# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 16:44:21 2020
#   Inital geometry file: a 132 line input string
#   Ligand name: ~{N}-[(4-chlorophenyl)methyl]-~{N}-methyl-3-[(3-methylphenyl)methyl]-6-oxidanyl-1~{H}-indazole-5-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(Cc1ccc(Cl)cc1)C(=O)c2cc3c(Cc4cccc(C)c4)n[nH]c3cc2O
#
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
 C4N  C4N  ~{N}-[(4-chlorophenyl)methyl]-~{N}-methyl-3-[(3-methylphenyl)methyl]-6-oxidanyl-1~{H}-indazole-5-carboxamide  ligand  52  30  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C4N
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
 C4N  C1   C   CR6   0  -0.211   0.7181   2.4875  -0.3798
 C4N  C2   C   CR6   0   0.358   1.3634   3.7627  -0.4038
 C4N  C3   C   CR16  0  -0.407   2.5472   3.9755   0.2754
 C4N  O5   O   OH1   0  -0.637   0.8440   4.7804  -1.1041
 C4N  C9   C   CR56  0  -0.108   2.3742   1.6859   1.1523
 C4N  C10  C   CR56  0   0.446   3.0438   2.9171   1.0399
 C4N  C13  C   CR5   0   0.245   3.1758   0.9125   2.0457
 C4N  C14  C   CH2   0  -0.590   2.9014  -0.4612   2.5664
 C4N  C15  C   CR6   0   0.114   2.3800  -1.4043   1.5098
 C4N  C16  C   CR16  0  -0.333   1.1426  -2.0191   1.6567
 C4N  C19  C   CR16  0  -0.208   0.6640  -2.8756   0.6718
 C4N  C20  C   CR16  0  -0.334   3.1256  -1.6617   0.3607
 C4N  C21  C   CH3   0  -0.553   0.2036   0.1229  -2.0253
 C4N  C22  C   CH2   0  -0.395  -2.1622   0.7523  -2.0709
 C4N  C24  C   CR16  0  -0.289  -2.6658  -0.6356  -0.0395
 C4N  C27  C   CR16  0  -0.192  -2.9551  -1.8386   0.5814
 C4N  C4   C   CR16  0  -0.323   1.2085   1.4768   0.4242
 C4N  C6   C   C     0   0.563  -0.5504   2.3091  -1.1272
 C4N  N7   N   NT    0  -0.443  -0.8095   1.1029  -1.6672
 C4N  O8   O   O     0  -0.522  -1.3428   3.2552  -1.2131
 C4N  N11  N   NR15  0  -0.562   4.1405   2.8032   1.8150
 C4N  N12  N   N     0  -0.259   4.2220   1.6020   2.4163
 C4N  C17  C   CR16  0  -0.309   1.4161  -3.1208  -0.4648
 C4N  C18  C   CR6   0   0.115   2.6600  -2.5114  -0.6365
 C4N  C23  C   CR6   0   0.120  -2.5566  -0.5517  -1.4253
 C4N  C25  C   CR6   0  -0.055  -3.1352  -2.9720  -0.1982
 C4N  C26  C   CR16  0  -0.196  -3.0440  -2.9155  -1.5778
 C4N  C28  C   CR16  0  -0.304  -2.7521  -1.6991  -2.1817
 C4N  CL   CL  CL    0  -0.130  -3.4585  -4.4898   0.5769
 C4N  H1   H   HCR6  0   0.276   3.0397   4.9383   0.2367
 C4N  H2   H   HOH1  0   0.473  -0.0825   4.5581  -1.3184
 C4N  H3   H   HCH2  0   0.272   3.8170  -0.8553   3.0144
 C4N  H4   H   HCH2  0   0.271   2.1660  -0.3942   3.3736
 C4N  H5   H   HCR6  0   0.249   0.5457  -1.8254   2.5401
 C4N  H6   H   HCR6  0   0.240  -0.3027  -3.3478   0.7925
 C4N  H7   H   HCR6  0   0.239   4.0927  -1.1848   0.2358
 C4N  H8   H   HCH3  0   0.263   0.2468  -0.7147  -1.3290
