# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 22:29:18 2022
#   Inital geometry file: a 119 line input string
#   Ligand name: methyl 5,7-dihydroxy-2-methyl-4,6,11-trioxo-3,4,6,11-tetrahydrotetracene-1-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)C1=C(C)CC(=O)c2c(O)c3C(=O)c4c(O)cccc4C(=O)c3cc12
#
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
 NGV  NGV  'methyl 5,7-dihydroxy-2-methyl-4,6,11-trioxo-3,4,6,11-tetrahydrotetracene-1-carboxylate'  ligand  42  28  .  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_NGV
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
 NGV  O17   O  O     0  -0.422   8.6506   2.7176  12.7320
 NGV  C14   C  C     0   0.443   9.3612   2.3252  13.6221
 NGV  O16   O  O2    0  -0.434  10.6804   2.3150  13.5744
 NGV  C15   C  CH3   0  -0.426  11.3024   2.8497  12.4006
 NGV  C10   C  C     0  -0.010   8.8361   1.7719  14.9079
 NGV  C9    C  C     0   0.063   9.0016   2.4339  16.0641
 NGV  C13   C  CH3   0  -0.722   9.7505   3.7125  16.2327
 NGV  C8    C  CH2   0  -0.635   8.4150   1.8840  17.3204
 NGV  C19   C  CR6   0   0.218   8.0967   0.5112  14.8423
 NGV  C20   C  CR6   0  -0.212   7.3549   0.0574  15.9433
 NGV  C7    C  C     0   0.383   7.2841   0.9094  17.1489
 NGV  O22   O  O     0  -0.375   6.4038   0.8299  17.9755
 NGV  C11   C  CR16  0  -0.417   8.1437  -0.2654  13.6790
 NGV  C18   C  CR66  0  -0.001   7.4967  -1.4780  13.6174
 NGV  C17   C  CR66  0  -0.202   6.7620  -1.9617  14.7061
 NGV  C5    C  CR6   0   0.486   6.1025  -3.2572  14.6406
 NGV  O20   O  O     0  -0.530   5.4608  -3.6824  15.6187
 NGV  C6    C  CR6   0   0.415   6.6766  -1.1774  15.8781
 NGV  O21   O  OH1   0  -0.584   6.0000  -1.5888  16.9281
 NGV  C12   C  CR6   0   0.323   7.6013  -2.2722  12.3613
 NGV  O18   O  O     0  -0.359   8.2232  -1.8465  11.4126
 NGV  C21   C  CR66  0  -0.030   6.9252  -3.5884  12.3144
 NGV  C1    C  CR16  0  -0.303   7.0183  -4.3454  11.1645
 NGV  C2    C  CR16  0  -0.217   6.3842  -5.5864  11.1082
 NGV  C3    C  CR16  0  -0.327   5.6696  -6.0658  12.1820
 NGV  C16   C  CR66  0  -0.175   6.2000  -4.0559  13.4275
 NGV  C4    C  CR6   0   0.391   5.5662  -5.3118  13.3579
 NGV  O19   O  OH1   0  -0.609   4.8662  -5.8311  14.3565
 NGV  H151  H  HCH3  0   0.245  11.0528   3.9014  12.2660
 NGV  H152  H  HCH3  0   0.257  12.3712   2.7471  12.5596
 NGV  H153  H  HCH3  0   0.246  11.0112   2.2910  11.5119
 NGV  H131  H  HCH3  0   0.258  10.1588   4.1226  15.3139
 NGV  H132  H  HCH3  0   0.266   9.0935   4.4632  16.6758
 NGV  H133  H  HCH3  0   0.268  10.5738   3.5677  16.9356
 NGV  H81   H  HCH2  0   0.297   8.1041   2.6873  17.9902
 NGV  H82   H  HCH2  0   0.325   9.2131   1.3442  17.8522
 NGV  H11   H  HCR6  0   0.271   8.7030   0.0599  12.8142
 NGV  H21   H  HOH1  0   0.496   5.6238  -2.4774  16.7198
 NGV  H1    H  HCR6  0   0.276   7.5776  -3.9829  10.3138
 NGV  H2    H  HCR6  0   0.284   6.4531  -6.1831  10.2087
 NGV  H3    H  HCR6  0   0.289   5.1792  -7.0294  12.1336
 NGV  H19   H  HOH1  0   0.491   4.8812  -5.2026  15.1092

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
 NGV  O17  C14   double    1.205  0.020  1.205
 NGV  C14  O16   single    1.320  0.020  1.320
 NGV  C14  C10   single    1.495  0.020  1.495
 NGV  O16  C15   single    1.432  0.020  1.432
 NGV  C15  H151  single    0.970  0.020  1.090
 NGV  C15  H152  single    0.970  0.020  1.090
 NGV  C15  H153  single    0.970  0.020  1.090
 NGV  C10  C9    double    1.343  0.020  1.343
 NGV  C10  C19   single    1.463  0.020  1.463
 NGV  C9   C13   single    1.491  0.020  1.491
