# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_P-CQ-ketone
_database_code_depnum_ccdc_archive 'CCDC 2551718'
loop_
_audit_author_name
_audit_author_address
'Frank Fronczek'
;LSU
United States of America
;
_audit_update_record             
;
2026-05-05 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
3-(diethylamino)-9-ethanone-6H-chromeno[4,3-b]quinolin-6-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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                   8.327(4)
_cell_length_b                   8.873(3)
_cell_length_c                   13.494(6)
_cell_angle_alpha                87.287(13)
_cell_angle_beta                 72.854(11)
_cell_angle_gamma                66.150(10)
_cell_volume                     868.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    2519
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.87
_exptl_crystal_description       'needle fragment'
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_radiation_source         'I\mS 3.0 microfocus'
_diffrn_measurement_device_type  'Bruker D8 Venture DUO with Photon III C14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40668
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.1485
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         21.975
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4306
_reflns_number_gt                2828
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0919P)²] 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         4306
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
O5 O 0.51654(17) 0.35471(15) 0.29068(9) 0.0228(3) Uani 1 1 d . . . . .
O17 O 0.23935(18) 0.36936(17) 0.37271(11) 0.0297(3) Uani 1 1 d . . . . .
O18 O -0.28399(19) 1.25977(17) 0.80950(11) 0.0327(3) Uani 1 1 d . . . . .
N12 N 0.43045(19) 0.76797(17) 0.46902(11) 0.0200(3) Uani 1 1 d . . . . .
N19 N 1.1155(2) 0.29998(18) 0.08876(12) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.7791(2) 0.5918(2) 0.31333(13) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.770019 0.680311 0.354703 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9396(2) 0.5100(2) 0.23422(13) 0.0221(3) Uani 1 1 d . . . . .
H2 H 1.038999 0.542327 0.222364 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9580(2) 0.3777(2) 0.17022(13) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.8115(2) 0.3282(2) 0.19394(13) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.821611 0.236476 0.155148 0.025 Uiso 1 1 calc R U . . .
C4A C 0.6515(2) 0.4139(2) 0.27442(13) 0.0189(3) Uani 1 1 d . . . . .
C4B C 0.6291(2) 0.5481(2) 0.33445(12) 0.0187(3) Uani 1 1 d . . . . .
C4C C 0.4541(2) 0.6366(2) 0.41314(12) 0.0183(3) Uani 1 1 d . . . . .
C4D C 0.3139(2) 0.5784(2) 0.42558(12) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.3482(2) 0.4300(2) 0.36389(13) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.1434(2) 0.6616(2) 0.49675(13) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.047866 0.624944 0.505574 0.023 Uiso 1 1 calc R U . . .
C8 C -0.0587(2) 0.8953(2) 0.63009(13) 0.0199(3) Uani 1 1 d . . . . .
H8 H -0.157842 0.862989 0.640616 0.024 Uiso 1 1 calc R U . . .
C7A C 0.1134(2) 0.8022(2) 0.55614(12) 0.0189(3) Uani 1 1 d . . . . .
C9 C -0.0833(2) 1.0322(2) 0.68682(13) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.0671(2) 1.0781(2) 0.67151(13) 0.0228(4) Uani 1 1 d . . . . .
H10 H 0.050740 1.171406 0.711519 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2349(2) 0.9908(2) 0.60045(14) 0.0228(4) Uani 1 1 d . . . . .
H11 H 0.332913 1.024222 0.591342 0.027 Uiso 1 1 calc R U . . .
C11A C 0.2623(2) 0.8504(2) 0.54035(12) 0.0191(3) Uani 1 1 d . . . . .
C13 C -0.2636(2) 1.1356(2) 0.76343(13) 0.0233(4) Uani 1 1 d . . . . .
C14 C -0.4195(3) 1.0816(2) 0.78145(15) 0.0282(4) Uani 1 1 d . . . . .
H14A H -0.381426 0.968949 0.803599 0.042 Uiso 1 1 calc R U . . .
H14B H -0.451053 1.084081 0.716760 0.042 Uiso 1 1 calc R U . . .
H14C H -0.527190 1.156790 0.835695 0.042 Uiso 1 1 calc R U . . .
C15 C 1.1566(2) 0.1422(2) 0.03731(14) 0.0251(4) Uani 1 1 d . . . . .
