# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 17:44:46 2022
#   Inital geometry file: a 119 line input string
#   Ligand name: 2-[[(2~{R})-2-butyl-6,7-bis(chloranyl)-2-cyclopentyl-1-oxidanylidene-3~{H}-inden-5-yl]oxy]ethanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC[C@@]1(Cc2cc(OCC(O)=O)c(Cl)c(Cl)c2C1=O)C3CCCC3
#
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
 EZC  EZC  '2-[[(2~{R})-2-butyl-6,7-bis(chloranyl)-2-cyclopentyl-1-oxidanylidene-3~{H}-inden-5-yl]oxy]ethanoic acid'  ligand  49  26  .  2022-03-18  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_EZC
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
 EZC  C10  C   CH2    0  -0.440  162.9480  170.3235  197.9107
 EZC  C13  C   CH2    0  -0.447  160.5055  170.0455  197.7378
 EZC  C15  C   CR5    0   0.416  164.2656  172.7190  199.2113
 EZC  C17  C   CR56   0   0.038  164.0919  173.3168  200.5413
 EZC  C21  C   CR6    0  -0.043  164.9211  173.2938  201.6625
 EZC  C22  C   CR6    0   0.486  163.3154  174.6882  202.8397
 EZC  C24  C   CH3    0  -0.660  165.1203  176.3643  195.3212
 EZC  C26  C   C      0   0.387  161.7928  176.7396  205.4935
 EZC  C07  C   CR5    0  -0.222  162.9604  172.9127  198.4321
 EZC  C08  C   CH1    0  -0.211  162.2104  171.5535  198.4638
 EZC  C09  C   CH2    0  -0.432  160.8833  171.5223  197.6990
 EZC  C11  C   CH2    0  -0.509  162.1700  173.9345  199.2768
 EZC  C12  C   CH2    0  -0.427  163.2380  173.4045  197.0077
 EZC  C14  C   CH2    0  -0.441  161.8421  169.3017  197.5634
 EZC  C16  C   CR56   0   0.122  162.8944  174.0150  200.5840
 EZC  C18  C   CH2    0  -0.421  164.0988  174.6605  196.8984
 EZC  C19  C   CR16   0  -0.463  162.4906  174.6993  201.7168
 EZC  C23  C   CR6    0  -0.154  164.5346  173.9700  202.8019
 EZC  C25  C   CH2    0  -0.342  161.8515  176.0570  204.1126
 EZC  O05  O   O      0  -0.608  160.7435  177.3845  205.6713
 EZC  O06  O   OC    -1  -0.583  162.7539  176.5953  206.2607
 EZC  CL1  CL  CL     0  -0.085  166.3999  172.4234  201.6429
 EZC  CL2  CL  CL     0  -0.075  165.5175  173.9652  204.2118
 EZC  H1   H   HCH2   0   0.233  163.6671  169.9183  198.6217
 EZC  H2   H   HCH2   0   0.226  163.5079  170.5888  197.0121
 EZC  H3   H   HCH2   0   0.229  159.7714  169.7779  196.9769
 EZC  H4   H   HCH2   0   0.221  160.0615  169.8068  198.7073
 EZC  H5   H   HCH2   0   0.211  163.3133  175.2450  194.9830
 EZC  H6   H   HCH2   0   0.212  164.7717  174.2847  194.8919
 EZC  H7   H   HCH3   0   0.225  165.2512  176.6531  194.2778
 EZC  H8   H   HCH3   0   0.216  164.6447  177.1996  195.8382
 EZC  H9   H   HCH3   0   0.216  166.1139  176.2330  195.7540
 EZC  H10  H   HCH1   0   0.236  161.9742  171.3525  199.5181
 EZC  H11  H   HCH2   0   0.224  161.0325  171.8392  196.6631
 EZC  H12  H   HCH2   0   0.234  160.1171  172.1685  198.1305
 EZC  H13  H   HCH2   0   0.278  162.1503  174.9209  198.8067
