# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 21:19:04 2020
#   Inital geometry file: a 91 line input string
#   Ligand name: 5-carbamimidamido-2-[(1S)-1-chloro-2-ethoxy-2-oxoethyl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOC(=O)[C@@H](Cl)c1ccc(NC(N)=N)cc1C(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
 GIS  GIS  '5-carbamimidamido-2-[(1S)-1-chloro-2-ethoxy-2-oxoethyl]benzoic acid'  ligand  34  20  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GIS
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
 GIS  C1    C   C     0   0.519  -1.8835   0.7648   0.0829
 GIS  O1    O   O     0  -0.438  -2.1213   0.5606   1.2521
 GIS  OXT   O   OH1   0  -0.584  -2.7617   1.3089  -0.7427
 GIS  C2    C   CR6   0  -0.056  -0.5961   0.4132  -0.5688
 GIS  C3    C   CR16  0  -0.339  -0.5918   0.2130  -1.9480
 GIS  C4    C   CR6   0   0.401   0.5616  -0.2197  -2.6007
 GIS  C6    C   CR16  0  -0.332   1.7043  -0.4378  -1.8273
 GIS  C7    C   CR16  0  -0.290   1.6980  -0.2145  -0.4655
 GIS  C8    C   CR6   0   0.168   0.5597   0.2207   0.2009
 GIS  C9    C   CH1   0  -0.543   0.5615   0.4745   1.6848
 GIS  C10   C   C     0   0.659   0.0102  -0.7097   2.4654
 GIS  O2    O   O     0  -0.431  -0.0258  -1.8307   2.0322
 GIS  O3    O   O2    0  -0.443  -0.3601  -0.3498   3.6749
 GIS  C11   C   CH2   0  -0.183  -0.8511  -1.3697   4.5632
 GIS  C12   C   CH3   0  -0.689  -1.1757  -0.7135   5.8822
 GIS  N1    N   NH1   0  -0.756   0.6552  -0.4693  -3.9565
 GIS  C5    C   C     0   0.569  -0.2703  -0.2571  -4.9568
 GIS  N2    N   N     0  -0.694  -1.3938   0.3053  -4.7262
 GIS  N3    N   NH2   0  -0.843   0.2041  -0.6589  -6.1842
 GIS  CL    CL  CL    0  -0.098   2.2248   0.7362   2.3417
 GIS  HXT   H   HOH1  0   0.491  -3.5970   1.4670  -0.2774
 GIS  H3    H   HCR6  0   0.307  -1.4820   0.3804  -2.5315
 GIS  H6    H   HCR6  0   0.278   2.6171  -0.7843  -2.2972
 GIS  H7    H   HCR6  0   0.263   2.6149  -0.3851   0.0797
 GIS  H9    H   HCH1  0   0.339   0.0235   1.3834   1.9437
 GIS  H111  H   HCH2  0   0.240  -0.0914  -2.1437   4.6856
 GIS  H112  H   HCH2  0   0.239  -1.7385  -1.8321   4.1273
 GIS  H121  H   HCH3  0   0.241  -1.5594  -1.4684   6.5679
 GIS  H122  H   HCH3  0   0.238  -0.2922  -0.2665   6.3375
 GIS  H123  H   HCH3  0   0.238  -1.9391   0.0559   5.7700
 GIS  HN1   H   HNH1  0   0.408   1.5637  -0.7799  -4.2618
 GIS  HN2   H   H     0   0.333  -1.9507   0.3489  -5.5714
 GIS  HN31  H   HNH2  0   0.393  -0.4835  -0.6917  -6.9196
 GIS  HN32  H   HNH2  0   0.392   0.8139  -1.4622  -6.2055

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
 GIS  C1   O1    double    1.211  0.020  1.211
 GIS  C1   OXT   single    1.322  0.020  1.322
 GIS  C1   C2    single    1.485  0.020  1.485
 GIS  OXT  HXT   single    0.850  0.020  0.980
 GIS  C2   C3    aromatic  1.394  0.020  1.394
 GIS  C2   C8    aromatic  1.402  0.020  1.402