H15A H 1.103903 0.078615 0.089022 0.030 Uiso 1 1 calc R U . . .
H15B H 1.291894 0.078772 0.013503 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0843(3) 0.1546(2) -0.05542(15) 0.0310(4) Uani 1 1 d . . . . .
H16A H 1.130326 0.044088 -0.089989 0.047 Uiso 1 1 calc R U . . .
H16B H 1.126597 0.225399 -0.104598 0.047 Uiso 1 1 calc R U . . .
H16C H 0.949334 0.202433 -0.031361 0.047 Uiso 1 1 calc R U . . .
C15A C 1.2403(3) 0.3799(2) 0.04118(14) 0.0273(4) Uani 1 1 d . . . . .
H15C H 1.174758 0.500118 0.061471 0.033 Uiso 1 1 calc R U . . .
H15D H 1.273026 0.364159 -0.035470 0.033 Uiso 1 1 calc R U . . .
C16B C 1.4160(3) 0.3138(3) 0.07209(17) 0.0349(4) Uani 1 1 d . . . . .
H16D H 1.490593 0.375044 0.039962 0.052 Uiso 1 1 calc R U . . .
H16E H 1.485961 0.196242 0.048291 0.052 Uiso 1 1 calc R U . . .
H16F H 1.385091 0.327442 0.147967 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
O5 C6 1.370(2) . ?
O5 C4A 1.381(2) . ?
O17 C6 1.204(2) . ?
O18 C13 1.217(2) . ?
N12 C4C 1.333(2) . ?
N12 C11A 1.366(2) . ?
N19 C3 1.376(2) . ?
N19 C15 1.457(2) . ?
N19 C15A 1.468(2) . ?
C1 C2 1.378(2) . ?
C1 C4B 1.402(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.421(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(2) . ?
C4 C4A 1.392(2) . ?
C4 H4 0.9500 . ?
C4A C4B 1.390(2) . ?
C4B C4C 1.452(2) . ?
C4C C4D 1.421(2) . ?
C4D C7 1.378(2) . ?
C4D C6 1.473(2) . ?
C7 C7A 1.409(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(2) . ?
C8 C7A 1.418(2) . ?
C8 H8 0.9500 . ?
C7A C11A 1.425(2) . ?
C9 C10 1.425(2) . ?
C9 C13 1.491(2) . ?
C10 C11 1.369(2) . ?
C10 H10 0.9500 . ?
C11 C11A 1.421(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.510(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15A C16B 1.517(3) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 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
C6 O5 C4A 121.93(13) . . ?
C4C N12 C11A 117.76(14) . . ?
C3 N19 C15 121.77(14) . . ?
C3 N19 C15A 121.83(15) . . ?
C15 N19 C15A 116.04(14) . . ?
C2 C1 C4B 121.88(16) . . ?
C2 C1 H1 119.1 . . ?
C4B C1 H1 119.1 . . ?
C1 C2 C3 120.68(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
N19 C3 C4 121.50(16) . . ?
N19 C3 C2 120.74(16) . . ?
C4 C3 C2 117.76(15) . . ?
C4A C4 C3 119.85(16) . . ?
C4A C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O5 C4A C4B 122.34(14) . . ?
O5 C4A C4 114.88(15) . . ?
C4B C4A C4 122.77(15) . . ?
C4A C4B C1 116.93(15) . . ?
C4A C4B C4C 119.38(15) . . ?
C1 C4B C4C 123.68(15) . . ?
N12 C4C C4D 123.04(15) . . ?
N12 C4C C4B 119.55(15) . . ?
C4D C4C C4B 117.40(15) . . ?
C7 C4D C4C 119.59(15) . . ?
C7 C4D C6 119.35(15) . . ?
C4C C4D C6 121.06(14) . . ?
O17 C6 O5 117.23(15) . . ?
O17 C6 C4D 125.03(15) . . ?
O5 C6 C4D 117.73(14) . . ?
C4D C7 C7A 118.69(15) . . ?
C4D C7 H7 120.7 . . ?
C7A C7 H7 120.7 . . ?
C9 C8 C7A 120.56(15) . . ?
C9 C8 H8 119.7 . . ?
C7A C8 H8 119.7 . . ?
C7 C7A C8 122.05(15) . . ?
