# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cu_kkd006b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2269893'
loop_
_audit_author_name
_audit_author_address
'Daisy Pooler'
;Rijksuniversiteit Groningen
Netherlands
;
_audit_update_record             
;
2023-06-14 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
5-(2-hydroxy-5-methoxy-2,7-dimethyl-2,3-dihydro-1H-inden-1-ylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
_chemical_formula_moiety         'C18 H20 N2 O5'
_chemical_formula_sum            'C18 H20 N2 O5'
_chemical_formula_weight         344.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1319(7)
_cell_length_b                   25.5792(18)
_cell_length_c                   12.5674(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.459(2)
_cell_angle_gamma                90
_cell_volume                     3256.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9736
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.22
_cell_measurement_theta_min      5.57
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.9175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, pentane'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            85279
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.215
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5866
_reflns_number_total             6416
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         6416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.046
_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)+(0.0405P)²+1.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0853
_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
O23B O 0.62542(9) 0.34017(4) 0.70145(7) 0.0244(2) Uani 1 1 d . . . . .
O21B O 0.30847(8) 0.34380(3) 0.44523(7) 0.01941(18) Uani 1 1 d . . . . .
O17B O 0.60610(8) 0.43911(3) 0.22431(7) 0.01837(18) Uani 1 1 d . . . . .
H17B H 0.6649(19) 0.4449(8) 0.2747(16) 0.038(5) Uiso 1 1 d . . . . .
O25B O 0.69238(8) 0.44829(4) 0.42293(7) 0.02263(19) Uani 1 1 d . . . . .
O18B O -0.10288(8) 0.46619(4) 0.21687(7) 0.02087(19) Uani 1 1 d . . . . .
N14B N 0.66030(9) 0.39186(4) 0.55696(8) 0.0177(2) Uani 1 1 d . . . . .
N12B N 0.46864(10) 0.34045(4) 0.57054(8) 0.0192(2) Uani 1 1 d . . . . .
C9B C 0.27704(11) 0.44164(4) 0.33204(9) 0.0155(2) Uani 1 1 d . . . . .
C10B C 0.47990(11) 0.40696(5) 0.43131(9) 0.0158(2) Uani 1 1 d . . . . .
C1B C 0.41814(11) 0.43522(4) 0.35140(9) 0.0152(2) Uani 1 1 d . . . . .
C15B C 0.61693(11) 0.41708(5) 0.46518(9) 0.0172(2) Uani 1 1 d . . . . .
C6B C 0.02457(11) 0.46037(5) 0.24840(10) 0.0171(2) Uani 1 1 d . . . . .
C8B C 0.16701(11) 0.44173(4) 0.40177(9) 0.0160(2) Uani 1 1 d . . . . .
C13B C 0.58705(11) 0.35652(5) 0.61557(10) 0.0178(2) Uani 1 1 d . . . . .
C4B C 0.25684(11) 0.45534(4) 0.22463(9) 0.0158(2) Uani 1 1 d . . . . .
C11B C 0.41023(11) 0.36263(5) 0.48050(9) 0.0162(2) Uani 1 1 d . . . . .
C20B C 0.17730(12) 0.43585(5) 0.52066(9) 0.0185(2) Uani 1 1 d . . . . .
H20A H 0.1648(15) 0.3995(7) 0.5407(13) 0.022(4) Uiso 1 1 d . . . . .
H20B H 0.2654(16) 0.4466(7) 0.5493(13) 0.027(4) Uiso 1 1 d . . . . .
H20C H 0.1088(16) 0.4568(7) 0.5554(14) 0.029(4) Uiso 1 1 d . . . . .
C24B C 0.79191(12) 0.40548(6) 0.59824(11) 0.0242(3) Uani 1 1 d . . . . .
H24A H 0.796(2) 0.4396(10) 0.6250(19) 0.058(6) Uiso 1 1 d . . . . .
H24B H 0.854(2) 0.4039(8) 0.5395(18) 0.049(6) Uiso 1 1 d . . . . .
H24C H 0.818(2) 0.3785(10) 0.648(2) 0.063(7) Uiso 1 1 d . . . . .
