# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 00:49:06 2020
#   Inital geometry file: a 145 line input string
#   Ligand name: (4~{S})-6-azanyl-4-[3-cyano-5-[5-(methoxymethyl)thiophen-2-yl]phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COCc1sc(cc1)c2cc(cc(c2)[C@@]3(C(C)C)C(=C(N)Oc4n[nH]c(C)c34)C#N)C#N
#
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
 GI8  GI8  (4~{S})-6-azanyl-4-[3-cyano-5-[5-(methoxymethyl)thiophen-2-yl]phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile  ligand  55  32  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_GI8
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
 GI8  N9   N  NS    0  -0.285   1.3042  -0.0647  -3.5889
 GI8  C8   C  CSP   0   0.031   1.5720   0.4182  -2.5705
 GI8  C3   C  CR6   0  -0.228   1.8580   1.0219  -1.3336
 GI8  C2   C  CR6   0   0.614   1.7874   2.3937  -1.2973
 GI8  N7   N  NH2   0  -0.835   1.6362   3.1962  -2.3553
 GI8  O1   O  O     0  -0.452   1.8923   3.1021  -0.1630
 GI8  C6   C  CR56  0   0.461   1.9199   2.3876   0.9869
 GI8  N12  N  N     0  -0.293   1.8251   2.9879   2.1434
 GI8  N11  N  NR15  0  -0.491   1.9004   1.9711   3.0065
 GI8  C10  C  CR5   0   0.372   2.0354   0.7641   2.4288
 GI8  C13  C  CH3   0  -0.752   2.1266  -0.4898   3.2194
 GI8  C5   C  CR56  0  -0.146   2.0530   1.0060   1.0663
 GI8  C4   C  CR6   0  -0.172   2.2164   0.1345  -0.1432
 GI8  C14  C  CH1   0  -0.221   3.6878  -0.3692  -0.2394
 GI8  C16  C  CH3   0  -0.677   3.9704  -1.2052  -1.4869
 GI8  C15  C  CH3   0  -0.661   4.6912   0.7762  -0.1682
 GI8  C17  C  CR6   0   0.210   1.1975  -1.0063  -0.0263
 GI8  C18  C  CR16  0  -0.359   1.5495  -2.2997   0.3278
 GI8  C19  C  CR6   0   0.063   0.5601  -3.2740   0.4702
 GI8  C23  C  CSP   0   0.050   0.9395  -4.6008   0.8386
 GI8  N24  N  NS    0  -0.247   1.2478  -5.6709   1.1337
 GI8  C22  C  CR16  0  -0.338  -0.1516  -0.7229  -0.2231
 GI8  C21  C  CR6   0   0.195  -1.1500  -1.6838  -0.0788
 GI8  C20  C  CR16  0  -0.349  -0.7818  -2.9807   0.2744
 GI8  C25  C  CR5   0  -0.227  -2.5570  -1.3582  -0.3006
 GI8  S29  S  S2    0   0.233  -3.1572   0.2427  -0.0477
 GI8  C28  C  CR5   0  -0.201  -4.7568  -0.2158  -0.4817
 GI8  C27  C  CR15  0  -0.198  -4.8196  -1.5399  -0.7954
 GI8  C26  C  CR15  0  -0.227  -3.5650  -2.1930  -0.6948
 GI8  C30  C  CH2   0  -0.179  -5.8412   0.8037  -0.5070
 GI8  O31  O  O2    0  -0.484  -5.7462   1.5881   0.6533
 GI8  C32  C  CH3   0  -0.399  -6.6913   2.6308   0.6750
 GI8  H1   H  HNH2  0   0.422   1.5043   2.8076  -3.2737
 GI8  H2   H  HNH2  0   0.418   1.3171   4.1419  -2.2207
 GI8  H4   H  HCH3  0   0.263   1.2721  -1.1393   3.0288
