# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 05:38:07 2020
#   Inital geometry file: a 133 line input string
#   Ligand name: 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-[4-(morpholin-4-ylmethyl)phenyl]isoxazole-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)c1noc(c2cc(Cl)c(O)cc2O)c1c3ccc(CN4CCOCC4)cc3
#
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
 2EQ  2EQ  5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-[4-(morpholin-4-ylmethyl)phenyl]isoxazole-3-carboxamide  ligand  56  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 OK
;

data_comp_2EQ
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
 2EQ  C20   C   CH2   0  -0.357  36.8364   4.8183  23.8059
 2EQ  C21   C   CH2   0  -0.146  37.4647   3.4573  23.4871
 2EQ  O4    O   O2    0  -0.487  36.8135   2.8070  22.4122
 2EQ  C22   C   CH2   0  -0.216  35.4437   3.1212  22.3699
 2EQ  C23   C   CH2   0  -0.287  35.2323   4.6018  22.0395
 2EQ  N4    N   NT    0  -0.402  36.3364   5.3800  22.5723
 2EQ  C19   C   CH2   0  -0.402  36.1219   6.8139  22.5625
 2EQ  C16   C   CR6   0   0.115  35.0371   7.3156  23.4884
 2EQ  C17   C   CR16  0  -0.288  35.3162   7.6023  24.8235
 2EQ  C18   C   CR16  0  -0.276  34.3181   8.0137  25.6911
 2EQ  C15   C   CR16  0  -0.283  33.7259   7.4660  23.0449
 2EQ  C14   C   CR16  0  -0.290  32.7211   7.8748  23.9085
 2EQ  C13   C   CR6   0   0.010  33.0068   8.1514  25.2428
 2EQ  C9    C   CR5   0  -0.132  31.9478   8.6171  26.1447
 2EQ  C8    C   CR5   0   0.129  31.5393   8.0891  27.3999
 2EQ  C10   C   C     0   0.513  32.0783   6.8815  28.0962
 2EQ  O3    O   O     0  -0.464  32.5885   5.9822  27.4495
 2EQ  N3    N   NH1   0  -0.626  31.9347   6.8874  29.4240
 2EQ  C11   C   CH2   0  -0.299  32.4104   5.8162  30.2768
 2EQ  C12   C   CH3   0  -0.660  33.8714   5.9783  30.6680
 2EQ  N2    N   N     0  -0.150  30.5381   8.7505  27.9012
 2EQ  O5    O   O     0  -0.362  30.2665   9.7424  27.0217
 2EQ  C7    C   CR5   0   0.476  31.1019   9.6728  25.9723
 2EQ  C5    C   CR6   0  -0.179  30.9714  10.6812  24.9329
 2EQ  C6    C   CR16  0  -0.240  32.1298  11.1551  24.3156
 2EQ  C4    C   CR6   0  -0.181  32.0719  12.0808  23.3014
 2EQ  CL1   CL  CL    0  -0.110  33.5267  12.6555  22.5548
 2EQ  C3    C   CR6   0   0.445  30.8383  12.5811  22.8658
 2EQ  O2    O   OH1   0  -0.601  30.7169  13.4810  21.8898
 2EQ  C2    C   CR16  0  -0.435  29.6824  12.1246  23.4809
 2EQ  C1    C   CR6   0   0.368  29.7300  11.1868  24.5056
 2EQ  O1    O   OH1   0  -0.611  28.5468  10.8062  25.0045
 2EQ  H201  H   HCH2  0   0.213  36.0636   4.7227  24.5845
 2EQ  H202  H   HCH2  0   0.252  37.6082   5.4706  24.2202
 2EQ  H211  H   HCH2  0   0.221  38.5058   3.5883  23.1852
 2EQ  H212  H   HCH2  0   0.201  37.4551   2.8291  24.3872
 2EQ  H221  H   HCH2  0   0.248  34.9818   2.4959  21.6048
 2EQ  H222  H   HCH2  0   0.209  34.9575   2.8703  23.3219
 2EQ  H231  H   HCH2  0   0.228  35.1858   4.7581  20.9570
