# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 17:46:44 2022
#   Inital geometry file: a 114 line input string
#   Ligand name: 6-(3,4-dihydroxybenzyl)-3-ethyl-1-(2,4,6-trichlorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1nn(c2N=C(Cc3ccc(O)c(O)c3)NC(=O)c12)c4c(Cl)cc(Cl)cc4Cl
#
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
 D05  D05  6-(3,4-dihydroxybenzyl)-3-ethyl-1-(2,4,6-trichlorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one  ligand  45  30  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_D05
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
 D05  N8    N   NR16  0  -0.712   2.4553  -2.8475  -0.4912
 D05  C7    C   CR6   0   0.532   1.1407  -2.4974  -0.4886
 D05  N6    N   N     0  -0.427   0.7343  -1.2847  -0.3015
 D05  C5    C   CR56  0   0.581   1.7279  -0.4130  -0.0709
 D05  C4    C   CR56  0  -0.347   3.0890  -0.6517  -0.0444
 D05  C9    C   CR6   0   0.514   3.5412  -1.9868  -0.2890
 D05  N1    N   NR5   0  -0.496   1.5618   0.8946   0.1969
 D05  N2    N   N     0  -0.277   2.7491   1.5180   0.3944
 D05  C3    C   CR5   0   0.289   3.6800   0.6061   0.2516
 D05  O9    O   OC    0  -0.454   4.6846  -2.4029  -0.3258
 D05  C11   C   CR6   0   0.483   0.3343   1.5613   0.3025
 D05  C16   C   CR6   0  -0.089  -0.0652   2.4789  -0.6645
 D05  C12   C   CR6   0  -0.081  -0.5391   1.2796   1.3505
 D05  C15   C   CR16  0  -0.181  -1.2909   3.1174  -0.5907
 D05  C13   C   CR16  0  -0.171  -1.7809   1.8847   1.4351
 D05  C14   C   CR6   0  -0.050  -2.1352   2.8034   0.4616
 D05  CL14  CL  CL    0  -0.088  -3.6736   3.5735   0.5583
 D05  C1    C   CH2   0  -0.513   5.1246   0.9243   0.4289
 D05  C2    C   CH3   0  -0.669   5.6842   0.3566   1.7317
 D05  C20   C   CH2   0  -0.643   0.1503  -3.6099  -0.6847
 D05  CL16  CL  CL    0  -0.065   0.9723   2.8068  -1.9936
 D05  CL12  CL  CL    0  -0.069  -0.0717   0.1686   2.5734
 D05  C21   C   CR6   0   0.130  -1.2689  -3.1234  -0.7268
 D05  C22   C   CR16  0  -0.337  -1.8746  -2.6373   0.4305
 D05  C23   C   CR6   0   0.307  -3.1577  -2.1239   0.4041
 D05  C24   C   CR6   0   0.241  -3.8700  -2.1119  -0.8041
 D05  C25   C   CR16  0  -0.363  -3.2784  -2.6072  -1.9523
 D05  C26   C   CR16  0  -0.332  -1.9800  -3.1072  -1.9152
 D05  O23   O   OH1   0  -0.636  -3.6977  -1.6445   1.5456
 D05  O24   O   OH1   0  -0.647  -5.1227  -1.5999  -0.7536
 D05  HN8   H   HNR6  0   0.432   2.6848  -3.8201  -0.6562
 D05  H15   H   HCR6  0   0.314  -1.5852   3.8289  -1.3488
 D05  H13   H   HCR6  0   0.311  -2.4513   1.6514   2.2493
 D05  H11   H   HCH2  0   0.251   5.2500   2.0077   0.4085
 D05  H12   H   HCH2  0   0.249   5.6855   0.5206  -0.4164
 D05  H21   H   HCH3  0   0.229   5.1639   0.7705   2.5954
 D05  H22A  H   HCH3  0   0.232   5.5860  -0.7280   1.7640
 D05  H23A  H   HCH3  0   0.238   6.7425   0.5973   1.8286
 D05  H201  H   HCH2  0   0.301   0.4027  -4.1464  -1.6032
 D05  H202  H   HCH2  0   0.301   0.2960  -4.3263   0.1309
 D05  H22   H   HCR6  0   0.245  -1.3295  -2.6253   1.3668
 D05  H25   H   HCR6  0   0.270  -3.8290  -2.5986  -2.8864
 D05  H26   H   HCR6  0   0.249  -1.5287  -3.4772  -2.8273
 D05  H23   H   HOH1  0   0.469  -4.5721  -1.2766   1.3747
 D05  H24   H   HOH1  0   0.480  -5.5132  -1.5651  -1.6334

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
