# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May 21 20:51:42 2020
#   Inital geometry file: a 100 line input string
#   Ligand name: 1-methyl-8-(phenylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1nc(C(O)=O)c2CCc3cnc(Nc4ccccc4)nc3c12
#
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
 P49  P49  '1-methyl-8-(phenylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid'  ligand  39  24  .  2021-08-20  2021-08-20  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_P49
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
 P49  C1    C  CR16  0  -0.033  -0.8573  -2.2275   0.2047
 P49  N2    N  N     0  -0.467  -1.9546  -1.4874   0.0778
 P49  C3    C  CR6   0   0.608  -1.7790  -0.1756   0.0003
 P49  N4    N  N     0  -0.490  -0.5969   0.4499   0.0099
 P49  C5    C  CR66  0  -0.036   0.4182  -1.7044   0.2524
 P49  C6    C  CR66  0   0.271   0.4762  -0.3076   0.1329
 P49  C7    C  C     0  -0.516   2.8846  -1.9632  -0.2468
 P49  C8    C  C     0  -0.521   1.6597  -2.5183   0.4849
 P49  C9    C  CR56  0  -0.125   2.9459  -0.4837  -0.0635
 P49  C10   C  CR56  0   0.418   1.8050   0.2698   0.1135
 P49  N11   N  NR5   0  -0.345   2.1877   1.5669   0.2086
 P49  N12   N  N     0  -0.252   3.4872   1.6975   0.1127
 P49  C13   C  CR5   0   0.066   3.9739   0.4697  -0.0629
 P49  C14   C  CH3   0  -0.518   1.3579   2.7364   0.4143
 P49  N15   N  NH1   0  -0.775  -2.8458   0.6639  -0.1092
 P49  C16   C  CR6   0   0.364  -4.2153   0.4278  -0.1274
 P49  C17   C  CR16  0  -0.355  -5.0370   1.5544  -0.2634
 P49  C18   C  CR16  0  -0.245  -6.4140   1.4299  -0.2867
 P49  C19   C  CR16  0  -0.279  -7.0113   0.1799  -0.1749
 P49  C20   C  CR16  0  -0.245  -6.2004  -0.9365  -0.0409
 P49  C21   C  CR16  0  -0.317  -4.8155  -0.8294  -0.0162
 P49  C22   C  C     0   0.495   5.4094   0.2291  -0.2221
 P49  O23   O  OH1   0  -0.593   6.1355   1.3309  -0.0960
 P49  O24   O  O     0  -0.438   5.8790  -0.8626  -0.4433
 P49  H1    H  HCR6  0   0.270  -1.0093  -3.3001   0.2736
 P49  H15   H  HNH1  0   0.408  -2.5745   1.6331  -0.1787
 P49  H81C  H  H     0   0.261   1.8704  -2.5287   1.5595
 P49  H82C  H  H     0   0.264   1.4876  -3.5553   0.1938
 P49  H71C  H  H     0   0.266   3.7863  -2.4470   0.1237
 P49  H72C  H  H     0   0.259   2.8233  -2.1909  -1.3157
 P49  H141  H  HCH3  0   0.264   0.7793   2.6343   1.3288
 P49  H142  H  HCH3  0   0.271   2.0158   3.5951   0.4955
 P49  H143  H  HCH3  0   0.265   0.6763   2.8726  -0.4204
 P49  H17   H  HCR6  0   0.265  -4.5882   2.5375  -0.3525
 P49  H21   H  HCR6  0   0.283  -4.2087  -1.7137   0.0883
 P49  H18   H  HCR6  0   0.257  -7.0234   2.3179  -0.3942
 P49  H19   H  HCR6  0   0.252  -8.0883   0.0812  -0.1920
 P49  H20   H  HCR6  0   0.254  -6.6453  -1.9196   0.0483
