# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 11:04:19 2020
#   Inital geometry file: a 111 line input string
#   Ligand name: N-(4-chloro-3-methoxyphenyl)-2-(4-oxochromeno[4,3-c]pyrazol-1(4H)-yl)acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(NC(=O)Cn2ncc3C(=O)Oc4ccccc4c23)ccc1Cl
#
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
 N09  N09  N-(4-chloro-3-methoxyphenyl)-2-(4-oxochromeno[4,3-c]pyrazol-1(4H)-yl)acetamide  ligand  41  27  .  2021-08-15  2021-08-15  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_N09
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
 N09  O4   O   O     0  -0.417   6.2621   1.1102  -1.4350
 N09  C22  C   CR6   0   0.539   5.3130   0.6564  -0.8511
 N09  C17  C   CR56  0  -0.425   4.1510   1.3599  -0.3953
 N09  C16  C   CR15  0  -0.061   3.7707   2.7113  -0.4819
 N09  N3   N   N     0  -0.240   2.6065   2.8899   0.0864
 N09  O3   O   O     0  -0.475   5.3093  -0.6745  -0.5736
 N09  C20  C   CR66  0   0.329   4.3072  -1.3292   0.0739
 N09  C26  C   CR16  0  -0.318   4.4913  -2.6936   0.2496
 N09  C25  C   CR16  0  -0.253   3.5190  -3.4320   0.8972
 N09  C24  C   CR16  0  -0.246   2.3643  -2.8137   1.3687
 N09  C23  C   CR16  0  -0.314   2.1833  -1.4570   1.1898
 N09  C19  C   CR66  0   0.052   3.1524  -0.6851   0.5410
 N09  C18  C   CR56  0   0.578   3.1145   0.7287   0.2721
 N09  N2   N   NR5   0  -0.384   2.2200   1.6893   0.5541
 N09  C13  C   CH2   0  -0.480   0.9262   1.5769   1.1599
 N09  C11  C   C     0   0.528  -0.0715   0.9240   0.2048
 N09  O2   O   O     0  -0.434   0.2519   0.5732  -0.9096
 N09  N1   N   NH1   0  -0.750  -1.3000   0.7900   0.7519
 N09  C4   C   CR6   0   0.422  -2.4605   0.2519   0.1851
 N09  C3   C   CR16  0  -0.348  -2.4977  -0.4103  -1.0376
 N09  C2   C   CR16  0  -0.196  -3.7100  -0.9129  -1.4920
 N09  C5   C   CR16  0  -0.506  -3.6311   0.3988   0.9342
 N09  C6   C   CR6   0   0.478  -4.8408  -0.1056   0.4776
 N09  C1   C   CR6   0  -0.167  -4.8664  -0.7670  -0.7555
 N09  CL   CL  CL    0  -0.113  -6.3654  -1.3969  -1.3423
 N09  O1   O   O2    0  -0.454  -6.0000  -0.0032   1.1342
 N09  C8   C   CH3   0  -0.443  -6.0165   0.6488   2.3919
 N09  H1   H   HCR5  0   0.290   4.3036   3.5360  -0.9287
 N09  H2   H   HCR6  0   0.288   5.3912  -3.1644  -0.1237
 N09  H3   H   HCR6  0   0.276   3.6616  -4.4951   1.0353
 N09  H4   H   HCR6  0   0.274   1.6039  -3.3915   1.8750
 N09  H5   H   HCR6  0   0.262   1.2808  -1.0067   1.5730
 N09  H6   H   HCH2  0   0.320   0.9887   1.0253   2.0995
 N09  H7   H   HCH2  0   0.345   0.5945   2.5848   1.4107
 N09  H8   H   HNH1  0   0.430  -1.4158   1.1575   1.6861
 N09  H9   H   HCR6  0   0.287  -1.6150  -0.5460  -1.6383
 N09  H10  H   HCR6  0   0.283  -3.7447  -1.4303  -2.4414
 N09  H11  H   HCR6  0   0.304  -3.5835   0.9192   1.8826
 N09  H12  H   HCH3  0   0.267  -7.0461   0.6173   2.7379
