# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 19:11:52 2020
#   Inital geometry file: a 86 line input string
#   Ligand name: ethyl 1-(2-chlorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1c(C)nn(c1C)c2ccccc2Cl
#
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
 6DE  6DE  'ethyl 1-(2-chlorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate'  ligand  34  19  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_6DE
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
 6DE  O14   O   O     0  -0.464   1.1037  -1.7245   2.9820
 6DE  C13   C   C     0   0.519   0.5750  -0.6472   2.8143
 6DE  O15   O   O2    0  -0.460   0.0986   0.0946   3.8049
 6DE  C16   C   CH2   0  -0.177   0.1914  -0.4154   5.1420
 6DE  C17   C   CH3   0  -0.684  -0.4509   0.5946   6.0618
 6DE  C12   C   CR5   0  -0.383   0.3866  -0.0178   1.5145
 6DE  C18   C   CR5   0   0.480   0.8419  -0.5422   0.3133
 6DE  C19   C   CH3   0  -0.735   1.6108  -1.7749   0.0098
 6DE  C10   C   CR5   0   0.321  -0.2683   1.1966   1.1733
 6DE  C11   C   CH3   0  -0.731  -0.9538   2.1895   2.0458
 6DE  N9    N   N     0  -0.301  -0.2163   1.3902  -0.1232
 6DE  N1    N   NR5   0  -0.440   0.4540   0.3362  -0.6262
 6DE  C2    C   CR6   0   0.366   0.6713   0.2657  -2.0201
 6DE  C3    C   CR6   0  -0.071  -0.0196  -0.6548  -2.8022
 6DE  CL4   CL  CL    0  -0.090  -1.1598  -1.7229  -2.0708
 6DE  C5    C   CR16  0  -0.220   0.1953  -0.7145  -4.1704
 6DE  C6    C   CR16  0  -0.248   1.0938   0.1628  -4.7582
 6DE  C7    C   CR16  0  -0.254   1.7755   1.0945  -3.9870
 6DE  C8    C   CR16  0  -0.263   1.5653   1.1420  -2.6184
 6DE  H161  H   HCH2  0   0.233   1.2395  -0.5725   5.4059
 6DE  H162  H   HCH2  0   0.233  -0.3183  -1.3791   5.2056
 6DE  H171  H   HCH3  0   0.238  -0.4064   0.2262   7.0863
 6DE  H172  H   HCH3  0   0.235   0.0663   1.5536   6.0285
 6DE  H173  H   HCH3  0   0.235  -1.4988   0.7553   5.8081
 6DE  H191  H   HCH3  0   0.257   1.9913  -1.7696  -1.0099
 6DE  H192  H   HCH3  0   0.271   2.4546  -1.8731   0.6882
 6DE  H193  H   HCH3  0   0.268   0.9867  -2.6597   0.1335
 6DE  H111  H   HCH3  0   0.249  -0.2632   2.6380   2.7595
 6DE  H112  H   HCH3  0   0.246  -1.3793   2.9852   1.4369
 6DE  H113  H   HCH3  0   0.249  -1.7558   1.7284   2.6212
 6DE  H5    H   HCR6  0   0.289  -0.3409  -1.4363  -4.7708
 6DE  H6    H   HCR6  0   0.278   1.2583   0.1153  -5.8262
 6DE  H7    H   HCR6  0   0.274   2.4741   1.7782  -4.4493
 6DE  H8    H   HCR6  0   0.284   2.0928   1.8569  -2.0011

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
 6DE  O14  C13   double    1.212  0.020  1.212
 6DE  C13  O15   single    1.326  0.020  1.326
 6DE  C13  C12   single    1.456  0.020  1.456
 6DE  O15  C16   single    1.434  0.020  1.434
 6DE  C16  C17   single    1.509  0.020  1.509
 6DE  C16  H161  single    0.970  0.020  1.090
 6DE  C16  H162  single    0.970  0.020  1.090
 6DE  C17  H171  single    0.970  0.020  1.090
 6DE  C17  H172  single    0.970  0.020  1.090
 6DE  C17  H173  single    0.970  0.020  1.090
