# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 04:28:39 2020
#   Inital geometry file: a 114 line input string
#   Ligand name: 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O
#
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
 CQA  CQA  4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol  ligand  47  25  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_CQA
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
 CQA  C1    C   CR6   0  -0.044   5.7214  -0.4100  -0.8945
 CQA  C2    C   CR16  0  -0.188   4.7292  -0.5895  -1.8723
 CQA  C3    C   CR16  0  -0.290   3.4283  -0.3037  -1.5611
 CQA  C4    C   CR66  0   0.027   3.0596   0.1596  -0.2808
 CQA  C5    C   CR66  0   0.193   4.0759   0.3610   0.6867
 CQA  C6    C   CR16  0  -0.241   5.4148   0.0570   0.3512
 CQA  C7    C   CR6   0   0.444   1.7077   0.4546   0.0947
 CQA  C8    C   CR16  0  -0.398   1.5034   0.9549   1.3685
 CQA  C9    C   CR16  0  -0.067   2.5960   1.1242   2.2227
 CQA  N1    N   N     0  -0.462   3.8404   0.8416   1.9292
 CQA  CL    CL  CL    0  -0.114   7.3614  -0.7803  -1.2992
 CQA  N2    N   NH1   0  -0.782   0.6974   0.2408  -0.7893
 CQA  C10   C   CR6   0   0.307  -0.6545   0.5778  -0.5802
 CQA  C11   C   CR16  0  -0.270  -1.0366   1.8935  -0.3397
 CQA  C12   C   CR16  0  -0.318  -2.3694   2.2103  -0.1516
 CQA  C13   C   CR6   0   0.326  -3.3521   1.2279  -0.2485
 CQA  C14   C   CR6   0  -0.030  -2.9818  -0.0956  -0.5270
 CQA  C15   C   CR16  0  -0.330  -1.6350  -0.4029  -0.6604
 CQA  O     O   OH1   0  -0.653  -4.6395   1.5749  -0.0775
 CQA  C16   C   CH2   0  -0.319  -4.0370  -1.1521  -0.7282
 CQA  N3    N   NT    0  -0.479  -5.1402  -1.0188   0.2231
 CQA  C17   C   CH2   0  -0.271  -6.3288  -1.7468  -0.2155
 CQA  C18   C   CH3   0  -0.662  -7.0735  -1.0574  -1.3457
 CQA  C19   C   CH2   0  -0.282  -4.7287  -1.3989   1.5760
 CQA  C20   C   CH3   0  -0.654  -5.5758  -0.7423   2.6518
 CQA  H2    H   HCR6  0   0.261   4.9923  -0.9398  -2.8598
 CQA  H3    H   HCR6  0   0.221   2.6948  -0.4279  -2.3462
 CQA  H6    H   HCR6  0   0.259   6.1786   0.2086   1.1015
 CQA  H8    H   HCR6  0   0.265   0.5145   1.1977   1.7279
 CQA  H9    H   HCR6  0   0.241   2.4109   1.5103   3.2200
 CQA  HN2   H   HNH1  0   0.376   0.8767  -0.3850  -1.5547
 CQA  H11   H   HCR6  0   0.254  -0.2915   2.6767  -0.2947
 CQA  H12   H   HCR6  0   0.247  -2.6595   3.2327   0.0527
 CQA  H15   H   HCR6  0   0.227  -1.3425  -1.4299  -0.8463
 CQA  HO    H   HOH1  0   0.463  -5.1385   0.7301   0.0755
 CQA  H161  H   HCH2  0   0.233  -3.5861  -2.1532  -0.6873
 CQA  H162  H   HCH2  0   0.256  -4.4418  -1.0476  -1.7378
 CQA  H171  H   HCH2  0   0.229  -7.0048  -1.8339   0.6360
 CQA  H172  H   HCH2  0   0.208  -6.0654  -2.7747  -0.5047
 CQA  H181  H   HCH3  0   0.222  -6.4751  -0.9661  -2.2522
 CQA  H182  H   HCH3  0   0.233  -7.9645  -1.6278  -1.6073
 CQA  H183  H   HCH3  0   0.226  -7.3925  -0.0573  -1.0515
 CQA  H191  H   HCH2  0   0.210  -4.7402  -2.4925   1.6876
 CQA  H192  H   HCH2  0   0.249  -3.6907  -1.0903   1.7118
