# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 15:23:37 2020
#   Inital geometry file: a 98 line input string
#   Ligand name: (7S,11S)-3-chloro-9-ethyl-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolin-12-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC1=C[C@H]2C[C@@H](C1)c3c(N)c4ccc(Cl)cc4nc3C2
#
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
 HUX  HUX  (7S,11S)-3-chloro-9-ethyl-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolin-12-amine  ligand  40  21  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_HUX
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
 HUX  CL1   CL  CL    0  -0.128  -0.5417   0.7653   5.4066
 HUX  C1    C   CR6   0  -0.053  -0.1067   0.2232   3.8183
 HUX  N1    N   N     0  -0.502  -1.5643   0.0330   0.5181
 HUX  C3    C   CR66  0   0.159  -0.6503  -0.1076   1.4966
 HUX  C4    C   CR6   0   0.161  -1.2478  -0.3729  -0.6938
 HUX  C14   C   CR6   0   0.359   0.9497  -1.1067  -0.0395
 HUX  C2    C   CR16  0  -0.265  -1.0015   0.3368   2.7940
 HUX  C17   C   CR16  0  -0.219   1.1731  -0.3240   3.6227
 HUX  C15   C   CR66  0   0.050   0.6300  -0.6688   1.2841
 HUX  C5    C   CH2   0  -0.489  -2.3344  -0.2140  -1.7260
 HUX  C13   C   CR6   0   0.038  -0.0091  -0.9524  -1.0386
 HUX  C6    C   CH1   0  -0.315  -1.8103  -0.3027  -3.1581
 HUX  C7    C   C1    0  -0.256  -0.9981   0.9178  -3.4913
 HUX  C12   C   CH2   0  -0.421  -0.9643  -1.5610  -3.2766
 HUX  C8    C   C     0   0.119   0.3343   0.9556  -3.4779
 HUX  C9    C   CH2   0  -0.462   1.1472  -0.2657  -3.1477
 HUX  C18   C   CH2   0  -0.496   1.1004   2.2188  -3.7534
 HUX  C11   C   CH1   0  -0.390   0.3054  -1.3497  -2.4634
 HUX  C10   C   CH3   0  -0.655   1.6391   2.8620  -2.4753
 HUX  C16   C   CR16  0  -0.322   1.5244  -0.7569   2.3727
 HUX  HN21  H   HNH2  0   0.401   2.7378  -1.9757   0.4474
 HUX  HN22  H   HNH2  0   0.402   2.3148  -2.1145  -1.1688
 HUX  HC2   H   HCR6  0   0.275  -1.9847   0.7626   2.9447
 HUX  H17   H   HCR6  0   0.281   1.8685  -0.3981   4.4465
 HUX  HC51  H   HCH2  0   0.250  -2.8460   0.7351  -1.5516
 HUX  HC52  H   HCH2  0   0.259  -3.0817  -0.9984  -1.5609
 HUX  HC6   H   HCH1  0   0.245  -2.6666  -0.3574  -3.8362
 HUX  HC7   H   H     0   0.227  -1.5511   1.8265  -3.7166
 HUX  H121  H   HCH2  0   0.240  -1.5186  -2.4303  -2.9128
 HUX  H122  H   HCH2  0   0.241  -0.7007  -1.7597  -4.3184
 HUX  HC91  H   HCH2  0   0.248   1.5881  -0.6663  -4.0687
 HUX  HC92  H   HCH2  0   0.243   1.9979   0.0136  -2.5195
 HUX  H181  H   HCH2  0   0.232   0.4597   2.9344  -4.2738
 HUX  H182  H   HCH2  0   0.226   1.9354   2.0015  -4.4278
 HUX  H11   H   HCH1  0   0.249   0.8708  -2.2881  -2.4646
 HUX  H101  H   HCH3  0   0.228   2.2202   3.7566  -2.7025
 HUX  H102  H   HCH3  0   0.223   0.8196   3.1508  -1.8167
 HUX  H103  H   HCH3  0   0.220   2.2857   2.1816  -1.9194
 HUX  H16   H   HCR6  0   0.258   2.5185  -1.1653   2.2462
 HUX  N2    N   NH2   0  -0.859   2.1801  -1.6143  -0.3067

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
 HUX  CL1  C1    single    1.734  0.020  1.734
 HUX  C1   C2    aromatic  1.365  0.020  1.365
 HUX  C1   C17   aromatic  1.406  0.020  1.406
 HUX  N1   C3    aromatic  1.346  0.020  1.346
 HUX  N1   C4    aromatic  1.317  0.020  1.317
 HUX  C3   C2    aromatic  1.416  0.020  1.416
 HUX  C3   C15   aromatic  1.414  0.020  1.414
 HUX  C4   C5    single    1.507  0.020  1.507
 HUX  C4   C13   aromatic  1.410  0.020  1.410
 HUX  N2   C14   single    1.358  0.020  1.358
