# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  2 18:12:46 2020
#   Inital geometry file: a 89 line input string
#   Ligand name: 4-(ethoxycarbonyl)-3,5-dimethyl-1-phenyl-1H-pyrazol-2-ium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1c(C)[nH+]n(c1C)c2ccccc2
#
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
 3DE  3DE  4-(ethoxycarbonyl)-3,5-dimethyl-1-phenyl-1H-pyrazol-2-ium  ligand  35  18  .  2021-08-04  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_3DE
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
 3DE  C14   C  C     0   0.597   1.7302   0.4096   7.4150
 3DE  O15   O  O2    0  -0.471   1.6838  -0.3177   8.5126
 3DE  C16   C  CH2   0  -0.198   1.6729   0.3584   9.7832
 3DE  C17   C  CH3   0  -0.720   1.6463  -0.6971  10.8600
 3DE  C10   C  CR5   0  -0.432   1.7265  -0.4255   6.2097
 3DE  C11   C  CR5   0   0.658   1.6786  -1.8209   6.1172
 3DE  N13   N  NR15  1  -0.499   1.6829  -2.1072   4.8250
 3DE  C12   C  CH3   0  -0.815   1.6292  -2.8917   7.1383
 3DE  C8    C  CR5   0   0.457   1.7679   0.0683   4.9018
 3DE  C9    C  CH3   0  -0.779   1.8377   1.4557   4.3936
 3DE  N1    N  NR5   0  -0.336   1.7346  -0.9865   4.0889
 3DE  C2    C  CR6   0   0.368   1.7817  -1.0479   2.6646
 3DE  C3    C  CR16  0  -0.263   2.9832  -1.3642   2.0498
 3DE  C4    C  CR16  0  -0.194   3.0234  -1.4296   0.6656
 3DE  C5    C  CR16  0  -0.298   1.8772  -1.1728  -0.0760
 3DE  C6    C  CR16  0  -0.220   0.6838  -0.8523   0.5580
 3DE  C7    C  CR16  0  -0.342   0.6268  -0.7927   1.9426
 3DE  O1    O  O     0  -0.373   1.7674   1.6156   7.3872
 3DE  H161  H  HCH2  0   0.239   2.5614   0.9863   9.8677
 3DE  H162  H  HCH2  0   0.261   0.7947   1.0038   9.8410
 3DE  H171  H  HCH3  0   0.250   1.6329  -0.2102  11.8345
 3DE  H172  H  HCH3  0   0.267   0.7569  -1.3224  10.7859
 3DE  H173  H  HCH3  0   0.197   2.5283  -1.3356  10.8163
 3DE  H13   H  HNR5  0   0.472   1.6346  -3.0126   4.3776
 3DE  H121  H  HCH3  0   0.313   2.5084  -2.8441   7.7775
 3DE  H122  H  HCH3  0   0.257   0.7518  -2.7744   7.7702
 3DE  H123  H  HCH3  0   0.320   1.5925  -3.8729   6.6715
 3DE  H91   H  HCH3  0   0.308   1.8893   1.4818   3.3081
 3DE  H92   H  HCH3  0   0.286   0.9607   2.0144   4.7149
 3DE  H93   H  HCH3  0   0.310   2.7152   1.9587   4.7952
 3DE  H3    H  HCR6  0   0.281   3.8673  -1.5525   2.6451
 3DE  H4    H  HCR6  0   0.277   3.9509  -1.6764   0.1677
 3DE  H5    H  HCR6  0   0.280   1.9147  -1.2200  -1.1560
 3DE  H6    H  HCR6  0   0.280  -0.2043  -0.6493  -0.0245
 3DE  H7    H  HCR6  0   0.261  -0.2940  -0.5449   2.4538

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
 3DE  C14  O15   single    1.318  0.020  1.318
 3DE  C14  C10   single    1.466  0.020  1.466
 3DE  C14  O1    double    1.207  0.020  1.207
 3DE  O15  C16   single    1.439  0.020  1.439
 3DE  C16  C17   single    1.508  0.020  1.508
 3DE  C16  H161  single    0.970  0.020  1.090
 3DE  C16  H162  single    0.970  0.020  1.090
 3DE  C17  H171  single    0.970  0.020  1.090
 3DE  C17  H172  single    0.970  0.020  1.090
