# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 17:05:41 2020
#   Inital geometry file: a 90 line input string
#   Ligand name: ethyl 1-(4-aminophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)c1c(C)nn(c1C)c2ccc(N)cc2
#
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
 5DE  5DE  'ethyl 1-(4-aminophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate'  ligand  36  19  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_5DE
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
 5DE  O19   O  O     0  -0.465   1.4043  -0.0345   3.9178
 5DE  C15   C  C     0   0.515   0.5365  -0.0542   3.0721
 5DE  O16   O  O2    0  -0.463  -0.7595  -0.0735   3.3603
 5DE  C17   C  CH2   0  -0.177  -1.1483  -0.0521   4.7399
 5DE  C18   C  CH3   0  -0.684  -2.6569  -0.0804   4.7896
 5DE  C7    C  CR5   0  -0.399   0.7947  -0.0736   1.6406
 5DE  C8    C  CR5   0   0.321   2.0725  -0.1724   1.0338
 5DE  N10   N  N     0  -0.303   1.9556  -0.1893  -0.2726
 5DE  C9    C  CH3   0  -0.727   3.4131  -0.2621   1.6740
 5DE  C5    C  CR5   0   0.479  -0.1105  -0.0168   0.5850
 5DE  C6    C  CH3   0  -0.742  -1.5877   0.1499   0.5584
 5DE  N4    N  NR5   0  -0.438   0.6374  -0.0990  -0.5292
 5DE  C3    C  CR6   0   0.267   0.2014  -0.1021  -1.8766
 5DE  C2    C  CR16  0  -0.262  -0.6991  -1.0577  -2.3282
 5DE  C1    C  CR16  0  -0.328  -1.1146  -1.0599  -3.6474
 5DE  C11   C  CR16  0  -0.263   0.6979   0.8430  -2.7656
 5DE  C12   C  CR16  0  -0.330   0.2972   0.8353  -4.0880
 5DE  C13   C  CR6   0   0.321  -0.6206  -0.1157  -4.5574
 5DE  N14   N  NH2   0  -0.858  -0.9807  -0.1536  -5.8802
 5DE  H171  H  HCH2  0   0.232  -0.7598   0.8483   5.2209
 5DE  H172  H  HCH2  0   0.232  -0.7262  -0.9166   5.2570
 5DE  H181  H  HCH3  0   0.237  -2.9814  -0.0613   5.8298
 5DE  H182  H  HCH3  0   0.235  -3.0902   0.7845   4.2873
 5DE  H183  H  HCH3  0   0.235  -3.0555  -0.9854   4.3311
 5DE  H91   H  HCH3  0   0.247   3.4829  -1.1293   2.3301
 5DE  H92   H  HCH3  0   0.243   4.1855  -0.3444   0.9115
 5DE  H93   H  HCH3  0   0.247   3.6225   0.6167   2.2831
 5DE  H61   H  HCH3  0   0.266  -2.0951  -0.7758   0.8311
 5DE  H62   H  HCH3  0   0.268  -1.8987   0.9116   1.2688
 5DE  H63   H  HCH3  0   0.261  -1.9353   0.4448  -0.4290
 5DE  H2    H  HCR6  0   0.272  -1.0802  -1.8128  -1.6519
 5DE  H1    H  HCR6  0   0.264  -1.8188  -1.8122  -3.9816
 5DE  H11   H  HCR6  0   0.267   1.3997   1.5930  -2.4238
 5DE  H12   H  HCR6  0   0.264   0.6952   1.5780  -4.7689
 5DE  H141  H  HNH2  0   0.384  -1.8513  -0.6094  -6.0993
 5DE  H142  H  HNH2  0   0.384  -0.8429   0.6923  -6.4085

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
 5DE  O19  C15   double    1.212  0.020  1.212
 5DE  C15  O16   single    1.328  0.020  1.328
 5DE  C15  C7    single    1.455  0.020  1.455
 5DE  O16  C17   single    1.434  0.020  1.434
 5DE  C17  C18   single    1.510  0.020  1.510
 5DE  C17  H171  single    0.970  0.020  1.090
 5DE  C17  H172  single    0.970  0.020  1.090
 5DE  C18  H181  single    0.970  0.020  1.090
 5DE  C18  H182  single    0.970  0.020  1.090
 5DE  C18  H183  single    0.970  0.020  1.090
