# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 10:14:19 2020
#   Inital geometry file: a 67 line input string
#   Ligand name: 5,6-dihydrobenzo[h]cinnolin-3-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1cc2CCc3ccccc3c2nn1
#
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
 DRG  DRG  5,6-dihydrobenzo[h]cinnolin-3-amine  ligand  26  15  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_DRG
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
 DRG  C4    C  CR16  0  -0.354  -0.9384  -0.1250   2.3925
 DRG  C14   C  CR66  0   0.121  -0.9369  -0.1559   1.0282
 DRG  C5    C  C     0  -0.521  -2.1569  -0.4044   0.1988
 DRG  C6    C  C     0  -0.521  -2.0994   0.3967  -1.0961
 DRG  C11   C  CR66  0   0.059  -0.8018   0.1702  -1.8219
 DRG  C7    C  CR16  0  -0.315  -0.7437   0.1503  -3.2109
 DRG  C8    C  CR16  0  -0.252   0.4639  -0.0227  -3.8717
 DRG  C9    C  CR16  0  -0.257   1.6349  -0.1803  -3.1400
 DRG  C10   C  CR16  0  -0.290   1.5909  -0.1662  -1.7557
 DRG  C12   C  CR66  0   0.073   0.3791   0.0076  -1.0863
 DRG  C13   C  CR66  0   0.136   0.3070   0.0290   0.3828
 DRG  N1    N  N     0  -0.280   1.4197   0.2063   1.0640
 DRG  N2    N  N     0  -0.324   1.4280   0.2219   2.3761
 DRG  C3    C  CR6   0   0.435   0.2912   0.0722   3.0508
 DRG  N3    N  NH2   0  -0.836   0.3611   0.1565   4.4029
 DRG  HC4   H  HCR6  0   0.277  -1.8511  -0.2567   2.9614
 DRG  HC51  H  H     0   0.267  -2.2054  -1.4731  -0.0360
 DRG  HC52  H  H     0   0.267  -3.0574  -0.1645   0.7647
 DRG  HC61  H  H     0   0.262  -2.9416   0.1335  -1.7371
 DRG  HC62  H  H     0   0.258  -2.2058   1.4626  -0.8667
 DRG  HC7   H  HCR6  0   0.250  -1.6567   0.2727  -3.7817
 DRG  HC8   H  HCR6  0   0.255   0.4907  -0.0389  -4.9535
 DRG  HC9   H  HCR6  0   0.255   2.5797  -0.3226  -3.6481
 DRG  H10C  H  HCR6  0   0.249   2.4997  -0.2983  -1.1834
 DRG  HN31  H  HNH2  0   0.388   1.2730   0.0572   4.8182
 DRG  HN32  H  HNH2  0   0.398  -0.3936  -0.2305   4.9439

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
 DRG  C4   C14   aromatic  1.365  0.020  1.365
 DRG  C4   C3    aromatic  1.409  0.020  1.409
 DRG  C4   HC4   single    0.930  0.020  1.080
 DRG  C14  C5    single    1.496  0.020  1.496
 DRG  C14  C13   aromatic  1.414  0.020  1.414
 DRG  C5   C6    single    1.524  0.020  1.524
 DRG  C5   HC51  single    0.970  0.020  1.090
 DRG  C5   HC52  single    0.970  0.020  1.090
 DRG  C6   C11   single    1.504  0.020  1.504
 DRG  C6   HC61  single    0.970  0.020  1.090
 DRG  C6   HC62  single    0.970  0.020  1.090
 DRG  C11  C7    aromatic  1.390  0.020  1.390
 DRG  C11  C12   aromatic  1.401  0.020  1.401
 DRG  C7   C8    aromatic  1.387  0.020  1.387
 DRG  C7   HC7   single    0.930  0.020  1.080
 DRG  C8   C9    aromatic  1.390  0.020  1.390
 DRG  C8   HC8   single    0.930  0.020  1.080
 DRG  C9   C10   aromatic  1.385  0.020  1.385
 DRG  C9   HC9   single    0.930  0.020  1.080
 DRG  C10  C12   aromatic  1.395  0.020  1.395
 DRG  C10  H10C  single    0.930  0.020  1.080
 DRG  C12  C13   aromatic  1.471  0.020  1.471
 DRG  C13  N1    aromatic  1.317  0.020  1.317
 DRG  N1   N2    aromatic  1.312  0.020  1.312
 DRG  N2   C3    aromatic  1.330  0.020  1.330
 DRG  C3   N3    single    1.356  0.020  1.356
 DRG  N3   HN31  single    0.890  0.020  1.040
 DRG  N3   HN32  single    0.890  0.020  1.040

