# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 16 23:24:08 2020
#   Inital geometry file: a 79 line input string
#   Ligand name: ~{N}-ethyl-5-pyridin-3-yl-pyrazolo[1,5-a]pyrimidin-7-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNc1cc(nc2ccnn12)c3cccnc3
#
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
 8HH  8HH  ~{N}-ethyl-5-pyridin-3-yl-pyrazolo[1,5-a]pyrimidin-7-amine  ligand  31  18  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8HH
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
 8HH  C1   C  CH2   0  -0.278  -2.1354  -2.9304  -0.0628
 8HH  C2   C  CR6   0   0.718  -1.4799  -0.5763   0.0330
 8HH  C3   C  CR16  0  -0.502  -0.1080  -0.7801   0.0299
 8HH  C7   C  CR15  0  -0.585  -1.7794   2.9168   0.1463
 8HH  C8   C  CR6   0  -0.039   2.2161   0.1353   0.0700
 8HH  C9   C  CR16  0  -0.171   3.0664   1.1373  -0.3933
 8HH  C10  C  CR16  0  -0.314   4.4322   0.9206  -0.3868
 8HH  C11  C  CR16  0  -0.065   4.9097  -0.2914   0.0912
 8HH  C12  C  CR16  0  -0.100   2.8074  -1.0374   0.5373
 8HH  C    C  CH3   0  -0.696  -3.4131  -3.7188  -0.2672
 8HH  N    N  NH1   0  -0.667  -2.4221  -1.5100  -0.0208
 8HH  N2   N  N     0  -0.437  -1.8824   0.7243   0.0844
 8HH  N3   N  N     0  -0.329  -3.1613   1.1148   0.0948
 8HH  C6   C  CR15  0  -0.004  -3.0910   2.4372   0.1320
 8HH  C5   C  CR56  0   0.580  -0.9882   1.7757   0.1132
 8HH  N1   N  N     0  -0.499   0.3348   1.5817   0.1110
 8HH  C4   C  CR6   0   0.242   0.7514   0.3311   0.0754
 8HH  N4   N  N     0  -0.399   4.1160  -1.2510   0.5507
 8HH  H1   H  HCH2  0   0.246  -1.6465  -3.2400   0.8653
 8HH  H2   H  HCH2  0   0.247  -1.4371  -3.1337  -0.8782
 8HH  H3   H  HCR6  0   0.288   0.2786  -1.7852  -0.0335
 8HH  H4   H  HCR5  0   0.267  -1.4446   3.9395   0.1755
 8HH  H5   H  HCR6  0   0.271   2.6576   2.0684  -0.7614
 8HH  H6   H  HCR6  0   0.275   5.1186   1.6743  -0.7474
 8HH  H7   H  HCR6  0   0.270   5.9747  -0.4936   0.1053
 8HH  H8   H  HCR6  0   0.262   2.1961  -1.8373   0.9411
 8HH  H9   H  HCH3  0   0.240  -3.9051  -3.4379  -1.1985
 8HH  H10  H  HCH3  0   0.251  -3.1845  -4.7820  -0.3137
 8HH  H11  H  HCH3  0   0.240  -4.1119  -3.5627   0.5552
 8HH  H12  H  HNH1  0   0.415  -3.3834  -1.2038   0.0186
 8HH  H13  H  HCR5  0   0.273  -4.0026   3.0157   0.1482

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
 8HH  C6   C7   aromatic  1.397  0.020  1.397
 8HH  C6   N3   aromatic  1.325  0.020  1.325
 8HH  C7   C5   aromatic  1.389  0.020  1.389
 8HH  N3   N2   aromatic  1.337  0.020  1.337
 8HH  C5   N2   aromatic  1.380  0.020  1.380
 8HH  C5   N1   aromatic  1.337  0.020  1.337
 8HH  N2   C2   aromatic  1.362  0.020  1.362
 8HH  N1   C4   aromatic  1.319  0.020  1.319
 8HH  C2   N    single    1.328  0.020  1.328
 8HH  C2   C3   aromatic  1.387  0.020  1.387
 8HH  C4   C3   aromatic  1.406  0.020  1.406
 8HH  C4   C8   single    1.478  0.020  1.478
 8HH  N    C1   single    1.450  0.020  1.450
