N00E 125.95(14) . . ?
C00H C00N N00I 126.49(14) . . ?
C00H C00N C00O 106.82(12) . . ?
C00O C00N N00I 126.68(14) . . ?
C00N C00O N00G 126.88(14) . . ?
C00P C00O N00G 125.05(14) . . ?
C00P C00O C00N 107.89(13) . . ?
N002 C00P C00O 108.40(13) . . ?
N003 C00Q N002 110.65(11) . . ?


# start Validation Reply Form
_vrf_PLAT430_vsp-c1              
;
PROBLEM:  Short Inter D...A Contact  O00A     ..O00D.2.80 Ang.
RESPONSE: Short NO2 O...O and O...N interactions
;
# end Validation Reply Form


####################################################################### 
# 
# 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_VSP-C8
_database_code_depnum_ccdc_archive 'CCDC 2476742'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-07-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N4 O4'
_chemical_formula_sum            'C9 H8 N4 O4'
_chemical_formula_weight         236.19
_chemical_melting_point          ?
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 1 21/c 1'
_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                   12.3802(6)
_cell_length_b                   8.4707(4)
_cell_length_c                   10.1162(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.237(2)
_cell_angle_gamma                90
_cell_volume                     1023.58(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1624 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.9101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.869
_diffrn_reflns_theta_min         1.705
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1935
_reflns_number_total             2436
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1341P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N001 N 0.76359(11) 0.58133(18) 0.57836(13) 0.0348(4) Uani 1 1 d . . . . .
N002 N 0.75273(12) 0.57796(18) 0.81348(13) 0.0362(4) Uani 1 1 d . . . . .
O003 O 0.60374(16) 0.2827(2) 1.08297(15) 0.0649(5) Uani 1 1 d . . . . .
O004 O 0.49321(13) 0.3241(3) 0.88223(19) 0.0702(6) Uani 1 1 d . . . . .
N005 N 0.58306(14) 0.3432(2) 0.96870(16) 0.0447(4) Uani 1 1 d . . . . .
O006 O 0.99534(15) 0.3358(3) 0.5849(2) 0.0767(6) Uani 1 1 d . . . . .
N007 N 0.93920(14) 0.4310(3) 0.63029(18) 0.0534(5) Uani 1 1 d . . . . .
C008 C 0.67196(15) 0.5923(2) 0.46923(17) 0.0405(4) Uani 1 1 d . . . . .
H008 H 0.610781 0.657862 0.464289 0.049 Uiso 1 1 calc R . . . .
O009 O 0.97173(16) 0.4912(4) 0.74291(19) 0.0981(9) Uani 1 1 d . . . . .
C00A C 0.82572(16) 0.5570(2) 0.94132(17) 0.0428(4) Uani 1 1 d . . . . .
H00A H 0.898285 0.596330 0.969679 0.051 Uiso 1 1 calc R . . . .
C00B C 0.65481(14) 0.5054(2) 0.80830(16) 0.0372(4) Uani 1 1 d . . . . .
H00B H 0.591795 0.502603 0.734088 0.045 Uiso 1 1 calc R . . . .
C00C C 0.68384(17) 0.4920(3) 0.36816(17) 0.0464(5) Uani 1 1 d . . . . .
H00C H 0.632596 0.477199 0.283593 0.056 Uiso 1 1 calc R . . . .
C00D C 0.66632(14) 0.4364(2) 0.93397(16) 0.0363(4) Uani 1 1 d . . . . .
C00E C 0.77493(15) 0.6730(2) 0.70334(16) 0.0398(4) Uani 1 1 d . . . . .
H00D H 0.850212 0.715485 0.732758 0.048 Uiso 1 1 calc R . . . .
H00E H 0.723106 0.761119 0.684259 0.048 Uiso 1 1 calc R . . . .
C00F C 0.78682(18) 0.4160(2) 0.41490(19) 0.0450(5) Uani 1 1 d . . . . .
H00F H 0.817464 0.341590 0.367638 0.054 Uiso 1 1 calc R . . . .
C00G C 0.83384(14) 0.4724(2) 0.54403(16) 0.0378(4) Uani 1 1 d . . . . .
C00H C 0.77376(16) 0.4693(2) 1.01863(17) 0.0432(4) Uani 1 1 d . . . . .
H00H H 0.803086 0.437513 1.108948 0.052 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
N001 C008 1.362(2) . ?
N001 C00E 1.459(2) . ?
N001 C00G 1.374(2) . ?
N002 C00A 1.381(2) . ?
N002 C00B 1.348(2) . ?
N002 C00E 1.458(2) . ?
O003 N005 1.228(2) . ?
O004 N005 1.232(2) . ?
N005 C00D 1.414(2) . ?
O006 N007 1.230(3) . ?
N007 O009 1.216(3) . ?
N007 C00G 1.410(2) . ?
C008 C00C 1.366(3) . ?
C00A C00H 1.357(3) . ?
C00B C00D 1.372(2) . ?
C00C C00F 1.395(3) . ?
C00D C00H 1.408(2) . ?
C00F C00G 1.369(3) . ?

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 N001 C00E 122.41(15) . . ?
C008 N001 C00G 106.77(14) . . ?
C00G N001 C00E 130.81(14) . . ?
C00A N002 C00E 125.34(15) . . ?
C00B N002 C00A 109.77(15) . . ?
C00B N002 C00E 124.77(14) . . ?
O003 N005 O004 122.65(18) . . ?
O003 N005 C00D 118.78(17) . . ?
O004 N005 C00D 118.56(16) . . ?
O006 N007 C00G 116.98(19) . . ?
O009 N007 O006 122.98(19) . . ?
O009 N007 C00G 120.03(19) . . ?
N001 C008 C00C 109.49(16) . . ?
C00H C00A N002 108.51(16) . . ?
N002 C00B C00D 106.55(14) . . ?
C008 C00C C00F 107.57(16) . . ?
C00B C00D N005 124.26(16) . . ?
C00B C00D C00H 109.32(16) . . ?
C00H C00D N005 126.39(16) . . ?
N002 C00E N001 111.95(14) . . ?
C00G C00F C00C 106.47(17) . . ?
N001 C00G N007 123.70(16) . . ?
C00F C00G N001 109.70(15) . . ?
C00F C00G N007 126.58(18) . . ?
C00A C00H C00D 105.85(15) . . ?

_olex2_exptl_crystal_mounting_method MULTI-scan
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_VSP-C9
_database_code_depnum_ccdc_archive 'CCDC 2476743'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N4 O4'
_chemical_formula_sum            'C9 H8 N4 O4'
_chemical_formula_weight         236.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.2722(5)
_cell_length_b                   8.8323(4)
_cell_length_c                   11.4857(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1042.06(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8507.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8480
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.686
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                1712
_reflns_number_total             1799
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.255
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+0.0498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.8036(2) 0.2223(3) 0.6819(2) 0.0676(7) Uani 1 1 d . . . . .
N002 N 0.2770(2) 0.1455(2) 0.5556(2) 0.0409(5) Uani 1 1 d . . . . .
N003 N 0.49343(19) 0.2493(2) 0.5502(2) 0.0369(5) Uani 1 1 d . . . . .
N004 N 0.5898(2) 0.4911(3) 0.3168(3) 0.0561(7) Uani 1 1 d . . . . .
N005 N 0.6855(2) 0.2068(3) 0.6742(2) 0.0481(6) Uani 1 1 d . . . . .
O006 O 0.6960(3) 0.5483(3) 0.2964(3) 0.0745(8) Uani 1 1 d . . . . .
O007 O 0.6207(3) 0.1378(4) 0.7444(2) 0.0808(9) Uani 1 1 d . . . . .
C008 C 0.4664(3) 0.3264(3) 0.4525(3) 0.0403(6) Uani 1 1 d . . . . .
H008 H 0.386127 0.330993 0.415268 0.048 Uiso 1 1 calc R U . . .
O009 O 0.4948(3) 0.5081(4) 0.2556(3) 0.0870(10) Uani 1 1 d . . . . .
C00A C 0.5790(3) 0.3975(3) 0.4174(3) 0.0431(6) Uani 1 1 d . . . . .
C00B C 0.3981(2) 0.1536(3) 0.6157(3) 0.0428(6) Uani 1 1 d . . . . .
H00A H 0.433202 0.052386 0.625180 0.051 Uiso 1 1 calc R U . . .
H00B H 0.384347 0.196234 0.692559 0.051 Uiso 1 1 calc R U . . .
C00C C 0.2504(3) 0.0508(3) 0.4649(3) 0.0451(6) Uani 1 1 d . . . . .
H00C H 0.307353 -0.019668 0.432901 0.054 Uiso 1 1 calc R U . . .
C00D C 0.6234(2) 0.2717(3) 0.5760(2) 0.0377(6) Uani 1 1 d . . . . .
C00E C 0.6786(2) 0.3636(3) 0.4944(2) 0.0426(6) Uani 1 1 d . . . . .
H00E H 0.764535 0.396405 0.491128 0.051 Uiso 1 1 calc R U . . .
C00F C 0.1695(3) 0.2329(3) 0.5780(3) 0.0521(8) Uani 1 1 d . . . . .
H00F H 0.162105 0.306826 0.635318 0.063 Uiso 1 1 calc R U . . .
C00G C 0.0759(3) 0.1913(4) 0.5010(4) 0.0631(9) Uani 1 1 d . . . . .
H00G H -0.007530 0.231798 0.496481 0.076 Uiso 1 1 calc R U . . .
C00H C 0.1264(3) 0.0770(4) 0.4295(3) 0.0567(8) Uani 1 1 d . . . . .
H00H H 0.083033 0.028270 0.369118 0.068 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 N005 1.224(3) . ?
N002 C00B 1.424(4) . ?
N002 C00C 1.364(4) . ?
N002 C00F 1.371(4) . ?
N003 C008 1.341(4) . ?
N003 C00B 1.497(3) . ?
N003 C00D 1.382(3) . ?
N004 O006 1.225(4) . ?
N004 O009 1.212(4) . ?
N004 C00A 1.425(4) . ?
N005 O007 1.210(4) . ?
N005 C00D 1.417(4) . ?
C008 H008 0.9300 . ?
C008 C00A 1.377(4) . ?
C00A C00E 1.385(4) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.357(4) . ?
C00D C00E 1.363(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00G 1.357(5) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.401(6) . ?
C00H H00H 0.9300 . ?

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
C00C N002 C00B 125.1(2) . . ?
C00C N002 C00F 109.1(3) . . ?
C00F N002 C00B 125.7(2) . . ?
C008 N003 C00B 124.9(2) . . ?
C008 N003 C00D 107.8(2) . . ?
C00D N003 C00B 127.3(2) . . ?
O006 N004 C00A 117.6(3) . . ?
O009 N004 O006 123.7(3) . . ?
O009 N004 C00A 118.7(2) . . ?
O001 N005 C00D 117.3(3) . . ?
O007 N005 O001 123.6(3) . . ?
O007 N005 C00D 119.1(2) . . ?
N003 C008 H008 126.2 . . ?
N003 C008 C00A 107.6(2) . . ?
C00A C008 H008 126.2 . . ?
C008 C00A N004 124.6(3) . . ?
C008 C00A C00E 109.6(2) . . ?
C00E C00A N004 125.9(2) . . ?
N002 C00B N003 110.9(2) . . ?
N002 C00B H00A 109.5 . . ?
N002 C00B H00B 109.5 . . ?
N003 C00B H00A 109.5 . . ?
N003 C00B H00B 109.5 . . ?
H00A C00B H00B 108.1 . . ?
N002 C00C H00C 125.9 . . ?
C00H C00C N002 108.2(3) . . ?
C00H C00C H00C 125.9 . . ?
N003 C00D N005 123.2(3) . . ?
C00E C00D N003 109.9(2) . . ?
C00E C00D N005 126.9(2) . . ?
C00A C00E H00E 127.5 . . ?
C00D C00E C00A 105.1(2) . . ?
C00D C00E H00E 127.5 . . ?
N002 C00F H00F 126.4 . . ?
C00G C00F N002 107.2(3) . . ?
C00G C00F H00F 126.4 . . ?
C00F C00G H00G 125.8 . . ?
C00F C00G C00H 108.4(3) . . ?
C00H C00G H00G 125.8 . . ?
C00C C00H C00G 107.2(3) . . ?
C00C C00H H00H 126.4 . . ?
C00G C00H H00H 126.4 . . ?

