# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May 10 20:17:08 2020
#   Inital geometry file: a 89 line input string
#   Ligand name: 2-methoxy-6,7-dimethyl-9-propylimidazo[1,5-a]pyrido[3,2-e]pyrazine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCc1nc(C)c2n1c3nc(OC)ccc3nc2C
#
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
 Z73  Z73  2-methoxy-6,7-dimethyl-9-propylimidazo[1,5-a]pyrido[3,2-e]pyrazine  ligand  38  20  .  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_Z73
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
 Z73  C1    C  CR6   0   0.161  -2.4509   1.3922   0.1476
 Z73  C2    C  CR56  0   0.294  -2.0639   0.0305  -0.0573
 Z73  N3    N  N     0  -0.449  -1.5793   2.3425   0.2286
 Z73  N4    N  N     0  -0.596  -0.7077  -0.2812  -0.1615
 Z73  C5    C  CR66  0   0.099  -0.2444   2.0245   0.1174
 Z73  C6    C  CR66  0   0.515   0.2411   0.7283  -0.0732
 Z73  C7    C  CR6   0   0.527   2.4075   1.3867  -0.0980
 Z73  N8    N  N     0  -0.496   1.5229   0.4189  -0.1747
 Z73  C9    C  CR16  0  -0.395   2.0573   2.7341   0.0870
 Z73  C10   C  CR16  0  -0.194   0.7240   3.0357   0.1949
 Z73  C11   C  CR5   0   0.452  -0.6110  -1.6210  -0.3647
 Z73  N12   N  N     0  -0.456  -1.8142  -2.1548  -0.3906
 Z73  C13   C  CR5   0   0.080  -2.7255  -1.1702  -0.2056
 Z73  C14   C  CH3   0  -0.754  -3.9003   1.7299   0.2762
 Z73  C15   C  CH3   0  -0.758  -4.1868  -1.4649  -0.1955
 Z73  C16   C  CH2   0  -0.504   0.6367  -2.4219  -0.4917
 Z73  C17   C  CH2   0  -0.433   1.2859  -2.7428   0.8574
 Z73  C18   C  CH3   0  -0.670   2.4918  -3.6574   0.6982
 Z73  O19   O  O2    0  -0.465   3.7031   1.1036  -0.1977
 Z73  C20   C  CH3   0  -0.423   4.0851  -0.2562  -0.3523
 Z73  H9    H  HCR6  0   0.281   2.8199   3.4979   0.1446
 Z73  H10   H  HCR6  0   0.281   0.3981   4.0572   0.3422
 Z73  H14   H  HCH3  0   0.257  -4.3475   1.2134   1.1268
 Z73  H14A  H  HCH3  0   0.266  -4.0217   2.8012   0.4173
 Z73  H14B  H  HCH3  0   0.257  -4.4564   1.4290  -0.6122
 Z73  H15   H  HCH3  0   0.250  -4.7124  -0.9620  -1.0085
 Z73  H15A  H  HCH3  0   0.260  -4.3408  -2.5360  -0.3137
 Z73  H15B  H  HCH3  0   0.249  -4.6626  -1.1588   0.7366
 Z73  H16   H  HCH2  0   0.253   0.3507  -3.3545  -0.9828
 Z73  H16A  H  HCH2  0   0.256   1.3570  -1.9227  -1.1390
 Z73  H17   H  HCH2  0   0.231   1.5870  -1.8137   1.3461
 Z73  H18   H  HCH3  0   0.224   2.2122  -4.6037   0.2320
 Z73  H18A  H  HCH3  0   0.218   3.2587  -3.1975   0.0723
 Z73  H20   H  HCH3  0   0.234   3.7797  -0.8566   0.5059
 Z73  H20A  H  HCH3  0   0.233   3.6635  -0.6951  -1.2574
