# Supplementary Information (SI) for CrystEngComm.
# 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. 
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data_he_36copy_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2428930'
loop_
_audit_author_name
_audit_author_address
'Kafeel Ahmad'
;National Institute of Technology Raipur
India
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-04-08 downloaded from the CCDC.
;
_audit_creation_date             2024-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 N3 O9'
_chemical_formula_sum            'C12 H15 N3 O9'
_chemical_formula_weight         345.27
_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      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                   8.6758(4)
_cell_length_b                   15.7644(6)
_cell_length_c                   10.9510(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.070(2)
_cell_angle_gamma                90
_cell_volume                     1489.36(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8531
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.730
_cell_measurement_theta_min      2.273
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1047 before and 0.0812 after correction. The Ratio of minimum to maximum transmission is 0.8825. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43863
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.946
_diffrn_reflns_theta_min         2.273
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             3223
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.061
_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)+(0.0601P)²+0.6737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1370
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: O9(0.75) H9(0.75) O11(0.75) O10(0.25) H8(0.25) O8(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,
 H12B)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O9(H9)
;
_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
O7 O 0.69902(19) 0.54420(8) 0.63170(12) 0.0524(4) Uani 1 1 d . . . . .
O5 O 0.83629(18) 0.42159(10) 1.00064(11) 0.0521(4) Uani 1 1 d . . . . .
O6 O 0.75845(19) 0.25921(8) 0.65903(13) 0.0543(4) Uani 1 1 d . . . . .
O3 O 0.87699(17) 0.17921(12) 1.13654(14) 0.0636(5) Uani 1 1 d . . . . .
O1 O 0.81458(16) 0.62300(12) 1.12657(13) 0.0620(5) Uani 1 1 d . . . . .
O4 O 0.62397(18) 0.15975(13) 1.13591(15) 0.0673(5) Uani 1 1 d . . . . .
N2 N 0.80683(17) 0.33830(9) 0.83176(13) 0.0351(3) Uani 1 1 d . . . . .
N3 N 0.72397(17) 0.40142(8) 0.64280(12) 0.0314(3) Uani 1 1 d . . . . .
N4 N 0.77530(17) 0.48537(9) 0.81804(12) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.56035(17) 0.61863(13) 1.13789(14) 0.0629(5) Uani 1 1 d . . . . .
H2 H 0.586004 0.638755 1.206059 0.094 Uiso 1 1 calc GR . . . .
C1 C 0.7444(2) 0.18736(12) 1.08756(17) 0.0413(4) Uani 1 1 d . . . . .
C2 C 0.7066(2) 0.23126(13) 0.96766(18) 0.0452(5) Uani 1 1 d . . . . .
H2A H 0.640006 0.279265 0.979953 0.054 Uiso 1 1 calc R . . . .
H2B H 0.648443 0.192542 0.911384 0.054 Uiso 1 1 calc R . . . .
C3 C 0.8466(2) 0.26272(12) 0.90836(18) 0.0429(4) Uani 1 1 d . . . . .
H3A H 0.929314 0.276747 0.971747 0.052 Uiso 1 1 calc R . . . .
H3B H 0.883402 0.218053 0.857876 0.052 Uiso 1 1 calc R . . . .
C4 C 0.7632(2) 0.32781(11) 0.70722(16) 0.0339(4) Uani 1 1 d . . . . .
C5 C 0.6794(2) 0.39425(12) 0.50975(15) 0.0365(4) Uani 1 1 d . . . . .
H5A H 0.596845 0.434185 0.485157 0.044 Uiso 1 1 calc R . . . .
H5B H 0.640796 0.337529 0.490538 0.044 Uiso 1 1 calc R . . . .
C6 C 0.8147(2) 0.41199(18) 0.44014(17) 0.0575(6) Uani 1 1 d . . . . .
H6A H 0.849341 0.469747 0.456811 0.069 Uiso 1 1 calc R . . . .
