# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 16:36:04 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: 5-(1-methylpyrazol-4-yl)-3-(3-phenoxyphenyl)furo[3,2-b]pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(cn1)c2ccc3occ(c4cccc(Oc5ccccc5)c4)c3n2
#
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
 H3N  H3N  5-(1-methylpyrazol-4-yl)-3-(3-phenoxyphenyl)furo[3,2-b]pyridine  ligand  45  28  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_H3N
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
 H3N  C11  C  CR16  0  -0.340  -0.4287   0.1179   1.1555
 H3N  C12  C  CR16  0  -0.211  -1.4621   0.8808   1.6801
 H3N  C14  C  CR6   0   0.360  -3.0592  -0.4418   0.4982
 H3N  C17  C  CR16  0  -0.231  -7.4839   0.9038  -0.4514
 H3N  N    N  NR5   0  -0.265   5.0175   2.7561   0.9385
 H3N  N1   N  N     0  -0.267   6.1932   2.2162   0.6279
 H3N  C3   C  CR15  0  -0.084   5.9153   1.0030   0.1971
 H3N  C2   C  CR5   0  -0.161   4.5297   0.7465   0.2280
 H3N  C1   C  CR15  0   0.077   3.9932   1.9211   0.7175
 H3N  C4   C  CR6   0   0.213   3.7856  -0.4435  -0.1674
 H3N  N2   N  N     0  -0.466   2.4749  -0.4217   0.0560
 H3N  C22  C  CR56  0   0.079   1.7817  -1.4903  -0.3146
 H3N  C7   C  CR56  0   0.349   2.3668  -2.6064  -0.9113
 H3N  C6   C  CR16  0  -0.208   3.7234  -2.6582  -1.1520
 H3N  C5   C  CR16  0  -0.323   4.4364  -1.5393  -0.7632
 H3N  C9   C  CR5   0   0.008   0.3665  -1.7787  -0.2399
 H3N  C8   C  CR15  0  -0.009   0.2472  -3.0139  -0.7883
 H3N  O    O  O     0  -0.420   1.4280  -3.5294  -1.1990
 H3N  C10  C  CR6   0   0.113  -0.7080  -0.9453   0.2969
 H3N  C21  C  CR16  0  -0.397  -2.0394  -1.2074  -0.0374
 H3N  C13  C  CR16  0  -0.307  -2.7828   0.6089   1.3656
 H3N  O1   O  O2    0  -0.511  -4.3445  -0.7866   0.1828
 H3N  C15  C  CR6   0   0.349  -5.2065   0.1705  -0.2709
 H3N  C20  C  CR16  0  -0.312  -4.7892   1.2594  -1.0277
 H3N  C19  C  CR16  0  -0.223  -5.7319   2.1697  -1.4848
 H3N  C18  C  CR16  0  -0.249  -7.0795   2.0003  -1.2008
 H3N  C16  C  CR16  0  -0.312  -6.5529  -0.0102   0.0183
 H3N  H1   H  HCR6  0   0.261   0.5943   0.3510   1.4119
 H3N  H2   H  HCR6  0   0.247  -1.2353   1.6988   2.3505
 H3N  H3   H  HCR6  0   0.245  -8.5311   0.7587  -0.2215
 H3N  H4   H  HCH3  0   0.253   5.6218   4.2443   2.2634
 H3N  H5   H  HCH3  0   0.248   5.2401   4.8099   0.6265
 H3N  H6   H  HCH3  0   0.238   3.9381   4.3333   1.7252
 H3N  H7   H  HCR5  0   0.230   6.7183   0.3490  -0.1068
 H3N  H8   H  HCR5  0   0.268   2.9708   2.1980   0.9119
 H3N  H9   H  HCR6  0   0.263   4.2048  -3.5075  -1.6160
 H3N  H10  H  HCR6  0   0.238   5.5030  -1.5106  -0.9339
