# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 22 14:22:00 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: 4-[2-(2,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethyl]-2-methoxyphenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(CCc2[nH]nc3c2Cc4ccccc34)ccc1O
#
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
 1HK  1HK  4-[2-(2,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethyl]-2-methoxyphenol  ligand  41  23  .  2021-08-03  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_1HK
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
 1HK  O1    O  OH1   0  -0.634  -6.6562   0.2024   0.2481
 1HK  C1    C  CR6   0   0.264  -5.3158   0.3182   0.3612
 1HK  C18   C  CR6   0   0.310  -4.4614  -0.7609   0.0777
 1HK  O2    O  O2    0  -0.490  -5.0910  -1.8927  -0.3088
 1HK  C19   C  CH3   0  -0.431  -4.3105  -3.0301  -0.6162
 1HK  C17   C  CR16  0  -0.429  -3.0907  -0.6094   0.2076
 1HK  C4    C  CR6   0   0.124  -2.5381   0.6083   0.6141
 1HK  C3    C  CR16  0  -0.332  -3.3903   1.6661   0.8887
 1HK  C2    C  CR16  0  -0.330  -4.7693   1.5223   0.7659
 1HK  C5    C  CH2   0  -0.514  -1.0458   0.7669   0.6993
 1HK  C6    C  CH2   0  -0.532  -0.4231   1.0566  -0.6743
 1HK  C7    C  CR5   0   0.358   1.0575   1.1979  -0.6020
 1HK  C9    C  CR55  0  -0.136   2.0636   0.3073  -0.3131
 1HK  C10   C  CH2   0  -0.556   2.3642  -1.1164   0.0271
 1HK  C11   C  CR56  0   0.030   3.8785  -1.0747   0.1452
 1HK  C16   C  CR56  0   0.108   4.3866   0.2148  -0.0977
 1HK  C8    C  CR55  0   0.171   3.2408   1.0644  -0.3801
 1HK  N2    N  N     0  -0.293   3.0224   2.3289  -0.6825
 1HK  N1    N  NR15  0  -0.499   1.6934   2.3781  -0.8088
 1HK  C15   C  CR16  0  -0.320   5.7490   0.4677  -0.0423
 1HK  C14   C  CR16  0  -0.262   6.6093  -0.5818   0.2600
 1HK  C13   C  CR16  0  -0.260   6.1121  -1.8583   0.5018
 1HK  C12   C  CR16  0  -0.316   4.7431  -2.1111   0.4457
 1HK  H2    H  HOH1  0   0.470  -6.8901  -0.6924  -0.0263
 1HK  H192  H  HCH3  0   0.230  -3.7430  -3.3784   0.2506
 1HK  H191  H  HCH3  0   0.262  -5.0044  -3.8095  -0.9202
 1HK  H193  H  HCH3  0   0.230  -3.6154  -2.8345  -1.4367
 1HK  H13   H  HCR6  0   0.274  -2.4285  -1.4420   0.0020
 1HK  H4    H  HCR6  0   0.245  -2.9846   2.6179   1.2092
 1HK  H3    H  HCR6  0   0.261  -5.4279   2.3525   0.9904
 1HK  H5    H  HCH2  0   0.255  -0.7983   1.5819   1.3828
 1HK  H14   H  HCH2  0   0.250  -0.5944  -0.1383   1.1139
 1HK  H6    H  HCH2  0   0.262  -0.6718   0.2456  -1.3630
 1HK  H15   H  HCH2  0   0.263  -0.8663   1.9640  -1.0919
 1HK  H7    H  HCH2  0   0.269   1.9006  -1.4441   0.9618
 1HK  H8    H  HCH2  0   0.271   2.0455  -1.8236  -0.7433
 1HK  H1    H  HNR5  0   0.414   1.2524   3.2545  -1.0402
 1HK  H12   H  HCR6  0   0.250   6.1370   1.4608  -0.2310
 1HK  H11   H  HCR6  0   0.256   7.6760  -0.4046   0.3076
