# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

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

data_12jund_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2419623'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_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         'C5 H4 N6 O2 S, 0.5(H2 O)'
_chemical_formula_sum            'C5 H5 N6 O2.50 S'
_chemical_formula_weight         221.21
_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'
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.6499(13)
_cell_length_b                   4.7759(5)
_cell_length_c                   13.2717(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.836(2)
_cell_angle_gamma                90
_cell_volume                     808.61(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4802
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.9304.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1975
_reflns_number_total             2021
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.209
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.084
_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)+(0.0180P)²+0.4825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H00A(0.5) H00B(0.5)
3.a Free rotating group:
 O002(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A)
3.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_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
S1 S 0.47908(3) 0.76859(10) 0.84582(3) 0.01257(11) Uani 1 1 d . . . . .
O002 O 0.000000 -0.1639(4) 0.500000 0.0142(4) Uani 1 2 d GS T P . .
H00A H -0.017155 -0.274049 0.541243 0.021 Uiso 0.5 1 d G U P . .
H00B H -0.003611 -0.263907 0.445790 0.021 Uiso 0.5 1 d G U P . .
O1 O 0.27458(13) 0.0658(3) 0.92754(12) 0.0224(4) Uani 1 1 d . . . . .
O2 O 0.38420(13) 0.3993(4) 0.93736(12) 0.0246(4) Uani 1 1 d . . . . .
N6 N 0.31304(13) 0.2424(4) 0.88556(13) 0.0145(3) Uani 1 1 d . . . . .
N5 N 0.61138(14) 1.1585(4) 0.82197(14) 0.0160(4) Uani 1 1 d . . . . .
H5A H 0.636228 1.267897 0.783344 0.019 Uiso 1 1 calc R U . . .
H5B H 0.641082 1.156780 0.892679 0.019 Uiso 1 1 calc R U . . .
N3 N 0.39899(12) 0.7896(4) 0.63989(12) 0.0136(3) Uani 1 1 d . . . . .
N1 N 0.17268(14) 0.1806(4) 0.61284(14) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.19368(13) 0.1051(4) 0.71509(14) 0.0132(3) Uani 1 1 d . . . . .
N4 N 0.47873(13) 0.9834(4) 0.66758(13) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.30575(15) 0.4519(4) 0.70412(16) 0.0112(4) Uani 1 1 d . . . . .
C3 C 0.27363(14) 0.2694(5) 0.76990(14) 0.0120(3) Uani 1 1 d . . . . .
C5 C 0.52839(15) 0.9948(4) 0.77317(16) 0.0121(4) Uani 1 1 d . . . . .
C1 C 0.23586(16) 0.3855(5) 0.60177(16) 0.0133(4) Uani 1 1 d . . . . .
H1A H 0.233193 0.469411 0.535947 0.016 Uiso 1 1 calc R U . . .
C4 C 0.38791(15) 0.6617(4) 0.72213(16) 0.0116(4) Uani 1 1 d . . . . .
H1 H 0.122(2) 0.098(6) 0.564(2) 0.020(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
S1 C5 1.735(2) . ?
S1 C4 1.747(2) . ?
O002 H00A 0.85(10) 2_556 ?
O002 H00A 0.8498 . ?
O002 H00B 0.85(10) 2_556 ?
O002 H00B 0.8502 . ?
O1 N6 1.227(2) . ?
O2 N6 1.226(2) . ?
N6 C3 1.440(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.339(3) . ?
N3 N4 1.375(2) . ?
N3 C4 1.306(3) . ?
N1 N2 1.333(2) . ?
N1 C1 1.346(3) . ?
N1 H1 0.86(3) . ?
N2 C3 1.331(3) . ?
N4 C5 1.323(3) . ?
C2 C3 1.410(3) . ?
C2 C1 1.391(3) . ?
C2 C4 1.459(3) . ?
C1 H1A 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
C5 S1 C4 86.97(10) . . ?
H00A O002 H00A 103.5 . 2_556 ?
H00A O002 H00B 104.5 2_556 2_556 ?
H00A O002 H00B 18.9 . 2_556 ?
H00A O002 H00B 104.5 . . ?
H00B O002 H00A 18.9 . 2_556 ?
H00B O002 H00B 111.7 . 2_556 ?
O1 N6 C3 119.18(18) . . ?