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
O001 N005 C00D N003 173.0(2) . . . . ?
O001 N005 C00D C00E -7.4(4) . . . . ?
N002 C00C C00H C00G 0.0(3) . . . . ?
N002 C00F C00G C00H -0.3(4) . . . . ?
N003 C008 C00A N004 -179.9(3) . . . . ?
N003 C008 C00A C00E 0.3(3) . . . . ?
N003 C00D C00E C00A 0.0(3) . . . . ?
N004 C00A C00E C00D 180.0(3) . . . . ?
N005 C00D C00E C00A -179.6(2) . . . . ?
O006 N004 C00A C008 179.4(3) . . . . ?
O006 N004 C00A C00E -0.7(5) . . . . ?
O007 N005 C00D N003 -5.9(4) . . . . ?
O007 N005 C00D C00E 173.8(3) . . . . ?
C008 N003 C00B N002 4.5(3) . . . . ?
C008 N003 C00D N005 179.8(2) . . . . ?
C008 N003 C00D C00E 0.1(3) . . . . ?
C008 C00A C00E C00D -0.2(3) . . . . ?
O009 N004 C00A C008 -1.5(5) . . . . ?
O009 N004 C00A C00E 178.3(3) . . . . ?
C00B N002 C00C C00H -179.1(3) . . . . ?
C00B N002 C00F C00G 179.2(3) . . . . ?
C00B N003 C008 C00A -178.8(2) . . . . ?
C00B N003 C00D N005 -1.7(4) . . . . ?
C00B N003 C00D C00E 178.6(2) . . . . ?
C00C N002 C00B N003 81.6(3) . . . . ?
C00C N002 C00F C00G 0.3(3) . . . . ?
C00D N003 C008 C00A -0.3(3) . . . . ?
C00D N003 C00B N002 -173.7(2) . . . . ?
C00F N002 C00B N003 -97.2(3) . . . . ?
C00F N002 C00C C00H -0.1(3) . . . . ?
C00F C00G C00H C00C 0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_VSP-c2
_database_code_depnum_ccdc_archive 'CCDC 2476736'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-04-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 N6 O8'
_chemical_formula_sum            'C9 H6 N6 O8'
_chemical_formula_weight         326.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.5849(17)
_cell_length_b                   10.4912(8)
_cell_length_c                   6.2223(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.21(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2890
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9001.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_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  0.0725
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1848
_reflns_number_total             2037
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.2441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0721
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.055) H3(0.055) H5A(0.045) H5B(0.045) H6(0.044) H8(0.045)
 Fixed X: H2(0.972021) H3(0.972877) H5A(0.773651) H5B(0.776297) H6(0.727381)
 H8(0.54104)
 Fixed Y: H2(0.448931) H3(0.319955) H5A(0.118184) H5B(0.194509) H6(0.354593)
 H8(0.338222)
 Fixed Z: H2(0.397659) H3(0.735563) H5A(0.43433) H5B(0.217454) H6(0.712376)
 H8(0.383841)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.87451(16) 0.3638(3) 0.3393(5) 0.0367(7) Uani 1 1 d . . . . .
C2 C 0.93665(17) 0.3924(3) 0.4432(6) 0.0458(8) Uani 1 1 d . . . . .
H2 H 0.972021 0.448931 0.397659 0.055 Uiso 1 1 calc R . . . .
C3 C 0.93714(17) 0.3206(3) 0.6309(6) 0.0462(8) Uani 1 1 d . . . . .
H3 H 0.972877 0.319955 0.735563 0.055 Uiso 1 1 calc R . . . .
C4 C 0.87526(16) 0.2517(3) 0.6319(5) 0.0373(7) Uani 1 1 d . . . . .
C5 C 0.77286(15) 0.2030(3) 0.3723(5) 0.0375(7) Uani 1 1 d . . . . .
H5A H 0.773651 0.118184 0.434330 0.045 Uiso 1 1 calc R . . . .
H5B H 0.776297 0.194509 0.217454 0.045 Uiso 1 1 calc R . . . .
C6 C 0.69337(16) 0.3354(3) 0.6076(5) 0.0370(7) Uani 1 1 d . . . . .
H6 H 0.727381 0.354593 0.712376 0.044 Uiso 1 1 calc R . . . .
C7 C 0.62258(15) 0.3722(3) 0.6078(5) 0.0339(6) Uani 1 1 d . . . . .
C8 C 0.58871(16) 0.3262(3) 0.4246(5) 0.0376(7) Uani 1 1 d . . . . .
H8 H 0.541040 0.338222 0.383841 0.045 Uiso 1 1 calc R . . . .
C9 C 0.64008(16) 0.2601(3) 0.3182(5) 0.0345(6) Uani 1 1 d . . . . .
N1 N 0.85054(17) 0.4227(2) 0.1435(4) 0.0470(7) Uani 1 1 d . . . . .
N2 N 0.85297(17) 0.1690(2) 0.8026(4) 0.0466(7) Uani 1 1 d . . . . .
N3 N 0.83440(12) 0.2759(2) 0.4519(4) 0.0330(5) Uani 1 1 d . . . . .
N4 N 0.70474(12) 0.2663(2) 0.4282(4) 0.0338(5) Uani 1 1 d . . . . .
N5 N 0.62909(16) 0.1877(3) 0.1275(4) 0.0460(7) Uani 1 1 d . . . . .
N6 N 0.58944(15) 0.4469(2) 0.7720(5) 0.0418(6) Uani 1 1 d . . . . .
O1 O 0.89303(16) 0.4962(2) 0.0577(5) 0.0719(8) Uani 1 1 d . . . . .
O2 O 0.79074(14) 0.3968(3) 0.0729(4) 0.0623(7) Uani 1 1 d . . . . .
O3 O 0.89325(15) 0.1630(3) 0.9578(4) 0.0667(7) Uani 1 1 d . . . . .
O4 O 0.79600(15) 0.1124(3) 0.7903(5) 0.0698(8) Uani 1 1 d . . . . .
O5 O 0.67747(14) 0.1194(3) 0.0607(5) 0.0769(9) Uani 1 1 d . . . . .
O6 O 0.56987(14) 0.1963(3) 0.0421(4) 0.0672(8) Uani 1 1 d . . . . .
O7 O 0.52560(13) 0.4714(2) 0.7522(5) 0.0653(7) Uani 1 1 d . . . . .
O8 O 0.62636(13) 0.4798(2) 0.9249(4) 0.0564(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 C2 1.357(4) . ?
C1 N1 1.437(4) . ?
C1 N3 1.377(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(4) . ?
C4 N2 1.433(4) . ?
C4 N3 1.377(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N3 1.462(4) . ?
C5 N4 1.471(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(4) . ?
C6 N4 1.348(4) . ?
C7 C8 1.389(4) . ?
C7 N6 1.427(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.353(4) . ?
C9 N4 1.385(4) . ?
C9 N5 1.424(4) . ?
N1 O1 1.226(4) . ?
N1 O2 1.226(4) . ?
N2 O3 1.223(4) . ?
N2 O4 1.216(4) . ?
N5 O5 1.222(4) . ?
N5 O6 1.226(3) . ?
N6 O7 1.220(3) . ?
N6 O8 1.223(4) . ?

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 C1 N1 124.9(3) . . ?
C2 C1 N3 111.5(3) . . ?
N3 C1 N1 123.5(3) . . ?
C1 C2 H2 126.7 . . ?
C1 C2 C3 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
C2 C3 H3 126.7 . . ?
C4 C3 C2 106.6(3) . . ?
C4 C3 H3 126.7 . . ?
C3 C4 N2 124.8(3) . . ?
C3 C4 N3 111.4(3) . . ?
N3 C4 N2 123.7(3) . . ?
H5A C5 H5B 108.0 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
N3 C5 N4 110.9(2) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C7 C6 H6 126.2 . . ?
N4 C6 H6 126.2 . . ?
N4 C6 C7 107.6(3) . . ?
C6 C7 C8 109.7(3) . . ?
C6 C7 N6 124.7(3) . . ?
C8 C7 N6 125.6(3) . . ?
C7 C8 H8 127.5 . . ?
C9 C8 C7 105.1(3) . . ?
C9 C8 H8 127.5 . . ?
C8 C9 N4 110.3(3) . . ?
C8 C9 N5 125.5(3) . . ?
N4 C9 N5 124.2(3) . . ?
O1 N1 C1 116.1(3) . . ?
O2 N1 C1 119.3(3) . . ?
O2 N1 O1 124.6(3) . . ?
O3 N2 C4 116.1(3) . . ?
O4 N2 C4 120.1(3) . . ?
O4 N2 O3 123.9(3) . . ?
C1 N3 C5 126.9(3) . . ?
C4 N3 C1 103.8(2) . . ?
C4 N3 C5 127.7(2) . . ?
C6 N4 C5 125.0(2) . . ?
C6 N4 C9 107.4(2) . . ?
C9 N4 C5 127.5(2) . . ?
O5 N5 C9 119.4(3) . . ?
O5 N5 O6 123.8(3) . . ?
O6 N5 C9 116.8(3) . . ?
O7 N6 C7 117.6(3) . . ?
O7 N6 O8 124.4(3) . . ?
O8 N6 C7 118.0(3) . . ?


# start Validation Reply Form
_vrf_PLAT430_VSP-c2              
;
PROBLEM: Short Inter D...A Contact O4 ..O5 . 2.77 Ang.
RESPONSE: Short NO2 O...O and O...N interactions
;
# end Validation Reply Form

####################################################################### 
# 
# 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_VSP-C5
_database_code_depnum_ccdc_archive 'CCDC 2476739'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.952(5)
_cell_length_b                   17.512(10)
_cell_length_c                   7.541(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.98(3)
_cell_angle_gamma                90
_cell_volume                     911.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    424
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      24.69