C22B C 0.40017(14) 0.29653(6) 0.62053(12) 0.0264(3) Uani 1 1 d . . . . .
H22A H 0.465(2) 0.2770(9) 0.6612(18) 0.054(6) Uiso 1 1 d . . . . .
H22B H 0.326(2) 0.3095(8) 0.6618(17) 0.048(5) Uiso 1 1 d . . . . .
H22C H 0.362(2) 0.2743(9) 0.5667(18) 0.050(6) Uiso 1 1 d . . . . .
C3B C 0.38605(11) 0.45730(5) 0.16783(9) 0.0169(2) Uani 1 1 d . . . . .
H3BA H 0.3925(15) 0.4864(6) 0.1143(13) 0.021(4) Uiso 1 1 d . . . . .
H3BB H 0.4002(15) 0.4243(7) 0.1324(13) 0.021(4) Uiso 1 1 d . . . . .
C2B C 0.48858(11) 0.46335(5) 0.25890(9) 0.0158(2) Uani 1 1 d . . . . .
C5B C 0.13306(11) 0.46460(5) 0.18115(9) 0.0168(2) Uani 1 1 d . . . . .
H5B H 0.1228(13) 0.4732(6) 0.1072(12) 0.014(3) Uiso 1 1 d . . . . .
C7B C 0.04337(11) 0.45077(5) 0.35757(10) 0.0177(2) Uani 1 1 d . . . . .
H7B H -0.0356(15) 0.4512(6) 0.4015(12) 0.019(4) Uiso 1 1 d . . . . .
C16B C 0.51029(12) 0.52128(5) 0.28439(10) 0.0200(2) Uani 1 1 d . . . . .
H16A H 0.5585(16) 0.5377(7) 0.2250(14) 0.028(4) Uiso 1 1 d . . . . .
H16B H 0.5639(16) 0.5243(7) 0.3516(14) 0.028(4) Uiso 1 1 d . . . . .
H16C H 0.4245(17) 0.5394(7) 0.2934(14) 0.031(4) Uiso 1 1 d . . . . .
C19B C -0.12752(12) 0.47484(5) 0.10552(10) 0.0206(2) Uani 1 1 d . . . . .
H19A H -0.0925(15) 0.4458(7) 0.0641(13) 0.022(4) Uiso 1 1 d . . . . .
H19B H -0.2223(17) 0.4771(7) 0.0994(13) 0.027(4) Uiso 1 1 d . . . . .
H19C H -0.0861(15) 0.5081(7) 0.0832(13) 0.024(4) Uiso 1 1 d . . . . .
O17 O 0.59207(9) 0.10621(3) 0.46697(7) 0.01881(18) Uani 1 1 d . . . . .
H17 H 0.676(2) 0.0955(8) 0.4637(16) 0.043(5) Uiso 1 1 d . . . . .
O21 O 0.76916(8) 0.27684(3) 0.50579(7) 0.01920(18) Uani 1 1 d . . . . .
O18 O 0.31409(8) 0.32688(3) 0.18795(7) 0.01976(18) Uani 1 1 d . . . . .
O25 O 0.84281(8) 0.10033(3) 0.42245(7) 0.02140(19) Uani 1 1 d . . . . .
O23 O 1.18161(8) 0.20905(4) 0.50025(8) 0.0239(2) Uani 1 1 d . . . . .
N12 N 0.97673(9) 0.24532(4) 0.49072(8) 0.0178(2) Uani 1 1 d . . . . .
N14 N 1.00911(9) 0.15497(4) 0.46353(8) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.66641(11) 0.18985(4) 0.38637(9) 0.0145(2) Uani 1 1 d . . . . .
C24 C 1.10166(12) 0.11073(5) 0.46125(11) 0.0209(2) Uani 1 1 d . . . . .
H24D H 1.055(2) 0.0792(9) 0.4710(17) 0.051(6) Uiso 1 1 d . . . . .
H24E H 1.164(2) 0.1159(9) 0.5143(19) 0.059(6) Uiso 1 1 d . . . . .
H24F H 1.143(2) 0.1082(9) 0.3922(18) 0.051(6) Uiso 1 1 d . . . . .