 D05  N8   C7    aromatic  1.360  0.020  1.360
 D05  N8   C9    aromatic  1.400  0.020  1.400
 D05  N8   HN8   single    0.860  0.020  1.020
 D05  C7   N6    aromatic  1.293  0.020  1.293
 D05  C7   C20   single    1.502  0.020  1.502
 D05  N6   C5    aromatic  1.342  0.020  1.342
 D05  C5   C4    aromatic  1.382  0.020  1.382
 D05  C5   N1    aromatic  1.345  0.020  1.345
 D05  C4   C9    aromatic  1.431  0.020  1.431
 D05  C4   C3    aromatic  1.421  0.020  1.421
 D05  C9   O9    double    1.217  0.020  1.217
 D05  N1   N2    aromatic  1.355  0.020  1.355
 D05  N1   C11   single    1.401  0.020  1.401
 D05  N2   C3    aromatic  1.311  0.020  1.311
 D05  C3   C1    single    1.490  0.020  1.490
 D05  C11  C16   aromatic  1.392  0.020  1.392
 D05  C11  C12   aromatic  1.393  0.020  1.393
 D05  C16  C15   aromatic  1.384  0.020  1.384
 D05  C16  CL16  single    1.718  0.020  1.718
 D05  C12  C13   aromatic  1.384  0.020  1.384
 D05  C12  CL12  single    1.717  0.020  1.717
 D05  C15  C14   aromatic  1.385  0.020  1.385
 D05  C15  H15   single    0.930  0.020  1.080
 D05  C13  C14   aromatic  1.385  0.020  1.385
 D05  C13  H13   single    0.930  0.020  1.080
 D05  C14  CL14  single    1.723  0.020  1.723
 D05  C1   C2    single    1.527  0.020  1.527
 D05  C1   H11   single    0.970  0.020  1.090
 D05  C1   H12   single    0.970  0.020  1.090
 D05  C2   H21   single    0.970  0.020  1.090
 D05  C2   H22A  single    0.970  0.020  1.090
 D05  C2   H23A  single    0.970  0.020  1.090
 D05  C20  C21   single    1.501  0.020  1.501
 D05  C20  H201  single    0.970  0.020  1.090
 D05  C20  H202  single    0.970  0.020  1.090
 D05  C21  C22   aromatic  1.394  0.020  1.394
 D05  C21  C26   aromatic  1.385  0.020  1.385
 D05  C22  C23   aromatic  1.382  0.020  1.382
 D05  C22  H22   single    0.930  0.020  1.080
 D05  C23  C24   aromatic  1.403  0.020  1.403
 D05  C23  O23   single    1.351  0.020  1.351
 D05  C24  C25   aromatic  1.383  0.020  1.383
 D05  C24  O24   single    1.354  0.020  1.354
 D05  C25  C26   aromatic  1.392  0.020  1.392
 D05  C25  H25   single    0.930  0.020  1.080
 D05  C26  H26   single    0.930  0.020  1.080
 D05  O23  H23   single    0.850  0.020  0.980
 D05  O24  H24   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
 D05  HN8   N8   C9    115.97  3.000
 D05  HN8   N8   C7    117.80  3.000
 D05  C9    N8   C7    126.22  3.000
 D05  C20   C7   N6    120.42  3.000
 D05  C20   C7   N8    116.50  3.000
 D05  N6    C7   N8    123.06  3.000
 D05  C5    N6   C7    113.68  3.000
 D05  N1    C5   C4    106.60  3.000
 D05  N1    C5   N6    125.05  3.000
 D05  C4    C5   N6    128.34  3.000
 D05  C3    C4   C9    136.91  3.000
 D05  C3    C4   C5    105.11  3.000
 D05  C9    C4   C5    117.98  3.000
 D05  O9    C9   C4    128.40  3.000
 D05  O9    C9   N8    120.92  3.000
 D05  C4    C9   N8    110.68  3.000
 D05  C11   N1   N2    122.52  3.000
 D05  C11   N1   C5    125.87  3.000
 D05  N2    N1   C5    111.59  3.000
 D05  C3    N2   N1    106.63  3.000
 D05  C1    C3   N2    121.81  3.000
 D05  C1    C3   C4    128.11  3.000
 D05  N2    C3   C4    110.07  3.000
 D05  C12   C11  C16   118.43  3.000
 D05  C12   C11  N1    120.65  3.000
 D05  C16   C11  N1    120.86  3.000
 D05  CL16  C16  C15   119.22  3.000