 GI8  H5   H  HCH3  0   0.261   3.0270  -1.0507   2.9708
 GI8  H6   H  HCH3  0   0.270   2.1523  -0.2791   4.2877
 GI8  H7   H  HCH1  0   0.234   3.8607  -0.9976   0.6411
 GI8  H8   H  HCH3  0   0.233   4.0222  -0.5806  -2.3791
 GI8  H9   H  HCH3  0   0.244   4.9373  -1.6999  -1.3862
 GI8  H10  H  HCH3  0   0.237   3.2240  -1.9788  -1.6667
 GI8  H11  H  HCH3  0   0.239   4.6193   1.3427   0.7598
 GI8  H12  H  HCH3  0   0.240   5.7050   0.3783  -0.2287
 GI8  H13  H  HCH3  0   0.225   4.5635   1.4673  -1.0034
 GI8  H14  H  HCR6  0   0.291   2.5783  -2.5765   0.5065
 GI8  H15  H  HCR6  0   0.255  -0.4278   0.2843  -0.5125
 GI8  H16  H  HCR6  0   0.281  -1.5290  -3.7506   0.4113
 GI8  H17  H  HCR5  0   0.268  -5.7342  -2.0345  -1.0917
 GI8  H18  H  HCR5  0   0.268  -3.4180  -3.2402  -0.9201
 GI8  H19  H  HCH2  0   0.229  -5.7486   1.4323  -1.4051
 GI8  H20  H  HCH2  0   0.231  -6.8106   0.2924  -0.5801
 GI8  H21  H  HCH3  0   0.209  -6.5653   3.3148  -0.1718
 GI8  H22  H  HCH3  0   0.210  -7.7192   2.2510   0.6542
 GI8  H23  H  HCH3  0   0.239  -6.5496   3.1900   1.5989
 GI8  H3   H  HNR5  0   0.423   1.8502   2.1596   3.9953

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
 GI8  N24  C23  triple    1.152  0.020  1.152
 GI8  N9   C8   triple    1.158  0.020  1.158
 GI8  C23  C19  single    1.428  0.020  1.428
 GI8  C8   C3   single    1.406  0.020  1.406
 GI8  C19  C18  aromatic  1.396  0.020  1.396
 GI8  C19  C20  aromatic  1.387  0.020  1.387
 GI8  N7   C2   single    1.337  0.020  1.337
 GI8  C18  C17  aromatic  1.386  0.020  1.386
 GI8  C3   C2   double    1.374  0.020  1.374
 GI8  C3   C4   single    1.527  0.020  1.527
 GI8  C14  C15  single    1.524  0.020  1.524
 GI8  C14  C4   single    1.558  0.020  1.558
 GI8  C14  C16  single    1.528  0.020  1.528
 GI8  C2   O1   single    1.341  0.020  1.341
 GI8  C20  C21  aromatic  1.394  0.020  1.394
 GI8  C17  C4   single    1.534  0.020  1.534
 GI8  C17  C22  aromatic  1.392  0.020  1.392
 GI8  C4   C5   single    1.500  0.020  1.500
 GI8  C21  C22  aromatic  1.393  0.020  1.393
 GI8  C21  C25  single    1.461  0.020  1.461
 GI8  O1   C6   single    1.354  0.020  1.354
 GI8  C5   C6   aromatic  1.390  0.020  1.390
 GI8  C5   C10  aromatic  1.384  0.020  1.384
 GI8  S29  C25  aromatic  1.728  0.020  1.728
 GI8  S29  C28  aromatic  1.720  0.020  1.720
 GI8  C6   N12  aromatic  1.306  0.020  1.306
 GI8  C25  C26  aromatic  1.367  0.020  1.367
 GI8  C10  C13  single    1.485  0.020  1.485
 GI8  C10  N11  aromatic  1.345  0.020  1.345
 GI8  N12  N11  aromatic  1.336  0.020  1.336
 GI8  C28  C30  single    1.489  0.020  1.489
 GI8  C28  C27  aromatic  1.362  0.020  1.362
