# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 04:54:05 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: (9Z,11S)-11-hydroxy-11-[(2R,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC[C@H]1O[C@@H]1[C@@H](O)\C=C/CCCCCCCC(O)=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
 11O  11O  '(9Z,11S)-11-hydroxy-11-[(2R,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid'  ligand  54  22  .  2022-09-22  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_11O
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
 11O  C1    C  C     0   0.549   0.8322  -0.0857   -9.2292
 11O  C2    C  CH2   0  -0.580   1.1223   0.3089   -7.8085
 11O  C3    C  CH2   0  -0.418  -0.0305   0.0669   -6.8482
 11O  C4    C  CH2   0  -0.414   0.3206   0.5007   -5.4306
 11O  C5    C  CH2   0  -0.413  -0.8059   0.2574   -4.4346
 11O  C6    C  CH2   0  -0.414  -0.4574   0.7118   -3.0230
 11O  C7    C  CH2   0  -0.417  -1.5600   0.4313   -2.0103
 11O  C8    C  CH2   0  -0.494  -1.2086   0.9294   -0.6079
 11O  C9    C  C1    0  -0.199  -2.2911   0.6336    0.3812
 11O  C10   C  C1    0  -0.259  -2.1864  -0.0076    1.5434
 11O  C11   C  CH1   0  -0.051  -0.9317  -0.5729    2.1490
 11O  C12   C  CH1   0  -0.052  -0.6062   0.1572    3.4366
 11O  C13   C  CH1   0   0.007   0.1077  -0.4626    4.5440
 11O  C14   C  CH2   0  -0.458   0.9341   0.3354    5.5101
 11O  C15   C  CH2   0  -0.422   1.0016  -0.3045    6.8926
 11O  C16   C  CH2   0  -0.409   1.8635   0.4865    7.8675
 11O  C17   C  CH2   0  -0.419   2.0107  -0.1885    9.2253
 11O  C18   C  CH3   0  -0.663   2.8637   0.6171   10.1950
 11O  O19   O  O     0  -0.446  -0.2001  -0.5680   -9.6244
 11O  O20   O  OH1   0  -0.599   1.8661   0.1610  -10.0304
 11O  O21   O  OH1   0  -0.662  -1.0363  -1.9665    2.3388
 11O  O22   O  O2    0  -0.497  -1.3092  -0.2733    4.5929
 11O  H21   H  HCH2  0   0.275   1.4112   1.3647   -7.8021
 11O  H22   H  HCH2  0   0.275   2.0139  -0.2358   -7.4807
 11O  H31   H  HCH2  0   0.225  -0.2988  -0.9927   -6.8494
 11O  H32   H  HCH2  0   0.225  -0.9167   0.6111   -7.1861
 11O  H41   H  HCH2  0   0.213   0.5824   1.5642   -5.4296
 11O  H42   H  HCH2  0   0.213   1.2180  -0.0321   -5.0971
 11O  H51   H  HCH2  0   0.210  -1.0557  -0.8090   -4.4235
 11O  H52   H  HCH2  0   0.210  -1.7098   0.7767   -4.7716
 11O  H61   H  HCH2  0   0.211  -0.2356   1.7845   -3.0311
 11O  H62   H  HCH2  0   0.211   0.4635   0.2149   -2.6983
 11O  H71   H  HCH2  0   0.219  -1.7570  -0.6447   -1.9740
 11O  H72   H  HCH2  0   0.216  -2.4921   0.9017   -2.3411
 11O  H81   H  HCH2  0   0.236  -1.0512   2.0130   -0.6496
 11O  H82   H  HCH2  0   0.234  -0.2556   0.4970   -0.2962
 11O  H91   H  H     0   0.238  -3.2799   0.9816    0.0921
 11O  H101  H  H     0   0.247  -3.0884  -0.1402    2.1371
 11O  H111  H  HCH1  0   0.258  -0.0853  -0.4215    1.4749
 11O  H121  H  HCH1  0   0.254  -0.5300   1.2391    3.3191