 3DE  C17  H173  single    0.970  0.020  1.090
 3DE  C10  C11   aromatic  1.399  0.020  1.399
 3DE  C10  C8    aromatic  1.399  0.020  1.399
 3DE  C11  N13   aromatic  1.323  0.020  1.323
 3DE  C11  C12   single    1.481  0.020  1.481
 3DE  N13  N1    aromatic  1.342  0.020  1.342
 3DE  N13  H13   single    0.860  0.020  1.020
 3DE  C12  H121  single    0.970  0.020  1.090
 3DE  C12  H122  single    0.970  0.020  1.090
 3DE  C12  H123  single    0.970  0.020  1.090
 3DE  C8   C9    single    1.479  0.020  1.479
 3DE  C8   N1    aromatic  1.332  0.020  1.332
 3DE  C9   H91   single    0.970  0.020  1.090
 3DE  C9   H92   single    0.970  0.020  1.090
 3DE  C9   H93   single    0.970  0.020  1.090
 3DE  N1   C2    single    1.426  0.020  1.426
 3DE  C2   C3    aromatic  1.386  0.020  1.386
 3DE  C2   C7    aromatic  1.386  0.020  1.386
 3DE  C3   C4    aromatic  1.386  0.020  1.386
 3DE  C3   H3    single    0.930  0.020  1.080
 3DE  C4   C5    aromatic  1.389  0.020  1.389
 3DE  C4   H4    single    0.930  0.020  1.080
 3DE  C5   C6    aromatic  1.389  0.020  1.389
 3DE  C5   H5    single    0.930  0.020  1.080
 3DE  C6   C7    aromatic  1.387  0.020  1.387
 3DE  C6   H6    single    0.930  0.020  1.080
 3DE  C7   H7    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
 3DE  O1    C14  C10   123.38  3.000
 3DE  O1    C14  O15   124.88  3.000
 3DE  C10   C14  O15   111.73  3.000
 3DE  C16   O15  C14   118.45  3.000
 3DE  H162  C16  H161  108.11  3.000
 3DE  H162  C16  C17   111.22  3.000
 3DE  H161  C16  C17   111.21  3.000
 3DE  H162  C16  O15   109.31  3.000
 3DE  H161  C16  O15   109.42  3.000
 3DE  C17   C16  O15   107.56  3.000
 3DE  H173  C17  H172  108.76  3.000
 3DE  H173  C17  H171  107.92  3.000
 3DE  H172  C17  H171  107.89  3.000
 3DE  H173  C17  C16   111.55  3.000
 3DE  H172  C17  C16   111.56  3.000
 3DE  H171  C17  C16   109.03  3.000
 3DE  C8    C10  C11   106.93  3.000
 3DE  C8    C10  C14   124.58  3.000
 3DE  C11   C10  C14   128.49  3.000
 3DE  C12   C11  N13   121.14  3.000
 3DE  C12   C11  C10   132.59  3.000
 3DE  N13   C11  C10   106.27  3.000
 3DE  H13   N13  N1    120.46  3.000
 3DE  H13   N13  C11   128.72  3.000
 3DE  N1    N13  C11   110.80  3.000
 3DE  H123  C12  H122  108.64  3.000
 3DE  H123  C12  H121  108.61  3.000
 3DE  H122  C12  H121  107.81  3.000
 3DE  H123  C12  C11   110.96  3.000
 3DE  H122  C12  C11   110.46  3.000
 3DE  H121  C12  C11   110.28  3.000
 3DE  N1    C8   C9    122.29  3.000
 3DE  N1    C8   C10   106.88  3.000
 3DE  C9    C8   C10   130.83  3.000
 3DE  H93   C9   H92   107.67  3.000
 3DE  H93   C9   H91   108.61  3.000
 3DE  H92   C9   H91   108.71  3.000
 3DE  H93   C9   C8    110.17  3.000
 3DE  H92   C9   C8    110.00  3.000
 3DE  H91   C9   C8    111.58  3.000
 3DE  C2    N1   C8    129.99  3.000
 3DE  C2    N1   N13   120.88  3.000
 3DE  C8    N1   N13   109.11  3.000
 3DE  C7    C2   C3    122.23  3.000
 3DE  C7    C2   N1    119.00  3.000
 3DE  C3    C2   N1    118.77  3.000
 3DE  H3    C3   C4    121.15  3.000
 3DE  H3    C3   C2    120.25  3.000
