# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 14:04:52 2020
#   Inital geometry file: a 90 line input string
#   Ligand name: 1-(5-ethyl-2,4-dihydroxyphenyl)-1,3-dihydro-2H-benzimidazol-2-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1cc(N2C(=O)Nc3ccccc23)c(O)cc1O
#
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
 4EO  4EO  1-(5-ethyl-2,4-dihydroxyphenyl)-1,3-dihydro-2H-benzimidazol-2-one  ligand  34  20  .  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_4EO
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
 4EO  O1   O  O     0  -0.470   0.6312  -2.7759   0.1988
 4EO  C6   C  CR5   0   0.643   1.3221  -1.7905   0.0601
 4EO  N2   N  NR15  0  -0.737   2.6698  -1.7295  -0.1773
 4EO  C7   C  CR56  0   0.355   3.0992  -0.4243  -0.2953
 4EO  C12  C  CR56  0   0.295   1.9734   0.3827  -0.1190
 4EO  C11  C  CR16  0  -0.290   2.0489   1.7579  -0.1862
 4EO  C10  C  CR16  0  -0.252   3.3018   2.3155  -0.4303
 4EO  C9   C  CR16  0  -0.243   4.4258   1.5150  -0.6004
 4EO  C8   C  CR16  0  -0.287   4.3417   0.1266  -0.5360
 4EO  N1   N  NR5   0  -0.708   0.9001  -0.4685   0.1168
 4EO  C5   C  CR6   0   0.179  -0.4515  -0.0768   0.2381
 4EO  C4   C  CR16  0  -0.291  -1.2854  -0.0302  -0.8723
 4EO  C13  C  CR6   0   0.338  -0.9487   0.2833   1.4876
 4EO  O2   O  OH1   0  -0.593  -0.2007   0.2644   2.6008
 4EO  C14  C  CR16  0  -0.456  -2.2739   0.6884   1.5961
 4EO  C15  C  CR6   0   0.361  -3.0895   0.7254   0.4745
 4EO  O3   O  OH1   0  -0.603  -4.3766   1.1155   0.5515
 4EO  C3   C  CR6   0   0.031  -2.6083   0.3620  -0.7920
 4EO  C2   C  CH2   0  -0.483  -3.4983   0.3649  -2.0039
 4EO  C1   C  CH3   0  -0.641  -4.4339  -0.8417  -2.0583
 4EO  H7   H  HNR5  0   0.390   3.2375  -2.5530  -0.2743
 4EO  H11  H  HCR6  0   0.255   1.1733   2.3802  -0.0593
 4EO  H10  H  HCR6  0   0.240   3.3993   3.3906  -0.4879
 4EO  H9   H  HCR6  0   0.235   5.3857   1.9773  -0.7845
 4EO  H8   H  HCR6  0   0.233   5.2174  -0.4931  -0.6737
 4EO  H6   H  HCR6  0   0.232  -0.8769  -0.3139  -1.8352
 4EO  H12  H  HOH1  0   0.454   0.6849  -0.0573   2.3996
 4EO  H13  H  HCR6  0   0.241  -2.6530   0.9708   2.5719
 4EO  H14  H  HOH1  0   0.444  -4.6083   1.3344   1.4582
 4EO  H5   H  HCH2  0   0.237  -4.0855   1.2849  -2.0401
 4EO  H4   H  HCH2  0   0.224  -2.8700   0.3718  -2.8975
 4EO  H2   H  HCH3  0   0.218  -5.0464  -0.8172  -2.9602
 4EO  H1   H  HCH3  0   0.218  -3.8684  -1.7739  -2.0639
 4EO  H3   H  HCH3  0   0.231  -5.1049  -0.8632  -1.2011

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
 4EO  O3   C15  single    1.347  0.020  1.347
 4EO  C15  C14  aromatic  1.387  0.020  1.387
 4EO  C15  C3   aromatic  1.403  0.020  1.403
 4EO  C2   C3   single    1.504  0.020  1.504
 4EO  C2   C1   single    1.528  0.020  1.528
 4EO  C14  C13  aromatic  1.390  0.020  1.390
 4EO  C3   C4   aromatic  1.382  0.020  1.382
 4EO  C13  O2   single    1.341  0.020  1.341
 4EO  C13  C5   aromatic  1.392  0.020  1.392
 4EO  C4   C5   aromatic  1.389  0.020  1.389
 4EO  C5   N1   single    1.412  0.020  1.412
 4EO  C11  C10  aromatic  1.393  0.020  1.393