 N09  H13  H   HCH3  0   0.236  -5.3814   0.1398   3.1206
 N09  H14  H   HCH3  0   0.236  -5.7019   1.6918   2.3117

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
 N09  CL   C1   single    1.729  0.020  1.729
 N09  C2   C1   aromatic  1.379  0.020  1.379
 N09  C2   C3   aromatic  1.389  0.020  1.389
 N09  C1   C6   aromatic  1.399  0.020  1.399
 N09  C3   C4   aromatic  1.391  0.020  1.391
 N09  C6   O1   single    1.336  0.020  1.336
 N09  C6   C5   aromatic  1.388  0.020  1.388
 N09  C4   C5   aromatic  1.398  0.020  1.398
 N09  C4   N1   single    1.399  0.020  1.399
 N09  O1   C8   single    1.417  0.020  1.417
 N09  N1   C11  single    1.351  0.020  1.351
 N09  C11  C13  single    1.528  0.020  1.528
 N09  C11  O2   double    1.212  0.020  1.212
 N09  C13  N2   single    1.433  0.020  1.433
 N09  N3   N2   aromatic  1.345  0.020  1.345
 N09  N3   C16  aromatic  1.308  0.020  1.308
 N09  N2   C18  aromatic  1.343  0.020  1.343
 N09  C23  C24  aromatic  1.380  0.020  1.380
 N09  C23  C19  aromatic  1.399  0.020  1.399
 N09  C16  C17  aromatic  1.407  0.020  1.407
 N09  C18  C19  aromatic  1.440  0.020  1.440
 N09  C18  C17  aromatic  1.385  0.020  1.385
 N09  C24  C25  aromatic  1.392  0.020  1.392
 N09  C19  C20  aromatic  1.402  0.020  1.402
 N09  C17  C22  single    1.433  0.020  1.433
 N09  C25  C26  aromatic  1.382  0.020  1.382
 N09  C20  C26  aromatic  1.388  0.020  1.388
 N09  C20  O3   single    1.361  0.020  1.361
 N09  C22  O3   single    1.360  0.020  1.360
 N09  C22  O4   double    1.203  0.020  1.203
 N09  C16  H1   single    0.930  0.020  1.080
 N09  C26  H2   single    0.930  0.020  1.080
 N09  C25  H3   single    0.930  0.020  1.080
 N09  C24  H4   single    0.930  0.020  1.080
 N09  C23  H5   single    0.930  0.020  1.080
 N09  C13  H6   single    0.970  0.020  1.090
 N09  C13  H7   single    0.970  0.020  1.090
 N09  N1   H8   single    0.860  0.020  1.020
 N09  C3   H9   single    0.930  0.020  1.080
 N09  C2   H10  single    0.930  0.020  1.080
 N09  C5   H11  single    0.930  0.020  1.080
 N09  C8   H12  single    0.970  0.020  1.090
 N09  C8   H13  single    0.970  0.020  1.090
 N09  C8   H14  single    0.970  0.020  1.090

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
 N09  O3   C22  C17  114.43  3.000
 N09  O3   C22  O4   118.06  3.000
 N09  C17  C22  O4   127.51  3.000
 N09  C18  C17  C16  105.38  3.000
 N09  C18  C17  C22  122.44  3.000
 N09  C16  C17  C22  132.18  3.000
 N09  H1   C16  N3   121.02  3.000
 N09  H1   C16  C17  128.79  3.000
 N09  N3   C16  C17  110.19  3.000
 N09  N2   N3   C16  106.56  3.000
 N09  C20  O3   C22  124.76  3.000
 N09  C19  C20  C26  121.24  3.000
 N09  C26  C20  O3   115.82  3.000
 N09  C19  C20  O3   122.94  3.000
 N09  H2   C26  C25  120.95  3.000
 N09  H2   C26  C20  119.63  3.000
 N09  C25  C26  C20  119.42  3.000
 N09  H3   C25  C24  120.18  3.000
 N09  H3   C25  C26  119.49  3.000