 Z73  H20B  H  HCH3  0   0.254   5.1694  -0.2555  -0.4238
 Z73  H171  H  HCH2  0   0.229   0.5463  -3.2175   1.5073
 Z73  H181  H  HCH3  0   0.233   2.9449  -3.8847   1.6634

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
 Z73  C1   C2    aromatic  1.430  0.020  1.430
 Z73  C2   N4    aromatic  1.395  0.020  1.395
 Z73  C2   C13   aromatic  1.379  0.020  1.379
 Z73  N3   C1    aromatic  1.292  0.020  1.292
 Z73  N3   C5    aromatic  1.377  0.020  1.377
 Z73  N4   C11   aromatic  1.359  0.020  1.359
 Z73  C5   C6    aromatic  1.397  0.020  1.397
 Z73  C6   N4    aromatic  1.388  0.020  1.388
 Z73  C6   N8    aromatic  1.323  0.020  1.323
 Z73  C7   O19   single    1.330  0.020  1.330
 Z73  C7   N8    aromatic  1.313  0.020  1.313
 Z73  C9   C7    aromatic  1.404  0.020  1.404
 Z73  C9   H9    single    0.930  0.020  1.080
 Z73  C10  C5    aromatic  1.402  0.020  1.402
 Z73  C10  C9    aromatic  1.371  0.020  1.371
 Z73  C10  H10   single    0.930  0.020  1.080
 Z73  C11  N12   aromatic  1.317  0.020  1.317
 Z73  C11  C16   single    1.488  0.020  1.488
 Z73  C13  N12   aromatic  1.354  0.020  1.354
 Z73  C13  C15   single    1.491  0.020  1.491
 Z73  C14  C1    single    1.494  0.020  1.494
 Z73  C14  H14   single    0.970  0.020  1.090
 Z73  C14  H14A  single    0.970  0.020  1.090
 Z73  C14  H14B  single    0.970  0.020  1.090
 Z73  C15  H15   single    0.970  0.020  1.090
 Z73  C15  H15A  single    0.970  0.020  1.090
 Z73  C15  H15B  single    0.970  0.020  1.090
 Z73  C16  C17   single    1.531  0.020  1.531
 Z73  C16  H16   single    0.970  0.020  1.090
 Z73  C16  H16A  single    0.970  0.020  1.090
 Z73  C17  C18   single    1.522  0.020  1.522
 Z73  C17  H17   single    0.970  0.020  1.090
 Z73  C18  H18   single    0.970  0.020  1.090
 Z73  C18  H18A  single    0.970  0.020  1.090
 Z73  O19  C20   single    1.421  0.020  1.421
 Z73  C20  H20   single    0.970  0.020  1.090
 Z73  C20  H20A  single    0.970  0.020  1.090
 Z73  C20  H20B  single    0.970  0.020  1.090
 Z73  C17  H171  single    0.970  0.020  1.090
 Z73  C18  H181  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
 Z73  C14   C1   N3    118.87  3.000
 Z73  C14   C1   C2    119.35  3.000
 Z73  N3    C1   C2    121.78  3.000
 Z73  C13   C2   N4    105.29  3.000
 Z73  C13   C2   C1    135.61  3.000
 Z73  N4    C2   C1    119.10  3.000
 Z73  C5    N3   C1    118.63  3.000
 Z73  C11   N4   C6    132.69  3.000
 Z73  C6    N4   C2    119.80  3.000
 Z73  C11   N4   C2    107.49  3.000
 Z73  C10   C5   C6    115.89  3.000
 Z73  C10   C5   N3    119.90  3.000
 Z73  C6    C5   N3    124.21  3.000
