# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 21:37:17 2022
#   Inital geometry file: a 112 line input string
#   Ligand name: 1-[(1R,2S)-2-hydroxy-1-(2-naphthalen-1-ylethyl)propyl]-1H-imidazole-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](O)[C@@H](CCc1cccc2ccccc12)n3cnc(c3)C(N)=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
 FR6  FR6  1-[(1R,2S)-2-hydroxy-1-(2-naphthalen-1-ylethyl)propyl]-1H-imidazole-4-carboxamide  ligand  45  24  .  2022-09-15  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_FR6
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
 FR6  C1    C  CR15  0  -0.058   2.7546  -0.0416  -0.7253
 FR6  N2    N  NR5   0  -0.403   1.8857  -0.6346   0.1330
 FR6  C3    C  CR15  0   0.084   1.7921   0.1679   1.2236
 FR6  N4    N  N     0  -0.454   2.5409   1.2298   1.1089
 FR6  C5    C  CR5   0  -0.014   3.1517   1.1147  -0.1072
 FR6  C8    C  C     0   0.443   4.0869   2.1192  -0.6414
 FR6  O9    O  O     0  -0.493   4.6168   1.9784  -1.7383
 FR6  N10   N  NH2   0  -0.810   4.2964   3.1707   0.1623
 FR6  C13   C  CH1   0  -0.158   1.1923  -1.9028  -0.0604
 FR6  C14   C  CH1   0   0.051   1.7001  -2.9396   0.9618
 FR6  O15   O  OH1   0  -0.653   1.0226  -4.1618   0.7872
 FR6  C18   C  CH2   0  -0.422  -0.3173  -1.6892  -0.0071
 FR6  C19   C  CH2   0  -0.546  -0.8221  -0.7833  -1.1332
 FR6  C22   C  CR6   0   0.121  -2.2874  -0.4799  -0.9865
 FR6  C25   C  CR16  0  -0.335  -3.2114  -1.2694  -1.6243
 FR6  C26   C  CR16  0  -0.242  -4.5967  -1.0577  -1.4783
 FR6  C27   C  CR16  0  -0.335  -5.0564  -0.0432  -0.6873
 FR6  C28   C  CR66  0   0.117  -4.1452   0.8013  -0.0114
 FR6  C29   C  CR66  0   0.083  -2.7467   0.5859  -0.1568
 FR6  C2    C  CR16  0  -0.310  -4.6041   1.8608   0.8069
 FR6  C4    C  CR16  0  -0.337  -1.8644   1.4534   0.5340
 FR6  C6    C  CR16  0  -0.262  -3.7235   2.6783   1.4595
 FR6  C7    C  CR16  0  -0.251  -2.3369   2.4700   1.3193
 FR6  C9    C  CH3   0  -0.694   3.2097  -3.1170   0.8978
 FR6  H1    H  HCR5  0   0.309   3.0105  -0.4748  -1.6777
 FR6  H3    H  HCR5  0   0.299   1.1645  -0.0706   2.0691
 FR6  H101  H  HNH2  0   0.406   3.8315   3.2402   1.0516
 FR6  H102  H  HNH2  0   0.403   4.9071   3.9194  -0.1187
 FR6  H13   H  HCH1  0   0.271   1.4684  -2.2466  -1.0627
 FR6  H14   H  HCH1  0   0.230   1.4251  -2.5940   1.9639
 FR6  HO    H  HOH1  0   0.448   1.3290  -4.5686  -0.0309
 FR6  H181  H  HCH2  0   0.263  -0.8098  -2.6582  -0.0863
 FR6  H182  H  HCH2  0   0.243  -0.5988  -1.2831   0.9694
 FR6  H191  H  HCH2  0   0.250  -0.2370   0.1385  -1.1718
 FR6  H192  H  HCH2  0   0.264  -0.6541  -1.2848  -2.0892
 FR6  H25   H  HCR6  0   0.249  -2.8680  -2.0807  -2.2555
 FR6  H26   H  HCR6  0   0.256  -5.2913  -1.7042  -1.9986
 FR6  H27   H  HCR6  0   0.253  -6.1197   0.1285  -0.5694
 FR6  H2    H  HCR6  0   0.255  -5.6717   2.0164   0.9075
 FR6  H4    H  HCR6  0   0.243  -0.7949   1.3215   0.4386
 FR6  H6    H  HCR6  0   0.258  -4.0867   3.4870   2.0802
