# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 18:56:59 2020
#   Inital geometry file: a 90 line input string
#   Ligand name: 3-fluoro-4-hydroxybenzaldehyde O-(cyclohexylcarbonyl)oxime
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(\C=N\OC(=O)C2CCCCC2)cc1F
#
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
 OX4  OX4  '3-fluoro-4-hydroxybenzaldehyde O-(cyclohexylcarbonyl)oxime'  ligand  35  19  .  2022-07-22  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_OX4
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
 OX4  O1    O  OH1   0  -0.615  -0.6228   7.4505   4.1065
 OX4  C1    C  CR6   0   0.235  -0.9330   6.4103   3.3239
 OX4  C2    C  CR6   0   0.457  -2.2285   6.1411   2.8917
 OX4  F2    F  F     0  -0.318  -3.2085   6.9767   3.2828
 OX4  C3    C  CR16  0  -0.447  -2.5272   5.0647   2.0910
 OX4  C4    C  CR6   0   0.030  -1.5080   4.2027   1.6876
 OX4  C5    C  CR16  0  -0.274  -0.2011   4.4590   2.1091
 OX4  C6    C  CR16  0  -0.325   0.0806   5.5450   2.9134
 OX4  C7    C  C1    0  -0.036  -1.8585   3.0682   0.8435
 OX4  N8    N  N     0  -0.113  -0.9722   2.2414   0.4651
 OX4  O9    O  O2    0  -0.386  -1.5414   1.2594  -0.3241
 OX4  C10   C  C     0   0.622  -0.6801   0.3104  -0.7480
 OX4  O10   O  O     0  -0.415   0.4912   0.3154  -0.4963
 OX4  C11   C  CH1   0  -0.408  -1.4236  -0.7341  -1.5386
 OX4  C12   C  CH2   0  -0.425  -2.2552  -1.6210  -0.5940
 OX4  C13   C  CH2   0  -0.435  -3.0247  -2.6726  -1.3859
 OX4  C14   C  CH2   0  -0.431  -2.0966  -3.5131  -2.2557
 OX4  C15   C  CH2   0  -0.438  -1.2576  -2.6302  -3.1738
 OX4  C16   C  CH2   0  -0.418  -0.4778  -1.5847  -2.3829
 OX4  HO1   H  HOH1  0   0.482  -1.4024   7.9756   4.3237
 OX4  H3    H  HCR6  0   0.290  -3.5526   4.8987   1.7837
 OX4  H5    H  HCR6  0   0.268   0.6043   3.8038   1.8059
 OX4  H6    H  HCR6  0   0.285   1.0956   5.7373   3.2364
 OX4  H7    H  H     0   0.269  -2.9050   2.9640   0.5580
 OX4  H11   H  HCH1  0   0.267  -2.1225  -0.2149  -2.2055
 OX4  H121  H  HCH2  0   0.247  -2.9480  -1.0127  -0.0098
 OX4  H122  H  HCH2  0   0.227  -1.5841  -2.1146   0.1171
 OX4  H131  H  HCH2  0   0.216  -3.7654  -2.1738  -2.0202
 OX4  H132  H  HCH2  0   0.236  -3.5835  -3.3106  -0.6976
 OX4  H141  H  HCH2  0   0.212  -1.4321  -4.1005  -1.6133
 OX4  H142  H  HCH2  0   0.231  -2.6754  -4.2294  -2.8435
 OX4  H151  H  HCH2  0   0.234  -0.5654  -3.2403  -3.7580
 OX4  H152  H  HCH2  0   0.214  -1.9128  -2.1281  -3.8940
 OX4  H161  H  HCH2  0   0.222   0.2441  -2.0859  -1.7312
 OX4  H162  H  HCH2  0   0.240   0.0960  -0.9500  -3.0617

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
 OX4  O1   C1    single    1.338  0.020  1.338
 OX4  O1   HO1   single    0.850  0.020  0.980
 OX4  C1   C6    aromatic  1.395  0.020  1.395
 OX4  C1   C2    aromatic  1.392  0.020  1.392
 OX4  C2   C3    aromatic  1.374  0.020  1.374