O2 N6 O1 123.18(17) . . ?
O2 N6 C3 117.64(18) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
C4 N3 N4 114.05(16) . . ?
N2 N1 C1 113.18(17) . . ?
N2 N1 H1 118.0(17) . . ?
C1 N1 H1 128.9(17) . . ?
C3 N2 N1 103.57(17) . . ?
C5 N4 N3 111.67(16) . . ?
C3 C2 C4 135.53(18) . . ?
C1 C2 C3 101.98(17) . . ?
C1 C2 C4 122.48(19) . . ?
N2 C3 N6 116.91(19) . . ?
N2 C3 C2 113.66(17) . . ?
C2 C3 N6 129.41(19) . . ?
N5 C5 S1 121.56(15) . . ?
N4 C5 S1 114.15(15) . . ?
N4 C5 N5 124.27(18) . . ?
N1 C1 C2 107.62(18) . . ?
N1 C1 H1A 126.2 . . ?
C2 C1 H1A 126.2 . . ?
N3 C4 S1 113.16(15) . . ?
N3 C4 C2 119.69(18) . . ?
C2 C4 S1 127.15(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N6 C3 N2 2.6(3) . . . . ?
O1 N6 C3 C2 -179.1(2) . . . . ?
O2 N6 C3 N2 -177.5(2) . . . . ?
O2 N6 C3 C2 0.8(3) . . . . ?
N3 N4 C5 S1 -0.6(2) . . . . ?
N3 N4 C5 N5 177.69(18) . . . . ?
N1 N2 C3 N6 178.25(18) . . . . ?
N1 N2 C3 C2 -0.3(2) . . . . ?
N2 N1 C1 C2 0.7(2) . . . . ?
N4 N3 C4 S1 -0.8(2) . . . . ?
N4 N3 C4 C2 179.66(17) . . . . ?
C3 C2 C1 N1 -0.8(2) . . . . ?
C3 C2 C4 S1 -2.4(4) . . . . ?
C3 C2 C4 N3 177.1(2) . . . . ?
C5 S1 C4 N3 0.40(16) . . . . ?
C5 S1 C4 C2 179.88(19) . . . . ?
C1 N1 N2 C3 -0.2(2) . . . . ?
C1 C2 C3 N6 -177.7(2) . . . . ?
C1 C2 C3 N2 0.7(2) . . . . ?
C1 C2 C4 S1 178.95(16) . . . . ?
C1 C2 C4 N3 -1.6(3) . . . . ?
C4 S1 C5 N5 -178.20(18) . . . . ?
C4 S1 C5 N4 0.11(16) . . . . ?
C4 N3 N4 C5 0.9(3) . . . . ?
C4 C2 C3 N6 3.5(4) . . . . ?
C4 C2 C3 N2 -178.2(2) . . . . ?
C4 C2 C1 N1 178.28(18) . . . . ?

_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_29feba_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2419625'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-07
_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         'C5 H3 N6 O2 S, H4 N'
_chemical_formula_sum            'C5 H7 N7 O2 S'
_chemical_formula_weight         229.24
_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'
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                   7.2255(3)
_cell_length_b                   8.2299(4)
_cell_length_c                   8.5296(3)
_cell_angle_alpha                76.9840(10)
_cell_angle_beta                 67.4560(10)
_cell_angle_gamma                79.1100(10)
_cell_volume                     453.44(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5005
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0797 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.8628.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7647
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.377
_diffrn_reflns_theta_min         2.557
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2076
_reflns_number_total             2255
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (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         0.429
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.068
_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)+(0.0464P)²+0.2436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All N(H,H) groups
2.a Free rotating group:
 N7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C1(H1A)
;
_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
S1 S 0.30711(5) 0.43753(4) 0.37505(4) 0.01702(12) Uani 1 1 d . . . . .
O1 O 0.13763(16) 0.87103(13) 0.04623(14) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.06916(16) 0.65220(16) 0.25014(17) 0.0319(3) Uani 1 1 d . . . . .
N3 N 0.69368(18) 0.39140(15) 0.27142(16) 0.0180(3) Uani 1 1 d . . . . .
N5 N 0.39192(18) 0.70183(15) 0.09243(16) 0.0172(3) Uani 1 1 d . . . . .
N4 N 0.64867(18) 0.52365(15) 0.15648(16) 0.0176(3) Uani 1 1 d . . . . .