C7 C7A C11A 118.19(15) . . ?
C8 C7A C11A 119.76(15) . . ?
C8 C9 C10 119.26(15) . . ?
C8 C9 C13 122.10(15) . . ?
C10 C9 C13 118.64(16) . . ?
C11 C10 C9 121.50(16) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C11A 120.05(16) . . ?
C10 C11 H11 120.0 . . ?
C11A C11 H11 120.0 . . ?
N12 C11A C11 118.44(15) . . ?
N12 C11A C7A 122.70(15) . . ?
C11 C11A C7A 118.86(15) . . ?
O18 C13 C9 120.85(16) . . ?
O18 C13 C14 121.24(16) . . ?
C9 C13 C14 117.91(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N19 C15 C16 115.07(16) . . ?
N19 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N19 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N19 C15A C16B 113.66(16) . . ?
N19 C15A H15C 108.8 . . ?
C16B C15A H15C 108.8 . . ?
N19 C15A H15D 108.8 . . ?
C16B C15A H15D 108.8 . . ?
H15C C15A H15D 107.7 . . ?
C15A C16B H16D 109.5 . . ?
C15A C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15A C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 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
C4B C1 C2 C3 0.4(3) . . . . ?
C15 N19 C3 C4 -13.5(3) . . . . ?
C15A N19 C3 C4 159.39(17) . . . . ?
C15 N19 C3 C2 165.64(16) . . . . ?
C15A N19 C3 C2 -21.5(3) . . . . ?
C1 C2 C3 N19 177.54(16) . . . . ?
C1 C2 C3 C4 -3.3(3) . . . . ?
N19 C3 C4 C4A -177.54(16) . . . . ?
C2 C3 C4 C4A 3.3(3) . . . . ?
C6 O5 C4A C4B 3.2(2) . . . . ?
C6 O5 C4A C4 -177.09(15) . . . . ?
C3 C4 C4A O5 179.84(14) . . . . ?
C3 C4 C4A C4B -0.5(3) . . . . ?
O5 C4A C4B C1 177.26(14) . . . . ?
C4 C4A C4B C1 -2.4(3) . . . . ?
O5 C4A C4B C4C -3.8(2) . . . . ?
C4 C4A C4B C4C 176.57(15) . . . . ?
C2 C1 C4B C4A 2.4(3) . . . . ?
C2 C1 C4B C4C -176.50(16) . . . . ?
C11A N12 C4C C4D -0.8(2) . . . . ?
C11A N12 C4C C4B 178.30(14) . . . . ?
C4A C4B C4C N12 -178.30(15) . . . . ?
C1 C4B C4C N12 0.6(3) . . . . ?
C4A C4B C4C C4D 0.9(2) . . . . ?
C1 C4B C4C C4D 179.74(15) . . . . ?
N12 C4C C4D C7 1.4(3) . . . . ?
C4B C4C C4D C7 -177.77(15) . . . . ?
N12 C4C C4D C6 -178.36(15) . . . . ?
C4B C4C C4D C6 2.5(2) . . . . ?
C4A O5 C6 O17 -179.83(16) . . . . ?
C4A O5 C6 C4D 0.2(2) . . . . ?
C7 C4D C6 O17 -2.8(3) . . . . ?
C4C C4D C6 O17 176.97(17) . . . . ?
C7 C4D C6 O5 177.17(14) . . . . ?
C4C C4D C6 O5 -3.1(2) . . . . ?
C4C C4D C7 C7A -0.6(2) . . . . ?
C6 C4D C7 C7A 179.18(14) . . . . ?
C4D C7 C7A C8 179.33(15) . . . . ?
C4D C7 C7A C11A -0.6(2) . . . . ?
C9 C8 C7A C7 -179.94(15) . . . . ?
C9 C8 C7A C11A 0.0(2) . . . . ?
C7A C8 C9 C10 -0.9(2) . . . . ?
C7A C8 C9 C13 178.50(15) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C13 C9 C10 C11 -178.34(16) . . . . ?
C9 C10 C11 C11A -0.4(3) . . . . ?
C4C N12 C11A C11 -179.93(15) . . . . ?
C4C N12 C11A C7A -0.5(2) . . . . ?
C10 C11 C11A N12 178.95(15) . . . . ?
C10 C11 C11A C7A -0.5(3) . . . . ?
