# Electronic Supplementary Material (ESI) 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_sba188
_database_code_depnum_ccdc_archive 'CCDC 2337430'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-04-22 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         ?
_chemical_formula_sum            'C28 H18 N2 O4'
_chemical_formula_weight         446.44

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                   10.0719(6)
_cell_length_b                   10.5354(7)
_cell_length_c                   10.8948(7)
_cell_angle_alpha                92.2576(15)
_cell_angle_beta                 111.1719(14)
_cell_angle_gamma                93.0417(15)
_cell_volume                     1074.38(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3255
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.33

_exptl_crystal_description       brick
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9267
_exptl_absorpt_correction_T_max  0.9590
_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            14852
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4431
_reflns_number_gt                2904
_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)+(0.0372P)²+0.4526P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4431
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C11 C 0.6057(2) 0.10703(18) 0.9613(2) 0.0272(5) Uani 1 1 d . . . . .
O11 O 0.50939(14) 0.19164(13) 0.97388(13) 0.0296(3) Uani 1 1 d . . . . .
C12 C 0.7229(2) 0.0890(2) 1.0719(2) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.736427 0.132623 1.153934 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8207(2) 0.0059(2) 1.0610(2) 0.0367(5) Uani 1 1 d . . . . .
H13 H 0.901675 -0.008245 1.136538 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8014(2) -0.0568(2) 0.9411(2) 0.0381(6) Uani 1 1 d . . . . .
H14 H 0.870130 -0.112339 0.934486 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6831(2) -0.0390(2) 0.8313(2) 0.0358(5) Uani 1 1 d . . . . .
H15 H 0.669548 -0.083158 0.749537 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5836(2) 0.04370(19) 0.8404(2) 0.0285(5) Uani 1 1 d . . . . .
N16 N 0.46016(18) 0.05740(16) 0.72947(16) 0.0317(4) Uani 1 1 d . . . . .
C17 C 0.3700(2) 0.13260(19) 0.74485(19) 0.0275(5) Uani 1 1 d . . . . .
C18 C 0.3920(2) 0.21185(19) 0.86510(19) 0.0267(5) Uani 1 1 d . . . . .
C21 C 0.1994(2) 0.46448(19) 0.9316(2) 0.0280(5) Uani 1 1 d . . . . .
O21 O 0.08612(14) 0.44399(13) 0.81023(13) 0.0323(4) Uani 1 1 d . . . . .
C22 C 0.1968(2) 0.5657(2) 1.0145(2) 0.0339(5) Uani 1 1 d . . . . .
H22 H 0.117506 0.616797 0.991160 0.041 Uiso 1 1 calc R U . . .
C23 C 0.3113(2) 0.5921(2) 1.1327(2) 0.0352(5) Uani 1 1 d . . . . .
H23 H 0.311361 0.662179 1.190332 0.042 Uiso 1 1 calc R U . . .
C24 C 0.4248(2) 0.5162(2) 1.1658(2) 0.0334(5) Uani 1 1 d . . . . .
H24 H 0.502534 0.533995 1.247031 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4272(2) 0.41449(19) 1.0824(2) 0.0309(5) Uani 1 1 d . . . . .
H25 H 0.506017 0.362793 1.107460 0.037 Uiso 1 1 calc R U . . .
N26 N 0.30518(17) 0.29548(15) 0.86144(16) 0.0279(4) Uani 1 1 d . . . . .
C26 C 0.3144(2) 0.38704(19) 0.9615(2) 0.0274(5) Uani 1 1 d . . . . .
C30 C 0.2268(2) 0.1352(2) 0.6323(2) 0.0299(5) Uani 1 1 d . . . . .
O30 O 0.12456(16) 0.07822(16) 0.64377(15) 0.0434(4) Uani 1 1 d . . . . .
C31 C 0.2189(2) 0.20182(19) 0.5132(2) 0.0280(5) Uani 1 1 d . . . . .
C32 C 0.0890(2) 0.1979(2) 0.4085(2) 0.0378(6) Uani 1 1 d . . . . .
