# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 05:58:10 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: (4~{S})-5-(3-chloranyl-2-fluoranyl-phenyl)-4-(4-chloranyl-2-methyl-phenyl)-3-propan-2-yl-1,4-dihydropyrrolo[3,4-c]pyrazol-6-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)c1n[nH]c2C(=O)N([C@@H](c3ccc(Cl)cc3C)c12)c4cccc(Cl)c4F
#
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
 HRH  HRH  (4~{S})-5-(3-chloranyl-2-fluoranyl-phenyl)-4-(4-chloranyl-2-methyl-phenyl)-3-propan-2-yl-1,4-dihydropyrrolo[3,4-c]pyrazol-6-one  ligand  46  28  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_HRH
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
 HRH  C2   C   CR6   0   0.628  -2.3385  -1.3938   1.0361
 HRH  C3   C   CR6   0  -0.243  -3.7142  -1.3474   0.8882
 HRH  C42  C   CH3   0  -0.762   0.3619   0.9435  -3.0511
 HRH  C12  C   CR15  0  -0.254   0.7703  -0.8322  -0.6806
 HRH  C14  C   CR55  0  -0.023   2.0929  -1.2257  -0.1172
 HRH  C15  C   CR55  0   0.221   1.9327  -2.2048   0.8156
 HRH  C19  C   CR5   0   0.227   3.4711  -0.9811  -0.1762
 HRH  C20  C   CH1   0  -0.338   4.2096   0.0440  -0.9817
 HRH  C22  C   CH3   0  -0.645   4.4981   1.2814  -0.1289
 HRH  C26  C   CH3   0  -0.650   5.4888  -0.5192  -1.5933
 HRH  C30  C   CR5   0   0.563   0.5211  -2.5534   0.9841
 HRH  F1   F   F     0  -0.281  -1.8057  -1.1631   2.2322
 HRH  C4   C   CR16  0  -0.217  -4.2840  -1.5316  -0.3615
 HRH  C6   C   CR16  0  -0.274  -3.4628  -1.7640  -1.4543
 HRH  C8   C   CR16  0  -0.284  -2.0878  -1.8355  -1.2986
 HRH  C10  C   CR6   0   0.188  -1.5094  -1.6554  -0.0474
 HRH  N11  N   NR5   0  -0.618  -0.1202  -1.6883   0.1229
 HRH  N16  N   NR15  0  -0.513   3.1482  -2.5222   1.2757
 HRH  N18  N   N     0  -0.264   4.0849  -1.7866   0.6855
 HRH  C32  C   CR6   0   0.148   0.4383   0.6334  -0.5307
 HRH  C33  C   CR6   0   0.058   0.2569   1.4584  -1.6431
 HRH  C34  C   CR16  0  -0.250  -0.0318   2.8063  -1.4353
 HRH  C36  C   CR6   0  -0.036  -0.1370   3.3118  -0.1521
 HRH  C37  C   CR16  0  -0.220   0.0420   2.5003   0.9567
 HRH  C39  C   CR16  0  -0.297   0.3327   1.1639   0.7503
 HRH  CL1  CL  CL    0  -0.128  -0.4985   4.9922   0.0703
 HRH  CL2  CL  CL    0  -0.084  -4.6902  -1.0302   2.2709
 HRH  H1   H   HCH3  0   0.253  -0.3887   0.1787  -3.2588
 HRH  H2   H   HCH3  0   0.267   0.2116   1.7473  -3.7690
 HRH  H3   H   HCH3  0   0.256   1.3392   0.5032  -3.2546
 HRH  H4   H   HCR5  0   0.304   0.7020  -1.1371  -1.7280
 HRH  H5   H   HCH1  0   0.242   3.5448   0.3502  -1.7965
 HRH  H6   H   HCH3  0   0.232   4.9941   2.0494  -0.7243
 HRH  H7   H   HCH3  0   0.231   3.5803   1.7103   0.2761
 HRH  H8   H   HCH3  0   0.223   5.1503   1.0314   0.7093
 HRH  H9   H   HCH3  0   0.233   5.2766  -1.3369  -2.2826
 HRH  H10  H   HCH3  0   0.230   6.0191   0.2568  -2.1462
 HRH  H11  H   HCH3  0   0.225   6.1601  -0.8967  -0.8214
 HRH  H12  H   HCR6  0   0.294  -5.3584  -1.4909  -0.4744
 HRH  H13  H   HCR6  0   0.280  -3.9015  -1.9110  -2.4312
 HRH  H14  H   HCR6  0   0.285  -1.4561  -2.0390  -2.1535
 HRH  H15  H   HNR5  0   0.425   3.4075  -3.2095   1.9661
