# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 15:03:26 2020
#   Inital geometry file: a 146 line input string
#   Ligand name: 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-{[(2R)-2-amino-3-phenylpropyl]oxy}-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methylbut-3-yn-2-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCn1c2cc(OC[C@H](N)Cc3ccccc3)nc(C#CC(C)(C)O)c2nc1c4nonc4N
#
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
 G96  G96  4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-{[(2R)-2-amino-3-phenylpropyl]oxy}-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methylbut-3-yn-2-ol  ligand  61  34  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G96
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
 G96  N1    N  N     0  -0.122    5.5766   2.6060  -0.2453
 G96  N3    N  NH2   0  -0.850    5.9472  -0.8853  -0.1530
 G96  C4    C  CR16  0  -0.274   -9.4660   1.2338  -0.3650
 G96  C5    C  CR16  0  -0.241   -8.6929   0.9427  -1.4816
 G96  C6    C  CR16  0  -0.313   -7.4237   0.4008  -1.3276
 G96  C7    C  CH2   0  -0.154   -3.0688  -0.0111   0.0220
 G96  C8    C  CR5   0   0.352    6.0780   0.4505  -0.2290
 G96  C10   C  CR6   0   0.515   -0.7940   0.6940  -0.0397
 G96  C15   C  CR56  0   0.426    1.4386   1.3810  -0.1154
 G96  C17   C  CSP   0   0.056    1.4822  -3.4847   0.0279
 G96  C20   C  CH3   0  -0.670    3.3732  -4.9689   0.4793
 G96  C22   C  CH3   0  -0.661    2.9025   4.1211   1.1999
 G96  C24   C  CH2   0  -0.529   -5.5177  -0.4196   0.0870
 G96  O3    O  OH1   0  -0.654    1.0803  -5.6290   0.9411
 G96  C18   C  CT    0   0.006    1.9048  -4.8967   0.0569
 G96  C19   C  CH3   0  -0.657    1.7122  -5.5081  -1.3287
 G96  C12   C  CR6   0   0.002    0.8240  -0.9404  -0.0318
 G96  N4    N  N     0  -0.481   -0.4596  -0.5887  -0.0131
 G96  C14   C  CR56  0   0.085    1.8201   0.0298  -0.0827
 G96  N6    N  N     0  -0.499    3.1788  -0.0754  -0.1118
 G96  C16   C  CR5   0   0.541    3.6091   1.1568  -0.1604
 G96  N5    N  NR5   0  -0.564    2.6042   2.0879  -0.1769
 G96  C9    C  CR5   0   0.086    5.0267   1.4343  -0.2065
 G96  O2    O  O     0  -0.213    6.8857   2.4150  -0.2965
 G96  N2    N  N     0  -0.188    7.2085   1.0937  -0.2905
 G96  C11   C  CR16  0  -0.450    0.1095   1.7571  -0.0910
 G96  C23   C  CH1   0  -0.132   -4.4341   0.6634   0.1039
 G96  N7    N  NH2   0  -0.776   -4.6132   1.5236   1.2572
 G96  C1    C  CR6   0   0.164   -6.9025   0.1419  -0.0615
 G96  C3    C  CR16  0  -0.245   -8.9594   0.9761   0.9024
 G96  C2    C  CR16  0  -0.307   -7.6875   0.4381   1.0500
 G96  HN3   H  HNH2  0   0.412    5.0245  -1.2543  -0.3240
 G96  HN3A  H  HNH2  0   0.405    6.7255  -1.4552  -0.4408
 G96  H4    H  HCR6  0   0.251  -10.4567   1.6540  -0.4826
 G96  H5    H  HCR6  0   0.251   -9.0800   1.1334  -2.4745
 G96  H6    H  HCR6  0   0.243   -6.8313   0.1718  -2.2064
 G96  H7    H  HCH2  0   0.224   -2.9981  -0.6362  -0.8736
 G96  H7A   H  HCH2  0   0.220   -2.9113  -0.6584   0.8915
 G96  H20   H  HCH3  0   0.243    3.5158  -4.5615   1.4817
 G96  H20A  H  HCH3  0   0.246    3.7074  -6.0074   0.4766
 G96  H20B  H  HCH3  0   0.237    4.0054  -4.4033  -0.2046