 4EO  C11  C12  aromatic  1.379  0.020  1.379
 4EO  C10  C9   aromatic  1.390  0.020  1.390
 4EO  C12  N1   single    1.390  0.020  1.390
 4EO  C12  C7   aromatic  1.396  0.020  1.396
 4EO  N1   C6   single    1.389  0.020  1.389
 4EO  C9   C8   aromatic  1.392  0.020  1.392
 4EO  C7   C8   aromatic  1.380  0.020  1.380
 4EO  C7   N2   single    1.379  0.020  1.379
 4EO  C6   O1   double    1.211  0.020  1.211
 4EO  C6   N2   single    1.370  0.020  1.370
 4EO  N2   H7   single    0.860  0.020  1.020
 4EO  C11  H11  single    0.930  0.020  1.080
 4EO  C10  H10  single    0.930  0.020  1.080
 4EO  C9   H9   single    0.930  0.020  1.080
 4EO  C8   H8   single    0.930  0.020  1.080
 4EO  C4   H6   single    0.930  0.020  1.080
 4EO  O2   H12  single    0.850  0.020  0.980
 4EO  C14  H13  single    0.930  0.020  1.080
 4EO  O3   H14  single    0.850  0.020  0.980
 4EO  C2   H5   single    0.970  0.020  1.090
 4EO  C2   H4   single    0.970  0.020  1.090
 4EO  C1   H2   single    0.970  0.020  1.090
 4EO  C1   H1   single    0.970  0.020  1.090
 4EO  C1   H3   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
 4EO  N1   C6   N2   105.29  3.000
 4EO  N2   C6   O1   128.11  3.000
 4EO  N1   C6   O1   126.60  3.000
 4EO  H7   N2   C7   126.26  3.000
 4EO  H7   N2   C6   122.42  3.000
 4EO  C7   N2   C6   111.31  3.000
 4EO  C8   C7   C12  121.14  3.000
 4EO  C8   C7   N2   132.30  3.000
 4EO  C12  C7   N2   106.57  3.000
 4EO  N1   C12  C11  131.39  3.000
 4EO  N1   C12  C7   106.86  3.000
 4EO  C11  C12  C7   121.74  3.000
 4EO  H11  C11  C10  121.22  3.000
 4EO  H11  C11  C12  121.59  3.000
 4EO  C10  C11  C12  117.20  3.000
 4EO  H10  C10  C9   119.55  3.000
 4EO  H10  C10  C11  119.25  3.000
 4EO  C9   C10  C11  121.20  3.000
 4EO  H9   C9   C8   119.20  3.000
 4EO  H9   C9   C10  119.49  3.000
 4EO  C8   C9   C10  121.31  3.000
 4EO  H8   C8   C9   121.10  3.000
 4EO  H8   C8   C7   121.49  3.000
 4EO  C9   C8   C7   117.41  3.000
 4EO  C5   N1   C12  125.71  3.000
 4EO  C12  N1   C6   109.96  3.000
 4EO  C5   N1   C6   123.93  3.000
 4EO  C13  C5   C4   119.62  3.000
 4EO  C4   C5   N1   121.00  3.000
 4EO  C13  C5   N1   119.38  3.000
 4EO  H6   C4   C3   119.12  3.000
 4EO  H6   C4   C5   118.36  3.000
 4EO  C3   C4   C5   122.51  3.000
 4EO  C14  C13  O2   118.10  3.000
 4EO  O2   C13  C5   122.82  3.000
 4EO  C14  C13  C5   119.07  3.000
 4EO  H12  O2   C13  110.12  3.000
 4EO  H13  C14  C15  121.00  3.000
 4EO  H13  C14  C13  118.65  3.000
 4EO  C15  C14  C13  120.35  3.000
 4EO  C3   C15  O3   117.03  3.000
 4EO  C3   C15  C14  121.42  3.000
 4EO  O3   C15  C14  121.55  3.000
 4EO  H14  O3   C15  110.50  3.000
 4EO  C2   C3   C15  121.61  3.000
 4EO  C2   C3   C4   121.35  3.000
 4EO  C15  C3   C4   117.03  3.000
 4EO  H4   C2   H5   106.07  3.000
 4EO  H4   C2   C1   109.15  3.000
 4EO  H5   C2   C1   109.57  3.000
 4EO  H4   C2   C3   108.60  3.000
 4EO  H5   C2   C3   110.28  3.000
 4EO  C1   C2   C3   112.93  3.000
 4EO  H3   C1   H1   107.86  3.000
 4EO  H3   C1   H2   107.78  3.000
 4EO  H1   C1   H2   107.84  3.000
