# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 04:11:09 2020
#   Inital geometry file: a 119 line input string
#   Ligand name: 4-[(6,7-dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethynyl]-2-methoxyphenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(ccc1O)C#Cc2[nH]nc3c2Cc4cc(OC)c(OC)cc34
#
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
 HK4  HK4  4-[(6,7-dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethynyl]-2-methoxyphenol  ligand  45  27  .  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_HK4
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
 HK4  O1    O  OH1   0  -0.621  -8.1995  -0.1625   0.0596
 HK4  C1    C  CR6   0   0.290  -6.8871   0.1219   0.0507
 HK4  C6    C  CR6   0   0.310  -5.9196  -0.9018   0.0574
 HK4  O2    O  O2    0  -0.487  -6.4248  -2.1510   0.0739
 HK4  C7    C  CH3   0  -0.435  -5.5292  -3.2464   0.0714
 HK4  C5    C  CR16  0  -0.442  -4.5767  -0.5804   0.0470
 HK4  C4    C  CR6   0  -0.108  -4.1714   0.7635   0.0301
 HK4  C3    C  CR16  0  -0.300  -5.1318   1.7715   0.0240
 HK4  C2    C  CR16  0  -0.339  -6.4801   1.4459   0.0345
 HK4  C8    C  CSP   0   0.130  -2.7849   1.0698   0.0182
 HK4  C9    C  CSP   0   0.085  -1.5998   1.3040   0.0164
 HK4  C10   C  CR5   0   0.183  -0.2106   1.5347   0.0068
 HK4  C12   C  CR55  0  -0.125   0.8634   0.6732  -0.0030
 HK4  C13   C  CH2   0  -0.556   1.2714  -0.7620  -0.0077
 HK4  C14   C  CR56  0   0.009   2.7842  -0.6271  -0.0192
 HK4  C21   C  CR56  0   0.107   3.1921   0.7060  -0.0216
 HK4  C11   C  CR55  0   0.154   1.9835   1.5129  -0.0110
 HK4  N2    N  N     0  -0.274   1.6660   2.7930  -0.0064
 HK4  N1    N  NR15  0  -0.496   0.3352   2.7852   0.0041
 HK4  C20   C  CR16  0  -0.458   4.5417   1.0477  -0.0325
 HK4  C18   C  CR6   0   0.315   5.4880   0.0361  -0.0403
 HK4  O4    O  O2    0  -0.466   6.8202   0.2316  -0.0510
 HK4  C19   C  CH3   0  -0.439   7.2952   1.5619  -0.0540
 HK4  C16   C  CR6   0   0.312   5.0797  -1.3192  -0.0369
 HK4  C15   C  CR16  0  -0.448   3.7298  -1.6437  -0.0268
 HK4  O3    O  O2    0  -0.463   6.0818  -2.2172  -0.0440
 HK4  C17   C  CH3   0  -0.439   5.7482  -3.5894  -0.0405
 HK4  H2    H  HOH1  0   0.476  -8.3358  -1.1184   0.0645
 HK4  H73   H  HCH3  0   0.234  -4.9019  -3.2527  -0.8231
 HK4  H72   H  HCH3  0   0.234  -4.8899  -3.2474   0.9574
 HK4  H71   H  HCH3  0   0.266  -6.1402  -4.1449   0.0782
 HK4  H5    H  HCR6  0   0.290  -3.8205  -1.3532   0.0517
 HK4  H4    H  HCR6  0   0.261  -4.8301   2.8099   0.0100
 HK4  H3    H  HCR6  0   0.274  -7.2294   2.2271   0.0294
 HK4  H6    H  HCH2  0   0.275   0.9194  -1.3081   0.8716
 HK4  H7    H  HCH2  0   0.275   0.9064  -1.3059  -0.8831
 HK4  H1    H  HNR5  0   0.423  -0.1721   3.6565   0.0128
 HK4  H9    H  HCR6  0   0.277   4.8342   2.0893  -0.0352
 HK4  H191  H  HCH3  0   0.228   6.9647   2.1107  -0.9399
 HK4  H192  H  HCH3  0   0.228   6.9778   2.1103   0.8371
 HK4  H193  H  HCH3  0   0.261   8.3809   1.5040  -0.0620
 HK4  H8    H  HCR6  0   0.281   3.4072  -2.6772  -0.0243
