# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 05:07:05 2020
#   Inital geometry file: a 153 line input string
#   Ligand name: (5S,18R,19R)-31-oxo-20-oxa-2,6,11,13-tetraazahexacyclo[19.6.2.1~2,5~.1~15,19~.0~9,13~.0~24,28~]hentriaconta-1(27),9,11,15,21,23,25,28-octaene-18-carbonitrile (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O=C1[C@@H]2CCN1c3cccc4ccc(O[C@@H]5CC(=CC[C@@H]5C#N)Cn6cncc6CCN2)cc34
#
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
 U66  U66  '(5S,18R,19R)-31-oxo-20-oxa-2,6,11,13-tetraazahexacyclo[19.6.2.1~2,5~.1~15,19~.0~9,13~.0~24,28~]hentriaconta-1(27),9,11,15,21,23,25,28-octaene-18-carbonitrile (non-preferred name)'  ligand  61  34  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_U66
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
 U66  C     C  CR66  0   0.162  -0.7801  -0.4927   -3.8591
 U66  C1    C  CR6   0   0.298  -0.5470   0.7976   -3.3134
 U66  C2    C  CR66  0   0.067  -0.1737  -1.6065   -3.2245
 U66  C3    C  CR16  0  -0.463  -1.5887  -0.6926   -5.0032
 U66  N     N  NR5   0  -0.584  -1.0643   1.9336   -3.9731
 U66  C4    C  CR16  0  -0.287   0.2046   0.9520   -2.1792
 U66  C5    C  CR16  0  -0.298  -0.3630  -2.8911   -3.7877
 U66  C6    C  CR16  0  -0.310   0.6002  -1.4146   -2.0589
 U66  C7    C  CR6   0   0.403  -1.7856  -1.9601   -5.4907
 U66  C8    C  CR5   0   0.533  -0.4094   2.5112   -5.0054
 U66  C9    C  CH2   0  -0.264  -2.3536   2.5412   -3.6781
 U66  C10   C  CR16  0  -0.275   0.7760  -0.1623   -1.5371
 U66  C11   C  CR16  0  -0.338  -1.1447  -3.0689   -4.8901
 U66  O     O  O2    0  -0.491  -2.5802  -2.2508   -6.5465
 U66  C12   C  CR15  0  -0.223  -1.3281   3.5786   -5.5900
 U66  O13   O  O     0  -0.468   0.6979   2.1985   -5.3992
 U66  C14   C  CH2   0  -0.490  -2.2570   3.8760   -4.4184
 U66  C15   C  CH1   0   0.034  -3.7548  -1.4831   -6.7480
 U66  N16   N  NH1   0  -0.604  -2.0788   2.9846   -6.6854
 U66  C17   C  CH1   0  -0.408  -4.8500  -2.5042   -7.0914
 U66  C18   C  CH2   0  -0.558  -3.5878  -0.4636   -7.8659
 U66  C19   C  CH2   0  -0.253  -1.2746   2.5226   -7.8043
 U66  C20   C  CH2   0  -0.456  -4.5229  -3.2368   -8.3957
 U66  C21   C  CSP   0   0.140  -6.1294  -1.8124   -7.2083
 U66  C22   C  C     0   0.177  -3.7491  -1.0247   -9.2497
 U66  C23   C  CH2   0  -0.580  -2.1331   2.3801   -9.0630
 U66  C24   C  C1    0  -0.302  -4.1559  -2.2721   -9.4769
 U66  N25   N  NS    0  -0.260  -7.1385  -1.2671   -7.2950
 U66  C26   C  CH2   0  -0.432  -3.5302  -0.0779  -10.3984
 U66  C27   C  CR5   0   0.303  -1.5143   1.4375  -10.0387
 U66  N28   N  NR5   0  -0.441  -2.1507   0.3447  -10.5760
 U66  C29   C  CR15  0  -0.260  -0.2442   1.3854  -10.5468
 U66  C30   C  CR15  0   0.085  -1.2530  -0.2953  -11.3602
 U66  NZ    N  N     0  -0.449  -0.0930   0.3040  -11.3675
 U66  H31   H  HCR6  0   0.263  -2.0483   0.1668   -5.4776
 U66  H41   H  HCR6  0   0.266   0.3662   1.9461   -1.7820
 U66  H51   H  HCR6  0   0.265   0.1110  -3.7450   -3.3197
 U66  H61   H  HCR6  0   0.261   1.0519  -2.2759   -1.5820
 U66  H91   H  HCH2  0   0.261  -2.4816   2.6653   -2.6030
 U66  H92   H  HCH2  0   0.241  -3.1751   1.9236   -4.0499
