# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 12:29:43 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: 2-chloro-5-(4-methyl-6-oxo-3-phenylpyrano[2,3-c]pyrazol-1(6H)-yl)benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1=CC(=O)Oc2n(nc(c3ccccc3)c12)c4ccc(Cl)c(c4)C(O)=O
#
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
 9ZY  9ZY  '2-chloro-5-(4-methyl-6-oxo-3-phenylpyrano[2,3-c]pyrazol-1(6H)-yl)benzoic acid'  ligand  40  27  .  2022-07-24  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_9ZY
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
 9ZY  O3   O   O     0  -0.415  -5.0496   1.9988   1.3820
 9ZY  C4   C   CR56  0   0.701   0.9595  -1.4216  -0.0082
 9ZY  C5   C   CR56  0  -0.236   2.2612  -0.9803   0.0523
 9ZY  C6   C   CR5   0   0.259   2.1396   0.4279  -0.1157
 9ZY  N1   N   NR5   0  -0.482   0.1542  -0.3707  -0.2136
 9ZY  C7   C   CR6   0   0.388  -1.2518  -0.3170  -0.2826
 9ZY  C8   C   CR16  0  -0.313  -1.9044   0.7728   0.2697
 9ZY  C9   C   CR6   0   0.021  -3.2926   0.8676   0.2297
 9ZY  C10  C   CR6   0  -0.076  -4.0161  -0.1600  -0.3797
 9ZY  C11  C   CR16  0  -0.193  -3.3561  -1.2392  -0.9472
 9ZY  C12  C   CR16  0  -0.295  -1.9764  -1.3236  -0.9055
 9ZY  C13  C   C     0   0.519  -3.9524   2.0297   0.8900
 9ZY  C14  C   CR6   0   0.035   3.1810   1.4637  -0.1397
 9ZY  C15  C   CR16  0  -0.282   3.2260   2.3840  -1.1856
 9ZY  O2   O   OH1   0  -0.587  -3.1736   3.1010   0.8898
 9ZY  CL   CL  CL    0  -0.090  -5.7333  -0.1254  -0.5230
 9ZY  O1   O   O     0  -0.457   0.5445  -2.6674   0.1110
 9ZY  C3   C   CR6   0   0.557   1.4929  -3.6723   0.2785
 9ZY  O    O   O     0  -0.416   1.0611  -4.7876   0.3944
 9ZY  C2   C   CR16  0  -0.558   2.8747  -3.2630   0.2804
 9ZY  N    N   N     0  -0.286   0.8815   0.7671  -0.2723
 9ZY  C1   C   CR6   0   0.203   3.2862  -1.9709   0.1752
 9ZY  C    C   CH3   0  -0.752   4.7338  -1.6198   0.1709
 9ZY  C19  C   CR16  0  -0.293   4.1037   1.5660   0.8993
 9ZY  C18  C   CR16  0  -0.242   5.0665   2.5643   0.8853
 9ZY  C17  C   CR16  0  -0.257   5.1142   3.4715  -0.1651
 9ZY  C16  C   CR16  0  -0.244   4.1911   3.3804  -1.1988
 9ZY  H1   H   HCR6  0   0.298  -1.3245   1.5479   0.7492
 9ZY  H2   H   HCR6  0   0.300  -3.9201  -2.0178  -1.4409
 9ZY  H3   H   HCR6  0   0.299  -1.4902  -2.1630  -1.3806
 9ZY  H4   H   HCR6  0   0.258   2.5126   2.3112  -1.9962
 9ZY  H5   H   HOH1  0   0.493  -3.5973   3.8196   1.3837
 9ZY  H6   H   HCR6  0   0.288   3.5951  -4.0647   0.3651
 9ZY  H7   H   HCH3  0   0.270   5.0189  -1.1704   1.1229
 9ZY  H8   H   HCH3  0   0.271   5.3502  -2.5028   0.0194
 9ZY  H9   H   HCH3  0   0.264   4.9605  -0.8917  -0.6072
 9ZY  H10  H   HCR6  0   0.262   4.0609   0.8747   1.7316
