# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sat May 30 20:03:21 2020
#   Inital geometry file: a 175 line input string
#   Ligand name: (2S)-2-({(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}carbonyl)-4,4-dimethylpentanenitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(C)C[C@@H](C#N)C(=O)N1CCC[C@H](C1)n2nc(c3ccc(Oc4ccccc4)cc3)c5c(N)ncnc25
#
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
 4C9  4C9  (2S)-2-({(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}carbonyl)-4,4-dimethylpentanenitrile  ligand  72  39  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_4C9
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
 4C9  C1   C  CH2   0  -0.380    6.8687   1.3122  -1.2122
 4C9  C2   C  CT    0  -0.104    8.2401   1.9190  -0.8662
 4C9  C3   C  CH3   0  -0.650    9.1920   0.9039  -0.2323
 4C9  C4   C  CSP   0   0.159    6.4952  -0.4884   0.4667
 4C9  C5   C  CR16  0  -0.338   -4.0566  -1.0515   1.0730
 4C9  C6   C  CR16  0  -0.286   -5.2627  -0.4009   1.2863
 4C9  C7   C  CR6   0   0.364   -7.3863   1.8323   0.2375
 4C9  C8   C  CR16  0  -0.327   -8.5166   2.5934   0.5224
 4C9  N1   N  N     0  -0.477   -1.4085  -4.3086  -1.5093
 4C9  C9   C  CR6   0   0.438   -2.1068  -3.2772  -1.0266
 4C9  C10  C  CR56  0  -0.270   -1.4190  -2.2753  -0.3004
 4C9  C11  C  CR56  0   0.589   -0.0331  -2.4343  -0.2287
 4C9  N3   N  NR5   0  -0.386    0.4459  -1.3566   0.4213
 4C9  C12  C  CH1   0  -0.091    1.8215  -1.0776   0.7688
 4C9  C13  C  CH2   0  -0.313    2.2413   0.2890   0.2225
 4C9  N4   N  NT    0  -0.458    3.6375   0.5274   0.5467
 4C9  C14  C  C     0   0.607    4.5491   0.5998  -0.4425
 4C9  C15  C  CH1   0  -0.545    6.0267   0.7983  -0.0341
 4C9  C16  C  CH3   0  -0.638    8.8443   2.4024  -2.1882
 4C9  C17  C  CH3   0  -0.651    8.0807   3.1205   0.0677
 4C9  N5   N  NS    0  -0.260    6.8320  -1.5265   0.8321
 4C9  C18  C  CH2   0  -0.333    3.8953   0.5340   1.9812
 4C9  C19  C  CH2   0  -0.443    3.5005  -0.8013   2.5979
 4C9  C20  C  CH2   0  -0.443    2.0525  -1.1496   2.2742
 4C9  N6   N  N     0  -0.275   -0.5406  -0.5241   0.7830
 4C9  C21  C  CR5   0   0.275   -1.6714  -1.0448   0.3671
 4C9  C22  C  CR6   0   0.035   -2.9432  -0.3550   0.6052
 4C9  C23  C  CR6   0   0.297   -5.3519   0.9608   1.0455
 4C9  O2   O  O2    0  -0.512   -6.5354   1.6103   1.2809
 4C9  C24  C  CR16  0  -0.340   -7.1791   1.3353  -1.0440
 4C9  C25  C  CR16  0  -0.245   -8.1144   1.6062  -2.0363
 4C9  C26  C  CR16  0  -0.273   -9.2442   2.3625  -1.7650
 4C9  C27  C  CR16  0  -0.246   -9.4385   2.8529  -0.4786
