# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 13:33:07 2022
#   Inital geometry file: a 133 line input string
#   Ligand name: (2~{S})-2-azanyl-7-[[2-(1,3-benzoxazol-2-yl)phenyl]methoxy]-3,4-dihydro-1~{H}-naphthalene-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: N[C@]1(CCc2ccc(OCc3ccccc3c4oc5ccccc5n4)cc2C1)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
 HO9  HO9  '(2~{S})-2-azanyl-7-[[2-(1,3-benzoxazol-2-yl)phenyl]methoxy]-3,4-dihydro-1~{H}-naphthalene-2-carboxylic acid'  ligand  52  31  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HO9
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
 HO9  C10  C  CH2    0  -0.514  144.6164  141.8722  134.8556
 HO9  N12  N  NH2    0  -0.803  148.2102  141.3774  134.2905
 HO9  C13  C  CH2    0  -0.298  145.9050  135.5541  135.5374
 HO9  C15  C  CR16   0  -0.304  146.3773  133.2045  134.8783
 HO9  C17  C  CR16   0  -0.247  144.9270  131.3687  135.3980
 HO9  C20  C  CR5    0   0.482  143.4510  134.4725  136.8697
 HO9  C22  C  CR56   0   0.343  141.5523  134.9748  137.7508
 HO9  C26  C  CR16   0  -0.266  139.8905  136.1420  138.9145
 HO9  C28  C  CR16   0  -0.328  142.1136  137.1111  138.7168
 HO9  C01  C  C1     0  -0.473  145.8420  138.3752  135.4735
 HO9  C02  C  C      0   0.146  145.7091  139.7599  135.4855
 HO9  C03  C  C      0   0.083  144.6181  140.3735  134.8703
 HO9  C04  C  C1     0  -0.316  143.6597  139.5785  134.2552
 HO9  C05  C  C1     0  -0.360  143.7715  138.1968  134.2547
 HO9  C06  C  C      0   0.396  144.8685  137.5877  134.8619
 HO9  C07  C  CH2    0  -0.536  146.6944  140.6704  136.1498
 HO9  C08  C  CT     0   0.007  147.1695  141.8208  135.2113
 HO9  C09  C  CH2    0  -0.426  145.9860  142.3546  134.3733
 HO9  C14  C  CR6    0   0.121  145.5404  134.0971  135.5340
 HO9  C16  C  CR16   0  -0.232  146.0855  131.8491  134.8104
 HO9  C18  C  CR16   0  -0.281  144.0750  132.2425  136.0538
 HO9  C19  C  CR6    0  -0.030  144.3697  133.6047  136.1368
 HO9  C23  C  CR56   0   0.172  142.4802  135.9814  137.9939
 HO9  C25  C  CR16   0  -0.339  140.2452  135.0102  138.1917
 HO9  C27  C  CR16   0  -0.262  140.8057  137.1708  139.1715
 HO9  C29  C  C      0   0.419  147.7522  142.9025  136.1650
 HO9  N24  N  N      0  -0.451  143.6782  135.6155  137.4165
 HO9  O11  O  O2     0  -0.476  144.9133  136.2388  134.7958
 HO9  O21  O  O      0  -0.451  142.1831  134.0171  137.0309
 HO9  O30  O  O      0  -0.596  146.9487  143.7366  136.6271
 HO9  O31  O  OC    -1  -0.603  148.9654  142.8054  136.4386
 HO9  H1   H  HCH2   0   0.239  143.8256  142.2526  134.2057
 HO9  H2   H  HCH2   0   0.227  144.4190  142.2706  135.8566
 HO9  H3   H  HNH2   0   0.327  149.0442  141.1713  134.8262
 HO9  H4   H  HNH2   0   0.324  147.9260  140.5109  133.8462