 CQA  H201  H   HCH3  0   0.229  -5.4898   0.3432   2.6032
 CQA  H202  H   HCH3  0   0.216  -6.6324  -0.9979   2.5688
 CQA  H203  H   HCH3  0   0.230  -5.2429  -1.0610   3.6390

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
 CQA  C1   C2    aromatic  1.405  0.020  1.405
 CQA  C1   C6    aromatic  1.365  0.020  1.365
 CQA  C1   CL    single    1.729  0.020  1.729
 CQA  C2   C3    aromatic  1.368  0.020  1.368
 CQA  C2   H2    single    0.930  0.020  1.080
 CQA  C3   C4    aromatic  1.411  0.020  1.411
 CQA  C3   H3    single    0.930  0.020  1.080
 CQA  C4   C5    aromatic  1.418  0.020  1.418
 CQA  C4   C7    aromatic  1.434  0.020  1.434
 CQA  C5   C6    aromatic  1.413  0.020  1.413
 CQA  C5   N1    aromatic  1.353  0.020  1.353
 CQA  C6   H6    single    0.930  0.020  1.080
 CQA  C7   C8    aromatic  1.384  0.020  1.384
 CQA  C7   N2    single    1.359  0.020  1.359
 CQA  C8   C9    aromatic  1.397  0.020  1.397
 CQA  C8   H8    single    0.930  0.020  1.080
 CQA  C9   N1    aromatic  1.309  0.020  1.309
 CQA  C9   H9    single    0.930  0.020  1.080
 CQA  N2   C10   single    1.409  0.020  1.409
 CQA  N2   HN2   single    0.860  0.020  1.020
 CQA  C10  C11   aromatic  1.391  0.020  1.391
 CQA  C10  C15   aromatic  1.389  0.020  1.389
 CQA  C11  C12   aromatic  1.383  0.020  1.383
 CQA  C11  H11   single    0.930  0.020  1.080
 CQA  C12  C13   aromatic  1.393  0.020  1.393
 CQA  C12  H12   single    0.930  0.020  1.080
 CQA  C13  C14   aromatic  1.402  0.020  1.402
 CQA  C13  O     single    1.344  0.020  1.344
 CQA  C14  C15   aromatic  1.388  0.020  1.388
 CQA  C14  C16   single    1.507  0.020  1.507
 CQA  C15  H15   single    0.930  0.020  1.080
 CQA  O    HO    single    0.850  0.020  0.980
 CQA  C16  N3    single    1.463  0.020  1.463
 CQA  C16  H161  single    0.970  0.020  1.090
 CQA  C16  H162  single    0.970  0.020  1.090
 CQA  N3   C17   single    1.461  0.020  1.461
 CQA  N3   C19   single    1.464  0.020  1.464
 CQA  C17  C18   single    1.519  0.020  1.519
 CQA  C17  H171  single    0.970  0.020  1.090
 CQA  C17  H172  single    0.970  0.020  1.090
 CQA  C18  H181  single    0.970  0.020  1.090
 CQA  C18  H182  single    0.970  0.020  1.090
 CQA  C18  H183  single    0.970  0.020  1.090
 CQA  C19  C20   single    1.519  0.020  1.519
 CQA  C19  H191  single    0.970  0.020  1.090
 CQA  C19  H192  single    0.970  0.020  1.090
 CQA  C20  H201  single    0.970  0.020  1.090
 CQA  C20  H202  single    0.970  0.020  1.090
 CQA  C20  H203  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
 CQA  CL    C1   C6    119.98  3.000
 CQA  CL    C1   C2    118.66  3.000
 CQA  C6    C1   C2    121.35  3.000
 CQA  H2    C2   C3    120.49  3.000
 CQA  H2    C2   C1    120.38  3.000
 CQA  C3    C2   C1    119.13  3.000
 CQA  H3    C3   C4    121.29  3.000
 CQA  H3    C3   C2    117.12  3.000
 CQA  C4    C3   C2    121.58  3.000
 CQA  C7    C4   C5    117.90  3.000
 CQA  C7    C4   C3    123.49  3.000
 CQA  C5    C4   C3    118.61  3.000
 CQA  N1    C5   C6    117.35  3.000
 CQA  N1    C5   C4    123.54  3.000