 HK4  H172  H  HCH3  0   0.228   5.1830  -3.8713   0.8522
 HK4  H171  H  HCH3  0   0.228   5.1721  -3.8735  -0.9255
 HK4  H173  H  HCH3  0   0.261   6.6883  -4.1360  -0.0456

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
 HK4  C19  O4    single    1.413  0.020  1.413
 HK4  O4   C18   single    1.347  0.020  1.347
 HK4  N2   N1    aromatic  1.331  0.020  1.331
 HK4  N2   C11   aromatic  1.319  0.020  1.319
 HK4  C20  C18   aromatic  1.385  0.020  1.385
 HK4  C20  C21   aromatic  1.392  0.020  1.392
 HK4  C18  C16   aromatic  1.415  0.020  1.415
 HK4  N1   C10   aromatic  1.364  0.020  1.364
 HK4  C11  C21   aromatic  1.453  0.020  1.453
 HK4  C11  C12   aromatic  1.400  0.020  1.400
 HK4  C21  C14   aromatic  1.394  0.020  1.394
 HK4  C10  C12   aromatic  1.377  0.020  1.377
 HK4  C10  C9    single    1.408  0.020  1.408
 HK4  C16  O3    single    1.346  0.020  1.346
 HK4  C16  C15   aromatic  1.388  0.020  1.388
 HK4  C12  C13   single    1.492  0.020  1.492
 HK4  C14  C15   aromatic  1.388  0.020  1.388
 HK4  C14  C13   single    1.519  0.020  1.519
 HK4  O3   C17   single    1.412  0.020  1.412
 HK4  C9   C8    triple    1.208  0.020  1.208
 HK4  C8   C4    single    1.420  0.020  1.420
 HK4  C4   C3    aromatic  1.392  0.020  1.392
 HK4  C4   C5    aromatic  1.404  0.020  1.404
 HK4  C3   C2    aromatic  1.387  0.020  1.387
 HK4  C5   C6    aromatic  1.381  0.020  1.381
 HK4  C2   C1    aromatic  1.385  0.020  1.385
 HK4  C6   C1    aromatic  1.409  0.020  1.409
 HK4  C6   O2    single    1.348  0.020  1.348
 HK4  C1   O1    single    1.343  0.020  1.343
 HK4  C7   O2    single    1.415  0.020  1.415
 HK4  O1   H2    single    0.850  0.020  0.980
 HK4  C7   H73   single    0.970  0.020  1.090
 HK4  C7   H72   single    0.970  0.020  1.090
 HK4  C7   H71   single    0.970  0.020  1.090
 HK4  C5   H5    single    0.930  0.020  1.080
 HK4  C3   H4    single    0.930  0.020  1.080
 HK4  C2   H3    single    0.930  0.020  1.080
 HK4  C13  H6    single    0.970  0.020  1.090
 HK4  C13  H7    single    0.970  0.020  1.090
 HK4  N1   H1    single    0.860  0.020  1.020
 HK4  C20  H9    single    0.930  0.020  1.080
 HK4  C19  H191  single    0.970  0.020  1.090
 HK4  C19  H192  single    0.970  0.020  1.090
 HK4  C19  H193  single    0.970  0.020  1.090
 HK4  C15  H8    single    0.930  0.020  1.080
 HK4  C17  H172  single    0.970  0.020  1.090
 HK4  C17  H171  single    0.970  0.020  1.090
 HK4  C17  H173  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
 HK4  H2    O1   C1    110.35  3.000
 HK4  C2    C1   C6    119.53  3.000
 HK4  C6    C1   O1    121.15  3.000
 HK4  C2    C1   O1    119.32  3.000
 HK4  C5    C6   O2    125.48  3.000
 HK4  O2    C6   C1    114.60  3.000
 HK4  C5    C6   C1    119.92  3.000
 HK4  C7    O2   C6    118.71  3.000
 HK4  H71   C7   H72   108.86  3.000
 HK4  H71   C7   H73   108.86  3.000
 HK4  H72   C7   H73   109.15  3.000
 HK4  H71   C7   O2    106.51  3.000
 HK4  H72   C7   O2    111.69  3.000
