# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 22:34:30 2022
#   Inital geometry file: a 142 line input string
#   Ligand name: 2-[[2-methoxy-4-(2-oxidanylidenepyrrolidin-1-yl)phenyl]amino]-4-(oxan-4-ylamino)-7~{H}-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(ccc1Nc2nc3[nH]cc(C#N)c3c(NC4CCOCC4)n2)N5CCCC5=O
#
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
 FZO  FZO  2-[[2-methoxy-4-(2-oxidanylidenepyrrolidin-1-yl)phenyl]amino]-4-(oxan-4-ylamino)-7~{H}-pyrrolo[2,3-d]pyrimidine-5-carbonitrile  ligand  58  33  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FZO
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
 FZO  C10  C  CH2   0  -0.286  -33.0374  -14.3130   -7.3805
 FZO  C13  C  CR16  0  -0.268  -34.0516  -18.0427   -9.1428
 FZO  C20  C  CR5   0  -0.120  -37.7444  -22.0951  -12.9482
 FZO  C21  C  CSP   0  -0.060  -38.6534  -21.6014  -13.9041
 FZO  C28  C  C     0  -0.468  -38.5486  -16.7862  -12.0436
 FZO  C01  C  CH3   0  -0.437  -34.5973  -20.0590   -4.8537
 FZO  C03  C  CR6   0   0.367  -34.3590  -19.0016   -6.9710
 FZO  C04  C  CR16  0  -0.459  -34.1445  -17.7584   -6.3920
 FZO  C05  C  CR6   0   0.387  -33.9227  -16.6355   -7.1940
 FZO  C07  C  CR5   0   0.524  -34.2838  -14.8997   -5.4808
 FZO  C08  C  CH2   0  -0.584  -33.9152  -13.4401   -5.3438
 FZO  C09  C  CH2   0  -0.475  -32.7612  -13.2559   -6.3173
 FZO  C12  C  CR16  0  -0.369  -33.8709  -16.7905   -8.5758
 FZO  C14  C  CR6   0   0.240  -34.3243  -19.1580   -8.3669
 FZO  C16  C  CR6   0   0.568  -35.3604  -20.7516   -9.9417
 FZO  C18  C  CR56  0   0.506  -36.2517  -22.2926  -11.2516
 FZO  C19  C  CR56  0  -0.072  -37.0077  -21.3596  -11.9589
 FZO  C23  C  CR15  0   0.031  -37.4045  -23.4163  -12.7936
 FZO  C25  C  CR6   0   0.516  -36.8515  -20.0197  -11.5352
 FZO  C27  C  CR16  0  -0.071  -37.3022  -17.6108  -11.7491
 FZO  C29  C  C     0  -0.182  -38.2769  -15.3195  -11.7378
 FZO  C31  C  C     0  -0.184  -35.9847  -15.5293  -12.1530
 FZO  C32  C  C     0  -0.464  -36.1106  -17.0070  -12.4902
 FZO  N06  N  NR5   0  -0.580  -33.7164  -15.3670   -6.6337
 FZO  N15  N  NH1   0  -0.748  -34.5238  -20.4299   -8.9139
 FZO  N17  N  N     0  -0.514  -35.4211  -22.0447  -10.2451
 FZO  N22  N  NS    0  -0.258  -39.3960  -21.1772  -14.6801
 FZO  N24  N  NR15  0  -0.666  -36.5125  -23.5227  -11.7776
 FZO  N26  N  NH1   0  -0.682  -37.5224  -19.0016  -12.0913
 FZO  N33  N  N     0  -0.521  -36.0224  -19.7560  -10.5322
 FZO  O11  O  O     0  -0.463  -34.9847  -15.5354   -4.7189
 FZO  O30  O  O     0  -0.477  -37.1669  -14.8198  -12.4486
 FZO  H1   H  HCH2  0   0.263  -32.1291  -14.6976   -7.8441
 FZO  H2   H  HCH2  0   0.248  -33.6824  -13.9221   -8.1732
 FZO  H3   H  HCR6  0   0.269  -33.9896  -18.1468  -10.2159
 FZO  H4   H  H     0   0.232  -38.8342  -16.8983  -13.0951
 FZO  H5   H  H     0   0.248  -39.3903  -17.1296  -11.4376
 FZO  H6   H  HCH3  0   0.261  -34.8032  -21.0667   -4.5014
 FZO  H7   H  HCH3  0   0.230  -33.6299  -19.7391   -4.4581
 FZO  H8   H  HCH3  0   0.230  -35.3736  -19.3890   -4.4750