C7 C7A C11A N12 1.2(2) . . . . ?
C8 C7A C11A N12 -178.76(15) . . . . ?
C7 C7A C11A C11 -179.33(15) . . . . ?
C8 C7A C11A C11 0.7(2) . . . . ?
C8 C9 C13 O18 -176.98(16) . . . . ?
C10 C9 C13 O18 2.4(3) . . . . ?
C8 C9 C13 C14 2.7(2) . . . . ?
C10 C9 C13 C14 -177.85(16) . . . . ?
C3 N19 C15 C16 90.5(2) . . . . ?
C15A N19 C15 C16 -82.7(2) . . . . ?
C3 N19 C15A C16B 104.5(2) . . . . ?
C15 N19 C15A C16B -82.2(2) . . . . ?

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
C7 H7 O17 0.95 2.45 3.269(2) 144.0 2_566 yes
C8 H8 O17 0.95 2.45 3.268(2) 144.7 2_566 yes

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_OCIketone
_database_code_depnum_ccdc_archive 'CCDC 2551719'
loop_
_audit_author_name
_audit_author_address
'Frank Fronczek'
;LSU
United States of America
;
_audit_update_record             
;
2026-05-05 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1464(3)
_cell_length_b                   7.5016(2)
_cell_length_c                   20.9742(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.301(2)
_cell_angle_gamma                90
_cell_volume                     1909.57(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      78.64
_exptl_crystal_description       lath
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS 3.0 microfocus'
_diffrn_measurement_device_type  'Bruker D8 Venture DUO with Photon III C14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45830
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.642
_diffrn_reflns_theta_max         79.653
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4094
_reflns_number_gt                3617
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0484P)²+0.6028P] 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         4094
_refine_ls_number_parameters     268
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_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
O1 O 0.41487(6) 0.79482(10) 0.51530(4) 0.01689(17) Uani 1 1 d . . . . .
O2 O 0.53608(7) 0.90528(10) 0.58467(4) 0.01968(18) Uani 1 1 d . . . . .
O3 O 0.80383(6) 0.74242(11) 0.49203(4) 0.02230(18) Uani 1 1 d . . . . .
O4 O 0.82654(6) 0.33279(11) 0.41157(4) 0.02209(18) Uani 1 1 d . . . . .
N1 N 0.66641(8) 0.60442(12) 0.40411(4) 0.01636(19) Uani 1 1 d . . . . .
H1N H 0.7314(13) 0.6195(19) 0.4243(7) 0.020 Uiso 1 1 d . U . . .
N2 N 0.12496(8) 0.55969(13) 0.38513(5) 0.0220(2) Uani 1 1 d D . . . .
C2 C 0.52300(9) 0.82208(13) 0.53514(5) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.60807(9) 0.75392(13) 0.49585(5) 0.0156(2) Uani 1 1 d . . . . .
C4 C 0.58176(9) 0.66146(13) 0.43861(5) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.42488(9) 0.51789(13) 0.37178(5) 0.0156(2) Uani 1 1 d . . . . .
H5 H 0.475219 0.458985 0.345399 0.019 Uiso 1 1 calc R U . . .
C4A C 0.46728(8) 0.62770(13) 0.42180(5) 0.0146(2) Uani 1 1 d . . . . .
C6 C 0.31428(9) 0.49294(14) 0.35981(5) 0.0173(2) Uani 1 1 d . . . . .
H6 H 0.290110 0.417001 0.325805 0.021 Uiso 1 1 calc R U . . .
C7 C 0.23472(9) 0.57887(14) 0.39746(5) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.27558(9) 0.68197(14) 0.44929(5) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.225682 0.738894 0.476475 0.020 Uiso 1 1 calc R U . . .
C9 C 0.71929(9) 0.79247(14) 0.51763(5) 0.0183(2) Uani 1 1 d . . . . .
H9 H 0.728651 0.862827 0.555122 0.022 Uiso 1 1 calc R U . . .
C8A C 0.38714(9) 0.70079(13) 0.46081(5) 0.0152(2) Uani 1 1 d . . . . .
C10 C 0.66335(8) 0.55091(14) 0.33911(5) 0.0153(2) Uani 1 1 d . . . . .
