# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 20 23:16:07 2022
#   Inital geometry file: a 102 line input string
#   Ligand name: ~{tert}-butyl 6-[5-oxidanyl-4-(1,2,3-triazol-1-yl)pyrazol-1-yl]pyridine-3-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(C)OC(=O)c1ccc(nc1)n2ncc(n3ccnn3)c2O
#
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
 QEE  QEE  '~{tert}-butyl 6-[5-oxidanyl-4-(1,2,3-triazol-1-yl)pyrazol-1-yl]pyridine-3-carboxylate'  ligand  40  24  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_QEE
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
 QEE  N12   N  NR5   0  -0.425  28.3219  -14.6859  42.9779
 QEE  C15   C  CR5   0   0.025  30.0598  -15.8713  42.4057
 QEE  C20   C  CR15  0  -0.079  31.8169  -17.3626  43.3000
 QEE  C21   C  CR5   0   0.590  29.5509  -15.0799  43.4041
 QEE  C24   C  CR16  0  -0.141  26.2861  -13.1411  45.6127
 QEE  C04   C  CT    0   0.181  23.6170  -10.5472  47.5119
 QEE  C05   C  CH3   0  -0.671  24.0693   -9.0939  47.4611
 QEE  C06   C  CH3   0  -0.658  23.8290  -11.1117  48.9101
 QEE  C07   C  CH3   0  -0.671  22.1598  -10.7081  47.0998
 QEE  C08   C  CR6   0  -0.163  25.5983  -12.2183  44.8323
 QEE  C09   C  CR16  0  -0.046  25.8568  -12.2095  43.4646
 QEE  C11   C  CR6   0   0.488  27.3896  -13.8662  43.6439
 QEE  C14   C  CR15  0  -0.008  29.0730  -15.8856  41.4040
 QEE  C19   C  CR15  0  -0.176  33.0540  -17.6617  42.8017
 QEE  C23   C  CR16  0  -0.355  27.1930  -13.9950  45.0127
 QEE  N10   N  N     0  -0.399  26.7383  -13.0056  42.8843
 QEE  N13   N  N     0  -0.270  28.0429  -15.1568  41.7464
 QEE  N16   N  NR5   0  -0.353  31.3079  -16.4972  42.4002
 QEE  N17   N  N     0  -0.103  32.1716  -16.2774  41.4121
 QEE  N18   N  N     0  -0.288  33.2206  -16.9794  41.6473
 QEE  O01   O  O     0  -0.438  24.0254  -10.4572  44.6869
 QEE  O03   O  O2    0  -0.477  24.4865  -11.3823  46.6858
 QEE  O22   O  OH1   0  -0.602  30.1070  -14.7901  44.5720
 QEE  H201  H  HCR5  0   0.314  31.2760  -17.6898  44.1713
 QEE  H241  H  HCR6  0   0.287  26.1140  -13.2154  46.6771
 QEE  H051  H  HCH3  0   0.241  23.5174   -8.5279  48.2121
 QEE  H053  H  HCH3  0   0.239  25.1311   -9.0045  47.6950
 QEE  H052  H  HCH3  0   0.246  23.8819   -8.6303  46.4951
 QEE  H061  H  HCH3  0   0.234  23.2243  -10.5536  49.6243
 QEE  H063  H  HCH3  0   0.240  23.5318  -12.1598  48.9664
 QEE  H062  H  HCH3  0   0.239  24.8721  -11.0297  49.2190
 QEE  H072  H  HCH3  0   0.241  21.5298  -10.2171  47.8423
 QEE  H073  H  HCH3  0   0.247  21.9437  -10.2590  46.1332
 QEE  H071  H  HCH3  0   0.239  21.8732  -11.7604  47.0703
 QEE  H091  H  HCR6  0   0.283  25.3339  -11.5195  42.8134
 QEE  H141  H  HCR5  0   0.291  29.1002  -16.3989  40.4550