 CQA  C6    C5   C4    119.11  3.000
 CQA  H6    C6   C5    118.31  3.000
 CQA  H6    C6   C1    121.50  3.000
 CQA  C5    C6   C1    120.19  3.000
 CQA  N2    C7   C8    123.08  3.000
 CQA  N2    C7   C4    119.87  3.000
 CQA  C8    C7   C4    117.05  3.000
 CQA  H8    C8   C9    119.04  3.000
 CQA  H8    C8   C7    121.53  3.000
 CQA  C9    C8   C7    119.42  3.000
 CQA  H9    C9   N1    116.41  3.000
 CQA  H9    C9   C8    118.14  3.000
 CQA  N1    C9   C8    125.45  3.000
 CQA  C9    N1   C5    116.61  3.000
 CQA  HN2   N2   C10   115.68  3.000
 CQA  HN2   N2   C7    117.43  3.000
 CQA  C10   N2   C7    125.38  3.000
 CQA  C15   C10  C11   118.94  3.000
 CQA  C15   C10  N2    119.99  3.000
 CQA  C11   C10  N2    121.03  3.000
 CQA  H11   C11  C12   119.49  3.000
 CQA  H11   C11  C10   120.18  3.000
 CQA  C12   C11  C10   120.33  3.000
 CQA  H12   C12  C13   119.36  3.000
 CQA  H12   C12  C11   120.03  3.000
 CQA  C13   C12  C11   120.60  3.000
 CQA  O     C13  C14   121.45  3.000
 CQA  O     C13  C12   119.00  3.000
 CQA  C14   C13  C12   119.55  3.000
 CQA  C16   C14  C15   120.77  3.000
 CQA  C16   C14  C13   120.22  3.000
 CQA  C15   C14  C13   118.97  3.000
 CQA  H15   C15  C14   119.22  3.000
 CQA  H15   C15  C10   119.23  3.000
 CQA  C14   C15  C10   121.54  3.000
 CQA  HO    O    C13   106.33  3.000
 CQA  H162  C16  H161  105.87  3.000
 CQA  H162  C16  N3    108.22  3.000
 CQA  H161  C16  N3    111.61  3.000
 CQA  H162  C16  C14   108.41  3.000
 CQA  H161  C16  C14   110.28  3.000
 CQA  N3    C16  C14   112.18  3.000
 CQA  C19   N3   C17   112.12  3.000
 CQA  C19   N3   C16   111.42  3.000
 CQA  C17   N3   C16   111.89  3.000
 CQA  H172  C17  H171  106.20  3.000
 CQA  H172  C17  C18   110.24  3.000
 CQA  H171  C17  C18   108.25  3.000
 CQA  H172  C17  N3    110.47  3.000
 CQA  H171  C17  N3    108.04  3.000
 CQA  C18   C17  N3    113.33  3.000
 CQA  H183  C18  H182  107.80  3.000
 CQA  H183  C18  H181  107.94  3.000
 CQA  H182  C18  H181  107.04  3.000
 CQA  H183  C18  C17   111.04  3.000
 CQA  H182  C18  C17   110.00  3.000
 CQA  H181  C18  C17   112.81  3.000
 CQA  H192  C19  H191  106.18  3.000
 CQA  H192  C19  C20   108.67  3.000
 CQA  H191  C19  C20   110.63  3.000
 CQA  H192  C19  N3    107.99  3.000
 CQA  H191  C19  N3    110.43  3.000
 CQA  C20   C19  N3    112.68  3.000
 CQA  H203  C20  H202  107.24  3.000
 CQA  H203  C20  H201  107.92  3.000
 CQA  H202  C20  H201  107.85  3.000
 CQA  H203  C20  C19   110.18  3.000
 CQA  H202  C20  C19   112.66  3.000
 CQA  H201  C20  C19   110.80  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
 CQA  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 CQA  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 CQA  CONST_03  N1    C5   C6   C1    180.00   0.0  0
 CQA  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 CQA  CONST_05  C5    C4   C3   C2      0.00   0.0  0
 CQA  CONST_06  C7    C4   C3   C2    180.00   0.0  0
 CQA  CONST_07  C6    C1   C2   C3      0.00   0.0  0
 CQA  CONST_08  C6    C5   C4   C3      0.00   0.0  0
 CQA  CONST_09  N1    C5   C4   C3    180.00   0.0  0