 NGV  C9   C8    single    1.492  0.020  1.492
 NGV  C13  H131  single    0.970  0.020  1.090
 NGV  C13  H132  single    0.970  0.020  1.090
 NGV  C13  H133  single    0.970  0.020  1.090
 NGV  C8   C7    single    1.503  0.020  1.503
 NGV  C8   H81   single    0.970  0.020  1.090
 NGV  C8   H82   single    0.970  0.020  1.090
 NGV  C19  C20   aromatic  1.403  0.020  1.403
 NGV  C19  C11   aromatic  1.400  0.020  1.400
 NGV  C20  C7    single    1.478  0.020  1.478
 NGV  C20  C6    aromatic  1.410  0.020  1.410
 NGV  C7   O22   double    1.210  0.020  1.210
 NGV  C11  C18   aromatic  1.376  0.020  1.376
 NGV  C11  H11   single    0.930  0.020  1.080
 NGV  C18  C17   aromatic  1.400  0.020  1.400
 NGV  C18  C12   single    1.490  0.020  1.490
 NGV  C17  C5    single    1.455  0.020  1.455
 NGV  C17  C6    aromatic  1.413  0.020  1.413
 NGV  C5   O20   double    1.245  0.020  1.245
 NGV  C5   C16   single    1.456  0.020  1.456
 NGV  C6   O21   single    1.315  0.020  1.315
 NGV  O21  H21   single    0.850  0.020  0.980
 NGV  C12  O18   double    1.212  0.020  1.212
 NGV  C12  C21   single    1.480  0.020  1.480
 NGV  C21  C1    aromatic  1.380  0.020  1.380
 NGV  C21  C16   aromatic  1.408  0.020  1.408
 NGV  C1   C2    aromatic  1.395  0.020  1.395
 NGV  C1   H1    single    0.930  0.020  1.080
 NGV  C2   C3    aromatic  1.376  0.020  1.376
 NGV  C2   H2    single    0.930  0.020  1.080
 NGV  C3   C4    aromatic  1.401  0.020  1.401
 NGV  C3   H3    single    0.930  0.020  1.080
 NGV  C16  C4    aromatic  1.408  0.020  1.408
 NGV  C4   O19   single    1.326  0.020  1.326
 NGV  O19  H19   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
 NGV  C10   C14  O16   112.29  3.000
 NGV  C10   C14  O17   123.29  3.000
 NGV  O16   C14  O17   124.42  3.000
 NGV  C15   O16  C14   117.44  3.000
 NGV  H153  C15  H152  109.53  3.000
 NGV  H153  C15  H151  109.45  3.000
 NGV  H152  C15  H151  109.58  3.000
 NGV  H153  C15  O16   111.16  3.000
 NGV  H152  C15  O16   105.80  3.000
 NGV  H151  C15  O16   111.24  3.000
 NGV  C19   C10  C9    121.73  3.000
 NGV  C19   C10  C14   117.25  3.000
 NGV  C9    C10  C14   120.99  3.000
 NGV  C8    C9   C13   114.73  3.000
 NGV  C8    C9   C10   119.67  3.000
 NGV  C13   C9   C10   125.59  3.000
 NGV  H133  C13  H132  106.48  3.000
 NGV  H133  C13  H131  108.12  3.000
 NGV  H132  C13  H131  108.06  3.000
 NGV  H133  C13  C9    109.74  3.000
 NGV  H132  C13  C9    109.47  3.000
 NGV  H131  C13  C9    114.64  3.000
 NGV  H82   C8   H81   105.73  3.000
 NGV  H82   C8   C7    106.43  3.000
 NGV  H81   C8   C7    109.46  3.000
 NGV  H82   C8   C9    107.62  3.000
 NGV  H81   C8   C9    110.95  3.000
 NGV  C7    C8   C9    116.04  3.000
 NGV  C11   C19  C20   119.38  3.000
 NGV  C11   C19  C10   119.90  3.000
 NGV  C20   C19  C10   120.71  3.000
 NGV  C6    C20  C7    121.29  3.000
 NGV  C6    C20  C19   120.08  3.000
 NGV  C7    C20  C19   118.62  3.000
 NGV  O22   C7   C20   123.66  3.000
 NGV  O22   C7   C8    120.80  3.000
 NGV  C20   C7   C8    115.52  3.000
 NGV  H11   C11  C18   118.24  3.000
 NGV  H11   C11  C19   121.05  3.000
 NGV  C18   C11  C19   120.70  3.000
 NGV  C12   C18  C17   120.56  3.000
 NGV  C12   C18  C11   118.33  3.000
 NGV  C17   C18  C11   121.10  3.000
 NGV  C6    C17  C5    120.28  3.000
 NGV  C6    C17  C18   119.02  3.000
 NGV  C5    C17  C18   120.70  3.000
 NGV  C16   C5   O20   120.13  3.000
 NGV  C16   C5   C17   119.71  3.000
 NGV  O20   C5   C17   120.16  3.000
 NGV  O21   C6   C17   121.31  3.000