 N09  C24  C25  C26  120.33  3.000
 N09  H4   C24  C23  119.59  3.000
 N09  H4   C24  C25  120.31  3.000
 N09  C23  C24  C25  120.09  3.000
 N09  H5   C23  C19  120.93  3.000
 N09  H5   C23  C24  118.29  3.000
 N09  C19  C23  C24  120.78  3.000
 N09  C18  C19  C23  127.62  3.000
 N09  C18  C19  C20  114.24  3.000
 N09  C23  C19  C20  118.14  3.000
 N09  N2   C18  C19  132.92  3.000
 N09  C19  C18  C17  121.19  3.000
 N09  N2   C18  C17  105.89  3.000
 N09  C13  N2   C18  129.36  3.000
 N09  C18  N2   N3   111.97  3.000
 N09  C13  N2   N3   118.45  3.000
 N09  H7   C13  H6   106.66  3.000
 N09  H7   C13  C11  109.89  3.000
 N09  H6   C13  C11  111.08  3.000
 N09  H7   C13  N2   107.42  3.000
 N09  H6   C13  N2   110.60  3.000
 N09  C11  C13  N2   111.03  3.000
 N09  N1   C11  O2   125.87  3.000
 N09  O2   C11  C13  121.61  3.000
 N09  N1   C11  C13  112.51  3.000
 N09  H8   N1   C4   114.79  3.000
 N09  H8   N1   C11  116.26  3.000
 N09  C4   N1   C11  128.91  3.000
 N09  C5   C4   C3   119.92  3.000
 N09  C5   C4   N1   115.93  3.000
 N09  C3   C4   N1   124.15  3.000
 N09  H9   C3   C2   119.18  3.000
 N09  H9   C3   C4   121.92  3.000
 N09  C2   C3   C4   118.90  3.000
 N09  H10  C2   C1   119.51  3.000
 N09  H10  C2   C3   119.22  3.000
 N09  C1   C2   C3   121.27  3.000
 N09  H11  C5   C6   120.07  3.000
 N09  H11  C5   C4   118.89  3.000
 N09  C6   C5   C4   121.04  3.000
 N09  O1   C6   C1   116.96  3.000
 N09  O1   C6   C5   124.52  3.000
 N09  C1   C6   C5   118.52  3.000
 N09  CL   C1   C6   119.16  3.000
 N09  C6   C1   C2   120.36  3.000
 N09  CL   C1   C2   120.49  3.000
 N09  C8   O1   C6   118.79  3.000
 N09  H14  C8   H13  109.05  3.000
 N09  H14  C8   H12  108.90  3.000
 N09  H13  C8   H12  108.96  3.000
 N09  H14  C8   O1   111.77  3.000
 N09  H13  C8   O1   111.77  3.000
 N09  H12  C8   O1   106.29  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
 N09  CONST_01  N2   N3   C16  C17     0.00   0.0  0
 N09  CONST_02  N3   N2   C18  C17     0.00   0.0  0
 N09  CONST_03  C23  C19  C18  C17   180.00   0.0  0
 N09  CONST_04  C20  C19  C18  C17     0.00   0.0  0
 N09  CONST_05  C18  N2   N3   C16     0.00   0.0  0
 N09  CONST_06  N2   C18  C17  C16     0.00   0.0  0
 N09  CONST_07  C19  C18  C17  C16   180.00   0.0  0
 N09  CONST_08  C19  C18  N2   N3    180.00   0.0  0
 N09  CONST_09  C18  C17  C16  N3      0.00   0.0  0
 N09  CONST_10  C24  C23  C19  C20     0.00   0.0  0
 N09  CONST_11  N2   C18  C19  C20   180.00   0.0  0
 N09  CONST_12  C24  C25  C26  C20     0.00   0.0  0
 N09  CONST_13  C23  C24  C25  C26     0.00   0.0  0
 N09  CONST_14  C23  C19  C20  C26     0.00   0.0  0
 N09  CONST_15  C18  C19  C20  C26   180.00   0.0  0
 N09  CONST_16  C19  C23  C24  C25     0.00   0.0  0
 N09  CONST_17  C19  C20  C26  C25     0.00   0.0  0
 N09  CONST_18  C18  C19  C23  C24   180.00   0.0  0
 N09  CONST_19  N2   C18  C19  C23     0.00   0.0  0
