# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 31 10:31:59 2021
#   Inital geometry file: a 228 line input string
#   Ligand name: (3-{(1R)-3-(3,4-dimethoxyphenyl)-1-[({(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidin-2-yl}carbonyl)oxy]propyl}phenoxy)acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@H](C(=O)N1CCCC[C@H]1C(=O)O[C@H](CCc2ccc(OC)c(OC)c2)c3cccc(OCC(O)=O)c3)c4cc(OC)c(OC)c(OC)c4
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 AP1  AP1  '(3-{(1R)-3-(3,4-dimethoxyphenyl)-1-[({(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidin-2-yl}carbonyl)oxy]propyl}phenoxy)acetic acid'  ligand  97  50  .  2021-08-06  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_AP1
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 AP1  C1    C  C     0   0.606  13.5819  13.5427  19.9307
 AP1  C2    C  CH1   0  -0.262  14.9926  14.1155  19.8251
 AP1  C3    C  CH2   0  -0.424  16.0652  13.0359  19.7110
 AP1  C4    C  CH2   0  -0.455  16.2945  12.2901  21.0201
 AP1  C5    C  CH2   0  -0.422  16.5240  13.2724  22.1604
 AP1  C6    C  CH2   0  -0.329  15.4083  14.3022  22.2204
 AP1  C9    C  CH1   0  -0.500  15.5039  17.2383  21.9755
 AP1  C10   C  CR6   0   0.210  14.2200  17.4303  22.7574
 AP1  C11   C  CR16  0  -0.455  13.1053  17.9874  22.1397
 AP1  C12   C  CR6   0   0.345  11.9429  18.2073  22.8743
 AP1  C13   C  CR6   0   0.165  11.8812  17.8374  24.2210
 AP1  C14   C  CR6   0   0.348  13.0046  17.2815  24.8350
 AP1  O15   O  O2    0  -0.469  12.8609  16.9570  26.1325
 AP1  O17   O  O2    0  -0.463  10.8198  18.7500  22.3720
 AP1  C18   C  CH3   0  -0.443  13.9423  16.3282  26.7920
 AP1  C19   C  CH3   0  -0.409  10.6213  19.2565  25.5825
 AP1  C20   C  CH3   0  -0.443  10.8383  19.2356  21.0445
 AP1  C21   C  CH3   0  -0.407   6.8707   9.8956  18.3078
 AP1  C22   C  CR16  0  -0.295  11.7279  14.2997  23.0704
 AP1  C23   C  CR16  0  -0.243  11.6087  13.7782  24.3448
 AP1  C24   C  CR16  0  -0.379  11.0744  12.5103  24.5573
 AP1  C25   C  CR6   0   0.109  11.3034  13.5429  21.9787
 AP1  C26   C  CH1   0  -0.015  11.3620  14.1146  20.5872
 AP1  C27   C  CH2   0  -0.477  10.5517  15.3941  20.4267
 AP1  C28   C  CH2   0  -0.510   9.1105  15.2868  20.9241
 AP1  C29   C  CR6   0   0.125   8.3209  14.1522  20.3269
 AP1  C30   C  CR16  0  -0.439   8.1172  14.0882  18.9466
 AP1  C31   C  CR6   0   0.338   7.3928  13.0479  18.3777
 AP1  C32   C  CR6   0   0.245   6.8536  12.0515  19.2087
 AP1  C33   C  CR16  0  -0.310   7.0600  12.1149  20.5731
 AP1  C34   C  CR16  0  -0.323   7.7851  13.1607  21.1339
 AP1  C35   C  CR6   0   0.414  10.6642  11.7558  23.4650
 AP1  O36   O  O2    0  -0.473  10.1450  10.5058  23.5425
 AP1  C37   C  CH2   0  -0.337   9.7850  10.0000  24.7960
 AP1  C38   C  C     0   0.511   8.5581  10.6496  25.4073
 AP1  O39   O  O     0  -0.440   8.2634  10.4970  26.5652