 GIS  C3   C4    aromatic  1.394  0.020  1.394
 GIS  C3   H3    single    0.930  0.020  1.080
 GIS  C4   C6    aromatic  1.397  0.020  1.397
 GIS  C4   N1    single    1.382  0.020  1.382
 GIS  C6   C7    aromatic  1.380  0.020  1.380
 GIS  C6   H6    single    0.930  0.020  1.080
 GIS  C7   C8    aromatic  1.389  0.020  1.389
 GIS  C7   H7    single    0.930  0.020  1.080
 GIS  C8   C9    single    1.505  0.020  1.505
 GIS  C9   C10   single    1.522  0.020  1.522
 GIS  C9   CL    single    1.807  0.020  1.807
 GIS  C9   H9    single    0.970  0.020  1.090
 GIS  C10  O2    double    1.202  0.020  1.202
 GIS  C10  O3    single    1.315  0.020  1.315
 GIS  O3   C11   single    1.439  0.020  1.439
 GIS  C11  C12   single    1.508  0.020  1.508
 GIS  C11  H111  single    0.970  0.020  1.090
 GIS  C11  H112  single    0.970  0.020  1.090
 GIS  C12  H121  single    0.970  0.020  1.090
 GIS  C12  H122  single    0.970  0.020  1.090
 GIS  C12  H123  single    0.970  0.020  1.090
 GIS  N1   C5    single    1.379  0.020  1.379
 GIS  N1   HN1   single    0.860  0.020  1.020
 GIS  C5   N2    double    1.277  0.020  1.277
 GIS  C5   N3    single    1.376  0.020  1.376
 GIS  N2   HN2   single    0.890  0.020  1.040
 GIS  N3   HN31  single    0.890  0.020  1.040
 GIS  N3   HN32  single    0.890  0.020  1.040

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
 GIS  C2    C1   OXT   113.53  3.000
 GIS  C2    C1   O1    123.66  3.000
 GIS  OXT   C1   O1    122.81  3.000
 GIS  HXT   OXT  C1    109.87  3.000
 GIS  C8    C2   C3    121.41  3.000
 GIS  C8    C2   C1    120.41  3.000
 GIS  C3    C2   C1    118.09  3.000
 GIS  H3    C3   C4    118.57  3.000
 GIS  H3    C3   C2    120.74  3.000
 GIS  C4    C3   C2    120.69  3.000
 GIS  N1    C4   C6    117.37  3.000
 GIS  N1    C4   C3    124.85  3.000
 GIS  C6    C4   C3    117.77  3.000
 GIS  H6    C6   C7    118.91  3.000
 GIS  H6    C6   C4    119.93  3.000
 GIS  C7    C6   C4    121.16  3.000
 GIS  H7    C7   C8    120.19  3.000
 GIS  H7    C7   C6    117.95  3.000
 GIS  C8    C7   C6    121.86  3.000
 GIS  C9    C8   C7    121.65  3.000
 GIS  C9    C8   C2    121.27  3.000
 GIS  C7    C8   C2    117.08  3.000
 GIS  H9    C9   CL    104.35  3.000
 GIS  H9    C9   C10   110.43  3.000
 GIS  CL    C9   C10   105.05  3.000
 GIS  H9    C9   C8    112.02  3.000
 GIS  CL    C9   C8    112.57  3.000
 GIS  C10   C9   C8    111.96  3.000
 GIS  O3    C10  O2    125.31  3.000
 GIS  O3    C10  C9    111.15  3.000
 GIS  O2    C10  C9    123.48  3.000
 GIS  C11   O3   C10   118.03  3.000
 GIS  H112  C11  H111  108.07  3.000
 GIS  H112  C11  C12   111.02  3.000
 GIS  H111  C11  C12   111.11  3.000
 GIS  H112  C11  O3    109.34  3.000
 GIS  H111  C11  O3    109.53  3.000
 GIS  C12   C11  O3    107.75  3.000
 GIS  H123  C12  H122  108.75  3.000
 GIS  H123  C12  H121  107.89  3.000
