# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 09:58:10 2021
#   Inital geometry file: a 131 line input string
#   Ligand name: ~{N}-(oxan-4-ylmethyl)-6-(5-propan-2-yloxypyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)Oc1cncc(c1)c2ccc3cnc(n3c2)C(=O)NCC4CCOCC4
#
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
 OHK  OHK  ~{N}-(oxan-4-ylmethyl)-6-(5-propan-2-yloxypyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxamide  ligand  55  29  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OHK
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
 OHK  C1   C  CH1   0  -0.260  23.2992   7.8624   4.2255
 OHK  C2   C  CH2   0  -0.446  22.0842   8.0209   3.3142
 OHK  C3   C  CH2   0  -0.180  22.4848   8.6784   2.0027
 OHK  C5   C  CH2   0  -0.177  24.2899   9.7958   2.9895
 OHK  C6   C  CH2   0  -0.442  23.9978   9.2124   4.3627
 OHK  C7   C  CH2   0  -0.268  22.8896   7.2688   5.5714
 OHK  C12  C  CR16  0  -0.024  25.4572   9.0497  10.1544
 OHK  C15  C  CR16  0  -0.370  27.9405   7.9312  10.7634
 OHK  C16  C  CR56  0   0.359  27.2265   7.5064   9.6251
 OHK  C17  C  CR15  0  -0.222  27.4371   6.5831   8.6124
 OHK  C19  C  CR6   0   0.016  25.5494  10.4921  12.1332
 OHK  C23  C  CR6   0   0.338  23.6837  11.4761  13.2754
 OHK  C24  C  CR16  0  -0.344  24.1912  10.4832  12.4476
 OHK  O25  O  O2    0  -0.476  22.4165  11.5810  13.6935
 OHK  C27  C  CH3   0  -0.678  20.9655  11.1351  11.7981
 OHK  O29  O  O     0  -0.493  23.5264   8.7094   7.9537
 OHK  O4   O  O2    0  -0.485  23.1226   9.9210   2.2058
 OHK  N8   N  NH1   0  -0.647  24.0097   7.0653   6.4591
 OHK  C9   C  C     0   0.525  24.2649   7.8221   7.5361
 OHK  C10  C  CR5   0   0.325  25.5362   7.4926   8.2006
 OHK  N11  N  N     0  -0.574  25.9959   8.0821   9.3466
 OHK  C13  C  CR6   0  -0.044  26.1342   9.4603  11.2592
 OHK  C14  C  CR16  0  -0.185  27.4084   8.8893  11.5646
 OHK  N18  N  N     0  -0.431  26.4005   6.5958   7.7658
 OHK  C20  C  CR16  0  -0.129  26.3429  11.5016  12.6664
 OHK  N21  N  N     0  -0.379  25.8598  12.4528  13.4558
 OHK  C22  C  CR16  0  -0.155  24.5744  12.4450  13.7530
 OHK  C26  C  CH1   0  -0.010  21.4028  10.7016  13.1865
 OHK  C28  C  CH3   0  -0.663  20.2650  10.7487  14.1855
 OHK  H1   H  HCH1  0   0.226  23.9961   7.1649   3.7406
 OHK  H2   H  HCH2  0   0.223  21.3252   8.6324   3.8142
 OHK  H3   H  HCH2  0   0.237  21.6273   7.0504   3.1021
 OHK  H4   H  HCH2  0   0.234  21.6086   8.8682   1.3803
 OHK  H5   H  HCH2  0   0.194  23.1464   7.9987   1.4443
 OHK  H6   H  HCH2  0   0.193  25.0267   9.1587   2.4763
 OHK  H7   H  HCH2  0   0.234  24.7231  10.7941   3.0753
 OHK  H8   H  HCH2  0   0.234  24.9396   9.1149   4.9084
 OHK  H9   H  HCH2  0   0.221  23.3644   9.9005   4.9329