C19 C 0.17469(12) 0.31647(5) 0.19560(11) 0.0234(3) Uani 1 1 d . . . . .
H19D H 0.1516(15) 0.2829(7) 0.1624(13) 0.023(4) Uiso 1 1 d . . . . .
H19E H 0.1306(16) 0.3461(7) 0.1578(14) 0.029(4) Uiso 1 1 d . . . . .
H19F H 0.1473(16) 0.3151(7) 0.2702(14) 0.026(4) Uiso 1 1 d . . . . .
C22 C 1.03048(13) 0.29515(5) 0.52850(12) 0.0240(3) Uani 1 1 d . . . . .
H22D H 1.025(2) 0.2975(11) 0.606(2) 0.074(8) Uiso 1 1 d . . . . .
H22E H 0.980(2) 0.3233(9) 0.4947(18) 0.056(6) Uiso 1 1 d . . . . .
H22F H 1.1207(19) 0.2999(8) 0.5052(15) 0.038(5) Uiso 1 1 d . . . . .
C2 C 0.57911(11) 0.14038(4) 0.37850(9) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.43904(11) 0.16376(5) 0.38153(10) 0.0177(2) Uani 1 1 d . . . . .
H3A H 0.4118(15) 0.1676(6) 0.4559(14) 0.023(4) Uiso 1 1 d . . . . .
H3B H 0.3730(16) 0.1413(7) 0.3433(13) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.45643(11) 0.21664(5) 0.33287(9) 0.0161(2) Uani 1 1 d . . . . .
C5 C 0.35904(11) 0.24628(5) 0.28426(9) 0.0171(2) Uani 1 1 d . . . . .
H5 H 0.2692(16) 0.2349(7) 0.2796(13) 0.025(4) Uiso 1 1 d . . . . .
C6 C 0.39711(11) 0.29352(5) 0.23939(9) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.52982(11) 0.30925(5) 0.24126(9) 0.0166(2) Uani 1 1 d . . . . .
H7 H 0.5545(15) 0.3414(6) 0.2061(12) 0.021(4) Uiso 1 1 d . . . . .
C8 C 0.62843(11) 0.27980(5) 0.28998(9) 0.0158(2) Uani 1 1 d . . . . .
C9 C 0.58981(11) 0.23229(5) 0.33966(9) 0.0153(2) Uani 1 1 d . . . . .
C10 C 0.79113(11) 0.19182(5) 0.43156(9) 0.0154(2) Uani 1 1 d . . . . .
C11 C 0.84029(11) 0.24115(5) 0.47766(9) 0.0158(2) Uani 1 1 d . . . . .
C13 C 1.06385(11) 0.20378(5) 0.48481(9) 0.0176(2) Uani 1 1 d . . . . .
C15 C 0.87736(11) 0.14573(5) 0.43979(9) 0.0164(2) Uani 1 1 d . . . . .
C16 C 0.60111(12) 0.11157(5) 0.27322(10) 0.0186(2) Uani 1 1 d . . . . .
H16D H 0.6918(17) 0.0991(7) 0.2679(13) 0.026(4) Uiso 1 1 d . . . . .
H16E H 0.5423(16) 0.0812(7) 0.2687(13) 0.025(4) Uiso 1 1 d . . . . .
H16F H 0.5818(16) 0.1348(7) 0.2134(14) 0.026(4) Uiso 1 1 d . . . . .
C20 C 0.76791(12) 0.29965(5) 0.27997(10) 0.0194(2) Uani 1 1 d . . . . .
H20D H 0.8344(15) 0.2717(7) 0.2851(13) 0.022(4) Uiso 1 1 d . . . . .
H20E H 0.7776(16) 0.3163(7) 0.2119(15) 0.031(4) Uiso 1 1 d . . . . .
H20F H 0.7879(16) 0.3248(7) 0.3339(14) 0.029(4) Uiso 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
O23B C13B 1.2183(15) . ?
O21B C11B 1.2183(15) . ?
O17B H17B 0.88(2) . ?
O17B C2B 1.4140(14) . ?
O25B C15B 1.2288(15) . ?
O18B C6B 1.3560(14) . ?