 11O  H131  H  HCH1  0   0.243   0.4093  -1.5038    4.4347
 11O  H141  H  HCH2  0   0.231   0.5417   1.3544    5.5833
 11O  H142  H  HCH2  0   0.231   1.9453   0.4213    5.0998
 11O  H151  H  HCH2  0   0.215   1.3989  -1.3208    6.7982
 11O  H152  H  HCH2  0   0.219  -0.0090  -0.4083    7.3000
 11O  H161  H  HCH2  0   0.210   1.4366   1.4864    8.0027
 11O  H162  H  HCH2  0   0.209   2.8573   0.6404    7.4319
 11O  H171  H  HCH2  0   0.211   2.4502  -1.1813    9.0866
 11O  H172  H  HCH2  0   0.211   1.0199  -0.3554    9.6594
 11O  H181  H  HCH3  0   0.226   2.9781   0.1049   11.1510
 11O  H182  H  HCH3  0   0.216   3.8634   0.7891    9.7912
 11O  H183  H  HCH3  0   0.216   2.4184   1.5934   10.3949
 11O  H2O1  H  HOH1  0   0.477   1.6495  -0.1001  -10.9376
 11O  H211  H  HOH1  0   0.444  -1.7381  -2.1336    2.9784

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
 11O  C1   C2    single  1.503  0.020  1.503
 11O  C1   O19   double  1.206  0.020  1.206
 11O  C1   O20   single  1.331  0.020  1.331
 11O  C2   C3    single  1.520  0.020  1.520
 11O  C2   H21   single  0.970  0.020  1.090
 11O  C2   H22   single  0.970  0.020  1.090
 11O  C3   C4    single  1.524  0.020  1.524
 11O  C3   H31   single  0.970  0.020  1.090
 11O  C3   H32   single  0.970  0.020  1.090
 11O  C4   C5    single  1.523  0.020  1.523
 11O  C4   H41   single  0.970  0.020  1.090
 11O  C4   H42   single  0.970  0.020  1.090
 11O  C5   C6    single  1.523  0.020  1.523
 11O  C5   H51   single  0.970  0.020  1.090
 11O  C5   H52   single  0.970  0.020  1.090
 11O  C6   C7    single  1.523  0.020  1.523
 11O  C6   H61   single  0.970  0.020  1.090
 11O  C6   H62   single  0.970  0.020  1.090
 11O  C7   C8    single  1.529  0.020  1.529
 11O  C7   H71   single  0.970  0.020  1.090
 11O  C7   H72   single  0.970  0.020  1.090
 11O  C8   C9    single  1.496  0.020  1.496
 11O  C8   H81   single  0.970  0.020  1.090
 11O  C8   H82   single  0.970  0.020  1.090
 11O  C9   C10   double  1.332  0.020  1.332
 11O  C9   H91   single  0.930  0.020  1.080
 11O  C10  C11   single  1.504  0.020  1.504
 11O  C10  H101  single  0.930  0.020  1.080
 11O  C11  C12   single  1.516  0.020  1.516
 11O  C11  O21   single  1.410  0.020  1.410
 11O  C11  H111  single  0.970  0.020  1.090
 11O  C12  C13   single  1.456  0.020  1.456
 11O  C12  O22   single  1.420  0.020  1.420
 11O  C12  H121  single  0.970  0.020  1.090
 11O  C13  C14   single  1.501  0.020  1.501
 11O  C13  O22   single  1.430  0.020  1.430
 11O  C13  H131  single  0.970  0.020  1.090
 11O  C14  C15   single  1.525  0.020  1.525
 11O  C14  H141  single  0.970  0.020  1.090
 11O  C14  H142  single  0.970  0.020  1.090
 11O  C15  C16   single  1.523  0.020  1.523
 11O  C15  H151  single  0.970  0.020  1.090
 11O  C15  H152  single  0.970  0.020  1.090
 11O  C16  C17   single  1.524  0.020  1.524