 QEE  H191  H  HCR5  0   0.280  33.8096  -18.3173  43.2012
 QEE  H231  H  HCR6  0   0.307  27.7038  -14.7469  45.5964
 QEE  H221  H  HOH1  0   0.501  30.0198  -13.8560  44.8101
 QEE  C02   C  C     0   0.607  24.6113  -11.2494  45.3835

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
 QEE  C14  N13   aromatic  1.308  0.020  1.308
 QEE  C14  C15   aromatic  1.406  0.020  1.406
 QEE  N13  N12   aromatic  1.348  0.020  1.348
 QEE  N17  N18   aromatic  1.284  0.020  1.284
 QEE  N17  N16   aromatic  1.331  0.020  1.331
 QEE  N18  C19   aromatic  1.351  0.020  1.351
 QEE  C15  N16   single    1.396  0.020  1.396
 QEE  C15  C21   aromatic  1.372  0.020  1.372
 QEE  N16  C20   aromatic  1.348  0.020  1.348
 QEE  N12  C21   aromatic  1.359  0.020  1.359
 QEE  N12  C11   single    1.409  0.020  1.409
 QEE  N10  C09   aromatic  1.322  0.020  1.322
 QEE  N10  C11   aromatic  1.320  0.020  1.320
 QEE  C19  C20   aromatic  1.367  0.020  1.367
 QEE  C21  O22   single    1.326  0.020  1.326
 QEE  C09  C08   aromatic  1.392  0.020  1.392
 QEE  C11  C23   aromatic  1.389  0.020  1.389
 QEE  C08  C02   single    1.489  0.020  1.489
 QEE  C08  C24   aromatic  1.391  0.020  1.391
 QEE  O01  C02   double    1.207  0.020  1.207
 QEE  C23  C24   aromatic  1.383  0.020  1.383
 QEE  C02  O03   single    1.315  0.020  1.315
 QEE  O03  C04   single    1.461  0.020  1.461
 QEE  C07  C04   single    1.523  0.020  1.523
 QEE  C05  C04   single    1.523  0.020  1.523
 QEE  C04  C06   single    1.523  0.020  1.523
 QEE  C20  H201  single    0.930  0.020  1.080
 QEE  C24  H241  single    0.930  0.020  1.080
 QEE  C05  H051  single    0.970  0.020  1.090
 QEE  C05  H053  single    0.970  0.020  1.090
 QEE  C05  H052  single    0.970  0.020  1.090
 QEE  C06  H061  single    0.970  0.020  1.090
 QEE  C06  H063  single    0.970  0.020  1.090
 QEE  C06  H062  single    0.970  0.020  1.090
 QEE  C07  H072  single    0.970  0.020  1.090
 QEE  C07  H073  single    0.970  0.020  1.090
 QEE  C07  H071  single    0.970  0.020  1.090
 QEE  C09  H091  single    0.930  0.020  1.080
 QEE  C14  H141  single    0.930  0.020  1.080
 QEE  C19  H191  single    0.930  0.020  1.080
 QEE  C23  H231  single    0.930  0.020  1.080
 QEE  O22  H221  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
 QEE  N13   N12  C11   119.89  3.000
 QEE  C11   N12  C21   128.23  3.000
 QEE  N13   N12  C21   111.87  3.000
 QEE  N16   C15  C14   128.31  3.000
 QEE  N16   C15  C21   126.37  3.000
 QEE  C14   C15  C21   105.31  3.000
 QEE  H201  C20  N16   123.07  3.000
 QEE  H201  C20  C19   133.11  3.000
 QEE  N16   C20  C19   103.82  3.000
 QEE  O22   C21  C15   127.71  3.000
