# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 19:19:41 2020
#   Inital geometry file: a 157 line input string
#   Ligand name: (3R,5R)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)pyridin-3-yl]-3,5-dihydroxyheptanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COCc1c(nc(C(C)C)c(CC[C@@H](O)C[C@@H](O)CC(O)=O)c1c2ccc(F)cc2)C(C)C
#
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
 116  116  '(3R,5R)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)pyridin-3-yl]-3,5-dihydroxyheptanoic acid'  ligand  68  33  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_116
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
 116  C14   C  CH3    0  -0.396   2.5644   2.1047   4.8235
 116  O13   O  O2     0  -0.473   1.4335   1.7093   4.0902
 116  C13   C  CH2    0  -0.256   1.2069   0.3211   4.1742
 116  C17   C  CH3    0  -0.649  -2.0595   2.1768   4.9521
 116  C16   C  CH3    0  -0.648  -2.7275  -0.0999   5.8085
 116  C8    C  CR6    0   0.166   0.2146  -0.4829   2.0062
 116  C10   C  CR6    0  -0.005  -0.8857  -0.7964   1.2028
 116  C9    C  CR6    0   0.219  -2.1558  -0.5873   1.7534
 116  N1    N  N      0  -0.426  -2.3222  -0.1356   2.9872
 116  C12   C  CR6    0   0.234  -1.2855   0.1439   3.7633
 116  C11   C  CR6    0  -0.055   0.0273  -0.0239   3.3139
 116  C83   C  CR16   0  -0.405   3.5598   0.4277   0.5128
 116  C82   C  CR16   0  -0.230   2.2709   0.5215   1.0182
 116  C81   C  CR6    0  -0.052   1.5938  -0.6094   1.4652
 116  C86   C  CR16   0  -0.254   2.2334  -1.8447   1.4043
 116  C85   C  CR16   0  -0.404   3.5228  -1.9575   0.9052
 116  C84   C  CR6    0   0.519   4.1621  -0.8138   0.4673
 116  F1    F  F      0  -0.316   5.4110  -0.9121  -0.0179
 116  O1B   O  O      0  -0.621   1.7845   1.3068  -7.1535
 116  O1A   O  OC    -1  -0.622  -0.0928   1.7940  -8.2468
 116  O3    O  OH1    0  -0.675  -0.1945  -0.7654  -5.5838
 116  C2    C  CH2    0  -0.576  -0.1828   1.6404  -5.8689
 116  C3    C  CH1    0   0.051   0.1140   0.4628  -4.9496
 116  C4    C  CH2    0  -0.491  -0.5869   0.6333  -3.6036
 116  C5    C  CH1    0   0.044  -0.5115  -0.5666  -2.6591
 116  C6    C  CH2    0  -0.457  -0.7496  -0.1310  -1.2158
 116  C92   C  CH3    0  -0.646  -4.0296  -2.2012   1.5151
 116  C93   C  CH3    0  -0.646  -4.4399   0.2557   1.1190
 116  O5    O  OH1    0  -0.666  -1.4057  -1.5988  -3.0405
 116  H141  H  HCH3   0   0.234   2.6705   3.1843   4.7235
 116  H142  H  HCH3   0   0.203   2.4709   1.8631   5.8893
 116  H143  H  HCH3   0   0.203   3.4804   1.6305   4.4508
 116  H131  H  HCH2   0   0.227   2.0939  -0.2329   3.8434
 116  H132  H  HCH2   0   0.221   1.0332   0.0195   5.2154
 116  H15   H  HCH1   0   0.233  -0.7554   0.6997   5.7625
 116  H171  H  HCH3   0   0.230  -1.2525   2.7696   4.5202
 116  H172  H  HCH3   0   0.222  -2.9281   2.2534   4.2960
 116  H173  H  HCH3   0   0.226  -2.3216   2.6174   5.9155
 116  H161  H  HCH3   0   0.224  -2.4010  -1.1243   5.9948
 116  H162  H  HCH3   0   0.222  -2.9820   0.3472   6.7706
 116  H163  H  HCH3   0   0.230  -3.6295  -0.1402   5.1989
 116  H83   H  HCR6   0   0.279   4.0842   1.3077   0.1641
 116  H82   H  HCR6   0   0.260   1.7893   1.4893   1.0633
