# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 03:07:24 2020
#   Inital geometry file: a 123 line input string
#   Ligand name: 5-{7-ethyl-6-[(3S)-tetrahydrofuran-3-yloxy]-2,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1cc2c(Cc3c([nH]nc23)c4ccc(nc4)C#N)cc1O[C@H]5CCOC5
#
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
 4HK  4HK  5-{7-ethyl-6-[(3S)-tetrahydrofuran-3-yloxy]-2,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile  ligand  48  28  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_4HK
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
 4HK  N1    N  NS    0  -0.235  -8.5485  -2.3179  -0.5831
 4HK  C1    C  CSP   0   0.062  -7.5852  -1.7009  -0.4557
 4HK  C2    C  CR6   0   0.187  -6.3897  -0.9236  -0.2882
 4HK  N2    N  N     0  -0.395  -5.2414  -1.5934  -0.3491
 4HK  C6    C  CR16  0  -0.134  -4.1250  -0.9129  -0.1974
 4HK  C5    C  CR6   0  -0.015  -4.0775   0.4717   0.0209
 4HK  C4    C  CR16  0  -0.179  -5.2926   1.1492   0.0751
 4HK  C3    C  CR16  0  -0.254  -6.4726   0.4446  -0.0780
 4HK  C7    C  CR5   0   0.384  -2.7911   1.1262   0.1709
 4HK  C9    C  CR55  0  -0.113  -1.5042   0.6616   0.0128
 4HK  C10   C  CH2   0  -0.571  -0.6718  -0.5292  -0.3376
 4HK  C11   C  CR56  0   0.040   0.7269   0.0532  -0.2358
 4HK  C22   C  CR56  0   0.103   0.7048   1.4034   0.1307
 4HK  C8    C  CR55  0   0.165  -0.6924   1.7707   0.2821
 4HK  N4    N  N     0  -0.265  -1.3868   2.8477   0.5910
 4HK  N3    N  NR15  0  -0.538  -2.6505   2.4369   0.5149
 4HK  C21   C  CR16  0  -0.363   1.8911   2.1053   0.2848
 4HK  C18   C  CR6   0   0.015   3.1112   1.4771   0.0773
 4HK  C19   C  CH2   0  -0.491   4.3956   2.2472   0.2239
 4HK  C20   C  CH3   0  -0.657   4.9355   2.7532  -1.1129
 4HK  C13   C  CR6   0   0.357   3.1200   0.1208  -0.2995
 4HK  C12   C  CR16  0  -0.444   1.9299  -0.5940  -0.4499
 4HK  O1    O  O2    0  -0.475   4.3406  -0.4119  -0.5114
 4HK  C14   C  CR15  0  -0.069   4.5000  -1.8141  -0.6721
 4HK  C17   C  CH2   0  -0.167   4.2992  -2.5659   0.6373
 4HK  O2    O  O     0  -0.501   5.5118  -2.4336   1.3576
 4HK  C16   C  CH2   0  -0.149   6.5532  -2.0005   0.4900
 4HK  C15   C  CH2   0  -0.518   5.9776  -2.0613  -0.9192
 4HK  H4    H  HCR6  0   0.288  -3.2094  -1.4905  -0.2469
 4HK  H3    H  HCR6  0   0.276  -5.3434   2.2187   0.2271
 4HK  H2    H  HCR6  0   0.304  -7.4296   0.9452  -0.0383
 4HK  H5    H  HCH2  0   0.281  -0.8060  -1.3637   0.3565
 4HK  H6    H  HCH2  0   0.282  -0.8787  -0.9156  -1.3395
 4HK  H1    H  HNR5  0   0.425  -3.3829   3.0918   0.7389
 4HK  H17   H  HCR6  0   0.244   1.8774   3.1490   0.5768
 4HK  H16   H  HCH2  0   0.238   4.2171   3.0988   0.8839
 4HK  H15   H  HCH2  0   0.239   5.1536   1.6329   0.7135
 4HK  H201  H  HCH3  0   0.228   5.1554   1.9295  -1.7919
 4HK  H202  H  HCH3  0   0.223   4.2135   3.4082  -1.6023
 4HK  H203  H  HCH3  0   0.229   5.8563   3.3196  -0.9686
 4HK  H7    H  HCR6  0   0.277   1.9306  -1.6391  -0.7322
 4HK  H8    H  HCR5  0   0.269   3.8689  -2.1925  -1.4812
 4HK  H14   H  HCH2  0   0.238   3.4737  -2.1776   1.2391
 4HK  H13   H  HCH2  0   0.221   4.0824  -3.6183   0.4177
 4HK  H12   H  HCH2  0   0.212   6.8551  -0.9814   0.7522
 4HK  H11   H  HCH2  0   0.224   7.4246  -2.6484   0.6080