 HRH  H16  H   HCR6  0   0.275  -0.1712   3.4603  -2.2863
 HRH  H17  H   HCR6  0   0.280  -0.0399   2.8990   1.9583
 HRH  H18  H   HCR6  0   0.261   0.4800   0.5248   1.6123
 HRH  O31  O   O     0  -0.447  -0.0075  -3.3918   1.6789

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
 HRH  C22  C20  single    1.530  0.020  1.530
 HRH  C42  C33  single    1.503  0.020  1.503
 HRH  C20  C26  single    1.526  0.020  1.526
 HRH  C20  C19  single    1.498  0.020  1.498
 HRH  C34  C33  aromatic  1.394  0.020  1.394
 HRH  C34  C36  aromatic  1.383  0.020  1.383
 HRH  C33  C32  aromatic  1.397  0.020  1.397
 HRH  CL1  C36  single    1.733  0.020  1.733
 HRH  C36  C37  aromatic  1.386  0.020  1.386
 HRH  C32  C12  single    1.510  0.020  1.510
 HRH  C32  C39  aromatic  1.391  0.020  1.391
 HRH  C19  C14  aromatic  1.401  0.020  1.401
 HRH  C19  N18  aromatic  1.330  0.020  1.330
 HRH  C12  C14  single    1.490  0.020  1.490
 HRH  C12  N11  single    1.474  0.020  1.474
 HRH  C14  C15  aromatic  1.362  0.020  1.362
 HRH  C37  C39  aromatic  1.383  0.020  1.383
 HRH  N18  N16  aromatic  1.329  0.020  1.329
 HRH  C8   C6   aromatic  1.386  0.020  1.386
 HRH  C8   C10  aromatic  1.390  0.020  1.390
 HRH  C6   C4   aromatic  1.387  0.020  1.387
 HRH  N11  C10  single    1.400  0.020  1.400
 HRH  N11  C30  single    1.379  0.020  1.379
 HRH  C10  C2   aromatic  1.389  0.020  1.389
 HRH  C15  N16  aromatic  1.338  0.020  1.338
 HRH  C15  C30  single    1.464  0.020  1.464
 HRH  C4   C3   aromatic  1.386  0.020  1.386
 HRH  C30  O31  double    1.210  0.020  1.210
 HRH  C2   C3   aromatic  1.384  0.020  1.384
 HRH  C2   F1   single    1.330  0.020  1.330
 HRH  C3   CL2  single    1.722  0.020  1.722
 HRH  C42  H1   single    0.970  0.020  1.090
 HRH  C42  H2   single    0.970  0.020  1.090
 HRH  C42  H3   single    0.970  0.020  1.090
 HRH  C12  H4   single    0.970  0.020  1.090
 HRH  C20  H5   single    0.970  0.020  1.090
 HRH  C22  H6   single    0.970  0.020  1.090
 HRH  C22  H7   single    0.970  0.020  1.090
 HRH  C22  H8   single    0.970  0.020  1.090
 HRH  C26  H9   single    0.970  0.020  1.090
 HRH  C26  H10  single    0.970  0.020  1.090
 HRH  C26  H11  single    0.970  0.020  1.090
 HRH  C4   H12  single    0.930  0.020  1.080
 HRH  C6   H13  single    0.930  0.020  1.080
 HRH  C8   H14  single    0.930  0.020  1.080
 HRH  N16  H15  single    0.860  0.020  1.020
 HRH  C34  H16  single    0.930  0.020  1.080
 HRH  C37  H17  single    0.930  0.020  1.080
 HRH  C39  H18  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
 HRH  C10  C2   F1   119.68  3.000
 HRH  F1   C2   C3   119.24  3.000
 HRH  C10  C2   C3   121.07  3.000
 HRH  CL2  C3   C4   121.04  3.000
 HRH  CL2  C3   C2   118.92  3.000
 HRH  C4   C3   C2   120.03  3.000
 HRH  H3   C42  H2   107.39  3.000
 HRH  H3   C42  H1   107.32  3.000
 HRH  H2   C42  H1   107.28  3.000
 HRH  H3   C42  C33  112.06  3.000
 HRH  H2   C42  C33  110.81  3.000
 HRH  H1   C42  C33  111.73  3.000
 HRH  H4   C12  C32  110.62  3.000
 HRH  H4   C12  N11  108.83  3.000
 HRH  C32  C12  N11  112.14  3.000