_exptl_crystal_description       Neddle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS
_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 ?
_diffrn_reflns_number            6092
_diffrn_reflns_av_unetI/netI     0.7248
_diffrn_reflns_av_R_equivalents  0.7985
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         25.153
_diffrn_reflns_theta_full        25.153
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.943
_reflns_number_total             1542
_reflns_number_gt                251
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0947P)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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.03(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1542
_refine_ls_number_parameters     255
_refine_ls_number_restraints     491
_refine_ls_R_factor_all          0.4566
_refine_ls_R_factor_gt           0.1849
_refine_ls_wR_factor_ref         0.5216
_refine_ls_wR_factor_gt          0.3717
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.775
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.203(6) 0.3187(13) 0.371(3) 0.105(9) Uani 0.61(5) 1 d D U P A 1
O1A O 0.288(7) 0.336(2) 0.363(5) 0.078(11) Uani 0.39(5) 1 d D U P A 2
O2 O 0.259(5) 0.4077(19) 0.176(3) 0.097(9) Uani 0.61(5) 1 d D U P A 1
O2A O 0.201(8) 0.433(2) 0.184(4) 0.095(12) Uani 0.39(5) 1 d D U P A 2
N1 N 0.237(5) 0.4274(13) 0.639(3) 0.077(6) Uani 0.61(5) 1 d D U P A 1
N1A N 0.268(9) 0.4266(17) 0.656(4) 0.081(9) Uani 0.39(5) 1 d D U P A 2
N2 N 0.482(4) 0.3436(18) 0.781(4) 0.081(7) Uani 0.61(5) 1 d D U P A 1
N2A N 0.491(7) 0.335(3) 0.802(6) 0.085(10) Uani 0.39(5) 1 d D U P A 2
N3 N 0.220(5) 0.3843(15) 0.326(3) 0.086(7) Uani 0.61(5) 1 d D U P A 1
N3A N 0.273(7) 0.404(2) 0.330(4) 0.086(10) Uani 0.39(5) 1 d D U P A 2
C1 C 0.262(9) 0.4431(16) 0.463(3) 0.083(7) Uani 0.61(5) 1 d D U P A 1
C1A C 0.242(14) 0.4525(18) 0.481(5) 0.084(9) Uani 0.39(5) 1 d D U P A 2
C2 C 0.252(7) 0.5187(15) 0.437(4) 0.083(7) Uani 0.61(5) 1 d D U P A 1
H2 H 0.250309 0.543367 0.327543 0.099 Uiso 0.61(5) 1 calc R U P A 1
C2A C 0.231(10) 0.5287(19) 0.480(6) 0.081(10) Uani 0.39(5) 1 d D U P A 2
H2A H 0.227758 0.560135 0.379831 0.097 Uiso 0.39(5) 1 calc R U P A 2
C3 C 0.246(6) 0.5548(14) 0.604(4) 0.074(7) Uani 0.61(5) 1 d D U P A 1
H3 H 0.251186 0.606906 0.627578 0.088 Uiso 0.61(5) 1 calc R U P A 1
C3A C 0.224(10) 0.5527(19) 0.658(7) 0.083(10) Uani 0.39(5) 1 d D U P A 2
H3A H 0.191899 0.601092 0.696198 0.100 Uiso 0.39(5) 1 calc R U P A 2
C4 C 0.229(5) 0.4965(15) 0.725(4) 0.081(7) Uani 0.61(5) 1 d D U P A 1
H4 H 0.214282 0.502962 0.844722 0.097 Uiso 0.61(5) 1 calc R U P A 1
C4A C 0.274(8) 0.490(2) 0.766(5) 0.086(10) Uani 0.39(5) 1 d D U P A 2
H4A H 0.305646 0.490000 0.889158 0.103 Uiso 0.39(5) 1 calc R U P A 2
C5 C 0.278(4) 0.3582(15) 0.748(4) 0.086(7) Uani 0.61(5) 1 d D U P A 1
H5A H 0.225560 0.364172 0.860299 0.103 Uiso 0.61(5) 1 calc R U P A 1
H5B H 0.213948 0.314851 0.685602 0.103 Uiso 0.61(5) 1 calc R U P A 1
C5A C 0.293(7) 0.350(2) 0.735(7) 0.086(10) Uani 0.39(5) 1 d D U P A 2
H5AA H 0.213952 0.345619 0.831590 0.104 Uiso 0.39(5) 1 calc R U P A 2
H5AB H 0.249104 0.312303 0.645171 0.104 Uiso 0.39(5) 1 calc R U P A 2
C6 C 0.602(5) 0.3634(19) 0.930(4) 0.080(8) Uani 0.61(5) 1 d D U P A 1
H6 H 0.566169 0.391668 1.024806 0.096 Uiso 0.61(5) 1 calc R U P A 1
C6A C 0.608(8) 0.379(3) 0.918(7) 0.084(10) Uani 0.39(5) 1 d D U P A 2
H6A H 0.567578 0.420489 0.981192 0.101 Uiso 0.39(5) 1 calc R U P A 2
C7 C 0.779(5) 0.336(2) 0.919(5) 0.083(8) Uani 0.61(5) 1 d D U P A 1
H7 H 0.889511 0.347689 0.996877 0.100 Uiso 0.61(5) 1 calc R U P A 1
C7A C 0.791(7) 0.354(3) 0.928(9) 0.083(11) Uani 0.39(5) 1 d D U P A 2
H7A H 0.891075 0.365100 1.017693 0.100 Uiso 0.39(5) 1 calc R U P A 2
C8 C 0.774(5) 0.288(2) 0.773(5) 0.080(8) Uani 0.61(5) 1 d D U P A 1
H8 H 0.873796 0.258007 0.738725 0.096 Uiso 0.61(5) 1 calc R U P A 1
C8A C 0.806(7) 0.308(3) 0.780(8) 0.085(11) Uani 0.39(5) 1 d D U P A 2
H8A H 0.917027 0.293137 0.731970 0.102 Uiso 0.39(5) 1 calc R U P A 2
C9 C 0.593(5) 0.295(2) 0.691(4) 0.082(7) Uani 0.61(5) 1 d D U P A 1
H9 H 0.547208 0.269673 0.585632 0.098 Uiso 0.61(5) 1 calc R U P A 1
C9A C 0.622(7) 0.289(3) 0.725(7) 0.086(10) Uani 0.39(5) 1 d D U P A 2
H9A H 0.585413 0.250475 0.643464 0.103 Uiso 0.39(5) 1 calc R U P A 2


_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 N3 1.21(2) . ?
O1A N3A 1.22(2) . ?
O2 N3 1.26(2) . ?
O2A N3A 1.26(2) . ?
N1 C4 1.376(19) . ?
N1 C1 1.39(2) . ?
N1 C5 1.470(17) . ?
N1A C4A 1.38(2) . ?
N1A C1A 1.38(2) . ?
N1A C5A 1.47(2) . ?
N2 C6 1.36(2) . ?
N2 C9 1.39(2) . ?
N2 C5 1.432(18) . ?
N2A C6A 1.36(2) . ?
N2A C9A 1.39(2) . ?
N2A C5A 1.43(2) . ?
N3 C1 1.46(3) . ?
N3A C1A 1.46(3) . ?
C1 C2 1.34(2) . ?
C1A C2A 1.34(2) . ?
C2 C3 1.41(2) . ?
C2 H2 0.9300 . ?
C2A C3A 1.42(3) . ?
C2A H2A 0.9300 . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C3A C4A 1.39(2) . ?
C3A H3A 0.9300 . ?
C4 H4 0.9300 . ?
C4A H4A 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6 C7 1.335(19) . ?
C6 H6 0.9300 . ?
C6A C7A 1.34(2) . ?
C6A H6A 0.9300 . ?
C7 C8 1.38(2) . ?
C7 H7 0.9300 . ?
C7A C8A 1.39(2) . ?
C7A H7A 0.9300 . ?
C8 C9 1.34(2) . ?
C8 H8 0.9300 . ?
C8A C9A 1.34(3) . ?
C8A H8A 0.9300 . ?
C9 H9 0.9300 . ?
C9A H9A 0.9300 . ?

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
C4 N1 C1 106.9(16) . . ?
C4 N1 C5 118.7(16) . . ?
C1 N1 C5 131.1(19) . . ?
C4A N1A C1A 107.5(18) . . ?
C4A N1A C5A 120(2) . . ?
C1A N1A C5A 133(2) . . ?
C6 N2 C9 103.7(17) . . ?
C6 N2 C5 127(2) . . ?
C9 N2 C5 128.5(19) . . ?
C6A N2A C9A 103(2) . . ?
C6A N2A C5A 127(3) . . ?
C9A N2A C5A 127(2) . . ?
O1 N3 O2 127(2) . . ?
O1 N3 C1 119.2(19) . . ?
O2 N3 C1 111(2) . . ?
O1A N3A O2A 126(3) . . ?
O1A N3A C1A 115(2) . . ?
O2A N3A C1A 112(3) . . ?
C2 C1 N1 109.1(18) . . ?
C2 C1 N3 126(2) . . ?
N1 C1 N3 120(3) . . ?
C2A C1A N1A 110(2) . . ?
C2A C1A N3A 126(3) . . ?
N1A C1A N3A 123(3) . . ?
C1 C2 C3 108.5(16) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
C1A C2A C3A 107(2) . . ?
C1A C2A H2A 126.5 . . ?
C3A C2A H2A 126.5 . . ?
C4 C3 C2 105.7(17) . . ?
C4 C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
C4A C3A C2A 107(2) . . ?
C4A C3A H3A 126.7 . . ?
C2A C3A H3A 126.7 . . ?
N1 C4 C3 109.2(17) . . ?
N1 C4 H4 125.4 . . ?
C3 C4 H4 125.4 . . ?
N1A C4A C3A 107(2) . . ?
N1A C4A H4A 126.3 . . ?
C3A C4A H4A 126.3 . . ?
N2 C5 N1 111.5(17) . . ?
N2 C5 H5A 109.3 . . ?
N1 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
N1 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N2A C5A N1A 112(2) . . ?
N2A C5A H5AA 109.2 . . ?
N1A C5A H5AA 109.2 . . ?
N2A C5A H5AB 109.2 . . ?
N1A C5A H5AB 109.2 . . ?
H5AA C5A H5AB 107.9 . . ?
C7 C6 N2 109.8(19) . . ?
C7 C6 H6 125.1 . . ?
N2 C6 H6 125.1 . . ?
N2A C6A C7A 110(2) . . ?
N2A C6A H6A 125.2 . . ?
C7A C6A H6A 125.2 . . ?
C6 C7 C8 109.4(19) . . ?
C6 C7 H7 125.3 . . ?
C8 C7 H7 125.3 . . ?
C6A C7A C8A 108(2) . . ?
C6A C7A H7A 126.0 . . ?
C8A C7A H7A 126.0 . . ?
C9 C8 C7 104(2) . . ?
C9 C8 H8 127.9 . . ?
C7 C8 H8 127.9 . . ?
C9A C8A C7A 103(2) . . ?
C9A C8A H8A 128.3 . . ?
C7A C8A H8A 128.3 . . ?
C8 C9 N2 112.3(18) . . ?
C8 C9 H9 123.9 . . ?
N2 C9 H9 123.9 . . ?
C8A C9A N2A 112(2) . . ?
C8A C9A H9A 123.9 . . ?
N2A C9A H9A 123.9 . . ?

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
C4 N1 C1 C2 -5(5) . . . . ?
C5 N1 C1 C2 -164(3) . . . . ?
C4 N1 C1 N3 -162(4) . . . . ?
C5 N1 C1 N3 39(8) . . . . ?
O1 N3 C1 C2 -168(4) . . . . ?
O2 N3 C1 C2 30(7) . . . . ?
O1 N3 C1 N1 -15(7) . . . . ?
O2 N3 C1 N1 -177(4) . . . . ?
C4A N1A C1A C2A 0(9) . . . . ?
C5A N1A C1A C2A -178(6) . . . . ?
C4A N1A C1A N3A 165(7) . . . . ?
C5A N1A C1A N3A -12(13) . . . . ?
O1A N3A C1A C2A 177(7) . . . . ?
O2A N3A C1A C2A -31(11) . . . . ?
O1A N3A C1A N1A 13(11) . . . . ?
O2A N3A C1A N1A 165(7) . . . . ?
N1 C1 C2 C3 8(5) . . . . ?
N3 C1 C2 C3 162(5) . . . . ?
N1A C1A C2A C3A -8(9) . . . . ?
N3A C1A C2A C3A -173(8) . . . . ?
C1 C2 C3 C4 -7(5) . . . . ?
C1A C2A C3A C4A 13(8) . . . . ?
C1 N1 C4 C3 1(4) . . . . ?
C5 N1 C4 C3 163(3) . . . . ?
C2 C3 C4 N1 4(4) . . . . ?
C1A N1A C4A C3A 9(7) . . . . ?
C5A N1A C4A C3A -173(5) . . . . ?
C2A C3A C4A N1A -13(6) . . . . ?
C6 N2 C5 N1 97(4) . . . . ?
C9 N2 C5 N1 -97(4) . . . . ?
C4 N1 C5 N2 -90(3) . . . . ?
C1 N1 C5 N2 67(5) . . . . ?
C6A N2A C5A N1A 53(7) . . . . ?
C9A N2A C5A N1A -104(6) . . . . ?
C4A N1A C5A N2A -75(5) . . . . ?
C1A N1A C5A N2A 103(9) . . . . ?
C9 N2 C6 C7 7(4) . . . . ?
C5 N2 C6 C7 176(3) . . . . ?
C9A N2A C6A C7A -8(7) . . . . ?
C5A N2A C6A C7A -170(5) . . . . ?
N2 C6 C7 C8 -8(4) . . . . ?
N2A C6A C7A C8A 18(7) . . . . ?
C6 C7 C8 C9 6(4) . . . . ?
C6A C7A C8A C9A -19(7) . . . . ?
C7 C8 C9 N2 -2(4) . . . . ?
C6 N2 C9 C8 -3(4) . . . . ?
C5 N2 C9 C8 -172(4) . . . . ?
C7A C8A C9A N2A 14(7) . . . . ?
C6A N2A C9A C8A -4(7) . . . . ?
C5A N2A C9A C8A 157(6) . . . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.064