O18B C19B 1.4366(15) . ?
N14B C15B 1.3898(15) . ?
N14B C13B 1.3854(16) . ?
N14B C24B 1.4688(15) . ?
N12B C13B 1.3848(16) . ?
N12B C11B 1.3935(15) . ?
N12B C22B 1.4646(16) . ?
C9B C1B 1.4575(16) . ?
C9B C8B 1.4235(16) . ?
C9B C4B 1.4080(16) . ?
C10B C1B 1.3829(16) . ?
C10B C15B 1.4719(16) . ?
C10B C11B 1.4741(16) . ?
C1B C2B 1.5466(16) . ?
C6B C5B 1.3961(17) . ?
C6B C7B 1.4053(17) . ?
C8B C20B 1.5045(16) . ?
C8B C7B 1.3857(16) . ?
C4B C3B 1.4969(15) . ?
C4B C5B 1.3844(16) . ?
C20B H20A 0.973(17) . ?
C20B H20B 0.998(17) . ?
C20B H20C 0.982(18) . ?
C24B H24A 0.94(3) . ?
C24B H24B 0.97(2) . ?
C24B H24C 0.96(3) . ?
C22B H22A 0.97(2) . ?
C22B H22B 0.97(2) . ?
C22B H22C 0.96(2) . ?
C3B H3BA 1.007(16) . ?
C3B H3BB 0.965(17) . ?
C3B C2B 1.5473(15) . ?
C2B C16B 1.5315(17) . ?
C5B H5B 0.960(15) . ?
C7B H7B 0.976(15) . ?
C16B H16A 0.989(18) . ?
C16B H16B 1.003(17) . ?
C16B H16C 0.992(18) . ?
C19B H19A 0.975(17) . ?
C19B H19B 0.965(17) . ?
C19B H19C 0.991(17) . ?
O17 H17 0.90(2) . ?
O17 C2 1.4196(14) . ?
O21 C11 1.2173(15) . ?
O18 C19 1.4412(15) . ?
O18 C6 1.3582(14) . ?
O25 C15 1.2318(15) . ?
O23 C13 1.2148(15) . ?
N12 C22 1.4636(15) . ?
N12 C11 1.3949(15) . ?
N12 C13 1.3838(16) . ?
N14 C24 1.4702(15) . ?
N14 C13 1.3910(16) . ?
N14 C15 1.3858(15) . ?
C1 C2 1.5467(15) . ?
C1 C9 1.4553(16) . ?
C1 C10 1.3822(16) . ?
C24 H24D 0.94(2) . ?
C24 H24E 0.93(2) . ?
C24 H24F 0.97(2) . ?
C19 H19D 0.983(17) . ?
C19 H19E 0.998(18) . ?
C19 H19F 0.980(18) . ?
C22 H22D 0.98(3) . ?
C22 H22E 0.98(2) . ?
C22 H22F 0.970(19) . ?
C2 C3 1.5408(16) . ?
C2 C16 1.5324(16) . ?
C3 H3A 0.981(17) . ?
C3 H3B 1.002(17) . ?
C3 C4 1.4956(16) . ?
C4 C5 1.3828(16) . ?
C4 C9 1.4113(16) . ?
C5 H5 0.958(17) . ?
C5 C6 1.3894(17) . ?
C6 C7 1.4035(17) . ?
C7 H7 0.968(16) . ?
C7 C8 1.3896(16) . ?
C8 C9 1.4225(16) . ?
C8 C20 1.5079(16) . ?
C10 C11 1.4736(16) . ?
C10 C15 1.4706(16) . ?
C16 H16D 0.975(17) . ?
C16 H16E 0.980(17) . ?
C16 H16F 0.977(18) . ?
C20 H20D 0.985(16) . ?
C20 H20E 0.962(19) . ?
C20 H20F 0.955(18) . ?

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
C2B O17B H17B 105.8(12) . . ?
C6B O18B C19B 117.34(9) . . ?
C15B N14B C24B 117.59(10) . . ?
C13B N14B C15B 125.24(10) . . ?
C13B N14B C24B 117.10(10) . . ?
C13B N12B C11B 124.88(10) . . ?