 HRH  H4   C12  C14  110.12  3.000
 HRH  N11  C12  C14  100.18  3.000
 HRH  C32  C12  C14  114.44  3.000
 HRH  C19  C14  C15  105.67  3.000
 HRH  C15  C14  C12  110.14  3.000
 HRH  C19  C14  C12  144.19  3.000
 HRH  N16  C15  C30  141.27  3.000
 HRH  C30  C15  C14  111.32  3.000
 HRH  N16  C15  C14  107.42  3.000
 HRH  N18  C19  C20  122.37  3.000
 HRH  N18  C19  C14  108.73  3.000
 HRH  C20  C19  C14  128.82  3.000
 HRH  H5   C20  C26  108.30  3.000
 HRH  H5   C20  C22  107.64  3.000
 HRH  C26  C20  C22  111.33  3.000
 HRH  H5   C20  C19  106.98  3.000
 HRH  C26  C20  C19  112.10  3.000
 HRH  C22  C20  C19  110.28  3.000
 HRH  H8   C22  H7   107.92  3.000
 HRH  H8   C22  H6   107.99  3.000
 HRH  H7   C22  H6   107.96  3.000
 HRH  H8   C22  C20  110.83  3.000
 HRH  H7   C22  C20  111.48  3.000
 HRH  H6   C22  C20  110.53  3.000
 HRH  H11  C26  H10  107.81  3.000
 HRH  H11  C26  H9   107.92  3.000
 HRH  H10  C26  H9   107.92  3.000
 HRH  H11  C26  C20  111.12  3.000
 HRH  H10  C26  C20  110.39  3.000
 HRH  H9   C26  C20  111.54  3.000
 HRH  O31  C30  N11  126.16  3.000
 HRH  O31  C30  C15  130.70  3.000
 HRH  N11  C30  C15  103.13  3.000
 HRH  H12  C4   C6   120.84  3.000
 HRH  H12  C4   C3   119.85  3.000
 HRH  C6   C4   C3   119.31  3.000
 HRH  H13  C6   C8   119.82  3.000
 HRH  H13  C6   C4   119.65  3.000
 HRH  C8   C6   C4   120.52  3.000
 HRH  H14  C8   C10  119.51  3.000
 HRH  H14  C8   C6   120.01  3.000
 HRH  C10  C8   C6   120.48  3.000
 HRH  N11  C10  C8   121.28  3.000
 HRH  N11  C10  C2   120.12  3.000
 HRH  C8   C10  C2   118.56  3.000
 HRH  C10  N11  C30  123.52  3.000
 HRH  C30  N11  C12  115.09  3.000
 HRH  C10  N11  C12  121.31  3.000
 HRH  H15  N16  N18  120.01  3.000
 HRH  H15  N16  C15  129.12  3.000
 HRH  N18  N16  C15  110.87  3.000
 HRH  N16  N18  C19  107.32  3.000
 HRH  C39  C32  C33  119.90  3.000
 HRH  C39  C32  C12  118.58  3.000
 HRH  C33  C32  C12  121.51  3.000
 HRH  C34  C33  C32  118.64  3.000
 HRH  C32  C33  C42  122.32  3.000
 HRH  C34  C33  C42  119.04  3.000
 HRH  H16  C34  C36  119.92  3.000
 HRH  H16  C34  C33  119.58  3.000
 HRH  C36  C34  C33  120.50  3.000
 HRH  CL1  C36  C37  119.48  3.000
 HRH  C37  C36  C34  121.23  3.000
 HRH  CL1  C36  C34  119.29  3.000
 HRH  H17  C37  C39  120.70  3.000
 HRH  H17  C37  C36  121.04  3.000
 HRH  C39  C37  C36  118.27  3.000
 HRH  H18  C39  C37  118.68  3.000
 HRH  H18  C39  C32  119.84  3.000
 HRH  C37  C39  C32  121.47  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
 HRH  CONST_01  C6   C8   C10  C2      0.00   0.0  0
 HRH  CONST_02  C6   C4   C3   C2      0.00   0.0  0
 HRH  CONST_03  C8   C6   C4   C3      0.00   0.0  0
 HRH  CONST_04  C8   C10  C2   C3      0.00   0.0  0
 HRH  CONST_05  N16  N18  C19  C14     0.00   0.0  0
 HRH  CONST_06  N18  N16  C15  C14     0.00   0.0  0
 HRH  CONST_07  N18  C19  C14  C15     0.00   0.0  0
 HRH  CONST_08  C19  N18  N16  C15     0.00   0.0  0
 HRH  CONST_09  N16  C15  C14  C19     0.00   0.0  0
 HRH  CONST_10  C10  C8   C6   C4      0.00   0.0  0
 HRH  CONST_11  C10  C2   C3   C4      0.00   0.0  0
