# 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_sba205
_database_code_depnum_ccdc_archive 'CCDC 2401252'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-11-07 deposited with the CCDC.	2026-02-18 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         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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                   6.1263(5)
_cell_length_b                   10.1800(8)
_cell_length_c                   12.5965(10)
_cell_angle_alpha                92.8750(18)
_cell_angle_beta                 98.3576(17)
_cell_angle_gamma                90.9987(19)
_cell_volume                     776.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.83

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7449
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10920
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.636
_diffrn_reflns_theta_max         27.827
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3292
_reflns_number_gt                2317
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_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)+(0.0358P)²+0.1716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3292
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.5481(3) 0.74515(16) 0.73815(13) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.6682(3) 0.66363(16) 0.68336(13) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.4136(3) 0.75001(17) 0.57101(14) 0.0296(4) Uani 1 1 d . . . . .
O3 O 0.58291(19) 0.66639(11) 0.57510(9) 0.0293(4) Uani 0.894(15) 1 d . . P A 1
N5 N 0.3848(2) 0.79933(13) 0.66505(11) 0.0303(4) Uani 0.894(15) 1 d . . P A 1
N3B N 0.58291(19) 0.66639(11) 0.57510(9) 0.0293(4) Uani 0.106(15) 1 d . . P A 2
O5B O 0.3848(2) 0.79933(13) 0.66505(11) 0.0303(4) Uani 0.106(15) 1 d . . P A 2
C6 C 0.2803(3) 0.77420(18) 0.46643(13) 0.0324(4) Uani 1 1 d . . . . .
H6A H 0.148106 0.823277 0.480025 0.039 Uiso 1 1 calc R U . . .
H6B H 0.228666 0.688358 0.430224 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4007(3) 0.85085(18) 0.39023(13) 0.0315(4) Uani 1 1 d . . . . .
H7A H 0.486364 0.925318 0.430735 0.038 Uiso 1 1 calc R U . . .
H7B H 0.505121 0.792675 0.358825 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2360(3) 0.90281(18) 0.30073(13) 0.0334(4) Uani 1 1 d . . . . .
H8A H 0.317385 0.938929 0.245895 0.040 Uiso 1 1 calc R U . . .
H8B H 0.140136 0.828963 0.265782 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0936(3) 1.00834(17) 0.34068(13) 0.0280(4) Uani 1 1 d . . . . .
O9 O 0.1456(2) 1.07767(12) 0.42043(10) 0.0381(3) Uani 1 1 d . . . . .
O10 O -0.0950(2) 1.01868(14) 0.27565(10) 0.0445(4) Uani 1 1 d . . . . .
H10 H -0.181(4) 1.082(2) 0.3009(17) 0.067 Uiso 1 1 d . U . . .
C11 C 0.5662(3) 0.78070(16) 0.85419(13) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.3861(3) 0.76165(18) 0.90733(14) 0.0348(4) Uani 1 1 d . . . . .
H12 H 0.252325 0.724429 0.869197 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4008(3) 0.79681(19) 1.01601(15) 0.0395(5) Uani 1 1 d . . . . .
H13 H 0.277063 0.783095 1.052048 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5932(3) 0.85142(18) 1.07193(14) 0.0358(4) Uani 1 1 d . . . . .
H14 H 0.602110 0.876314 1.146159 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7734(3) 0.86984(18) 1.01960(14) 0.0338(4) Uani 1 1 d . . . . .
H15 H 0.906921 0.907015 1.058094 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7606(3) 0.83445(17) 0.91142(14) 0.0307(4) Uani 1 1 d . . . . .
H16 H 0.885571 0.847010 0.876062 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8530(3) 0.57757(16) 0.71262(13) 0.0272(4) Uani 1 1 d . . . . .
C22 C 0.8807(3) 0.51897(18) 0.81110(15) 0.0366(5) Uani 1 1 d . . . . .
H22 H 0.776878 0.533464 0.859355 0.044 Uiso 1 1 calc R U . . .
C23 C 1.0589(3) 0.43978(19) 0.83884(16) 0.0448(5) Uani 1 1 d . . . . .
H23 H 1.077882 0.400591 0.906342 0.054 Uiso 1 1 calc R U . . .
C24 C 1.2094(3) 0.41754(19) 0.76859(17) 0.0445(5) Uani 1 1 d . . . . .
H24 H 1.332400 0.363749 0.788205 0.053 Uiso 1 1 calc R U . . .
C25 C 1.1817(3) 0.47301(19) 0.67034(16) 0.0399(5) Uani 1 1 d . . . . .
H25 H 1.283921 0.456213 0.621636 0.048 Uiso 1 1 calc R U . . .
C26 C 1.0049(3) 0.55328(17) 0.64251(14) 0.0325(4) Uani 1 1 d . . . . .
H26 H 0.987184 0.592163 0.574892 0.039 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
C1 C2 1.348(2) . ?
C1 O5B 1.398(2) . ?
C1 N5 1.398(2) . ?
C1 C11 1.476(2) . ?
C2 N3B 1.3896(19) . ?
C2 O3 1.3896(19) . ?
C2 C21 1.460(2) . ?
