# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  2 23:55:37 2020
#   Inital geometry file: a 85 line input string
#   Ligand name: 4-chloro-6-(4-piperazin-1-yl-1H-pyrazol-5-yl)benzene-1,3-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(O)c(cc1Cl)c2[nH]ncc2N3CCNCC3
#
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
 4BH  4BH  4-chloro-6-(4-piperazin-1-yl-1H-pyrazol-5-yl)benzene-1,3-diol  ligand  35  20  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4BH
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
 4BH  CL    CL  CL    0  -0.117   4.3302   0.9056  -1.1714
 4BH  C1    C   CR6   0  -0.166   2.9527   0.6632  -0.1524
 4BH  C2    C   CR6   0   0.441   3.1137   0.0034   1.0658
 4BH  O2    O   OH1   0  -0.608   4.3377  -0.4171   1.3996
 4BH  C3    C   CR16  0  -0.521   2.0016  -0.1855   1.8788
 4BH  C4    C   CR6   0   0.371   0.7486   0.2717   1.4871
 4BH  O4    O   OH1   0  -0.612  -0.3365   0.1174   2.2591
 4BH  C5    C   CR16  0  -0.225   1.7050   1.1090  -0.5431
 4BH  C6    C   CR6   0  -0.117   0.5834   0.9180   0.2571
 4BH  C7    C   CR5   0   0.398  -0.7270   1.4176  -0.1712
 4BH  N1    N   NR15  0  -0.487  -0.9319   2.7443  -0.3571
 4BH  N2    N   N     0  -0.256  -2.1565   3.0435  -0.7527
 4BH  C8    C   CR15  0  -0.127  -2.7720   1.8812  -0.8597
 4BH  C9    C   CR5   0   0.023  -1.9260   0.8068  -0.5092
 4BH  N3    N   NT    0  -0.518  -2.2860  -0.5411  -0.5704
 4BH  C11   C   CH2   0  -0.288  -3.2947  -0.9607   0.3926
 4BH  C12   C   CH2   0  -0.302  -3.8615  -2.3105  -0.0067
 4BH  C15   C   CH2   0  -0.291  -1.2254  -1.5192  -0.7184
 4BH  C14   C   CH2   0  -0.297  -1.8237  -2.8559  -1.1209
 4BH  N4    N   NH1   0  -0.600  -2.7825  -3.2744  -0.1158
 4BH  H2    H   HOH1  0   0.485   4.3235  -0.8628   2.2547
 4BH  H3    H   HCR6  0   0.294   2.1184  -0.6899   2.8334
 4BH  H4    H   HOH1  0   0.480  -0.1220  -0.3873   3.0521
 4BH  H5    H   HCR6  0   0.280   1.5962   1.6041  -1.4996
 4BH  H1    H   HNR5  0   0.414  -0.2618   3.4789  -0.1917
 4BH  H8    H   HCR5  0   0.257  -3.8008   1.8303  -1.1860
 4BH  H111  H   HCH2  0   0.204  -2.8753  -1.0232   1.4075
 4BH  H112  H   HCH2  0   0.240  -4.0985  -0.2237   0.4158
 4BH  H121  H   HCH2  0   0.233  -4.5699  -2.6425   0.7550
 4BH  H122  H   HCH2  0   0.191  -4.4225  -2.1931  -0.9476
 4BH  H151  H   HCH2  0   0.238  -0.5286  -1.1822  -1.4882
 4BH  H152  H   HCH2  0   0.206  -0.6526  -1.6602   0.2088
 4BH  H141  H   HCH2  0   0.232  -1.0262  -3.5983  -1.1905
 4BH  H142  H   HCH2  0   0.191  -2.2710  -2.7577  -2.1229
 4BH  HA    H   HNH1  0   0.354  -3.1572  -4.1829  -0.3547

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
 4BH  CL   C1    single    1.731  0.020  1.731
 4BH  C1   C2    aromatic  1.395  0.020  1.395
 4BH  C1   C5    aromatic  1.381  0.020  1.381
 4BH  C2   O2    single    1.337  0.020  1.337
 4BH  C2   C3    aromatic  1.390  0.020  1.390
 4BH  O2   H2    single    0.850  0.020  0.980
 4BH  C3   C4    aromatic  1.390  0.020  1.390
 4BH  C3   H3    single    0.930  0.020  1.080
 4BH  C4   O4    single    1.341  0.020  1.341