 AP1  O40   O  OH1   0  -0.568   7.8482  11.3401  24.5353
 AP1  C41   C  CR16  0  -0.387  10.7891  12.2753  22.1783
 AP1  C42   C  CH3   0  -0.438   7.6393  13.9058  16.1832
 AP1  N7    N  NT    0  -0.456  15.2671  14.9962  20.9484
 AP1  O43   O  O2    0  -0.453  12.7202  14.4810  20.2859
 AP1  O44   O  O     0  -0.431  13.2846  12.4019  19.6871
 AP1  C46   C  CH2   0  -0.393  16.0996  18.5833  21.5471
 AP1  C47   C  CR16  0  -0.499  14.1729  17.0828  24.1009
 AP1  O48   O  O2    0  -0.479  10.7292  18.0031  24.9217
 AP1  O49   O  O2    0  -0.464   7.1463  12.9149  17.0615
 AP1  O50   O  O2    0  -0.492   6.1164  11.0459  18.6589
 AP1  H2    H  HCH1  0   0.317  15.0056  14.7194  18.9145
 AP1  H31   H  HCH2  0   0.249  15.8096  12.3463  18.9058
 AP1  H32   H  HCH2  0   0.244  16.9911  13.5328  19.4104
 AP1  H41A  H  HCH2  0   0.225  15.4342  11.6552  21.2493
 AP1  H42   H  HCH2  0   0.243  17.1505  11.6207  20.9169
 AP1  H51   H  HCH2  0   0.243  16.5713  12.7495  23.1176
 AP1  H52   H  HCH2  0   0.226  17.4796  13.7886  22.0286
 AP1  H61   H  HCH2  0   0.248  14.4581  13.8164  22.4723
 AP1  H62   H  HCH2  0   0.270  15.5914  15.0090  23.0211
 AP1  H9    H  HCH1  0   0.270  16.2359  16.7672  22.6350
 AP1  H11   H  HCR6  0   0.274  13.1536  18.2463  21.0907
 AP1  H161  H  HCH3  0   0.234  17.9128  19.4411  20.7319
 AP1  H162  H  HCH3  0   0.220  18.1822  18.0039  21.7115
 AP1  H163  H  HCH3  0   0.226  17.5341  17.8527  20.0793
 AP1  H181  H  HCH3  0   0.264  13.6073  16.1240  27.8057
 AP1  H182  H  HCH3  0   0.226  14.2153  15.3830  26.3153
 AP1  H183  H  HCH3  0   0.234  14.8261  16.9695  26.8358
 AP1  H191  H  HCH3  0   0.236   9.6548  19.2729  26.0834
 AP1  H192  H  HCH3  0   0.221  11.4052  19.3891  26.3324
 AP1  H193  H  HCH3  0   0.221  10.6638  20.0914  24.8789
 AP1  H201  H  HCH3  0   0.262   9.8619  19.6790  20.8660
 AP1  H202  H  HCH3  0   0.233  11.6055  20.0003  20.8992
 AP1  H203  H  HCH3  0   0.225  10.9969  18.4369  20.3149
 AP1  H211  H  HCH3  0   0.237   6.1769   9.1711  17.8847
 AP1  H212  H  HCH3  0   0.221   7.6386  10.1205  17.5630
 AP1  H213  H  HCH3  0   0.218   7.3530   9.4496  19.1822
 AP1  H22   H  HCR6  0   0.261  12.1361  15.2918  22.9260
 AP1  H23   H  HCR6  0   0.257  11.9209  14.3640  25.1998
 AP1  H24   H  HCR6  0   0.277  10.9958  12.1470  25.5731
 AP1  H26   H  HCH1  0   0.261  11.0144  13.3651  19.8719
 AP1  H271  H  HCH2  0   0.253  11.0437  16.1990  20.9769
 AP1  H272  H  HCH2  0   0.251  10.5663  15.6844  19.3727
 AP1  H281  H  HCH2  0   0.249   9.1062  15.1887  22.0114
 AP1  H282  H  HCH2  0   0.258   8.6156  16.2358  20.7003
 AP1  H30   H  HCR6  0   0.274   8.5330  14.8712  18.3240
 AP1  H33   H  HCR6  0   0.257   6.6398  11.3418  21.2054
 AP1  H34   H  HCR6  0   0.246   7.9412  13.1910  22.2044
 AP1  H371  H  HCH2  0   0.314   9.5478   8.9441  24.6450
 AP1  H372  H  HCH2  0   0.273  10.6001  10.0349  25.5243