 N09  CONST_20  C1   C2   C3   C4      0.00   0.0  0
 N09  CONST_21  C1   C6   C5   C4      0.00   0.0  0
 N09  CONST_22  C6   C1   C2   C3      0.00   0.0  0
 N09  CONST_23  C6   C5   C4   C3      0.00   0.0  0
 N09  CONST_24  C5   C6   C1   C2      0.00   0.0  0
 N09  CONST_25  C5   C4   C3   C2      0.00   0.0  0
 N09  CONST_26  C13  N2   C18  C17   180.00   0.0  0
 N09  CONST_27  C13  N2   N3   C16   180.00   0.0  0
 N09  CONST_28  C13  N2   C18  C19     0.00   0.0  0
 N09  CONST_29  C2   C3   C4   N1    180.00   0.0  0
 N09  CONST_30  C6   C5   C4   N1    180.00   0.0  0
 N09  CONST_31  O1   C6   C5   C4    180.00   0.0  0
 N09  CONST_32  CL   C1   C2   C3    180.00   0.0  0
 N09  CONST_33  O1   C6   C1   C2    180.00   0.0  0
 N09  CONST_34  CL   C1   C6   C5    180.00   0.0  0
 N09  CONST_35  H1   C16  C17  C22     0.00   0.0  0
 N09  CONST_36  H2   C26  C20  O3      0.00   0.0  0
 N09  CONST_37  H5   C23  C19  C20   180.00   0.0  0
 N09  CONST_38  H3   C25  C26  C20   180.00   0.0  0
 N09  CONST_39  H4   C24  C25  C26   180.00   0.0  0
 N09  CONST_40  H10  C2   C3   C4    180.00   0.0  0
 N09  CONST_41  H11  C5   C4   C3    180.00   0.0  0
 N09  CONST_42  H9   C3   C4   C5    180.00   0.0  0
 N09  CONST_43  C3   C4   N1   C11     0.00   0.0  0
 N09  CONST_44  C5   C4   N1   C11   180.00   0.0  0
 N09  CONST_45  H8   N1   C4   C3    180.00   0.0  0
 N09  CONST_46  C4   N1   C11  C13   180.00   0.0  0
 N09  CONST_47  C4   N1   C11  O2      0.00   0.0  0
 N09  Var_01    C19  C20  O3   C22    -0.46  30.0  1
 N09  Var_02    O3   C22  C17  C16  -179.83  30.0  1
 N09  Var_03    C11  C13  N2   N3    102.72  30.0  1
 N09  Var_04    N1   C11  C13  N2    179.34  30.0  2
 N09  Var_05    H12  C8   O1   C6    179.95  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
 N09  plan-1  N1   0.020
 N09  plan-1  C4   0.020
 N09  plan-1  C3   0.020
 N09  plan-1  C2   0.020
 N09  plan-1  C5   0.020
 N09  plan-1  C6   0.020
 N09  plan-1  C1   0.020
 N09  plan-1  CL   0.020
 N09  plan-1  O1   0.020
 N09  plan-1  H9   0.020
 N09  plan-1  H10  0.020
 N09  plan-1  H11  0.020
 N09  plan-2  C22  0.020
 N09  plan-2  C17  0.020
 N09  plan-2  C16  0.020
 N09  plan-2  N3   0.020
 N09  plan-2  C19  0.020
 N09  plan-2  C18  0.020
 N09  plan-2  N2   0.020
 N09  plan-2  C13  0.020
 N09  plan-2  H1   0.020
 N09  plan-3  O3   0.020
 N09  plan-3  C20  0.020
 N09  plan-3  C26  0.020
 N09  plan-3  C25  0.020
 N09  plan-3  C24  0.020
 N09  plan-3  C23  0.020
 N09  plan-3  C19  0.020
 N09  plan-3  C18  0.020
 N09  plan-3  H2   0.020
 N09  plan-3  H3   0.020
 N09  plan-3  H4   0.020
 N09  plan-3  H5   0.020
 N09  plan-4  C13  0.020
 N09  plan-4  C11  0.020
 N09  plan-4  O2   0.020
 N09  plan-4  N1   0.020
 N09  plan-4  C4   0.020
 N09  plan-4  H8   0.020
 N09  plan-5  O4   0.020
 N09  plan-5  C22  0.020
 N09  plan-5  C17  0.020
 N09  plan-5  O3   0.020