 4BH  C4   C6    aromatic  1.399  0.020  1.399
 4BH  O4   H4    single    0.850  0.020  0.980
 4BH  C5   C6    aromatic  1.391  0.020  1.391
 4BH  C5   H5    single    0.930  0.020  1.080
 4BH  C6   C7    single    1.466  0.020  1.466
 4BH  C7   N1    aromatic  1.355  0.020  1.355
 4BH  C7   C9    aromatic  1.387  0.020  1.387
 4BH  N1   N2    aromatic  1.321  0.020  1.321
 4BH  N1   H1    single    0.860  0.020  1.020
 4BH  N2   C8    aromatic  1.320  0.020  1.320
 4BH  C8   C9    aromatic  1.412  0.020  1.412
 4BH  C8   H8    single    0.930  0.020  1.080
 4BH  C9   N3    single    1.396  0.020  1.396
 4BH  N3   C11   single    1.456  0.020  1.456
 4BH  N3   C15   single    1.450  0.020  1.450
 4BH  C11  C12   single    1.517  0.020  1.517
 4BH  C11  H111  single    0.970  0.020  1.090
 4BH  C11  H112  single    0.970  0.020  1.090
 4BH  C12  N4    single    1.451  0.020  1.451
 4BH  C12  H121  single    0.970  0.020  1.090
 4BH  C12  H122  single    0.970  0.020  1.090
 4BH  C15  C14   single    1.519  0.020  1.519
 4BH  C15  H151  single    0.970  0.020  1.090
 4BH  C15  H152  single    0.970  0.020  1.090
 4BH  C14  N4    single    1.451  0.020  1.451
 4BH  C14  H141  single    0.970  0.020  1.090
 4BH  C14  H142  single    0.970  0.020  1.090
 4BH  N4   HA    single    0.890  0.020  1.040

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
 4BH  C5    C1   C2    120.27  3.000
 4BH  C5    C1   CL    120.48  3.000
 4BH  C2    C1   CL    119.25  3.000
 4BH  C3    C2   O2    122.93  3.000
 4BH  C3    C2   C1    118.85  3.000
 4BH  O2    C2   C1    118.21  3.000
 4BH  H2    O2   C2    110.69  3.000
 4BH  H3    C3   C4    119.83  3.000
 4BH  H3    C3   C2    119.41  3.000
 4BH  C4    C3   C2    120.76  3.000
 4BH  C6    C4   O4    117.64  3.000
 4BH  C6    C4   C3    120.40  3.000
 4BH  O4    C4   C3    121.97  3.000
 4BH  H4    O4   C4    110.72  3.000
 4BH  H5    C5   C6    119.34  3.000
 4BH  H5    C5   C1    119.23  3.000
 4BH  C6    C5   C1    121.42  3.000
 4BH  C7    C6   C5    120.39  3.000
 4BH  C7    C6   C4    121.31  3.000
 4BH  C5    C6   C4    118.29  3.000
 4BH  C9    C7   N1    105.48  3.000
 4BH  C9    C7   C6    133.90  3.000
 4BH  N1    C7   C6    120.58  3.000
 4BH  H1    N1   N2    120.01  3.000
 4BH  H1    N1   C7    126.18  3.000
 4BH  N2    N1   C7    113.76  3.000
 4BH  C8    N2   N1    104.89  3.000
 4BH  H8    C8   C9    127.56  3.000
 4BH  H8    C8   N2    120.67  3.000
 4BH  C9    C8   N2    111.76  3.000
 4BH  N3    C9   C8    124.70  3.000
 4BH  N3    C9   C7    131.18  3.000
 4BH  C8    C9   C7    104.08  3.000
 4BH  C15   N3   C11   112.31  3.000
 4BH  C15   N3   C9    117.83  3.000
 4BH  C11   N3   C9    115.32  3.000
 4BH  H112  C11  H111  107.45  3.000
 4BH  H112  C11  C12   109.35  3.000
 4BH  H111  C11  C12   109.55  3.000
 4BH  H112  C11  N3    109.26  3.000
 4BH  H111  C11  N3    111.25  3.000
 4BH  C12   C11  N3    109.94  3.000
 4BH  H122  C12  H121  107.33  3.000
 4BH  H122  C12  N4    112.66  3.000
 4BH  H121  C12  N4    109.45  3.000
 4BH  H122  C12  C11   108.67  3.000
 4BH  H121  C12  C11   109.23  3.000