 P49  H23   H  HOH1  0   0.487   7.0730   1.1153  -0.2065

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
 P49  C1   N2    aromatic  1.330  0.020  1.330
 P49  C1   C5    aromatic  1.379  0.020  1.379
 P49  N2   C3    aromatic  1.326  0.020  1.326
 P49  C3   N4    aromatic  1.337  0.020  1.337
 P49  C3   N15   single    1.362  0.020  1.362
 P49  N4   C6    aromatic  1.319  0.020  1.319
 P49  C5   C6    aromatic  1.403  0.020  1.403
 P49  C5   C8    single    1.503  0.020  1.503
 P49  C6   C10   aromatic  1.449  0.020  1.449
 P49  C7   C8    single    1.531  0.020  1.531
 P49  C7   C9    single    1.492  0.020  1.492
 P49  C9   C10   aromatic  1.379  0.020  1.379
 P49  C9   C13   aromatic  1.402  0.020  1.402
 P49  C10  N11   aromatic  1.356  0.020  1.356
 P49  N11  N12   aromatic  1.310  0.020  1.310
 P49  N11  C14   single    1.449  0.020  1.449
 P49  N12  C13   aromatic  1.332  0.020  1.332
 P49  C13  C22   single    1.464  0.020  1.464
 P49  N15  C16   single    1.390  0.020  1.390
 P49  C16  C17   aromatic  1.401  0.020  1.401
 P49  C16  C21   aromatic  1.398  0.020  1.398
 P49  C17  C18   aromatic  1.383  0.020  1.383
 P49  C18  C19   aromatic  1.390  0.020  1.390
 P49  C19  C20   aromatic  1.386  0.020  1.386
 P49  C20  C21   aromatic  1.389  0.020  1.389
 P49  C22  O23   single    1.325  0.020  1.325
 P49  C22  O24   double    1.209  0.020  1.209
 P49  C1   H1    single    0.930  0.020  1.080
 P49  N15  H15   single    0.860  0.020  1.020
 P49  C8   H81C  single    0.970  0.020  1.090
 P49  C8   H82C  single    0.970  0.020  1.090
 P49  C7   H71C  single    0.970  0.020  1.090
 P49  C7   H72C  single    0.970  0.020  1.090
 P49  C14  H141  single    0.970  0.020  1.090
 P49  C14  H142  single    0.970  0.020  1.090
 P49  C14  H143  single    0.970  0.020  1.090
 P49  C17  H17   single    0.930  0.020  1.080
 P49  C21  H21   single    0.930  0.020  1.080
 P49  C18  H18   single    0.930  0.020  1.080
 P49  C19  H19   single    0.930  0.020  1.080
 P49  C20  H20   single    0.930  0.020  1.080
 P49  O23  H23   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
 P49  H1    C1   C5    120.13  3.000
 P49  H1    C1   N2    116.14  3.000
 P49  C5    C1   N2    123.73  3.000
 P49  C3    N2   C1    116.55  3.000
 P49  N15   C3   N4    113.87  3.000
 P49  N15   C3   N2    120.72  3.000
 P49  N4    C3   N2    125.41  3.000
 P49  C6    N4   C3    116.81  3.000
 P49  C8    C5   C6    121.21  3.000
 P49  C8    C5   C1    124.33  3.000
 P49  C6    C5   C1    114.38  3.000
 P49  C10   C6   C5    115.83  3.000
 P49  C10   C6   N4    121.06  3.000
 P49  C5    C6   N4    123.09  3.000
 P49  H72C  C7   H71C  106.64  3.000
 P49  H72C  C7   C9    109.18  3.000
 P49  H71C  C7   C9    111.40  3.000
 P49  H72C  C7   C8    110.27  3.000
