# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 06:45:18 2020
#   Inital geometry file: a 101 line input string
#   Ligand name: 4-(6,7-dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2Cc3c([nH]nc3c2cc1OC)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
 HK1  HK1  4-(6,7-dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol  ligand  39  23  .  2021-08-11  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HK1
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
 HK1  O1    O  OH1   0  -0.626  -7.1172   1.1875   0.1052
 HK1  C1    C  CR6   0   0.348  -5.8840   0.6529   0.0659
 HK1  C6    C  CR16  0  -0.371  -5.6539  -0.7195   0.1230
 HK1  C5    C  CR16  0  -0.284  -4.3609  -1.2118   0.0787
 HK1  C4    C  CR6   0   0.041  -3.2626  -0.3578  -0.0269
 HK1  C3    C  CR16  0  -0.339  -3.5118   1.0164  -0.0809
 HK1  C2    C  CR16  0  -0.317  -4.7975   1.5205  -0.0349
 HK1  C7    C  CR5   0   0.381  -1.8909  -0.8467  -0.0758
 HK1  C9    C  CR55  0  -0.134  -0.6792  -0.1932  -0.0293
 HK1  C10   C  CH2   0  -0.562  -0.0197   1.1433   0.0880
 HK1  C11   C  CR56  0   0.024   1.4454   0.7464   0.0565
 HK1  C18   C  CR56  0   0.115   1.6118  -0.6329  -0.0579
 HK1  C8    C  CR55  0   0.159   0.2802  -1.2118  -0.1095
 HK1  N2    N  N     0  -0.282  -0.2517  -2.4125  -0.2033
 HK1  N1    N  NR15  0  -0.542  -1.5657  -2.1649  -0.1797
 HK1  C17   C  CR16  0  -0.461   2.8805  -1.2046  -0.1051
 HK1  C15   C  CR6   0   0.314   3.9906  -0.3784  -0.0406
 HK1  O3    O  O2    0  -0.467   5.2678  -0.8042  -0.0776
 HK1  C16   C  CH3   0  -0.439   5.5033  -2.1929  -0.1807
 HK1  C13   C  CR6   0   0.313   3.8273   1.0230   0.0723
 HK1  C12   C  CR16  0  -0.456   2.5554   1.5774   0.1209
 HK1  O2    O  O2    0  -0.464   4.9722   1.7292   0.1256
 HK1  C14   C  CH3   0  -0.438   4.8852   3.1362   0.2163
 HK1  H2    H  HOH1  0   0.477  -7.7844   0.4951   0.1726
 HK1  H6    H  HCR6  0   0.278  -6.4845  -1.4106   0.2054
 HK1  H5    H  HCR6  0   0.249  -4.2309  -2.2851   0.1359
 HK1  H4    H  HCR6  0   0.268  -2.6886   1.7141  -0.1644
 HK1  H3    H  HCR6  0   0.269  -4.9629   2.5896  -0.0791
 HK1  H8    H  HCH2  0   0.270  -0.2671   1.8219  -0.7337
 HK1  H7    H  HCH2  0   0.272  -0.2775   1.6663   1.0135
 HK1  H1    H  HNR5  0   0.417  -2.2029  -2.9399  -0.2663
 HK1  H10   H  HCR6  0   0.276   2.9844  -2.2777  -0.1927
 HK1  H161  H  HCH3  0   0.227   5.0980  -2.7417   0.6741
 HK1  H162  H  HCH3  0   0.227   5.0833  -2.6133  -1.0987
 HK1  H163  H  HCH3  0   0.261   6.5826  -2.3227  -0.1988
 HK1  H9    H  HCR6  0   0.280   2.4209   2.6478   0.2075
 HK1  H143  H  HCH3  0   0.261   5.9065   3.5084   0.2333
 HK1  H141  H  HCH3  0   0.228   4.3661   3.5695  -0.6432
 HK1  H142  H  HCH3  0   0.228   4.3780   3.4569   1.1303

