# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_25augc
_database_code_depnum_ccdc_archive 'CCDC 2513812'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2025-12-06 deposited with the CCDC.	2026-06-19 downloaded from the CCDC.
;
_audit_creation_date             2025-12-04
_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        SEN145
_chemical_formula_moiety         'C2 H N9'
_chemical_formula_sum            'C2 H N9'
_chemical_formula_weight         151.12
_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'

_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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   12.0395(10)
_cell_length_b                   23.364(2)
_cell_length_c                   8.0029(6)
_cell_angle_alpha                90
_cell_angle_beta                 125.292(2)
_cell_angle_gamma                90
_cell_volume                     1837.5(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1145 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.9458.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear grayish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.17
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14578
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.464
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_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         0.989
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4473
_reflns_number_total             4580
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (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         0.213
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.2(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.058
_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)+(0.0379P)²+0.4091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.2(17)
 1.2(17)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N19(H19), N1(H1), N10(H10)
;
_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
N21 N 0.71559(14) 0.57271(6) 0.9557(2) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.23138(14) 0.65257(6) -0.0937(2) 0.0169(3) Uani 1 1 d . . . . .
N11 N 0.58721(15) 0.77398(6) 0.6940(2) 0.0192(3) Uani 1 1 d . . . . .
N19 N 0.64396(15) 0.65823(6) 0.8073(2) 0.0189(3) Uani 1 1 d . . . . .
H19 H 0.634434 0.695625 0.793257 0.023 Uiso 1 1 calc R U . . .
N12 N 0.58879(15) 0.87040(6) 0.6749(2) 0.0179(3) Uani 1 1 d . . . . .
N20 N 0.58040(15) 0.61823(6) 0.6532(2) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.36048(15) 0.70514(6) 0.1938(2) 0.0191(3) Uani 1 1 d . . . . .
N23 N 0.88262(15) 0.62864(7) 1.3157(2) 0.0198(3) Uani 1 1 d . . . . .
N17 N 0.78806(16) 0.87007(7) 1.0781(2) 0.0220(3) Uani 1 1 d . . . . .
N13 N 0.40799(16) 0.87594(6) 0.3074(2) 0.0218(3) Uani 1 1 d . . . . .
N5 N 0.24452(16) 0.53588(7) -0.0934(2) 0.0243(3) Uani 1 1 d . . . . .
N8 N 0.11996(16) 0.75340(6) -0.2920(2) 0.0198(3) Uani 1 1 d . . . . .
N1 N 0.39510(14) 0.64867(6) 0.2411(2) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.457394 0.634462 0.362484 0.023 Uiso 1 1 calc R U . . .
N7 N 0.20625(16) 0.75690(6) -0.1026(2) 0.0216(3) Uani 1 1 d . . . . .
N26 N 0.62549(15) 0.47405(6) 0.7417(2) 0.0189(3) Uani 1 1 d . . . . .
N9 N 0.04037(17) 0.75744(8) -0.4612(3) 0.0282(4) Uani 1 1 d . . . . .
N10 N 0.49080(14) 0.79063(6) 0.4961(2) 0.0184(3) Uani 1 1 d . . . . .
H10 H 0.436038 0.768036 0.391796 0.022 Uiso 1 1 calc R U . . .
N14 N 0.42404(16) 0.92928(7) 0.3228(2) 0.0238(3) Uani 1 1 d . . . . .
N24 N 0.96020(17) 0.60636(8) 1.4617(2) 0.0275(3) Uani 1 1 d . . . . .
N27 N 0.65737(17) 0.43076(7) 0.8164(3) 0.0252(3) Uani 1 1 d . . . . .
N4 N 0.33032(16) 0.56024(7) 0.0728(2) 0.0243(3) Uani 1 1 d . . . . .
N22 N 0.80109(16) 0.65981(6) 1.1652(2) 0.0217(3) Uani 1 1 d . . . . .
N16 N 0.74583(16) 0.82147(7) 1.0003(2) 0.0228(3) Uani 1 1 d . . . . .
N25 N 0.57986(16) 0.51859(6) 0.6360(2) 0.0209(3) Uani 1 1 d . . . . .
N6 N 0.1755(2) 0.50839(7) -0.2299(3) 0.0367(4) Uani 1 1 d . . . . .
N15 N 0.42634(19) 0.97677(7) 0.3128(3) 0.0355(4) Uani 1 1 d . . . . .
N18 N 0.83511(18) 0.91052(8) 1.1672(3) 0.0311(4) Uani 1 1 d . . . . .
C6 C 0.62620(17) 0.56889(7) 0.7497(3) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.72244(17) 0.62952(7) 0.9812(3) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.31617(17) 0.61948(7) 0.0677(3) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.49589(17) 0.84731(7) 0.4922(3) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.26396(17) 0.70489(7) -0.0055(3) 0.0170(3) Uani 1 1 d . . . . .
C4 C 0.64101(17) 0.82280(7) 0.7911(3) 0.0177(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N21 C6 1.354(2) . ?
N21 C5 1.338(2) . ?
N3 C1 1.336(2) . ?
N3 C2 1.352(2) . ?
N11 N10 1.372(2) . ?
N11 C4 1.320(2) . ?
N19 H19 0.8800 . ?
N19 N20 1.374(2) . ?
N19 C5 1.327(2) . ?
N12 C3 1.338(2) . ?
N12 C4 1.350(2) . ?
N20 C6 1.318(2) . ?
N2 N1 1.370(2) . ?
N2 C2 1.324(2) . ?
