# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 01:46:52 2020
#   Inital geometry file: a 97 line input string
#   Ligand name: 5-[(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)methyl]-1,3-benzodioxole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1c(CN2C(=O)Cc3cc(Cl)ccc23)ccc4OCOc14
#
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
 CIW  CIW  '5-[(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)methyl]-1,3-benzodioxole-4-carboxylic acid'  ligand  35  24  .  2022-03-15  2022-03-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_CIW
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
 CIW  C1    C   CR6    0  -0.034   4.0149  -0.9957  -0.4393
 CIW  C2    C   CR16   0  -0.261   2.8445  -1.2187  -1.1453
 CIW  C3    C   CR16   0  -0.329   1.7434  -0.3844  -0.9612
 CIW  C4    C   CR56   0   0.509   1.8692   0.6600  -0.0655
 CIW  C5    C   CR56   0   0.067   3.0544   0.8804   0.6370
 CIW  C6    C   CR16   0  -0.347   4.1342   0.0580   0.4671
 CIW  C7    C   CH2    0  -0.605   2.8554   2.0691   1.5185
 CIW  C8    C   CR5    0   0.452   1.4218   2.4790   1.2330
 CIW  O9    O   O      0  -0.437   0.8141   3.4051   1.7247
 CIW  N10   N   NR5    0  -0.598   0.9227   1.6109   0.2979
 CIW  C11   C   CH2    0  -0.316  -0.4092   1.6752  -0.2536
 CIW  C12   C   CR6    0  -0.084  -1.3088   0.5522   0.2258
 CIW  C13   C   CR16   0  -0.234  -0.9657  -0.1779   1.3548
 CIW  C14   C   CR16   0  -0.373  -1.7588  -1.2219   1.8442
 CIW  C15   C   CR56   0   0.328  -2.8985  -1.5047   1.1405
 CIW  C16   C   CR56   0   0.197  -3.2418  -0.7965  -0.0013
 CIW  C17   C   CR6    0  -0.145  -2.4914   0.2512  -0.4910
 CIW  C18   C   C      0   0.320  -2.9514   1.0098  -1.7284
 CIW  O19   O   O      0  -0.410  -3.4488   0.3230  -2.6354
 CIW  O20   O   OC    -1  -0.698  -2.7998   2.2449  -1.7056
 CIW  O21   O   O      0  -0.498  -4.4009  -1.3044  -0.4960
 CIW  C22   C   CH2    0   0.063  -4.9020  -2.1829   0.4966
 CIW  O23   O   O      0  -0.397  -3.8255  -2.4671   1.3778
 CIW  CL24  CL  CL     0  -0.123   5.3701  -2.0518  -0.6854
 CIW  H2    H   HCR6   0   0.275   2.7784  -2.0447  -1.8400
 CIW  H3    H   HCR6   0   0.257   0.8255  -0.5693  -1.5032
 CIW  H6    H   HCR6   0   0.248   5.0560   0.2192   1.0112
 CIW  H7    H   HCH2   0   0.300   2.9737   1.8423   2.5809
 CIW  H7A   H   HCH2   0   0.345   3.5337   2.8949   1.2910
 CIW  H11   H   HCH2   0   0.305  -0.8281   2.6443   0.0111
 CIW  H11A  H   HCH2   0   0.248  -0.3280   1.6648  -1.3409
 CIW  H13   H   HCR6   0   0.252  -0.0567   0.0536   1.8935
 CIW  H14   H   HCR6   0   0.249  -1.4752  -1.7733   2.7302
 CIW  H22   H   HCH2   0   0.254  -5.7160  -1.6989   1.0494
 CIW  H22A  H   HCH2   0   0.221  -5.2532  -3.1043   0.0329

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
 CIW  C1   C2    aromatic  1.385  0.020  1.385
 CIW  C1   C6    aromatic  1.395  0.020  1.395
 CIW  C1   CL24  single    1.736  0.020  1.736
 CIW  C2   C3    aromatic  1.394  0.020  1.394
 CIW  C3   C4    aromatic  1.382  0.020  1.382
 CIW  C4   C5    aromatic  1.395  0.020  1.395
 CIW  C4   N10   single    1.390  0.020  1.390
 CIW  C5   C6    aromatic  1.368  0.020  1.368
 CIW  C5   C7    single    1.493  0.020  1.493