 AP1  H40   H  HOH1  0   0.487   7.0640  11.7150  24.9650
 AP1  H41   H  HCR6  0   0.259  10.4507  11.6858  21.3345
 AP1  H421  H  HCH3  0   0.260   7.3193  13.6205  15.1842
 AP1  H422  H  HCH3  0   0.227   7.2329  14.8943  16.4134
 AP1  H423  H  HCH3  0   0.228   8.7309  13.9620  16.2005
 AP1  H461  H  HCH2  0   0.229  15.4413  19.0708  20.8264
 AP1  H462  H  HCH2  0   0.233  16.1191  19.2251  22.4311
 AP1  H47   H  HCR6  0   0.274  15.0538  16.6627  24.5669
 AP1  C8    C  C     0   0.617  15.2402  16.3380  20.7670
 AP1  C16   C  CH3   0  -0.674  17.5083  18.4605  20.9839
 AP1  O45   O  O     0  -0.494  15.0082  16.8337  19.6734

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 AP1  C1   C2    single    1.526  0.020  1.526
 AP1  C1   O43   single    1.323  0.020  1.323
 AP1  C1   O44   double    1.204  0.020  1.204
 AP1  C2   C3    single    1.526  0.020  1.526
 AP1  C2   N7    single    1.454  0.020  1.454
 AP1  C2   H2    single    0.970  0.020  1.090
 AP1  C3   C4    single    1.524  0.020  1.524
 AP1  C3   H31   single    0.970  0.020  1.090
 AP1  C3   H32   single    0.970  0.020  1.090
 AP1  C4   C5    single    1.523  0.020  1.523
 AP1  C4   H41A  single    0.970  0.020  1.090
 AP1  C4   H42   single    0.970  0.020  1.090
 AP1  C5   C6    single    1.519  0.020  1.519
 AP1  C5   H51   single    0.970  0.020  1.090
 AP1  C5   H52   single    0.970  0.020  1.090
 AP1  C6   N7    single    1.456  0.020  1.456
 AP1  C6   H61   single    0.970  0.020  1.090
 AP1  C6   H62   single    0.970  0.020  1.090
 AP1  C8   C9    single    1.530  0.020  1.530
 AP1  C8   N7    single    1.354  0.020  1.354
 AP1  C8   O45   double    1.223  0.020  1.223
 AP1  C9   C10   single    1.515  0.020  1.515
 AP1  C9   C46   single    1.532  0.020  1.532
 AP1  C9   H9    single    0.970  0.020  1.090
 AP1  C10  C11   aromatic  1.391  0.020  1.391
 AP1  C10  C47   aromatic  1.388  0.020  1.388
 AP1  C11  C12   aromatic  1.393  0.020  1.393
 AP1  C11  H11   single    0.930  0.020  1.080
 AP1  C12  C13   aromatic  1.398  0.020  1.398
 AP1  C12  O17   single    1.345  0.020  1.345
 AP1  C13  C14   aromatic  1.396  0.020  1.396
 AP1  C13  O48   single    1.359  0.020  1.359
 AP1  C14  O15   single    1.345  0.020  1.345
 AP1  C14  C47   aromatic  1.394  0.020  1.394
 AP1  O15  C18   single    1.414  0.020  1.414
 AP1  C16  C46   single    1.522  0.020  1.522
 AP1  C16  H161  single    0.970  0.020  1.090
 AP1  C16  H162  single    0.970  0.020  1.090
 AP1  C16  H163  single    0.970  0.020  1.090
 AP1  O17  C20   single    1.414  0.020  1.414
 AP1  C18  H181  single    0.970  0.020  1.090
 AP1  C18  H182  single    0.970  0.020  1.090
 AP1  C18  H183  single    0.970  0.020  1.090
 AP1  C19  O48   single    1.421  0.020  1.421
 AP1  C19  H191  single    0.970  0.020  1.090
 AP1  C19  H192  single    0.970  0.020  1.090