 2EQ  H232  H   HCH2  0   0.207  34.2542   4.8985  22.4465
 2EQ  H191  H   HCH2  0   0.253  37.0689   7.2952  22.8220
 2EQ  H192  H   HCH2  0   0.247  35.8872   7.1077  21.5349
 2EQ  H17   H   HCR6  0   0.251  36.3324   7.5153  25.1900
 2EQ  H15   H   HCR6  0   0.255  33.4846   7.2646  22.0078
 2EQ  H18   H   HCR6  0   0.246  34.5648   8.2499  26.7185
 2EQ  H14   H   HCR6  0   0.251  31.7074   7.9806  23.5420
 2EQ  H3    H   HNH1  0   0.410  31.5537   7.7087  29.8666
 2EQ  H111  H   HCH2  0   0.255  31.7785   5.8077  31.1641
 2EQ  H112  H   HCH2  0   0.246  32.2556   4.8658  29.7670
 2EQ  H121  H   HCH3  0   0.232  34.5180   5.9556  29.7912
 2EQ  H122  H   HCH3  0   0.229  34.0353   6.9207  31.1912
 2EQ  H123  H   HCH3  0   0.234  34.1744   5.1686  31.3321
 2EQ  H6    H   HCR6  0   0.294  33.0944  10.7961  24.6475
 2EQ  H2    H   HOH1  0   0.474  31.5782  13.7289  21.5286
 2EQ  HA    H   HCR6  0   0.291  28.7229  12.5059  23.1540
 2EQ  H1    H   HOH1  0   0.482  28.6320  10.2158  25.7613

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
 2EQ  C20  C21   single    1.533  0.020  1.533
 2EQ  C20  N4    single    1.445  0.020  1.445
 2EQ  C21  O4    single    1.415  0.020  1.415
 2EQ  O4   C22   single    1.406  0.020  1.406
 2EQ  C22  C23   single    1.532  0.020  1.532
 2EQ  C23  N4    single    1.452  0.020  1.452
 2EQ  N4   C19   single    1.450  0.020  1.450
 2EQ  C19  C16   single    1.512  0.020  1.512
 2EQ  C16  C17   aromatic  1.394  0.020  1.394
 2EQ  C16  C15   aromatic  1.392  0.020  1.392
 2EQ  C17  C18   aromatic  1.385  0.020  1.385
 2EQ  C18  C13   aromatic  1.393  0.020  1.393
 2EQ  C15  C14   aromatic  1.387  0.020  1.387
 2EQ  C14  C13   aromatic  1.392  0.020  1.392
 2EQ  C13  C9    single    1.467  0.020  1.467
 2EQ  C9   C8    aromatic  1.422  0.020  1.422
 2EQ  C9   C7    aromatic  1.364  0.020  1.364
 2EQ  C8   C10   single    1.495  0.020  1.495
 2EQ  C8   N2    aromatic  1.300  0.020  1.300
 2EQ  C10  O3    double    1.220  0.020  1.220
 2EQ  C10  N3    single    1.336  0.020  1.336
 2EQ  N3   C11   single    1.449  0.020  1.449
 2EQ  C11  C12   single    1.521  0.020  1.521
 2EQ  N2   O5    aromatic  1.353  0.020  1.353
 2EQ  O5   C7    aromatic  1.343  0.020  1.343
 2EQ  C7   C5    single    1.454  0.020  1.454
 2EQ  C5   C6    aromatic  1.396  0.020  1.396
 2EQ  C5   C1    aromatic  1.407  0.020  1.407
 2EQ  C6   C4    aromatic  1.374  0.020  1.374
 2EQ  C4   CL1   single    1.733  0.020  1.733
 2EQ  C4   C3    aromatic  1.401  0.020  1.401
 2EQ  C3   O2    single    1.333  0.020  1.333
 2EQ  C3   C2    aromatic  1.387  0.020  1.387
 2EQ  C2   C1    aromatic  1.390  0.020  1.390
 2EQ  C1   O1    single    1.339  0.020  1.339
 2EQ  C20  H201  single    0.970  0.020  1.090
 2EQ  C20  H202  single    0.970  0.020  1.090
 2EQ  C21  H211  single    0.970  0.020  1.090
 2EQ  C21  H212  single    0.970  0.020  1.090
 2EQ  C22  H221  single    0.970  0.020  1.090
