# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 00:02:00 2022
#   Inital geometry file: a 247 line input string
#   Ligand name: (1R,2S,5S)-3-[N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl]-N-[(2R,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC[C@H](NC(=O)[C@@H]1[C@@H]2[C@H](CN1C(=O)[C@@H](NC(=O)NC3(CCCCC3)C[S](=O)(=O)C(C)(C)C)C(C)(C)C)C2(C)C)[C@@H](O)C(=O)NC4CC4
#
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
 NNA  NNA  (1R,2S,5S)-3-[N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl]-N-[(2R,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide  ligand  112  49  .  2022-09-22  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_NNA
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
 NNA  C1    C  C     0   0.768   2.8590  -0.5212   0.2082
 NNA  O2    O  O     0  -0.535   2.9831  -1.2204   1.2082
 NNA  N3    N  NH1   0  -0.692   3.7516  -0.5169  -0.8226
 NNA  C4    C  CT    0   0.110   5.0711  -1.1238  -0.7750
 NNA  C5    C  CH2   0  -0.411   4.9827  -2.6558  -0.6258
 NNA  C6    C  CH2   0  -0.459   5.7551  -0.8097  -2.1156
 NNA  C7    C  CH2   0  -0.432   4.2742  -3.3204  -1.7974
 NNA  C8    C  CH2   0  -0.428   5.0842  -1.4903  -3.3062
 NNA  C9    C  CH2   0  -0.430   4.9732  -2.9962  -3.1111
 NNA  C10   C  CH2   0  -0.615   5.9147  -0.6266   0.4202
 NNA  S11   S  S     0   1.227   6.3198   1.1281   0.4123
 NNA  O12   O  OS    0  -0.688   7.4664   1.3299  -0.4830
 NNA  O13   O  OS    0  -0.673   5.1104   1.9114   0.1365
 NNA  C14   C  CT    0  -0.267   6.8800   1.5168   2.1143
 NNA  C15   C  CH3   0  -0.658   7.9838   0.5387   2.4986
 NNA  C16   C  CH3   0  -0.645   7.4109   2.9484   2.0489
 NNA  C17   C  CH3   0  -0.647   5.7004   1.4295   3.0736
 NNA  N18   N  NH1   0  -0.683   1.7980   0.3076   0.0176
 NNA  C19   C  CH1   0  -0.164   0.6814   0.3749   0.9250
 NNA  C20   C  CT    0  -0.081   0.5940   1.7328   1.6754
 NNA  C21   C  CH3   0  -0.654   0.4090   2.9226   0.7331
 NNA  C22   C  CH3   0  -0.674  -0.5678   1.6816   2.6685
 NNA  C23   C  CH3   0  -0.655   1.8997   1.9183   2.4519
 NNA  C24   C  C     0   0.589  -0.5723   0.0593   0.1119
 NNA  O25   O  O     0  -0.488  -0.7918   0.6562  -0.9357
 NNA  N26   N  NR5   0  -0.478  -1.4018  -0.9045   0.5467
 NNA  C27   C  CH2   0  -0.284  -1.2739  -1.7077   1.7612
 NNA  C28   C  CR15  0  -0.202  -2.6212  -1.1624  -0.1949
 NNA  C29   C  CR15  0  -0.270  -3.2178  -2.3898   0.4589
 NNA  C30   C  CR15  0  -0.263  -2.3921  -2.7137   1.6695
 NNA  C31   C  CT    0   0.001  -2.4172  -3.6616   0.5033
 NNA  C32   C  CH3   0  -0.659  -3.2298  -4.9195   0.7114
 NNA  C33   C  CH3   0  -0.683  -1.2023  -3.8761  -0.3682
 NNA  C34   C  C     0   0.590  -3.5887   0.0085  -0.0345
 NNA  O35   O  O     0  -0.475  -3.6747   0.6103   1.0228
 NNA  N36   N  NH1   0  -0.636  -4.3528   0.2500  -1.1087
 NNA  C37   C  CH1   0  -0.107  -5.3616   1.2847  -1.1744
 NNA  C38   C  CH2   0  -0.417  -5.0207   2.3159  -2.2474
 NNA  C39   C  CH2   0  -0.418  -3.7016   3.0263  -1.9680
