# 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. 
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#######################################################################

data_20076_73_1_p_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2425248'
loop_
_audit_author_name
_audit_author_address
'Dr. Shibaji Ghosh'
;CSIR Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2025-02-19 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_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         'C20 H22 N4 O'
_chemical_formula_sum            'C20 H22 N4 O'
_chemical_formula_weight         334.41
_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                   11.6746(6)
_cell_length_b                   11.1003(6)
_cell_length_c                   13.6168(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.287(2)
_cell_angle_gamma                90
_cell_volume                     1741.49(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9574
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      28.596
_cell_measurement_theta_min      2.380
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0967 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.9248. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            126285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      278
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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                4196
_reflns_number_total             5334
_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         0.312
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.120
_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)+(0.0790P)²+0.3072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_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
O1 O 0.39958(9) 0.29522(9) 0.44773(8) 0.0507(3) Uani 1 1 d . . . . .
N1 N 0.66420(10) 0.03961(10) 0.24781(9) 0.0435(3) Uani 1 1 d . . . . .
N2 N 0.49705(10) 0.29456(9) 0.31582(8) 0.0391(2) Uani 1 1 d . . . . .
N3 N 0.42673(9) 0.51536(9) 0.25821(8) 0.0370(2) Uani 1 1 d . . . . .
N4 N 0.65593(9) 0.22787(10) 0.18717(8) 0.0421(2) Uani 1 1 d . . . . .
C1 C 0.73326(13) 0.04320(15) 0.17448(12) 0.0540(4) Uani 1 1 d . . . . .
H1 H 0.775895 -0.019911 0.153606 0.065 Uiso 1 1 calc R . . . .
C2 C 0.61899(10) 0.15438(10) 0.25186(9) 0.0352(2) Uani 1 1 d . . . . .
C0AA C 0.53870(10) 0.17631(11) 0.31818(9) 0.0362(2) Uani 1 1 d . . . . .
C4 C 0.43293(10) 0.34676(11) 0.37851(9) 0.0365(2) Uani 1 1 d . . . . .
C5 C 0.41491(10) 0.48284(11) 0.36077(9) 0.0343(2) Uani 1 1 d . . . . .
H5 H 0.480572 0.521575 0.402956 0.041 Uiso 1 1 calc R . . . .
C6 C 0.32580(12) 0.48448(14) 0.18408(10) 0.0464(3) Uani 1 1 d . . . . .
H6A H 0.260245 0.534114 0.193993 0.056 Uiso 1 1 calc R . . . .
H6B H 0.305032 0.400814 0.191872 0.056 Uiso 1 1 calc R . . . .
C7 C 0.35327(17) 0.50457(16) 0.07983(11) 0.0596(4) Uani 1 1 d . . . . .
H7A H 0.413842 0.449211 0.067929 0.071 Uiso 1 1 calc R . . . .
H7B H 0.284689 0.487903 0.031329 0.071 Uiso 1 1 calc R . . . .
C8 C 0.39275(19) 0.63302(17) 0.06677(13) 0.0677(5) Uani 1 1 d . . . . .
H8A H 0.417653 0.641213 0.002496 0.081 Uiso 1 1 calc R . . . .
H8B H 0.328385 0.687795 0.068602 0.081 Uiso 1 1 calc R . . . .
C9 C 0.63554(17) -0.05320(14) 0.30583(13) 0.0598(4) Uani 1 1 d . . . . .
H9 H 0.668293 -0.129150 0.302400 0.072 Uiso 1 1 calc R . . . .
C10 C 0.55935(18) -0.03195(14) 0.36749(13) 0.0621(4) Uani 1 1 d . . . . .
H10 H 0.539027 -0.094462 0.406773 0.075 Uiso 1 1 calc R . . . .
C11 C 0.50864(14) 0.08360(13) 0.37455(11) 0.0494(3) Uani 1 1 d . . . . .
H11 H 0.455255 0.095839 0.417414 0.059 Uiso 1 1 calc R . . . .
C12 C 0.72615(12) 0.15708(15) 0.13936(11) 0.0510(3) Uani 1 1 d . . . . .