 U66  H101  H  HCR6  0   0.262   1.3658  -0.0186   -0.6420
 U66  H111  H  HCR6  0   0.272  -1.3004  -4.0560   -5.3059
 U66  H121  H  HCR5  0   0.253  -0.7365   4.4515   -5.8982
 U66  H141  H  HCH2  0   0.262  -3.2299   4.2535   -4.7315
 U66  H142  H  HCH2  0   0.258  -1.7983   4.6244   -3.7702
 U66  H151  H  HCH1  0   0.286  -4.0236  -0.9681   -5.8205
 U66  H161  H  HNH1  0   0.361  -2.7481   3.6732   -7.0087
 U66  H117  H  HCH1  0   0.341  -4.9497  -3.2178   -6.2692
 U66  H181  H  HCH2  0   0.281  -2.6089   0.0120   -7.7625
 U66  H182  H  HCH2  0   0.271  -4.3175   0.3397   -7.7166
 U66  H191  H  HCH2  0   0.222  -0.8458   1.5495   -7.5538
 U66  H192  H  HCH2  0   0.216  -0.4252   3.1858   -8.0211
 U66  H201  H  HCH2  0   0.276  -5.3781  -3.8391   -8.7055
 U66  H202  H  HCH2  0   0.283  -3.7112  -3.9449   -8.2111
 U66  H231  H  HCH2  0   0.258  -3.1243   2.0273   -8.7741
 U66  H232  H  HCH2  0   0.276  -2.2880   3.3623   -9.5179
 U66  H241  H  H     0   0.257  -4.2628  -2.6193  -10.4990
 U66  H261  H  HCH2  0   0.292  -3.8504  -0.5435  -11.3299
 U66  H262  H  HCH2  0   0.283  -4.1477   0.8144  -10.2746
 U66  H291  H  HCR5  0   0.249   0.5651   2.0752  -10.3581
 U66  H301  H  HCR5  0   0.275  -1.5114  -1.1900  -11.9076

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
 U66  C    C1    aromatic  1.420  0.020  1.420
 U66  C    C2    single    1.418  0.020  1.418
 U66  C    C3    aromatic  1.415  0.020  1.415
 U66  C1   N     single    1.412  0.020  1.412
 U66  C1   C4    single    1.369  0.020  1.369
 U66  C2   C5    aromatic  1.415  0.020  1.415
 U66  C2   C6    aromatic  1.412  0.020  1.412
 U66  C3   C7    aromatic  1.372  0.020  1.372
 U66  C3   H31   single    0.930  0.020  1.080
 U66  N    C8    single    1.352  0.020  1.352
 U66  N    C9    single    1.456  0.020  1.456
 U66  C4   C10   aromatic  1.407  0.020  1.407
 U66  C4   H41   single    0.930  0.020  1.080
 U66  C5   C11   aromatic  1.363  0.020  1.363
 U66  C5   H51   single    0.930  0.020  1.080
 U66  C6   C10   aromatic  1.368  0.020  1.368
 U66  C6   H61   single    0.930  0.020  1.080
 U66  C7   C11   single    1.415  0.020  1.415
 U66  C7   O     single    1.353  0.020  1.353
 U66  C8   C12   single    1.525  0.020  1.525
 U66  C8   O13   double    1.216  0.020  1.216
 U66  C9   C14   single    1.529  0.020  1.529
 U66  C9   H91   single    0.970  0.020  1.090
 U66  C9   H92   single    0.970  0.020  1.090
 U66  C10  H101  single    0.930  0.020  1.080
 U66  C11  H111  single    0.930  0.020  1.080
 U66  O    C15   single    1.418  0.020  1.418
 U66  C12  C14   single    1.525  0.020  1.525
 U66  C12  N16   single    1.455  0.020  1.455
 U66  C12  H121  single    0.970  0.020  1.090
 U66  C14  H141  single    0.970  0.020  1.090
 U66  C14  H142  single    0.970  0.020  1.090
 U66  C15  C17   single    1.536  0.020  1.536
 U66  C15  C18   single    1.522  0.020  1.522
 U66  C15  H151  single    0.970  0.020  1.090
 U66  N16  C19   single    1.453  0.020  1.453
 U66  N16  H161  single    0.890  0.020  1.040
 U66  C17  C20   single    1.531  0.020  1.531
 U66  C17  C21   single    1.459  0.020  1.459
