# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 14:11:49 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: (2S)-2-(4-chlorophenyl)-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC[C@H](c1ccc(Cl)cc1)c2ccc(cc2)c3c[nH]nc3
#
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
 GVO  GVO  (2S)-2-(4-chlorophenyl)-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine  ligand  37  21  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_GVO
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
 GVO  N1    N   NH2   0  -0.791   0.7261  -3.3857   4.3498
 GVO  C2    C   CH2   0  -0.259   0.5988  -2.0058   4.7785
 GVO  C3    C   CH1   0  -0.451   1.7609  -1.1756   4.2298
 GVO  C4    C   CR6   0   0.184   1.8095   0.2306   4.7881
 GVO  C5    C   CR16  0  -0.305   3.0432   0.8617   4.9339
 GVO  C6    C   CR16  0  -0.195   3.1438   2.1598   5.4083
 GVO  C7    C   CR6   0  -0.059   1.9859   2.8433   5.7462
 GVO  CL8   CL  CL    0  -0.135   2.0945   4.4687   6.3435
 GVO  C9    C   CR16  0  -0.192   0.7446   2.2442   5.6172
 GVO  C10   C   CR16  0  -0.337   0.6659   0.9427   5.1395
 GVO  C11   C   CR6   0   0.210   1.7757  -1.1398   2.7176
 GVO  C12   C   CR16  0  -0.320   2.8656  -1.6209   2.0026
 GVO  C13   C   CR16  0  -0.325   2.8957  -1.5740   0.6162
 GVO  C14   C   CR6   0   0.091   1.8310  -1.0375  -0.1070
 GVO  C15   C   CR16  0  -0.322   0.7359  -0.5527   0.6141
 GVO  C16   C   CR16  0  -0.282   0.7103  -0.6048   1.9968
 GVO  C17   C   CR5   0  -0.107   1.8644  -0.9806  -1.5665
 GVO  C18   C   CR15  0  -0.119   2.9785  -1.1206  -2.4232
 GVO  N19   N   N     0  -0.263   2.6379  -1.0071  -3.6921
 GVO  N20   N   NR15  0  -0.425   1.3273  -0.7997  -3.6748
 GVO  C21   C   CR15  0  -0.012   0.8117  -0.7723  -2.4385
 GVO  H1N1  H   HNH2  0   0.350  -0.0681  -3.9157   4.6848
 GVO  H1N2  H   HNH2  0   0.339   1.5381  -3.8006   4.7909
 GVO  H2C1  H   HCH2  0   0.213   0.5692  -1.8783   5.8697
 GVO  H2C2  H   HCH2  0   0.218  -0.3503  -1.6202   4.3975
 GVO  H3    H   HCH1  0   0.266   2.6844  -1.6702   4.5518
 GVO  H5    H   HCR6  0   0.258   3.9510   0.3298   4.6746
 GVO  H10   H   HCR6  0   0.259  -0.3150   0.4941   5.0483
 GVO  H6    H   HCR6  0   0.278   4.1127   2.6277   5.5181
 GVO  H9    H   HCR6  0   0.278  -0.1565   2.7790   5.8852
 GVO  H12   H   HCR6  0   0.248   3.7083  -2.0458   2.5350
 GVO  H16   H   HCR6  0   0.246  -0.1560  -0.2126   2.5165
 GVO  H13   H   HCR6  0   0.246   3.7578  -1.9740   0.0971
 GVO  H15   H   HCR6  0   0.245  -0.1058  -0.1163   0.0906
 GVO  H18   H   HCR5  0   0.258   4.0107  -1.2862  -2.1525
 GVO  H21   H   HCR5  0   0.290  -0.2423  -0.6237  -2.2687
 GVO  H20   H   HNR5  0   0.423   0.8260  -0.6804  -4.5407

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
 GVO  N1   C2    single    1.451  0.020  1.451
 GVO  C2   C3    single    1.530  0.020  1.530
 GVO  C3   C4    single    1.514  0.020  1.514
 GVO  C4   C5    aromatic  1.393  0.020  1.393
 GVO  C5   C6    aromatic  1.386  0.020  1.386
 GVO  C6   C7    aromatic  1.386  0.020  1.386
 GVO  C7   CL8   single    1.735  0.020  1.735
 GVO  C7   C9    aromatic  1.384  0.020  1.384
 GVO  C4   C10   aromatic  1.392  0.020  1.392
 GVO  C9   C10   aromatic  1.389  0.020  1.389
