# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 25 18:55:44 2020
#   Inital geometry file: a 132 line input string
#   Ligand name: 2-(2-chloro-4-fluorophenoxy)-2-methyl-N-[(1R,2S,3S,5S,7s)-5-(methylsulfonyl)tricyclo[3.3.1.1~3,7~]dec-2-yl]propanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(Oc1ccc(F)cc1Cl)C(=O)NC2[C@H]3CC4C[C@@H]2CC(C4)(C3)[S](C)(=O)=O
#
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
 NN1  NN1  2-(2-chloro-4-fluorophenoxy)-2-methyl-N-[(1R,2S,3S,5S,7s)-5-(methylsulfonyl)tricyclo[3.3.1.1~3,7~]dec-2-yl]propanamide  ligand  56  29  .  2021-08-15  2021-08-15  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_NN1
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
 NN1  C4    C   CR6   0   0.410   3.8077  -2.4515   2.8544
 NN1  C5    C   CH3   0  -0.795  -1.5803  -2.8790  -4.8977
 NN1  C6    C   CR6   0  -0.113   4.4782  -2.1677   4.0431
 NN1  C7    C   CR16  0  -0.315   2.4274  -2.6127   2.8972
 NN1  C8    C   CR16  0  -0.402   1.7274  -2.4830   4.0863
 NN1  C10   C   CR6   0   0.525   2.4276  -2.1827   5.2374
 NN1  C15   C   CH1   0  -0.041   1.9142  -2.6050  -1.4489
 NN1  C17   C   CH2   0  -0.447   0.7032  -0.7605  -0.2366
 NN1  C20   C   CH1   0  -0.257   2.2673  -1.6099  -2.5617
 NN1  C21   C   CH2   0  -0.426   1.1647  -1.6585  -3.6252
 NN1  C22   C   CT    0  -0.326  -0.1629  -1.2537  -2.9804
 NN1  C24   C   CH2   0  -0.421  -0.5184  -2.2247  -1.8515
 NN1  C1    C   CH3   0  -0.649   5.9127  -3.6489   0.1845
 NN1  C2    C   CT    0   0.057   4.6214  -3.7588   0.9897
 NN1  C3    C   CH3   0  -0.686   4.6721  -4.9575   1.9244
 NN1  O3    O   O2    0  -0.503   4.5279  -2.5150   1.7093
 NN1  C14   C   C     0   0.547   3.4553  -3.8792  -0.0096
 NN1  O1    O   O     0  -0.478   3.0595  -4.9751  -0.3750
 NN1  N4    N   NH1   0  -0.656   2.9814  -2.7138  -0.4770
 NN1  C16   C   CH1   0  -0.260   0.5906  -2.1787  -0.7969
 NN1  C18   C   CH1   0  -0.244   1.0444   0.2105  -1.3684
 NN1  C19   C   CH2   0  -0.454   2.3750  -0.1882  -2.0073
 NN1  C23   C   CH2   0  -0.411  -0.0619   0.1738  -2.4256
 NN1  S1    S   S     0   1.237  -1.4862  -1.2312  -4.2253
 NN1  O2    O   OS    0  -0.685  -1.0882  -0.3249  -5.3068
 NN1  O4    O   OS    0  -0.685  -2.7536  -0.9550  -3.5416
 NN1  C9    C   CR16  0  -0.378   3.7983  -2.0193   5.2416
 NN1  CL1   CL  CL    0  -0.087   6.1932  -1.9971   4.0172
 NN1  F1    F   F     0  -0.311   1.7613  -2.0435   6.3915
 NN1  H51   H   HCH3  0   0.292  -0.6540  -3.1364  -5.4042
 NN1  H52   H   HCH3  0   0.292  -1.7962  -3.5957  -4.1094
 NN1  H53   H   HCH3  0   0.317  -2.3993  -2.8670  -5.6157
 NN1  H7    H   HCR6  0   0.285   1.8802  -2.8397   1.9925
 NN1  H8    H   HCR6  0   0.292   0.6533  -2.6071   4.1090
 NN1  H15   H   HCH1  0   0.264   1.7913  -3.5969  -1.8894
 NN1  H171  H   HCH2  0   0.235   1.4616  -0.7077   0.5514
 NN1  H172  H   HCH2  0   0.246  -0.2414  -0.4751   0.2345
 NN1  H20   H   HCH1  0   0.260   3.2121  -1.9099  -3.0217
 NN1  H211  H   HCH2  0   0.266   1.4162  -0.9840  -4.4466
 NN1  H212  H   HCH2  0   0.260   1.1050  -2.6701  -4.0365
 NN1  H241  H   HCH2  0   0.258  -0.6220  -3.2455  -2.2306
 NN1  H242  H   HCH2  0   0.265  -1.4716  -1.9470  -1.3978
 NN1  H11   H   HCH3  0   0.245   6.0221  -4.5100  -0.4738
 NN1  H12   H   HCH3  0   0.252   6.7715  -3.6200   0.8555
