# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2428670'
loop_
_audit_author_name
_audit_author_address
'Han Zhangang'
;H
China
;
_audit_update_record             
;
2025-03-04 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 N2 O4'
_chemical_formula_sum            'C21 N2 O4'
_chemical_formula_weight         344.23
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6618(18)
_cell_length_b                   9.7333(19)
_cell_length_c                   12.207(3)
_cell_angle_alpha                96.900(10)
_cell_angle_beta                 104.419(11)
_cell_angle_gamma                106.168(10)
_cell_volume                     937.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15872
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        63.886
_diffrn_reflns_theta_max         63.886
_diffrn_reflns_theta_min         4.832
_diffrn_ambient_temperature      278.4
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2380
_reflns_number_total             3082
_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+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.231
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0916
_refine_ls_restrained_S_all      1.026
_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)+(0.2000P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2639
_refine_ls_wR_factor_ref         0.2858
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_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 0.5766(3) 0.9721(2) 0.76407(19) 0.0609(7) Uani 1 1 d . . . . .
N002 N 0.5037(3) 0.6841(2) 0.3755(2) 0.0398(6) Uani 1 1 d . . . . .
O003 O 0.9927(3) 1.3298(3) 0.7853(2) 0.0752(8) Uani 1 1 d . . . . .
O004 O 0.3797(4) 0.7645(3) 0.7518(2) 0.0806(10) Uani 1 1 d . . . . .
O005 O 1.0166(4) 1.3411(3) 0.6080(3) 0.0805(9) Uani 1 1 d . . . . .
C006 C 0.3895(3) 0.6060(3) 0.4218(2) 0.0372(7) Uani 1 1 d . . . . .
C007 C 0.6097(3) 0.8750(3) 0.5458(2) 0.0372(7) Uani 1 1 d . . . . .
C008 C 0.2741(3) 0.4630(3) 0.3505(2) 0.0385(7) Uani 1 1 d . . . . .
C009 C 0.4934(4) 0.7938(3) 0.5941(2) 0.0398(7) Uani 1 1 d . . . . .
C00A C 0.3833(4) 0.6582(3) 0.5313(3) 0.0417(7) Uani 1 1 d . . . . .
C00B C 0.6102(3) 0.8130(3) 0.4352(2) 0.0393(7) Uani 1 1 d . . . . .
C00C C 0.7289(3) 1.0163(3) 0.6004(3) 0.0413(7) Uani 1 1 d . . . . .
C00D C 0.0617(4) 0.1919(3) 0.2163(3) 0.0466(8) Uani 1 1 d . . . . .
C00E C 0.8320(4) 1.1351(3) 0.6369(3) 0.0474(8) Uani 1 1 d . . . . .
C00F C 0.9569(4) 1.2782(3) 0.6732(3) 0.0481(8) Uani 1 1 d . . . . .
N00G N -0.1371(4) -0.0607(3) 0.0967(3) 0.0760(10) Uani 1 1 d . . . . .
C00H C 0.2884(4) 0.4137(3) 0.2424(3) 0.0518(8) Uani 1 1 d . . . . .
C00I C 0.4763(4) 0.8399(3) 0.7119(3) 0.0463(8) Uani 1 1 d . . . . .
C00J C 0.1514(4) 0.3758(3) 0.3894(3) 0.0489(8) Uani 1 1 d . . . . .
C00K C 0.1831(4) 0.2784(4) 0.1753(3) 0.0564(9) Uani 1 1 d . . . . .
C00L C 0.0456(4) 0.2405(3) 0.3231(3) 0.0515(8) Uani 1 1 d . . . . .
C00M C 0.7354(4) 0.8926(4) 0.3786(3) 0.0579(9) Uani 1 1 d . . . . .
C00N C -0.0479(4) 0.0506(4) 0.1491(3) 0.0574(9) Uani 1 1 d . . . . .
C00O C 0.5690(5) 1.0246(4) 0.8799(3) 0.0695(11) Uani 1 1 d . . . . .
C00P C 1.2876(6) 1.4543(5) 0.8807(6) 0.1113(19) Uani 1 1 d . . . . .
C00Q C 1.1222(6) 1.4724(4) 0.8346(4) 0.0897(14) Uani 1 1 d . . . . .
C00R C 0.6871(8) 1.1793(5) 0.9194(4) 0.1019(18) Uani 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 C00I 1.312(4) . ?
O001 C00O 1.469(4) . ?
N002 C006 1.355(4) . ?
N002 C00B 1.326(3) . ?
O003 C00F 1.326(4) . ?
O003 C00Q 1.464(4) . ?
O004 C00I 1.193(4) . ?
O005 C00F 1.192(4) . ?
C006 C008 1.482(4) . ?
C006 C00A 1.392(4) . ?
C007 C009 1.396(4) . ?
C007 C00B 1.413(4) . ?
C007 C00C 1.432(4) . ?
C008 C00H 1.396(4) . ?
C008 C00J 1.386(4) . ?
C009 C00A 1.389(4) . ?
C009 C00I 1.510(4) . ?
C00B C00M 1.512(4) . ?
C00C C00E 1.198(4) . ?
C00D C00K 1.392(5) . ?
C00D C00L 1.387(5) . ?
C00D C00N 1.441(4) . ?
C00E C00F 1.443(4) . ?
N00G C00N 1.141(4) . ?
C00H C00K 1.391(4) . ?
C00J C00L 1.389(4) . ?
C00O C00R 1.507(5) . ?
C00P C00Q 1.471(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
C00I O001 C00O 116.1(3) . . ?
C00B N002 C006 119.4(2) . . ?
C00F O003 C00Q 117.5(3) . . ?
N002 C006 C008 116.7(2) . . ?
N002 C006 C00A 121.1(3) . . ?
C00A C006 C008 122.2(3) . . ?
C009 C007 C00B 117.7(2) . . ?
C009 C007 C00C 124.8(3) . . ?
C00B C007 C00C 117.5(3) . . ?
C00H C008 C006 120.0(3) . . ?
C00J C008 C006 121.1(3) . . ?
C00J C008 C00H 118.9(3) . . ?
C007 C009 C00I 125.4(3) . . ?
C00A C009 C007 119.0(3) . . ?
C00A C009 C00I 115.6(3) . . ?
C009 C00A C006 119.8(3) . . ?
N002 C00B C007 122.9(3) . . ?
N002 C00B C00M 116.3(3) . . ?
C007 C00B C00M 120.8(3) . . ?
C00E C00C C007 174.1(3) . . ?
C00K C00D C00N 120.7(3) . . ?
C00L C00D C00K 120.1(3) . . ?
C00L C00D C00N 119.2(3) . . ?
C00C C00E C00F 176.3(3) . . ?
O003 C00F C00E 111.8(3) . . ?
O005 C00F O003 125.4(3) . . ?
O005 C00F C00E 122.8(3) . . ?
C00K C00H C008 120.7(3) . . ?
O001 C00I C009 112.7(3) . . ?
O004 C00I O001 124.0(3) . . ?
O004 C00I C009 123.3(3) . . ?
C008 C00J C00L 120.8(3) . . ?
C00H C00K C00D 119.5(3) . . ?
C00D C00L C00J 119.9(3) . . ?
N00G C00N C00D 178.6(4) . . ?
O001 C00O C00R 106.5(3) . . ?
O003 C00Q C00P 110.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
