# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 13 11:52:49 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  39  27  .  2022-07-24  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_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  -0.576  -4.8577   2.6324   0.2555
 9ZY  C4   C   CR56   0   0.694   0.9554  -1.4158   0.0338
 9ZY  C5   C   CR56   0  -0.235   2.2627  -0.9861   0.0837
 9ZY  C6   C   CR5    0   0.251   2.1533   0.4184  -0.1165
 9ZY  N1   N   NR5    0  -0.475   0.1604  -0.3647  -0.1938
 9ZY  C7   C   C      0   0.364  -1.2487  -0.3096  -0.2815
 9ZY  C8   C   C1     0  -0.333  -1.9189   0.7321   0.3396
 9ZY  C9   C   C      0   0.017  -3.3012   0.8617   0.2460
 9ZY  C10  C   C      0  -0.100  -3.9908  -0.1292  -0.4487
 9ZY  C11  C   C1     0  -0.201  -3.3293  -1.1957  -1.0420
 9ZY  C12  C   C1     0  -0.314  -1.9496  -1.2807  -0.9829
 9ZY  C13  C   C      0   0.382  -3.9515   2.0833   0.8978
 9ZY  C14  C   CR6    0   0.036   3.2033   1.4445  -0.1665
 9ZY  C15  C   CR16   0  -0.283   3.2489   2.3454  -1.2294
 9ZY  O2   O   OC    -1  -0.588  -3.4741   2.4193   1.9955
 9ZY  CL   CL  CL     0  -0.122  -5.7207  -0.1194  -0.5590
 9ZY  O1   O   O      0  -0.455   0.5283  -2.6559   0.1809
 9ZY  C3   C   CR6    0   0.556   1.4661  -3.6641   0.3702
 9ZY  O    O   O      0  -0.420   1.0246  -4.7733   0.5127
 9ZY  C2   C   CR16   0  -0.559   2.8523  -3.2696   0.3612
 9ZY  N    N   N      0  -0.285   0.8969   0.7643  -0.2804
 9ZY  C1   C   CR6    0   0.202   3.2770  -1.9841   0.2266
 9ZY  C    C   CH3    0  -0.752   4.7286  -1.6491   0.2124
 9ZY  C19  C   CR16   0  -0.294   4.1365   1.5573   0.8620
 9ZY  C18  C   CR16   0  -0.242   5.1096   2.5449   0.8210
 9ZY  C17  C   CR16   0  -0.258   5.1572   3.4323  -0.2462
 9ZY  C16  C   CR16   0  -0.244   4.2236   3.3317  -1.2696
 9ZY  H1   H   H      0   0.275  -1.3609   1.4699   0.8999
 9ZY  H2   H   H      0   0.284  -3.8878  -1.9576  -1.5683
 9ZY  H3   H   H      0   0.285  -1.4457  -2.0907  -1.4906
 9ZY  H4   H   HCR6   0   0.257   2.5278   2.2646  -2.0324
 9ZY  H6   H   HCR6   0   0.286   3.5648  -4.0765   0.4622
 9ZY  H7   H   HCH3   0   0.269   5.0221  -1.1896   1.1570
 9ZY  H8   H   HCH3   0   0.270   5.3349  -2.5411   0.0715
 9ZY  H9   H   HCH3   0   0.263   4.9608  -0.9346  -0.5766
 9ZY  H10  H   HCR6   0   0.261   4.0952   0.8815   1.7070
 9ZY  H11  H   HCR6   0   0.262   5.8265   2.6249   1.6274
 9ZY  H12  H   HCR6   0   0.262   5.9179   4.2011  -0.2792
 9ZY  H13  H   HCR6   0   0.261   4.2559   4.0198  -2.1041

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  deloc     1.239  0.020  1.239
 9ZY  O2   C13  deloc     1.243  0.020  1.243
 9ZY  C13  C9   single    1.530  0.020  1.530
 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  1.393  0.020  1.393
 9ZY  C15  C14  aromatic  1.394  0.020  1.394
 9ZY  C17  C18  aromatic  1.389  0.020  1.389
 9ZY  CL   C10  single    1.733  0.020  1.733
 9ZY  C8   C7   aromatic  1.386  0.020  1.386
 9ZY  C10  C11  aromatic  1.388  0.020  1.388
 9ZY  N    C6   aromatic  1.313  0.020  1.313
 9ZY  N    N1   aromatic  1.351  0.020  1.351
 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    1.413  0.020  1.413
 9ZY  C7   C12  aromatic  1.388  0.020  1.388
 9ZY  C6   C5   aromatic  1.423  0.020  1.423
