# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 13 01:34:34 2020
#   Inital geometry file: a 80 line input string
#   Ligand name: N-(2-chlorophenyl)pyrazolo[1,5-a]pyridine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccccc1NC(=O)c2cnn3ccccc23
#
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
 9WS  9WS  N-(2-chlorophenyl)pyrazolo[1,5-a]pyridine-3-carboxamide  ligand  29  19  .  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_9WS
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
 9WS  C1    C   CR5   0  -0.370   1.4150  -0.1788  -0.2034
 9WS  C2    C   CR56  0   0.606   2.7060   0.2867   0.0837
 9WS  C3    C   C     0   0.494   0.1909   0.6006  -0.0666
 9WS  C12   C   CR6   0  -0.132  -3.2849  -0.3301   0.3431
 9WS  C13   C   CR16  0  -0.137   4.6374   1.5436   0.7155
 9WS  C14   C   CR16  0  -0.383   5.4529   0.4308   0.4032
 9WS  C16   C   CR16  0  -0.298  -2.5774   1.6961  -0.7141
 9WS  C17   C   CR16  0  -0.213  -4.5872   0.1385   0.4025
 9WS  C18   C   CR16  0  -0.246  -3.8744   2.1762  -0.6393
 9WS  C19   C   CR16  0  -0.273  -4.8831   1.4020  -0.0828
 9WS  N4    N   N     0  -0.402   3.5383  -0.7655  -0.2015
 9WS  N5    N   N     0  -0.290   2.8838  -1.8475  -0.6464
 9WS  C6    C   CR15  0  -0.034   1.6157  -1.4955  -0.6466
 9WS  N7    N   NH1   0  -0.768  -0.9658  -0.0924  -0.2945
 9WS  C8    C   CR6   0   0.446  -2.2560   0.4337  -0.2140
 9WS  C9    C   CR16  0  -0.405   3.2817   1.4805   0.5599
 9WS  C10   C   CR16  0   0.039   4.8864  -0.7155  -0.0534
 9WS  O11   O   O     0  -0.466   0.2030   1.7849   0.2303
 9WS  H1    H   HCR6  0   0.283   5.0955   2.4521   1.0808
 9WS  H2    H   HCR6  0   0.288   6.5249   0.4773   0.5227
 9WS  H3    H   HCR6  0   0.277  -1.8119   2.2987  -1.1788
 9WS  H4    H   HCR6  0   0.282  -5.3620  -0.4805   0.8340
 9WS  H5    H   HCR6  0   0.267  -4.0986   3.1582  -1.0333
 9WS  H6    H   HCR6  0   0.268  -5.8979   1.7721  -0.0312
 9WS  H7    H   HCR5  0   0.279   0.8791  -2.2120  -0.9813
 9WS  H8    H   HNH1  0   0.402  -0.9025  -1.0952  -0.3714
 9WS  H9    H   HCR6  0   0.282   2.6447   2.3194   0.7925
 9WS  H10   H   HCR6  0   0.320   5.4295  -1.6107  -0.3155
 9WS  CL15  CL  CL    0  -0.115  -2.9332  -1.9077   0.9735

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
 9WS  C19  C17   aromatic  1.385  0.020  1.385
 9WS  C19  C18   aromatic  1.388  0.020  1.388
 9WS  C13  C9    aromatic  1.366  0.020  1.366
 9WS  C13  C14   aromatic  1.415  0.020  1.415
 9WS  C17  C12   aromatic  1.385  0.020  1.385
 9WS  C9   C2    aromatic  1.408  0.020  1.408
 9WS  O11  C3    double    1.221  0.020  1.221
 9WS  C18  C16   aromatic  1.385  0.020  1.385
 9WS  C12  CL15  single    1.735  0.020  1.735
 9WS  C12  C8    aromatic  1.397  0.020  1.397
 9WS  C16  C8    aromatic  1.395  0.020  1.395
 9WS  C14  C10   aromatic  1.358  0.020  1.358
 9WS  C8   N7    single    1.396  0.020  1.396