 P49  H71C  C7   C8    109.82  3.000
 P49  C9    C7   C8    109.49  3.000
 P49  H82C  C8   H81C  106.45  3.000
 P49  H82C  C8   C7    110.08  3.000
 P49  H81C  C8   C7    108.57  3.000
 P49  H82C  C8   C5    110.08  3.000
 P49  H81C  C8   C5    108.42  3.000
 P49  C7    C8   C5    113.00  3.000
 P49  C13   C9   C10   103.59  3.000
 P49  C13   C9   C7    134.79  3.000
 P49  C10   C9   C7    121.58  3.000
 P49  N11   C10  C9    107.36  3.000
 P49  N11   C10  C6    129.73  3.000
 P49  C9    C10  C6    122.88  3.000
 P49  C14   N11  N12   119.89  3.000
 P49  C14   N11  C10   128.36  3.000
 P49  N12   N11  C10   111.74  3.000
 P49  C13   N12  N11   106.28  3.000
 P49  C22   C13  N12   121.60  3.000
 P49  C22   C13  C9    127.37  3.000
 P49  N12   C13  C9    111.03  3.000
 P49  H143  C14  H142  109.81  3.000
 P49  H143  C14  H141  108.92  3.000
 P49  H142  C14  H141  109.53  3.000
 P49  H143  C14  N11   110.58  3.000
 P49  H142  C14  N11   107.59  3.000
 P49  H141  C14  N11   110.40  3.000
 P49  H15   N15  C16   115.29  3.000
 P49  H15   N15  C3    112.78  3.000
 P49  C16   N15  C3    131.93  3.000
 P49  C21   C16  C17   118.63  3.000
 P49  C21   C16  N15   125.10  3.000
 P49  C17   C16  N15   116.27  3.000
 P49  H17   C17  C18   119.50  3.000
 P49  H17   C17  C16   119.62  3.000
 P49  C18   C17  C16   120.88  3.000
 P49  H18   C18  C19   120.25  3.000
 P49  H18   C18  C17   119.24  3.000
 P49  C19   C18  C17   120.51  3.000
 P49  H19   C19  C20   120.69  3.000
 P49  H19   C19  C18   120.58  3.000
 P49  C20   C19  C18   118.72  3.000
 P49  H20   C20  C21   118.56  3.000
 P49  H20   C20  C19   119.92  3.000
 P49  C21   C20  C19   121.52  3.000
 P49  H21   C21  C20   119.98  3.000
 P49  H21   C21  C16   120.27  3.000
 P49  C20   C21  C16   119.74  3.000
 P49  O24   C22  O23   123.73  3.000
 P49  O24   C22  C13   123.31  3.000
 P49  O23   C22  C13   112.96  3.000
 P49  H23   O23  C22   109.54  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
 P49  CONST_01  N4    C3   N2   C1      0.00   0.0  0
 P49  CONST_02  N4    C6   C5   C1      0.00   0.0  0
 P49  CONST_03  C10   C6   C5   C1    180.00   0.0  0
 P49  CONST_04  C6    C5   C1   N2      0.00   0.0  0
 P49  CONST_05  C6    N4   C3   N2      0.00   0.0  0
 P49  CONST_06  C5    C1   N2   C3      0.00   0.0  0
 P49  CONST_07  C5    C6   N4   C3      0.00   0.0  0
 P49  CONST_08  C10   C6   N4   C3    180.00   0.0  0
 P49  CONST_10  N11   C10  C6   N4      0.00   0.0  0
 P49  CONST_11  C9    C10  C6   C5      0.00   0.0  0
 P49  CONST_12  N11   C10  C6   C5    180.00   0.0  0
 P49  CONST_13  C13   C9   C10  C6    180.00   0.0  0
 P49  CONST_14  N12   N11  C10  C6    180.00   0.0  0
 P49  CONST_15  N12   N11  C10  C9      0.00   0.0  0
 P49  CONST_16  N11   N12  C13  C9      0.00   0.0  0