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
 HK1  C16  O3    single    1.412  0.020  1.412
 HK1  O3   C15   single    1.347  0.020  1.347
 HK1  C17  C15   aromatic  1.385  0.020  1.385
 HK1  C17  C18   aromatic  1.392  0.020  1.392
 HK1  N2   N1    aromatic  1.337  0.020  1.337
 HK1  N2   C8    aromatic  1.317  0.020  1.317
 HK1  C15  C13   aromatic  1.415  0.020  1.415
 HK1  N1   C7    aromatic  1.362  0.020  1.362
 HK1  C8   C18   aromatic  1.453  0.020  1.453
 HK1  C8   C9    aromatic  1.402  0.020  1.402
 HK1  C18  C11   aromatic  1.394  0.020  1.394
 HK1  C13  O2    single    1.346  0.020  1.346
 HK1  C13  C12   aromatic  1.388  0.020  1.388
 HK1  O2   C14   single    1.413  0.020  1.413
 HK1  C7   C9    aromatic  1.377  0.020  1.377
 HK1  C7   C4    single    1.457  0.020  1.457
 HK1  C9   C10   single    1.495  0.020  1.495
 HK1  C11  C12   aromatic  1.388  0.020  1.388
 HK1  C11  C10   single    1.518  0.020  1.518
 HK1  C3   C4    aromatic  1.398  0.020  1.398
 HK1  C3   C2    aromatic  1.382  0.020  1.382
 HK1  C4   C5    aromatic  1.395  0.020  1.395
 HK1  C2   C1    aromatic  1.394  0.020  1.394
 HK1  C5   C6    aromatic  1.384  0.020  1.384
 HK1  C1   C6    aromatic  1.393  0.020  1.393
 HK1  C1   O1    single    1.345  0.020  1.345
 HK1  O1   H2    single    0.850  0.020  0.980
 HK1  C6   H6    single    0.930  0.020  1.080
 HK1  C5   H5    single    0.930  0.020  1.080
 HK1  C3   H4    single    0.930  0.020  1.080
 HK1  C2   H3    single    0.930  0.020  1.080
 HK1  C10  H8    single    0.970  0.020  1.090
 HK1  C10  H7    single    0.970  0.020  1.090
 HK1  N1   H1    single    0.860  0.020  1.020
 HK1  C17  H10   single    0.930  0.020  1.080
 HK1  C16  H161  single    0.970  0.020  1.090
 HK1  C16  H162  single    0.970  0.020  1.090
 HK1  C16  H163  single    0.970  0.020  1.090
 HK1  C12  H9    single    0.930  0.020  1.080
 HK1  C14  H143  single    0.970  0.020  1.090
 HK1  C14  H141  single    0.970  0.020  1.090
 HK1  C14  H142  single    0.970  0.020  1.090

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
 HK1  H2    O1   C1    110.56  3.000
 HK1  C2    C1   C6    119.17  3.000
 HK1  C6    C1   O1    122.83  3.000
 HK1  C2    C1   O1    118.00  3.000
 HK1  H6    C6   C5    119.44  3.000
 HK1  H6    C6   C1    120.32  3.000
 HK1  C5    C6   C1    120.23  3.000
 HK1  H5    C5   C4    121.08  3.000
 HK1  H5    C5   C6    117.59  3.000
 HK1  C4    C5   C6    121.33  3.000
 HK1  C7    C4   C3    119.77  3.000
 HK1  C3    C4   C5    117.67  3.000
 HK1  C7    C4   C5    122.57  3.000
 HK1  H4    C3   C2    118.37  3.000
 HK1  H4    C3   C4    120.08  3.000
 HK1  C2    C3   C4    121.56  3.000
 HK1  H3    C2   C3    120.07  3.000
 HK1  H3    C2   C1    119.90  3.000
