# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_md-100_autored
_database_code_depnum_ccdc_archive 'CCDC 2393742'
loop_
_audit_author_name
_audit_author_address
'Mangal Singh Yadav'
;BANARAS HINDU UNIVERSITY VARANASI 
India
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 N4'
_chemical_formula_sum            'C9 H10 N4'
_chemical_formula_weight         174.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.98700(10)
_cell_length_b                   9.0189(2)
_cell_length_c                   19.7788(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.055(2)
_cell_angle_gamma                90
_cell_volume                     888.33(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6413
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7520
_cell_measurement_theta_min      4.4540
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11682
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.073
_diffrn_reflns_theta_min         4.477
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 170.00   0.50    0.52    --   96.04  96.00 -30.00  130
  2  ω    -35.00  24.00   0.50    0.20    --   40.83 -11.00  90.00  118
  3  ω    -27.00  37.00   0.50    0.20    --   40.83 -32.00  30.00  128
  4  ω    -31.00  28.00   0.50    0.20    --   40.83 -21.00 -60.00  118
  5  ω    -31.00  27.00   0.50    0.20    --   40.83 -20.00 -96.00  116
  6  ω     23.00 106.00   0.50    0.52    --   96.04 -96.00   0.00  166
  7  ω     23.00 106.00   0.50    0.52    --   96.04 -96.00 -90.00  166
  8  ω     44.00 127.00   0.50    0.52    --   96.04-145.00 -60.00  166
  9  ω     41.00 100.00   0.50    0.20    --   40.83-138.00  30.00  118
 10  ω     41.00 100.00   0.50    0.20    --   40.83-138.00 150.00  118
 11  ω     32.00 110.00   0.50    0.52    --   96.04-117.00 120.00  156
 12  ω     27.00 105.00   0.50    0.52    --   96.04 -77.00  90.00  156
 13  ω     27.00 105.00   0.50    0.52    --   96.04 -77.00 120.00  156
 14  ω     28.00  68.00   0.50    0.52    --   96.04 -59.00 150.00   80
 15  ω     28.00  68.00   0.50    0.52    --   96.04 -59.00 120.00   80
 16  ω     28.00  83.00   0.50    0.52    --   96.04 -68.00   0.00  110
 17  ω     29.00  57.00   0.50    0.52    --   96.04 -50.00-120.00   56
 18  ω     28.00  68.00   0.50    0.52    --   96.04 -59.00 -90.00   80
 19  ω     29.00  57.00   0.50    0.52    --   96.04 -50.00-180.00   56
 20  ω     28.00  68.00   0.50    0.52    --   96.04 -59.00 -60.00   80
 21  ω     28.00  68.00   0.50    0.52    --   96.04 -59.00 -30.00   80
 22  ω     29.00  57.00   0.50    0.52    --   96.04 -50.00 150.00   56
 23  ω     71.00 169.00   0.50    0.52    --   96.04  17.00 -90.00  196
 24  ω     69.00 165.00   0.50    0.52    --   96.04  77.00-180.00  192
 25  ω     69.00 165.00   0.50    0.52    --   96.04  77.00-150.00  192
 26  ω     69.00 165.00   0.50    0.52    --   96.04  77.00-120.00  192
 27  ω     72.00 144.00   0.50    0.52    --   96.04  68.00  60.00  144
 28  ω     74.00 163.00   0.50    0.52    --   96.04  59.00  90.00  178
 29  ω     72.00 164.00   0.50    0.52    --   96.04  68.00 120.00  184
 30  ω     69.00 165.00   0.50    0.52    --   96.04  77.00 150.00  192
 31  ω     79.00 162.00   0.50    0.52    --   96.04  42.00 150.00  166