 C4N  H9   H   HCH3  0   0.264  -0.0396  -0.2732  -3.0122
 C4N  H10  H   HCH3  0   0.272   1.1853   0.5823  -2.0842
 C4N  H11  H   HCH2  0   0.286  -2.8395   1.5506  -1.7739
 C4N  H12  H   HCH2  0   0.268  -2.2159   0.6666  -3.1599
 C4N  H14  H   HCR6  0   0.280  -3.0309  -1.8939   1.6588
 C4N  H18  H   HCR6  0   0.273   0.6896   0.5303   0.4914
 C4N  H19  H   HNR5  0   0.416   4.8514   3.4942   1.9886
 C4N  H20  H   HCR6  0   0.243   1.0319  -3.7839  -1.2312
 C4N  H21  H   HCR6  0   0.279  -3.1863  -3.8035  -2.1787
 C4N  H22  H   HCR6  0   0.265  -2.6660  -1.6555  -3.2607
 C4N  C30  C   CH3   0  -0.723   3.4602  -2.7502  -1.8840
 C4N  H13  H   HCR6  0   0.261  -2.5179   0.2454   0.5738
 C4N  H15  H   HCH3  0   0.246   3.0178  -2.2318  -2.7373
 C4N  H16  H   HCH3  0   0.243   4.4838  -2.3929  -1.7782
 C4N  H17  H   HCH3  0   0.244   3.4977  -3.8097  -2.1389

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
 C4N  C21  N7   single    1.454  0.020  1.454
 C4N  O8   C6   double    1.237  0.020  1.237
 C4N  N7   C6   single    1.347  0.020  1.347
 C4N  N7   C22  single    1.455  0.020  1.455
 C4N  C6   C1   single    1.483  0.020  1.483
 C4N  C17  C19  aromatic  1.385  0.020  1.385
 C4N  C17  C18  aromatic  1.396  0.020  1.396
 C4N  C19  C16  aromatic  1.390  0.020  1.390
 C4N  C28  C26  aromatic  1.389  0.020  1.389
 C4N  C28  C23  aromatic  1.388  0.020  1.388
 C4N  C22  C23  single    1.508  0.020  1.508
 C4N  C26  C25  aromatic  1.384  0.020  1.384
 C4N  C1   C4   aromatic  1.381  0.020  1.381
 C4N  C1   C2   aromatic  1.429  0.020  1.429
 C4N  C30  C18  single    1.501  0.020  1.501
 C4N  C18  C20  aromatic  1.390  0.020  1.390
 C4N  C16  C15  aromatic  1.390  0.020  1.390
 C4N  C23  C24  aromatic  1.393  0.020  1.393
 C4N  O5   C2   single    1.340  0.020  1.340
 C4N  C4   C9   aromatic  1.390  0.020  1.390
 C4N  C2   C3   aromatic  1.381  0.020  1.381
 C4N  C15  C20  aromatic  1.394  0.020  1.394
 C4N  C15  C14  single    1.509  0.020  1.509
 C4N  C25  CL   single    1.735  0.020  1.735
 C4N  C25  C27  aromatic  1.387  0.020  1.387
 C4N  C24  C27  aromatic  1.384  0.020  1.384
 C4N  C9   C10  aromatic  1.406  0.020  1.406
 C4N  C9   C13  aromatic  1.428  0.020  1.428
 C4N  C3   C10  aromatic  1.397  0.020  1.397
 C4N  C14  C13  single    1.495  0.020  1.495
 C4N  C10  N11  aromatic  1.348  0.020  1.348
 C4N  C13  N12  aromatic  1.307  0.020  1.307
 C4N  N11  N12  aromatic  1.346  0.020  1.346
 C4N  C3   H1   single    0.930  0.020  1.080
 C4N  O5   H2   single    0.850  0.020  0.980
 C4N  C14  H3   single    0.970  0.020  1.090
 C4N  C14  H4   single    0.970  0.020  1.090
 C4N  C16  H5   single    0.930  0.020  1.080
 C4N  C19  H6   single    0.930  0.020  1.080
 C4N  C20  H7   single    0.930  0.020  1.080
 C4N  C21  H8   single    0.970  0.020  1.090