 4HK  H9    H  HCH2  0   0.258   6.1024  -3.0563  -1.3499
 4HK  H10   H  HCH2  0   0.267   6.4238  -1.3401  -1.6033

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
 4HK  C20  C19   single    1.528  0.020  1.528
 4HK  C19  C18   single    1.505  0.020  1.505
 4HK  C15  C14   single    1.518  0.020  1.518
 4HK  C15  C16   single    1.523  0.020  1.523
 4HK  C21  C18   aromatic  1.388  0.020  1.388
 4HK  C21  C22   aromatic  1.387  0.020  1.387
 4HK  C18  C13   aromatic  1.408  0.020  1.408
 4HK  C14  C17   single    1.523  0.020  1.523
 4HK  C14  O1    single    1.420  0.020  1.420
 4HK  N4   C8    aromatic  1.318  0.020  1.318
 4HK  N4   N3    aromatic  1.331  0.020  1.331
 4HK  C16  O2    single    1.423  0.020  1.423
 4HK  C22  C8    aromatic  1.453  0.020  1.453
 4HK  C22  C11   aromatic  1.399  0.020  1.399
 4HK  C8   C9    aromatic  1.401  0.020  1.401
 4HK  N3   C7    aromatic  1.362  0.020  1.362
 4HK  C13  O1    single    1.349  0.020  1.349
 4HK  C13  C12   aromatic  1.396  0.020  1.396
 4HK  C17  O2    single    1.417  0.020  1.417
 4HK  C11  C12   aromatic  1.383  0.020  1.383
 4HK  C11  C10   single    1.518  0.020  1.518
 4HK  C9   C7    aromatic  1.377  0.020  1.377
 4HK  C9   C10   single    1.495  0.020  1.495
 4HK  C7   C5    single    1.451  0.020  1.451
 4HK  C5   C6    aromatic  1.402  0.020  1.402
 4HK  C5   C4    aromatic  1.392  0.020  1.392
 4HK  C6   N2    aromatic  1.316  0.020  1.316
 4HK  C4   C3    aromatic  1.383  0.020  1.383
 4HK  N2   C2    aromatic  1.331  0.020  1.331
 4HK  C3   C2    aromatic  1.387  0.020  1.387
 4HK  C2   C1    single    1.436  0.020  1.436
 4HK  C1   N1    triple    1.151  0.020  1.151
 4HK  C6   H4    single    0.930  0.020  1.080
 4HK  C4   H3    single    0.930  0.020  1.080
 4HK  C3   H2    single    0.930  0.020  1.080
 4HK  C10  H5    single    0.970  0.020  1.090
 4HK  C10  H6    single    0.970  0.020  1.090
 4HK  N3   H1    single    0.860  0.020  1.020
 4HK  C21  H17   single    0.930  0.020  1.080
 4HK  C19  H16   single    0.970  0.020  1.090
 4HK  C19  H15   single    0.970  0.020  1.090
 4HK  C20  H201  single    0.970  0.020  1.090
 4HK  C20  H202  single    0.970  0.020  1.090
 4HK  C20  H203  single    0.970  0.020  1.090
 4HK  C12  H7    single    0.930  0.020  1.080
 4HK  C14  H8    single    0.970  0.020  1.090
 4HK  C17  H14   single    0.970  0.020  1.090
 4HK  C17  H13   single    0.970  0.020  1.090
 4HK  C16  H12   single    0.970  0.020  1.090
 4HK  C16  H11   single    0.970  0.020  1.090
 4HK  C15  H9    single    0.970  0.020  1.090
 4HK  C15  H10   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
 4HK  C2    C1   N1    180.00  3.000
 4HK  C3    C2   N2    123.72  3.000
 4HK  C3    C2   C1    120.14  3.000
 4HK  N2    C2   C1    116.14  3.000
 4HK  C6    N2   C2    117.80  3.000
 4HK  H4    C6   C5    120.31  3.000
 4HK  H4    C6   N2    115.84  3.000
 4HK  C5    C6   N2    123.85  3.000
 4HK  C7    C5   C4    123.38  3.000
 4HK  C4    C5   C6    117.19  3.000
 4HK  C7    C5   C6    119.44  3.000
 4HK  H3    C4   C3    118.64  3.000
 4HK  H3    C4   C5    121.85  3.000
 4HK  C3    C4   C5    119.51  3.000
 4HK  H2    C3   C4    121.03  3.000
 4HK  H2    C3   C2    121.04  3.000
 4HK  C4    C3   C2    117.93  3.000