 2EQ  C22  H222  single    0.970  0.020  1.090
 2EQ  C23  H231  single    0.970  0.020  1.090
 2EQ  C23  H232  single    0.970  0.020  1.090
 2EQ  C19  H191  single    0.970  0.020  1.090
 2EQ  C19  H192  single    0.970  0.020  1.090
 2EQ  C17  H17   single    0.930  0.020  1.080
 2EQ  C15  H15   single    0.930  0.020  1.080
 2EQ  C18  H18   single    0.930  0.020  1.080
 2EQ  C14  H14   single    0.930  0.020  1.080
 2EQ  N3   H3    single    0.860  0.020  1.020
 2EQ  C11  H111  single    0.970  0.020  1.090
 2EQ  C11  H112  single    0.970  0.020  1.090
 2EQ  C12  H121  single    0.970  0.020  1.090
 2EQ  C12  H122  single    0.970  0.020  1.090
 2EQ  C12  H123  single    0.970  0.020  1.090
 2EQ  C6   H6    single    0.930  0.020  1.080
 2EQ  O2   H2    single    0.850  0.020  0.980
 2EQ  C2   HA    single    0.930  0.020  1.080
 2EQ  O1   H1    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
 2EQ  H202  C20  H201  106.24  3.000
 2EQ  H202  C20  N4    109.64  3.000
 2EQ  H201  C20  N4    113.24  3.000
 2EQ  H202  C20  C21   108.64  3.000
 2EQ  H201  C20  C21   110.96  3.000
 2EQ  N4    C20  C21   108.03  3.000
 2EQ  H212  C21  H211  107.68  3.000
 2EQ  H212  C21  O4    110.84  3.000
 2EQ  H211  C21  O4    106.49  3.000
 2EQ  H212  C21  C20   109.51  3.000
 2EQ  H211  C21  C20   109.99  3.000
 2EQ  O4    C21  C20   112.18  3.000
 2EQ  C22   O4   C21   111.62  3.000
 2EQ  H222  C22  H221  106.83  3.000
 2EQ  H222  C22  C23   110.30  3.000
 2EQ  H221  C22  C23   110.14  3.000
 2EQ  H222  C22  O4    110.75  3.000
 2EQ  H221  C22  O4    107.79  3.000
 2EQ  C23   C22  O4    110.92  3.000
 2EQ  H232  C23  H231  106.84  3.000
 2EQ  H232  C23  N4    113.31  3.000
 2EQ  H231  C23  N4    108.57  3.000
 2EQ  H232  C23  C22   107.68  3.000
 2EQ  H231  C23  C22   110.93  3.000
 2EQ  N4    C23  C22   109.51  3.000
 2EQ  C19   N4   C23   114.52  3.000
 2EQ  C19   N4   C20   116.20  3.000
 2EQ  C23   N4   C20   111.60  3.000
 2EQ  H192  C19  H191  106.88  3.000
 2EQ  H192  C19  C16   109.40  3.000
 2EQ  H191  C19  C16   109.27  3.000
 2EQ  H192  C19  N4    107.68  3.000
 2EQ  H191  C19  N4    107.79  3.000
 2EQ  C16   C19  N4    115.48  3.000
 2EQ  C15   C16  C17   118.13  3.000
 2EQ  C15   C16  C19   121.10  3.000
 2EQ  C17   C16  C19   120.75  3.000
 2EQ  H17   C17  C18   119.19  3.000
 2EQ  H17   C17  C16   119.68  3.000
 2EQ  C18   C17  C16   121.12  3.000
 2EQ  H18   C18  C13   119.90  3.000
 2EQ  H18   C18  C17   119.67  3.000
 2EQ  C13   C18  C17   120.41  3.000
 2EQ  H15   C15  C14   119.31  3.000
 2EQ  H15   C15  C16   119.63  3.000
 2EQ  C14   C15  C16   121.06  3.000
 2EQ  H14   C14  C13   119.80  3.000
 2EQ  H14   C14  C15   119.76  3.000
 2EQ  C13   C14  C15   120.45  3.000
 2EQ  C9    C13  C14   120.27  3.000
 2EQ  C9    C13  C18   120.88  3.000
 2EQ  C14   C13  C18   118.82  3.000
 2EQ  C7    C9   C8    102.76  3.000
 2EQ  C7    C9   C13   128.02  3.000
 2EQ  C8    C9   C13   129.22  3.000
