# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_29deca_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2173450'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'PKBSD 26'
_chemical_formula_moiety         '2(C2 H6 O S), C4 H4 N8 O2'
_chemical_formula_sum            'C8 H16 N8 O4 S2'
_chemical_formula_weight         352.41
_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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0576(8)
_cell_length_b                   7.4466(10)
_cell_length_c                   8.8862(13)
_cell_angle_alpha                75.730(4)
_cell_angle_beta                 86.042(4)
_cell_angle_gamma                77.998(4)
_cell_volume                     379.92(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3954
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         2.879
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_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                1739
_reflns_number_total             1853
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.111
_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)+0.2796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1.a X=CH2 refined with riding coordinates:
 N14(H14A,H14B)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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
S01 S 0.74044(6) 0.10007(5) 0.11700(4) 0.01149(11) Uani 1 1 d . . . . .
O12 O 0.38496(16) 0.31101(14) 0.51982(11) 0.0120(2) Uani 1 1 d . . . . .
O1 O 0.83327(17) 0.02035(15) 0.28004(12) 0.0162(2) Uani 1 1 d . . . . .
N10 N 0.5281(2) 0.26807(17) 0.75480(14) 0.0138(2) Uani 1 1 d . . . . .
N7 N 0.0215(2) 0.49780(17) 0.57013(14) 0.0124(2) Uani 1 1 d . . . . .
N9 N 0.3120(2) 0.37771(17) 0.75189(14) 0.0139(2) Uani 1 1 d . . . . .
N14 N 0.7442(2) 0.13028(18) 0.56415(14) 0.0158(3) Uani 1 1 d . . . . .
H14A H 0.860285 0.077857 0.625061 0.019 Uiso 1 1 calc R U . . .
H14B H 0.748874 0.115201 0.468745 0.019 Uiso 1 1 calc R U . . .
C11 C 0.5631(2) 0.23143(19) 0.61583(16) 0.0117(3) Uani 1 1 d . . . . .
C8 C 0.2329(2) 0.39857(19) 0.61524(16) 0.0118(3) Uani 1 1 d . . . . .
C1 C 0.8897(2) 0.2828(2) 0.02658(17) 0.0149(3) Uani 1 1 d . . . . .
H1A H 0.879090 0.371769 0.092903 0.022 Uiso 1 1 calc R U . . .
H1B H 0.823354 0.349804 -0.074325 0.022 Uiso 1 1 calc R U . . .
H1C H 1.048631 0.227016 0.011516 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4734(2) 0.2468(2) 0.14163(17) 0.0148(3) Uani 1 1 d . . . . .
H2A H 0.371396 0.168802 0.202611 0.022 Uiso 1 1 calc R U . . .
H2B H 0.408521 0.310468 0.039650 0.022 Uiso 1 1 calc R U . . .
H2C H 0.493813 0.341491 0.196132 0.022 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
S01 O1 1.5223(10) . ?
S01 C1 1.7851(15) . ?
S01 C2 1.7866(14) . ?
O12 C11 1.3622(16) . ?
O12 C8 1.3811(16) . ?
N10 N9 1.3895(17) . ?
N10 C11 1.3230(18) . ?
N7 N7 1.282(2) 2_566 ?
N7 C8 1.3702(18) . ?
N9 C8 1.2978(18) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C11 1.3185(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

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 S01 C1 106.09(7) . . ?
O1 S01 C2 105.11(6) . . ?
C1 S01 C2 98.01(7) . . ?
C11 O12 C8 101.49(11) . . ?
C11 N10 N9 105.59(11) . . ?
N7 N7 C8 113.35(15) 2_566 . ?
C8 N9 N10 106.99(12) . . ?
H14A N14 H14B 120.0 . . ?
C11 N14 H14A 120.0 . . ?
C11 N14 H14B 120.0 . . ?
N10 C11 O12 113.09(12) . . ?
N14 C11 O12 119.08(12) . . ?
