# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 06:53:09 2020
#   Inital geometry file: a 136 line input string
#   Ligand name: 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}-N-[(1S)-1-(hydroxymethyl)propyl]acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@H](CO)NC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c3ccc(OC)cc13
#
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
 IMS  IMS  2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}-N-[(1S)-1-(hydroxymethyl)propyl]acetamide  ligand  55  30  .  2021-08-11  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_IMS
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
 IMS  C2    C   CR16  0  -0.477   1.2072   3.2918   0.4008
 IMS  C3    C   CR6   0   0.395   0.6232   4.4463  -0.1060
 IMS  C4    C   CR16  0  -0.400  -0.5831   4.3719  -0.8165
 IMS  C5    C   CR16  0  -0.275  -1.2180   3.1560  -1.0330
 IMS  C6    C   CH3   0  -0.436   0.7321   6.8087  -0.3510
 IMS  C7    C   CR5   0   0.005   0.9039   0.7388   0.5993
 IMS  C8    C   CR5   0   0.307  -0.0707  -0.0916   0.1486
 IMS  O2    O   O     0  -0.486   3.5685   0.7227  -0.5571
 IMS  C18   C   C     0   0.554   3.2605  -0.0220   0.3612
 IMS  N2    N   NH1   0  -0.622   3.8549  -1.1997   0.6091
 IMS  C19   C   CH1   0  -0.121   4.9330  -1.7737  -0.1719
 IMS  C21   C   CH2   0  -0.419   6.1771  -1.9889   0.6913
 IMS  C22   C   CH3   0  -0.664   6.7586  -0.6899   1.2290
 IMS  C20   C   CH2   0  -0.145   4.4597  -3.0454  -0.8579
 IMS  O3    O   OH1   0  -0.673   4.0797  -3.9831   0.1238
 IMS  C17   C   CH2   0  -0.724   2.1437   0.3404   1.3283
 IMS  C1    C   CR56  0   0.083   0.5713   2.0749   0.1930
 IMS  C16   C   CH3   0  -0.729  -0.0657  -1.5799   0.2165
 IMS  N     N   NR5   0  -0.671  -1.0420   0.6700  -0.5253
 IMS  C     C   CR56  0   0.329  -0.6295   2.0083  -0.5263
 IMS  O     O   O2    0  -0.478   1.2851   5.6007   0.1273
 IMS  O1    O   O     0  -0.408  -2.6295   0.7994  -2.1343
 IMS  C10   C   CR6   0  -0.067  -2.8812  -0.9570  -0.5961
 IMS  C15   C   CR16  0  -0.264  -3.1018  -1.0587   0.7740
 IMS  C14   C   CR16  0  -0.196  -3.8523  -2.1039   1.2870
 IMS  C13   C   CR6   0  -0.035  -4.3625  -3.0561   0.4176
 IMS  CL    CL  CL    0  -0.111  -5.2787  -4.3767   1.0529
 IMS  C12   C   CR16  0  -0.202  -4.1558  -2.9694  -0.9521
 IMS  C11   C   CR16  0  -0.259  -3.4295  -1.9045  -1.4557
 IMS  H2    H   HCR6  0   0.251   2.1372   3.3486   0.9538
 IMS  H4    H   HCR6  0   0.279  -1.0458   5.2623  -1.2186
 IMS  H5    H   HCR6  0   0.274  -2.1404   3.1388  -1.5925
 IMS  H61   H   HCH3  0   0.258   1.4078   7.6021  -0.0402
 IMS  H62   H   HCH3  0   0.226   0.6545   6.8227  -1.4416
 IMS  H63   H   HCH3  0   0.226  -0.2563   7.0047   0.0732
 IMS  HN2   H   HNH1  0   0.393   3.5096  -1.7540   1.3766
 IMS  H19   H   HCH1  0   0.255   5.1761  -1.0590  -0.9604