 H3N  H11  H  HCR5  0   0.266  -0.6108  -3.6492  -0.9385
 H3N  H12  H  HCR6  0   0.232  -2.2954  -2.0103  -0.7173
 H3N  H13  H  HCR6  0   0.259  -3.5812   1.2042   1.7888
 H3N  H14  H  HCR6  0   0.262  -3.7436   1.4049  -1.2650
 H3N  H15  H  HCR6  0   0.241  -5.4035   3.0169  -2.0715
 H3N  H16  H  HCR6  0   0.237  -7.8067   2.7160  -1.5582
 H3N  H17  H  HCR6  0   0.245  -6.8662  -0.8617   0.6081
 H3N  C    C  CH3   0  -0.487   4.9552   4.1133   1.4138

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
 H3N  C    N    single    1.439  0.020  1.439
 H3N  N1   N    aromatic  1.330  0.020  1.330
 H3N  N1   C3   aromatic  1.317  0.020  1.317
 H3N  N    C1   aromatic  1.340  0.020  1.340
 H3N  C3   C2   aromatic  1.409  0.020  1.409
 H3N  C17  C16  aromatic  1.387  0.020  1.387
 H3N  C17  C18  aromatic  1.388  0.020  1.388
 H3N  C16  C15  aromatic  1.389  0.020  1.389
 H3N  C1   C2   aromatic  1.381  0.020  1.381
 H3N  C18  C19  aromatic  1.388  0.020  1.388
 H3N  C2   C4   single    1.458  0.020  1.458
 H3N  C15  O1   single    1.366  0.020  1.366
 H3N  C15  C20  aromatic  1.390  0.020  1.390
 H3N  C4   C5   aromatic  1.407  0.020  1.407
 H3N  C4   N2   aromatic  1.330  0.020  1.330
 H3N  C19  C20  aromatic  1.388  0.020  1.388
 H3N  O1   C14  single    1.368  0.020  1.368
 H3N  C5   C6   aromatic  1.383  0.020  1.383
 H3N  N2   C22  aromatic  1.327  0.020  1.327
 H3N  C21  C14  aromatic  1.383  0.020  1.383
 H3N  C21  C10  aromatic  1.397  0.020  1.397
 H3N  C6   C7   aromatic  1.379  0.020  1.379
 H3N  C14  C13  aromatic  1.390  0.020  1.390
 H3N  C22  C7   aromatic  1.394  0.020  1.394
 H3N  C22  C9   aromatic  1.446  0.020  1.446
 H3N  C7   O    aromatic  1.348  0.020  1.348
 H3N  C9   C10  single    1.462  0.020  1.462
 H3N  C9   C8   aromatic  1.357  0.020  1.357
 H3N  C10  C11  aromatic  1.395  0.020  1.395
 H3N  C13  C12  aromatic  1.385  0.020  1.385
 H3N  O    C8   aromatic  1.352  0.020  1.352
 H3N  C11  C12  aromatic  1.388  0.020  1.388
 H3N  C11  H1   single    0.930  0.020  1.080
 H3N  C12  H2   single    0.930  0.020  1.080
 H3N  C17  H3   single    0.930  0.020  1.080
 H3N  C    H4   single    0.970  0.020  1.090
 H3N  C    H5   single    0.970  0.020  1.090
 H3N  C    H6   single    0.970  0.020  1.090
 H3N  C3   H7   single    0.930  0.020  1.080
 H3N  C1   H8   single    0.930  0.020  1.080
 H3N  C6   H9   single    0.930  0.020  1.080
 H3N  C5   H10  single    0.930  0.020  1.080
 H3N  C8   H11  single    0.930  0.020  1.080
 H3N  C21  H12  single    0.930  0.020  1.080
 H3N  C13  H13  single    0.930  0.020  1.080
 H3N  C20  H14  single    0.930  0.020  1.080