 2EQ  N2    C8   C10   120.60  3.000
 2EQ  N2    C8   C9    111.88  3.000
 2EQ  C10   C8   C9    127.43  3.000
 2EQ  N3    C10  O3    125.13  3.000
 2EQ  N3    C10  C8    114.89  3.000
 2EQ  O3    C10  C8    119.98  3.000
 2EQ  H3    N3   C11   117.90  3.000
 2EQ  H3    N3   C10   118.74  3.000
 2EQ  C11   N3   C10   123.12  3.000
 2EQ  H112  C11  H111  106.97  3.000
 2EQ  H112  C11  C12   110.47  3.000
 2EQ  H111  C11  C12   110.40  3.000
 2EQ  H112  C11  N3    108.83  3.000
 2EQ  H111  C11  N3    107.13  3.000
 2EQ  C12   C11  N3    112.81  3.000
 2EQ  H123  C12  H122  107.94  3.000
 2EQ  H123  C12  H121  108.04  3.000
 2EQ  H122  C12  H121  108.36  3.000
 2EQ  H123  C12  C11   110.15  3.000
 2EQ  H122  C12  C11   111.09  3.000
 2EQ  H121  C12  C11   111.15  3.000
 2EQ  O5    N2   C8    106.07  3.000
 2EQ  C7    O5   N2    110.18  3.000
 2EQ  C5    C7   O5    117.82  3.000
 2EQ  C5    C7   C9    133.07  3.000
 2EQ  O5    C7   C9    109.10  3.000
 2EQ  C1    C5   C6    118.43  3.000
 2EQ  C1    C5   C7    123.06  3.000
 2EQ  C6    C5   C7    118.50  3.000
 2EQ  H6    C6   C4    119.19  3.000
 2EQ  H6    C6   C5    119.47  3.000
 2EQ  C4    C6   C5    121.34  3.000
 2EQ  C3    C4   CL1   119.14  3.000
 2EQ  C3    C4   C6    120.47  3.000
 2EQ  CL1   C4   C6    120.39  3.000
 2EQ  C2    C3   O2    118.10  3.000
 2EQ  C2    C3   C4    118.60  3.000
 2EQ  O2    C3   C4    123.30  3.000
 2EQ  H2    O2   C3    111.45  3.000
 2EQ  HA    C2   C1    119.37  3.000
 2EQ  HA    C2   C3    119.26  3.000
 2EQ  C1    C2   C3    121.37  3.000
 2EQ  O1    C1   C2    115.85  3.000
 2EQ  O1    C1   C5    124.35  3.000
 2EQ  C2    C1   C5    119.78  3.000
 2EQ  H1    O1   C1    112.87  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
 2EQ  CONST_01  C13   C18  C17  C16     0.00   0.0  0
 2EQ  CONST_02  C13   C14  C15  C16     0.00   0.0  0
 2EQ  CONST_03  C14   C15  C16  C17     0.00   0.0  0
 2EQ  CONST_04  C14   C13  C18  C17     0.00   0.0  0
 2EQ  CONST_05  C9    C13  C18  C17   180.00   0.0  0
 2EQ  CONST_06  C15   C16  C17  C18     0.00   0.0  0
 2EQ  CONST_07  C15   C14  C13  C18     0.00   0.0  0
 2EQ  CONST_10  C9    C13  C14  C15   180.00   0.0  0
 2EQ  CONST_13  N2    C8   C9   C13   180.00   0.0  0
 2EQ  CONST_14  O5    C7   C9   C13   180.00   0.0  0
 2EQ  CONST_15  C5    C7   C9   C13     0.00   0.0  0
 2EQ  CONST_16  O5    N2   C8   C9      0.00   0.0  0
 2EQ  CONST_17  N2    O5   C7   C9      0.00   0.0  0
 2EQ  CONST_20  O5    C7   C9   C8      0.00   0.0  0
 2EQ  CONST_21  C5    C7   C9   C8    180.00   0.0  0
 2EQ  CONST_22  C7    O5   N2   C8      0.00   0.0  0
 2EQ  CONST_23  C7    C9   C8   N2      0.00   0.0  0
 2EQ  CONST_24  C5    C7   O5   N2    180.00   0.0  0
 2EQ  CONST_27  C4    C6   C5   C7    180.00   0.0  0
 2EQ  CONST_28  C2    C1   C5   C7    180.00   0.0  0
 2EQ  CONST_29  C3    C4   C6   C5      0.00   0.0  0
 2EQ  CONST_30  C3    C2   C1   C5      0.00   0.0  0