 GVO  C3   C11   single    1.513  0.020  1.513
 GVO  C11  C12   aromatic  1.389  0.020  1.389
 GVO  C12  C13   aromatic  1.388  0.020  1.388
 GVO  C13  C14   aromatic  1.394  0.020  1.394
 GVO  C14  C15   aromatic  1.398  0.020  1.398
 GVO  C11  C16   aromatic  1.393  0.020  1.393
 GVO  C15  C16   aromatic  1.384  0.020  1.384
 GVO  C14  C17   single    1.461  0.020  1.461
 GVO  C17  C18   single    1.412  0.020  1.412
 GVO  C18  N19   double    1.319  0.020  1.319
 GVO  N19  N20   single    1.327  0.020  1.327
 GVO  C17  C21   double    1.383  0.020  1.383
 GVO  N20  C21   single    1.340  0.020  1.340
 GVO  N1   H1N1  single    0.890  0.020  1.040
 GVO  N1   H1N2  single    0.890  0.020  1.040
 GVO  C2   H2C1  single    0.970  0.020  1.090
 GVO  C2   H2C2  single    0.970  0.020  1.090
 GVO  C3   H3    single    0.970  0.020  1.090
 GVO  C5   H5    single    0.930  0.020  1.080
 GVO  C10  H10   single    0.930  0.020  1.080
 GVO  C6   H6    single    0.930  0.020  1.080
 GVO  C9   H9    single    0.930  0.020  1.080
 GVO  C12  H12   single    0.930  0.020  1.080
 GVO  C16  H16   single    0.930  0.020  1.080
 GVO  C13  H13   single    0.930  0.020  1.080
 GVO  C15  H15   single    0.930  0.020  1.080
 GVO  C18  H18   single    0.930  0.020  1.080
 GVO  C21  H21   single    0.930  0.020  1.080
 GVO  N20  H20   single    0.860  0.020  1.020

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
 GVO  H1N2  N1   H1N1  105.69  3.000
 GVO  H1N2  N1   C2    109.35  3.000
 GVO  H1N1  N1   C2    109.36  3.000
 GVO  H2C2  C2   H2C1  106.37  3.000
 GVO  H2C2  C2   C3    110.07  3.000
 GVO  H2C1  C2   C3    108.28  3.000
 GVO  H2C2  C2   N1    107.99  3.000
 GVO  H2C1  C2   N1    113.96  3.000
 GVO  C3    C2   N1    110.09  3.000
 GVO  H3    C3   C11   107.23  3.000
 GVO  H3    C3   C4    106.49  3.000
 GVO  C11   C3   C4    110.27  3.000
 GVO  H3    C3   C2    106.84  3.000
 GVO  C11   C3   C2    112.26  3.000
 GVO  C4    C3   C2    113.33  3.000
 GVO  C10   C4   C5    117.99  3.000
 GVO  C10   C4   C3    122.81  3.000
 GVO  C5    C4   C3    119.19  3.000
 GVO  H5    C5   C6    118.75  3.000
 GVO  H5    C5   C4    119.63  3.000
 GVO  C6    C5   C4    121.62  3.000
 GVO  H6    C6   C7    120.67  3.000
 GVO  H6    C6   C5    120.34  3.000
 GVO  C7    C6   C5    118.99  3.000
 GVO  C9    C7   CL8   119.58  3.000
 GVO  C9    C7   C6    120.85  3.000
 GVO  CL8   C7   C6    119.57  3.000
 GVO  H9    C9   C10   120.09  3.000
 GVO  H9    C9   C7    120.67  3.000
 GVO  C10   C9   C7    119.24  3.000
 GVO  H10   C10  C9    117.95  3.000
 GVO  H10   C10  C4    120.74  3.000
 GVO  C9    C10  C4    121.31  3.000
 GVO  C16   C11  C12   117.82  3.000
 GVO  C16   C11  C3    121.25  3.000
 GVO  C12   C11  C3    120.92  3.000
 GVO  H12   C12  C13   119.16  3.000
 GVO  H12   C12  C11   119.54  3.000
 GVO  C13   C12  C11   121.30  3.000
 GVO  H13   C13  C14   120.09  3.000
 GVO  H13   C13  C12   118.94  3.000
 GVO  C14   C13  C12   120.97  3.000
 GVO  C17   C14  C15   121.31  3.000
 GVO  C17   C14  C13   121.04  3.000
 GVO  C15   C14  C13   117.65  3.000
 GVO  H15   C15  C16   118.92  3.000
 GVO  H15   C15  C14   119.96  3.000
 GVO  C16   C15  C14   121.12  3.000