 1HK  H10   H  HCR6  0   0.255   6.7964  -2.6641   0.7348
 1HK  H9    H  HCR6  0   0.253   4.3663  -3.1092   0.6351

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
 1HK  N2   N1    aromatic  1.336  0.020  1.336
 1HK  N2   C8    aromatic  1.318  0.020  1.318
 1HK  C15  C14   aromatic  1.390  0.020  1.390
 1HK  C15  C16   aromatic  1.387  0.020  1.387
 1HK  N1   C7    aromatic  1.356  0.020  1.356
 1HK  C8   C16   aromatic  1.454  0.020  1.454
 1HK  C8   C9    aromatic  1.401  0.020  1.401
 1HK  C14  C13   aromatic  1.391  0.020  1.391
 1HK  C16  C11   aromatic  1.407  0.020  1.407
 1HK  C7   C9    aromatic  1.374  0.020  1.374
 1HK  C7   C6    single    1.489  0.020  1.489
 1HK  C9   C10   single    1.494  0.020  1.494
 1HK  C13  C12   aromatic  1.393  0.020  1.393
 1HK  C11  C10   single    1.519  0.020  1.519
 1HK  C11  C12   aromatic  1.383  0.020  1.383
 1HK  C6   C5    single    1.536  0.020  1.536
 1HK  C5   C4    single    1.503  0.020  1.503
 1HK  C4   C17   aromatic  1.398  0.020  1.398
 1HK  C4   C3    aromatic  1.386  0.020  1.386
 1HK  C17  C18   aromatic  1.385  0.020  1.385
 1HK  C3   C2    aromatic  1.392  0.020  1.392
 1HK  C18  C1    aromatic  1.405  0.020  1.405
 1HK  C18  O2    single    1.352  0.020  1.352
 1HK  C2   C1    aromatic  1.383  0.020  1.383
 1HK  C19  O2    single    1.413  0.020  1.413
 1HK  C1   O1    single    1.350  0.020  1.350
 1HK  O1   H2    single    0.850  0.020  0.980
 1HK  C19  H192  single    0.970  0.020  1.090
 1HK  C19  H191  single    0.970  0.020  1.090
 1HK  C19  H193  single    0.970  0.020  1.090
 1HK  C17  H13   single    0.930  0.020  1.080
 1HK  C3   H4    single    0.930  0.020  1.080
 1HK  C2   H3    single    0.930  0.020  1.080
 1HK  C5   H5    single    0.970  0.020  1.090
 1HK  C5   H14   single    0.970  0.020  1.090
 1HK  C6   H6    single    0.970  0.020  1.090
 1HK  C6   H15   single    0.970  0.020  1.090
 1HK  C10  H7    single    0.970  0.020  1.090
 1HK  C10  H8    single    0.970  0.020  1.090
 1HK  N1   H1    single    0.860  0.020  1.020
 1HK  C15  H12   single    0.930  0.020  1.080
 1HK  C14  H11   single    0.930  0.020  1.080
 1HK  C13  H10   single    0.930  0.020  1.080
 1HK  C12  H9    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
 1HK  H2    O1   C1    110.12  3.000
 1HK  C2    C1   C18   119.17  3.000
 1HK  C2    C1   O1    119.44  3.000
 1HK  C18   C1   O1    121.39  3.000
 1HK  C17   C18  O2    125.41  3.000
 1HK  O2    C18  C1    114.68  3.000
 1HK  C17   C18  C1    119.92  3.000
 1HK  C19   O2   C18   118.61  3.000
 1HK  H193  C19  H191  108.93  3.000
 1HK  H193  C19  H192  108.80  3.000
 1HK  H191  C19  H192  108.95  3.000
 1HK  H193  C19  O2    111.74  3.000
 1HK  H191  C19  O2    106.58  3.000
 1HK  H192  C19  O2    111.76  3.000
 1HK  H13   C17  C4    118.88  3.000
