# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2241660'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.03.24 svn.rc9df729e for OlexSys, GUI svn.r6758)
;
_chemical_formula_moiety         'C5 H3 N8 Na O7'
_chemical_formula_sum            'C5 H3 N8 Na O7'
_chemical_formula_weight         310.119
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
Na 0.03705 0.02512 4.76260 3.17360 1.26740 1.11280 3.28500 8.84220 0.31360
129.42400 0.67600 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
brennan

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   11.4210(11)
_cell_length_b                   9.3158(10)
_cell_length_c                   21.599(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.498(4)
_cell_angle_gamma                90
_cell_volume                     2283.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.83
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10 
_exptl_special_details 
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1249.498
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.059
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.9956
_diffrn_reflns_Laue_measured_fraction_max 0.9968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26458
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9968
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.83
_diffrn_ambient_temperature      108.00
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2553
_reflns_number_total             2829
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3491
_refine_diff_density_min         -0.2611
_refine_diff_density_rms         0.0488
_refine_ls_d_res_high            0.7501
_refine_ls_d_res_low             7.2003
_refine_ls_goodness_of_fit_ref   1.0597
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.0597
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+1.8518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0789
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
;
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_refinement_flags_posn
Na2 Na 0.67686(4) 1.10525(5) 0.53419(2) 0.01839(12) Uani 1.000000 .
O1 O 0.64741(7) 1.25542(9) 0.44513(4) 0.01927(17) Uani 1.000000 .
O3 O 0.85095(7) 0.97336(9) 0.49207(4) 0.02374(18) Uani 1.000000 .
O4 O 0.90446(7) 0.84004(10) 0.41728(4) 0.02329(19) Uani 1.000000 .
O7 O 0.35717(7) 0.66654(10) 0.37775(5) 0.0285(2) Uani 1.000000 .
O5 O 0.86404(8) 0.74495(10) 0.18979(4) 0.0288(2) Uani 1.000000 .
O2 O 0.48598(9) 0.57102(12) 0.32322(5) 0.0356(2) Uani 1.000000 .
O6 O 0.90066(9) 0.51620(11) 0.19037(4) 0.0324(2) Uani 1.000000 .
N3 N 0.73125(8) 0.66088(10) 0.34790(4) 0.01632(19) Uani 1.000000 .
N7 N 0.82994(8) 0.88830(10) 0.44870(4) 0.01788(19) Uani 1.000000 .
N2 N 0.62495(8) 0.89399(10) 0.46437(4) 0.01821(19) Uani 1.000000 .
N5 N 0.75517(8) 0.71585(11) 0.29414(4) 0.0191(2) Uani 1.000000 .
N6 N 0.45847(9) 0.65183(11) 0.36376(5) 0.0220(2) Uani 1.000000 .
N8 N 0.86248(8) 0.62513(11) 0.21283(4) 0.0206(2) Uani 1.000000 .
N1 N 0.52376(8) 0.82941(10) 0.44119(4) 0.01893(19) Uani 1.000000 .
N4 N 0.77197(9) 0.52762(10) 0.36110(5) 0.0220(2) Uani 1.000000 .
C1 C 0.54976(9) 0.73728(12) 0.39697(5) 0.0177(2) Uani 1.000000 .
C4 C 0.81423(9) 0.60944(12) 0.27127(5) 0.0183(2) Uani 1.000000 .
C2 C 0.66900(9) 0.73938(12) 0.38926(5) 0.0163(2) Uani 1.000000 .
C3 C 0.71074(9) 0.84048(12) 0.43335(5) 0.0165(2) Uani 1.000000 .
C5 C 0.82446(11) 0.49294(13) 0.31117(6) 0.0247(2) Uani 1.000000 .
H1a H 0.5862(17) 1.303(2) 0.4475(9) 0.040(5) Uiso 1.000000 .
H1b H 0.6391(19) 1.230(2) 0.4065(11) 0.059(6) Uiso 1.000000 .
H5 H 0.86207(11) 0.40435(13) 0.30423(6) 0.0296(3) Uiso 1.000000 R


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
Na2 O1 2.3714(9) . y
Na2 O1 2.3894(9) 7_676 y
Na2 O3 2.5884(10) . y
Na2 O7 2.9078(11) 3_676 y
Na2 N2 2.5093(11) . y
Na2 N1 2.4858(10) 3_676 y
Na2 N4 2.5864(11) 7_666 y
O1 H1a 0.83(2) . ?
O1 H1b 0.86(2) . ?
O3 N7 1.2298(12) . ?
O4 N7 1.2320(12) . ?
O7 N6 1.2360(13) . ?
O5 N8 1.2230(14) . ?
O2 N6 1.2225(14) . ?
O6 N8 1.2260(14) . ?
N3 N5 1.3256(12) . ?
N3 N4 1.3449(13) . ?
N3 C2 1.4077(13) . ?
N7 C3 1.4350(14) . ?
N2 N1 1.3482(14) . ?
N2 C3 1.3439(14) . ?
N5 C4 1.3257(14) . ?
N6 C1 1.4373(15) . ?
N8 C4 1.4407(14) . ?
N1 C1 1.3420(14) . ?
N4 C5 1.3316(15) . ?
C1 C2 1.3908(14) . ?
C4 C5 1.3825(16) . ?
C2 C3 1.3852(15) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Na2 O1 92.23(3) . . y
O3 Na2 O1 70.19(3) . 7_676 y
O7 Na2 O1 94.71(3) 3_676 . y
O7 Na2 O1 69.65(3) 3_676 7_676 y
O7 Na2 O3 137.88(3) 3_676 . y
N2 Na2 O1 132.43(3) . 7_676 y
N2 Na2 O1 88.45(3) . . y
N2 Na2 O3 63.59(3) . . y
N2 Na2 O7 157.90(3) . 3_676 y
N1 Na2 O1 127.02(4) 3_676 7_676 y
N1 Na2 O1 88.83(3) 3_676 . y
N1 Na2 O3 162.70(4) 3_676 . y
N1 Na2 O7 59.09(3) 3_676 3_676 y
N1 Na2 N2 99.20(3) 3_676 . y
N4 Na2 O1 171.44(4) 7_666 . y
N4 Na2 O1 89.69(3) 7_666 7_676 y
N4 Na2 O3 88.49(3) 7_666 . y
N4 Na2 O7 79.14(3) 7_666 3_676 y
N4 Na2 N2 99.49(3) 7_666 . y
N4 Na2 N1 93.02(3) 7_666 3_676 y
H1a O1 Na2 107.8(13) . . ?