 FZO  H9   H  HCR6  0   0.293  -34.1555  -17.6556   -5.3194
 FZO  H10  H  HCH2  0   0.277  -33.6797  -13.1917   -4.3097
 FZO  H11  H  HCH2  0   0.276  -34.7866  -12.8448   -5.6335
 FZO  H12  H  HCH2  0   0.253  -31.8119  -13.4658   -5.8232
 FZO  H13  H  HCH2  0   0.260  -32.7059  -12.2559   -6.7420
 FZO  H14  H  HCR6  0   0.268  -33.6861  -15.9481   -9.2274
 FZO  H15  H  HCR5  0   0.315  -37.7427  -24.2797  -13.3421
 FZO  H16  H  HCR6  0   0.248  -37.1012  -17.5641  -10.6757
 FZO  H17  H  H     0   0.199  -38.1227  -15.1999  -10.6549
 FZO  H18  H  H     0   0.239  -39.1366  -14.7075  -12.0144
 FZO  H19  H  H     0   0.198  -35.7264  -15.4191  -11.0881
 FZO  H20  H  H     0   0.237  -35.1818  -15.0692  -12.7311
 FZO  H21  H  H     0   0.229  -36.2488  -17.1336  -13.5684
 FZO  H22  H  H     0   0.250  -35.1878  -17.5225  -12.2153
 FZO  H23  H  HNH1  0   0.394  -34.1672  -21.2198   -8.3991
 FZO  H24  H  HNR5  0   0.423  -36.1005  -24.3870  -11.4599
 FZO  H25  H  HNH1  0   0.402  -38.0782  -19.1863  -12.9115
 FZO  O02  O  O2    0  -0.469  -34.5970  -20.1229   -6.2653

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
 FZO  N22  C21  triple    1.155  0.020  1.155
 FZO  C21  C20  single    1.408  0.020  1.408
 FZO  C20  C23  aromatic  1.373  0.020  1.373
 FZO  C20  C19  aromatic  1.436  0.020  1.436
 FZO  C23  N24  aromatic  1.356  0.020  1.356
 FZO  C32  C31  single    1.521  0.020  1.521
 FZO  C32  C27  single    1.528  0.020  1.528
 FZO  O30  C31  single    1.410  0.020  1.410
 FZO  O30  C29  single    1.410  0.020  1.410
 FZO  N26  C27  single    1.449  0.020  1.449
 FZO  N26  C25  single    1.340  0.020  1.340
 FZO  C28  C27  single    1.523  0.020  1.523
 FZO  C28  C29  single    1.523  0.020  1.523
 FZO  C19  C25  aromatic  1.414  0.020  1.414
 FZO  C19  C18  aromatic  1.394  0.020  1.394
 FZO  N24  C18  aromatic  1.363  0.020  1.363
 FZO  C25  N33  aromatic  1.328  0.020  1.328
 FZO  C18  N17  aromatic  1.328  0.020  1.328
 FZO  N33  C16  aromatic  1.333  0.020  1.333
 FZO  N17  C16  aromatic  1.330  0.020  1.330
 FZO  C16  N15  single    1.364  0.020  1.364
 FZO  C13  C12  aromatic  1.386  0.020  1.386
 FZO  C13  C14  aromatic  1.386  0.020  1.386
 FZO  N15  C14  single    1.399  0.020  1.399
 FZO  C12  C05  aromatic  1.391  0.020  1.391
 FZO  C14  C03  aromatic  1.405  0.020  1.405
 FZO  C10  N06  single    1.459  0.020  1.459
 FZO  C10  C09  single    1.524  0.020  1.524
 FZO  C05  N06  single    1.402  0.020  1.402
 FZO  C05  C04  aromatic  1.398  0.020  1.398
 FZO  C03  C04  aromatic  1.388  0.020  1.388
 FZO  C03  O02  single    1.346  0.020  1.346
 FZO  N06  C07  single    1.367  0.020  1.367
 FZO  C09  C08  single    1.521  0.020  1.521
 FZO  O02  C01  single    1.413  0.020  1.413
 FZO  C08  C07  single    1.512  0.020  1.512
 FZO  C07  O11  double    1.215  0.020  1.215
 FZO  C10  H1   single    0.970  0.020  1.090
 FZO  C10  H2   single    0.970  0.020  1.090
 FZO  C13  H3   single    0.930  0.020  1.080
 FZO  C28  H4   single    0.970  0.020  1.090
 FZO  C28  H5   single    0.970  0.020  1.090