 HK1  C3    C2   C1    120.04  3.000
 HK1  N1    C7   C9    104.58  3.000
 HK1  C9    C7   C4    131.90  3.000
 HK1  N1    C7   C4    123.52  3.000
 HK1  C8    C9   C10   110.62  3.000
 HK1  C10   C9   C7    144.57  3.000
 HK1  C8    C9   C7    104.80  3.000
 HK1  H7    C10  H8    106.59  3.000
 HK1  H7    C10  C11   111.71  3.000
 HK1  H8    C10  C11   111.40  3.000
 HK1  H7    C10  C9    112.95  3.000
 HK1  H8    C10  C9    113.32  3.000
 HK1  C11   C10  C9    100.97  3.000
 HK1  C12   C11  C18   120.05  3.000
 HK1  C12   C11  C10   127.89  3.000
 HK1  C18   C11  C10   112.06  3.000
 HK1  C17   C18  C8    132.09  3.000
 HK1  C8    C18  C11   106.72  3.000
 HK1  C17   C18  C11   121.19  3.000
 HK1  N2    C8   C18   137.41  3.000
 HK1  C18   C8   C9    109.62  3.000
 HK1  N2    C8   C9    112.97  3.000
 HK1  N1    N2   C8    103.11  3.000
 HK1  H1    N1   N2    118.53  3.000
 HK1  H1    N1   C7    126.90  3.000
 HK1  N2    N1   C7    114.54  3.000
 HK1  H10   C17  C15   121.23  3.000
 HK1  H10   C17  C18   119.84  3.000
 HK1  C15   C17  C18   118.93  3.000
 HK1  C13   C15  O3    115.13  3.000
 HK1  C13   C15  C17   120.11  3.000
 HK1  O3    C15  C17   124.76  3.000
 HK1  C16   O3   C15   118.10  3.000
 HK1  H163  C16  H162  108.75  3.000
 HK1  H163  C16  H161  108.73  3.000
 HK1  H162  C16  H161  108.72  3.000
 HK1  H163  C16  O3    106.51  3.000
 HK1  H162  C16  O3    112.03  3.000
 HK1  H161  C16  O3    112.00  3.000
 HK1  O2    C13  C12   124.63  3.000
 HK1  C12   C13  C15   120.26  3.000
 HK1  O2    C13  C15   115.11  3.000
 HK1  H9    C12  C13   120.77  3.000
 HK1  H9    C12  C11   119.77  3.000
 HK1  C13   C12  C11   119.47  3.000
 HK1  C14   O2   C13   118.20  3.000
 HK1  H142  C14  H141  108.70  3.000
 HK1  H142  C14  H143  108.80  3.000
 HK1  H141  C14  H143  108.82  3.000
 HK1  H142  C14  O2    111.98  3.000
 HK1  H141  C14  O2    111.93  3.000
 HK1  H143  C14  O2    106.50  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
 HK1  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 HK1  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 HK1  CONST_03  C7    C4   C5   C6    180.00   0.0  0
 HK1  CONST_04  C3    C4   C5   C6      0.00   0.0  0
 HK1  CONST_05  C3    C2   C1   C6      0.00   0.0  0
 HK1  CONST_06  N1    C7   C4   C5      0.00   0.0  0
 HK1  CONST_07  C9    C7   C4   C5    180.00   0.0  0
 HK1  CONST_08  C2    C3   C4   C5      0.00   0.0  0
 HK1  CONST_09  C2    C1   C6   C5      0.00   0.0  0
 HK1  CONST_10  N2    N1   C7   C4    180.00   0.0  0
 HK1  CONST_11  C8    C9   C7   C4    180.00   0.0  0
 HK1  CONST_12  N1    C7   C4   C3    180.00   0.0  0
 HK1  CONST_13  C9    C7   C4   C3      0.00   0.0  0
 HK1  CONST_14  C7    C4   C3   C2    180.00   0.0  0
 HK1  CONST_15  C8    N2   N1   C7      0.00   0.0  0
