# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  8 10:11:21 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 5-chloro-N-{(2R)-2-[cyclopentyl(2-hydroxyethyl)amino]-2-hydroxyethyl}-1H-indole-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCN([C@H](O)CNC(=O)c1[nH]c2ccc(Cl)cc2c1)C3CCCC3
#
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
 288  288  5-chloro-N-{(2R)-2-[cyclopentyl(2-hydroxyethyl)amino]-2-hydroxyethyl}-1H-indole-2-carboxamide  ligand  49  25  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_288
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
 288  C1    C   CR56  0   0.062   3.4515  -0.2768  -0.3162
 288  C2    C   CR56  0   0.359   2.6348  -0.4491   0.8225
 288  C3    C   CR15  0  -0.396   2.6410  -0.5589  -1.4517
 288  C4    C   CR16  0  -0.302   4.7903   0.1030  -0.1560
 288  N5    N   NR15  0  -0.738   1.3899  -0.7906   0.3900
 288  C6    C   CR16  0  -0.307   3.1234  -0.2737   2.1165
 288  C7    C   CR5   0   0.225   1.3949  -0.8696  -0.9804
 288  C8    C   CR6   0  -0.049   5.2553   0.2810   1.1260
 288  C9    C   CR16  0  -0.237   4.4433   0.0957   2.2577
 288  C10   C   C     0   0.519   0.1980  -1.1846  -1.7885
 288  CL11  CL  CL    0  -0.140   6.9119   0.7491   1.3725
 288  N12   N   NH1   0  -0.666  -0.9799  -0.9792  -1.1736
 288  O13   O   O     0  -0.478   0.3066  -1.5982  -2.9334
 288  C14   C   CH2   0  -0.328  -2.2574  -1.1276  -1.8326
 288  C15   C   CH1   0   0.178  -3.3468  -1.2115  -0.7503
 288  N16   N   NT    0  -0.488  -3.1415  -0.1558   0.2576
 288  O17   O   OH1   0  -0.650  -3.3197  -2.4916  -0.1927
 288  C18   C   CR15  0  -0.040  -3.7616   1.1226  -0.0835
 288  C19   C   CH2   0  -0.334  -3.3996  -0.5364   1.6436
 288  C20   C   CH2   0  -0.466  -3.3481   2.2506   0.8755
 288  C21   C   CH2   0  -0.469  -3.4085   1.7229  -1.4466
 288  C22   C   CH2   0  -0.171  -4.8477  -0.5352   2.1127
 288  C23   C   CH2   0  -0.442  -3.6088   3.5657   0.1170
 288  C24   C   CH2   0  -0.446  -3.9278   3.1523  -1.3301
 288  O25   O   OH1   0  -0.659  -5.6310  -1.4077   1.3308
 288  H3    H   HCR5  0   0.264   2.9305  -0.5068  -2.4889
 288  H4    H   HCR6  0   0.275   5.4355   0.2463  -1.0125
 288  HN5   H   HNR5  0   0.409   0.6480  -1.1097   0.9921
 288  H6    H   HCR6  0   0.276   2.4941  -0.4160   2.9851
 288  H9    H   HCR6  0   0.278   4.8565   0.2471   3.2454
 288  H12   H   HNH1  0   0.388  -1.0327  -0.3837  -0.3540
 288  H141  H   HCH2  0   0.269  -2.2760  -2.0479  -2.4174
 288  H142  H   HCH2  0   0.256  -2.4331  -0.3102  -2.5314
 288  H15   H   HCH1  0   0.224  -4.3293  -1.1072  -1.2275
 288  H17   H   HOH1  0   0.445  -2.4017  -2.7472  -0.0429
 288  H18   H   HCR5  0   0.206  -4.8611   1.0291  -0.0632
 288  H191  H   HCH2  0   0.243  -2.8608   0.1594   2.2910
 288  H192  H   HCH2  0   0.242  -2.9567  -1.5103   1.8401
 288  H201  H   HCH2  0   0.236  -3.8816   2.2141   1.8260
 288  H202  H   HCH2  0   0.228  -2.2837   2.1389   1.0984
 288  H211  H   HCH2  0   0.219  -2.3223   1.7253  -1.5821