H6B H 0.899106 0.374325 0.469272 0.069 Uiso 1 1 calc R . . . .
C7 C 0.7793(3) 0.40091(18) 0.30498(18) 0.0591(6) Uani 1 1 d . . . . .
O9 O 0.8990(7) 0.4127(4) 0.2458(5) 0.105(2) Uani 0.75 1 d . . P A 1
H9 H 0.873808 0.406903 0.172001 0.157 Uiso 0.75 1 calc GR . P A 1
C9 C 0.7307(2) 0.48170(11) 0.69281(14) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.8077(2) 0.41501(11) 0.88972(15) 0.0352(4) Uani 1 1 d . . . . .
C11 C 0.7848(2) 0.56860(12) 0.87922(17) 0.0407(4) Uani 1 1 d . . . . .
H11A H 0.792947 0.612526 0.818197 0.049 Uiso 1 1 calc R . . . .
H11B H 0.877903 0.570649 0.936618 0.049 Uiso 1 1 calc R . . . .
C12 C 0.6449(2) 0.58653(13) 0.94777(17) 0.0429(4) Uani 1 1 d . . . . .
H12A H 0.585195 0.631997 0.905997 0.051 Uiso 1 1 calc R . . . .
H12B H 0.579700 0.536395 0.943831 0.051 Uiso 1 1 calc R . . . .
C13 C 0.6826(2) 0.61057(12) 1.07865(17) 0.0388(4) Uani 1 1 d . . . . .
O11 O 0.6688(4) 0.3621(3) 0.2564(2) 0.0928(11) Uani 0.75 1 d . . P A 1
O10 O 0.6549(9) 0.4316(8) 0.2555(7) 0.080(3) Uani 0.25 1 d . . P A 2
H8 H 0.849(7) 0.427(5) 0.157(7) 0.021(18) Uiso 0.25 1 d . . P B 2
O8 O 0.8656(17) 0.4485(7) 0.2429(15) 0.065(4) Uani 0.25 1 d . . P A 2
H4 H 0.647(5) 0.146(2) 1.218(4) 0.128(13) 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
O7 C9 1.206(2) . ?
O5 C10 1.218(2) . ?
O6 C4 1.202(2) . ?
O3 C1 1.223(2) . ?
O1 C13 1.224(2) . ?
O4 C1 1.296(2) . ?
O4 H4 0.92(4) . ?
N2 C3 1.477(2) . ?
N2 C4 1.386(2) . ?
N2 C10 1.365(2) . ?
N3 C4 1.382(2) . ?
N3 C5 1.472(2) . ?
N3 C9 1.378(2) . ?
N4 C9 1.386(2) . ?
N4 C10 1.371(2) . ?
N4 C11 1.472(2) . ?
O2 H2 0.8200 . ?
O2 C13 1.306(2) . ?
C1 C2 1.490(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.492(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.490(3) . ?
C7 O9 1.294(6) . ?
C7 O11 1.212(3) . ?
C7 O10 1.252(8) . ?
C7 O8 1.302(14) . ?
O9 H9 0.8200 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.520(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.485(2) . ?
O8 H8 1.00(7) . ?

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
C1 O4 H4 112(3) . . ?
C4 N2 C3 119.05(15) . . ?
C10 N2 C3 117.46(15) . . ?
C10 N2 C4 123.41(14) . . ?
C4 N3 C5 117.76(14) . . ?
C9 N3 C4 124.80(14) . . ?
C9 N3 C5 117.37(13) . . ?
C9 N4 C11 118.94(14) . . ?
C10 N4 C9 123.48(14) . . ?
C10 N4 C11 117.55(14) . . ?
C13 O2 H2 109.5 . . ?
O3 C1 O4 123.16(17) . . ?
O3 C1 C2 123.01(17) . . ?