 G96  H21   H  HCH2  0   0.278    1.7776   3.9149  -0.6298
 G96  H21A  H  HCH2  0   0.282    3.5051   3.8316  -0.8578
 G96  H22   H  HCH3  0   0.247    2.9407   5.2079   1.1354
 G96  H22A  H  HCH3  0   0.239    2.0831   3.8518   1.8660
 G96  H22B  H  HCH3  0   0.238    3.8369   3.7797   1.6444
 G96  H24   H  HCH2  0   0.252   -5.3155  -1.1109  -0.7352
 G96  H24A  H  HCH2  0   0.246   -5.4467  -1.0069   1.0084
 G96  HO3   H  HOH1  0   0.453    1.2607  -5.3396   1.8425
 G96  H19   H  HCH3  0   0.239    2.3059  -4.9747  -2.0691
 G96  H19A  H  HCH3  0   0.245    2.0327  -6.5506  -1.3185
 G96  H19B  H  HCH3  0   0.245    0.6668  -5.4671  -1.6347
 G96  H11   H  HCR6  0   0.288   -0.2301   2.7838  -0.1092
 G96  H23   H  HCH1  0   0.239   -4.5573   1.2813  -0.7933
 G96  HN7   H  HNH2  0   0.336   -4.5141   0.9837   2.1097
 G96  HN7A  H  HNH2  0   0.348   -3.8910   2.2320   1.2839
 G96  H3    H  HCR6  0   0.250   -9.5554   1.1942   1.7796
 G96  H2    H  HCR6  0   0.240   -7.3027   0.2386   2.0426
 G96  O1    O  O2    0  -0.486   -2.0891   1.0202  -0.0192
 G96  C13   C  CSP   0   0.172    1.1615  -2.3237  -0.0013
 G96  C21   C  CH2   0  -0.337    2.7001   3.5412  -0.1874

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
 G96  N1   C9    aromatic  1.295  0.020  1.295
 G96  N1   O2    aromatic  1.324  0.020  1.324
 G96  N3   C8    single    1.344  0.020  1.344
 G96  C4   C5    aromatic  1.389  0.020  1.389
 G96  C4   C3    aromatic  1.389  0.020  1.389
 G96  C5   C6    aromatic  1.389  0.020  1.389
 G96  C6   C1    aromatic  1.393  0.020  1.393
 G96  C7   O1    single    1.423  0.020  1.423
 G96  C7   C23   single    1.525  0.020  1.525
 G96  C8   C9    aromatic  1.440  0.020  1.440
 G96  C8   N2    aromatic  1.302  0.020  1.302
 G96  C10  N4    aromatic  1.326  0.020  1.326
 G96  C10  C11   aromatic  1.396  0.020  1.396
 G96  C10  O1    single    1.336  0.020  1.336
 G96  C13  C17   triple    1.205  0.020  1.205
 G96  C13  C12   single    1.424  0.020  1.424
 G96  C15  C14   aromatic  1.404  0.020  1.404
 G96  C15  N5    aromatic  1.365  0.020  1.365
 G96  C15  C11   aromatic  1.382  0.020  1.382
 G96  C17  C18   single    1.474  0.020  1.474
 G96  C20  C18   single    1.530  0.020  1.530
 G96  C21  C22   single    1.517  0.020  1.517
 G96  C21  N5    single    1.457  0.020  1.457
 G96  C24  C23   single    1.532  0.020  1.532
 G96  C24  C1    single    1.502  0.020  1.502
 G96  O3   C18   single    1.413  0.020  1.413
 G96  C18  C19   single    1.527  0.020  1.527
 G96  C12  N4    aromatic  1.331  0.020  1.331
 G96  C12  C14   aromatic  1.391  0.020  1.391
 G96  C14  N6    aromatic  1.363  0.020  1.363
 G96  N6   C16   aromatic  1.306  0.020  1.306
 G96  C16  N5    aromatic  1.370  0.020  1.370
 G96  C16  C9    single    1.445  0.020  1.445
 G96  O2   N2    aromatic  1.360  0.020  1.360
 G96  C23  N7    single    1.450  0.020  1.450
 G96  C1   C2    aromatic  1.393  0.020  1.393
 G96  C3   C2    aromatic  1.389  0.020  1.389
 G96  N3   HN3   single    0.890  0.020  1.040
 G96  N3   HN3A  single    0.890  0.020  1.040
 G96  C4   H4    single    0.930  0.020  1.080
 G96  C5   H5    single    0.930  0.020  1.080
 G96  C6   H6    single    0.930  0.020  1.080
