# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 23:37:45 2020
#   Inital geometry file: a 109 line input string
#   Ligand name: 2-[(4-chlorobenzyl)amino]-7-oxo-5-propyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC1=CC(=O)n2nc(NCc3ccc(Cl)cc3)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
 775  775  2-[(4-chlorobenzyl)amino]-7-oxo-5-propyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile  ligand  40  24  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_775
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
 775  C1   C   CH3   0  -0.666   7.9349   1.5286  -1.1474
 775  C2   C   CH2   0  -0.426   6.5156   0.9822  -1.1115
 775  C3   C   CH2   0  -0.528   6.1667   0.4125   0.2684
 775  C4   C   CR6   0   0.424   4.7880  -0.1562   0.3103
 775  C5   C   CR16  0  -0.544   4.5162  -1.4824   0.2265
 775  C6   C   CR6   0   0.579   3.1750  -2.0054   0.2131
 775  O7   O   O     0  -0.447   2.8477  -3.1714   0.1431
 775  N8   N   N     0  -0.456   2.2077  -0.9954   0.2902
 775  N9   N   N     0  -0.347   0.8743  -1.2500   0.3051
 775  C10  C   CR5   0   0.618   0.3017  -0.0716   0.3912
 775  N11  N   NH1   0  -0.685  -1.0382   0.0972   0.3785
 775  C12  C   CH2   0  -0.330  -1.9270  -1.0414   0.4776
 775  C13  C   CR6   0   0.084  -3.3322  -0.6476   0.1146
 775  C14  C   CR16  0  -0.288  -3.6008  -0.0091  -1.0943
 775  C15  C   CR16  0  -0.196  -4.8949   0.3404  -1.4438
 775  C16  C   CR6   0  -0.053  -5.9330   0.0444  -0.5716
 775  CL1  CL  CL    0  -0.130  -7.5557   0.4777  -1.0031
 775  C18  C   CR16  0  -0.195  -5.6940  -0.5888   0.6360
 775  C19  C   CR16  0  -0.313  -4.3896  -0.9277   0.9712
 775  C20  C   CR5   0  -0.359   1.2691   0.9839   0.4526
 775  C21  C   CSP   0  -0.014   1.0445   2.3626   0.5395
 775  N22  N   NS    0  -0.250   0.8467   3.4990   0.6065
 775  C23  C   CR56  0   0.800   2.4838   0.3223   0.3825
 775  N24  N   NR16  0  -0.727   3.7614   0.7393   0.3892
 775  H1   H   HCH3  0   0.225   8.0680   2.3353  -0.4249
 775  H2   H   HCH3  0   0.225   8.6633   0.7504  -0.9136
 775  H3   H   HCH3  0   0.238   8.1746   1.9235  -2.1345
 775  H4   H   HCH2  0   0.234   5.8110   1.7738  -1.3784
 775  H5   H   HCH2  0   0.239   6.3989   0.1958  -1.8607
 775  H6   H   HCH2  0   0.273   6.8748  -0.3749   0.5289
 775  H7   H   HCH2  0   0.271   6.2641   1.1938   1.0275
 775  H8   H   HCR6  0   0.290   5.3290  -2.1908   0.1653
 775  H10  H   HNH1  0   0.399  -1.3811   0.9577   0.7770
 775  H11  H   HCH2  0   0.268  -1.5710  -1.8116  -0.2099
 775  H12  H   HCH2  0   0.253  -1.9109  -1.4845   1.4792
 775  H13  H   HCR6  0   0.265  -2.7915   0.2210  -1.7764
 775  H14  H   HCR6  0   0.280  -5.0925   0.8362  -2.3844
 775  H15  H   HCR6  0   0.280  -6.5078  -0.8126   1.3126
 775  H16  H   HCR6  0   0.266  -4.2000  -1.4184   1.9181
 775  H9   H   HNR6  0   0.446   3.9539   1.7269   0.4811

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
 775  CL1  C16  single    1.734  0.020  1.734
 775  C18  C16  aromatic  1.384  0.020  1.384
 775  C18  C19  aromatic  1.389  0.020  1.389
 775  C16  C15  aromatic  1.388  0.020  1.388
 775  C19  C13  aromatic  1.389  0.020  1.389
 775  C15  C14  aromatic  1.385  0.020  1.385
 775  C13  C14  aromatic  1.393  0.020  1.393
 775  C13  C12  single    1.504  0.020  1.504