H12 H 0.764317 0.184408 0.088732 0.061 Uiso 1 1 calc R . . . .
C13 C 0.45879(14) 0.64215(12) 0.24962(11) 0.0481(3) Uani 1 1 d . . . . .
H13A H 0.524070 0.661525 0.300767 0.058 Uiso 1 1 calc R . . . .
H13B H 0.394124 0.693278 0.259210 0.058 Uiso 1 1 calc R . . . .
C14 C 0.49104(18) 0.66543(16) 0.14765(14) 0.0663(5) Uani 1 1 d . . . . .
H14A H 0.510367 0.749860 0.141941 0.080 Uiso 1 1 calc R . . . .
H14B H 0.558920 0.618136 0.140040 0.080 Uiso 1 1 calc R . . . .
C15 C 0.30750(10) 0.53053(11) 0.39731(9) 0.0360(2) Uani 1 1 d . . . . .
C16 C 0.20072(11) 0.47278(13) 0.37739(10) 0.0435(3) Uani 1 1 d . . . . .
H16 H 0.194672 0.399040 0.344537 0.052 Uiso 1 1 calc R . . . .
C17 C 0.10317(12) 0.52421(17) 0.40608(12) 0.0548(4) Uani 1 1 d . . . . .
H17 H 0.032068 0.484893 0.392067 0.066 Uiso 1 1 calc R . . . .
C18 C 0.11060(15) 0.63266(18) 0.45501(12) 0.0625(5) Uani 1 1 d . . . . .
H18 H 0.044603 0.667027 0.473456 0.075 Uiso 1 1 calc R . . . .
C19 C 0.21528(16) 0.69014(15) 0.47660(12) 0.0597(4) Uani 1 1 d . . . . .
H19 H 0.220549 0.762966 0.510795 0.072 Uiso 1 1 calc R . . . .
C20 C 0.31403(13) 0.64007(13) 0.44758(10) 0.0460(3) Uani 1 1 d . . . . .
H20 H 0.384739 0.680101 0.461904 0.055 Uiso 1 1 calc R . . . .
H2 H 0.5141(14) 0.3423(16) 0.2683(12) 0.049(4) 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
O1 C4 1.2189(14) . ?
N1 C1 1.381(2) . ?
N1 C2 1.3835(15) . ?
N1 C9 1.372(2) . ?
N2 C0AA 1.3984(15) . ?
N2 C4 1.3532(15) . ?
N3 C5 1.4704(15) . ?
N3 C6 1.4632(17) . ?
N3 C13 1.4658(17) . ?
N4 C2 1.3229(16) . ?
N4 C12 1.3732(17) . ?
C1 C12 1.349(2) . ?
C2 C0AA 1.4236(16) . ?
C0AA C11 1.3633(18) . ?
C4 C5 1.5388(17) . ?
C5 C15 1.5170(16) . ?
C6 C7 1.521(2) . ?
C7 C8 1.518(3) . ?
C8 C14 1.500(3) . ?
C9 C10 1.339(3) . ?
C10 C11 1.422(2) . ?
C13 C14 1.518(2) . ?
C15 C16 1.3890(18) . ?
C15 C20 1.3914(18) . ?
C16 C17 1.3854(19) . ?
C17 C18 1.372(3) . ?
C18 C19 1.368(3) . ?
C19 C20 1.393(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
C1 N1 C2 105.85(12) . . ?
C9 N1 C1 131.51(13) . . ?
C9 N1 C2 122.57(13) . . ?
C4 N2 C0AA 127.82(10) . . ?
C6 N3 C5 114.15(10) . . ?
C6 N3 C13 110.94(11) . . ?
C13 N3 C5 112.08(10) . . ?
C2 N4 C12 104.27(12) . . ?
C12 C1 N1 105.87(12) . . ?
N1 C2 C0AA 118.51(11) . . ?
N4 C2 N1 111.95(11) . . ?
N4 C2 C0AA 129.47(11) . . ?
N2 C0AA C2 114.08(10) . . ?
C11 C0AA N2 126.97(12) . . ?
C11 C0AA C2 118.93(11) . . ?
O1 C4 N2 124.41(11) . . ?
O1 C4 C5 121.97(11) . . ?