 4C9  C28  C  CR16  0  -0.287   -4.2487   1.6769   0.6026
 4C9  C29  C  CR16  0  -0.282   -3.0498   1.0183   0.3871
 4C9  N7   N  N     0  -0.466    0.6741  -3.4552  -0.7191
 4C9  C30  C  CR16  0   0.058   -0.0904  -4.3408  -1.3240
 4C9  H1   H  HCH2  0   0.256    6.2778   2.0885  -1.7036
 4C9  H3   H  HCH3  0   0.227    9.2902   0.0051  -0.8444
 4C9  H4   H  HCH3  0   0.233   10.1861   1.3431  -0.1248
 4C9  H5   H  HCH3  0   0.229    8.8715   0.5980   0.7646
 4C9  H6   H  HCR6  0   0.281   -3.9837  -2.1096   1.2935
 4C9  H7   H  HCR6  0   0.280   -6.1234  -0.9475   1.6496
 4C9  H8   H  HCR6  0   0.269   -8.6677   2.9767   1.5238
 4C9  H9   H  HNH2  0   0.407   -3.8276  -3.9649  -1.8410
 4C9  H10  H  HNH2  0   0.415   -3.9882  -2.4590  -1.0249
 4C9  H11  H  HCH1  0   0.276    2.4135  -1.8492   0.2712
 4C9  H12  H  HCH2  0   0.285    2.0967   0.3363  -0.8532
 4C9  H13  H  HCH2  0   0.263    1.6379   1.0771   0.6826
 4C9  H15  H  HCH3  0   0.225    8.2087   3.1540  -2.6613
 4C9  H16  H  HCH3  0   0.228    9.8264   2.8503  -2.0254
 4C9  H17  H  HCH3  0   0.226    8.9701   1.5796  -2.8955
 4C9  H18  H  HCH3  0   0.228    7.7055   2.8347   1.0524
 4C9  H19  H  HCH3  0   0.234    9.0432   3.6108   0.2255
 4C9  H20  H  HCH3  0   0.227    7.3951   3.8601  -0.3521
 4C9  H21  H  HCH2  0   0.277    4.9351   0.7588   2.1970
 4C9  H22  H  HCH2  0   0.264    3.3035   1.3397   2.4259
 4C9  H23  H  HCH2  0   0.238    4.1678  -1.5834   2.2258
 4C9  H24  H  HCH2  0   0.257    3.6411  -0.7470   3.6785
 4C9  H25  H  HCH2  0   0.239    1.3813  -0.4442   2.7726
 4C9  H26  H  HCH2  0   0.259    1.8084  -2.1477   2.6423
 4C9  H27  H  HCR6  0   0.276   -6.3077   0.7409  -1.2845
 4C9  H28  H  HCR6  0   0.262   -7.9489   1.2152  -3.0319
 4C9  H29  H  HCR6  0   0.256   -9.9646   2.5697  -2.5449
 4C9  H30  H  HCR6  0   0.261  -10.3148   3.4454  -0.2493
 4C9  H31  H  HCR6  0   0.280   -4.3273   2.7416   0.4227
 4C9  H32  H  HCR6  0   0.263   -2.1928   1.5735   0.0292
 4C9  H33  H  HCR6  0   0.256    0.4146  -5.2082  -1.7358
 4C9  H34  H  HCH1  0   0.350    6.0858   1.5157   0.7876
 4C9  H35  H  HCH2  0   0.253    6.9964   0.5117  -1.9439
 4C9  O1   O  O     0  -0.466    4.2618   0.5128  -1.6227
 4C9  N2   N  NH2   0  -0.815   -3.4186  -3.2527  -1.2594

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
 4C9  C1   C15  single    1.536  0.020  1.536
 4C9  C2   C3   single    1.529  0.020  1.529
 4C9  C2   C16  single    1.532  0.020  1.532
 4C9  C2   C17  single    1.530  0.020  1.530
 4C9  C4   C15  single    1.458  0.020  1.458
 4C9  C4   N5   triple    1.151  0.020  1.151