 HK4  H73   C7   O2    111.68  3.000
 HK4  H5    C5   C4    118.84  3.000
 HK4  H5    C5   C6    120.91  3.000
 HK4  C4    C5   C6    120.24  3.000
 HK4  C8    C4   C3    121.15  3.000
 HK4  C3    C4   C5    119.60  3.000
 HK4  C8    C4   C5    119.24  3.000
 HK4  H4    C3   C2    119.78  3.000
 HK4  H4    C3   C4    120.19  3.000
 HK4  C2    C3   C4    120.04  3.000
 HK4  H3    C2   C3    120.23  3.000
 HK4  H3    C2   C1    119.11  3.000
 HK4  C3    C2   C1    120.67  3.000
 HK4  C9    C8   C4    180.00  3.000
 HK4  C10   C9   C8    180.00  3.000
 HK4  N1    C10  C12   105.15  3.000
 HK4  C12   C10  C9    131.84  3.000
 HK4  N1    C10  C9    123.01  3.000
 HK4  C11   C12  C13   110.99  3.000
 HK4  C13   C12  C10   144.60  3.000
 HK4  C11   C12  C10   104.41  3.000
 HK4  H7    C13  H6    106.73  3.000
 HK4  H7    C13  C14   111.75  3.000
 HK4  H6    C13  C14   111.79  3.000
 HK4  H7    C13  C12   112.94  3.000
 HK4  H6    C13  C12   112.95  3.000
 HK4  C14   C13  C12   100.78  3.000
 HK4  C15   C14  C21   120.06  3.000
 HK4  C15   C14  C13   127.83  3.000
 HK4  C21   C14  C13   112.11  3.000
 HK4  C20   C21  C11   132.07  3.000
 HK4  C11   C21  C14   106.71  3.000
 HK4  C20   C21  C14   121.22  3.000
 HK4  N2    C11  C21   137.66  3.000
 HK4  C21   C11  C12   109.42  3.000
 HK4  N2    C11  C12   112.93  3.000
 HK4  N1    N2   C11   103.59  3.000
 HK4  H1    N1   N2    119.87  3.000
 HK4  H1    N1   C10   126.21  3.000
 HK4  N2    N1   C10   113.92  3.000
 HK4  H9    C20  C18   121.23  3.000
 HK4  H9    C20  C21   119.89  3.000
 HK4  C18   C20  C21   118.88  3.000
 HK4  C16   C18  O4    115.11  3.000
 HK4  C16   C18  C20   120.15  3.000
 HK4  O4    C18  C20   124.74  3.000
 HK4  C19   O4   C18   118.00  3.000
 HK4  H193  C19  H192  108.82  3.000
 HK4  H193  C19  H191  108.82  3.000
 HK4  H192  C19  H191  108.71  3.000
 HK4  H193  C19  O4    106.60  3.000
 HK4  H192  C19  O4    111.90  3.000
 HK4  H191  C19  O4    111.89  3.000
 HK4  O3    C16  C15   124.62  3.000
 HK4  C15   C16  C18   120.28  3.000
 HK4  O3    C16  C18   115.10  3.000
 HK4  H8    C15  C16   120.85  3.000
 HK4  H8    C15  C14   119.74  3.000
 HK4  C16   C15  C14   119.41  3.000
 HK4  C17   O3   C16   118.20  3.000
 HK4  H173  C17  H171  108.73  3.000
 HK4  H173  C17  H172  108.73  3.000
 HK4  H171  C17  H172  108.74  3.000
 HK4  H173  C17  O3    106.51  3.000
 HK4  H171  C17  O3    112.02  3.000
 HK4  H172  C17  O3    112.00  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
 HK4  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 HK4  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 HK4  CONST_03  C3    C4   C5   C6      0.00   0.0  0
 HK4  CONST_04  C3    C2   C1   C6      0.00   0.0  0
 HK4  CONST_05  C2    C3   C4   C5      0.00   0.0  0
 HK4  CONST_06  C2    C1   C6   C5      0.00   0.0  0
 HK4  CONST_07  C11   N2   N1   C10     0.00   0.0  0
 HK4  CONST_08  N2    C11  C12  C10     0.00   0.0  0
 HK4  CONST_09  C21   C11  C12  C10   180.00   0.0  0
 HK4  CONST_10  N1    N2   C11  C12     0.00   0.0  0