 2EQ  CONST_31  C2    C1   C5   C6      0.00   0.0  0
 2EQ  CONST_32  C2    C3   C4   C6      0.00   0.0  0
 2EQ  CONST_33  C1    C5   C6   C4      0.00   0.0  0
 2EQ  CONST_34  C1    C2   C3   C4      0.00   0.0  0
 2EQ  CONST_35  C18   C17  C16  C19   180.00   0.0  0
 2EQ  CONST_36  C14   C15  C16  C19   180.00   0.0  0
 2EQ  CONST_37  C10   C8   C9   C13     0.00   0.0  0
 2EQ  CONST_38  C7    C9   C8   C10   180.00   0.0  0
 2EQ  CONST_39  O5    N2   C8   C10   180.00   0.0  0
 2EQ  CONST_40  O1    C1   C5   C7      0.00   0.0  0
 2EQ  CONST_41  CL1   C4   C6   C5    180.00   0.0  0
 2EQ  CONST_42  O1    C1   C5   C6    180.00   0.0  0
 2EQ  CONST_43  O2    C3   C4   C6    180.00   0.0  0
 2EQ  CONST_44  C2    C3   C4   CL1   180.00   0.0  0
 2EQ  CONST_45  O1    C1   C2   C3    180.00   0.0  0
 2EQ  CONST_46  C1    C2   C3   O2    180.00   0.0  0
 2EQ  CONST_47  H18   C18  C17  C16   180.00   0.0  0
 2EQ  CONST_48  H14   C14  C15  C16   180.00   0.0  0
 2EQ  CONST_49  H15   C15  C16  C17   180.00   0.0  0
 2EQ  CONST_50  H17   C17  C16  C15   180.00   0.0  0
 2EQ  CONST_51  H6    C6   C5   C7      0.00   0.0  0
 2EQ  CONST_52  HA    C2   C1   C5    180.00   0.0  0
 2EQ  CONST_53  C11   N3   C10  C8    180.00   0.0  0
 2EQ  CONST_54  H3    N3   C10  C8      0.00   0.0  0
 2EQ  CONST_55  C11   N3   C10  O3      0.00   0.0  0
 2EQ  Var_01    C22   C23  N4   C20   -33.51  30.0  1
 2EQ  Var_02    C23   N4   C20  C21    66.36  30.0  1
 2EQ  Var_03    C23   C22  O4   C21    66.35  30.0  1
 2EQ  Var_04    N4    C20  C21  O4    -32.09  30.0  1
 2EQ  Var_05    N4    C23  C22  O4    -31.44  30.0  1
 2EQ  Var_06    C16   C19  N4   C20   -65.53  30.0  3
 2EQ  Var_07    C17   C16  C19  N4     86.11  30.0  2
 2EQ  Var_08    H211  C21  O4   C22  -152.30  30.0  1
 2EQ  Var_09    O3    C10  C8   C9    -26.01  30.0  2
 2EQ  Var_10    C12   C11  N3   C10    85.62  30.0  3
 2EQ  Var_11    H121  C12  C11  N3    -62.04  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
 2EQ  plan-1  C13  0.020
 2EQ  plan-1  C9   0.020
 2EQ  plan-1  C8   0.020
 2EQ  plan-1  C10  0.020
 2EQ  plan-1  N2   0.020
 2EQ  plan-1  O5   0.020
 2EQ  plan-1  C7   0.020
 2EQ  plan-1  C5   0.020
 2EQ  plan-2  C19  0.020
 2EQ  plan-2  C16  0.020
 2EQ  plan-2  C17  0.020
 2EQ  plan-2  C18  0.020
 2EQ  plan-2  C15  0.020
 2EQ  plan-2  C14  0.020
 2EQ  plan-2  C13  0.020
 2EQ  plan-2  C9   0.020
 2EQ  plan-2  H17  0.020
 2EQ  plan-2  H15  0.020
 2EQ  plan-2  H18  0.020
 2EQ  plan-2  H14  0.020
 2EQ  plan-3  C7   0.020
 2EQ  plan-3  C5   0.020
 2EQ  plan-3  C6   0.020
 2EQ  plan-3  C4   0.020
 2EQ  plan-3  CL1  0.020
 2EQ  plan-3  C3   0.020
 2EQ  plan-3  O2   0.020
 2EQ  plan-3  C2   0.020
 2EQ  plan-3  C1   0.020
 2EQ  plan-3  O1   0.020
 2EQ  plan-3  H6   0.020
 2EQ  plan-3  HA   0.020
 2EQ  plan-4  C8   0.020
 2EQ  plan-4  C10  0.020
 2EQ  plan-4  O3   0.020
 2EQ  plan-4  N3   0.020
 2EQ  plan-4  C11  0.020
 2EQ  plan-4  H3   0.020