 GIS  H122  C12  H121  107.86  3.000
 GIS  H123  C12  C11   111.58  3.000
 GIS  H122  C12  C11   111.67  3.000
 GIS  H121  C12  C11   108.95  3.000
 GIS  HN1   N1   C5    115.64  3.000
 GIS  HN1   N1   C4    114.47  3.000
 GIS  C5    N1   C4    129.67  3.000
 GIS  N3    C5   N2    126.36  3.000
 GIS  N3    C5   N1    111.76  3.000
 GIS  N2    C5   N1    121.81  3.000
 GIS  HN2   N2   C5    110.60  3.000
 GIS  HN32  N3   HN31  111.80  3.000
 GIS  HN32  N3   C5    117.37  3.000
 GIS  HN31  N3   C5    115.18  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
 GIS  CONST_01  C6    C4   C3   C2     0.00   0.0  0
 GIS  CONST_02  C6    C7   C8   C2     0.00   0.0  0
 GIS  CONST_03  C7    C8   C2   C3     0.00   0.0  0
 GIS  CONST_04  C7    C6   C4   C3     0.00   0.0  0
 GIS  CONST_05  C8    C2   C3   C4     0.00   0.0  0
 GIS  CONST_06  C8    C7   C6   C4     0.00   0.0  0
 GIS  CONST_07  C4    C3   C2   C1   180.00   0.0  0
 GIS  CONST_08  C7    C8   C2   C1   180.00   0.0  0
 GIS  CONST_09  N1    C4   C3   C2   180.00   0.0  0
 GIS  CONST_10  C9    C8   C2   C3   180.00   0.0  0
 GIS  CONST_11  C9    C8   C7   C6   180.00   0.0  0
 GIS  CONST_12  N1    C4   C6   C7   180.00   0.0  0
 GIS  CONST_13  H7    C7   C8   C2   180.00   0.0  0
 GIS  CONST_14  H6    C6   C4   C3   180.00   0.0  0
 GIS  CONST_15  H3    C3   C4   C6   180.00   0.0  0
 GIS  CONST_16  C5    N1   C4   C3     0.00   0.0  0
 GIS  CONST_17  C5    N1   C4   C6   180.00   0.0  0
 GIS  CONST_18  HN1   N1   C4   C3   180.00   0.0  0
 GIS  CONST_19  N2    C5   N1   C4     0.00   0.0  0
 GIS  CONST_20  N3    C5   N1   C4   180.00   0.0  0
 GIS  CONST_21  HXT   OXT  C1   C2   180.00   0.0  0
 GIS  CONST_22  HN2   N2   C5   N1   180.00   0.0  0
 GIS  CONST_23  HN31  N3   C5   N1   180.00   0.0  0
 GIS  Var_01    C3    C2   C1   O1   156.09  30.0  2
 GIS  Var_02    C12   C11  O3   C10  178.73  30.0  3
 GIS  Var_03    H121  C12  C11  O3   179.44  30.0  3

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
 GIS  chir_01  C9  C8  C10  CL  negativ

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
 GIS  plan-1  C1    0.020
 GIS  plan-1  C2    0.020
 GIS  plan-1  C3    0.020
 GIS  plan-1  C4    0.020
 GIS  plan-1  C6    0.020
 GIS  plan-1  C7    0.020
 GIS  plan-1  C8    0.020
 GIS  plan-1  C9    0.020
 GIS  plan-1  N1    0.020
 GIS  plan-1  H3    0.020
 GIS  plan-1  H6    0.020
 GIS  plan-1  H7    0.020
 GIS  plan-2  C4    0.020
 GIS  plan-2  N1    0.020
 GIS  plan-2  C5    0.020
 GIS  plan-2  N2    0.020
 GIS  plan-2  N3    0.020
 GIS  plan-2  HN1   0.020
 GIS  plan-2  HN2   0.020
 GIS  plan-2  HN31  0.020
 GIS  plan-2  HN32  0.020
 GIS  plan-3  C1    0.020
 GIS  plan-3  O1    0.020
 GIS  plan-3  OXT   0.020
 GIS  plan-3  C2    0.020
 GIS  plan-3  HXT   0.020
 GIS  plan-4  C9    0.020
 GIS  plan-4  C10   0.020
 GIS  plan-4  O2    0.020
 GIS  plan-4  O3    0.020