N7 N 0.89956(19) 0.75808(17) -0.10518(17) 0.0205(3) Uani 1 1 d G . . . .
H7A H 0.826834 0.686401 -0.030164 0.031 Uiso 1 1 d G U . . .
H7B H 0.930469 0.812774 -0.047081 0.031 Uiso 1 1 d G U . . .
N6 N 0.19644(19) 0.73863(16) 0.13340(17) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.47156(19) 0.00580(16) 0.76369(16) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.401570 -0.056869 0.858691 0.024 Uiso 1 1 calc R U . . .
N2 N 0.6761(2) -0.01032(16) 0.69669(17) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.5440(2) 0.19768(17) 0.53169(18) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.5326(2) 0.33394(17) 0.39297(18) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.4530(2) 0.56416(17) 0.19370(18) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.7201(2) 0.10636(19) 0.5562(2) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.853411 0.126033 0.481351 0.024 Uiso 1 1 calc R U . . .
C1 C 0.3874(2) 0.12767(18) 0.66945(19) 0.0191(3) Uani 1 1 d . . . . .
H1A H 0.247275 0.159682 0.692861 0.023 Uiso 1 1 calc R U . . .
H7C H 1.009(4) 0.701(3) -0.175(3) 0.046(6) Uiso 1 1 d . . . . .
H7D H 0.829(4) 0.829(3) -0.171(3) 0.045(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
S1 C4 1.7355(14) . ?
S1 C5 1.7404(14) . ?
O1 N6 1.2740(15) . ?
O2 N6 1.2527(17) . ?
N3 N4 1.3717(16) . ?
N3 C4 1.3096(18) . ?
N5 N6 1.3101(17) . ?
N5 C5 1.3738(17) . ?
N4 C5 1.3174(18) . ?
N7 H7A 0.8502 . ?
N7 H7B 0.8493 . ?
N7 H7C 0.91(3) . ?
N7 H7D 0.94(2) . ?
N1 H1 0.8800 . ?
N1 N2 1.3568(18) . ?
N1 C1 1.3428(19) . ?
N2 C3 1.328(2) . ?
C2 C4 1.451(2) . ?
C2 C3 1.4140(19) . ?
C2 C1 1.384(2) . ?
C3 H3 0.9500 . ?
C1 H1A 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
C4 S1 C5 86.73(7) . . ?
C4 N3 N4 112.80(11) . . ?
N6 N5 C5 115.55(12) . . ?
C5 N4 N3 112.66(12) . . ?
H7A N7 H7B 104.5 . . ?
H7A N7 H7C 107.7 . . ?
H7A N7 H7D 111.2 . . ?
H7B N7 H7C 112.6 . . ?
H7B N7 H7D 111.2 . . ?
H7C N7 H7D 109(2) . . ?
O1 N6 N5 116.17(12) . . ?
O2 N6 O1 119.82(12) . . ?
O2 N6 N5 124.02(12) . . ?
N2 N1 H1 123.6 . . ?
C1 N1 H1 123.6 . . ?
C1 N1 N2 112.74(12) . . ?
C3 N2 N1 104.49(12) . . ?
C3 C2 C4 127.31(13) . . ?
C1 C2 C4 128.42(13) . . ?
C1 C2 C3 104.27(13) . . ?
N3 C4 S1 114.12(11) . . ?
N3 C4 C2 122.36(12) . . ?
C2 C4 S1 123.51(11) . . ?
N5 C5 S1 129.01(11) . . ?
N4 C5 S1 113.68(11) . . ?
N4 C5 N5 117.22(13) . . ?
N2 C3 C2 111.65(13) . . ?
N2 C3 H3 124.2 . . ?
C2 C3 H3 124.2 . . ?
N1 C1 C2 106.85(13) . . ?
N1 C1 H1A 126.6 . . ?
C2 C1 H1A 126.6 . . ?

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 C5 S1 -0.94(16) . . . . ?
N3 N4 C5 N5 176.11(11) . . . . ?
N4 N3 C4 S1 0.79(16) . . . . ?
N4 N3 C4 C2 -178.03(13) . . . . ?
N6 N5 C5 S1 -3.33(19) . . . . ?
N6 N5 C5 N4 -179.85(12) . . . . ?
N1 N2 C3 C2 -0.25(17) . . . . ?
