# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_30decb_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2288301'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT Kanpur
India
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_audit_creation_date             2023-06-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N8 O2'
_chemical_formula_sum            'C4 H6 N8 O2'
_chemical_formula_weight         198.17
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   6.744(2)
_cell_length_b                   11.212(2)
_cell_length_c                   9.487(2)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     717.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1443 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.7952.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_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  0.0690
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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         0.890
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1609
_reflns_number_total             1788
_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         0.307
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.049
_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)+(0.0430P)²+0.2947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Rotating group:
 N009(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N008(H008)
;
_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
O001 O 0.2544(4) 0.67252(19) 0.8323(3) 0.0211(5) Uani 1 1 d . . . . .
O002 O 0.2774(3) 0.86591(18) 0.7935(3) 0.0214(5) Uani 1 1 d . . . . .
N003 N 0.2990(4) 0.7581(2) 0.7540(3) 0.0165(5) Uani 1 1 d . . . . .
N004 N 0.4554(4) 0.7646(2) 0.4018(3) 0.0155(5) Uani 1 1 d . . . . .
N005 N 0.4688(4) 0.9497(2) 0.3556(3) 0.0172(6) Uani 1 1 d . . . . .
H005 H 0.482207 1.017161 0.309143 0.021 Uiso 1 1 calc R U . . .
N006 N 0.4589(4) 0.6395(2) 0.4171(3) 0.0153(5) Uani 1 1 d . . . . .
N007 N 0.4157(4) 0.9445(2) 0.4982(3) 0.0174(5) Uani 1 1 d . . . . .
N008 N 0.3920(4) 0.5191(2) 0.6134(3) 0.0174(5) Uani 1 1 d . . . . .
H008 H 0.335357 0.512375 0.696643 0.021 Uiso 1 1 calc R U . . .
N009 N 0.4684(4) 0.4173(2) 0.5457(3) 0.0197(6) Uani 1 1 d . . . . .
H00A H 0.391853 0.398210 0.476492 0.024 Uiso 1 1 d R U . . .
N00A N 0.5544(4) 0.8173(3) 0.1671(3) 0.0221(6) Uani 1 1 d . . . . .
C1 C 0.4975(4) 0.8423(3) 0.2965(3) 0.0167(6) Uani 1 1 d . . . . .
C4 C 0.4053(4) 0.6269(3) 0.5510(3) 0.0157(6) Uani 1 1 d . . . . .
C2 C 0.4078(4) 0.8287(3) 0.5199(3) 0.0153(6) Uani 1 1 d . . . . .
C3 C 0.3670(4) 0.7396(2) 0.6222(3) 0.0157(6) Uani 1 1 d . . . . .
H00B H 0.595(5) 0.429(3) 0.518(4) 0.022(9) Uiso 1 1 d . . . . .
H00C H 0.573(6) 0.872(4) 0.102(5) 0.030(11) Uiso 1 1 d . . . . .
H00D H 0.551(7) 0.740(5) 0.136(5) 0.049(14) 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
O001 N003 1.251(3) . ?
O002 N003 1.274(3) . ?
N003 C3 1.348(4) . ?
N004 N006 1.410(3) . ?
N004 C1 1.355(4) . ?
N004 C2 1.369(4) . ?
N005 H005 0.8800 . ?
N005 N007 1.400(4) . ?
N005 C1 1.343(4) . ?
N006 C4 1.328(4) . ?
N007 C2 1.315(4) . ?
N008 H008 0.8800 . ?
N008 N009 1.407(4) . ?
N008 C4 1.349(4) . ?
N009 H00A 0.8621 . ?
N009 H00B 0.90(4) . ?
N00A C1 1.316(4) . ?
N00A H00C 0.88(5) . ?
N00A H00D 0.92(5) . ?
C4 C3 1.455(4) . ?
C2 C3 1.419(4) . ?

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
O001 N003 O002 121.7(3) . . ?
O001 N003 C3 121.0(2) . . ?
O002 N003 C3 117.3(2) . . ?
C1 N004 N006 135.4(3) . . ?
C1 N004 C2 108.4(2) . . ?
C2 N004 N006 116.2(2) . . ?
N007 N005 H005 123.1 . . ?
C1 N005 H005 123.1 . . ?
C1 N005 N007 113.7(3) . . ?
C4 N006 N004 101.5(2) . . ?
C2 N007 N005 101.7(2) . . ?
N009 N008 H008 119.9 . . ?
C4 N008 H008 119.9 . . ?
C4 N008 N009 120.1(3) . . ?
N008 N009 H00A 109.3 . . ?
N008 N009 H00B 111(2) . . ?
H00A N009 H00B 112.7 . . ?
C1 N00A H00C 123(3) . . ?
C1 N00A H00D 120(3) . . ?
H00C N00A H00D 116(4) . . ?
N005 C1 N004 103.8(3) . . ?
N00A C1 N004 127.7(3) . . ?
N00A C1 N005 128.5(3) . . ?
N006 C4 N008 122.2(3) . . ?
N006 C4 C3 113.6(3) . . ?
N008 C4 C3 124.2(3) . . ?
N004 C2 C3 103.6(3) . . ?
N007 C2 N004 112.3(3) . . ?
N007 C2 C3 144.1(3) . . ?
N003 C3 C4 128.7(3) . . ?
N003 C3 C2 126.2(3) . . ?
C2 C3 C4 105.1(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
O001 N003 C3 C4 -1.9(4) . . . . ?
O001 N003 C3 C2 174.8(3) . . . . ?
O002 N003 C3 C4 179.9(3) . . . . ?
O002 N003 C3 C2 -3.4(4) . . . . ?
N004 N006 C4 N008 -178.8(3) . . . . ?
N004 N006 C4 C3 0.2(3) . . . . ?
N004 C2 C3 N003 -174.9(3) . . . . ?
N004 C2 C3 C4 2.5(3) . . . . ?
N005 N007 C2 N004 1.0(3) . . . . ?
N005 N007 C2 C3 -178.7(4) . . . . ?
N006 N004 C1 N005 -177.9(3) . . . . ?
N006 N004 C1 N00A 1.7(6) . . . . ?
N006 N004 C2 N007 177.5(3) . . . . ?
N006 N004 C2 C3 -2.7(3) . . . . ?
N006 C4 C3 N003 175.5(3) . . . . ?
N006 C4 C3 C2 -1.8(3) . . . . ?
N007 N005 C1 N004 2.1(3) . . . . ?
N007 N005 C1 N00A -177.5(3) . . . . ?
N007 C2 C3 N003 4.9(7) . . . . ?
N007 C2 C3 C4 -177.8(4) . . . . ?
N008 C4 C3 N003 -5.5(5) . . . . ?
N008 C4 C3 C2 177.2(3) . . . . ?
N009 N008 C4 N006 11.3(4) . . . . ?
N009 N008 C4 C3 -167.5(3) . . . . ?
C1 N004 N006 C4 178.0(3) . . . . ?
C1 N004 C2 N007 0.2(4) . . . . ?
C1 N004 C2 C3 180.0(2) . . . . ?
C1 N005 N007 C2 -1.9(3) . . . . ?
C2 N004 N006 C4 1.6(3) . . . . ?
C2 N004 C1 N005 -1.3(3) . . . . ?
C2 N004 C1 N00A 178.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