 HO9  H6   H  HCH2   0   0.250  146.8903  135.6862  135.0773
 HO9  H7   H  HCH2   0   0.245  145.9612  135.9357  136.5592
 HO9  H8   H  HCR6   0   0.265  147.2748  133.5805  134.4028
 HO9  H9   H  HCR6   0   0.267  144.6825  130.3160  135.3507
 HO9  H10  H  HCR6   0   0.265  138.8795  136.2304  139.2893
 HO9  H11  H  HCR6   0   0.265  142.8202  137.9060  138.9145
 HO9  H12  H  H      0   0.266  146.7119  137.9317  135.9423
 HO9  H13  H  H      0   0.240  142.8099  140.0415  133.7665
 HO9  H14  H  H      0   0.249  143.0160  137.5840  133.7782
 HO9  H15  H  HCH2   0   0.238  146.2079  141.1027  137.0319
 HO9  H16  H  HCH2   0   0.245  147.5631  140.1173  136.5140
 HO9  H17  H  HCH2   0   0.213  146.1093  142.0106  133.3429
 HO9  H18  H  HCH2   0   0.228  146.0081  143.4439  134.3408
 HO9  H19  H  HCR6   0   0.267  146.7570  131.1771  134.2928
 HO9  H20  H  HCR6   0   0.266  143.1797  131.8500  136.5160
 HO9  H21  H  HCR6   0   0.276  139.5405  134.2147  137.9912
 HO9  H22  H  HCR6   0   0.261  140.4795  138.0322  139.7391

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
 HO9  C04  C05  aromatic  1.386  0.020  1.386
 HO9  C04  C03  aromatic  1.389  0.020  1.389
 HO9  C05  C06  aromatic  1.394  0.020  1.394
 HO9  C03  C10  single    1.499  0.020  1.499
 HO9  C03  C02  aromatic  1.395  0.020  1.395
 HO9  C10  C09  single    1.530  0.020  1.530
 HO9  C16  C15  aromatic  1.388  0.020  1.388
 HO9  C16  C17  aromatic  1.385  0.020  1.385
 HO9  C06  O11  single    1.351  0.020  1.351
 HO9  C06  C01  aromatic  1.394  0.020  1.394
 HO9  O11  C13  single    1.415  0.020  1.415
 HO9  C15  C14  aromatic  1.388  0.020  1.388
 HO9  C09  C08  single    1.545  0.020  1.545
 HO9  C17  C18  aromatic  1.385  0.020  1.385
 HO9  C14  C13  single    1.502  0.020  1.502
 HO9  C14  C19  aromatic  1.406  0.020  1.406
 HO9  C02  C01  aromatic  1.391  0.020  1.391
 HO9  C02  C07  single    1.497  0.020  1.497
 HO9  C18  C19  aromatic  1.396  0.020  1.396
 HO9  C19  C20  single    1.461  0.020  1.461
 HO9  C08  N12  single    1.459  0.020  1.459
 HO9  C08  C07  single    1.559  0.020  1.559
 HO9  C08  C29  single    1.555  0.020  1.555
 HO9  N24  C20  aromatic  1.287  0.020  1.287
 HO9  N24  C23  aromatic  1.379  0.020  1.379
 HO9  C20  O21  aromatic  1.357  0.020  1.357
 HO9  O30  C29  deloc     1.247  0.020  1.247
 HO9  C29  O31  deloc     1.247  0.020  1.247
 HO9  C23  C28  aromatic  1.390  0.020  1.390
 HO9  C23  C22  aromatic  1.390  0.020  1.390
 HO9  C28  C27  aromatic  1.386  0.020  1.386
 HO9  O21  C22  aromatic  1.354  0.020  1.354
 HO9  C22  C25  aromatic  1.380  0.020  1.380
 HO9  C27  C26  aromatic  1.401  0.020  1.401
 HO9  C25  C26  aromatic  1.389  0.020  1.389
 HO9  C10  H1   single    0.970  0.020  1.090
 HO9  C10  H2   single    0.970  0.020  1.090
 HO9  N12  H3   single    0.890  0.020  1.040