H32 H 0.007495 0.152637 0.414031 0.045 Uiso 1 1 calc R U . . .
C33 C 0.0782(2) 0.2597(2) 0.2966(2) 0.0427(6) Uani 1 1 d . . . . .
H33 H -0.010643 0.255934 0.224816 0.051 Uiso 1 1 calc R U . . .
C34 C 0.1950(3) 0.3266(2) 0.2880(2) 0.0418(6) Uani 1 1 d . . . . .
H34 H 0.186526 0.369738 0.210876 0.050 Uiso 1 1 calc R U . . .
C35 C 0.3250(2) 0.3313(2) 0.3916(2) 0.0403(6) Uani 1 1 d . . . . .
H35 H 0.405920 0.377222 0.385595 0.048 Uiso 1 1 calc R U . . .
C36 C 0.3369(2) 0.2689(2) 0.5041(2) 0.0340(5) Uani 1 1 d . . . . .
H36 H 0.426158 0.272062 0.575366 0.041 Uiso 1 1 calc R U . . .
C40 C 0.0006(2) 0.3343(2) 0.7932(2) 0.0310(5) Uani 1 1 d . . . . .
O40 O 0.01026(15) 0.26695(14) 0.88202(15) 0.0389(4) Uani 1 1 d . . . . .
C41 C -0.1040(2) 0.3123(2) 0.6568(2) 0.0328(5) Uani 1 1 d . . . . .
C42 C -0.1931(2) 0.2011(2) 0.6270(3) 0.0470(6) Uani 1 1 d . . . . .
H42 H -0.183674 0.141785 0.692545 0.056 Uiso 1 1 calc R U . . .
C43 C -0.2950(3) 0.1766(3) 0.5024(3) 0.0569(7) Uani 1 1 d . . . . .
H43 H -0.356342 0.100876 0.482251 0.068 Uiso 1 1 calc R U . . .
C44 C -0.3077(3) 0.2623(3) 0.4074(3) 0.0593(8) Uani 1 1 d . . . . .
H44 H -0.377887 0.245142 0.321577 0.071 Uiso 1 1 calc R U . . .
C45 C -0.2198(3) 0.3727(3) 0.4354(3) 0.0560(7) Uani 1 1 d . . . . .
H45 H -0.229304 0.431212 0.369113 0.067 Uiso 1 1 calc R U . . .
C46 C -0.1172(2) 0.3983(2) 0.5609(2) 0.0433(6) Uani 1 1 d . . . . .
H46 H -0.056454 0.474440 0.580822 0.052 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
C11 C12 1.377(3) . ?
C11 C16 1.390(3) . ?
C11 O11 1.390(2) . ?
O11 C18 1.372(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 N16 1.405(2) . ?
N16 C17 1.287(3) . ?
C17 C18 1.465(3) . ?
C17 C30 1.521(3) . ?
C18 N26 1.266(2) . ?
C21 C22 1.377(3) . ?
C21 O21 1.400(2) . ?
C21 C26 1.400(3) . ?
O21 C40 1.369(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(3) . ?
C25 H25 0.9500 . ?
N26 C26 1.401(3) . ?
C30 O30 1.212(2) . ?
C30 C31 1.478(3) . ?
C31 C36 1.387(3) . ?
C31 C32 1.388(3) . ?
C32 C33 1.376(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C40 O40 1.201(2) . ?
C40 C41 1.479(3) . ?
C41 C46 1.384(3) . ?
C41 C42 1.390(3) . ?
C42 C43 1.378(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.376(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.378(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9500 . ?
C46 H46 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
C12 C11 C16 121.62(19) . . ?
C12 C11 O11 117.78(18) . . ?
C16 C11 O11 120.60(17) . . ?
C18 O11 C11 118.99(16) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 118.92(19) . . ?
C15 C16 N16 119.62(19) . . ?
C11 C16 N16 121.40(18) . . ?
C17 N16 C16 116.80(18) . . ?
N16 C17 C18 124.95(19) . . ?
N16 C17 C30 117.74(18) . . ?
C18 C17 C30 117.25(17) . . ?
