# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 10:09:19 2021
#   Inital geometry file: a 114 line input string
#   Ligand name: [(1S)-1-(chloromethyl)-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5-methoxy-1H-indol-2-yl)methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc2[nH]c(cc2c1)C(=O)N3C[C@@H](CCl)c4c3ccc5[nH]ccc45
#
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
 Q4M  Q4M  '[(1S)-1-(chloromethyl)-1,6-dihydropyrrolo[3,2-e]indol-3(2H)-yl](5-methoxy-1H-indol-2-yl)methanone'  ligand  45  27  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_Q4M
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
 Q4M  C10   C   CR56  0   0.335  14.5751  -58.5081  -29.8821
 Q4M  C13   C   CR6   0   0.382  11.9987  -58.9949  -30.7754
 Q4M  C15   C   CH3   0  -0.435  10.0775  -58.3727  -32.0391
 Q4M  C20   C   CR56  0  -0.065  17.8084  -63.4086  -27.5514
 Q4M  C21   C   CR56  0   0.040  17.7588  -64.6907  -28.0966
 Q4M  C22   C   CR56  0   0.338  17.3170  -64.8193  -29.4338
 Q4M  C24   C   CR16  0  -0.295  17.0123  -62.4572  -29.6463
 Q4M  C26   C   CR15  0  -0.017  17.8042  -66.8537  -28.6685
 Q4M  C02   C   CH2   0  -0.447  17.1093  -63.2414  -25.1991
 Q4M  C03   C   CR15  0  -0.328  18.2337  -62.9537  -26.1832
 Q4M  C04   C   CH2   0  -0.284  18.4665  -61.4560  -26.4198
 Q4M  C06   C   C     0   0.465  17.1555  -59.8831  -27.7611
 Q4M  C07   C   CR5   0   0.223  15.9561  -59.6849  -28.5950
 Q4M  C08   C   CR15  0  -0.402  14.8063  -60.4268  -28.6810
 Q4M  C09   C   CR56  0   0.089  13.9056  -59.6934  -29.5035
 Q4M  C11   C   CR16  0  -0.294  13.9686  -57.5675  -30.7084
 Q4M  C12   C   CR16  0  -0.397  12.6832  -57.8181  -31.1478
 Q4M  C16   C   CR16  0  -0.450  12.6029  -59.9307  -29.9550
 Q4M  C19   C   CR56  0   0.367  17.4086  -62.3242  -28.3086
 Q4M  C23   C   CR16  0  -0.311  16.9584  -63.7185  -30.2105
 Q4M  C27   C   CR15  0  -0.463  18.0666  -66.0035  -27.6301
 Q4M  N05   N   NR5   0  -0.592  17.5827  -61.1474  -27.5465
 Q4M  N17   N   NR15  0  -0.721  15.8100  -58.5267  -29.3051
 Q4M  N25   N   NR15  0  -0.679  17.3581  -66.1485  -29.7457
 Q4M  O14   O   O2    0  -0.482  10.7403  -59.2817  -31.1873
 Q4M  O18   O   O     0  -0.472  17.6925  -58.9225  -27.2243
 Q4M  CL1   CL  CL    0  -0.172  17.5534  -62.7277  -23.5305
 Q4M  H151  H   HCH3  0   0.257   9.1064  -58.8093  -32.2607
 Q4M  H152  H   HCH3  0   0.224   9.9218  -57.3991  -31.5659
 Q4M  H153  H   HCH3  0   0.224  10.6132  -58.2216  -32.9803
 Q4M  H241  H   HCR6  0   0.272  16.7586  -61.5964  -30.2459
 Q4M  H261  H   HCR5  0   0.285  17.9032  -67.9259  -28.7206
 Q4M  H022  H   HCH2  0   0.288  16.1986  -62.7076  -25.4674
 Q4M  H021  H   HCH2  0   0.301  16.8908  -64.3061  -25.1517
 Q4M  H031  H   HCR5  0   0.288  19.1481  -63.4453  -25.8473
 Q4M  H041  H   HCH2  0   0.261  18.2215  -60.8389  -25.5576
 Q4M  H042  H   HCH2  0   0.270  19.5082  -61.2697  -26.6916
 Q4M  H081  H   HCR5  0   0.263  14.6234  -61.3800  -28.2112
