# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 24 01:30:29 2020
#   Inital geometry file: a 120 line input string
#   Ligand name: 2-(2-chlorophenyl)-N-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-1,3-thiazole-5-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1ccc(cc1NC(=O)c2sc(nc2)c3ccccc3Cl)C(=O)NC4CC4
#
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
 1R9  1R9  2-(2-chlorophenyl)-N-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-1,3-thiazole-5-carboxamide  ligand  46  28  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1R9
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
 1R9  C1   C   CR6   0   0.072  -2.4651   2.5213   0.5566
 1R9  C2   C   CR6   0   0.324  -2.1419   1.2626   0.0352
 1R9  C3   C   CR16  0  -0.297  -3.1325   0.4079  -0.4258
 1R9  C4   C   CR6   0  -0.051  -4.4724   0.7685  -0.3362
 1R9  C5   C   CR16  0  -0.291  -4.8046   2.0189   0.1762
 1R9  C6   C   CR16  0  -0.295  -3.8072   2.8808   0.6025
 1R9  C7   C   CH3   0  -0.751  -1.3986   3.4555   1.0418
 1R9  C8   C   C     0   0.536  -5.4917  -0.1978  -0.8506
 1R9  N9   N   NH1   0  -0.658  -6.7165  -0.1118  -0.3030
 1R9  O10  O   O     0  -0.483  -5.2100  -1.0179  -1.7125
 1R9  C11  C   CH1   0  -0.078  -7.8042  -0.9246  -0.7374
 1R9  C12  C   CH2   0  -0.516  -8.7811  -1.3855   0.2937
 1R9  C13  C   CH2   0  -0.482  -7.8482  -2.3680  -0.3454
 1R9  C14  C   C     0   0.548  -0.2819  -0.2888   0.3937
 1R9  C15  C   CR5   0  -0.388   1.1848  -0.4431   0.3161
 1R9  C16  C   CR15  0   0.025   1.8610  -1.5690   0.6942
 1R9  N17  N   N     0  -0.354   3.2064  -1.5244   0.5669
 1R9  C18  C   CR5   0   0.033   3.6008  -0.3816   0.0941
 1R9  S19  S   S2    0   0.268   2.3196   0.7329  -0.2200
 1R9  C20  C   CR6   0   0.159   4.9867  -0.0035  -0.1911
 1R9  C21  C   CR16  0  -0.311   5.2856   0.6267  -1.4009
 1R9  C22  C   CR16  0  -0.228   6.5813   0.9970  -1.7167
 1R9  C23  C   CR16  0  -0.260   7.6068   0.7397  -0.8190
 1R9  C24  C   CR16  0  -0.192   7.3336   0.1223   0.3920
 1R9  C25  C   CR6   0  -0.091   6.0335  -0.2457   0.7023
 1R9  N26  N   NH1   0  -0.774  -0.7831   0.8961  -0.0357
 1R9  O27  O   O     0  -0.448  -0.9693  -1.1934   0.8298
 1R9  CL1  CL  CL    0  -0.110   5.7431  -0.9600   2.2480
 1R9  H1   H   HCR6  0   0.268  -2.8657  -0.5426  -0.8644
 1R9  H2   H   HCR6  0   0.260  -5.8335   2.3518   0.2252
 1R9  H3   H   HCR6  0   0.262  -4.0790   3.8550   0.9886
 1R9  H4   H   HCH3  0   0.256  -0.7678   3.8085   0.2219
 1R9  H5   H   HCH3  0   0.265  -1.8357   4.3338   1.5124
 1R9  H6   H   HCH3  0   0.256  -0.7432   2.9745   1.7700
 1R9  H7   H   HNH1  0   0.409  -6.8879   0.5532   0.4330
 1R9  H8   H   HCH1  0   0.270  -8.2018  -0.6691  -1.7146
 1R9  H9   H   HCH2  0   0.259  -8.5938  -1.1101   1.3244
 1R9  H10  H   HCH2  0   0.260  -9.8272  -1.4049   0.0189
 1R9  H11  H   HCH2  0   0.255  -8.2481  -3.0708  -1.0646
 1R9  H12  H   HCH2  0   0.256  -7.0308  -2.7494   0.2525
 1R9  H13  H   HCR5  0   0.290   1.3869  -2.4631   1.0722
 1R9  H14  H   HCR6  0   0.274   4.4904   0.8085  -2.1132
 1R9  H15  H   HCR6  0   0.274   6.7889   1.4780  -2.6625