 9WS  C3   N7    single    1.368  0.020  1.368
 9WS  C3   C1    single    1.458  0.020  1.458
 9WS  C2   C1    aromatic  1.402  0.020  1.402
 9WS  C2   N4    aromatic  1.372  0.020  1.372
 9WS  C1   C6    aromatic  1.404  0.020  1.404
 9WS  C10  N4    aromatic  1.357  0.020  1.357
 9WS  N4   N5    aromatic  1.341  0.020  1.341
 9WS  C6   N5    aromatic  1.316  0.020  1.316
 9WS  C13  H1    single    0.930  0.020  1.080
 9WS  C14  H2    single    0.930  0.020  1.080
 9WS  C16  H3    single    0.930  0.020  1.080
 9WS  C17  H4    single    0.930  0.020  1.080
 9WS  C18  H5    single    0.930  0.020  1.080
 9WS  C19  H6    single    0.930  0.020  1.080
 9WS  C6   H7    single    0.930  0.020  1.080
 9WS  N7   H8    single    0.860  0.020  1.020
 9WS  C9   H9    single    0.930  0.020  1.080
 9WS  C10  H10   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
 9WS  C6    C1   C3   130.64  3.000
 9WS  C6    C1   C2   104.15  3.000
 9WS  C3    C1   C2   125.21  3.000
 9WS  C9    C2   N4   118.20  3.000
 9WS  N4    C2   C1   105.16  3.000
 9WS  C9    C2   C1   136.64  3.000
 9WS  O11   C3   N7   122.71  3.000
 9WS  N7    C3   C1   115.07  3.000
 9WS  O11   C3   C1   122.22  3.000
 9WS  CL15  C12  C8   119.52  3.000
 9WS  C8    C12  C17  121.63  3.000
 9WS  CL15  C12  C17  118.85  3.000
 9WS  H1    C13  C9   119.86  3.000
 9WS  H1    C13  C14  119.43  3.000
 9WS  C9    C13  C14  120.71  3.000
 9WS  H2    C14  C10  119.20  3.000
 9WS  H2    C14  C13  120.94  3.000
 9WS  C10   C14  C13  119.86  3.000
 9WS  H3    C16  C8   119.73  3.000
 9WS  H3    C16  C18  119.60  3.000
 9WS  C8    C16  C18  120.66  3.000
 9WS  H4    C17  C19  120.58  3.000
 9WS  H4    C17  C12  119.80  3.000
 9WS  C19   C17  C12  119.62  3.000
 9WS  H5    C18  C19  120.12  3.000
 9WS  H5    C18  C16  119.28  3.000
 9WS  C19   C18  C16  120.59  3.000
 9WS  H6    C19  C18  120.68  3.000
 9WS  H6    C19  C17  119.72  3.000
 9WS  C18   C19  C17  119.60  3.000
 9WS  C10   N4   N5   123.43  3.000
 9WS  N5    N4   C2   113.07  3.000
 9WS  C10   N4   C2   123.49  3.000
 9WS  C6    N5   N4   104.75  3.000
 9WS  H7    C6   N5   118.65  3.000
 9WS  H7    C6   C1   128.48  3.000
 9WS  N5    C6   C1   112.87  3.000
 9WS  H8    N7   C8   115.95  3.000
 9WS  H8    N7   C3   117.63  3.000
 9WS  C8    N7   C3   125.54  3.000
 9WS  N7    C8   C16  122.23  3.000
 9WS  N7    C8   C12  119.84  3.000
 9WS  C16   C8   C12  117.89  3.000
 9WS  H9    C9   C13  121.70  3.000
 9WS  H9    C9   C2   119.39  3.000
 9WS  C13   C9   C2   118.91  3.000
 9WS  H10   C10  N4   116.28  3.000
 9WS  H10   C10  C14  124.89  3.000
 9WS  N4    C10  C14  118.83  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
 9WS  CONST_01  C13   C9   C2   C1   180.00   0.0  0
 9WS  CONST_02  C10   N4   C2   C1   180.00   0.0  0
 9WS  CONST_03  N5    N4   C2   C1     0.00   0.0  0
 9WS  CONST_04  N4    N5   C6   C1     0.00   0.0  0