 4C9  C5   C6   aromatic  1.387  0.020  1.387
 4C9  C5   C22  aromatic  1.394  0.020  1.394
 4C9  C6   C23  aromatic  1.386  0.020  1.386
 4C9  C7   C8   aromatic  1.392  0.020  1.392
 4C9  C7   O2   single    1.365  0.020  1.365
 4C9  C7   C24  aromatic  1.390  0.020  1.390
 4C9  C8   C27  aromatic  1.385  0.020  1.385
 4C9  N1   C9   aromatic  1.336  0.020  1.336
 4C9  N1   C30  aromatic  1.331  0.020  1.331
 4C9  N2   C9   single    1.333  0.020  1.333
 4C9  C9   C10  aromatic  1.416  0.020  1.416
 4C9  C10  C11  aromatic  1.397  0.020  1.397
 4C9  C10  C21  aromatic  1.422  0.020  1.422
 4C9  C11  N3   aromatic  1.347  0.020  1.347
 4C9  C11  N7   aromatic  1.335  0.020  1.335
 4C9  N3   C12  single    1.446  0.020  1.446
 4C9  N3   N6   aromatic  1.341  0.020  1.341
 4C9  C12  C13  single    1.531  0.020  1.531
 4C9  C12  C20  single    1.525  0.020  1.525
 4C9  C13  N4   single    1.453  0.020  1.453
 4C9  N4   C14  single    1.347  0.020  1.347
 4C9  N4   C18  single    1.458  0.020  1.458
 4C9  C14  C15  single    1.546  0.020  1.546
 4C9  C14  O1   double    1.218  0.020  1.218
 4C9  C18  C19  single    1.523  0.020  1.523
 4C9  C19  C20  single    1.524  0.020  1.524
 4C9  N6   C21  aromatic  1.313  0.020  1.313
 4C9  C21  C22  single    1.466  0.020  1.466
 4C9  C22  C29  aromatic  1.395  0.020  1.395
 4C9  C23  O2   single    1.370  0.020  1.370
 4C9  C23  C28  aromatic  1.388  0.020  1.388
 4C9  C24  C25  aromatic  1.390  0.020  1.390
 4C9  C25  C26  aromatic  1.386  0.020  1.386
 4C9  C26  C27  aromatic  1.390  0.020  1.390
 4C9  C28  C29  aromatic  1.385  0.020  1.385
 4C9  N7   C30  aromatic  1.317  0.020  1.317
 4C9  C1   C2   single    1.539  0.020  1.539
 4C9  C1   H1   single    0.970  0.020  1.090
 4C9  C3   H3   single    0.970  0.020  1.090
 4C9  C3   H4   single    0.970  0.020  1.090
 4C9  C3   H5   single    0.970  0.020  1.090
 4C9  C5   H6   single    0.930  0.020  1.080
 4C9  C6   H7   single    0.930  0.020  1.080
 4C9  C8   H8   single    0.930  0.020  1.080
 4C9  N2   H9   single    0.860  0.020  1.020
 4C9  N2   H10  single    0.860  0.020  1.020
 4C9  C12  H11  single    0.970  0.020  1.090
 4C9  C13  H12  single    0.970  0.020  1.090
 4C9  C13  H13  single    0.970  0.020  1.090
 4C9  C16  H15  single    0.970  0.020  1.090
 4C9  C16  H16  single    0.970  0.020  1.090
 4C9  C16  H17  single    0.970  0.020  1.090
 4C9  C17  H18  single    0.970  0.020  1.090
 4C9  C17  H19  single    0.970  0.020  1.090
 4C9  C17  H20  single    0.970  0.020  1.090
 4C9  C18  H21  single    0.970  0.020  1.090
 4C9  C18  H22  single    0.970  0.020  1.090
