# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 18 17:11:57 2020
#   Inital geometry file: a 142 line input string
#   Ligand name: 2-(diethylamino)ethyl 4-[[3-(4-nitrophenyl)-3-oxidanylidene-propyl]amino]benzoate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CC)CCOC(=O)c1ccc(NCCC(=O)c2ccc(cc2)[N+]([O-])=O)cc1
#
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
 BVN  BVN  '2-(diethylamino)ethyl 4-[[3-(4-nitrophenyl)-3-oxidanylidene-propyl]amino]benzoate'  ligand  57  30  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_BVN
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
 BVN  CAH  C  CH3    0  -0.662  -8.0531  -1.5411   2.7262
 BVN  CAG  C  CH2    0  -0.286  -8.6117  -0.9006   1.4658
 BVN  NAW  N  NT     0  -0.399  -7.7444  -1.0781   0.3124
 BVN  CAV  C  CH2    0  -0.288  -7.8541  -2.4079  -0.2657
 BVN  CAU  C  CH3    0  -0.662  -6.6313  -2.7975  -1.0809
 BVN  CAX  C  CH2    0  -0.326  -7.9282  -0.0309  -0.6735
 BVN  CAY  C  CH2    0  -0.172  -7.1492   1.2250  -0.3526
 BVN  OAZ  O  O2     0  -0.452  -5.7612   0.8929  -0.3958
 BVN  CBA  C  C      0   0.591  -4.8743   1.8587  -0.2090
 BVN  OAI  O  O      0  -0.473  -5.1816   3.0192  -0.0369
 BVN  CBB  C  CR6    0  -0.135  -3.4885   1.3655  -0.2320
 BVN  CAJ  C  CR16   0  -0.258  -3.1666   0.0063  -0.3339
 BVN  CAK  C  CR16   0  -0.339  -1.8571  -0.4143  -0.3364
 BVN  CBC  C  CR16   0  -0.245  -2.4406   2.2810  -0.1420
 BVN  CBD  C  CR16   0  -0.349  -1.1214   1.8756  -0.1526
 BVN  CAL  C  CR6    0   0.406  -0.7973   0.5098  -0.2406
 BVN  NAM  N  NH1    0  -0.699   0.4835   0.0661  -0.2167
 BVN  CAN  C  CH2    0  -0.241   1.6313   0.9376  -0.2913
 BVN  CAO  C  CH2    0  -0.636   2.8967   0.1124  -0.1485
 BVN  CAP  C  C      0   0.398   4.1515   0.9408  -0.1994
 BVN  OAA  O  O      0  -0.378   4.1188   2.1436  -0.3282
 BVN  CAQ  C  CR6    0   0.009   5.4670   0.2347  -0.0832
 BVN  CAR  C  CR16   0  -0.287   5.5514  -1.1466   0.0731
 BVN  CAS  C  CR16   0  -0.247   6.7818  -1.7723   0.1783
 BVN  CAD  C  CR6    0   0.259   7.9280  -0.9971   0.1216
 BVN  NAE  N  N      1   0.332   9.2294  -1.6486   0.2270
 BVN  OAT  O  O     -1  -0.370   9.2513  -2.8354   0.4468
 BVN  OAF  O  O      0  -0.370  10.2152  -0.9657   0.0883
 BVN  CAC  C  CR16   0  -0.254   7.8752   0.3802  -0.0343
 BVN  CAB  C  CR16   0  -0.255   6.6386   0.9889  -0.1330
 BVN  H1   H  HCH3   0   0.223  -8.7351  -1.3905   3.5637
 BVN  H2   H  HCH3   0   0.222  -7.9072  -2.6164   2.6159
 BVN  H3   H  HCH3   0   0.222  -7.0919  -1.0967   2.9847
 BVN  H4   H  HCH2   0   0.196  -9.6289  -1.2768   1.2667
 BVN  H5   H  HCH2   0   0.226  -8.7248   0.1694   1.6525
 BVN  H7   H  HCH2   0   0.229  -7.9640  -3.1272   0.5479
 BVN  H8   H  HCH2   0   0.193  -8.7630  -2.5079  -0.8825
