# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 14:40:02 2020
#   Inital geometry file: a 120 line input string
#   Ligand name: N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(8-methyl[1]benzopyrano[4,3-c]pyrazol-1(4H)-yl)acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1ccc2OCc3cnn(CC(=O)Nc4ccc5OCCOc5c4)c3c2c1
#
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
 O4A  O4A  N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(8-methyl[1]benzopyrano[4,3-c]pyrazol-1(4H)-yl)acetamide  ligand  47  28  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_O4A
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
 O4A  C2   C  CR56  0   0.461   3.1189  -0.8852   0.2221
 O4A  C3   C  CR66  0   0.048   3.1965   0.4686  -0.2920
 O4A  C11  C  CR6   0   0.348  -4.1589   0.1283   0.7968
 O4A  C12  C  CR16  0  -0.450  -2.8564  -0.3128   0.5949
 O4A  C13  C  C     0  -0.233   5.1516  -0.4734   1.5636
 O4A  C14  C  CR16  0  -0.353   2.1938   1.1763  -0.9506
 O4A  C16  C  CR6   0   0.303  -5.0448   0.2539  -0.2749
 O4A  C17  C  CR6   0   0.373  -2.4212  -0.6283  -0.6881
 O4A  C21  C  CR16  0  -0.333   4.6587   2.3738  -0.5660
 O4A  C22  C  CR16  0  -0.352  -4.5964  -0.0519  -1.5520
 O4A  C23  C  CR6   0   0.101   2.3979   2.4644  -1.4325
 O4A  C24  C  CR16  0  -0.357  -3.2997  -0.4820  -1.7626
 O4A  C25  C  CR16  0  -0.301   3.6484   3.0445  -1.2393
 O4A  C26  C  CH2   0  -0.226  -5.7325   1.1750   2.1635
 O4A  C27  C  CH2   0  -0.226  -6.7786   0.6032   1.2372
 O4A  C28  C  CH3   0  -0.722   1.2889   3.2114  -2.1155
 O4A  C5   C  CR56  0  -0.221   4.0596  -1.3675   1.1012
 O4A  C7   C  CR15  0  -0.110   3.6889  -2.6960   1.3340
 O4A  C8   C  C     0   0.509  -0.0971  -1.3338  -0.1516
 O4A  C9   C  CR66  0   0.300   4.4401   1.0935  -0.0821
 O4A  N1   N  NR5   0  -0.363   2.2756  -1.9094  -0.0367
 O4A  N15  N  NH1   0  -0.744  -1.1291  -1.0867  -0.9855
 O4A  N4   N  N     0  -0.266   2.6056  -3.0064   0.6458
 O4A  O10  O  O     0  -0.484   5.4699   0.4610   0.5310
 O4A  O18  O  O2    0  -0.481  -4.5273   0.4297   2.0633
 O4A  O19  O  O2    0  -0.481  -6.3264   0.6628  -0.1069
 O4A  O20  O  O     0  -0.442  -0.0903  -1.1325   1.0458
 O4A  H33  H  H     0   0.237   4.8670   0.0714   2.4722
 O4A  H34  H  H     0   0.260   6.0706  -1.0172   1.7771
 O4A  H35  H  HCR6  0   0.232   1.2215   0.7275  -1.1038
 O4A  H37  H  HCR6  0   0.267   5.6239   2.8418  -0.4184
 O4A  H38  H  HCR6  0   0.272  -5.2757   0.0488  -2.3890
 O4A  H39  H  HCR6  0   0.273  -2.9735  -0.7141  -2.7688
 O4A  H40  H  HCR6  0   0.255   3.8390   4.0445  -1.6095
 O4A  H42  H  HCH2  0   0.244  -5.5439   2.2267   1.9229
 O4A  H41  H  HCH2  0   0.261  -6.0637   1.1120   3.1990
 O4A  H44  H  HCH2  0   0.243  -7.0068  -0.4321   1.5132
 O4A  H43  H  HCH2  0   0.261  -7.6966   1.1863   1.2951
 O4A  H46  H  HCH3  0   0.250   0.6632   3.7368  -1.3912
 O4A  H47  H  HCH3  0   0.246   1.6790   3.9569  -2.8075
 O4A  H45  H  HCH3  0   0.243   0.6398   2.5388  -2.6758
 O4A  H31  H  HCR5  0   0.269   4.1622  -3.4303   1.9681
 O4A  H36  H  HNH1  0   0.424  -0.9744  -1.2962  -1.9611
 O4A  C6   C  CH2   0  -0.465   1.1124  -1.9277  -0.8698
