# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 18:57:53 2020
#   Inital geometry file: a 153 line input string
#   Ligand name: 4,4'-(2-{3-[(3-methylphenyl)amino]phenyl}but-1-ene-1,1-diyl)diphenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(c1cccc(Nc2cccc(C)c2)c1)=C(c3ccc(O)cc3)c4ccc(O)cc4
#
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
 5C9  5C9  4,4'-(2-{3-[(3-methylphenyl)amino]phenyl}but-1-ene-1,1-diyl)diphenol  ligand  59  32  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_5C9
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
 5C9  C01  C  CH3   0  -0.659  -1.2122   1.8994  -3.1663
 5C9  C02  C  CH2   0  -0.516  -1.0697   1.9109  -1.6459
 5C9  C03  C  C     0   0.052  -1.0177   0.5328  -1.0401
 5C9  C04  C  C     0   0.041  -1.9729   0.0225  -0.2386
 5C9  C05  C  CR6   0   0.007  -3.2664   0.7046   0.0045
 5C9  C06  C  CR16  0  -0.282  -4.1049   1.0791  -1.0455
 5C9  C07  C  CR16  0  -0.326  -5.3310   1.6820  -0.8177
 5C9  C08  C  CR6   0   0.342  -5.7537   1.9240   0.4868
 5C9  O09  O  OH1   0  -0.631  -6.9551   2.5074   0.6630
 5C9  C10  C  CR16  0  -0.370  -4.9346   1.5494   1.5501
 5C9  C11  C  CR16  0  -0.279  -3.7148   0.9403   1.3038
 5C9  C12  C  CR6   0   0.016  -1.8020  -1.2640   0.4783
 5C9  C13  C  CR16  0  -0.275  -0.6649  -1.5363   1.2356
 5C9  C14  C  CR16  0  -0.373  -0.5154  -2.7353   1.9137
 5C9  C15  C  CR6   0   0.339  -1.5145  -3.7028   1.8462
 5C9  O16  O  OH1   0  -0.633  -1.4234  -4.8907   2.4779
 5C9  C17  C  CR16  0  -0.325  -2.6665  -3.4432   1.1065
 5C9  C18  C  CR16  0  -0.279  -2.8040  -2.2350   0.4453
 5C9  C19  C  CR6   0   0.054   0.1793  -0.2639  -1.4126
 5C9  C20  C  CR16  0  -0.297   0.0315  -1.4662  -2.1022
 5C9  C21  C  CR16  0  -0.229   1.1543  -2.1749  -2.5003
 5C9  C22  C  CR16  0  -0.360   2.4260  -1.7188  -2.1941
 5C9  C23  C  CR6   0   0.382   2.5912  -0.5172  -1.5005
 5C9  N24  N  NH1   0  -0.804   3.8766  -0.0627  -1.2404
 5C9  C25  C  CR6   0   0.372   4.3259   0.6396  -0.1353
 5C9  C26  C  CR16  0  -0.346   3.6094   0.7265   1.0629
 5C9  C27  C  CR16  0  -0.235   4.1425   1.4303   2.1313
 5C9  C28  C  CR16  0  -0.335   5.3851   2.0428   2.0445
 5C9  C29  C  CR6   0   0.111   6.1202   1.9491   0.8645
 5C9  C30  C  CH3   0  -0.723   7.4825   2.5707   0.7495
 5C9  C31  C  CR16  0  -0.397   5.5782   1.2581  -0.2121
 5C9  C32  C  CR16  0  -0.388   1.4575   0.2144  -1.1413
 5C9  H1   H  HCH3  0   0.232  -1.2056   2.9163  -3.5595
 5C9  H2   H  HCH3  0   0.227  -0.3957   1.3538  -3.6400
 5C9  H3   H  HCH3  0   0.225  -2.1469   1.4285  -3.4727