 NNA  C40   C  CH2   0  -0.420  -3.3468   4.0676  -3.0211
 NNA  C41   C  CH3   0  -0.660  -2.0146   4.7475  -2.7358
 NNA  O42   O  OH1   0  -0.670  -6.8204  -0.0228  -2.6088
 NNA  C43   C  CH1   0  -0.061  -6.7431   0.6434  -1.3831
 NNA  C46   C  CH1   0  -0.083  -7.4314  -0.6106   2.1263
 NNA  C47   C  CH2   0  -0.511  -6.8754  -0.0963   3.4128
 NNA  C48   C  CH2   0  -0.495  -6.2608  -1.2950   2.7586
 NNA  C49   C  C     0   0.516  -7.0139  -0.3480  -0.2502
 NNA  HN3   H  HNH1  0   0.384   3.6688   0.2510  -1.4703
 NNA  H5    H  HCH2  0   0.223   6.0059  -3.0399  -0.5654
 NNA  H5A   H  HCH2  0   0.251   4.4990  -2.9127   0.3151
 NNA  H6    H  HCH2  0   0.246   5.7856   0.2697  -2.2822
 NNA  H6A   H  HCH2  0   0.242   6.7950  -1.1391  -2.0472
 NNA  H7    H  HCH2  0   0.231   4.2525  -4.4005  -1.6347
 NNA  H7A   H  HCH2  0   0.217   3.2324  -2.9907  -1.8392
 NNA  H8    H  HCH2  0   0.217   4.0875  -1.0700  -3.4706
 NNA  H8A   H  HCH2  0   0.235   5.6600  -1.2639  -4.2065
 NNA  H9    H  HCH2  0   0.210   5.9766  -3.4351  -3.1025
 NNA  H9A   H  HCH2  0   0.229   4.4419  -3.4486  -3.9516
 NNA  H10   H  HCH2  0   0.312   5.3953  -0.8450   1.3534
 NNA  H10A  H  HCH2  0   0.307   6.8696  -1.1534   0.4345
 NNA  H15   H  HCH3  0   0.253   8.7923   0.5220   1.7684
 NNA  H15A  H  HCH3  0   0.261   8.4072   0.8481   3.4552
 NNA  H15B  H  HCH3  0   0.253   7.6061  -0.4763   2.6248
 NNA  H16   H  HCH3  0   0.249   6.6423   3.6518   1.7280
 NNA  H16A  H  HCH3  0   0.257   7.7288   3.2409   3.0499
 NNA  H16B  H  HCH3  0   0.253   8.2694   3.0385   1.3854
 NNA  H17   H  HCH3  0   0.244   5.2573   0.4343   3.1119
 NNA  H17A  H  HCH3  0   0.256   6.0580   1.6615   4.0777
 NNA  H17B  H  HCH3  0   0.259   4.9200   2.1461   2.8251
 NNA  HN18  H  HNH1  0   0.387   1.7149   0.8139  -0.8496
 NNA  H19   H  HCH1  0   0.272   0.8453  -0.3907   1.6829
 NNA  H21   H  HCH3  0   0.242  -0.5490   2.9055   0.2154
 NNA  H21A  H  HCH3  0   0.221   0.4548   3.8490   1.3096
 NNA  H21B  H  HCH3  0   0.218   1.1973   2.9739  -0.0206
 NNA  H22   H  HCH3  0   0.222  -0.4245   0.8826   3.3996
 NNA  H22A  H  HCH3  0   0.233  -0.6293   2.6206   3.2216
 NNA  H22B  H  HCH3  0   0.250  -1.5303   1.5222   2.1800
 NNA  H23   H  HCH3  0   0.243   2.7620   1.9774   1.7876
 NNA  H23A  H  HCH3  0   0.225   1.8633   2.8436   3.0313
 NNA  H23B  H  HCH3  0   0.221   2.0706   1.0972   3.1516
 NNA  H27   H  HCH2  0   0.252  -0.2929  -2.1871   1.8069
 NNA  H27A  H  HCH2  0   0.263  -1.3930  -1.0977   2.6577
 NNA  H28   H  HCR5  0   0.275  -2.3924  -1.3287  -1.2527
 NNA  H29   H  HCR5  0   0.270  -4.3000  -2.4644   0.4713
 NNA  H30   H  HCR5  0   0.265  -2.8522  -3.0201   2.6012
 NNA  H32   H  HCH3  0   0.231  -3.5913  -5.3127  -0.2406
 NNA  H32A  H  HCH3  0   0.232  -2.6287  -5.6962   1.1880
 NNA  H32B  H  HCH3  0   0.227  -4.0989  -4.7397   1.3463
 NNA  H33   H  HCH3  0   0.235  -0.6509  -2.9627  -0.5849
 NNA  H33A  H  HCH3  0   0.235  -0.5096  -4.5708   0.1109
 NNA  H33B  H  HCH3  0   0.234  -1.4960  -4.3119  -1.3250