C11 C 0.61245(9) 0.65986(14) 0.29292(5) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.582731 0.771637 0.304786 0.022 Uiso 1 1 calc R U . . .
C12 C 0.60502(9) 0.60558(15) 0.22955(5) 0.0201(2) Uani 1 1 d . . . . .
H12 H 0.568908 0.679401 0.198416 0.024 Uiso 1 1 calc R U . . .
C13 C 0.65010(10) 0.44398(16) 0.21147(5) 0.0220(2) Uani 1 1 d . . . . .
H13 H 0.645741 0.407697 0.168048 0.026 Uiso 1 1 calc R U . . .
C14 C 0.70144(10) 0.33623(15) 0.25729(5) 0.0214(2) Uani 1 1 d . . . . .
H14 H 0.731898 0.225486 0.244881 0.026 Uiso 1 1 calc R U . . .
C15 C 0.70938(9) 0.38703(14) 0.32141(5) 0.0166(2) Uani 1 1 d . . . . .
C16 C 0.76598(9) 0.26872(14) 0.36991(5) 0.0178(2) Uani 1 1 d . . . . .
C17 C 0.74381(10) 0.07166(15) 0.36593(6) 0.0241(2) Uani 1 1 d . . . . .
H17A H 0.789259 0.009612 0.398590 0.036 Uiso 1 1 calc R U . . .
H17B H 0.761943 0.027879 0.323596 0.036 Uiso 1 1 calc R U . . .
H17C H 0.665768 0.049112 0.373003 0.036 Uiso 1 1 calc R U . . .
C18A C 0.0857(13) 0.3764(19) 0.3596(7) 0.027(4) Uiso 0.081(4) 1 d D . P A 1
H18A H 0.149174 0.294761 0.355623 0.033 Uiso 0.081(4) 1 calc R U P A 1
H18B H 0.033246 0.321968 0.388781 0.033 Uiso 0.081(4) 1 calc R U P A 1
C19A C 0.0296(19) 0.410(3) 0.2942(9) 0.052(6) Uiso 0.081(4) 1 d D . P A 1
H19D H 0.003175 0.297348 0.275916 0.078 Uiso 0.081(4) 1 calc R U P A 1
H19E H -0.032813 0.491510 0.298863 0.078 Uiso 0.081(4) 1 calc R U P A 1
H19F H 0.082538 0.464438 0.265869 0.078 Uiso 0.081(4) 1 calc R U P A 1
C18 C 0.08095(10) 0.46482(17) 0.32887(6) 0.0225(3) Uani 0.919(4) 1 d D . P A 2
H18C H 0.129198 0.487182 0.292783 0.027 Uiso 0.919(4) 1 calc R U P A 2
H18D H 0.006936 0.512476 0.316999 0.027 Uiso 0.919(4) 1 calc R U P A 2
C19 C 0.07234(12) 0.26411(19) 0.33964(7) 0.0297(4) Uani 0.919(4) 1 d D . P A 2
H19A H 0.035766 0.208433 0.302198 0.045 Uiso 0.919(4) 1 calc R U P A 2
H19B H 0.029362 0.241315 0.377346 0.045 Uiso 0.919(4) 1 calc R U P A 2
H19C H 0.146355 0.213739 0.346280 0.045 Uiso 0.919(4) 1 calc R U P A 2
C20 C 0.04461(9) 0.64154(16) 0.42662(6) 0.0235(2) Uani 1 1 d . . . . .
H20A H 0.071567 0.630857 0.471635 0.028 Uiso 1 1 calc R U . . .
H20B H -0.026118 0.576344 0.421919 0.028 Uiso 1 1 calc R U . . .
C21 C 0.02527(11) 0.83739(17) 0.41072(8) 0.0328(3) Uani 1 1 d . . . . .
H21A H -0.026906 0.887995 0.440228 0.049 Uiso 1 1 calc R U . . .
H21B H -0.004993 0.848082 0.366865 0.049 Uiso 1 1 calc R U . . .
H21C H 0.095273 0.902141 0.414822 0.049 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
O1 C8A 1.3734(13) . ?
O1 C2 1.3770(13) . ?
O2 C2 1.2169(13) . ?
O3 C9 1.2362(14) . ?
O4 C16 1.2182(14) . ?
N1 C4 1.3503(14) . ?
N1 C10 1.4203(13) . ?
