# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 22:56:47 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 5-butyl-2-[(4-chloro-2-fluorobenzyl)amino]-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC1=CC(=O)n2nc(NCc3ccc(Cl)cc3F)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
 4W4  4W4  5-butyl-2-[(4-chloro-2-fluorobenzyl)amino]-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile  ligand  43  26  .  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_4W4
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
 4W4  C1   C   CH3   0  -0.663   8.5864   1.7951  -1.4329
 4W4  C2   C   CH2   0  -0.425   7.9567   1.1955  -0.1840
 4W4  C3   C   CH2   0  -0.417   6.5347   0.7073  -0.4299
 4W4  C4   C   CH2   0  -0.534   5.9156   0.0982   0.8320
 4W4  C5   C   CR6   0   0.427   4.5325  -0.4102   0.5977
 4W4  C6   C   CR16  0  -0.547   4.2235  -1.7236   0.4630
 4W4  C7   C   CR6   0   0.579   2.8855  -2.1880   0.2032
 4W4  O8   O   O     0  -0.447   2.5260  -3.3390   0.0724
 4W4  N9   N   N     0  -0.456   1.9654  -1.1366   0.1062
 4W4  N10  N   N     0  -0.350   0.6453  -1.3327  -0.1412
 4W4  C11  C   CR5   0   0.616   0.1163  -0.1310  -0.1498
 4W4  N12  N   NH1   0  -0.680  -1.2058   0.0867  -0.3141
 4W4  C13  C   CH2   0  -0.332  -2.0891  -0.9961  -0.6978
 4W4  C14  C   CR6   0  -0.123  -3.5193  -0.5978  -0.4798
 4W4  C15  C   CR16  0  -0.285  -4.3752  -0.3500  -1.5457
 4W4  C16  C   CR16  0  -0.212  -5.6949   0.0334  -1.3525
 4W4  C17  C   CR6   0  -0.033  -6.1639   0.1739  -0.0573
 4W4  CL1  CL  CL    0  -0.114  -7.8046   0.6500   0.2125
 4W4  C19  C   CR16  0  -0.361  -5.3459  -0.0617   1.0377
 4W4  C20  C   CR6   0   0.546  -4.0411  -0.4412   0.7966
 4W4  F21  F   F     0  -0.299  -3.2488  -0.6766   1.8491
 4W4  C22  C   CR5   0  -0.358   1.1023   0.8832   0.0784
 4W4  C23  C   CSP   0  -0.013   0.9215   2.2694   0.1453
 4W4  N24  N   NS    0  -0.250   0.7547   3.4114   0.2017
 4W4  C25  C   CR56  0   0.800   2.2788   0.1696   0.2365
 4W4  N26  N   NR16  0  -0.728   3.5503   0.5303   0.4804
 4W4  H1   H   HCH3  0   0.230   9.6025   2.1397  -1.2395
 4W4  H2   H   HCH3  0   0.220   8.6331   1.0651  -2.2429
 4W4  H3   H   HCH3  0   0.220   8.0102   2.6500  -1.7913
 4W4  H4   H   HCH2  0   0.221   8.5678   0.3624   0.1761
 4W4  H5   H   HCH2  0   0.221   7.9505   1.9393   0.6179
 4W4  H6   H   HCH2  0   0.230   5.9232   1.5422  -0.7858
 4W4  H7   H   HCH2  0   0.237   6.5342  -0.0416  -1.2266
 4W4  H8   H   HCH2  0   0.274   6.5333  -0.7296   1.1814
 4W4  H9   H   HCH2  0   0.273   5.8962   0.8420   1.6339
 4W4  H10  H   HCR6  0   0.290   5.0024  -2.4666   0.5506
