# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 18:46:06 2020
#   Inital geometry file: a 82 line input string
#   Ligand name: ethyl (1S,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropanecarboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)[C@H]1C[C@@H]1c2ccc(O)c(OC)c2
#
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
 EMF  EMF  'ethyl (1S,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropanecarboxylate'  ligand  33  17  .  2022-09-22  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_EMF
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
 EMF  O9    O  O     0  -0.466   3.3151   0.6843   1.6505
 EMF  C9    C  C     0   0.632   3.0232  -0.0475   0.7336
 EMF  O10   O  O2    0  -0.461   3.7552  -0.1848  -0.3621
 EMF  C11   C  CH2   0  -0.182   4.9519   0.6017  -0.4805
 EMF  C12   C  CH3   0  -0.689   5.5798   0.2849  -1.8160
 EMF  C8    C  CH1   0  -0.409   1.8080  -0.8878   0.6844
 EMF  C14   C  CH2   0  -0.453   1.2252  -1.3872   1.9750
 EMF  C7    C  CH1   0  -0.358   0.5247  -0.2963   1.2489
 EMF  C1    C  CR6   0   0.230  -0.7592  -0.5003   0.5323
 EMF  C2    C  CR16  0  -0.456  -1.5995   0.6003   0.3445
 EMF  C3    C  CR6   0   0.316  -2.8044   0.4736  -0.3282
 EMF  O3    O  O2    0  -0.489  -3.6788   1.4774  -0.5573
 EMF  C13   C  CH3   0  -0.433  -3.3430   2.7809  -0.1254
 EMF  C6    C  CR16  0  -0.370  -1.1546  -1.7316   0.0274
 EMF  C5    C  CR16  0  -0.325  -2.3600  -1.8650  -0.6517
 EMF  C4    C  CR6   0   0.262  -3.1935  -0.7757  -0.8357
 EMF  O4    O  OH1   0  -0.633  -4.3590  -0.9369  -1.4975
 EMF  H111  H  HCH2  0   0.235   4.7015   1.6621  -0.4100
 EMF  H112  H  HCH2  0   0.236   5.6330   0.3624   0.3386
 EMF  H121  H  HCH3  0   0.240   6.4822   0.8834  -1.9369
 EMF  H122  H  HCH3  0   0.236   5.8624  -0.7652  -1.8894
 EMF  H123  H  HCH3  0   0.236   4.9083   0.5251  -2.6405
 EMF  H8    H  HCH1  0   0.291   1.7009  -1.5228  -0.1868
 EMF  H141  H  HCH2  0   0.273   0.7943  -2.3802   1.9604
 EMF  H142  H  HCH2  0   0.274   1.7411  -1.1312   2.8911
 EMF  H7    H  HCH1  0   0.274   0.6388   0.6935   1.6772
 EMF  H2    H  HCR6  0   0.280  -1.2919   1.5630   0.7332
 EMF  H131  H  HCH3  0   0.263  -4.1612   3.4288  -0.4294
 EMF  H132  H  HCH3  0   0.231  -3.2366   2.8337   0.9611
 EMF  H133  H  HCH3  0   0.231  -2.4193   3.1355  -0.5895
 EMF  H6    H  HCR6  0   0.248  -0.5314  -2.6090   0.1502
 EMF  H5    H  HCR6  0   0.264  -2.6596  -2.8290  -1.0441
 EMF  HO4   H  HOH1  0   0.471  -4.8177  -0.0915  -1.5731

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
 EMF  C13  O3    single    1.414  0.020  1.414
 EMF  O3   C3    single    1.351  0.020  1.351
 EMF  C12  C11   single    1.509  0.020  1.509
 EMF  C3   C2    aromatic  1.386  0.020  1.386
 EMF  C3   C4    aromatic  1.404  0.020  1.404
 EMF  C2   C1    aromatic  1.397  0.020  1.397
 EMF  C11  O10   single    1.437  0.020  1.437
 EMF  O10  C9    single    1.325  0.020  1.325
 EMF  O4   C4    single    1.350  0.020  1.350
 EMF  C4   C5    aromatic  1.384  0.020  1.384
 EMF  C1   C7    single    1.485  0.020  1.485
 EMF  C1   C6    aromatic  1.388  0.020  1.388
 EMF  C7   C8    single    1.522  0.020  1.522
 EMF  C7   C14   single    1.486  0.020  1.486
 EMF  C9   C8    single    1.478  0.020  1.478
 EMF  C9   O9    double    1.209  0.020  1.209
 EMF  C8   C14   single    1.501  0.020  1.501
 EMF  C5   C6    aromatic  1.390  0.020  1.390
 EMF  C11  H111  single    0.970  0.020  1.090
 EMF  C11  H112  single    0.970  0.020  1.090
 EMF  C12  H121  single    0.970  0.020  1.090
 EMF  C12  H122  single    0.970  0.020  1.090
 EMF  C12  H123  single    0.970  0.020  1.090
 EMF  C8   H8    single    0.970  0.020  1.090
 EMF  C14  H141  single    0.970  0.020  1.090
 EMF  C14  H142  single    0.970  0.020  1.090
 EMF  C7   H7    single    0.970  0.020  1.090
 EMF  C2   H2    single    0.930  0.020  1.080
 EMF  C13  H131  single    0.970  0.020  1.090
 EMF  C13  H132  single    0.970  0.020  1.090
 EMF  C13  H133  single    0.970  0.020  1.090
 EMF  C6   H6    single    0.930  0.020  1.080
 EMF  C5   H5    single    0.930  0.020  1.080