 OHK  H10  H  HCH2  0   0.242  22.1745   7.9255   6.0669
 OHK  H11  H  HCH2  0   0.251  22.3911   6.3093   5.4117
 OHK  H12  H  HCR6  0   0.316  24.5080   9.4582   9.8498
 OHK  H13  H  HCR6  0   0.283  28.8971   7.4777  10.9816
 OHK  H14  H  HCR5  0   0.271  28.2903   5.9356   8.4847
 OHK  H15  H  HCR6  0   0.288  23.5668   9.6868  12.0643
 OHK  H16  H  HCH3  0   0.239  21.7813  11.1171  11.0751
 OHK  H17  H  HCH3  0   0.242  20.1890  10.4640  11.4309
 OHK  H18  H  HCH3  0   0.236  20.5544  12.1455  11.8220
 OHK  H19  H  HNH1  0   0.402  24.7030   6.3794   6.2002
 OHK  H20  H  HCR6  0   0.274  27.9366   9.2102  12.4519
 OHK  H21  H  HCR6  0   0.261  27.4004  11.5549  12.4322
 OHK  H22  H  HCR6  0   0.269  24.2070  13.2308  14.4057
 OHK  H23  H  HCH1  0   0.236  21.7933   9.6788  13.1533
 OHK  H24  H  HCH3  0   0.243  20.5909  10.4252  15.1740
 OHK  H25  H  HCH3  0   0.232  19.8514  11.7552  14.2660
 OHK  H26  H  HCH3  0   0.237  19.4648  10.0834  13.8622

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
 OHK  O4   C5   single    1.412  0.020  1.412
 OHK  O4   C3   single    1.411  0.020  1.411
 OHK  C5   C6   single    1.520  0.020  1.520
 OHK  C3   C2   single    1.521  0.020  1.521
 OHK  C2   C1   single    1.527  0.020  1.527
 OHK  C6   C1   single    1.526  0.020  1.526
 OHK  C1   C7   single    1.527  0.020  1.527
 OHK  C7   N8   single    1.444  0.020  1.444
 OHK  N8   C9   single    1.341  0.020  1.341
 OHK  C9   O29  double    1.228  0.020  1.228
 OHK  C9   C10  single    1.472  0.020  1.472
 OHK  N18  C10  aromatic  1.319  0.020  1.319
 OHK  N18  C17  aromatic  1.338  0.020  1.338
 OHK  C10  N11  aromatic  1.368  0.020  1.368
 OHK  C17  C16  aromatic  1.386  0.020  1.386
 OHK  N11  C16  aromatic  1.387  0.020  1.387
 OHK  N11  C12  aromatic  1.371  0.020  1.371
 OHK  C16  C15  aromatic  1.409  0.020  1.409
 OHK  C12  C13  aromatic  1.359  0.020  1.359
 OHK  C15  C14  aromatic  1.357  0.020  1.357
 OHK  C27  C26  single    1.519  0.020  1.519
 OHK  C13  C14  aromatic  1.429  0.020  1.429
 OHK  C13  C19  single    1.473  0.020  1.473
 OHK  C26  C28  single    1.515  0.020  1.515
 OHK  C26  O25  single    1.434  0.020  1.434
 OHK  C24  C19  aromatic  1.394  0.020  1.394
 OHK  C24  C23  aromatic  1.389  0.020  1.389
 OHK  C19  C20  aromatic  1.390  0.020  1.390
 OHK  O25  C23  single    1.338  0.020  1.338
 OHK  C23  C22  aromatic  1.400  0.020  1.400
 OHK  C20  N21  aromatic  1.327  0.020  1.327
 OHK  C22  N21  aromatic  1.319  0.020  1.319
 OHK  C1   H1   single    0.970  0.020  1.090
 OHK  C2   H2   single    0.970  0.020  1.090
 OHK  C2   H3   single    0.970  0.020  1.090
 OHK  C3   H4   single    0.970  0.020  1.090
 OHK  C3   H5   single    0.970  0.020  1.090