 5C9  H4   H  HCH2  0   0.243  -0.1415   2.4316  -1.3888
 5C9  H5   H  HCH2  0   0.244  -1.8760   2.4951  -1.2019
 5C9  H8   H  HCR6  0   0.256  -3.8039   0.8777  -2.0657
 5C9  H9   H  HCR6  0   0.261  -5.9684   1.9542  -1.6501
 5C9  H10  H  HOH1  0   0.474  -7.1525   2.5946   1.6020
 5C9  H11  H  HCR6  0   0.270  -5.2510   1.7265   2.5720
 5C9  H12  H  HCR6  0   0.249  -3.0983   0.6469   2.1452
 5C9  H13  H  HCR6  0   0.257   0.1211  -0.7957   1.3082
 5C9  H14  H  HCR6  0   0.266   0.3789  -2.9132   2.5011
 5C9  H15  H  HOH1  0   0.473  -0.5956  -4.9469   2.9677
 5C9  H16  H  HCR6  0   0.260  -3.4519  -4.1871   1.0551
 5C9  H17  H  HCR6  0   0.244  -3.7106  -2.0485  -0.1180
 5C9  H18  H  HCR6  0   0.241  -0.9588  -1.8348  -2.3346
 5C9  H19  H  HCR6  0   0.251   1.0403  -3.1015  -3.0487
 5C9  H20  H  HCR6  0   0.258   3.2967  -2.2915  -2.4915
 5C9  H21  H  HNH1  0   0.396   4.5950  -0.4069  -1.8570
 5C9  H22  H  HCR6  0   0.272   2.6506   0.2390   1.1741
 5C9  H23  H  HCR6  0   0.251   3.5767   1.4896   3.0527
 5C9  H24  H  HCR6  0   0.241   5.7841   2.5888   2.8905
 5C9  H25  H  HCH3  0   0.248   8.2654   1.8205   0.8783
 5C9  H26  H  HCH3  0   0.243   7.6331   3.0269  -0.2291
 5C9  H27  H  HCH3  0   0.243   7.6372   3.3375   1.5075
 5C9  H28  H  HCR6  0   0.251   6.1383   1.1970  -1.1398
 5C9  H29  H  HCR6  0   0.269   1.5706   1.1685  -0.6418

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
 5C9  C30  C29  single    1.502  0.020  1.502
 5C9  C28  C29  aromatic  1.393  0.020  1.393
 5C9  C28  C27  aromatic  1.388  0.020  1.388
 5C9  C29  C31  aromatic  1.389  0.020  1.389
 5C9  C27  C26  aromatic  1.386  0.020  1.386
 5C9  C31  C25  aromatic  1.399  0.020  1.399
 5C9  C26  C25  aromatic  1.399  0.020  1.399
 5C9  C25  N24  single    1.384  0.020  1.384
 5C9  C22  C21  aromatic  1.385  0.020  1.385
 5C9  C22  C23  aromatic  1.397  0.020  1.397
 5C9  C21  C20  aromatic  1.386  0.020  1.386
 5C9  N24  C23  single    1.388  0.020  1.388
 5C9  C23  C32  aromatic  1.396  0.020  1.396
 5C9  C20  C19  aromatic  1.394  0.020  1.394
 5C9  C32  C19  aromatic  1.391  0.020  1.391
 5C9  C19  C03  single    1.485  0.020  1.485
 5C9  C01  C02  single    1.527  0.020  1.527
 5C9  O09  C08  single    1.347  0.020  1.347
 5C9  C03  C02  single    1.506  0.020  1.506
 5C9  C03  C04  double    1.347  0.020  1.347
 5C9  C08  C07  aromatic  1.392  0.020  1.392
 5C9  C08  C10  aromatic  1.393  0.020  1.393
 5C9  C07  C06  aromatic  1.385  0.020  1.385
 5C9  C10  C11  aromatic  1.386  0.020  1.386