 FZO  C01  H6   single    0.970  0.020  1.090
 FZO  C01  H7   single    0.970  0.020  1.090
 FZO  C01  H8   single    0.970  0.020  1.090
 FZO  C04  H9   single    0.930  0.020  1.080
 FZO  C08  H10  single    0.970  0.020  1.090
 FZO  C08  H11  single    0.970  0.020  1.090
 FZO  C09  H12  single    0.970  0.020  1.090
 FZO  C09  H13  single    0.970  0.020  1.090
 FZO  C12  H14  single    0.930  0.020  1.080
 FZO  C23  H15  single    0.930  0.020  1.080
 FZO  C27  H16  single    0.970  0.020  1.090
 FZO  C29  H17  single    0.970  0.020  1.090
 FZO  C29  H18  single    0.970  0.020  1.090
 FZO  C31  H19  single    0.970  0.020  1.090
 FZO  C31  H20  single    0.970  0.020  1.090
 FZO  C32  H21  single    0.970  0.020  1.090
 FZO  C32  H22  single    0.970  0.020  1.090
 FZO  N15  H23  single    0.860  0.020  1.020
 FZO  N24  H24  single    0.860  0.020  1.020
 FZO  N26  H25  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
 FZO  H2   C10  H1   108.01  3.000
 FZO  H2   C10  N06  110.76  3.000
 FZO  H1   C10  N06  110.52  3.000
 FZO  H2   C10  C09  111.37  3.000
 FZO  H1   C10  C09  112.97  3.000
 FZO  N06  C10  C09  103.19  3.000
 FZO  H3   C13  C14  119.34  3.000
 FZO  H3   C13  C12  119.08  3.000
 FZO  C14  C13  C12  121.58  3.000
 FZO  C23  C20  C19  106.75  3.000
 FZO  C19  C20  C21  128.25  3.000
 FZO  C23  C20  C21  124.99  3.000
 FZO  N22  C21  C20  180.00  3.000
 FZO  H5   C28  H4   107.42  3.000
 FZO  H5   C28  C29  109.20  3.000
 FZO  H4   C28  C29  109.75  3.000
 FZO  H5   C28  C27  110.67  3.000
 FZO  H4   C28  C27  110.09  3.000
 FZO  C29  C28  C27  109.67  3.000
 FZO  H8   C01  H7   108.89  3.000
 FZO  H8   C01  H6   108.75  3.000
 FZO  H7   C01  H6   108.76  3.000
 FZO  H8   C01  O02  111.96  3.000
 FZO  H7   C01  O02  112.00  3.000
 FZO  H6   C01  O02  106.37  3.000
 FZO  O02  C03  C14  115.62  3.000
 FZO  O02  C03  C04  123.70  3.000
 FZO  C14  C03  C04  120.68  3.000
 FZO  H9   C04  C05  119.74  3.000
 FZO  H9   C04  C03  119.94  3.000
 FZO  C05  C04  C03  120.32  3.000
 FZO  N06  C05  C12  119.49  3.000
 FZO  N06  C05  C04  121.40  3.000
 FZO  C12  C05  C04  119.09  3.000
 FZO  O11  C07  N06  126.12  3.000
 FZO  O11  C07  C08  126.09  3.000
 FZO  N06  C07  C08  107.77  3.000
 FZO  H11  C08  H10  107.42  3.000
 FZO  H11  C08  C09  111.64  3.000
 FZO  H10  C08  C09  114.58  3.000
 FZO  H11  C08  C07  107.88  3.000
 FZO  H10  C08  C07  111.04  3.000
 FZO  C09  C08  C07  104.12  3.000
 FZO  H13  C09  H12  108.03  3.000
 FZO  H13  C09  C08  113.56  3.000
 FZO  H12  C09  C08  110.32  3.000
 FZO  H13  C09  C10  111.98  3.000
 FZO  H12  C09  C10  109.89  3.000
 FZO  C08  C09  C10  103.00  3.000
 FZO  H14  C12  C05  121.21  3.000
 FZO  H14  C12  C13  118.66  3.000
 FZO  C05  C12  C13  120.13  3.000
 FZO  N15  C14  C03  119.09  3.000
 FZO  C03  C14  C13  118.13  3.000
 FZO  N15  C14  C13  122.75  3.000
 FZO  N33  C16  N17  127.04  3.000
 FZO  N17  C16  N15  115.43  3.000
 FZO  N33  C16  N15  117.53  3.000
 FZO  N24  C18  N17  125.48  3.000
 FZO  N17  C18  C19  126.78  3.000