H1a O1 Na2 113.2(13) . 7_676 ?
H1b O1 Na2 127.5(14) . . ?
H1b O1 Na2 109.3(14) . 7_676 ?
H1b O1 H1a 101.8(19) . . ?
N7 O3 Na2 118.83(7) . . ?
N6 O7 Na2 116.04(7) . 3_676 ?
N4 N3 N5 116.21(9) . . ?
C2 N3 N5 121.61(9) . . ?
C2 N3 N4 122.17(9) . . ?
O4 N7 O3 124.57(10) . . ?
C3 N7 O3 118.31(9) . . ?
C3 N7 O4 117.12(9) . . ?
N1 N2 Na2 135.04(7) . . ?
C3 N2 Na2 117.04(7) . . ?
C3 N2 N1 106.98(9) . . ?
C4 N5 N3 101.63(9) . . ?
O2 N6 O7 124.54(11) . . ?
C1 N6 O7 117.57(10) . . ?
C1 N6 O2 117.89(10) . . ?
O6 N8 O5 124.91(10) . . ?
C4 N8 O5 118.27(10) . . ?
C4 N8 O6 116.81(10) . . ?
N2 N1 Na2 125.69(7) . 3_676 ?
C1 N1 Na2 126.33(7) . 3_676 ?
C1 N1 N2 107.48(9) . . ?
N3 N4 Na2 131.72(7) . 7_666 ?
C5 N4 Na2 120.94(8) . 7_666 ?
C5 N4 N3 103.24(9) . . ?
N1 C1 N6 120.19(10) . . ?
C2 C1 N6 127.80(10) . . ?
C2 C1 N1 112.01(10) . . ?
N8 C4 N5 120.79(10) . . ?
C5 C4 N5 111.43(10) . . ?
C5 C4 N8 127.74(10) . . ?
C1 C2 N3 129.82(10) . . ?
C3 C2 N3 129.07(10) . . ?
C3 C2 C1 101.11(9) . . ?
N2 C3 N7 119.72(10) . . ?
C2 C3 N7 127.85(10) . . ?
C2 C3 N2 112.42(10) . . ?
C4 C5 N4 107.48(10) . . ?
H5 C5 N4 126.26(7) . . ?
H5 C5 C4 126.26(7) . . ?


_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_9
_database_code_depnum_ccdc_archive 'CCDC 2241662'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_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         'C5 H2 N8 O6'
_chemical_formula_sum            'C5 H2 N8 O6'
_chemical_formula_weight         270.15
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.9516(2)
_cell_length_b                   8.6036(2)
_cell_length_c                   10.7241(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.5010(10)
_cell_angle_gamma                90
_cell_volume                     1067.60(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.42
_cell_measurement_theta_min      3.82
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_T_max  0.9150
_exptl_absorpt_correction_T_min  0.7760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10 
_exptl_special_details 

Final HKLF 4 output contains 44136 reflections, Rint = 0.0385
 (27156 with I > 3sig(I), Rint = 0.0344)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3634
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.562
_diffrn_reflns_theta_max         67.562
_diffrn_reflns_theta_min         3.820
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1779
_reflns_number_total             1926
_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 (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.057
_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)+(0.0458P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
N3 N 0.25203(11) 0.45713(13) 0.67550(11) 0.0398(3) Uani 1 1 d . . . . .
N5 N 0.22593(11) 0.31691(13) 0.70956(11) 0.0409(3) Uani 1 1 d . . . . .
N1 N 0.28834(12) 0.76494(15) 0.90329(12) 0.0473(3) Uani 1 1 d . . . . .
N4 N 0.24089(12) 0.47739(14) 0.54902(11) 0.0477(3) Uani 1 1 d . . . . .
O2 O 0.12906(13) 0.02941(15) 0.48328(13) 0.0720(4) Uani 1 1 d . . . . .
N6 N 0.16150(12) 0.08373(15) 0.59095(14) 0.0501(3) Uani 1 1 d . . . . .
O1 O 0.16767(14) 0.01364(14) 0.69062(13) 0.0741(4) Uani 1 1 d . . . . .
N7 N 0.09701(12) 0.70199(16) 0.77577(15) 0.0544(4) Uani 1 1 d . . . . .
O5 O 0.05675(12) 0.78969(15) 0.84230(15) 0.0743(4) Uani 1 1 d . . . . .
N2 N 0.39913(12) 0.72589(16) 0.92340(12) 0.0516(3) Uani 1 1 d . . . . .
O4 O 0.59312(11) 0.57505(18) 0.91624(15) 0.0808(4) Uani 1 1 d . . . . .
O6 O 0.04358(12) 0.63002(18) 0.68221(15) 0.0836(5) Uani 1 1 d . . . . .
C4 C 0.19573(12) 0.24496(16) 0.59781(12) 0.0381(3) Uani 1 1 d . . . . .
C2 C 0.28779(12) 0.57643(15) 0.76683(13) 0.0393(3) Uani 1 1 d . . . . .
N8 N 0.50554(13) 0.5364(2) 0.83732(16) 0.0656(4) Uani 1 1 d . . . . .
C1 C 0.22000(13) 0.68023(16) 0.81106(14) 0.0410(3) Uani 1 1 d . . . . .
C5 C 0.20451(14) 0.34140(18) 0.49831(14) 0.0467(4) Uani 1 1 d . . . . .
H5 H 0.187859 0.315398 0.411430 0.056 Uiso 1 1 calc R . . . .
C3 C 0.39812(13) 0.61161(18) 0.84075(14) 0.0458(4) Uani 1 1 d . . . . .
O3 O 0.50007(15) 0.4360(3) 0.7576(2) 0.1227(8) Uani 1 1 d . . . . .
H1 H 0.2699(18) 0.838(3) 0.947(2) 0.074(6) Uiso 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
N3 N5 1.3203(16) . ?
N3 N4 1.3407(16) . ?
N3 C2 1.4091(18) . ?
N5 C4 1.3165(17) . ?
N1 N2 1.330(2) . ?
N1 C1 1.3312(19) . ?
N4 C5 1.317(2) . ?
O2 N6 1.2157(17) . ?
N6 O1 1.2133(18) . ?
N6 C4 1.4429(19) . ?
N7 O5 1.2172(18) . ?
N7 O6 1.2153(19) . ?
N7 C1 1.435(2) . ?
N2 C3 1.322(2) . ?
O4 N8 1.216(2) . ?
C4 C5 1.376(2) . ?
C2 C1 1.368(2) . ?
C2 C3 1.391(2) . ?