 EMF  O4   HO4   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
 EMF  C8    C9   O10   111.58  3.000
 EMF  C8    C9   O9    124.60  3.000
 EMF  O10   C9   O9    123.82  3.000
 EMF  C11   O10  C9    118.14  3.000
 EMF  H112  C11  H111  107.91  3.000
 EMF  H112  C11  C12   110.99  3.000
 EMF  H111  C11  C12   110.88  3.000
 EMF  H112  C11  O10   109.74  3.000
 EMF  H111  C11  O10   109.59  3.000
 EMF  C12   C11  O10   107.73  3.000
 EMF  H123  C12  H122  108.73  3.000
 EMF  H123  C12  H121  107.77  3.000
 EMF  H122  C12  H121  107.88  3.000
 EMF  H123  C12  C11   111.51  3.000
 EMF  H122  C12  C11   111.70  3.000
 EMF  H121  C12  C11   109.11  3.000
 EMF  H8    C8   C7    116.29  3.000
 EMF  H8    C8   C14   117.26  3.000
 EMF  C7    C8   C14    58.88  3.000
 EMF  H8    C8   C9    116.17  3.000
 EMF  C14   C8   C9    118.65  3.000
 EMF  C7    C8   C9    117.39  3.000
 EMF  H142  C14  H141  114.72  3.000
 EMF  H142  C14  C7    117.69  3.000
 EMF  H141  C14  C7    118.63  3.000
 EMF  H142  C14  C8    117.64  3.000
 EMF  H141  C14  C8    116.61  3.000
 EMF  C7    C14  C8     61.24  3.000
 EMF  H7    C7   C1    114.02  3.000
 EMF  H7    C7   C14   115.31  3.000
 EMF  C1    C7   C14   122.87  3.000
 EMF  H7    C7   C8    114.37  3.000
 EMF  C14   C7   C8     59.89  3.000
 EMF  C1    C7   C8    119.80  3.000
 EMF  C6    C1   C2    118.58  3.000
 EMF  C6    C1   C7    122.94  3.000
 EMF  C2    C1   C7    118.47  3.000
 EMF  H2    C2   C3    120.17  3.000
 EMF  H2    C2   C1    118.76  3.000
 EMF  C3    C2   C1    121.07  3.000
 EMF  C4    C3   O3    114.87  3.000
 EMF  C4    C3   C2    119.87  3.000
 EMF  O3    C3   C2    125.26  3.000
 EMF  C13   O3   C3    118.66  3.000
 EMF  H133  C13  H132  108.92  3.000
 EMF  H133  C13  H131  108.90  3.000
 EMF  H132  C13  H131  108.81  3.000
 EMF  H133  C13  O3    111.73  3.000
 EMF  H132  C13  O3    111.80  3.000
 EMF  H131  C13  O3    106.58  3.000
 EMF  H6    C6   C5    118.47  3.000
 EMF  H6    C6   C1    120.88  3.000
 EMF  C5    C6   C1    120.65  3.000
 EMF  H5    C5   C4    119.06  3.000
 EMF  H5    C5   C6    120.16  3.000
 EMF  C4    C5   C6    120.78  3.000
 EMF  O4    C4   C5    119.42  3.000
 EMF  C5    C4   C3    119.05  3.000
 EMF  O4    C4   C3    121.53  3.000
 EMF  HO4   O4   C4    110.14  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
 EMF  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 EMF  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 EMF  CONST_03  C5    C4   C3   C2      0.00   0.0  0
 EMF  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 EMF  CONST_05  C6    C1   C2   C3      0.00   0.0  0
 EMF  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 EMF  CONST_07  C3    C2   C1   C7    180.00   0.0  0
 EMF  CONST_08  C5    C6   C1   C7    180.00   0.0  0
 EMF  CONST_09  O3    C3   C2   C1    180.00   0.0  0
 EMF  CONST_10  O4    C4   C3   C2    180.00   0.0  0
 EMF  CONST_11  C5    C4   C3   O3    180.00   0.0  0
 EMF  CONST_12  O4    C4   C5   C6    180.00   0.0  0
 EMF  CONST_13  H2    C2   C1   C7      0.00   0.0  0
 EMF  CONST_14  H6    C6   C1   C7      0.00   0.0  0
 EMF  CONST_15  H5    C5   C6   C1    180.00   0.0  0
 EMF  Var_01    C2    C1   C7   C8   -133.65  30.0  2
 EMF  Var_02    C1    C7   C14  C8    108.01  30.0  1
 EMF  Var_03    C7    C8   C9   O9     38.21  30.0  3
 EMF  Var_04    C4    C3   O3   C13  -177.61  30.0  2
 EMF  Var_05    C8    C9   O10  C11   178.15  30.0  3
 EMF  Var_06    H131  C13  O3   C3    178.53  30.0  3
 EMF  Var_07    C12   C11  O10  C9   -178.84  30.0  1
 EMF  Var_08    H121  C12  C11  O10   179.04  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
 EMF  chir_01  C8  C7  C9  C14  both
 EMF  chir_02  C7  C1  C8  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
 EMF  plan-1  C7   0.020
 EMF  plan-1  C1   0.020
 EMF  plan-1  C2   0.020
 EMF  plan-1  C3   0.020
 EMF  plan-1  O3   0.020
 EMF  plan-1  C6   0.020
 EMF  plan-1  C5   0.020
 EMF  plan-1  C4   0.020
 EMF  plan-1  O4   0.020
 EMF  plan-1  H2   0.020
 EMF  plan-1  H6   0.020
 EMF  plan-1  H5   0.020
 EMF  plan-2  O9   0.020
 EMF  plan-2  C9   0.020
 EMF  plan-2  O10  0.020
 EMF  plan-2  C8   0.020

