# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Jun  2 12:22:58 2020
#   Inital geometry file: a 62 line input string
#   Ligand name: 1-butyl-1H-pyrazole-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCn1nccc1C(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
 XXB  XXB  '1-butyl-1H-pyrazole-5-carboxylic acid'  ligand  24  12  .  2021-08-25  2021-08-25  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_XXB
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
 XXB  C1   C  C     0   0.522  -1.4265  -1.5298  -0.0406
 XXB  N1   N  NR5   0  -0.336  -0.4339   0.7731   0.4297
 XXB  O1   O  O     0  -0.433  -2.3672  -2.1462  -0.4787
 XXB  C2   C  CR5   0   0.283  -1.4124  -0.0615  -0.0122
 XXB  N2   N  N     0  -0.253  -0.7809   2.0389   0.2891
 XXB  O2   O  OH1   0  -0.591  -0.3366  -2.0985   0.4470
 XXB  C3   C  CR15  0  -0.465  -2.4497   0.7417  -0.4466
 XXB  C4   C  CR15  0  -0.067  -1.9975   2.0421  -0.2339
 XXB  C6   C  CH2   0  -0.428   1.9010   0.2899  -0.2338
 XXB  C7   C  CH2   0  -0.429   3.3055   0.0111   0.2866
 XXB  C8   C  CH3   0  -0.661   4.3229  -0.1402  -0.8353
 XXB  HO2  H  HOH1  0   0.494  -0.4117  -3.0638   0.3931
 XXB  H3   H  HCR5  0   0.280  -3.3944   0.4203  -0.8514
 XXB  H4   H  HCR5  0   0.272  -2.5032   2.9737  -0.4337
 XXB  H5   H  HCH2  0   0.268   1.1992   1.3496   1.5093
 XXB  H5A  H  HCH2  0   0.265   0.8876  -0.3747   1.5647
 XXB  H6   H  HCH2  0   0.229   1.5733  -0.5376  -0.8675
 XXB  H6A  H  HCH2  0   0.229   1.9065   1.1865  -0.8608
 XXB  H7   H  HCH2  0   0.220   3.6147   0.8233   0.9508
 XXB  H7A  H  HCH2  0   0.221   3.2946  -0.8958   0.8986
 XXB  H8   H  HCH3  0   0.219   4.0752  -0.9786  -1.4886
 XXB  H8A  H  HCH3  0   0.219   4.3633   0.7591  -1.4527
 XXB  H8B  H  HCH3  0   0.230   5.3241  -0.3150  -0.4402
 XXB  C5   C  CH2   0  -0.290   0.9123   0.4896   0.9065

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
 XXB  C1  O1   double    1.207  0.020  1.207
 XXB  C1  C2   single    1.469  0.020  1.469
 XXB  C1  O2   single    1.322  0.020  1.322
 XXB  N1  C2   aromatic  1.360  0.020  1.360
 XXB  N1  N2   aromatic  1.320  0.020  1.320
 XXB  N1  C5   single    1.456  0.020  1.456
 XXB  C2  C3   aromatic  1.382  0.020  1.382
 XXB  N2  C4   aromatic  1.324  0.020  1.324
 XXB  C3  C4   aromatic  1.393  0.020  1.393
 XXB  C5  C6   single    1.522  0.020  1.522
 XXB  C6  C7   single    1.524  0.020  1.524
 XXB  C7  C8   single    1.522  0.020  1.522
 XXB  O2  HO2  single    0.850  0.020  0.980
 XXB  C3  H3   single    0.930  0.020  1.080
 XXB  C4  H4   single    0.930  0.020  1.080
 XXB  C5  H5   single    0.970  0.020  1.090
 XXB  C5  H5A  single    0.970  0.020  1.090
 XXB  C6  H6   single    0.970  0.020  1.090
 XXB  C6  H6A  single    0.970  0.020  1.090
 XXB  C7  H7   single    0.970  0.020  1.090
 XXB  C7  H7A  single    0.970  0.020  1.090