 NN1  H13   H   HCH3  0   0.245   5.9233  -2.7491  -0.4314
 NN1  H31   H   HCH3  0   0.251   3.7413  -5.1137   2.4690
 NN1  H32   H   HCH3  0   0.247   5.4789  -4.8260   2.6463
 NN1  H33   H   HCH3  0   0.261   4.8782  -5.8626   1.3574
 NN1  HN4   H   HNH1  0   0.402   3.3720  -1.8645  -0.0996
 NN1  H16   H   HCH1  0   0.256   0.3383  -2.8854  -0.0005
 NN1  H18   H   HCH1  0   0.250   1.1123   1.2272  -0.9740
 NN1  H191  H   HCH2  0   0.248   2.6310   0.5008  -2.8173
 NN1  H192  H   HCH2  0   0.240   3.1873  -0.1036  -1.2778
 NN1  H231  H   HCH2  0   0.258  -1.0128   0.4751  -1.9799
 NN1  H232  H   HCH2  0   0.258   0.1650   0.8800  -3.2280
 NN1  H9    H   HCR6  0   0.305   4.3266  -1.7890   6.1570

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
 NN1  C4   O3    single    1.354  0.020  1.354
 NN1  C4   C6    aromatic  1.394  0.020  1.394
 NN1  C4   C7    aromatic  1.390  0.020  1.390
 NN1  C5   S1    single    1.782  0.020  1.782
 NN1  C5   H51   single    0.970  0.020  1.090
 NN1  C5   H52   single    0.970  0.020  1.090
 NN1  C5   H53   single    0.970  0.020  1.090
 NN1  C6   CL1   single    1.724  0.020  1.724
 NN1  C6   C9    aromatic  1.386  0.020  1.386
 NN1  C7   C8    aromatic  1.386  0.020  1.386
 NN1  C7   H7    single    0.930  0.020  1.080
 NN1  C8   C10   aromatic  1.380  0.020  1.380
 NN1  C8   H8    single    0.930  0.020  1.080
 NN1  C10  C9    aromatic  1.380  0.020  1.380
 NN1  C10  F1    single    1.340  0.020  1.340
 NN1  C15  C20   single    1.534  0.020  1.534
 NN1  C15  N4    single    1.448  0.020  1.448
 NN1  C15  C16   single    1.536  0.020  1.536
 NN1  C15  H15   single    0.970  0.020  1.090
 NN1  C17  C18   single    1.530  0.020  1.530
 NN1  C17  C16   single    1.529  0.020  1.529
 NN1  C17  H171  single    0.970  0.020  1.090
 NN1  C17  H172  single    0.970  0.020  1.090
 NN1  C20  C19   single    1.530  0.020  1.530
 NN1  C20  C21   single    1.533  0.020  1.533
 NN1  C20  H20   single    0.970  0.020  1.090
 NN1  C21  C22   single    1.530  0.020  1.530
 NN1  C21  H211  single    0.970  0.020  1.090
 NN1  C21  H212  single    0.970  0.020  1.090
 NN1  C22  C23   single    1.535  0.020  1.535
 NN1  C22  S1    single    1.817  0.020  1.817
 NN1  C22  C24   single    1.531  0.020  1.531
 NN1  C24  C16   single    1.531  0.020  1.531
 NN1  C24  H241  single    0.970  0.020  1.090
 NN1  C24  H242  single    0.970  0.020  1.090
 NN1  C1   C2    single    1.526  0.020  1.526
 NN1  C1   H11   single    0.970  0.020  1.090
 NN1  C1   H12   single    0.970  0.020  1.090
 NN1  C1   H13   single    0.970  0.020  1.090
 NN1  C2   O3    single    1.440  0.020  1.440
 NN1  C2   C14   single    1.540  0.020  1.540
 NN1  C2   C3    single    1.521  0.020  1.521
 NN1  C3   H31   single    0.970  0.020  1.090
 NN1  C3   H32   single    0.970  0.020  1.090
 NN1  C3   H33   single    0.970  0.020  1.090
 NN1  C14  N4    single    1.342  0.020  1.342
 NN1  C14  O1    double    1.221  0.020  1.221
 NN1  N4   HN4   single    0.860  0.020  1.020
 NN1  C16  H16   single    0.970  0.020  1.090
 NN1  C18  C19   single    1.529  0.020  1.529
 NN1  C18  C23   single    1.531  0.020  1.531
 NN1  C18  H18   single    0.970  0.020  1.090
 NN1  C19  H191  single    0.970  0.020  1.090
