# Supplementary Information (SI) 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. 
# 
#######################################################################

data_24009_002
_database_code_depnum_ccdc_archive 'CCDC 2380342'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2024-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.831(6)
_cell_length_b                   9.067(6)
_cell_length_c                   13.811(9)
_cell_angle_alpha                73.42(2)
_cell_angle_beta                 81.83(2)
_cell_angle_gamma                86.68(2)
_cell_volume                     1049.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    6825
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6624
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'IuS 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28678
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4081
_reflns_number_gt                2719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX5'
_computing_cell_refinement       'Bruker APEX5'
_computing_data_reduction        'Bruker APEX5'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0755P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4081
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N1 N 0.0226(2) 0.7870(2) 0.15201(14) 0.0607(5) Uani 1 1 d . . . . .
H1A H 0.052(3) 0.881(3) 0.115(2) 0.091 Uiso 1 1 d . U . . .
H1B H -0.019(3) 0.723(3) 0.129(2) 0.091 Uiso 1 1 d . U . . .
C2 C 0.0807(2) 0.7269(2) 0.24219(14) 0.0453(4) Uani 1 1 d . . . . .
C3 C 0.0709(2) 0.5690(2) 0.29417(14) 0.0476(5) Uani 1 1 d . . . . .
H3 H 0.022137 0.503017 0.267272 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1322(2) 0.5102(2) 0.38405(14) 0.0448(4) Uani 1 1 d . . . . .
H4 H 0.126061 0.404100 0.416885 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2037(2) 0.6052(2) 0.42768(13) 0.0416(4) Uani 1 1 d . . . . .
C6 C 0.2093(2) 0.7644(2) 0.37777(14) 0.0434(4) Uani 1 1 d . . . . .
C7 C 0.1496(2) 0.8236(2) 0.28629(14) 0.0472(5) Uani 1 1 d . . . . .
H7 H 0.155411 0.929709 0.253412 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2781(2) 0.5428(2) 0.52081(14) 0.0451(4) Uani 1 1 d . . . . .
O9 O 0.3507(2) 0.61890(18) 0.55667(12) 0.0689(5) Uani 1 1 d . . . . .
O10 O 0.25915(17) 0.39094(16) 0.56143(10) 0.0540(4) Uani 1 1 d . . . . .
C11 C 0.3268(3) 0.3223(3) 0.65398(16) 0.0612(6) Uani 1 1 d . . . . .
H11A H 0.300628 0.214397 0.679719 0.092 Uiso 1 1 calc R U . . .
H11B H 0.287826 0.375026 0.704682 0.092 Uiso 1 1 calc R U . . .
H11C H 0.437092 0.331469 0.639509 0.092 Uiso 1 1 calc R U . . .
C12 C 0.2738(2) 0.8801(2) 0.41937(15) 0.0487(5) Uani 1 1 d . . . . .
O13 O 0.39378(18) 0.94502(18) 0.38451(12) 0.0628(4) Uani 1 1 d . . . . .
O14 O 0.17499(19) 0.91171(18) 0.49394(12) 0.0636(4) Uani 1 1 d . . . . .
C15 C 0.2225(3) 1.0266(3) 0.5379(2) 0.0767(8) Uani 1 1 d . . . . .
H15A H 0.142525 1.042294 0.590031 0.115 Uiso 1 1 calc R U . . .
H15B H 0.241240 1.122818 0.484935 0.115 Uiso 1 1 calc R U . . .
H15C H 0.315620 0.991378 0.567925 0.115 Uiso 1 1 calc R U . . .
N21 N 0.5295(3) 0.7138(3) 0.69371(15) 0.0655(6) Uani 1 1 d . . . . .
H21A H 0.499(3) 0.658(3) 0.663(2) 0.098 Uiso 1 1 d . U . . .
H21B H 0.529(3) 0.817(3) 0.664(2) 0.098 Uiso 1 1 d . U . . .
C22 C 0.5868(2) 0.6525(2) 0.78413(14) 0.0482(5) Uani 1 1 d . . . . .
C23 C 0.5950(2) 0.4937(2) 0.82991(15) 0.0509(5) Uani 1 1 d . . . . .
H23 H 0.557523 0.425542 0.799243 0.061 Uiso 1 1 calc R U . . .
C24 C 0.6575(2) 0.4362(2) 0.91943(15) 0.0489(5) Uani 1 1 d . . . . .