C4 O5B 1.300(2) . ?
C4 N5 1.300(2) . ?
C4 O3 1.350(2) . ?
C4 N3B 1.350(2) . ?
C4 C6 1.480(2) . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.508(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O9 1.1987(19) . ?
C9 O10 1.325(2) . ?
O10 H10 0.91(2) . ?
C11 C12 1.387(2) . ?
C11 C16 1.388(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.390(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 C1 O5B 108.60(14) . . ?
C2 C1 N5 108.60(14) . . ?
C2 C1 C11 130.87(15) . . ?
O5B C1 C11 120.53(14) . . ?
N5 C1 C11 120.53(14) . . ?
C1 C2 N3B 107.49(14) . . ?
C1 C2 O3 107.49(14) . . ?
C1 C2 C21 135.04(16) . . ?
N3B C2 C21 117.46(14) . . ?
O3 C2 C21 117.46(14) . . ?
N5 C4 O3 113.13(14) . . ?
O5B C4 N3B 113.13(14) . . ?
O5B C4 C6 127.02(16) . . ?
N5 C4 C6 127.02(16) . . ?
O3 C4 C6 119.83(15) . . ?
N3B C4 C6 119.83(15) . . ?
C4 O3 C2 105.24(12) . . ?
C4 N5 C1 105.54(14) . . ?
C4 N3B C2 105.24(12) . . ?
C4 O5B C1 105.54(14) . . ?
C4 C6 C7 114.90(15) . . ?
C4 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C4 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 110.31(14) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 112.71(14) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O9 C9 O10 123.35(16) . . ?
O9 C9 C8 124.45(16) . . ?
O10 C9 C8 112.18(15) . . ?
C9 O10 H10 111.8(14) . . ?
C12 C11 C16 119.05(16) . . ?
C12 C11 C1 119.84(16) . . ?
C16 C11 C1 121.10(15) . . ?
C11 C12 C13 120.18(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.42(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.64(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.30(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.39(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C26 C21 C22 118.92(16) . . ?
C26 C21 C2 120.35(15) . . ?
C22 C21 C2 120.73(15) . . ?
C23 C22 C21 120.20(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.13(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.21(18) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.93(18) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.59(17) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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
O5B C1 C2 N3B 0.45(19) . . . . ?
C11 C1 C2 N3B -179.49(17) . . . . ?
N5 C1 C2 O3 0.45(19) . . . . ?
C11 C1 C2 O3 -179.49(17) . . . . ?
O5B C1 C2 C21 -178.18(18) . . . . ?
N5 C1 C2 C21 -178.18(18) . . . . ?
C11 C1 C2 C21 1.9(3) . . . . ?
N5 C4 O3 C2 -0.03(19) . . . . ?
C6 C4 O3 C2 -178.58(15) . . . . ?
C1 C2 O3 C4 -0.27(18) . . . . ?
C21 C2 O3 C4 178.64(14) . . . . ?
O3 C4 N5 C1 0.29(19) . . . . ?
C6 C4 N5 C1 178.72(17) . . . . ?
C2 C1 N5 C4 -0.46(19) . . . . ?
C11 C1 N5 C4 179.48(16) . . . . ?
O5B C4 N3B C2 -0.03(19) . . . . ?
C6 C4 N3B C2 -178.58(15) . . . . ?
C1 C2 N3B C4 -0.27(18) . . . . ?
C21 C2 N3B C4 178.64(14) . . . . ?
N3B C4 O5B C1 0.29(19) . . . . ?
C6 C4 O5B C1 178.72(17) . . . . ?
C2 C1 O5B C4 -0.46(19) . . . . ?
C11 C1 O5B C4 179.48(16) . . . . ?
O5B C4 C6 C7 112.5(2) . . . . ?
N5 C4 C6 C7 112.5(2) . . . . ?
O3 C4 C6 C7 -69.2(2) . . . . ?
N3B C4 C6 C7 -69.2(2) . . . . ?
C4 C6 C7 C8 -164.27(15) . . . . ?
C6 C7 C8 C9 68.1(2) . . . . ?
C7 C8 C9 O9 25.1(3) . . . . ?
C7 C8 C9 O10 -156.70(15) . . . . ?
C2 C1 C11 C12 -123.6(2) . . . . ?
O5B C1 C11 C12 56.5(2) . . . . ?
N5 C1 C11 C12 56.5(2) . . . . ?
C2 C1 C11 C16 57.1(3) . . . . ?
O5B C1 C11 C16 -122.86(18) . . . . ?
N5 C1 C11 C16 -122.86(18) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C1 C11 C12 C13 -178.95(16) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
C1 C11 C16 C15 178.61(15) . . . . ?
C1 C2 C21 C26 -149.9(2) . . . . ?
N3B C2 C21 C26 31.6(2) . . . . ?
O3 C2 C21 C26 31.6(2) . . . . ?
C1 C2 C21 C22 29.8(3) . . . . ?
N3B C2 C21 C22 -148.70(16) . . . . ?
O3 C2 C21 C22 -148.70(16) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
C2 C21 C22 C23 -178.67(17) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C2 C21 C26 C25 179.26(16) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042