N2 C4 C5 113.38(10) . . ?
N3 C5 C4 111.02(9) . . ?
N3 C5 C15 115.79(9) . . ?
C15 C5 C4 112.98(10) . . ?
N3 C6 C7 109.99(13) . . ?
C8 C7 C6 111.15(14) . . ?
C14 C8 C7 110.48(14) . . ?
C10 C9 N1 118.50(13) . . ?
C9 C10 C11 121.81(14) . . ?
C0AA C11 C10 119.66(14) . . ?
C1 C12 N4 112.05(13) . . ?
N3 C13 C14 109.92(13) . . ?
C8 C14 C13 110.93(15) . . ?
C16 C15 C5 122.56(11) . . ?
C16 C15 C20 118.40(12) . . ?
C20 C15 C5 118.93(11) . . ?
C17 C16 C15 120.49(14) . . ?
C18 C17 C16 120.54(15) . . ?
C19 C18 C17 119.87(13) . . ?
C18 C19 C20 120.29(15) . . ?
C15 C20 C19 120.39(14) . . ?

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
O1 C4 C5 N3 -161.38(12) . . . . ?
O1 C4 C5 C15 -29.37(17) . . . . ?
N1 C1 C12 N4 0.36(17) . . . . ?
N1 C2 C0AA N2 -179.25(11) . . . . ?
N1 C2 C0AA C11 -0.50(18) . . . . ?
N1 C9 C10 C11 -0.4(3) . . . . ?
N2 C0AA C11 C10 179.74(14) . . . . ?
N2 C4 C5 N3 24.00(14) . . . . ?
N2 C4 C5 C15 156.01(11) . . . . ?
N3 C5 C15 C16 83.38(15) . . . . ?
N3 C5 C15 C20 -92.63(14) . . . . ?
N3 C6 C7 C8 -56.13(18) . . . . ?
N3 C13 C14 C8 57.78(18) . . . . ?
N4 C2 C0AA N2 -2.50(19) . . . . ?
N4 C2 C0AA C11 176.24(13) . . . . ?
C1 N1 C2 N4 -0.50(15) . . . . ?
C1 N1 C2 C0AA 176.79(11) . . . . ?
C1 N1 C9 C10 -175.62(16) . . . . ?
C2 N1 C1 C12 0.07(15) . . . . ?
C2 N1 C9 C10 1.1(2) . . . . ?
C2 N4 C12 C1 -0.66(16) . . . . ?
C2 C0AA C11 C10 1.2(2) . . . . ?
C0AA N2 C4 O1 -1.3(2) . . . . ?
C0AA N2 C4 C5 173.17(12) . . . . ?
C4 N2 C0AA C2 -170.41(12) . . . . ?
C4 N2 C0AA C11 11.0(2) . . . . ?
C4 C5 C15 C16 -46.24(16) . . . . ?
C4 C5 C15 C20 137.76(12) . . . . ?
C5 N3 C6 C7 -171.73(11) . . . . ?
C5 N3 C13 C14 169.81(12) . . . . ?
C5 C15 C16 C17 -175.30(12) . . . . ?
C5 C15 C20 C19 175.93(12) . . . . ?
C6 N3 C5 C4 76.84(12) . . . . ?
C6 N3 C5 C15 -53.72(14) . . . . ?
C6 N3 C13 C14 -61.29(16) . . . . ?
C6 C7 C8 C14 53.1(2) . . . . ?
C7 C8 C14 C13 -53.78(19) . . . . ?
C9 N1 C1 C12 177.21(16) . . . . ?
C9 N1 C2 N4 -177.96(13) . . . . ?
C9 N1 C2 C0AA -0.67(19) . . . . ?
C9 C10 C11 C0AA -0.7(3) . . . . ?
C12 N4 C2 N1 0.70(14) . . . . ?
C12 N4 C2 C0AA -176.22(13) . . . . ?
C13 N3 C5 C4 -155.96(11) . . . . ?
C13 N3 C5 C15 73.48(14) . . . . ?
C13 N3 C6 C7 60.49(15) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C15 -0.7(2) . . . . ?
C20 C15 C16 C17 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