 OHK  C5   H6   single    0.970  0.020  1.090
 OHK  C5   H7   single    0.970  0.020  1.090
 OHK  C6   H8   single    0.970  0.020  1.090
 OHK  C6   H9   single    0.970  0.020  1.090
 OHK  C7   H10  single    0.970  0.020  1.090
 OHK  C7   H11  single    0.970  0.020  1.090
 OHK  C12  H12  single    0.930  0.020  1.080
 OHK  C15  H13  single    0.930  0.020  1.080
 OHK  C17  H14  single    0.930  0.020  1.080
 OHK  C24  H15  single    0.930  0.020  1.080
 OHK  C27  H16  single    0.970  0.020  1.090
 OHK  C27  H17  single    0.970  0.020  1.090
 OHK  C27  H18  single    0.970  0.020  1.090
 OHK  N8   H19  single    0.860  0.020  1.020
 OHK  C14  H20  single    0.930  0.020  1.080
 OHK  C20  H21  single    0.930  0.020  1.080
 OHK  C22  H22  single    0.930  0.020  1.080
 OHK  C26  H23  single    0.970  0.020  1.090
 OHK  C28  H24  single    0.970  0.020  1.090
 OHK  C28  H25  single    0.970  0.020  1.090
 OHK  C28  H26  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
 OHK  H1   C1   C7   108.20  3.000
 OHK  H1   C1   C6   108.11  3.000
 OHK  C7   C1   C6   112.80  3.000
 OHK  H1   C1   C2   107.89  3.000
 OHK  C7   C1   C2   110.66  3.000
 OHK  C6   C1   C2   109.03  3.000
 OHK  H3   C2   H2   107.13  3.000
 OHK  H3   C2   C3   109.06  3.000
 OHK  H2   C2   C3   109.56  3.000
 OHK  H3   C2   C1   110.86  3.000
 OHK  H2   C2   C1   109.68  3.000
 OHK  C3   C2   C1   110.48  3.000
 OHK  H5   C3   H4   107.50  3.000
 OHK  H5   C3   O4   110.19  3.000
 OHK  H4   C3   O4   106.96  3.000
 OHK  H5   C3   C2   109.20  3.000
 OHK  H4   C3   C2   110.82  3.000
 OHK  O4   C3   C2   112.06  3.000
 OHK  H7   C5   H6   107.47  3.000
 OHK  H7   C5   O4   106.90  3.000
 OHK  H6   C5   O4   110.24  3.000
 OHK  H7   C5   C6   110.86  3.000
 OHK  H6   C5   C6   109.12  3.000
 OHK  O4   C5   C6   112.13  3.000
 OHK  H9   C6   H8   107.12  3.000
 OHK  H9   C6   C5   109.89  3.000
 OHK  H8   C6   C5   108.65  3.000
 OHK  H9   C6   C1   109.74  3.000
 OHK  H8   C6   C1   111.13  3.000
 OHK  C5   C6   C1   110.25  3.000
 OHK  H11  C7   H10  107.22  3.000
 OHK  H11  C7   N8   108.66  3.000
 OHK  H10  C7   N8   108.33  3.000
 OHK  H11  C7   C1   109.56  3.000
 OHK  H10  C7   C1   110.03  3.000
 OHK  N8   C7   C1   112.87  3.000
 OHK  H12  C12  C13  123.65  3.000
 OHK  H12  C12  N11  116.57  3.000
 OHK  C13  C12  N11  119.77  3.000
 OHK  H13  C15  C14  121.59  3.000
 OHK  H13  C15  C16  119.01  3.000
 OHK  C14  C15  C16  119.40  3.000
 OHK  N11  C16  C17  105.34  3.000
 OHK  N11  C16  C15  119.12  3.000
 OHK  C17  C16  C15  135.55  3.000
 OHK  H14  C17  N18  122.92  3.000
 OHK  H14  C17  C16  127.32  3.000
 OHK  N18  C17  C16  109.76  3.000
 OHK  C20  C19  C13  120.63  3.000
 OHK  C20  C19  C24  118.30  3.000