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
 DRG  HC4   C4   C3    120.46  3.000
 DRG  HC4   C4   C14   121.54  3.000
 DRG  C3    C4   C14   118.00  3.000
 DRG  C13   C14  C5    119.09  3.000
 DRG  C13   C14  C4    117.03  3.000
 DRG  C5    C14  C4    123.86  3.000
 DRG  HC52  C5   HC51  106.82  3.000
 DRG  HC52  C5   C6    110.89  3.000
 DRG  HC51  C5   C6    109.42  3.000
 DRG  HC52  C5   C14   110.45  3.000
 DRG  HC51  C5   C14   108.48  3.000
 DRG  C6    C5   C14   110.68  3.000
 DRG  HC62  C6   HC61  106.43  3.000
 DRG  HC62  C6   C11   109.35  3.000
 DRG  HC61  C6   C11   110.25  3.000
 DRG  HC62  C6   C5    109.27  3.000
 DRG  HC61  C6   C5    110.09  3.000
 DRG  C11   C6   C5    111.31  3.000
 DRG  C12   C11  C7    119.19  3.000
 DRG  C12   C11  C6    119.43  3.000
 DRG  C7    C11  C6    121.36  3.000
 DRG  HC7   C7   C8    119.77  3.000
 DRG  HC7   C7   C11   119.30  3.000
 DRG  C8    C7   C11   120.93  3.000
 DRG  HC8   C8   C9    120.25  3.000
 DRG  HC8   C8   C7    119.97  3.000
 DRG  C9    C8   C7    119.79  3.000
 DRG  HC9   C9   C10   119.89  3.000
 DRG  HC9   C9   C8    120.22  3.000
 DRG  C10   C9   C8    119.89  3.000
 DRG  H10C  C10  C12   119.40  3.000
 DRG  H10C  C10  C9    120.05  3.000
 DRG  C12   C10  C9    120.55  3.000
 DRG  C13   C12  C10   121.57  3.000
 DRG  C13   C12  C11   118.78  3.000
 DRG  C10   C12  C11   119.65  3.000
 DRG  N1    C13  C12   118.50  3.000
 DRG  N1    C13  C14   121.68  3.000
 DRG  C12   C13  C14   119.82  3.000
 DRG  N2    N1   C13   121.61  3.000
 DRG  C3    N2   N1    120.03  3.000
 DRG  N3    C3   N2    117.03  3.000
 DRG  N3    C3   C4    121.30  3.000
 DRG  N2    C3   C4    121.64  3.000
 DRG  HN32  N3   HN31  114.81  3.000
 DRG  HN32  N3   C3    118.25  3.000
 DRG  HN31  N3   C3    116.85  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
 DRG  CONST_01  C12   C13  C14  C4   180.00   0.0  0
 DRG  CONST_02  N1    C13  C14  C4     0.00   0.0  0
 DRG  CONST_03  N1    N2   C3   C4     0.00   0.0  0
 DRG  CONST_04  N2    C3   C4   C14    0.00   0.0  0
 DRG  CONST_07  N2    N1   C13  C14    0.00   0.0  0
 DRG  CONST_08  C9    C8   C7   C11    0.00   0.0  0
 DRG  CONST_09  C9    C10  C12  C11    0.00   0.0  0
 DRG  CONST_11  C10   C12  C11  C7     0.00   0.0  0
 DRG  CONST_12  C13   C12  C11  C7   180.00   0.0  0
 DRG  CONST_13  C10   C9   C8   C7     0.00   0.0  0
 DRG  CONST_14  C12   C11  C7   C8     0.00   0.0  0
 DRG  CONST_15  C12   C10  C9   C8     0.00   0.0  0
 DRG  CONST_16  C13   C12  C10  C9   180.00   0.0  0
 DRG  CONST_18  N2    N1   C13  C12  180.00   0.0  0
 DRG  CONST_19  C3    C4   C14  C13    0.00   0.0  0
 DRG  CONST_20  C3    N2   N1   C13    0.00   0.0  0
 DRG  CONST_21  N3    C3   C4   C14  180.00   0.0  0
 DRG  CONST_22  N3    C3   N2   N1   180.00   0.0  0
 DRG  CONST_23  HC4   C4   C14  C5     0.00   0.0  0
 DRG  CONST_24  HC7   C7   C11  C6     0.00   0.0  0
 DRG  CONST_25  HC8   C8   C7   C11  180.00   0.0  0
 DRG  CONST_26  H10C  C10  C12  C11  180.00   0.0  0
 DRG  CONST_27  HC9   C9   C8   C7   180.00   0.0  0
 DRG  Var_01    C6    C5   C14  C4   145.59  30.0  1
 DRG  Var_02    C11   C6   C5   C14   51.77  30.0  1
 DRG  Var_03    C7    C11  C6   C5   145.28  30.0  1

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
 DRG  plan-1  C6    0.020
 DRG  plan-1  C11   0.020
 DRG  plan-1  C7    0.020
 DRG  plan-1  C8    0.020
 DRG  plan-1  C9    0.020
 DRG  plan-1  C10   0.020
 DRG  plan-1  C12   0.020
 DRG  plan-1  C13   0.020
 DRG  plan-1  HC7   0.020
 DRG  plan-1  HC8   0.020
 DRG  plan-1  HC9   0.020
 DRG  plan-1  H10C  0.020
 DRG  plan-2  C3    0.020
 DRG  plan-2  N3    0.020
 DRG  plan-2  HN31  0.020
 DRG  plan-2  HN32  0.020
 DRG  plan-3  C4    0.020
 DRG  plan-3  C14   0.020
 DRG  plan-3  C5    0.020
 DRG  plan-3  C12   0.020
 DRG  plan-3  C13   0.020
 DRG  plan-3  N1    0.020
 DRG  plan-3  N2    0.020
 DRG  plan-3  C3    0.020
 DRG  plan-3  N3    0.020
 DRG  plan-3  HC4   0.020