 IMS  H211  H   HCH2  0   0.227   6.9262  -2.5015   0.0817
 IMS  H212  H   HCH2  0   0.225   5.9438  -2.6649   1.5181
 IMS  H221  H   HCH3  0   0.232   7.6494  -0.8800   1.8279
 IMS  H222  H   HCH3  0   0.219   7.0441  -0.0198   0.4160
 IMS  H223  H   HCH3  0   0.222   6.0444  -0.1603   1.8608
 IMS  H201  H   HCH2  0   0.212   3.6229  -2.7974  -1.5219
 IMS  H202  H   HCH2  0   0.200   5.2738  -3.4244  -1.4897
 IMS  HO3   H   HOH1  0   0.459   3.6036  -4.6976  -0.3075
 IMS  H171  H   HCH2  0   0.278   1.9462  -0.4677   2.0343
 IMS  H172  H   HCH2  0   0.296   2.4989   1.1822   1.9289
 IMS  H161  H   HCH3  0   0.270  -0.7046  -1.9772   1.0046
 IMS  H162  H   HCH3  0   0.266  -0.3750  -2.0393  -0.7217
 IMS  H163  H   HCH3  0   0.255   0.9477  -1.9209   0.4203
 IMS  H15   H   HCR6  0   0.289  -2.7010  -0.3173   1.4538
 IMS  H14   H   HCR6  0   0.291  -4.0335  -2.1743   2.3505
 IMS  H12   H   HCR6  0   0.289  -4.5609  -3.7182  -1.6185
 IMS  H11   H   HCR6  0   0.280  -3.2737  -1.8270  -2.5237
 IMS  C9    C   C     0   0.518  -2.1823   0.2179  -1.1708

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
 IMS  C2   C3    aromatic  1.390  0.020  1.390
 IMS  C2   C1    aromatic  1.389  0.020  1.389
 IMS  C2   H2    single    0.930  0.020  1.080
 IMS  C3   C4    aromatic  1.402  0.020  1.402
 IMS  C3   O     single    1.351  0.020  1.351
 IMS  C4   C5    aromatic  1.389  0.020  1.389
 IMS  C4   H4    single    0.930  0.020  1.080
 IMS  C5   C     aromatic  1.386  0.020  1.386
 IMS  C5   H5    single    0.930  0.020  1.080
 IMS  C6   O     single    1.412  0.020  1.412
 IMS  C6   H61   single    0.970  0.020  1.090
 IMS  C6   H62   single    0.970  0.020  1.090
 IMS  C6   H63   single    0.970  0.020  1.090
 IMS  C7   C8    aromatic  1.357  0.020  1.357
 IMS  C7   C17   single    1.492  0.020  1.492
 IMS  C7   C1    aromatic  1.436  0.020  1.436
 IMS  C8   C16   single    1.490  0.020  1.490
 IMS  C8   N     aromatic  1.406  0.020  1.406
 IMS  C9   N     single    1.386  0.020  1.386
 IMS  C9   O1    double    1.211  0.020  1.211
 IMS  C9   C10   single    1.483  0.020  1.483
 IMS  O2   C18   double    1.222  0.020  1.222
 IMS  C18  N2    single    1.342  0.020  1.342
 IMS  C18  C17   single    1.521  0.020  1.521
 IMS  N2   C19   single    1.450  0.020  1.450
 IMS  N2   HN2   single    0.860  0.020  1.020
 IMS  C19  C21   single    1.529  0.020  1.529
 IMS  C19  C20   single    1.521  0.020  1.521
 IMS  C19  H19   single    0.970  0.020  1.090
 IMS  C21  C22   single    1.521  0.020  1.521
 IMS  C21  H211  single    0.970  0.020  1.090
 IMS  C21  H212  single    0.970  0.020  1.090
 IMS  C22  H221  single    0.970  0.020  1.090
 IMS  C22  H222  single    0.970  0.020  1.090
 IMS  C22  H223  single    0.970  0.020  1.090
 IMS  C20  O3    single    1.410  0.020  1.410
 IMS  C20  H201  single    0.970  0.020  1.090