 6DE  C12  C18   aromatic  1.388  0.020  1.388
 6DE  C12  C10   aromatic  1.421  0.020  1.421
 6DE  C18  C19   single    1.484  0.020  1.484
 6DE  C18  N1    aromatic  1.343  0.020  1.343
 6DE  C19  H191  single    0.970  0.020  1.090
 6DE  C19  H192  single    0.970  0.020  1.090
 6DE  C19  H193  single    0.970  0.020  1.090
 6DE  C10  C11   single    1.489  0.020  1.489
 6DE  C10  N9    aromatic  1.312  0.020  1.312
 6DE  C11  H111  single    0.970  0.020  1.090
 6DE  C11  H112  single    0.970  0.020  1.090
 6DE  C11  H113  single    0.970  0.020  1.090
 6DE  N9   N1    aromatic  1.347  0.020  1.347
 6DE  N1   C2    single    1.412  0.020  1.412
 6DE  C2   C3    aromatic  1.391  0.020  1.391
 6DE  C2   C8    aromatic  1.388  0.020  1.388
 6DE  C3   CL4   single    1.725  0.020  1.725
 6DE  C3   C5    aromatic  1.386  0.020  1.386
 6DE  C5   C6    aromatic  1.387  0.020  1.387
 6DE  C5   H5    single    0.930  0.020  1.080
 6DE  C6   C7    aromatic  1.388  0.020  1.388
 6DE  C6   H6    single    0.930  0.020  1.080
 6DE  C7   C8    aromatic  1.385  0.020  1.385
 6DE  C7   H7    single    0.930  0.020  1.080
 6DE  C8   H8    single    0.930  0.020  1.080

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
 6DE  C12   C13  O15   112.24  3.000
 6DE  C12   C13  O14   124.35  3.000
 6DE  O15   C13  O14   123.41  3.000
 6DE  C16   O15  C13   118.32  3.000
 6DE  H162  C16  H161  107.87  3.000
 6DE  H162  C16  C17   110.88  3.000
 6DE  H161  C16  C17   110.94  3.000
 6DE  H162  C16  O15   109.75  3.000
 6DE  H161  C16  O15   109.79  3.000
 6DE  C17   C16  O15   107.62  3.000
 6DE  H173  C17  H172  108.63  3.000
 6DE  H173  C17  H171  107.93  3.000
 6DE  H172  C17  H171  107.87  3.000
 6DE  H173  C17  C16   111.46  3.000
 6DE  H172  C17  C16   111.60  3.000
 6DE  H171  C17  C16   109.22  3.000
 6DE  C10   C12  C18   105.45  3.000
 6DE  C10   C12  C13   130.03  3.000
 6DE  C18   C12  C13   124.53  3.000
 6DE  N1    C18  C19   123.34  3.000
 6DE  N1    C18  C12   105.28  3.000
 6DE  C19   C18  C12   131.37  3.000
 6DE  H193  C19  H192  107.48  3.000
 6DE  H193  C19  H191  108.09  3.000
 6DE  H192  C19  H191  108.28  3.000
 6DE  H193  C19  C18   110.76  3.000
 6DE  H192  C19  C18   110.46  3.000
 6DE  H191  C19  C18   111.64  3.000
 6DE  N9    C10  C11   119.93  3.000
 6DE  N9    C10  C12   110.19  3.000
 6DE  C11   C10  C12   129.88  3.000
 6DE  H113  C11  H112  108.48  3.000
 6DE  H113  C11  H111  107.14  3.000
 6DE  H112  C11  H111  108.26  3.000
 6DE  H113  C11  C10   111.48  3.000
 6DE  H112  C11  C10   109.85  3.000
 6DE  H111  C11  C10   111.50  3.000
 6DE  N1    N9   C10   105.86  3.000
 6DE  C2    N1   N9    118.96  3.000
 6DE  C2    N1   C18   127.81  3.000
 6DE  N9    N1   C18   113.22  3.000
 6DE  C8    C2   C3    119.69  3.000
 6DE  C8    C2   N1    119.54  3.000
 6DE  C3    C2   N1    120.75  3.000
 6DE  C5    C3   CL4   119.62  3.000
 6DE  C5    C3   C2    120.42  3.000
 6DE  CL4   C3   C2    119.96  3.000
 6DE  H5    C5   C6    120.55  3.000