 XXB  C8  H8   single    0.970  0.020  1.090
 XXB  C8  H8A  single    0.970  0.020  1.090
 XXB  C8  H8B  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
 XXB  O2   C1  C2   114.51  3.000
 XXB  O2   C1  O1   123.82  3.000
 XXB  C2   C1  O1   121.67  3.000
 XXB  C5   N1  N2   117.69  3.000
 XXB  C5   N1  C2   130.71  3.000
 XXB  N2   N1  C2   111.39  3.000
 XXB  C3   C2  N1   106.59  3.000
 XXB  C3   C2  C1   124.60  3.000
 XXB  N1   C2  C1   128.81  3.000
 XXB  C4   N2  N1   106.61  3.000
 XXB  HO2  O2  C1   110.11  3.000
 XXB  H3   C3  C4   128.37  3.000
 XXB  H3   C3  C2   127.10  3.000
 XXB  C4   C3  C2   104.53  3.000
 XXB  H4   C4  C3   128.74  3.000
 XXB  H4   C4  N2   120.39  3.000
 XXB  C3   C4  N2   110.87  3.000
 XXB  H6A  C6  H6   106.85  3.000
 XXB  H6A  C6  C7   109.94  3.000
 XXB  H6   C6  C7   109.63  3.000
 XXB  H6A  C6  C5   108.97  3.000
 XXB  H6   C6  C5   109.81  3.000
 XXB  C7   C6  C5   111.52  3.000
 XXB  H7A  C7  H7   106.18  3.000
 XXB  H7A  C7  C8   109.67  3.000
 XXB  H7   C7  C8   109.41  3.000
 XXB  H7A  C7  C6   109.49  3.000
 XXB  H7   C7  C6   109.40  3.000
 XXB  C8   C7  C6   112.50  3.000
 XXB  H8B  C8  H8A  107.64  3.000
 XXB  H8B  C8  H8   107.59  3.000
 XXB  H8A  C8  H8   107.62  3.000
 XXB  H8B  C8  C7   111.26  3.000
 XXB  H8A  C8  C7   111.08  3.000
 XXB  H8   C8  C7   111.46  3.000
 XXB  H5A  C5  H5   107.39  3.000
 XXB  H5A  C5  C6   111.35  3.000
 XXB  H5   C5  C6   110.32  3.000
 XXB  H5A  C5  N1   109.40  3.000
 XXB  H5   C5  N1   105.73  3.000
 XXB  C6   C5  N1   112.38  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
 XXB  CONST_01  C4   C3  C2  N1     0.00   0.0  0
 XXB  CONST_02  C3   C4  N2  N1     0.00   0.0  0
 XXB  CONST_03  C4   N2  N1  C2     0.00   0.0  0
 XXB  CONST_04  N2   C4  C3  C2     0.00   0.0  0
 XXB  CONST_05  C3   C2  N1  N2     0.00   0.0  0
 XXB  CONST_06  N2   N1  C2  C1   180.00   0.0  0
 XXB  CONST_07  C4   C3  C2  C1   180.00   0.0  0
 XXB  CONST_08  C5   N1  C2  C3   180.00   0.0  0
 XXB  CONST_09  C5   N1  N2  C4   180.00   0.0  0
 XXB  CONST_10  H3   C3  C2  N1   180.00   0.0  0
 XXB  CONST_11  H4   C4  N2  N1   180.00   0.0  0
 XXB  CONST_12  HO2  O2  C1  C2   180.00   0.0  0
 XXB  Var_01    O1   C1  C2  N1  -179.19  30.0  2
 XXB  Var_02    C6   C5  N1  C2    81.39  30.0  2
 XXB  Var_03    C7   C6  C5  N1   179.32  30.0  3
 XXB  Var_04    C8   C7  C6  C5  -177.84  30.0  3
 XXB  Var_05    H8   C8  C7  C6   -61.29  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
 XXB  plan-1  C1   0.020
 XXB  plan-1  N1   0.020
 XXB  plan-1  C2   0.020
 XXB  plan-1  N2   0.020
 XXB  plan-1  C3   0.020
 XXB  plan-1  C4   0.020
 XXB  plan-1  H3   0.020
 XXB  plan-1  H4   0.020
 XXB  plan-1  C5   0.020
 XXB  plan-2  C1   0.020
 XXB  plan-2  O1   0.020
 XXB  plan-2  C2   0.020
 XXB  plan-2  O2   0.020
 XXB  plan-2  HO2  0.020

