# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 03:49:06 2021
#   Inital geometry file: a 122 line input string
#   Ligand name: 7-[3-(aminomethyl)-4-(cyclobutylmethoxy)phenyl]-4-methylquinolin-2-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc(N)nc2cc(ccc12)c3ccc(OCC4CCC4)c(CN)c3
#
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
 OUP  OUP  7-[3-(aminomethyl)-4-(cyclobutylmethoxy)phenyl]-4-methylquinolin-2-amine  ligand  51  26  .  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_OUP
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
 OUP  C02  C  CR6   0   0.448  116.7336  246.9921  361.6500
 OUP  C03  C  CR16  0  -0.451  115.9833  247.6487  362.6734
 OUP  C04  C  CR6   0   0.213  116.1311  248.9856  362.8782
 OUP  C05  C  CR66  0   0.006  117.0458  249.6954  362.0391
 OUP  C06  C  CR16  0  -0.321  117.2841  251.0788  362.1442
 OUP  C07  C  CR16  0  -0.319  118.1731  251.7109  361.3143
 OUP  C08  C  CR6   0   0.095  118.8801  250.9874  360.3277
 OUP  C09  C  CR16  0  -0.393  118.6566  249.6310  360.2172
 OUP  C10  C  CR66  0   0.241  117.7435  248.9572  361.0533
 OUP  C11  C  CR6   0   0.104  119.8358  251.6727  359.4351
 OUP  C12  C  CR16  0  -0.324  120.0340  251.2417  358.1236
 OUP  C13  C  CR16  0  -0.312  120.9394  251.8842  357.2959
 OUP  C14  C  CR6   0   0.321  121.6685  252.9732  357.7595
 OUP  C15  C  CR6   0   0.046  121.4885  253.4320  359.0664
 OUP  C16  C  CR16  0  -0.373  120.5705  252.7747  359.8760
 OUP  C17  C  CH2   0  -0.358  122.2900  254.5835  359.6097
 OUP  C20  C  CH2   0  -0.140  123.7624  252.9412  356.6900
 OUP  C21  C  C     0  -0.283  124.6390  253.8325  355.8506
 OUP  C22  C  C     0  -0.450  125.2245  255.0589  356.5876
 OUP  C23  C  C     0  -0.451  126.6451  254.4729  356.4365
 OUP  C24  C  C     0  -0.453  126.0680  253.2788  355.6460
 OUP  C4A  C  CH3   0  -0.750  115.3595  249.6956  363.9452
 OUP  N01  N  N     0  -0.516  117.5836  247.6234  360.8765
 OUP  N02  N  NH2   0  -0.839  116.5347  245.6666  361.4396
 OUP  N18  N  NH2   0  -0.777  123.6253  254.1415  359.9922
 OUP  O19  O  O2    0  -0.498  122.5308  253.6207  356.9327
 OUP  H1   H  HCR6  0   0.265  115.2974  247.0699  363.2802
 OUP  H2   H  HCR6  0   0.256  116.7531  251.6624  362.8851
 OUP  H3   H  HCR6  0   0.251  118.3157  252.7797  361.4063
 OUP  H4   H  HCR6  0   0.246  119.1954  249.0379  359.4880
 OUP  H5   H  HCR6  0   0.255  119.4608  250.4117  357.7301
 OUP  H6   H  HCR6  0   0.264  121.0653  251.5508  356.2729
 OUP  H7   H  HCR6  0   0.249  120.4458  253.1255  360.8945
 OUP  H8   H  HCH2  0   0.237  122.3980  255.3520  358.8437
