# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 19:36:33 2020
#   Inital geometry file: a 73 line input string
#   Ligand name: 5-ethyl-2-methyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC1=CC(=O)n2nc(C)c(C#N)c2N1
#
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
 4VS  4VS  5-ethyl-2-methyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile  ligand  25  15  .  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 (reasonable std)
;

data_comp_4VS
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
 4VS  N3   N  NS    0  -0.247  -2.5150  -3.0515   0.0334
 4VS  C9   C  CSP   0  -0.025  -2.0944  -1.9765   0.0200
 4VS  C8   C  CR5   0  -0.320  -1.5898  -0.6672   0.0063
 4VS  C6   C  CR5   0   0.365  -2.3121   0.5562   0.1098
 4VS  C7   C  CH3   0  -0.741  -3.7823   0.6991   0.2498
 4VS  N2   N  N     0  -0.292  -1.5090   1.5861   0.0649
 4VS  C10  C  CR56  0   0.793  -0.2672  -0.2746  -0.1046
 4VS  N1   N  N     0  -0.457  -0.2659   1.0767  -0.0669
 4VS  C5   C  CR6   0   0.584   0.8895   1.8761  -0.1568
 4VS  O    O  O     0  -0.438   0.8058   3.0836  -0.1222
 4VS  C4   C  CR16  0  -0.538   2.0869   1.0901  -0.2834
 4VS  N4   N  NR16  0  -0.727   0.8957  -0.9399  -0.2268
 4VS  C3   C  CR6   0   0.418   2.0775  -0.2668  -0.3143
 4VS  C2   C  CH2   0  -0.529   3.3127  -1.1021  -0.3962
 4VS  C1   C  CH3   0  -0.662   3.6561  -1.7460   0.9478
 4VS  H1   H  HCH3  0   0.263  -4.1501   0.1105   1.0902
 4VS  H2   H  HCH3  0   0.268  -4.0538   1.7400   0.4096
 4VS  H3   H  HCH3  0   0.267  -4.2922   0.3433  -0.6463
 4VS  H4   H  HCR6  0   0.292   3.0258   1.6187  -0.3552
 4VS  H6   H  HCH2  0   0.276   3.1753  -1.8738  -1.1575
 4VS  H7   H  HCH2  0   0.276   4.1354  -0.4707  -0.7278
 4VS  H8   H  HCH3  0   0.253   4.5735  -2.3253   0.8557
 4VS  H9   H  HCH3  0   0.241   3.8101  -0.9882   1.7154
 4VS  H10  H  HCH3  0   0.234   2.8718  -2.4211   1.2902
 4VS  H5   H  HNR6  0   0.446   0.8811  -1.9491  -0.2733

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
 4VS  N3   C9   triple    1.154  0.020  1.154
 4VS  C9   C8   single    1.403  0.020  1.403
 4VS  C8   C10  aromatic  1.384  0.020  1.384
 4VS  C8   C6   aromatic  1.425  0.020  1.425
 4VS  C1   C2   single    1.529  0.020  1.529
 4VS  N4   C10  single    1.345  0.020  1.345
 4VS  N4   C3   single    1.363  0.020  1.363
 4VS  C7   C6   single    1.484  0.020  1.484
 4VS  C10  N1   aromatic  1.352  0.020  1.352
 4VS  C2   C3   single    1.493  0.020  1.493
 4VS  C6   N2   aromatic  1.307  0.020  1.307
 4VS  C3   C4   double    1.357  0.020  1.357
 4VS  N1   N2   aromatic  1.350  0.020  1.350
 4VS  N1   C5   single    1.408  0.020  1.408
 4VS  C4   C5   single    1.438  0.020  1.438
 4VS  C5   O    double    1.211  0.020  1.211
 4VS  C7   H1   single    0.970  0.020  1.090
 4VS  C7   H2   single    0.970  0.020  1.090
 4VS  C7   H3   single    0.970  0.020  1.090
 4VS  C4   H4   single    0.930  0.020  1.080
 4VS  C2   H6   single    0.970  0.020  1.090
 4VS  C2   H7   single    0.970  0.020  1.090
 4VS  C1   H8   single    0.970  0.020  1.090
 4VS  C1   H9   single    0.970  0.020  1.090
 4VS  C1   H10  single    0.970  0.020  1.090
 4VS  N4   H5   single    0.860  0.020  1.020