 32  ω     77.00 168.00   0.50    0.52    --   96.04  20.00  70.00  182
 33  ω     79.00 162.00   0.50    0.52    --   96.04  42.00   0.00  166
 34  ω     77.00 163.00   0.50    0.52    --   96.04  50.00 -60.00  172
 35  ω     14.00 110.00   0.50    0.20    --   40.83  77.00   0.00  192
 36  ω     14.00 110.00   0.50    0.20    --   40.83  77.00  60.00  192
 37  ω     14.00 110.00   0.50    0.20    --   40.83  77.00  90.00  192
 38  ω     22.00 113.00   0.50    0.20    --   40.83  20.00  70.00  182
 39  ω     21.00 108.00   0.50    0.20    --   40.83  54.00-180.00  174
 40  ω    -48.00  26.00   0.50    0.20    --  -40.83  43.00 -60.00  148
 41  ω    -68.00 -14.00   0.50    0.52    --  -82.50  59.00-120.00  108
 42  ω    -57.00 -16.00   0.50    0.52    --  -82.50  50.00-180.00   82
 43  ω    -47.00 -15.00   0.50    0.52    --  -82.50  42.00-120.00   64
 44  ω    -57.00 -16.00   0.50    0.52    --  -82.50  50.00 -60.00   82
 45  ω    -27.00  31.00   0.50    0.20    --  -40.83  20.00  70.00  116
 46  ω    -28.00  31.00   0.50    0.20    --  -40.83  21.00 120.00  118
 47  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 150.00  190
 48  ω   -108.00 -17.00   0.50    0.20    --  -40.83 -65.00-150.00  182
 49  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -90.00  190
 50  ω   -113.00 -22.00   0.50    0.20    --  -40.83 -20.00 -96.00  182
 51  ω   -155.00 -64.00   0.50    0.52    --  -82.50 -20.00 -96.00  182
 52  ω   -151.00 -55.00   0.50    0.52    --  -82.50 -77.00  30.00  192
 53  ω   -151.00 -55.00   0.50    0.52    --  -82.50 -77.00 -30.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2300666000
_diffrn_orient_matrix_UB_12      0.0439061000
_diffrn_orient_matrix_UB_13      -0.0512067000
_diffrn_orient_matrix_UB_21      0.1936279000
_diffrn_orient_matrix_UB_22      -0.0098804000
_diffrn_orient_matrix_UB_23      -0.0579690000
_diffrn_orient_matrix_UB_31      -0.0731401000
_diffrn_orient_matrix_UB_32      -0.1646963000
_diffrn_orient_matrix_UB_33      -0.0101509000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1380
_reflns_number_total             1599
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.116
_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)+(0.1023P)²+1.3894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.2646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-N1
 0.98 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C1(H1A), C3(H3)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6863(7) 0.5736(3) 0.27209(16) 0.0560(9) Uani 1 1 d D . . . .
N2 N 0.7599(7) 0.4450(4) 0.24673(18) 0.0611(9) Uani 1 1 d . . . . .
N4 N 0.1293(7) 0.4005(4) 0.40609(17) 0.0635(10) Uani 1 1 d . . . . .
N3 N 0.6173(7) 0.3442(4) 0.27795(17) 0.0608(9) Uani 1 1 d . . . . .
C5 C 0.2725(7) 0.3244(4) 0.36242(18) 0.0512(9) Uani 1 1 d . . . . .
C7 C 0.4972(7) 0.5610(4) 0.31845(19) 0.0532(9) Uani 1 1 d . . . . .
C6 C 0.4544(7) 0.4102(4) 0.32189(19) 0.0539(9) Uani 1 1 d . . . . .
C4 C 0.2547(8) 0.1713(5) 0.3566(2) 0.0618(11) Uani 1 1 d . . . . .
H4 H 0.358123 0.120481 0.326429 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3915(8) 0.6936(5) 0.3539(2) 0.0655(11) Uani 1 1 d . . . . .
H8A H 0.378416 0.776215 0.322493 0.079 Uiso 1 1 calc R U . . .
H8B H 0.212303 0.672011 0.367987 0.079 Uiso 1 1 calc R U . . .