 C4N  C21  H9   single    0.970  0.020  1.090
 C4N  C21  H10  single    0.970  0.020  1.090
 C4N  C22  H11  single    0.970  0.020  1.090
 C4N  C22  H12  single    0.970  0.020  1.090
 C4N  C24  H13  single    0.930  0.020  1.080
 C4N  C27  H14  single    0.930  0.020  1.080
 C4N  C30  H15  single    0.970  0.020  1.090
 C4N  C30  H16  single    0.970  0.020  1.090
 C4N  C30  H17  single    0.970  0.020  1.090
 C4N  C4   H18  single    0.930  0.020  1.080
 C4N  N11  H19  single    0.860  0.020  1.020
 C4N  C17  H20  single    0.930  0.020  1.080
 C4N  C26  H21  single    0.930  0.020  1.080
 C4N  C28  H22  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
 C4N  C6   C1   C4   120.59  3.000
 C4N  C4   C1   C2   120.15  3.000
 C4N  C6   C1   C2   119.01  3.000
 C4N  O5   C2   C3   118.18  3.000
 C4N  C3   C2   C1   121.07  3.000
 C4N  O5   C2   C1   120.75  3.000
 C4N  H1   C3   C10  122.14  3.000
 C4N  H1   C3   C2   120.63  3.000
 C4N  C10  C3   C2   117.20  3.000
 C4N  H2   O5   C2   108.03  3.000
 C4N  C4   C9   C13  135.81  3.000
 C4N  C13  C9   C10  104.89  3.000
 C4N  C4   C9   C10  119.28  3.000
 C4N  N11  C10  C9   105.52  3.000
 C4N  N11  C10  C3   131.92  3.000
 C4N  C9   C10  C3   122.54  3.000
 C4N  N12  C13  C14  122.22  3.000
 C4N  N12  C13  C9   109.95  3.000
 C4N  C14  C13  C9   127.79  3.000
 C4N  H4   C14  H3   106.42  3.000
 C4N  H4   C14  C15  108.82  3.000
 C4N  H3   C14  C15  110.56  3.000
 C4N  H4   C14  C13  108.92  3.000
 C4N  H3   C14  C13  108.69  3.000
 C4N  C15  C14  C13  113.20  3.000
 C4N  C20  C15  C16  118.80  3.000
 C4N  C20  C15  C14  120.52  3.000
 C4N  C16  C15  C14  120.68  3.000
 C4N  H5   C16  C19  119.87  3.000
 C4N  H5   C16  C15  119.84  3.000
 C4N  C19  C16  C15  120.29  3.000
 C4N  H6   C19  C17  119.95  3.000
 C4N  H6   C19  C16  119.81  3.000
 C4N  C17  C19  C16  120.24  3.000
 C4N  H7   C20  C18  118.97  3.000
 C4N  H7   C20  C15  119.36  3.000
 C4N  C18  C20  C15  121.67  3.000
 C4N  H10  C21  H9   107.83  3.000
 C4N  H10  C21  H8   108.90  3.000
 C4N  H9   C21  H8   107.92  3.000
 C4N  H10  C21  N7   110.99  3.000
 C4N  H9   C21  N7   108.19  3.000
 C4N  H8   C21  N7   112.84  3.000
 C4N  H12  C22  H11  107.38  3.000
 C4N  H12  C22  C23  110.23  3.000
 C4N  H11  C22  C23  110.78  3.000
 C4N  H12  C22  N7   109.93  3.000
 C4N  H11  C22  N7   109.04  3.000
 C4N  C23  C22  N7   109.44  3.000
 C4N  H13  C24  C23  120.24  3.000
 C4N  H13  C24  C27  118.76  3.000
 C4N  C23  C24  C27  121.00  3.000
 C4N  H14  C27  C25  120.60  3.000
 C4N  H14  C27  C24  120.39  3.000
 C4N  C25  C27  C24  119.01  3.000
 C4N  H18  C4   C9   120.09  3.000
 C4N  H18  C4   C1   120.41  3.000
 C4N  C9   C4   C1   119.50  3.000
 C4N  O8   C6   N7   122.27  3.000
 C4N  N7   C6   C1   118.32  3.000
 C4N  O8   C6   C1   119.40  3.000