 Z73  N8    C6   C5    124.35  3.000
 Z73  N8    C6   N4    119.17  3.000
 Z73  C5    C6   N4    116.48  3.000
 Z73  O19   C7   C9    117.20  3.000
 Z73  C9    C7   N8    123.14  3.000
 Z73  O19   C7   N8    119.67  3.000
 Z73  C7    N8   C6    118.42  3.000
 Z73  H9    C9   C10   121.76  3.000
 Z73  C10   C9   C7    117.64  3.000
 Z73  H9    C9   C7    120.60  3.000
 Z73  H10   C10  C9    120.74  3.000
 Z73  H10   C10  C5    118.70  3.000
 Z73  C9    C10  C5    120.56  3.000
 Z73  C16   C11  N12   123.12  3.000
 Z73  C16   C11  N4    127.10  3.000
 Z73  N12   C11  N4    109.74  3.000
 Z73  C13   N12  C11   108.51  3.000
 Z73  C15   C13  N12   121.12  3.000
 Z73  C15   C13  C2    129.92  3.000
 Z73  N12   C13  C2    108.96  3.000
 Z73  H14B  C14  H14A  108.70  3.000
 Z73  H14B  C14  H14   107.19  3.000
 Z73  H14A  C14  H14   108.63  3.000
 Z73  H14B  C14  C1    111.24  3.000
 Z73  H14A  C14  C1    110.02  3.000
 Z73  H14   C14  C1    110.97  3.000
 Z73  H15B  C15  H15A  107.90  3.000
 Z73  H15B  C15  H15   107.31  3.000
 Z73  H15A  C15  H15   107.73  3.000
 Z73  H15B  C15  C13   112.21  3.000
 Z73  H15A  C15  C13   109.41  3.000
 Z73  H15   C15  C13   112.09  3.000
 Z73  H16A  C16  H16   107.29  3.000
 Z73  H16A  C16  C17   109.83  3.000
 Z73  H16   C16  C17   109.16  3.000
 Z73  H16A  C16  C11   111.00  3.000
 Z73  H16   C16  C11   106.17  3.000
 Z73  C17   C16  C11   113.15  3.000
 Z73  H171  C17  H17   106.86  3.000
 Z73  H171  C17  C18   109.71  3.000
 Z73  H17   C17  C18   109.85  3.000
 Z73  H171  C17  C16   109.15  3.000
 Z73  H17   C17  C16   109.44  3.000
 Z73  C18   C17  C16   111.70  3.000
 Z73  H181  C18  H18A  107.67  3.000
 Z73  H181  C18  H18   107.69  3.000
 Z73  H18A  C18  H18   107.48  3.000
 Z73  H181  C18  C17   111.22  3.000
 Z73  H18A  C18  C17   111.31  3.000
 Z73  H18   C18  C17   111.27  3.000
 Z73  C20   O19  C7    118.28  3.000
 Z73  H20B  C20  H20A  109.35  3.000
 Z73  H20B  C20  H20   109.35  3.000
 Z73  H20A  C20  H20   108.85  3.000
 Z73  H20B  C20  O19   105.95  3.000
 Z73  H20A  C20  O19   111.80  3.000
 Z73  H20   C20  O19   111.46  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
 Z73  CONST_01  C11  N4   C2   C1   180.00   0.0  0
 Z73  CONST_02  C6   N4   C2   C1     0.00   0.0  0
 Z73  CONST_03  N12  C13  C2   C1   180.00   0.0  0
 Z73  CONST_04  C6   C5   N3   C1     0.00   0.0  0
 Z73  CONST_05  C10  C5   N3   C1   180.00   0.0  0
 Z73  CONST_06  C5   N3   C1   C2     0.00   0.0  0
 Z73  CONST_07  N12  C11  N4   C2     0.00   0.0  0
 Z73  CONST_08  C5   C6   N4   C2     0.00   0.0  0
 Z73  CONST_09  N8   C6   N4   C2   180.00   0.0  0