 4HK  N3    C7   C9    104.90  3.000
 4HK  C9    C7   C5    131.62  3.000
 4HK  N3    C7   C5    123.48  3.000
 4HK  C8    C9   C10   110.68  3.000
 4HK  C10   C9   C7    144.70  3.000
 4HK  C8    C9   C7    104.62  3.000
 4HK  H6    C10  H5    106.77  3.000
 4HK  H6    C10  C11   111.79  3.000
 4HK  H5    C10  C11   111.29  3.000
 4HK  H6    C10  C9    113.01  3.000
 4HK  H5    C10  C9    113.00  3.000
 4HK  C11   C10  C9    101.06  3.000
 4HK  C12   C11  C22   120.39  3.000
 4HK  C12   C11  C10   127.70  3.000
 4HK  C22   C11  C10   111.91  3.000
 4HK  C21   C22  C8    133.08  3.000
 4HK  C8    C22  C11   106.65  3.000
 4HK  C21   C22  C11   120.27  3.000
 4HK  N4    C8   C22   137.54  3.000
 4HK  C22   C8   C9    109.71  3.000
 4HK  N4    C8   C9    112.75  3.000
 4HK  N3    N4   C8    103.57  3.000
 4HK  H1    N3   N4    118.47  3.000
 4HK  H1    N3   C7    127.33  3.000
 4HK  N4    N3   C7    114.17  3.000
 4HK  H17   C21  C18   119.16  3.000
 4HK  H17   C21  C22   120.43  3.000
 4HK  C18   C21  C22   120.41  3.000
 4HK  C13   C18  C19   120.93  3.000
 4HK  C13   C18  C21   118.79  3.000
 4HK  C19   C18  C21   120.27  3.000
 4HK  H15   C19  H16   106.34  3.000
 4HK  H15   C19  C20   109.48  3.000
 4HK  H16   C19  C20   109.16  3.000
 4HK  H15   C19  C18   110.39  3.000
 4HK  H16   C19  C18   108.57  3.000
 4HK  C20   C19  C18   112.70  3.000
 4HK  H203  C20  H202  107.84  3.000
 4HK  H203  C20  H201  107.73  3.000
 4HK  H202  C20  H201  107.93  3.000
 4HK  H203  C20  C19   110.77  3.000
 4HK  H202  C20  C19   110.95  3.000
 4HK  H201  C20  C19   111.47  3.000
 4HK  O1    C13  C12   123.52  3.000
 4HK  C12   C13  C18   121.12  3.000
 4HK  O1    C13  C18   115.36  3.000
 4HK  H7    C12  C13   121.45  3.000
 4HK  H7    C12  C11   119.53  3.000
 4HK  C13   C12  C11   119.03  3.000
 4HK  C14   O1   C13   120.62  3.000
 4HK  H8    C14  C15   112.63  3.000
 4HK  H8    C14  C17   112.90  3.000
 4HK  C15   C14  C17   100.83  3.000
 4HK  H8    C14  O1    111.14  3.000
 4HK  C17   C14  O1    112.04  3.000
 4HK  C15   C14  O1    106.76  3.000
 4HK  H13   C17  H14   107.57  3.000
 4HK  H13   C17  O2    111.14  3.000
 4HK  H14   C17  O2    109.47  3.000
 4HK  H13   C17  C14   109.13  3.000
 4HK  H14   C17  C14   113.43  3.000
 4HK  O2    C17  C14   106.15  3.000
 4HK  C16   O2   C17   110.17  3.000
 4HK  H11   C16  H12   107.84  3.000
 4HK  H11   C16  C15   112.19  3.000
 4HK  H12   C16  C15   111.28  3.000
 4HK  H11   C16  O2    109.72  3.000
 4HK  H12   C16  O2    109.82  3.000
 4HK  C15   C16  O2    105.98  3.000
 4HK  H10   C15  H9    107.99  3.000
 4HK  H10   C15  C16   113.56  3.000
 4HK  H9    C15  C16   110.99  3.000
 4HK  H10   C15  C14   113.14  3.000
 4HK  H9    C15  C14   108.90  3.000
 4HK  C16   C15  C14   102.16  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
 4HK  CONST_01  C5    C6   N2   C2      0.00   0.0  0
 4HK  CONST_02  C5    C4   C3   C2      0.00   0.0  0
 4HK  CONST_03  C7    C5   C6   N2    180.00   0.0  0
 4HK  CONST_04  C4    C5   C6   N2      0.00   0.0  0
 4HK  CONST_05  C4    C3   C2   N2      0.00   0.0  0
 4HK  CONST_06  N3    C7   C5   C6    180.00   0.0  0
 4HK  CONST_07  C9    C7   C5   C6      0.00   0.0  0
 4HK  CONST_08  C3    C4   C5   C6      0.00   0.0  0
