# Supplementary Information (SI) for ChemComm.
# 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_5octb_a
_database_code_depnum_ccdc_archive 'CCDC 2406898'
loop_
_audit_author_name
_audit_author_address
'Abhishek Kumar Yadav'
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-17
_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 H7 N5 O2'
_chemical_formula_sum            'C2 H7 N5 O2'
_chemical_formula_weight         133.13
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   10.8075(5)
_cell_length_b                   27.3498(15)
_cell_length_c                   7.4467(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2201.1(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6496
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4859
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1425 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.6516.
The λ/2 correction factor is Not present.
;
_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    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8453
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         2.979
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1353
_reflns_number_total             1367
_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         0.188
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 615 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1367
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.069
_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)+(0.0513P)²+1.5174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0843
_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:
 N2(H2), N3(H3), C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O -0.77027(12) -0.51361(5) -1.38036(18) 0.0175(3) Uani 1 1 d . . . . .
O1 O -0.65367(13) -0.54876(5) -1.17627(19) 0.0180(3) Uani 1 1 d . . . . .
N2 N -0.82351(14) -0.64731(6) -1.6224(2) 0.0129(3) Uani 1 1 d . . . . .
H2 H -0.860064 -0.651342 -1.726996 0.015 Uiso 1 1 calc R U . . .
N5 N -0.72183(14) -0.55274(5) -1.3166(2) 0.0130(3) Uani 1 1 d . . . . .
N3 N -0.84478(15) -0.56447(6) -1.6548(2) 0.0132(3) Uani 1 1 d . . . . .
H3 H -0.838287 -0.534500 -1.612765 0.016 Uiso 1 1 calc R U . . .
N1 N -0.78497(15) -0.68862(6) -1.5224(2) 0.0149(3) Uani 1 1 d . . . . .
N4 N -0.89818(15) -0.57321(6) -1.8257(2) 0.0161(3) Uani 1 1 d . . . . .
C1 C -0.80467(14) -0.60233(6) -1.5590(2) 0.0109(3) Uani 1 1 d . . . . .
C2 C -0.74028(16) -0.59623(7) -1.3917(2) 0.0125(4) Uani 1 1 d . . . . .
H2A H -0.709595 -0.624466 -1.332294 0.015 Uiso 1 1 calc R U . . .
H4A H -0.978(2) -0.5643(9) -1.817(4) 0.014(6) Uiso 1 1 d . . . . .
H1A H -0.850(2) -0.7082(10) -1.522(4) 0.018(6) Uiso 1 1 d . . . . .
H4B H -0.858(3) -0.5552(12) -1.901(5) 0.037(9) Uiso 1 1 d . . . . .
H1B H -0.728(3) -0.7025(10) -1.587(5) 0.029(8) 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
O2 N5 1.283(2) . ?
O1 N5 1.283(2) . ?
N2 H2 0.8800 . ?
N2 N1 1.416(2) . ?
N2 C1 1.333(2) . ?
N5 C2 1.329(2) . ?
N3 H3 0.8800 . ?
N3 N4 1.418(2) . ?
N3 C1 1.330(2) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.87(3) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.86(3) . ?
C1 C2 1.437(2) . ?
C2 H2A 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
N1 N2 H2 119.8 . . ?
C1 N2 H2 119.8 . . ?
C1 N2 N1 120.33(15) . . ?
O2 N5 O1 117.71(14) . . ?
O2 N5 C2 121.98(15) . . ?
O1 N5 C2 120.31(15) . . ?
N4 N3 H3 120.6 . . ?
C1 N3 H3 120.6 . . ?
C1 N3 N4 118.85(16) . . ?
N2 N1 H1A 104.6(18) . . ?
N2 N1 H1B 105(2) . . ?
H1A N1 H1B 108(3) . . ?
N3 N4 H4A 106.3(18) . . ?
N3 N4 H4B 107(2) . . ?
H4A N4 H4B 112(3) . . ?
N2 C1 C2 119.22(16) . . ?
N3 C1 N2 118.61(16) . . ?
N3 C1 C2 122.16(16) . . ?
N5 C2 C1 122.78(16) . . ?
N5 C2 H2A 118.6 . . ?
C1 C2 H2A 118.6 . . ?

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
O2 N5 C2 C1 6.5(3) . . . . ?
O1 N5 C2 C1 -173.29(16) . . . . ?
N2 C1 C2 N5 -177.52(16) . . . . ?
N3 C1 C2 N5 3.5(3) . . . . ?
N1 N2 C1 N3 -178.40(15) . . . . ?
N1 N2 C1 C2 2.6(2) . . . . ?
N4 N3 C1 N2 -4.3(2) . . . . ?
N4 N3 C1 C2 174.70(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