 9WS  CONST_05  C14   C13  C9   C2     0.00   0.0  0
 9WS  CONST_06  N5    C6   C1   C2     0.00   0.0  0
 9WS  CONST_07  C14   C10  N4   C2     0.00   0.0  0
 9WS  CONST_08  C6    N5   N4   C2     0.00   0.0  0
 9WS  CONST_09  C18   C19  C17  C12    0.00   0.0  0
 9WS  CONST_10  C18   C16  C8   C12    0.00   0.0  0
 9WS  CONST_11  N4    C2   C9   C13    0.00   0.0  0
 9WS  CONST_12  N4    C10  C14  C13    0.00   0.0  0
 9WS  CONST_13  N5    N4   C10  C14  180.00   0.0  0
 9WS  CONST_14  C17   C19  C18  C16    0.00   0.0  0
 9WS  CONST_15  C17   C12  C8   C16    0.00   0.0  0
 9WS  CONST_16  C8    C12  C17  C19    0.00   0.0  0
 9WS  CONST_17  C8    C16  C18  C19    0.00   0.0  0
 9WS  CONST_18  C6    C1   C2   N4     0.00   0.0  0
 9WS  CONST_19  C9    C2   N4   N5   180.00   0.0  0
 9WS  CONST_20  C9    C2   C1   C6   180.00   0.0  0
 9WS  CONST_21  C10   N4   N5   C6   180.00   0.0  0
 9WS  CONST_22  C10   C14  C13  C9     0.00   0.0  0
 9WS  CONST_23  C10   N4   C2   C9     0.00   0.0  0
 9WS  CONST_24  C9    C2   C1   C3     0.00   0.0  0
 9WS  CONST_25  N4    C2   C1   C3   180.00   0.0  0
 9WS  CONST_26  N5    C6   C1   C3   180.00   0.0  0
 9WS  CONST_27  CL15  C12  C8   C16  180.00   0.0  0
 9WS  CONST_28  N7    C8   C12  C17  180.00   0.0  0
 9WS  CONST_29  N7    C8   C16  C18  180.00   0.0  0
 9WS  CONST_30  CL15  C12  C17  C19  180.00   0.0  0
 9WS  CONST_31  H9    C9   C2   C1     0.00   0.0  0
 9WS  CONST_32  H1    C13  C9   C2   180.00   0.0  0
 9WS  CONST_33  H7    C6   C1   C2   180.00   0.0  0
 9WS  CONST_34  H10   C10  N4   C2   180.00   0.0  0
 9WS  CONST_35  H6    C19  C17  C12  180.00   0.0  0
 9WS  CONST_36  H3    C16  C8   C12  180.00   0.0  0
 9WS  CONST_37  H5    C18  C19  C17  180.00   0.0  0
 9WS  CONST_38  H4    C17  C19  C18  180.00   0.0  0
 9WS  CONST_39  H2    C14  C10  N4   180.00   0.0  0
 9WS  CONST_40  C8    N7   C3   C1   180.00   0.0  0
 9WS  CONST_44  O11   C3   N7   C8     0.00   0.0  0
 9WS  Var_01    O11   C3   C1   C2     5.31  30.0  2

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
 9WS  plan-1  C12   0.020
 9WS  plan-1  C16   0.020
 9WS  plan-1  C17   0.020
 9WS  plan-1  C18   0.020
 9WS  plan-1  C19   0.020
 9WS  plan-1  N7    0.020
 9WS  plan-1  C8    0.020
 9WS  plan-1  H3    0.020
 9WS  plan-1  H4    0.020
 9WS  plan-1  H5    0.020
 9WS  plan-1  H6    0.020
 9WS  plan-1  CL15  0.020
 9WS  plan-2  C1    0.020
 9WS  plan-2  C2    0.020
 9WS  plan-2  C3    0.020
 9WS  plan-2  C13   0.020
 9WS  plan-2  C14   0.020
 9WS  plan-2  N4    0.020
 9WS  plan-2  N5    0.020
 9WS  plan-2  C6    0.020
 9WS  plan-2  C9    0.020
 9WS  plan-2  C10   0.020
 9WS  plan-2  H1    0.020
 9WS  plan-2  H2    0.020
 9WS  plan-2  H7    0.020
 9WS  plan-2  H9    0.020
 9WS  plan-2  H10   0.020
 9WS  plan-3  C1    0.020
 9WS  plan-3  C3    0.020
 9WS  plan-3  N7    0.020
 9WS  plan-3  C8    0.020
 9WS  plan-3  O11   0.020
 9WS  plan-3  H8    0.020