 AP1  C19  H193  single    0.970  0.020  1.090
 AP1  C20  H201  single    0.970  0.020  1.090
 AP1  C20  H202  single    0.970  0.020  1.090
 AP1  C20  H203  single    0.970  0.020  1.090
 AP1  C21  O50   single    1.420  0.020  1.420
 AP1  C21  H211  single    0.970  0.020  1.090
 AP1  C21  H212  single    0.970  0.020  1.090
 AP1  C21  H213  single    0.970  0.020  1.090
 AP1  C22  C23   aromatic  1.382  0.020  1.382
 AP1  C22  C25   aromatic  1.394  0.020  1.394
 AP1  C22  H22   single    0.930  0.020  1.080
 AP1  C23  C24   aromatic  1.392  0.020  1.392
 AP1  C23  H23   single    0.930  0.020  1.080
 AP1  C24  C35   aromatic  1.389  0.020  1.389
 AP1  C24  H24   single    0.930  0.020  1.080
 AP1  C25  C26   single    1.505  0.020  1.505
 AP1  C25  C41   aromatic  1.383  0.020  1.383
 AP1  C26  C27   single    1.523  0.020  1.523
 AP1  C26  O43   single    1.439  0.020  1.439
 AP1  C26  H26   single    0.970  0.020  1.090
 AP1  C27  C28   single    1.528  0.020  1.528
 AP1  C27  H271  single    0.970  0.020  1.090
 AP1  C27  H272  single    0.970  0.020  1.090
 AP1  C28  C29   single    1.506  0.020  1.506
 AP1  C28  H281  single    0.970  0.020  1.090
 AP1  C28  H282  single    0.970  0.020  1.090
 AP1  C29  C30   aromatic  1.397  0.020  1.397
 AP1  C29  C34   aromatic  1.386  0.020  1.386
 AP1  C30  C31   aromatic  1.390  0.020  1.390
 AP1  C30  H30   single    0.930  0.020  1.080
 AP1  C31  C32   aromatic  1.405  0.020  1.405
 AP1  C31  O49   single    1.346  0.020  1.346
 AP1  C32  C33   aromatic  1.381  0.020  1.381
 AP1  C32  O50   single    1.363  0.020  1.363
 AP1  C33  C34   aromatic  1.391  0.020  1.391
 AP1  C33  H33   single    0.930  0.020  1.080
 AP1  C34  H34   single    0.930  0.020  1.080
 AP1  C35  O36   single    1.356  0.020  1.356
 AP1  C35  C41   aromatic  1.393  0.020  1.393
 AP1  O36  C37   single    1.399  0.020  1.399
 AP1  C37  C38   single    1.517  0.020  1.517
 AP1  C37  H371  single    0.970  0.020  1.090
 AP1  C37  H372  single    0.970  0.020  1.090
 AP1  C38  O39   double    1.205  0.020  1.205
 AP1  C38  O40   single    1.320  0.020  1.320
 AP1  O40  H40   single    0.850  0.020  0.980
 AP1  C41  H41   single    0.930  0.020  1.080
 AP1  C42  O49   single    1.413  0.020  1.413
 AP1  C42  H421  single    0.970  0.020  1.090
 AP1  C42  H422  single    0.970  0.020  1.090
 AP1  C42  H423  single    0.970  0.020  1.090
 AP1  C46  H461  single    0.970  0.020  1.090
 AP1  C46  H462  single    0.970  0.020  1.090
 AP1  C47  H47   single    0.930  0.020  1.080

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 AP1  O44   C1   O43   124.46  3.000
 AP1  O44   C1   C2    124.75  3.000
 AP1  O43   C1   C2    110.76  3.000
 AP1  H2    C2   N7    107.87  3.000
 AP1  H2    C2   C3    108.68  3.000
 AP1  N7    C2   C3    110.71  3.000
 AP1  H2    C2   C1    106.03  3.000