 HUX  N2   HN21  single    0.890  0.020  1.040
 HUX  N2   HN22  single    0.890  0.020  1.040
 HUX  C14  C15   aromatic  1.430  0.020  1.430
 HUX  C14  C13   aromatic  1.393  0.020  1.393
 HUX  C2   HC2   single    0.930  0.020  1.080
 HUX  C17  C16   aromatic  1.369  0.020  1.369
 HUX  C17  H17   single    0.930  0.020  1.080
 HUX  C15  C16   aromatic  1.412  0.020  1.412
 HUX  C5   C6    single    1.528  0.020  1.528
 HUX  C5   HC51  single    0.970  0.020  1.090
 HUX  C5   HC52  single    0.970  0.020  1.090
 HUX  C13  C11   single    1.512  0.020  1.512
 HUX  C6   C7    single    1.503  0.020  1.503
 HUX  C6   C12   single    1.521  0.020  1.521
 HUX  C6   HC6   single    0.970  0.020  1.090
 HUX  C7   C8    double    1.333  0.020  1.333
 HUX  C7   HC7   single    0.930  0.020  1.080
 HUX  C12  C11   single    1.523  0.020  1.523
 HUX  C12  H121  single    0.970  0.020  1.090
 HUX  C12  H122  single    0.970  0.020  1.090
 HUX  C8   C9    single    1.504  0.020  1.504
 HUX  C8   C18   single    1.503  0.020  1.503
 HUX  C9   C11   single    1.534  0.020  1.534
 HUX  C9   HC91  single    0.970  0.020  1.090
 HUX  C9   HC92  single    0.970  0.020  1.090
 HUX  C18  C10   single    1.529  0.020  1.529
 HUX  C18  H181  single    0.970  0.020  1.090
 HUX  C18  H182  single    0.970  0.020  1.090
 HUX  C11  H11   single    0.970  0.020  1.090
 HUX  C10  H101  single    0.970  0.020  1.090
 HUX  C10  H102  single    0.970  0.020  1.090
 HUX  C10  H103  single    0.970  0.020  1.090
 HUX  C16  H16   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
 HUX  C17   C1   C2    121.66  3.000
 HUX  C17   C1   CL1   118.54  3.000
 HUX  C2    C1   CL1   119.80  3.000
 HUX  C4    N1   C3    118.27  3.000
 HUX  C15   C3   C2    119.14  3.000
 HUX  C15   C3   N1    123.15  3.000
 HUX  C2    C3   N1    117.70  3.000
 HUX  C13   C4   C5    120.60  3.000
 HUX  C13   C4   N1    124.25  3.000
 HUX  C5    C4   N1    115.12  3.000
 HUX  C13   C14  C15   118.41  3.000
 HUX  C13   C14  N2    121.60  3.000
 HUX  C15   C14  N2    119.95  3.000
 HUX  HC2   C2   C3    118.47  3.000
 HUX  HC2   C2   C1    121.59  3.000
 HUX  C3    C2   C1    119.94  3.000
 HUX  H17   C17  C16   120.62  3.000
 HUX  H17   C17  C1    120.44  3.000
 HUX  C16   C17  C1    118.94  3.000
 HUX  C16   C15  C14   123.56  3.000
 HUX  C16   C15  C3    118.85  3.000
 HUX  C14   C15  C3    117.58  3.000
 HUX  HC52  C5   HC51  106.17  3.000
 HUX  HC52  C5   C6    109.49  3.000
 HUX  HC51  C5   C6    111.15  3.000
 HUX  HC52  C5   C4    108.24  3.000
 HUX  HC51  C5   C4    108.66  3.000
 HUX  C6    C5   C4    112.87  3.000
 HUX  C11   C13  C14   120.23  3.000
 HUX  C11   C13  C4    121.40  3.000
 HUX  C14   C13  C4    118.33  3.000
 HUX  HC6   C6   C12   110.23  3.000
 HUX  HC6   C6   C7    109.04  3.000
 HUX  C12   C6   C7    110.73  3.000
 HUX  HC6   C6   C5    108.40  3.000
 HUX  C12   C6   C5    108.18  3.000
 HUX  C7    C6   C5    110.24  3.000
 HUX  HC7   C7   C8    119.13  3.000
 HUX  HC7   C7   C6    116.72  3.000
 HUX  C8    C7   C6    124.11  3.000
 HUX  H122  C12  H121  107.16  3.000
 HUX  H122  C12  C11   109.46  3.000
 HUX  H121  C12  C11   110.82  3.000
 HUX  H122  C12  C6    111.03  3.000
 HUX  H121  C12  C6    110.48  3.000
 HUX  C11   C12  C6    107.91  3.000
 HUX  C18   C8   C9    116.57  3.000
 HUX  C18   C8   C7    122.11  3.000
 HUX  C9    C8   C7    121.30  3.000
 HUX  HC92  C9   HC91  105.24  3.000
 HUX  HC92  C9   C11   110.56  3.000
 HUX  HC91  C9   C11   109.71  3.000