 FZO  N24  C18  C19  107.73  3.000
 FZO  C25  C19  C18  114.99  3.000
 FZO  C18  C19  C20  106.56  3.000
 FZO  C25  C19  C20  138.45  3.000
 FZO  H15  C23  N24  121.67  3.000
 FZO  H15  C23  C20  129.51  3.000
 FZO  N24  C23  C20  108.82  3.000
 FZO  N33  C25  N26  118.37  3.000
 FZO  N33  C25  C19  118.91  3.000
 FZO  N26  C25  C19  122.70  3.000
 FZO  H16  C27  N26  107.50  3.000
 FZO  H16  C27  C32  108.42  3.000
 FZO  N26  C27  C32  112.54  3.000
 FZO  H16  C27  C28  108.50  3.000
 FZO  N26  C27  C28  110.46  3.000
 FZO  C32  C27  C28  109.30  3.000
 FZO  H18  C29  H17  107.39  3.000
 FZO  H18  C29  O30  107.09  3.000
 FZO  H17  C29  O30  110.33  3.000
 FZO  H18  C29  C28  110.42  3.000
 FZO  H17  C29  C28  109.11  3.000
 FZO  O30  C29  C28  112.38  3.000
 FZO  H20  C31  H19  107.32  3.000
 FZO  H20  C31  O30  107.08  3.000
 FZO  H19  C31  O30  110.42  3.000
 FZO  H20  C31  C32  110.68  3.000
 FZO  H19  C31  C32  109.33  3.000
 FZO  O30  C31  C32  111.90  3.000
 FZO  H22  C32  H21  107.46  3.000
 FZO  H22  C32  C31  109.44  3.000
 FZO  H21  C32  C31  109.95  3.000
 FZO  H22  C32  C27  110.51  3.000
 FZO  H21  C32  C27  109.50  3.000
 FZO  C31  C32  C27  109.94  3.000
 FZO  C07  N06  C05  125.81  3.000
 FZO  C07  N06  C10  112.19  3.000
 FZO  C05  N06  C10  121.16  3.000
 FZO  H23  N15  C16  114.65  3.000
 FZO  H23  N15  C14  117.54  3.000
 FZO  C16  N15  C14  126.63  3.000
 FZO  C18  N17  C16  112.51  3.000
 FZO  H24  N24  C23  124.87  3.000
 FZO  H24  N24  C18  125.00  3.000
 FZO  C23  N24  C18  110.13  3.000
 FZO  H25  N26  C27  116.86  3.000
 FZO  H25  N26  C25  118.33  3.000
 FZO  C27  N26  C25  123.72  3.000
 FZO  C25  N33  C16  119.75  3.000
 FZO  C31  O30  C29  112.09  3.000
 FZO  C03  O02  C01  119.08  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
 FZO  CONST_01  C04  C05  C12  C13     0.00   0.0  0
 FZO  CONST_02  C04  C03  C14  C13     0.00   0.0  0
 FZO  CONST_03  C18  N24  C23  C20     0.00   0.0  0
 FZO  CONST_04  N33  C25  C19  C20   180.00   0.0  0
 FZO  CONST_05  N24  C18  C19  C20     0.00   0.0  0
 FZO  CONST_06  N17  C18  C19  C20   180.00   0.0  0
 FZO  CONST_07  C12  C13  C14  C03     0.00   0.0  0
 FZO  CONST_08  C12  C05  C04  C03     0.00   0.0  0
 FZO  CONST_09  C14  C13  C12  C05     0.00   0.0  0
 FZO  CONST_10  C14  C03  C04  C05     0.00   0.0  0
 FZO  CONST_11  C19  C25  N33  C16     0.00   0.0  0
 FZO  CONST_12  C19  C18  N17  C16     0.00   0.0  0
 FZO  CONST_13  N24  C18  N17  C16   180.00   0.0  0
 FZO  CONST_14  C23  C20  C19  C18     0.00   0.0  0
 FZO  CONST_15  N33  C25  C19  C18     0.00   0.0  0
 FZO  CONST_16  N33  C16  N17  C18     0.00   0.0  0
 FZO  CONST_17  N24  C23  C20  C19     0.00   0.0  0
 FZO  CONST_18  C23  N24  C18  C19     0.00   0.0  0
 FZO  CONST_19  C25  C19  C20  C23   180.00   0.0  0
 FZO  CONST_20  N17  C18  N24  C23   180.00   0.0  0
 FZO  CONST_21  N24  C18  C19  C25   180.00   0.0  0
 FZO  CONST_22  N17  C18  C19  C25     0.00   0.0  0
 FZO  CONST_23  N17  C16  N33  C25     0.00   0.0  0