N2 N1 C1 C2 -0.16(17) . . . . ?
C4 S1 C5 N5 -175.50(14) . . . . ?
C4 S1 C5 N4 1.12(11) . . . . ?
C4 N3 N4 C5 0.10(17) . . . . ?
C4 C2 C3 N2 -179.97(14) . . . . ?
C4 C2 C1 N1 -179.87(14) . . . . ?
C5 S1 C4 N3 -1.07(11) . . . . ?
C5 S1 C4 C2 177.74(13) . . . . ?
C5 N5 N6 O1 176.47(12) . . . . ?
C5 N5 N6 O2 -3.7(2) . . . . ?
C3 C2 C4 S1 179.85(12) . . . . ?
C3 C2 C4 N3 -1.4(2) . . . . ?
C3 C2 C1 N1 0.00(16) . . . . ?
C1 N1 N2 C3 0.25(17) . . . . ?
C1 C2 C4 S1 -0.3(2) . . . . ?
C1 C2 C4 N3 178.40(14) . . . . ?
C1 C2 C3 N2 0.16(17) . . . . ?

_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_8julc_a
_database_code_depnum_ccdc_archive 'CCDC 2419624'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_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         'C5 H3 N7 O4 S, C2 H6 O S'
_chemical_formula_sum            'C7 H9 N7 O5 S2'
_chemical_formula_weight         335.33
_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      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                   9.3112(3)
_cell_length_b                   16.9168(5)
_cell_length_c                   8.2596(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.7140(10)
_cell_angle_gamma                90
_cell_volume                     1300.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1183 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8459.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19845
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.744
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2670
_reflns_number_total             3225
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.875
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+1.2991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1214
_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:
 C1(H1A)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_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
S1 S 0.70638(5) 0.71402(3) 0.52436(6) 0.02314(14) Uani 1 1 d . . . . .
S2 S 0.14069(6) 0.70852(3) 0.94895(7) 0.02934(16) Uani 1 1 d . . . . .
O5 O 0.25744(17) 0.75503(9) 0.8614(2) 0.0314(4) Uani 1 1 d . . . . .
O1 O 0.96824(18) 0.51718(9) 0.2461(2) 0.0332(4) Uani 1 1 d . . . . .
O2 O 0.87903(19) 0.62815(9) 0.3297(2) 0.0373(4) Uani 1 1 d . . . . .
O3 O 0.72546(19) 0.86305(10) 0.4894(2) 0.0364(4) Uani 1 1 d . . . . .
O4 O 0.6123(2) 0.95741(10) 0.6127(2) 0.0410(4) Uani 1 1 d . . . . .
N2 N 0.8224(2) 0.43730(10) 0.4656(2) 0.0266(4) Uani 1 1 d . . . . .
N5 N 0.4841(2) 0.70491(10) 0.6936(2) 0.0255(4) Uani 1 1 d . . . . .
N4 N 0.52039(19) 0.62773(10) 0.6719(2) 0.0262(4) Uani 1 1 d . . . . .
N3 N 0.8895(2) 0.55554(11) 0.3340(2) 0.0276(4) Uani 1 1 d . . . . .
N1 N 0.7301(2) 0.41695(11) 0.5816(2) 0.0262(4) Uani 1 1 d . . . . .
N7 N 0.6298(2) 0.88685(11) 0.5807(2) 0.0296(4) Uani 1 1 d . . . . .
N6 N 0.53756(19) 0.83584(10) 0.6530(2) 0.0258(4) Uani 1 1 d . . . . .
C3 C 0.8027(2) 0.51470(12) 0.4507(3) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.6984(2) 0.54504(12) 0.5565(3) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.6541(2) 0.47804(12) 0.6387(3) 0.0248(4) Uani 1 1 d . . . . .
H1A H 0.583185 0.475824 0.720203 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6362(2) 0.62285(11) 0.5859(3) 0.0223(4) Uani 1 1 d . . . . .
C5 C 0.5689(2) 0.75934(12) 0.6283(2) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.0088(2) 0.68414(13) 0.8011(3) 0.0310(5) Uani 1 1 d . . . . .
H7A H -0.036262 0.732653 0.760145 0.046 Uiso 1 1 calc R U . . .
H7B H -0.064476 0.650347 0.849815 0.046 Uiso 1 1 calc R U . . .