 116  H86   H  HCR6   0   0.267   1.7217  -2.7339   1.7504
 116  H85   H  HCR6   0   0.280   4.0185  -2.9183   0.8578
 116  HO3   H  HOH1   0   0.432  -1.1352  -0.9363  -5.4778
 116  H21   H  HCH2   0   0.199  -1.2631   1.7159  -6.0311
 116  H22   H  HCH2   0   0.220   0.1176   2.5648  -5.3613
 116  H3    H  HCH1   0   0.207   1.1934   0.4323  -4.7711
 116  H41   H  HCH2   0   0.221  -1.6439   0.8900  -3.7567
 116  H42   H  HCH2   0   0.234  -0.1431   1.5051  -3.1137
 116  H5    H  HCH1   0   0.222   0.4879  -1.0127  -2.7206
 116  H61   H  HCH2   0   0.228  -1.7095   0.3978  -1.1499
 116  H62   H  HCH2   0   0.240   0.0142   0.6051  -0.9495
 116  H71   H  HCH2   0   0.256   0.2424  -1.8045  -0.3101
 116  H72   H  HCH2   0   0.248  -1.4762  -2.0214  -0.4467
 116  H91   H  HCH1   0   0.230  -3.2119  -1.0158  -0.0574
 116  H921  H  HCH3   0   0.228  -4.9364  -2.4567   0.9645
 116  H922  H  HCH3   0   0.228  -3.3262  -3.0281   1.4010
 116  H923  H  HCH3   0   0.226  -4.2866  -2.1215   2.5726
 116  H931  H  HCH3   0   0.230  -4.7008   0.4454   2.1594
 116  H932  H  HCH3   0   0.224  -4.0398   1.1804   0.6995
 116  H933  H  HCH3   0   0.223  -5.3526   0.0098   0.5739
 116  HO5   H  HOH1   0   0.438  -2.3036  -1.2641  -2.9394
 116  C7    C  CH2    0  -0.557  -0.7100  -1.2820  -0.2108
 116  C15   C  CH1    0  -0.302  -1.6369   0.7157   5.1200
 116  C91   C  CH1    0  -0.311  -3.4359  -0.8877   1.0031
 116  C1    C  C      0   0.405   0.5646   1.5663  -7.2107

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
 116  C14  O13   single    1.405  0.020  1.405
 116  C14  H141  single    0.970  0.020  1.090
 116  C14  H142  single    0.970  0.020  1.090
 116  C14  H143  single    0.970  0.020  1.090
 116  O13  C13   single    1.409  0.020  1.409
 116  C13  C11   single    1.500  0.020  1.500
 116  C13  H131  single    0.970  0.020  1.090
 116  C13  H132  single    0.970  0.020  1.090
 116  C15  C17   single    1.530  0.020  1.530
 116  C15  C16   single    1.526  0.020  1.526
 116  C15  C12   single    1.514  0.020  1.514
 116  C15  H15   single    0.970  0.020  1.090
 116  C17  H171  single    0.970  0.020  1.090
 116  C17  H172  single    0.970  0.020  1.090
 116  C17  H173  single    0.970  0.020  1.090
 116  C16  H161  single    0.970  0.020  1.090
 116  C16  H162  single    0.970  0.020  1.090
 116  C16  H163  single    0.970  0.020  1.090
 116  C8   C10   aromatic  1.398  0.020  1.398
 116  C8   C11   aromatic  1.398  0.020  1.398
 116  C8   C81   single    1.487  0.020  1.487
 116  C10  C9    aromatic  1.400  0.020  1.400
 116  C10  C7    single    1.505  0.020  1.505
 116  C9   N1    aromatic  1.324  0.020  1.324
 116  C9   C91   single    1.514  0.020  1.514
 116  N1   C12   aromatic  1.325  0.020  1.325
 116  C12  C11   aromatic  1.398  0.020  1.398
 116  C83  C82   aromatic  1.388  0.020  1.388
 116  C83  C84   aromatic  1.381  0.020  1.381
 116  C83  H83   single    0.930  0.020  1.080
 116  C82  C81   aromatic  1.392  0.020  1.392
 116  C82  H82   single    0.930  0.020  1.080
 116  C81  C86   aromatic  1.392  0.020  1.392
 116  C86  C85   aromatic  1.387  0.020  1.387
 116  C86  H86   single    0.930  0.020  1.080
