# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 19 21:40:36 2022
#   Inital geometry file: a 126 line input string
#   Ligand name: methyl 4-[[(1~{S},6~{S})-6-(dimethylcarbamoyl)cyclohex-2-en-1-yl]carbamoyloxymethyl]benzoate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)c1ccc(COC(=O)N[C@H]2C=CCC[C@@H]2C(=O)N(C)C)cc1
#
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
 HOF  HOF  'methyl 4-[[(1~{S},6~{S})-6-(dimethylcarbamoyl)cyclohex-2-en-1-yl]carbamoyloxymethyl]benzoate'  ligand  50  26  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_HOF
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
 HOF  C1   C  CH3   0  -0.519   4.7297  -32.2488  26.9550
 HOF  C2   C  CH3   0  -0.529   3.3801  -31.6278  25.0209
 HOF  C3   C  C     0   0.607   4.6979  -29.9355  26.2837
 HOF  N1   N  NT    0  -0.453   4.3484  -31.2127  26.0146
 HOF  C4   C  CH1   0  -0.458   4.2325  -28.8459  25.3284
 HOF  C5   C  CH1   0  -0.074   5.2111  -27.6738  25.3210
 HOF  N2   N  NH1   0  -0.663   6.4574  -28.1016  24.7029
 HOF  C6   C  C     0   0.733   7.6786  -27.5731  24.9168
 HOF  O1   O  O2    0  -0.475   7.7012  -26.7797  25.9976
 HOF  C7   C  CH2   0  -0.238   8.8866  -26.0217  26.2138
 HOF  C8   C  CR6   0   0.063   8.9635  -24.8525  25.2711
 HOF  C9   C  CR16  0  -0.281  10.1109  -24.6058  24.5273
 HOF  C10  C  CR16  0  -0.240  10.1771  -23.5172  23.6728
 HOF  C11  C  CR6   0  -0.094   9.0876  -22.6612  23.5396
 HOF  C12  C  C     0   0.592   9.1986  -21.5176  22.5990
 HOF  O2   O  O2    0  -0.455   8.0992  -20.7813  22.5613
 HOF  C13  C  CH3   0  -0.421   8.0763  -19.6729  21.6641
 HOF  O3   O  O     0  -0.440  10.1815  -21.2851  21.9378
 HOF  C14  C  CR16  0  -0.252   7.9333  -22.9066  24.2826
 HOF  C15  C  CR16  0  -0.262   7.8770  -23.9900  25.1413
 HOF  O4   O  O     0  -0.504   8.6550  -27.8040  24.2352
 HOF  C16  C  C1    0  -0.221   4.6259  -26.4907  24.5929
 HOF  C17  C  C1    0  -0.221   3.3347  -26.3592  24.3060
 HOF  C18  C  CH2   0  -0.477   2.2994  -27.3622  24.7064
 HOF  C19  C  CH2   0  -0.440   2.8389  -28.3498  25.7312
 HOF  O5   O  O     0  -0.494   5.3549  -29.6502  27.2777
 HOF  H1   H  HCH3  0   0.251   5.7148  -32.0552  27.3695
 HOF  H2   H  HCH3  0   0.236   4.0165  -32.3330  27.7789
 HOF  H3   H  HCH3  0   0.240   4.7581  -33.2037  26.4331
 HOF  H4   H  HCH3  0   0.259   3.1878  -30.8564  24.2835
 HOF  H5   H  HCH3  0   0.251   3.7506  -32.5056  24.4912
 HOF  H6   H  HCH3  0   0.241   2.4277  -31.8916  25.4873
 HOF  H7   H  HCH1  0   0.271   4.1754  -29.2280  24.3041
 HOF  H8   H  HCH1  0   0.271   5.4254  -27.3942  26.3525
 HOF  H9   H  HNH1  0   0.398   6.3773  -28.6202  23.8404
 HOF  H10  H  HCH2  0   0.257   9.7784  -26.6455  26.1400
 HOF  H11  H  HCH2  0   0.270   8.8087  -25.6711  27.2433
 HOF  H12  H  HCR6  0   0.261  10.9610  -25.2713  24.6112