 NNA  HN36  H  HNH1  0   0.396  -4.1635  -0.2648  -1.9554
 NNA  H37   H  HCH1  0   0.260  -5.3635   1.7927  -0.2081
 NNA  H38   H  HCH2  0   0.226  -4.9846   1.8359  -3.2303
 NNA  H38A  H  HCH2  0   0.228  -5.8319   3.0496  -2.2910
 NNA  H39   H  HCH2  0   0.207  -3.7482   3.5076  -0.9849
 NNA  H39A  H  HCH2  0   0.233  -2.8938   2.2925  -1.9033
 NNA  H40   H  HCH2  0   0.210  -3.3128   3.5909  -4.0059
 NNA  H40A  H  HCH2  0   0.211  -4.1392   4.8206  -3.0766
 NNA  H41   H  HCH3  0   0.215  -2.0318   5.2555  -1.7695
 NNA  H41A  H  HCH3  0   0.216  -1.2003   4.0211  -2.7069
 NNA  H41B  H  HCH3  0   0.225  -1.7706   5.4910  -3.4957
 NNA  HO42  H  HOH1  0   0.446  -6.7795  -0.9705  -2.4122
 NNA  H43   H  HCH1  0   0.258  -7.4959   1.4412  -1.3559
 NNA  HN45  H  HNH1  0   0.406  -7.3120   1.1835   1.0433
 NNA  H46   H  HCH1  0   0.270  -8.3862  -1.1251   2.1722
 NNA  H47   H  HCH2  0   0.259  -6.3153   0.8304   3.3801
 NNA  H47A  H  HCH2  0   0.260  -7.4705  -0.2311   4.3060
 NNA  H48   H  HCH2  0   0.253  -6.4278  -2.2712   3.1947
 NNA  H48A  H  HCH2  0   0.269  -5.2934  -1.1611   2.2939
 NNA  O44   O  O     0  -0.486  -6.9959  -1.5510  -0.4739
 NNA  N45   N  NH1   0  -0.629  -7.2322   0.1822   0.9565

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
 NNA  C1   O2    double  1.227  0.020  1.227
 NNA  C1   N3    single  1.364  0.020  1.364
 NNA  C1   N18   single  1.360  0.020  1.360
 NNA  N3   C4    single  1.453  0.020  1.453
 NNA  C4   C5    single  1.542  0.020  1.542
 NNA  C4   C6    single  1.537  0.020  1.537
 NNA  C4   C10   single  1.545  0.020  1.545
 NNA  C5   C7    single  1.522  0.020  1.522
 NNA  C6   C8    single  1.527  0.020  1.527
 NNA  C7   C9    single  1.523  0.020  1.523
 NNA  C8   C9    single  1.523  0.020  1.523
 NNA  C10  S11   single  1.801  0.020  1.801
 NNA  S11  O12   double  1.469  0.020  1.469
 NNA  S11  O13   double  1.467  0.020  1.467
 NNA  S11  C14   single  1.834  0.020  1.834
 NNA  C14  C15   single  1.524  0.020  1.524
 NNA  C14  C16   single  1.528  0.020  1.528
 NNA  C14  C17   single  1.523  0.020  1.523
 NNA  N18  C19   single  1.440  0.020  1.440
 NNA  C19  C20   single  1.554  0.020  1.554
 NNA  C19  C24   single  1.527  0.020  1.527
 NNA  C20  C21   single  1.529  0.020  1.529
 NNA  C20  C22   single  1.529  0.020  1.529
 NNA  C20  C23   single  1.530  0.020  1.530
 NNA  C24  O25   double  1.226  0.020  1.226
 NNA  C24  N26   single  1.344  0.020  1.344
 NNA  N26  C27   single  1.462  0.020  1.462
 NNA  N26  C28   single  1.450  0.020  1.450
 NNA  C27  C30   single  1.507  0.020  1.507
 NNA  C28  C29   single  1.513  0.020  1.513
 NNA  C28  C34   single  1.527  0.020  1.527
 NNA  C29  C30   single  1.501  0.020  1.501
 NNA  C29  C31   single  1.504  0.020  1.504
 NNA  C30  C31   single  1.503  0.020  1.503
 NNA  C31  C32   single  1.512  0.020  1.512
 NNA  C31  C33   single  1.510  0.020  1.510
 NNA  C34  O35   double  1.220  0.020  1.220
 NNA  C34  N36   single  1.340  0.020  1.340
 NNA  N36  C37   single  1.447  0.020  1.447