 U66  C17  H117  single    0.970  0.020  1.090
 U66  C18  C22   single    1.502  0.020  1.502
 U66  C18  H181  single    0.970  0.020  1.090
 U66  C18  H182  single    0.970  0.020  1.090
 U66  C19  C23   single    1.530  0.020  1.530
 U66  C19  H191  single    0.970  0.020  1.090
 U66  C19  H192  single    0.970  0.020  1.090
 U66  C20  C24   single    1.495  0.020  1.495
 U66  C20  H201  single    0.970  0.020  1.090
 U66  C20  H202  single    0.970  0.020  1.090
 U66  C21  N25   triple    1.150  0.020  1.150
 U66  C22  C24   double    1.332  0.020  1.332
 U66  C22  C26   single    1.505  0.020  1.505
 U66  C23  C27   single    1.491  0.020  1.491
 U66  C23  H231  single    0.970  0.020  1.090
 U66  C23  H232  single    0.970  0.020  1.090
 U66  C24  H241  single    0.930  0.020  1.080
 U66  C26  N28   single    1.454  0.020  1.454
 U66  C26  H261  single    0.970  0.020  1.090
 U66  C26  H262  single    0.970  0.020  1.090
 U66  C27  N28   aromatic  1.374  0.020  1.374
 U66  C27  C29   single    1.369  0.020  1.369
 U66  N28  C30   single    1.353  0.020  1.353
 U66  C29  NZ    aromatic  1.366  0.020  1.366
 U66  C29  H291  single    0.930  0.020  1.080
 U66  C30  NZ    aromatic  1.306  0.020  1.306
 U66  C30  H301  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
 U66  C3    C    C2    119.68  3.000
 U66  C3    C    C1    122.19  3.000
 U66  C2    C    C1    118.13  3.000
 U66  C4    C1   N     119.83  3.000
 U66  C4    C1   C     120.72  3.000
 U66  N     C1   C     119.43  3.000
 U66  C6    C2   C5    121.68  3.000
 U66  C6    C2   C     119.80  3.000
 U66  C5    C2   C     118.53  3.000
 U66  H31   C3   C7    121.07  3.000
 U66  H31   C3   C     118.95  3.000
 U66  C7    C3   C     119.98  3.000
 U66  C9    N    C8    113.92  3.000
 U66  C9    N    C1    124.46  3.000
 U66  C8    N    C1    121.53  3.000
 U66  H41   C4   C10   119.93  3.000
 U66  H41   C4   C1    119.30  3.000
 U66  C10   C4   C1    120.76  3.000
 U66  H51   C5   C11   119.85  3.000
 U66  H51   C5   C2    119.02  3.000
 U66  C11   C5   C2    121.12  3.000
 U66  H61   C6   C10   120.42  3.000
 U66  H61   C6   C2    118.93  3.000
 U66  C10   C6   C2    120.64  3.000
 U66  O     C7   C11   115.41  3.000
 U66  O     C7   C3    124.06  3.000
 U66  C11   C7   C3    120.54  3.000
 U66  O13   C8   C12   127.19  3.000
 U66  O13   C8   N     125.34  3.000
 U66  C12   C8   N     107.45  3.000
 U66  H92   C9   H91   108.16  3.000
 U66  H92   C9   C14   112.09  3.000
 U66  H91   C9   C14   112.68  3.000
 U66  H92   C9   N     111.16  3.000
 U66  H91   C9   N     110.58  3.000
 U66  C14   C9   N     102.14  3.000
 U66  H101  C10  C6    120.49  3.000
 U66  H101  C10  C4    119.60  3.000
 U66  C6    C10  C4    119.91  3.000
 U66  H111  C11  C7    119.12  3.000
 U66  H111  C11  C5    120.80  3.000
 U66  C7    C11  C5    120.07  3.000
 U66  C15   O    C7    118.76  3.000
 U66  H121  C12  N16   113.02  3.000
 U66  H121  C12  C14   112.87  3.000
 U66  N16   C12  C14   110.12  3.000
 U66  H121  C12  C8    109.83  3.000
 U66  N16   C12  C8    108.29  3.000
 U66  C14   C12  C8    102.06  3.000
