# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_wpu23007
_database_code_depnum_ccdc_archive 'CCDC 2391160'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2024-10-15 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N3 O4'
_chemical_formula_sum            'C20 H25 N3 O4'
_chemical_formula_weight         371.43
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H25 N3 O4'
_chemical_oxdiff_usercomment     'Owen Hughes OH25a'
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'
H H 0.0000 0.0000 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.14295(10)
_cell_length_b                   10.25505(13)
_cell_length_c                   20.8149(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1951.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7660
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      76.4760
_cell_measurement_theta_min      4.2280
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0183
0 0 -1 0.0247
1 1 0 0.1021
0 1 0 0.1122
1 -2 0 0.0828
1 -1 0 0.0825
2 -1 0 0.0956
-1 -1 0 0.1035
-1 1 0 0.0730

_exptl_crystal_recrystallization_method 
'evaporation of an ethyl acetate solution'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 1.0000 -0.0246 -0.0698 0.0014
0.0000 -0.0000 -1.0000 0.0246 0.0698 -0.0014
1.0000 1.0000 -0.0001 -0.1497 0.0561 0.1594
0.0000 1.0000 -0.0001 -0.1416 0.0497 -0.0088
0.9999 -2.0000 0.0001 0.2750 -0.0931 0.1858
0.9999 -1.0000 0.0000 0.1334 -0.0434 0.1770
1.9999 -1.0000 -0.0000 0.1253 -0.0371 0.3452
-1.0000 -1.0000 0.0001 0.1497 -0.0561 -0.1594
-0.9999 1.0000 -0.0000 -0.1334 0.0434 -0.1770

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -80.00   0.50    0.80    --  -48.95-138.00-140.00   52
  2  ω     40.00  98.00   0.50    0.80    --   48.95-131.00  35.00  116
  3  ω     44.00 124.00   0.50    3.20    --  107.75-143.00 -46.00  160
  4  ω     68.00 166.00   0.50    3.20    --  107.75   5.00  48.00  196
  5  ω   -100.00 -74.00   0.50    0.80    --  -48.95-125.00 150.00   52
  6  ω    -52.00 -15.00   0.50    0.80    --  -48.95  37.00  60.00   74
  7  ω   -116.00 -86.00   0.50    0.80    --  -48.95-125.00 -90.00   60
  8  ω    -61.00  27.00   0.50    0.80    --  -48.95  19.00-180.00  176
  9  ω     38.00  98.00   0.50    3.20    --  107.75 -99.00  30.00  120
 10  ω     42.00 107.00   0.50    3.20    --  107.75-125.00-150.00  130
 11  ω     89.00 116.00   0.50    3.20    --  107.75  77.00  90.00   54
 12  ω     37.00  77.00   0.50    3.20    --  107.75 -99.00 -30.00   80
 13  ω     99.00 124.00   0.50    3.20    --  107.75 125.00-180.00   50
 14  ω     37.00  80.00   0.50    3.20    --  107.75 -99.00 -60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0081269000
_diffrn_orient_matrix_UB_12      -0.1415615000
_diffrn_orient_matrix_UB_13      -0.0245599000
_diffrn_orient_matrix_UB_21      0.0063293000
_diffrn_orient_matrix_UB_22      0.0497132000
_diffrn_orient_matrix_UB_23      -0.0697670000
_diffrn_orient_matrix_UB_31      0.1681819000
_diffrn_orient_matrix_UB_32      -0.0088317000
_diffrn_orient_matrix_UB_33      0.0014157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3360
_reflns_number_total             3479
_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       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.58980(19) 0.26642(18) 0.74315(8) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.43616(18) 0.28584(19) 0.71571(8) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.410(2) 0.201(2) 0.7022(10) 0.018(5) Uiso 1 1 d . . . . .
C3 C 0.4274(2) 0.37597(19) 0.65671(9) 0.0211(4) Uani 1 1 d . . . . .