 9ZY  H11  H   HCR6  0   0.262   5.7752   2.6367   1.6996
 9ZY  H12  H   HCR6  0   0.262   5.8671   4.2486  -0.1768
 9ZY  H13  H   HCR6  0   0.262   4.2239   4.0840  -2.0202

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
 9ZY  O3   C13  double    1.203  0.020  1.203
 9ZY  O2   C13  single    1.325  0.020  1.325
 9ZY  C13  C9   single    1.491  0.020  1.491
 9ZY  C16  C15  aromatic  1.387  0.020  1.387
 9ZY  C16  C17  aromatic  1.389  0.020  1.389
 9ZY  C9   C8   aromatic  1.392  0.020  1.392
 9ZY  C9   C10  aromatic  1.397  0.020  1.397
 9ZY  C15  C14  aromatic  1.394  0.020  1.394
 9ZY  C17  C18  aromatic  1.389  0.020  1.389
 9ZY  CL   C10  single    1.724  0.020  1.724
 9ZY  C8   C7   aromatic  1.385  0.020  1.385
 9ZY  C10  C11  aromatic  1.386  0.020  1.386
 9ZY  N    C6   aromatic  1.312  0.020  1.312
 9ZY  N    N1   aromatic  1.352  0.020  1.352
 9ZY  C14  C6   single    1.469  0.020  1.469
 9ZY  C14  C19  aromatic  1.393  0.020  1.393
 9ZY  C18  C19  aromatic  1.387  0.020  1.387
 9ZY  C7   N1   single    1.409  0.020  1.409
 9ZY  C7   C12  aromatic  1.388  0.020  1.388
 9ZY  C6   C5   aromatic  1.423  0.020  1.423
 9ZY  C11  C12  aromatic  1.383  0.020  1.383
 9ZY  N1   C4   aromatic  1.340  0.020  1.340
 9ZY  C5   C4   aromatic  1.376  0.020  1.376
 9ZY  C5   C1   single    1.431  0.020  1.431
 9ZY  C4   O1   single    1.319  0.020  1.319
 9ZY  O1   C3   single    1.392  0.020  1.392
 9ZY  C1   C    single    1.490  0.020  1.490
 9ZY  C1   C2   double    1.360  0.020  1.360
 9ZY  C3   C2   single    1.441  0.020  1.441
 9ZY  C3   O    double    1.202  0.020  1.202
 9ZY  C8   H1   single    0.930  0.020  1.080
 9ZY  C11  H2   single    0.930  0.020  1.080
 9ZY  C12  H3   single    0.930  0.020  1.080
 9ZY  C15  H4   single    0.930  0.020  1.080
 9ZY  O2   H5   single    0.850  0.020  0.980
 9ZY  C2   H6   single    0.930  0.020  1.080
 9ZY  C    H7   single    0.970  0.020  1.090
 9ZY  C    H8   single    0.970  0.020  1.090
 9ZY  C    H9   single    0.970  0.020  1.090
 9ZY  C19  H10  single    0.930  0.020  1.080
 9ZY  C18  H11  single    0.930  0.020  1.080
 9ZY  C17  H12  single    0.930  0.020  1.080
 9ZY  C16  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
 9ZY  O1   C4   N1   124.45  3.000
 9ZY  O1   C4   C5   126.65  3.000
 9ZY  N1   C4   C5   108.90  3.000
 9ZY  C1   C5   C6   139.14  3.000
 9ZY  C1   C5   C4   117.36  3.000
 9ZY  C6   C5   C4   103.38  3.000
 9ZY  N    C6   C14  119.70  3.000
 9ZY  C14  C6   C5   129.72  3.000
 9ZY  N    C6   C5   110.59  3.000
 9ZY  N    N1   C7   120.19  3.000
 9ZY  C7   N1   C4   129.59  3.000
 9ZY  N    N1   C4   110.08  3.000
 9ZY  C12  C7   C8   120.24  3.000
 9ZY  C12  C7   N1   121.03  3.000
 9ZY  C8   C7   N1   118.73  3.000