 FR6  H7    H  HCR6  0   0.258  -1.6428   3.1206   1.8352
 FR6  H91   H  HCH3  0   0.229   3.5324  -3.4070  -0.1054
 FR6  H92   H  HCH3  0   0.240   3.7395  -2.2036   1.1663
 FR6  H93   H  HCH3  0   0.251   3.5237  -3.8940   1.5947

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
 FR6  C1   N2    aromatic  1.358  0.020  1.358
 FR6  C1   C5    aromatic  1.370  0.020  1.370
 FR6  C1   H1    single    0.930  0.020  1.080
 FR6  N2   C3    aromatic  1.357  0.020  1.357
 FR6  N2   C13   single    1.458  0.020  1.458
 FR6  C3   N4    aromatic  1.304  0.020  1.304
 FR6  C3   H3    single    0.930  0.020  1.080
 FR6  N4   C5    aromatic  1.366  0.020  1.366
 FR6  C5   C8    single    1.473  0.020  1.473
 FR6  C8   O9    double    1.226  0.020  1.226
 FR6  C8   N10   single    1.340  0.020  1.340
 FR6  N10  H101  single    0.860  0.020  1.020
 FR6  N10  H102  single    0.860  0.020  1.020
 FR6  C13  C14   single    1.542  0.020  1.542
 FR6  C13  C18   single    1.526  0.020  1.526
 FR6  C13  H13   single    0.970  0.020  1.090
 FR6  C14  O15   single    1.408  0.020  1.408
 FR6  C14  C9    single    1.521  0.020  1.521
 FR6  C14  H14   single    0.970  0.020  1.090
 FR6  O15  HO    single    0.850  0.020  0.980
 FR6  C18  C19   single    1.531  0.020  1.531
 FR6  C18  H181  single    0.970  0.020  1.090
 FR6  C18  H182  single    0.970  0.020  1.090
 FR6  C19  C22   single    1.504  0.020  1.504
 FR6  C19  H191  single    0.970  0.020  1.090
 FR6  C19  H192  single    0.970  0.020  1.090
 FR6  C22  C25   aromatic  1.373  0.020  1.373
 FR6  C22  C29   aromatic  1.427  0.020  1.427
 FR6  C25  C26   aromatic  1.409  0.020  1.409
 FR6  C25  H25   single    0.930  0.020  1.080
 FR6  C26  C27   aromatic  1.366  0.020  1.366
 FR6  C26  H26   single    0.930  0.020  1.080
 FR6  C27  C28   aromatic  1.414  0.020  1.414
 FR6  C27  H27   single    0.930  0.020  1.080
 FR6  C28  C29   aromatic  1.422  0.020  1.422
 FR6  C28  C2    aromatic  1.415  0.020  1.415
 FR6  C29  C4    aromatic  1.417  0.020  1.417
 FR6  C2   C6    aromatic  1.367  0.020  1.367
 FR6  C2   H2    single    0.930  0.020  1.080
 FR6  C4   C7    aromatic  1.369  0.020  1.369
 FR6  C4   H4    single    0.930  0.020  1.080
 FR6  C6   C7    aromatic  1.409  0.020  1.409
 FR6  C6   H6    single    0.930  0.020  1.080
 FR6  C7   H7    single    0.930  0.020  1.080
 FR6  C9   H91   single    0.970  0.020  1.090
 FR6  C9   H92   single    0.970  0.020  1.090
 FR6  C9   H93   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
 FR6  H1    C1   C5    132.02  3.000
 FR6  H1    C1   N2    122.37  3.000
 FR6  C5    C1   N2    105.60  3.000
 FR6  C13   N2   C3    126.01  3.000
 FR6  C13   N2   C1    126.89  3.000
 FR6  C3    N2   C1    107.09  3.000
 FR6  H3    C3   N4    125.62  3.000
 FR6  H3    C3   N2    122.60  3.000
 FR6  N4    C3   N2    111.79  3.000
 FR6  C5    N4   C3    105.45  3.000
 FR6  C8    C5   N4    123.34  3.000
 FR6  C8    C5   C1    126.59  3.000
 FR6  N4    C5   C1    110.07  3.000