H7C H 0.053984 0.655910 0.711549 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2150(3) 0.61229(15) 0.9781(3) 0.0372(6) Uani 1 1 d . . . . .
H6A H 0.241312 0.589945 0.873074 0.056 Uiso 1 1 calc R U . . .
H6B H 0.143886 0.578122 1.029482 0.056 Uiso 1 1 calc R U . . .
H6C H 0.300781 0.615959 1.047715 0.056 Uiso 1 1 calc R U . . .
H1 H 0.727(3) 0.3698(19) 0.615(3) 0.038(8) Uiso 1 1 d . . . . .
H5 H 0.409(4) 0.7177(19) 0.751(4) 0.049(9) 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
S1 C4 1.753(2) . ?
S1 C5 1.730(2) . ?
S2 O5 1.5309(16) . ?
S2 C7 1.770(3) . ?
S2 C6 1.784(3) . ?
O1 N3 1.224(2) . ?
O2 N3 1.233(2) . ?
O3 N7 1.241(2) . ?
O4 N7 1.234(2) . ?
N2 N1 1.340(3) . ?
N2 C3 1.328(3) . ?
N5 N4 1.361(2) . ?
N5 C5 1.332(3) . ?
N5 H5 0.88(3) . ?
N4 C4 1.301(3) . ?
N3 C3 1.442(3) . ?
N1 C1 1.341(3) . ?
N1 H1 0.84(3) . ?
N7 N6 1.360(2) . ?
N6 C5 1.343(3) . ?
C3 C2 1.411(3) . ?
C2 C1 1.387(3) . ?
C2 C4 1.460(3) . ?
C1 H1A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C5 S1 C4 88.00(10) . . ?
O5 S2 C7 106.54(10) . . ?
O5 S2 C6 104.84(11) . . ?
C7 S2 C6 98.35(11) . . ?
C3 N2 N1 103.34(17) . . ?
N4 N5 H5 121(2) . . ?
C5 N5 N4 117.42(18) . . ?
C5 N5 H5 122(2) . . ?
C4 N4 N5 109.98(17) . . ?
O1 N3 O2 124.02(19) . . ?
O1 N3 C3 119.15(18) . . ?
O2 N3 C3 116.83(17) . . ?
N2 N1 C1 113.51(18) . . ?
N2 N1 H1 120(2) . . ?
C1 N1 H1 127(2) . . ?
O3 N7 N6 121.50(18) . . ?
O4 N7 O3 122.77(19) . . ?
O4 N7 N6 115.73(18) . . ?
C5 N6 N7 113.91(17) . . ?
N2 C3 N3 117.17(18) . . ?
N2 C3 C2 113.36(18) . . ?
C2 C3 N3 129.46(19) . . ?
C3 C2 C4 135.14(19) . . ?
C1 C2 C3 102.54(18) . . ?
C1 C2 C4 122.31(19) . . ?
N1 C1 C2 107.25(19) . . ?
N1 C1 H1A 126.4 . . ?
C2 C1 H1A 126.4 . . ?
N4 C4 S1 114.64(15) . . ?
N4 C4 C2 118.78(18) . . ?
C2 C4 S1 126.51(15) . . ?
N5 C5 S1 109.93(15) . . ?
N5 C5 N6 118.29(18) . . ?
N6 C5 S1 131.77(16) . . ?
S2 C7 H7A 109.5 . . ?
S2 C7 H7B 109.5 . . ?
S2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
S2 C6 H6A 109.5 . . ?
S2 C6 H6B 109.5 . . ?
S2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O1 N3 C3 N2 5.6(3) . . . . ?
O1 N3 C3 C2 -175.5(2) . . . . ?
O2 N3 C3 N2 -174.4(2) . . . . ?
O2 N3 C3 C2 4.5(3) . . . . ?
O3 N7 N6 C5 5.9(3) . . . . ?
O4 N7 N6 C5 -173.7(2) . . . . ?
N2 N1 C1 C2 -0.4(3) . . . . ?
N2 C3 C2 C1 -0.4(3) . . . . ?
N2 C3 C2 C4 -178.6(2) . . . . ?
N5 N4 C4 S1 -0.7(2) . . . . ?
N5 N4 C4 C2 176.45(19) . . . . ?
N4 N5 C5 S1 1.5(3) . . . . ?
N4 N5 C5 N6 -177.81(19) . . . . ?
