# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 09:30:20 2020
#   Inital geometry file: a 123 line input string
#   Ligand name: 2-(5-chloranyl-2-piperidin-4-yloxy-phenyl)-5-[(1,3,5-trimethylpyrazol-4-yl)methyl]-1,3,4-oxadiazole
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1nc(C)c(Cc2oc(nn2)c3cc(Cl)ccc3OC4CCNCC4)c1C
#
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
 TUQ  TUQ  2-(5-chloranyl-2-piperidin-4-yloxy-phenyl)-5-[(1,3,5-trimethylpyrazol-4-yl)methyl]-1,3,4-oxadiazole  ligand  52  28  .  2022-07-22  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_TUQ
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
 TUQ  CL    CL  CL    0  -0.128  -0.8236  -4.4784   1.3028
 TUQ  C11   C   CR6   0  -0.053  -1.3687  -2.9181   0.7828
 TUQ  C10   C   CR16  0  -0.236  -0.4903  -2.0668   0.1443
 TUQ  C12   C   CR16  0  -0.193  -2.6794  -2.5334   1.0104
 TUQ  C13   C   CR16  0  -0.382  -3.1101  -1.2863   0.5952
 TUQ  C14   C   CR6   0   0.416  -2.2440  -0.4062  -0.0557
 TUQ  O1    O   O2    0  -0.462  -2.5914   0.8001  -0.4976
 TUQ  C15   C   CH1   0   0.026  -3.8781   1.3572  -0.2188
 TUQ  C19   C   CH2   0  -0.457  -4.0938   2.4884  -1.2089
 TUQ  C18   C   CH2   0  -0.329  -5.4258   3.1830  -0.9161
 TUQ  N4    N   NH1   0  -0.572  -5.5558   3.6583   0.4505
 TUQ  C17   C   CH2   0  -0.324  -5.3065   2.5973   1.4102
 TUQ  C16   C   CH2   0  -0.482  -3.9684   1.8797   1.2076
 TUQ  C9    C   CR6   0  -0.150  -0.9118  -0.8059  -0.2812
 TUQ  C8    C   CR5   0   0.487   0.0456   0.0652  -0.9459
 TUQ  N3    N   N     0  -0.301  -0.0932   1.2143  -1.5158
 TUQ  N2    N   N     0  -0.311   1.1458   1.5773  -1.9780
 TUQ  O     O   O     0  -0.419   1.3254  -0.3537  -1.0122
 TUQ  C7    C   CR5   0   0.497   1.9566   0.6316  -1.6658
 TUQ  C6    C   CH2   0  -0.680   3.4151   0.5219  -1.9113
 TUQ  C5    C   CR5   0  -0.207   4.1912   0.3405  -0.6454
 TUQ  C1    C   CR5   0   0.254   4.5725  -0.8680  -0.0295
 TUQ  C     C   CH3   0  -0.746   4.2925  -2.2568  -0.4906
 TUQ  C3    C   CR5   0   0.419   4.6801   1.3328   0.1823
 TUQ  C4    C   CH3   0  -0.749   4.5884   2.8120   0.0721
 TUQ  N1    N   NR5   0  -0.323   5.3094   0.6986   1.1904
 TUQ  N     N   N     0  -0.314   5.2478  -0.6303   1.0794
 TUQ  C2    C   CH3   0  -0.521   5.9331   1.2936   2.3464
 TUQ  H10   H   HCR6  0   0.286   0.5280  -2.3886  -0.0240
 TUQ  H12   H   HCR6  0   0.292  -3.3711  -3.1968   1.5112
 TUQ  H13   H   HCR6  0   0.295  -4.1391  -1.0178   0.7853
 TUQ  H15   H   HCH1  0   0.232  -4.6538   0.5997  -0.3884
 TUQ  H191  H   HCH2  0   0.231  -3.2743   3.2084  -1.1231
 TUQ  H192  H   HCH2  0   0.243  -4.0888   2.1041  -2.2318
 TUQ  H161  H   HCH2  0   0.246  -3.8667   1.0752   1.9400
 TUQ  H162  H   HCH2  0   0.235  -3.1482   2.5842   1.3810