 HO9  N12  H4   single    0.890  0.020  1.040
 HO9  C13  H6   single    0.970  0.020  1.090
 HO9  C13  H7   single    0.970  0.020  1.090
 HO9  C15  H8   single    0.930  0.020  1.080
 HO9  C17  H9   single    0.930  0.020  1.080
 HO9  C26  H10  single    0.930  0.020  1.080
 HO9  C28  H11  single    0.930  0.020  1.080
 HO9  C01  H12  single    0.930  0.020  1.080
 HO9  C04  H13  single    0.930  0.020  1.080
 HO9  C05  H14  single    0.930  0.020  1.080
 HO9  C07  H15  single    0.970  0.020  1.090
 HO9  C07  H16  single    0.970  0.020  1.090
 HO9  C09  H17  single    0.970  0.020  1.090
 HO9  C09  H18  single    0.970  0.020  1.090
 HO9  C16  H19  single    0.930  0.020  1.080
 HO9  C18  H20  single    0.930  0.020  1.080
 HO9  C25  H21  single    0.930  0.020  1.080
 HO9  C27  H22  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
 HO9  H2   C10  H1   106.66  3.000
 HO9  H2   C10  C09  109.55  3.000
 HO9  H1   C10  C09  110.53  3.000
 HO9  H2   C10  C03  110.80  3.000
 HO9  H1   C10  C03  110.80  3.000
 HO9  C09  C10  C03  108.50  3.000
 HO9  H4   N12  H3   106.78  3.000
 HO9  H4   N12  C08  109.65  3.000
 HO9  H3   N12  C08  108.40  3.000
 HO9  H7   C13  H6   107.73  3.000
 HO9  H7   C13  O11  110.94  3.000
 HO9  H6   C13  O11  110.61  3.000
 HO9  H7   C13  C14  110.70  3.000
 HO9  H6   C13  C14  109.54  3.000
 HO9  O11  C13  C14  107.34  3.000
 HO9  H8   C15  C16  119.46  3.000
 HO9  H8   C15  C14  118.93  3.000
 HO9  C16  C15  C14  121.62  3.000
 HO9  H9   C17  C18  119.70  3.000
 HO9  H9   C17  C16  120.53  3.000
 HO9  C18  C17  C16  119.77  3.000
 HO9  O21  C20  N24  114.36  3.000
 HO9  O21  C20  C19  116.61  3.000
 HO9  N24  C20  C19  129.02  3.000
 HO9  O21  C22  C25  129.00  3.000
 HO9  C25  C22  C23  123.90  3.000
 HO9  O21  C22  C23  107.11  3.000
 HO9  H10  C26  C27  119.15  3.000
 HO9  H10  C26  C25  119.04  3.000
 HO9  C27  C26  C25  121.81  3.000
 HO9  H11  C28  C27  121.65  3.000
 HO9  H11  C28  C23  121.32  3.000
 HO9  C27  C28  C23  117.03  3.000
 HO9  H12  C01  C06  121.31  3.000
 HO9  H12  C01  C02  118.72  3.000
 HO9  C06  C01  C02  119.97  3.000
 HO9  C07  C02  C03  116.30  3.000
 HO9  C07  C02  C01  123.12  3.000
 HO9  C03  C02  C01  120.59  3.000
 HO9  C04  C03  C02  118.90  3.000
 HO9  C02  C03  C10  116.43  3.000
 HO9  C04  C03  C10  124.56  3.000
 HO9  H13  C04  C05  119.26  3.000
 HO9  H13  C04  C03  119.74  3.000
 HO9  C05  C04  C03  121.00  3.000
 HO9  H14  C05  C06  119.56  3.000
 HO9  H14  C05  C04  120.51  3.000
 HO9  C06  C05  C04  119.93  3.000
 HO9  O11  C06  C05  116.17  3.000
 HO9  O11  C06  C01  124.22  3.000
 HO9  C05  C06  C01  119.61  3.000
 HO9  H16  C07  H15  106.52  3.000
 HO9  H16  C07  C08  109.39  3.000
 HO9  H15  C07  C08  109.19  3.000
 HO9  H16  C07  C02  111.31  3.000