 HRH  CONST_12  C36  C34  C33  C32     0.00   0.0  0
 HRH  CONST_13  C36  C37  C39  C32     0.00   0.0  0
 HRH  CONST_14  C37  C36  C34  C33     0.00   0.0  0
 HRH  CONST_15  C37  C39  C32  C33     0.00   0.0  0
 HRH  CONST_16  C39  C32  C33  C34     0.00   0.0  0
 HRH  CONST_17  C39  C37  C36  C34     0.00   0.0  0
 HRH  CONST_18  N11  C10  C2   C3    180.00   0.0  0
 HRH  CONST_19  C34  C33  C32  C12   180.00   0.0  0
 HRH  CONST_20  C37  C39  C32  C12   180.00   0.0  0
 HRH  CONST_21  N11  C10  C8   C6    180.00   0.0  0
 HRH  CONST_22  C15  C30  N11  C12     0.00   0.0  0
 HRH  CONST_23  C10  N11  C30  C15   180.00   0.0  0
 HRH  CONST_24  C36  C34  C33  C42   180.00   0.0  0
 HRH  CONST_25  C12  C32  C33  C42     0.00   0.0  0
 HRH  CONST_26  C39  C32  C33  C42   180.00   0.0  0
 HRH  CONST_27  C20  C19  C14  C12     0.00   0.0  0
 HRH  CONST_28  C20  C19  C14  C15   180.00   0.0  0
 HRH  CONST_29  N16  N18  C19  C20   180.00   0.0  0
 HRH  CONST_30  C8   C10  C2   F1    180.00   0.0  0
 HRH  CONST_31  N11  C10  C2   F1      0.00   0.0  0
 HRH  CONST_32  C4   C3   C2   F1    180.00   0.0  0
 HRH  CONST_33  CL2  C3   C4   C6    180.00   0.0  0
 HRH  CONST_34  CL2  C3   C2   C10   180.00   0.0  0
 HRH  CONST_35  CL1  C36  C34  C33   180.00   0.0  0
 HRH  CONST_36  CL1  C36  C37  C39   180.00   0.0  0
 HRH  CONST_37  O31  C30  N11  C12   180.00   0.0  0
 HRH  CONST_38  O31  C30  N11  C10     0.00   0.0  0
 HRH  CONST_39  H14  C8   C10  C2    180.00   0.0  0
 HRH  CONST_40  H12  C4   C3   C2    180.00   0.0  0
 HRH  CONST_41  H13  C6   C4   C3    180.00   0.0  0
 HRH  CONST_42  H18  C39  C32  C12     0.00   0.0  0
 HRH  CONST_43  H15  N16  C15  C14   180.00   0.0  0
 HRH  CONST_44  H16  C34  C33  C32   180.00   0.0  0
 HRH  CONST_45  H17  C37  C39  C32   180.00   0.0  0
 HRH  Var_01    C12  N11  C10  C2   -124.23  30.0  2
 HRH  Var_02    C22  C20  C19  C14    96.75  30.0  2
 HRH  Var_03    H1   C42  C33  C32    61.80  30.0  2
 HRH  Var_04    H6   C22  C20  C19  -177.33  30.0  3
 HRH  Var_05    H9   C26  C20  C19    61.80  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
 HRH  chir_01  C12  C32  C14  N11  negativ

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
 HRH  plan-1  C2   0.020
 HRH  plan-1  C3   0.020
 HRH  plan-1  F1   0.020
 HRH  plan-1  C4   0.020
 HRH  plan-1  C6   0.020
 HRH  plan-1  C8   0.020
 HRH  plan-1  C10  0.020
 HRH  plan-1  N11  0.020
 HRH  plan-1  CL2  0.020
 HRH  plan-1  H12  0.020
 HRH  plan-1  H13  0.020
 HRH  plan-1  H14  0.020
 HRH  plan-2  C42  0.020
 HRH  plan-2  C12  0.020
 HRH  plan-2  C32  0.020
 HRH  plan-2  C33  0.020
 HRH  plan-2  C34  0.020
 HRH  plan-2  C36  0.020
 HRH  plan-2  C37  0.020
 HRH  plan-2  C39  0.020
 HRH  plan-2  CL1  0.020
 HRH  plan-2  H16  0.020
 HRH  plan-2  H17  0.020
 HRH  plan-2  H18  0.020
 HRH  plan-3  C12  0.020
 HRH  plan-3  C14  0.020
 HRH  plan-3  C15  0.020
 HRH  plan-3  C19  0.020
 HRH  plan-3  C20  0.020
 HRH  plan-3  C30  0.020
 HRH  plan-3  C10  0.020
 HRH  plan-3  N11  0.020
 HRH  plan-3  N16  0.020
 HRH  plan-3  N18  0.020
 HRH  plan-3  H15  0.020
 HRH  plan-3  O31  0.020