 11O  C16  H161  single  0.970  0.020  1.090
 11O  C16  H162  single  0.970  0.020  1.090
 11O  C17  C18   single  1.522  0.020  1.522
 11O  C17  H171  single  0.970  0.020  1.090
 11O  C17  H172  single  0.970  0.020  1.090
 11O  C18  H181  single  0.970  0.020  1.090
 11O  C18  H182  single  0.970  0.020  1.090
 11O  C18  H183  single  0.970  0.020  1.090
 11O  O20  H2O1  single  0.850  0.020  0.980
 11O  O21  H211  single  0.850  0.020  0.980

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
 11O  O20   C1   O19   122.80  3.000
 11O  O20   C1   C2    111.74  3.000
 11O  O19   C1   C2    125.45  3.000
 11O  H22   C2   H21   105.25  3.000
 11O  H22   C2   C3    110.45  3.000
 11O  H21   C2   C3    110.50  3.000
 11O  H22   C2   C1    108.04  3.000
 11O  H21   C2   C1    108.04  3.000
 11O  C3    C2   C1    114.15  3.000
 11O  H32   C3   H31   106.46  3.000
 11O  H32   C3   C4    109.43  3.000
 11O  H31   C3   C4    109.48  3.000
 11O  H32   C3   C2    109.89  3.000
 11O  H31   C3   C2    109.87  3.000
 11O  C4    C3   C2    111.58  3.000
 11O  H42   C4   H41   106.02  3.000
 11O  H42   C4   C5    109.21  3.000
 11O  H41   C4   C5    109.35  3.000
 11O  H42   C4   C3    109.49  3.000
 11O  H41   C4   C3    109.41  3.000
 11O  C5    C4   C3    113.11  3.000
 11O  H52   C5   H51   106.06  3.000
 11O  H52   C5   C6    109.41  3.000
 11O  H51   C5   C6    109.46  3.000
 11O  H52   C5   C4    109.47  3.000
 11O  H51   C5   C4    109.32  3.000
 11O  C6    C5   C4    112.89  3.000
 11O  H62   C6   H61   106.04  3.000
 11O  H62   C6   C7    109.14  3.000
 11O  H61   C6   C7    109.38  3.000
 11O  H62   C6   C5    109.37  3.000
 11O  H61   C6   C5    109.36  3.000
 11O  C7    C6   C5    113.30  3.000
 11O  H72   C7   H71   106.21  3.000
 11O  H72   C7   C8    109.43  3.000
 11O  H71   C7   C8    109.34  3.000
 11O  H72   C7   C6    109.65  3.000
 11O  H71   C7   C6    109.48  3.000
 11O  C8    C7   C6    112.54  3.000
 11O  H82   C8   H81   106.08  3.000
 11O  H82   C8   C9    111.38  3.000
 11O  H81   C8   C9    108.95  3.000
 11O  H82   C8   C7    109.47  3.000
 11O  H81   C8   C7    108.68  3.000
 11O  C9    C8   C7    112.07  3.000
 11O  H91   C9   C10   117.23  3.000
 11O  H91   C9   C8    114.77  3.000
 11O  C10   C9   C8    127.99  3.000
 11O  H101  C10  C11   115.23  3.000
 11O  H101  C10  C9    118.02  3.000
 11O  C11   C10  C9    126.74  3.000
 11O  H111  C11  O21   106.11  3.000
 11O  H111  C11  C12   106.92  3.000
 11O  O21   C11  C12   112.19  3.000
 11O  H111  C11  C10   110.23  3.000
 11O  O21   C11  C10   111.33  3.000
 11O  C12   C11  C10   109.89  3.000
 11O  H121  C12  O22   115.02  3.000
 11O  H121  C12  C13   118.02  3.000
 11O  O22   C12  C13    59.63  3.000
 11O  H121  C12  C11   113.66  3.000
 11O  O22   C12  C11   116.06  3.000
 11O  C13   C12  C11   123.12  3.000
 11O  H131  C13  O22   113.84  3.000