 HO9  H15  C07  C02  107.75  3.000
 HO9  C08  C07  C02  112.47  3.000
 HO9  C29  C08  C09  112.28  3.000
 HO9  C29  C08  C07  104.97  3.000
 HO9  C09  C08  C07  110.36  3.000
 HO9  C29  C08  N12  109.34  3.000
 HO9  C07  C08  N12  111.91  3.000
 HO9  C09  C08  N12  108.01  3.000
 HO9  H18  C09  H17  106.50  3.000
 HO9  H18  C09  C08  110.24  3.000
 HO9  H17  C09  C08  108.42  3.000
 HO9  H18  C09  C10  110.04  3.000
 HO9  H17  C09  C10  107.39  3.000
 HO9  C08  C09  C10  113.94  3.000
 HO9  C19  C14  C15  118.64  3.000
 HO9  C19  C14  C13  122.75  3.000
 HO9  C15  C14  C13  118.59  3.000
 HO9  H19  C16  C17  120.44  3.000
 HO9  H19  C16  C15  119.96  3.000
 HO9  C17  C16  C15  119.59  3.000
 HO9  H20  C18  C19  120.23  3.000
 HO9  H20  C18  C17  118.85  3.000
 HO9  C19  C18  C17  120.91  3.000
 HO9  C18  C19  C14  119.47  3.000
 HO9  C18  C19  C20  118.47  3.000
 HO9  C14  C19  C20  122.06  3.000
 HO9  N24  C23  C28  131.47  3.000
 HO9  C28  C23  C22  120.21  3.000
 HO9  N24  C23  C22  108.32  3.000
 HO9  H21  C25  C26  121.97  3.000
 HO9  H21  C25  C22  122.62  3.000
 HO9  C26  C25  C22  115.41  3.000
 HO9  H22  C27  C28  119.40  3.000
 HO9  H22  C27  C26  118.95  3.000
 HO9  C28  C27  C26  121.65  3.000
 HO9  O31  C29  O30  126.69  3.000
 HO9  O31  C29  C08  116.40  3.000
 HO9  O30  C29  C08  116.81  3.000
 HO9  C23  N24  C20  105.07  3.000
 HO9  C06  O11  C13  118.73  3.000
 HO9  C22  O21  C20  105.13  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
 HO9  CONST_01  C18  C17  C16  C15     0.00   0.0  0
 HO9  CONST_02  C18  C19  C14  C15     0.00   0.0  0
 HO9  CONST_03  C20  C19  C14  C15   180.00   0.0  0
 HO9  CONST_04  C14  C15  C16  C17     0.00   0.0  0
 HO9  CONST_05  C14  C19  C18  C17     0.00   0.0  0
 HO9  CONST_06  C20  C19  C18  C17   180.00   0.0  0
 HO9  CONST_07  C28  C23  N24  C20   180.00   0.0  0
 HO9  CONST_08  C22  C23  N24  C20     0.00   0.0  0
 HO9  CONST_09  C23  C22  O21  C20     0.00   0.0  0
 HO9  CONST_10  C25  C22  O21  C20   180.00   0.0  0
 HO9  CONST_11  C27  C28  C23  C22     0.00   0.0  0
 HO9  CONST_12  C19  C20  O21  C22   180.00   0.0  0
 HO9  CONST_13  N24  C20  O21  C22     0.00   0.0  0
 HO9  CONST_14  C27  C26  C25  C22     0.00   0.0  0
 HO9  CONST_15  C23  C28  C27  C26     0.00   0.0  0
 HO9  CONST_16  C23  C22  C25  C26     0.00   0.0  0
 HO9  CONST_17  O21  C22  C25  C26   180.00   0.0  0
 HO9  CONST_18  O21  C22  C23  C28   180.00   0.0  0
 HO9  CONST_19  C25  C22  C23  C28     0.00   0.0  0
 HO9  CONST_20  C25  C26  C27  C28     0.00   0.0  0
 HO9  CONST_21  C04  C05  C06  C01     0.00   0.0  0
 HO9  CONST_22  C04  C03  C02  C01     0.00   0.0  0
 HO9  CONST_23  C05  C04  C03  C02     0.00   0.0  0
 HO9  CONST_24  C05  C06  C01  C02     0.00   0.0  0
 HO9  CONST_25  C06  C05  C04  C03     0.00   0.0  0