 H3N  C19  H15  single    0.930  0.020  1.080
 H3N  C18  H16  single    0.930  0.020  1.080
 H3N  C16  H17  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
 H3N  H1   C11  C10  120.02  3.000
 H3N  H1   C11  C12  119.80  3.000
 H3N  C10  C11  C12  120.18  3.000
 H3N  H2   C12  C13  119.29  3.000
 H3N  H2   C12  C11  119.60  3.000
 H3N  C13  C12  C11  121.10  3.000
 H3N  O1   C14  C13  121.42  3.000
 H3N  C13  C14  C21  120.89  3.000
 H3N  O1   C14  C21  117.65  3.000
 H3N  H3   C17  C16  119.31  3.000
 H3N  H3   C17  C18  120.17  3.000
 H3N  C16  C17  C18  120.52  3.000
 H3N  C1   N    N1   112.60  3.000
 H3N  C1   N    C    127.51  3.000
 H3N  N1   N    C    119.86  3.000
 H3N  C3   N1   N    105.28  3.000
 H3N  H7   C3   C2   128.85  3.000
 H3N  H7   C3   N1   119.55  3.000
 H3N  C2   C3   N1   111.59  3.000
 H3N  C4   C2   C1   126.30  3.000
 H3N  C4   C2   C3   130.11  3.000
 H3N  C1   C2   C3   103.59  3.000
 H3N  H8   C1   C2   130.66  3.000
 H3N  H8   C1   N    122.40  3.000
 H3N  C2   C1   N    106.94  3.000
 H3N  C5   C4   N2   122.67  3.000
 H3N  N2   C4   C2   116.36  3.000
 H3N  C5   C4   C2   120.96  3.000
 H3N  C22  N2   C4   117.06  3.000
 H3N  C9   C22  C7   105.85  3.000
 H3N  C9   C22  N2   131.12  3.000
 H3N  C7   C22  N2   123.03  3.000
 H3N  O    C7   C6   128.50  3.000
 H3N  O    C7   C22  110.32  3.000
 H3N  C6   C7   C22  121.18  3.000
 H3N  H9   C6   C5   121.80  3.000
 H3N  H9   C6   C7   122.87  3.000
 H3N  C5   C6   C7   115.34  3.000
 H3N  H10  C5   C6   119.09  3.000
 H3N  H10  C5   C4   120.18  3.000
 H3N  C6   C5   C4   120.72  3.000
 H3N  C10  C9   C8   127.07  3.000
 H3N  C8   C9   C22  104.28  3.000
 H3N  C10  C9   C22  128.65  3.000
 H3N  H11  C8   O    115.34  3.000
 H3N  H11  C8   C9   131.51  3.000
 H3N  O    C8   C9   113.15  3.000
 H3N  C8   O    C7   106.40  3.000
 H3N  C21  C10  C9   120.37  3.000
 H3N  C9   C10  C11  120.88  3.000
 H3N  C21  C10  C11  118.75  3.000
 H3N  H12  C21  C10  120.96  3.000
 H3N  H12  C21  C14  118.64  3.000
 H3N  C10  C21  C14  120.40  3.000
 H3N  H13  C13  C14  120.87  3.000
 H3N  H13  C13  C12  120.46  3.000
 H3N  C14  C13  C12  118.67  3.000
 H3N  C15  O1   C14  119.54  3.000
 H3N  C16  C15  C20  120.42  3.000
 H3N  C20  C15  O1   122.71  3.000
 H3N  C16  C15  O1   116.84  3.000
 H3N  H14  C20  C19  119.73  3.000
 H3N  H14  C20  C15  120.99  3.000
 H3N  C19  C20  C15  119.29  3.000
 H3N  H15  C19  C18  120.10  3.000
 H3N  H15  C19  C20  119.10  3.000
 H3N  C18  C19  C20  120.81  3.000
 H3N  H16  C18  C19  120.32  3.000
 H3N  H16  C18  C17  120.35  3.000
 H3N  C19  C18  C17  119.33  3.000