 4C9  C19  H23  single    0.970  0.020  1.090
 4C9  C19  H24  single    0.970  0.020  1.090
 4C9  C20  H25  single    0.970  0.020  1.090
 4C9  C20  H26  single    0.970  0.020  1.090
 4C9  C24  H27  single    0.930  0.020  1.080
 4C9  C25  H28  single    0.930  0.020  1.080
 4C9  C26  H29  single    0.930  0.020  1.080
 4C9  C27  H30  single    0.930  0.020  1.080
 4C9  C28  H31  single    0.930  0.020  1.080
 4C9  C29  H32  single    0.930  0.020  1.080
 4C9  C30  H33  single    0.930  0.020  1.080
 4C9  C15  H34  single    0.970  0.020  1.090
 4C9  C1   H35  single    0.970  0.020  1.090

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
 4C9  H35  C1   H1   106.43  3.000
 4C9  H35  C1   C15  109.43  3.000
 4C9  H1   C1   C15  106.63  3.000
 4C9  H35  C1   C2   109.60  3.000
 4C9  H1   C1   C2   107.64  3.000
 4C9  C15  C1   C2   116.60  3.000
 4C9  C17  C2   C16  108.66  3.000
 4C9  C17  C2   C3   109.46  3.000
 4C9  C16  C2   C3   108.77  3.000
 4C9  C17  C2   C1   110.73  3.000
 4C9  C16  C2   C1   106.37  3.000
 4C9  C3   C2   C1   112.72  3.000
 4C9  H5   C3   H4   106.88  3.000
 4C9  H5   C3   H3   107.93  3.000
 4C9  H4   C3   H3   107.72  3.000
 4C9  H5   C3   C2   112.46  3.000
 4C9  H4   C3   C2   109.90  3.000
 4C9  H3   C3   C2   111.71  3.000
 4C9  N5   C4   C15  180.00  3.000
 4C9  H6   C5   C22  120.17  3.000
 4C9  H6   C5   C6   119.04  3.000
 4C9  C22  C5   C6   120.78  3.000
 4C9  H7   C6   C23  120.22  3.000
 4C9  H7   C6   C5   120.42  3.000
 4C9  C23  C6   C5   119.36  3.000
 4C9  C24  C7   O2   123.63  3.000
 4C9  C24  C7   C8   120.35  3.000
 4C9  O2   C7   C8   116.02  3.000
 4C9  H8   C8   C27  120.60  3.000
 4C9  H8   C8   C7   119.74  3.000
 4C9  C27  C8   C7   119.66  3.000
 4C9  C30  N1   C9   119.07  3.000
 4C9  C10  C9   N2   123.70  3.000
 4C9  C10  C9   N1   118.54  3.000
 4C9  N2   C9   N1   117.76  3.000
 4C9  C21  C10  C11  104.50  3.000
 4C9  C21  C10  C9   140.06  3.000
 4C9  C11  C10  C9   115.33  3.000
 4C9  N7   C11  N3   126.93  3.000
 4C9  N7   C11  C10  126.42  3.000
 4C9  N3   C11  C10  106.66  3.000
 4C9  N6   N3   C12  121.02  3.000
 4C9  N6   N3   C11  111.44  3.000
 4C9  C12  N3   C11  127.51  3.000
 4C9  H11  C12  C20  109.53  3.000
 4C9  H11  C12  C13  108.63  3.000
 4C9  C20  C12  C13  110.67  3.000
 4C9  H11  C12  N3   105.65  3.000
 4C9  C20  C12  N3   111.86  3.000
 4C9  C13  C12  N3   110.33  3.000
 4C9  H13  C13  H12  108.16  3.000
 4C9  H13  C13  N4   108.54  3.000
 4C9  H12  C13  N4   109.98  3.000
 4C9  H13  C13  C12  109.99  3.000
 4C9  H12  C13  C12  110.84  3.000