 BVN  H9   H  HCH3   0   0.222  -6.4576  -2.1203  -1.9178
 BVN  H10  H  HCH3   0   0.222  -5.7368  -2.7926  -0.4570
 BVN  H11  H  HCH3   0   0.224  -6.7531  -3.7999  -1.4929
 BVN  H12  H  HCH2   0   0.243  -7.6033  -0.3893  -1.6520
 BVN  H13  H  HCH2   0   0.217  -8.9866   0.2503  -0.7940
 BVN  H14  H  HCH2   0   0.235  -7.3802   1.9992  -1.0883
 BVN  H15  H  HCH2   0   0.230  -7.4045   1.6192   0.6347
 BVN  H16  H  HCR6   0   0.262  -3.9490  -0.7374  -0.4044
 BVN  H17  H  HCR6   0   0.262  -1.6359  -1.4725  -0.4103
 BVN  H18  H  HCR6   0   0.255  -2.6566   3.3391  -0.0686
 BVN  H19  H  HCR6   0   0.271  -0.3446   2.6252  -0.0941
 BVN  H20  H  HNH1   0   0.393   0.6280  -0.9009  -0.4590
 BVN  H21  H  HCH2   0   0.239   1.6469   1.4968  -1.2338
 BVN  H22  H  HCH2   0   0.245   1.5843   1.6738   0.5143
 BVN  H23  H  HCH2   0   0.294   2.8787  -0.4403   0.7968
 BVN  H24  H  HCH2   0   0.290   2.9496  -0.6467  -0.9367
 BVN  H25  H  HCR6   0   0.285   4.6633  -1.7612   0.1158
 BVN  H26  H  HCR6   0   0.307   6.8308  -2.8443   0.2975
 BVN  H27  H  HCR6   0   0.305   8.7737   0.9778  -0.0759
 BVN  H28  H  HCR6   0   0.282   6.5882   2.0623  -0.2499

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
 BVN  OAA  CAP  double    1.210  0.020  1.210
 BVN  CAP  CAQ  single    1.498  0.020  1.498
 BVN  CAP  CAO  single    1.504  0.020  1.504
 BVN  CAR  CAQ  aromatic  1.393  0.020  1.393
 BVN  CAR  CAS  aromatic  1.384  0.020  1.384
 BVN  CAQ  CAB  aromatic  1.394  0.020  1.394
 BVN  CAS  CAD  aromatic  1.385  0.020  1.385
 BVN  OAF  NAE  double    1.207  0.020  1.207
 BVN  CAB  CAC  aromatic  1.382  0.020  1.382
 BVN  CAN  CAO  single    1.518  0.020  1.518
 BVN  CAN  NAM  single    1.443  0.020  1.443
 BVN  CAD  CAC  aromatic  1.387  0.020  1.387
 BVN  CAD  NAE  single    1.459  0.020  1.459
 BVN  NAE  OAT  single    1.207  0.020  1.207
 BVN  NAM  CAL  single    1.356  0.020  1.356
 BVN  CAK  CAL  aromatic  1.409  0.020  1.409
 BVN  CAK  CAJ  aromatic  1.375  0.020  1.375
 BVN  CAL  CBD  aromatic  1.406  0.020  1.406
 BVN  CAJ  CBB  aromatic  1.401  0.020  1.401
 BVN  CBD  CBC  aromatic  1.380  0.020  1.380
 BVN  CAH  CAG  single    1.520  0.020  1.520
 BVN  CBB  CBC  aromatic  1.394  0.020  1.394
 BVN  CBB  CBA  single    1.471  0.020  1.471
 BVN  CAG  NAW  single    1.454  0.020  1.454
 BVN  CAY  OAZ  single    1.428  0.020  1.428
 BVN  CAY  CAX  single    1.512  0.020  1.512
 BVN  CBA  OAZ  single    1.324  0.020  1.324
 BVN  CBA  OAI  double    1.213  0.020  1.213
 BVN  NAW  CAX  single    1.450  0.020  1.450
 BVN  NAW  CAV  single    1.454  0.020  1.454
 BVN  CAV  CAU  single    1.520  0.020  1.520
 BVN  CAH  H1   single    0.970  0.020  1.090
 BVN  CAH  H2   single    0.970  0.020  1.090
 BVN  CAH  H3   single    0.970  0.020  1.090