 NN1  C19  H192  single    0.970  0.020  1.090
 NN1  C23  H231  single    0.970  0.020  1.090
 NN1  C23  H232  single    0.970  0.020  1.090
 NN1  S1   O4    double    1.466  0.020  1.466
 NN1  S1   O2    double    1.466  0.020  1.466
 NN1  C9   H9    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
 NN1  O3    C4   C7    123.27  3.000
 NN1  C7    C4   C6    118.35  3.000
 NN1  O3    C4   C6    118.35  3.000
 NN1  H53   C5   H52   109.63  3.000
 NN1  H53   C5   H51   109.65  3.000
 NN1  H52   C5   H51   110.55  3.000
 NN1  H53   C5   S1    106.15  3.000
 NN1  H52   C5   S1    110.27  3.000
 NN1  H51   C5   S1    110.48  3.000
 NN1  CL1   C6   C9    119.37  3.000
 NN1  C9    C6   C4    121.55  3.000
 NN1  CL1   C6   C4    119.07  3.000
 NN1  H7    C7   C8    118.81  3.000
 NN1  H7    C7   C4    120.06  3.000
 NN1  C8    C7   C4    121.13  3.000
 NN1  H8    C8   C10   120.75  3.000
 NN1  H8    C8   C7    120.59  3.000
 NN1  C10   C8   C7    118.66  3.000
 NN1  F1    C10  C9    118.61  3.000
 NN1  F1    C10  C8    119.25  3.000
 NN1  C9    C10  C8    122.14  3.000
 NN1  H15   C15  C16   109.04  3.000
 NN1  H15   C15  N4    106.59  3.000
 NN1  C16   C15  N4    111.79  3.000
 NN1  H15   C15  C20   108.81  3.000
 NN1  C16   C15  C20   109.04  3.000
 NN1  N4    C15  C20   111.47  3.000
 NN1  H172  C17  H171  106.00  3.000
 NN1  H172  C17  C18   110.22  3.000
 NN1  H171  C17  C18   110.33  3.000
 NN1  H172  C17  C16   109.65  3.000
 NN1  H171  C17  C16   111.07  3.000
 NN1  C18   C17  C16   109.52  3.000
 NN1  H20   C20  C19   110.29  3.000
 NN1  H20   C20  C21   108.73  3.000
 NN1  C19   C20  C21   109.36  3.000
 NN1  H20   C20  C15   109.04  3.000
 NN1  C21   C20  C15   108.49  3.000
 NN1  C19   C20  C15   110.87  3.000
 NN1  H212  C21  H211  107.52  3.000
 NN1  H212  C21  C22   110.84  3.000
 NN1  H211  C21  C22   110.69  3.000
 NN1  H212  C21  C20   109.24  3.000
 NN1  H211  C21  C20   109.67  3.000
 NN1  C22   C21  C20   108.86  3.000
 NN1  S1    C22  C23   106.50  3.000
 NN1  S1    C22  C24   110.12  3.000
 NN1  C23   C22  C24   109.79  3.000
 NN1  C24   C22  C21   110.14  3.000
 NN1  S1    C22  C21   110.26  3.000
 NN1  C23   C22  C21   109.95  3.000
 NN1  H242  C24  H241  107.38  3.000
 NN1  H242  C24  C16   109.79  3.000
 NN1  H241  C24  C16   109.59  3.000
 NN1  H242  C24  C22   110.36  3.000
 NN1  H241  C24  C22   111.00  3.000
 NN1  C16   C24  C22   108.71  3.000
 NN1  H13   C1   H12   108.55  3.000
 NN1  H13   C1   H11   108.05  3.000
 NN1  H12   C1   H11   108.29  3.000
 NN1  H13   C1   C2    111.45  3.000
 NN1  H12   C1   C2    110.11  3.000
 NN1  H11   C1   C2    110.30  3.000
 NN1  C14   C2   O3    110.03  3.000
 NN1  C14   C2   C3    111.24  3.000
 NN1  O3    C2   C3    112.08  3.000
 NN1  C3    C2   C1    110.66  3.000
 NN1  C14   C2   C1    107.69  3.000
 NN1  O3    C2   C1    104.86  3.000
 NN1  H33   C3   H32   107.77  3.000
 NN1  H33   C3   H31   107.64  3.000
 NN1  H32   C3   H31   108.57  3.000
 NN1  H33   C3   C2    109.99  3.000
 NN1  H32   C3   C2    109.66  3.000
 NN1  H31   C3   C2    113.05  3.000
 NN1  C2    O3   C4    119.84  3.000
 NN1  N4    C14  O1    124.10  3.000
 NN1  O1    C14  C2    120.64  3.000
 NN1  N4    C14  C2    115.17  3.000
 NN1  HN4   N4   C14   117.67  3.000
 NN1  HN4   N4   C15   118.28  3.000
