# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 21:06:47 2020
#   Inital geometry file: a 101 line input string
#   Ligand name: 2-{5-[(4-chloro-2-methylphenyl)methoxy]-1H-pyrazol-1-yl}pyridine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc(Cl)ccc1COc2ccnn2c3cc(ccn3)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
 6EP  6EP  '2-{5-[(4-chloro-2-methylphenyl)methoxy]-1H-pyrazol-1-yl}pyridine-4-carboxylic acid'  ligand  37  24  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_6EP
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
 6EP  C10  C   CR15   0  -0.573  -0.6093   3.4962  -0.2017
 6EP  C13  C   CH2    0  -0.197   1.7163   1.7924   0.0083
 6EP  C15  C   CR16   0  -0.314   2.3697  -0.6201  -0.3537
 6EP  C17  C   CR6    0  -0.037   4.6086  -1.3510   0.0205
 6EP  C20  C   CR6    0   0.086   4.0368   0.9573   0.3903
 6EP  C21  C   CH3    0  -0.752   4.4436   2.3447   0.7916
 6EP  C24  C   CR16   0  -0.366  -3.2174  -2.1862  -0.5300
 6EP  O01  O   O      0  -0.580  -5.9356  -0.7354   1.3857
 6EP  O03  O   OC    -1  -0.581  -5.6492  -2.8400   0.6980
 6EP  C04  C   CR6    0   0.009  -3.9999  -1.2515   0.1415
 6EP  C05  C   CR16   0  -0.392  -3.5369   0.0537   0.2081
 6EP  C06  C   CR6    0   0.489  -2.3290   0.3577  -0.4081
 6EP  N07  N   NR5    0  -0.455  -1.8492   1.6828  -0.3649
 6EP  N08  N   N      0  -0.288  -2.7223   2.7109  -0.3637
 6EP  C09  C   CR15   0  -0.042  -1.9844   3.7903  -0.2711
 6EP  C11  C   CR5    0   0.663  -0.5680   2.1231  -0.2632
 6EP  O12  O   O2     0  -0.450   0.4260   1.2525  -0.2041
 6EP  C14  C   CR6    0   0.009   2.7167   0.6735   0.0157
 6EP  C16  C   CR16   0  -0.218   3.3101  -1.6416  -0.3531
 6EP  C19  C   CR16   0  -0.257   4.9763  -0.0665   0.3886
 6EP  N22  N   N      0  -0.418  -1.5870  -0.5203  -1.0551
 6EP  C23  C   CR16   0  -0.060  -2.0265  -1.7735  -1.1008
 6EP  H1   H   HCR5   0   0.284   0.2138   4.1844  -0.1123
 6EP  H2   H   HCH2   0   0.258   1.9569   2.5133  -0.7832
 6EP  H3   H   HCH2   0   0.250   1.7374   2.3404   0.9577
 6EP  H4   H   HCR6   0   0.275   1.3552  -0.8530  -0.6482
 6EP  H5   H   HCH3   0   0.254   3.8844   2.6886   1.6643
 6EP  H6   H   HCH3   0   0.263   5.5021   2.3882   1.0406
 6EP  H7   H   HCH3   0   0.254   4.2617   3.0642  -0.0091
 6EP  H8   H   HCR6   0   0.261  -3.5291  -3.2181  -0.6067
 6EP  H10  H   HCR6   0   0.269  -4.0983   0.8120   0.7335
 6EP  H11  H   HCR5   0   0.267  -2.4492   4.7647  -0.2622
 6EP  H12  H   HCR6   0   0.278   3.0252  -2.6442  -0.6406
 6EP  H13  H   HCR6   0   0.273   5.9981   0.1451   0.6768
 6EP  H14  H   HCR6   0   0.263  -1.3981  -2.4797  -1.6311
 6EP  C02  C   C      0   0.412  -5.3209  -1.6461   0.8043
 6EP  CL1  CL  CL     0  -0.135   5.8021  -2.6106   0.0306

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
 6EP  C09  C10  aromatic  1.408  0.020  1.408
 6EP  C09  N08  aromatic  1.311  0.020  1.311
 6EP  C10  C11  aromatic  1.375  0.020  1.375
 6EP  N08  N07  aromatic  1.349  0.020  1.349
 6EP  C11  N07  aromatic  1.359  0.020  1.359
 6EP  C11  O12  single    1.323  0.020  1.323
 6EP  N07  C06  single    1.410  0.020  1.410
 6EP  C21  C20  single    1.500  0.020  1.500
 6EP  C13  O12  single    1.415  0.020  1.415
 6EP  C13  C14  single    1.501  0.020  1.501
 6EP  N22  C06  aromatic  1.319  0.020  1.319
 6EP  N22  C23  aromatic  1.329  0.020  1.329
 6EP  C06  C05  aromatic  1.390  0.020  1.390