 O4A  H32  H  HCR6  0   0.291  -2.2061  -0.3959   1.4512
 O4A  H29  H  HCH2  0   0.336   0.8977  -2.9678  -1.1202
 O4A  H30  H  HCH2  0   0.304   1.3154  -1.4142  -1.8114

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
 O4A  C13  O10  single    1.428  0.020  1.428
 O4A  C13  C5   single    1.485  0.020  1.485
 O4A  O10  C9   single    1.355  0.020  1.355
 O4A  C7   C5   aromatic  1.399  0.020  1.399
 O4A  C7   N4   aromatic  1.320  0.020  1.320
 O4A  C5   C2   aromatic  1.375  0.020  1.375
 O4A  C9   C21  aromatic  1.386  0.020  1.386
 O4A  C9   C3   aromatic  1.407  0.020  1.407
 O4A  N4   N1   aromatic  1.333  0.020  1.333
 O4A  C21  C25  aromatic  1.387  0.020  1.387
 O4A  C2   C3   aromatic  1.450  0.020  1.450
 O4A  C2   N1   aromatic  1.352  0.020  1.352
 O4A  C3   C14  aromatic  1.393  0.020  1.393
 O4A  N1   C6   single    1.431  0.020  1.431
 O4A  C25  C23  aromatic  1.392  0.020  1.392
 O4A  O20  C8   double    1.214  0.020  1.214
 O4A  C14  C23  aromatic  1.390  0.020  1.390
 O4A  C23  C28  single    1.501  0.020  1.501
 O4A  C24  C22  aromatic  1.382  0.020  1.382
 O4A  C24  C17  aromatic  1.396  0.020  1.396
 O4A  C8   C6   single    1.527  0.020  1.527
 O4A  C8   N15  single    1.350  0.020  1.350
 O4A  C22  C16  aromatic  1.388  0.020  1.388
 O4A  N15  C17  single    1.403  0.020  1.403
 O4A  C17  C12  aromatic  1.391  0.020  1.391
 O4A  C16  O19  single    1.356  0.020  1.356
 O4A  C16  C11  aromatic  1.396  0.020  1.396
 O4A  O19  C27  single    1.419  0.020  1.419
 O4A  C12  C11  aromatic  1.390  0.020  1.390
 O4A  C11  O18  single    1.353  0.020  1.353
 O4A  C27  C26  single    1.510  0.020  1.510
 O4A  O18  C26  single    1.421  0.020  1.421
 O4A  C12  H32  single    0.930  0.020  1.080
 O4A  C13  H33  single    0.970  0.020  1.090
 O4A  C13  H34  single    0.970  0.020  1.090
 O4A  C14  H35  single    0.930  0.020  1.080
 O4A  C21  H37  single    0.930  0.020  1.080
 O4A  C22  H38  single    0.930  0.020  1.080
 O4A  C24  H39  single    0.930  0.020  1.080
 O4A  C25  H40  single    0.930  0.020  1.080
 O4A  C26  H42  single    0.970  0.020  1.090
 O4A  C26  H41  single    0.970  0.020  1.090
 O4A  C27  H44  single    0.970  0.020  1.090
 O4A  C27  H43  single    0.970  0.020  1.090
 O4A  C28  H46  single    0.970  0.020  1.090
 O4A  C28  H47  single    0.970  0.020  1.090
 O4A  C28  H45  single    0.970  0.020  1.090
 O4A  C6   H29  single    0.970  0.020  1.090
 O4A  C6   H30  single    0.970  0.020  1.090
 O4A  C7   H31  single    0.930  0.020  1.080
 O4A  N15  H36  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
 O4A  N1   C2   C5   106.47  3.000
 O4A  N1   C2   C3   132.29  3.000
 O4A  C5   C2   C3   121.16  3.000
 O4A  C9   C3   C14  118.75  3.000
 O4A  C14  C3   C2   127.11  3.000
 O4A  C9   C3   C2   114.14  3.000
 O4A  O18  C11  C16  121.72  3.000
 O4A  O18  C11  C12  117.51  3.000
 O4A  C16  C11  C12  120.77  3.000
 O4A  H32  C12  C17  121.75  3.000
 O4A  H32  C12  C11  118.30  3.000
 O4A  C17  C12  C11  119.95  3.000
 O4A  H34  C13  H33  107.73  3.000
 O4A  H34  C13  O10  106.28  3.000