 CQA  CONST_10  C8    C7   C4   C3    180.00   0.0  0
 CQA  CONST_11  C9    N1   C5   C4      0.00   0.0  0
 CQA  CONST_12  C9    C8   C7   C4      0.00   0.0  0
 CQA  CONST_13  C8    C7   C4   C5      0.00   0.0  0
 CQA  CONST_14  C8    C9   N1   C5      0.00   0.0  0
 CQA  CONST_15  C7    C4   C5   C6    180.00   0.0  0
 CQA  CONST_16  C9    N1   C5   C6    180.00   0.0  0
 CQA  CONST_17  N1    C5   C4   C7      0.00   0.0  0
 CQA  CONST_18  N1    C9   C8   C7      0.00   0.0  0
 CQA  CONST_19  C13   C12  C11  C10     0.00   0.0  0
 CQA  CONST_20  C13   C14  C15  C10     0.00   0.0  0
 CQA  CONST_21  C14   C15  C10  C11     0.00   0.0  0
 CQA  CONST_22  C14   C13  C12  C11     0.00   0.0  0
 CQA  CONST_23  C15   C10  C11  C12     0.00   0.0  0
 CQA  CONST_24  C15   C14  C13  C12     0.00   0.0  0
 CQA  CONST_25  CL    C1   C2   C3    180.00   0.0  0
 CQA  CONST_26  N2    C7   C4   C3      0.00   0.0  0
 CQA  CONST_27  N2    C7   C4   C5    180.00   0.0  0
 CQA  CONST_28  CL    C1   C6   C5    180.00   0.0  0
 CQA  CONST_29  N2    C7   C8   C9    180.00   0.0  0
 CQA  CONST_30  C12   C11  C10  N2    180.00   0.0  0
 CQA  CONST_31  C14   C15  C10  N2    180.00   0.0  0
 CQA  CONST_32  C16   C14  C15  C10   180.00   0.0  0
 CQA  CONST_33  O     C13  C12  C11   180.00   0.0  0
 CQA  CONST_34  C16   C14  C13  C12   180.00   0.0  0
 CQA  CONST_35  O     C13  C14  C15   180.00   0.0  0
 CQA  CONST_36  H3    C3   C2   C1    180.00   0.0  0
 CQA  CONST_37  H6    C6   C1   C2    180.00   0.0  0
 CQA  CONST_38  H2    C2   C3   C4    180.00   0.0  0
 CQA  CONST_39  H8    C8   C7   C4    180.00   0.0  0
 CQA  CONST_40  H9    C9   N1   C5    180.00   0.0  0
 CQA  CONST_41  H12   C12  C11  C10   180.00   0.0  0
 CQA  CONST_42  H15   C15  C10  C11   180.00   0.0  0
 CQA  CONST_43  H11   C11  C12  C13   180.00   0.0  0
 CQA  Var_01    C10   N2   C7   C4   -175.15  30.0  2
 CQA  Var_02    C11   C10  N2   C7     59.41  30.0  2
 CQA  Var_03    N3    C16  C14  C13   -40.95  30.0  2
 CQA  Var_04    C17   N3   C16  C14   162.26  30.0  3
 CQA  Var_05    C18   C17  N3   C16   -75.01  30.0  3
 CQA  Var_06    C20   C19  N3   C16   155.24  30.0  3
 CQA  Var_07    H181  C18  C17  N3     62.39  30.0  3
 CQA  Var_08    H201  C20  C19  N3    -61.29  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
 CQA  plan-1  N2   0.020
 CQA  plan-1  C10  0.020
 CQA  plan-1  C11  0.020
 CQA  plan-1  C12  0.020
 CQA  plan-1  C13  0.020
 CQA  plan-1  C14  0.020
 CQA  plan-1  C15  0.020
 CQA  plan-1  O    0.020
 CQA  plan-1  C16  0.020
 CQA  plan-1  H11  0.020
 CQA  plan-1  H12  0.020
 CQA  plan-1  H15  0.020
 CQA  plan-2  C1   0.020
 CQA  plan-2  C2   0.020
 CQA  plan-2  C3   0.020
 CQA  plan-2  C4   0.020
 CQA  plan-2  C5   0.020
 CQA  plan-2  C6   0.020
 CQA  plan-2  C7   0.020
 CQA  plan-2  C8   0.020
 CQA  plan-2  C9   0.020
 CQA  plan-2  N1   0.020
 CQA  plan-2  CL   0.020
 CQA  plan-2  N2   0.020
 CQA  plan-2  H2   0.020
 CQA  plan-2  H3   0.020
 CQA  plan-2  H6   0.020
 CQA  plan-2  H8   0.020
 CQA  plan-2  H9   0.020

