# 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_N2H2Nakdong_a
_audit_block_doi                 10.5517/ccdc.csd.cc2pvxcv
_database_code_depnum_ccdc_archive 'CCDC 2498518'
loop_
_audit_author_name
_audit_author_address
'Huiyeong Ju'
;Korea Basic Science Institute
South Korea
;
_audit_update_record             
;
2025-11-23 deposited with the CCDC.	2025-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H29 N O4, C H4 O '
_chemical_formula_sum            'C20 H33 N O5'
_chemical_formula_weight         367.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.744(2)
_cell_length_b                   5.1551(7)
_cell_length_c                   25.863(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.926(4)
_cell_angle_gamma                90
_cell_volume                     2220.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5812
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.62

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6774
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40501
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5577
_reflns_number_gt                2691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1599P)²+0.7032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.6(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5577
_refine_ls_number_parameters     236
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.0860
_refine_ls_wR_factor_ref         0.3008
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3807(3) 0.3702(14) 0.4085(2) 0.106(2) Uani 1 1 d . . . . .
H1O H 0.383409 0.340277 0.440181 0.160 Uiso 1 1 calc R U . . .
O2 O 0.5131(3) 0.3882(13) 0.42479(17) 0.0942(16) Uani 1 1 d . . . . .
O3 O 0.5497(2) 0.9467(8) 0.32818(19) 0.0768(14) Uani 1 1 d . . . . .
O4 O 0.6967(2) 0.4553(8) 0.32415(19) 0.0736(13) Uani 1 1 d . . . . .
O5 O 0.3775(3) 0.1952(13) 0.50235(17) 0.108(2) Uani 1 1 d . . . . .
H5O H 0.406142 0.261883 0.526903 0.161 Uiso 1 1 calc R U . . .
N1 N 0.5349(2) 0.5111(9) 0.32575(18) 0.0524(11) Uani 1 1 d . . . . .
H1N H 0.557138 0.363416 0.319491 0.063 Uiso 1 1 calc R U . . .
C1 C 0.4541(3) 0.4096(12) 0.3948(2) 0.0604(14) Uani 1 1 d . . . . .
C2 C 0.4541(3) 0.5105(11) 0.3399(2) 0.0525(13) Uani 1 1 d . . . . .
H2 H 0.435826 0.693129 0.339887 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3954(3) 0.3614(12) 0.3008(2) 0.0597(14) Uani 1 1 d . . . . .
H3A H 0.413500 0.181234 0.298817 0.072 Uiso 1 1 calc R U . . .
H3AB H 0.342157 0.359970 0.313337 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3892(3) 0.4785(12) 0.2477(2) 0.0588(14) Uani 1 1 d . . . . .
C5 C 0.3395(4) 0.6893(14) 0.2363(2) 0.0725(17) Uani 1 1 d . . . . .
H5 H 0.309758 0.759238 0.261876 0.087 Uiso 1 1 calc R U . . .
