# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 10:45:17 2021
#   Inital geometry file: a 107 line input string
#   Ligand name: methyl 4-(cyclopropylmethyl)-1-prop-2-enoyl-2,3-dihydroquinoxaline-6-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)c1ccc2N(CCN(CC3CC3)c2c1)C(=O)C=C
#
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
 OWN  OWN  'methyl 4-(cyclopropylmethyl)-1-prop-2-enoyl-2,3-dihydroquinoxaline-6-carboxylate'  ligand  42  22  .  2022-07-22  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_OWN
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
 OWN  N1   N  NT    0  -0.555  -2.8117   -4.5630  -25.2793
 OWN  C2   C  CR6   0  -0.073   0.6199   -4.8084  -27.6379
 OWN  O2   O  O     0  -0.471  -4.9398   -3.9754  -24.8150
 OWN  C4   C  CR6   0   0.411  -0.8389   -5.7522  -25.9337
 OWN  C6   C  CH1   0  -0.266  -1.3475   -9.1529  -24.6288
 OWN  C7   C  CH2   0  -0.497  -0.7008  -10.4085  -24.1312
 OWN  C8   C  CH2   0  -0.476  -1.5478   -9.5872  -23.2093
 OWN  C    C  C     0   0.598   1.8459   -4.8650  -28.4737
 OWN  C1   C  CH3   0  -0.422   3.7856   -6.0931  -28.9923
 OWN  C10  C  CH2   0  -0.373  -2.5106   -4.9955  -23.9244
 OWN  C11  C  C     0   0.510  -4.0723   -4.1923  -25.6464
 OWN  C12  C  C1    0  -0.334  -4.3536   -4.1190  -27.1034
 OWN  C13  C  C2    0  -0.470  -5.4168   -3.4679  -27.5627
 OWN  C14  C  CR6   0   0.258  -1.6908   -4.6395  -26.1189
 OWN  C15  C  CR16  0  -0.273  -1.3614   -3.6288  -27.0079
 OWN  C16  C  CR16  0  -0.305  -0.2276   -3.7173  -27.7961
 OWN  C3   C  CR16  0  -0.411   0.3304   -5.7979  -26.7018
 OWN  C9   C  CH2   0  -0.245  -2.1231   -6.4586  -23.9641
 OWN  N    N  NT    0  -0.539  -1.1903   -6.7322  -25.0441
 OWN  O    O  O     0  -0.451   2.1427   -4.0221  -29.2872
 OWN  O1   O  O2    0  -0.457   2.5837   -5.9385  -28.2387
 OWN  H1   H  HCH2  0   0.255  -0.0075   -8.1811  -25.9385
 OWN  H2   H  HCH2  0   0.224   0.3592   -7.9208  -24.2372
 OWN  H3   H  HCH1  0   0.263  -2.1910   -9.2798  -25.2998
 OWN  H4   H  HCH2  0   0.254  -1.0871  -11.3556  -24.4840
 OWN  H5   H  HCH2  0   0.245   0.3722  -10.3979  -23.9783
 OWN  H6   H  HCH2  0   0.244  -1.0444   -9.0255  -22.4311
 OWN  H7   H  HCH2  0   0.252  -2.5200   -9.9676  -22.9242
 OWN  H8   H  HCH3  0   0.253   4.2440   -7.0106  -28.6360
 OWN  H9   H  HCH3  0   0.240   3.5766   -6.1837  -30.0580
 OWN  H10  H  HCH3  0   0.240   4.4686   -5.2600  -28.8291
 OWN  H11  H  HCH2  0   0.266  -1.6985   -4.3830  -23.5276
 OWN  H12  H  HCH2  0   0.288  -3.3766   -4.8587  -23.2841
 OWN  H13  H  H     0   0.288  -3.6937   -4.6357  -27.7882
 OWN  H15  H  H     0   0.262  -5.6400   -3.4446  -28.6202
 OWN  H16  H  H     0   0.261  -6.0918   -2.9338  -26.9068
 OWN  H18  H  HCR6  0   0.276  -2.0057   -2.7627  -27.0853
 OWN  H19  H  HCR6  0   0.258   0.0022   -2.9332  -28.5031
 OWN  H20  H  HCR6  0   0.277   1.0264   -6.6115  -26.5663
 OWN  H21  H  HCH2  0   0.242  -3.0209   -7.0733  -24.0698
 OWN  H22  H  HCH2  0   0.243  -1.6674   -6.7240  -23.0048
 OWN  C5   C  CH2   0  -0.288  -0.4607   -7.9821  -24.9673

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
 OWN  C1   O1   single    1.427  0.020  1.427
 OWN  O    C    double    1.208  0.020  1.208
 OWN  O1   C    single    1.324  0.020  1.324
 OWN  C    C2   single    1.485  0.020  1.485
 OWN  C13  C12  double    1.329  0.020  1.329
 OWN  C16  C2   aromatic  1.391  0.020  1.391