 CIW  C7   C8    single    1.518  0.020  1.518
 CIW  C8   O9    double    1.212  0.020  1.212
 CIW  C8   N10   single    1.370  0.020  1.370
 CIW  N10  C11   single    1.443  0.020  1.443
 CIW  C11  C12   single    1.517  0.020  1.517
 CIW  C12  C13   aromatic  1.388  0.020  1.388
 CIW  C12  C17   aromatic  1.415  0.020  1.415
 CIW  C13  C14   aromatic  1.399  0.020  1.399
 CIW  C14  C15   aromatic  1.369  0.020  1.369
 CIW  C15  C16   aromatic  1.387  0.020  1.387
 CIW  C15  O23   single    1.357  0.020  1.357
 CIW  C16  C17   aromatic  1.379  0.020  1.379
 CIW  C16  O21   single    1.359  0.020  1.359
 CIW  C17  C18   single    1.523  0.020  1.523
 CIW  C18  O19   deloc     1.242  0.020  1.242
 CIW  C18  O20   deloc     1.245  0.020  1.245
 CIW  O21  C22   single    1.417  0.020  1.417
 CIW  C22  O23   single    1.420  0.020  1.420
 CIW  C2   H2    single    0.930  0.020  1.080
 CIW  C3   H3    single    0.930  0.020  1.080
 CIW  C6   H6    single    0.930  0.020  1.080
 CIW  C7   H7    single    0.970  0.020  1.090
 CIW  C7   H7A   single    0.970  0.020  1.090
 CIW  C11  H11   single    0.970  0.020  1.090
 CIW  C11  H11A  single    0.970  0.020  1.090
 CIW  C13  H13   single    0.930  0.020  1.080
 CIW  C14  H14   single    0.930  0.020  1.080
 CIW  C22  H22   single    0.970  0.020  1.090
 CIW  C22  H22A  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
 CIW  CL24  C1   C6   119.01  3.000
 CIW  CL24  C1   C2   119.31  3.000
 CIW  C6    C1   C2   121.68  3.000
 CIW  H2    C2   C3   119.59  3.000
 CIW  H2    C2   C1   120.14  3.000
 CIW  C3    C2   C1   120.26  3.000
 CIW  H3    C3   C4   122.09  3.000
 CIW  H3    C3   C2   120.12  3.000
 CIW  C4    C3   C2   117.79  3.000
 CIW  N10   C4   C5   109.80  3.000
 CIW  N10   C4   C3   128.66  3.000
 CIW  C5    C4   C3   121.54  3.000
 CIW  C7    C5   C6   131.08  3.000
 CIW  C7    C5   C4   108.05  3.000
 CIW  C6    C5   C4   120.86  3.000
 CIW  H6    C6   C5   121.34  3.000
 CIW  H6    C6   C1   120.80  3.000
 CIW  C5    C6   C1   117.86  3.000
 CIW  H7A   C7   H7   106.98  3.000
 CIW  H7A   C7   C8   110.06  3.000
 CIW  H7    C7   C8   109.94  3.000
 CIW  H7A   C7   C5   113.33  3.000
 CIW  H7    C7   C5   113.22  3.000
 CIW  C8    C7   C5   103.29  3.000
 CIW  N10   C8   O9   125.33  3.000
 CIW  N10   C8   C7   107.54  3.000
 CIW  O9    C8   C7   127.13  3.000
 CIW  C11   N10  C8   124.67  3.000
 CIW  C11   N10  C4   123.99  3.000
 CIW  C8    N10  C4   111.33  3.000
 CIW  H11A  C11  H11  106.24  3.000
 CIW  H11A  C11  C12  110.63  3.000
 CIW  H11   C11  C12  110.74  3.000
 CIW  H11A  C11  N10  108.18  3.000
 CIW  H11   C11  N10  107.57  3.000
 CIW  C12   C11  N10  113.18  3.000
 CIW  C17   C12  C13  120.45  3.000
 CIW  C17   C12  C11  119.54  3.000
 CIW  C13   C12  C11  120.00  3.000
 CIW  H13   C13  C14  117.50  3.000
 CIW  H13   C13  C12  120.03  3.000
 CIW  C14   C13  C12  122.47  3.000
 CIW  H14   C14  C15  122.29  3.000
 CIW  H14   C14  C13  121.22  3.000
 CIW  C15   C14  C13  116.50  3.000
 CIW  O23   C15  C16  109.70  3.000
 CIW  O23   C15  C14  128.70  3.000
 CIW  C16   C15  C14  121.59  3.000
 CIW  O21   C16  C17  128.25  3.000
 CIW  O21   C16  C15  108.67  3.000
 CIW  C17   C16  C15  123.08  3.000