 8HH  C12  C8   aromatic  1.394  0.020  1.394
 8HH  C12  N4   aromatic  1.326  0.020  1.326
 8HH  C8   C9   aromatic  1.393  0.020  1.393
 8HH  C    C1   single    1.515  0.020  1.515
 8HH  N4   C11  aromatic  1.327  0.020  1.327
 8HH  C9   C10  aromatic  1.383  0.020  1.383
 8HH  C11  C10  aromatic  1.388  0.020  1.388
 8HH  C1   H1   single    0.970  0.020  1.090
 8HH  C1   H2   single    0.970  0.020  1.090
 8HH  C3   H3   single    0.930  0.020  1.080
 8HH  C7   H4   single    0.930  0.020  1.080
 8HH  C9   H5   single    0.930  0.020  1.080
 8HH  C10  H6   single    0.930  0.020  1.080
 8HH  C11  H7   single    0.930  0.020  1.080
 8HH  C12  H8   single    0.930  0.020  1.080
 8HH  C    H9   single    0.970  0.020  1.090
 8HH  C    H10  single    0.970  0.020  1.090
 8HH  C    H11  single    0.970  0.020  1.090
 8HH  N    H12  single    0.860  0.020  1.020
 8HH  C6   H13  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
 8HH  H2   C1   H1   107.15  3.000
 8HH  H2   C1   N    109.29  3.000
 8HH  H1   C1   N    109.95  3.000
 8HH  H2   C1   C    109.97  3.000
 8HH  H1   C1   C    110.13  3.000
 8HH  N    C1   C    110.30  3.000
 8HH  N2   C2   N    117.60  3.000
 8HH  N    C2   C3   126.77  3.000
 8HH  N2   C2   C3   115.63  3.000
 8HH  H3   C3   C4   121.29  3.000
 8HH  H3   C3   C2   119.44  3.000
 8HH  C4   C3   C2   119.25  3.000
 8HH  H4   C7   C5   127.15  3.000
 8HH  H4   C7   C6   128.22  3.000
 8HH  C5   C7   C6   104.63  3.000
 8HH  C4   C8   C12  122.05  3.000
 8HH  C12  C8   C9   117.23  3.000
 8HH  C4   C8   C9   120.71  3.000
 8HH  H5   C9   C10  120.65  3.000
 8HH  H5   C9   C8   120.11  3.000
 8HH  C10  C9   C8   119.24  3.000
 8HH  H6   C10  C11  120.35  3.000
 8HH  H6   C10  C9   121.08  3.000
 8HH  C11  C10  C9   118.58  3.000
 8HH  H7   C11  N4   116.62  3.000
 8HH  H7   C11  C10  120.36  3.000
 8HH  N4   C11  C10  123.02  3.000
 8HH  H8   C12  N4   115.69  3.000
 8HH  H8   C12  C8   120.41  3.000
 8HH  N4   C12  C8   123.88  3.000
 8HH  H11  C    H10  107.86  3.000
 8HH  H11  C    H9   108.56  3.000
 8HH  H10  C    H9   108.06  3.000
 8HH  H11  C    C1   111.36  3.000
 8HH  H10  C    C1   109.68  3.000
 8HH  H9   C    C1   111.21  3.000
 8HH  H12  N    C2   117.44  3.000
 8HH  H12  N    C1   119.12  3.000
 8HH  C2   N    C1   123.36  3.000
 8HH  C5   N2   N3   113.39  3.000
 8HH  C5   N2   C2   122.45  3.000
 8HH  N3   N2   C2   124.16  3.000
 8HH  C6   N3   N2   103.94  3.000
 8HH  H13  C6   N3   119.37  3.000
 8HH  H13  C6   C7   127.50  3.000
 8HH  N3   C6   C7   113.14  3.000
 8HH  N1   C5   N2   122.03  3.000
 8HH  N1   C5   C7   133.07  3.000
 8HH  N2   C5   C7   104.90  3.000
 8HH  C4   N1   C5   116.76  3.000
 8HH  N1   C4   C8   116.04  3.000
 8HH  C8   C4   C3   120.08  3.000
 8HH  N1   C4   C3   123.88  3.000
 8HH  C12  N4   C11  118.04  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
 8HH  CONST_01  C6   N3   N2   C2    180.00   0.0  0