 FR6  N10   C8   O9    123.99  3.000
 FR6  N10   C8   C5    114.64  3.000
 FR6  O9    C8   C5    121.37  3.000
 FR6  H102  N10  H101  118.42  3.000
 FR6  H102  N10  C8    120.75  3.000
 FR6  H101  N10  C8    120.81  3.000
 FR6  H13   C13  C18   108.99  3.000
 FR6  H13   C13  C14   108.22  3.000
 FR6  C18   C13  C14   113.38  3.000
 FR6  H13   C13  N2    105.93  3.000
 FR6  C18   C13  N2    110.13  3.000
 FR6  C14   C13  N2    109.89  3.000
 FR6  H14   C14  C9    108.93  3.000
 FR6  H14   C14  O15   105.46  3.000
 FR6  C9    C14  O15   111.77  3.000
 FR6  H14   C14  C13   108.17  3.000
 FR6  C9    C14  C13   112.17  3.000
 FR6  O15   C14  C13   110.05  3.000
 FR6  HO    O15  C14   108.58  3.000
 FR6  H182  C18  H181  106.18  3.000
 FR6  H182  C18  C19   110.60  3.000
 FR6  H181  C18  C19   108.88  3.000
 FR6  H182  C18  C13   109.73  3.000
 FR6  H181  C18  C13   108.68  3.000
 FR6  C19   C18  C13   112.55  3.000
 FR6  H192  C19  H191  105.91  3.000
 FR6  H192  C19  C22   109.14  3.000
 FR6  H191  C19  C22   110.80  3.000
 FR6  H192  C19  C18   108.74  3.000
 FR6  H191  C19  C18   110.40  3.000
 FR6  C22   C19  C18   111.65  3.000
 FR6  C29   C22  C25   118.90  3.000
 FR6  C29   C22  C19   121.42  3.000
 FR6  C25   C22  C19   119.65  3.000
 FR6  H25   C25  C26   118.97  3.000
 FR6  H25   C25  C22   119.20  3.000
 FR6  C26   C25  C22   121.82  3.000
 FR6  H26   C26  C27   120.40  3.000
 FR6  H26   C26  C25   119.43  3.000
 FR6  C27   C26  C25   120.16  3.000
 FR6  H27   C27  C28   119.05  3.000
 FR6  H27   C27  C26   120.73  3.000
 FR6  C28   C27  C26   120.22  3.000
 FR6  C2    C28  C29   119.43  3.000
 FR6  C2    C28  C27   120.96  3.000
 FR6  C29   C28  C27   119.62  3.000
 FR6  C4    C29  C28   118.01  3.000
 FR6  C4    C29  C22   122.71  3.000
 FR6  C28   C29  C22   119.28  3.000
 FR6  H2    C2   C6    120.29  3.000
 FR6  H2    C2   C28   118.73  3.000
 FR6  C6    C2   C28   120.97  3.000
 FR6  H4    C4   C7    118.85  3.000
 FR6  H4    C4   C29   119.86  3.000
 FR6  C7    C4   C29   121.30  3.000
 FR6  H6    C6   C7    119.85  3.000
 FR6  H6    C6   C2    120.28  3.000
 FR6  C7    C6   C2    119.86  3.000
 FR6  H7    C7   C6    119.66  3.000
 FR6  H7    C7   C4    119.91  3.000
 FR6  C6    C7   C4    120.43  3.000
 FR6  H93   C9   H92   107.46  3.000
 FR6  H93   C9   H91   108.22  3.000
 FR6  H92   C9   H91   107.76  3.000
 FR6  H93   C9   C14   110.00  3.000
 FR6  H92   C9   C14   111.99  3.000
 FR6  H91   C9   C14   111.26  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
 FR6  CONST_01  N4    C3   N2   C1      0.00   0.0  0
 FR6  CONST_02  C3    N4   C5   C1      0.00   0.0  0
 FR6  CONST_03  N4    C5   C1   N2      0.00   0.0  0
 FR6  CONST_04  C5    N4   C3   N2      0.00   0.0  0
 FR6  CONST_05  C5    C1   N2   C3      0.00   0.0  0
 FR6  CONST_06  C27   C26  C25  C22     0.00   0.0  0
 FR6  CONST_07  C27   C28  C29  C22     0.00   0.0  0
 FR6  CONST_08  C2    C28  C29  C22   180.00   0.0  0