 NNA  C37  C38   single  1.527  0.020  1.527
 NNA  C37  C43   single  1.537  0.020  1.537
 NNA  C38  C39   single  1.524  0.020  1.524
 NNA  C39  C40   single  1.523  0.020  1.523
 NNA  C40  C41   single  1.523  0.020  1.523
 NNA  O42  C43   single  1.397  0.020  1.397
 NNA  C43  C49   single  1.530  0.020  1.530
 NNA  O44  C49   double  1.224  0.020  1.224
 NNA  N45  C46   single  1.427  0.020  1.427
 NNA  N45  C49   single  1.336  0.020  1.336
 NNA  C46  C47   single  1.493  0.020  1.493
 NNA  C46  C48   single  1.496  0.020  1.496
 NNA  C47  C48   single  1.498  0.020  1.498
 NNA  N3   HN3   single  0.890  0.020  1.040
 NNA  C5   H5    single  0.970  0.020  1.090
 NNA  C5   H5A   single  0.970  0.020  1.090
 NNA  C6   H6    single  0.970  0.020  1.090
 NNA  C6   H6A   single  0.970  0.020  1.090
 NNA  C7   H7    single  0.970  0.020  1.090
 NNA  C7   H7A   single  0.970  0.020  1.090
 NNA  C8   H8    single  0.970  0.020  1.090
 NNA  C8   H8A   single  0.970  0.020  1.090
 NNA  C9   H9    single  0.970  0.020  1.090
 NNA  C9   H9A   single  0.970  0.020  1.090
 NNA  C10  H10   single  0.970  0.020  1.090
 NNA  C10  H10A  single  0.970  0.020  1.090
 NNA  C15  H15   single  0.970  0.020  1.090
 NNA  C15  H15A  single  0.970  0.020  1.090
 NNA  C15  H15B  single  0.970  0.020  1.090
 NNA  C16  H16   single  0.970  0.020  1.090
 NNA  C16  H16A  single  0.970  0.020  1.090
 NNA  C16  H16B  single  0.970  0.020  1.090
 NNA  C17  H17   single  0.970  0.020  1.090
 NNA  C17  H17A  single  0.970  0.020  1.090
 NNA  C17  H17B  single  0.970  0.020  1.090
 NNA  N18  HN18  single  0.860  0.020  1.020
 NNA  C19  H19   single  0.970  0.020  1.090
 NNA  C21  H21   single  0.970  0.020  1.090
 NNA  C21  H21A  single  0.970  0.020  1.090
 NNA  C21  H21B  single  0.970  0.020  1.090
 NNA  C22  H22   single  0.970  0.020  1.090
 NNA  C22  H22A  single  0.970  0.020  1.090
 NNA  C22  H22B  single  0.970  0.020  1.090
 NNA  C23  H23   single  0.970  0.020  1.090
 NNA  C23  H23A  single  0.970  0.020  1.090
 NNA  C23  H23B  single  0.970  0.020  1.090
 NNA  C27  H27   single  0.970  0.020  1.090
 NNA  C27  H27A  single  0.970  0.020  1.090
 NNA  C28  H28   single  0.970  0.020  1.090
 NNA  C29  H29   single  0.970  0.020  1.090
 NNA  C30  H30   single  0.970  0.020  1.090
 NNA  C32  H32   single  0.970  0.020  1.090
 NNA  C32  H32A  single  0.970  0.020  1.090
 NNA  C32  H32B  single  0.970  0.020  1.090
 NNA  C33  H33   single  0.970  0.020  1.090
 NNA  C33  H33A  single  0.970  0.020  1.090
 NNA  C33  H33B  single  0.970  0.020  1.090
 NNA  N36  HN36  single  0.860  0.020  1.020
 NNA  C37  H37   single  0.970  0.020  1.090
 NNA  C38  H38   single  0.970  0.020  1.090
 NNA  C38  H38A  single  0.970  0.020  1.090
 NNA  C39  H39   single  0.970  0.020  1.090
 NNA  C39  H39A  single  0.970  0.020  1.090
 NNA  C40  H40   single  0.970  0.020  1.090
 NNA  C40  H40A  single  0.970  0.020  1.090
 NNA  C41  H41   single  0.970  0.020  1.090