 IMS  C20  H202  single    0.970  0.020  1.090
 IMS  O3   HO3   single    0.850  0.020  0.980
 IMS  C17  H171  single    0.970  0.020  1.090
 IMS  C17  H172  single    0.970  0.020  1.090
 IMS  C1   C     aromatic  1.401  0.020  1.401
 IMS  C16  H161  single    0.970  0.020  1.090
 IMS  C16  H162  single    0.970  0.020  1.090
 IMS  C16  H163  single    0.970  0.020  1.090
 IMS  N    C     aromatic  1.400  0.020  1.400
 IMS  C10  C15   aromatic  1.391  0.020  1.391
 IMS  C10  C11   aromatic  1.392  0.020  1.392
 IMS  C15  C14   aromatic  1.385  0.020  1.385
 IMS  C15  H15   single    0.930  0.020  1.080
 IMS  C14  C13   aromatic  1.387  0.020  1.387
 IMS  C14  H14   single    0.930  0.020  1.080
 IMS  C13  CL    single    1.728  0.020  1.728
 IMS  C13  C12   aromatic  1.388  0.020  1.388
 IMS  C12  C11   aromatic  1.384  0.020  1.384
 IMS  C12  H12   single    0.930  0.020  1.080
 IMS  C11  H11   single    0.930  0.020  1.080

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
 IMS  H2    C2   C1    121.02  3.000
 IMS  H2    C2   C3    120.22  3.000
 IMS  C1    C2   C3    118.76  3.000
 IMS  O     C3   C4    123.67  3.000
 IMS  O     C3   C2    116.17  3.000
 IMS  C4    C3   C2    120.15  3.000
 IMS  H4    C4   C5    117.87  3.000
 IMS  H4    C4   C3    120.87  3.000
 IMS  C5    C4   C3    121.26  3.000
 IMS  H5    C5   C     122.65  3.000
 IMS  H5    C5   C4    119.05  3.000
 IMS  C     C5   C4    118.29  3.000
 IMS  H63   C6   H62   108.70  3.000
 IMS  H63   C6   H61   108.66  3.000
 IMS  H62   C6   H61   108.65  3.000
 IMS  H63   C6   O     112.08  3.000
 IMS  H62   C6   O     112.12  3.000
 IMS  H61   C6   O     106.50  3.000
 IMS  C1    C7   C17   125.39  3.000
 IMS  C1    C7   C8    108.00  3.000
 IMS  C17   C7   C8    126.54  3.000
 IMS  N     C8   C16   124.42  3.000
 IMS  N     C8   C7    108.89  3.000
 IMS  C16   C8   C7    126.41  3.000
 IMS  C17   C18  N2    114.63  3.000
 IMS  C17   C18  O2    121.18  3.000
 IMS  N2    C18  O2    124.19  3.000
 IMS  HN2   N2   C19   116.57  3.000
 IMS  HN2   N2   C18   118.14  3.000
 IMS  C19   N2   C18   125.25  3.000
 IMS  H19   C19  C20   106.92  3.000
 IMS  H19   C19  C21   108.58  3.000
 IMS  C20   C19  C21   112.96  3.000
 IMS  H19   C19  N2    107.19  3.000
 IMS  C20   C19  N2    110.04  3.000
 IMS  C21   C19  N2    110.89  3.000
 IMS  H212  C21  H211  106.14  3.000
 IMS  H212  C21  C22   110.01  3.000
 IMS  H211  C21  C22   109.60  3.000
 IMS  H212  C21  C19   109.90  3.000
 IMS  H211  C21  C19   107.97  3.000
 IMS  C22   C21  C19   112.97  3.000
 IMS  H223  C22  H222  107.74  3.000
 IMS  H223  C22  H221  107.54  3.000
 IMS  H222  C22  H221  107.61  3.000
 IMS  H223  C22  C21   111.66  3.000
 IMS  H222  C22  C21   111.15  3.000
 IMS  H221  C22  C21   110.95  3.000
 IMS  H202  C20  H201  107.18  3.000
 IMS  H202  C20  O3    111.78  3.000