C13B N12B C22B 117.65(10) . . ?
C11B N12B C22B 117.46(10) . . ?
C8B C9B C1B 132.02(11) . . ?
C4B C9B C1B 108.84(10) . . ?
C4B C9B C8B 118.77(10) . . ?
C1B C10B C15B 122.57(11) . . ?
C1B C10B C11B 119.42(10) . . ?
C15B C10B C11B 117.89(10) . . ?
C9B C1B C2B 106.26(9) . . ?
C10B C1B C9B 128.14(11) . . ?
C10B C1B C2B 125.46(10) . . ?
O25B C15B N14B 117.81(10) . . ?
O25B C15B C10B 125.30(11) . . ?
N14B C15B C10B 116.72(10) . . ?
O18B C6B C5B 124.55(11) . . ?
O18B C6B C7B 115.20(10) . . ?
C5B C6B C7B 120.22(11) . . ?
C9B C8B C20B 124.25(10) . . ?
C7B C8B C9B 117.61(10) . . ?
C7B C8B C20B 118.04(10) . . ?
O23B C13B N14B 121.77(11) . . ?
O23B C13B N12B 121.97(11) . . ?
N12B C13B N14B 116.26(10) . . ?
C9B C4B C3B 110.15(10) . . ?
C5B C4B C9B 123.04(10) . . ?
C5B C4B C3B 126.80(10) . . ?
O21B C11B N12B 119.15(11) . . ?
O21B C11B C10B 123.93(10) . . ?
N12B C11B C10B 116.88(10) . . ?
C8B C20B H20A 110.1(9) . . ?
C8B C20B H20B 112.7(10) . . ?
C8B C20B H20C 110.0(10) . . ?
H20A C20B H20B 106.7(13) . . ?
H20A C20B H20C 108.3(14) . . ?
H20B C20B H20C 108.8(14) . . ?
N14B C24B H24A 112.4(14) . . ?
N14B C24B H24B 108.1(12) . . ?
N14B C24B H24C 107.3(14) . . ?
H24A C24B H24B 106.7(19) . . ?
H24A C24B H24C 115(2) . . ?
H24B C24B H24C 106.8(19) . . ?
N12B C22B H22A 107.6(13) . . ?
N12B C22B H22B 109.7(13) . . ?
N12B C22B H22C 109.9(13) . . ?
H22A C22B H22B 114.6(18) . . ?
H22A C22B H22C 109.4(18) . . ?
H22B C22B H22C 105.7(17) . . ?
C4B C3B H3BA 113.9(9) . . ?
C4B C3B H3BB 108.9(9) . . ?
C4B C3B C2B 103.60(9) . . ?
H3BA C3B H3BB 109.2(13) . . ?
C2B C3B H3BA 111.9(9) . . ?
C2B C3B H3BB 109.1(9) . . ?
O17B C2B C1B 114.95(9) . . ?
O17B C2B C3B 106.90(9) . . ?
O17B C2B C16B 111.64(9) . . ?
C3B C2B C1B 101.44(9) . . ?
C16B C2B C1B 111.05(10) . . ?
C16B C2B C3B 110.24(10) . . ?
C6B C5B H5B 121.6(8) . . ?
C4B C5B C6B 117.58(11) . . ?
C4B C5B H5B 120.8(8) . . ?
C6B C7B H7B 116.4(9) . . ?
C8B C7B C6B 122.38(11) . . ?
C8B C7B H7B 121.2(9) . . ?
C2B C16B H16A 108.9(10) . . ?
C2B C16B H16B 109.1(10) . . ?
C2B C16B H16C 110.6(10) . . ?
H16A C16B H16B 109.6(14) . . ?
H16A C16B H16C 109.0(14) . . ?
H16B C16B H16C 109.7(14) . . ?
O18B C19B H19A 110.0(9) . . ?
O18B C19B H19B 104.6(10) . . ?
O18B C19B H19C 109.8(9) . . ?
H19A C19B H19B 111.7(13) . . ?
H19A C19B H19C 110.2(13) . . ?
H19B C19B H19C 110.5(13) . . ?
C2 O17 H17 103.6(13) . . ?