 5C9  C06  C05  aromatic  1.395  0.020  1.395
 5C9  C11  C05  aromatic  1.395  0.020  1.395
 5C9  C05  C04  single    1.482  0.020  1.482
 5C9  C04  C12  single    1.483  0.020  1.483
 5C9  C13  C12  aromatic  1.393  0.020  1.393
 5C9  C13  C14  aromatic  1.386  0.020  1.386
 5C9  C12  C18  aromatic  1.396  0.020  1.396
 5C9  C14  C15  aromatic  1.392  0.020  1.392
 5C9  C18  C17  aromatic  1.384  0.020  1.384
 5C9  C15  C17  aromatic  1.394  0.020  1.394
 5C9  C15  O16  single    1.349  0.020  1.349
 5C9  C01  H1   single    0.970  0.020  1.090
 5C9  C01  H2   single    0.970  0.020  1.090
 5C9  C01  H3   single    0.970  0.020  1.090
 5C9  C02  H4   single    0.970  0.020  1.090
 5C9  C02  H5   single    0.970  0.020  1.090
 5C9  C06  H8   single    0.930  0.020  1.080
 5C9  C07  H9   single    0.930  0.020  1.080
 5C9  O09  H10  single    0.850  0.020  0.980
 5C9  C10  H11  single    0.930  0.020  1.080
 5C9  C11  H12  single    0.930  0.020  1.080
 5C9  C13  H13  single    0.930  0.020  1.080
 5C9  C14  H14  single    0.930  0.020  1.080
 5C9  O16  H15  single    0.850  0.020  0.980
 5C9  C17  H16  single    0.930  0.020  1.080
 5C9  C18  H17  single    0.930  0.020  1.080
 5C9  C20  H18  single    0.930  0.020  1.080
 5C9  C21  H19  single    0.930  0.020  1.080
 5C9  C22  H20  single    0.930  0.020  1.080
 5C9  N24  H21  single    0.860  0.020  1.020
 5C9  C26  H22  single    0.930  0.020  1.080
 5C9  C27  H23  single    0.930  0.020  1.080
 5C9  C28  H24  single    0.930  0.020  1.080
 5C9  C30  H25  single    0.970  0.020  1.090
 5C9  C30  H26  single    0.970  0.020  1.090
 5C9  C30  H27  single    0.970  0.020  1.090
 5C9  C31  H28  single    0.930  0.020  1.080
 5C9  C32  H29  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
 5C9  H3   C01  H2   107.68  3.000
 5C9  H3   C01  H1   107.85  3.000
 5C9  H2   C01  H1   107.79  3.000
 5C9  H3   C01  C02  111.28  3.000
 5C9  H2   C01  C02  111.50  3.000
 5C9  H1   C01  C02  110.58  3.000
 5C9  H5   C02  H4   106.05  3.000
 5C9  H5   C02  C03  110.60  3.000
 5C9  H4   C02  C03  108.14  3.000
 5C9  H5   C02  C01  109.91  3.000
 5C9  H4   C02  C01  108.45  3.000
 5C9  C03  C02  C01  113.38  3.000
 5C9  C19  C03  C04  121.16  3.000
 5C9  C04  C03  C02  124.15  3.000
 5C9  C19  C03  C02  114.68  3.000
 5C9  C12  C04  C05  114.87  3.000
 5C9  C12  C04  C03  122.32  3.000
 5C9  C05  C04  C03  122.81  3.000
 5C9  C11  C05  C06  117.56  3.000
 5C9  C11  C05  C04  120.74  3.000
 5C9  C06  C05  C04  121.65  3.000
 5C9  H8   C06  C07  118.82  3.000