 775  C12  N11  single    1.448  0.020  1.448
 775  O7   C6   double    1.213  0.020  1.213
 775  N11  C10  single    1.351  0.020  1.351
 775  N9   C10  aromatic  1.313  0.020  1.313
 775  N9   N8   aromatic  1.358  0.020  1.358
 775  C10  C20  aromatic  1.433  0.020  1.433
 775  C6   N8   single    1.401  0.020  1.401
 775  C6   C5   single    1.440  0.020  1.440
 775  N8   C23  aromatic  1.349  0.020  1.349
 775  C20  C23  aromatic  1.385  0.020  1.385
 775  C20  C21  single    1.400  0.020  1.400
 775  C5   C4   double    1.356  0.020  1.356
 775  C23  N24  single    1.344  0.020  1.344
 775  C21  N22  triple    1.155  0.020  1.155
 775  C1   C2   single    1.521  0.020  1.521
 775  C4   N24  single    1.365  0.020  1.365
 775  C4   C3   single    1.492  0.020  1.492
 775  C2   C3   single    1.533  0.020  1.533
 775  C1   H1   single    0.970  0.020  1.090
 775  C1   H2   single    0.970  0.020  1.090
 775  C1   H3   single    0.970  0.020  1.090
 775  C2   H4   single    0.970  0.020  1.090
 775  C2   H5   single    0.970  0.020  1.090
 775  C3   H6   single    0.970  0.020  1.090
 775  C3   H7   single    0.970  0.020  1.090
 775  C5   H8   single    0.930  0.020  1.080
 775  N11  H10  single    0.890  0.020  1.040
 775  C12  H11  single    0.970  0.020  1.090
 775  C12  H12  single    0.970  0.020  1.090
 775  C14  H13  single    0.930  0.020  1.080
 775  C15  H14  single    0.930  0.020  1.080
 775  C18  H15  single    0.930  0.020  1.080
 775  C19  H16  single    0.930  0.020  1.080
 775  N24  H9   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
 775  H3   C1   H2   107.80  3.000
 775  H3   C1   H1   107.76  3.000
 775  H2   C1   H1   107.69  3.000
 775  H3   C1   C2   110.90  3.000
 775  H2   C1   C2   111.20  3.000
 775  H1   C1   C2   111.33  3.000
 775  H5   C2   H4   106.56  3.000
 775  H5   C2   C3   109.00  3.000
 775  H4   C2   C3   110.01  3.000
 775  H5   C2   C1   110.00  3.000
 775  H4   C2   C1   109.61  3.000
 775  C3   C2   C1   111.53  3.000
 775  H7   C3   H6   106.99  3.000
 775  H7   C3   C4   109.58  3.000
 775  H6   C3   C4   108.54  3.000
 775  H7   C3   C2   109.82  3.000
 775  H6   C3   C2   109.61  3.000
 775  C4   C3   C2   112.16  3.000
 775  N24  C4   C5   119.64  3.000
 775  N24  C4   C3   116.53  3.000
 775  C5   C4   C3   123.79  3.000
 775  H8   C5   C6   117.54  3.000
 775  H8   C5   C4   119.61  3.000
 775  C6   C5   C4   122.85  3.000
 775  N8   C6   O7   120.67  3.000
 775  N8   C6   C5   112.39  3.000
 775  O7   C6   C5   126.94  3.000
 775  C23  N8   N9   112.54  3.000
 775  C23  N8   C6   124.51  3.000
 775  N9   N8   C6   122.94  3.000
 775  C10  N9   N8   105.11  3.000
 775  C20  C10  N11  125.31  3.000
 775  C20  C10  N9   111.69  3.000
 775  N11  C10  N9   122.97  3.000
 775  H10  N11  C12  115.80  3.000
 775  H10  N11  C10  116.12  3.000
 775  C12  N11  C10  120.67  3.000
 775  H12  C12  H11  106.59  3.000
 775  H12  C12  C13  109.90  3.000
 775  H11  C12  C13  109.72  3.000
 775  H12  C12  N11  111.82  3.000
 775  H11  C12  N11  108.14  3.000
 775  C13  C12  N11  110.55  3.000
 775  C19  C13  C14  118.73  3.000
 775  C14  C13  C12  120.64  3.000
 775  C19  C13  C12  120.63  3.000
 775  H13  C14  C15  119.05  3.000
 775  H13  C14  C13  119.98  3.000
 775  C15  C14  C13  120.97  3.000