 GI8  C26  C27  aromatic  1.418  0.020  1.418
 GI8  C30  O31  single    1.404  0.020  1.404
 GI8  O31  C32  single    1.407  0.020  1.407
 GI8  N7   H1   single    0.890  0.020  1.040
 GI8  N7   H2   single    0.890  0.020  1.040
 GI8  C13  H4   single    0.970  0.020  1.090
 GI8  C13  H5   single    0.970  0.020  1.090
 GI8  C13  H6   single    0.970  0.020  1.090
 GI8  C14  H7   single    0.970  0.020  1.090
 GI8  C16  H8   single    0.970  0.020  1.090
 GI8  C16  H9   single    0.970  0.020  1.090
 GI8  C16  H10  single    0.970  0.020  1.090
 GI8  C15  H11  single    0.970  0.020  1.090
 GI8  C15  H12  single    0.970  0.020  1.090
 GI8  C15  H13  single    0.970  0.020  1.090
 GI8  C18  H14  single    0.930  0.020  1.080
 GI8  C22  H15  single    0.930  0.020  1.080
 GI8  C20  H16  single    0.930  0.020  1.080
 GI8  C27  H17  single    0.930  0.020  1.080
 GI8  C26  H18  single    0.930  0.020  1.080
 GI8  C30  H19  single    0.970  0.020  1.090
 GI8  C30  H20  single    0.970  0.020  1.090
 GI8  C32  H21  single    0.970  0.020  1.090
 GI8  C32  H22  single    0.970  0.020  1.090
 GI8  C32  H23  single    0.970  0.020  1.090
 GI8  N11  H3   single    0.860  0.020  1.020

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
 GI8  C3   C8   N9   180.00  3.000
 GI8  C4   C3   C2   124.85  3.000
 GI8  C4   C3   C8   118.95  3.000
 GI8  C2   C3   C8   116.20  3.000
 GI8  O1   C2   N7   111.17  3.000
 GI8  O1   C2   C3   123.06  3.000
 GI8  N7   C2   C3   125.75  3.000
 GI8  H2   N7   H1   116.31  3.000
 GI8  H2   N7   C2   119.59  3.000
 GI8  H1   N7   C2   120.38  3.000
 GI8  C6   O1   C2   116.17  3.000
 GI8  C5   C6   N12  114.40  3.000
 GI8  N12  C6   O1   120.51  3.000
 GI8  C5   C6   O1   125.09  3.000
 GI8  N11  N12  C6   102.60  3.000
 GI8  H3   N11  C10  126.46  3.000
 GI8  H3   N11  N12  119.26  3.000
 GI8  C10  N11  N12  114.28  3.000
 GI8  C5   C10  C13  132.13  3.000
 GI8  C13  C10  N11  122.36  3.000
 GI8  C5   C10  N11  105.50  3.000
 GI8  H6   C13  H5   107.69  3.000
 GI8  H6   C13  H4   107.77  3.000
 GI8  H5   C13  H4   107.53  3.000
 GI8  H6   C13  C10  111.11  3.000
 GI8  H5   C13  C10  111.34  3.000
 GI8  H4   C13  C10  111.21  3.000
 GI8  C4   C5   C10  133.93  3.000
 GI8  C10  C5   C6   103.22  3.000
 GI8  C4   C5   C6   122.81  3.000
 GI8  C17  C4   C14  113.05  3.000
 GI8  C17  C4   C5   107.36  3.000
 GI8  C14  C4   C5   109.91  3.000
 GI8  C5   C4   C3   105.39  3.000
 GI8  C17  C4   C3   109.61  3.000
 GI8  C14  C4   C3   111.18  3.000
 GI8  H7   C14  C15  106.83  3.000
 GI8  H7   C14  C16  108.25  3.000
 GI8  C15  C14  C16  109.11  3.000
 GI8  H7   C14  C4   106.55  3.000
