# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 01:02:04 2021
#   Inital geometry file: a 80 line input string
#   Ligand name: 2-{4-[(1S)-2,2-dichlorocyclopropyl]phenoxy}-2-methylpropanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(Oc1ccc(cc1)[C@@H]2CC2(Cl)Cl)C(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
 C5F  C5F  '2-{4-[(1S)-2,2-dichlorocyclopropyl]phenoxy}-2-methylpropanoic acid'  ligand  32  18  .  2022-09-16  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C5F
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
 C5F  C06  C   CH1   0  -0.280  -15.7643   8.6965  33.0403
 C5F  C07  C   CT    0  -0.102  -15.8809   9.7260  34.1201
 C5F  C08  C   CH2   0  -0.450  -16.7588   9.8252  32.9307
 C5F  C09  C   CR6   0   0.110  -14.5454   8.6114  32.1955
 C5F  C10  C   CR16  0  -0.298  -14.4300   9.2591  30.9703
 C5F  C11  C   CR16  0  -0.277  -13.4708   7.8446  32.6293
 C5F  C12  C   CR16  0  -0.335  -13.2811   9.1441  30.2074
 C5F  C13  C   CR16  0  -0.353  -12.3106   7.7202  31.8790
 C5F  C14  C   CR6   0   0.385  -12.2065   8.3761  30.6537
 C5F  C15  C   CT    0   0.068  -10.0329   7.4812  30.0144
 C5F  C16  C   CH3   0  -0.666  -10.4336   6.0160  29.8951
 C5F  C17  C   CH3   0  -0.665   -9.0597   7.8388  28.8876
 C5F  C18  C   C     0   0.532   -9.2988   7.7714  31.3260
 C5F  O03  O   O2    0  -0.487  -11.1334   8.3588  29.8314
 C5F  O04  O   OH1   0  -0.577   -9.3623   9.0466  31.6660
 C5F  O05  O   O     0  -0.427   -8.6800   6.9384  31.9379
 C5F  CL1  CL  CL    0  -0.064  -14.5906  10.8925  34.3160
 C5F  CL2  CL  CL    0  -0.071  -16.5830   9.2511  35.6579
 C5F  H16  H   HCH1  0   0.309  -16.1876   7.7352  33.3150
 C5F  H82  H   HCH2  0   0.291  -16.5605  10.6330  32.2377
 C5F  H81  H   HCH2  0   0.296  -17.8076   9.5907  33.0553
 C5F  H10  H   HCR6  0   0.253  -15.2475   9.8591  30.5913
 C5F  H11  H   HCR6  0   0.259  -13.5306   7.3231  33.5770
 C5F  H21  H   HCR6  0   0.265  -13.2096   9.6543  29.2550
 C5F  H31  H   HCR6  0   0.277  -11.5202   7.1012  32.2788
 C5F  H62  H   HCH3  0   0.253  -11.1182   5.6839  30.6730
 C5F  H61  H   HCH3  0   0.253  -10.9134   5.8550  28.9297
 C5F  H63  H   HCH3  0   0.253   -9.5510   5.3814  29.9354
 C5F  H72  H   HCH3  0   0.256   -8.7662   8.8876  28.9233
 C5F  H71  H   HCH3  0   0.248   -8.1609   7.2266  28.9531
 C5F  H73  H   HCH3  0   0.259   -9.5304   7.6424  27.9241
 C5F  H1   H   HOH1  0   0.487   -8.8486   9.2000  32.4737

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
 C5F  C17  C15  single    1.531  0.020  1.531
 C5F  C16  C15  single    1.524  0.020  1.524
 C5F  C15  O03  single    1.419  0.020  1.419
 C5F  C15  C18  single    1.531  0.020  1.531
 C5F  O03  C14  single    1.352  0.020  1.352
 C5F  C12  C14  aromatic  1.394  0.020  1.394
 C5F  C12  C10  aromatic  1.384  0.020  1.384
 C5F  C14  C13  aromatic  1.394  0.020  1.394
 C5F  C10  C09  aromatic  1.391  0.020  1.391
 C5F  C18  O05  double    1.205  0.020  1.205
 C5F  C18  O04  single    1.321  0.020  1.321
 C5F  C13  C11  aromatic  1.387  0.020  1.387
 C5F  C09  C11  aromatic  1.390  0.020  1.390
 C5F  C09  C06  single    1.486  0.020  1.486
 C5F  C08  C06  single    1.508  0.020  1.508
 C5F  C08  C07  single    1.482  0.020  1.482
 C5F  C06  C07  single    1.496  0.020  1.496
 C5F  CL1  C07  single    1.750  0.020  1.750
 C5F  C07  CL2  single    1.756  0.020  1.756
 C5F  C06  H16  single    0.970  0.020  1.090
 C5F  C08  H82  single    0.970  0.020  1.090
 C5F  C08  H81  single    0.970  0.020  1.090
 C5F  C10  H10  single    0.930  0.020  1.080
 C5F  C11  H11  single    0.930  0.020  1.080
 C5F  C12  H21  single    0.930  0.020  1.080
 C5F  C13  H31  single    0.930  0.020  1.080
 C5F  C16  H62  single    0.970  0.020  1.090
 C5F  C16  H61  single    0.970  0.020  1.090
 C5F  C16  H63  single    0.970  0.020  1.090
 C5F  C17  H72  single    0.970  0.020  1.090
 C5F  C17  H71  single    0.970  0.020  1.090