 775  H14  C15  C16  120.51  3.000
 775  H14  C15  C14  120.38  3.000
 775  C16  C15  C14  119.11  3.000
 775  C18  C16  CL1  119.53  3.000
 775  C18  C16  C15  121.11  3.000
 775  CL1  C16  C15  119.36  3.000
 775  H15  C18  C19  120.34  3.000
 775  H15  C18  C16  120.69  3.000
 775  C19  C18  C16  118.97  3.000
 775  H16  C19  C18  119.07  3.000
 775  H16  C19  C13  119.81  3.000
 775  C18  C19  C13  121.12  3.000
 775  C23  C20  C21  127.91  3.000
 775  C21  C20  C10  128.31  3.000
 775  C23  C20  C10  103.77  3.000
 775  N22  C21  C20  180.00  3.000
 775  N24  C23  C20  133.26  3.000
 775  N24  C23  N8   119.85  3.000
 775  C20  C23  N8   106.89  3.000
 775  H9   N24  C23  119.00  3.000
 775  H9   N24  C4   120.23  3.000
 775  C23  N24  C4   120.75  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
 775  CONST_01  C20  C10  N9   N8      0.00   0.0  0
 775  CONST_02  C10  C20  C23  N8      0.00   0.0  0
 775  CONST_03  C23  C20  C10  N9      0.00   0.0  0
 775  CONST_04  C20  C23  N8   N9      0.00   0.0  0
 775  CONST_05  C23  N8   N9   C10     0.00   0.0  0
 775  CONST_06  C16  C18  C19  C13     0.00   0.0  0
 775  CONST_07  C16  C15  C14  C13     0.00   0.0  0
 775  CONST_08  C18  C16  C15  C14     0.00   0.0  0
 775  CONST_09  C18  C19  C13  C14     0.00   0.0  0
 775  CONST_10  C19  C18  C16  C15     0.00   0.0  0
 775  CONST_11  C19  C13  C14  C15     0.00   0.0  0
 775  CONST_12  N11  C10  N9   N8    180.00   0.0  0
 775  CONST_13  C21  C20  C23  N8    180.00   0.0  0
 775  CONST_14  C21  C20  C10  N9    180.00   0.0  0
 775  CONST_15  C23  C20  C10  N11   180.00   0.0  0
 775  CONST_16  C18  C19  C13  C12   180.00   0.0  0
 775  CONST_17  C15  C14  C13  C12   180.00   0.0  0
 775  CONST_18  CL1  C16  C15  C14   180.00   0.0  0
 775  CONST_19  C19  C18  C16  CL1   180.00   0.0  0
 775  CONST_20  N24  C23  C20  C21     0.00   0.0  0
 775  CONST_21  H15  C18  C19  C13   180.00   0.0  0
 775  CONST_22  H14  C15  C14  C13   180.00   0.0  0
 775  CONST_23  H16  C19  C13  C14   180.00   0.0  0
 775  CONST_24  H13  C14  C15  C16   180.00   0.0  0
 775  CONST_25  C12  N11  C10  N9      0.00   0.0  0
 775  CONST_26  C20  C10  N11  C12   180.00   0.0  0
 775  Var_01    C5   C4   C3   C2    100.75  30.0  2
 775  Var_02    C13  C12  N11  C10  -166.46  30.0  2
 775  Var_03    C19  C13  C12  N11  -127.38  30.0  2
 775  Var_04    C4   C3   C2   C1   -178.67  30.0  3
 775  Var_05    H1   C1   C2   C3    -60.47  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
 775  plan-1  C12  0.020
 775  plan-1  C13  0.020
 775  plan-1  C14  0.020
 775  plan-1  C15  0.020
 775  plan-1  C16  0.020
 775  plan-1  CL1  0.020
 775  plan-1  C18  0.020
 775  plan-1  C19  0.020
 775  plan-1  H13  0.020
 775  plan-1  H14  0.020
 775  plan-1  H15  0.020
 775  plan-1  H16  0.020
 775  plan-2  C3   0.020
 775  plan-2  C4   0.020
 775  plan-2  C5   0.020
 775  plan-2  C6   0.020
 775  plan-2  O7   0.020
 775  plan-2  N8   0.020
 775  plan-2  N9   0.020
 775  plan-2  C10  0.020
 775  plan-2  N11  0.020
 775  plan-2  C20  0.020
 775  plan-2  C21  0.020
 775  plan-2  N22  0.020
 775  plan-2  C23  0.020
 775  plan-2  N24  0.020
 775  plan-2  H8   0.020
 775  plan-2  H9   0.020
 775  plan-3  C10  0.020
 775  plan-3  N11  0.020
 775  plan-3  C12  0.020
 775  plan-3  H10  0.020