 AP1  N7    C2   C1    110.39  3.000
 AP1  C3    C2   C1    112.91  3.000
 AP1  H32   C3   H31   106.44  3.000
 AP1  H32   C3   C4    109.34  3.000
 AP1  H31   C3   C4    111.11  3.000
 AP1  H32   C3   C2    107.12  3.000
 AP1  H31   C3   C2    109.74  3.000
 AP1  C4    C3   C2    112.81  3.000
 AP1  H42   C4   H41A  106.31  3.000
 AP1  H42   C4   C5    110.38  3.000
 AP1  H41A  C4   C5    109.64  3.000
 AP1  H42   C4   C3    109.69  3.000
 AP1  H41A  C4   C3    110.23  3.000
 AP1  C5    C4   C3    110.51  3.000
 AP1  H52   C5   H51   107.08  3.000
 AP1  H52   C5   C6    109.05  3.000
 AP1  H51   C5   C6    108.77  3.000
 AP1  H52   C5   C4    110.23  3.000
 AP1  H51   C5   C4    110.75  3.000
 AP1  C6    C5   C4    110.86  3.000
 AP1  H62   C6   H61   105.40  3.000
 AP1  H62   C6   N7    110.55  3.000
 AP1  H61   C6   N7    109.14  3.000
 AP1  H62   C6   C5    110.31  3.000
 AP1  H61   C6   C5    110.19  3.000
 AP1  N7    C6   C5    111.09  3.000
 AP1  H9    C9   C46   106.67  3.000
 AP1  H9    C9   C10   108.11  3.000
 AP1  C46   C9   C10   111.25  3.000
 AP1  H9    C9   C8    109.80  3.000
 AP1  C46   C9   C8    111.27  3.000
 AP1  C10   C9   C8    109.64  3.000
 AP1  C47   C10  C11   120.18  3.000
 AP1  C47   C10  C9    119.76  3.000
 AP1  C11   C10  C9    120.04  3.000
 AP1  H11   C11  C12   120.74  3.000
 AP1  H11   C11  C10   119.40  3.000
 AP1  C12   C11  C10   119.87  3.000
 AP1  O17   C12  C13   115.45  3.000
 AP1  O17   C12  C11   124.32  3.000
 AP1  C13   C12  C11   120.21  3.000
 AP1  O48   C13  C14   120.28  3.000
 AP1  O48   C13  C12   120.13  3.000
 AP1  C14   C13  C12   119.58  3.000
 AP1  C47   C14  O15   124.27  3.000
 AP1  C47   C14  C13   119.97  3.000
 AP1  O15   C14  C13   115.75  3.000
 AP1  C18   O15  C14   118.39  3.000
 AP1  C20   O17  C12   118.59  3.000
 AP1  H183  C18  H182  108.84  3.000
 AP1  H183  C18  H181  108.79  3.000
 AP1  H182  C18  H181  108.74  3.000
 AP1  H183  C18  O15   112.09  3.000
 AP1  H182  C18  O15   111.84  3.000
 AP1  H181  C18  O15   106.43  3.000
 AP1  H193  C19  H192  108.73  3.000
 AP1  H193  C19  H191  108.62  3.000
 AP1  H192  C19  H191  108.62  3.000
 AP1  H193  C19  O48   111.81  3.000
 AP1  H192  C19  O48   111.81  3.000
 AP1  H191  C19  O48   107.14  3.000
 AP1  H203  C20  H202  108.71  3.000
 AP1  H203  C20  H201  108.58  3.000
 AP1  H202  C20  H201  108.86  3.000
 AP1  H203  C20  O17   112.18  3.000
 AP1  H202  C20  O17   111.98  3.000
 AP1  H201  C20  O17   106.41  3.000
 AP1  H213  C21  H212  108.59  3.000
 AP1  H213  C21  H211  108.69  3.000
 AP1  H212  C21  H211  108.65  3.000
 AP1  H213  C21  O50   111.53  3.000
 AP1  H212  C21  O50   112.03  3.000
 AP1  H211  C21  O50   107.26  3.000
 AP1  H22   C22  C25   120.52  3.000
 AP1  H22   C22  C23   120.08  3.000
 AP1  C25   C22  C23   119.40  3.000
 AP1  H23   C23  C24   118.88  3.000
 AP1  H23   C23  C22   119.96  3.000