 5DE  C7   C8    aromatic  1.418  0.020  1.418
 5DE  C7   C5    aromatic  1.392  0.020  1.392
 5DE  C8   N10   aromatic  1.312  0.020  1.312
 5DE  C8   C9    single    1.488  0.020  1.488
 5DE  N10  N4    aromatic  1.346  0.020  1.346
 5DE  C9   H91   single    0.970  0.020  1.090
 5DE  C9   H92   single    0.970  0.020  1.090
 5DE  C9   H93   single    0.970  0.020  1.090
 5DE  C5   C6    single    1.487  0.020  1.487
 5DE  C5   N4    aromatic  1.344  0.020  1.344
 5DE  C6   H61   single    0.970  0.020  1.090
 5DE  C6   H62   single    0.970  0.020  1.090
 5DE  C6   H63   single    0.970  0.020  1.090
 5DE  N4   C3    single    1.416  0.020  1.416
 5DE  C3   C2    aromatic  1.389  0.020  1.389
 5DE  C3   C11   aromatic  1.389  0.020  1.389
 5DE  C2   C1    aromatic  1.383  0.020  1.383
 5DE  C2   H2    single    0.930  0.020  1.080
 5DE  C1   C13   aromatic  1.401  0.020  1.401
 5DE  C1   H1    single    0.930  0.020  1.080
 5DE  C11  C12   aromatic  1.382  0.020  1.382
 5DE  C11  H11   single    0.930  0.020  1.080
 5DE  C12  C13   aromatic  1.403  0.020  1.403
 5DE  C12  H12   single    0.930  0.020  1.080
 5DE  C13  N14   single    1.371  0.020  1.371
 5DE  N14  H141  single    0.890  0.020  1.040
 5DE  N14  H142  single    0.890  0.020  1.040

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
 5DE  C7    C15  O16   112.75  3.000
 5DE  C7    C15  O19   124.04  3.000
 5DE  O16   C15  O19   123.21  3.000
 5DE  C17   O16  C15   118.26  3.000
 5DE  H172  C17  H171  107.85  3.000
 5DE  H172  C17  C18   110.84  3.000
 5DE  H171  C17  C18   110.88  3.000
 5DE  H172  C17  O16   109.81  3.000
 5DE  H171  C17  O16   109.85  3.000
 5DE  C18   C17  O16   107.60  3.000
 5DE  H183  C18  H182  108.64  3.000
 5DE  H183  C18  H181  107.89  3.000
 5DE  H182  C18  H181  107.91  3.000
 5DE  H183  C18  C17   111.55  3.000
 5DE  H182  C18  C17   111.54  3.000
 5DE  H181  C18  C17   109.18  3.000
 5DE  C5    C7   C8    105.33  3.000
 5DE  C5    C7   C15   129.08  3.000
 5DE  C8    C7   C15   125.59  3.000
 5DE  C9    C8   N10   120.53  3.000
 5DE  C9    C8   C7    129.18  3.000
 5DE  N10   C8   C7    110.29  3.000
 5DE  N4    N10  C8    106.04  3.000
 5DE  H93   C9   H92   108.44  3.000
 5DE  H93   C9   H91   107.04  3.000
 5DE  H92   C9   H91   108.43  3.000
 5DE  H93   C9   C8    111.41  3.000
 5DE  H92   C9   C8    110.02  3.000
 5DE  H91   C9   C8    111.38  3.000
 5DE  N4    C5   C6    123.00  3.000
 5DE  N4    C5   C7    105.32  3.000
 5DE  C6    C5   C7    131.64  3.000
 5DE  H63   C6   H62   108.17  3.000
 5DE  H63   C6   H61   107.97  3.000
 5DE  H62   C6   H61   107.36  3.000
 5DE  H63   C6   C5    111.36  3.000
 5DE  H62   C6   C5    110.56  3.000
 5DE  H61   C6   C5    111.27  3.000
 5DE  C3    N4   C5    128.13  3.000
 5DE  C3    N4   N10   118.86  3.000
 5DE  C5    N4   N10   113.01  3.000
 5DE  C11   C3   C2    119.46  3.000
 5DE  C11   C3   N4    119.82  3.000
 5DE  C2    C3   N4    120.70  3.000
 5DE  H2    C2   C1    119.27  3.000
 5DE  H2    C2   C3    120.33  3.000
 5DE  C1    C2   C3    120.41  3.000
 5DE  H1    C1   C13   119.79  3.000
 5DE  H1    C1   C2    119.38  3.000
 5DE  C13   C1   C2    120.83  3.000