 TUQ  H181  H   HCH2  0   0.246  -5.5625   4.0218  -1.6001
 TUQ  H182  H   HCH2  0   0.222  -6.2460   2.4837  -1.1124
 TUQ  H4    H   HNH1  0   0.341  -4.8903   4.4073   0.6057
 TUQ  H171  H   HCH2  0   0.246  -5.3524   3.0113   2.4186
 TUQ  H172  H   HCH2  0   0.224  -6.1220   1.8704   1.3345
 TUQ  H61C  H   HCH2  0   0.298   3.5979  -0.3131  -2.5942
 TUQ  H62C  H   HCH2  0   0.300   3.7238   1.4245  -2.4394
 TUQ  HC1   H   HCH3  0   0.244   4.4875  -2.3698  -1.5578
 TUQ  HC2   H   HCH3  0   0.251   4.9113  -2.9767   0.0425
 TUQ  HC3   H   HCH3  0   0.247   3.2485  -2.5301  -0.3263
 TUQ  H41C  H   HCH3  0   0.262   4.0917   3.2539   0.9371
 TUQ  H42C  H   HCH3  0   0.261   5.5726   3.2756  -0.0142
 TUQ  H43C  H   HCH3  0   0.260   4.0162   3.0884  -0.8114
 TUQ  H21C  H   HCH3  0   0.254   5.2372   1.3562   3.1833
 TUQ  H22C  H   HCH3  0   0.264   6.7893   0.6924   2.6404
 TUQ  H23C  H   HCH3  0   0.259   6.2799   2.2949   2.1051

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
 TUQ  CL   C11   single    1.733  0.020  1.733
 TUQ  C11  C10   aromatic  1.380  0.020  1.380
 TUQ  C11  C12   aromatic  1.385  0.020  1.385
 TUQ  C10  C9    aromatic  1.396  0.020  1.396
 TUQ  C12  C13   aromatic  1.383  0.020  1.383
 TUQ  C13  C14   aromatic  1.396  0.020  1.396
 TUQ  C14  O1    single    1.331  0.020  1.331
 TUQ  C14  C9    aromatic  1.409  0.020  1.409
 TUQ  O1   C15   single    1.430  0.020  1.430
 TUQ  C15  C19   single    1.519  0.020  1.519
 TUQ  C15  C16   single    1.522  0.020  1.522
 TUQ  C19  C18   single    1.530  0.020  1.530
 TUQ  C18  N4    single    1.453  0.020  1.453
 TUQ  N4   C17   single    1.452  0.020  1.452
 TUQ  C17  C16   single    1.532  0.020  1.532
 TUQ  C9   C8    single    1.455  0.020  1.455
 TUQ  C8   N3    aromatic  1.290  0.020  1.290
 TUQ  C8   O     aromatic  1.348  0.020  1.348
 TUQ  N3   N2    aromatic  1.371  0.020  1.371
 TUQ  N2   C7    aromatic  1.284  0.020  1.284
 TUQ  O    C7    aromatic  1.340  0.020  1.340
 TUQ  C7   C6    single    1.483  0.020  1.483
 TUQ  C6   C5    single    1.496  0.020  1.496
 TUQ  C5   C1    aromatic  1.409  0.020  1.409
 TUQ  C5   C3    aromatic  1.382  0.020  1.382
 TUQ  C1   C     single    1.490  0.020  1.490
 TUQ  C1   N     aromatic  1.320  0.020  1.320
 TUQ  C3   C4    single    1.486  0.020  1.486
 TUQ  C3   N1    aromatic  1.347  0.020  1.347
 TUQ  N1   N     aromatic  1.335  0.020  1.335
 TUQ  N1   C2    single    1.442  0.020  1.442
 TUQ  C10  H10   single    0.930  0.020  1.080
 TUQ  C12  H12   single    0.930  0.020  1.080
 TUQ  C13  H13   single    0.930  0.020  1.080
 TUQ  C15  H15   single    0.970  0.020  1.090
 TUQ  C19  H191  single    0.970  0.020  1.090