 AP1  C24   C23  C22   121.16  3.000
 AP1  H24   C24  C35   122.31  3.000
 AP1  H24   C24  C23   118.50  3.000
 AP1  C35   C24  C23   119.19  3.000
 AP1  C41   C25  C26   119.74  3.000
 AP1  C41   C25  C22   119.86  3.000
 AP1  C26   C25  C22   120.38  3.000
 AP1  H26   C26  O43   109.74  3.000
 AP1  H26   C26  C27   109.75  3.000
 AP1  O43   C26  C27   105.44  3.000
 AP1  H26   C26  C25   109.40  3.000
 AP1  O43   C26  C25   109.09  3.000
 AP1  C27   C26  C25   113.31  3.000
 AP1  H272  C27  H271  106.50  3.000
 AP1  H272  C27  C28   110.18  3.000
 AP1  H271  C27  C28   108.22  3.000
 AP1  H272  C27  C26   108.51  3.000
 AP1  H271  C27  C26   109.05  3.000
 AP1  C28   C27  C26   114.10  3.000
 AP1  H282  C28  H281  106.26  3.000
 AP1  H282  C28  C29   109.60  3.000
 AP1  H281  C28  C29   108.98  3.000
 AP1  H282  C28  C27   107.41  3.000
 AP1  H281  C28  C27   109.52  3.000
 AP1  C29   C28  C27   114.73  3.000
 AP1  C34   C29  C30   119.09  3.000
 AP1  C34   C29  C28   120.72  3.000
 AP1  C30   C29  C28   120.19  3.000
 AP1  H30   C30  C31   120.39  3.000
 AP1  H30   C30  C29   118.62  3.000
 AP1  C31   C30  C29   121.00  3.000
 AP1  O49   C31  C32   115.99  3.000
 AP1  O49   C31  C30   124.75  3.000
 AP1  C32   C31  C30   119.26  3.000
 AP1  O50   C32  C33   120.88  3.000
 AP1  O50   C32  C31   119.49  3.000
 AP1  C33   C32  C31   119.62  3.000
 AP1  H33   C33  C34   120.23  3.000
 AP1  H33   C33  C32   119.05  3.000
 AP1  C34   C33  C32   120.71  3.000
 AP1  H34   C34  C33   119.68  3.000
 AP1  H34   C34  C29   120.00  3.000
 AP1  C33   C34  C29   120.31  3.000
 AP1  C41   C35  O36   115.52  3.000
 AP1  C41   C35  C24   119.81  3.000
 AP1  O36   C35  C24   124.66  3.000
 AP1  C37   O36  C35   118.89  3.000
 AP1  H372  C37  H371  106.54  3.000
 AP1  H372  C37  C38   108.72  3.000
 AP1  H371  C37  C38   107.10  3.000
 AP1  H372  C37  O36   113.16  3.000
 AP1  H371  C37  O36   106.34  3.000
 AP1  C38   C37  O36   114.48  3.000
 AP1  O40   C38  O39   124.74  3.000
 AP1  O40   C38  C37   113.14  3.000
 AP1  O39   C38  C37   122.08  3.000
 AP1  H40   O40  C38   110.16  3.000
 AP1  H41   C41  C35   119.24  3.000
 AP1  H41   C41  C25   120.18  3.000
 AP1  C35   C41  C25   120.56  3.000
 AP1  H423  C42  H422  108.75  3.000
 AP1  H423  C42  H421  108.78  3.000
 AP1  H422  C42  H421  108.75  3.000
 AP1  H423  C42  O49   112.00  3.000
 AP1  H422  C42  O49   111.93  3.000
 AP1  H421  C42  O49   106.52  3.000
 AP1  C8    N7   C6    126.24  3.000
 AP1  C8    N7   C2    119.54  3.000
 AP1  C6    N7   C2    113.87  3.000
 AP1  C26   O43  C1    119.38  3.000
 AP1  H462  C46  H461  106.42  3.000
 AP1  H462  C46  C16   109.28  3.000
 AP1  H461  C46  C16   110.49  3.000
 AP1  H462  C46  C9    107.24  3.000
 AP1  H461  C46  C9    110.02  3.000
 AP1  C16   C46  C9    113.11  3.000
 AP1  H47   C47  C14   120.73  3.000