N8 C3 1.446(2) . ?
N8 O3 1.205(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
N5 N3 N4 115.35(11) . . ?
N5 N3 C2 121.65(11) . . ?
N4 N3 C2 122.99(11) . . ?
C4 N5 N3 101.99(11) . . ?
N2 N1 C1 112.51(13) . . ?
C5 N4 N3 103.95(12) . . ?
O2 N6 C4 115.91(13) . . ?
O1 N6 O2 125.47(14) . . ?
O1 N6 C4 118.62(13) . . ?
O5 N7 C1 117.09(15) . . ?
O6 N7 O5 126.63(16) . . ?
O6 N7 C1 116.28(14) . . ?
C3 N2 N1 103.75(12) . . ?
N5 C4 N6 120.53(12) . . ?
N5 C4 C5 111.44(13) . . ?
C5 C4 N6 128.01(13) . . ?
C1 C2 N3 127.85(13) . . ?
C1 C2 C3 102.68(13) . . ?
C3 C2 N3 129.33(13) . . ?
O4 N8 C3 118.34(16) . . ?
O3 N8 O4 125.03(17) . . ?
O3 N8 C3 116.60(16) . . ?
N1 C1 N7 121.45(13) . . ?
N1 C1 C2 107.97(13) . . ?
C2 C1 N7 130.55(14) . . ?
N4 C5 C4 107.26(12) . . ?
N2 C3 C2 113.09(14) . . ?
N2 C3 N8 119.39(14) . . ?
C2 C3 N8 127.51(14) . . ?

_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_8
_database_code_depnum_ccdc_archive 'CCDC 2241661'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-11
_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         'C6 H4 N8 O6'
_chemical_formula_sum            'C6 H4 N8 O6'
_chemical_formula_weight         284.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1552(5)
_cell_length_b                   8.1515(4)
_cell_length_c                   15.7139(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.884(5)
_cell_angle_gamma                90
_cell_volume                     1122.16(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    297.8
_cell_measurement_theta_max      26.7240
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.219
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.898
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.8
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -7.00   0.50    3.70    --   16.22 -29.00 -46.00   50
  2  ω    -40.00  -1.00   0.50    3.70    --  -14.97 -29.00 -46.00   78
  3  ω      5.00  41.00   0.50    3.70    --   16.22 -30.00 -90.00   72
  4  ω    -37.00  18.00   0.50    3.70    --  -14.97 -94.00   0.00  110
  5  ω     -6.00  35.00   0.50    3.70    --   16.22 -61.00  60.00   82
  6  ω     -8.00  52.00   0.50    3.70    --  -14.97  29.00 114.00  120
  7  ω     16.00  41.00   0.50    3.70    --   16.22 -30.00 120.00   50
  8  ω      8.00  90.00   0.50    3.70    --   16.22  29.00 114.00  164
  9  ω    -21.00  22.00   0.50    3.70    --  -14.97 -94.00 120.00   86
 10  ω     39.00  64.00   0.50    3.70    --   16.22-125.00 120.00   50
 11  ω    -57.00 -15.00   0.50    3.70    --   16.22 -30.00 120.00   84
 12  ω    -83.00   9.00   0.50    3.70    --  -14.97 -45.00 120.00  184
 13  ω    -61.00 -12.00   0.50    3.70    --  -14.97 125.00 120.00   98
 14  ω    -56.00 -31.00   0.50    3.70    --  -14.97 125.00  90.00   50
 15  ω    -65.00 -21.00   0.50    3.70    --  -14.97 125.00  60.00   88
 16  ω    -88.00 -63.00   0.50    3.70    --  -14.97 -29.00 -46.00   50
 17  ω    -62.00   9.00   0.50    3.70    --  -14.97 -45.00 -30.00  142
 18  ω    -55.00 -11.00   0.50    3.70    --   16.22 -30.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0762721000
_diffrn_orient_matrix_UB_12      -0.0269962000
_diffrn_orient_matrix_UB_13      -0.0074310000
_diffrn_orient_matrix_UB_21      0.0155940000
_diffrn_orient_matrix_UB_22      -0.0182505000
_diffrn_orient_matrix_UB_23      0.0459386000
_diffrn_orient_matrix_UB_31      -0.0219729000
_diffrn_orient_matrix_UB_32      0.0807253000
_diffrn_orient_matrix_UB_33      0.0078798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1974
_reflns_number_total             2347
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0883P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O6 O 0.25408(13) 0.93564(14) 0.44778(8) 0.0530(3) Uani 1 1 d . . . . .
O5 O 0.11722(14) 0.72078(16) 0.45412(8) 0.0552(3) Uani 1 1 d . . . . .
N5 N 0.32104(14) 0.63373(15) 0.60956(8) 0.0402(3) Uani 1 1 d . . . . .
N1 N 0.51812(14) 0.30696(15) 0.83629(8) 0.0401(3) Uani 1 1 d . . . . .
N3 N 0.45108(14) 0.62880(15) 0.67464(8) 0.0411(3) Uani 1 1 d . . . . .
N6 N 0.22965(14) 0.80694(16) 0.48190(8) 0.0416(3) Uani 1 1 d . . . . .
N2 N 0.44022(14) 0.40957(15) 0.87281(8) 0.0425(3) Uani 1 1 d . . . . .
O4 O 0.31930(17) 0.79663(17) 0.79292(10) 0.0676(4) Uani 1 1 d . . . . .
O1 O 0.62003(18) 0.13509(16) 0.71148(10) 0.0683(4) Uani 1 1 d . . . . .
N7 N 0.32200(15) 0.67234(18) 0.83684(10) 0.0507(4) Uani 1 1 d . . . . .
N8 N 0.60279(16) 0.28205(18) 0.70178(9) 0.0496(4) Uani 1 1 d . . . . .
O2 O 0.6324(2) 0.36290(18) 0.64381(11) 0.0807(5) Uani 1 1 d . . . . .
N4 N 0.55551(17) 0.74133(19) 0.67063(11) 0.0600(4) Uani 1 1 d . . . . .
O3 O 0.2560(2) 0.6545(2) 0.89267(12) 0.0829(5) Uani 1 1 d . . . . .
C2 C 0.46985(15) 0.52220(18) 0.74744(9) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.53766(16) 0.37061(18) 0.76085(9) 0.0394(3) Uani 1 1 d . . . . .
C3 C 0.41097(15) 0.53789(18) 0.81902(10) 0.0392(3) Uani 1 1 d . . . . .
C4 C 0.34529(16) 0.75595(18) 0.56084(9) 0.0389(3) Uani 1 1 d . . . . .