 O4A  H33  C13  O10  109.37  3.000
 O4A  H34  C13  C5   112.39  3.000
 O4A  H33  C13  C5   111.48  3.000
 O4A  O10  C13  C5   109.42  3.000
 O4A  H35  C14  C23  117.85  3.000
 O4A  H35  C14  C3   120.21  3.000
 O4A  C23  C14  C3   121.94  3.000
 O4A  O19  C16  C22  119.08  3.000
 O4A  O19  C16  C11  122.13  3.000
 O4A  C22  C16  C11  118.79  3.000
 O4A  N15  C17  C24  116.80  3.000
 O4A  N15  C17  C12  123.91  3.000
 O4A  C24  C17  C12  119.30  3.000
 O4A  H37  C21  C9   119.49  3.000
 O4A  H37  C21  C25  120.43  3.000
 O4A  C9   C21  C25  120.08  3.000
 O4A  H38  C22  C24  119.98  3.000
 O4A  H38  C22  C16  119.23  3.000
 O4A  C24  C22  C16  120.79  3.000
 O4A  C28  C23  C25  121.29  3.000
 O4A  C28  C23  C14  120.68  3.000
 O4A  C25  C23  C14  118.02  3.000
 O4A  H39  C24  C22  119.39  3.000
 O4A  H39  C24  C17  120.21  3.000
 O4A  C22  C24  C17  120.39  3.000
 O4A  H40  C25  C23  119.69  3.000
 O4A  H40  C25  C21  118.96  3.000
 O4A  C23  C25  C21  121.35  3.000
 O4A  H41  C26  H42  108.47  3.000
 O4A  H41  C26  O18  107.14  3.000
 O4A  H42  C26  O18  110.01  3.000
 O4A  H41  C26  C27  110.53  3.000
 O4A  H42  C26  C27  110.38  3.000
 O4A  O18  C26  C27  110.24  3.000
 O4A  H43  C27  H44  108.48  3.000
 O4A  H43  C27  O19  107.24  3.000
 O4A  H44  C27  O19  110.16  3.000
 O4A  H43  C27  C26  110.41  3.000
 O4A  H44  C27  C26  110.35  3.000
 O4A  O19  C27  C26  110.14  3.000
 O4A  H45  C28  H47  108.01  3.000
 O4A  H45  C28  H46  107.26  3.000
 O4A  H47  C28  H46  107.29  3.000
 O4A  H45  C28  C23  111.52  3.000
 O4A  H47  C28  C23  111.40  3.000
 O4A  H46  C28  C23  111.15  3.000
 O4A  C7   C5   C13  135.63  3.000
 O4A  C7   C5   C2   104.96  3.000
 O4A  C13  C5   C2   119.41  3.000
 O4A  H31  C7   N4   120.39  3.000
 O4A  H31  C7   C5   128.88  3.000
 O4A  N4   C7   C5   110.73  3.000
 O4A  O20  C8   N15  125.68  3.000
 O4A  N15  C8   C6   112.73  3.000
 O4A  O20  C8   C6   121.59  3.000
 O4A  O10  C9   C21  117.98  3.000
 O4A  C21  C9   C3   119.83  3.000
 O4A  O10  C9   C3   122.12  3.000
 O4A  N4   N1   C6   119.25  3.000
 O4A  C6   N1   C2   128.93  3.000
 O4A  N4   N1   C2   111.77  3.000
 O4A  H36  N15  C8   116.22  3.000
 O4A  H36  N15  C17  114.44  3.000
 O4A  C8   N15  C17  129.28  3.000
 O4A  N1   N4   C7   106.04  3.000
 O4A  C9   O10  C13  117.59  3.000
 O4A  C26  O18  C11  114.45  3.000
 O4A  C27  O19  C16  113.94  3.000
 O4A  H30  C6   H29  106.68  3.000
 O4A  H30  C6   N1   110.18  3.000
 O4A  H29  C6   N1   107.80  3.000
 O4A  H30  C6   C8   111.72  3.000
 O4A  H29  C6   C8   108.84  3.000
 O4A  N1   C6   C8   111.42  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
 O4A  CONST_01  N4   C7   C5   C2     0.00   0.0  0
 O4A  CONST_02  C21  C9   C3   C2   180.00   0.0  0
 O4A  CONST_03  C23  C14  C3   C2   180.00   0.0  0
 O4A  CONST_04  C7   N4   N1   C2     0.00   0.0  0
 O4A  CONST_05  C25  C21  C9   C3     0.00   0.0  0
 O4A  CONST_06  C7   C5   C2   C3   180.00   0.0  0
 O4A  CONST_07  N4   N1   C2   C3   180.00   0.0  0
 O4A  CONST_08  C25  C23  C14  C3     0.00   0.0  0
 O4A  CONST_09  C24  C22  C16  C11    0.00   0.0  0
 O4A  CONST_10  C24  C17  C12  C11    0.00   0.0  0