 H3N  H17  C16  C15  119.77  3.000
 H3N  H17  C16  C17  120.59  3.000
 H3N  C15  C16  C17  119.64  3.000
 H3N  H6   C    H5   108.82  3.000
 H3N  H6   C    H4   108.99  3.000
 H3N  H5   C    H4   109.10  3.000
 H3N  H6   C    N    109.04  3.000
 H3N  H5   C    N    110.68  3.000
 H3N  H4   C    N    110.18  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
 H3N  CONST_01  C14  C21  C10  C11     0.00   0.0  0
 H3N  CONST_04  C14  C13  C12  C11     0.00   0.0  0
 H3N  CONST_05  C21  C14  C13  C12     0.00   0.0  0
 H3N  CONST_06  C21  C10  C11  C12     0.00   0.0  0
 H3N  CONST_07  C9   C10  C11  C12   180.00   0.0  0
 H3N  CONST_08  C9   C10  C21  C14   180.00   0.0  0
 H3N  CONST_09  C20  C15  C16  C17     0.00   0.0  0
 H3N  CONST_10  C20  C19  C18  C17     0.00   0.0  0
 H3N  CONST_11  C2   C3   N1   N       0.00   0.0  0
 H3N  CONST_12  C3   C2   C1   N       0.00   0.0  0
 H3N  CONST_13  C4   C2   C1   N     180.00   0.0  0
 H3N  CONST_14  C2   C1   N    N1      0.00   0.0  0
 H3N  CONST_15  C1   C2   C3   N1      0.00   0.0  0
 H3N  CONST_16  C4   C2   C3   N1    180.00   0.0  0
 H3N  CONST_17  C1   N    N1   C3      0.00   0.0  0
 H3N  CONST_18  C5   C4   C2   C3      0.00   0.0  0
 H3N  CONST_19  N2   C4   C2   C3    180.00   0.0  0
 H3N  CONST_20  C6   C5   C4   C2    180.00   0.0  0
 H3N  CONST_21  C22  N2   C4   C2    180.00   0.0  0
 H3N  CONST_22  C5   C4   C2   C1    180.00   0.0  0
 H3N  CONST_23  N2   C4   C2   C1      0.00   0.0  0
 H3N  CONST_24  C7   C6   C5   C4      0.00   0.0  0
 H3N  CONST_25  C7   C22  N2   C4      0.00   0.0  0
 H3N  CONST_26  C9   C22  N2   C4    180.00   0.0  0
 H3N  CONST_27  C6   C5   C4   N2      0.00   0.0  0
 H3N  CONST_28  C6   C7   C22  N2      0.00   0.0  0
 H3N  CONST_29  O    C7   C22  N2    180.00   0.0  0
 H3N  CONST_30  C10  C9   C22  N2      0.00   0.0  0
 H3N  CONST_31  C8   C9   C22  N2    180.00   0.0  0
 H3N  CONST_32  C5   C4   N2   C22     0.00   0.0  0
 H3N  CONST_33  C5   C6   C7   C22     0.00   0.0  0
 H3N  CONST_34  C8   O    C7   C22     0.00   0.0  0
 H3N  CONST_36  O    C8   C9   C22     0.00   0.0  0
 H3N  CONST_37  C10  C9   C22  C7    180.00   0.0  0
 H3N  CONST_38  C8   C9   C22  C7      0.00   0.0  0
 H3N  CONST_39  C9   C8   O    C7      0.00   0.0  0
 H3N  CONST_40  C9   C22  C7   C6    180.00   0.0  0
 H3N  CONST_41  C8   O    C7   C6    180.00   0.0  0
 H3N  CONST_42  O    C7   C6   C5    180.00   0.0  0
 H3N  CONST_43  O    C7   C22  C9      0.00   0.0  0
 H3N  CONST_45  C10  C9   C8   O     180.00   0.0  0
 H3N  CONST_46  C13  C14  C21  C10     0.00   0.0  0
 H3N  CONST_47  C13  C12  C11  C10     0.00   0.0  0