 1R9  H16  H   HCR6  0   0.278   8.6244   1.0199  -1.0551
 1R9  H17  H   HCR6  0   0.288   8.1295  -0.0682   1.0988
 1R9  H18  H   HNH1  0   0.413  -0.1441   1.6225  -0.3215

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
 1R9  C13  C12  single    1.498  0.020  1.498
 1R9  C13  C11  single    1.496  0.020  1.496
 1R9  C12  C11  single    1.493  0.020  1.493
 1R9  C11  N9   single    1.426  0.020  1.426
 1R9  N9   C8   single    1.344  0.020  1.344
 1R9  C8   O10  double    1.223  0.020  1.223
 1R9  C8   C4   single    1.496  0.020  1.496
 1R9  C5   C4   aromatic  1.391  0.020  1.391
 1R9  C5   C6   aromatic  1.385  0.020  1.385
 1R9  C4   C3   aromatic  1.390  0.020  1.390
 1R9  C6   C1   aromatic  1.390  0.020  1.390
 1R9  C3   C2   aromatic  1.387  0.020  1.387
 1R9  C1   C2   aromatic  1.400  0.020  1.400
 1R9  C1   C7   single    1.499  0.020  1.499
 1R9  C2   N26  single    1.409  0.020  1.409
 1R9  N26  C14  single    1.356  0.020  1.356
 1R9  C14  O27  double    1.217  0.020  1.217
 1R9  C14  C15  single    1.477  0.020  1.477
 1R9  C16  C15  aromatic  1.367  0.020  1.367
 1R9  C16  N17  aromatic  1.352  0.020  1.352
 1R9  C15  S19  aromatic  1.720  0.020  1.720
 1R9  N17  C18  aromatic  1.298  0.020  1.298
 1R9  S19  C18  aromatic  1.727  0.020  1.727
 1R9  C18  C20  single    1.465  0.020  1.465
 1R9  CL1  C25  single    1.727  0.020  1.727
 1R9  C20  C25  aromatic  1.397  0.020  1.397
 1R9  C20  C21  aromatic  1.396  0.020  1.396
 1R9  C25  C24  aromatic  1.386  0.020  1.386
 1R9  C21  C22  aromatic  1.384  0.020  1.384
 1R9  C24  C23  aromatic  1.387  0.020  1.387
 1R9  C22  C23  aromatic  1.387  0.020  1.387
 1R9  C3   H1   single    0.930  0.020  1.080
 1R9  C5   H2   single    0.930  0.020  1.080
 1R9  C6   H3   single    0.930  0.020  1.080
 1R9  C7   H4   single    0.970  0.020  1.090
 1R9  C7   H5   single    0.970  0.020  1.090
 1R9  C7   H6   single    0.970  0.020  1.090
 1R9  N9   H7   single    0.860  0.020  1.020
 1R9  C11  H8   single    0.970  0.020  1.090
 1R9  C12  H9   single    0.970  0.020  1.090
 1R9  C12  H10  single    0.970  0.020  1.090
 1R9  C13  H11  single    0.970  0.020  1.090
 1R9  C13  H12  single    0.970  0.020  1.090
 1R9  C16  H13  single    0.930  0.020  1.080
 1R9  C21  H14  single    0.930  0.020  1.080
 1R9  C22  H15  single    0.930  0.020  1.080
 1R9  C23  H16  single    0.930  0.020  1.080
 1R9  C24  H17  single    0.930  0.020  1.080
 1R9  N26  H18  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
 1R9  C7   C1   C6   121.01  3.000
 1R9  C7   C1   C2   121.11  3.000
 1R9  C6   C1   C2   117.88  3.000
 1R9  N26  C2   C3   120.77  3.000
 1R9  N26  C2   C1   118.37  3.000
 1R9  C3   C2   C1   120.85  3.000
 1R9  H1   C3   C4   119.50  3.000
 1R9  H1   C3   C2   120.04  3.000
 1R9  C4   C3   C2   120.46  3.000
 1R9  C8   C4   C5   122.99  3.000
 1R9  C5   C4   C3   119.13  3.000
 1R9  C8   C4   C3   117.83  3.000
 1R9  H2   C5   C6   118.62  3.000
 1R9  H2   C5   C4   121.32  3.000
 1R9  C6   C5   C4   120.03  3.000
 1R9  H3   C6   C5   119.26  3.000
 1R9  H3   C6   C1   119.14  3.000
 1R9  C5   C6   C1   121.60  3.000