H24 H 0.663369 0.329046 0.948140 0.059 Uiso 1 1 calc R U . . .
C25 C 0.7127(2) 0.5338(2) 0.96905(14) 0.0434(4) Uani 1 1 d . . . . .
C26 C 0.6983(2) 0.6940(2) 0.92510(14) 0.0429(4) Uani 1 1 d . . . . .
C27 C 0.6390(2) 0.7517(2) 0.83398(14) 0.0467(5) Uani 1 1 d . . . . .
H27 H 0.633485 0.858794 0.804802 0.056 Uiso 1 1 calc R U . . .
C28 C 0.7851(2) 0.4739(2) 1.06248(15) 0.0464(4) Uani 1 1 d . . . . .
O29 O 0.84162(19) 0.55337(17) 1.10471(12) 0.0650(5) Uani 1 1 d . . . . .
O30 O 0.78437(19) 0.31974(17) 1.09750(11) 0.0622(4) Uani 1 1 d . . . . .
C31 C 0.8566(3) 0.2534(3) 1.18850(18) 0.0703(7) Uani 1 1 d . . . . .
H31A H 0.848475 0.142243 1.208043 0.105 Uiso 1 1 calc R U . . .
H31B H 0.806109 0.292745 1.243376 0.105 Uiso 1 1 calc R U . . .
H31C H 0.963707 0.280711 1.174966 0.105 Uiso 1 1 calc R U . . .
C32 C 0.7398(2) 0.8117(2) 0.97446(15) 0.0477(5) Uani 1 1 d . . . . .
O33 O 0.8527(2) 0.88983(19) 0.94663(12) 0.0696(5) Uani 1 1 d . . . . .
O34 O 0.62885(18) 0.82861(17) 1.04761(11) 0.0594(4) Uani 1 1 d . . . . .
C35 C 0.6517(3) 0.9465(3) 1.0960(2) 0.0731(8) Uani 1 1 d . . . . .
H35A H 0.567638 0.945974 1.149530 0.110 Uiso 1 1 calc R U . . .
H35B H 0.655728 1.046356 1.045729 0.110 Uiso 1 1 calc R U . . .
H35C H 0.747126 0.926003 1.125037 0.110 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
N1 C2 1.368(2) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.85(3) . ?
C2 C7 1.408(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.404(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.411(3) . ?
C5 C8 1.479(2) . ?
C6 C7 1.390(3) . ?
C6 C12 1.505(3) . ?
C7 H7 0.9400 . ?
C8 O9 1.212(2) . ?
C8 O10 1.341(2) . ?
O10 C11 1.448(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 O13 1.211(3) . ?
C12 O14 1.337(3) . ?
O14 C15 1.454(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
N21 C22 1.369(3) . ?
N21 H21A 0.82(3) . ?
N21 H21B 0.91(3) . ?
C22 C23 1.400(3) . ?
C22 C27 1.410(3) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.408(2) . ?
C24 H24 0.9400 . ?
C25 C26 1.411(3) . ?
C25 C28 1.471(3) . ?
C26 C27 1.382(3) . ?
C26 C32 1.506(3) . ?
C27 H27 0.9400 . ?
C28 O29 1.214(2) . ?
C28 O30 1.342(2) . ?
O30 C31 1.449(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C32 O33 1.209(2) . ?
C32 O34 1.339(3) . ?
O34 C35 1.449(2) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 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
C2 N1 H1A 116.9(18) . . ?
C2 N1 H1B 116.5(18) . . ?
H1A N1 H1B 125(3) . . ?
N1 C2 C7 120.23(19) . . ?
N1 C2 C3 121.47(17) . . ?
C7 C2 C3 118.29(17) . . ?
C4 C3 C2 120.66(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.45(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.17(17) . . ?
C4 C5 C8 122.17(18) . . ?
C6 C5 C8 119.60(16) . . ?
C7 C6 C5 120.48(17) . . ?
C7 C6 C12 115.86(17) . . ?
C5 C6 C12 123.64(16) . . ?
C6 C7 C2 120.89(19) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O9 C8 O10 122.88(18) . . ?
O9 C8 C5 124.30(19) . . ?
O10 C8 C5 112.81(16) . . ?
C8 O10 C11 115.88(16) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 O14 124.44(19) . . ?
O13 C12 C6 124.4(2) . . ?
O14 C12 C6 110.94(19) . . ?