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
 4VS  C8   C9   N3   180.00  3.000
 4VS  C10  C8   C6   104.29  3.000
 4VS  C6   C8   C9   128.19  3.000
 4VS  C10  C8   C9   127.53  3.000
 4VS  N2   C6   C7   122.43  3.000
 4VS  N2   C6   C8   111.26  3.000
 4VS  C7   C6   C8   126.30  3.000
 4VS  H3   C7   H2   108.43  3.000
 4VS  H3   C7   H1   107.43  3.000
 4VS  H2   C7   H1   108.62  3.000
 4VS  H3   C7   C6   110.76  3.000
 4VS  H2   C7   C6   110.70  3.000
 4VS  H1   C7   C6   110.80  3.000
 4VS  N1   N2   C6   105.78  3.000
 4VS  N4   C10  N1   119.74  3.000
 4VS  N1   C10  C8   106.40  3.000
 4VS  N4   C10  C8   133.87  3.000
 4VS  C5   N1   C10  124.51  3.000
 4VS  C5   N1   N2   123.21  3.000
 4VS  C10  N1   N2   112.28  3.000
 4VS  C4   C5   O    127.24  3.000
 4VS  O    C5   N1   120.50  3.000
 4VS  C4   C5   N1   112.25  3.000
 4VS  H4   C4   C3   119.59  3.000
 4VS  H4   C4   C5   117.54  3.000
 4VS  C3   C4   C5   122.87  3.000
 4VS  H5   N4   C3   120.19  3.000
 4VS  H5   N4   C10  119.06  3.000
 4VS  C3   N4   C10  120.74  3.000
 4VS  C2   C3   N4   116.39  3.000
 4VS  C2   C3   C4   123.69  3.000
 4VS  N4   C3   C4   119.89  3.000
 4VS  H7   C2   H6   107.00  3.000
 4VS  H7   C2   C1   110.01  3.000
 4VS  H6   C2   C1   110.07  3.000
 4VS  H7   C2   C3   108.50  3.000
 4VS  H6   C2   C3   109.22  3.000
 4VS  C1   C2   C3   111.90  3.000
 4VS  H10  C1   H9   108.13  3.000
 4VS  H10  C1   H8   107.66  3.000
 4VS  H9   C1   H8   108.09  3.000
 4VS  H10  C1   C2   112.04  3.000
 4VS  H9   C1   C2   110.98  3.000
 4VS  H8   C1   C2   109.80  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
 4VS  CONST_01  N2   N1   C10  C8     0.00   0.0  0
 4VS  CONST_02  N1   N2   C6   C8     0.00   0.0  0
 4VS  CONST_03  N1   C10  C8   C6     0.00   0.0  0
 4VS  CONST_04  C10  N1   N2   C6     0.00   0.0  0
 4VS  CONST_05  C10  C8   C6   N2     0.00   0.0  0
 4VS  CONST_06  N4   C10  C8   C9     0.00   0.0  0
 4VS  CONST_07  N1   C10  C8   C9   180.00   0.0  0
 4VS  CONST_08  N2   C6   C8   C9   180.00   0.0  0
 4VS  CONST_09  C10  C8   C6   C7   180.00   0.0  0
 4VS  CONST_10  N1   N2   C6   C7   180.00   0.0  0
 4VS  Var_01    C1   C2   C3   C4   104.43  30.0  2
 4VS  Var_02    H1   C7   C6   C8    53.62  30.0  2
 4VS  Var_03    H8   C1   C2   C3  -178.58  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
 4VS  plan-1  N3   0.020
 4VS  plan-1  C9   0.020
 4VS  plan-1  C8   0.020
 4VS  plan-1  C6   0.020
 4VS  plan-1  C7   0.020
 4VS  plan-1  N2   0.020
 4VS  plan-1  C10  0.020
 4VS  plan-1  N1   0.020
 4VS  plan-1  C5   0.020
 4VS  plan-1  O    0.020
 4VS  plan-1  C4   0.020
 4VS  plan-1  N4   0.020
 4VS  plan-1  C3   0.020
 4VS  plan-1  C2   0.020
 4VS  plan-1  H4   0.020
 4VS  plan-1  H5   0.020