 5C9  H8   C06  C05  119.49  3.000
 5C9  C07  C06  C05  121.68  3.000
 5C9  H9   C07  C08  119.84  3.000
 5C9  H9   C07  C06  120.26  3.000
 5C9  C08  C07  C06  119.89  3.000
 5C9  C10  C08  O09  122.74  3.000
 5C9  C10  C08  C07  119.32  3.000
 5C9  O09  C08  C07  117.94  3.000
 5C9  H10  O09  C08  110.45  3.000
 5C9  H11  C10  C11  119.75  3.000
 5C9  H11  C10  C08  120.24  3.000
 5C9  C11  C10  C08  120.00  3.000
 5C9  H12  C11  C10  118.81  3.000
 5C9  H12  C11  C05  119.66  3.000
 5C9  C10  C11  C05  121.53  3.000
 5C9  C18  C12  C13  117.57  3.000
 5C9  C18  C12  C04  120.63  3.000
 5C9  C13  C12  C04  121.77  3.000
 5C9  H13  C13  C14  118.74  3.000
 5C9  H13  C13  C12  119.70  3.000
 5C9  C14  C13  C12  121.56  3.000
 5C9  H14  C14  C15  120.26  3.000
 5C9  H14  C14  C13  119.73  3.000
 5C9  C15  C14  C13  120.01  3.000
 5C9  C17  C15  O16  117.94  3.000
 5C9  O16  C15  C14  122.75  3.000
 5C9  C17  C15  C14  119.31  3.000
 5C9  H15  O16  C15  110.33  3.000
 5C9  H16  C17  C18  120.32  3.000
 5C9  H16  C17  C15  119.79  3.000
 5C9  C18  C17  C15  119.89  3.000
 5C9  H17  C18  C17  118.80  3.000
 5C9  H17  C18  C12  119.55  3.000
 5C9  C17  C18  C12  121.65  3.000
 5C9  C32  C19  C20  119.36  3.000
 5C9  C32  C19  C03  120.47  3.000
 5C9  C20  C19  C03  120.08  3.000
 5C9  H18  C20  C21  120.37  3.000
 5C9  H18  C20  C19  119.81  3.000
 5C9  C21  C20  C19  119.82  3.000
 5C9  H19  C21  C22  119.36  3.000
 5C9  H19  C21  C20  119.85  3.000
 5C9  C22  C21  C20  120.78  3.000
 5C9  H20  C22  C23  119.72  3.000
 5C9  H20  C22  C21  120.19  3.000
 5C9  C23  C22  C21  120.09  3.000
 5C9  C32  C23  N24  122.15  3.000
 5C9  C32  C23  C22  118.84  3.000
 5C9  N24  C23  C22  118.95  3.000
 5C9  H21  N24  C25  115.50  3.000
 5C9  H21  N24  C23  115.72  3.000
 5C9  C25  N24  C23  128.05  3.000
 5C9  C31  C25  C26  118.56  3.000
 5C9  C26  C25  N24  123.31  3.000
 5C9  C31  C25  N24  118.10  3.000
 5C9  H22  C26  C27  119.39  3.000
 5C9  H22  C26  C25  120.94  3.000
 5C9  C27  C26  C25  119.66  3.000
 5C9  H23  C27  C28  119.79  3.000
 5C9  H23  C27  C26  118.86  3.000
 5C9  C28  C27  C26  121.35  3.000
 5C9  H24  C28  C29  120.07  3.000
 5C9  H24  C28  C27  120.23  3.000
 5C9  C29  C28  C27  119.71  3.000
 5C9  C31  C29  C30  120.03  3.000
 5C9  C31  C29  C28  118.94  3.000
 5C9  C30  C29  C28  121.04  3.000
 5C9  H27  C30  H26  108.09  3.000
 5C9  H27  C30  H25  107.44  3.000
 5C9  H26  C30  H25  107.12  3.000
 5C9  H27  C30  C29  111.52  3.000
 5C9  H26  C30  C29  111.54  3.000