 G96  C7   H7    single    0.970  0.020  1.090
 G96  C7   H7A   single    0.970  0.020  1.090
 G96  C20  H20   single    0.970  0.020  1.090
 G96  C20  H20A  single    0.970  0.020  1.090
 G96  C20  H20B  single    0.970  0.020  1.090
 G96  C21  H21   single    0.970  0.020  1.090
 G96  C21  H21A  single    0.970  0.020  1.090
 G96  C22  H22   single    0.970  0.020  1.090
 G96  C22  H22A  single    0.970  0.020  1.090
 G96  C22  H22B  single    0.970  0.020  1.090
 G96  C24  H24   single    0.970  0.020  1.090
 G96  C24  H24A  single    0.970  0.020  1.090
 G96  O3   HO3   single    0.850  0.020  0.980
 G96  C19  H19   single    0.970  0.020  1.090
 G96  C19  H19A  single    0.970  0.020  1.090
 G96  C19  H19B  single    0.970  0.020  1.090
 G96  C11  H11   single    0.930  0.020  1.080
 G96  C23  H23   single    0.970  0.020  1.090
 G96  N7   HN7   single    0.890  0.020  1.040
 G96  N7   HN7A  single    0.890  0.020  1.040
 G96  C3   H3    single    0.930  0.020  1.080
 G96  C2   H2    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
 G96  O2    N1   C9    106.89  3.000
 G96  HN3A  N3   HN3   116.86  3.000
 G96  HN3A  N3   C8    118.11  3.000
 G96  HN3   N3   C8    116.29  3.000
 G96  H4    C4   C3    120.32  3.000
 G96  H4    C4   C5    120.23  3.000
 G96  C3    C4   C5    119.45  3.000
 G96  H5    C5   C6    119.82  3.000
 G96  H5    C5   C4    120.09  3.000
 G96  C6    C5   C4    120.09  3.000
 G96  H6    C6   C1    119.53  3.000
 G96  H6    C6   C5    119.46  3.000
 G96  C1    C6   C5    121.01  3.000
 G96  H7A   C7   H7    107.62  3.000
 G96  H7A   C7   C23   110.33  3.000
 G96  H7    C7   C23   110.75  3.000
 G96  H7A   C7   O1    110.63  3.000
 G96  H7    C7   O1    110.23  3.000
 G96  C23   C7   O1    107.30  3.000
 G96  N2    C8   C9    107.28  3.000
 G96  N2    C8   N3    125.31  3.000
 G96  C9    C8   N3    127.37  3.000
 G96  O1    C10  C11   116.23  3.000
 G96  O1    C10  N4    118.72  3.000
 G96  C11   C10  N4    125.04  3.000
 G96  C11   C15  N5    132.96  3.000
 G96  C11   C15  C14   121.52  3.000
 G96  N5    C15  C14   105.51  3.000
 G96  C18   C17  C13   180.00  3.000
 G96  H20B  C20  H20A  108.35  3.000
 G96  H20B  C20  H20   107.87  3.000
 G96  H20A  C20  H20   108.52  3.000
 G96  H20B  C20  C18   111.05  3.000
 G96  H20A  C20  C18   109.77  3.000
 G96  H20   C20  C18   111.19  3.000
 G96  H22B  C22  H22A  108.54  3.000
 G96  H22B  C22  H22   107.86  3.000
 G96  H22A  C22  H22   108.00  3.000
 G96  H22B  C22  C21   111.58  3.000
 G96  H22A  C22  C21   111.35  3.000
 G96  H22   C22  C21   109.38  3.000
 G96  H24A  C24  H24   106.37  3.000
 G96  H24A  C24  C1    110.10  3.000
 G96  H24   C24  C1    109.43  3.000
 G96  H24A  C24  C23   108.91  3.000
 G96  H24   C24  C23   108.93  3.000
 G96  C1    C24  C23   112.89  3.000
 G96  HO3   O3   C18   108.68  3.000
 G96  C19   C18  O3    106.66  3.000
 G96  C19   C18  C20   110.66  3.000
 G96  O3    C18  C20   111.27  3.000
 G96  C19   C18  C17   109.25  3.000
 G96  O3    C18  C17   109.96  3.000
 G96  C20   C18  C17   109.01  3.000
 G96  H19B  C19  H19A  108.69  3.000
 G96  H19B  C19  H19   108.27  3.000
 G96  H19A  C19  H19   108.32  3.000
 G96  H19B  C19  C18   111.14  3.000