 OHK  C13  C19  C24  121.06  3.000
 OHK  C22  C23  O25  116.20  3.000
 OHK  C22  C23  C24  117.75  3.000
 OHK  O25  C23  C24  126.03  3.000
 OHK  H15  C24  C23  121.76  3.000
 OHK  H15  C24  C19  119.14  3.000
 OHK  C23  C24  C19  119.07  3.000
 OHK  C26  O25  C23  120.70  3.000
 OHK  H18  C27  H17  108.01  3.000
 OHK  H18  C27  H16  108.17  3.000
 OHK  H17  C27  H16  107.43  3.000
 OHK  H18  C27  C26  110.66  3.000
 OHK  H17  C27  C26  109.72  3.000
 OHK  H16  C27  C26  112.71  3.000
 OHK  C5   O4   C3   112.05  3.000
 OHK  H19  N8   C9   117.32  3.000
 OHK  H19  N8   C7   118.11  3.000
 OHK  C9   N8   C7   124.19  3.000
 OHK  C10  C9   N8   113.62  3.000
 OHK  C10  C9   O29  121.86  3.000
 OHK  N8   C9   O29  124.52  3.000
 OHK  N18  C10  N11  110.41  3.000
 OHK  N11  C10  C9   124.88  3.000
 OHK  N18  C10  C9   124.70  3.000
 OHK  C10  N11  C16  106.71  3.000
 OHK  C16  N11  C12  121.56  3.000
 OHK  C10  N11  C12  131.73  3.000
 OHK  C14  C13  C19  120.46  3.000
 OHK  C19  C13  C12  119.74  3.000
 OHK  C14  C13  C12  119.80  3.000
 OHK  H20  C14  C13  119.48  3.000
 OHK  H20  C14  C15  120.15  3.000
 OHK  C13  C14  C15  120.35  3.000
 OHK  C10  N18  C17  107.78  3.000
 OHK  H21  C20  N21  116.63  3.000
 OHK  H21  C20  C19  120.62  3.000
 OHK  N21  C20  C19  122.74  3.000
 OHK  C22  N21  C20  118.97  3.000
 OHK  H22  C22  N21  117.44  3.000
 OHK  H22  C22  C23  119.39  3.000
 OHK  N21  C22  C23  123.17  3.000
 OHK  H23  C26  C28  108.47  3.000
 OHK  H23  C26  C27  109.97  3.000
 OHK  C28  C26  C27  112.19  3.000
 OHK  H23  C26  O25  109.34  3.000
 OHK  C28  C26  O25  106.18  3.000
 OHK  C27  C26  O25  110.58  3.000
 OHK  H26  C28  H25  107.86  3.000
 OHK  H26  C28  H24  107.90  3.000
 OHK  H25  C28  H24  108.68  3.000
 OHK  H26  C28  C26  109.69  3.000
 OHK  H25  C28  C26  111.22  3.000
 OHK  H24  C28  C26  111.36  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
 OHK  CONST_01  N18  C10  N11  C12   180.00   0.0  0
 OHK  CONST_02  C17  C16  N11  C12   180.00   0.0  0
 OHK  CONST_03  C15  C16  N11  C12     0.00   0.0  0
 OHK  CONST_04  C15  C14  C13  C12     0.00   0.0  0
 OHK  CONST_07  N18  C17  C16  C15   180.00   0.0  0
 OHK  CONST_08  C10  N11  C16  C15   180.00   0.0  0
 OHK  CONST_09  C19  C13  C14  C15   180.00   0.0  0
 OHK  CONST_10  C10  N18  C17  C16     0.00   0.0  0
 OHK  CONST_11  N18  C10  N11  C16     0.00   0.0  0
 OHK  CONST_12  C13  C12  N11  C16     0.00   0.0  0
 OHK  CONST_13  C13  C14  C15  C16     0.00   0.0  0
 OHK  CONST_14  N11  C10  N18  C17     0.00   0.0  0
 OHK  CONST_15  C10  N11  C16  C17     0.00   0.0  0
 OHK  CONST_16  C14  C15  C16  C17   180.00   0.0  0
 OHK  CONST_17  N11  C12  C13  C19   180.00   0.0  0
 OHK  CONST_18  C22  C23  C24  C19     0.00   0.0  0