# start Validation Reply Form
_vrf_RINTA01_VSP-C5              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Lack of the crystal quality for this compound.
 Weakly diffracting crystals.
;
_vrf_PLAT020_VSP-C5              
;
PROBLEM: The Value of Rint is Greater Than 0.12 
RESPONSE: Lack of the crystal quality for this compound.Though we crystalise 
many time we were not able to obtain crystals of better quality.
Weakly diffracting crystals.
;
_vrf_PLAT026_VSP-C5              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low 
RESPONSE: The crystal data from this compound were poorly diffracting
crystals beyond certain resolution limit. 
;
_vrf_PLAT084_VSP-C5              
;
PROBLEM: High wR2 Value (i.e. > 0.25) 
RESPONSE: Lack of the crystal quality for this compound.
 Weakly diffracting crystals.
;
_vrf_PLAT029_VSP-C5              
;
PROBLEM: diffrn_measured_fraction_theta_full value Low
RESPONSE: Few scans were removed during integration due to very low intensity
 of diffraction patterns beyond certain resolution limit.
;
_vrf_PLAT031_VSP-C5              
;
PROBLEM: Refined Extinction Parameter Within Range of ... 1.000
RESPONSE: Lack of the crystal quality for this class of compounds. Weakly 
diffracting crystals.
;
_vrf_PLAT082_VSP-C5              
;
PROBLEM:  High R1 Value .................................. 0.18
RESPONSE: Lack of the crystal quality for this class of compounds. Weakly 
diffracting crystals. 
;
_vrf_PLAT088_VSP-C5              
;
PROBLEM:  Poor Data / Parameter Ratio .................... 6.05 Note
RESPONSE: Due to disorder/twinning in the crystal, some low-angle reflections
 were poorly defined and omitted during data processing. 
;
_vrf_PLAT911_VSP-C5              
;
PROBLEM:  Missing FCF Refl Between Thmin & STh/L= 0.598 92 
RESPONSE: Due to disorder/twinning in the crystal, some low-angle reflections 
were poorly defined and omitted during data processing. 
;
# end Validation Reply Form



####################################################################### 
# 
# 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_VSP-c3
_database_code_depnum_ccdc_archive 'CCDC 2476737'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-03-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 N6 O8'
_chemical_formula_sum            'C9 H6 N6 O8'
_chemical_formula_weight         326.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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 1 21/c 1'
_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                   10.5972(10)
_cell_length_b                   8.9758(8)
_cell_length_c                   13.1358(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.377(3)
_cell_angle_gamma                90
_cell_volume                     1247.29(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32.536
_cell_measurement_theta_min      4.386
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absortion correction'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21994
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         4.386
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2765
_reflns_number_total             3027
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.055) H4(0.047) H5A(0.044) H5B(0.044) H6(0.044) H8(0.05)
 Fixed X: H2(0.107958) H4(0.193992) H5A(0.169861) H5B(0.11189) H6(0.251758)
 H8(0.598633)
 Fixed Y: H2(0.349958) H4(0.586904) H5A(0.847306) H5B(0.874654) H6(0.967855)
 H8(0.890207)
 Fixed Z: H2(0.666545) H4(0.41986) H5A(0.47968) H5B(0.585194) H6(0.727313)
 H8(0.628503)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.15760(10) 0.66018(12) 0.56272(8) 0.0329(2) Uani 1 1 d . . . . .
O1 O 0.14742(17) 0.16957(15) 0.50505(15) 0.0888(5) Uani 1 1 d . . . . .
C1 C 0.12731(12) 0.57721(15) 0.64681(10) 0.0378(3) Uani 1 1 d . . . . .
N2 N 0.30128(10) 0.86953(12) 0.59476(8) 0.0347(2) Uani 1 1 d . . . . .
O2 O 0.16959(15) 0.30239(17) 0.36945(12) 0.0768(4) Uani 1 1 d . . . . .
C2 C 0.12503(14) 0.42890(16) 0.62361(12) 0.0457(3) Uani 1 1 d . . . . .
H2 H 0.107958 0.349958 0.666545 0.055 Uiso 1 1 calc R . . . .
O3 O 0.0734(2) 0.5534(2) 0.81003(11) 0.1062(7) Uani 1 1 d . . . . .
N3 N 0.09990(13) 0.63919(16) 0.74236(9) 0.0518(3) Uani 1 1 d . . . . .
C3 C 0.15377(12) 0.42161(15) 0.52192(12) 0.0410(3) Uani 1 1 d . . . . .
O4 O 0.10252(12) 0.77382(14) 0.75364(9) 0.0581(3) Uani 1 1 d . . . . .
N4 N 0.49499(12) 1.02075(14) 0.80239(10) 0.0459(3) Uani 1 1 d . . . . .
C4 C 0.17343(12) 0.56256(15) 0.48568(10) 0.0394(3) Uani 1 1 d . . . . .
H4 H 0.193992 0.586904 0.419860 0.047 Uiso 1 1 calc R . . . .
C5 C 0.17738(13) 0.82156(14) 0.55150(10) 0.0370(3) Uani 1 1 d . . . . .
H5A H 0.169861 0.847306 0.479680 0.044 Uiso 1 1 calc R . . . .
H5B H 0.111890 0.874654 0.585194 0.044 Uiso 1 1 calc R . . . .
N5 N 0.44530(14) 0.78727(14) 0.46320(10) 0.0492(3) Uani 1 1 d . . . . .
O5 O 0.42327(13) 1.05336(15) 0.86792(9) 0.0616(3) Uani 1 1 d . . . . .
O6 O 0.60849(12) 1.04246(17) 0.80979(11) 0.0693(4) Uani 1 1 d . . . . .
N6 N 0.15820(12) 0.28849(15) 0.46100(14) 0.0565(4) Uani 1 1 d . . . . .
C6 C 0.31627(12) 0.93725(14) 0.68706(10) 0.0363(3) Uani 1 1 d . . . . .
H6 H 0.251758 0.967855 0.727313 0.044 Uiso 1 1 calc R . . . .
O7 O 0.35556(14) 0.77294(15) 0.40009(9) 0.0654(4) Uani 1 1 d . . . . .
C7 C 0.44328(13) 0.95251(14) 0.71038(10) 0.0381(3) Uani 1 1 d . . . . .
C8 C 0.51130(13) 0.89414(15) 0.63200(11) 0.0414(3) Uani 1 1 d . . . . .
H8 H 0.598633 0.890207 0.628503 0.050 Uiso 1 1 calc R . . . .
O8 O 0.55595(14) 0.76226(16) 0.44563(11) 0.0679(4) Uani 1 1 d . . . . .
C9 C 0.42156(13) 0.84405(14) 0.56158(10) 0.0385(3) 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
N1 C1 1.3854(16) . ?
N1 C4 1.3565(16) . ?
N1 C5 1.4722(16) . ?
O1 N6 1.223(2) . ?
C1 C2 1.3656(19) . ?
C1 N3 1.4186(18) . ?
N2 C5 1.4644(16) . ?
N2 C6 1.3573(16) . ?
N2 C9 1.3901(17) . ?
O2 N6 1.222(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
O3 N3 1.2211(19) . ?
N3 O4 1.2175(19) . ?
C3 C4 1.3720(19) . ?
C3 N6 1.4403(18) . ?
N4 O5 1.2172(18) . ?
N4 O6 1.2167(17) . ?
N4 C7 1.4346(18) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N5 O7 1.231(2) . ?
N5 O8 1.2290(19) . ?
N5 C9 1.4253(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.3696(18) . ?
C7 C8 1.393(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(2) . ?

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
C1 N1 C5 130.52(11) . . ?
C4 N1 C1 106.99(11) . . ?
C4 N1 C5 122.43(11) . . ?
N1 C1 N3 124.31(12) . . ?
C2 C1 N1 110.37(12) . . ?
C2 C1 N3 125.30(13) . . ?
C6 N2 C5 122.23(11) . . ?
C6 N2 C9 107.01(11) . . ?
C9 N2 C5 130.37(11) . . ?
C1 C2 H2 127.5 . . ?
C1 C2 C3 104.98(12) . . ?
C3 C2 H2 127.5 . . ?
O3 N3 C1 117.70(15) . . ?
O4 N3 C1 119.50(13) . . ?
O4 N3 O3 122.79(15) . . ?
C2 C3 N6 126.13(14) . . ?
C4 C3 C2 109.67(12) . . ?
C4 C3 N6 124.17(14) . . ?
O5 N4 C7 118.37(12) . . ?
O6 N4 O5 124.09(14) . . ?
O6 N4 C7 117.54(14) . . ?
N1 C4 C3 107.99(12) . . ?
N1 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
N2 C5 N1 112.34(10) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
O7 N5 C9 118.51(13) . . ?
O8 N5 O7 124.22(14) . . ?
O8 N5 C9 117.19(15) . . ?
O1 N6 C3 117.01(17) . . ?
O2 N6 O1 124.91(16) . . ?
O2 N6 C3 118.06(15) . . ?
N2 C6 H6 126.1 . . ?
N2 C6 C7 107.84(11) . . ?
C7 C6 H6 126.1 . . ?
C6 C7 N4 123.55(13) . . ?
C6 C7 C8 109.97(12) . . ?
C8 C7 N4 126.48(13) . . ?
C7 C8 H8 127.6 . . ?
C9 C8 C7 104.76(12) . . ?
C9 C8 H8 127.6 . . ?
N2 C9 N5 123.86(13) . . ?
C8 C9 N2 110.42(12) . . ?
C8 C9 N5 125.44(13) . . ?