 C5F  C17  H73  single    0.970  0.020  1.090
 C5F  O04  H1   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
 C5F  H16  C06  C09  114.40  3.000
 C5F  H16  C06  C08  115.08  3.000
 C5F  C09  C06  C08  122.86  3.000
 C5F  H16  C06  C07  113.34  3.000
 C5F  C08  C06  C07   59.09  3.000
 C5F  C09  C06  C07  120.91  3.000
 C5F  CL2  C07  CL1  112.15  3.000
 C5F  CL2  C07  C08  118.96  3.000
 C5F  CL1  C07  C08  118.81  3.000
 C5F  CL2  C07  C06  118.49  3.000
 C5F  CL1  C07  C06  118.80  3.000
 C5F  C08  C07  C06   60.85  3.000
 C5F  H81  C08  H82  114.39  3.000
 C5F  H81  C08  C07  117.87  3.000
 C5F  H82  C08  C07  117.08  3.000
 C5F  H81  C08  C06  117.94  3.000
 C5F  H82  C08  C06  118.96  3.000
 C5F  C07  C08  C06   60.06  3.000
 C5F  C11  C09  C10  117.90  3.000
 C5F  C11  C09  C06  119.25  3.000
 C5F  C10  C09  C06  122.85  3.000
 C5F  H10  C10  C12  118.68  3.000
 C5F  H10  C10  C09  120.26  3.000
 C5F  C12  C10  C09  121.06  3.000
 C5F  H11  C11  C13  118.44  3.000
 C5F  H11  C11  C09  119.74  3.000
 C5F  C13  C11  C09  121.83  3.000
 C5F  H21  C12  C14  119.36  3.000
 C5F  H21  C12  C10  120.04  3.000
 C5F  C14  C12  C10  120.61  3.000
 C5F  H31  C13  C14  122.70  3.000
 C5F  H31  C13  C11  117.58  3.000
 C5F  C14  C13  C11  119.72  3.000
 C5F  O03  C14  C13  126.01  3.000
 C5F  C13  C14  C12  118.89  3.000
 C5F  O03  C14  C12  115.09  3.000
 C5F  O03  C15  C18  111.41  3.000
 C5F  C18  C15  C17  106.34  3.000
 C5F  O03  C15  C17  104.69  3.000
 C5F  C18  C15  C16  112.06  3.000
 C5F  O03  C15  C16  112.37  3.000
 C5F  C17  C15  C16  109.52  3.000
 C5F  H63  C16  H61  107.68  3.000
 C5F  H63  C16  H62  107.81  3.000
 C5F  H61  C16  H62  108.13  3.000
 C5F  H63  C16  C15  110.16  3.000
 C5F  H61  C16  C15  109.10  3.000
 C5F  H62  C16  C15  113.77  3.000
 C5F  H73  C17  H71  107.95  3.000
 C5F  H73  C17  H72  108.58  3.000
 C5F  H71  C17  H72  108.47  3.000
 C5F  H73  C17  C15  109.50  3.000
 C5F  H71  C17  C15  110.42  3.000
 C5F  H72  C17  C15  111.83  3.000
 C5F  O05  C18  O04  124.15  3.000
 C5F  O04  C18  C15  112.36  3.000
 C5F  O05  C18  C15  123.40  3.000
 C5F  C15  O03  C14  123.02  3.000
 C5F  H1   O04  C18  109.97  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
 C5F  CONST_01  C14  C12  C10  C09     0.00   0.0  0
 C5F  CONST_02  C14  C13  C11  C09     0.00   0.0  0
 C5F  CONST_03  C13  C14  C12  C10     0.00   0.0  0
 C5F  CONST_04  C13  C11  C09  C10     0.00   0.0  0
 C5F  CONST_05  C12  C14  C13  C11     0.00   0.0  0
 C5F  CONST_06  C12  C10  C09  C11     0.00   0.0  0
 C5F  CONST_07  C12  C10  C09  C06   180.00   0.0  0
 C5F  CONST_08  C13  C11  C09  C06   180.00   0.0  0
 C5F  CONST_09  O03  C14  C12  C10   180.00   0.0  0
 C5F  CONST_10  O03  C14  C13  C11   180.00   0.0  0
 C5F  CONST_11  H10  C10  C09  C06     0.00   0.0  0
 C5F  CONST_12  H11  C11  C09  C06     0.00   0.0  0
 C5F  CONST_13  H21  C12  C10  C09   180.00   0.0  0
 C5F  CONST_14  H31  C13  C11  C09   180.00   0.0  0
 C5F  CONST_15  H1   O04  C18  C15   180.00   0.0  0
 C5F  Var_01    C09  C06  C08  C07  -109.03  30.0  1
 C5F  Var_02    C10  C09  C06  C07   -93.43  30.0  2
 C5F  Var_03    CL1  C07  C08  C06   108.84  30.0  1
 C5F  Var_04    C17  C15  O03  C14  -178.57  30.0  3
 C5F  Var_05    O05  C18  C15  C16    25.78  30.0  3
 C5F  Var_06    H72  C17  C15  C16   178.64  30.0  3
 C5F  Var_07    H62  C16  C15  C17   179.30  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
 C5F  chir_01  C06  C09  C08  C07  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
 C5F  plan-1  C06  0.020
 C5F  plan-1  C09  0.020
 C5F  plan-1  C10  0.020
 C5F  plan-1  C11  0.020
 C5F  plan-1  C12  0.020
 C5F  plan-1  C13  0.020
 C5F  plan-1  C14  0.020
 C5F  plan-1  O03  0.020
 C5F  plan-1  H10  0.020
 C5F  plan-1  H11  0.020
 C5F  plan-1  H21  0.020
 C5F  plan-1  H31  0.020
 C5F  plan-2  C15  0.020
 C5F  plan-2  C18  0.020
 C5F  plan-2  O04  0.020
 C5F  plan-2  O05  0.020
 C5F  plan-2  H1   0.020