N14 C11 N10 127.83(13) . . ?
N7 C8 O12 123.58(12) . . ?
N9 C8 O12 112.83(12) . . ?
N9 C8 N7 123.59(13) . . ?
S01 C1 H1A 109.5 . . ?
S01 C1 H1B 109.5 . . ?
S01 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S01 C2 H2A 109.5 . . ?
S01 C2 H2B 109.5 . . ?
S01 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
N10 N9 C8 O12 -0.99(16) . . . . ?
N10 N9 C8 N7 179.35(13) . . . . ?
N7 N7 C8 O12 -0.2(2) 2_566 . . . ?
N7 N7 C8 N9 179.39(15) 2_566 . . . ?
N9 N10 C11 O12 0.55(16) . . . . ?
N9 N10 C11 N14 -179.30(14) . . . . ?
C11 O12 C8 N7 -179.08(13) . . . . ?
C11 O12 C8 N9 1.26(15) . . . . ?
C11 N10 N9 C8 0.27(15) . . . . ?
C8 O12 C11 N10 -1.08(15) . . . . ?
C8 O12 C11 N14 178.79(13) . . . . ?

_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_17febb_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2173452'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'PKBSD 34'
_chemical_formula_moiety         'C2 H N5 O3, H2 O'
_chemical_formula_sum            'C2 H3 N5 O4'
_chemical_formula_weight         161.09
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   24.416(3)
_cell_length_b                   5.2920(7)
_cell_length_c                   9.1744(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.558(4)
_cell_angle_gamma                90
_cell_volume                     1152.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3548
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.43
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7923
_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         28.321
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_temperature      100
_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                1210
_reflns_number_total             1430
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.061
_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)+(0.0376P)²+1.5743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0916
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O3 O 0.30417(4) 0.1475(2) 0.31610(11) 0.0136(2) Uani 1 1 d . . . . .
O2 O 0.41791(5) -0.0497(2) 0.01767(12) 0.0188(3) Uani 1 1 d . . . . .
O4 O 0.47038(5) 0.6652(3) 0.36762(14) 0.0208(3) Uani 1 1 d . . . . .
O1 O 0.43878(5) 0.2720(2) 0.16572(13) 0.0228(3) Uani 1 1 d . . . . .
N3 N 0.36845(5) 0.4297(2) 0.31255(14) 0.0135(3) Uani 1 1 d . . . . .
N5 N 0.26538(5) 0.3483(2) 0.50647(14) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.36047(5) 0.0376(2) 0.16310(14) 0.0141(3) Uani 1 1 d . . . . .
N1 N 0.40784(5) 0.0939(2) 0.11452(13) 0.0144(3) Uani 1 1 d . . . . .
N4 N 0.33957(5) 0.5148(2) 0.41427(14) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.30232(6) 0.3418(3) 0.41347(16) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.34853(6) 0.2049(3) 0.25702(15) 0.0122(3) Uani 1 1 d . . . . .
H4A H 0.497(3) 0.618(12) 0.383(7) 0.25(3) Uiso 1 1 d . . . . .
H4B H 0.4678(12) 0.805(5) 0.413(3) 0.056(8) Uiso 1 1 d . . . . .
H3 H 0.4027(11) 0.506(5) 0.310(3) 0.044(7) 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
O3 C2 1.3696(18) . ?
O3 C1 1.3544(17) . ?
O2 N1 1.2368(16) . ?
O4 H4A 0.67(8) . ?
O4 H4B 0.85(3) . ?
O1 N1 1.2300(17) . ?
N3 N4 1.3709(17) . ?
N3 C1 1.340(2) . ?
N3 H3 0.93(3) . ?
N5 N5 1.272(3) 7_556 ?
N5 C2 1.3796(19) . ?
N2 N1 1.3663(17) . ?
N2 C1 1.3151(19) . ?
N4 C2 1.289(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 O3 C2 104.16(11) . . ?