N26 C18 O11 124.51(19) . . ?
N26 C18 C17 118.69(18) . . ?
O11 C18 C17 116.77(17) . . ?
C22 C21 O21 118.07(18) . . ?
C22 C21 C26 122.36(19) . . ?
O21 C21 C26 119.47(18) . . ?
C40 O21 C21 116.27(15) . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C18 N26 C26 127.32(18) . . ?
C21 C26 N26 114.84(18) . . ?
C21 C26 C25 117.09(19) . . ?
N26 C26 C25 127.96(19) . . ?
O30 C30 C31 123.14(19) . . ?
O30 C30 C17 117.44(19) . . ?
C31 C30 C17 119.38(18) . . ?
C36 C31 C32 119.4(2) . . ?
C36 C31 C30 121.86(19) . . ?
C32 C31 C30 118.77(19) . . ?
C33 C32 C31 120.1(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.5(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.0(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 120.2(2) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
O40 C40 O21 122.2(2) . . ?
O40 C40 C41 125.3(2) . . ?
O21 C40 C41 112.44(18) . . ?
C46 C41 C42 119.9(2) . . ?
C46 C41 C40 122.7(2) . . ?
C42 C41 C40 117.4(2) . . ?
C43 C42 C41 120.1(3) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C44 C43 C42 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.7(2) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 119.9(3) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 119.6(2) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?

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
C12 C11 O11 C18 179.70(17) . . . . ?
C16 C11 O11 C18 -0.1(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
O11 C11 C12 C13 -179.47(18) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C14 C15 C16 N16 -177.36(19) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
O11 C11 C16 C15 179.25(18) . . . . ?
C12 C11 C16 N16 176.67(19) . . . . ?
O11 C11 C16 N16 -3.6(3) . . . . ?
C15 C16 N16 C17 178.11(19) . . . . ?
C11 C16 N16 C17 0.9(3) . . . . ?
C16 N16 C17 C18 5.2(3) . . . . ?
C16 N16 C17 C30 -171.82(17) . . . . ?
C11 O11 C18 N26 -172.63(18) . . . . ?
C11 O11 C18 C17 5.5(2) . . . . ?
N16 C17 C18 N26 169.6(2) . . . . ?
C30 C17 C18 N26 -13.3(3) . . . . ?
N16 C17 C18 O11 -8.7(3) . . . . ?
C30 C17 C18 O11 168.39(17) . . . . ?
C22 C21 O21 C40 -114.1(2) . . . . ?
C26 C21 O21 C40 69.5(2) . . . . ?
O21 C21 C22 C23 -176.77(18) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
O11 C18 N26 C26 4.0(3) . . . . ?
C17 C18 N26 C26 -174.18(18) . . . . ?
C22 C21 C26 N26 -174.75(18) . . . . ?
O21 C21 C26 N26 1.5(3) . . . . ?
C22 C21 C26 C25 1.6(3) . . . . ?
O21 C21 C26 C25 177.88(17) . . . . ?
C18 N26 C26 C21 -177.62(19) . . . . ?
C18 N26 C26 C25 6.5(3) . . . . ?
C24 C25 C26 C21 -1.7(3) . . . . ?
C24 C25 C26 N26 174.14(19) . . . . ?
N16 C17 C30 O30 102.4(2) . . . . ?
C18 C17 C30 O30 -74.9(2) . . . . ?
N16 C17 C30 C31 -75.3(2) . . . . ?
C18 C17 C30 C31 107.4(2) . . . . ?
O30 C30 C31 C36 178.4(2) . . . . ?
C17 C30 C31 C36 -4.0(3) . . . . ?
O30 C30 C31 C32 -0.8(3) . . . . ?
C17 C30 C31 C32 176.74(19) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
C30 C31 C32 C33 179.6(2) . . . . ?
C31 C32 C33 C34 -0.7(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 0.0(3) . . . . ?
C30 C31 C36 C35 -179.25(19) . . . . ?
C21 O21 C40 O40 9.0(3) . . . . ?
C21 O21 C40 C41 -172.47(16) . . . . ?