 5C9  H25  C30  C29  110.92  3.000
 5C9  H28  C31  C29  119.27  3.000
 5C9  H28  C31  C25  118.95  3.000
 5C9  C29  C31  C25  121.78  3.000
 5C9  H29  C32  C23  119.70  3.000
 5C9  H29  C32  C19  119.26  3.000
 5C9  C23  C32  C19  121.04  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
 5C9  CONST_01  C08  C07  C06  C05     0.00   0.0  0
 5C9  CONST_02  C08  C10  C11  C05     0.00   0.0  0
 5C9  CONST_03  C10  C08  C07  C06     0.00   0.0  0
 5C9  CONST_04  C10  C11  C05  C06     0.00   0.0  0
 5C9  CONST_05  C11  C10  C08  C07     0.00   0.0  0
 5C9  CONST_06  C11  C05  C06  C07     0.00   0.0  0
 5C9  CONST_07  C15  C14  C13  C12     0.00   0.0  0
 5C9  CONST_08  C15  C17  C18  C12     0.00   0.0  0
 5C9  CONST_09  C17  C18  C12  C13     0.00   0.0  0
 5C9  CONST_10  C17  C15  C14  C13     0.00   0.0  0
 5C9  CONST_11  C18  C12  C13  C14     0.00   0.0  0
 5C9  CONST_12  C18  C17  C15  C14     0.00   0.0  0
 5C9  CONST_13  C22  C21  C20  C19     0.00   0.0  0
 5C9  CONST_14  C22  C23  C32  C19     0.00   0.0  0
 5C9  CONST_15  C23  C22  C21  C20     0.00   0.0  0
 5C9  CONST_16  C23  C32  C19  C20     0.00   0.0  0
 5C9  CONST_17  C32  C23  C22  C21     0.00   0.0  0
 5C9  CONST_18  C32  C19  C20  C21     0.00   0.0  0
 5C9  CONST_19  C28  C29  C31  C25     0.00   0.0  0
 5C9  CONST_20  C28  C27  C26  C25     0.00   0.0  0
 5C9  CONST_21  C29  C28  C27  C26     0.00   0.0  0
 5C9  CONST_22  C29  C31  C25  C26     0.00   0.0  0
 5C9  CONST_23  C31  C29  C28  C27     0.00   0.0  0
 5C9  CONST_24  C31  C25  C26  C27     0.00   0.0  0
 5C9  CONST_25  C21  C20  C19  C03   180.00   0.0  0
 5C9  CONST_26  C23  C32  C19  C03   180.00   0.0  0
 5C9  CONST_27  C07  C06  C05  C04   180.00   0.0  0
 5C9  CONST_28  C10  C11  C05  C04   180.00   0.0  0
 5C9  CONST_29  C14  C13  C12  C04   180.00   0.0  0
 5C9  CONST_30  C17  C18  C12  C04   180.00   0.0  0
 5C9  CONST_31  O09  C08  C07  C06   180.00   0.0  0
 5C9  CONST_32  C11  C10  C08  O09   180.00   0.0  0
 5C9  CONST_33  O16  C15  C14  C13   180.00   0.0  0
 5C9  CONST_34  C18  C17  C15  O16   180.00   0.0  0
 5C9  CONST_35  N24  C23  C32  C19   180.00   0.0  0
 5C9  CONST_36  N24  C23  C22  C21   180.00   0.0  0
 5C9  CONST_37  C29  C31  C25  N24   180.00   0.0  0
 5C9  CONST_38  C27  C26  C25  N24   180.00   0.0  0
 5C9  CONST_39  C30  C29  C31  C25   180.00   0.0  0
 5C9  CONST_40  C30  C29  C28  C27   180.00   0.0  0
 5C9  CONST_41  H9   C07  C06  C05   180.00   0.0  0
 5C9  CONST_42  H11  C10  C11  C05   180.00   0.0  0