 288  H212  H   HCH2  0   0.241  -3.8557   1.1956  -2.2898
 288  H221  H   HCH2  0   0.193  -5.2458   0.4866   2.0816
 288  H222  H   HCH2  0   0.200  -4.8430  -0.8293   3.1720
 288  H231  H   HCH2  0   0.229  -4.4289   4.1319   0.5594
 288  H232  H   HCH2  0   0.230  -2.7298   4.2096   0.1558
 288  H241  H   HCH2  0   0.225  -5.0069   3.1652  -1.5003
 288  H242  H   HCH2  0   0.235  -3.4830   3.8179  -2.0704
 288  H25   H   HOH1  0   0.450  -6.5525  -1.2595   1.5603

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
 288  C1   C2    aromatic  1.412  0.020  1.412
 288  C1   C3    aromatic  1.423  0.020  1.423
 288  C1   C4    aromatic  1.401  0.020  1.401
 288  C2   N5    aromatic  1.361  0.020  1.361
 288  C2   C6    aromatic  1.394  0.020  1.394
 288  C3   C7    aromatic  1.368  0.020  1.368
 288  C3   H3    single    0.930  0.020  1.080
 288  C4   C8    aromatic  1.375  0.020  1.375
 288  C4   H4    single    0.930  0.020  1.080
 288  N5   C7    aromatic  1.373  0.020  1.373
 288  N5   HN5   single    0.860  0.020  1.020
 288  C6   C9    aromatic  1.378  0.020  1.378
 288  C6   H6    single    0.930  0.020  1.080
 288  C7   C10   single    1.478  0.020  1.478
 288  C8   C9    aromatic  1.405  0.020  1.405
 288  C8   CL11  single    1.739  0.020  1.739
 288  C9   H9    single    0.930  0.020  1.080
 288  C10  N12   single    1.345  0.020  1.345
 288  C10  O13   double    1.222  0.020  1.222
 288  N12  C14   single    1.445  0.020  1.445
 288  N12  H12   single    0.890  0.020  1.040
 288  C14  C15   single    1.538  0.020  1.538
 288  C14  H141  single    0.970  0.020  1.090
 288  C14  H142  single    0.970  0.020  1.090
 288  C15  N16   single    1.474  0.020  1.474
 288  C15  O17   single    1.397  0.020  1.397
 288  C15  H15   single    0.970  0.020  1.090
 288  N16  C18   single    1.461  0.020  1.461
 288  N16  C19   single    1.460  0.020  1.460
 288  O17  H17   single    0.850  0.020  0.980
 288  C18  C20   single    1.537  0.020  1.537
 288  C18  C21   single    1.531  0.020  1.531
 288  C18  H18   single    0.970  0.020  1.090
 288  C19  C22   single    1.522  0.020  1.522
 288  C19  H191  single    0.970  0.020  1.090
 288  C19  H192  single    0.970  0.020  1.090
 288  C20  C23   single    1.540  0.020  1.540
 288  C20  H201  single    0.970  0.020  1.090
 288  C20  H202  single    0.970  0.020  1.090
 288  C21  C24   single    1.525  0.020  1.525
 288  C21  H211  single    0.970  0.020  1.090
 288  C21  H212  single    0.970  0.020  1.090
 288  C22  O25   single    1.409  0.020  1.409
 288  C22  H221  single    0.970  0.020  1.090
 288  C22  H222  single    0.970  0.020  1.090
 288  C23  C24   single    1.538  0.020  1.538
 288  C23  H231  single    0.970  0.020  1.090
 288  C23  H232  single    0.970  0.020  1.090
 288  C24  H241  single    0.970  0.020  1.090
 288  C24  H242  single    0.970  0.020  1.090
 288  O25  H25   single    0.850  0.020  0.980

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
 288  C4    C1   C3    133.57  3.000