# start Validation Reply Form
_vrf_PLAT910_VSP-c3              
;
PROBLEM: Missing FCF Reflection(s) Below Theta(Min)[Deg]=
RESPONSE: 11 low angle reflections missing from >3000 unique reflections in a 
monoclinic structure is reasonable. This has no impact on the overall accuracy 
of the structure.
;
# end Validation Reply Form


####################################################################### 
# 
# 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_vsp-c6
_database_code_depnum_ccdc_archive 'CCDC 2476740'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-07-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19
_chemical_melting_point          ?
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 1 21/c 1'
_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                   20.760(3)
_cell_length_b                   10.7770(15)
_cell_length_c                   8.4910(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.119(5)
_cell_angle_gamma                90
_cell_volume                     1864.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7604
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.41
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1721 before and 0.0905 after correction. The Ratio of minimum to maximum transmission is 0.6672. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         1.000
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2244
_reflns_number_total             3828
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+3.1658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.2502
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00C,H00N), C00R(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00S(H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N001 N 0.54530(16) 0.8765(3) 0.6045(4) 0.0541(9) Uani 1 1 d . . . . .
N002 N 0.84792(16) 0.2843(3) 0.4449(4) 0.0515(9) Uani 1 1 d . . . . .
N003 N 0.95089(16) 0.3815(3) 0.5542(4) 0.0513(9) Uani 1 1 d . . . . .
N004 N 0.65092(17) 0.7884(4) 0.5972(4) 0.0592(10) Uani 1 1 d . . . . .
O005 O 0.67397(18) 0.1497(3) 0.6258(5) 0.0897(12) Uani 1 1 d . . . . .
N006 N 0.80145(19) 0.7585(4) 0.8755(5) 0.0681(11) Uani 1 1 d . . . . .
N007 N 0.69850(19) 0.2420(4) 0.5809(5) 0.0670(11) Uani 1 1 d . . . . .
O008 O 0.81827(17) 0.8640(3) 0.9208(5) 0.0956(13) Uani 1 1 d . . . . .
O009 O 0.83391(19) 0.6678(4) 0.9216(6) 0.1086(15) Uani 1 1 d . . . . .
C00A C 0.75889(18) 0.2323(3) 0.5271(5) 0.0484(10) Uani 1 1 d . . . . .
C00B C 0.74147(19) 0.7445(4) 0.7626(5) 0.0510(10) Uani 1 1 d . . . . .
O00C O 0.67315(19) 0.3456(3) 0.5794(6) 0.1095(16) Uani 1 1 d . . . . .
C00D C 0.7019(2) 0.8396(4) 0.6984(5) 0.0569(11) Uani 1 1 d . . . . .
H00D H 0.708805 0.923639 0.720212 0.068 Uiso 1 1 calc R . . . .
C00E C 0.7921(2) 0.1221(4) 0.5083(5) 0.0598(12) Uani 1 1 d . . . . .
H00E H 0.779043 0.041711 0.526767 0.072 Uiso 1 1 calc R . . . .
C00F C 0.79419(19) 0.3316(4) 0.4886(5) 0.0535(11) Uani 1 1 d . . . . .
H00F H 0.783103 0.414991 0.492024 0.064 Uiso 1 1 calc R . . . .
C00G C 0.5445(2) 0.9708(4) 0.7116(6) 0.0618(12) Uani 1 1 d . . . . .
H00G H 0.574957 1.034767 0.733832 0.074 Uiso 1 1 calc R . . . .
C00H C 0.4925(2) 0.8026(4) 0.6063(6) 0.0619(12) Uani 1 1 d . . . . .
H00H H 0.481691 0.731826 0.544007 0.074 Uiso 1 1 calc R . . . .
C00I C 0.8471(2) 0.1574(4) 0.4574(6) 0.0626(12) Uani 1 1 d . . . . .
H00I H 0.879318 0.104076 0.434530 0.075 Uiso 1 1 calc R . . . .
C00J C 0.7138(2) 0.6326(4) 0.7002(6) 0.0628(12) Uani 1 1 d . . . . .
H00J H 0.730723 0.553372 0.723459 0.075 Uiso 1 1 calc R . . . .
C00K C 0.4918(3) 0.9543(5) 0.7787(6) 0.0721(14) Uani 1 1 d . . . . .
H00K H 0.479465 1.004929 0.856458 0.086 Uiso 1 1 calc R . . . .
C00L C 0.9473(3) 0.4758(4) 0.6583(6) 0.0645(13) Uani 1 1 d . . . . .
H00L H 0.915019 0.536701 0.647854 0.077 Uiso 1 1 calc R . . . .
C00M C 0.6575(2) 0.6629(5) 0.5990(6) 0.0664(13) Uani 1 1 d . . . . .
H00M H 0.628035 0.607117 0.540396 0.080 Uiso 1 1 calc R . . . .
C00N C 0.9032(2) 0.3569(5) 0.4117(5) 0.0608(12) Uani 1 1 d . . . . .
H00C H 0.923969 0.312060 0.335959 0.073 Uiso 1 1 calc R . . . .
H00N H 0.886993 0.434909 0.362501 0.073 Uiso 1 1 calc R . . . .
C00O C 1.0049(2) 0.3114(4) 0.6103(6) 0.0625(12) Uani 1 1 d . . . . .
H00O H 1.018107 0.241454 0.560749 0.075 Uiso 1 1 calc R . . . .
C00P C 0.4584(2) 0.8478(5) 0.7119(6) 0.0692(13) Uani 1 1 d . . . . .
H00P H 0.420092 0.815113 0.736427 0.083 Uiso 1 1 calc R . . . .
C00Q C 0.9998(3) 0.4642(5) 0.7808(6) 0.0757(15) Uani 1 1 d . . . . .
H00Q H 1.009789 0.516063 0.869623 0.091 Uiso 1 1 calc R . . . .
C00R C 0.5946(2) 0.8580(5) 0.5102(6) 0.0722(14) Uani 1 1 d . . . . .
H00A H 0.609485 0.938048 0.479042 0.087 Uiso 1 1 calc R . . . .
H00B H 0.575690 0.813370 0.413082 0.087 Uiso 1 1 calc R . . . .
C00S C 1.0360(3) 0.3609(6) 0.7501(7) 0.0804(16) Uani 1 1 d . . . . .
H00S H 1.074462 0.331685 0.814181 0.096 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
N001 C00G 1.366(6) . ?
N001 C00H 1.358(6) . ?
N001 C00R 1.430(6) . ?
N002 C00F 1.342(5) . ?
N002 C00I 1.372(5) . ?
N002 C00N 1.459(5) . ?
N003 C00L 1.358(6) . ?
N003 C00N 1.433(5) . ?
N003 C00O 1.360(5) . ?
N004 C00D 1.347(6) . ?
N004 C00M 1.360(6) . ?
N004 C00R 1.463(5) . ?
O005 N007 1.212(5) . ?
N006 O008 1.229(5) . ?
N006 O009 1.208(5) . ?
N006 C00B 1.426(5) . ?
N007 C00A 1.419(5) . ?
N007 O00C 1.233(5) . ?
C00A C00E 1.397(6) . ?
C00A C00F 1.371(5) . ?
C00B C00D 1.360(6) . ?
C00B C00J 1.395(6) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00I 1.352(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00K 1.338(7) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.337(7) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.351(6) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.403(7) . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.359(7) . ?
C00M H00M 0.9300 . ?
C00N H00C 0.9700 . ?
C00N H00N 0.9700 . ?
C00O H00O 0.9300 . ?
C00O C00S 1.347(7) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.396(8) . ?
C00R H00A 0.9700 . ?
C00R H00B 0.9700 . ?
C00S H00S 0.9300 . ?

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
C00G N001 C00R 125.3(4) . . ?
C00H N001 C00G 108.4(4) . . ?
C00H N001 C00R 126.3(4) . . ?
C00F N002 C00I 109.5(3) . . ?
C00F N002 C00N 125.2(4) . . ?
C00I N002 C00N 124.8(4) . . ?
C00L N003 C00N 124.9(4) . . ?
C00L N003 C00O 109.4(4) . . ?
C00O N003 C00N 125.6(4) . . ?
C00D N004 C00M 109.6(4) . . ?
C00D N004 C00R 124.5(4) . . ?
C00M N004 C00R 125.7(4) . . ?
O008 N006 C00B 117.8(4) . . ?
O009 N006 O008 122.7(4) . . ?
O009 N006 C00B 119.5(4) . . ?
O005 N007 C00A 119.5(4) . . ?
O005 N007 O00C 122.8(4) . . ?
O00C N007 C00A 117.7(4) . . ?
C00E C00A N007 125.8(4) . . ?
C00F C00A N007 124.4(4) . . ?
C00F C00A C00E 109.7(4) . . ?
C00D C00B N006 124.8(4) . . ?
C00D C00B C00J 109.1(4) . . ?
C00J C00B N006 126.1(4) . . ?
N004 C00D C00B 106.7(4) . . ?
N004 C00D H00D 126.7 . . ?
C00B C00D H00D 126.7 . . ?
C00A C00E H00E 127.4 . . ?
C00I C00E C00A 105.3(4) . . ?
C00I C00E H00E 127.4 . . ?
N002 C00F C00A 106.3(3) . . ?
N002 C00F H00F 126.8 . . ?
C00A C00F H00F 126.8 . . ?
N001 C00G H00G 126.3 . . ?
C00K C00G N001 107.5(4) . . ?
C00K C00G H00G 126.3 . . ?
N001 C00H H00H 125.5 . . ?
C00P C00H N001 109.0(4) . . ?
C00P C00H H00H 125.5 . . ?
N002 C00I H00I 125.4 . . ?
C00E C00I N002 109.2(4) . . ?
C00E C00I H00I 125.4 . . ?
C00B C00J H00J 127.0 . . ?
C00M C00J C00B 106.0(4) . . ?
C00M C00J H00J 127.0 . . ?
C00G C00K H00K 125.8 . . ?
C00G C00K C00P 108.5(4) . . ?
C00P C00K H00K 125.8 . . ?
N003 C00L H00L 126.5 . . ?
N003 C00L C00Q 107.0(5) . . ?
C00Q C00L H00L 126.5 . . ?
N004 C00M H00M 125.7 . . ?
C00J C00M N004 108.7(4) . . ?
C00J C00M H00M 125.7 . . ?
N002 C00N H00C 109.2 . . ?
N002 C00N H00N 109.2 . . ?
N003 C00N N002 112.2(3) . . ?
N003 C00N H00C 109.2 . . ?
N003 C00N H00N 109.2 . . ?
H00C C00N H00N 107.9 . . ?
N003 C00O H00O 125.9 . . ?
C00S C00O N003 108.2(5) . . ?
C00S C00O H00O 125.9 . . ?
C00H C00P C00K 106.6(5) . . ?
C00H C00P H00P 126.7 . . ?
C00K C00P H00P 126.7 . . ?
C00L C00Q H00Q 125.9 . . ?
C00L C00Q C00S 108.2(5) . . ?
C00S C00Q H00Q 125.9 . . ?
N001 C00R N004 112.2(3) . . ?
N001 C00R H00A 109.2 . . ?
N001 C00R H00B 109.2 . . ?
N004 C00R H00A 109.2 . . ?
N004 C00R H00B 109.2 . . ?
H00A C00R H00B 107.9 . . ?
C00O C00S C00Q 107.2(5) . . ?
C00O C00S H00S 126.4 . . ?
C00Q C00S H00S 126.4 . . ?