 4EO  H3   C1   C2   111.40  3.000
 4EO  H1   C1   C2   110.97  3.000
 4EO  H2   C1   C2   110.84  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
 4EO  CONST_01  C10  C11  C12  C7      0.00   0.0  0
 4EO  CONST_02  C10  C9   C8   C7      0.00   0.0  0
 4EO  CONST_03  C9   C10  C11  C12     0.00   0.0  0
 4EO  CONST_04  C9   C8   C7   C12     0.00   0.0  0
 4EO  CONST_05  C8   C9   C10  C11     0.00   0.0  0
 4EO  CONST_06  C8   C7   C12  C11     0.00   0.0  0
 4EO  CONST_07  C15  C14  C13  C5      0.00   0.0  0
 4EO  CONST_08  C15  C3   C4   C5      0.00   0.0  0
 4EO  CONST_09  C14  C15  C3   C4      0.00   0.0  0
 4EO  CONST_10  C14  C13  C5   C4      0.00   0.0  0
 4EO  CONST_11  C3   C15  C14  C13     0.00   0.0  0
 4EO  CONST_12  C3   C4   C5   C13     0.00   0.0  0
 4EO  CONST_13  C14  C13  C5   N1    180.00   0.0  0
 4EO  CONST_14  C3   C4   C5   N1    180.00   0.0  0
 4EO  CONST_15  C7   C12  N1   C6      0.00   0.0  0
 4EO  CONST_16  C12  C7   N2   C6      0.00   0.0  0
 4EO  CONST_17  N1   C12  C7   N2      0.00   0.0  0
 4EO  CONST_18  C5   N1   C6   N2    180.00   0.0  0
 4EO  CONST_19  C12  N1   C6   N2      0.00   0.0  0
 4EO  CONST_20  C5   N1   C12  C7    180.00   0.0  0
 4EO  CONST_21  N1   C6   N2   C7      0.00   0.0  0
 4EO  CONST_22  O2   C13  C5   N1      0.00   0.0  0
 4EO  CONST_23  C2   C3   C4   C5    180.00   0.0  0
 4EO  CONST_24  O3   C15  C3   C4    180.00   0.0  0
 4EO  CONST_25  O2   C13  C5   C4    180.00   0.0  0
 4EO  CONST_26  O3   C15  C14  C13   180.00   0.0  0
 4EO  CONST_27  C15  C14  C13  O2    180.00   0.0  0
 4EO  CONST_28  C2   C3   C15  C14   180.00   0.0  0
 4EO  CONST_29  C5   N1   C6   O1      0.00   0.0  0
 4EO  CONST_30  C12  N1   C6   O1    180.00   0.0  0
 4EO  CONST_31  C7   N2   C6   O1    180.00   0.0  0
 4EO  CONST_32  H8   C8   C7   N2      0.00   0.0  0
 4EO  CONST_33  H11  C11  C12  C7    180.00   0.0  0
 4EO  CONST_34  H9   C9   C8   C7    180.00   0.0  0
 4EO  CONST_35  H10  C10  C11  C12   180.00   0.0  0
 4EO  CONST_36  H6   C4   C5   N1      0.00   0.0  0
 4EO  CONST_37  H13  C14  C13  C5    180.00   0.0  0
 4EO  CONST_38  H7   N2   C7   C12   180.00   0.0  0
 4EO  Var_01    C13  C5   N1   C6     99.36  30.0  3
 4EO  Var_02    C1   C2   C3   C4    101.53  30.0  3
 4EO  Var_03    H2   C1   C2   C3   -178.71  30.0  3

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
 4EO  plan-1  N1   0.020
 4EO  plan-1  C5   0.020
 4EO  plan-1  C4   0.020
 4EO  plan-1  C13  0.020
 4EO  plan-1  O2   0.020
 4EO  plan-1  C14  0.020
 4EO  plan-1  C15  0.020
 4EO  plan-1  O3   0.020
 4EO  plan-1  C3   0.020
 4EO  plan-1  C2   0.020
 4EO  plan-1  H6   0.020
 4EO  plan-1  H13  0.020
 4EO  plan-2  O1   0.020
 4EO  plan-2  C6   0.020
 4EO  plan-2  N2   0.020
 4EO  plan-2  C7   0.020
 4EO  plan-2  C12  0.020
 4EO  plan-2  C11  0.020
 4EO  plan-2  C10  0.020
 4EO  plan-2  C9   0.020
 4EO  plan-2  C8   0.020
 4EO  plan-2  N1   0.020
 4EO  plan-2  C5   0.020
 4EO  plan-2  H7   0.020
 4EO  plan-2  H11  0.020
 4EO  plan-2  H10  0.020
 4EO  plan-2  H9   0.020
 4EO  plan-2  H8   0.020