N1 H1N 0.888(16) . ?
N2 C7 1.3555(14) . ?
N2 C18 1.4607(16) . ?
N2 C20 1.4681(15) . ?
N2 C18A 1.544(13) . ?
C2 C3 1.4410(14) . ?
C3 C4 1.4121(14) . ?
C3 C9 1.4380(15) . ?
C4 C4A 1.4432(14) . ?
C5 C6 1.3696(15) . ?
C5 C4A 1.4145(15) . ?
C5 H5 0.9500 . ?
C4A C8A 1.4077(14) . ?
C6 C7 1.4262(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4082(15) . ?
C8 C8A 1.3742(15) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3931(15) . ?
C10 C15 1.4066(15) . ?
C11 C12 1.3896(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3892(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3849(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3973(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.4964(15) . ?
C16 C17 1.5043(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18A C19A 1.528(17) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C18 C19 1.5267(19) . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5228(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C8A O1 C2 121.79(8) . . ?
C4 N1 C10 127.79(9) . . ?
C4 N1 H1N 112.7(9) . . ?
C10 N1 H1N 118.9(9) . . ?
C7 N2 C18 122.07(10) . . ?
C7 N2 C20 120.98(10) . . ?
C18 N2 C20 116.89(9) . . ?
C7 N2 C18A 116.6(6) . . ?
C20 N2 C18A 112.0(6) . . ?
O2 C2 O1 115.12(9) . . ?
O2 C2 C3 126.74(10) . . ?
O1 C2 C3 118.14(9) . . ?
C4 C3 C9 123.13(9) . . ?
C4 C3 C2 121.17(9) . . ?
C9 C3 C2 115.66(9) . . ?
N1 C4 C3 117.39(9) . . ?
N1 C4 C4A 124.08(9) . . ?
C3 C4 C4A 118.48(9) . . ?
C6 C5 C4A 122.74(10) . . ?
C6 C5 H5 118.6 . . ?
C4A C5 H5 118.6 . . ?
C8A C4A C5 114.72(9) . . ?
C8A C4A C4 118.14(9) . . ?
C5 C4A C4 127.01(9) . . ?
C5 C6 C7 121.21(10) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
N2 C7 C8 121.26(10) . . ?
N2 C7 C6 121.97(10) . . ?
C8 C7 C6 116.75(10) . . ?
C8A C8 C7 120.44(10) . . ?
C8A C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O3 C9 C3 125.94(10) . . ?
O3 C9 H9 117.0 . . ?
C3 C9 H9 117.0 . . ?
O1 C8A C8 113.97(9) . . ?
O1 C8A C4A 122.11(9) . . ?
C8 C8A C4A 123.91(10) . . ?
C11 C10 C15 119.94(10) . . ?
C11 C10 N1 119.70(9) . . ?
C15 C10 N1 120.34(9) . . ?
C12 C11 C10 120.21(10) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.37(10) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.43(10) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.36(10) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.67(10) . . ?
C14 C15 C16 120.30(9) . . ?
C10 C15 C16 121.03(9) . . ?
O4 C16 C15 120.09(10) . . ?
O4 C16 C17 121.95(10) . . ?
C15 C16 C17 117.95(10) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19A C18A N2 106.4(13) . . ?
C19A C18A H18A 110.4 . . ?
N2 C18A H18A 110.4 . . ?
C19A C18A H18B 110.4 . . ?
N2 C18A H18B 110.4 . . ?
H18A C18A H18B 108.6 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
N2 C18 C19 112.71(11) . . ?
N2 C18 H18C 109.1 . . ?
C19 C18 H18C 109.1 . . ?
N2 C18 H18D 109.1 . . ?
C19 C18 H18D 109.1 . . ?
H18C C18 H18D 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 111.96(10) . . ?
N2 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C8A O1 C2 O2 -178.97(9) . . . . ?
C8A O1 C2 C3 2.04(14) . . . . ?
O2 C2 C3 C4 -178.95(10) . . . . ?
O1 C2 C3 C4 -0.08(14) . . . . ?
O2 C2 C3 C9 -1.23(16) . . . . ?
O1 C2 C3 C9 177.63(9) . . . . ?
C10 N1 C4 C3 -162.57(10) . . . . ?
C10 N1 C4 C4A 19.93(16) . . . . ?