 AP1  H47   C47  C10   119.11  3.000
 AP1  C14   C47  C10   120.16  3.000
 AP1  C19   O48  C13   114.32  3.000
 AP1  C42   O49  C31   118.35  3.000
 AP1  C32   O50  C21   114.22  3.000
 AP1  O45   C8   N7    121.68  3.000
 AP1  O45   C8   C9    120.04  3.000
 AP1  N7    C8   C9    118.28  3.000
 AP1  H163  C16  H162  107.77  3.000
 AP1  H163  C16  H161  107.51  3.000
 AP1  H162  C16  H161  107.53  3.000
 AP1  H163  C16  C46   111.96  3.000
 AP1  H162  C16  C46   111.00  3.000
 AP1  H161  C16  C46   110.87  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 AP1  CONST_01  C13   C12  C11  C10     0.00   0.0  0
 AP1  CONST_02  C13   C14  C47  C10     0.00   0.0  0
 AP1  CONST_03  C14   C47  C10  C11     0.00   0.0  0
 AP1  CONST_04  C14   C13  C12  C11     0.00   0.0  0
 AP1  CONST_05  C47   C10  C11  C12     0.00   0.0  0
 AP1  CONST_06  C47   C14  C13  C12     0.00   0.0  0
 AP1  CONST_07  C35   C24  C23  C22     0.00   0.0  0
 AP1  CONST_08  C35   C41  C25  C22     0.00   0.0  0
 AP1  CONST_09  C41   C25  C22  C23     0.00   0.0  0
 AP1  CONST_10  C41   C35  C24  C23     0.00   0.0  0
 AP1  CONST_11  C25   C22  C23  C24     0.00   0.0  0
 AP1  CONST_12  C25   C41  C35  C24     0.00   0.0  0
 AP1  CONST_13  C32   C31  C30  C29     0.00   0.0  0
 AP1  CONST_14  C32   C33  C34  C29     0.00   0.0  0
 AP1  CONST_15  C33   C34  C29  C30     0.00   0.0  0
 AP1  CONST_16  C33   C32  C31  C30     0.00   0.0  0
 AP1  CONST_17  C34   C29  C30  C31     0.00   0.0  0
 AP1  CONST_18  C34   C33  C32  C31     0.00   0.0  0
 AP1  CONST_19  C12   C11  C10  C9    180.00   0.0  0
 AP1  CONST_20  C14   C47  C10  C9    180.00   0.0  0
 AP1  CONST_21  O17   C12  C11  C10   180.00   0.0  0
 AP1  CONST_22  O15   C14  C47  C10   180.00   0.0  0
 AP1  CONST_23  O48   C13  C12  C11   180.00   0.0  0
 AP1  CONST_24  O15   C14  C13  C12   180.00   0.0  0
 AP1  CONST_25  O17   C12  C13  C14   180.00   0.0  0
 AP1  CONST_26  C26   C25  C22  C23   180.00   0.0  0
 AP1  CONST_27  O36   C35  C24  C23   180.00   0.0  0
 AP1  CONST_28  O36   C35  C41  C25   180.00   0.0  0
 AP1  CONST_29  C35   C41  C25  C26   180.00   0.0  0
 AP1  CONST_30  C31   C30  C29  C28   180.00   0.0  0
 AP1  CONST_31  C33   C34  C29  C28   180.00   0.0  0
 AP1  CONST_32  O49   C31  C30  C29   180.00   0.0  0
 AP1  CONST_33  O50   C32  C31  C30   180.00   0.0  0
 AP1  CONST_34  O49   C31  C32  C33   180.00   0.0  0
 AP1  CONST_35  O50   C32  C33  C34   180.00   0.0  0
 AP1  CONST_36  O48   C13  C14  C47   180.00   0.0  0
 AP1  CONST_37  H47   C47  C10  C11   180.00   0.0  0
 AP1  CONST_38  H11   C11  C12  C13   180.00   0.0  0
 AP1  CONST_39  H24   C24  C23  C22   180.00   0.0  0
 AP1  CONST_40  H41   C41  C25  C22   180.00   0.0  0
 AP1  CONST_41  H22   C22  C23  C24   180.00   0.0  0
 AP1  CONST_42  H23   C23  C22  C25   180.00   0.0  0
 AP1  CONST_43  H33   C33  C34  C29   180.00   0.0  0