 Q4M  H111  H   HCR6  0   0.268  14.4779  -56.6598  -31.0051
 Q4M  H121  H   HCR6  0   0.278  12.2100  -57.0867  -31.7882
 Q4M  H161  H   HCR6  0   0.253  12.0733  -60.8332  -29.6744
 Q4M  H231  H   HCR6  0   0.267  16.6586  -63.8385  -31.2437
 Q4M  H271  H   HCR5  0   0.247  18.4313  -66.2867  -26.6558
 Q4M  H171  H   HNR5  0   0.410  16.5105  -57.8082  -29.3869
 Q4M  H251  H   HNR5  0   0.412  17.0998  -66.5508  -30.6312

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
 Q4M  C10  C09   aromatic  1.413  0.020  1.413
 Q4M  C10  C11   aromatic  1.391  0.020  1.391
 Q4M  C10  N17   aromatic  1.363  0.020  1.363
 Q4M  C13  C12   aromatic  1.411  0.020  1.411
 Q4M  C13  C16   aromatic  1.383  0.020  1.383
 Q4M  C13  O14   single    1.355  0.020  1.355
 Q4M  C15  O14   single    1.411  0.020  1.411
 Q4M  C20  C21   aromatic  1.394  0.020  1.394
 Q4M  C20  C03   single    1.503  0.020  1.503
 Q4M  C20  C19   aromatic  1.382  0.020  1.382
 Q4M  C21  C22   aromatic  1.414  0.020  1.414
 Q4M  C21  C27   aromatic  1.427  0.020  1.427
 Q4M  C22  C23   aromatic  1.394  0.020  1.394
 Q4M  C22  N25   aromatic  1.366  0.020  1.366
 Q4M  C24  C19   aromatic  1.401  0.020  1.401
 Q4M  C24  C23   aromatic  1.383  0.020  1.383
 Q4M  C26  C27   aromatic  1.367  0.020  1.367
 Q4M  C26  N25   aromatic  1.363  0.020  1.363
 Q4M  C02  C03   single    1.522  0.020  1.522
 Q4M  C03  C04   single    1.534  0.020  1.534
 Q4M  C04  N05   single    1.465  0.020  1.465
 Q4M  C06  C07   single    1.474  0.020  1.474
 Q4M  C06  N05   single    1.352  0.020  1.352
 Q4M  C06  O18   double    1.224  0.020  1.224
 Q4M  C07  C08   aromatic  1.371  0.020  1.371
 Q4M  C07  N17   aromatic  1.366  0.020  1.366
 Q4M  C08  C09   aromatic  1.423  0.020  1.423
 Q4M  C09  C16   aromatic  1.399  0.020  1.399
 Q4M  C11  C12   aromatic  1.381  0.020  1.381
 Q4M  C19  N05   single    1.413  0.020  1.413
 Q4M  C02  CL1   single    1.802  0.020  1.802
 Q4M  C15  H151  single    0.970  0.020  1.090
 Q4M  C15  H152  single    0.970  0.020  1.090
 Q4M  C15  H153  single    0.970  0.020  1.090
 Q4M  C24  H241  single    0.930  0.020  1.080
 Q4M  C26  H261  single    0.930  0.020  1.080
 Q4M  C02  H022  single    0.970  0.020  1.090
 Q4M  C02  H021  single    0.970  0.020  1.090
 Q4M  C03  H031  single    0.970  0.020  1.090
 Q4M  C04  H041  single    0.970  0.020  1.090
 Q4M  C04  H042  single    0.970  0.020  1.090
 Q4M  C08  H081  single    0.930  0.020  1.080
 Q4M  C11  H111  single    0.930  0.020  1.080
 Q4M  C12  H121  single    0.930  0.020  1.080
 Q4M  C16  H161  single    0.930  0.020  1.080
 Q4M  C23  H231  single    0.930  0.020  1.080
 Q4M  C27  H271  single    0.930  0.020  1.080
 Q4M  N17  H171  single    0.860  0.020  1.020
 Q4M  N25  H251  single    0.860  0.020  1.020

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
 Q4M  N17   C10  C11   130.97  3.000
 Q4M  N17   C10  C09   107.71  3.000