C9 C3 C4 N1 1.45(15) . . . . ?
C2 C3 C4 N1 178.99(9) . . . . ?
C9 C3 C4 C4A 179.10(9) . . . . ?
C2 C3 C4 C4A -3.36(14) . . . . ?
C6 C5 C4A C8A 3.71(15) . . . . ?
C6 C5 C4A C4 179.47(10) . . . . ?
N1 C4 C4A C8A -177.66(9) . . . . ?
C3 C4 C4A C8A 4.87(14) . . . . ?
N1 C4 C4A C5 6.72(16) . . . . ?
C3 C4 C4A C5 -170.76(10) . . . . ?
C4A C5 C6 C7 0.49(16) . . . . ?
C18 N2 C7 C8 175.20(10) . . . . ?
C20 N2 C7 C8 -1.86(16) . . . . ?
C18A N2 C7 C8 -144.1(7) . . . . ?
C18 N2 C7 C6 -6.29(16) . . . . ?
C20 N2 C7 C6 176.64(10) . . . . ?
C18A N2 C7 C6 34.4(7) . . . . ?
C5 C6 C7 N2 178.08(10) . . . . ?
C5 C6 C7 C8 -3.35(15) . . . . ?
N2 C7 C8 C8A -179.59(10) . . . . ?
C6 C7 C8 C8A 1.83(15) . . . . ?
C4 C3 C9 O3 -4.44(17) . . . . ?
C2 C3 C9 O3 177.90(10) . . . . ?
C2 O1 C8A C8 178.12(9) . . . . ?
C2 O1 C8A C4A -0.41(14) . . . . ?
C7 C8 C8A O1 -175.84(9) . . . . ?
C7 C8 C8A C4A 2.66(16) . . . . ?
C5 C4A C8A O1 173.05(9) . . . . ?
C4 C4A C8A O1 -3.11(14) . . . . ?
C5 C4A C8A C8 -5.34(15) . . . . ?
C4 C4A C8A C8 178.50(9) . . . . ?
C4 N1 C10 C11 49.80(15) . . . . ?
C4 N1 C10 C15 -128.89(11) . . . . ?
C15 C10 C11 C12 1.30(16) . . . . ?
N1 C10 C11 C12 -177.39(10) . . . . ?
C10 C11 C12 C13 -1.26(17) . . . . ?
C11 C12 C13 C14 0.76(17) . . . . ?
C12 C13 C14 C15 -0.32(18) . . . . ?
C13 C14 C15 C10 0.35(17) . . . . ?
C13 C14 C15 C16 -179.57(10) . . . . ?
C11 C10 C15 C14 -0.84(15) . . . . ?
N1 C10 C15 C14 177.84(10) . . . . ?
C11 C10 C15 C16 179.08(9) . . . . ?
N1 C10 C15 C16 -2.23(15) . . . . ?
C14 C15 C16 O4 138.71(11) . . . . ?
C10 C15 C16 O4 -41.21(14) . . . . ?
C14 C15 C16 C17 -42.40(14) . . . . ?
C10 C15 C16 C17 137.68(11) . . . . ?
C7 N2 C18A C19A -119.8(12) . . . . ?
C20 N2 C18A C19A 94.7(12) . . . . ?
C7 N2 C18 C19 85.91(14) . . . . ?
C20 N2 C18 C19 -96.91(12) . . . . ?
C7 N2 C20 C21 81.96(14) . . . . ?
C18 N2 C20 C21 -95.25(13) . . . . ?
C18A N2 C20 C21 -134.3(6) . . . . ?

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 H1N O3 0.888(16) 1.882(16) 2.6477(12) 143.3(13) . yes
C8 H8 O4 0.95 2.51 3.2184(13) 130.9 3_666 yes
C17 H17C O2 0.98 2.66 3.5978(14) 159.6 3_666 yes
C18A H18B O4 0.99 2.58 3.389(16) 139.4 1_455 yes
C19 H19B O4 0.98 2.68 3.4375(16) 134.1 1_455 yes
C20 H20A O4 0.99 2.71 3.6848(15) 166.9 3_666 yes
C20 H20B O4 0.99 2.56 3.5231(14) 164.1 1_455 yes
C21 H21A O3 0.98 2.60 3.3195(16) 130.0 1_455 yes

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047