 OX4  C2   F2    single    1.346  0.020  1.346
 OX4  C3   C4    aromatic  1.395  0.020  1.395
 OX4  C3   H3    single    0.930  0.020  1.080
 OX4  C4   C7    single    1.457  0.020  1.457
 OX4  C4   C5    aromatic  1.397  0.020  1.397
 OX4  C5   C6    aromatic  1.380  0.020  1.380
 OX4  C5   H5    single    0.930  0.020  1.080
 OX4  C6   H6    single    0.930  0.020  1.080
 OX4  C7   N8    double    1.270  0.020  1.270
 OX4  C7   H7    single    0.930  0.020  1.080
 OX4  N8   O9    single    1.382  0.020  1.382
 OX4  O9   C10   single    1.350  0.020  1.350
 OX4  C10  O10   double    1.198  0.020  1.198
 OX4  C10  C11   single    1.506  0.020  1.506
 OX4  C11  C12   single    1.540  0.020  1.540
 OX4  C11  C16   single    1.527  0.020  1.527
 OX4  C11  H11   single    0.970  0.020  1.090
 OX4  C12  C13   single    1.525  0.020  1.525
 OX4  C12  H121  single    0.970  0.020  1.090
 OX4  C12  H122  single    0.970  0.020  1.090
 OX4  C13  C14   single    1.525  0.020  1.525
 OX4  C13  H131  single    0.970  0.020  1.090
 OX4  C13  H132  single    0.970  0.020  1.090
 OX4  C14  C15   single    1.525  0.020  1.525
 OX4  C14  H141  single    0.970  0.020  1.090
 OX4  C14  H142  single    0.970  0.020  1.090
 OX4  C15  C16   single    1.525  0.020  1.525
 OX4  C15  H151  single    0.970  0.020  1.090
 OX4  C15  H152  single    0.970  0.020  1.090
 OX4  C16  H161  single    0.970  0.020  1.090
 OX4  C16  H162  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
 OX4  HO1   O1   C1    111.56  3.000
 OX4  C6    C1   C2    117.71  3.000
 OX4  C2    C1   O1    123.21  3.000
 OX4  C6    C1   O1    119.08  3.000
 OX4  C3    C2   F2    119.82  3.000
 OX4  F2    C2   C1    117.86  3.000
 OX4  C3    C2   C1    122.32  3.000
 OX4  H3    C3   C4    121.00  3.000
 OX4  H3    C3   C2    119.41  3.000
 OX4  C4    C3   C2    119.59  3.000
 OX4  C7    C4   C5    122.88  3.000
 OX4  C5    C4   C3    118.89  3.000
 OX4  C7    C4   C3    118.24  3.000
 OX4  H5    C5   C6    119.20  3.000
 OX4  H5    C5   C4    120.06  3.000
 OX4  C6    C5   C4    120.73  3.000
 OX4  H6    C6   C5    120.33  3.000
 OX4  H6    C6   C1    118.91  3.000
 OX4  C5    C6   C1    120.76  3.000
 OX4  H7    C7   N8    122.00  3.000
 OX4  H7    C7   C4    117.22  3.000
 OX4  N8    C7   C4    120.78  3.000
 OX4  O9    N8   C7    110.20  3.000
 OX4  C10   O9   N8    114.58  3.000
 OX4  C11   C10  O10   126.57  3.000
 OX4  C11   C10  O9    109.72  3.000
 OX4  O10   C10  O9    123.70  3.000
 OX4  H11   C11  C16   108.80  3.000
 OX4  H11   C11  C12   107.55  3.000
 OX4  C16   C11  C12   110.67  3.000
 OX4  H11   C11  C10   107.79  3.000
 OX4  C16   C11  C10   111.76  3.000
 OX4  C12   C11  C10   110.12  3.000
 OX4  H122  C12  H121  107.02  3.000
 OX4  H122  C12  C13   109.61  3.000
 OX4  H121  C12  C13   110.00  3.000