 OUP  H9   H  HCH2  0   0.214  121.7262  255.0399  360.4336
 OUP  H10  H  HCH2  0   0.217  123.5770  251.9918  356.1719
 OUP  H11  H  HCH2  0   0.213  124.2484  252.7166  357.6464
 OUP  H12  H  H     0   0.237  124.1279  254.0757  354.9157
 OUP  H13  H  H     0   0.227  125.0704  256.0078  356.0742
 OUP  H14  H  H     0   0.241  124.8796  255.1678  357.6168
 OUP  H15  H  H     0   0.227  127.1205  254.1990  357.3785
 OUP  H16  H  H     0   0.228  127.3428  255.0956  355.8769
 OUP  H17  H  H     0   0.229  126.2497  252.2972  356.0885
 OUP  H18  H  H     0   0.235  126.3798  253.2342  354.6028
 OUP  H19  H  HCH3  0   0.255  114.7325  250.4812  363.5208
 OUP  H20  H  HCH3  0   0.260  114.7159  249.0071  364.4890
 OUP  H21  H  HCH3  0   0.255  116.0263  250.1735  364.6648
 OUP  H22  H  HNH2  0   0.385  117.2082  245.1833  360.8689
 OUP  H23  H  HNH2  0   0.396  116.1170  245.1161  362.1700
 OUP  H24  H  HNH2  0   0.350  124.1677  254.9437  360.2874
 OUP  H25  H  HNH2  0   0.341  123.5592  253.5386  360.8034

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
 OUP  C24  C21  single    1.546  0.020  1.546
 OUP  C24  C23  single    1.544  0.020  1.544
 OUP  C21  C22  single    1.546  0.020  1.546
 OUP  C21  C20  single    1.506  0.020  1.506
 OUP  C23  C22  single    1.544  0.020  1.544
 OUP  C20  O19  single    1.427  0.020  1.427
 OUP  O19  C14  single    1.359  0.020  1.359
 OUP  C13  C14  aromatic  1.390  0.020  1.390
 OUP  C13  C12  aromatic  1.385  0.020  1.385
 OUP  C14  C15  aromatic  1.397  0.020  1.397
 OUP  C12  C11  aromatic  1.395  0.020  1.395
 OUP  C15  C17  single    1.504  0.020  1.504
 OUP  C15  C16  aromatic  1.389  0.020  1.389
 OUP  C11  C16  aromatic  1.396  0.020  1.396
 OUP  C11  C08  single    1.476  0.020  1.476
 OUP  C17  N18  single    1.458  0.020  1.458
 OUP  C09  C08  aromatic  1.379  0.020  1.379
 OUP  C09  C10  aromatic  1.410  0.020  1.410
 OUP  C08  C07  aromatic  1.413  0.020  1.413
 OUP  N01  C10  aromatic  1.355  0.020  1.355
 OUP  N01  C02  aromatic  1.311  0.020  1.311
 OUP  C10  C05  aromatic  1.415  0.020  1.415
 OUP  N02  C02  single    1.357  0.020  1.357
 OUP  C02  C03  aromatic  1.429  0.020  1.429
 OUP  C07  C06  aromatic  1.371  0.020  1.371
 OUP  C05  C06  aromatic  1.408  0.020  1.408
 OUP  C05  C04  aromatic  1.430  0.020  1.430
 OUP  C03  C04  aromatic  1.361  0.020  1.361
 OUP  C04  C4A  single    1.496  0.020  1.496
 OUP  C03  H1   single    0.930  0.020  1.080
 OUP  C06  H2   single    0.930  0.020  1.080
 OUP  C07  H3   single    0.930  0.020  1.080
 OUP  C09  H4   single    0.930  0.020  1.080
 OUP  C12  H5   single    0.930  0.020  1.080
 OUP  C13  H6   single    0.930  0.020  1.080