 D05  CL16  C16  C11   119.35  3.000
 D05  C15   C16  C11   121.42  3.000
 D05  CL12  C12  C13   118.92  3.000
 D05  CL12  C12  C11   119.74  3.000
 D05  C13   C12  C11   121.34  3.000
 D05  H15   C15  C14   121.08  3.000
 D05  H15   C15  C16   120.50  3.000
 D05  C14   C15  C16   118.41  3.000
 D05  H13   C13  C14   120.96  3.000
 D05  H13   C13  C12   120.56  3.000
 D05  C14   C13  C12   118.48  3.000
 D05  CL14  C14  C13   119.05  3.000
 D05  CL14  C14  C15   119.05  3.000
 D05  C13   C14  C15   121.90  3.000
 D05  H12   C1   H11   107.08  3.000
 D05  H12   C1   C2    109.56  3.000
 D05  H11   C1   C2    110.06  3.000
 D05  H12   C1   C3    109.09  3.000
 D05  H11   C1   C3    108.74  3.000
 D05  C2    C1   C3    112.17  3.000
 D05  H23A  C2   H22A  107.75  3.000
 D05  H23A  C2   H21   108.01  3.000
 D05  H22A  C2   H21   108.15  3.000
 D05  H23A  C2   C1    110.46  3.000
 D05  H22A  C2   C1    111.24  3.000
 D05  H21   C2   C1    111.10  3.000
 D05  H202  C20  H201  105.90  3.000
 D05  H202  C20  C21   111.02  3.000
 D05  H201  C20  C21   110.72  3.000
 D05  H202  C20  C7    107.42  3.000
 D05  H201  C20  C7    108.71  3.000
 D05  C21   C20  C7    112.77  3.000
 D05  C26   C21  C22   119.03  3.000
 D05  C26   C21  C20   120.88  3.000
 D05  C22   C21  C20   120.05  3.000
 D05  H22   C22  C23   118.65  3.000
 D05  H22   C22  C21   120.18  3.000
 D05  C23   C22  C21   121.14  3.000
 D05  O23   C23  C24   121.46  3.000
 D05  O23   C23  C22   119.13  3.000
 D05  C24   C23  C22   119.41  3.000
 D05  O24   C24  C25   124.19  3.000
 D05  O24   C24  C23   116.16  3.000
 D05  C25   C24  C23   119.66  3.000
 D05  H25   C25  C26   119.97  3.000
 D05  H25   C25  C24   119.67  3.000
 D05  C26   C25  C24   120.36  3.000
 D05  H26   C26  C25   119.28  3.000
 D05  H26   C26  C21   120.33  3.000
 D05  C25   C26  C21   120.40  3.000
 D05  H23   O23  C23   110.38  3.000
 D05  H24   O24  C24   110.77  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
 D05  CONST_01  C5    N6   C7   N8      0.00   0.0  0
 D05  CONST_02  C5    C4   C9   N8      0.00   0.0  0
 D05  CONST_03  C3    C4   C9   N8    180.00   0.0  0
 D05  CONST_04  C4    C9   N8   C7      0.00   0.0  0
 D05  CONST_05  C4    C5   N6   C7      0.00   0.0  0
 D05  CONST_06  N1    C5   N6   C7    180.00   0.0  0
 D05  CONST_07  C9    N8   C7   N6      0.00   0.0  0
 D05  CONST_08  C9    C4   C5   N6      0.00   0.0  0
 D05  CONST_09  C3    C4   C5   N6    180.00   0.0  0
 D05  CONST_10  N2    N1   C5   N6    180.00   0.0  0
 D05  CONST_11  C11   N1   C5   N6      0.00   0.0  0
 D05  CONST_12  N2    C3   C4   C5      0.00   0.0  0
 D05  CONST_13  C3    N2   N1   C5      0.00   0.0  0
 D05  CONST_16  N2    N1   C5   C4      0.00   0.0  0
 D05  CONST_17  C11   N1   C5   C4    180.00   0.0  0
 D05  CONST_18  N1    N2   C3   C4      0.00   0.0  0
 D05  CONST_19  N1    C5   C4   C9    180.00   0.0  0
 D05  CONST_20  N2    C3   C4   C9    180.00   0.0  0
 D05  CONST_21  C3    C4   C5   N1      0.00   0.0  0
 D05  CONST_22  C15   C16  C11  N1    180.00   0.0  0
 D05  CONST_23  C13   C12  C11  N1    180.00   0.0  0
 D05  CONST_26  C11   N1   N2   C3    180.00   0.0  0
 D05  CONST_27  C14   C15  C16  C11     0.00   0.0  0
 D05  CONST_28  C14   C13  C12  C11     0.00   0.0  0