 116  C85  C84   aromatic  1.382  0.020  1.382
 116  C85  H85   single    0.930  0.020  1.080
 116  C84  F1    single    1.343  0.020  1.343
 116  O1B  C1    deloc     1.249  0.020  1.249
 116  O1A  C1    deloc     1.248  0.020  1.248
 116  O3   C3    single    1.416  0.020  1.416
 116  O3   HO3   single    0.850  0.020  0.980
 116  C1   C2    single    1.538  0.020  1.538
 116  C2   C3    single    1.523  0.020  1.523
 116  C2   H21   single    0.970  0.020  1.090
 116  C2   H22   single    0.970  0.020  1.090
 116  C3   C4    single    1.527  0.020  1.527
 116  C3   H3    single    0.970  0.020  1.090
 116  C4   C5    single    1.529  0.020  1.529
 116  C4   H41   single    0.970  0.020  1.090
 116  C4   H42   single    0.970  0.020  1.090
 116  C5   C6    single    1.526  0.020  1.526
 116  C5   O5    single    1.418  0.020  1.418
 116  C5   H5    single    0.970  0.020  1.090
 116  C6   C7    single    1.529  0.020  1.529
 116  C6   H61   single    0.970  0.020  1.090
 116  C6   H62   single    0.970  0.020  1.090
 116  C7   H71   single    0.970  0.020  1.090
 116  C7   H72   single    0.970  0.020  1.090
 116  C91  C92   single    1.530  0.020  1.530
 116  C91  C93   single    1.526  0.020  1.526
 116  C91  H91   single    0.970  0.020  1.090
 116  C92  H921  single    0.970  0.020  1.090
 116  C92  H922  single    0.970  0.020  1.090
 116  C92  H923  single    0.970  0.020  1.090
 116  C93  H931  single    0.970  0.020  1.090
 116  C93  H932  single    0.970  0.020  1.090
 116  C93  H933  single    0.970  0.020  1.090
 116  O5   HO5   single    0.850  0.020  0.980

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
 116  H143  C14  H142  107.83  3.000
 116  H143  C14  H141  108.42  3.000
 116  H142  C14  H141  108.41  3.000
 116  H143  C14  O13   111.92  3.000
 116  H142  C14  O13   112.12  3.000
 116  H141  C14  O13   108.03  3.000
 116  C13   O13  C14   112.07  3.000
 116  H132  C13  H131  105.98  3.000
 116  H132  C13  C11   110.88  3.000
 116  H131  C13  C11   110.29  3.000
 116  H132  C13  O13   110.65  3.000
 116  H131  C13  O13   110.46  3.000
 116  C11   C13  O13   108.59  3.000
 116  H173  C17  H172  108.13  3.000
 116  H173  C17  H171  107.94  3.000
 116  H172  C17  H171  108.23  3.000
 116  H173  C17  C15   110.79  3.000
 116  H172  C17  C15   110.66  3.000
 116  H171  C17  C15   110.98  3.000
 116  H163  C16  H162  108.39  3.000
 116  H163  C16  H161  107.97  3.000
 116  H162  C16  H161  107.70  3.000
 116  H163  C16  C15   111.04  3.000
 116  H162  C16  C15   110.22  3.000
 116  H161  C16  C15   111.40  3.000
 116  C81   C8   C11   119.50  3.000
 116  C81   C8   C10   120.12  3.000
 116  C11   C8   C10   120.36  3.000
 116  C7    C10  C9    121.57  3.000
 116  C7    C10  C8    121.35  3.000
 116  C9    C10  C8    117.03  3.000
 116  C91   C9   N1    115.03  3.000
 116  C91   C9   C10   122.86  3.000
 116  N1    C9   C10   122.10  3.000
 116  C12   N1   C9    121.29  3.000
 116  C11   C12  N1    121.42  3.000
 116  C11   C12  C15   123.48  3.000
 116  N1    C12  C15   115.03  3.000
 116  C12   C11  C8    117.77  3.000
 116  C12   C11  C13   121.77  3.000
 116  C8    C11  C13   120.42  3.000