 G96  H19A  C19  C18   109.71  3.000
 G96  H19   C19  C18   110.63  3.000
 G96  C14   C12  N4    120.44  3.000
 G96  C14   C12  C13   120.56  3.000
 G96  N4    C12  C13   119.01  3.000
 G96  C12   N4   C10   119.91  3.000
 G96  N6    C14  C12   131.34  3.000
 G96  N6    C14  C15   110.15  3.000
 G96  C12   C14  C15   118.51  3.000
 G96  C16   N6   C14   104.85  3.000
 G96  C9    C16  N5    126.06  3.000
 G96  C9    C16  N6    120.36  3.000
 G96  N5    C16  N6    113.58  3.000
 G96  C16   N5   C21   129.04  3.000
 G96  C16   N5   C15   105.90  3.000
 G96  C21   N5   C15   124.99  3.000
 G96  C16   C9   C8    125.83  3.000
 G96  C16   C9   N1    126.24  3.000
 G96  C8    C9   N1    107.92  3.000
 G96  N2    O2   N1    112.00  3.000
 G96  O2    N2   C8    105.90  3.000
 G96  H11   C11  C15   124.07  3.000
 G96  H11   C11  C10   121.35  3.000
 G96  C15   C11  C10   114.58  3.000
 G96  H23   C23  N7    107.62  3.000
 G96  H23   C23  C24   108.06  3.000
 G96  N7    C23  C24   109.92  3.000
 G96  H23   C23  C7    107.81  3.000
 G96  N7    C23  C7    114.56  3.000
 G96  C24   C23  C7    108.66  3.000
 G96  HN7A  N7   HN7   106.31  3.000
 G96  HN7A  N7   C23   110.38  3.000
 G96  HN7   N7   C23   109.93  3.000
 G96  C2    C1   C24   121.36  3.000
 G96  C2    C1   C6    118.35  3.000
 G96  C24   C1   C6    120.29  3.000
 G96  H3    C3   C2    119.73  3.000
 G96  H3    C3   C4    120.08  3.000
 G96  C2    C3   C4    120.19  3.000
 G96  H2    C2   C3    119.61  3.000
 G96  H2    C2   C1    119.47  3.000
 G96  C3    C2   C1    120.92  3.000
 G96  C10   O1   C7    119.40  3.000
 G96  C12   C13  C17   180.00  3.000
 G96  H21A  C21  H21   106.56  3.000
 G96  H21A  C21  N5    108.65  3.000
 G96  H21   C21  N5    106.83  3.000
 G96  H21A  C21  C22   111.28  3.000
 G96  H21   C21  C22   110.68  3.000
 G96  N5    C21  C22   112.55  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
 G96  CONST_01  N2   C8   C9   N1      0.00   0.0  0
 G96  CONST_02  N6   C16  C9   N1    180.00   0.0  0
 G96  CONST_03  N5   C16  C9   N1      0.00   0.0  0
 G96  CONST_04  C8   N2   O2   N1      0.00   0.0  0
 G96  CONST_05  C1   C6   C5   C4      0.00   0.0  0
 G96  CONST_06  C1   C2   C3   C4      0.00   0.0  0
 G96  CONST_07  C2   C3   C4   C5      0.00   0.0  0
 G96  CONST_08  C2   C1   C6   C5      0.00   0.0  0
 G96  CONST_09  C3   C4   C5   C6      0.00   0.0  0
 G96  CONST_10  C3   C2   C1   C6      0.00   0.0  0
 G96  CONST_11  O2   N1   C9   C8      0.00   0.0  0
 G96  CONST_12  N6   C16  C9   C8      0.00   0.0  0
 G96  CONST_13  N5   C16  C9   C8    180.00   0.0  0
 G96  CONST_14  C14  C12  N4   C10     0.00   0.0  0
 G96  CONST_15  C14  C15  C11  C10     0.00   0.0  0
 G96  CONST_16  N5   C15  C11  C10   180.00   0.0  0
 G96  CONST_17  N4   C12  C14  C15     0.00   0.0  0
 G96  CONST_18  C16  N6   C14  C15     0.00   0.0  0
 G96  CONST_19  N6   C16  N5   C15     0.00   0.0  0
 G96  CONST_20  C9   C16  N5   C15   180.00   0.0  0
 G96  CONST_21  N4   C10  C11  C15     0.00   0.0  0
 G96  CONST_22  C11  C10  N4   C12     0.00   0.0  0
 G96  CONST_23  N5   C15  C14  C12   180.00   0.0  0
 G96  CONST_24  C11  C15  C14  C12     0.00   0.0  0
 G96  CONST_25  C16  N6   C14  C12   180.00   0.0  0