O40 C40 C41 C46 175.0(2) . . . . ?
O21 C40 C41 C46 -3.5(3) . . . . ?
O40 C40 C41 C42 -3.8(3) . . . . ?
O21 C40 C41 C42 177.73(19) . . . . ?
C46 C41 C42 C43 -0.4(3) . . . . ?
C40 C41 C42 C43 178.5(2) . . . . ?
C41 C42 C43 C44 0.4(4) . . . . ?
C42 C43 C44 C45 -0.2(4) . . . . ?
C43 C44 C45 C46 -0.1(4) . . . . ?
C42 C41 C46 C45 0.1(3) . . . . ?
C40 C41 C46 C45 -178.7(2) . . . . ?
C44 C45 C46 C41 0.2(4) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045



#==========================================================================

####################################################################### 
# 
# 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_sba200
_database_code_depnum_ccdc_archive 'CCDC 2337863'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2024-04-22 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         ?
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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                   6.7066(7)
_cell_length_b                   8.7863(9)
_cell_length_c                   12.6844(13)
_cell_angle_alpha                100.298(2)
_cell_angle_beta                 96.3058(19)
_cell_angle_gamma                111.3892(18)
_cell_volume                     672.14(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3607
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.13

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  0.9598
_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            12848
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.662
_diffrn_reflns_theta_max         29.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3342
_reflns_number_gt                2185
_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)+(0.0441P)²+0.2865P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3342
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.5701(3) 0.3912(2) 0.28482(14) 0.0345(4) Uani 1 1 d . . . . .
O2 O 0.7225(2) 0.32163(15) 0.29774(9) 0.0385(3) Uani 1 1 d . . . . .
O1 O 0.4185(2) 0.33183(17) 0.20985(11) 0.0504(4) Uani 1 1 d . . . . .
C11 C 0.6203(3) 0.5423(2) 0.37191(13) 0.0314(4) Uani 1 1 d . . . . .
C12 C 0.8129(3) 0.6159(2) 0.44754(14) 0.0361(4) Uani 1 1 d . . . . .
H12 H 0.918615 0.567771 0.444260 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8547(3) 0.7584(2) 0.52806(14) 0.0369(4) Uani 1 1 d . . . . .
H13 H 0.987774 0.807545 0.579819 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7002(3) 0.8289(2) 0.53245(14) 0.0340(4) Uani 1 1 d . . . . .
C15 C 0.5069(3) 0.7577(2) 0.45530(14) 0.0378(4) Uani 1 1 d . . . . .
H15 H 0.402611 0.807355 0.457299 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4673(3) 0.6153(2) 0.37619(14) 0.0360(4) Uani 1 1 d . . . . .
H16 H 0.334777 0.566252 0.324074 0.043 Uiso 1 1 calc R U . . .
O18 O 0.7222(2) 0.96721(16) 0.60859(11) 0.0454(4) Uani 1 1 d . . . . .
C18 C 0.9084(4) 1.0348(3) 0.69564(17) 0.0505(5) Uani 1 1 d . . . . .
H18A H 0.903282 1.131396 0.745920 0.076 Uiso 1 1 calc R U . . .
H18B H 1.041934 1.071045 0.665500 0.076 Uiso 1 1 calc R U . . .
H18C H 0.907297 0.948290 0.735028 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7195(3) 0.2017(2) 0.20811(13) 0.0321(4) Uani 1 1 d . . . . .
C22 C 0.8236(3) 0.2593(2) 0.12513(14) 0.0320(4) Uani 1 1 d . . . . .
C23 C 0.8329(3) 0.1428(2) 0.03770(14) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.901741 0.179775 -0.019914 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7418(3) -0.0265(2) 0.03502(14) 0.0330(4) Uani 1 1 d . . . . .
H24 H 0.747914 -0.105382 -0.025088 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6414(3) -0.0837(2) 0.11831(14) 0.0329(4) Uani 1 1 d . . . . .
C26 C 0.6301(3) 0.0329(2) 0.20558(14) 0.0341(4) Uani 1 1 d . . . . .