 TUQ  C19  H192  single    0.970  0.020  1.090
 TUQ  C16  H161  single    0.970  0.020  1.090
 TUQ  C16  H162  single    0.970  0.020  1.090
 TUQ  C18  H181  single    0.970  0.020  1.090
 TUQ  C18  H182  single    0.970  0.020  1.090
 TUQ  N4   H4    single    0.890  0.020  1.040
 TUQ  C17  H171  single    0.970  0.020  1.090
 TUQ  C17  H172  single    0.970  0.020  1.090
 TUQ  C6   H61C  single    0.970  0.020  1.090
 TUQ  C6   H62C  single    0.970  0.020  1.090
 TUQ  C    HC1   single    0.970  0.020  1.090
 TUQ  C    HC2   single    0.970  0.020  1.090
 TUQ  C    HC3   single    0.970  0.020  1.090
 TUQ  C4   H41C  single    0.970  0.020  1.090
 TUQ  C4   H42C  single    0.970  0.020  1.090
 TUQ  C4   H43C  single    0.970  0.020  1.090
 TUQ  C2   H21C  single    0.970  0.020  1.090
 TUQ  C2   H22C  single    0.970  0.020  1.090
 TUQ  C2   H23C  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
 TUQ  C12   C11  C10   120.48  3.000
 TUQ  C12   C11  CL    119.91  3.000
 TUQ  C10   C11  CL    119.62  3.000
 TUQ  H10   C10  C9    120.39  3.000
 TUQ  H10   C10  C11   119.21  3.000
 TUQ  C9    C10  C11   120.40  3.000
 TUQ  H12   C12  C13   119.53  3.000
 TUQ  H12   C12  C11   120.74  3.000
 TUQ  C13   C12  C11   119.73  3.000
 TUQ  H13   C13  C14   121.09  3.000
 TUQ  H13   C13  C12   117.90  3.000
 TUQ  C14   C13  C12   121.01  3.000
 TUQ  C9    C14  O1    116.79  3.000
 TUQ  C9    C14  C13   118.85  3.000
 TUQ  O1    C14  C13   124.36  3.000
 TUQ  C15   O1   C14   121.56  3.000
 TUQ  H15   C15  C16   109.87  3.000
 TUQ  H15   C15  C19   108.24  3.000
 TUQ  C16   C15  C19   110.30  3.000
 TUQ  H15   C15  O1    109.69  3.000
 TUQ  C16   C15  O1    111.72  3.000
 TUQ  C19   C15  O1    106.92  3.000
 TUQ  H192  C19  H191  107.54  3.000
 TUQ  H192  C19  C18   110.04  3.000
 TUQ  H191  C19  C18   109.76  3.000
 TUQ  H192  C19  C15   110.35  3.000
 TUQ  H191  C19  C15   109.43  3.000
 TUQ  C18   C19  C15   109.69  3.000
 TUQ  H182  C18  H181  106.53  3.000
 TUQ  H182  C18  N4    108.08  3.000
 TUQ  H181  C18  N4    109.09  3.000
 TUQ  H182  C18  C19   109.13  3.000
 TUQ  H181  C18  C19   109.76  3.000
 TUQ  N4    C18  C19   113.98  3.000
 TUQ  H4    N4   C17   109.02  3.000
 TUQ  H4    N4   C18   109.09  3.000
 TUQ  C17   N4   C18   111.55  3.000
 TUQ  H172  C17  H171  106.53  3.000
 TUQ  H172  C17  C16   109.30  3.000
 TUQ  H171  C17  C16   109.68  3.000
 TUQ  H172  C17  N4    108.14  3.000
 TUQ  H171  C17  N4    109.05  3.000
 TUQ  C16   C17  N4    113.88  3.000
 TUQ  H162  C16  H161  107.33  3.000
 TUQ  H162  C16  C17   109.39  3.000
 TUQ  H161  C16  C17   109.73  3.000
 TUQ  H162  C16  C15   108.96  3.000
 TUQ  H161  C16  C15   111.71  3.000
 TUQ  C17   C16  C15   109.68  3.000
 TUQ  C8    C9   C14   121.70  3.000