 288  C4    C1   C2    119.58  3.000
 288  C3    C1   C2    106.85  3.000
 288  C6    C2   N5    130.30  3.000
 288  C6    C2   C1    122.04  3.000
 288  N5    C2   C1    107.66  3.000
 288  H3    C3   C7    125.94  3.000
 288  H3    C3   C1    127.24  3.000
 288  C7    C3   C1    106.79  3.000
 288  H4    C4   C8    121.28  3.000
 288  H4    C4   C1    121.02  3.000
 288  C8    C4   C1    117.70  3.000
 288  HN5   N5   C7    125.54  3.000
 288  HN5   N5   C2    124.26  3.000
 288  C7    N5   C2    109.16  3.000
 288  H6    C6   C9    120.67  3.000
 288  H6    C6   C2    121.65  3.000
 288  C9    C6   C2    117.68  3.000
 288  C10   C7   N5    123.72  3.000
 288  C10   C7   C3    126.70  3.000
 288  N5    C7   C3    109.52  3.000
 288  CL11  C8   C9    118.15  3.000
 288  CL11  C8   C4    119.28  3.000
 288  C9    C8   C4    122.57  3.000
 288  H9    C9   C8    119.77  3.000
 288  H9    C9   C6    119.81  3.000
 288  C8    C9   C6    120.42  3.000
 288  O13   C10  N12   123.91  3.000
 288  O13   C10  C7    120.82  3.000
 288  N12   C10  C7    115.26  3.000
 288  H12   N12  C14   112.50  3.000
 288  H12   N12  C10   120.31  3.000
 288  C14   N12  C10   123.38  3.000
 288  H142  C14  H141  106.64  3.000
 288  H142  C14  C15   112.21  3.000
 288  H141  C14  C15   108.62  3.000
 288  H142  C14  N12   110.98  3.000
 288  H141  C14  N12   110.26  3.000
 288  C15   C14  N12   108.11  3.000
 288  H15   C15  O17   106.15  3.000
 288  H15   C15  N16   110.73  3.000
 288  O17   C15  N16   112.38  3.000
 288  H15   C15  C14   108.85  3.000
 288  O17   C15  C14   108.50  3.000
 288  N16   C15  C14   110.09  3.000
 288  C19   N16  C18   112.00  3.000
 288  C19   N16  C15   115.96  3.000
 288  C18   N16  C15   114.07  3.000
 288  H17   O17  C15   108.87  3.000
 288  H18   C18  C21   106.22  3.000
 288  H18   C18  C20   108.59  3.000
 288  C21   C18  C20   101.87  3.000
 288  H18   C18  N16   110.14  3.000
 288  C21   C18  N16   116.94  3.000
 288  C20   C18  N16   112.47  3.000
 288  H192  C19  H191  105.21  3.000
 288  H192  C19  C22   109.41  3.000
 288  H191  C19  C22   106.62  3.000
 288  H192  C19  N16   109.44  3.000
 288  H191  C19  N16   108.02  3.000
 288  C22   C19  N16   117.41  3.000
 288  H202  C20  H201  107.17  3.000
 288  H202  C20  C23   110.64  3.000
 288  H201  C20  C23   112.02  3.000
 288  H202  C20  C18   108.31  3.000
 288  H201  C20  C18   112.80  3.000
 288  C23   C20  C18   105.89  3.000
 288  H212  C21  H211  108.20  3.000
 288  H212  C21  C24   111.88  3.000
 288  H211  C21  C24   110.20  3.000
 288  H212  C21  C18   113.85  3.000
 288  H211  C21  C18   109.87  3.000
 288  C24   C21  C18   102.77  3.000
 288  H222  C22  H221  106.14  3.000
 288  H222  C22  O25   111.80  3.000
 288  H221  C22  O25   111.05  3.000
 288  H222  C22  C19   107.01  3.000
 288  H221  C22  C19   109.71  3.000
 288  O25   C22  C19   110.93  3.000
 288  H232  C23  H231  106.57  3.000
 288  H232  C23  C24   111.06  3.000
 288  H231  C23  C24   111.42  3.000
 288  H232  C23  C20   110.50  3.000