 QEE  O22   C21  N12   126.32  3.000
 QEE  C15   C21  N12   105.93  3.000
 QEE  H241  C24  C23   119.30  3.000
 QEE  H241  C24  C08   121.31  3.000
 QEE  C23   C24  C08   119.39  3.000
 QEE  O03   C04  C07   110.85  3.000
 QEE  C07   C04  C06   110.03  3.000
 QEE  O03   C04  C06   102.96  3.000
 QEE  C06   C04  C05   110.07  3.000
 QEE  C07   C04  C05   112.09  3.000
 QEE  O03   C04  C05   110.47  3.000
 QEE  H052  C05  H053  108.86  3.000
 QEE  H052  C05  H051  107.65  3.000
 QEE  H053  C05  H051  107.60  3.000
 QEE  H052  C05  C04   112.66  3.000
 QEE  H053  C05  C04   111.11  3.000
 QEE  H051  C05  C04   108.79  3.000
 QEE  H062  C06  H063  108.55  3.000
 QEE  H062  C06  H061  107.85  3.000
 QEE  H063  C06  H061  107.89  3.000
 QEE  H062  C06  C04   111.42  3.000
 QEE  H063  C06  C04   111.44  3.000
 QEE  H061  C06  C04   109.55  3.000
 QEE  H071  C07  H073  108.79  3.000
 QEE  H071  C07  H072  107.51  3.000
 QEE  H073  C07  H072  107.72  3.000
 QEE  H071  C07  C04   111.14  3.000
 QEE  H073  C07  C04   112.77  3.000
 QEE  H072  C07  C04   108.72  3.000
 QEE  C09   C08  C02   118.86  3.000
 QEE  C02   C08  C24   123.50  3.000
 QEE  C09   C08  C24   117.63  3.000
 QEE  H091  C09  N10   116.21  3.000
 QEE  H091  C09  C08   120.33  3.000
 QEE  N10   C09  C08   123.46  3.000
 QEE  N10   C11  C23   123.91  3.000
 QEE  C23   C11  N12   120.38  3.000
 QEE  N10   C11  N12   115.71  3.000
 QEE  H141  C14  N13   121.01  3.000
 QEE  H141  C14  C15   127.84  3.000
 QEE  N13   C14  C15   111.14  3.000
 QEE  H191  C19  N18   122.52  3.000
 QEE  H191  C19  C20   129.26  3.000
 QEE  N18   C19  C20   108.21  3.000
 QEE  H231  C23  C11   122.01  3.000
 QEE  H231  C23  C24   120.37  3.000
 QEE  C11   C23  C24   117.60  3.000
 QEE  C11   N10  C09   117.98  3.000
 QEE  C14   N13  N12   105.72  3.000
 QEE  N17   N16  C20   110.89  3.000
 QEE  C20   N16  C15   128.50  3.000
 QEE  N17   N16  C15   120.60  3.000
 QEE  N18   N17  N16   107.70  3.000
 QEE  N17   N18  C19   109.38  3.000
 QEE  C04   O03  C02   123.95  3.000
 QEE  H221  O22  C21   112.95  3.000
 QEE  O03   C02  O01   126.29  3.000
 QEE  O03   C02  C08   111.33  3.000
 QEE  O01   C02  C08   122.37  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
 QEE  CONST_01  C15   C14  N13  N12     0.00   0.0  0
 QEE  CONST_02  C14   C15  C21  N12     0.00   0.0  0
 QEE  CONST_03  N16   C15  C21  N12   180.00   0.0  0
 QEE  CONST_04  C09   N10  C11  N12   180.00   0.0  0
 QEE  CONST_05  C24   C23  C11  N12   180.00   0.0  0
 QEE  CONST_06  N18   N17  N16  C15   180.00   0.0  0
 QEE  CONST_07  C19   C20  N16  C15   180.00   0.0  0
 QEE  CONST_08  N13   N12  C21  C15     0.00   0.0  0
 QEE  CONST_09  C11   N12  C21  C15   180.00   0.0  0