 HO9  CONST_26  C06  C01  C02  C03     0.00   0.0  0
 HO9  CONST_29  C19  C14  C15  C16     0.00   0.0  0
 HO9  CONST_30  C19  C18  C17  C16     0.00   0.0  0
 HO9  CONST_33  C23  N24  C20  C19   180.00   0.0  0
 HO9  CONST_34  O21  C20  N24  C23     0.00   0.0  0
 HO9  CONST_35  N24  C23  C22  C25   180.00   0.0  0
 HO9  CONST_36  N24  C23  C28  C27   180.00   0.0  0
 HO9  CONST_37  O21  C22  C23  N24     0.00   0.0  0
 HO9  CONST_38  C16  C15  C14  C13   180.00   0.0  0
 HO9  CONST_39  C18  C19  C14  C13   180.00   0.0  0
 HO9  CONST_40  C20  C19  C14  C13     0.00   0.0  0
 HO9  CONST_41  O11  C06  C01  C02   180.00   0.0  0
 HO9  CONST_42  O11  C06  C05  C04   180.00   0.0  0
 HO9  CONST_43  H13  C04  C03  C10     0.00   0.0  0
 HO9  CONST_44  H9   C17  C16  C15   180.00   0.0  0
 HO9  CONST_45  H8   C15  C16  C17   180.00   0.0  0
 HO9  CONST_46  H20  C18  C19  C20     0.00   0.0  0
 HO9  CONST_47  H11  C28  C23  C22   180.00   0.0  0
 HO9  CONST_48  H10  C26  C25  C22   180.00   0.0  0
 HO9  CONST_49  H14  C05  C06  C01   180.00   0.0  0
 HO9  CONST_50  H12  C01  C02  C03   180.00   0.0  0
 HO9  CONST_51  H19  C16  C15  C14   180.00   0.0  0
 HO9  CONST_52  H22  C27  C28  C23   180.00   0.0  0
 HO9  CONST_53  H21  C25  C22  C23   180.00   0.0  0
 HO9  Var_01    C08  C07  C02  C01   129.42  30.0  1
 HO9  Var_02    C09  C10  C03  C02    48.41  30.0  1
 HO9  Var_03    C08  C09  C10  C03   -56.34  30.0  1
 HO9  Var_04    C05  C06  O11  C13  -171.97  30.0  3
 HO9  Var_05    O11  C13  C14  C15   114.20  30.0  2
 HO9  Var_06    C14  C13  O11  C06   167.49  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
 HO9  chir_01  C08  C09  C07  C29  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
 HO9  plan-1  C13  0.020
 HO9  plan-1  C15  0.020
 HO9  plan-1  C17  0.020
 HO9  plan-1  C20  0.020
 HO9  plan-1  C14  0.020
 HO9  plan-1  C16  0.020
 HO9  plan-1  C18  0.020
 HO9  plan-1  C19  0.020
 HO9  plan-1  H8   0.020
 HO9  plan-1  H9   0.020
 HO9  plan-1  H19  0.020
 HO9  plan-1  H20  0.020
 HO9  plan-2  C20  0.020
 HO9  plan-2  C22  0.020
 HO9  plan-2  C26  0.020
 HO9  plan-2  C28  0.020
 HO9  plan-2  C19  0.020
 HO9  plan-2  C23  0.020
 HO9  plan-2  C25  0.020
 HO9  plan-2  C27  0.020
 HO9  plan-2  N24  0.020
 HO9  plan-2  O21  0.020
 HO9  plan-2  H10  0.020
 HO9  plan-2  H11  0.020
 HO9  plan-2  H21  0.020
 HO9  plan-2  H22  0.020
 HO9  plan-3  C10  0.020
 HO9  plan-3  C01  0.020
 HO9  plan-3  C02  0.020
 HO9  plan-3  C03  0.020
 HO9  plan-3  C04  0.020
 HO9  plan-3  C05  0.020
 HO9  plan-3  C06  0.020
 HO9  plan-3  C07  0.020
 HO9  plan-3  O11  0.020
 HO9  plan-3  H12  0.020
 HO9  plan-3  H13  0.020
 HO9  plan-3  H14  0.020
 HO9  plan-4  C08  0.020
 HO9  plan-4  C29  0.020
 HO9  plan-4  O30  0.020
 HO9  plan-4  O31  0.020