 AP1  CONST_44  H34   C34  C29  C30   180.00   0.0  0
 AP1  CONST_45  H30   C30  C31  C32   180.00   0.0  0
 AP1  CONST_46  C9    C8   N7   C2    180.00   0.0  0
 AP1  CONST_47  O45   C8   N7   C2      0.00   0.0  0
 AP1  CONST_48  C9    C8   N7   C6      0.00   0.0  0
 AP1  CONST_49  O45   C8   N7   C6    180.00   0.0  0
 AP1  CONST_50  H40   O40  C38  C37   180.00   0.0  0
 AP1  Var_01    C5    C4   C3   C2    -51.08  30.0  1
 AP1  Var_02    C5    C6   N7   C2     58.33  30.0  1
 AP1  Var_03    C6    C5   C4   C3     52.48  30.0  1
 AP1  Var_04    N7    C6   C5   C4    -55.84  30.0  1
 AP1  Var_05    C47   C14  O15  C18    -2.43  30.0  2
 AP1  Var_06    C31   C32  O50  C21    91.62  30.0  2
 AP1  Var_07    C30   C29  C28  C27   -60.11  30.0  2
 AP1  Var_08    C41   C35  O36  C37  -169.68  30.0  2
 AP1  Var_09    C29   C28  C27  C26   -54.36  30.0  3
 AP1  Var_10    C38   C37  O36  C35    70.78  30.0  3
 AP1  Var_11    H201  C20  O17  C12  -176.68  30.0  3
 AP1  Var_12    H191  C19  O48  C13   178.75  30.0  3
 AP1  Var_13    H181  C18  O15  C14  -178.02  30.0  3
 AP1  Var_14    H421  C42  O49  C31  -179.04  30.0  3
 AP1  Var_15    H211  C21  O50  C32   179.94  30.0  3
 AP1  Var_16    O44   C1   O43  C26     8.95  30.0  2
 AP1  Var_17    O39   C38  C37  O36  -166.59  30.0  3
 AP1  Var_18    H161  C16  C46  C9   -177.52  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 AP1  chir_01  C2   C1   C3   N7   positiv
 AP1  chir_02  C9   C46  C10  C8   negativ
 AP1  chir_03  C26  O43  C25  C27  negativ

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 AP1  plan-1  C9   0.020
 AP1  plan-1  C10  0.020
 AP1  plan-1  C11  0.020
 AP1  plan-1  C12  0.020
 AP1  plan-1  C13  0.020
 AP1  plan-1  C14  0.020
 AP1  plan-1  O15  0.020
 AP1  plan-1  O17  0.020
 AP1  plan-1  C47  0.020
 AP1  plan-1  O48  0.020
 AP1  plan-1  H11  0.020
 AP1  plan-1  H47  0.020
 AP1  plan-2  C22  0.020
 AP1  plan-2  C23  0.020
 AP1  plan-2  C24  0.020
 AP1  plan-2  C25  0.020
 AP1  plan-2  C26  0.020
 AP1  plan-2  C35  0.020
 AP1  plan-2  O36  0.020
 AP1  plan-2  C41  0.020
 AP1  plan-2  H22  0.020
 AP1  plan-2  H23  0.020
 AP1  plan-2  H24  0.020
 AP1  plan-2  H41  0.020
 AP1  plan-3  C28  0.020
 AP1  plan-3  C29  0.020
 AP1  plan-3  C30  0.020
 AP1  plan-3  C31  0.020
 AP1  plan-3  C32  0.020
 AP1  plan-3  C33  0.020
 AP1  plan-3  C34  0.020
 AP1  plan-3  O49  0.020
 AP1  plan-3  O50  0.020
 AP1  plan-3  H30  0.020
 AP1  plan-3  H33  0.020
 AP1  plan-3  H34  0.020
 AP1  plan-4  C2   0.020
 AP1  plan-4  C6   0.020
 AP1  plan-4  C9   0.020
 AP1  plan-4  N7   0.020
 AP1  plan-4  C8   0.020
 AP1  plan-4  O45  0.020
 AP1  plan-5  C37  0.020
 AP1  plan-5  C38  0.020
 AP1  plan-5  O39  0.020
 AP1  plan-5  O40  0.020
 AP1  plan-5  H40  0.020
 AP1  plan-6  C1   0.020
 AP1  plan-6  C2   0.020
 AP1  plan-6  O43  0.020
 AP1  plan-6  O44  0.020