 6EP  C20  C14  aromatic  1.401  0.020  1.401
 6EP  C20  C19  aromatic  1.390  0.020  1.390
 6EP  C14  C15  aromatic  1.389  0.020  1.389
 6EP  C23  C24  aromatic  1.384  0.020  1.384
 6EP  C05  C04  aromatic  1.386  0.020  1.386
 6EP  C19  C17  aromatic  1.386  0.020  1.386
 6EP  C15  C16  aromatic  1.388  0.020  1.388
 6EP  C24  C04  aromatic  1.392  0.020  1.392
 6EP  C04  C02  single    1.530  0.020  1.530
 6EP  C17  C16  aromatic  1.382  0.020  1.382
 6EP  C17  CL1  single    1.735  0.020  1.735
 6EP  C02  O01  deloc     1.243  0.020  1.243
 6EP  C02  O03  deloc     1.243  0.020  1.243
 6EP  C10  H1   single    0.930  0.020  1.080
 6EP  C13  H2   single    0.970  0.020  1.090
 6EP  C13  H3   single    0.970  0.020  1.090
 6EP  C15  H4   single    0.930  0.020  1.080
 6EP  C21  H5   single    0.970  0.020  1.090
 6EP  C21  H6   single    0.970  0.020  1.090
 6EP  C21  H7   single    0.970  0.020  1.090
 6EP  C24  H8   single    0.930  0.020  1.080
 6EP  C05  H10  single    0.930  0.020  1.080
 6EP  C09  H11  single    0.930  0.020  1.080
 6EP  C16  H12  single    0.930  0.020  1.080
 6EP  C19  H13  single    0.930  0.020  1.080
 6EP  C23  H14  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
 6EP  H1   C10  C11  128.25  3.000
 6EP  H1   C10  C09  128.12  3.000
 6EP  C11  C10  C09  103.63  3.000
 6EP  H3   C13  H2   106.98  3.000
 6EP  H3   C13  C14  110.82  3.000
 6EP  H2   C13  C14  110.32  3.000
 6EP  H3   C13  O12  109.77  3.000
 6EP  H2   C13  O12  110.03  3.000
 6EP  C14  C13  O12  108.91  3.000
 6EP  H4   C15  C16  118.48  3.000
 6EP  H4   C15  C14  120.47  3.000
 6EP  C16  C15  C14  121.05  3.000
 6EP  C19  C17  CL1  119.25  3.000
 6EP  CL1  C17  C16  119.68  3.000
 6EP  C19  C17  C16  121.06  3.000
 6EP  C19  C20  C14  119.17  3.000
 6EP  C19  C20  C21  119.88  3.000
 6EP  C14  C20  C21  120.94  3.000
 6EP  H7   C21  H6   107.67  3.000
 6EP  H7   C21  H5   107.05  3.000
 6EP  H6   C21  H5   107.62  3.000
 6EP  H7   C21  C20  111.59  3.000
 6EP  H6   C21  C20  111.22  3.000
 6EP  H5   C21  C20  111.48  3.000
 6EP  H8   C24  C23  120.25  3.000
 6EP  H8   C24  C04  120.89  3.000
 6EP  C23  C24  C04  118.86  3.000
 6EP  C05  C04  C02  120.69  3.000
 6EP  C02  C04  C24  121.42  3.000
 6EP  C05  C04  C24  117.88  3.000
 6EP  H10  C05  C06  120.92  3.000
 6EP  H10  C05  C04  120.72  3.000
 6EP  C06  C05  C04  118.36  3.000
 6EP  N22  C06  N07  116.69  3.000
 6EP  N22  C06  C05  124.11  3.000
 6EP  N07  C06  C05  119.20  3.000
 6EP  C11  N07  N08  111.31  3.000
 6EP  C11  N07  C06  128.89  3.000
 6EP  N08  N07  C06  119.74  3.000
 6EP  C09  N08  N07  105.26  3.000
 6EP  H11  C09  N08  120.09  3.000
 6EP  H11  C09  C10  127.49  3.000
 6EP  N08  C09  C10  112.42  3.000
 6EP  O12  C11  N07  119.92  3.000
 6EP  O12  C11  C10  132.67  3.000
 6EP  N07  C11  C10  107.38  3.000
 6EP  C11  O12  C13  116.16  3.000
 6EP  C20  C14  C15  119.67  3.000
 6EP  C15  C14  C13  121.76  3.000
 6EP  C20  C14  C13  118.57  3.000
 6EP  H12  C16  C17  120.96  3.000
 6EP  H12  C16  C15  120.24  3.000
 6EP  C17  C16  C15  118.80  3.000
 6EP  H13  C19  C20  119.59  3.000
 6EP  H13  C19  C17  120.16  3.000
 6EP  C20  C19  C17  120.25  3.000
 6EP  C23  N22  C06  117.29  3.000
 6EP  H14  C23  N22  116.07  3.000
 6EP  H14  C23  C24  120.43  3.000
 6EP  N22  C23  C24  123.49  3.000
 6EP  C04  C02  O03  116.03  3.000
 6EP  O03  C02  O01  127.83  3.000