N23 N24 1.117(2) . ?
N23 N22 1.257(2) . ?
N17 N16 1.253(2) . ?
N17 N18 1.121(2) . ?
N13 N14 1.256(2) . ?
N13 C3 1.395(2) . ?
N5 N4 1.254(2) . ?
N5 N6 1.117(2) . ?
N8 N7 1.250(2) . ?
N8 N9 1.123(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.331(2) . ?
N7 C2 1.393(2) . ?
N26 N27 1.123(2) . ?
N26 N25 1.250(2) . ?
N10 H10 0.8800 . ?
N10 C3 1.327(2) . ?
N14 N15 1.114(2) . ?
N4 C1 1.392(2) . ?
N22 C5 1.398(2) . ?
N16 C4 1.398(2) . ?
N25 C6 1.391(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 N21 C6 100.76(14) . . ?
C1 N3 C2 100.91(14) . . ?
C4 N11 N10 103.58(14) . . ?
N20 N19 H19 126.6 . . ?
C5 N19 H19 126.6 . . ?
C5 N19 N20 106.71(14) . . ?
C3 N12 C4 100.56(14) . . ?
C6 N20 N19 103.96(13) . . ?
C2 N2 N1 104.11(14) . . ?
N24 N23 N22 172.31(19) . . ?
N18 N17 N16 172.5(2) . . ?
N14 N13 C3 113.10(15) . . ?
N6 N5 N4 171.83(19) . . ?
N9 N8 N7 171.30(19) . . ?
N2 N1 H1 126.7 . . ?
C1 N1 N2 106.60(14) . . ?
C1 N1 H1 126.7 . . ?
N8 N7 C2 114.64(15) . . ?
N27 N26 N25 172.12(18) . . ?
N11 N10 H10 126.6 . . ?
C3 N10 N11 106.89(14) . . ?
C3 N10 H10 126.6 . . ?
N15 N14 N13 171.84(19) . . ?
N5 N4 C1 114.08(15) . . ?
N23 N22 C5 113.27(14) . . ?
N17 N16 C4 113.66(15) . . ?
N26 N25 C6 114.02(14) . . ?
N21 C6 N25 126.06(15) . . ?
N20 C6 N21 115.14(14) . . ?
N20 C6 N25 118.80(14) . . ?
N21 C5 N22 127.39(15) . . ?
N19 C5 N21 113.43(15) . . ?
N19 C5 N22 119.18(15) . . ?
N3 C1 N4 128.04(15) . . ?
N1 C1 N3 113.46(15) . . ?
N1 C1 N4 118.50(15) . . ?
N12 C3 N13 127.47(15) . . ?
N10 C3 N12 113.40(15) . . ?
N10 C3 N13 119.12(15) . . ?
N3 C2 N7 126.64(16) . . ?
N2 C2 N3 114.91(15) . . ?
N2 C2 N7 118.45(15) . . ?
N11 C4 N12 115.56(15) . . ?
N11 C4 N16 118.83(15) . . ?
N12 C4 N16 125.60(16) . . ?

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 N10 C3 N12 -0.52(18) . . . . ?
N11 N10 C3 N13 179.72(14) . . . . ?
N19 N20 C6 N21 -0.25(19) . . . . ?
N19 N20 C6 N25 179.38(14) . . . . ?
N20 N19 C5 N21 -0.51(19) . . . . ?
N20 N19 C5 N22 179.35(14) . . . . ?
N2 N1 C1 N3 0.51(19) . . . . ?
N2 N1 C1 N4 -179.76(15) . . . . ?
N23 N22 C5 N21 7.7(3) . . . . ?
N23 N22 C5 N19 -172.17(15) . . . . ?
N17 N16 C4 N11 -178.91(15) . . . . ?
N17 N16 C4 N12 1.8(2) . . . . ?
N5 N4 C1 N3 -5.9(3) . . . . ?
N5 N4 C1 N1 174.44(16) . . . . ?
N8 N7 C2 N3 -3.1(3) . . . . ?
N8 N7 C2 N2 177.20(15) . . . . ?
N1 N2 C2 N3 0.37(18) . . . . ?
N1 N2 C2 N7 -179.91(15) . . . . ?
N26 N25 C6 N21 1.9(3) . . . . ?
N26 N25 C6 N20 -177.69(15) . . . . ?
N10 N11 C4 N12 -0.07(18) . . . . ?
N10 N11 C4 N16 -179.42(14) . . . . ?
N14 N13 C3 N12 1.3(3) . . . . ?
N14 N13 C3 N10 -178.96(16) . . . . ?
C6 N21 C5 N19 0.34(19) . . . . ?
C6 N21 C5 N22 -179.51(17) . . . . ?
C5 N21 C6 N20 0.0(2) . . . . ?
C5 N21 C6 N25 -179.64(16) . . . . ?
C5 N19 N20 C6 0.44(17) . . . . ?
C1 N3 C2 N2 -0.08(18) . . . . ?
C1 N3 C2 N7 -179.77(16) . . . . ?
C3 N12 C4 N11 -0.23(18) . . . . ?
C3 N12 C4 N16 179.08(16) . . . . ?
C2 N3 C1 N1 -0.27(18) . . . . ?
C2 N3 C1 N4 -179.97(17) . . . . ?
C2 N2 N1 C1 -0.51(17) . . . . ?
C4 N11 N10 C3 0.34(17) . . . . ?
C4 N12 C3 N13 -179.82(16) . . . . ?
C4 N12 C3 N10 0.45(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.2(17)
2 1.2(17)