C5 C 0.4877(2) 0.8237(2) 0.59729(12) 0.0564(5) Uani 1 1 d . . . . .
H5 H 0.528822 0.911741 0.574388 0.068 Uiso 1 1 calc R . . . .
C6 C 0.5733(2) 0.1523(2) 0.88330(13) 0.0593(5) Uani 1 1 d . . . . .
H6A H 0.564033 0.157631 0.942534 0.089 Uiso 1 1 calc GR . . . .
H6B H 0.678449 0.136125 0.886003 0.089 Uiso 1 1 calc GR . . . .
H6C H 0.513480 0.062548 0.851970 0.089 Uiso 1 1 calc GR . . . .


_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
O6 N6 1.2279(17) . ?
O5 N6 1.2175(18) . ?
N5 N3 1.3257(17) . ?
N5 C4 1.3141(18) . ?
N1 N2 1.3323(17) . ?
N1 C1 1.3527(19) . ?
N1 C6 1.474(2) . ?
N3 N4 1.3396(18) . ?
N3 C2 1.4069(19) . ?
N6 C4 1.4386(19) . ?
N2 C3 1.3224(19) . ?
O4 N7 1.2221(19) . ?
O1 N8 1.2122(19) . ?
N7 O3 1.210(2) . ?
N7 C3 1.4407(19) . ?
N8 O2 1.2170(18) . ?
N8 C1 1.4352(19) . ?
N4 C5 1.322(2) . ?
C2 C1 1.371(2) . ?
C2 C3 1.387(2) . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 N3 101.92(12) . . ?
N2 N1 C1 111.11(12) . . ?
N2 N1 C6 118.00(13) . . ?
C1 N1 C6 130.82(13) . . ?
N5 N3 N4 115.87(12) . . ?
N5 N3 C2 121.08(12) . . ?
N4 N3 C2 122.75(12) . . ?
O6 N6 C4 116.21(13) . . ?
O5 N6 O6 125.35(13) . . ?
O5 N6 C4 118.44(13) . . ?
C3 N2 N1 104.81(12) . . ?
O4 N7 C3 116.15(14) . . ?
O3 N7 O4 125.23(15) . . ?
O3 N7 C3 118.62(15) . . ?
O1 N8 O2 125.46(15) . . ?
O1 N8 C1 118.63(14) . . ?
O2 N8 C1 115.87(14) . . ?
C5 N4 N3 103.18(13) . . ?
C1 C2 N3 128.64(13) . . ?
C1 C2 C3 102.93(12) . . ?
C3 C2 N3 128.17(13) . . ?
N1 C1 N8 124.02(14) . . ?
N1 C1 C2 108.12(13) . . ?
C2 C1 N8 127.48(13) . . ?
N2 C3 N7 119.90(14) . . ?
N2 C3 C2 113.02(13) . . ?
C2 C3 N7 127.05(14) . . ?
N5 C4 N6 120.99(13) . . ?
N5 C4 C5 111.17(13) . . ?
C5 C4 N6 127.81(14) . . ?
N4 C5 C4 107.86(14) . . ?
N4 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.573
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2241851'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-11-26 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 N6 O2'
_chemical_formula_sum            'C5 H4 N6 O2'
_chemical_formula_weight         180.14
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6812(10)
_cell_length_b                   7.0171(11)
_cell_length_c                   7.8472(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.571(5)
_cell_angle_gamma                90
_cell_volume                     356.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6659
_cell_measurement_temperature    104(2)
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      6.41
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10 
_exptl_special_details 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       CUBIC
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8420
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.072
_diffrn_reflns_theta_min         6.406
_diffrn_ambient_temperature      104.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                1924
_reflns_number_total             1941
_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 SMART'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.064
_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)+(0.0448P)²+0.0416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), N3(H3A), C4(H4), C5(H5)
;
_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
O1 O 0.33850(17) 0.68458(18) 0.78027(16) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.6451(2) 0.52273(19) 0.84843(17) 0.0144(3) Uani 1 1 d . . . . .
N1 N 0.52397(19) 0.69171(18) 0.85203(16) 0.0165(2) Uani 1 1 d . . . . .
O3 O 0.61269(17) 0.83264(15) 0.92943(15) 0.0203(2) Uani 1 1 d . . . . .
C3 C 0.7656(2) 0.2401(2) 0.80762(19) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.784440 0.114508 0.769310 0.021 Uiso 1 1 calc R U . . .
N3 N 0.90333(19) 0.34494(17) 0.92563(17) 0.0181(3) Uani 1 1 d . . . . .
H3A H 1.027174 0.303014 0.979651 0.022 Uiso 1 1 calc R U . . .
N8 N 0.1740(2) 0.32964(19) 0.38640(17) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.83483(19) 0.51818(18) 0.95315(16) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.5917(2) 0.35233(19) 0.75381(18) 0.0150(3) Uani 1 1 d . . . . .
N4 N 0.40695(18) 0.30505(17) 0.62919(15) 0.0153(2) Uani 1 1 d . . . . .
C4 C 0.2672(2) 0.1669(2) 0.63686(18) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.271031 0.077950 0.728917 0.023 Uiso 1 1 calc R U . . .
N7 N 0.34983(19) 0.4030(2) 0.47608(16) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.1194(2) 0.1853(2) 0.48100(18) 0.0200(3) Uani 1 1 d . . . . .
H5 H -0.001598 0.109393 0.444977 0.024 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 N1 1.2264(16) . ?
C1 N1 1.4398(17) . ?
C1 N2 1.3264(17) . ?
C1 C2 1.4053(19) . ?
N1 O3 1.2317(17) . ?
C3 H3 0.9500 . ?
C3 N3 1.3478(18) . ?
C3 C2 1.3785(19) . ?
N3 H3A 0.8800 . ?
N3 N2 1.3355(17) . ?
N8 N7 1.3129(17) . ?
N8 C5 1.3589(19) . ?
C2 N4 1.4083(17) . ?
N4 C4 1.3577(17) . ?
N4 N7 1.3531(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3711(19) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 117.51(12) . . ?
N2 C1 C2 112.50(12) . . ?
C2 C1 N1 129.94(12) . . ?
O1 N1 C1 117.73(12) . . ?
O1 N1 O3 124.36(13) . . ?
O3 N1 C1 117.89(12) . . ?
N3 C3 H3 127.0 . . ?
N3 C3 C2 106.02(13) . . ?
C2 C3 H3 127.0 . . ?
C3 N3 H3A 123.0 . . ?
N2 N3 C3 113.90(12) . . ?