 G96  CONST_26  N6   C14  C12  N4    180.00   0.0  0
 G96  CONST_27  C16  N5   C15  C14     0.00   0.0  0
 G96  CONST_28  N5   C16  N6   C14     0.00   0.0  0
 G96  CONST_29  C9   C16  N6   C14   180.00   0.0  0
 G96  CONST_30  N5   C15  C14  N6      0.00   0.0  0
 G96  CONST_31  C11  C15  C14  N6    180.00   0.0  0
 G96  CONST_32  C11  C15  N5   C16   180.00   0.0  0
 G96  CONST_33  O2   N1   C9   C16   180.00   0.0  0
 G96  CONST_34  N2   C8   C9   C16   180.00   0.0  0
 G96  CONST_35  N2   O2   N1   C9      0.00   0.0  0
 G96  CONST_36  O2   N2   C8   C9      0.00   0.0  0
 G96  CONST_37  N3   C8   C9   N1    180.00   0.0  0
 G96  CONST_38  C16  C9   C8   N3      0.00   0.0  0
 G96  CONST_39  O2   N2   C8   N3    180.00   0.0  0
 G96  CONST_40  C24  C1   C6   C5    180.00   0.0  0
 G96  CONST_41  C13  C12  N4   C10   180.00   0.0  0
 G96  CONST_42  C15  C14  C12  C13   180.00   0.0  0
 G96  CONST_43  N6   C14  C12  C13     0.00   0.0  0
 G96  CONST_44  O1   C10  C11  C15   180.00   0.0  0
 G96  CONST_45  C14  C15  N5   C21   180.00   0.0  0
 G96  CONST_46  C11  C15  N5   C21     0.00   0.0  0
 G96  CONST_47  N6   C16  N5   C21   180.00   0.0  0
 G96  CONST_48  C9   C16  N5   C21     0.00   0.0  0
 G96  CONST_49  C3   C2   C1   C24   180.00   0.0  0
 G96  CONST_50  O1   C10  N4   C12   180.00   0.0  0
 G96  CONST_51  H6   C6   C5   C4    180.00   0.0  0
 G96  CONST_52  H2   C2   C3   C4    180.00   0.0  0
 G96  CONST_53  H3   C3   C4   C5    180.00   0.0  0
 G96  CONST_54  H4   C4   C5   C6    180.00   0.0  0
 G96  CONST_55  H11  C11  C10  N4    180.00   0.0  0
 G96  CONST_56  H5   C5   C6   C1    180.00   0.0  0
 G96  Var_01    C23  C24  C1   C6     86.18  30.0  2
 G96  Var_02    N4   C10  O1   C7     -0.38  30.0  2
 G96  Var_03    C22  C21  N5   C15    93.86  30.0  2
 G96  Var_04    C23  C7   O1   C10   177.37  30.0  1
 G96  Var_05    H22  C22  C21  N5   -178.52  30.0  3
 G96  Var_06    C20  C18  C17  C13    28.69  30.0  3
 G96  Var_07    H20  C20  C18  C17    61.56  30.0  3
 G96  Var_08    H19  C19  C18  C17    59.95  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
 G96  chir_01  C23  C7  C24  N7  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
 G96  plan-1  N1    0.020
 G96  plan-1  N3    0.020
 G96  plan-1  C8    0.020
 G96  plan-1  C16   0.020
 G96  plan-1  C9    0.020
 G96  plan-1  O2    0.020
 G96  plan-1  N2    0.020
 G96  plan-2  C4    0.020
 G96  plan-2  C5    0.020
 G96  plan-2  C6    0.020
 G96  plan-2  C24   0.020
 G96  plan-2  C1    0.020
 G96  plan-2  C3    0.020
 G96  plan-2  C2    0.020
 G96  plan-2  H4    0.020
 G96  plan-2  H5    0.020
 G96  plan-2  H6    0.020
 G96  plan-2  H3    0.020
 G96  plan-2  H2    0.020
 G96  plan-3  C10   0.020
 G96  plan-3  C15   0.020
 G96  plan-3  C17   0.020
 G96  plan-3  C12   0.020
 G96  plan-3  N4    0.020
 G96  plan-3  C14   0.020
 G96  plan-3  N6    0.020
 G96  plan-3  C16   0.020
 G96  plan-3  N5    0.020
 G96  plan-3  C9    0.020
 G96  plan-3  C11   0.020
 G96  plan-3  H11   0.020
 G96  plan-3  O1    0.020
 G96  plan-3  C13   0.020
 G96  plan-3  C21   0.020
 G96  plan-4  N3    0.020
 G96  plan-4  C8    0.020
 G96  plan-4  HN3   0.020
 G96  plan-4  HN3A  0.020