H26 H 0.560883 -0.004359 0.263032 0.041 Uiso 1 1 calc R U . . .
N28 N 0.9887(3) 0.5781(2) 0.13809(16) 0.0558(5) Uani 1 1 d . . . . .
C28 C 0.9166(3) 0.4366(2) 0.13141(15) 0.0385(4) Uani 1 1 d . . . . .
C29 C 0.5473(3) -0.2691(2) 0.11417(17) 0.0458(5) Uani 1 1 d . . . . .
H29A H 0.403519 -0.300355 0.134687 0.069 Uiso 1 1 calc R U . . .
H29B H 0.644456 -0.294779 0.165151 0.069 Uiso 1 1 calc R U . . .
H29C H 0.532611 -0.332903 0.039969 0.069 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 O1 1.197(2) . ?
C1 O2 1.378(2) . ?
C1 C11 1.472(2) . ?
O2 C21 1.3979(19) . ?
C11 C12 1.380(2) . ?
C11 C16 1.395(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 O18 1.3601(19) . ?
C14 C15 1.393(2) . ?
C15 C16 1.376(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O18 C18 1.433(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C26 1.375(2) . ?
C21 C22 1.395(2) . ?
C22 C23 1.392(2) . ?
C22 C28 1.435(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(2) . ?
C25 C29 1.506(2) . ?
C26 H26 0.9500 . ?
N28 C28 1.141(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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 O2 121.90(15) . . ?
O1 C1 C11 126.25(16) . . ?
O2 C1 C11 111.84(14) . . ?
C1 O2 C21 116.49(13) . . ?
C12 C11 C16 119.06(15) . . ?
C12 C11 C1 122.82(15) . . ?
C16 C11 C1 118.11(15) . . ?
C11 C12 C13 121.20(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 119.29(16) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
O18 C14 C13 124.48(16) . . ?
O18 C14 C15 115.46(15) . . ?
C13 C14 C15 120.06(16) . . ?
C16 C15 C14 119.85(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 120.52(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 O18 C18 117.33(14) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C21 C22 121.08(15) . . ?
C26 C21 O2 120.93(15) . . ?
C22 C21 O2 117.83(15) . . ?
C23 C22 C21 119.00(16) . . ?
C23 C22 C28 121.66(16) . . ?
C21 C22 C28 119.34(15) . . ?
C24 C23 C22 119.77(17) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.29(16) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 119.03(16) . . ?
C24 C25 C29 120.07(16) . . ?
C26 C25 C29 120.90(17) . . ?
C21 C26 C25 119.82(16) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N28 C28 C22 178.7(2) . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O1 C1 O2 C21 13.3(3) . . . . ?
C11 C1 O2 C21 -166.13(14) . . . . ?
O1 C1 C11 C12 -171.22(19) . . . . ?
O2 C1 C11 C12 8.2(2) . . . . ?
O1 C1 C11 C16 7.5(3) . . . . ?
O2 C1 C11 C16 -173.04(15) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
C1 C11 C12 C13 179.76(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O18 179.10(17) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
O18 C14 C15 C16 -178.66(17) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C1 C11 C16 C15 -179.38(17) . . . . ?
C13 C14 O18 C18 -6.0(3) . . . . ?
C15 C14 O18 C18 174.10(17) . . . . ?
C1 O2 C21 C26 -103.01(18) . . . . ?
C1 O2 C21 C22 81.46(19) . . . . ?
C26 C21 C22 C23 1.2(2) . . . . ?
O2 C21 C22 C23 176.67(14) . . . . ?
C26 C21 C22 C28 -179.38(16) . . . . ?
O2 C21 C22 C28 -3.9(2) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C28 C22 C23 C24 179.86(16) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 1.0(2) . . . . ?
C23 C24 C25 C29 -178.81(16) . . . . ?
C22 C21 C26 C25 -0.6(2) . . . . ?
O2 C21 C26 C25 -175.94(14) . . . . ?
C24 C25 C26 C21 -0.5(2) . . . . ?
C29 C25 C26 C21 179.28(16) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039



#==========================================================================