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
N001 C00G C00K C00P -0.4(5) . . . . ?
N001 C00H C00P C00K -0.1(5) . . . . ?
N003 C00L C00Q C00S 0.1(5) . . . . ?
N003 C00O C00S C00Q 0.2(5) . . . . ?
O005 N007 C00A C00E 5.2(7) . . . . ?
O005 N007 C00A C00F -173.4(4) . . . . ?
N006 C00B C00D N004 179.6(4) . . . . ?
N006 C00B C00J C00M 179.8(4) . . . . ?
N007 C00A C00E C00I -179.1(4) . . . . ?
N007 C00A C00F N002 179.5(4) . . . . ?
O008 N006 C00B C00D 1.4(7) . . . . ?
O008 N006 C00B C00J -178.6(5) . . . . ?
O009 N006 C00B C00D -177.8(5) . . . . ?
O009 N006 C00B C00J 2.2(8) . . . . ?
C00A C00E C00I N002 -0.1(5) . . . . ?
C00B C00J C00M N004 0.8(5) . . . . ?
O00C N007 C00A C00E -174.6(5) . . . . ?
O00C N007 C00A C00F 6.8(7) . . . . ?
C00D N004 C00M C00J -1.1(5) . . . . ?
C00D N004 C00R N001 -84.9(5) . . . . ?
C00D C00B C00J C00M -0.2(5) . . . . ?
C00E C00A C00F N002 0.7(5) . . . . ?
C00F N002 C00I C00E 0.5(5) . . . . ?
C00F N002 C00N N003 86.6(5) . . . . ?
C00F C00A C00E C00I -0.3(5) . . . . ?
C00G N001 C00H C00P -0.1(5) . . . . ?
C00G N001 C00R N004 85.3(6) . . . . ?
C00G C00K C00P C00H 0.3(5) . . . . ?
C00H N001 C00G C00K 0.3(5) . . . . ?
C00H N001 C00R N004 -93.0(5) . . . . ?
C00I N002 C00F C00A -0.7(5) . . . . ?
C00I N002 C00N N003 -84.0(5) . . . . ?
C00J C00B C00D N004 -0.4(5) . . . . ?
C00L N003 C00N N002 -83.5(5) . . . . ?
C00L N003 C00O C00S -0.2(5) . . . . ?
C00L C00Q C00S C00O -0.2(6) . . . . ?
C00M N004 C00D C00B 0.9(5) . . . . ?
C00M N004 C00R N001 89.5(6) . . . . ?
C00N N002 C00F C00A -172.6(4) . . . . ?
C00N N002 C00I C00E 172.4(4) . . . . ?
C00N N003 C00L C00Q 177.1(4) . . . . ?
C00N N003 C00O C00S -177.2(4) . . . . ?
C00O N003 C00L C00Q 0.0(5) . . . . ?
C00O N003 C00N N002 93.1(5) . . . . ?
C00R N001 C00G C00K -178.3(4) . . . . ?
C00R N001 C00H C00P 178.4(4) . . . . ?
C00R N004 C00D C00B 176.1(4) . . . . ?
C00R N004 C00M C00J -176.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_VSP-C7
_database_code_depnum_ccdc_archive 'CCDC 2476741'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N4 O4'
_chemical_formula_sum            'C9 H8 N4 O4'
_chemical_formula_weight         236.19

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                   7.4622(8)
_cell_length_b                   10.6054(12)
_cell_length_c                   13.7873(16)
_cell_angle_alpha                71.770(4)
_cell_angle_beta                 76.216(4)
_cell_angle_gamma                79.495(3)
_cell_volume                     999.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.42

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_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 ?
_diffrn_reflns_number            22093
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3513
_reflns_number_gt                2793
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0785P)²+0.2128P] 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         3513
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.9672(3) 0.68841(18) 0.10649(16) 0.0824(6) Uani 1 1 d . . . . .
O4 O 0.3071(2) 0.15420(19) 0.41114(15) 0.0832(6) Uani 1 1 d . . . . .
O5 O 0.3421(2) 0.67624(16) 0.38246(14) 0.0645(5) Uani 1 1 d . . . . .
O7 O -0.3366(2) 0.92260(18) 0.27677(16) 0.0729(5) Uani 1 1 d . . . . .
N1 N 0.6306(2) 0.47914(16) 0.12626(12) 0.0419(4) Uani 1 1 d . . . . .
N2 N 0.7247(2) 0.26244(16) 0.24340(12) 0.0415(4) Uani 1 1 d . . . . .
O2 O 1.0138(2) 0.47957(18) 0.11161(13) 0.0666(5) Uani 1 1 d . . . . .
O3 O 0.3514(2) 0.24945(17) 0.24569(14) 0.0659(5) Uani 1 1 d . . . . .
N6 N 0.0476(2) 0.90598(16) 0.26838(13) 0.0434(4) Uani 1 1 d . . . . .
N5 N -0.0321(2) 0.68366(16) 0.37301(12) 0.0414(4) Uani 1 1 d . . . . .
O6 O 0.3995(2) 0.47655(17) 0.36482(13) 0.0648(5) Uani 1 1 d . . . . .
C3 C 0.4228(3) 0.6614(2) 0.11041(16) 0.0530(6) Uani 1 1 d . . . . .
H3 H 0.311641 0.716903 0.104880 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4503(3) 0.5274(2) 0.12100(15) 0.0479(5) Uani 1 1 d . . . . .
H4 H 0.358907 0.476406 0.124166 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7029(3) 0.3389(2) 0.13762(15) 0.0450(5) Uani 1 1 d . . . . .
H5A H 0.822598 0.334261 0.091245 0.054 Uiso 1 1 calc R U . . .
H5B H 0.619546 0.297405 0.115906 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5947(3) 0.20761(19) 0.32911(16) 0.0446(5) Uani 1 1 d . . . . .
C8 C 0.6810(3) 0.1460(2) 0.41213(17) 0.0540(6) Uani 1 1 d . . . . .
H8 H 0.624775 0.102336 0.479255 0.065 Uiso 1 1 calc R U . . .
N3 N 0.9094(3) 0.5839(2) 0.11239(14) 0.0546(5) Uani 1 1 d . . . . .
C1 C 0.7181(3) 0.5874(2) 0.11845(15) 0.0454(5) Uani 1 1 d . . . . .
C7 C 0.8674(3) 0.1612(2) 0.37698(18) 0.0539(6) Uani 1 1 d . . . . .
H7 H 0.960152 0.128581 0.416197 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8913(3) 0.2324(2) 0.27494(17) 0.0479(5) Uani 1 1 d . . . . .
H6 H 1.004089 0.256895 0.232938 0.057 Uiso 1 1 calc R U . . .
N4 N 0.4083(2) 0.20411(18) 0.32759(16) 0.0544(5) Uani 1 1 d . . . . .
C2 C 0.5914(3) 0.6993(2) 0.10944(17) 0.0540(6) Uani 1 1 d . . . . .
H2 H 0.614295 0.784954 0.103725 0.065 Uiso 1 1 calc R U . . .
O9 O -0.2983(3) 1.0315(2) 0.11341(15) 0.0817(6) Uani 1 1 d . . . . .
N8 N -0.2363(3) 0.97263(18) 0.19372(17) 0.0548(5) Uani 1 1 d . . . . .
C18 C -0.0452(3) 0.9690(2) 0.18698(16) 0.0454(5) Uani 1 1 d . . . . .
C14 C -0.0189(3) 0.8197(2) 0.37177(16) 0.0470(5) Uani 1 1 d . . . . .
H14A H 0.064366 0.816331 0.417060 0.056 Uiso 1 1 calc R U . . .
H14B H -0.140575 0.858750 0.399808 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1054(3) 0.5780(2) 0.36728(14) 0.0412(5) Uani 1 1 d . . . . .
C11 C 0.0267(3) 0.4709(2) 0.36755(16) 0.0468(5) Uani 1 1 d . . . . .
H11 H 0.088634 0.387512 0.364096 0.056 Uiso 1 1 calc R U . . .
N7 N 0.2927(2) 0.57766(18) 0.37135(13) 0.0475(4) Uani 1 1 d . . . . .
C17 C 0.0749(3) 1.0388(2) 0.10402(18) 0.0543(6) Uani 1 1 d . . . . .
H17 H 0.047763 1.089479 0.039665 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2446(3) 1.0193(2) 0.13444(19) 0.0593(6) Uani 1 1 d . . . . .
H16 H 0.352552 1.054675 0.094185 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2237(3) 0.9388(2) 0.23424(18) 0.0523(6) Uani 1 1 d . . . . .
H15 H 0.316839 0.910385 0.273314 0.063 Uiso 1 1 calc R U . . .
C13 C -0.1947(3) 0.6389(2) 0.37738(15) 0.0465(5) Uani 1 1 d . . . . .
H13 H -0.310771 0.689111 0.382037 0.056 Uiso 1 1 calc R U . . .
C12 C -0.1618(3) 0.5098(2) 0.37391(16) 0.0490(5) Uani 1 1 d . . . . .
H12 H -0.250120 0.457289 0.375526 0.059 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 N3 1.234(2) . ?
O4 N4 1.236(2) . ?
O5 N7 1.233(2) . ?
O7 N8 1.228(2) . ?
N1 C4 1.360(3) . ?
N1 C1 1.385(3) . ?
N1 C5 1.459(3) . ?
N2 C6 1.364(3) . ?
N2 C9 1.380(3) . ?
N2 C5 1.462(3) . ?
O2 N3 1.232(2) . ?
O3 N4 1.225(2) . ?
N6 C15 1.356(3) . ?
N6 C18 1.385(3) . ?
N6 C14 1.459(3) . ?
N5 C13 1.363(3) . ?
N5 C10 1.383(2) . ?
N5 C14 1.458(3) . ?
O6 N7 1.228(2) . ?
C3 C4 1.364(3) . ?
C3 C2 1.385(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 C8 1.372(3) . ?
C9 N4 1.404(3) . ?
C8 C7 1.381(3) . ?
C8 H8 0.9300 . ?
N3 C1 1.404(3) . ?
C1 C2 1.368(3) . ?
C7 C6 1.359(3) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
O9 N8 1.239(3) . ?
N8 C18 1.401(3) . ?
C18 C17 1.372(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C10 C11 1.369(3) . ?
C10 N7 1.411(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C17 C16 1.387(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.363(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C13 C12 1.360(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

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
C4 N1 C1 106.14(17) . . ?
C4 N1 C5 123.08(17) . . ?
C1 N1 C5 130.78(16) . . ?
C6 N2 C9 106.33(16) . . ?
C6 N2 C5 123.32(17) . . ?
C9 N2 C5 130.35(17) . . ?
C15 N6 C18 106.31(17) . . ?
C15 N6 C14 123.79(18) . . ?
C18 N6 C14 129.89(17) . . ?
C13 N5 C10 106.33(16) . . ?
C13 N5 C14 123.47(17) . . ?
C10 N5 C14 130.17(17) . . ?
C4 C3 C2 107.23(19) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
N1 C4 C3 110.19(19) . . ?
N1 C4 H4 124.9 . . ?
C3 C4 H4 124.9 . . ?
N1 C5 N2 114.18(15) . . ?
N1 C5 H5A 108.7 . . ?
N2 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
N2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C8 C9 N2 109.17(19) . . ?
C8 C9 N4 125.79(19) . . ?
N2 C9 N4 124.73(18) . . ?
C9 C8 C7 106.9(2) . . ?
C9 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
O2 N3 O1 122.21(19) . . ?
O2 N3 C1 120.21(19) . . ?
O1 N3 C1 117.6(2) . . ?
C2 C1 N1 109.19(18) . . ?
C2 C1 N3 125.7(2) . . ?
N1 C1 N3 124.92(19) . . ?
C6 C7 C8 107.9(2) . . ?
C6 C7 H7 126.1 . . ?
C8 C7 H7 126.1 . . ?
C7 C6 N2 109.73(19) . . ?
C7 C6 H6 125.1 . . ?
N2 C6 H6 125.1 . . ?
O3 N4 O4 122.5(2) . . ?
O3 N4 C9 120.16(18) . . ?
O4 N4 C9 117.4(2) . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
O7 N8 O9 122.3(2) . . ?
O7 N8 C18 120.7(2) . . ?
O9 N8 C18 116.9(2) . . ?
C17 C18 N6 109.13(19) . . ?
C17 C18 N8 125.9(2) . . ?
N6 C18 N8 124.62(19) . . ?
N5 C14 N6 113.76(15) . . ?
N5 C14 H14A 108.8 . . ?
N6 C14 H14A 108.8 . . ?
N5 C14 H14B 108.8 . . ?
N6 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C11 C10 N5 109.01(17) . . ?
C11 C10 N7 125.86(18) . . ?
N5 C10 N7 124.84(18) . . ?
C10 C11 C12 107.23(18) . . ?
C10 C11 H11 126.4 . . ?
C12 C11 H11 126.4 . . ?
O6 N7 O5 122.81(18) . . ?
O6 N7 C10 117.55(18) . . ?
O5 N7 C10 119.64(17) . . ?
C18 C17 C16 107.0(2) . . ?
C18 C17 H17 126.5 . . ?
C16 C17 H17 126.5 . . ?
C15 C16 C17 107.3(2) . . ?
C15 C16 H16 126.3 . . ?
C17 C16 H16 126.3 . . ?
N6 C15 C16 110.3(2) . . ?
N6 C15 H15 124.9 . . ?
C16 C15 H15 124.9 . . ?
C12 C13 N5 109.84(18) . . ?
C12 C13 H13 125.1 . . ?
N5 C13 H13 125.1 . . ?
C13 C12 C11 107.59(19) . . ?
C13 C12 H12 126.2 . . ?
C11 C12 H12 126.2 . . ?