 OHK  CONST_19  C22  N21  C20  C19     0.00   0.0  0
 OHK  CONST_20  C13  C19  C24  C23   180.00   0.0  0
 OHK  CONST_21  C20  C19  C24  C23     0.00   0.0  0
 OHK  CONST_22  C20  N21  C22  C23     0.00   0.0  0
 OHK  CONST_24  N21  C20  C19  C24     0.00   0.0  0
 OHK  CONST_25  N21  C22  C23  C24     0.00   0.0  0
 OHK  CONST_26  C13  C12  N11  C10   180.00   0.0  0
 OHK  CONST_27  N18  C17  C16  N11     0.00   0.0  0
 OHK  CONST_28  C14  C15  C16  N11     0.00   0.0  0
 OHK  CONST_29  C14  C13  C12  N11     0.00   0.0  0
 OHK  CONST_30  N21  C20  C19  C13   180.00   0.0  0
 OHK  CONST_32  C9   C10  N11  C12     0.00   0.0  0
 OHK  CONST_33  C9   C10  N11  C16   180.00   0.0  0
 OHK  CONST_34  C9   C10  N18  C17   180.00   0.0  0
 OHK  CONST_35  O25  C23  C24  C19   180.00   0.0  0
 OHK  CONST_36  N21  C22  C23  O25   180.00   0.0  0
 OHK  CONST_37  H20  C14  C13  C12   180.00   0.0  0
 OHK  CONST_38  H14  C17  C16  C15     0.00   0.0  0
 OHK  CONST_39  H12  C12  N11  C16   180.00   0.0  0
 OHK  CONST_40  H13  C15  C16  C17     0.00   0.0  0
 OHK  CONST_41  H21  C20  C19  C24   180.00   0.0  0
 OHK  CONST_42  H22  C22  C23  C24   180.00   0.0  0
 OHK  CONST_43  H15  C24  C19  C13     0.00   0.0  0
 OHK  CONST_44  C10  C9   N8   C7    180.00   0.0  0
 OHK  CONST_45  H19  N8   C9   C10     0.00   0.0  0
 OHK  CONST_46  O29  C9   N8   C7      0.00   0.0  0
 OHK  Var_01    O4   C3   C2   C1    -56.01  30.0  1
 OHK  Var_02    O4   C5   C6   C1     56.44  30.0  1
 OHK  Var_03    C6   C5   O4   C3    -59.47  30.0  1
 OHK  Var_04    N18  C10  C9   O29  -176.66  30.0  2
 OHK  Var_05    C9   N8   C7   C1    106.70  30.0  3
 OHK  Var_06    C27  C26  O25  C23   -77.80  30.0  2
 OHK  Var_07    H16  C27  C26  O25    60.90  30.0  3
 OHK  Var_08    H24  C28  C26  O25   -59.69  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
 OHK  chir_01  C1  C2  C6  C7  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
 OHK  plan-1  C19  0.020
 OHK  plan-1  C23  0.020
 OHK  plan-1  C24  0.020
 OHK  plan-1  O25  0.020
 OHK  plan-1  C13  0.020
 OHK  plan-1  C20  0.020
 OHK  plan-1  N21  0.020
 OHK  plan-1  C22  0.020
 OHK  plan-1  H15  0.020
 OHK  plan-1  H21  0.020
 OHK  plan-1  H22  0.020
 OHK  plan-2  C12  0.020
 OHK  plan-2  C15  0.020
 OHK  plan-2  C16  0.020
 OHK  plan-2  C17  0.020
 OHK  plan-2  C19  0.020
 OHK  plan-2  C9   0.020
 OHK  plan-2  C10  0.020
 OHK  plan-2  N11  0.020
 OHK  plan-2  C13  0.020
 OHK  plan-2  C14  0.020
 OHK  plan-2  N18  0.020
 OHK  plan-2  H12  0.020
 OHK  plan-2  H13  0.020
 OHK  plan-2  H14  0.020
 OHK  plan-2  H20  0.020
 OHK  plan-3  C7   0.020
 OHK  plan-3  O29  0.020
 OHK  plan-3  N8   0.020
 OHK  plan-3  C9   0.020
 OHK  plan-3  C10  0.020
 OHK  plan-3  H19  0.020