 1HK  H13   C17  C18   120.19  3.000
 1HK  C4    C17  C18   120.92  3.000
 1HK  C5    C4   C3    121.25  3.000
 1HK  C3    C4   C17   118.65  3.000
 1HK  C5    C4   C17   120.06  3.000
 1HK  H4    C3   C2    119.20  3.000
 1HK  H4    C3   C4    119.94  3.000
 1HK  C2    C3   C4    120.86  3.000
 1HK  H3    C2   C3    120.33  3.000
 1HK  H3    C2   C1    119.19  3.000
 1HK  C3    C2   C1    120.48  3.000
 1HK  H14   C5   H5    106.68  3.000
 1HK  H14   C5   C6    109.15  3.000
 1HK  H5    C5   C6    109.09  3.000
 1HK  H14   C5   C4    110.13  3.000
 1HK  H5    C5   C4    109.83  3.000
 1HK  C6    C5   C4    111.82  3.000
 1HK  H15   C6   H6    106.45  3.000
 1HK  H15   C6   C7    110.06  3.000
 1HK  H6    C6   C7    109.10  3.000
 1HK  H15   C6   C5    109.51  3.000
 1HK  H6    C6   C5    109.36  3.000
 1HK  C7    C6   C5    112.18  3.000
 1HK  N1    C7   C9    104.63  3.000
 1HK  C9    C7   C6    132.58  3.000
 1HK  N1    C7   C6    122.77  3.000
 1HK  C8    C9   C10   110.89  3.000
 1HK  C10   C9   C7    144.34  3.000
 1HK  C8    C9   C7    104.77  3.000
 1HK  H8    C10  H7    106.55  3.000
 1HK  H8    C10  C11   111.29  3.000
 1HK  H7    C10  C11   111.37  3.000
 1HK  H8    C10  C9    113.40  3.000
 1HK  H7    C10  C9    113.25  3.000
 1HK  C11   C10  C9    101.07  3.000
 1HK  C12   C11  C16   119.91  3.000
 1HK  C12   C11  C10   128.27  3.000
 1HK  C16   C11  C10   111.82  3.000
 1HK  C15   C16  C8    132.48  3.000
 1HK  C8    C16  C11   106.52  3.000
 1HK  C15   C16  C11   121.00  3.000
 1HK  N2    C8   C16   137.35  3.000
 1HK  C16   C8   C9    109.70  3.000
 1HK  N2    C8   C9    112.95  3.000
 1HK  N1    N2   C8    102.82  3.000
 1HK  H1    N1   N2    119.27  3.000
 1HK  H1    N1   C7    125.90  3.000
 1HK  N2    N1   C7    114.83  3.000
 1HK  H12   C15  C14   120.56  3.000
 1HK  H12   C15  C16   120.82  3.000
 1HK  C14   C15  C16   118.61  3.000
 1HK  H11   C14  C13   119.66  3.000
 1HK  H11   C14  C15   119.72  3.000
 1HK  C13   C14  C15   120.62  3.000
 1HK  H10   C13  C12   119.65  3.000
 1HK  H10   C13  C14   119.64  3.000
 1HK  C12   C13  C14   120.71  3.000
 1HK  H9    C12  C13   120.12  3.000
 1HK  H9    C12  C11   120.73  3.000
 1HK  C13   C12  C11   119.15  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
 1HK  CONST_01  C4    C17  C18  C1      0.00   0.0  0
 1HK  CONST_02  C4    C3   C2   C1      0.00   0.0  0
 1HK  CONST_03  C3    C4   C17  C18     0.00   0.0  0
 1HK  CONST_04  C3    C2   C1   C18     0.00   0.0  0
 1HK  CONST_05  C2    C3   C4   C17     0.00   0.0  0
 1HK  CONST_06  C2    C1   C18  C17     0.00   0.0  0
 1HK  CONST_07  C8    N2   N1   C7      0.00   0.0  0
 1HK  CONST_08  N2    C8   C9   C7      0.00   0.0  0
 1HK  CONST_09  C16   C8   C9   C7    180.00   0.0  0
 1HK  CONST_10  N1    N2   C8   C9      0.00   0.0  0