C6 C 0.3335(5) 0.7985(18) 0.1863(3) 0.099(3) Uani 1 1 d . . . . .
H6 H 0.299776 0.942003 0.178607 0.118 Uiso 1 1 calc R U . . .
C7 C 0.3758(6) 0.700(2) 0.1493(3) 0.108(3) Uani 1 1 d . . . . .
H7 H 0.371167 0.772239 0.115830 0.129 Uiso 1 1 calc R U . . .
C8 C 0.4249(6) 0.494(3) 0.1609(3) 0.119(3) Uani 1 1 d . . . . .
H8 H 0.454536 0.425705 0.135097 0.143 Uiso 1 1 calc R U . . .
C9 C 0.4323(4) 0.3856(18) 0.2085(3) 0.088(2) Uani 1 1 d . . . . .
H9 H 0.467341 0.244401 0.215365 0.106 Uiso 1 1 calc R U . . .
C10 C 0.5776(3) 0.7289(11) 0.3217(2) 0.0541(13) Uani 1 1 d . . . . .
C11 C 0.6623(3) 0.6929(12) 0.3064(2) 0.0610(14) Uani 1 1 d . . . . .
H11 H 0.696731 0.838344 0.320246 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7175(4) 0.4432(17) 0.3778(3) 0.090(2) Uani 1 1 d . . . . .
H12A H 0.740594 0.274684 0.386851 0.135 Uiso 1 1 calc R U . . .
H12B H 0.756351 0.577706 0.388111 0.135 Uiso 1 1 calc R U . . .
H12C H 0.669851 0.468636 0.395586 0.135 Uiso 1 1 calc R U . . .
C13 C 0.6648(4) 0.6719(17) 0.2478(3) 0.091(2) Uani 1 1 d . . . . .
H13A H 0.721257 0.663151 0.240994 0.109 Uiso 1 1 calc R U . . .
H13B H 0.639694 0.507358 0.236279 0.109 Uiso 1 1 calc R U . . .
C14 C 0.6261(5) 0.8802(19) 0.2157(3) 0.099(2) Uani 1 1 d . . . . .
H14A H 0.646163 1.047412 0.229575 0.119 Uiso 1 1 calc R U . . .
H14B H 0.568174 0.874842 0.218464 0.119 Uiso 1 1 calc R U . . .
C15 C 0.6397(6) 0.866(2) 0.1589(3) 0.110(3) Uani 1 1 d . . . . .
H15A H 0.697697 0.854998 0.156801 0.132 Uiso 1 1 calc R U . . .
H15B H 0.616103 0.703029 0.144889 0.132 Uiso 1 1 calc R U . . .
C16 C 0.6078(9) 1.078(3) 0.1247(4) 0.159(5) Uani 1 1 d D . . . .
H16A H 0.549194 1.082190 0.123855 0.191 Uiso 1 1 calc R U . . .
H16B H 0.628574 1.243926 0.139103 0.191 Uiso 1 1 calc R U . . .
C17 C 0.6296(9) 1.052(3) 0.0716(4) 0.173(5) Uani 1 1 d D U . . .
H17A H 0.686365 1.002535 0.074093 0.207 Uiso 1 1 calc R U . . .
H17B H 0.598962 0.904739 0.055730 0.207 Uiso 1 1 calc R U . . .
C18 C 0.619(2) 1.267(4) 0.0355(7) 0.39(2) Uani 1 1 d D U . . .
H18A H 0.652983 1.411525 0.048583 0.469 Uiso 1 1 calc R U . . .
H18B H 0.562758 1.325402 0.033215 0.469 Uiso 1 1 calc R U . . .
C19 C 0.6386(15) 1.194(7) -0.0161(7) 0.315(13) Uani 1 1 d D U . . .
H19A H 0.630710 1.341622 -0.039257 0.472 Uiso 1 1 calc R U . . .
H19B H 0.694205 1.138598 -0.013997 0.472 Uiso 1 1 calc R U . . .
H19C H 0.604058 1.052549 -0.029352 0.472 Uiso 1 1 calc R U . . .
C20 C 0.3646(8) -0.062(2) 0.5132(4) 0.143(4) Uani 1 1 d . . . . .
H20A H 0.359756 -0.161489 0.481175 0.215 Uiso 1 1 calc R U . . .
H20B H 0.315480 -0.079063 0.529871 0.215 Uiso 1 1 calc R U . . .
H20C H 0.409375 -0.127976 0.536314 0.215 Uiso 1 1 calc R U . . .