 TUQ  C8    C9   C10   118.77  3.000
 TUQ  C14   C9   C10   119.53  3.000
 TUQ  O     C8   N3    110.92  3.000
 TUQ  O     C8   C9    117.45  3.000
 TUQ  N3    C8   C9    131.62  3.000
 TUQ  N2    N3   C8    106.71  3.000
 TUQ  C7    N2   N3    107.07  3.000
 TUQ  C7    O    C8    104.04  3.000
 TUQ  C6    C7   O     119.31  3.000
 TUQ  C6    C7   N2    129.43  3.000
 TUQ  O     C7   N2    111.26  3.000
 TUQ  H62C  C6   H61C  106.39  3.000
 TUQ  H62C  C6   C5    111.30  3.000
 TUQ  H61C  C6   C5    110.43  3.000
 TUQ  H62C  C6   C7    107.30  3.000
 TUQ  H61C  C6   C7    108.91  3.000
 TUQ  C5    C6   C7    112.27  3.000
 TUQ  C3    C5   C1    104.97  3.000
 TUQ  C3    C5   C6    127.12  3.000
 TUQ  C1    C5   C6    127.90  3.000
 TUQ  N     C1   C     121.60  3.000
 TUQ  N     C1   C5    110.56  3.000
 TUQ  C     C1   C5    127.84  3.000
 TUQ  HC3   C    HC2   107.72  3.000
 TUQ  HC3   C    HC1   107.00  3.000
 TUQ  HC2   C    HC1   108.00  3.000
 TUQ  HC3   C    C1    111.50  3.000
 TUQ  HC2   C    C1    110.98  3.000
 TUQ  HC1   C    C1    111.46  3.000
 TUQ  N1    C3   C4    123.57  3.000
 TUQ  N1    C3   C5    106.00  3.000
 TUQ  C4    C3   C5    130.44  3.000
 TUQ  H43C  C4   H42C  107.58  3.000
 TUQ  H43C  C4   H41C  107.54  3.000
 TUQ  H42C  C4   H41C  107.53  3.000
 TUQ  H43C  C4   C3    110.21  3.000
 TUQ  H42C  C4   C3    111.90  3.000
 TUQ  H41C  C4   C3    111.87  3.000
 TUQ  C2    N1   N     119.83  3.000
 TUQ  C2    N1   C3    127.43  3.000
 TUQ  N     N1   C3    112.64  3.000
 TUQ  N1    N    C1    105.83  3.000
 TUQ  H23C  C2   H22C  108.57  3.000
 TUQ  H23C  C2   H21C  108.74  3.000
 TUQ  H22C  C2   H21C  109.08  3.000
 TUQ  H23C  C2   N1    109.89  3.000
 TUQ  H22C  C2   N1    109.23  3.000
 TUQ  H21C  C2   N1    111.28  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
 TUQ  CONST_01  C14   C9   C10  C11     0.00   0.0  0
 TUQ  CONST_02  C8    C9   C10  C11   180.00   0.0  0
 TUQ  CONST_03  C14   C13  C12  C11     0.00   0.0  0
 TUQ  CONST_04  C13   C12  C11  C10     0.00   0.0  0
 TUQ  CONST_05  C13   C14  C9   C10     0.00   0.0  0
 TUQ  CONST_06  N3    C8   C9   C10   180.00   0.0  0
 TUQ  CONST_07  O     C8   C9   C10     0.00   0.0  0
 TUQ  CONST_08  C9    C10  C11  C12     0.00   0.0  0
 TUQ  CONST_09  C9    C14  C13  C12     0.00   0.0  0
 TUQ  CONST_10  C8    C9   C14  C13   180.00   0.0  0
 TUQ  CONST_11  N3    C8   C9   C14     0.00   0.0  0
 TUQ  CONST_12  O     C8   C9   C14   180.00   0.0  0
 TUQ  CONST_13  N2    N3   C8   C9    180.00   0.0  0
 TUQ  CONST_14  C7    O    C8   C9    180.00   0.0  0
 TUQ  CONST_15  C7    N2   N3   C8      0.00   0.0  0
 TUQ  CONST_16  N2    C7   O    C8      0.00   0.0  0
 TUQ  CONST_17  C7    O    C8   N3      0.00   0.0  0