 C4N  C6   N7   C22  120.40  3.000
 C4N  C22  N7   C21  114.65  3.000
 C4N  C6   N7   C21  124.63  3.000
 C4N  H19  N11  N12  119.53  3.000
 C4N  H19  N11  C10  128.02  3.000
 C4N  N12  N11  C10  112.44  3.000
 C4N  N11  N12  C13  107.20  3.000
 C4N  H20  C17  C18  119.74  3.000
 C4N  H20  C17  C19  119.75  3.000
 C4N  C18  C17  C19  120.51  3.000
 C4N  C17  C18  C30  120.52  3.000
 C4N  C30  C18  C20  120.98  3.000
 C4N  C17  C18  C20  118.49  3.000
 C4N  C28  C23  C24  118.78  3.000
 C4N  C24  C23  C22  119.92  3.000
 C4N  C28  C23  C22  121.23  3.000
 C4N  CL   C25  C26  119.57  3.000
 C4N  CL   C25  C27  119.20  3.000
 C4N  C26  C25  C27  121.22  3.000
 C4N  H21  C26  C28  120.33  3.000
 C4N  H21  C26  C25  120.78  3.000
 C4N  C28  C26  C25  118.88  3.000
 C4N  H22  C28  C26  119.01  3.000
 C4N  H22  C28  C23  119.89  3.000
 C4N  C26  C28  C23  121.10  3.000
 C4N  H17  C30  H16  108.01  3.000
 C4N  H17  C30  H15  107.01  3.000
 C4N  H16  C30  H15  107.51  3.000
 C4N  H17  C30  C18  111.54  3.000
 C4N  H16  C30  C18  111.59  3.000
 C4N  H15  C30  C18  110.97  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
 C4N  CONST_01  C10  C9   C4   C1      0.00   0.0  0
 C4N  CONST_02  C13  C9   C4   C1    180.00   0.0  0
 C4N  CONST_03  C10  C3   C2   C1      0.00   0.0  0
 C4N  CONST_04  C9   C4   C1   C2      0.00   0.0  0
 C4N  CONST_05  C9   C10  C3   C2      0.00   0.0  0
 C4N  CONST_06  N11  C10  C3   C2    180.00   0.0  0
 C4N  CONST_07  C4   C1   C2   C3      0.00   0.0  0
 C4N  CONST_08  C4   C9   C10  C3      0.00   0.0  0
 C4N  CONST_09  C13  C9   C10  C3    180.00   0.0  0
 C4N  CONST_10  N12  N11  C10  C3    180.00   0.0  0
 C4N  CONST_11  N12  N11  C10  C9      0.00   0.0  0
 C4N  CONST_12  N11  N12  C13  C9      0.00   0.0  0
 C4N  CONST_13  N12  C13  C9   C10     0.00   0.0  0
 C4N  CONST_14  C13  N12  N11  C10     0.00   0.0  0
 C4N  CONST_15  N11  C10  C9   C13     0.00   0.0  0
 C4N  CONST_16  C17  C19  C16  C15     0.00   0.0  0
 C4N  CONST_17  C17  C18  C20  C15     0.00   0.0  0
 C4N  CONST_18  C18  C17  C19  C16     0.00   0.0  0
 C4N  CONST_19  C18  C20  C15  C16     0.00   0.0  0
 C4N  CONST_20  C20  C18  C17  C19     0.00   0.0  0
 C4N  CONST_21  C20  C15  C16  C19     0.00   0.0  0
 C4N  CONST_22  C26  C28  C23  C24     0.00   0.0  0
 C4N  CONST_23  C26  C25  C27  C24     0.00   0.0  0
 C4N  CONST_24  C28  C26  C25  C27     0.00   0.0  0
 C4N  CONST_25  C28  C23  C24  C27     0.00   0.0  0
 C4N  CONST_26  N11  C10  C9   C4    180.00   0.0  0
 C4N  CONST_27  N12  C13  C9   C4    180.00   0.0  0
 C4N  CONST_28  C25  C26  C28  C23     0.00   0.0  0
 C4N  CONST_29  C25  C27  C24  C23     0.00   0.0  0
 C4N  CONST_30  C6   C1   C2   C3    180.00   0.0  0
 C4N  CONST_31  C4   C1   C2   O5    180.00   0.0  0