 116  H83   C83  C84   120.61  3.000
 116  H83   C83  C82   120.83  3.000
 116  C84   C83  C82   118.56  3.000
 116  H82   C82  C81   119.79  3.000
 116  H82   C82  C83   119.28  3.000
 116  C81   C82  C83   120.93  3.000
 116  C86   C81  C82   118.90  3.000
 116  C86   C81  C8    121.17  3.000
 116  C82   C81  C8    119.93  3.000
 116  H86   C86  C85   119.18  3.000
 116  H86   C86  C81   119.83  3.000
 116  C85   C86  C81   120.99  3.000
 116  H85   C85  C84   120.61  3.000
 116  H85   C85  C86   120.91  3.000
 116  C84   C85  C86   118.48  3.000
 116  F1    C84  C85   118.95  3.000
 116  F1    C84  C83   118.90  3.000
 116  C85   C84  C83   122.15  3.000
 116  HO3   O3   C3    108.53  3.000
 116  H22   C2   H21   106.30  3.000
 116  H22   C2   C3    108.60  3.000
 116  H21   C2   C3    109.57  3.000
 116  H22   C2   C1    108.14  3.000
 116  H21   C2   C1    110.71  3.000
 116  C3    C2   C1    113.25  3.000
 116  H3    C3   C4    108.18  3.000
 116  H3    C3   C2    108.19  3.000
 116  C4    C3   C2    110.87  3.000
 116  H3    C3   O3    105.30  3.000
 116  C4    C3   O3    113.05  3.000
 116  C2    C3   O3    110.96  3.000
 116  H42   C4   H41   105.46  3.000
 116  H42   C4   C5    109.19  3.000
 116  H41   C4   C5    108.48  3.000
 116  H42   C4   C3    107.30  3.000
 116  H41   C4   C3    110.18  3.000
 116  C5    C4   C3    115.74  3.000
 116  H5    C5   O5    105.28  3.000
 116  H5    C5   C6    108.14  3.000
 116  O5    C5   C6    111.33  3.000
 116  H5    C5   C4    109.25  3.000
 116  O5    C5   C4    111.97  3.000
 116  C6    C5   C4    110.64  3.000
 116  H62   C6   H61   105.77  3.000
 116  H62   C6   C7    109.18  3.000
 116  H61   C6   C7    110.23  3.000
 116  H62   C6   C5    108.27  3.000
 116  H61   C6   C5    109.31  3.000
 116  C7    C6   C5    113.75  3.000
 116  H923  C92  H922  107.96  3.000
 116  H923  C92  H921  108.08  3.000
 116  H922  C92  H921  107.77  3.000
 116  H923  C92  C91   110.68  3.000
 116  H922  C92  C91   111.43  3.000
 116  H921  C92  C91   110.78  3.000
 116  H933  C93  H932  107.79  3.000
 116  H933  C93  H931  108.42  3.000
 116  H932  C93  H931  107.90  3.000
 116  H933  C93  C91   110.09  3.000
 116  H932  C93  C91   111.37  3.000
 116  H931  C93  C91   111.14  3.000
 116  HO5   O5   C5    107.85  3.000
 116  H72   C7   H71   105.60  3.000
 116  H72   C7   C6    110.50  3.000
 116  H71   C7   C6    108.87  3.000
 116  H72   C7   C10   109.87  3.000
 116  H71   C7   C10   109.99  3.000
 116  C6    C7   C10   111.82  3.000
 116  H15   C15  C12   109.56  3.000
 116  H15   C15  C16   107.69  3.000
 116  C12   C15  C16   111.62  3.000
 116  H15   C15  C17   107.56  3.000
 116  C12   C15  C17   109.05  3.000
 116  C16   C15  C17   111.25  3.000
 116  H91   C91  C93   107.27  3.000
 116  H91   C91  C92   107.70  3.000
 116  C93   C91  C92   111.26  3.000
 116  H91   C91  C9    109.35  3.000
 116  C93   C91  C9    111.71  3.000
 116  C92   C91  C9    109.43  3.000
 116  C2    C1   O1A   117.36  3.000
 116  C2    C1   O1B   116.42  3.000
 116  O1A   C1   O1B   126.20  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
 116  CONST_01  N1    C9   C10  C8      0.00   0.0  0