 4BH  N4    C12  C11   109.45  3.000
 4BH  H152  C15  H151  107.57  3.000
 4BH  H152  C15  C14   108.42  3.000
 4BH  H151  C15  C14   109.65  3.000
 4BH  H152  C15  N3    112.43  3.000
 4BH  H151  C15  N3    109.30  3.000
 4BH  C14   C15  N3    109.42  3.000
 4BH  H142  C14  H141  107.41  3.000
 4BH  H142  C14  N4    112.80  3.000
 4BH  H141  C14  N4    109.32  3.000
 4BH  H142  C14  C15   108.82  3.000
 4BH  H141  C14  C15   109.12  3.000
 4BH  N4    C14  C15   109.31  3.000
 4BH  HA    N4   C14   109.90  3.000
 4BH  HA    N4   C12   109.82  3.000
 4BH  C14   N4   C12   110.61  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
 4BH  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 4BH  CONST_02  C4   C6   C5   C1      0.00   0.0  0
 4BH  CONST_03  C7   C6   C5   C1    180.00   0.0  0
 4BH  CONST_04  C6   C5   C1   C2      0.00   0.0  0
 4BH  CONST_05  C6   C4   C3   C2      0.00   0.0  0
 4BH  CONST_06  C5   C1   C2   C3      0.00   0.0  0
 4BH  CONST_07  C5   C6   C4   C3      0.00   0.0  0
 4BH  CONST_08  C7   C6   C4   C3    180.00   0.0  0
 4BH  CONST_13  N2   N1   C7   C6    180.00   0.0  0
 4BH  CONST_14  C8   C9   C7   C6    180.00   0.0  0
 4BH  CONST_15  C8   N2   N1   C7      0.00   0.0  0
 4BH  CONST_16  N2   C8   C9   C7      0.00   0.0  0
 4BH  CONST_17  C8   C9   C7   N1      0.00   0.0  0
 4BH  CONST_18  C9   C8   N2   N1      0.00   0.0  0
 4BH  CONST_19  C9   C7   N1   N2      0.00   0.0  0
 4BH  CONST_20  N3   C9   C7   C6      0.00   0.0  0
 4BH  CONST_21  N3   C9   C7   N1    180.00   0.0  0
 4BH  CONST_22  N3   C9   C8   N2    180.00   0.0  0
 4BH  CONST_23  C3   C2   C1   CL    180.00   0.0  0
 4BH  CONST_24  C6   C5   C1   CL    180.00   0.0  0
 4BH  CONST_25  O4   C4   C3   C2    180.00   0.0  0
 4BH  CONST_26  C5   C1   C2   O2    180.00   0.0  0
 4BH  CONST_27  C4   C3   C2   O2    180.00   0.0  0
 4BH  CONST_28  C5   C6   C4   O4    180.00   0.0  0
 4BH  CONST_29  C7   C6   C4   O4      0.00   0.0  0
 4BH  CONST_30  H3   C3   C2   C1    180.00   0.0  0
 4BH  CONST_31  H5   C5   C1   C2    180.00   0.0  0
 4BH  CONST_32  H1   N1   C7   C6      0.00   0.0  0
 4BH  CONST_33  H8   C8   C9   C7    180.00   0.0  0
 4BH  Var_01    C11  N3   C9   C7    114.55  30.0  2
 4BH  Var_02    C12  C11  N3   C9    164.93  30.0  1
 4BH  Var_03    C14  C15  N3   C9   -165.49  30.0  1
 4BH  Var_04    N4   C12  C11  N3     56.68  30.0  1
 4BH  Var_05    N4   C14  C15  N3    -58.17  30.0  1
 4BH  Var_06    C14  N4   C12  C11   -60.22  30.0  1
 4BH  Var_07    C15  C14  N4   C12    61.02  30.0  1

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
 4BH  plan-1  C6  0.020
 4BH  plan-1  C7  0.020
 4BH  plan-1  N1  0.020
 4BH  plan-1  N2  0.020
 4BH  plan-1  C8  0.020
 4BH  plan-1  C9  0.020
 4BH  plan-1  N3  0.020
 4BH  plan-1  H1  0.020
 4BH  plan-1  H8  0.020
 4BH  plan-2  CL  0.020
 4BH  plan-2  C1  0.020
 4BH  plan-2  C2  0.020
 4BH  plan-2  O2  0.020
 4BH  plan-2  C3  0.020
 4BH  plan-2  C4  0.020
 4BH  plan-2  O4  0.020
 4BH  plan-2  C5  0.020
 4BH  plan-2  C6  0.020
 4BH  plan-2  C7  0.020
 4BH  plan-2  H3  0.020
 4BH  plan-2  H5  0.020