 C4N  CONST_32  C10  C3   C2   O5    180.00   0.0  0
 C4N  CONST_33  C6   C1   C4   C9    180.00   0.0  0
 C4N  CONST_34  C14  C13  C9   C10   180.00   0.0  0
 C4N  CONST_35  C19  C16  C15  C14   180.00   0.0  0
 C4N  CONST_36  C18  C20  C15  C14   180.00   0.0  0
 C4N  CONST_37  C4   C9   C13  C14     0.00   0.0  0
 C4N  CONST_38  N11  N12  C13  C14   180.00   0.0  0
 C4N  CONST_39  C30  C18  C20  C15   180.00   0.0  0
 C4N  CONST_40  C30  C18  C17  C19   180.00   0.0  0
 C4N  CONST_41  C26  C28  C23  C22   180.00   0.0  0
 C4N  CONST_42  C27  C24  C23  C22   180.00   0.0  0
 C4N  CONST_43  CL   C25  C27  C24   180.00   0.0  0
 C4N  CONST_44  CL   C25  C26  C28   180.00   0.0  0
 C4N  CONST_45  H1   C3   C2   C1    180.00   0.0  0
 C4N  CONST_46  H18  C4   C1   C2    180.00   0.0  0
 C4N  CONST_47  H19  N11  C10  C3      0.00   0.0  0
 C4N  CONST_48  H6   C19  C16  C15   180.00   0.0  0
 C4N  CONST_49  H20  C17  C19  C16   180.00   0.0  0
 C4N  CONST_50  H7   C20  C15  C16   180.00   0.0  0
 C4N  CONST_51  H5   C16  C15  C20   180.00   0.0  0
 C4N  CONST_52  H22  C28  C23  C24   180.00   0.0  0
 C4N  CONST_53  H21  C26  C25  C27   180.00   0.0  0
 C4N  CONST_54  H14  C27  C24  C23   180.00   0.0  0
 C4N  CONST_55  H13  C24  C27  C25   180.00   0.0  0
 C4N  Var_01    C15  C14  C13  C9     42.57  30.0  1
 C4N  Var_02    C16  C15  C14  C13  -120.91  30.0  2
 C4N  Var_03    O8   C6   C1   C2    -33.91  30.0  2
 C4N  Var_04    N7   C22  C23  C24    64.27  30.0  2
 C4N  Var_05    H15  C30  C18  C20  -106.08  30.0  2
 C4N  Var_06    C23  C22  N7   C21    59.57  30.0  3
 C4N  Var_07    H8   C21  N7   C22   -80.87  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
 C4N  plan-1  C14  0.020
 C4N  plan-1  C15  0.020
 C4N  plan-1  C16  0.020
 C4N  plan-1  C19  0.020
 C4N  plan-1  C20  0.020
 C4N  plan-1  C17  0.020
 C4N  plan-1  C18  0.020
 C4N  plan-1  H5   0.020
 C4N  plan-1  H6   0.020
 C4N  plan-1  H7   0.020
 C4N  plan-1  H20  0.020
 C4N  plan-1  C30  0.020
 C4N  plan-2  C22  0.020
 C4N  plan-2  C24  0.020
 C4N  plan-2  C27  0.020
 C4N  plan-2  C23  0.020
 C4N  plan-2  C25  0.020
 C4N  plan-2  C26  0.020
 C4N  plan-2  C28  0.020
 C4N  plan-2  CL   0.020
 C4N  plan-2  H14  0.020
 C4N  plan-2  H21  0.020
 C4N  plan-2  H22  0.020
 C4N  plan-2  H13  0.020
 C4N  plan-3  C1   0.020
 C4N  plan-3  C2   0.020
 C4N  plan-3  C3   0.020
 C4N  plan-3  O5   0.020
 C4N  plan-3  C9   0.020
 C4N  plan-3  C10  0.020
 C4N  plan-3  C13  0.020
 C4N  plan-3  C14  0.020
 C4N  plan-3  C4   0.020
 C4N  plan-3  C6   0.020
 C4N  plan-3  N11  0.020
 C4N  plan-3  N12  0.020
 C4N  plan-3  H1   0.020
 C4N  plan-3  H18  0.020
 C4N  plan-3  H19  0.020
 C4N  plan-4  C1   0.020
 C4N  plan-4  C21  0.020
 C4N  plan-4  C22  0.020
 C4N  plan-4  C6   0.020
 C4N  plan-4  N7   0.020
 C4N  plan-4  O8   0.020