 9ZY  C11  C12  aromatic  1.384  0.020  1.384
 9ZY  N1   C4   aromatic  1.337  0.020  1.337
 9ZY  C5   C4   aromatic  1.377  0.020  1.377
 9ZY  C5   C1   single    1.430  0.020  1.430
 9ZY  C4   O1   single    1.320  0.020  1.320
 9ZY  O1   C3   single    1.390  0.020  1.390
 9ZY  C1   C    single    1.490  0.020  1.490
 9ZY  C1   C2   double    1.361  0.020  1.361
 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  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   124.41  3.000
 9ZY  O1   C4   C5   126.61  3.000
 9ZY  N1   C4   C5   108.98  3.000
 9ZY  C1   C5   C6   139.24  3.000
 9ZY  C1   C5   C4   117.34  3.000
 9ZY  C6   C5   C4   103.29  3.000
 9ZY  N    C6   C14  119.71  3.000
 9ZY  C14  C6   C5   129.74  3.000
 9ZY  N    C6   C5   110.55  3.000
 9ZY  N    N1   C7   120.48  3.000
 9ZY  C7   N1   C4   129.35  3.000
 9ZY  N    N1   C4   110.10  3.000
 9ZY  C12  C7   C8   120.54  3.000
 9ZY  C12  C7   N1   120.52  3.000
 9ZY  C8   C7   N1   118.94  3.000
 9ZY  H1   C8   C9   118.93  3.000
 9ZY  H1   C8   C7   119.71  3.000
 9ZY  C9   C8   C7   121.36  3.000
 9ZY  C13  C9   C10  124.76  3.000
 9ZY  C10  C9   C8   117.33  3.000
 9ZY  C13  C9   C8   117.90  3.000
 9ZY  CL   C10  C11  116.92  3.000
 9ZY  C11  C10  C9   121.59  3.000
 9ZY  CL   C10  C9   121.46  3.000
 9ZY  H2   C11  C12  119.51  3.000
 9ZY  H2   C11  C10  120.21  3.000
 9ZY  C12  C11  C10  120.27  3.000
 9ZY  H3   C12  C11  119.40  3.000
 9ZY  H3   C12  C7   121.76  3.000
 9ZY  C11  C12  C7   118.83  3.000
 9ZY  O2   C13  C9   115.39  3.000
 9ZY  C9   C13  O3   116.36  3.000
 9ZY  O2   C13  O3   128.22  3.000
 9ZY  C19  C14  C15  119.25  3.000
 9ZY  C19  C14  C6   120.68  3.000
 9ZY  C15  C14  C6   120.05  3.000
 9ZY  H4   C15  C16  119.98  3.000
 9ZY  H4   C15  C14  119.71  3.000
 9ZY  C16  C15  C14  120.30  3.000
 9ZY  C3   O1   C4   118.59  3.000
 9ZY  C2   C3   O    127.33  3.000
 9ZY  O    C3   O1   115.95  3.000
 9ZY  C2   C3   O1   116.72  3.000
 9ZY  H6   C2   C1   120.58  3.000
 9ZY  H6   C2   C3   115.41  3.000
 9ZY  C1   C2   C3   124.02  3.000
 9ZY  N1   N    C6   107.07  3.000
 9ZY  C    C1   C2   121.17  3.000
 9ZY  C2   C1   C5   116.61  3.000
 9ZY  C    C1   C5   122.22  3.000
 9ZY  H9   C    H8   108.98  3.000
 9ZY  H9   C    H7   107.07  3.000
 9ZY  H8   C    H7   107.92  3.000
 9ZY  H9   C    C1   111.22  3.000
 9ZY  H8   C    C1   111.10  3.000
 9ZY  H7   C    C1   110.41  3.000
 9ZY  H10  C19  C18  119.62  3.000
 9ZY  H10  C19  C14  119.99  3.000
 9ZY  C18  C19  C14  120.38  3.000
 9ZY  H11  C18  C17  120.18  3.000
 9ZY  H11  C18  C19  119.70  3.000
 9ZY  C17  C18  C19  120.12  3.000
 9ZY  H12  C17  C16  120.10  3.000
 9ZY  H12  C17  C18  120.11  3.000
 9ZY  C16  C17  C18  119.79  3.000
 9ZY  H13  C16  C17  120.14  3.000
 9ZY  H13  C16  C15  119.70  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  Var_01    C2   C1   C5   C4    -2.87  30.0  1
 9ZY  Var_02    C2   C3   O1   C4    -1.33  30.0  1
 9ZY  Var_03    C3   C2   C1   C5    -0.17  30.0  1
 9ZY  Var_04    C1   C2   C3   O1     2.34  30.0  1
 9ZY  Var_05    C8   C9   C13  O3   138.70  30.0  2
 9ZY  Var_06    H7   C    C1   C5    75.20  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-5  O1   0.020
 9ZY  plan-5  C3   0.020
 9ZY  plan-5  O    0.020
 9ZY  plan-5  C2   0.020