 4C9  N4   C13  C12  109.29  3.000
 4C9  C18  N4   C14  127.07  3.000
 4C9  C18  N4   C13  112.97  3.000
 4C9  C14  N4   C13  119.68  3.000
 4C9  O1   C14  C15  119.38  3.000
 4C9  O1   C14  N4   123.25  3.000
 4C9  C15  C14  N4   117.37  3.000
 4C9  H34  C15  C14  109.56  3.000
 4C9  H34  C15  C4   107.69  3.000
 4C9  C14  C15  C4   106.53  3.000
 4C9  H34  C15  C1   109.12  3.000
 4C9  C14  C15  C1   111.36  3.000
 4C9  C4   C15  C1   112.49  3.000
 4C9  H17  C16  H16  107.58  3.000
 4C9  H17  C16  H15  107.76  3.000
 4C9  H16  C16  H15  107.81  3.000
 4C9  H17  C16  C2   111.50  3.000
 4C9  H16  C16  C2   110.83  3.000
 4C9  H15  C16  C2   111.19  3.000
 4C9  H20  C17  H19  107.75  3.000
 4C9  H20  C17  H18  107.95  3.000
 4C9  H19  C17  H18  106.87  3.000
 4C9  H20  C17  C2   111.25  3.000
 4C9  H19  C17  C2   110.43  3.000
 4C9  H18  C17  C2   112.38  3.000
 4C9  H22  C18  H21  106.56  3.000
 4C9  H22  C18  C19  109.93  3.000
 4C9  H21  C18  C19  110.45  3.000
 4C9  H22  C18  N4   107.92  3.000
 4C9  H21  C18  N4   111.47  3.000
 4C9  C19  C18  N4   110.41  3.000
 4C9  H24  C19  H23  107.10  3.000
 4C9  H24  C19  C20  110.13  3.000
 4C9  H23  C19  C20  110.13  3.000
 4C9  H24  C19  C18  108.90  3.000
 4C9  H23  C19  C18  109.34  3.000
 4C9  C20  C19  C18  111.15  3.000
 4C9  H26  C20  H25  107.39  3.000
 4C9  H26  C20  C19  110.48  3.000
 4C9  H25  C20  C19  109.81  3.000
 4C9  H26  C20  C12  110.01  3.000
 4C9  H25  C20  C12  109.05  3.000
 4C9  C19  C20  C12  110.05  3.000
 4C9  C21  N6   N3   107.59  3.000
 4C9  C22  C21  N6   120.61  3.000
 4C9  C22  C21  C10  129.57  3.000
 4C9  N6   C21  C10  109.81  3.000
 4C9  C29  C22  C21  120.28  3.000
 4C9  C29  C22  C5   118.91  3.000
 4C9  C21  C22  C5   120.81  3.000
 4C9  C28  C23  O2   119.79  3.000
 4C9  C28  C23  C6   120.75  3.000
 4C9  O2   C23  C6   119.44  3.000
 4C9  C23  O2   C7   118.96  3.000
 4C9  H27  C24  C25  119.36  3.000
 4C9  H27  C24  C7   121.43  3.000
 4C9  C25  C24  C7   119.21  3.000
 4C9  H28  C25  C26  120.11  3.000
 4C9  H28  C25  C24  118.90  3.000
 4C9  C26  C25  C24  120.99  3.000
 4C9  H29  C26  C27  120.43  3.000
 4C9  H29  C26  C25  120.41  3.000
 4C9  C27  C26  C25  119.17  3.000
 4C9  H30  C27  C26  120.14  3.000
 4C9  H30  C27  C8   119.23  3.000
 4C9  C26  C27  C8   120.63  3.000
 4C9  H31  C28  C29  120.32  3.000
 4C9  H31  C28  C23  120.18  3.000
 4C9  C29  C28  C23  119.50  3.000
 4C9  H32  C29  C28  119.55  3.000
 4C9  H32  C29  C22  119.76  3.000
 4C9  C28  C29  C22  120.68  3.000
 4C9  C30  N7   C11  112.05  3.000
 4C9  H33  C30  N7   116.21  3.000
 4C9  H33  C30  N1   115.30  3.000