H3A H 0.494(3) 0.343(2) 0.6242(11) 0.025(6) Uiso 1 1 d . . . . .
H3B H 0.459(2) 0.463(2) 0.6686(11) 0.024(6) Uiso 1 1 d . . . . .
C4 C 0.27611(19) 0.3851(2) 0.62937(9) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.1928(2) 0.4954(2) 0.62587(9) 0.0247(4) Uani 1 1 d . . . . .
H5 H 0.218(2) 0.582(2) 0.6401(11) 0.024(6) Uiso 1 1 d . . . . .
C6 C 0.0606(2) 0.3404(2) 0.57800(9) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.19319(19) 0.2827(2) 0.59918(9) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.2171(2) 0.1500(2) 0.58775(10) 0.0276(4) Uani 1 1 d . . . . .
H8 H 0.300(3) 0.111(3) 0.6037(12) 0.034(6) Uiso 1 1 d . . . . .
C9 C 0.1135(2) 0.0795(2) 0.55442(11) 0.0360(5) Uani 1 1 d . . . . .
H9 H 0.133(3) -0.016(3) 0.5470(13) 0.046(7) Uiso 1 1 d . . . . .
C10 C -0.0156(2) 0.1390(3) 0.53253(11) 0.0377(6) Uani 1 1 d . . . . .
H10 H -0.084(3) 0.089(3) 0.5085(13) 0.047(8) Uiso 1 1 d . . . . .
C11 C -0.0447(2) 0.2684(3) 0.54432(10) 0.0327(5) Uani 1 1 d . . . . .
H11 H -0.131(3) 0.310(3) 0.5298(12) 0.037(7) Uiso 1 1 d . . . . .
C12 C 0.37675(19) 0.42671(19) 0.80498(9) 0.0210(4) Uani 1 1 d . . . . .
C13 C 0.2872(2) 0.4630(2) 0.86356(10) 0.0235(4) Uani 1 1 d . . . . .
H13A H 0.219(3) 0.392(3) 0.8766(11) 0.028(6) Uiso 1 1 d . . . . .
H13B H 0.227(3) 0.540(3) 0.8520(11) 0.028(6) Uiso 1 1 d . . . . .
C14 C 0.3865(2) 0.4982(2) 0.92062(10) 0.0256(4) Uani 1 1 d . . . . .
H14A H 0.322(3) 0.511(2) 0.9581(12) 0.028(6) Uiso 1 1 d . . . . .
H14B H 0.438(3) 0.584(3) 0.9118(11) 0.028(6) Uiso 1 1 d . . . . .
C15 C 0.5016(2) 0.3970(2) 0.93900(9) 0.0246(4) Uani 1 1 d . . . . .
H15A H 0.571(2) 0.387(2) 0.9048(11) 0.023(5) Uiso 1 1 d . . . . .
H15B H 0.557(3) 0.432(2) 0.9743(11) 0.021(5) Uiso 1 1 d . . . . .
C16 C 0.4435(2) 0.2616(2) 0.95661(10) 0.0273(4) Uani 1 1 d . . . . .
H16A H 0.355(3) 0.266(2) 0.9856(11) 0.029(6) Uiso 1 1 d . . . . .
H16B H 0.520(3) 0.212(2) 0.9781(11) 0.029(6) Uiso 1 1 d . . . . .
C17 C 0.2667(2) 0.15187(18) 0.88458(9) 0.0229(4) Uani 1 1 d . . . . .
C18 C 0.2400(2) 0.1174(2) 0.81492(9) 0.0242(4) Uani 1 1 d . . . . .
H18A H 0.325(3) 0.073(2) 0.7950(11) 0.025(6) Uiso 1 1 d . . . . .
H18B H 0.155(3) 0.062(2) 0.8134(11) 0.025(6) Uiso 1 1 d . . . . .
C19 C 0.20728(19) 0.2422(2) 0.77662(9) 0.0225(4) Uani 1 1 d . . . . .