 EZC  H14  H   HCH2   0   0.275  161.1276  173.6473  199.4237
 EZC  H15  H   HCH2   0   0.234  162.2796  173.6035  196.5205
 EZC  H16  H   HCH2   0   0.232  163.7093  172.6046  196.4313
 EZC  H17  H   HCH2   0   0.226  161.8913  168.4205  198.2039
 EZC  H18  H   HCH2   0   0.225  161.9587  168.9461  196.5388
 EZC  H19  H   HCH2   0   0.218  165.0820  174.4968  197.3489
 EZC  H20  H   HCH2   0   0.216  163.6431  175.4862  197.4544
 EZC  H21  H   HCR6   0   0.290  161.5517  175.2361  201.7199
 EZC  H22  H   HCH2   0   0.238  161.7921  176.8230  203.3313
 EZC  H23  H   HCH2   0   0.239  160.9858  175.3969  203.9905
 EZC  O03  O   O      0  -0.393  165.2550  172.1687  198.7851
 EZC  C20  C   CH2    0  -0.415  164.2917  175.0944  195.4497
 EZC  O04  O   O2     0  -0.433  163.0561  175.3099  203.9768

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
 EZC  C20  C24  single    1.522  0.020  1.522
 EZC  C20  C18  single    1.525  0.020  1.525
 EZC  C18  C12  single    1.527  0.020  1.527
 EZC  C12  C07  single    1.532  0.020  1.532
 EZC  C14  C13  single    1.540  0.020  1.540
 EZC  C14  C10  single    1.545  0.020  1.545
 EZC  C13  C09  single    1.525  0.020  1.525
 EZC  C10  C08  single    1.537  0.020  1.537
 EZC  C09  C08  single    1.532  0.020  1.532
 EZC  C07  C08  single    1.553  0.020  1.553
 EZC  C07  C11  single    1.543  0.020  1.543
 EZC  C07  C15  single    1.532  0.020  1.532
 EZC  O03  C15  double    1.210  0.020  1.210
 EZC  C11  C16  single    1.497  0.020  1.497
 EZC  C15  C17  single    1.468  0.020  1.468
 EZC  C17  C16  aromatic  1.387  0.020  1.387
 EZC  C17  C21  aromatic  1.395  0.020  1.395
 EZC  C16  C19  aromatic  1.384  0.020  1.384
 EZC  CL1  C21  single    1.716  0.020  1.716
 EZC  C21  C23  aromatic  1.380  0.020  1.380
 EZC  C19  C22  aromatic  1.393  0.020  1.393
 EZC  C23  C22  aromatic  1.416  0.020  1.416
 EZC  C23  CL2  single    1.719  0.020  1.719
 EZC  C22  O04  single    1.322  0.020  1.322
 EZC  C25  O04  single    1.424  0.020  1.424
 EZC  C25  C26  single    1.541  0.020  1.541
 EZC  C26  O05  deloc     1.244  0.020  1.244
 EZC  C26  O06  deloc     1.238  0.020  1.238
 EZC  C10  H1   single    0.970  0.020  1.090
 EZC  C10  H2   single    0.970  0.020  1.090
 EZC  C13  H3   single    0.970  0.020  1.090
 EZC  C13  H4   single    0.970  0.020  1.090
 EZC  C20  H5   single    0.970  0.020  1.090
 EZC  C20  H6   single    0.970  0.020  1.090
 EZC  C24  H7   single    0.970  0.020  1.090
 EZC  C24  H8   single    0.970  0.020  1.090
 EZC  C24  H9   single    0.970  0.020  1.090
 EZC  C08  H10  single    0.970  0.020  1.090
 EZC  C09  H11  single    0.970  0.020  1.090
 EZC  C09  H12  single    0.970  0.020  1.090
 EZC  C11  H13  single    0.970  0.020  1.090
 EZC  C11  H14  single    0.970  0.020  1.090
 EZC  C12  H15  single    0.970  0.020  1.090
 EZC  C12  H16  single    0.970  0.020  1.090