 HOF  H13  H  HCR6  0   0.263  11.0769  -23.3414  23.0987
 HOF  H14  H  HCH3  0   0.253   7.0980  -19.2160  21.7801
 HOF  H15  H  HCH3  0   0.240   8.8475  -18.9435  21.9105
 HOF  H16  H  HCH3  0   0.240   8.2040  -19.9957  20.6310
 HOF  H17  H  HCR6  0   0.264   7.0734  -22.2566  24.2010
 HOF  H18  H  HCR6  0   0.263   6.9742  -24.1618  25.7143
 HOF  H19  H  H     0   0.249   5.3272  -25.7188  24.2925
 HOF  H21  H  H     0   0.243   2.9999  -25.4863  23.7560
 HOF  H23  H  HCH2  0   0.244   1.9445  -27.8953  23.8174
 HOF  H24  H  HCH2  0   0.250   1.4238  -26.8474  25.1099
 HOF  H25  H  HCH2  0   0.258   2.1469  -29.1873  25.8386
 HOF  H26  H  HCH2  0   0.243   2.9042  -27.8704  26.7122

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
 HOF  C13  O2   single    1.426  0.020  1.426
 HOF  O2   C12  single    1.324  0.020  1.324
 HOF  O3   C12  double    1.207  0.020  1.207
 HOF  C12  C11  single    1.485  0.020  1.485
 HOF  C11  C10  aromatic  1.392  0.020  1.392
 HOF  C11  C14  aromatic  1.395  0.020  1.395
 HOF  C10  C9   aromatic  1.386  0.020  1.386
 HOF  C14  C15  aromatic  1.384  0.020  1.384
 HOF  C9   C8   aromatic  1.390  0.020  1.390
 HOF  C15  C8   aromatic  1.393  0.020  1.393
 HOF  C2   N1   single    1.448  0.020  1.448
 HOF  O4   C6   double    1.213  0.020  1.213
 HOF  C8   C7   single    1.504  0.020  1.504
 HOF  C6   N2   single    1.348  0.020  1.348
 HOF  C6   O1   single    1.341  0.020  1.341
 HOF  N2   C5   single    1.455  0.020  1.455
 HOF  O1   C7   single    1.423  0.020  1.423
 HOF  N1   C1   single    1.450  0.020  1.450
 HOF  N1   C3   single    1.351  0.020  1.351
 HOF  C4   C5   single    1.527  0.020  1.527
 HOF  C4   C19  single    1.533  0.020  1.533
 HOF  C4   C3   single    1.522  0.020  1.522
 HOF  C18  C19  single    1.522  0.020  1.522
 HOF  C18  C17  single    1.496  0.020  1.496
 HOF  C5   C16  single    1.507  0.020  1.507
 HOF  C3   O5   double    1.225  0.020  1.225
 HOF  C17  C16  double    1.329  0.020  1.329
 HOF  C1   H1   single    0.970  0.020  1.090
 HOF  C1   H2   single    0.970  0.020  1.090
 HOF  C1   H3   single    0.970  0.020  1.090
 HOF  C2   H4   single    0.970  0.020  1.090
 HOF  C2   H5   single    0.970  0.020  1.090
 HOF  C2   H6   single    0.970  0.020  1.090
 HOF  C4   H7   single    0.970  0.020  1.090
 HOF  C5   H8   single    0.970  0.020  1.090
 HOF  N2   H9   single    0.890  0.020  1.040
 HOF  C7   H10  single    0.970  0.020  1.090
 HOF  C7   H11  single    0.970  0.020  1.090
 HOF  C9   H12  single    0.930  0.020  1.080
 HOF  C10  H13  single    0.930  0.020  1.080
 HOF  C13  H14  single    0.970  0.020  1.090
 HOF  C13  H15  single    0.970  0.020  1.090
 HOF  C13  H16  single    0.970  0.020  1.090
 HOF  C14  H17  single    0.930  0.020  1.080
 HOF  C15  H18  single    0.930  0.020  1.080
 HOF  C16  H19  single    0.930  0.020  1.080