 5C9  CONST_43  H12  C11  C05  C06   180.00   0.0  0
 5C9  CONST_44  H8   C06  C07  C08   180.00   0.0  0
 5C9  CONST_45  H14  C14  C13  C12   180.00   0.0  0
 5C9  CONST_46  H16  C17  C18  C12   180.00   0.0  0
 5C9  CONST_47  H17  C18  C12  C13   180.00   0.0  0
 5C9  CONST_48  H13  C13  C14  C15   180.00   0.0  0
 5C9  CONST_49  H19  C21  C20  C19   180.00   0.0  0
 5C9  CONST_50  H20  C22  C21  C20   180.00   0.0  0
 5C9  CONST_51  H29  C32  C19  C20   180.00   0.0  0
 5C9  CONST_52  H18  C20  C21  C22   180.00   0.0  0
 5C9  CONST_53  H23  C27  C26  C25   180.00   0.0  0
 5C9  CONST_54  H24  C28  C27  C26   180.00   0.0  0
 5C9  CONST_55  H28  C31  C25  C26   180.00   0.0  0
 5C9  CONST_56  H22  C26  C27  C28   180.00   0.0  0
 5C9  Var_01    C13  C12  C04  C05  -129.59  30.0  2
 5C9  Var_02    C12  C04  C05  C06  -125.23  30.0  2
 5C9  Var_03    C25  N24  C23  C22  -146.20  30.0  3
 5C9  Var_04    C31  C25  N24  C23  -165.74  30.0  3
 5C9  Var_05    C19  C03  C04  C05  -171.19   0.0  2
 5C9  Var_06    C20  C19  C03  C02  -118.67  30.0  2
 5C9  Var_07    H25  C30  C29  C28   100.11  30.0  2
 5C9  Var_08    H1   C01  C02  C03  -177.77  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
 5C9  plan-1  C04  0.020
 5C9  plan-1  C05  0.020
 5C9  plan-1  C06  0.020
 5C9  plan-1  C07  0.020
 5C9  plan-1  C08  0.020
 5C9  plan-1  O09  0.020
 5C9  plan-1  C10  0.020
 5C9  plan-1  C11  0.020
 5C9  plan-1  H8   0.020
 5C9  plan-1  H9   0.020
 5C9  plan-1  H11  0.020
 5C9  plan-1  H12  0.020
 5C9  plan-2  C04  0.020
 5C9  plan-2  C12  0.020
 5C9  plan-2  C13  0.020
 5C9  plan-2  C14  0.020
 5C9  plan-2  C15  0.020
 5C9  plan-2  O16  0.020
 5C9  plan-2  C17  0.020
 5C9  plan-2  C18  0.020
 5C9  plan-2  H13  0.020
 5C9  plan-2  H14  0.020
 5C9  plan-2  H16  0.020
 5C9  plan-2  H17  0.020
 5C9  plan-3  C03  0.020
 5C9  plan-3  C19  0.020
 5C9  plan-3  C20  0.020
 5C9  plan-3  C21  0.020
 5C9  plan-3  C22  0.020
 5C9  plan-3  C23  0.020
 5C9  plan-3  N24  0.020
 5C9  plan-3  C32  0.020
 5C9  plan-3  H18  0.020
 5C9  plan-3  H19  0.020
 5C9  plan-3  H20  0.020
 5C9  plan-3  H29  0.020
 5C9  plan-4  N24  0.020
 5C9  plan-4  C25  0.020
 5C9  plan-4  C26  0.020
 5C9  plan-4  C27  0.020
 5C9  plan-4  C28  0.020
 5C9  plan-4  C29  0.020
 5C9  plan-4  C30  0.020
 5C9  plan-4  C31  0.020
 5C9  plan-4  H22  0.020
 5C9  plan-4  H23  0.020
 5C9  plan-4  H24  0.020
 5C9  plan-4  H28  0.020
 5C9  plan-5  C02  0.020
 5C9  plan-5  C03  0.020
 5C9  plan-5  C04  0.020
 5C9  plan-5  C05  0.020
 5C9  plan-5  C12  0.020
 5C9  plan-5  C19  0.020