 8HH  CONST_02  C7   C5   N2   C2    180.00   0.0  0
 8HH  CONST_03  N1   C5   N2   C2      0.00   0.0  0
 8HH  CONST_04  N1   C4   C3   C2      0.00   0.0  0
 8HH  CONST_05  C8   C4   C3   C2    180.00   0.0  0
 8HH  CONST_06  N3   N2   C2   C3    180.00   0.0  0
 8HH  CONST_07  C5   N2   C2   C3      0.00   0.0  0
 8HH  CONST_08  C5   N1   C4   C3      0.00   0.0  0
 8HH  CONST_11  N2   N3   C6   C7      0.00   0.0  0
 8HH  CONST_12  N3   N2   C5   C7      0.00   0.0  0
 8HH  CONST_13  C4   N1   C5   C7    180.00   0.0  0
 8HH  CONST_14  C5   N1   C4   C8    180.00   0.0  0
 8HH  CONST_15  C11  N4   C12  C8      0.00   0.0  0
 8HH  CONST_16  C11  C10  C9   C8      0.00   0.0  0
 8HH  CONST_18  N4   C12  C8   C9      0.00   0.0  0
 8HH  CONST_19  N4   C11  C10  C9      0.00   0.0  0
 8HH  CONST_20  C4   C8   C9   C10   180.00   0.0  0
 8HH  CONST_21  C12  C8   C9   C10     0.00   0.0  0
 8HH  CONST_22  C12  N4   C11  C10     0.00   0.0  0
 8HH  CONST_24  C6   C7   C5   N2      0.00   0.0  0
 8HH  CONST_25  C4   N1   C5   N2      0.00   0.0  0
 8HH  CONST_26  C4   C3   C2   N2      0.00   0.0  0
 8HH  CONST_27  C5   C7   C6   N3      0.00   0.0  0
 8HH  CONST_28  N1   C5   N2   N3    180.00   0.0  0
 8HH  CONST_29  N1   C5   C7   C6    180.00   0.0  0
 8HH  CONST_30  C5   N2   N3   C6      0.00   0.0  0
 8HH  CONST_31  N4   C12  C8   C4    180.00   0.0  0
 8HH  CONST_32  N3   N2   C2   N       0.00   0.0  0
 8HH  CONST_33  C5   N2   C2   N     180.00   0.0  0
 8HH  CONST_34  C4   C3   C2   N     180.00   0.0  0
 8HH  CONST_35  H3   C3   C4   C8      0.00   0.0  0
 8HH  CONST_36  H6   C10  C9   C8    180.00   0.0  0
 8HH  CONST_37  H8   C12  C8   C9    180.00   0.0  0
 8HH  CONST_38  H7   C11  C10  C9    180.00   0.0  0
 8HH  CONST_39  H5   C9   C10  C11   180.00   0.0  0
 8HH  CONST_40  H13  C6   N3   N2    180.00   0.0  0
 8HH  CONST_41  H4   C7   C5   N2    180.00   0.0  0
 8HH  CONST_42  N2   C2   N    C1    180.00   0.0  0
 8HH  CONST_43  C3   C2   N    C1      0.00   0.0  0
 8HH  CONST_44  H12  N    C2   C3    180.00   0.0  0
 8HH  Var_01    C    C1   N    C2   -174.04  30.0  3
 8HH  Var_02    H9   C    C1   N      59.60  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
 8HH  plan-1  C8   0.020
 8HH  plan-1  C9   0.020
 8HH  plan-1  C10  0.020
 8HH  plan-1  C11  0.020
 8HH  plan-1  C12  0.020
 8HH  plan-1  C4   0.020
 8HH  plan-1  N4   0.020
 8HH  plan-1  H5   0.020
 8HH  plan-1  H6   0.020
 8HH  plan-1  H7   0.020
 8HH  plan-1  H8   0.020
 8HH  plan-2  C2   0.020
 8HH  plan-2  C3   0.020
 8HH  plan-2  C7   0.020
 8HH  plan-2  C8   0.020
 8HH  plan-2  N    0.020
 8HH  plan-2  N2   0.020
 8HH  plan-2  N3   0.020
 8HH  plan-2  C6   0.020
 8HH  plan-2  C5   0.020
 8HH  plan-2  N1   0.020
 8HH  plan-2  C4   0.020
 8HH  plan-2  H3   0.020
 8HH  plan-2  H4   0.020
 8HH  plan-2  H13  0.020
 8HH  plan-3  C1   0.020
 8HH  plan-3  C2   0.020
 8HH  plan-3  N    0.020
 8HH  plan-3  H12  0.020