C6 O18 C19 117.12(10) . . ?
C11 N12 C22 118.07(10) . . ?
C13 N12 C22 116.77(10) . . ?
C13 N12 C11 124.53(10) . . ?
C13 N14 C24 116.18(10) . . ?
C15 N14 C24 118.54(10) . . ?
C15 N14 C13 125.20(10) . . ?
C9 C1 C2 106.36(9) . . ?
C10 C1 C2 125.21(10) . . ?
C10 C1 C9 128.42(11) . . ?
N14 C24 H24D 109.6(13) . . ?
N14 C24 H24E 108.0(15) . . ?
N14 C24 H24F 110.5(13) . . ?
H24D C24 H24E 111.7(19) . . ?
H24D C24 H24F 106.2(18) . . ?
H24E C24 H24F 110.9(19) . . ?
O18 C19 H19D 111.3(9) . . ?
O18 C19 H19E 105.3(10) . . ?
O18 C19 H19F 110.8(9) . . ?
H19D C19 H19E 111.0(13) . . ?
H19D C19 H19F 107.8(14) . . ?
H19E C19 H19F 110.7(14) . . ?
N12 C22 H22D 110.5(16) . . ?
N12 C22 H22E 108.0(13) . . ?
N12 C22 H22F 111.1(12) . . ?
H22D C22 H22E 111(2) . . ?
H22D C22 H22F 111.0(18) . . ?
H22E C22 H22F 105.6(18) . . ?
O17 C2 C1 113.86(9) . . ?
O17 C2 C3 107.40(9) . . ?
O17 C2 C16 111.53(9) . . ?
C3 C2 C1 101.96(9) . . ?
C16 C2 C1 111.20(9) . . ?
C16 C2 C3 110.39(9) . . ?
C2 C3 H3A 109.2(9) . . ?
C2 C3 H3B 112.2(9) . . ?
H3A C3 H3B 108.8(13) . . ?
C4 C3 C2 103.26(9) . . ?
C4 C3 H3A 109.5(10) . . ?
C4 C3 H3B 113.8(10) . . ?
C5 C4 C3 126.19(11) . . ?
C5 C4 C9 123.42(11) . . ?
C9 C4 C3 110.35(10) . . ?
C4 C5 H5 122.3(10) . . ?
C4 C5 C6 117.17(11) . . ?
C6 C5 H5 120.5(10) . . ?
O18 C6 C5 124.51(11) . . ?
O18 C6 C7 114.67(11) . . ?
C5 C6 C7 120.77(11) . . ?
C6 C7 H7 119.1(9) . . ?
C8 C7 C6 122.50(11) . . ?
C8 C7 H7 118.4(9) . . ?
C7 C8 C9 117.21(10) . . ?
C7 C8 C20 116.85(11) . . ?
C9 C8 C20 125.85(10) . . ?
C4 C9 C1 108.67(10) . . ?
C4 C9 C8 118.84(10) . . ?
C8 C9 C1 131.80(10) . . ?
C1 C10 C11 119.85(10) . . ?
C1 C10 C15 122.72(10) . . ?
C15 C10 C11 117.39(10) . . ?
O21 C11 N12 119.80(10) . . ?
O21 C11 C10 123.87(10) . . ?
N12 C11 C10 116.32(10) . . ?
O23 C13 N12 122.15(11) . . ?
O23 C13 N14 121.33(11) . . ?
N12 C13 N14 116.49(10) . . ?
O25 C15 N14 118.09(10) . . ?
O25 C15 C10 125.14(10) . . ?
N14 C15 C10 116.68(10) . . ?
C2 C16 H16D 111.1(10) . . ?
C2 C16 H16E 109.8(10) . . ?
C2 C16 H16F 110.0(10) . . ?
H16D C16 H16E 108.1(14) . . ?
H16D C16 H16F 109.3(14) . . ?
H16E C16 H16F 108.7(14) . . ?
C8 C20 H20D 113.0(9) . . ?
C8 C20 H20E 109.0(10) . . ?
C8 C20 H20F 111.2(10) . . ?
H20D C20 H20E 107.7(14) . . ?