N2 N3 H3A 123.0 . . ?
N7 N8 C5 109.04(12) . . ?
C1 N2 N3 103.57(11) . . ?
C1 C2 N4 128.96(12) . . ?
C3 C2 C1 104.00(12) . . ?
C3 C2 N4 127.02(13) . . ?
C4 N4 C2 129.04(12) . . ?
N7 N4 C2 119.94(11) . . ?
N7 N4 C4 111.02(11) . . ?
N4 C4 H4 128.0 . . ?
N4 C4 C5 104.00(12) . . ?
C5 C4 H4 128.0 . . ?
N8 N7 N4 106.93(12) . . ?
N8 C5 C4 109.00(13) . . ?
N8 C5 H5 125.5 . . ?
C4 C5 H5 125.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N4 C4 -116.98(17) . . . . ?
C1 C2 N4 N7 63.62(19) . . . . ?
N1 C1 N2 N3 177.82(11) . . . . ?
N1 C1 C2 C3 -177.74(13) . . . . ?
N1 C1 C2 N4 3.6(2) . . . . ?
C3 N3 N2 C1 0.26(16) . . . . ?
C3 C2 N4 C4 64.7(2) . . . . ?
C3 C2 N4 N7 -114.71(16) . . . . ?
N3 C3 C2 C1 0.45(15) . . . . ?
N3 C3 C2 N4 179.11(13) . . . . ?
N2 C1 N1 O1 -167.49(12) . . . . ?
N2 C1 N1 O3 11.32(18) . . . . ?
N2 C1 C2 C3 -0.32(16) . . . . ?
N2 C1 C2 N4 -178.95(13) . . . . ?
C2 C1 N1 O1 9.8(2) . . . . ?
C2 C1 N1 O3 -171.37(13) . . . . ?
C2 C1 N2 N3 0.05(15) . . . . ?
C2 C3 N3 N2 -0.47(17) . . . . ?
C2 N4 C4 C5 -179.95(13) . . . . ?
C2 N4 N7 N8 179.99(12) . . . . ?
N4 C4 C5 N8 0.33(16) . . . . ?
C4 N4 N7 N8 0.49(16) . . . . ?
N7 N8 C5 C4 -0.05(17) . . . . ?
N7 N4 C4 C5 -0.50(16) . . . . ?
C5 N8 N7 N4 -0.26(16) . . . . ?

_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_aks181
_database_code_depnum_ccdc_archive 'CCDC 2289671'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-11
_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         'C6 H4 N8 O6'
_chemical_formula_sum            'C6 H4 N8 O6'
_chemical_formula_weight         284.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1552(5)
_cell_length_b                   8.1515(4)
_cell_length_c                   15.7139(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.884(5)
_cell_angle_gamma                90
_cell_volume                     1122.16(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    297.8
_cell_measurement_theta_max      26.7240
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.219
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.898
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.8
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -7.00   0.50    3.70    --   16.22 -29.00 -46.00   50
  2  ω    -40.00  -1.00   0.50    3.70    --  -14.97 -29.00 -46.00   78
  3  ω      5.00  41.00   0.50    3.70    --   16.22 -30.00 -90.00   72
  4  ω    -37.00  18.00   0.50    3.70    --  -14.97 -94.00   0.00  110
  5  ω     -6.00  35.00   0.50    3.70    --   16.22 -61.00  60.00   82
  6  ω     -8.00  52.00   0.50    3.70    --  -14.97  29.00 114.00  120
  7  ω     16.00  41.00   0.50    3.70    --   16.22 -30.00 120.00   50
  8  ω      8.00  90.00   0.50    3.70    --   16.22  29.00 114.00  164
  9  ω    -21.00  22.00   0.50    3.70    --  -14.97 -94.00 120.00   86
 10  ω     39.00  64.00   0.50    3.70    --   16.22-125.00 120.00   50
 11  ω    -57.00 -15.00   0.50    3.70    --   16.22 -30.00 120.00   84
 12  ω    -83.00   9.00   0.50    3.70    --  -14.97 -45.00 120.00  184
 13  ω    -61.00 -12.00   0.50    3.70    --  -14.97 125.00 120.00   98
 14  ω    -56.00 -31.00   0.50    3.70    --  -14.97 125.00  90.00   50
 15  ω    -65.00 -21.00   0.50    3.70    --  -14.97 125.00  60.00   88
 16  ω    -88.00 -63.00   0.50    3.70    --  -14.97 -29.00 -46.00   50
 17  ω    -62.00   9.00   0.50    3.70    --  -14.97 -45.00 -30.00  142
 18  ω    -55.00 -11.00   0.50    3.70    --   16.22 -30.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0762721000
_diffrn_orient_matrix_UB_12      -0.0269962000
_diffrn_orient_matrix_UB_13      -0.0074310000
_diffrn_orient_matrix_UB_21      0.0155940000
_diffrn_orient_matrix_UB_22      -0.0182505000
_diffrn_orient_matrix_UB_23      0.0459386000
_diffrn_orient_matrix_UB_31      -0.0219729000
_diffrn_orient_matrix_UB_32      0.0807253000
_diffrn_orient_matrix_UB_33      0.0078798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1974
_reflns_number_total             2347
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0883P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O6 O 0.25408(13) 0.93564(14) 0.44778(8) 0.0530(3) Uani 1 1 d . . . . .
O5 O 0.11722(14) 0.72078(16) 0.45412(8) 0.0552(3) Uani 1 1 d . . . . .
N5 N 0.32104(14) 0.63373(15) 0.60956(8) 0.0402(3) Uani 1 1 d . . . . .
N1 N 0.51812(14) 0.30696(15) 0.83629(8) 0.0401(3) Uani 1 1 d . . . . .
N3 N 0.45108(14) 0.62880(15) 0.67464(8) 0.0411(3) Uani 1 1 d . . . . .
N6 N 0.22965(14) 0.80694(16) 0.48190(8) 0.0416(3) Uani 1 1 d . . . . .
N2 N 0.44022(14) 0.40957(15) 0.87281(8) 0.0425(3) Uani 1 1 d . . . . .
O4 O 0.31930(17) 0.79663(17) 0.79292(10) 0.0676(4) Uani 1 1 d . . . . .
O1 O 0.62003(18) 0.13509(16) 0.71148(10) 0.0683(4) Uani 1 1 d . . . . .
N7 N 0.32200(15) 0.67234(18) 0.83684(10) 0.0507(4) Uani 1 1 d . . . . .
N8 N 0.60279(16) 0.28205(18) 0.70178(9) 0.0496(4) Uani 1 1 d . . . . .