 6DE  H5    C5   C3    120.00  3.000
 6DE  C6    C5   C3    119.45  3.000
 6DE  H6    C6   C7    120.22  3.000
 6DE  H6    C6   C5    119.30  3.000
 6DE  C7    C6   C5    120.48  3.000
 6DE  H7    C7   C8    119.91  3.000
 6DE  H7    C7   C6    120.27  3.000
 6DE  C8    C7   C6    119.82  3.000
 6DE  H8    C8   C7    120.82  3.000
 6DE  H8    C8   C2    119.04  3.000
 6DE  C7    C8   C2    120.14  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
 6DE  CONST_01  N9    N1   C18  C12     0.00   0.0  0
 6DE  CONST_02  C2    N1   C18  C12   180.00   0.0  0
 6DE  CONST_03  N1    N9   C10  C12     0.00   0.0  0
 6DE  CONST_04  N9    C10  C12  C18     0.00   0.0  0
 6DE  CONST_05  C10   N9   N1   C18     0.00   0.0  0
 6DE  CONST_08  N1    C18  C12  C10     0.00   0.0  0
 6DE  CONST_09  C2    N1   N9   C10   180.00   0.0  0
 6DE  CONST_12  C5    C3   C2   N1    180.00   0.0  0
 6DE  CONST_13  C7    C8   C2   N1    180.00   0.0  0
 6DE  CONST_14  C6    C5   C3   C2      0.00   0.0  0
 6DE  CONST_15  C6    C7   C8   C2      0.00   0.0  0
 6DE  CONST_16  C7    C8   C2   C3      0.00   0.0  0
 6DE  CONST_17  C7    C6   C5   C3      0.00   0.0  0
 6DE  CONST_18  C8    C2   C3   C5      0.00   0.0  0
 6DE  CONST_19  C8    C7   C6   C5      0.00   0.0  0
 6DE  CONST_20  N1    C18  C12  C13   180.00   0.0  0
 6DE  CONST_21  N9    C10  C12  C13   180.00   0.0  0
 6DE  CONST_22  C11   C10  C12  C18   180.00   0.0  0
 6DE  CONST_23  C10   C12  C18  C19   180.00   0.0  0
 6DE  CONST_24  N9    N1   C18  C19   180.00   0.0  0
 6DE  CONST_25  C2    N1   C18  C19     0.00   0.0  0
 6DE  CONST_26  N1    N9   C10  C11   180.00   0.0  0
 6DE  CONST_27  CL4   C3   C2   N1      0.00   0.0  0
 6DE  CONST_28  C8    C2   C3   CL4   180.00   0.0  0
 6DE  CONST_29  C6    C5   C3   CL4   180.00   0.0  0
 6DE  CONST_30  H8    C8   C2   N1      0.00   0.0  0
 6DE  CONST_31  H5    C5   C3   C2    180.00   0.0  0
 6DE  CONST_32  H7    C7   C8   C2    180.00   0.0  0
 6DE  CONST_33  H6    C6   C5   C3    180.00   0.0  0
 6DE  Var_01    C18   C12  C13  O14    -3.10  30.0  2
 6DE  Var_02    H191  C19  C18  C12  -167.22  30.0  2
 6DE  Var_03    H111  C11  C10  C12    62.23  30.0  2
 6DE  Var_04    C12   C13  O15  C16   178.74  30.0  2
 6DE  Var_05    C17   C16  O15  C13  -178.45  30.0  3
 6DE  Var_06    H171  C17  C16  O15   179.26  30.0  3

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
 6DE  plan-1  C13  0.020
 6DE  plan-1  C12  0.020
 6DE  plan-1  C18  0.020
 6DE  plan-1  C19  0.020
 6DE  plan-1  C10  0.020
 6DE  plan-1  C11  0.020
 6DE  plan-1  N9   0.020
 6DE  plan-1  N1   0.020
 6DE  plan-1  C2   0.020
 6DE  plan-2  N1   0.020
 6DE  plan-2  C2   0.020
 6DE  plan-2  C3   0.020
 6DE  plan-2  CL4  0.020
 6DE  plan-2  C5   0.020
 6DE  plan-2  C6   0.020
 6DE  plan-2  C7   0.020
 6DE  plan-2  C8   0.020
 6DE  plan-2  H5   0.020
 6DE  plan-2  H6   0.020
 6DE  plan-2  H7   0.020
 6DE  plan-2  H8   0.020
 6DE  plan-3  O14  0.020
 6DE  plan-3  C13  0.020
 6DE  plan-3  O15  0.020
 6DE  plan-3  C12  0.020