 288  H231  C23  C20   111.77  3.000
 288  C24   C23  C20   105.60  3.000
 288  H242  C24  H241  106.85  3.000
 288  H242  C24  C23   112.96  3.000
 288  H241  C24  C23   110.38  3.000
 288  H242  C24  C21   112.41  3.000
 288  H241  C24  C21   109.60  3.000
 288  C23   C24  C21   104.66  3.000
 288  H25   O25  C22   107.76  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
 288  CONST_01  C7    N5   C2   C1      0.00   0.0  0
 288  CONST_02  C9    C6   C2   C1      0.00   0.0  0
 288  CONST_03  N5    C7   C3   C1      0.00   0.0  0
 288  CONST_04  C9    C8   C4   C1      0.00   0.0  0
 288  CONST_05  C7    C3   C1   C2      0.00   0.0  0
 288  CONST_06  C8    C4   C1   C2      0.00   0.0  0
 288  CONST_07  C3    C7   N5   C2      0.00   0.0  0
 288  CONST_08  C8    C9   C6   C2      0.00   0.0  0
 288  CONST_09  N5    C2   C1   C3      0.00   0.0  0
 288  CONST_10  C6    C2   C1   C3    180.00   0.0  0
 288  CONST_11  C8    C4   C1   C3    180.00   0.0  0
 288  CONST_12  N5    C2   C1   C4    180.00   0.0  0
 288  CONST_13  C6    C2   C1   C4      0.00   0.0  0
 288  CONST_14  C7    C3   C1   C4    180.00   0.0  0
 288  CONST_15  C6    C9   C8   C4      0.00   0.0  0
 288  CONST_16  C9    C6   C2   N5    180.00   0.0  0
 288  CONST_17  C7    N5   C2   C6    180.00   0.0  0
 288  CONST_18  C10   C7   C3   C1    180.00   0.0  0
 288  CONST_19  CL11  C8   C4   C1    180.00   0.0  0
 288  CONST_20  C10   C7   N5   C2    180.00   0.0  0
 288  CONST_21  CL11  C8   C9   C6    180.00   0.0  0
 288  CONST_22  HN5   N5   C2   C1    180.00   0.0  0
 288  CONST_23  H6    C6   C2   C1    180.00   0.0  0
 288  CONST_24  H3    C3   C1   C2    180.00   0.0  0
 288  CONST_25  H4    C4   C1   C2    180.00   0.0  0
 288  CONST_26  H9    C9   C6   C2    180.00   0.0  0
 288  CONST_27  C14   N12  C10  C7    180.00   0.0  0
 288  CONST_29  C14   N12  C10  O13     0.00   0.0  0
 288  Var_01    C24   C23  C20  C18    -9.62  30.0  1
 288  Var_02    C23   C24  C21  C18    38.31  30.0  1
 288  Var_03    C21   C24  C23  C20   -17.61  30.0  1
 288  Var_04    N12   C10  C7   C3   -156.67  30.0  2
 288  Var_05    C22   C19  N16  C18    52.16  30.0  3
 288  Var_06    C15   C14  N12  C10   164.03  30.0  3
 288  Var_07    O25   C22  C19  N16    58.64  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
 288  chir_01  C15  C14  N16  O17  positiv
 288  chir_02  C18  N16  C20  C21  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
 288  plan-1  C1    0.020
 288  plan-1  C2    0.020
 288  plan-1  C3    0.020
 288  plan-1  C4    0.020
 288  plan-1  N5    0.020
 288  plan-1  C6    0.020
 288  plan-1  C7    0.020
 288  plan-1  C8    0.020
 288  plan-1  C9    0.020
 288  plan-1  C10   0.020
 288  plan-1  CL11  0.020
 288  plan-1  H3    0.020
 288  plan-1  H4    0.020
 288  plan-1  HN5   0.020
 288  plan-1  H6    0.020
 288  plan-1  H9    0.020
 288  plan-2  C7    0.020
 288  plan-2  C10   0.020
 288  plan-2  N12   0.020
 288  plan-2  O13   0.020
 288  plan-2  C14   0.020
 288  plan-2  H12   0.020