O2 O 0.6324(2) 0.36290(18) 0.64381(11) 0.0807(5) Uani 1 1 d . . . . .
N4 N 0.55551(17) 0.74133(19) 0.67063(11) 0.0600(4) Uani 1 1 d . . . . .
O3 O 0.2560(2) 0.6545(2) 0.89267(12) 0.0829(5) Uani 1 1 d . . . . .
C2 C 0.46985(15) 0.52220(18) 0.74744(9) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.53766(16) 0.37061(18) 0.76085(9) 0.0394(3) Uani 1 1 d . . . . .
C3 C 0.41097(15) 0.53789(18) 0.81902(10) 0.0392(3) Uani 1 1 d . . . . .
C4 C 0.34529(16) 0.75595(18) 0.56084(9) 0.0389(3) Uani 1 1 d . . . . .
C5 C 0.4877(2) 0.8237(2) 0.59729(12) 0.0564(5) Uani 1 1 d . . . . .
H5 H 0.528822 0.911741 0.574388 0.068 Uiso 1 1 calc R . . . .
C6 C 0.5733(2) 0.1523(2) 0.88330(13) 0.0593(5) Uani 1 1 d . . . . .
H6A H 0.564033 0.157631 0.942534 0.089 Uiso 1 1 calc GR . . . .
H6B H 0.678449 0.136125 0.886003 0.089 Uiso 1 1 calc GR . . . .
H6C H 0.513480 0.062548 0.851970 0.089 Uiso 1 1 calc GR . . . .


_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
O6 N6 1.2279(17) . ?
O5 N6 1.2175(18) . ?
N5 N3 1.3257(17) . ?
N5 C4 1.3141(18) . ?
N1 N2 1.3323(17) . ?
N1 C1 1.3527(19) . ?
N1 C6 1.474(2) . ?
N3 N4 1.3396(18) . ?
N3 C2 1.4069(19) . ?
N6 C4 1.4386(19) . ?
N2 C3 1.3224(19) . ?
O4 N7 1.2221(19) . ?
O1 N8 1.2122(19) . ?
N7 O3 1.210(2) . ?
N7 C3 1.4407(19) . ?
N8 O2 1.2170(18) . ?
N8 C1 1.4352(19) . ?
N4 C5 1.322(2) . ?
C2 C1 1.371(2) . ?
C2 C3 1.387(2) . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 N3 101.92(12) . . ?
N2 N1 C1 111.11(12) . . ?
N2 N1 C6 118.00(13) . . ?
C1 N1 C6 130.82(13) . . ?
N5 N3 N4 115.87(12) . . ?
N5 N3 C2 121.08(12) . . ?
N4 N3 C2 122.75(12) . . ?
O6 N6 C4 116.21(13) . . ?
O5 N6 O6 125.35(13) . . ?
O5 N6 C4 118.44(13) . . ?
C3 N2 N1 104.81(12) . . ?
O4 N7 C3 116.15(14) . . ?
O3 N7 O4 125.23(15) . . ?
O3 N7 C3 118.62(15) . . ?
O1 N8 O2 125.46(15) . . ?
O1 N8 C1 118.63(14) . . ?
O2 N8 C1 115.87(14) . . ?
C5 N4 N3 103.18(13) . . ?
C1 C2 N3 128.64(13) . . ?
C1 C2 C3 102.93(12) . . ?
C3 C2 N3 128.17(13) . . ?
N1 C1 N8 124.02(14) . . ?
N1 C1 C2 108.12(13) . . ?
C2 C1 N8 127.48(13) . . ?
N2 C3 N7 119.90(14) . . ?
N2 C3 C2 113.02(13) . . ?
C2 C3 N7 127.05(14) . . ?
N5 C4 N6 120.99(13) . . ?
N5 C4 C5 111.17(13) . . ?
C5 C4 N6 127.81(14) . . ?
N4 C5 C4 107.86(14) . . ?
N4 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.573
####################################################################### 
# 
# 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_aks180
_database_code_depnum_ccdc_archive 'CCDC 2289806'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-03
_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         'C5 H3 N9 O6'
_chemical_formula_sum            'C5 H3 N9 O6'
_chemical_formula_weight         285.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8502(4)
_cell_length_b                   7.3093(4)
_cell_length_c                   16.7588(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.440(4)
_cell_angle_gamma                90
_cell_volume                     1072.37(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    298.35
_cell_measurement_theta_max      21.7870
_cell_measurement_theta_min      2.4320
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11964
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.928
_diffrn_reflns_theta_min         2.457
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.35
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  40.00   0.50    7.00    --   16.22  45.00 -30.00   56
  2  ω     43.00  83.00   0.50    7.00    --   16.22  45.00 -30.00   80
  3  ω     69.00  94.00   0.50    7.00    --   16.22  14.00  -7.00   50
  4  ω     11.00  40.00   0.50    7.00    --   16.22-125.00  60.00   58
  5  ω     45.00  71.00   0.50    7.00    --   16.22-125.00  60.00   52
  6  ω    -88.00  52.00   0.50    7.00    --  -14.97  14.00  -7.00  280
  7  ω    -52.00  41.00   0.50    7.00    --   16.22 -61.00 -90.00  186
  8  ω    -19.00  13.00   0.50    7.00    --  -14.97 -94.00-120.00   64
  9  ω     20.00  46.00   0.50    7.00    --   16.22 -77.00-180.00   52
 10  ω     10.00  71.00   0.50    7.00    --   16.22-125.00-180.00  122
 11  ω    -63.00  90.00   0.50    7.00    --   16.22 -14.00-178.00  306
 12  ω    -51.00 -10.00   0.50    7.00    --   16.22 -77.00-180.00   82
 13  ω    -94.00  59.00   0.50    7.00    --  -14.97 -14.00-178.00  306
 14  ω    -69.00 -38.00   0.50    7.00    --  -14.97 125.00 -90.00   62
 15  ω    -88.00 -63.00   0.50    7.00    --  -14.97 -30.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0538453000
_diffrn_orient_matrix_UB_12      -0.0001950000
_diffrn_orient_matrix_UB_13      -0.0274515000
_diffrn_orient_matrix_UB_21      -0.0592368000
_diffrn_orient_matrix_UB_22      0.0197700000
_diffrn_orient_matrix_UB_23      -0.0321378000
_diffrn_orient_matrix_UB_31      0.0124166000
_diffrn_orient_matrix_UB_32      0.0950308000
_diffrn_orient_matrix_UB_33      0.0066226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1129
_reflns_number_total             2204
_reflns_odcompleteness_completeness 98.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.011
_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)+(0.1216P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.2247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N3 N 0.4789(3) 0.3392(4) 0.61517(14) 0.0501(8) Uani 1 1 d . . . . .