 FZO  CONST_24  N06  C05  C12  C13   180.00   0.0  0
 FZO  CONST_25  N06  C05  C04  C03   180.00   0.0  0
 FZO  CONST_26  C08  C07  N06  C10     0.00   0.0  0
 FZO  CONST_27  C08  C07  N06  C05   180.00   0.0  0
 FZO  CONST_28  O02  C03  C14  C13   180.00   0.0  0
 FZO  CONST_29  N26  C25  C19  C20     0.00   0.0  0
 FZO  CONST_30  N24  C23  C20  C21   180.00   0.0  0
 FZO  CONST_31  C25  C19  C20  C21     0.00   0.0  0
 FZO  CONST_32  C18  C19  C20  C21   180.00   0.0  0
 FZO  CONST_33  N15  C14  C03  C04   180.00   0.0  0
 FZO  CONST_34  O02  C03  C04  C05   180.00   0.0  0
 FZO  CONST_35  N15  C14  C13  C12   180.00   0.0  0
 FZO  CONST_36  N26  C25  N33  C16   180.00   0.0  0
 FZO  CONST_37  N26  C25  C19  C18   180.00   0.0  0
 FZO  CONST_38  N15  C16  N17  C18   180.00   0.0  0
 FZO  CONST_39  N15  C16  N33  C25   180.00   0.0  0
 FZO  CONST_40  C27  N26  C25  C19   180.00   0.0  0
 FZO  CONST_41  N33  C25  N26  C27     0.00   0.0  0
 FZO  CONST_42  O11  C07  N06  C10   180.00   0.0  0
 FZO  CONST_43  O11  C07  N06  C05     0.00   0.0  0
 FZO  CONST_44  H24  N24  C23  C20   180.00   0.0  0
 FZO  CONST_45  H3   C13  C14  C03   180.00   0.0  0
 FZO  CONST_46  H14  C12  C05  C04   180.00   0.0  0
 FZO  CONST_47  H9   C04  C05  C12   180.00   0.0  0
 FZO  CONST_48  H15  C23  N24  C18   180.00   0.0  0
 FZO  CONST_49  H25  N26  C25  C19     0.00   0.0  0
 FZO  Var_01    C12  C05  N06  C10   -20.06  30.0  1
 FZO  Var_02    C07  C08  C09  C10    28.33  30.0  1
 FZO  Var_03    C09  C10  N06  C05  -167.91  30.0  1
 FZO  Var_04    N06  C10  C09  C08   -30.27  30.0  1
 FZO  Var_05    N06  C07  C08  C09   -16.02  30.0  1
 FZO  Var_06    O30  C31  C32  C27   -56.56  30.0  1
 FZO  Var_07    O30  C29  C28  C27    56.30  30.0  1
 FZO  Var_08    C32  C31  O30  C29    59.36  30.0  1
 FZO  Var_09    C16  N15  C14  C13   -49.96  30.0  1
 FZO  Var_10    N33  C16  N15  C14     2.94  30.0  2
 FZO  Var_11    C14  C03  O02  C01   177.63  30.0  1
 FZO  Var_12    H6   C01  O02  C03  -179.71  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
 FZO  chir_01  C27  C32  N26  C28  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
 FZO  plan-1  C13  0.020
 FZO  plan-1  C03  0.020
 FZO  plan-1  C04  0.020
 FZO  plan-1  C05  0.020
 FZO  plan-1  C12  0.020
 FZO  plan-1  C14  0.020
 FZO  plan-1  N06  0.020
 FZO  plan-1  N15  0.020
 FZO  plan-1  H3   0.020
 FZO  plan-1  H9   0.020
 FZO  plan-1  H14  0.020
 FZO  plan-1  O02  0.020
 FZO  plan-2  C25  0.020
 FZO  plan-2  C27  0.020
 FZO  plan-2  N26  0.020
 FZO  plan-2  H25  0.020
 FZO  plan-3  C20  0.020
 FZO  plan-3  C21  0.020
 FZO  plan-3  C16  0.020
 FZO  plan-3  C18  0.020
 FZO  plan-3  C19  0.020
 FZO  plan-3  C23  0.020
 FZO  plan-3  C25  0.020
 FZO  plan-3  N15  0.020
 FZO  plan-3  N17  0.020
 FZO  plan-3  N22  0.020
 FZO  plan-3  N24  0.020
 FZO  plan-3  N26  0.020
 FZO  plan-3  N33  0.020
 FZO  plan-3  H15  0.020
 FZO  plan-3  H24  0.020
 FZO  plan-4  C10  0.020
 FZO  plan-4  C05  0.020
 FZO  plan-4  C07  0.020
 FZO  plan-4  C08  0.020
 FZO  plan-4  N06  0.020
 FZO  plan-4  O11  0.020