C12 O14 C15 116.02(19) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 N21 H21A 121(2) . . ?
C22 N21 H21B 120.7(18) . . ?
H21A N21 H21B 118(3) . . ?
N21 C22 C23 122.36(19) . . ?
N21 C22 C27 119.4(2) . . ?
C23 C22 C27 118.23(18) . . ?
C24 C23 C22 120.68(18) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 121.67(19) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 117.52(18) . . ?
C24 C25 C28 122.20(18) . . ?
C26 C25 C28 120.27(16) . . ?
C27 C26 C25 120.79(17) . . ?
C27 C26 C32 115.93(17) . . ?
C25 C26 C32 123.24(16) . . ?
C26 C27 C22 121.01(19) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
O29 C28 O30 122.21(19) . . ?
O29 C28 C25 124.47(19) . . ?
O30 C28 C25 113.32(16) . . ?
C28 O30 C31 115.97(17) . . ?
O30 C31 H31A 109.5 . . ?
O30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O33 C32 O34 123.90(19) . . ?
O33 C32 C26 124.6(2) . . ?
O34 C32 C26 111.26(18) . . ?
C32 O34 C35 116.16(19) . . ?
O34 C35 H35A 109.5 . . ?
O34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
N1 C2 C3 C4 178.9(2) . . . . ?
C7 C2 C3 C4 -2.2(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C8 -176.30(19) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C8 C5 C6 C7 175.39(18) . . . . ?
C4 C5 C6 C12 176.20(18) . . . . ?
C8 C5 C6 C12 -6.4(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C12 C6 C7 C2 -177.45(19) . . . . ?
N1 C2 C7 C6 -179.9(2) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
C4 C5 C8 O9 174.3(2) . . . . ?
C6 C5 C8 O9 -3.0(3) . . . . ?
C4 C5 C8 O10 -4.7(3) . . . . ?
C6 C5 C8 O10 178.01(17) . . . . ?
O9 C8 O10 C11 2.0(3) . . . . ?
C5 C8 O10 C11 -178.93(17) . . . . ?
C7 C6 C12 O13 -73.5(3) . . . . ?
C5 C6 C12 O13 108.3(2) . . . . ?
C7 C6 C12 O14 101.1(2) . . . . ?
C5 C6 C12 O14 -77.2(2) . . . . ?
O13 C12 O14 C15 -3.4(3) . . . . ?
C6 C12 O14 C15 -177.92(17) . . . . ?
N21 C22 C23 C24 178.1(2) . . . . ?
C27 C22 C23 C24 -2.2(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 1.6(3) . . . . ?
C23 C24 C25 C28 -177.56(19) . . . . ?
C24 C25 C26 C27 -3.2(3) . . . . ?
C28 C25 C26 C27 176.01(18) . . . . ?
C24 C25 C26 C32 174.59(18) . . . . ?
C28 C25 C26 C32 -6.2(3) . . . . ?
C25 C26 C27 C22 2.1(3) . . . . ?
C32 C26 C27 C22 -175.85(18) . . . . ?
N21 C22 C27 C26 -179.7(2) . . . . ?
C23 C22 C27 C26 0.7(3) . . . . ?
C24 C25 C28 O29 175.9(2) . . . . ?
C26 C25 C28 O29 -3.3(3) . . . . ?
C24 C25 C28 O30 -3.6(3) . . . . ?
C26 C25 C28 O30 177.21(18) . . . . ?
O29 C28 O30 C31 -0.6(3) . . . . ?
C25 C28 O30 C31 178.91(19) . . . . ?
C27 C26 C32 O33 -76.2(3) . . . . ?
C25 C26 C32 O33 105.9(2) . . . . ?
C27 C26 C32 O34 98.3(2) . . . . ?
C25 C26 C32 O34 -79.6(2) . . . . ?
O33 C32 O34 C35 -1.5(3) . . . . ?
C26 C32 O34 C35 -176.05(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O33 0.89(3) 2.17(3) 3.054(3) 168(2) 2_676 yes
N1 H1B O29 0.85(3) 2.15(3) 2.991(3) 166(3) 1_454 yes
N21 H21A O9 0.82(3) 2.21(3) 2.958(3) 151(3) . yes
N21 H21B O13 0.91(3) 2.18(3) 3.053(3) 159(3) 2_676 yes

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041

