 QEE  CONST_10  N18   N17  N16  C20     0.00   0.0  0
 QEE  CONST_13  N17   N18  C19  C20     0.00   0.0  0
 QEE  CONST_14  N13   C14  C15  C21     0.00   0.0  0
 QEE  CONST_16  C14   N13  N12  C21     0.00   0.0  0
 QEE  CONST_19  N10   C09  C08  C24     0.00   0.0  0
 QEE  CONST_20  N10   C11  C23  C24     0.00   0.0  0
 QEE  CONST_21  C11   N10  C09  C08     0.00   0.0  0
 QEE  CONST_22  C11   C23  C24  C08     0.00   0.0  0
 QEE  CONST_23  C23   C11  N10  C09     0.00   0.0  0
 QEE  CONST_24  C23   C24  C08  C09     0.00   0.0  0
 QEE  CONST_25  C14   N13  N12  C11   180.00   0.0  0
 QEE  CONST_27  N16   N17  N18  C19     0.00   0.0  0
 QEE  CONST_28  N17   N16  C20  C19     0.00   0.0  0
 QEE  CONST_31  N16   C15  C14  N13   180.00   0.0  0
 QEE  CONST_32  N18   C19  C20  N16     0.00   0.0  0
 QEE  CONST_33  N10   C09  C08  C02   180.00   0.0  0
 QEE  CONST_34  C23   C24  C08  C02   180.00   0.0  0
 QEE  CONST_35  O22   C21  N12  C11     0.00   0.0  0
 QEE  CONST_36  O22   C21  C15  C14   180.00   0.0  0
 QEE  CONST_37  O22   C21  N12  N13   180.00   0.0  0
 QEE  CONST_38  O22   C21  C15  N16     0.00   0.0  0
 QEE  CONST_39  H141  C14  N13  N12   180.00   0.0  0
 QEE  CONST_40  H231  C23  C11  N12     0.00   0.0  0
 QEE  CONST_41  H201  C20  N16  C15     0.00   0.0  0
 QEE  CONST_42  H091  C09  C08  C24   180.00   0.0  0
 QEE  CONST_43  H241  C24  C08  C09   180.00   0.0  0
 QEE  CONST_44  H191  C19  C20  N16   180.00   0.0  0
 QEE  Var_01    O01   C02  C08  C24  -179.98  30.0  2
 QEE  Var_02    C08   C02  O03  C04   178.36  30.0  1
 QEE  Var_03    C07   C04  O03  C02    61.89  30.0  3
 QEE  Var_04    H072  C07  C04  C05   -66.06  30.0  3
 QEE  Var_05    H061  C06  C04  C05    61.90  30.0  3
 QEE  Var_06    H051  C05  C04  C06   -57.33  30.0  3

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
 QEE  plan-1  N12   0.020
 QEE  plan-1  C15   0.020
 QEE  plan-1  C21   0.020
 QEE  plan-1  C11   0.020
 QEE  plan-1  C14   0.020
 QEE  plan-1  N13   0.020
 QEE  plan-1  N16   0.020
 QEE  plan-1  O22   0.020
 QEE  plan-1  H141  0.020
 QEE  plan-2  C15   0.020
 QEE  plan-2  C20   0.020
 QEE  plan-2  C19   0.020
 QEE  plan-2  N16   0.020
 QEE  plan-2  N17   0.020
 QEE  plan-2  N18   0.020
 QEE  plan-2  H201  0.020
 QEE  plan-2  H191  0.020
 QEE  plan-3  N12   0.020
 QEE  plan-3  C24   0.020
 QEE  plan-3  C08   0.020
 QEE  plan-3  C09   0.020
 QEE  plan-3  C11   0.020
 QEE  plan-3  C23   0.020
 QEE  plan-3  N10   0.020
 QEE  plan-3  H241  0.020
 QEE  plan-3  H091  0.020
 QEE  plan-3  H231  0.020
 QEE  plan-3  C02   0.020
 QEE  plan-4  C08   0.020
 QEE  plan-4  O01   0.020
 QEE  plan-4  O03   0.020
 QEE  plan-4  C02   0.020