 BVN  CAG  H4   single    0.970  0.020  1.090
 BVN  CAG  H5   single    0.970  0.020  1.090
 BVN  CAV  H7   single    0.970  0.020  1.090
 BVN  CAV  H8   single    0.970  0.020  1.090
 BVN  CAU  H9   single    0.970  0.020  1.090
 BVN  CAU  H10  single    0.970  0.020  1.090
 BVN  CAU  H11  single    0.970  0.020  1.090
 BVN  CAX  H12  single    0.970  0.020  1.090
 BVN  CAX  H13  single    0.970  0.020  1.090
 BVN  CAY  H14  single    0.970  0.020  1.090
 BVN  CAY  H15  single    0.970  0.020  1.090
 BVN  CAJ  H16  single    0.930  0.020  1.080
 BVN  CAK  H17  single    0.930  0.020  1.080
 BVN  CBC  H18  single    0.930  0.020  1.080
 BVN  CBD  H19  single    0.930  0.020  1.080
 BVN  NAM  H20  single    0.890  0.020  1.040
 BVN  CAN  H21  single    0.970  0.020  1.090
 BVN  CAN  H22  single    0.970  0.020  1.090
 BVN  CAO  H23  single    0.970  0.020  1.090
 BVN  CAO  H24  single    0.970  0.020  1.090
 BVN  CAR  H25  single    0.930  0.020  1.080
 BVN  CAS  H26  single    0.930  0.020  1.080
 BVN  CAC  H27  single    0.930  0.020  1.080
 BVN  CAB  H28  single    0.930  0.020  1.080

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
 BVN  H3   CAH  H2   107.93  3.000
 BVN  H3   CAH  H1   108.24  3.000
 BVN  H2   CAH  H1   107.30  3.000
 BVN  H3   CAH  CAG  110.42  3.000
 BVN  H2   CAH  CAG  112.37  3.000
 BVN  H1   CAH  CAG  110.41  3.000
 BVN  H5   CAG  H4   105.64  3.000
 BVN  H5   CAG  NAW  108.48  3.000
 BVN  H4   CAG  NAW  111.43  3.000
 BVN  H5   CAG  CAH  108.01  3.000
 BVN  H4   CAG  CAH  110.18  3.000
 BVN  NAW  CAG  CAH  112.78  3.000
 BVN  CAX  NAW  CAV  112.37  3.000
 BVN  CAV  NAW  CAG  112.46  3.000
 BVN  CAX  NAW  CAG  112.06  3.000
 BVN  H8   CAV  H7   105.91  3.000
 BVN  H8   CAV  CAU  109.85  3.000
 BVN  H7   CAV  CAU  108.16  3.000
 BVN  H8   CAV  NAW  111.56  3.000
 BVN  H7   CAV  NAW  108.30  3.000
 BVN  CAU  CAV  NAW  112.76  3.000
 BVN  H11  CAU  H10  108.17  3.000
 BVN  H11  CAU  H9   107.37  3.000
 BVN  H10  CAU  H9   107.80  3.000
 BVN  H11  CAU  CAV  110.38  3.000
 BVN  H10  CAU  CAV  110.60  3.000
 BVN  H9   CAU  CAV  112.36  3.000
 BVN  H13  CAX  H12  105.76  3.000
 BVN  H13  CAX  CAY  107.82  3.000
 BVN  H12  CAX  CAY  108.03  3.000
 BVN  H13  CAX  NAW  112.37  3.000
 BVN  H12  CAX  NAW  109.56  3.000
 BVN  CAY  CAX  NAW  112.97  3.000
 BVN  H15  CAY  H14  107.65  3.000
 BVN  H15  CAY  OAZ  109.77  3.000
 BVN  H14  CAY  OAZ  110.48  3.000
 BVN  H15  CAY  CAX  111.76  3.000
 BVN  H14  CAY  CAX  109.67  3.000
 BVN  OAZ  CAY  CAX  107.53  3.000
 BVN  CBA  OAZ  CAY  118.50  3.000
 BVN  CBB  CBA  OAI  124.17  3.000
 BVN  OAI  CBA  OAZ  123.23  3.000
 BVN  CBB  CBA  OAZ  112.59  3.000
 BVN  CBC  CBB  CAJ  117.98  3.000
 BVN  CBC  CBB  CBA  119.13  3.000