 U66  H142  C14  H141  107.96  3.000
 U66  H142  C14  C12   109.53  3.000
 U66  H141  C14  C12   113.01  3.000
 U66  H142  C14  C9    109.73  3.000
 U66  H141  C14  C9    112.65  3.000
 U66  C12   C14  C9    103.90  3.000
 U66  H151  C15  C18   109.53  3.000
 U66  H151  C15  C17   109.09  3.000
 U66  C18   C15  C17   111.05  3.000
 U66  H151  C15  O     109.75  3.000
 U66  C18   C15  O     112.10  3.000
 U66  C17   C15  O     105.22  3.000
 U66  H161  N16  C19   109.63  3.000
 U66  H161  N16  C12   107.68  3.000
 U66  C19   N16  C12   115.09  3.000
 U66  H117  C17  C21   106.85  3.000
 U66  H117  C17  C20   110.35  3.000
 U66  C21   C17  C20   110.24  3.000
 U66  H117  C17  C15   109.31  3.000
 U66  C21   C17  C15   109.14  3.000
 U66  C20   C17  C15   110.86  3.000
 U66  H182  C18  H181  105.34  3.000
 U66  H182  C18  C22   109.15  3.000
 U66  H181  C18  C22   110.24  3.000
 U66  H182  C18  C15   108.54  3.000
 U66  H181  C18  C15   108.67  3.000
 U66  C22   C18  C15   114.50  3.000
 U66  H192  C19  H191  106.22  3.000
 U66  H192  C19  C23   109.11  3.000
 U66  H191  C19  C23   109.02  3.000
 U66  H192  C19  N16   112.81  3.000
 U66  H191  C19  N16   108.89  3.000
 U66  C23   C19  N16   110.64  3.000
 U66  H202  C20  H201  105.81  3.000
 U66  H202  C20  C24   110.98  3.000
 U66  H201  C20  C24   110.08  3.000
 U66  H202  C20  C17   108.95  3.000
 U66  H201  C20  C17   109.79  3.000
 U66  C24   C20  C17   111.08  3.000
 U66  N25   C21  C17   180.00  3.000
 U66  C26   C22  C24   120.24  3.000
 U66  C26   C22  C18   116.92  3.000
 U66  C24   C22  C18   122.68  3.000
 U66  H232  C23  H231  105.78  3.000
 U66  H232  C23  C27   110.75  3.000
 U66  H231  C23  C27   110.23  3.000
 U66  H232  C23  C19   109.76  3.000
 U66  H231  C23  C19   108.78  3.000
 U66  C27   C23  C19   111.36  3.000
 U66  H241  C24  C22   119.39  3.000
 U66  H241  C24  C20   116.79  3.000
 U66  C22   C24  C20   123.79  3.000
 U66  H262  C26  H261  106.26  3.000
 U66  H262  C26  N28   108.23  3.000
 U66  H261  C26  N28   107.38  3.000
 U66  H262  C26  C22   110.20  3.000
 U66  H261  C26  C22   109.95  3.000
 U66  N28   C26  C22   114.47  3.000
 U66  C29   C27  N28   104.74  3.000
 U66  C29   C27  C23   130.69  3.000
 U66  N28   C27  C23   124.50  3.000
 U66  C30   N28  C27   107.19  3.000
 U66  C30   N28  C26   124.26  3.000
 U66  C27   N28  C26   128.54  3.000
 U66  H291  C29  NZ    121.85  3.000
 U66  H291  C29  C27   127.31  3.000
 U66  NZ    C29  C27   110.84  3.000
 U66  H301  C30  NZ    126.14  3.000
 U66  H301  C30  N28   121.79  3.000
 U66  NZ    C30  N28   112.06  3.000
 U66  C30   NZ   C29   105.17  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
 U66  CONST_01  C10   C4   C1   C       0.00   0.0  0
 U66  CONST_02  C11   C5   C2   C       0.00   0.0  0
 U66  CONST_03  C10   C6   C2   C       0.00   0.0  0
 U66  CONST_04  C11   C7   C3   C       0.00   0.0  0
 U66  CONST_05  C5    C2   C    C1    180.00   0.0  0
 U66  CONST_06  C6    C2   C    C1      0.00   0.0  0
 U66  CONST_07  C7    C3   C    C1    180.00   0.0  0
 U66  CONST_08  C6    C10  C4   C1      0.00   0.0  0