H19A H 0.174(2) 0.219(2) 0.7333(11) 0.019(5) Uiso 1 1 d . . . . .
H19B H 0.127(2) 0.296(2) 0.7968(11) 0.026(5) Uiso 1 1 d . . . . .
C20 C 0.8420(2) 0.2756(3) 0.72463(11) 0.0306(5) Uani 1 1 d . . . . .
H20A H 0.901(3) 0.295(3) 0.6893(13) 0.040(7) Uiso 1 1 d . . . . .
H20B H 0.854(3) 0.183(3) 0.7385(12) 0.033(6) Uiso 1 1 d . . . . .
H20C H 0.858(3) 0.333(3) 0.7609(13) 0.031(6) Uiso 1 1 d . . . . .
N1 N 0.06228(19) 0.46870(19) 0.59516(8) 0.0274(4) Uani 1 1 d . . . . .
H1 H -0.004(3) 0.524(3) 0.5865(13) 0.043(7) Uiso 1 1 d . . . . .
N2 N 0.33711(15) 0.32435(15) 0.76737(7) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.40212(18) 0.18924(16) 0.89876(8) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.463(3) 0.192(2) 0.8687(12) 0.024(6) Uiso 1 1 d . . . . .
O1 O 0.61461(13) 0.22267(13) 0.79575(6) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.69451(13) 0.29540(14) 0.70087(6) 0.0251(3) Uani 1 1 d . . . . .
O3 O 0.48922(13) 0.48847(13) 0.79198(6) 0.0233(3) Uani 1 1 d . . . . .
O4 O 0.16455(15) 0.15523(15) 0.92367(7) 0.0291(3) 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
C1 C2 1.529(2) . ?
C1 O1 1.205(2) . ?
C1 O2 1.334(2) . ?
C2 H2 0.95(2) . ?
C2 C3 1.539(3) . ?
C2 N2 1.460(2) . ?
C3 H3A 0.97(2) . ?
C3 H3B 0.97(3) . ?
C3 C4 1.499(3) . ?
C4 C5 1.365(3) . ?
C4 C7 1.439(3) . ?
C5 H5 0.96(3) . ?
C5 N1 1.381(3) . ?
C6 C7 1.419(3) . ?
C6 C11 1.402(3) . ?
C6 N1 1.363(3) . ?
C7 C8 1.399(3) . ?
C8 H8 0.92(3) . ?
C8 C9 1.379(3) . ?
C9 H9 1.01(3) . ?
C9 C10 1.405(4) . ?
C10 H10 0.95(3) . ?
C10 C11 1.375(4) . ?
C11 H11 0.94(3) . ?
C12 C13 1.515(3) . ?
C12 N2 1.359(2) . ?
C12 O3 1.238(2) . ?
C13 H13A 1.00(3) . ?
C13 H13B 0.99(3) . ?
C13 C14 1.538(3) . ?
C14 H14A 0.99(2) . ?
C14 H14B 1.01(3) . ?
C14 C15 1.527(3) . ?
C15 H15A 0.96(2) . ?
C15 H15B 0.96(2) . ?
C15 C16 1.532(3) . ?
C16 H16A 1.01(2) . ?
C16 H16B 0.98(3) . ?
C16 N3 1.464(3) . ?
C17 C18 1.512(3) . ?
C17 N3 1.329(3) . ?
C17 O4 1.239(2) . ?
C18 H18A 0.99(2) . ?
C18 H18B 0.97(2) . ?
C18 C19 1.537(3) . ?
C19 H19A 0.98(2) . ?
C19 H19B 1.01(2) . ?
C19 N2 1.468(2) . ?
C20 H20A 0.93(3) . ?
C20 H20B 1.00(3) . ?
C20 H20C 0.97(3) . ?
C20 O2 1.451(2) . ?
N1 H1 0.85(3) . ?
N3 H3 0.84(3) . ?

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
O1 C1 C2 124.11(16) . . ?
O1 C1 O2 123.19(16) . . ?