 HK1  CONST_16  N2    C8   C9   C7      0.00   0.0  0
 HK1  CONST_17  C18   C8   C9   C7    180.00   0.0  0
 HK1  CONST_18  N1    N2   C8   C9      0.00   0.0  0
 HK1  CONST_19  C17   C18  C8   C9    180.00   0.0  0
 HK1  CONST_20  C11   C18  C8   C9      0.00   0.0  0
 HK1  CONST_21  N2    N1   C7   C9      0.00   0.0  0
 HK1  CONST_22  C15   C17  C18  C11     0.00   0.0  0
 HK1  CONST_23  N2    C8   C18  C11   180.00   0.0  0
 HK1  CONST_24  C15   C13  C12  C11     0.00   0.0  0
 HK1  CONST_25  C13   C15  C17  C18     0.00   0.0  0
 HK1  CONST_26  N1    N2   C8   C18   180.00   0.0  0
 HK1  CONST_27  C13   C12  C11  C18     0.00   0.0  0
 HK1  CONST_28  C15   C17  C18  C8    180.00   0.0  0
 HK1  CONST_29  C12   C11  C18  C8    180.00   0.0  0
 HK1  CONST_30  N1    C7   C9   C8      0.00   0.0  0
 HK1  CONST_31  C17   C18  C8   N2      0.00   0.0  0
 HK1  CONST_32  C12   C13  C15  C17     0.00   0.0  0
 HK1  CONST_33  C12   C11  C18  C17     0.00   0.0  0
 HK1  CONST_34  C10   C9   C7   C4      0.00   0.0  0
 HK1  CONST_35  C3    C2   C1   O1    180.00   0.0  0
 HK1  CONST_36  C5    C6   C1   O1    180.00   0.0  0
 HK1  CONST_37  O2    C13  C12  C11   180.00   0.0  0
 HK1  CONST_38  O3    C15  C17  C18   180.00   0.0  0
 HK1  CONST_39  O2    C13  C15  C17   180.00   0.0  0
 HK1  CONST_40  C12   C13  C15  O3    180.00   0.0  0
 HK1  CONST_41  H4    C3   C2   C1    180.00   0.0  0
 HK1  CONST_42  H5    C5   C6   C1    180.00   0.0  0
 HK1  CONST_43  H3    C2   C1   C6    180.00   0.0  0
 HK1  CONST_44  H1    N1   C7   C4      0.00   0.0  0
 HK1  CONST_45  H6    C6   C5   C4    180.00   0.0  0
 HK1  CONST_46  H9    C12  C11  C10     0.00   0.0  0
 HK1  CONST_47  H10   C17  C18  C11   180.00   0.0  0
 HK1  Var_01    H8    C10  C9   C7    -61.68  30.0  1
 HK1  Var_02    C13   C15  O3   C16   179.59  30.0  2
 HK1  Var_03    H161  C16  O3   C15   -61.46  30.0  3
 HK1  Var_04    H143  C14  O2   C13  -179.24  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
 HK1  plan-1  O1   0.020
 HK1  plan-1  C1   0.020
 HK1  plan-1  C6   0.020
 HK1  plan-1  C5   0.020
 HK1  plan-1  C4   0.020
 HK1  plan-1  C3   0.020
 HK1  plan-1  C2   0.020
 HK1  plan-1  C7   0.020
 HK1  plan-1  H6   0.020
 HK1  plan-1  H5   0.020
 HK1  plan-1  H4   0.020
 HK1  plan-1  H3   0.020
 HK1  plan-2  C4   0.020
 HK1  plan-2  C7   0.020
 HK1  plan-2  C9   0.020
 HK1  plan-2  C10  0.020
 HK1  plan-2  C11  0.020
 HK1  plan-2  C18  0.020
 HK1  plan-2  C8   0.020
 HK1  plan-2  N2   0.020
 HK1  plan-2  N1   0.020
 HK1  plan-2  C17  0.020
 HK1  plan-2  C15  0.020
 HK1  plan-2  O3   0.020
 HK1  plan-2  C13  0.020
 HK1  plan-2  C12  0.020
 HK1  plan-2  O2   0.020
 HK1  plan-2  H1   0.020
 HK1  plan-2  H10  0.020
 HK1  plan-2  H9   0.020