 H3N  CONST_48  C18  C17  C16  C15     0.00   0.0  0
 H3N  CONST_49  C18  C19  C20  C15     0.00   0.0  0
 H3N  CONST_50  C16  C17  C18  C19     0.00   0.0  0
 H3N  CONST_51  C16  C15  C20  C19     0.00   0.0  0
 H3N  CONST_52  O1   C14  C13  C12   180.00   0.0  0
 H3N  CONST_53  O1   C15  C16  C17   180.00   0.0  0
 H3N  CONST_54  C3   N1   N    C     180.00   0.0  0
 H3N  CONST_55  C2   C1   N    C     180.00   0.0  0
 H3N  CONST_56  O1   C14  C21  C10   180.00   0.0  0
 H3N  CONST_57  C19  C20  C15  O1    180.00   0.0  0
 H3N  CONST_58  H12  C21  C10  C11   180.00   0.0  0
 H3N  CONST_59  H13  C13  C12  C11   180.00   0.0  0
 H3N  CONST_60  H2   C12  C13  C14   180.00   0.0  0
 H3N  CONST_61  H15  C19  C18  C17   180.00   0.0  0
 H3N  CONST_62  H7   C3   N1   N     180.00   0.0  0
 H3N  CONST_63  H8   C1   N    N1    180.00   0.0  0
 H3N  CONST_64  H10  C5   C4   C2      0.00   0.0  0
 H3N  CONST_65  H9   C6   C5   C4    180.00   0.0  0
 H3N  CONST_66  H11  C8   C9   C22   180.00   0.0  0
 H3N  CONST_67  H1   C11  C10  C9      0.00   0.0  0
 H3N  CONST_68  H3   C17  C16  C15   180.00   0.0  0
 H3N  CONST_69  H17  C16  C15  C20   180.00   0.0  0
 H3N  CONST_70  H16  C18  C19  C20   180.00   0.0  0
 H3N  CONST_71  H14  C20  C19  C18   180.00   0.0  0
 H3N  Var_01    C16  C15  O1   C14  -150.14  30.0  2
 H3N  Var_02    H4   C    N    N1    -53.69  30.0  2

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
 H3N  plan-1  N    0.020
 H3N  plan-1  N1   0.020
 H3N  plan-1  C3   0.020
 H3N  plan-1  C2   0.020
 H3N  plan-1  C1   0.020
 H3N  plan-1  C4   0.020
 H3N  plan-1  H7   0.020
 H3N  plan-1  H8   0.020
 H3N  plan-1  C    0.020
 H3N  plan-2  C17  0.020
 H3N  plan-2  O1   0.020
 H3N  plan-2  C15  0.020
 H3N  plan-2  C20  0.020
 H3N  plan-2  C19  0.020
 H3N  plan-2  C18  0.020
 H3N  plan-2  C16  0.020
 H3N  plan-2  H3   0.020
 H3N  plan-2  H14  0.020
 H3N  plan-2  H15  0.020
 H3N  plan-2  H16  0.020
 H3N  plan-2  H17  0.020
 H3N  plan-3  C11  0.020
 H3N  plan-3  C12  0.020
 H3N  plan-3  C14  0.020
 H3N  plan-3  C9   0.020
 H3N  plan-3  C10  0.020
 H3N  plan-3  C21  0.020
 H3N  plan-3  C13  0.020
 H3N  plan-3  O1   0.020
 H3N  plan-3  H1   0.020
 H3N  plan-3  H2   0.020
 H3N  plan-3  H12  0.020
 H3N  plan-3  H13  0.020
 H3N  plan-4  C2   0.020
 H3N  plan-4  C4   0.020
 H3N  plan-4  N2   0.020
 H3N  plan-4  C22  0.020
 H3N  plan-4  C7   0.020
 H3N  plan-4  C6   0.020
 H3N  plan-4  C5   0.020
 H3N  plan-4  C9   0.020
 H3N  plan-4  C8   0.020
 H3N  plan-4  O    0.020
 H3N  plan-4  C10  0.020
 H3N  plan-4  H9   0.020
 H3N  plan-4  H10  0.020
 H3N  plan-4  H11  0.020