 6EP  C04  C02  O01  116.14  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
 6EP  CONST_01  N07  N08  C09  C10     0.00   0.0  0
 6EP  CONST_02  N08  N07  C11  C10     0.00   0.0  0
 6EP  CONST_03  C06  N07  C11  C10   180.00   0.0  0
 6EP  CONST_04  C19  C20  C14  C15     0.00   0.0  0
 6EP  CONST_05  C19  C17  C16  C15     0.00   0.0  0
 6EP  CONST_06  C14  C20  C19  C17     0.00   0.0  0
 6EP  CONST_07  C14  C15  C16  C17     0.00   0.0  0
 6EP  CONST_08  C16  C15  C14  C20     0.00   0.0  0
 6EP  CONST_09  C16  C17  C19  C20     0.00   0.0  0
 6EP  CONST_10  C06  N22  C23  C24     0.00   0.0  0
 6EP  CONST_11  C06  C05  C04  C24     0.00   0.0  0
 6EP  CONST_12  N07  C06  C05  C04   180.00   0.0  0
 6EP  CONST_13  N22  C06  C05  C04     0.00   0.0  0
 6EP  CONST_14  N22  C23  C24  C04     0.00   0.0  0
 6EP  CONST_17  C23  N22  C06  C05     0.00   0.0  0
 6EP  CONST_18  C23  C24  C04  C05     0.00   0.0  0
 6EP  CONST_19  C09  N08  N07  C06   180.00   0.0  0
 6EP  CONST_20  C09  C10  C11  N07     0.00   0.0  0
 6EP  CONST_21  C23  N22  C06  N07   180.00   0.0  0
 6EP  CONST_22  C11  C10  C09  N08     0.00   0.0  0
 6EP  CONST_24  C11  N07  N08  C09     0.00   0.0  0
 6EP  CONST_26  C19  C20  C14  C13   180.00   0.0  0
 6EP  CONST_27  C16  C15  C14  C13   180.00   0.0  0
 6EP  CONST_28  C21  C20  C14  C15   180.00   0.0  0
 6EP  CONST_29  CL1  C17  C16  C15   180.00   0.0  0
 6EP  CONST_30  C21  C20  C19  C17   180.00   0.0  0
 6EP  CONST_31  CL1  C17  C19  C20   180.00   0.0  0
 6EP  CONST_32  C06  C05  C04  C02   180.00   0.0  0
 6EP  CONST_33  C23  C24  C04  C02   180.00   0.0  0
 6EP  CONST_34  O12  C11  N07  C06     0.00   0.0  0
 6EP  CONST_35  O12  C11  N07  N08   180.00   0.0  0
 6EP  CONST_36  O12  C11  C10  C09   180.00   0.0  0
 6EP  CONST_37  H4   C15  C16  C17   180.00   0.0  0
 6EP  CONST_38  H10  C05  C04  C24   180.00   0.0  0
 6EP  CONST_39  H14  C23  C24  C04   180.00   0.0  0
 6EP  CONST_40  H8   C24  C04  C05   180.00   0.0  0
 6EP  CONST_41  H11  C09  N08  N07   180.00   0.0  0
 6EP  CONST_42  H1   C10  C11  N07   180.00   0.0  0
 6EP  CONST_43  H13  C19  C20  C14   180.00   0.0  0
 6EP  CONST_44  H12  C16  C15  C14   180.00   0.0  0
 6EP  Var_01    N07  C11  O12  C13  -175.12  30.0  1
 6EP  Var_02    O12  C13  C14  C15     9.37  30.0  3
 6EP  Var_03    O01  C02  C04  C24   179.48  30.0  2
 6EP  Var_04    C14  C13  O12  C11  -178.71  30.0  1
 6EP  Var_05    H5   C21  C20  C14    60.47  30.0  2

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
 6EP  plan-1  C10  0.020
 6EP  plan-1  C06  0.020
 6EP  plan-1  N07  0.020
 6EP  plan-1  N08  0.020
 6EP  plan-1  C09  0.020
 6EP  plan-1  C11  0.020
 6EP  plan-1  O12  0.020
 6EP  plan-1  H1   0.020
 6EP  plan-1  H11  0.020
 6EP  plan-2  C13  0.020
 6EP  plan-2  C15  0.020
 6EP  plan-2  C17  0.020
 6EP  plan-2  C20  0.020
 6EP  plan-2  C21  0.020
 6EP  plan-2  C14  0.020
 6EP  plan-2  C16  0.020
 6EP  plan-2  C19  0.020
 6EP  plan-2  H4   0.020
 6EP  plan-2  H12  0.020
 6EP  plan-2  H13  0.020
 6EP  plan-2  CL1  0.020
 6EP  plan-3  C24  0.020
 6EP  plan-3  C04  0.020
 6EP  plan-3  C05  0.020
 6EP  plan-3  C06  0.020
 6EP  plan-3  N07  0.020
 6EP  plan-3  N22  0.020
 6EP  plan-3  C23  0.020
 6EP  plan-3  H8   0.020
 6EP  plan-3  H10  0.020
 6EP  plan-3  H14  0.020
 6EP  plan-3  C02  0.020
 6EP  plan-4  O01  0.020
 6EP  plan-4  O03  0.020
 6EP  plan-4  C04  0.020
 6EP  plan-4  C02  0.020