 HK4  CONST_11  C20   C21  C11  C12   180.00   0.0  0
 HK4  CONST_12  C14   C21  C11  C12     0.00   0.0  0
 HK4  CONST_13  N2    N1   C10  C12     0.00   0.0  0
 HK4  CONST_14  C18   C20  C21  C14     0.00   0.0  0
 HK4  CONST_15  N2    C11  C21  C14   180.00   0.0  0
 HK4  CONST_16  C18   C16  C15  C14     0.00   0.0  0
 HK4  CONST_17  C16   C18  C20  C21     0.00   0.0  0
 HK4  CONST_18  N1    N2   C11  C21   180.00   0.0  0
 HK4  CONST_19  C16   C15  C14  C21     0.00   0.0  0
 HK4  CONST_20  C18   C20  C21  C11   180.00   0.0  0
 HK4  CONST_21  C15   C14  C21  C11   180.00   0.0  0
 HK4  CONST_22  N1    C10  C12  C11     0.00   0.0  0
 HK4  CONST_23  C20   C21  C11  N2      0.00   0.0  0
 HK4  CONST_24  C15   C16  C18  C20     0.00   0.0  0
 HK4  CONST_25  C15   C14  C21  C20     0.00   0.0  0
 HK4  CONST_26  C3    C2   C1   O1    180.00   0.0  0
 HK4  CONST_27  C5    C6   C1   O1    180.00   0.0  0
 HK4  CONST_28  C8    C4   C5   C6    180.00   0.0  0
 HK4  CONST_29  C4    C5   C6   O2    180.00   0.0  0
 HK4  CONST_30  C2    C1   C6   O2    180.00   0.0  0
 HK4  CONST_31  C8    C4   C3   C2    180.00   0.0  0
 HK4  CONST_32  N2    N1   C10  C9    180.00   0.0  0
 HK4  CONST_33  C11   C12  C10  C9    180.00   0.0  0
 HK4  CONST_34  C13   C12  C10  C9      0.00   0.0  0
 HK4  CONST_35  O3    C16  C15  C14   180.00   0.0  0
 HK4  CONST_36  O4    C18  C20  C21   180.00   0.0  0
 HK4  CONST_37  O3    C16  C18  C20   180.00   0.0  0
 HK4  CONST_38  C15   C16  C18  O4    180.00   0.0  0
 HK4  CONST_39  H4    C3   C2   C1    180.00   0.0  0
 HK4  CONST_40  H5    C5   C6   C1    180.00   0.0  0
 HK4  CONST_41  H3    C2   C1   C6    180.00   0.0  0
 HK4  CONST_42  H1    N1   C10  C12   180.00   0.0  0
 HK4  CONST_43  H8    C15  C14  C13     0.00   0.0  0
 HK4  CONST_44  H9    C20  C21  C14   180.00   0.0  0
 HK4  Var_01    H6    C13  C12  C10   -60.56  30.0  1
 HK4  Var_02    C5    C6   O2   C7     -0.47  30.0  3
 HK4  Var_03    C16   C18  O4   C19  -179.96  30.0  2
 HK4  Var_04    H73   C7   O2   C6    -60.82  30.0  3
 HK4  Var_05    H191  C19  O4   C18   -61.19  30.0  3
 HK4  Var_06    H172  C17  O3   C16   -61.15  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
 HK4  plan-1  O1   0.020
 HK4  plan-1  C1   0.020
 HK4  plan-1  C6   0.020
 HK4  plan-1  O2   0.020
 HK4  plan-1  C5   0.020
 HK4  plan-1  C4   0.020
 HK4  plan-1  C3   0.020
 HK4  plan-1  C2   0.020
 HK4  plan-1  C8   0.020
 HK4  plan-1  C9   0.020
 HK4  plan-1  H5   0.020
 HK4  plan-1  H4   0.020
 HK4  plan-1  H3   0.020
 HK4  plan-2  C8   0.020
 HK4  plan-2  C9   0.020
 HK4  plan-2  C10  0.020
 HK4  plan-2  C12  0.020
 HK4  plan-2  C13  0.020
 HK4  plan-2  C14  0.020
 HK4  plan-2  C21  0.020
 HK4  plan-2  C11  0.020
 HK4  plan-2  N2   0.020
 HK4  plan-2  N1   0.020
 HK4  plan-2  C20  0.020
 HK4  plan-2  C18  0.020
 HK4  plan-2  O4   0.020
 HK4  plan-2  C16  0.020
 HK4  plan-2  C15  0.020
 HK4  plan-2  O3   0.020
 HK4  plan-2  H1   0.020
 HK4  plan-2  H9   0.020
 HK4  plan-2  H8   0.020