H4A O4 H4B 113(6) . . ?
N4 N3 H3 118.6(15) . . ?
C1 N3 N4 110.58(12) . . ?
C1 N3 H3 128.6(15) . . ?
N5 N5 C2 112.26(16) 7_556 . ?
C1 N2 N1 113.65(12) . . ?
O2 N1 N2 115.23(12) . . ?
O1 N1 O2 122.49(13) . . ?
O1 N1 N2 122.26(12) . . ?
C2 N4 N3 103.76(12) . . ?
O3 C2 N5 123.27(13) . . ?
N4 C2 O3 113.92(13) . . ?
N4 C2 N5 122.76(14) . . ?
N3 C1 O3 107.46(12) . . ?
N2 C1 O3 115.60(13) . . ?
N2 C1 N3 136.94(14) . . ?

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
N3 N4 C2 O3 -0.68(17) . . . . ?
N3 N4 C2 N5 177.12(13) . . . . ?
N5 N5 C2 O3 1.6(2) 7_556 . . . ?
N5 N5 C2 N4 -176.01(16) 7_556 . . . ?
N1 N2 C1 O3 -175.58(12) . . . . ?
N1 N2 C1 N3 5.5(2) . . . . ?
N4 N3 C1 O3 3.36(16) . . . . ?
N4 N3 C1 N2 -177.65(17) . . . . ?
C2 O3 C1 N3 -3.52(15) . . . . ?
C2 O3 C1 N2 177.25(12) . . . . ?
C1 O3 C2 N5 -175.11(14) . . . . ?
C1 O3 C2 N4 2.68(17) . . . . ?
C1 N3 N4 C2 -1.67(16) . . . . ?
C1 N2 N1 O2 -174.90(12) . . . . ?
C1 N2 N1 O1 6.4(2) . . . . ?

_olex2_submission_original_sample_id 'PKBSD 26'
_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_25apra_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2173451'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N5 O3, C3 H7 N8'
_chemical_formula_sum            'C5 H7 N13 O3'
_chemical_formula_weight         297.24
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7799(6)
_cell_length_b                   6.8854(6)
_cell_length_c                   12.8125(12)
_cell_angle_alpha                77.172(3)
_cell_angle_beta                 89.270(3)
_cell_angle_gamma                69.344(2)
_cell_volume                     544.29(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3661
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.22
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8556
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         3.219
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                2278
_reflns_number_total             2708
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.433
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.060
_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)+(0.0682P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N1(H1A)
2.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_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
O5 O 0.76086(17) 0.45159(17) 0.13653(9) 0.0142(3) Uani 1 1 d . . . . .
O2 O 0.18890(18) 0.50175(19) 0.23005(9) 0.0185(3) Uani 1 1 d . . . . .
N11 N 0.9180(2) 0.5825(2) -0.01887(10) 0.0141(3) Uani 1 1 d . . . . .
N2 N -0.0437(2) 0.9440(2) 0.22934(10) 0.0141(3) Uani 1 1 d . . . . .
N9 N 0.5424(2) 0.4034(2) 0.26409(11) 0.0150(3) Uani 1 1 d . . . . .
N5 N -0.0056(2) 0.8210(2) 0.40119(10) 0.0137(3) Uani 1 1 d . . . . .
N13 N 0.4270(2) 0.6684(2) 0.08960(10) 0.0145(3) Uani 1 1 d . . . . .
N4 N -0.2115(2) 0.8373(2) 0.37451(11) 0.0149(3) Uani 1 1 d . . . . .
N10 N 0.3488(2) 0.4191(2) 0.29323(11) 0.0147(3) Uani 1 1 d . . . . .
N12 N 0.5532(2) 0.7200(2) 0.01019(10) 0.0146(3) Uani 1 1 d . . . . .
N8 N 0.2875(2) 0.8704(2) 0.34116(11) 0.0171(3) Uani 1 1 d . . . . .