 OX4  H122  C12  C11   109.09  3.000
 OX4  H121  C12  C11   110.49  3.000
 OX4  C13   C12  C11   110.56  3.000
 OX4  H132  C13  H131  106.56  3.000
 OX4  H132  C13  C14   110.42  3.000
 OX4  H131  C13  C14   109.41  3.000
 OX4  H132  C13  C12   109.50  3.000
 OX4  H131  C13  C12   109.14  3.000
 OX4  C14   C13  C12   111.67  3.000
 OX4  H142  C14  H141  106.59  3.000
 OX4  H142  C14  C15   110.31  3.000
 OX4  H141  C14  C15   109.26  3.000
 OX4  H142  C14  C13   110.23  3.000
 OX4  H141  C14  C13   109.29  3.000
 OX4  C15   C14  C13   111.05  3.000
 OX4  H152  C15  H151  106.46  3.000
 OX4  H152  C15  C16   109.42  3.000
 OX4  H151  C15  C16   109.65  3.000
 OX4  H152  C15  C14   109.39  3.000
 OX4  H151  C15  C14   110.32  3.000
 OX4  C16   C15  C14   111.46  3.000
 OX4  H162  C16  H161  106.85  3.000
 OX4  H162  C16  C15   110.16  3.000
 OX4  H161  C16  C15   109.40  3.000
 OX4  H162  C16  C11   110.20  3.000
 OX4  H161  C16  C11   109.55  3.000
 OX4  C15   C16  C11   110.60  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
 OX4  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 OX4  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 OX4  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 OX4  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 OX4  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 OX4  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 OX4  CONST_07  C5   C6   C1   O1    180.00   0.0  0
 OX4  CONST_08  C3   C2   C1   O1    180.00   0.0  0
 OX4  CONST_09  C7   C4   C3   C2    180.00   0.0  0
 OX4  CONST_10  C6   C1   C2   F2    180.00   0.0  0
 OX4  CONST_11  C4   C3   C2   F2    180.00   0.0  0
 OX4  CONST_12  C7   C4   C5   C6    180.00   0.0  0
 OX4  CONST_13  H5   C5   C6   C1    180.00   0.0  0
 OX4  CONST_14  H3   C3   C2   C1    180.00   0.0  0
 OX4  CONST_15  H6   C6   C1   C2    180.00   0.0  0
 OX4  Var_01    C14  C13  C12  C11    55.65  30.0  1
 OX4  Var_02    C14  C15  C16  C11   -56.58  30.0  1
 OX4  Var_03    C15  C14  C13  C12   -55.05  30.0  1
 OX4  Var_04    C16  C15  C14  C13    55.35  30.0  1
 OX4  Var_05    N8   C7   C4   C3   -178.91  30.0  2
 OX4  Var_06    C11  C10  O9   N8    177.30  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
 OX4  chir_01  C11  C10  C12  C16  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
 OX4  plan-1  O1   0.020
 OX4  plan-1  C1   0.020
 OX4  plan-1  C2   0.020
 OX4  plan-1  F2   0.020
 OX4  plan-1  C3   0.020
 OX4  plan-1  C4   0.020
 OX4  plan-1  C5   0.020
 OX4  plan-1  C6   0.020
 OX4  plan-1  C7   0.020
 OX4  plan-1  H3   0.020
 OX4  plan-1  H5   0.020
 OX4  plan-1  H6   0.020
 OX4  plan-2  C4   0.020
 OX4  plan-2  C7   0.020
 OX4  plan-2  N8   0.020
 OX4  plan-2  O9   0.020
 OX4  plan-2  H7   0.020
 OX4  plan-3  O9   0.020
 OX4  plan-3  C10  0.020
 OX4  plan-3  O10  0.020
 OX4  plan-3  C11  0.020