 NNA  C41  H41A  single  0.970  0.020  1.090
 NNA  C41  H41B  single  0.970  0.020  1.090
 NNA  O42  HO42  single  0.850  0.020  0.980
 NNA  C43  H43   single  0.970  0.020  1.090
 NNA  N45  HN45  single  0.860  0.020  1.020
 NNA  C46  H46   single  0.970  0.020  1.090
 NNA  C47  H47   single  0.970  0.020  1.090
 NNA  C47  H47A  single  0.970  0.020  1.090
 NNA  C48  H48   single  0.970  0.020  1.090
 NNA  C48  H48A  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
 NNA  N18   C1   N3    113.76  3.000
 NNA  N18   C1   O2    122.73  3.000
 NNA  N3    C1   O2    123.50  3.000
 NNA  HN3   N3   C4    114.44  3.000
 NNA  HN3   N3   C1    115.75  3.000
 NNA  C4    N3   C1    124.64  3.000
 NNA  C10   C4   C6    111.46  3.000
 NNA  C10   C4   C5    106.03  3.000
 NNA  C6    C4   C5    108.23  3.000
 NNA  C10   C4   N3    112.75  3.000
 NNA  C6    C4   N3    106.87  3.000
 NNA  C5    C4   N3    111.48  3.000
 NNA  H5A   C5   H5    106.54  3.000
 NNA  H5A   C5   C7    110.82  3.000
 NNA  H5    C5   C7    108.93  3.000
 NNA  H5A   C5   C4    110.09  3.000
 NNA  H5    C5   C4    107.48  3.000
 NNA  C7    C5   C4    112.71  3.000
 NNA  H6A   C6   H6    106.30  3.000
 NNA  H6A   C6   C8    109.43  3.000
 NNA  H6    C6   C8    109.50  3.000
 NNA  H6A   C6   C4    107.89  3.000
 NNA  H6    C6   C4    110.32  3.000
 NNA  C8    C6   C4    113.17  3.000
 NNA  H7A   C7   H7    106.55  3.000
 NNA  H7A   C7   C9    109.88  3.000
 NNA  H7    C7   C9    110.37  3.000
 NNA  H7A   C7   C5    109.95  3.000
 NNA  H7    C7   C5    109.05  3.000
 NNA  C9    C7   C5    110.94  3.000
 NNA  H8A   C8   H8    106.06  3.000
 NNA  H8A   C8   C9    110.43  3.000
 NNA  H8    C8   C9    109.44  3.000
 NNA  H8A   C8   C6    108.58  3.000
 NNA  H8    C8   C6    110.26  3.000
 NNA  C9    C8   C6    111.90  3.000
 NNA  H9A   C9   H9    106.60  3.000
 NNA  H9A   C9   C8    110.27  3.000
 NNA  H9    C9   C8    109.30  3.000
 NNA  H9A   C9   C7    110.63  3.000
 NNA  H9    C9   C7    109.17  3.000
 NNA  C8    C9   C7    110.77  3.000
 NNA  H10A  C10  H10   108.01  3.000
 NNA  H10A  C10  S11   105.89  3.000
 NNA  H10   C10  S11   107.82  3.000
 NNA  H10A  C10  C4    109.44  3.000
 NNA  H10   C10  C4    109.73  3.000
 NNA  S11   C10  C4    115.66  3.000
 NNA  C14   S11  O13   108.25  3.000
 NNA  C14   S11  O12   107.35  3.000
 NNA  O13   S11  O12   117.10  3.000
 NNA  C14   S11  C10   105.74  3.000
 NNA  O13   S11  C10   109.61  3.000
 NNA  O12   S11  C10   108.19  3.000
 NNA  C17   C14  C16   110.47  3.000
 NNA  C17   C14  C15   111.43  3.000
 NNA  C16   C14  C15   111.12  3.000
 NNA  C17   C14  S11   109.62  3.000
 NNA  C16   C14  S11   105.37  3.000
 NNA  C15   C14  S11   108.62  3.000
 NNA  H15B  C15  H15A  107.28  3.000
 NNA  H15B  C15  H15   108.68  3.000
 NNA  H15A  C15  H15   107.69  3.000
 NNA  H15B  C15  C14   112.07  3.000
 NNA  H15A  C15  C14   108.68  3.000
 NNA  H15   C15  C14   112.23  3.000
 NNA  H16B  C16  H16A  107.91  3.000
 NNA  H16B  C16  H16   108.85  3.000
 NNA  H16A  C16  H16   107.62  3.000