 OUP  C16  H7   single    0.930  0.020  1.080
 OUP  C17  H8   single    0.970  0.020  1.090
 OUP  C17  H9   single    0.970  0.020  1.090
 OUP  C20  H10  single    0.970  0.020  1.090
 OUP  C20  H11  single    0.970  0.020  1.090
 OUP  C21  H12  single    0.970  0.020  1.090
 OUP  C22  H13  single    0.970  0.020  1.090
 OUP  C22  H14  single    0.970  0.020  1.090
 OUP  C23  H15  single    0.970  0.020  1.090
 OUP  C23  H16  single    0.970  0.020  1.090
 OUP  C24  H17  single    0.970  0.020  1.090
 OUP  C24  H18  single    0.970  0.020  1.090
 OUP  C4A  H19  single    0.970  0.020  1.090
 OUP  C4A  H20  single    0.970  0.020  1.090
 OUP  C4A  H21  single    0.970  0.020  1.090
 OUP  N02  H22  single    0.890  0.020  1.040
 OUP  N02  H23  single    0.890  0.020  1.040
 OUP  N18  H24  single    0.890  0.020  1.040
 OUP  N18  H25  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
 OUP  N02  C02  N01  118.29  3.000
 OUP  N02  C02  C03  118.88  3.000
 OUP  N01  C02  C03  122.80  3.000
 OUP  H1   C03  C04  120.63  3.000
 OUP  H1   C03  C02  119.22  3.000
 OUP  C04  C03  C02  120.15  3.000
 OUP  C4A  C04  C05  120.85  3.000
 OUP  C4A  C04  C03  121.18  3.000
 OUP  C05  C04  C03  117.97  3.000
 OUP  C10  C05  C06  118.75  3.000
 OUP  C06  C05  C04  123.53  3.000
 OUP  C10  C05  C04  117.72  3.000
 OUP  H2   C06  C07  118.94  3.000
 OUP  H2   C06  C05  119.87  3.000
 OUP  C07  C06  C05  121.19  3.000
 OUP  H3   C07  C08  119.94  3.000
 OUP  H3   C07  C06  119.31  3.000
 OUP  C08  C07  C06  120.74  3.000
 OUP  C11  C08  C09  120.86  3.000
 OUP  C09  C08  C07  118.58  3.000
 OUP  C11  C08  C07  120.55  3.000
 OUP  H4   C09  C10  117.37  3.000
 OUP  H4   C09  C08  120.78  3.000
 OUP  C10  C09  C08  121.84  3.000
 OUP  N01  C10  C09  118.01  3.000
 OUP  N01  C10  C05  123.10  3.000
 OUP  C09  C10  C05  118.89  3.000
 OUP  C16  C11  C12  117.79  3.000
 OUP  C16  C11  C08  121.08  3.000
 OUP  C12  C11  C08  121.14  3.000
 OUP  H5   C12  C13  118.99  3.000
 OUP  H5   C12  C11  120.23  3.000
 OUP  C13  C12  C11  120.77  3.000
 OUP  H6   C13  C14  119.68  3.000
 OUP  H6   C13  C12  119.84  3.000
 OUP  C14  C13  C12  120.47  3.000
 OUP  O19  C14  C15  119.65  3.000
 OUP  C15  C14  C13  120.12  3.000
 OUP  O19  C14  C13  120.21  3.000
 OUP  C17  C15  C16  120.24  3.000
 OUP  C16  C15  C14  118.36  3.000
 OUP  C17  C15  C14  121.37  3.000
 OUP  H7   C16  C15  118.05  3.000
 OUP  H7   C16  C11  119.44  3.000
 OUP  C15  C16  C11  122.49  3.000
 OUP  H9   C17  H8   106.56  3.000
 OUP  H9   C17  N18  113.55  3.000
 OUP  H8   C17  N18  107.90  3.000
 OUP  H9   C17  C15  108.40  3.000