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
C1 N1 C4 C3 -0.1(2) . . . . ?
C5 N1 C4 C3 -179.94(17) . . . . ?
C2 C3 C4 N1 -0.3(2) . . . . ?
C4 N1 C5 N2 -101.4(2) . . . . ?
C1 N1 C5 N2 78.8(2) . . . . ?
C6 N2 C5 N1 -100.6(2) . . . . ?
C9 N2 C5 N1 79.1(2) . . . . ?
C6 N2 C9 C8 0.6(2) . . . . ?
C5 N2 C9 C8 -179.21(18) . . . . ?
C6 N2 C9 N4 -173.34(18) . . . . ?
C5 N2 C9 N4 6.9(3) . . . . ?
N2 C9 C8 C7 -0.9(2) . . . . ?
N4 C9 C8 C7 172.98(19) . . . . ?
C4 N1 C1 C2 0.5(2) . . . . ?
C5 N1 C1 C2 -179.70(17) . . . . ?
C4 N1 C1 N3 -174.84(18) . . . . ?
C5 N1 C1 N3 5.0(3) . . . . ?
O2 N3 C1 C2 -173.0(2) . . . . ?
O1 N3 C1 C2 6.0(3) . . . . ?
O2 N3 C1 N1 1.5(3) . . . . ?
O1 N3 C1 N1 -179.46(19) . . . . ?
C9 C8 C7 C6 0.8(2) . . . . ?
C8 C7 C6 N2 -0.5(2) . . . . ?
C9 N2 C6 C7 -0.1(2) . . . . ?
C5 N2 C6 C7 179.74(17) . . . . ?
C8 C9 N4 O3 -171.4(2) . . . . ?
N2 C9 N4 O3 1.5(3) . . . . ?
C8 C9 N4 O4 8.6(3) . . . . ?
N2 C9 N4 O4 -178.45(19) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
N3 C1 C2 C3 174.61(19) . . . . ?
C4 C3 C2 C1 0.6(2) . . . . ?
C15 N6 C18 C17 0.3(2) . . . . ?
C14 N6 C18 C17 -179.26(18) . . . . ?
C15 N6 C18 N8 -172.87(19) . . . . ?
C14 N6 C18 N8 7.5(3) . . . . ?
O7 N8 C18 C17 -169.0(2) . . . . ?
O9 N8 C18 C17 9.0(3) . . . . ?
O7 N8 C18 N6 3.1(3) . . . . ?
O9 N8 C18 N6 -178.98(18) . . . . ?
C13 N5 C14 N6 -100.5(2) . . . . ?
C10 N5 C14 N6 77.3(2) . . . . ?
C15 N6 C14 N5 -102.2(2) . . . . ?
C18 N6 C14 N5 77.4(2) . . . . ?
C13 N5 C10 C11 0.4(2) . . . . ?
C14 N5 C10 C11 -177.80(18) . . . . ?
C13 N5 C10 N7 -173.71(18) . . . . ?
C14 N5 C10 N7 8.1(3) . . . . ?
N5 C10 C11 C12 -0.2(2) . . . . ?
N7 C10 C11 C12 173.76(18) . . . . ?
C11 C10 N7 O6 7.3(3) . . . . ?
N5 C10 N7 O6 -179.67(17) . . . . ?
C11 C10 N7 O5 -171.85(19) . . . . ?
N5 C10 N7 O5 1.2(3) . . . . ?
N6 C18 C17 C16 -0.2(2) . . . . ?
N8 C18 C17 C16 172.86(19) . . . . ?
C18 C17 C16 C15 0.1(2) . . . . ?
C18 N6 C15 C16 -0.3(2) . . . . ?
C14 N6 C15 C16 179.32(18) . . . . ?
C17 C16 C15 N6 0.2(3) . . . . ?
C10 N5 C13 C12 -0.4(2) . . . . ?
C14 N5 C13 C12 177.95(17) . . . . ?
N5 C13 C12 C11 0.2(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_vsp-c4
_database_code_depnum_ccdc_archive 'CCDC 2476738'
loop_
_audit_author_name
_audit_author_address
'V Shanmugapriya'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2025-03-28
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 N6 O8'
_chemical_formula_sum            'C9 H6 N6 O8'
_chemical_formula_weight         326.20
_chemical_melting_point          ?
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 1 21/c 1'
_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                   8.6057(4)
_cell_length_b                   23.5270(9)
_cell_length_c                   12.9863(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.6950(10)
_cell_angle_gamma                90
_cell_volume                     2504.89(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41866
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3573
_reflns_number_total             4368
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+1.2784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.045) H3(0.051) H5A(0.046) H5B(0.046) H6(0.044) H9(0.047)
 H10(0.048) H12(0.048) H14A(0.047) H14B(0.047) H15(0.048) H18(0.043)
 Fixed X: H1(-0.047556) H3(-0.286208) H5A(0.227401) H5B(0.254017) H6(0.221364)
 H9(0.487355) H10(0.160825) H12(0.198175) H14A(0.39813) H14B(0.348237)
 H15(0.703923) H18(0.545199)
 Fixed Y: H1(0.528299) H3(0.671983) H5A(0.563769) H5B(0.629717) H6(0.528387)
 H9(0.658017) H10(0.598456) H12(0.676964) H14A(0.714154) H14B(0.653477)
 H15(0.727381) H18(0.569484)
 Fixed Z: H1(0.198611) H3(0.225903) H5A(0.220317) H5B(0.22194) H6(0.431642)
 H9(0.379198) H10(0.802268) H12(0.535191) H14A(0.918929) H14B(0.948145)
 H15(0.974833) H18(0.890517)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.5860(2) 0.52749(7) 0.69545(13) 0.0634(5) Uani 1 1 d . . . . .
O2 O 0.3336(3) 0.50091(10) 0.63327(16) 0.0887(7) Uani 1 1 d . . . . .
O5 O 0.1873(2) 0.71137(7) 0.32155(16) 0.0659(5) Uani 1 1 d . . . . .
O6 O -0.0485(3) 0.75164(8) 0.2810(2) 0.0959(8) Uani 1 1 d . . . . .
O7 O -0.3621(2) 0.50850(8) 0.13449(15) 0.0654(5) Uani 1 1 d . . . . .
O8 O -0.4965(2) 0.58391(9) 0.15090(17) 0.0765(6) Uani 1 1 d . . . . .
O15 O 0.6603(2) 0.64183(8) 0.68854(13) 0.0655(5) Uani 1 1 d . . . . .
O16 O 0.7348(2) 0.67260(8) 0.55316(15) 0.0691(5) Uani 1 1 d . . . . .
N00P N 0.0379(2) 0.70991(7) 0.28805(16) 0.0514(5) Uani 1 1 d . . . . .
N1 N 0.04362(19) 0.60752(6) 0.24629(12) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.31737(19) 0.59528(6) 0.36927(12) 0.0350(4) Uani 1 1 d . . . . .
N3 N 0.6486(2) 0.64337(8) 0.59240(15) 0.0479(4) Uani 1 1 d . . . . .
N4 N 0.4501(3) 0.52953(8) 0.62879(14) 0.0482(5) Uani 1 1 d . . . . .
N5 N -0.3696(2) 0.55828(9) 0.15978(15) 0.0488(5) Uani 1 1 d . . . . .
C1 C -0.0689(2) 0.56590(8) 0.21188(15) 0.0372(4) Uani 1 1 d . . . . .
H1 H -0.047556 0.528299 0.198611 0.045 Uiso 1 1 calc R U . . .
C2 C -0.2196(2) 0.58889(9) 0.20004(15) 0.0384(4) Uani 1 1 d . . . . .
C3 C -0.2035(2) 0.64634(9) 0.22688(17) 0.0424(5) Uani 1 1 d . . . . .
H3 H -0.286208 0.671983 0.225903 0.051 Uiso 1 1 calc R U . . .
C4 C -0.0406(2) 0.65681(8) 0.25484(16) 0.0382(4) Uani 1 1 d . . . . .
C5 C 0.2159(2) 0.59867(9) 0.25709(15) 0.0381(4) Uani 1 1 d . . . . .
H5A H 0.227401 0.563769 0.220317 0.046 Uiso 1 1 calc R U . . .
H5B H 0.254017 0.629717 0.221940 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3013(2) 0.55632(8) 0.44295(15) 0.0367(4) Uani 1 1 d . . . . .
H6 H 0.221364 0.528387 0.431642 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4243(2) 0.56590(8) 0.53653(15) 0.0363(4) Uani 1 1 d . . . . .
C8 C 0.5197(2) 0.61169(8) 0.51767(15) 0.0372(4) Uani 1 1 d . . . . .
C9 C 0.4505(2) 0.62872(8) 0.41384(16) 0.0392(5) Uani 1 1 d . . . . .
H9 H 0.487355 0.658017 0.379198 0.047 Uiso 1 1 calc R U . . .
O3 O -0.0491(2) 0.55270(8) 0.62845(16) 0.0738(5) Uani 1 1 d . . . . .
O4 O -0.0223(2) 0.59112(9) 0.48312(14) 0.0696(5) Uani 1 1 d . . . . .
O9 O 0.50599(19) 0.75813(6) 0.78347(13) 0.0534(4) Uani 1 1 d . . . . .
O10 O 0.4378(2) 0.75225(8) 0.60866(14) 0.0680(5) Uani 1 1 d . . . . .
O11 O 1.1104(2) 0.64181(9) 1.02061(15) 0.0731(5) Uani 1 1 d . . . . .
O12 O 1.0186(3) 0.72630(10) 1.0230(2) 0.1104(9) Uani 1 1 d . . . . .
O13 O 0.9701(2) 0.55768(8) 0.87012(16) 0.0731(5) Uani 1 1 d . . . . .
O14 O 0.8152(2) 0.50459(7) 0.93018(14) 0.0602(4) Uani 1 1 d . . . . .
N6 N 0.4277(2) 0.73667(7) 0.69660(15) 0.0431(4) Uani 1 1 d . . . . .
N7 N 0.30883(18) 0.66430(7) 0.78898(12) 0.0348(4) Uani 1 1 d . . . . .
N8 N 0.56821(18) 0.65506(7) 0.92573(12) 0.0354(4) Uani 1 1 d . . . . .
N9 N 0.9988(2) 0.67630(9) 1.00346(16) 0.0542(5) Uani 1 1 d . . . . .
N10 N 0.8625(2) 0.55095(8) 0.91094(13) 0.0439(4) Uani 1 1 d . . . . .
N11 N 0.0129(2) 0.58685(9) 0.58122(16) 0.0510(5) Uani 1 1 d . . . . .
C10 C 0.1941(2) 0.62312(9) 0.75709(16) 0.0401(5) Uani 1 1 d . . . . .
H10 H 0.160825 0.598456 0.802268 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1357(2) 0.62427(9) 0.64643(16) 0.0390(4) Uani 1 1 d . . . . .
C12 C 0.2145(2) 0.66694(8) 0.60698(16) 0.0400(5) Uani 1 1 d . . . . .
H12 H 0.198175 0.676964 0.535191 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3207(2) 0.69079(8) 0.69666(15) 0.0349(4) Uani 1 1 d . . . . .
C14 C 0.3999(2) 0.67398(9) 0.90256(15) 0.0391(5) Uani 1 1 d . . . . .
H14A H 0.398130 0.714154 0.918929 0.047 Uiso 1 1 calc R U . . .
H14B H 0.348237 0.653477 0.948145 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7026(2) 0.68890(9) 0.95822(16) 0.0402(5) Uani 1 1 d . . . . .
H15 H 0.703923 0.727381 0.974833 0.048 Uiso 1 1 calc R U . . .
C16 C 0.8347(2) 0.65622(9) 0.96197(15) 0.0381(4) Uani 1 1 d . . . . .
C17 C 0.7784(2) 0.60036(8) 0.93270(14) 0.0351(4) Uani 1 1 d . . . . .
C18 C 0.6142(2) 0.60062(8) 0.91128(14) 0.0356(4) Uani 1 1 d . . . . .
H18 H 0.545199 0.569484 0.890517 0.043 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 N4 1.226(2) . ?
O2 N4 1.224(3) . ?
O5 N00P 1.226(2) . ?
O6 N00P 1.218(2) . ?
O7 N5 1.223(3) . ?
O8 N5 1.222(3) . ?
O15 N3 1.222(2) . ?
O16 N3 1.230(2) . ?
N00P C4 1.423(3) . ?
N1 C1 1.354(2) . ?
N1 C4 1.390(2) . ?
N1 C5 1.461(2) . ?
N2 C5 1.455(2) . ?
N2 C6 1.362(2) . ?
N2 C9 1.365(2) . ?
N3 C8 1.440(3) . ?
N4 C7 1.433(3) . ?
N5 C2 1.431(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(3) . ?
C2 C3 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.366(3) . ?
C7 C8 1.420(3) . ?
C8 C9 1.358(3) . ?
C9 H9 0.9300 . ?
O3 N11 1.227(3) . ?
O4 N11 1.221(2) . ?
O9 N6 1.232(2) . ?
O10 N6 1.228(2) . ?
O11 N9 1.225(3) . ?
O12 N9 1.204(3) . ?
O13 N10 1.209(2) . ?
O14 N10 1.216(2) . ?
N6 C13 1.419(3) . ?
N7 C10 1.355(2) . ?
N7 C13 1.382(2) . ?
N7 C14 1.462(2) . ?
N8 C14 1.456(2) . ?
N8 C15 1.361(2) . ?
N8 C18 1.370(2) . ?
N9 C16 1.430(3) . ?
N10 C17 1.442(3) . ?
N11 C11 1.437(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C11 C12 1.393(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C16 1.361(3) . ?
C16 C17 1.412(3) . ?
C17 C18 1.354(3) . ?
C18 H18 0.9300 . ?