 4C9  N7   C30  N1   128.49  3.000
 4C9  H10  N2   H9   117.62  3.000
 4C9  H10  N2   C9   122.13  3.000
 4C9  H9   N2   C9   119.21  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
 4C9  CONST_01  C28  C23  C6   C5     0.00   0.0  0
 4C9  CONST_04  C28  C29  C22  C5     0.00   0.0  0
 4C9  CONST_05  C21  C22  C5   C6   180.00   0.0  0
 4C9  CONST_06  C29  C22  C5   C6     0.00   0.0  0
 4C9  CONST_07  C29  C28  C23  C6     0.00   0.0  0
 4C9  CONST_08  C26  C27  C8   C7     0.00   0.0  0
 4C9  CONST_09  C26  C25  C24  C7     0.00   0.0  0
 4C9  CONST_10  C25  C24  C7   C8     0.00   0.0  0
 4C9  CONST_11  C25  C26  C27  C8     0.00   0.0  0
 4C9  CONST_12  C11  C10  C9   N1     0.00   0.0  0
 4C9  CONST_13  C21  C10  C9   N1   180.00   0.0  0
 4C9  CONST_14  C11  N7   C30  N1     0.00   0.0  0
 4C9  CONST_15  N7   C30  N1   C9     0.00   0.0  0
 4C9  CONST_16  N3   C11  C10  C9   180.00   0.0  0
 4C9  CONST_17  N7   C11  C10  C9     0.00   0.0  0
 4C9  CONST_18  N6   C21  C10  C9   180.00   0.0  0
 4C9  CONST_19  C22  C21  C10  C9     0.00   0.0  0
 4C9  CONST_20  C30  N1   C9   C10    0.00   0.0  0
 4C9  CONST_21  N6   N3   C11  C10    0.00   0.0  0
 4C9  CONST_22  C30  N7   C11  C10    0.00   0.0  0
 4C9  CONST_23  N3   N6   C21  C10    0.00   0.0  0
 4C9  CONST_25  N6   C21  C10  C11    0.00   0.0  0
 4C9  CONST_26  C22  C21  C10  C11  180.00   0.0  0
 4C9  CONST_27  C21  N6   N3   C11    0.00   0.0  0
 4C9  CONST_28  C21  C10  C11  N3     0.00   0.0  0
 4C9  CONST_29  C30  N7   C11  N3   180.00   0.0  0
 4C9  CONST_30  C22  C21  N6   N3   180.00   0.0  0
 4C9  CONST_31  N7   C11  N3   N6   180.00   0.0  0
 4C9  CONST_33  N7   C11  C10  C21  180.00   0.0  0
 4C9  CONST_34  C28  C29  C22  C21  180.00   0.0  0
 4C9  CONST_35  C23  C6   C5   C22    0.00   0.0  0
 4C9  CONST_36  C23  C28  C29  C22    0.00   0.0  0
 4C9  CONST_37  C27  C8   C7   C24    0.00   0.0  0
 4C9  CONST_38  C27  C26  C25  C24    0.00   0.0  0
 4C9  CONST_39  C12  N3   C11  C10  180.00   0.0  0
 4C9  CONST_40  N7   C11  N3   C12    0.00   0.0  0
 4C9  CONST_41  C21  N6   N3   C12  180.00   0.0  0
 4C9  CONST_42  O2   C23  C6   C5   180.00   0.0  0
 4C9  CONST_43  C30  N1   C9   N2   180.00   0.0  0
 4C9  CONST_44  C11  C10  C9   N2   180.00   0.0  0
 4C9  CONST_45  C21  C10  C9   N2     0.00   0.0  0
 4C9  CONST_46  C27  C8   C7   O2   180.00   0.0  0
 4C9  CONST_47  C25  C24  C7   O2   180.00   0.0  0
 4C9  CONST_48  C29  C28  C23  O2   180.00   0.0  0
 4C9  CONST_49  H32  C29  C22  C5   180.00   0.0  0
 4C9  CONST_50  H31  C28  C23  C6   180.00   0.0  0