 IMS  H201  C20  O3    111.49  3.000
 IMS  H202  C20  C19   108.51  3.000
 IMS  H201  C20  C19   108.76  3.000
 IMS  O3    C20  C19   109.03  3.000
 IMS  HO3   O3   C20   108.40  3.000
 IMS  H172  C17  H171  105.88  3.000
 IMS  H172  C17  C18   107.11  3.000
 IMS  H171  C17  C18   111.58  3.000
 IMS  H172  C17  C7    109.43  3.000
 IMS  H171  C17  C7    111.31  3.000
 IMS  C18   C17  C7    111.29  3.000
 IMS  C     C1   C7    107.43  3.000
 IMS  C     C1   C2    120.72  3.000
 IMS  C7    C1   C2    131.85  3.000
 IMS  H163  C16  H162  107.06  3.000
 IMS  H163  C16  H161  107.23  3.000
 IMS  H162  C16  H161  107.62  3.000
 IMS  H163  C16  C8    108.94  3.000
 IMS  H162  C16  C8    112.39  3.000
 IMS  H161  C16  C8    113.29  3.000
 IMS  C     N    C9    123.62  3.000
 IMS  C     N    C8    108.33  3.000
 IMS  C9    N    C8    127.93  3.000
 IMS  N     C    C1    107.30  3.000
 IMS  N     C    C5    131.81  3.000
 IMS  C1    C    C5    120.82  3.000
 IMS  C6    O    C3    118.73  3.000
 IMS  C11   C10  C15   119.73  3.000
 IMS  C11   C10  C9    119.05  3.000
 IMS  C15   C10  C9    120.94  3.000
 IMS  H15   C15  C14   119.00  3.000
 IMS  H15   C15  C10   120.63  3.000
 IMS  C14   C15  C10   120.37  3.000
 IMS  H14   C14  C13   120.69  3.000
 IMS  H14   C14  C15   120.27  3.000
 IMS  C13   C14  C15   119.03  3.000
 IMS  C12   C13  CL    119.30  3.000
 IMS  C12   C13  C14   121.40  3.000
 IMS  CL    C13  C14   119.29  3.000
 IMS  H12   C12  C11   120.35  3.000
 IMS  H12   C12  C13   120.61  3.000
 IMS  C11   C12  C13   119.03  3.000
 IMS  H11   C11  C12   119.33  3.000
 IMS  H11   C11  C10   120.27  3.000
 IMS  C12   C11  C10   120.39  3.000
 IMS  C10   C9   O1    120.98  3.000
 IMS  C10   C9   N     117.75  3.000
 IMS  O1    C9   N     121.18  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
 IMS  CONST_01  C5    C4   C3   C2      0.00   0.0  0
 IMS  CONST_02  C8    C7   C1   C2    180.00   0.0  0
 IMS  CONST_03  C5    C    C1   C2      0.00   0.0  0
 IMS  CONST_04  N     C    C1   C2    180.00   0.0  0
 IMS  CONST_05  C7    C1   C2   C3    180.00   0.0  0
 IMS  CONST_06  C     C1   C2   C3      0.00   0.0  0
 IMS  CONST_07  C     C5   C4   C3      0.00   0.0  0
 IMS  CONST_08  C1    C2   C3   C4      0.00   0.0  0
 IMS  CONST_09  C1    C    C5   C4      0.00   0.0  0
 IMS  CONST_10  N     C    C5   C4    180.00   0.0  0
 IMS  CONST_11  C7    C1   C    C5    180.00   0.0  0
 IMS  CONST_12  C8    N    C    C5    180.00   0.0  0
 IMS  CONST_13  C     N    C8   C7      0.00   0.0  0
 IMS  CONST_14  N     C    C1   C7      0.00   0.0  0
 IMS  CONST_15  C     C1   C7   C8      0.00   0.0  0
 IMS  CONST_16  C1    C    N    C8      0.00   0.0  0
 IMS  CONST_17  N     C8   C7   C1      0.00   0.0  0
 IMS  CONST_18  C13   C14  C15  C10     0.00   0.0  0
 IMS  CONST_19  C13   C12  C11  C10     0.00   0.0  0