 1R9  H6   C7   H5   107.96  3.000
 1R9  H6   C7   H4   107.23  3.000
 1R9  H5   C7   H4   107.19  3.000
 1R9  H6   C7   C1   111.63  3.000
 1R9  H5   C7   C1   110.94  3.000
 1R9  H4   C7   C1   111.67  3.000
 1R9  O10  C8   N9   122.68  3.000
 1R9  O10  C8   C4   121.25  3.000
 1R9  N9   C8   C4   116.07  3.000
 1R9  H7   N9   C11  118.01  3.000
 1R9  H7   N9   C8   119.67  3.000
 1R9  C11  N9   C8   122.31  3.000
 1R9  H8   C11  C13  116.88  3.000
 1R9  H8   C11  C12  117.04  3.000
 1R9  C13  C11  C12   60.14  3.000
 1R9  H8   C11  N9   114.81  3.000
 1R9  C12  C11  N9   117.69  3.000
 1R9  C13  C11  N9   119.51  3.000
 1R9  H10  C12  H9   114.42  3.000
 1R9  H10  C12  C13  118.82  3.000
 1R9  H9   C12  C13  117.71  3.000
 1R9  H10  C12  C11  117.57  3.000
 1R9  H9   C12  C11  117.74  3.000
 1R9  C13  C12  C11   60.03  3.000
 1R9  H12  C13  H11  114.67  3.000
 1R9  H12  C13  C12  117.76  3.000
 1R9  H11  C13  C12  118.64  3.000
 1R9  H12  C13  C11  117.55  3.000
 1R9  H11  C13  C11  117.59  3.000
 1R9  C12  C13  C11   59.83  3.000
 1R9  O27  C14  N26  123.65  3.000
 1R9  O27  C14  C15  120.14  3.000
 1R9  N26  C14  C15  116.21  3.000
 1R9  S19  C15  C16  108.85  3.000
 1R9  S19  C15  C14  126.88  3.000
 1R9  C16  C15  C14  124.26  3.000
 1R9  H13  C16  N17  119.79  3.000
 1R9  H13  C16  C15  124.16  3.000
 1R9  N17  C16  C15  116.05  3.000
 1R9  C18  N17  C16  111.44  3.000
 1R9  C20  C18  S19  120.00  3.000
 1R9  C20  C18  N17  125.85  3.000
 1R9  S19  C18  N17  114.14  3.000
 1R9  C18  S19  C15   89.51  3.000
 1R9  C25  C20  C21  118.15  3.000
 1R9  C21  C20  C18  119.19  3.000
 1R9  C25  C20  C18  122.66  3.000
 1R9  H14  C21  C22  119.50  3.000
 1R9  H14  C21  C20  119.24  3.000
 1R9  C22  C21  C20  121.25  3.000
 1R9  H15  C22  C23  120.44  3.000
 1R9  H15  C22  C21  119.89  3.000
 1R9  C23  C22  C21  119.66  3.000
 1R9  H16  C23  C24  119.44  3.000
 1R9  H16  C23  C22  120.42  3.000
 1R9  C24  C23  C22  120.14  3.000
 1R9  H17  C24  C25  119.82  3.000
 1R9  H17  C24  C23  120.28  3.000
 1R9  C25  C24  C23  119.90  3.000
 1R9  CL1  C25  C24  117.89  3.000
 1R9  C24  C25  C20  120.89  3.000
 1R9  CL1  C25  C20  121.19  3.000
 1R9  H18  N26  C14  118.99  3.000
 1R9  H18  N26  C2   115.96  3.000
 1R9  C14  N26  C2   124.59  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
 1R9  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 1R9  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 1R9  CONST_03  C5   C4   C3   C2      0.00   0.0  0
 1R9  CONST_04  C5   C6   C1   C2      0.00   0.0  0
 1R9  CONST_05  C6   C5   C4   C3      0.00   0.0  0
 1R9  CONST_06  C6   C1   C2   C3      0.00   0.0  0
 1R9  CONST_07  C18  N17  C16  C15     0.00   0.0  0
 1R9  CONST_08  N17  C18  S19  C15     0.00   0.0  0
 1R9  CONST_09  C20  C18  S19  C15   180.00   0.0  0
 1R9  CONST_10  C18  S19  C15  C16     0.00   0.0  0
 1R9  CONST_11  S19  C18  N17  C16     0.00   0.0  0
 1R9  CONST_12  C20  C18  N17  C16   180.00   0.0  0
 1R9  CONST_13  S19  C15  C16  N17     0.00   0.0  0
 1R9  CONST_16  C24  C25  C20  C18   180.00   0.0  0
 1R9  CONST_17  C22  C21  C20  C18   180.00   0.0  0