 O4A  CONST_11  C22  C24  C17  C12    0.00   0.0  0
 O4A  CONST_12  C22  C16  C11  C12    0.00   0.0  0
 O4A  CONST_13  C21  C9   C3   C14    0.00   0.0  0
 O4A  CONST_14  C5   C2   C3   C14  180.00   0.0  0
 O4A  CONST_16  C21  C25  C23  C14    0.00   0.0  0
 O4A  CONST_17  C17  C24  C22  C16    0.00   0.0  0
 O4A  CONST_18  C17  C12  C11  C16    0.00   0.0  0
 O4A  CONST_19  C9   C21  C25  C23    0.00   0.0  0
 O4A  CONST_20  C9   C3   C14  C23    0.00   0.0  0
 O4A  CONST_21  N1   N4   C7   C5     0.00   0.0  0
 O4A  CONST_22  C9   C3   C2   C5     0.00   0.0  0
 O4A  CONST_23  N4   N1   C2   C5     0.00   0.0  0
 O4A  CONST_24  N1   C2   C5   C7     0.00   0.0  0
 O4A  CONST_26  C6   N1   C2   C3     0.00   0.0  0
 O4A  CONST_27  C28  C23  C14  C3   180.00   0.0  0
 O4A  CONST_28  N15  C17  C12  C11  180.00   0.0  0
 O4A  CONST_29  C28  C23  C25  C21  180.00   0.0  0
 O4A  CONST_30  N15  C17  C24  C22  180.00   0.0  0
 O4A  CONST_31  C6   N1   C2   C5   180.00   0.0  0
 O4A  CONST_32  C7   N4   N1   C6   180.00   0.0  0
 O4A  CONST_33  H31  C7   C5   C2   180.00   0.0  0
 O4A  CONST_34  H35  C14  C3   C2     0.00   0.0  0
 O4A  CONST_35  H37  C21  C9   C3   180.00   0.0  0
 O4A  CONST_36  H38  C22  C16  C11  180.00   0.0  0
 O4A  CONST_37  H39  C24  C17  C12  180.00   0.0  0
 O4A  CONST_38  H40  C25  C23  C14  180.00   0.0  0
 O4A  CONST_39  H32  C12  C11  C16  180.00   0.0  0
 O4A  CONST_40  C8   N15  C17  C12    0.00   0.0  0
 O4A  CONST_41  C8   N15  C17  C24  180.00   0.0  0
 O4A  CONST_42  H36  N15  C17  C12  180.00   0.0  0
 O4A  CONST_43  O20  C8   N15  C17    0.00   0.0  0
 O4A  CONST_44  C6   C8   N15  C17  180.00   0.0  0
 O4A  Var_01    O10  C13  C5   C2   -31.24  30.0  1
 O4A  Var_02    C27  C26  O18  C11   44.12  30.0  1
 O4A  Var_03    C21  C9   O10  C13  149.51  30.0  1
 O4A  Var_04    C26  C27  O19  C16   45.21  30.0  1
 O4A  Var_05    O19  C27  C26  O18  -60.47  30.0  1
 O4A  Var_06    C8   C6   N1   C2   -80.46  30.0  2
 O4A  Var_07    H46  C28  C23  C14   86.26  30.0  2
 O4A  Var_08    O20  C8   C6   N1   -13.17  30.0  2

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
 O4A  plan-1  C11  0.020
 O4A  plan-1  C12  0.020
 O4A  plan-1  C16  0.020
 O4A  plan-1  C17  0.020
 O4A  plan-1  C22  0.020
 O4A  plan-1  C24  0.020
 O4A  plan-1  N15  0.020
 O4A  plan-1  O18  0.020
 O4A  plan-1  O19  0.020
 O4A  plan-1  H38  0.020
 O4A  plan-1  H39  0.020
 O4A  plan-1  H32  0.020
 O4A  plan-2  C2   0.020
 O4A  plan-2  C3   0.020
 O4A  plan-2  C13  0.020
 O4A  plan-2  C5   0.020
 O4A  plan-2  C7   0.020
 O4A  plan-2  N1   0.020
 O4A  plan-2  N4   0.020
 O4A  plan-2  H31  0.020
 O4A  plan-2  C6   0.020
 O4A  plan-3  C2   0.020
 O4A  plan-3  C3   0.020
 O4A  plan-3  C14  0.020
 O4A  plan-3  C21  0.020
 O4A  plan-3  C23  0.020
 O4A  plan-3  C25  0.020
 O4A  plan-3  C28  0.020
 O4A  plan-3  C9   0.020
 O4A  plan-3  O10  0.020
 O4A  plan-3  H35  0.020
 O4A  plan-3  H37  0.020
 O4A  plan-3  H40  0.020
 O4A  plan-4  C17  0.020
 O4A  plan-4  C8   0.020
 O4A  plan-4  N15  0.020
 O4A  plan-4  O20  0.020
 O4A  plan-4  H36  0.020
 O4A  plan-4  C6   0.020