 NGV  O21   C6   C20   118.98  3.000
 NGV  C17   C6   C20   119.69  3.000
 NGV  H21   O21  C6    108.01  3.000
 NGV  C21   C12  O18   121.46  3.000
 NGV  C21   C12  C18   117.94  3.000
 NGV  O18   C12  C18   120.59  3.000
 NGV  C16   C21  C1    120.75  3.000
 NGV  C16   C21  C12   120.35  3.000
 NGV  C1    C21  C12   118.90  3.000
 NGV  H1    C1   C2    120.13  3.000
 NGV  H1    C1   C21   120.46  3.000
 NGV  C2    C1   C21   119.41  3.000
 NGV  H2    C2   C3    119.33  3.000
 NGV  H2    C2   C1    119.70  3.000
 NGV  C3    C2   C1    120.97  3.000
 NGV  H3    C3   C4    118.91  3.000
 NGV  H3    C3   C2    120.71  3.000
 NGV  C4    C3   C2    120.39  3.000
 NGV  C4    C16  C21   119.25  3.000
 NGV  C4    C16  C5    120.02  3.000
 NGV  C21   C16  C5    120.73  3.000
 NGV  O19   C4   C16   123.35  3.000
 NGV  O19   C4   C3    117.42  3.000
 NGV  C16   C4   C3    119.23  3.000
 NGV  H19   O19  C4    108.60  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
 NGV  CONST_01  C17   C6   C20  C19     0.00   0.0  0
 NGV  CONST_02  C17   C18  C11  C19     0.00   0.0  0
 NGV  CONST_03  C18   C11  C19  C20     0.00   0.0  0
 NGV  CONST_04  C18   C17  C6   C20     0.00   0.0  0
 NGV  CONST_05  C6    C20  C19  C11     0.00   0.0  0
 NGV  CONST_06  C6    C17  C18  C11     0.00   0.0  0
 NGV  CONST_07  C3    C2   C1   C21     0.00   0.0  0
 NGV  CONST_08  C3    C4   C16  C21     0.00   0.0  0
 NGV  CONST_09  C4    C16  C21  C1      0.00   0.0  0
 NGV  CONST_10  C4    C3   C2   C1      0.00   0.0  0
 NGV  CONST_11  C16   C21  C1   C2      0.00   0.0  0
 NGV  CONST_12  C16   C4   C3   C2      0.00   0.0  0
 NGV  CONST_13  O21   C6   C20  C19   180.00   0.0  0
 NGV  CONST_14  O21   C6   C20  C7      0.00   0.0  0
 NGV  CONST_15  O21   C6   C17  C18   180.00   0.0  0
 NGV  CONST_16  O21   C6   C17  C5      0.00   0.0  0
 NGV  CONST_17  O19   C4   C16  C5      0.00   0.0  0
 NGV  CONST_18  O19   C4   C16  C21   180.00   0.0  0
 NGV  CONST_19  O19   C4   C3   C2    180.00   0.0  0
 NGV  CONST_20  H11   C11  C19  C10     0.00   0.0  0
 NGV  CONST_21  H1    C1   C21  C12     0.00   0.0  0
 NGV  CONST_22  H2    C2   C1   C21   180.00   0.0  0
 NGV  CONST_23  H3    C3   C2   C1    180.00   0.0  0
 NGV  Var_01    C7    C8   C9   C10   -21.13  30.0  1
 NGV  Var_02    C20   C19  C10  C9     10.20  30.0  1
 NGV  Var_03    C20   C7   C8   C9     32.68  30.0  1
 NGV  Var_04    C19   C10  C9   C8     -0.33  30.0  1
 NGV  Var_05    C19   C20  C7   C8    -23.85  30.0  1
 NGV  Var_06    C9    C10  C14  O17  -111.78  30.0  2
 NGV  Var_07    H131  C13  C9   C10     1.66  30.0  3
 NGV  Var_08    C10   C14  O16  C15  -178.64  30.0  1
 NGV  Var_09    H151  C15  O16  C14    61.16  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
 NGV  plan-1  C8   0.020
 NGV  plan-1  C20  0.020
 NGV  plan-1  C7   0.020
 NGV  plan-1  O22  0.020
 NGV  plan-2  C10  0.020
 NGV  plan-2  C19  0.020
 NGV  plan-2  C20  0.020
 NGV  plan-2  C7   0.020
 NGV  plan-2  C11  0.020
 NGV  plan-2  C18  0.020
 NGV  plan-2  C17  0.020
 NGV  plan-2  C5   0.020
 NGV  plan-2  O20  0.020
 NGV  plan-2  C6   0.020
 NGV  plan-2  O21  0.020
 NGV  plan-2  C12  0.020
 NGV  plan-2  O18  0.020
 NGV  plan-2  C21  0.020
 NGV  plan-2  C1   0.020
 NGV  plan-2  C2   0.020
 NGV  plan-2  C3   0.020
 NGV  plan-2  C16  0.020
 NGV  plan-2  C4   0.020
 NGV  plan-2  O19  0.020
 NGV  plan-2  H11  0.020
 NGV  plan-2  H1   0.020
 NGV  plan-2  H2   0.020
 NGV  plan-2  H3   0.020
 NGV  plan-3  O17  0.020
 NGV  plan-3  C14  0.020
 NGV  plan-3  O16  0.020
 NGV  plan-3  C10  0.020