 TUQ  CONST_18  O     C7   N2   N3      0.00   0.0  0
 TUQ  CONST_19  O     C8   N3   N2      0.00   0.0  0
 TUQ  CONST_20  N1    N    C1   C5      0.00   0.0  0
 TUQ  CONST_21  N     N1   C3   C5      0.00   0.0  0
 TUQ  CONST_22  N1    C3   C5   C1      0.00   0.0  0
 TUQ  CONST_23  C3    N1   N    C1      0.00   0.0  0
 TUQ  CONST_24  N     C1   C5   C3      0.00   0.0  0
 TUQ  CONST_25  C9    C10  C11  CL    180.00   0.0  0
 TUQ  CONST_26  C13   C12  C11  CL    180.00   0.0  0
 TUQ  CONST_27  O1    C14  C9   C10   180.00   0.0  0
 TUQ  CONST_28  O1    C14  C13  C12   180.00   0.0  0
 TUQ  CONST_29  C8    C9   C14  O1      0.00   0.0  0
 TUQ  CONST_30  C6    C7   O    C8    180.00   0.0  0
 TUQ  CONST_31  C6    C7   N2   N3    180.00   0.0  0
 TUQ  CONST_32  N     C1   C5   C6    180.00   0.0  0
 TUQ  CONST_33  N1    C3   C5   C6    180.00   0.0  0
 TUQ  CONST_34  C2    N1   C3   C5    180.00   0.0  0
 TUQ  CONST_35  C4    C3   C5   C1    180.00   0.0  0
 TUQ  CONST_36  C2    N1   N    C1    180.00   0.0  0
 TUQ  CONST_37  C3    C5   C1   C     180.00   0.0  0
 TUQ  CONST_38  N1    N    C1   C     180.00   0.0  0
 TUQ  CONST_39  N     N1   C3   C4    180.00   0.0  0
 TUQ  CONST_40  H13   C13  C12  C11   180.00   0.0  0
 TUQ  CONST_41  H12   C12  C11  C10   180.00   0.0  0
 TUQ  CONST_42  H10   C10  C11  C12   180.00   0.0  0
 TUQ  Var_01    N4    C18  C19  C15    54.97  30.0  1
 TUQ  Var_02    N4    C17  C16  C15   -54.93  30.0  1
 TUQ  Var_03    C17   N4   C18  C19   -53.64  30.0  1
 TUQ  Var_04    C16   C17  N4   C18    53.61  30.0  1
 TUQ  Var_05    C9    C14  O1   C15  -174.27  30.0  2
 TUQ  Var_06    C5    C6   C7   N2    122.29  30.0  2
 TUQ  Var_07    C1    C5   C6   C7     91.91  30.0  2
 TUQ  Var_08    HC1   C    C1   C5     45.54  30.0  2
 TUQ  Var_09    H41C  C4   C3   C5    120.95  30.0  2
 TUQ  Var_10    H21C  C2   N1   C3     92.22  30.0  2

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
 TUQ  chir_01  C15  O1  C19  C16  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
 TUQ  plan-1  C9   0.020
 TUQ  plan-1  C8   0.020
 TUQ  plan-1  N3   0.020
 TUQ  plan-1  N2   0.020
 TUQ  plan-1  O    0.020
 TUQ  plan-1  C7   0.020
 TUQ  plan-1  C6   0.020
 TUQ  plan-2  C6   0.020
 TUQ  plan-2  C5   0.020
 TUQ  plan-2  C1   0.020
 TUQ  plan-2  C    0.020
 TUQ  plan-2  C3   0.020
 TUQ  plan-2  C4   0.020
 TUQ  plan-2  N1   0.020
 TUQ  plan-2  N    0.020
 TUQ  plan-2  C2   0.020
 TUQ  plan-3  CL   0.020
 TUQ  plan-3  C11  0.020
 TUQ  plan-3  C10  0.020
 TUQ  plan-3  C12  0.020
 TUQ  plan-3  C13  0.020
 TUQ  plan-3  C14  0.020
 TUQ  plan-3  O1   0.020
 TUQ  plan-3  C9   0.020
 TUQ  plan-3  C8   0.020
 TUQ  plan-3  H10  0.020
 TUQ  plan-3  H12  0.020
 TUQ  plan-3  H13  0.020