 CIW  C18   C17  C16  120.19  3.000
 CIW  C18   C17  C12  123.92  3.000
 CIW  C16   C17  C12  115.89  3.000
 CIW  O20   C18  O19  127.67  3.000
 CIW  O20   C18  C17  116.28  3.000
 CIW  O19   C18  C17  116.05  3.000
 CIW  C22   O21  C16  106.16  3.000
 CIW  H22A  C22  H22  110.39  3.000
 CIW  H22A  C22  O23  109.83  3.000
 CIW  H22   C22  O23  109.77  3.000
 CIW  H22A  C22  O21  109.88  3.000
 CIW  H22   C22  O21  110.00  3.000
 CIW  O23   C22  O21  106.91  3.000
 CIW  C22   O23  C15  105.50  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
 CIW  CONST_01  C4    C3   C2   C1     0.00   0.0  0
 CIW  CONST_02  C4    C5   C6   C1     0.00   0.0  0
 CIW  CONST_03  C5    C6   C1   C2     0.00   0.0  0
 CIW  CONST_04  C5    C4   C3   C2     0.00   0.0  0
 CIW  CONST_05  C6    C1   C2   C3     0.00   0.0  0
 CIW  CONST_06  C6    C5   C4   C3     0.00   0.0  0
 CIW  CONST_07  C15   C14  C13  C12    0.00   0.0  0
 CIW  CONST_08  C15   C16  C17  C12    0.00   0.0  0
 CIW  CONST_09  C16   C17  C12  C13    0.00   0.0  0
 CIW  CONST_10  C16   C15  C14  C13    0.00   0.0  0
 CIW  CONST_11  C17   C12  C13  C14    0.00   0.0  0
 CIW  CONST_12  C17   C16  C15  C14    0.00   0.0  0
 CIW  CONST_13  C7    C8   N10  C4     0.00   0.0  0
 CIW  CONST_14  CL24  C1   C2   C3   180.00   0.0  0
 CIW  CONST_15  CL24  C1   C6   C5   180.00   0.0  0
 CIW  CONST_16  C14   C13  C12  C11  180.00   0.0  0
 CIW  CONST_17  C16   C17  C12  C11  180.00   0.0  0
 CIW  CONST_18  C18   C17  C12  C13  180.00   0.0  0
 CIW  CONST_19  C18   C17  C16  C15  180.00   0.0  0
 CIW  CONST_20  O21   C16  C17  C18    0.00   0.0  0
 CIW  CONST_21  O9    C8   N10  C4   180.00   0.0  0
 CIW  CONST_22  C11   N10  C8   C7   180.00   0.0  0
 CIW  CONST_23  H3    C3   C2   C1   180.00   0.0  0
 CIW  CONST_24  H6    C6   C1   C2   180.00   0.0  0
 CIW  CONST_25  H2    C2   C3   C4   180.00   0.0  0
 CIW  CONST_26  H14   C14  C13  C12  180.00   0.0  0
 CIW  CONST_27  H13   C13  C14  C15  180.00   0.0  0
 CIW  CONST_28  C11   N10  C8   O9     0.00   0.0  0
 CIW  Var_01    O21   C22  O23  C15   17.07  30.0  1
 CIW  Var_02    O23   C22  O21  C16  -17.01  30.0  1
 CIW  Var_03    C12   C11  N10  C4    71.64  30.0  3
 CIW  Var_04    C13   C12  C11  N10   17.42  30.0  2
 CIW  Var_05    H7    C7   C5   C4   119.21  30.0  1
 CIW  Var_06    O19   C18  C17  C12  140.75  30.0  2

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
 CIW  plan-1  C11   0.020
 CIW  plan-1  C12   0.020
 CIW  plan-1  C13   0.020
 CIW  plan-1  C14   0.020
 CIW  plan-1  C15   0.020
 CIW  plan-1  C16   0.020
 CIW  plan-1  C17   0.020
 CIW  plan-1  C18   0.020
 CIW  plan-1  O21   0.020
 CIW  plan-1  O23   0.020
 CIW  plan-1  H13   0.020
 CIW  plan-1  H14   0.020
 CIW  plan-2  C1    0.020
 CIW  plan-2  C2    0.020
 CIW  plan-2  C3    0.020
 CIW  plan-2  C4    0.020
 CIW  plan-2  C5    0.020
 CIW  plan-2  C6    0.020
 CIW  plan-2  C7    0.020
 CIW  plan-2  C8    0.020
 CIW  plan-2  O9    0.020
 CIW  plan-2  N10   0.020
 CIW  plan-2  C11   0.020
 CIW  plan-2  CL24  0.020
 CIW  plan-2  H2    0.020
 CIW  plan-2  H3    0.020
 CIW  plan-2  H6    0.020
 CIW  plan-3  C17   0.020
 CIW  plan-3  C18   0.020
 CIW  plan-3  O19   0.020
 CIW  plan-3  O20   0.020