 11O  H131  C13  C14   114.85  3.000
 11O  O22   C13  C14   116.94  3.000
 11O  H131  C13  C12   117.79  3.000
 11O  O22   C13  C12    58.93  3.000
 11O  C14   C13  C12   122.21  3.000
 11O  H142  C14  H141  106.45  3.000
 11O  H142  C14  C15   109.38  3.000
 11O  H141  C14  C15   110.24  3.000
 11O  H142  C14  C13   108.01  3.000
 11O  H141  C14  C13   109.92  3.000
 11O  C15   C14  C13   112.63  3.000
 11O  H152  C15  H151  106.20  3.000
 11O  H152  C15  C16   109.48  3.000
 11O  H151  C15  C16   109.38  3.000
 11O  H152  C15  C14   109.66  3.000
 11O  H151  C15  C14   109.11  3.000
 11O  C16   C15  C14   112.80  3.000
 11O  H162  C16  H161  105.92  3.000
 11O  H162  C16  C17   109.20  3.000
 11O  H161  C16  C17   109.39  3.000
 11O  H162  C16  C15   109.37  3.000
 11O  H161  C16  C15   109.42  3.000
 11O  C17   C16  C15   113.27  3.000
 11O  H172  C17  H171  105.99  3.000
 11O  H172  C17  C18   109.60  3.000
 11O  H171  C17  C18   109.62  3.000
 11O  H172  C17  C16   109.48  3.000
 11O  H171  C17  C16   109.13  3.000
 11O  C18   C17  C16   112.79  3.000
 11O  H183  C18  H182  107.48  3.000
 11O  H183  C18  H181  107.60  3.000
 11O  H182  C18  H181  107.59  3.000
 11O  H183  C18  C17   111.19  3.000
 11O  H182  C18  C17   111.16  3.000
 11O  H181  C18  C17   111.63  3.000
 11O  H2O1  O20  C1    109.89  3.000
 11O  H211  O21  C11   108.33  3.000
 11O  C13   O22  C12    61.44  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
 11O  CONST_01  H2O1  O20  C1   C2    180.00   0.0  0
 11O  Var_01    O22   C13  C12  C11  -103.05  30.0  1
 11O  Var_02    C14   C13  O22  C12   113.07  30.0  1
 11O  Var_03    C15   C14  C13  C12   151.27  30.0  3
 11O  Var_04    C16   C15  C14  C13   178.77  30.0  3
 11O  Var_05    C11   C10  C9   C8      1.02   0.0  2
 11O  Var_06    C4    C3   C2   C1   -179.38  30.0  3
 11O  Var_07    C5    C4   C3   C2   -179.29  30.0  3
 11O  Var_08    O19   C1   C2   C3     -0.74  30.0  2
 11O  Var_09    C6    C5   C4   C3   -179.15  30.0  3
 11O  Var_10    C7    C6   C5   C4   -178.12  30.0  3
 11O  Var_11    C8    C7   C6   C5   -178.38  30.0  3
 11O  Var_12    C9    C8   C7   C6   -179.30  30.0  3
 11O  Var_13    C10   C9   C8   C7    126.11  30.0  3
 11O  Var_14    C17   C16  C15  C14  -176.34  30.0  3
 11O  Var_15    C18   C17  C16  C15  -179.49  30.0  3
 11O  Var_16    H181  C18  C17  C16  -178.51  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
 11O  chir_01  C11  C10  C12  O21  negativ
 11O  chir_02  C12  C11  C13  O22  both
 11O  chir_03  C13  O22  C12  C14  both

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
 11O  plan-1  C1    0.020
 11O  plan-1  C2    0.020
 11O  plan-1  O19   0.020
 11O  plan-1  O20   0.020
 11O  plan-1  H2O1  0.020
 11O  plan-2  C8    0.020
 11O  plan-2  C9    0.020
 11O  plan-2  C10   0.020
 11O  plan-2  C11   0.020
 11O  plan-2  H91   0.020
 11O  plan-2  H101  0.020