O2 C1 C2 112.56(14) . . ?
C1 C2 H2 102.8(12) . . ?
C1 C2 C3 115.09(14) . . ?
C3 C2 H2 107.7(13) . . ?
N2 C2 C1 109.26(14) . . ?
N2 C2 H2 108.1(12) . . ?
N2 C2 C3 113.13(15) . . ?
C2 C3 H3A 108.3(14) . . ?
C2 C3 H3B 109.5(13) . . ?
H3A C3 H3B 108(2) . . ?
C4 C3 C2 112.86(15) . . ?
C4 C3 H3A 109.8(13) . . ?
C4 C3 H3B 108.3(13) . . ?
C5 C4 C3 125.93(18) . . ?
C5 C4 C7 106.67(17) . . ?
C7 C4 C3 127.34(18) . . ?
C4 C5 H5 128.0(14) . . ?
C4 C5 N1 110.04(18) . . ?
N1 C5 H5 121.9(14) . . ?
C11 C6 C7 121.5(2) . . ?
N1 C6 C7 108.14(18) . . ?
N1 C6 C11 130.3(2) . . ?
C6 C7 C4 106.36(18) . . ?
C8 C7 C4 134.53(18) . . ?
C8 C7 C6 119.10(19) . . ?
C7 C8 H8 119.5(17) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 121.3(17) . . ?
C8 C9 H9 117.9(16) . . ?
C8 C9 C10 120.8(2) . . ?
C10 C9 H9 121.2(16) . . ?
C9 C10 H10 119.1(18) . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.3(18) . . ?
C6 C11 H11 119.6(16) . . ?
C10 C11 C6 117.7(2) . . ?
C10 C11 H11 122.7(16) . . ?
N2 C12 C13 120.60(16) . . ?
O3 C12 C13 119.96(17) . . ?
O3 C12 N2 119.41(17) . . ?
C12 C13 H13A 112.3(14) . . ?
C12 C13 H13B 107.4(14) . . ?
C12 C13 C14 111.11(16) . . ?
H13A C13 H13B 107.4(19) . . ?
C14 C13 H13A 109.4(13) . . ?
C14 C13 H13B 109.1(14) . . ?
C13 C14 H14A 106.9(13) . . ?
C13 C14 H14B 109.9(13) . . ?
H14A C14 H14B 108.0(19) . . ?
C15 C14 C13 116.14(17) . . ?
C15 C14 H14A 107.6(14) . . ?
C15 C14 H14B 108.0(13) . . ?
C14 C15 H15A 109.9(14) . . ?
C14 C15 H15B 107.4(14) . . ?
C14 C15 C16 115.91(17) . . ?
H15A C15 H15B 104.9(19) . . ?
C16 C15 H15A 108.4(15) . . ?
C16 C15 H15B 109.8(13) . . ?
C15 C16 H16A 112.2(14) . . ?
C15 C16 H16B 109.5(15) . . ?
H16A C16 H16B 108.9(19) . . ?
N3 C16 C15 110.63(16) . . ?
N3 C16 H16A 108.0(14) . . ?
N3 C16 H16B 107.4(14) . . ?
N3 C17 C18 115.51(17) . . ?
O4 C17 C18 120.96(17) . . ?
O4 C17 N3 123.24(18) . . ?
C17 C18 H18A 112.5(13) . . ?
C17 C18 H18B 107.4(14) . . ?
C17 C18 C19 109.49(16) . . ?
H18A C18 H18B 110.1(19) . . ?
C19 C18 H18A 108.7(14) . . ?
C19 C18 H18B 108.5(14) . . ?
C18 C19 H19A 109.5(13) . . ?
C18 C19 H19B 112.5(13) . . ?
H19A C19 H19B 107.0(18) . . ?
N2 C19 C18 112.87(15) . . ?
N2 C19 H19A 105.5(12) . . ?
N2 C19 H19B 109.1(13) . . ?
H20A C20 H20B 112(2) . . ?