N2 N 0.4580(3) 0.2396(4) 0.67816(15) 0.0529(8) Uani 1 1 d . . . . .
N7 N 0.8160(3) 0.6050(5) 0.62071(17) 0.0614(9) Uani 1 1 d . . . . .
N6 N 0.8637(3) 0.4604(5) 0.58402(18) 0.0658(10) Uani 1 1 d . . . . .
N4 N 0.3586(3) 0.3536(5) 0.55655(16) 0.0681(10) Uani 1 1 d . . . . .
N5 N 0.7559(4) 0.1720(5) 0.5389(2) 0.0746(10) Uani 1 1 d . . . . .
O3 O 0.6526(3) 0.0653(4) 0.54288(19) 0.0970(11) Uani 1 1 d . . . . .
N8 N 0.5917(4) 0.7282(5) 0.67214(19) 0.0755(10) Uani 1 1 d . . . . .
O5 O 0.4544(3) 0.7410(5) 0.64879(19) 0.1008(11) Uani 1 1 d . . . . .
O1 O 0.3122(4) 0.0399(5) 0.77846(18) 0.1044(12) Uani 1 1 d . . . . .
N1 N 0.2410(4) 0.0796(5) 0.7129(2) 0.0795(11) Uani 1 1 d . . . . .
O4 O 0.8657(3) 0.1438(5) 0.5040(2) 0.1049(12) Uani 1 1 d . . . . .
C4 C 0.6221(3) 0.4178(5) 0.60897(18) 0.0516(9) Uani 1 1 d . . . . .
O2 O 0.1079(4) 0.0385(5) 0.68953(18) 0.1167(14) Uani 1 1 d . . . . .
O6 O 0.6636(4) 0.8258(5) 0.7218(2) 0.1153(13) Uani 1 1 d . . . . .
C5 C 0.6710(4) 0.5870(6) 0.63544(19) 0.0571(10) Uani 1 1 d . . . . .
C3 C 0.7448(3) 0.3460(6) 0.5773(2) 0.0570(10) Uani 1 1 d . . . . .
N9 N 0.9067(4) 0.7612(5) 0.63318(18) 0.0861(12) Uani 1 1 d . . . . .
H9A H 0.988028 0.742170 0.611707 0.103 Uiso 1 1 d GR . . . .
H9B H 0.858128 0.853301 0.609735 0.103 Uiso 1 1 d GR . . . .
C1 C 0.3148(4) 0.1874(5) 0.65808(19) 0.0524(9) Uani 1 1 d . . . . .
C2 C 0.2538(4) 0.2555(6) 0.5841(2) 0.0683(12) Uani 1 1 d . . . . .
H2 H 0.155057 0.235493 0.557926 0.082 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
N3 N2 1.318(3) . ?
N3 N4 1.343(3) . ?
N3 C4 1.409(4) . ?
N2 C1 1.319(4) . ?
N7 N6 1.323(4) . ?
N7 C5 1.348(4) . ?
N7 N9 1.394(4) . ?
N6 C3 1.335(4) . ?
N4 C2 1.308(4) . ?
N5 O3 1.211(4) . ?
N5 O4 1.223(4) . ?
N5 C3 1.436(5) . ?
N8 O5 1.224(4) . ?
N8 O6 1.204(4) . ?
N8 C5 1.436(5) . ?
O1 N1 1.219(4) . ?
N1 O2 1.223(4) . ?
N1 C1 1.438(4) . ?
C4 C5 1.363(5) . ?
C4 C3 1.380(5) . ?
N9 H9A 0.8616 . ?
N9 H9B 0.8621 . ?
C1 C2 1.372(5) . ?
C2 H2 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
N2 N3 N4 116.1(2) . . ?
N2 N3 C4 121.2(2) . . ?
N4 N3 C4 122.7(3) . . ?
N3 N2 C1 101.4(2) . . ?
N6 N7 C5 112.6(3) . . ?
N6 N7 N9 120.5(3) . . ?
C5 N7 N9 126.5(4) . . ?
N7 N6 C3 103.8(3) . . ?
C2 N4 N3 103.1(3) . . ?
O3 N5 O4 125.2(4) . . ?
O3 N5 C3 116.3(3) . . ?
O4 N5 C3 118.4(4) . . ?
O5 N8 C5 116.3(3) . . ?
O6 N8 O5 125.0(4) . . ?
O6 N8 C5 118.7(3) . . ?
O1 N1 O2 125.2(4) . . ?
O1 N1 C1 118.9(3) . . ?
O2 N1 C1 115.9(4) . . ?
C5 C4 N3 126.3(3) . . ?
C5 C4 C3 103.9(3) . . ?
C3 C4 N3 129.8(4) . . ?
N7 C5 N8 123.1(4) . . ?
N7 C5 C4 107.1(4) . . ?
C4 C5 N8 129.8(3) . . ?
N6 C3 N5 119.2(3) . . ?
N6 C3 C4 112.6(4) . . ?
C4 C3 N5 128.2(3) . . ?
N7 N9 H9A 107.7 . . ?
N7 N9 H9B 109.5 . . ?
H9A N9 H9B 109.1 . . ?
N2 C1 N1 120.3(3) . . ?
N2 C1 C2 111.2(3) . . ?
C2 C1 N1 128.4(3) . . ?
N4 C2 C1 108.2(3) . . ?
N4 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.642
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2241663'
loop_
_audit_author_name
_audit_author_address
'Muntha Balaraju'
;University of hyderabad
India
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-11-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_chemical_formula_moiety         'C5 H N8 O6, H4 N'
_chemical_formula_sum            'C5 H5 N9 O6'
_chemical_formula_weight         287.15
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.1838(8)
_cell_length_b                   9.1275(12)
_cell_length_c                   12.3907(18)
_cell_angle_alpha                107.311(4)
_cell_angle_beta                 99.537(5)
_cell_angle_gamma                102.736(4)
_cell_volume                     528.83(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    107(2)
_cell_measurement_theta_max      2.44
_cell_measurement_theta_min      33.15
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10 
_exptl_special_details 
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.8032
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             292.1784
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.068
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30771
_diffrn_reflns_theta_full        33.2020
_diffrn_reflns_theta_max         33.20
_diffrn_reflns_theta_min         2.44
_diffrn_ambient_temperature      107.0
_diffrn_measured_fraction_theta_full 0.9943
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3603
_reflns_number_total             3999
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4794
_refine_diff_density_min         -0.2731
_refine_diff_density_rms         0.0599
_refine_ls_d_res_high            0.6490
_refine_ls_d_res_low             8.3487
_refine_ls_goodness_of_fit_ref   1.0514
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.0514
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.1801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0904
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O2 O 0.05996(13) -0.00896(7) 0.18974(5) 0.01497(12) Uani 1.000000 .