 OUP  H8   C17  C15  109.79  3.000
 OUP  N18  C17  C15  110.53  3.000
 OUP  H11  C20  H10  108.03  3.000
 OUP  H11  C20  O19  109.38  3.000
 OUP  H10  C20  O19  110.27  3.000
 OUP  H11  C20  C21  110.46  3.000
 OUP  H10  C20  C21  110.32  3.000
 OUP  O19  C20  C21  108.38  3.000
 OUP  H12  C21  C24  113.50  3.000
 OUP  H12  C21  C22  114.10  3.000
 OUP  C24  C21  C22   89.84  3.000
 OUP  H12  C21  C20  109.65  3.000
 OUP  C22  C21  C20  115.11  3.000
 OUP  C24  C21  C20  113.57  3.000
 OUP  H14  C22  H13  108.23  3.000
 OUP  H14  C22  C23  114.90  3.000
 OUP  H13  C22  C23  114.48  3.000
 OUP  H14  C22  C21  114.16  3.000
 OUP  H13  C22  C21  114.36  3.000
 OUP  C23  C22  C21   90.04  3.000
 OUP  H16  C23  H15  107.94  3.000
 OUP  H16  C23  C24  114.73  3.000
 OUP  H15  C23  C24  114.28  3.000
 OUP  H16  C23  C22  114.99  3.000
 OUP  H15  C23  C22  114.33  3.000
 OUP  C24  C23  C22   89.99  3.000
 OUP  H18  C24  H17  107.67  3.000
 OUP  H18  C24  C23  114.51  3.000
 OUP  H17  C24  C23  115.19  3.000
 OUP  H18  C24  C21  113.94  3.000
 OUP  H17  C24  C21  114.96  3.000
 OUP  C23  C24  C21   90.04  3.000
 OUP  H21  C4A  H20  107.99  3.000
 OUP  H21  C4A  H19  107.00  3.000
 OUP  H20  C4A  H19  108.06  3.000
 OUP  H21  C4A  C04  111.29  3.000
 OUP  H20  C4A  C04  111.17  3.000
 OUP  H19  C4A  C04  111.15  3.000
 OUP  C10  N01  C02  118.26  3.000
 OUP  H23  N02  H22  115.28  3.000
 OUP  H23  N02  C02  118.89  3.000
 OUP  H22  N02  C02  117.32  3.000
 OUP  H25  N18  H24  105.85  3.000
 OUP  H25  N18  C17  109.32  3.000
 OUP  H24  N18  C17  109.09  3.000
 OUP  C20  O19  C14  115.10  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
 OUP  CONST_01  C09  C10  N01  C02   180.00   0.0  0
 OUP  CONST_02  C05  C10  N01  C02     0.00   0.0  0
 OUP  CONST_03  C05  C04  C03  C02     0.00   0.0  0
 OUP  CONST_04  C10  N01  C02  C03     0.00   0.0  0
 OUP  CONST_05  C10  C05  C04  C03     0.00   0.0  0
 OUP  CONST_06  C06  C05  C04  C03   180.00   0.0  0
 OUP  CONST_07  C09  C10  C05  C04   180.00   0.0  0
 OUP  CONST_08  N01  C10  C05  C04     0.00   0.0  0
 OUP  CONST_09  C07  C06  C05  C04   180.00   0.0  0
 OUP  CONST_10  N01  C02  C03  C04     0.00   0.0  0
 OUP  CONST_11  C08  C09  C10  C05     0.00   0.0  0
 OUP  CONST_12  C08  C07  C06  C05     0.00   0.0  0
 OUP  CONST_13  C11  C08  C07  C06   180.00   0.0  0
 OUP  CONST_14  C09  C08  C07  C06     0.00   0.0  0
 OUP  CONST_15  C09  C10  C05  C06     0.00   0.0  0
 OUP  CONST_16  N01  C10  C05  C06   180.00   0.0  0
 OUP  CONST_19  C10  C09  C08  C07     0.00   0.0  0
 OUP  CONST_20  C10  C05  C06  C07     0.00   0.0  0
 OUP  CONST_21  C13  C12  C11  C08   180.00   0.0  0