 HOF  C17  H21  single    0.930  0.020  1.080
 HOF  C18  H23  single    0.970  0.020  1.090
 HOF  C18  H24  single    0.970  0.020  1.090
 HOF  C19  H25  single    0.970  0.020  1.090
 HOF  C19  H26  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
 HOF  H3   C1   H2   108.11  3.000
 HOF  H3   C1   H1   108.40  3.000
 HOF  H2   C1   H1   108.53  3.000
 HOF  H3   C1   N1   108.82  3.000
 HOF  H2   C1   N1   111.86  3.000
 HOF  H1   C1   N1   111.02  3.000
 HOF  H6   C2   H5   108.01  3.000
 HOF  H6   C2   H4   107.91  3.000
 HOF  H5   C2   H4   107.62  3.000
 HOF  H6   C2   N1   111.04  3.000
 HOF  H5   C2   N1   109.69  3.000
 HOF  H4   C2   N1   112.41  3.000
 HOF  O5   C3   C4   120.43  3.000
 HOF  O5   C3   N1   121.36  3.000
 HOF  C4   C3   N1   118.20  3.000
 HOF  C3   N1   C2   125.48  3.000
 HOF  C3   N1   C1   118.56  3.000
 HOF  C2   N1   C1   114.58  3.000
 HOF  H7   C4   C19  108.14  3.000
 HOF  H7   C4   C5   107.26  3.000
 HOF  C19  C4   C5   109.60  3.000
 HOF  H7   C4   C3   110.69  3.000
 HOF  C19  C4   C3   110.17  3.000
 HOF  C5   C4   C3   110.89  3.000
 HOF  H8   C5   C16  109.40  3.000
 HOF  H8   C5   N2   108.00  3.000
 HOF  C16  C5   N2   110.97  3.000
 HOF  H8   C5   C4   108.56  3.000
 HOF  C16  C5   C4   110.85  3.000
 HOF  N2   C5   C4   108.98  3.000
 HOF  H9   N2   C6   114.14  3.000
 HOF  H9   N2   C5   116.48  3.000
 HOF  C6   N2   C5   126.39  3.000
 HOF  O4   C6   O1   123.50  3.000
 HOF  O1   C6   N2   112.04  3.000
 HOF  O4   C6   N2   124.44  3.000
 HOF  C7   O1   C6   116.84  3.000
 HOF  H11  C7   H10  107.83  3.000
 HOF  H11  C7   C8   110.22  3.000
 HOF  H10  C7   C8   111.12  3.000
 HOF  H11  C7   O1   104.78  3.000
 HOF  H10  C7   O1   111.47  3.000
 HOF  C8   C7   O1   111.19  3.000
 HOF  C15  C8   C9   118.96  3.000
 HOF  C15  C8   C7   119.99  3.000
 HOF  C9   C8   C7   121.05  3.000
 HOF  H12  C9   C10  119.55  3.000
 HOF  H12  C9   C8   119.85  3.000
 HOF  C10  C9   C8   120.60  3.000
 HOF  H13  C10  C11  120.02  3.000
 HOF  H13  C10  C9   119.66  3.000
 HOF  C11  C10  C9   120.32  3.000
 HOF  C14  C11  C12  122.34  3.000
 HOF  C14  C11  C10  119.25  3.000
 HOF  C12  C11  C10  118.41  3.000
 HOF  O3   C12  O2   123.61  3.000
 HOF  O3   C12  C11  123.78  3.000
 HOF  O2   C12  C11  112.60  3.000
 HOF  C13  O2   C12  117.61  3.000
 HOF  H16  C13  H15  109.25  3.000
 HOF  H16  C13  H14  109.36  3.000
 HOF  H15  C13  H14  109.38  3.000
 HOF  H16  C13  O2   111.36  3.000
 HOF  H15  C13  O2   111.50  3.000
 HOF  H14  C13  O2   105.92  3.000
 HOF  H17  C14  C15  119.03  3.000
 HOF  H17  C14  C11  120.82  3.000
 HOF  C15  C14  C11  120.14  3.000
 HOF  H18  C15  C14  119.11  3.000
 HOF  H18  C15  C8   120.17  3.000
 HOF  C14  C15  C8   120.72  3.000
 HOF  H19  C16  C17  119.84  3.000
 HOF  H19  C16  C5   116.17  3.000
 HOF  C17  C16  C5   123.99  3.000
 HOF  H21  C17  C18  117.49  3.000