 HUX  HC92  C9   C8    109.82  3.000
 HUX  HC91  C9   C8    109.24  3.000
 HUX  C11   C9   C8    112.04  3.000
 HUX  H182  C18  H181  106.49  3.000
 HUX  H182  C18  C10   109.24  3.000
 HUX  H181  C18  C10   109.22  3.000
 HUX  H182  C18  C8    109.56  3.000
 HUX  H181  C18  C8    109.82  3.000
 HUX  C10   C18  C8    112.34  3.000
 HUX  H11   C11  C9    108.76  3.000
 HUX  H11   C11  C12   108.12  3.000
 HUX  C9    C11  C12   108.51  3.000
 HUX  H11   C11  C13   109.48  3.000
 HUX  C9    C11  C13   110.42  3.000
 HUX  C12   C11  C13   111.48  3.000
 HUX  H103  C10  H102  107.63  3.000
 HUX  H103  C10  H101  107.58  3.000
 HUX  H102  C10  H101  108.00  3.000
 HUX  H103  C10  C18   111.87  3.000
 HUX  H102  C10  C18   110.58  3.000
 HUX  H101  C10  C18   111.02  3.000
 HUX  H16   C16  C15   121.03  3.000
 HUX  H16   C16  C17   117.51  3.000
 HUX  C15   C16  C17   121.46  3.000
 HUX  HN22  N2   HN21  112.95  3.000
 HUX  HN22  N2   C14   118.43  3.000
 HUX  HN21  N2   C14   119.32  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
 HUX  CONST_01  N1    C3   C2   C1   180.00   0.0  0
 HUX  CONST_02  C15   C3   C2   C1     0.00   0.0  0
 HUX  CONST_03  C15   C16  C17  C1     0.00   0.0  0
 HUX  CONST_04  C14   C15  C3   N1     0.00   0.0  0
 HUX  CONST_05  C16   C15  C3   N1   180.00   0.0  0
 HUX  CONST_06  C14   C13  C4   N1     0.00   0.0  0
 HUX  CONST_07  C13   C4   N1   C3     0.00   0.0  0
 HUX  CONST_08  C17   C1   C2   C3     0.00   0.0  0
 HUX  CONST_09  C13   C14  C15  C3     0.00   0.0  0
 HUX  CONST_10  C17   C16  C15  C3     0.00   0.0  0
 HUX  CONST_11  C2    C3   N1   C4   180.00   0.0  0
 HUX  CONST_12  C15   C3   N1   C4     0.00   0.0  0
 HUX  CONST_13  C15   C14  C13  C4     0.00   0.0  0
 HUX  CONST_14  C2    C3   C15  C14  180.00   0.0  0
 HUX  CONST_15  C17   C16  C15  C14  180.00   0.0  0
 HUX  CONST_16  C16   C17  C1   C2     0.00   0.0  0
 HUX  CONST_17  C16   C15  C3   C2     0.00   0.0  0
 HUX  CONST_18  C16   C15  C14  C13  180.00   0.0  0
 HUX  CONST_19  C3    C2   C1   CL1  180.00   0.0  0
 HUX  CONST_20  C16   C17  C1   CL1  180.00   0.0  0
 HUX  CONST_21  N2    C14  C15  C3   180.00   0.0  0
 HUX  CONST_22  N2    C14  C13  C4   180.00   0.0  0
 HUX  CONST_23  C16   C15  C14  N2     0.00   0.0  0
 HUX  CONST_24  C11   C13  C14  N2     0.00   0.0  0
 HUX  CONST_25  H16   C16  C17  C1   180.00   0.0  0
 HUX  CONST_26  HC2   C2   C3   N1     0.00   0.0  0
 HUX  CONST_27  H17   C17  C1   C2   180.00   0.0  0
 HUX  CONST_29  HN22  N2   C14  C15  180.00   0.0  0
 HUX  Var_01    C6    C5   C4   N1   163.12  30.0  1
 HUX  Var_02    C9    C8   C7   C6     1.40  30.0  2
 HUX  Var_03    C11   C9   C8   C7   -16.55  30.0  3
 HUX  Var_04    C10   C18  C8   C7   102.57  30.0  3
 HUX  Var_05    H101  C10  C18  C8   178.01  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
 HUX  chir_01  C6   C5  C7   C12  negativ
 HUX  chir_02  C11  C9  C12  C13  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
 HUX  plan-1  CL1   0.020
 HUX  plan-1  C1    0.020
 HUX  plan-1  N1    0.020
 HUX  plan-1  C3    0.020
 HUX  plan-1  C4    0.020
 HUX  plan-1  C14   0.020
 HUX  plan-1  C2    0.020
 HUX  plan-1  C17   0.020
 HUX  plan-1  C15   0.020
 HUX  plan-1  C5    0.020
 HUX  plan-1  C13   0.020
 HUX  plan-1  C11   0.020
 HUX  plan-1  C16   0.020
 HUX  plan-1  HC2   0.020
 HUX  plan-1  H17   0.020
 HUX  plan-1  H16   0.020
 HUX  plan-1  N2    0.020
 HUX  plan-2  C14   0.020
 HUX  plan-2  HN21  0.020
 HUX  plan-2  HN22  0.020
 HUX  plan-2  N2    0.020