 3DE  C4    C3   C2    118.60  3.000
 3DE  H4    C4   C5    120.27  3.000
 3DE  H4    C4   C3    119.69  3.000
 3DE  C5    C4   C3    120.03  3.000
 3DE  H5    C5   C6    119.71  3.000
 3DE  H5    C5   C4    119.76  3.000
 3DE  C6    C5   C4    120.52  3.000
 3DE  H6    C6   C7    119.73  3.000
 3DE  H6    C6   C5    120.21  3.000
 3DE  C7    C6   C5    120.06  3.000
 3DE  H7    C7   C6    121.10  3.000
 3DE  H7    C7   C2    120.35  3.000
 3DE  C6    C7   C2    118.55  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
 3DE  CONST_01  N1    N13  C11  C10     0.00   0.0  0
 3DE  CONST_02  N13   N1   C8   C10     0.00   0.0  0
 3DE  CONST_03  C2    N1   C8   C10   180.00   0.0  0
 3DE  CONST_04  N1    C8   C10  C11     0.00   0.0  0
 3DE  CONST_05  C8    N1   N13  C11     0.00   0.0  0
 3DE  CONST_06  C2    N1   N13  C11   180.00   0.0  0
 3DE  CONST_07  C8    C10  C11  N13     0.00   0.0  0
 3DE  CONST_12  C4    C3   C2   N1    180.00   0.0  0
 3DE  CONST_13  C6    C7   C2   N1    180.00   0.0  0
 3DE  CONST_14  C5    C4   C3   C2      0.00   0.0  0
 3DE  CONST_15  C5    C6   C7   C2      0.00   0.0  0
 3DE  CONST_16  C6    C7   C2   C3      0.00   0.0  0
 3DE  CONST_17  C6    C5   C4   C3      0.00   0.0  0
 3DE  CONST_18  C7    C2   C3   C4      0.00   0.0  0
 3DE  CONST_19  C7    C6   C5   C4      0.00   0.0  0
 3DE  CONST_20  N13   C11  C10  C14   180.00   0.0  0
 3DE  CONST_21  N1    C8   C10  C14   180.00   0.0  0
 3DE  CONST_22  C9    C8   C10  C11   180.00   0.0  0
 3DE  CONST_23  C9    C8   N1   N13   180.00   0.0  0
 3DE  CONST_24  C8    C10  C11  C12   180.00   0.0  0
 3DE  CONST_25  N1    N13  C11  C12   180.00   0.0  0
 3DE  CONST_26  C2    N1   C8   C9      0.00   0.0  0
 3DE  CONST_27  H13   N13  C11  C10   180.00   0.0  0
 3DE  CONST_28  H3    C3   C2   N1      0.00   0.0  0
 3DE  CONST_29  H7    C7   C2   N1      0.00   0.0  0
 3DE  CONST_30  H4    C4   C3   C2    180.00   0.0  0
 3DE  CONST_31  H6    C6   C7   C2    180.00   0.0  0
 3DE  CONST_32  H5    C5   C4   C3    180.00   0.0  0
 3DE  Var_01    C11   C10  C14  O15     0.16  30.0  2
 3DE  Var_02    H121  C12  C11  C10   -60.05  30.0  2
 3DE  Var_03    H91   C9   C8   C10   178.05  30.0  2
 3DE  Var_04    C10   C14  O15  C16  -179.64  30.0  1
 3DE  Var_05    C17   C16  O15  C14  -178.86  30.0  3
 3DE  Var_06    H171  C17  C16  O15  -179.74  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
 3DE  plan-1  C14  0.020
 3DE  plan-1  C10  0.020
 3DE  plan-1  C11  0.020
 3DE  plan-1  N13  0.020
 3DE  plan-1  C12  0.020
 3DE  plan-1  C8   0.020
 3DE  plan-1  C9   0.020
 3DE  plan-1  N1   0.020
 3DE  plan-1  C2   0.020
 3DE  plan-1  H13  0.020
 3DE  plan-2  N1   0.020
 3DE  plan-2  C2   0.020
 3DE  plan-2  C3   0.020
 3DE  plan-2  C4   0.020
 3DE  plan-2  C5   0.020
 3DE  plan-2  C6   0.020
 3DE  plan-2  C7   0.020
 3DE  plan-2  H3   0.020
 3DE  plan-2  H4   0.020
 3DE  plan-2  H5   0.020
 3DE  plan-2  H6   0.020
 3DE  plan-2  H7   0.020
 3DE  plan-3  C14  0.020
 3DE  plan-3  O15  0.020
 3DE  plan-3  C10  0.020
 3DE  plan-3  O1   0.020