 U66  CONST_09  C4    C1   C    C2      0.00   0.0  0
 U66  CONST_10  C7    C3   C    C2      0.00   0.0  0
 U66  CONST_11  C7    C11  C5   C2      0.00   0.0  0
 U66  CONST_12  C4    C10  C6   C2      0.00   0.0  0
 U66  CONST_13  C4    C1   C    C3    180.00   0.0  0
 U66  CONST_14  C5    C2   C    C3      0.00   0.0  0
 U66  CONST_15  C6    C2   C    C3    180.00   0.0  0
 U66  CONST_16  C5    C11  C7   C3      0.00   0.0  0
 U66  CONST_17  C10   C6   C2   C5    180.00   0.0  0
 U66  CONST_18  C11   C5   C2   C6    180.00   0.0  0
 U66  CONST_19  NZ    C30  N28  C27     0.00   0.0  0
 U66  CONST_20  C30   NZ   C29  C27     0.00   0.0  0
 U66  CONST_21  NZ    C29  C27  N28     0.00   0.0  0
 U66  CONST_22  C29   NZ   C30  N28     0.00   0.0  0
 U66  CONST_23  C30   N28  C27  C29     0.00   0.0  0
 U66  CONST_24  C12   C8   N    C1    180.00   0.0  0
 U66  CONST_25  C12   C8   N    C9      0.00   0.0  0
 U66  CONST_26  O13   C8   N    C1      0.00   0.0  0
 U66  CONST_27  O13   C8   N    C9    180.00   0.0  0
 U66  CONST_28  H41   C4   C1   C     180.00   0.0  0
 U66  CONST_29  H51   C5   C2   C     180.00   0.0  0
 U66  CONST_30  H61   C6   C2   C     180.00   0.0  0
 U66  CONST_31  H31   C3   C    C1      0.00   0.0  0
 U66  CONST_32  H101  C10  C4   C1    180.00   0.0  0
 U66  CONST_33  H111  C11  C5   C2    180.00   0.0  0
 U66  CONST_34  H291  C29  C27  C23     0.00   0.0  0
 U66  CONST_35  H301  C30  N28  C26     0.00   0.0  0
 U66  Var_01    C8    N    C1   C     -83.60  30.0  1
 U66  Var_02    C14   C9   N    C1    167.27  30.0  1
 U66  Var_03    C12   C14  C9   N      29.32  30.0  1
 U66  Var_04    C23   C19  N16  C12  -160.20  30.0  1
 U66  Var_05    C24   C22  C18  C15     7.39  30.0  1
 U66  Var_06    C27   C23  C19  N16  -157.64  30.0  1
 U66  Var_07    C22   C24  C20  C17    20.07  30.0  1
 U66  Var_08    C20   C24  C22  C18     1.37  30.0  2
 U66  Var_09    N28   C26  C22  C18    69.40  30.0  1
 U66  Var_10    N28   C27  C23  C19   125.83  30.0  1
 U66  Var_11    C27   N28  C26  C22   -90.90  30.0  1

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
 U66  chir_01  C12  C8   C14  N16  positiv
 U66  chir_02  C15  O    C17  C18  positiv
 U66  chir_03  C17  C15  C20  C21  positiv

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
 U66  plan-1  C23   0.020
 U66  plan-1  C26   0.020
 U66  plan-1  C27   0.020
 U66  plan-1  N28   0.020
 U66  plan-1  C29   0.020
 U66  plan-1  C30   0.020
 U66  plan-1  NZ    0.020
 U66  plan-1  H291  0.020
 U66  plan-1  H301  0.020
 U66  plan-2  C     0.020
 U66  plan-2  C1    0.020
 U66  plan-2  C2    0.020
 U66  plan-2  C3    0.020
 U66  plan-2  N     0.020
 U66  plan-2  C4    0.020
 U66  plan-2  C5    0.020
 U66  plan-2  C6    0.020
 U66  plan-2  C7    0.020
 U66  plan-2  C10   0.020
 U66  plan-2  C11   0.020
 U66  plan-2  O     0.020
 U66  plan-2  H31   0.020
 U66  plan-2  H41   0.020
 U66  plan-2  H51   0.020
 U66  plan-2  H61   0.020
 U66  plan-2  H101  0.020
 U66  plan-2  H111  0.020
 U66  plan-3  C1    0.020
 U66  plan-3  N     0.020
 U66  plan-3  C8    0.020
 U66  plan-3  C9    0.020
 U66  plan-3  C12   0.020
 U66  plan-3  O13   0.020