N6 N 0.0837(2) 0.6997(2) 0.59020(11) 0.0174(3) Uani 1 1 d . . . . .
H6A H 0.178397 0.670724 0.643227 0.021 Uiso 1 1 calc R U . . .
H6B H -0.038955 0.686074 0.603807 0.021 Uiso 1 1 calc R U . . .
N7 N 0.3018(2) 0.7939(2) 0.45319(11) 0.0177(3) Uani 1 1 d . . . . .
N1 N -0.0083(2) 0.9859(2) 0.12003(10) 0.0158(3) Uani 1 1 d . . . . .
H1A H 0.106198 0.883403 0.107537 0.019 Uiso 1 1 d R U . . .
C5 C 0.7456(3) 0.5894(2) 0.04009(12) 0.0139(3) Uani 1 1 d . . . . .
C2 C 0.0960(2) 0.8836(2) 0.31646(12) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.5560(2) 0.5108(2) 0.16385(12) 0.0135(3) Uani 1 1 d . . . . .
C3 C -0.2225(2) 0.9072(2) 0.26838(12) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.1257(2) 0.7637(2) 0.48986(13) 0.0147(3) Uani 1 1 d . . . . .
N3 N -0.3851(2) 0.9360(2) 0.20167(12) 0.0172(3) Uani 1 1 d . . . . .
H3A H -0.495(3) 0.927(3) 0.2345(17) 0.020(5) Uiso 1 1 d . . . . .
H3B H -0.404(3) 1.016(4) 0.1368(19) 0.022(5) Uiso 1 1 d . . . . .
O1 O 0.33681(19) 0.3399(2) 0.39100(9) 0.0195(3) Uani 1 1 d . . . . .
H1B H 0.022(4) 1.107(4) 0.1050(18) 0.028(6) Uiso 1 1 d . . . . .
H7 H 0.414(4) 0.764(4) 0.489(2) 0.035(7) 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
O5 C5 1.3608(18) . ?
O5 C4 1.3672(18) . ?
O2 N10 1.2396(17) . ?
N11 N11 1.281(3) 2_765 ?
N11 C5 1.376(2) . ?
N2 N1 1.4011(18) . ?
N2 C2 1.363(2) . ?
N2 C3 1.389(2) . ?
N9 N10 1.3339(18) . ?
N9 C4 1.352(2) . ?
N5 N4 1.4010(18) . ?
N5 C2 1.350(2) . ?
N5 C1 1.348(2) . ?
N13 N12 1.3878(19) . ?
N13 C4 1.3194(19) . ?
N4 C3 1.332(2) . ?
N10 O1 1.2641(17) . ?
N12 C5 1.300(2) . ?
N8 N7 1.4068(19) . ?
N8 C2 1.307(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C1 1.325(2) . ?
N7 C1 1.344(2) . ?
N7 H7 0.83(3) . ?
N1 H1A 0.8872 . ?
N1 H1B 0.91(2) . ?
C3 N3 1.334(2) . ?
N3 H3A 0.86(2) . ?
N3 H3B 0.87(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
C5 O5 C4 102.38(12) . . ?
N11 N11 C5 112.81(16) 2_765 . ?
C2 N2 N1 129.22(13) . . ?
C2 N2 C3 105.67(13) . . ?
C3 N2 N1 123.52(13) . . ?
N10 N9 C4 116.60(13) . . ?
C2 N5 N4 114.06(13) . . ?
C1 N5 N4 138.37(14) . . ?
C1 N5 C2 107.55(14) . . ?
C4 N13 N12 105.96(13) . . ?
C3 N4 N5 100.40(12) . . ?
O2 N10 N9 123.52(13) . . ?
O2 N10 O1 120.89(13) . . ?
O1 N10 N9 115.58(13) . . ?
C5 N12 N13 106.76(12) . . ?
C2 N8 N7 100.73(13) . . ?