 116  CONST_02  N1    C12  C11  C8      0.00   0.0  0
 116  CONST_03  C83   C82  C81  C8    180.00   0.0  0
 116  CONST_04  C85   C86  C81  C8    180.00   0.0  0
 116  CONST_05  C12   C11  C8   C10     0.00   0.0  0
 116  CONST_08  C12   N1   C9   C10     0.00   0.0  0
 116  CONST_09  C11   C8   C10  C9      0.00   0.0  0
 116  CONST_10  C81   C8   C10  C9    180.00   0.0  0
 116  CONST_11  C11   C12  N1   C9      0.00   0.0  0
 116  CONST_12  C81   C8   C11  C12   180.00   0.0  0
 116  CONST_15  C86   C81  C82  C83     0.00   0.0  0
 116  CONST_16  C86   C85  C84  C83     0.00   0.0  0
 116  CONST_17  C85   C84  C83  C82     0.00   0.0  0
 116  CONST_18  C85   C86  C81  C82     0.00   0.0  0
 116  CONST_19  C84   C83  C82  C81     0.00   0.0  0
 116  CONST_20  C84   C85  C86  C81     0.00   0.0  0
 116  CONST_21  C10   C8   C11  C13   180.00   0.0  0
 116  CONST_22  C81   C8   C11  C13     0.00   0.0  0
 116  CONST_23  N1    C12  C11  C13   180.00   0.0  0
 116  CONST_24  C9    N1   C12  C15   180.00   0.0  0
 116  CONST_25  C8    C11  C12  C15   180.00   0.0  0
 116  CONST_26  C91   C9   C10  C8    180.00   0.0  0
 116  CONST_27  C7    C10  C9   N1    180.00   0.0  0
 116  CONST_28  C91   C9   N1   C12   180.00   0.0  0
 116  CONST_29  C7    C10  C8   C11   180.00   0.0  0
 116  CONST_30  F1    C84  C83  C82   180.00   0.0  0
 116  CONST_31  C7    C10  C8   C81     0.00   0.0  0
 116  CONST_32  F1    C84  C85  C86   180.00   0.0  0
 116  CONST_33  H82   C82  C81  C8      0.00   0.0  0
 116  CONST_34  H86   C86  C81  C8      0.00   0.0  0
 116  CONST_35  H85   C85  C84  C83   180.00   0.0  0
 116  CONST_36  H83   C83  C82  C81   180.00   0.0  0
 116  Var_01    C8    C11  C13  O13    95.95  30.0  2
 116  Var_02    N1    C12  C15  C17   -75.32  30.0  2
 116  Var_03    C6    C7   C10  C8    -92.60  30.0  2
 116  Var_04    C92   C91  C9   C10   102.76  30.0  2
 116  Var_05    C11   C13  O13  C14  -177.28  30.0  3
 116  Var_06    C5    C6   C7   C10   177.35  30.0  2
 116  Var_07    H921  C92  C91  C9   -178.05  30.0  3
 116  Var_08    H931  C93  C91  C9    -59.58  30.0  3
 116  Var_09    H171  C17  C15  C12   -60.22  30.0  3
 116  Var_10    H161  C16  C15  C12    62.06  30.0  3
 116  Var_11    C3    C2   C1   O1B   -47.65  30.0  3
 116  Var_12    H141  C14  O13  C13  -179.32  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
 116  chir_01  C3  O3  C2  C4  negativ
 116  chir_02  C5  O5  C4  C6  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
 116  plan-1  C13  0.020
 116  plan-1  C8   0.020
 116  plan-1  C10  0.020
 116  plan-1  C9   0.020
 116  plan-1  N1   0.020
 116  plan-1  C12  0.020
 116  plan-1  C11  0.020
 116  plan-1  C81  0.020
 116  plan-1  C7   0.020
 116  plan-1  C15  0.020
 116  plan-1  C91  0.020
 116  plan-2  C8   0.020
 116  plan-2  C83  0.020
 116  plan-2  C82  0.020
 116  plan-2  C81  0.020
 116  plan-2  C86  0.020
 116  plan-2  C85  0.020
 116  plan-2  C84  0.020
 116  plan-2  F1   0.020
 116  plan-2  H83  0.020
 116  plan-2  H82  0.020
 116  plan-2  H86  0.020
 116  plan-2  H85  0.020
 116  plan-3  O1B  0.020
 116  plan-3  O1A  0.020
 116  plan-3  C2   0.020
 116  plan-3  C1   0.020