 EZC  C14  H17  single    0.970  0.020  1.090
 EZC  C14  H18  single    0.970  0.020  1.090
 EZC  C18  H19  single    0.970  0.020  1.090
 EZC  C18  H20  single    0.970  0.020  1.090
 EZC  C19  H21  single    0.930  0.020  1.080
 EZC  C25  H22  single    0.970  0.020  1.090
 EZC  C25  H23  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
 EZC  H2   C10  H1   106.81  3.000
 EZC  H2   C10  C14  110.05  3.000
 EZC  H1   C10  C14  111.91  3.000
 EZC  H2   C10  C08  110.36  3.000
 EZC  H1   C10  C08  112.30  3.000
 EZC  C14  C10  C08  105.46  3.000
 EZC  H4   C13  H3   106.98  3.000
 EZC  H4   C13  C14  110.35  3.000
 EZC  H3   C13  C14  112.75  3.000
 EZC  H4   C13  C09  109.56  3.000
 EZC  H3   C13  C09  112.75  3.000
 EZC  C14  C13  C09  104.47  3.000
 EZC  O03  C15  C07  125.10  3.000
 EZC  O03  C15  C17  126.94  3.000
 EZC  C07  C15  C17  107.96  3.000
 EZC  C16  C17  C21  119.79  3.000
 EZC  C21  C17  C15  130.62  3.000
 EZC  C16  C17  C15  109.57  3.000
 EZC  CL1  C21  C23  119.95  3.000
 EZC  C23  C21  C17  119.28  3.000
 EZC  CL1  C21  C17  120.76  3.000
 EZC  O04  C22  C23  115.51  3.000
 EZC  O04  C22  C19  125.00  3.000
 EZC  C23  C22  C19  119.50  3.000
 EZC  H9   C24  H8   107.50  3.000
 EZC  H9   C24  H7   107.58  3.000
 EZC  H8   C24  H7   107.63  3.000
 EZC  H9   C24  C20  111.21  3.000
 EZC  H8   C24  C20  111.18  3.000
 EZC  H7   C24  C20  111.54  3.000
 EZC  O06  C26  O05  128.78  3.000
 EZC  O06  C26  C25  118.29  3.000
 EZC  O05  C26  C25  112.93  3.000
 EZC  C12  C07  C11  112.89  3.000
 EZC  C11  C07  C08  108.73  3.000
 EZC  C12  C07  C08  112.80  3.000
 EZC  C11  C07  C15  103.98  3.000
 EZC  C08  C07  C15  106.88  3.000
 EZC  C12  C07  C15  111.04  3.000
 EZC  H10  C08  C09  106.80  3.000
 EZC  H10  C08  C07  106.47  3.000
 EZC  C09  C08  C07  115.22  3.000
 EZC  H10  C08  C10  107.58  3.000
 EZC  C07  C08  C10  117.47  3.000
 EZC  C09  C08  C10  102.69  3.000
 EZC  H12  C09  H11  107.38  3.000
 EZC  H12  C09  C08  113.50  3.000
 EZC  H11  C09  C08  110.41  3.000
 EZC  H12  C09  C13  112.92  3.000
 EZC  H11  C09  C13  109.79  3.000
 EZC  C08  C09  C13  102.81  3.000
 EZC  H14  C11  H13  106.15  3.000
 EZC  H14  C11  C16  111.04  3.000
 EZC  H13  C11  C16  109.63  3.000
 EZC  H14  C11  C07  112.87  3.000
 EZC  H13  C11  C07  111.80  3.000
 EZC  C16  C11  C07  105.41  3.000
 EZC  H16  C12  H15  106.03  3.000
 EZC  H16  C12  C18  108.74  3.000
 EZC  H15  C12  C18  108.22  3.000
 EZC  H16  C12  C07  109.48  3.000
 EZC  H15  C12  C07  108.29  3.000
 EZC  C18  C12  C07  115.64  3.000
 EZC  H18  C14  H17  106.47  3.000
 EZC  H18  C14  C13  110.90  3.000
 EZC  H17  C14  C13  111.29  3.000
 EZC  H18  C14  C10  110.50  3.000
 EZC  H17  C14  C10  111.72  3.000
 EZC  C13  C14  C10  106.05  3.000
 EZC  C19  C16  C11  126.90  3.000
 EZC  C19  C16  C17  121.75  3.000
 EZC  C11  C16  C17  111.34  3.000