 9ZY  H1   C8   C9   119.95  3.000
 9ZY  H1   C8   C7   119.25  3.000
 9ZY  C9   C8   C7   120.79  3.000
 9ZY  C13  C9   C10  122.52  3.000
 9ZY  C10  C9   C8   118.62  3.000
 9ZY  C13  C9   C8   118.80  3.000
 9ZY  CL   C10  C11  117.12  3.000
 9ZY  C11  C10  C9   120.31  3.000
 9ZY  CL   C10  C9   122.52  3.000
 9ZY  H2   C11  C12  119.37  3.000
 9ZY  H2   C11  C10  119.96  3.000
 9ZY  C12  C11  C10  120.67  3.000
 9ZY  H3   C12  C11  118.90  3.000
 9ZY  H3   C12  C7   121.73  3.000
 9ZY  C11  C12  C7   119.35  3.000
 9ZY  O2   C13  C9   111.73  3.000
 9ZY  C9   C13  O3   124.40  3.000
 9ZY  O2   C13  O3   123.87  3.000
 9ZY  C19  C14  C15  119.32  3.000
 9ZY  C19  C14  C6   120.60  3.000
 9ZY  C15  C14  C6   120.04  3.000
 9ZY  H4   C15  C16  119.98  3.000
 9ZY  H4   C15  C14  119.76  3.000
 9ZY  C16  C15  C14  120.25  3.000
 9ZY  H5   O2   C13  110.02  3.000
 9ZY  C3   O1   C4   118.59  3.000
 9ZY  C2   C3   O    127.45  3.000
 9ZY  O    C3   O1   115.91  3.000
 9ZY  C2   C3   O1   116.65  3.000
 9ZY  H6   C2   C1   120.59  3.000
 9ZY  H6   C2   C3   115.37  3.000
 9ZY  C1   C2   C3   124.04  3.000
 9ZY  N1   N    C6   107.05  3.000
 9ZY  C    C1   C2   121.21  3.000
 9ZY  C2   C1   C5   116.59  3.000
 9ZY  C    C1   C5   122.19  3.000
 9ZY  H9   C    H8   108.97  3.000
 9ZY  H9   C    H7   107.08  3.000
 9ZY  H8   C    H7   107.94  3.000
 9ZY  H9   C    C1   111.21  3.000
 9ZY  H8   C    C1   111.09  3.000
 9ZY  H7   C    C1   110.41  3.000
 9ZY  H10  C19  C18  119.65  3.000
 9ZY  H10  C19  C14  120.01  3.000
 9ZY  C18  C19  C14  120.34  3.000
 9ZY  H11  C18  C17  120.20  3.000
 9ZY  H11  C18  C19  119.69  3.000
 9ZY  C17  C18  C19  120.11  3.000
 9ZY  H12  C17  C16  120.10  3.000
 9ZY  H12  C17  C18  120.08  3.000
 9ZY  C16  C17  C18  119.82  3.000
 9ZY  H13  C16  C17  120.15  3.000
 9ZY  H13  C16  C15  119.69  3.000
 9ZY  C17  C16  C15  120.16  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
 9ZY  CONST_01  C6   N    N1   C4      0.00   0.0  0
 9ZY  CONST_04  N    C6   C5   C4      0.00   0.0  0
 9ZY  CONST_05  C14  C6   C5   C4    180.00   0.0  0
 9ZY  CONST_06  N1   N    C6   C5      0.00   0.0  0
 9ZY  CONST_09  N    N1   C4   C5      0.00   0.0  0
 9ZY  CONST_10  C7   N1   C4   C5    180.00   0.0  0
 9ZY  CONST_11  C7   N1   N    C6    180.00   0.0  0
 9ZY  CONST_12  C16  C15  C14  C6    180.00   0.0  0
 9ZY  CONST_13  C18  C19  C14  C6    180.00   0.0  0
 9ZY  CONST_14  N1   C4   C5   C6      0.00   0.0  0
 9ZY  CONST_15  C14  C6   N    N1    180.00   0.0  0
 9ZY  CONST_16  C9   C8   C7   N1    180.00   0.0  0
 9ZY  CONST_17  C11  C12  C7   N1    180.00   0.0  0
 9ZY  CONST_18  C10  C9   C8   C7      0.00   0.0  0
 9ZY  CONST_19  C10  C11  C12  C7      0.00   0.0  0