H20D C20 H20F 107.5(14) . . ?
H20E C20 H20F 108.2(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
O17B H17B O25B 0.88(2) 1.88(2) 2.6485(12) 144.5(17) . yes
O17 H17 O25 0.90(2) 1.78(2) 2.6101(12) 153.9(19) . 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
O18B C6B C5B C4B -177.25(11) . . . . ?
O18B C6B C7B C8B 177.22(11) . . . . ?
C9B C1B C2B O17B -144.34(10) . . . . ?
C9B C1B C2B C3B -29.42(11) . . . . ?
C9B C1B C2B C16B 87.72(11) . . . . ?
C9B C8B C7B C6B -0.91(17) . . . . ?
C9B C4B C3B C2B -20.11(13) . . . . ?
C9B C4B C5B C6B 0.54(18) . . . . ?
C10B C1B C2B O17B 31.75(16) . . . . ?
C10B C1B C2B C3B 146.67(11) . . . . ?
C10B C1B C2B C16B -96.19(13) . . . . ?
C1B C9B C8B C20B 1.6(2) . . . . ?
C1B C9B C8B C7B 177.83(12) . . . . ?
C1B C9B C4B C3B 1.29(13) . . . . ?
C1B C9B C4B C5B -179.53(11) . . . . ?
C1B C10B C15B O25B -5.09(19) . . . . ?
C1B C10B C15B N14B 170.06(11) . . . . ?
C1B C10B C11B O21B 11.41(18) . . . . ?
C1B C10B C11B N12B -170.90(11) . . . . ?
C15B N14B C13B O23B -171.83(11) . . . . ?
C15B N14B C13B N12B 8.81(17) . . . . ?
C15B C10B C1B C9B -158.74(11) . . . . ?
C15B C10B C1B C2B 26.04(18) . . . . ?
C15B C10B C11B O21B -164.68(11) . . . . ?
C15B C10B C11B N12B 13.01(15) . . . . ?
C8B C9B C1B C10B 29.7(2) . . . . ?
C8B C9B C1B C2B -154.35(12) . . . . ?
C8B C9B C4B C3B 175.09(10) . . . . ?
C8B C9B C4B C5B -5.73(17) . . . . ?
C13B N14B C15B O25B 178.58(11) . . . . ?
C13B N14B C15B C10B 3.05(17) . . . . ?
C13B N12B C11B O21B 176.88(11) . . . . ?
C13B N12B C11B C10B -0.92(17) . . . . ?
C4B C9B C1B C10B -157.63(12) . . . . ?
C4B C9B C1B C2B 18.32(12) . . . . ?
C4B C9B C8B C20B -170.45(11) . . . . ?
C4B C9B C8B C7B 5.74(16) . . . . ?
C4B C3B C2B O17B 150.00(9) . . . . ?
C4B C3B C2B C1B 29.25(11) . . . . ?
C4B C3B C2B C16B -88.48(11) . . . . ?
C11B N12B C13B O23B 170.72(11) . . . . ?
C11B N12B C13B N14B -9.93(17) . . . . ?
C11B C10B C1B C9B 25.37(18) . . . . ?
C11B C10B C1B C2B -149.85(11) . . . . ?
C11B C10B C15B O25B 170.87(12) . . . . ?
C11B C10B C15B N14B -13.98(15) . . . . ?
C20B C8B C7B C6B 175.52(11) . . . . ?
C24B N14B C15B O25B 1.60(17) . . . . ?
C24B N14B C15B C10B -173.92(11) . . . . ?
C24B N14B C13B O23B 5.16(17) . . . . ?
C24B N14B C13B N12B -174.20(11) . . . . ?
C22B N12B C13B O23B -9.93(18) . . . . ?
C22B N12B C13B N14B 169.42(11) . . . . ?
C22B N12B C11B O21B -2.47(17) . . . . ?
C22B N12B C11B C10B 179.72(11) . . . . ?
C3B C4B C5B C6B 179.58(11) . . . . ?
C5B C6B C7B C8B -4.34(18) . . . . ?
C5B C4B C3B C2B 160.75(11) . . . . ?
C7B C6B C5B C4B 4.46(17) . . . . ?