 NNA  H16B  C16  C14   112.18  3.000
 NNA  H16A  C16  C14   108.26  3.000
 NNA  H16   C16  C14   111.85  3.000
 NNA  H17B  C17  H17A  107.77  3.000
 NNA  H17B  C17  H17   108.52  3.000
 NNA  H17A  C17  H17   107.16  3.000
 NNA  H17B  C17  C14   111.96  3.000
 NNA  H17A  C17  C14   108.28  3.000
 NNA  H17   C17  C14   112.92  3.000
 NNA  HN18  N18  C19   117.04  3.000
 NNA  HN18  N18  C1    119.42  3.000
 NNA  C19   N18  C1    123.03  3.000
 NNA  H19   C19  C24   110.41  3.000
 NNA  H19   C19  C20   106.65  3.000
 NNA  C24   C19  C20   113.05  3.000
 NNA  H19   C19  N18   106.78  3.000
 NNA  C24   C19  N18   106.94  3.000
 NNA  C20   C19  N18   112.87  3.000
 NNA  C23   C20  C22   108.83  3.000
 NNA  C23   C20  C21   108.76  3.000
 NNA  C22   C20  C21   109.53  3.000
 NNA  C23   C20  C19   107.64  3.000
 NNA  C22   C20  C19   109.09  3.000
 NNA  C21   C20  C19   112.91  3.000
 NNA  H21B  C21  H21A  107.12  3.000
 NNA  H21B  C21  H21   107.92  3.000
 NNA  H21A  C21  H21   107.53  3.000
 NNA  H21B  C21  C20   111.99  3.000
 NNA  H21A  C21  C20   109.25  3.000
 NNA  H21   C21  C20   112.78  3.000
 NNA  H22B  C22  H22A  107.63  3.000
 NNA  H22B  C22  H22   107.98  3.000
 NNA  H22A  C22  H22   107.30  3.000
 NNA  H22B  C22  C20   112.60  3.000
 NNA  H22A  C22  C20   110.06  3.000
 NNA  H22   C22  C20   111.06  3.000
 NNA  H23B  C23  H23A  107.59  3.000
 NNA  H23B  C23  H23   107.90  3.000
 NNA  H23A  C23  H23   107.68  3.000
 NNA  H23B  C23  C20   111.56  3.000
 NNA  H23A  C23  C20   110.08  3.000
 NNA  H23   C23  C20   111.85  3.000
 NNA  N26   C24  O25   121.02  3.000
 NNA  N26   C24  C19   118.85  3.000
 NNA  O25   C24  C19   120.10  3.000
 NNA  C28   N26  C27   113.62  3.000
 NNA  C28   N26  C24   118.75  3.000
 NNA  C27   N26  C24   127.51  3.000
 NNA  H27A  C27  H27   107.99  3.000
 NNA  H27A  C27  C30   110.02  3.000
 NNA  H27   C27  C30   112.07  3.000
 NNA  H27A  C27  N26   111.47  3.000
 NNA  H27   C27  N26   110.76  3.000
 NNA  C30   C27  N26   104.56  3.000
 NNA  H28   C28  C34   110.50  3.000
 NNA  H28   C28  C29   112.13  3.000
 NNA  C34   C28  C29   109.07  3.000
 NNA  H28   C28  N26   110.20  3.000
 NNA  C34   C28  N26   110.03  3.000
 NNA  C29   C28  N26   104.76  3.000
 NNA  H29   C29  C31   118.21  3.000
 NNA  H29   C29  C30   121.66  3.000
 NNA  C31   C29  C30    60.04  3.000
 NNA  H29   C29  C28   117.00  3.000
 NNA  C31   C29  C28   119.27  3.000
 NNA  C30   C29  C28   107.86  3.000
 NNA  H30   C30  C31   118.80  3.000
 NNA  H30   C30  C29   121.41  3.000
 NNA  C31   C30  C29    60.07  3.000
 NNA  H30   C30  C27   116.85  3.000
 NNA  C31   C30  C27   118.72  3.000
 NNA  C29   C30  C27   108.26  3.000
 NNA  C33   C31  C32   113.18  3.000
 NNA  C33   C31  C30   121.59  3.000
 NNA  C32   C31  C30   115.27  3.000
 NNA  C33   C31  C29   122.10  3.000
 NNA  C32   C31  C29   114.94  3.000
 NNA  C30   C31  C29    59.89  3.000
 NNA  H32B  C32  H32A  107.56  3.000
 NNA  H32B  C32  H32   107.64  3.000
 NNA  H32A  C32  H32   107.87  3.000