 4W4  H12  H   HNH1  0   0.401  -1.4718   1.0062  -0.6305
 4W4  H13  H   HCH2  0   0.260  -1.9497  -1.2790  -1.7461
 4W4  H14  H   HCH2  0   0.270  -1.8374  -1.8736  -0.1008
 4W4  H15  H   HCR6  0   0.280  -4.0014  -0.4614  -2.5557
 4W4  H16  H   HCR6  0   0.286  -6.3407   0.2196  -2.1989
 4W4  H17  H   HCR6  0   0.302  -5.7091   0.0442   2.0511
 4W4  H11  H   HNR6  0   0.446   3.7683   1.5093   0.6035

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
 4W4  CL1  C17  single    1.729  0.020  1.729
 4W4  N24  C23  triple    1.155  0.020  1.155
 4W4  C17  C19  aromatic  1.387  0.020  1.387
 4W4  C17  C16  aromatic  1.385  0.020  1.385
 4W4  C23  C22  single    1.400  0.020  1.400
 4W4  C19  C20  aromatic  1.380  0.020  1.380
 4W4  C16  C15  aromatic  1.388  0.020  1.388
 4W4  C20  F21  single    1.338  0.020  1.338
 4W4  C20  C14  aromatic  1.388  0.020  1.388
 4W4  C1   C2   single    1.522  0.020  1.522
 4W4  C22  C25  aromatic  1.385  0.020  1.385
 4W4  C22  C11  aromatic  1.433  0.020  1.433
 4W4  C15  C14  aromatic  1.389  0.020  1.389
 4W4  C3   C2   single    1.523  0.020  1.523
 4W4  C3   C4   single    1.532  0.020  1.532
 4W4  C14  C13  single    1.500  0.020  1.500
 4W4  N26  C25  single    1.344  0.020  1.344
 4W4  N26  C5   single    1.365  0.020  1.365
 4W4  N12  C11  single    1.350  0.020  1.350
 4W4  N12  C13  single    1.449  0.020  1.449
 4W4  C25  N9   aromatic  1.350  0.020  1.350
 4W4  C11  N10  aromatic  1.313  0.020  1.313
 4W4  C4   C5   single    1.492  0.020  1.492
 4W4  C5   C6   double    1.356  0.020  1.356
 4W4  N9   N10  aromatic  1.357  0.020  1.357
 4W4  N9   C7   single    1.401  0.020  1.401
 4W4  C6   C7   single    1.440  0.020  1.440
 4W4  C7   O8   double    1.213  0.020  1.213
 4W4  C1   H1   single    0.970  0.020  1.090
 4W4  C1   H2   single    0.970  0.020  1.090
 4W4  C1   H3   single    0.970  0.020  1.090
 4W4  C2   H4   single    0.970  0.020  1.090
 4W4  C2   H5   single    0.970  0.020  1.090
 4W4  C3   H6   single    0.970  0.020  1.090
 4W4  C3   H7   single    0.970  0.020  1.090
 4W4  C4   H8   single    0.970  0.020  1.090
 4W4  C4   H9   single    0.970  0.020  1.090
 4W4  C6   H10  single    0.930  0.020  1.080
 4W4  N12  H12  single    0.890  0.020  1.040
 4W4  C13  H13  single    0.970  0.020  1.090
 4W4  C13  H14  single    0.970  0.020  1.090
 4W4  C15  H15  single    0.930  0.020  1.080
 4W4  C16  H16  single    0.930  0.020  1.080
 4W4  C19  H17  single    0.930  0.020  1.080
 4W4  N26  H11  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
 4W4  H3   C1   H2   107.63  3.000
 4W4  H3   C1   H1   107.62  3.000