 EZC  H20  C18  H19  106.14  3.000
 EZC  H20  C18  C12  110.45  3.000
 EZC  H19  C18  C12  110.75  3.000
 EZC  H20  C18  C20  108.70  3.000
 EZC  H19  C18  C20  108.68  3.000
 EZC  C12  C18  C20  111.93  3.000
 EZC  H21  C19  C16  120.07  3.000
 EZC  H21  C19  C22  121.04  3.000
 EZC  C16  C19  C22  118.89  3.000
 EZC  CL2  C23  C22  118.17  3.000
 EZC  CL2  C23  C21  121.05  3.000
 EZC  C22  C23  C21  120.78  3.000
 EZC  H23  C25  H22  107.40  3.000
 EZC  H23  C25  O04  109.98  3.000
 EZC  H22  C25  O04  110.16  3.000
 EZC  H23  C25  C26  109.67  3.000
 EZC  H22  C25  C26  109.09  3.000
 EZC  O04  C25  C26  110.48  3.000
 EZC  H6   C20  H5   106.06  3.000
 EZC  H6   C20  C18  109.22  3.000
 EZC  H5   C20  C18  109.35  3.000
 EZC  H6   C20  C24  109.61  3.000
 EZC  H5   C20  C24  109.64  3.000
 EZC  C18  C20  C24  112.74  3.000
 EZC  C25  O04  C22  119.66  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
 EZC  CONST_01  C22  C19  C16  C17     0.00   0.0  0
 EZC  CONST_02  C22  C23  C21  C17     0.00   0.0  0
 EZC  CONST_03  C19  C16  C17  C21     0.00   0.0  0
 EZC  CONST_04  C19  C22  C23  C21     0.00   0.0  0
 EZC  CONST_05  C23  C21  C17  C16     0.00   0.0  0
 EZC  CONST_06  C23  C22  C19  C16     0.00   0.0  0
 EZC  CONST_07  CL1  C21  C17  C15     0.00   0.0  0
 EZC  CONST_08  CL2  C23  C21  C17   180.00   0.0  0
 EZC  CONST_09  O04  C22  C23  C21   180.00   0.0  0
 EZC  CONST_10  CL1  C21  C23  C22   180.00   0.0  0
 EZC  CONST_11  CL1  C21  C17  C16   180.00   0.0  0
 EZC  CONST_12  O04  C22  C19  C16   180.00   0.0  0
 EZC  CONST_13  CL2  C23  C22  C19   180.00   0.0  0
 EZC  CONST_14  H21  C19  C16  C17   180.00   0.0  0
 EZC  Var_01    C09  C13  C14  C10    18.76  30.0  1
 EZC  Var_02    C08  C10  C14  C13     7.83  30.0  1
 EZC  Var_03    C07  C11  C16  C17     8.07  30.0  1
 EZC  Var_04    C07  C15  C17  C21   172.90  30.0  1
 EZC  Var_05    C14  C13  C09  C08   -38.29  30.0  1
 EZC  Var_06    C07  C12  C18  C20  -178.54  30.0  3
 EZC  Var_07    C26  C25  O04  C22  -177.59  30.0  2
 EZC  Var_08    C12  C18  C20  C24   178.65  30.0  3
 EZC  Var_09    O05  C26  C25  O04  -178.64  30.0  3
 EZC  Var_10    H7   C24  C20  C18   179.65  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
 EZC  chir_01  C07  C08  C11  C15  negativ
 EZC  chir_02  C08  C10  C09  C07  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
 EZC  plan-1  C15  0.020
 EZC  plan-1  C17  0.020
 EZC  plan-1  C07  0.020
 EZC  plan-1  O03  0.020
 EZC  plan-2  C15  0.020
 EZC  plan-2  C17  0.020
 EZC  plan-2  C21  0.020
 EZC  plan-2  C22  0.020
 EZC  plan-2  C11  0.020
 EZC  plan-2  C16  0.020
 EZC  plan-2  C19  0.020
 EZC  plan-2  C23  0.020
 EZC  plan-2  CL1  0.020
 EZC  plan-2  CL2  0.020
 EZC  plan-2  H21  0.020
 EZC  plan-2  O04  0.020
 EZC  plan-3  C26  0.020
 EZC  plan-3  C25  0.020
 EZC  plan-3  O05  0.020
 EZC  plan-3  O06  0.020