 GI8  C16  C14  C4   113.70  3.000
 GI8  C15  C14  C4   112.07  3.000
 GI8  H10  C16  H9   107.48  3.000
 GI8  H10  C16  H8   107.70  3.000
 GI8  H9   C16  H8   107.05  3.000
 GI8  H10  C16  C14  113.35  3.000
 GI8  H9   C16  C14  109.68  3.000
 GI8  H8   C16  C14  111.32  3.000
 GI8  H13  C15  H12  107.30  3.000
 GI8  H13  C15  H11  108.35  3.000
 GI8  H12  C15  H11  107.35  3.000
 GI8  H13  C15  C14  111.28  3.000
 GI8  H12  C15  C14  109.58  3.000
 GI8  H11  C15  C14  112.77  3.000
 GI8  C22  C17  C18  118.16  3.000
 GI8  C22  C17  C4   118.78  3.000
 GI8  C18  C17  C4   123.00  3.000
 GI8  H14  C18  C19  118.64  3.000
 GI8  H14  C18  C17  121.54  3.000
 GI8  C19  C18  C17  119.82  3.000
 GI8  C20  C19  C23  119.32  3.000
 GI8  C20  C19  C18  121.57  3.000
 GI8  C23  C19  C18  119.10  3.000
 GI8  N24  C23  C19  180.00  3.000
 GI8  H15  C22  C21  119.08  3.000
 GI8  H15  C22  C17  118.28  3.000
 GI8  C21  C22  C17  122.64  3.000
 GI8  C25  C21  C20  120.02  3.000
 GI8  C25  C21  C22  121.38  3.000
 GI8  C20  C21  C22  118.60  3.000
 GI8  H16  C20  C21  120.79  3.000
 GI8  H16  C20  C19  119.99  3.000
 GI8  C21  C20  C19  119.21  3.000
 GI8  C26  C25  S29  110.60  3.000
 GI8  C26  C25  C21  128.15  3.000
 GI8  S29  C25  C21  121.24  3.000
 GI8  C28  S29  C25   92.24  3.000
 GI8  C30  C28  C27  128.92  3.000
 GI8  C27  C28  S29  111.11  3.000
 GI8  C30  C28  S29  119.95  3.000
 GI8  H17  C27  C26  123.86  3.000
 GI8  H17  C27  C28  123.15  3.000
 GI8  C26  C27  C28  112.99  3.000
 GI8  H18  C26  C27  123.47  3.000
 GI8  H18  C26  C25  123.46  3.000
 GI8  C27  C26  C25  113.06  3.000
 GI8  H20  C30  H19  106.62  3.000
 GI8  H20  C30  O31  112.01  3.000
 GI8  H19  C30  O31  110.47  3.000
 GI8  H20  C30  C28  108.98  3.000
 GI8  H19  C30  C28  110.11  3.000
 GI8  O31  C30  C28  108.62  3.000
 GI8  C32  O31  C30  112.42  3.000
 GI8  H23  C32  H22  108.42  3.000
 GI8  H23  C32  H21  108.67  3.000
 GI8  H22  C32  H21  108.02  3.000
 GI8  H23  C32  O31  107.83  3.000
 GI8  H22  C32  O31  111.88  3.000
 GI8  H21  C32  O31  111.92  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
 GI8  CONST_01  N11  C10  C5   C6     0.00   0.0  0
 GI8  CONST_02  C10  N11  N12  C6     0.00   0.0  0
 GI8  CONST_03  C10  C5   C6   N12    0.00   0.0  0
 GI8  CONST_04  C5   C10  N11  N12    0.00   0.0  0
 GI8  CONST_05  C5   C6   N12  N11    0.00   0.0  0
 GI8  CONST_06  C20  C19  C18  C17    0.00   0.0  0
 GI8  CONST_07  C20  C21  C22  C17    0.00   0.0  0
 GI8  CONST_08  C25  C21  C22  C17  180.00   0.0  0
 GI8  CONST_09  C21  C20  C19  C18    0.00   0.0  0
 GI8  CONST_10  C21  C22  C17  C18    0.00   0.0  0
 GI8  CONST_11  C22  C17  C18  C19    0.00   0.0  0