 4W4  H2   C1   H1   107.65  3.000
 4W4  H3   C1   C2   111.08  3.000
 4W4  H2   C1   C2   111.30  3.000
 4W4  H1   C1   C2   111.38  3.000
 4W4  H5   C2   H4   106.24  3.000
 4W4  H5   C2   C3   109.33  3.000
 4W4  H4   C2   C3   109.29  3.000
 4W4  H5   C2   C1   109.64  3.000
 4W4  H4   C2   C1   109.82  3.000
 4W4  C3   C2   C1   112.33  3.000
 4W4  H7   C3   H6   106.58  3.000
 4W4  H7   C3   C4   109.13  3.000
 4W4  H6   C3   C4   110.21  3.000
 4W4  H7   C3   C2   109.73  3.000
 4W4  H6   C3   C2   109.24  3.000
 4W4  C4   C3   C2   111.82  3.000
 4W4  H9   C4   H8   106.94  3.000
 4W4  H9   C4   C5   109.29  3.000
 4W4  H8   C4   C5   108.47  3.000
 4W4  H9   C4   C3   109.92  3.000
 4W4  H8   C4   C3   109.69  3.000
 4W4  C5   C4   C3   112.38  3.000
 4W4  N26  C5   C6   119.67  3.000
 4W4  C6   C5   C4   123.84  3.000
 4W4  N26  C5   C4   116.47  3.000
 4W4  H10  C6   C7   117.57  3.000
 4W4  H10  C6   C5   119.61  3.000
 4W4  C7   C6   C5   122.82  3.000
 4W4  N9   C7   O8   120.68  3.000
 4W4  O8   C7   C6   126.94  3.000
 4W4  N9   C7   C6   112.39  3.000
 4W4  C25  N9   N10  112.54  3.000
 4W4  N10  N9   C7   122.90  3.000
 4W4  C25  N9   C7   124.56  3.000
 4W4  C11  N10  N9   105.12  3.000
 4W4  C22  C11  N12  125.39  3.000
 4W4  N12  C11  N10  122.89  3.000
 4W4  C22  C11  N10  111.69  3.000
 4W4  H12  N12  C13  115.95  3.000
 4W4  H12  N12  C11  116.35  3.000
 4W4  C13  N12  C11  120.58  3.000
 4W4  H14  C13  H13  106.67  3.000
 4W4  H14  C13  C14  110.73  3.000
 4W4  H13  C13  C14  109.21  3.000
 4W4  H14  C13  N12  108.40  3.000
 4W4  H13  C13  N12  111.65  3.000
 4W4  C14  C13  N12  110.13  3.000
 4W4  C20  C14  C15  116.99  3.000
 4W4  C15  C14  C13  121.54  3.000
 4W4  C20  C14  C13  121.47  3.000
 4W4  H15  C15  C16  119.12  3.000
 4W4  H15  C15  C14  118.99  3.000
 4W4  C16  C15  C14  121.89  3.000
 4W4  H16  C16  C17  120.84  3.000
 4W4  H16  C16  C15  120.45  3.000
 4W4  C17  C16  C15  118.71  3.000
 4W4  C19  C17  CL1  118.89  3.000
 4W4  C19  C17  C16  121.43  3.000
 4W4  CL1  C17  C16  119.68  3.000
 4W4  H17  C19  C20  120.54  3.000
 4W4  H17  C19  C17  121.66  3.000
 4W4  C20  C19  C17  117.81  3.000
 4W4  F21  C20  C19  118.08  3.000
 4W4  F21  C20  C14  118.74  3.000
 4W4  C19  C20  C14  123.18  3.000
 4W4  C25  C22  C23  127.92  3.000
 4W4  C25  C22  C11  103.77  3.000
 4W4  C23  C22  C11  128.30  3.000
 4W4  N24  C23  C22  180.00  3.000
 4W4  N26  C25  C22  133.32  3.000
 4W4  N26  C25  N9   119.80  3.000
 4W4  C22  C25  N9   106.88  3.000
 4W4  H11  N26  C25  119.09  3.000
 4W4  H11  N26  C5   120.13  3.000
 4W4  C25  N26  C5   120.76  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