 1R9  CONST_20  C23  C24  C25  C20     0.00   0.0  0
 1R9  CONST_21  C23  C22  C21  C20     0.00   0.0  0
 1R9  CONST_22  C24  C25  C20  C21     0.00   0.0  0
 1R9  CONST_23  C24  C23  C22  C21     0.00   0.0  0
 1R9  CONST_24  C25  C20  C21  C22     0.00   0.0  0
 1R9  CONST_25  C25  C24  C23  C22     0.00   0.0  0
 1R9  CONST_26  C8   C4   C3   C2    180.00   0.0  0
 1R9  CONST_27  C7   C1   C2   C3    180.00   0.0  0
 1R9  CONST_28  N26  C2   C3   C4    180.00   0.0  0
 1R9  CONST_29  C7   C1   C6   C5    180.00   0.0  0
 1R9  CONST_30  C8   C4   C5   C6    180.00   0.0  0
 1R9  CONST_31  N26  C2   C1   C6    180.00   0.0  0
 1R9  CONST_32  N17  C16  C15  C14   180.00   0.0  0
 1R9  CONST_33  C18  S19  C15  C14   180.00   0.0  0
 1R9  CONST_34  CL1  C25  C20  C18     0.00   0.0  0
 1R9  CONST_35  CL1  C25  C20  C21   180.00   0.0  0
 1R9  CONST_36  CL1  C25  C24  C23   180.00   0.0  0
 1R9  CONST_37  H2   C5   C6   C1    180.00   0.0  0
 1R9  CONST_38  H1   C3   C2   C1    180.00   0.0  0
 1R9  CONST_39  H3   C6   C1   C2    180.00   0.0  0
 1R9  CONST_40  H13  C16  N17  C18   180.00   0.0  0
 1R9  CONST_41  H14  C21  C20  C18     0.00   0.0  0
 1R9  CONST_42  H17  C24  C25  C20   180.00   0.0  0
 1R9  CONST_43  H15  C22  C21  C20   180.00   0.0  0
 1R9  CONST_44  H16  C23  C22  C21   180.00   0.0  0
 1R9  CONST_45  C15  C14  N26  C2    180.00   0.0  0
 1R9  CONST_46  C11  N9   C8   C4    180.00   0.0  0
 1R9  CONST_50  O27  C14  N26  C2      0.00   0.0  0
 1R9  CONST_51  C11  N9   C8   O10     0.00   0.0  0
 1R9  CONST_52  H7   N9   C8   C4      0.00   0.0  0
 1R9  Var_01    C12  C13  C11  N9    106.90  30.0  1
 1R9  Var_02    H9   C12  C13  C11  -107.70  30.0  1
 1R9  Var_03    N9   C8   C4   C3    154.27  30.0  2
 1R9  Var_04    C13  C11  N9   C8     74.91  30.0  1
 1R9  Var_05    N26  C14  C15  C16  -179.49  30.0  2
 1R9  Var_06    H4   C7   C1   C2     66.84  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 1R9  chir_01  C11  C13  C12  N9  both

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
 1R9  plan-1  C14  0.020
 1R9  plan-1  C15  0.020
 1R9  plan-1  C16  0.020
 1R9  plan-1  N17  0.020
 1R9  plan-1  C18  0.020
 1R9  plan-1  S19  0.020
 1R9  plan-1  C20  0.020
 1R9  plan-1  H13  0.020
 1R9  plan-2  C1   0.020
 1R9  plan-2  C2   0.020
 1R9  plan-2  C3   0.020
 1R9  plan-2  C4   0.020
 1R9  plan-2  C5   0.020
 1R9  plan-2  C6   0.020
 1R9  plan-2  C7   0.020
 1R9  plan-2  C8   0.020
 1R9  plan-2  N26  0.020
 1R9  plan-2  H1   0.020
 1R9  plan-2  H2   0.020
 1R9  plan-2  H3   0.020
 1R9  plan-3  C18  0.020
 1R9  plan-3  C20  0.020
 1R9  plan-3  C21  0.020
 1R9  plan-3  C22  0.020
 1R9  plan-3  C23  0.020
 1R9  plan-3  C24  0.020
 1R9  plan-3  C25  0.020
 1R9  plan-3  CL1  0.020
 1R9  plan-3  H14  0.020
 1R9  plan-3  H15  0.020
 1R9  plan-3  H16  0.020
 1R9  plan-3  H17  0.020
 1R9  plan-4  C2   0.020
 1R9  plan-4  C14  0.020
 1R9  plan-4  C15  0.020
 1R9  plan-4  N26  0.020
 1R9  plan-4  O27  0.020
 1R9  plan-4  H18  0.020
 1R9  plan-5  C4   0.020
 1R9  plan-5  C8   0.020
 1R9  plan-5  N9   0.020
 1R9  plan-5  O10  0.020
 1R9  plan-5  C11  0.020
 1R9  plan-5  H7   0.020