 P49  CONST_17  N12   C13  C9   C10     0.00   0.0  0
 P49  CONST_18  C13   N12  N11  C10     0.00   0.0  0
 P49  CONST_19  C13   C9   C10  N11     0.00   0.0  0
 P49  CONST_20  C19   C18  C17  C16     0.00   0.0  0
 P49  CONST_21  C19   C20  C21  C16     0.00   0.0  0
 P49  CONST_22  C20   C21  C16  C17     0.00   0.0  0
 P49  CONST_23  C20   C19  C18  C17     0.00   0.0  0
 P49  CONST_24  C21   C16  C17  C18     0.00   0.0  0
 P49  CONST_25  C21   C20  C19  C18     0.00   0.0  0
 P49  CONST_26  N15   C3   N2   C1    180.00   0.0  0
 P49  CONST_27  N15   C3   N4   C6    180.00   0.0  0
 P49  CONST_28  C14   N11  C10  C6      0.00   0.0  0
 P49  CONST_29  C22   C13  C9   C7      0.00   0.0  0
 P49  CONST_30  C14   N11  C10  C9    180.00   0.0  0
 P49  CONST_31  C22   C13  C9   C10   180.00   0.0  0
 P49  CONST_32  C22   C13  N12  N11   180.00   0.0  0
 P49  CONST_33  C14   N11  N12  C13   180.00   0.0  0
 P49  CONST_34  C18   C17  C16  N15   180.00   0.0  0
 P49  CONST_35  C20   C21  C16  N15   180.00   0.0  0
 P49  CONST_36  H1    C1   N2   C3    180.00   0.0  0
 P49  CONST_37  H18   C18  C17  C16   180.00   0.0  0
 P49  CONST_38  H20   C20  C21  C16   180.00   0.0  0
 P49  CONST_39  H21   C21  C16  C17   180.00   0.0  0
 P49  CONST_40  H19   C19  C18  C17   180.00   0.0  0
 P49  CONST_41  H17   C17  C18  C19   180.00   0.0  0
 P49  CONST_42  H23   O23  C22  C13   180.00   0.0  0
 P49  Var_01    C7    C8   C5   C1    147.41  30.0  1
 P49  Var_02    C9    C7   C8   C5     44.92  30.0  1
 P49  Var_03    C10   C9   C7   C8    -29.35  30.0  1
 P49  Var_04    C16   N15  C3   N2      1.99  30.0  2
 P49  Var_05    C17   C16  N15  C3   -179.69  30.0  2
 P49  Var_06    O23   C22  C13  C9   -176.18  30.0  2
 P49  Var_07    H141  C14  N11  C10    57.25  30.0  2

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
 P49  plan-1  N15  0.020
 P49  plan-1  C16  0.020
 P49  plan-1  C17  0.020
 P49  plan-1  C18  0.020
 P49  plan-1  C19  0.020
 P49  plan-1  C20  0.020
 P49  plan-1  C21  0.020
 P49  plan-1  H17  0.020
 P49  plan-1  H21  0.020
 P49  plan-1  H18  0.020
 P49  plan-1  H19  0.020
 P49  plan-1  H20  0.020
 P49  plan-2  C6   0.020
 P49  plan-2  C7   0.020
 P49  plan-2  C9   0.020
 P49  plan-2  C10  0.020
 P49  plan-2  N11  0.020
 P49  plan-2  N12  0.020
 P49  plan-2  C13  0.020
 P49  plan-2  C14  0.020
 P49  plan-2  C22  0.020
 P49  plan-3  C1   0.020
 P49  plan-3  N2   0.020
 P49  plan-3  C3   0.020
 P49  plan-3  N4   0.020
 P49  plan-3  C5   0.020
 P49  plan-3  C6   0.020
 P49  plan-3  C8   0.020
 P49  plan-3  C10  0.020
 P49  plan-3  N15  0.020
 P49  plan-3  H1   0.020
 P49  plan-4  C13  0.020
 P49  plan-4  C22  0.020
 P49  plan-4  O23  0.020
 P49  plan-4  O24  0.020
 P49  plan-4  H23  0.020