N3 C3 C2 C1 -179.3(2) . . . . ?
N3 C3 C2 C4 2.5(4) . . . . ?
N1 N2 C3 N3 179.23(18) . . . . ?
N1 N2 C3 C2 0.1(2) . . . . ?
N7 N6 C5 S1 1.2(3) . . . . ?
N7 N6 C5 N5 -179.65(19) . . . . ?
C3 N2 N1 C1 0.2(3) . . . . ?
C3 C2 C1 N1 0.5(2) . . . . ?
C3 C2 C4 S1 -16.7(4) . . . . ?
C3 C2 C4 N4 166.5(2) . . . . ?
C1 C2 C4 S1 165.42(18) . . . . ?
C1 C2 C4 N4 -11.4(3) . . . . ?
C4 S1 C5 N5 -1.49(16) . . . . ?
C4 S1 C5 N6 177.7(2) . . . . ?
C4 C2 C1 N1 179.0(2) . . . . ?
C5 S1 C4 N4 1.31(18) . . . . ?
C5 S1 C4 C2 -175.6(2) . . . . ?
C5 N5 N4 C4 -0.5(3) . . . . ?

_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_7mayc_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2419626'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_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         'C5 H3 N8 O2 S, N O3'
_chemical_formula_sum            'C5 H3 N9 O5 S'
_chemical_formula_weight         301.22
_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      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                   5.3298(2)
_cell_length_b                   13.0514(4)
_cell_length_c                   15.3353(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.4230(10)
_cell_angle_gamma                90
_cell_volume                     1060.05(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1288 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8768.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22696
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2498
_reflns_number_total             2646
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (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         0.375
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+0.6361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0654
_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:
 N4(H4), C1(H1A)
;
_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
S1 S 0.73532(5) 0.43183(2) 0.26335(2) 0.01281(8) Uani 1 1 d . . . . .
O3 O -0.04042(16) 0.42952(6) 0.58305(6) 0.01692(17) Uani 1 1 d . . . . .
O1 O 0.83764(17) 0.55270(7) 0.14519(6) 0.02026(19) Uani 1 1 d . . . . .
O5 O -0.01925(17) 0.29146(7) 0.66395(6) 0.02196(19) Uani 1 1 d . . . . .
O4 O -0.25739(16) 0.41808(7) 0.69457(6) 0.02012(19) Uani 1 1 d . . . . .
O2 O 1.15732(19) 0.55345(7) 0.06878(7) 0.0265(2) Uani 1 1 d . . . . .
N7 N 0.82081(18) 0.17769(7) 0.50110(6) 0.01370(19) Uani 1 1 d . . . . .
N9 N -0.10535(18) 0.37931(7) 0.64814(6) 0.01435(19) Uani 1 1 d . . . . .
N2 N 0.47535(18) 0.26951(7) 0.53912(6) 0.01439(19) Uani 1 1 d . . . . .
N5 N 1.11431(18) 0.41933(7) 0.15243(6) 0.0152(2) Uani 1 1 d . . . . .
N4 N 1.06519(18) 0.29427(8) 0.25499(6) 0.01517(19) Uani 1 1 d . . . . .
H4 H 1.187673 0.257776 0.236541 0.018 Uiso 1 1 calc R U . . .
N1 N 0.34493(18) 0.34958(8) 0.50403(7) 0.01473(19) Uani 1 1 d . . . . .
N3 N 0.94640(19) 0.26325(8) 0.32454(6) 0.01526(19) Uani 1 1 d . . . . .
N6 N 1.03117(19) 0.51243(8) 0.12168(6) 0.0166(2) Uani 1 1 d . . . . .
N8 N 0.9663(2) 0.12020(8) 0.52012(7) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.6403(2) 0.25314(8) 0.48095(7) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.6196(2) 0.32098(8) 0.40930(7) 0.0129(2) Uani 1 1 d . . . . .
C5 C 0.9889(2) 0.38244(8) 0.21557(7) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.7705(2) 0.32891(8) 0.33666(7) 0.0130(2) Uani 1 1 d . . . . .
C1 C 0.4224(2) 0.38322(9) 0.42801(7) 0.0147(2) Uani 1 1 d . . . . .
H1A H 0.353872 0.439309 0.393732 0.018 Uiso 1 1 calc R U . . .