 1HK  CONST_11  C15   C16  C8   C9    180.00   0.0  0
 1HK  CONST_12  C11   C16  C8   C9      0.00   0.0  0
 1HK  CONST_13  N2    N1   C7   C9      0.00   0.0  0
 1HK  CONST_14  C14   C15  C16  C11     0.00   0.0  0
 1HK  CONST_15  N2    C8   C16  C11   180.00   0.0  0
 1HK  CONST_16  C14   C13  C12  C11     0.00   0.0  0
 1HK  CONST_17  C13   C14  C15  C16     0.00   0.0  0
 1HK  CONST_18  N1    N2   C8   C16   180.00   0.0  0
 1HK  CONST_19  C13   C12  C11  C16     0.00   0.0  0
 1HK  CONST_20  C14   C15  C16  C8    180.00   0.0  0
 1HK  CONST_21  C12   C11  C16  C8    180.00   0.0  0
 1HK  CONST_22  N1    C7   C9   C8      0.00   0.0  0
 1HK  CONST_23  C15   C16  C8   N2      0.00   0.0  0
 1HK  CONST_24  C12   C13  C14  C15     0.00   0.0  0
 1HK  CONST_25  C12   C11  C16  C15     0.00   0.0  0
 1HK  CONST_26  C17   C18  C1   O1    180.00   0.0  0
 1HK  CONST_27  C3    C2   C1   O1    180.00   0.0  0
 1HK  CONST_28  C5    C4   C17  C18   180.00   0.0  0
 1HK  CONST_29  C4    C17  C18  O2    180.00   0.0  0
 1HK  CONST_30  C2    C1   C18  O2    180.00   0.0  0
 1HK  CONST_31  C5    C4   C3   C2    180.00   0.0  0
 1HK  CONST_32  N2    N1   C7   C6    180.00   0.0  0
 1HK  CONST_33  C8    C9   C7   C6    180.00   0.0  0
 1HK  CONST_34  C10   C9   C7   C6      0.00   0.0  0
 1HK  CONST_35  H13   C17  C18  C1    180.00   0.0  0
 1HK  CONST_36  H4    C3   C2   C1    180.00   0.0  0
 1HK  CONST_37  H3    C2   C1   C18   180.00   0.0  0
 1HK  CONST_38  H1    N1   C7   C9    180.00   0.0  0
 1HK  CONST_39  H9    C12  C11  C10     0.00   0.0  0
 1HK  CONST_40  H12   C15  C16  C11   180.00   0.0  0
 1HK  CONST_41  H10   C13  C12  C11   180.00   0.0  0
 1HK  CONST_42  H11   C14  C15  C16   180.00   0.0  0
 1HK  Var_01    H7    C10  C9   C7    -61.29  30.0  1
 1HK  Var_02    C17   C18  O2   C19    -0.21  30.0  2
 1HK  Var_03    C6    C5   C4   C17    81.30  30.0  2
 1HK  Var_04    C7    C6   C5   C4   -179.27  30.0  2
 1HK  Var_05    N1    C7   C6   C5   -111.57  30.0  3
 1HK  Var_06    H192  C19  O2   C18    62.27  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
 1HK  plan-1  O1   0.020
 1HK  plan-1  C1   0.020
 1HK  plan-1  C18  0.020
 1HK  plan-1  O2   0.020
 1HK  plan-1  C17  0.020
 1HK  plan-1  C4   0.020
 1HK  plan-1  C3   0.020
 1HK  plan-1  C2   0.020
 1HK  plan-1  C5   0.020
 1HK  plan-1  H13  0.020
 1HK  plan-1  H4   0.020
 1HK  plan-1  H3   0.020
 1HK  plan-2  C6   0.020
 1HK  plan-2  C7   0.020
 1HK  plan-2  C9   0.020
 1HK  plan-2  C10  0.020
 1HK  plan-2  C11  0.020
 1HK  plan-2  C16  0.020
 1HK  plan-2  C8   0.020
 1HK  plan-2  N2   0.020
 1HK  plan-2  N1   0.020
 1HK  plan-2  C15  0.020
 1HK  plan-2  C14  0.020
 1HK  plan-2  C13  0.020
 1HK  plan-2  C12  0.020
 1HK  plan-2  H1   0.020
 1HK  plan-2  H12  0.020
 1HK  plan-2  H11  0.020
 1HK  plan-2  H10  0.020
 1HK  plan-2  H9   0.020