 OWN  C16  C15  aromatic  1.384  0.020  1.384
 OWN  C2   C3   aromatic  1.393  0.020  1.393
 OWN  C12  C11  single    1.486  0.020  1.486
 OWN  C15  C14  aromatic  1.386  0.020  1.386
 OWN  C3   C4   aromatic  1.400  0.020  1.400
 OWN  C14  C4   aromatic  1.414  0.020  1.414
 OWN  C14  N1   single    1.403  0.020  1.403
 OWN  C4   N    single    1.369  0.020  1.369
 OWN  C11  N1   single    1.364  0.020  1.364
 OWN  C11  O2   double    1.221  0.020  1.221
 OWN  N1   C10  single    1.454  0.020  1.454
 OWN  N    C5   single    1.449  0.020  1.449
 OWN  N    C9   single    1.453  0.020  1.453
 OWN  C5   C6   single    1.507  0.020  1.507
 OWN  C9   C10  single    1.514  0.020  1.514
 OWN  C6   C7   single    1.497  0.020  1.497
 OWN  C6   C8   single    1.498  0.020  1.498
 OWN  C7   C8   single    1.497  0.020  1.497
 OWN  C5   H1   single    0.970  0.020  1.090
 OWN  C5   H2   single    0.970  0.020  1.090
 OWN  C6   H3   single    0.970  0.020  1.090
 OWN  C7   H4   single    0.970  0.020  1.090
 OWN  C7   H5   single    0.970  0.020  1.090
 OWN  C8   H6   single    0.970  0.020  1.090
 OWN  C8   H7   single    0.970  0.020  1.090
 OWN  C1   H8   single    0.970  0.020  1.090
 OWN  C1   H9   single    0.970  0.020  1.090
 OWN  C1   H10  single    0.970  0.020  1.090
 OWN  C10  H11  single    0.970  0.020  1.090
 OWN  C10  H12  single    0.970  0.020  1.090
 OWN  C12  H13  single    0.930  0.020  1.080
 OWN  C13  H15  single    0.930  0.020  1.080
 OWN  C13  H16  single    0.930  0.020  1.080
 OWN  C15  H18  single    0.930  0.020  1.080
 OWN  C16  H19  single    0.930  0.020  1.080
 OWN  C3   H20  single    0.930  0.020  1.080
 OWN  C9   H21  single    0.970  0.020  1.090
 OWN  C9   H22  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
 OWN  C14  N1   C11  126.31  3.000
 OWN  C11  N1   C10  121.53  3.000
 OWN  C14  N1   C10  112.10  3.000
 OWN  C3   C2   C16  120.48  3.000
 OWN  C3   C2   C    121.53  3.000
 OWN  C16  C2   C    117.98  3.000
 OWN  N    C4   C3   123.19  3.000
 OWN  N    C4   C14  119.59  3.000
 OWN  C3   C4   C14  117.21  3.000
 OWN  H3   C6   C8   116.62  3.000
 OWN  H3   C6   C7   116.30  3.000
 OWN  C8   C6   C7    59.98  3.000
 OWN  H3   C6   C5   114.16  3.000
 OWN  C8   C6   C5   121.12  3.000
 OWN  C7   C6   C5   118.15  3.000
 OWN  H5   C7   H4   114.08  3.000
 OWN  H5   C7   C8   117.90  3.000
 OWN  H4   C7   C8   118.61  3.000
 OWN  H5   C7   C6   117.79  3.000
 OWN  H4   C7   C6   118.12  3.000
 OWN  C8   C7   C6    60.02  3.000
 OWN  H7   C8   H6   114.22  3.000
 OWN  H7   C8   C7   118.53  3.000
 OWN  H6   C8   C7   117.62  3.000
 OWN  H7   C8   C6   118.15  3.000
 OWN  H6   C8   C6   117.91  3.000
 OWN  C7   C8   C6    60.00  3.000
 OWN  O1   C    O    123.25  3.000
 OWN  O1   C    C2   113.03  3.000
 OWN  O    C    C2   123.72  3.000
 OWN  H10  C1   H9   109.29  3.000
 OWN  H10  C1   H8   109.41  3.000
 OWN  H9   C1   H8   109.37  3.000
 OWN  H10  C1   O1   111.47  3.000
 OWN  H9   C1   O1   111.34  3.000
 OWN  H8   C1   O1   105.89  3.000
 OWN  H12  C10  H11  107.95  3.000
 OWN  H12  C10  C9   109.96  3.000
 OWN  H11  C10  C9   111.18  3.000
 OWN  H12  C10  N1   110.30  3.000
 OWN  H11  C10  N1   109.02  3.000
 OWN  C9   C10  N1   108.43  3.000
 OWN  C12  C11  O2   121.63  3.000
 OWN  O2   C11  N1   121.43  3.000
 OWN  C12  C11  N1   116.89  3.000
 OWN  H13  C12  C13  120.21  3.000
 OWN  H13  C12  C11  118.78  3.000
 OWN  C13  C12  C11  120.98  3.000