 4W4  CONST_01  C11  C22  C25  N9      0.00   0.0  0
 4W4  CONST_02  C22  C11  N10  N9      0.00   0.0  0
 4W4  CONST_03  C25  C22  C11  N10     0.00   0.0  0
 4W4  CONST_04  C22  C25  N9   N10     0.00   0.0  0
 4W4  CONST_05  C25  N9   N10  C11     0.00   0.0  0
 4W4  CONST_06  C17  C19  C20  C14     0.00   0.0  0
 4W4  CONST_07  C17  C16  C15  C14     0.00   0.0  0
 4W4  CONST_08  C19  C17  C16  C15     0.00   0.0  0
 4W4  CONST_09  C19  C20  C14  C15     0.00   0.0  0
 4W4  CONST_10  C20  C19  C17  C16     0.00   0.0  0
 4W4  CONST_11  C20  C14  C15  C16     0.00   0.0  0
 4W4  CONST_12  C23  C22  C25  N9    180.00   0.0  0
 4W4  CONST_13  N12  C11  N10  N9    180.00   0.0  0
 4W4  CONST_14  C23  C22  C11  N10   180.00   0.0  0
 4W4  CONST_15  C25  C22  C11  N12   180.00   0.0  0
 4W4  CONST_16  C19  C20  C14  C13   180.00   0.0  0
 4W4  CONST_17  C16  C15  C14  C13   180.00   0.0  0
 4W4  CONST_18  CL1  C17  C16  C15   180.00   0.0  0
 4W4  CONST_19  F21  C20  C14  C15   180.00   0.0  0
 4W4  CONST_20  F21  C20  C19  C17   180.00   0.0  0
 4W4  CONST_21  C20  C19  C17  CL1   180.00   0.0  0
 4W4  CONST_22  N26  C25  C22  C23     0.00   0.0  0
 4W4  CONST_23  H17  C19  C20  C14   180.00   0.0  0
 4W4  CONST_24  H16  C16  C15  C14   180.00   0.0  0
 4W4  CONST_25  H15  C15  C16  C17   180.00   0.0  0
 4W4  CONST_26  C13  N12  C11  N10     0.00   0.0  0
 4W4  CONST_27  C22  C11  N12  C13   180.00   0.0  0
 4W4  Var_01    N26  C5   C4   C3    -74.32  30.0  3
 4W4  Var_02    C14  C13  N12  C11   165.75  30.0  3
 4W4  Var_03    C20  C14  C13  N12   -69.67  30.0  2
 4W4  Var_04    C5   C4   C3   C2   -178.80  30.0  3
 4W4  Var_05    C4   C3   C2   C1    179.64  30.0  1
 4W4  Var_06    H1   C1   C2   C3    179.96  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
 4W4  plan-1  C13  0.020
 4W4  plan-1  C14  0.020
 4W4  plan-1  C15  0.020
 4W4  plan-1  C16  0.020
 4W4  plan-1  C17  0.020
 4W4  plan-1  CL1  0.020
 4W4  plan-1  C19  0.020
 4W4  plan-1  C20  0.020
 4W4  plan-1  F21  0.020
 4W4  plan-1  H15  0.020
 4W4  plan-1  H16  0.020
 4W4  plan-1  H17  0.020
 4W4  plan-2  C4   0.020
 4W4  plan-2  C5   0.020
 4W4  plan-2  C6   0.020
 4W4  plan-2  C7   0.020
 4W4  plan-2  O8   0.020
 4W4  plan-2  N9   0.020
 4W4  plan-2  N10  0.020
 4W4  plan-2  C11  0.020
 4W4  plan-2  N12  0.020
 4W4  plan-2  C22  0.020
 4W4  plan-2  C23  0.020
 4W4  plan-2  N24  0.020
 4W4  plan-2  C25  0.020
 4W4  plan-2  N26  0.020
 4W4  plan-2  H10  0.020
 4W4  plan-2  H11  0.020
 4W4  plan-3  C11  0.020
 4W4  plan-3  N12  0.020
 4W4  plan-3  C13  0.020
 4W4  plan-3  H12  0.020