 4HK  CONST_09  C3    C2   N2   C6      0.00   0.0  0
 4HK  CONST_10  N4    N3   C7   C5    180.00   0.0  0
 4HK  CONST_11  C8    C9   C7   C5    180.00   0.0  0
 4HK  CONST_12  N3    C7   C5   C4      0.00   0.0  0
 4HK  CONST_13  C9    C7   C5   C4    180.00   0.0  0
 4HK  CONST_14  C7    C5   C4   C3    180.00   0.0  0
 4HK  CONST_15  C8    N4   N3   C7      0.00   0.0  0
 4HK  CONST_16  N4    C8   C9   C7      0.00   0.0  0
 4HK  CONST_17  C22   C8   C9   C7    180.00   0.0  0
 4HK  CONST_18  N3    N4   C8   C9      0.00   0.0  0
 4HK  CONST_19  C21   C22  C8   C9    180.00   0.0  0
 4HK  CONST_20  C11   C22  C8   C9      0.00   0.0  0
 4HK  CONST_21  N4    N3   C7   C9      0.00   0.0  0
 4HK  CONST_22  C18   C21  C22  C11     0.00   0.0  0
 4HK  CONST_23  N4    C8   C22  C11   180.00   0.0  0
 4HK  CONST_24  C18   C13  C12  C11     0.00   0.0  0
 4HK  CONST_25  C13   C18  C21  C22     0.00   0.0  0
 4HK  CONST_26  N3    N4   C8   C22   180.00   0.0  0
 4HK  CONST_27  C13   C12  C11  C22     0.00   0.0  0
 4HK  CONST_28  C18   C21  C22  C8    180.00   0.0  0
 4HK  CONST_29  C12   C11  C22  C8    180.00   0.0  0
 4HK  CONST_30  N3    C7   C9   C8      0.00   0.0  0
 4HK  CONST_31  C21   C22  C8   N4      0.00   0.0  0
 4HK  CONST_32  C12   C13  C18  C21     0.00   0.0  0
 4HK  CONST_33  C12   C11  C22  C21     0.00   0.0  0
 4HK  CONST_34  C10   C9   C7   C5      0.00   0.0  0
 4HK  CONST_35  C6    N2   C2   C1    180.00   0.0  0
 4HK  CONST_36  C4    C3   C2   C1    180.00   0.0  0
 4HK  CONST_37  O1    C13  C12  C11   180.00   0.0  0
 4HK  CONST_38  C19   C18  C21  C22   180.00   0.0  0
 4HK  CONST_39  O1    C13  C18  C21   180.00   0.0  0
 4HK  CONST_40  C12   C13  C18  C19   180.00   0.0  0
 4HK  CONST_41  H4    C6   N2   C2    180.00   0.0  0
 4HK  CONST_42  H3    C4   C3   C2    180.00   0.0  0
 4HK  CONST_43  H2    C3   C2   N2    180.00   0.0  0
 4HK  CONST_44  H1    N3   C7   C5      0.00   0.0  0
 4HK  CONST_45  H7    C12  C11  C10     0.00   0.0  0
 4HK  CONST_46  H17   C21  C22  C11   180.00   0.0  0
 4HK  Var_01    O2    C16  C15  C14    29.26  30.0  1
 4HK  Var_02    C15   C16  O2   C17    -8.50  30.0  1
 4HK  Var_03    H5    C10  C9   C7    -62.08  30.0  1
 4HK  Var_04    H14   C17  O2   C16  -138.76  30.0  1
 4HK  Var_05    C20   C19  C18  C21   -96.99  30.0  3
 4HK  Var_06    H201  C20  C19  C18   -60.98  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 4HK  chir_01  C14  C15  C17  O1  negativ

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
 4HK  plan-1  N1   0.020
 4HK  plan-1  C1   0.020
 4HK  plan-1  C2   0.020
 4HK  plan-1  N2   0.020
 4HK  plan-1  C6   0.020
 4HK  plan-1  C5   0.020
 4HK  plan-1  C4   0.020
 4HK  plan-1  C3   0.020
 4HK  plan-1  C7   0.020
 4HK  plan-1  H4   0.020
 4HK  plan-1  H3   0.020
 4HK  plan-1  H2   0.020
 4HK  plan-2  C5   0.020
 4HK  plan-2  C7   0.020
 4HK  plan-2  C9   0.020
 4HK  plan-2  C10  0.020
 4HK  plan-2  C11  0.020
 4HK  plan-2  C22  0.020
 4HK  plan-2  C8   0.020
 4HK  plan-2  N4   0.020
 4HK  plan-2  N3   0.020
 4HK  plan-2  C21  0.020
 4HK  plan-2  C18  0.020
 4HK  plan-2  C19  0.020
 4HK  plan-2  C13  0.020
 4HK  plan-2  C12  0.020
 4HK  plan-2  O1   0.020
 4HK  plan-2  H1   0.020
 4HK  plan-2  H17  0.020
 4HK  plan-2  H7   0.020