H6A N6 H6B 120.0 . . ?
C1 N6 H6A 120.0 . . ?
C1 N6 H6B 120.0 . . ?
N8 N7 H7 120.3(17) . . ?
C1 N7 N8 113.03(13) . . ?
C1 N7 H7 126.5(17) . . ?
N2 N1 H1A 109.8 . . ?
N2 N1 H1B 107.1(14) . . ?
H1A N1 H1B 106.1 . . ?
O5 C5 N11 122.18(14) . . ?
N12 C5 O5 112.80(14) . . ?
N12 C5 N11 124.99(14) . . ?
N5 C2 N2 105.50(14) . . ?
N8 C2 N2 140.26(15) . . ?
N8 C2 N5 114.24(14) . . ?
N9 C4 O5 110.97(13) . . ?
N13 C4 O5 112.08(13) . . ?
N13 C4 N9 136.68(15) . . ?
N4 C3 N2 114.28(14) . . ?
N4 C3 N3 124.90(15) . . ?
N3 C3 N2 120.79(14) . . ?
N6 C1 N5 126.73(15) . . ?
N6 C1 N7 128.79(15) . . ?
N7 C1 N5 104.44(14) . . ?
C3 N3 H3A 113.1(14) . . ?
C3 N3 H3B 121.7(14) . . ?
H3A N3 H3B 119(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
N11 N11 C5 O5 9.3(2) 2_765 . . . ?
N11 N11 C5 N12 -168.59(16) 2_765 . . . ?
N5 N4 C3 N2 -2.89(17) . . . . ?
N5 N4 C3 N3 175.29(15) . . . . ?
N13 N12 C5 O5 -0.79(17) . . . . ?
N13 N12 C5 N11 177.31(15) . . . . ?
N4 N5 C2 N2 -0.12(17) . . . . ?
N4 N5 C2 N8 179.43(13) . . . . ?
N4 N5 C1 N6 -0.6(3) . . . . ?
N4 N5 C1 N7 -178.54(17) . . . . ?
N10 N9 C4 O5 -168.76(12) . . . . ?
N10 N9 C4 N13 18.0(3) . . . . ?
N12 N13 C4 O5 -1.52(17) . . . . ?
N12 N13 C4 N9 171.63(18) . . . . ?
N8 N7 C1 N5 -0.02(18) . . . . ?
N8 N7 C1 N6 -177.89(15) . . . . ?
N7 N8 C2 N2 178.6(2) . . . . ?
N7 N8 C2 N5 -0.76(18) . . . . ?
N1 N2 C2 N5 -167.37(14) . . . . ?
N1 N2 C2 N8 13.3(3) . . . . ?
N1 N2 C3 N4 169.82(13) . . . . ?
N1 N2 C3 N3 -8.5(2) . . . . ?
C5 O5 C4 N9 -173.94(13) . . . . ?
C5 O5 C4 N13 1.04(17) . . . . ?
C2 N2 C3 N4 3.02(18) . . . . ?
C2 N2 C3 N3 -175.25(14) . . . . ?
C2 N5 N4 C3 1.82(17) . . . . ?
C2 N5 C1 N6 177.49(15) . . . . ?
C2 N5 C1 N7 -0.43(17) . . . . ?
C2 N8 N7 C1 0.47(18) . . . . ?
C4 O5 C5 N11 -178.27(14) . . . . ?
C4 O5 C5 N12 -0.11(17) . . . . ?
C4 N9 N10 O2 9.5(2) . . . . ?
C4 N9 N10 O1 -171.63(13) . . . . ?
C4 N13 N12 C5 1.38(16) . . . . ?
C3 N2 C2 N5 -1.60(16) . . . . ?
C3 N2 C2 N8 179.0(2) . . . . ?
C1 N5 N4 C3 179.85(18) . . . . ?
C1 N5 C2 N2 -178.75(12) . . . . ?
C1 N5 C2 N8 0.81(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