 OUP  CONST_22  C15  C16  C11  C08   180.00   0.0  0
 OUP  CONST_23  N01  C10  C09  C08   180.00   0.0  0
 OUP  CONST_26  C11  C08  C09  C10   180.00   0.0  0
 OUP  CONST_27  C14  C13  C12  C11     0.00   0.0  0
 OUP  CONST_28  C14  C15  C16  C11     0.00   0.0  0
 OUP  CONST_29  C15  C14  C13  C12     0.00   0.0  0
 OUP  CONST_30  C15  C16  C11  C12     0.00   0.0  0
 OUP  CONST_31  C16  C15  C14  C13     0.00   0.0  0
 OUP  CONST_32  C16  C11  C12  C13     0.00   0.0  0
 OUP  CONST_33  C4A  C04  C03  C02   180.00   0.0  0
 OUP  CONST_34  N02  C02  C03  C04   180.00   0.0  0
 OUP  CONST_35  C4A  C04  C05  C06     0.00   0.0  0
 OUP  CONST_36  N02  C02  N01  C10   180.00   0.0  0
 OUP  CONST_37  C4A  C04  C05  C10   180.00   0.0  0
 OUP  CONST_38  C17  C15  C16  C11   180.00   0.0  0
 OUP  CONST_39  O19  C14  C13  C12   180.00   0.0  0
 OUP  CONST_40  C17  C15  C14  C13   180.00   0.0  0
 OUP  CONST_41  O19  C14  C15  C16   180.00   0.0  0
 OUP  CONST_42  H2   C06  C05  C04     0.00   0.0  0
 OUP  CONST_43  H4   C09  C10  C05   180.00   0.0  0
 OUP  CONST_44  H3   C07  C06  C05   180.00   0.0  0
 OUP  CONST_45  H1   C03  C04  C05   180.00   0.0  0
 OUP  CONST_46  H5   C12  C11  C08     0.00   0.0  0
 OUP  CONST_47  H7   C16  C11  C08     0.00   0.0  0
 OUP  CONST_48  H6   C13  C12  C11   180.00   0.0  0
 OUP  CONST_49  H22  N02  C02  C03   180.00   0.0  0
 OUP  Var_01    C22  C23  C24  C21    -2.34  30.0  1
 OUP  Var_02    C21  C20  O19  C14  -175.65  30.0  1
 OUP  Var_03    N18  C17  C15  C14   -78.84  30.0  2
 OUP  Var_04    H19  C4A  C04  C03  -120.07  30.0  2
 OUP  Var_05    H24  N18  C17  C15   175.72  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
 OUP  chir_01  C21  C24  C22  C20  positiv

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
 OUP  plan-1  C08  0.020
 OUP  plan-1  C11  0.020
 OUP  plan-1  C12  0.020
 OUP  plan-1  C13  0.020
 OUP  plan-1  C14  0.020
 OUP  plan-1  C15  0.020
 OUP  plan-1  C16  0.020
 OUP  plan-1  C17  0.020
 OUP  plan-1  O19  0.020
 OUP  plan-1  H5   0.020
 OUP  plan-1  H6   0.020
 OUP  plan-1  H7   0.020
 OUP  plan-2  C02  0.020
 OUP  plan-2  C03  0.020
 OUP  plan-2  C04  0.020
 OUP  plan-2  C05  0.020
 OUP  plan-2  C06  0.020
 OUP  plan-2  C07  0.020
 OUP  plan-2  C08  0.020
 OUP  plan-2  C09  0.020
 OUP  plan-2  C10  0.020
 OUP  plan-2  C11  0.020
 OUP  plan-2  C4A  0.020
 OUP  plan-2  N01  0.020
 OUP  plan-2  N02  0.020
 OUP  plan-2  H1   0.020
 OUP  plan-2  H2   0.020
 OUP  plan-2  H3   0.020
 OUP  plan-2  H4   0.020
 OUP  plan-3  C02  0.020
 OUP  plan-3  N02  0.020
 OUP  plan-3  H22  0.020
 OUP  plan-3  H23  0.020