 IMS  CONST_20  C12   C11  C10  C15     0.00   0.0  0
 IMS  CONST_21  C12   C13  C14  C15     0.00   0.0  0
 IMS  CONST_22  C11   C10  C15  C14     0.00   0.0  0
 IMS  CONST_23  C11   C12  C13  C14     0.00   0.0  0
 IMS  CONST_24  C17   C7   C1   C2      0.00   0.0  0
 IMS  CONST_25  O     C3   C4   C5    180.00   0.0  0
 IMS  CONST_26  C9    N    C    C5      0.00   0.0  0
 IMS  CONST_27  C9    N    C8   C7    180.00   0.0  0
 IMS  CONST_28  C1    C    N    C9    180.00   0.0  0
 IMS  CONST_29  C14   C15  C10  C9    180.00   0.0  0
 IMS  CONST_30  C12   C11  C10  C9    180.00   0.0  0
 IMS  CONST_31  N     C8   C7   C17   180.00   0.0  0
 IMS  CONST_32  C     C1   C7   C17   180.00   0.0  0
 IMS  CONST_33  O     C3   C2   C1    180.00   0.0  0
 IMS  CONST_34  C16   C8   C7   C1    180.00   0.0  0
 IMS  CONST_35  C     N    C8   C16   180.00   0.0  0
 IMS  CONST_36  CL    C13  C14  C15   180.00   0.0  0
 IMS  CONST_37  C11   C12  C13  CL    180.00   0.0  0
 IMS  CONST_40  H4    C4   C3   C2    180.00   0.0  0
 IMS  CONST_41  H5    C5   C4   C3    180.00   0.0  0
 IMS  CONST_42  H2    C2   C3   C4    180.00   0.0  0
 IMS  CONST_43  H14   C14  C15  C10   180.00   0.0  0
 IMS  CONST_44  H12   C12  C11  C10   180.00   0.0  0
 IMS  CONST_45  H11   C11  C10  C15   180.00   0.0  0
 IMS  CONST_46  H15   C15  C14  C13   180.00   0.0  0
 IMS  CONST_49  C19   N2   C18  O2      0.00   0.0  0
 IMS  CONST_50  C17   C18  N2   C19   180.00   0.0  0
 IMS  CONST_51  HN2   N2   C18  O2    180.00   0.0  0
 IMS  Var_01    C15   C10  C9   N      44.25  30.0  2
 IMS  Var_02    C18   C17  C7   C8     86.49  30.0  2
 IMS  Var_03    H161  C16  C8   C7    103.24  30.0  2
 IMS  Var_04    O2    C18  C17  C7     50.38  30.0  1
 IMS  Var_05    H61   C6   O    C3    178.94  30.0  3
 IMS  Var_06    H221  C22  C21  C19  -179.28  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
 IMS  chir_01  C19  N2  C21  C20  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
 IMS  plan-1  C10  0.020
 IMS  plan-1  C15  0.020
 IMS  plan-1  C14  0.020
 IMS  plan-1  C13  0.020
 IMS  plan-1  CL   0.020
 IMS  plan-1  C12  0.020
 IMS  plan-1  C11  0.020
 IMS  plan-1  H15  0.020
 IMS  plan-1  H14  0.020
 IMS  plan-1  H12  0.020
 IMS  plan-1  H11  0.020
 IMS  plan-1  C9   0.020
 IMS  plan-2  C2   0.020
 IMS  plan-2  C3   0.020
 IMS  plan-2  C4   0.020
 IMS  plan-2  C5   0.020
 IMS  plan-2  C7   0.020
 IMS  plan-2  C8   0.020
 IMS  plan-2  C17  0.020
 IMS  plan-2  C1   0.020
 IMS  plan-2  C16  0.020
 IMS  plan-2  N    0.020
 IMS  plan-2  C    0.020
 IMS  plan-2  O    0.020
 IMS  plan-2  O1   0.020
 IMS  plan-2  C10  0.020
 IMS  plan-2  H2   0.020
 IMS  plan-2  H4   0.020
 IMS  plan-2  H5   0.020
 IMS  plan-2  C9   0.020
 IMS  plan-3  O2   0.020
 IMS  plan-3  C18  0.020
 IMS  plan-3  N2   0.020
 IMS  plan-3  C19  0.020
 IMS  plan-3  C17  0.020
 IMS  plan-3  HN2  0.020