 HOF  H21  C17  C16  119.27  3.000
 HOF  C18  C17  C16  123.24  3.000
 HOF  H24  C18  H23  105.62  3.000
 HOF  H24  C18  C19  109.94  3.000
 HOF  H23  C18  C19  110.20  3.000
 HOF  H24  C18  C17  109.72  3.000
 HOF  H23  C18  C17  109.47  3.000
 HOF  C19  C18  C17  111.72  3.000
 HOF  H26  C19  H25  106.61  3.000
 HOF  H26  C19  C18  109.91  3.000
 HOF  H25  C19  C18  109.84  3.000
 HOF  H26  C19  C4   108.86  3.000
 HOF  H25  C19  C4   110.72  3.000
 HOF  C18  C19  C4   110.81  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
 HOF  CONST_01  C11  C10  C9   C8      0.00   0.0  0
 HOF  CONST_02  C11  C14  C15  C8      0.00   0.0  0
 HOF  CONST_03  C14  C11  C10  C9      0.00   0.0  0
 HOF  CONST_04  C14  C15  C8   C9      0.00   0.0  0
 HOF  CONST_05  C15  C14  C11  C10     0.00   0.0  0
 HOF  CONST_06  C15  C8   C9   C10     0.00   0.0  0
 HOF  CONST_07  C10  C9   C8   C7    180.00   0.0  0
 HOF  CONST_08  C14  C15  C8   C7    180.00   0.0  0
 HOF  CONST_09  C12  C11  C10  C9    180.00   0.0  0
 HOF  CONST_10  C15  C14  C11  C12   180.00   0.0  0
 HOF  CONST_11  H13  C10  C9   C8    180.00   0.0  0
 HOF  CONST_12  H17  C14  C15  C8    180.00   0.0  0
 HOF  CONST_13  H18  C15  C8   C9    180.00   0.0  0
 HOF  CONST_14  H12  C9   C10  C11   180.00   0.0  0
 HOF  CONST_15  C4   C3   N1   C1    180.00   0.0  0
 HOF  CONST_16  C4   C3   N1   C2      0.00   0.0  0
 HOF  CONST_17  O5   C3   N1   C1      0.00   0.0  0
 HOF  CONST_18  O5   C3   N1   C2    180.00   0.0  0
 HOF  Var_01    C17  C18  C19  C4    -45.02  30.0  1
 HOF  Var_02    C18  C17  C16  C5      1.61  30.0  1
 HOF  Var_03    C19  C18  C17  C16    13.18  30.0  1
 HOF  Var_04    C9   C8   C7   O1   -130.09  30.0  2
 HOF  Var_05    O2   C12  C11  C10   179.93  30.0  3
 HOF  Var_06    O4   C6   N2   C5   -167.59  30.0  1
 HOF  Var_07    C8   C7   O1   C6     75.55  30.0  3
 HOF  Var_08    H4   C2   N1   C1   -174.81  30.0  3
 HOF  Var_09    H1   C1   N1   C2    155.13  30.0  3
 HOF  Var_10    H14  C13  O2   C12   179.49  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
 HOF  chir_01  C4  C5  C19  C3  positiv
 HOF  chir_02  C5  N2  C16  C4  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
 HOF  plan-1  C7   0.020
 HOF  plan-1  C8   0.020
 HOF  plan-1  C9   0.020
 HOF  plan-1  C10  0.020
 HOF  plan-1  C11  0.020
 HOF  plan-1  C12  0.020
 HOF  plan-1  C14  0.020
 HOF  plan-1  C15  0.020
 HOF  plan-1  H12  0.020
 HOF  plan-1  H13  0.020
 HOF  plan-1  H17  0.020
 HOF  plan-1  H18  0.020
 HOF  plan-2  C1   0.020
 HOF  plan-2  C2   0.020
 HOF  plan-2  C3   0.020
 HOF  plan-2  N1   0.020
 HOF  plan-2  C4   0.020
 HOF  plan-2  O5   0.020
 HOF  plan-3  C11  0.020
 HOF  plan-3  C12  0.020
 HOF  plan-3  O2   0.020
 HOF  plan-3  O3   0.020
 HOF  plan-4  N2   0.020
 HOF  plan-4  C6   0.020
 HOF  plan-4  O1   0.020
 HOF  plan-4  O4   0.020