_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 C1 1.331(7) . ?
O1 H1O 0.8300 . ?
O2 C1 1.196(7) . ?
O3 C10 1.234(6) . ?
O4 C12 1.396(8) . ?
O4 C11 1.410(8) . ?
O5 C20 1.379(13) . ?
O5 H5O 0.8300 . ?
N1 C10 1.340(7) . ?
N1 C2 1.437(6) . ?
N1 H1N 0.8700 . ?
C1 C2 1.512(8) . ?
C2 C3 1.541(7) . ?
C2 H2 0.9900 . ?
C3 C4 1.495(8) . ?
C3 H3A 0.9800 . ?
C3 H3AB 0.9800 . ?
C4 C5 1.382(8) . ?
C4 C9 1.389(9) . ?
C5 C6 1.403(10) . ?
C5 H5 0.9400 . ?
C6 C7 1.347(13) . ?
C6 H6 0.9400 . ?
C7 C8 1.356(15) . ?
C7 H7 0.9400 . ?
C8 C9 1.346(12) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.523(8) . ?
C11 C13 1.524(10) . ?
C11 H11 0.9900 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.468(11) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.510(11) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.475(15) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.463(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.449(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.458(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?

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 O1 H1O 109.5 . . ?
C12 O4 C11 114.4(5) . . ?
C20 O5 H5O 109.5 . . ?
C10 N1 C2 123.0(4) . . ?
C10 N1 H1N 118.5 . . ?
C2 N1 H1N 118.5 . . ?
O2 C1 O1 122.4(5) . . ?
O2 C1 C2 124.1(5) . . ?
O1 C1 C2 113.1(4) . . ?
N1 C2 C1 109.3(4) . . ?
N1 C2 C3 112.8(4) . . ?
C1 C2 C3 112.5(4) . . ?
N1 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C2 112.4(5) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3AB 109.1 . . ?
C2 C3 H3AB 109.1 . . ?
H3A C3 H3AB 107.9 . . ?
C5 C4 C9 117.6(6) . . ?
C5 C4 C3 119.8(5) . . ?
C9 C4 C3 122.6(6) . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.6(8) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.4(8) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 121.5(8) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 121.2(8) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
O3 C10 N1 122.6(5) . . ?
O3 C10 C11 121.5(5) . . ?
N1 C10 C11 115.9(5) . . ?
O4 C11 C10 112.4(4) . . ?
O4 C11 C13 102.1(5) . . ?
C10 C11 C13 112.9(5) . . ?
O4 C11 H11 109.7 . . ?
C10 C11 H11 109.7 . . ?
C13 C11 H11 109.7 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 117.1(6) . . ?
C14 C13 H13A 108.0 . . ?
C11 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C11 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C15 114.3(7) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 117.7(9) . . ?
C16 C15 H15A 107.9 . . ?
C14 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
C14 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C17 C16 C15 112.5(11) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 120.3(14) . . ?
C18 C17 H17A 107.2 . . ?
C16 C17 H17A 107.2 . . ?
C18 C17 H17B 107.2 . . ?
C16 C17 H17B 107.2 . . ?
H17A C17 H17B 106.9 . . ?
C17 C18 C19 111.5(17) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.060



_vrf_PLAT234_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good (very thin and weak). Also crystals diffracted extremely weakly. 
Additionally, although we attempted to refine the structure disorder treatment, the R-values remained unacceptably high, preventing completion of refinement. 
So we cannot find disordered part. This is likely related to the weak diffraction of the crystal.
;


_vrf_PLAT220_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good and slightly decomposed in the air. Also crystals diffracted extremely weakly. 
This is likely related to the weak diffraction of the crystal.
;

_vrf_PLAT230_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good (very thin and weak). Also crystals diffracted extremely weakly. 
Additionally, although we attempted to refine the structure disorder treatment, the R-values remained unacceptably high, preventing completion of refinement. 
So we cannot find disordered part. This is likely related to the weak diffraction of the crystal.
;

_vrf_PLAT241_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good (very thin and weak). Also crystals diffracted extremely weakly. 
Additionally, although we attempted to refine the structure disorder treatment, the R-values remained unacceptably high, preventing completion of refinement. 
So we cannot find disordered part. This is likely related to the weak diffraction of the crystal.
;

_vrf_PLAT242_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good (very thin and weak). Also crystals diffracted extremely weakly. 
Additionally, although we attempted to refine the structure disorder treatment, the R-values remained unacceptably high, preventing completion of refinement. 
So we cannot find disordered part. This is likely related to the weak diffraction of the crystal.
;

_vrf_PLAT340_N2H2Nakdong_a       
;
RESPONSE: The crystal quality was not good (very thin and weak). Also crystals diffracted extremely weakly. 
Additionally, although we attempted to refine the structure disorder treatment, the R-values remained unacceptably high, preventing completion of refinement. 
So we cannot find disordered part. This is likely related to the weak diffraction of the crystal.
;

_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Heat-sensitive