C19B O18B C6B C5B 3.09(17) . . . . ?
C19B O18B C6B C7B -178.55(11) . . . . ?
O17 C2 C3 C4 149.24(9) . . . . ?
O18 C6 C7 C8 -179.71(10) . . . . ?
C1 C2 C3 C4 29.26(11) . . . . ?
C1 C10 C11 O21 21.02(17) . . . . ?
C1 C10 C11 N12 -160.41(10) . . . . ?
C1 C10 C15 O25 -10.92(18) . . . . ?
C1 C10 C15 N14 165.52(10) . . . . ?
C24 N14 C13 O23 0.17(17) . . . . ?
C24 N14 C13 N12 -177.83(10) . . . . ?
C24 N14 C15 O25 3.16(16) . . . . ?
C24 N14 C15 C10 -173.53(10) . . . . ?
C19 O18 C6 C5 10.41(17) . . . . ?
C19 O18 C6 C7 -171.92(10) . . . . ?
C22 N12 C11 O21 -6.01(17) . . . . ?
C22 N12 C11 C10 175.35(11) . . . . ?
C22 N12 C13 O23 -6.80(17) . . . . ?
C22 N12 C13 N14 171.18(11) . . . . ?
C2 C1 C9 C4 16.20(12) . . . . ?
C2 C1 C9 C8 -153.89(12) . . . . ?
C2 C1 C10 C11 -152.77(11) . . . . ?
C2 C1 C10 C15 24.83(17) . . . . ?
C2 C3 C4 C5 156.55(11) . . . . ?
C2 C3 C4 C9 -21.37(12) . . . . ?
C3 C4 C5 C6 -176.98(11) . . . . ?
C3 C4 C9 C1 3.39(13) . . . . ?
C3 C4 C9 C8 174.98(10) . . . . ?
C4 C5 C6 O18 179.32(11) . . . . ?
C4 C5 C6 C7 1.79(17) . . . . ?
C5 C4 C9 C1 -174.59(11) . . . . ?
C5 C4 C9 C8 -3.01(17) . . . . ?
C5 C6 C7 C8 -1.94(18) . . . . ?
C6 C7 C8 C9 -0.42(17) . . . . ?
C6 C7 C8 C20 176.24(11) . . . . ?
C7 C8 C9 C1 172.05(12) . . . . ?
C7 C8 C9 C4 2.77(16) . . . . ?
C9 C1 C2 O17 -143.67(10) . . . . ?
C9 C1 C2 C3 -28.33(11) . . . . ?
C9 C1 C2 C16 89.33(11) . . . . ?
C9 C1 C10 C11 25.76(18) . . . . ?
C9 C1 C10 C15 -156.64(11) . . . . ?
C9 C4 C5 C6 0.68(17) . . . . ?
C10 C1 C2 O17 35.13(15) . . . . ?
C10 C1 C2 C3 150.47(11) . . . . ?
C10 C1 C2 C16 -91.88(13) . . . . ?
C10 C1 C9 C4 -162.54(11) . . . . ?
C10 C1 C9 C8 27.4(2) . . . . ?
C11 N12 C13 O23 -177.51(11) . . . . ?
C11 N12 C13 N14 0.48(17) . . . . ?
C11 C10 C15 O25 166.74(11) . . . . ?
C11 C10 C15 N14 -16.83(15) . . . . ?
C13 N12 C11 O21 164.58(11) . . . . ?
C13 N12 C11 C10 -14.06(17) . . . . ?
C13 N14 C15 O25 179.87(11) . . . . ?
C13 N14 C15 C10 3.18(16) . . . . ?
C15 N14 C13 O23 -176.61(11) . . . . ?
C15 N14 C13 N12 5.39(17) . . . . ?
C15 C10 C11 O21 -156.71(11) . . . . ?
C15 C10 C11 N12 21.86(15) . . . . ?
C16 C2 C3 C4 -88.97(11) . . . . ?
C20 C8 C9 C1 -4.3(2) . . . . ?
C20 C8 C9 C4 -173.56(11) . . . . ?

_olex2_submission_original_sample_id KKD006b
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