 D05  CONST_29  C13   C12  C11  C16     0.00   0.0  0
 D05  CONST_30  C13   C14  C15  C16     0.00   0.0  0
 D05  CONST_31  C15   C16  C11  C12     0.00   0.0  0
 D05  CONST_32  C15   C14  C13  C12     0.00   0.0  0
 D05  CONST_33  C24   C23  C22  C21     0.00   0.0  0
 D05  CONST_34  C24   C25  C26  C21     0.00   0.0  0
 D05  CONST_35  C25   C26  C21  C22     0.00   0.0  0
 D05  CONST_36  C25   C24  C23  C22     0.00   0.0  0
 D05  CONST_37  C26   C21  C22  C23     0.00   0.0  0
 D05  CONST_38  C26   C25  C24  C23     0.00   0.0  0
 D05  CONST_39  O9    C9   N8   C7    180.00   0.0  0
 D05  CONST_40  C20   C7   N6   C5    180.00   0.0  0
 D05  CONST_41  O9    C9   C4   C5    180.00   0.0  0
 D05  CONST_42  C1    C3   C4   C5    180.00   0.0  0
 D05  CONST_43  C20   C7   N8   C9    180.00   0.0  0
 D05  CONST_44  C1    C3   C4   C9      0.00   0.0  0
 D05  CONST_45  C1    C3   N2   N1    180.00   0.0  0
 D05  CONST_46  CL16  C16  C11  N1      0.00   0.0  0
 D05  CONST_47  CL12  C12  C11  N1      0.00   0.0  0
 D05  CONST_48  O9    C9   C4   C3      0.00   0.0  0
 D05  CONST_49  CL12  C12  C11  C16   180.00   0.0  0
 D05  CONST_50  CL14  C14  C15  C16   180.00   0.0  0
 D05  CONST_51  CL16  C16  C11  C12   180.00   0.0  0
 D05  CONST_52  CL14  C14  C13  C12   180.00   0.0  0
 D05  CONST_53  CL16  C16  C15  C14   180.00   0.0  0
 D05  CONST_54  CL12  C12  C13  C14   180.00   0.0  0
 D05  CONST_55  C23   C22  C21  C20   180.00   0.0  0
 D05  CONST_56  C25   C26  C21  C20   180.00   0.0  0
 D05  CONST_57  O23   C23  C22  C21   180.00   0.0  0
 D05  CONST_58  O24   C24  C23  C22   180.00   0.0  0
 D05  CONST_59  O23   C23  C24  C25   180.00   0.0  0
 D05  CONST_60  O24   C24  C25  C26   180.00   0.0  0
 D05  CONST_61  HN8   N8   C7   N6    180.00   0.0  0
 D05  CONST_62  H15   C15  C16  C11   180.00   0.0  0
 D05  CONST_63  H13   C13  C12  C11   180.00   0.0  0
 D05  CONST_64  H25   C25  C26  C21   180.00   0.0  0
 D05  CONST_65  H26   C26  C21  C22   180.00   0.0  0
 D05  CONST_66  H22   C22  C23  C24   180.00   0.0  0
 D05  Var_01    C21   C20  C7   N8   -177.52  30.0  2
 D05  Var_02    C22   C21  C20  C7    -69.92  30.0  2
 D05  Var_03    C2    C1   C3   C4    -71.45  30.0  2
 D05  Var_04    H21   C2   C1   C3    -60.67  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
 D05  plan-1  N1    0.020
 D05  plan-1  C11   0.020
 D05  plan-1  C16   0.020
 D05  plan-1  C12   0.020
 D05  plan-1  C15   0.020
 D05  plan-1  C13   0.020
 D05  plan-1  C14   0.020
 D05  plan-1  CL14  0.020
 D05  plan-1  CL16  0.020
 D05  plan-1  CL12  0.020
 D05  plan-1  H15   0.020
 D05  plan-1  H13   0.020
 D05  plan-2  C20   0.020
 D05  plan-2  C21   0.020
 D05  plan-2  C22   0.020
 D05  plan-2  C23   0.020
 D05  plan-2  C24   0.020
 D05  plan-2  C25   0.020
 D05  plan-2  C26   0.020
 D05  plan-2  O23   0.020
 D05  plan-2  O24   0.020
 D05  plan-2  H22   0.020
 D05  plan-2  H25   0.020
 D05  plan-2  H26   0.020
 D05  plan-3  N8    0.020
 D05  plan-3  C7    0.020
 D05  plan-3  N6    0.020
 D05  plan-3  C5    0.020
 D05  plan-3  C4    0.020
 D05  plan-3  C9    0.020
 D05  plan-3  N1    0.020
 D05  plan-3  N2    0.020
 D05  plan-3  C3    0.020
 D05  plan-3  O9    0.020
 D05  plan-3  C11   0.020
 D05  plan-3  C1    0.020
 D05  plan-3  C20   0.020
 D05  plan-3  HN8   0.020