O1 O -0.23730(12) 0.03493(7) 0.06621(5) 0.01549(12) Uani 1.000000 .
O4 O 0.96460(13) 0.52411(8) 0.31345(6) 0.01956(13) Uani 1.000000 .
O6 O 0.72074(14) 0.12477(8) 0.62758(6) 0.01988(13) Uani 1.000000 .
O3 O 0.86552(14) 0.62117(8) 0.17597(6) 0.01919(13) Uani 1.000000 .
O5 O 0.40986(16) 0.24997(10) 0.62593(6) 0.02439(15) Uani 1.000000 .
N6 N -0.01210(13) 0.07349(8) 0.13493(6) 0.01130(12) Uani 1.000000 .
N5 N 0.45870(14) 0.26570(8) 0.41404(6) 0.01222(12) Uani 1.000000 .
N3 N 0.55587(13) 0.25114(8) 0.32014(6) 0.01077(12) Uani 1.000000 .
N1 N 0.13067(14) 0.30214(8) 0.07754(6) 0.01219(12) Uani 1.000000 .
N7 N 0.80781(14) 0.53029(8) 0.23005(6) 0.01325(12) Uani 1.000000 .
N2 N 0.35607(14) 0.42481(8) 0.10230(6) 0.01250(12) Uani 1.000000 .
N8 N 0.58148(15) 0.19565(9) 0.58402(6) 0.01507(13) Uani 1.000000 .
N4 N 0.77025(15) 0.19193(10) 0.31790(7) 0.01673(14) Uani 1.000000 .
N9 N 0.63819(15) 0.24900(9) 0.89849(6) 0.01405(13) Uani 1.000000 .
C2 C 0.43689(15) 0.29273(9) 0.22708(6) 0.01022(12) Uani 1.000000 .
C1 C 0.17967(15) 0.22217(9) 0.15030(6) 0.01065(12) Uani 1.000000 .
C4 C 0.62330(16) 0.21106(9) 0.47573(6) 0.01200(13) Uani 1.000000 .
C3 C 0.53849(15) 0.41914(9) 0.19054(6) 0.01117(13) Uani 1.000000 .
C5 C 0.81704(17) 0.16527(11) 0.41805(8) 0.01703(15) Uani 1.000000 .
H5 H 0.959(3) 0.1228(19) 0.4415(14) 0.034(4) Uiso 1.000000 .
H9a H 0.498(3) 0.1805(19) 0.9050(14) 0.032(4) Uiso 1.000000 .
H9b H 0.793(3) 0.2605(18) 0.9533(14) 0.029(4) Uiso 1.000000 .
H9c H 0.612(3) 0.345(2) 0.9063(14) 0.033(4) Uiso 1.000000 .
H9d H 0.667(3) 0.2116(17) 0.8266(13) 0.026(3) Uiso 1.000000 .


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
O2 N6 1.2293(8) . ?
O1 N6 1.2340(9) . ?
O4 N7 1.2281(9) . ?
O6 N8 1.2311(10) . ?
O3 N7 1.2306(9) . ?
O5 N8 1.2253(10) . ?
N6 C1 1.4334(10) . ?
N5 N3 1.3254(9) . ?
N5 C4 1.3264(10) . ?
N3 N4 1.3394(9) . ?
N3 C2 1.4079(9) . ?
N1 N2 1.3465(9) . ?
N1 C1 1.3446(9) . ?
N7 C3 1.4393(10) . ?
N2 C3 1.3435(10) . ?
N8 C4 1.4362(10) . ?
N4 C5 1.3282(10) . ?
N9 H9a 0.882(16) . ?
N9 H9b 0.924(16) . ?
N9 H9c 0.899(16) . ?
N9 H9d 0.904(15) . ?
C2 C1 1.3907(10) . ?
C2 C3 1.3913(10) . ?
C4 C5 1.3925(11) . ?
C5 H5 0.950(16) . ?

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
O1 N6 O2 124.06(7) . . ?
C1 N6 O2 117.83(6) . . ?
C1 N6 O1 118.10(6) . . ?
C4 N5 N3 101.64(6) . . ?
N4 N3 N5 116.24(6) . . ?
C2 N3 N5 121.80(6) . . ?
C2 N3 N4 121.95(6) . . ?
C1 N1 N2 107.35(6) . . ?
O3 N7 O4 125.07(7) . . ?
C3 N7 O4 117.28(7) . . ?
C3 N7 O3 117.62(7) . . ?
C3 N2 N1 107.47(6) . . ?
O5 N8 O6 124.33(7) . . ?
C4 N8 O6 116.54(7) . . ?
C4 N8 O5 119.11(7) . . ?
C5 N4 N3 103.83(7) . . ?
H9b N9 H9a 109.5(14) . . ?
H9c N9 H9a 113.1(14) . . ?
H9c N9 H9b 109.8(14) . . ?
H9d N9 H9a 109.6(14) . . ?
H9d N9 H9b 108.6(13) . . ?
H9d N9 H9c 106.0(13) . . ?
C1 C2 N3 129.05(7) . . ?
C3 C2 N3 129.63(7) . . ?
C3 C2 C1 101.26(6) . . ?
N1 C1 N6 119.93(6) . . ?
C2 C1 N6 127.78(7) . . ?
C2 C1 N1 111.97(6) . . ?
N8 C4 N5 121.05(7) . . ?
C5 C4 N5 111.30(7) . . ?
C5 C4 N8 127.54(7) . . ?
N2 C3 N7 119.60(7) . . ?
C2 C3 N7 128.33(7) . . ?
C2 C3 N2 111.93(7) . . ?
C4 C5 N4 106.99(7) . . ?
H5 C5 N4 123.4(9) . . ?
H5 C5 C4 129.6(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9a O1 0.882(16) 2.285(16) 3.1349(10) 161.9(14) 2_556
N9 H9b N1 0.924(16) 2.012(16) 2.9345(10) 175.9(14) 1_656
N9 H9c N2 0.899(16) 2.103(16) 2.9738(11) 162.8(14) 2_666

_olex2_submission_special_instructions 'No special instructions were received'