 Z73  CONST_10  C11  N12  C13  C2     0.00   0.0  0
 Z73  CONST_11  N4   C2   C1   N3     0.00   0.0  0
 Z73  CONST_12  C13  C2   C1   N3   180.00   0.0  0
 Z73  CONST_13  N4   C6   C5   N3     0.00   0.0  0
 Z73  CONST_14  N8   C6   C5   N3   180.00   0.0  0
 Z73  CONST_15  C9   C10  C5   N3   180.00   0.0  0
 Z73  CONST_16  N12  C13  C2   N4     0.00   0.0  0
 Z73  CONST_17  C13  N12  C11  N4     0.00   0.0  0
 Z73  CONST_18  C10  C5   C6   N4   180.00   0.0  0
 Z73  CONST_19  C7   N8   C6   N4   180.00   0.0  0
 Z73  CONST_20  C11  N4   C6   C5   180.00   0.0  0
 Z73  CONST_21  C7   N8   C6   C5     0.00   0.0  0
 Z73  CONST_22  C7   C9   C10  C5     0.00   0.0  0
 Z73  CONST_23  C9   C10  C5   C6     0.00   0.0  0
 Z73  CONST_24  C13  C2   N4   C6   180.00   0.0  0
 Z73  CONST_25  N12  C11  N4   C6   180.00   0.0  0
 Z73  CONST_26  C9   C7   N8   C6     0.00   0.0  0
 Z73  CONST_27  C10  C5   C6   N8     0.00   0.0  0
 Z73  CONST_28  C11  N4   C6   N8     0.00   0.0  0
 Z73  CONST_29  C10  C9   C7   N8     0.00   0.0  0
 Z73  CONST_30  C13  C2   N4   C11    0.00   0.0  0
 Z73  CONST_31  C15  C13  C2   C1     0.00   0.0  0
 Z73  CONST_32  C16  C11  N4   C2   180.00   0.0  0
 Z73  CONST_33  C14  C1   C2   N4   180.00   0.0  0
 Z73  CONST_34  C15  C13  C2   N4   180.00   0.0  0
 Z73  CONST_35  C14  C1   N3   C5   180.00   0.0  0
 Z73  CONST_36  C16  C11  N4   C6     0.00   0.0  0
 Z73  CONST_37  O19  C7   N8   C6   180.00   0.0  0
 Z73  CONST_38  O19  C7   C9   C10  180.00   0.0  0
 Z73  CONST_39  C15  C13  N12  C11  180.00   0.0  0
 Z73  CONST_40  C14  C1   C2   C13    0.00   0.0  0
 Z73  CONST_41  C16  C11  N12  C13  180.00   0.0  0
 Z73  CONST_42  H10  C10  C5   N3     0.00   0.0  0
 Z73  CONST_43  H9   C9   C10  C5   180.00   0.0  0
 Z73  Var_01    C17  C16  C11  N4    79.63  30.0  2
 Z73  Var_02    H14  C14  C1   C2    60.28  30.0  2
 Z73  Var_03    H15  C15  C13  C2    62.20  30.0  2
 Z73  Var_04    C18  C17  C16  C11  175.28  30.0  3
 Z73  Var_05    H20  C20  O19  C7   -61.76  30.0  3
 Z73  Var_06    H18  C18  C17  C16  -59.65  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
 Z73  plan-1  C1   0.020
 Z73  plan-1  C2   0.020
 Z73  plan-1  N3   0.020
 Z73  plan-1  N4   0.020
 Z73  plan-1  C5   0.020
 Z73  plan-1  C6   0.020
 Z73  plan-1  C7   0.020
 Z73  plan-1  N8   0.020
 Z73  plan-1  C9   0.020
 Z73  plan-1  C10  0.020
 Z73  plan-1  C11  0.020
 Z73  plan-1  N12  0.020
 Z73  plan-1  C13  0.020
 Z73  plan-1  C14  0.020
 Z73  plan-1  C15  0.020
 Z73  plan-1  C16  0.020
 Z73  plan-1  O19  0.020
 Z73  plan-1  H9   0.020
 Z73  plan-1  H10  0.020