 OWN  H16  C13  H15  116.97  3.000
 OWN  H16  C13  C12  122.11  3.000
 OWN  H15  C13  C12  120.93  3.000
 OWN  C15  C14  C4   120.99  3.000
 OWN  C4   C14  N1   116.50  3.000
 OWN  C15  C14  N1   122.29  3.000
 OWN  H18  C15  C16  119.89  3.000
 OWN  H18  C15  C14  119.21  3.000
 OWN  C16  C15  C14  120.90  3.000
 OWN  H19  C16  C15  120.04  3.000
 OWN  H19  C16  C2   120.94  3.000
 OWN  C15  C16  C2   119.00  3.000
 OWN  H20  C3   C4   119.64  3.000
 OWN  H20  C3   C2   119.08  3.000
 OWN  C4   C3   C2   121.28  3.000
 OWN  H22  C9   H21  106.88  3.000
 OWN  H22  C9   N    109.78  3.000
 OWN  H21  C9   N    110.46  3.000
 OWN  H22  C9   C10  108.53  3.000
 OWN  H21  C9   C10  109.61  3.000
 OWN  N    C9   C10  111.45  3.000
 OWN  C9   N    C5   116.50  3.000
 OWN  C9   N    C4   120.85  3.000
 OWN  C5   N    C4   121.50  3.000
 OWN  C1   O1   C    117.62  3.000
 OWN  H2   C5   H1   106.96  3.000
 OWN  H2   C5   N    111.25  3.000
 OWN  H1   C5   N    108.63  3.000
 OWN  H2   C5   C6   109.45  3.000
 OWN  H1   C5   C6   107.63  3.000
 OWN  N    C5   C6   112.68  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
 OWN  CONST_01  C14  C15  C16  C2      0.00   0.0  0
 OWN  CONST_02  C14  C4   C3   C2      0.00   0.0  0
 OWN  CONST_03  C16  C2   C3   C4      0.00   0.0  0
 OWN  CONST_04  C16  C15  C14  C4      0.00   0.0  0
 OWN  CONST_05  C3   C2   C16  C15     0.00   0.0  0
 OWN  CONST_06  C3   C4   C14  C15     0.00   0.0  0
 OWN  CONST_07  C    C2   C3   C4    180.00   0.0  0
 OWN  CONST_08  C15  C16  C2   C     180.00   0.0  0
 OWN  CONST_09  H18  C15  C14  N1      0.00   0.0  0
 OWN  CONST_10  H19  C16  C15  C14   180.00   0.0  0
 OWN  CONST_11  H20  C3   C4   C14   180.00   0.0  0
 OWN  CONST_12  C14  N1   C11  O2    180.00   0.0  0
 OWN  CONST_13  C10  N1   C11  O2      0.00   0.0  0
 OWN  CONST_15  C14  N1   C11  C12     0.00   0.0  0
 OWN  Var_01    N    C9   C10  N1     45.46  30.0  1
 OWN  Var_02    C10  N1   C14  C4     38.50  30.0  1
 OWN  Var_03    C10  C9   N    C4     -4.63  30.0  1
 OWN  Var_04    C9   N    C4   C14   -22.25  30.0  1
 OWN  Var_05    C9   C10  N1   C14   -63.53  30.0  1
 OWN  Var_06    C6   C5   N    C4   -145.88  30.0  3
 OWN  Var_07    C8   C7   C6   C5    111.57  30.0  1
 OWN  Var_08    N    C5   C6   C7   -162.59  30.0  2
 OWN  Var_09    H6   C8   C7   C6   -107.94  30.0  1
 OWN  Var_10    O    C    C2   C16    -0.47  30.0  3
 OWN  Var_11    C13  C12  C11  N1   -163.40  30.0  1
 OWN  Var_12    H15  C13  C12  C11  -177.82   0.0  2
 OWN  Var_13    H8   C1   O1   C     178.78  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
 OWN  chir_01  C6  C5  C7  C8  both

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
 OWN  plan-1  N1   0.020
 OWN  plan-1  O2   0.020
 OWN  plan-1  C10  0.020
 OWN  plan-1  C11  0.020
 OWN  plan-1  C12  0.020
 OWN  plan-1  C14  0.020
 OWN  plan-2  N1   0.020
 OWN  plan-2  C2   0.020
 OWN  plan-2  C4   0.020
 OWN  plan-2  C    0.020
 OWN  plan-2  C14  0.020
 OWN  plan-2  C15  0.020
 OWN  plan-2  C16  0.020
 OWN  plan-2  C3   0.020
 OWN  plan-2  N    0.020
 OWN  plan-2  H18  0.020
 OWN  plan-2  H19  0.020
 OWN  plan-2  H20  0.020
 OWN  plan-3  C2   0.020
 OWN  plan-3  C    0.020
 OWN  plan-3  O    0.020
 OWN  plan-3  O1   0.020
 OWN  plan-4  C11  0.020
 OWN  plan-4  C12  0.020
 OWN  plan-4  C13  0.020
 OWN  plan-4  H13  0.020
 OWN  plan-4  H15  0.020
 OWN  plan-4  H16  0.020