 BVN  CAJ  CBB  CBA  122.89  3.000
 BVN  H16  CAJ  CAK  118.57  3.000
 BVN  H16  CAJ  CBB  120.38  3.000
 BVN  CAK  CAJ  CBB  121.05  3.000
 BVN  H17  CAK  CAL  119.43  3.000
 BVN  H17  CAK  CAJ  119.55  3.000
 BVN  CAL  CAK  CAJ  121.02  3.000
 BVN  H18  CBC  CBD  118.58  3.000
 BVN  H18  CBC  CBB  119.75  3.000
 BVN  CBD  CBC  CBB  121.67  3.000
 BVN  H19  CBD  CAL  120.74  3.000
 BVN  H19  CBD  CBC  118.86  3.000
 BVN  CAL  CBD  CBC  120.40  3.000
 BVN  NAM  CAL  CBD  122.31  3.000
 BVN  CBD  CAL  CAK  117.88  3.000
 BVN  NAM  CAL  CAK  119.80  3.000
 BVN  H20  NAM  CAN  116.95  3.000
 BVN  H20  NAM  CAL  116.45  3.000
 BVN  CAN  NAM  CAL  123.56  3.000
 BVN  H22  CAN  H21  106.91  3.000
 BVN  H22  CAN  CAO  109.45  3.000
 BVN  H21  CAN  CAO  110.27  3.000
 BVN  H22  CAN  NAM  109.56  3.000
 BVN  H21  CAN  NAM  111.34  3.000
 BVN  CAO  CAN  NAM  109.27  3.000
 BVN  H24  CAO  H23  105.80  3.000
 BVN  H24  CAO  CAP  108.48  3.000
 BVN  H23  CAO  CAP  108.71  3.000
 BVN  H24  CAO  CAN  110.44  3.000
 BVN  H23  CAO  CAN  109.99  3.000
 BVN  CAP  CAO  CAN  113.13  3.000
 BVN  CAQ  CAP  OAA  120.05  3.000
 BVN  CAQ  CAP  CAO  118.06  3.000
 BVN  OAA  CAP  CAO  121.90  3.000
 BVN  CAB  CAQ  CAR  119.32  3.000
 BVN  CAB  CAQ  CAP  118.71  3.000
 BVN  CAR  CAQ  CAP  121.98  3.000
 BVN  H25  CAR  CAS  118.05  3.000
 BVN  H25  CAR  CAQ  121.24  3.000
 BVN  CAS  CAR  CAQ  120.71  3.000
 BVN  H26  CAS  CAD  121.51  3.000
 BVN  H26  CAS  CAR  119.83  3.000
 BVN  CAD  CAS  CAR  118.65  3.000
 BVN  CAC  CAD  NAE  119.04  3.000
 BVN  NAE  CAD  CAS  119.03  3.000
 BVN  CAC  CAD  CAS  121.93  3.000
 BVN  OAF  NAE  OAT  124.22  3.000
 BVN  OAT  NAE  CAD  117.92  3.000
 BVN  OAF  NAE  CAD  117.87  3.000
 BVN  H27  CAC  CAB  119.88  3.000
 BVN  H27  CAC  CAD  121.47  3.000
 BVN  CAB  CAC  CAD  118.65  3.000
 BVN  H28  CAB  CAC  119.14  3.000
 BVN  H28  CAB  CAQ  120.12  3.000
 BVN  CAC  CAB  CAQ  120.74  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
 BVN  CONST_01  CAL  CAK  CAJ  CBB     0.00   0.0  0
 BVN  CONST_02  CAL  CBD  CBC  CBB     0.00   0.0  0
 BVN  CONST_03  CBD  CAL  CAK  CAJ     0.00   0.0  0
 BVN  CONST_04  CBD  CBC  CBB  CAJ     0.00   0.0  0
 BVN  CONST_05  CBC  CBD  CAL  CAK     0.00   0.0  0
 BVN  CONST_06  CBC  CBB  CAJ  CAK     0.00   0.0  0
 BVN  CONST_07  CAD  CAS  CAR  CAQ     0.00   0.0  0
 BVN  CONST_08  CAD  CAC  CAB  CAQ     0.00   0.0  0
 BVN  CONST_09  CAC  CAB  CAQ  CAR     0.00   0.0  0
 BVN  CONST_10  CAC  CAD  CAS  CAR     0.00   0.0  0
 BVN  CONST_11  CAB  CAQ  CAR  CAS     0.00   0.0  0
 BVN  CONST_12  CAB  CAC  CAD  CAS     0.00   0.0  0
 BVN  CONST_13  CAK  CAJ  CBB  CBA   180.00   0.0  0
 BVN  CONST_14  CBD  CBC  CBB  CBA   180.00   0.0  0
 BVN  CONST_15  NAM  CAL  CAK  CAJ   180.00   0.0  0