 NNA  H32B  C32  C31   111.78  3.000
 NNA  H32A  C32  C31   110.86  3.000
 NNA  H32   C32  C31   110.95  3.000
 NNA  H33B  C33  H33A  107.53  3.000
 NNA  H33B  C33  H33   107.26  3.000
 NNA  H33A  C33  H33   107.45  3.000
 NNA  H33B  C33  C31   110.24  3.000
 NNA  H33A  C33  C31   110.34  3.000
 NNA  H33   C33  C31   113.77  3.000
 NNA  N36   C34  O35   124.45  3.000
 NNA  N36   C34  C28   114.52  3.000
 NNA  O35   C34  C28   120.93  3.000
 NNA  HN36  N36  C37   117.24  3.000
 NNA  HN36  N36  C34   118.28  3.000
 NNA  C37   N36  C34   124.25  3.000
 NNA  H37   C37  C43   108.22  3.000
 NNA  H37   C37  C38   107.95  3.000
 NNA  C43   C37  C38   112.77  3.000
 NNA  H37   C37  N36   107.09  3.000
 NNA  C43   C37  N36   109.54  3.000
 NNA  C38   C37  N36   111.06  3.000
 NNA  H38A  C38  H38   106.41  3.000
 NNA  H38A  C38  C39   109.65  3.000
 NNA  H38   C38  C39   109.91  3.000
 NNA  H38A  C38  C37   108.37  3.000
 NNA  H38   C38  C37   110.02  3.000
 NNA  C39   C38  C37   112.29  3.000
 NNA  H39A  C39  H39   105.85  3.000
 NNA  H39A  C39  C40   109.13  3.000
 NNA  H39   C39  C40   109.27  3.000
 NNA  H39A  C39  C38   109.73  3.000
 NNA  H39   C39  C38   109.42  3.000
 NNA  C40   C39  C38   113.18  3.000
 NNA  H40A  C40  H40   106.05  3.000
 NNA  H40A  C40  C41   109.62  3.000
 NNA  H40   C40  C41   109.62  3.000
 NNA  H40A  C40  C39   109.68  3.000
 NNA  H40   C40  C39   109.36  3.000
 NNA  C41   C40  C39   112.31  3.000
 NNA  H41B  C41  H41A  107.77  3.000
 NNA  H41B  C41  H41   107.63  3.000
 NNA  H41A  C41  H41   107.33  3.000
 NNA  H41B  C41  C40   111.69  3.000
 NNA  H41A  C41  C40   111.13  3.000
 NNA  H41   C41  C40   111.09  3.000
 NNA  HO42  O42  C43   106.62  3.000
 NNA  H43   C43  C49   109.36  3.000
 NNA  H43   C43  O42   109.30  3.000
 NNA  C49   C43  O42   109.32  3.000
 NNA  H43   C43  C37   108.05  3.000
 NNA  C49   C43  C37   109.21  3.000
 NNA  O42   C43  C37   111.57  3.000
 NNA  H46   C46  C48   116.97  3.000
 NNA  H46   C46  C47   117.03  3.000
 NNA  C48   C46  C47    60.13  3.000
 NNA  H46   C46  N45   114.88  3.000
 NNA  C48   C46  N45   119.42  3.000
 NNA  C47   C46  N45   117.58  3.000
 NNA  H47A  C47  H47   114.58  3.000
 NNA  H47A  C47  C48   119.13  3.000
 NNA  H47   C47  C48   117.35  3.000
 NNA  H47A  C47  C46   117.62  3.000
 NNA  H47   C47  C46   117.47  3.000
 NNA  C48   C47  C46    60.04  3.000
 NNA  H48A  C48  H48   115.01  3.000
 NNA  H48A  C48  C47   117.11  3.000
 NNA  H48   C48  C47   118.87  3.000
 NNA  H48A  C48  C46   117.49  3.000
 NNA  H48   C48  C46   117.53  3.000
 NNA  C47   C48  C46    59.83  3.000
 NNA  N45   C49  O44   123.89  3.000
 NNA  N45   C49  C43   116.14  3.000
 NNA  O44   C49  C43   119.95  3.000
 NNA  HN45  N45  C49   119.00  3.000
 NNA  HN45  N45  C46   118.04  3.000
 NNA  C49   N45  C46   122.87  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
 NNA  CONST_01  C27   N26  C24  C19     0.00   0.0  0
 NNA  CONST_02  C28   N26  C24  C19   180.00   0.0  0
 NNA  CONST_03  C27   N26  C24  O25   180.00   0.0  0