 4C9  CONST_51  H30  C27  C8   C7   180.00   0.0  0
 4C9  CONST_52  H28  C25  C24  C7   180.00   0.0  0
 4C9  CONST_53  H27  C24  C7   C8   180.00   0.0  0
 4C9  CONST_54  H29  C26  C27  C8   180.00   0.0  0
 4C9  CONST_55  H33  C30  N1   C9   180.00   0.0  0
 4C9  CONST_56  H6   C5   C22  C21    0.00   0.0  0
 4C9  CONST_57  H7   C6   C5   C22  180.00   0.0  0
 4C9  CONST_58  H8   C8   C7   C24  180.00   0.0  0
 4C9  CONST_59  C15  C14  N4   C13  180.00   0.0  0
 4C9  CONST_60  O1   C14  N4   C13    0.00   0.0  0
 4C9  CONST_61  C18  N4   C14  C15    0.00   0.0  0
 4C9  CONST_62  C18  N4   C14  O1   180.00   0.0  0
 4C9  CONST_63  H9   N2   C9   N1     0.00   0.0  0
 4C9  CONST_64  H10  N2   C9   N1   180.00   0.0  0
 4C9  Var_01    C18  N4   C13  C12  -60.51  30.0  1
 4C9  Var_02    C18  C19  C20  C12   53.14  30.0  1
 4C9  Var_03    C19  C18  N4   C13   59.44  30.0  1
 4C9  Var_04    C20  C19  C18  N4   -54.80  30.0  1
 4C9  Var_05    C28  C23  O2   C7    84.50  30.0  2
 4C9  Var_06    C24  C7   O2   C23    5.77  30.0  2
 4C9  Var_07    C15  C1   C2   C3    63.21  30.0  2
 4C9  Var_08    H3   C3   C2   C1    53.20  30.0  3
 4C9  Var_09    H15  C16  C2   C1    60.05  30.0  3
 4C9  Var_10    H18  C17  C2   C1    66.75  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
 4C9  chir_01  C12  N3   C13  C20  negativ
 4C9  chir_02  C15  C14  C4   C1   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
 4C9  plan-1  C5   0.020
 4C9  plan-1  C6   0.020
 4C9  plan-1  C21  0.020
 4C9  plan-1  C22  0.020
 4C9  plan-1  C23  0.020
 4C9  plan-1  O2   0.020
 4C9  plan-1  C28  0.020
 4C9  plan-1  C29  0.020
 4C9  plan-1  H6   0.020
 4C9  plan-1  H7   0.020
 4C9  plan-1  H31  0.020
 4C9  plan-1  H32  0.020
 4C9  plan-2  C7   0.020
 4C9  plan-2  C8   0.020
 4C9  plan-2  O2   0.020
 4C9  plan-2  C24  0.020
 4C9  plan-2  C25  0.020
 4C9  plan-2  C26  0.020
 4C9  plan-2  C27  0.020
 4C9  plan-2  H8   0.020
 4C9  plan-2  H27  0.020
 4C9  plan-2  H28  0.020
 4C9  plan-2  H29  0.020
 4C9  plan-2  H30  0.020
 4C9  plan-3  N1   0.020
 4C9  plan-3  C9   0.020
 4C9  plan-3  C10  0.020
 4C9  plan-3  C11  0.020
 4C9  plan-3  N3   0.020
 4C9  plan-3  C12  0.020
 4C9  plan-3  N6   0.020
 4C9  plan-3  C21  0.020
 4C9  plan-3  C22  0.020
 4C9  plan-3  N7   0.020
 4C9  plan-3  C30  0.020
 4C9  plan-3  H33  0.020
 4C9  plan-3  N2   0.020
 4C9  plan-4  C9   0.020
 4C9  plan-4  H9   0.020
 4C9  plan-4  H10  0.020
 4C9  plan-4  N2   0.020
 4C9  plan-5  C13  0.020
 4C9  plan-5  N4   0.020
 4C9  plan-5  C14  0.020
 4C9  plan-5  C15  0.020
 4C9  plan-5  C18  0.020
 4C9  plan-5  O1   0.020