 FR6  CONST_09  C7    C4   C29  C22   180.00   0.0  0
 FR6  CONST_10  C28   C29  C22  C25     0.00   0.0  0
 FR6  CONST_11  C4    C29  C22  C25   180.00   0.0  0
 FR6  CONST_12  C28   C27  C26  C25     0.00   0.0  0
 FR6  CONST_13  C29   C22  C25  C26     0.00   0.0  0
 FR6  CONST_14  C29   C28  C27  C26     0.00   0.0  0
 FR6  CONST_15  C2    C28  C27  C26   180.00   0.0  0
 FR6  CONST_16  C4    C29  C28  C27   180.00   0.0  0
 FR6  CONST_17  C6    C2   C28  C27   180.00   0.0  0
 FR6  CONST_18  C7    C4   C29  C28     0.00   0.0  0
 FR6  CONST_19  C7    C6   C2   C28     0.00   0.0  0
 FR6  CONST_20  C6    C2   C28  C29     0.00   0.0  0
 FR6  CONST_21  C6    C7   C4   C29     0.00   0.0  0
 FR6  CONST_22  C4    C29  C28  C2      0.00   0.0  0
 FR6  CONST_23  C4    C7   C6   C2      0.00   0.0  0
 FR6  CONST_24  C8    C5   C1   N2    180.00   0.0  0
 FR6  CONST_25  C8    C5   N4   C3    180.00   0.0  0
 FR6  CONST_26  C13   N2   C3   N4    180.00   0.0  0
 FR6  CONST_27  C13   N2   C1   C5    180.00   0.0  0
 FR6  CONST_28  C26   C25  C22  C19   180.00   0.0  0
 FR6  CONST_29  C28   C29  C22  C19   180.00   0.0  0
 FR6  CONST_30  C4    C29  C22  C19     0.00   0.0  0
 FR6  CONST_31  H3    C3   N2   C1    180.00   0.0  0
 FR6  CONST_32  H1    C1   N2   C3    180.00   0.0  0
 FR6  CONST_33  H26   C26  C25  C22   180.00   0.0  0
 FR6  CONST_34  H4    C4   C29  C22     0.00   0.0  0
 FR6  CONST_35  H27   C27  C26  C25   180.00   0.0  0
 FR6  CONST_36  H25   C25  C26  C27   180.00   0.0  0
 FR6  CONST_37  H2    C2   C28  C27     0.00   0.0  0
 FR6  CONST_38  H6    C6   C2   C28   180.00   0.0  0
 FR6  CONST_39  H7    C7   C4   C29   180.00   0.0  0
 FR6  CONST_40  H101  N10  C8   C5      0.00   0.0  0
 FR6  CONST_41  H102  N10  C8   C5    180.00   0.0  0
 FR6  Var_01    O9    C8   C5   C1     -0.64  30.0  2
 FR6  Var_02    C25   C22  C19  C18   -92.91  30.0  2
 FR6  Var_03    C22   C19  C18  C13  -174.56  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
 FR6  chir_01  C13  N2   C14  C18  negativ
 FR6  chir_02  C14  O15  C13  C9   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
 FR6  plan-1  C1    0.020
 FR6  plan-1  N2    0.020
 FR6  plan-1  C3    0.020
 FR6  plan-1  N4    0.020
 FR6  plan-1  C5    0.020
 FR6  plan-1  C8    0.020
 FR6  plan-1  C13   0.020
 FR6  plan-1  H1    0.020
 FR6  plan-1  H3    0.020
 FR6  plan-2  C19   0.020
 FR6  plan-2  C22   0.020
 FR6  plan-2  C25   0.020
 FR6  plan-2  C26   0.020
 FR6  plan-2  C27   0.020
 FR6  plan-2  C28   0.020
 FR6  plan-2  C29   0.020
 FR6  plan-2  C2    0.020
 FR6  plan-2  C4    0.020
 FR6  plan-2  C6    0.020
 FR6  plan-2  C7    0.020
 FR6  plan-2  H25   0.020
 FR6  plan-2  H26   0.020
 FR6  plan-2  H27   0.020
 FR6  plan-2  H2    0.020
 FR6  plan-2  H4    0.020
 FR6  plan-2  H6    0.020
 FR6  plan-2  H7    0.020
 FR6  plan-3  C5    0.020
 FR6  plan-3  C8    0.020
 FR6  plan-3  O9    0.020
 FR6  plan-3  N10   0.020
 FR6  plan-3  H101  0.020
 FR6  plan-3  H102  0.020