 GVO  H16   C16  C15   118.71  3.000
 GVO  H16   C16  C11   120.15  3.000
 GVO  C15   C16  C11   121.15  3.000
 GVO  C21   C17  C18   103.47  3.000
 GVO  C21   C17  C14   128.21  3.000
 GVO  C18   C17  C14   128.32  3.000
 GVO  H18   C18  N19   120.09  3.000
 GVO  H18   C18  C17   128.10  3.000
 GVO  N19   C18  C17   111.80  3.000
 GVO  N20   N19  C18   104.84  3.000
 GVO  H20   N20  C21   126.80  3.000
 GVO  H20   N20  N19   119.92  3.000
 GVO  C21   N20  N19   113.28  3.000
 GVO  H21   C21  N20   121.64  3.000
 GVO  H21   C21  C17   131.75  3.000
 GVO  N20   C21  C17   106.61  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
 GVO  CONST_01  C7    C6   C5   C4      0.00   0.0  0
 GVO  CONST_02  C7    C9   C10  C4      0.00   0.0  0
 GVO  CONST_03  C9    C10  C4   C5      0.00   0.0  0
 GVO  CONST_04  C9    C7   C6   C5      0.00   0.0  0
 GVO  CONST_05  C10   C4   C5   C6      0.00   0.0  0
 GVO  CONST_06  C10   C9   C7   C6      0.00   0.0  0
 GVO  CONST_07  C14   C13  C12  C11     0.00   0.0  0
 GVO  CONST_08  C14   C15  C16  C11     0.00   0.0  0
 GVO  CONST_09  C15   C16  C11  C12     0.00   0.0  0
 GVO  CONST_10  C15   C14  C13  C12     0.00   0.0  0
 GVO  CONST_11  C16   C11  C12  C13     0.00   0.0  0
 GVO  CONST_12  C16   C15  C14  C13     0.00   0.0  0
 GVO  CONST_13  C17   C14  C13  C12   180.00   0.0  0
 GVO  CONST_14  C17   C14  C15  C16   180.00   0.0  0
 GVO  CONST_15  C6    C5   C4   C3    180.00   0.0  0
 GVO  CONST_16  C9    C10  C4   C3    180.00   0.0  0
 GVO  CONST_17  C13   C12  C11  C3    180.00   0.0  0
 GVO  CONST_18  C15   C16  C11  C3    180.00   0.0  0
 GVO  CONST_19  CL8   C7   C6   C5    180.00   0.0  0
 GVO  CONST_20  C10   C9   C7   CL8   180.00   0.0  0
 GVO  CONST_21  H6    C6   C5   C4    180.00   0.0  0
 GVO  CONST_22  H9    C9   C10  C4    180.00   0.0  0
 GVO  CONST_23  H10   C10  C4   C5    180.00   0.0  0
 GVO  CONST_24  H5    C5   C6   C7    180.00   0.0  0
 GVO  CONST_25  H13   C13  C12  C11   180.00   0.0  0
 GVO  CONST_26  H15   C15  C16  C11   180.00   0.0  0
 GVO  CONST_27  H16   C16  C11  C12   180.00   0.0  0
 GVO  CONST_28  H12   C12  C13  C14   180.00   0.0  0
 GVO  Var_01    C18   C17  C14  C13   -16.17  30.0  2
 GVO  Var_02    H1N1  N1   C2   C3   -177.57  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
 GVO  chir_01  C3  C2  C4  C11  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
 GVO  plan-1  C14  0.020
 GVO  plan-1  C17  0.020
 GVO  plan-1  C18  0.020
 GVO  plan-1  N19  0.020
 GVO  plan-1  N20  0.020
 GVO  plan-1  C21  0.020
 GVO  plan-1  H18  0.020
 GVO  plan-1  H21  0.020
 GVO  plan-1  H20  0.020
 GVO  plan-2  C3   0.020
 GVO  plan-2  C4   0.020
 GVO  plan-2  C5   0.020
 GVO  plan-2  C6   0.020
 GVO  plan-2  C7   0.020
 GVO  plan-2  CL8  0.020
 GVO  plan-2  C9   0.020
 GVO  plan-2  C10  0.020
 GVO  plan-2  H5   0.020
 GVO  plan-2  H10  0.020
 GVO  plan-2  H6   0.020
 GVO  plan-2  H9   0.020
 GVO  plan-3  C3   0.020
 GVO  plan-3  C11  0.020
 GVO  plan-3  C12  0.020
 GVO  plan-3  C13  0.020
 GVO  plan-3  C14  0.020
 GVO  plan-3  C15  0.020
 GVO  plan-3  C16  0.020
 GVO  plan-3  C17  0.020
 GVO  plan-3  H12  0.020
 GVO  plan-3  H16  0.020
 GVO  plan-3  H13  0.020
 GVO  plan-3  H15  0.020