 BVN  CONST_16  NAM  CAL  CBD  CBC   180.00   0.0  0
 BVN  CONST_17  CAS  CAR  CAQ  CAP   180.00   0.0  0
 BVN  CONST_18  CAC  CAB  CAQ  CAP   180.00   0.0  0
 BVN  CONST_19  NAE  CAD  CAS  CAR   180.00   0.0  0
 BVN  CONST_20  CAB  CAC  CAD  NAE   180.00   0.0  0
 BVN  CONST_21  H17  CAK  CAJ  CBB   180.00   0.0  0
 BVN  CONST_22  H19  CBD  CBC  CBB   180.00   0.0  0
 BVN  CONST_23  H18  CBC  CBB  CAJ   180.00   0.0  0
 BVN  CONST_24  H16  CAJ  CBB  CBC   180.00   0.0  0
 BVN  CONST_25  H26  CAS  CAR  CAQ   180.00   0.0  0
 BVN  CONST_26  H27  CAC  CAB  CAQ   180.00   0.0  0
 BVN  CONST_27  H28  CAB  CAQ  CAR   180.00   0.0  0
 BVN  CONST_28  H25  CAR  CAS  CAD   180.00   0.0  0
 BVN  CONST_29  CAN  NAM  CAL  CAK   180.00   0.0  0
 BVN  CONST_30  CAN  NAM  CAL  CBD     0.00   0.0  0
 BVN  CONST_31  OAF  NAE  CAD  CAS   180.00   0.0  0
 BVN  CONST_32  OAT  NAE  CAD  CAS     0.00   0.0  0
 BVN  CONST_33  CAC  CAD  NAE  OAT   180.00   0.0  0
 BVN  CONST_34  CAC  CAD  NAE  OAF     0.00   0.0  0
 BVN  CONST_35  H20  NAM  CAL  CAK     0.00   0.0  0
 BVN  Var_01    CAJ  CBB  CBA  OAZ    -4.77  30.0  2
 BVN  Var_02    CAR  CAQ  CAP  CAO    -0.24  30.0  2
 BVN  Var_03    CBB  CBA  OAZ  CAY   177.95  30.0  2
 BVN  Var_04    CAO  CAN  NAM  CAL   176.41  30.0  2
 BVN  Var_05    CAQ  CAP  CAO  CAN  -179.38  30.0  2
 BVN  Var_06    CAX  NAW  CAG  CAH  -154.18  30.0  3
 BVN  Var_07    CAY  CAX  NAW  CAG    82.66  30.0  3
 BVN  Var_08    CAU  CAV  NAW  CAG  -157.72  30.0  3
 BVN  Var_09    OAZ  CAY  CAX  NAW    63.76  30.0  2
 BVN  Var_10    CAP  CAO  CAN  NAM  -179.39  30.0  3
 BVN  Var_11    H1   CAH  CAG  NAW  -179.65  30.0  3
 BVN  Var_12    H9   CAU  CAV  NAW   -60.34  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
 BVN  plan-1  CBA  0.020
 BVN  plan-1  CBB  0.020
 BVN  plan-1  CAJ  0.020
 BVN  plan-1  CAK  0.020
 BVN  plan-1  CBC  0.020
 BVN  plan-1  CBD  0.020
 BVN  plan-1  CAL  0.020
 BVN  plan-1  NAM  0.020
 BVN  plan-1  H16  0.020
 BVN  plan-1  H17  0.020
 BVN  plan-1  H18  0.020
 BVN  plan-1  H19  0.020
 BVN  plan-2  CAP  0.020
 BVN  plan-2  CAQ  0.020
 BVN  plan-2  CAR  0.020
 BVN  plan-2  CAS  0.020
 BVN  plan-2  CAD  0.020
 BVN  plan-2  NAE  0.020
 BVN  plan-2  CAC  0.020
 BVN  plan-2  CAB  0.020
 BVN  plan-2  H25  0.020
 BVN  plan-2  H26  0.020
 BVN  plan-2  H27  0.020
 BVN  plan-2  H28  0.020
 BVN  plan-3  CAL  0.020
 BVN  plan-3  NAM  0.020
 BVN  plan-3  CAN  0.020
 BVN  plan-3  H20  0.020
 BVN  plan-4  CAD  0.020
 BVN  plan-4  NAE  0.020
 BVN  plan-4  OAT  0.020
 BVN  plan-4  OAF  0.020
 BVN  plan-5  CAO  0.020
 BVN  plan-5  CAP  0.020
 BVN  plan-5  OAA  0.020
 BVN  plan-5  CAQ  0.020
 BVN  plan-6  OAZ  0.020
 BVN  plan-6  CBA  0.020
 BVN  plan-6  OAI  0.020
 BVN  plan-6  CBB  0.020