 NN1  C14   N4   C15   124.01  3.000
 NN1  H16   C16  C24   108.36  3.000
 NN1  H16   C16  C17   110.45  3.000
 NN1  C24   C16  C17   109.49  3.000
 NN1  H16   C16  C15   109.17  3.000
 NN1  C24   C16  C15   108.87  3.000
 NN1  C17   C16  C15   110.46  3.000
 NN1  H18   C18  C23   108.46  3.000
 NN1  H18   C18  C19   109.84  3.000
 NN1  C23   C18  C19   109.52  3.000
 NN1  H18   C18  C17   109.73  3.000
 NN1  C23   C18  C17   109.55  3.000
 NN1  C19   C18  C17   109.74  3.000
 NN1  H192  C19  H191  105.73  3.000
 NN1  H192  C19  C18   110.31  3.000
 NN1  H191  C19  C18   110.42  3.000
 NN1  H192  C19  C20   111.43  3.000
 NN1  H191  C19  C20   109.48  3.000
 NN1  C18   C19  C20   109.42  3.000
 NN1  H232  C23  H231  107.58  3.000
 NN1  H232  C23  C18   109.97  3.000
 NN1  H231  C23  C18   109.92  3.000
 NN1  H232  C23  C22   110.45  3.000
 NN1  H231  C23  C22   110.28  3.000
 NN1  C18   C23  C22   108.63  3.000
 NN1  O4    S1   O2    117.53  3.000
 NN1  O2    S1   C22   108.39  3.000
 NN1  O4    S1   C22   108.20  3.000
 NN1  O2    S1   C5    107.91  3.000
 NN1  O4    S1   C5    107.72  3.000
 NN1  C22   S1   C5    106.59  3.000
 NN1  H9    C9   C10   120.85  3.000
 NN1  H9    C9   C6    121.00  3.000
 NN1  C10   C9   C6    118.15  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
 NN1  CONST_01  C10  C9   C6   C4      0.00   0.0  0
 NN1  CONST_02  C10  C8   C7   C4      0.00   0.0  0
 NN1  CONST_03  C8   C7   C4   C6      0.00   0.0  0
 NN1  CONST_04  C8   C10  C9   C6      0.00   0.0  0
 NN1  CONST_05  C9   C6   C4   C7      0.00   0.0  0
 NN1  CONST_06  C9   C10  C8   C7      0.00   0.0  0
 NN1  CONST_07  F1   C10  C9   C6    180.00   0.0  0
 NN1  CONST_08  CL1  C6   C4   C7    180.00   0.0  0
 NN1  CONST_09  F1   C10  C8   C7    180.00   0.0  0
 NN1  CONST_10  O3   C4   C7   C8    180.00   0.0  0
 NN1  CONST_11  CL1  C6   C9   C10   180.00   0.0  0
 NN1  CONST_12  C9   C6   C4   O3    180.00   0.0  0
 NN1  CONST_13  H9   C9   C6   C4    180.00   0.0  0
 NN1  CONST_14  H8   C8   C7   C4    180.00   0.0  0
 NN1  CONST_15  H7   C7   C4   C6    180.00   0.0  0
 NN1  CONST_16  C2   C14  N4   C15   180.00   0.0  0
 NN1  CONST_17  O1   C14  N4   C15     0.00   0.0  0
 NN1  CONST_18  HN4  N4   C14  C2      0.00   0.0  0
 NN1  Var_01    C1   C2   O3   C4   -155.90  30.0  2
 NN1  Var_02    H51  C5   S1   C22   -63.24  30.0  3
 NN1  Var_03    N4   C14  C2   C1    -84.89  30.0  3
 NN1  Var_04    H31  C3   C2   C1   -176.00  30.0  3
 NN1  Var_05    H11  C1   C2   C3     64.53  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
 NN1  chir_01  C15  C20  N4   C16  negativ
 NN1  chir_02  C20  C21  C19  C15  negativ
 NN1  chir_03  C22  C24  C23  C21  negativ
 NN1  chir_04  C16  C15  C17  C24  negativ
 NN1  chir_05  C18  C17  C19  C23  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
 NN1  plan-1  C4   0.020
 NN1  plan-1  C6   0.020
 NN1  plan-1  C7   0.020
 NN1  plan-1  C8   0.020
 NN1  plan-1  C10  0.020
 NN1  plan-1  O3   0.020
 NN1  plan-1  C9   0.020
 NN1  plan-1  CL1  0.020
 NN1  plan-1  F1   0.020
 NN1  plan-1  H7   0.020
 NN1  plan-1  H8   0.020
 NN1  plan-1  H9   0.020
 NN1  plan-2  C15  0.020
 NN1  plan-2  C2   0.020
 NN1  plan-2  C14  0.020
 NN1  plan-2  O1   0.020
 NN1  plan-2  N4   0.020
 NN1  plan-2  HN4  0.020