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
O5 N00P C4 118.83(17) . . ?
O6 N00P O5 123.67(19) . . ?
O6 N00P C4 117.49(19) . . ?
C1 N1 C4 106.97(16) . . ?
C1 N1 C5 122.10(16) . . ?
C4 N1 C5 130.55(16) . . ?
C6 N2 C5 125.57(16) . . ?
C6 N2 C9 109.96(16) . . ?
C9 N2 C5 124.33(16) . . ?
O15 N3 O16 124.5(2) . . ?
O15 N3 C8 118.71(19) . . ?
O16 N3 C8 116.64(19) . . ?
O1 N4 C7 119.1(2) . . ?
O2 N4 O1 124.34(19) . . ?
O2 N4 C7 116.54(19) . . ?
O7 N5 C2 117.67(19) . . ?
O8 N5 O7 124.5(2) . . ?
O8 N5 C2 117.9(2) . . ?
N1 C1 H1 126.0 . . ?
N1 C1 C2 108.00(17) . . ?
C2 C1 H1 126.0 . . ?
C1 C2 N5 124.08(19) . . ?
C1 C2 C3 109.65(18) . . ?
C3 C2 N5 126.18(19) . . ?
C2 C3 H3 127.5 . . ?
C4 C3 C2 105.01(18) . . ?
C4 C3 H3 127.5 . . ?
N1 C4 N00P 123.04(17) . . ?
C3 C4 N00P 126.59(18) . . ?
C3 C4 N1 110.38(17) . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
N2 C5 N1 112.75(15) . . ?
N2 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N2 C6 H6 126.4 . . ?
N2 C6 C7 107.29(17) . . ?
C7 C6 H6 126.4 . . ?
C6 C7 N4 121.78(19) . . ?
C6 C7 C8 107.70(17) . . ?
C8 C7 N4 130.23(18) . . ?
C7 C8 N3 130.07(18) . . ?
C9 C8 N3 122.13(18) . . ?
C9 C8 C7 107.03(17) . . ?
N2 C9 H9 126.0 . . ?
C8 C9 N2 108.01(17) . . ?
C8 C9 H9 126.0 . . ?
O9 N6 C13 119.03(17) . . ?
O10 N6 O9 123.76(18) . . ?
O10 N6 C13 117.20(18) . . ?
C10 N7 C13 107.23(16) . . ?
C10 N7 C14 122.48(16) . . ?
C13 N7 C14 130.26(16) . . ?
C15 N8 C14 125.67(17) . . ?
C15 N8 C18 109.60(16) . . ?
C18 N8 C14 124.61(16) . . ?
O11 N9 C16 118.7(2) . . ?
O12 N9 O11 123.8(2) . . ?
O12 N9 C16 117.5(2) . . ?
O13 N10 O14 123.78(19) . . ?
O13 N10 C17 118.51(18) . . ?
O14 N10 C17 117.62(17) . . ?
O3 N11 C11 117.40(19) . . ?
O4 N11 O3 124.6(2) . . ?
O4 N11 C11 118.01(19) . . ?
N7 C10 H10 126.1 . . ?
N7 C10 C11 107.90(17) . . ?
C11 C10 H10 126.1 . . ?
C10 C11 N11 125.13(19) . . ?
C10 C11 C12 109.59(18) . . ?
C12 C11 N11 125.28(19) . . ?
C11 C12 H12 127.5 . . ?
C13 C12 C11 104.91(18) . . ?
C13 C12 H12 127.5 . . ?
N7 C13 N6 124.22(17) . . ?
C12 C13 N6 125.40(18) . . ?
C12 C13 N7 110.38(17) . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
N8 C14 N7 110.81(15) . . ?
N8 C14 H14A 109.5 . . ?
N8 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N8 C15 H15 126.2 . . ?
C16 C15 N8 107.60(17) . . ?
C16 C15 H15 126.2 . . ?
C15 C16 N9 123.04(19) . . ?
C15 C16 C17 107.56(17) . . ?
C17 C16 N9 128.87(19) . . ?
C16 C17 N10 130.64(18) . . ?
C18 C17 N10 121.18(18) . . ?
C18 C17 C16 107.59(17) . . ?
N8 C18 H18 126.2 . . ?
C17 C18 N8 107.64(17) . . ?
C17 C18 H18 126.2 . . ?

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
O1 N4 C7 C6 156.33(19) . . . . ?
O1 N4 C7 C8 -16.6(3) . . . . ?
O2 N4 C7 C6 -21.4(3) . . . . ?
O2 N4 C7 C8 165.7(2) . . . . ?
O5 N00P C4 N1 -7.9(3) . . . . ?
O5 N00P C4 C3 172.4(2) . . . . ?
O6 N00P C4 N1 171.8(2) . . . . ?
O6 N00P C4 C3 -7.8(3) . . . . ?
O7 N5 C2 C1 0.0(3) . . . . ?
O7 N5 C2 C3 176.0(2) . . . . ?
O8 N5 C2 C1 -178.5(2) . . . . ?
O8 N5 C2 C3 -2.5(3) . . . . ?
O15 N3 C8 C7 -18.7(3) . . . . ?
O15 N3 C8 C9 149.9(2) . . . . ?
O16 N3 C8 C7 164.8(2) . . . . ?
O16 N3 C8 C9 -26.6(3) . . . . ?
N1 C1 C2 N5 176.83(17) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
N2 C6 C7 N4 -175.42(17) . . . . ?
N2 C6 C7 C8 -1.1(2) . . . . ?
N3 C8 C9 N2 -170.81(17) . . . . ?
N4 C7 C8 N3 -15.8(3) . . . . ?
N4 C7 C8 C9 174.30(19) . . . . ?
N5 C2 C3 C4 -176.52(18) . . . . ?
C1 N1 C4 N00P -179.35(18) . . . . ?
C1 N1 C4 C3 0.4(2) . . . . ?
C1 N1 C5 N2 -107.6(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 N00P 179.50(19) . . . . ?
C2 C3 C4 N1 -0.2(2) . . . . ?
C4 N1 C1 C2 -0.4(2) . . . . ?
C4 N1 C5 N2 80.4(2) . . . . ?
C5 N1 C1 C2 -173.98(16) . . . . ?
C5 N1 C4 N00P -6.5(3) . . . . ?
C5 N1 C4 C3 173.23(18) . . . . ?
C5 N2 C6 C7 177.09(17) . . . . ?
C5 N2 C9 C8 -176.75(17) . . . . ?
C6 N2 C5 N1 59.7(2) . . . . ?
C6 N2 C9 C8 -0.8(2) . . . . ?
C6 C7 C8 N3 170.56(19) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C8 C9 N2 0.1(2) . . . . ?
C9 N2 C5 N1 -124.99(19) . . . . ?
C9 N2 C6 C7 1.2(2) . . . . ?
O3 N11 C11 C10 3.0(3) . . . . ?
O3 N11 C11 C12 -177.5(2) . . . . ?
O4 N11 C11 C10 -176.9(2) . . . . ?
O4 N11 C11 C12 2.6(3) . . . . ?
O9 N6 C13 N7 -6.5(3) . . . . ?
O9 N6 C13 C12 172.76(19) . . . . ?
O10 N6 C13 N7 172.64(18) . . . . ?
O10 N6 C13 C12 -8.1(3) . . . . ?
O11 N9 C16 C15 168.0(2) . . . . ?
O11 N9 C16 C17 -2.5(3) . . . . ?
O12 N9 C16 C15 -9.5(3) . . . . ?
O12 N9 C16 C17 180.0(2) . . . . ?
O13 N10 C17 C16 -32.8(3) . . . . ?
O13 N10 C17 C18 137.3(2) . . . . ?
O14 N10 C17 C16 150.7(2) . . . . ?
O14 N10 C17 C18 -39.3(3) . . . . ?
N7 C10 C11 N11 179.51(18) . . . . ?
N7 C10 C11 C12 0.0(2) . . . . ?
N8 C15 C16 N9 -173.45(17) . . . . ?
N8 C15 C16 C17 -1.1(2) . . . . ?
N9 C16 C17 N10 -16.8(3) . . . . ?
N9 C16 C17 C18 172.12(19) . . . . ?
N10 C17 C18 N8 -171.63(16) . . . . ?
N11 C11 C12 C13 -179.40(19) . . . . ?
C10 N7 C13 N6 179.58(18) . . . . ?
C10 N7 C13 C12 0.2(2) . . . . ?
C10 N7 C14 N8 107.8(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 N6 -179.59(18) . . . . ?
C11 C12 C13 N7 -0.2(2) . . . . ?
C13 N7 C10 C11 -0.1(2) . . . . ?
C13 N7 C14 N8 -70.0(2) . . . . ?
C14 N7 C10 C11 -178.33(16) . . . . ?
C14 N7 C13 N6 -2.4(3) . . . . ?
C14 N7 C13 C12 178.24(18) . . . . ?
C14 N8 C15 C16 -174.71(17) . . . . ?
C14 N8 C18 C17 175.02(16) . . . . ?
C15 N8 C14 N7 116.7(2) . . . . ?
C15 N8 C18 C17 -1.2(2) . . . . ?
C15 C16 C17 N10 171.51(19) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C16 C17 C18 N8 0.5(2) . . . . ?
C18 N8 C14 N7 -59.0(2) . . . . ?
C18 N8 C15 C16 1.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