 5DE  H11   C11  C12   119.60  3.000
 5DE  H11   C11  C3    120.06  3.000
 5DE  C12   C11  C3    120.33  3.000
 5DE  H12   C12  C13   119.66  3.000
 5DE  H12   C12  C11   119.42  3.000
 5DE  C13   C12  C11   120.92  3.000
 5DE  N14   C13  C12   120.89  3.000
 5DE  N14   C13  C1    121.01  3.000
 5DE  C12   C13  C1    118.05  3.000
 5DE  H142  N14  H141  112.61  3.000
 5DE  H142  N14  C13   116.55  3.000
 5DE  H141  N14  C13   116.71  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
 5DE  CONST_01  N4    N10  C8   C7      0.00   0.0  0
 5DE  CONST_02  N10   N4   C5   C7      0.00   0.0  0
 5DE  CONST_03  C3    N4   C5   C7    180.00   0.0  0
 5DE  CONST_04  N4    C5   C7   C8      0.00   0.0  0
 5DE  CONST_05  C5    N4   N10  C8      0.00   0.0  0
 5DE  CONST_06  C3    N4   N10  C8    180.00   0.0  0
 5DE  CONST_07  C5    C7   C8   N10     0.00   0.0  0
 5DE  CONST_12  C1    C2   C3   N4    180.00   0.0  0
 5DE  CONST_13  C12   C11  C3   N4    180.00   0.0  0
 5DE  CONST_14  C13   C1   C2   C3      0.00   0.0  0
 5DE  CONST_15  C13   C12  C11  C3      0.00   0.0  0
 5DE  CONST_16  C12   C11  C3   C2      0.00   0.0  0
 5DE  CONST_17  C12   C13  C1   C2      0.00   0.0  0
 5DE  CONST_18  C11   C3   C2   C1      0.00   0.0  0
 5DE  CONST_19  C11   C12  C13  C1      0.00   0.0  0
 5DE  CONST_20  N10   C8   C7   C15   180.00   0.0  0
 5DE  CONST_21  N4    C5   C7   C15   180.00   0.0  0
 5DE  CONST_22  C6    C5   C7   C8    180.00   0.0  0
 5DE  CONST_23  C6    C5   N4   N10   180.00   0.0  0
 5DE  CONST_24  C5    C7   C8   C9    180.00   0.0  0
 5DE  CONST_25  N4    N10  C8   C9    180.00   0.0  0
 5DE  CONST_26  C3    N4   C5   C6      0.00   0.0  0
 5DE  CONST_27  N14   C13  C1   C2    180.00   0.0  0
 5DE  CONST_28  N14   C13  C12  C11   180.00   0.0  0
 5DE  CONST_29  H2    C2   C3   N4      0.00   0.0  0
 5DE  CONST_30  H11   C11  C3   N4      0.00   0.0  0
 5DE  CONST_31  H1    C1   C2   C3    180.00   0.0  0
 5DE  CONST_32  H12   C12  C11  C3    180.00   0.0  0
 5DE  Var_01    C8    C7   C15  O19     4.98  30.0  2
 5DE  Var_02    H91   C9   C8   C7     58.71  30.0  2
 5DE  Var_03    H61   C6   C5   C7    -76.50  30.0  2
 5DE  Var_04    C7    C15  O16  C17  -179.76  30.0  1
 5DE  Var_05    C18   C17  O16  C15   179.99  30.0  3
 5DE  Var_06    H181  C18  C17  O16  -179.80  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
 5DE  plan-1  C15   0.020
 5DE  plan-1  C7    0.020
 5DE  plan-1  C8    0.020
 5DE  plan-1  N10   0.020
 5DE  plan-1  C9    0.020
 5DE  plan-1  C5    0.020
 5DE  plan-1  C6    0.020
 5DE  plan-1  N4    0.020
 5DE  plan-1  C3    0.020
 5DE  plan-2  N4    0.020
 5DE  plan-2  C3    0.020
 5DE  plan-2  C2    0.020
 5DE  plan-2  C1    0.020
 5DE  plan-2  C11   0.020
 5DE  plan-2  C12   0.020
 5DE  plan-2  C13   0.020
 5DE  plan-2  N14   0.020
 5DE  plan-2  H2    0.020
 5DE  plan-2  H1    0.020
 5DE  plan-2  H11   0.020
 5DE  plan-2  H12   0.020
 5DE  plan-3  C13   0.020
 5DE  plan-3  N14   0.020
 5DE  plan-3  H141  0.020
 5DE  plan-3  H142  0.020
 5DE  plan-4  O19   0.020
 5DE  plan-4  C15   0.020
 5DE  plan-4  O16   0.020
 5DE  plan-4  C7    0.020