 NNA  CONST_04  C28   N26  C24  O25     0.00   0.0  0
 NNA  CONST_05  C4    N3   C1   O2      0.00   0.0  0
 NNA  CONST_06  C37   N36  C34  C28   180.00   0.0  0
 NNA  CONST_07  C46   N45  C49  C43   180.00   0.0  0
 NNA  CONST_08  C46   N45  C49  O44     0.00   0.0  0
 NNA  CONST_09  N18   C1   N3   C4    180.00   0.0  0
 NNA  CONST_10  HN36  N36  C34  C28     0.00   0.0  0
 NNA  CONST_11  C19   N18  C1   O2      0.00   0.0  0
 NNA  CONST_12  C37   N36  C34  O35     0.00   0.0  0
 NNA  CONST_13  C19   N18  C1   N3    180.00   0.0  0
 NNA  CONST_14  HN3   N3   C1   O2    180.00   0.0  0
 NNA  CONST_15  HN18  N18  C1   O2    180.00   0.0  0
 NNA  CONST_16  HN45  N45  C49  C43     0.00   0.0  0
 NNA  Var_01    C9    C7   C5   C4     57.78  30.0  1
 NNA  Var_02    C9    C8   C6   C4    -54.70  30.0  1
 NNA  Var_03    C7    C9   C8   C6     54.13  30.0  1
 NNA  Var_04    C29   C30  C27  N26    -4.96  30.0  1
 NNA  Var_05    C28   C29  C30  C27    -0.82  30.0  1
 NNA  Var_06    C30   C27  N26  C28     9.57  30.0  1
 NNA  Var_07    C48   C47  C46  N45  -109.83  30.0  1
 NNA  Var_08    H48   C48  C47  C46  -106.86  30.0  1
 NNA  Var_09    C49   N45  C46  C47   144.09  30.0  2
 NNA  Var_10    H32   C32  C31  C29    86.74  30.0  3
 NNA  Var_11    H33   C33  C31  C29    31.64  30.0  3
 NNA  Var_12    O12   S11  C10  C4    -80.85  30.0  3
 NNA  Var_13    C15   C14  S11  C10    52.90  30.0  3
 NNA  Var_14    C40   C39  C38  C37  -179.56  30.0  3
 NNA  Var_15    C41   C40  C39  C38  -179.00  30.0  3
 NNA  Var_16    H15   C15  C14  S11    53.70  30.0  3
 NNA  Var_17    H16   C16  C14  S11    59.78  30.0  3
 NNA  Var_18    H17   C17  C14  S11    61.36  30.0  3
 NNA  Var_19    H21   C21  C20  C19    66.06  30.0  3
 NNA  Var_20    H22   C22  C20  C19    60.01  30.0  3
 NNA  Var_21    H23   C23  C20  C19    62.81  30.0  3
 NNA  Var_22    H41   C41  C40  C39   -59.81  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
 NNA  chir_01  C4   C5   C6   C10  positiv
 NNA  chir_02  C19  N18  C20  C24  negativ
 NNA  chir_03  C28  N26  C29  C34  negativ
 NNA  chir_06  C37  N36  C38  C43  negativ
 NNA  chir_07  C43  O42  C37  C49  positiv
 NNA  chir_08  C29  C28  C30  C31  both
 NNA  chir_09  C30  C27  C29  C31  both
 NNA  chir_10  C46  N45  C47  C48  both

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
 NNA  plan-1  C1    0.020
 NNA  plan-1  O2    0.020
 NNA  plan-1  N3    0.020
 NNA  plan-1  C4    0.020
 NNA  plan-1  N18   0.020
 NNA  plan-1  C19   0.020
 NNA  plan-1  HN3   0.020
 NNA  plan-1  HN18  0.020
 NNA  plan-2  C19   0.020
 NNA  plan-2  C24   0.020
 NNA  plan-2  O25   0.020
 NNA  plan-2  N26   0.020
 NNA  plan-2  C27   0.020
 NNA  plan-2  C28   0.020
 NNA  plan-3  C28   0.020
 NNA  plan-3  C34   0.020
 NNA  plan-3  O35   0.020
 NNA  plan-3  N36   0.020
 NNA  plan-3  C37   0.020
 NNA  plan-3  HN36  0.020
 NNA  plan-4  C43   0.020
 NNA  plan-4  C46   0.020
 NNA  plan-4  C49   0.020
 NNA  plan-4  HN45  0.020
 NNA  plan-4  O44   0.020
 NNA  plan-4  N45   0.020