H20A C20 H20C 113(2) . . ?
H20B C20 H20C 110(2) . . ?
O2 C20 H20A 103.8(16) . . ?
O2 C20 H20B 109.7(14) . . ?
O2 C20 H20C 108.9(14) . . ?
C5 N1 H1 125(2) . . ?
C6 N1 C5 108.78(17) . . ?
C6 N1 H1 126(2) . . ?
C2 N2 C19 116.29(14) . . ?
C12 N2 C2 117.89(15) . . ?
C12 N2 C19 125.68(16) . . ?
C16 N3 H3 115.2(16) . . ?
C17 N3 C16 124.69(18) . . ?
C17 N3 H3 117.5(16) . . ?
C1 O2 C20 114.27(15) . . ?

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 H1 O4 0.85(3) 2.00(3) 2.849(2) 174(3) 3_556 yes

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
C1 C2 C3 C4 176.48(16) . . . . ?
C1 C2 N2 C12 52.0(2) . . . . ?
C1 C2 N2 C19 -123.96(16) . . . . ?
C2 C1 O2 C20 -178.77(17) . . . . ?
C2 C3 C4 C5 117.2(2) . . . . ?
C2 C3 C4 C7 -66.0(2) . . . . ?
C3 C2 N2 C12 -77.6(2) . . . . ?
C3 C2 N2 C19 106.42(17) . . . . ?
C3 C4 C5 N1 177.24(17) . . . . ?
C3 C4 C7 C6 -176.69(17) . . . . ?
C3 C4 C7 C8 3.0(4) . . . . ?
C4 C5 N1 C6 -0.5(2) . . . . ?
C4 C7 C8 C9 -177.6(2) . . . . ?
C5 C4 C7 C6 0.6(2) . . . . ?
C5 C4 C7 C8 -179.7(2) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
C7 C4 C5 N1 -0.1(2) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
C7 C6 N1 C5 0.8(2) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C6 1.3(3) . . . . ?
C11 C6 C7 C4 177.87(17) . . . . ?
C11 C6 C7 C8 -1.9(3) . . . . ?
C11 C6 N1 C5 -177.77(19) . . . . ?
C12 C13 C14 C15 -53.7(2) . . . . ?
C13 C12 N2 C2 -173.62(16) . . . . ?
C13 C12 N2 C19 1.9(3) . . . . ?
C13 C14 C15 C16 -58.2(2) . . . . ?
C14 C15 C16 N3 76.7(2) . . . . ?
C15 C16 N3 C17 -115.5(2) . . . . ?
C17 C18 C19 N2 72.0(2) . . . . ?
C18 C17 N3 C16 161.50(18) . . . . ?
C18 C19 N2 C2 80.51(19) . . . . ?
C18 C19 N2 C12 -95.1(2) . . . . ?
N1 C6 C7 C4 -0.9(2) . . . . ?
N1 C6 C7 C8 179.35(17) . . . . ?
N1 C6 C11 C10 178.7(2) . . . . ?
N2 C2 C3 C4 -56.9(2) . . . . ?
N2 C12 C13 C14 138.43(18) . . . . ?
N3 C17 C18 C19 -84.1(2) . . . . ?
O1 C1 C2 C3 164.00(17) . . . . ?
O1 C1 C2 N2 35.5(2) . . . . ?
O1 C1 O2 C20 -2.8(3) . . . . ?
O2 C1 C2 C3 -20.1(2) . . . . ?
O2 C1 C2 N2 -148.60(15) . . . . ?
O3 C12 C13 C14 -39.7(2) . . . . ?
O3 C12 N2 C2 4.5(2) . . . . ?
O3 C12 N2 C19 -179.96(17) . . . . ?
O4 C17 C18 C19 89.9(2) . . . . ?
O4 C17 N3 C16 -12.4(3) . . . . ?

_olex2_date_sample_data_collection 2023-02-22
_olex2_date_sample_submission    2023-02-20
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id OH25a
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.872