 9ZY  CONST_20  C11  C10  C9   C8      0.00   0.0  0
 9ZY  CONST_22  C11  C12  C7   C8      0.00   0.0  0
 9ZY  CONST_23  C12  C7   C8   C9      0.00   0.0  0
 9ZY  CONST_24  C12  C11  C10  C9      0.00   0.0  0
 9ZY  CONST_26  C17  C16  C15  C14     0.00   0.0  0
 9ZY  CONST_27  C17  C18  C19  C14     0.00   0.0  0
 9ZY  CONST_28  C18  C17  C16  C15     0.00   0.0  0
 9ZY  CONST_30  C18  C19  C14  C15     0.00   0.0  0
 9ZY  CONST_32  C16  C15  C14  C19     0.00   0.0  0
 9ZY  CONST_33  C16  C17  C18  C19     0.00   0.0  0
 9ZY  CONST_34  O1   C4   N1   C7      0.00   0.0  0
 9ZY  CONST_35  C1   C5   C6   C14     0.00   0.0  0
 9ZY  CONST_36  C13  C9   C8   C7    180.00   0.0  0
 9ZY  CONST_37  CL   C10  C9   C8    180.00   0.0  0
 9ZY  CONST_38  C13  C9   C10  C11   180.00   0.0  0
 9ZY  CONST_39  CL   C10  C11  C12   180.00   0.0  0
 9ZY  CONST_40  H4   C15  C14  C6      0.00   0.0  0
 9ZY  CONST_41  H10  C19  C14  C6      0.00   0.0  0
 9ZY  CONST_42  H1   C8   C7   N1      0.00   0.0  0
 9ZY  CONST_43  H3   C12  C7   N1      0.00   0.0  0
 9ZY  CONST_44  H2   C11  C12  C7    180.00   0.0  0
 9ZY  CONST_45  H13  C16  C15  C14   180.00   0.0  0
 9ZY  CONST_46  H11  C18  C19  C14   180.00   0.0  0
 9ZY  CONST_47  H12  C17  C16  C15   180.00   0.0  0
 9ZY  CONST_48  H5   O2   C13  C9    180.00   0.0  0
 9ZY  Var_01    C2   C1   C5   C4     -2.80  30.0  1
 9ZY  Var_02    C2   C3   O1   C4     -1.25  30.0  1
 9ZY  Var_03    C3   C2   C1   C5     -0.20  30.0  1
 9ZY  Var_04    C1   C2   C3   O1      2.29  30.0  1
 9ZY  Var_05    C8   C9   C13  O3   -149.65  30.0  2
 9ZY  Var_06    H7   C    C1   C5     74.74  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
 9ZY  plan-1  N1   0.020
 9ZY  plan-1  C7   0.020
 9ZY  plan-1  C8   0.020
 9ZY  plan-1  C9   0.020
 9ZY  plan-1  C10  0.020
 9ZY  plan-1  C11  0.020
 9ZY  plan-1  C12  0.020
 9ZY  plan-1  C13  0.020
 9ZY  plan-1  CL   0.020
 9ZY  plan-1  H1   0.020
 9ZY  plan-1  H2   0.020
 9ZY  plan-1  H3   0.020
 9ZY  plan-2  C6   0.020
 9ZY  plan-2  C14  0.020
 9ZY  plan-2  C15  0.020
 9ZY  plan-2  C19  0.020
 9ZY  plan-2  C18  0.020
 9ZY  plan-2  C17  0.020
 9ZY  plan-2  C16  0.020
 9ZY  plan-2  H4   0.020
 9ZY  plan-2  H10  0.020
 9ZY  plan-2  H11  0.020
 9ZY  plan-2  H12  0.020
 9ZY  plan-2  H13  0.020
 9ZY  plan-3  C4   0.020
 9ZY  plan-3  C5   0.020
 9ZY  plan-3  C6   0.020
 9ZY  plan-3  N1   0.020
 9ZY  plan-3  C7   0.020
 9ZY  plan-3  C14  0.020
 9ZY  plan-3  O1   0.020
 9ZY  plan-3  N    0.020
 9ZY  plan-3  C1   0.020
 9ZY  plan-4  O3   0.020
 9ZY  plan-4  C9   0.020
 9ZY  plan-4  C13  0.020
 9ZY  plan-4  O2   0.020
 9ZY  plan-4  H5   0.020
 9ZY  plan-5  O1   0.020
 9ZY  plan-5  C3   0.020
 9ZY  plan-5  O    0.020
 9ZY  plan-5  C2   0.020