C2 C -0.0691(9) 0.1737(6) 0.4394(2) 0.0714(13) Uani 1 1 d . . . . .
H2 H -0.190010 0.124851 0.465900 0.086 Uiso 1 1 calc R U . . .
C1 C -0.0400(9) 0.3234(6) 0.4432(2) 0.0701(12) Uani 1 1 d . . . . .
H1A H -0.142983 0.375145 0.473157 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0828(9) 0.0963(5) 0.3959(2) 0.0679(12) Uani 1 1 d . . . . .
H3 H 0.069217 -0.006390 0.393165 0.082 Uiso 1 1 calc R U . . .
C9 C 0.5654(11) 0.7371(6) 0.4144(3) 0.0876(17) Uani 1 1 d . . . . .
H9A H 0.744876 0.754753 0.400972 0.131 Uiso 1 1 calc R U . . .
H9B H 0.567256 0.658736 0.447220 0.131 Uiso 1 1 calc R U . . .
H9C H 0.496010 0.825815 0.433767 0.131 Uiso 1 1 calc R U . . .
H1 H 0.769(10) 0.659(4) 0.248(2) 0.094(15) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.323(5) . ?
N1 C7 1.355(5) . ?
N1 H1 1.00(2) . ?
N2 N3 1.327(4) . ?
N4 C5 1.339(5) . ?
N4 C1 1.343(5) . ?
N3 C6 1.358(5) . ?
C5 C6 1.463(5) . ?
C5 C4 1.389(6) . ?
C7 C6 1.379(5) . ?
C7 C8 1.496(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.367(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.360(7) . ?
C2 C3 1.367(6) . ?
C1 H1A 0.9300 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 113.6(3) . . ?
N2 N1 H1 111(3) . . ?
C7 N1 H1 135(3) . . ?
N1 N2 N3 104.9(3) . . ?
C5 N4 C1 117.4(4) . . ?
N2 N3 C6 110.6(3) . . ?
N4 C5 C6 116.7(4) . . ?
N4 C5 C4 122.0(3) . . ?
C4 C5 C6 121.3(3) . . ?
N1 C7 C6 103.4(3) . . ?
N1 C7 C8 121.7(3) . . ?
C6 C7 C8 134.9(4) . . ?
N3 C6 C5 121.9(4) . . ?
N3 C6 C7 107.5(3) . . ?
C7 C6 C5 130.6(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.4(4) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
N4 C1 C2 123.6(4) . . ?
N4 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N1 N2 N3 C6 0.6(4) . . . . ?
N1 C7 C6 N3 -0.2(4) . . . . ?
N1 C7 C6 C5 -179.6(4) . . . . ?
N1 C7 C8 C9 -84.5(5) . . . . ?
N2 N1 C7 C6 0.6(4) . . . . ?
N2 N1 C7 C8 178.8(4) . . . . ?
N2 N3 C6 C5 179.2(3) . . . . ?
N2 N3 C6 C7 -0.3(4) . . . . ?
N4 C5 C6 N3 177.3(3) . . . . ?
N4 C5 C6 C7 -3.3(6) . . . . ?
N4 C5 C4 C3 1.0(6) . . . . ?
C5 N4 C1 C2 1.1(6) . . . . ?
C5 C4 C3 C2 0.7(6) . . . . ?
C7 N1 N2 N3 -0.8(4) . . . . ?
C6 C5 C4 C3 179.6(4) . . . . ?
C6 C7 C8 C9 93.1(6) . . . . ?
C4 C5 C6 N3 -1.4(5) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
C8 C7 C6 N3 -178.1(4) . . . . ?
C8 C7 C6 C5 2.5(8) . . . . ?
C1 N4 C5 C6 179.5(4) . . . . ?
C1 N4 C5 C4 -1.9(6) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C3 C2 C1 N4 0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.911
_oxdiff_exptl_absorpt_empirical_full_min 0.624