O4 C1 C2 113.82(17) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.61(16) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
N2 C3 C2 110.92(15) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
O6 C4 N2 122.17(16) . . ?
O6 C4 N3 122.42(16) . . ?
N3 C4 N2 115.40(14) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
N3 C5 C6 110.65(14) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.23(17) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
O9 C7 C6 112.8(3) . . ?
O11 C7 C6 124.5(2) . . ?
O11 C7 O9 119.5(3) . . ?
O10 C7 C6 117.6(4) . . ?
O10 C7 O8 93.9(8) . . ?
O8 C7 C6 112.4(7) . . ?
C7 O9 H9 109.5 . . ?
O7 C9 N3 122.15(15) . . ?
O7 C9 N4 122.56(15) . . ?
N3 C9 N4 115.29(14) . . ?
O5 C10 N2 121.97(16) . . ?
O5 C10 N4 120.66(17) . . ?
N2 C10 N4 117.37(14) . . ?
N4 C11 H11A 109.1 . . ?
N4 C11 H11B 109.1 . . ?
N4 C11 C12 112.41(15) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.71(16) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
O1 C13 O2 122.90(17) . . ?
O1 C13 C12 123.73(17) . . ?
O2 C13 C12 113.36(16) . . ?
C7 O8 H8 105(4) . . ?

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
O3 C1 C2 C3 2.0(3) . . . . ?
O4 C1 C2 C3 -178.95(19) . . . . ?
N3 C5 C6 C7 176.71(19) . . . . ?
N4 C11 C12 C13 126.84(18) . . . . ?
C1 C2 C3 N2 -151.05(18) . . . . ?
C3 N2 C4 O6 -1.0(3) . . . . ?
C3 N2 C4 N3 178.35(14) . . . . ?
C3 N2 C10 O5 -1.7(3) . . . . ?
C3 N2 C10 N4 178.10(15) . . . . ?
C4 N2 C3 C2 -94.3(2) . . . . ?
C4 N2 C10 O5 174.85(17) . . . . ?
C4 N2 C10 N4 -5.4(3) . . . . ?
C4 N3 C5 C6 -96.2(2) . . . . ?
C4 N3 C9 O7 177.98(17) . . . . ?
C4 N3 C9 N4 -2.4(2) . . . . ?
C5 N3 C4 O6 -1.8(3) . . . . ?
C5 N3 C4 N2 178.92(15) . . . . ?
C5 N3 C9 O7 1.3(3) . . . . ?
C5 N3 C9 N4 -179.12(14) . . . . ?
C5 C6 C7 O9 -177.1(4) . . . . ?
C5 C6 C7 O11 -17.6(5) . . . . ?
C5 C6 C7 O10 44.8(7) . . . . ?
C5 C6 C7 O8 152.2(7) . . . . ?
C9 N3 C4 O6 -178.45(18) . . . . ?
C9 N3 C4 N2 2.2(2) . . . . ?
C9 N3 C5 C6 80.7(2) . . . . ?
C9 N4 C10 O5 -175.06(17) . . . . ?
C9 N4 C10 N2 5.2(3) . . . . ?
C9 N4 C11 C12 101.24(18) . . . . ?
C10 N2 C3 C2 82.4(2) . . . . ?
C10 N2 C4 O6 -177.46(18) . . . . ?
C10 N2 C4 N3 1.9(3) . . . . ?
C10 N4 C9 O7 178.16(18) . . . . ?
C10 N4 C9 N3 -1.5(2) . . . . ?
C10 N4 C11 C12 -77.1(2) . . . . ?
C11 N4 C9 O7 -0.1(3) . . . . ?
C11 N4 C9 N3 -179.70(15) . . . . ?
C11 N4 C10 O5 3.2(3) . . . . ?
C11 N4 C10 N2 -176.57(15) . . . . ?
C11 C12 C13 O1 6.5(3) . . . . ?
C11 C12 C13 O2 -174.57(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