H1 H 0.219(3) 0.3738(13) 0.5316(11) 0.028(4) 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
S1 C5 1.7322(11) . ?
S1 C4 1.7482(11) . ?
O3 N9 1.2738(13) . ?
O1 N6 1.2464(13) . ?
O5 N9 1.2486(13) . ?
O4 N9 1.2445(13) . ?
O2 N6 1.2325(13) . ?
N7 N8 1.0948(14) . ?
N7 C3 1.3870(14) . ?
N2 N1 1.3346(13) . ?
N2 C3 1.3380(14) . ?
N5 N6 1.3595(14) . ?
N5 C5 1.3271(14) . ?
N4 H4 0.8800 . ?
N4 N3 1.3614(13) . ?
N4 C5 1.3417(15) . ?
N1 C1 1.3528(15) . ?
N1 H1 0.888(18) . ?
N3 C4 1.2986(14) . ?
C3 C2 1.4058(15) . ?
C2 C4 1.4489(15) . ?
C2 C1 1.3838(15) . ?
C1 H1A 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
C5 S1 C4 87.33(5) . . ?
N8 N7 C3 177.09(12) . . ?
O5 N9 O3 119.89(10) . . ?
O4 N9 O3 119.37(10) . . ?
O4 N9 O5 120.73(10) . . ?
N1 N2 C3 101.99(9) . . ?
C5 N5 N6 113.96(9) . . ?
N3 N4 H4 121.2 . . ?
C5 N4 H4 121.2 . . ?
C5 N4 N3 117.64(9) . . ?
N2 N1 C1 113.97(9) . . ?
N2 N1 H1 118.2(11) . . ?
C1 N1 H1 127.8(11) . . ?
C4 N3 N4 108.80(9) . . ?
O1 N6 N5 121.65(9) . . ?
O2 N6 O1 122.50(10) . . ?
O2 N6 N5 115.85(10) . . ?
N7 C3 C2 127.82(10) . . ?
N2 C3 N7 117.12(10) . . ?
N2 C3 C2 114.87(10) . . ?
C3 C2 C4 130.10(10) . . ?
C1 C2 C3 101.70(9) . . ?
C1 C2 C4 128.13(10) . . ?
N5 C5 S1 130.86(9) . . ?
N5 C5 N4 119.21(10) . . ?
N4 C5 S1 109.88(8) . . ?
N3 C4 S1 116.25(8) . . ?
N3 C4 C2 122.31(10) . . ?
C2 C4 S1 121.36(8) . . ?
N1 C1 C2 107.48(10) . . ?
N1 C1 H1A 126.3 . . ?
C2 C1 H1A 126.3 . . ?

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
N7 C3 C2 C4 2.4(2) . . . . ?
N7 C3 C2 C1 -174.69(11) . . . . ?
N2 N1 C1 C2 0.46(13) . . . . ?
N2 C3 C2 C4 177.19(11) . . . . ?
N2 C3 C2 C1 0.10(13) . . . . ?
N4 N3 C4 S1 0.81(12) . . . . ?
N4 N3 C4 C2 -176.11(10) . . . . ?
N1 N2 C3 N7 175.53(9) . . . . ?
N1 N2 C3 C2 0.15(13) . . . . ?
N3 N4 C5 S1 -3.19(13) . . . . ?
N3 N4 C5 N5 174.37(10) . . . . ?
N6 N5 C5 S1 1.38(16) . . . . ?
N6 N5 C5 N4 -175.58(10) . . . . ?
C3 N2 N1 C1 -0.37(12) . . . . ?
C3 C2 C4 S1 -170.78(10) . . . . ?
C3 C2 C4 N3 5.98(19) . . . . ?
C3 C2 C1 N1 -0.31(12) . . . . ?
C5 S1 C4 N3 -2.15(9) . . . . ?
C5 S1 C4 C2 174.80(10) . . . . ?
C5 N5 N6 O1 -7.14(15) . . . . ?
C5 N5 N6 O2 173.60(10) . . . . ?
C5 N4 N3 C4 1.59(14) . . . . ?
C4 S1 C5 N5 -174.38(12) . . . . ?
C4 S1 C5 N4 2.80(8) . . . . ?
C4 C2 C1 N1 -177.48(11) . . . . ?
C1 C2 C4 S1 5.59(17) . . . . ?
C1 C2 C4 N3 -177.65(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