 GI8  CONST_12  C22  C21  C20  C19    0.00   0.0  0
 GI8  CONST_13  C25  C21  C20  C19  180.00   0.0  0
 GI8  CONST_16  C28  S29  C25  C21  180.00   0.0  0
 GI8  CONST_17  C27  C26  C25  C21  180.00   0.0  0
 GI8  CONST_20  C27  C28  S29  C25    0.00   0.0  0
 GI8  CONST_21  C28  C27  C26  C25    0.00   0.0  0
 GI8  CONST_22  C27  C26  C25  S29    0.00   0.0  0
 GI8  CONST_23  C26  C27  C28  S29    0.00   0.0  0
 GI8  CONST_24  C26  C25  S29  C28    0.00   0.0  0
 GI8  CONST_25  C19  C18  C17  C4   180.00   0.0  0
 GI8  CONST_26  C21  C22  C17  C4   180.00   0.0  0
 GI8  CONST_27  C13  C10  C5   C6   180.00   0.0  0
 GI8  CONST_28  C13  C10  N11  N12  180.00   0.0  0
 GI8  CONST_29  C4   C5   C10  C13    0.00   0.0  0
 GI8  CONST_30  C23  C19  C18  C17  180.00   0.0  0
 GI8  CONST_31  C21  C20  C19  C23  180.00   0.0  0
 GI8  CONST_32  C30  C28  S29  C25  180.00   0.0  0
 GI8  CONST_33  C30  C28  C27  C26  180.00   0.0  0
 GI8  CONST_34  H3   N11  N12  C6   180.00   0.0  0
 GI8  CONST_35  H14  C18  C17  C4     0.00   0.0  0
 GI8  CONST_36  H15  C22  C17  C4     0.00   0.0  0
 GI8  CONST_37  H16  C20  C19  C18  180.00   0.0  0
 GI8  CONST_38  H18  C26  C25  C21    0.00   0.0  0
 GI8  CONST_39  H17  C27  C26  C25  180.00   0.0  0
 GI8  Var_01    C5   C6   O1   C2    10.32  30.0  1
 GI8  Var_02    C4   C3   C2   O1    -7.22  30.0  1
 GI8  Var_03    C2   C3   C8   N9   -59.60  30.0  3
 GI8  Var_04    O31  C30  C28  S29  -45.06  30.0  2
 GI8  Var_05    H1   N7   C2   C3     3.90  30.0  2
 GI8  Var_06    H4   C13  C10  N11  115.38  30.0  2
 GI8  Var_07    H11  C15  C14  C4    59.91  30.0  3
 GI8  Var_08    H8   C16  C14  C4    73.95  30.0  3
 GI8  Var_09    H21  C32  O31  C30  -60.33  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
 GI8  chir_01  C4  C3  C17  C5  positiv

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
 GI8  plan-1  C21  0.020
 GI8  plan-1  C25  0.020
 GI8  plan-1  S29  0.020
 GI8  plan-1  C28  0.020
 GI8  plan-1  C27  0.020
 GI8  plan-1  C26  0.020
 GI8  plan-1  C30  0.020
 GI8  plan-1  H17  0.020
 GI8  plan-1  H18  0.020
 GI8  plan-2  C4   0.020
 GI8  plan-2  C17  0.020
 GI8  plan-2  C18  0.020
 GI8  plan-2  C19  0.020
 GI8  plan-2  C23  0.020
 GI8  plan-2  N24  0.020
 GI8  plan-2  C22  0.020
 GI8  plan-2  C21  0.020
 GI8  plan-2  C20  0.020
 GI8  plan-2  C25  0.020
 GI8  plan-2  H14  0.020
 GI8  plan-2  H15  0.020
 GI8  plan-2  H16  0.020
 GI8  plan-3  O1   0.020
 GI8  plan-3  C6   0.020
 GI8  plan-3  N12  0.020
 GI8  plan-3  N11  0.020
 GI8  plan-3  C10  0.020
 GI8  plan-3  C13  0.020
 GI8  plan-3  C5   0.020
 GI8  plan-3  C4   0.020
 GI8  plan-3  H3   0.020