 Q4M  C11   C10  C09   121.32  3.000
 Q4M  O14   C13  C16   116.28  3.000
 Q4M  O14   C13  C12   123.14  3.000
 Q4M  C16   C13  C12   120.58  3.000
 Q4M  H153  C15  H152  108.62  3.000
 Q4M  H153  C15  H151  108.52  3.000
 Q4M  H152  C15  H151  108.57  3.000
 Q4M  H153  C15  O14   112.23  3.000
 Q4M  H152  C15  O14   112.28  3.000
 Q4M  H151  C15  O14   106.49  3.000
 Q4M  C19   C20  C03   110.07  3.000
 Q4M  C19   C20  C21   119.81  3.000
 Q4M  C03   C20  C21   130.11  3.000
 Q4M  C27   C21  C22   107.03  3.000
 Q4M  C27   C21  C20   135.29  3.000
 Q4M  C22   C21  C20   117.68  3.000
 Q4M  N25   C22  C23   130.46  3.000
 Q4M  N25   C22  C21   107.16  3.000
 Q4M  C23   C22  C21   122.37  3.000
 Q4M  H241  C24  C23   119.45  3.000
 Q4M  H241  C24  C19   121.40  3.000
 Q4M  C23   C24  C19   119.15  3.000
 Q4M  H261  C26  N25   120.43  3.000
 Q4M  H261  C26  C27   129.61  3.000
 Q4M  N25   C26  C27   109.96  3.000
 Q4M  H021  C02  H022  108.81  3.000
 Q4M  H021  C02  CL1   106.75  3.000
 Q4M  H022  C02  CL1   107.13  3.000
 Q4M  H021  C02  C03   111.20  3.000
 Q4M  H022  C02  C03   111.46  3.000
 Q4M  CL1   C02  C03   111.28  3.000
 Q4M  H031  C03  C04   111.11  3.000
 Q4M  H031  C03  C02   109.57  3.000
 Q4M  C04   C03  C02   113.36  3.000
 Q4M  H031  C03  C20   112.40  3.000
 Q4M  C04   C03  C20   101.42  3.000
 Q4M  C02   C03  C20   108.80  3.000
 Q4M  H042  C04  H041  108.37  3.000
 Q4M  H042  C04  N05   110.36  3.000
 Q4M  H041  C04  N05   110.74  3.000
 Q4M  H042  C04  C03   110.46  3.000
 Q4M  H041  C04  C03   113.41  3.000
 Q4M  N05   C04  C03   103.46  3.000
 Q4M  O18   C06  N05   121.70  3.000
 Q4M  O18   C06  C07   119.96  3.000
 Q4M  N05   C06  C07   118.21  3.000
 Q4M  N17   C07  C08   109.66  3.000
 Q4M  N17   C07  C06   119.67  3.000
 Q4M  C08   C07  C06   130.17  3.000
 Q4M  H081  C08  C09   126.86  3.000
 Q4M  H081  C08  C07   126.39  3.000
 Q4M  C09   C08  C07   106.75  3.000
 Q4M  C16   C09  C08   133.50  3.000
 Q4M  C16   C09  C10   119.80  3.000
 Q4M  C08   C09  C10   106.70  3.000
 Q4M  H111  C11  C12   120.19  3.000
 Q4M  H111  C11  C10   121.65  3.000
 Q4M  C12   C11  C10   118.16  3.000
 Q4M  H121  C12  C11   118.22  3.000
 Q4M  H121  C12  C13   120.54  3.000
 Q4M  C11   C12  C13   121.24  3.000
 Q4M  H161  C16  C09   120.86  3.000
 Q4M  H161  C16  C13   120.24  3.000
 Q4M  C09   C16  C13   118.90  3.000
 Q4M  N05   C19  C24   128.96  3.000
 Q4M  N05   C19  C20   108.81  3.000
 Q4M  C24   C19  C20   122.03  3.000
 Q4M  H231  C23  C24   120.09  3.000
 Q4M  H231  C23  C22   121.03  3.000
 Q4M  C24   C23  C22   118.87  3.000
 Q4M  H271  C27  C26   126.00  3.000
 Q4M  H271  C27  C21   127.60  3.000
 Q4M  C26   C27  C21   106.40  3.000
 Q4M  C19   N05  C06   130.88  3.000
 Q4M  C19   N05  C04   108.29  3.000
 Q4M  C06   N05  C04   120.66  3.000
 Q4M  H171  N17  C07   124.94  3.000
 Q4M  H171  N17  C10   125.88  3.000
 Q4M  C07   N17  C10   109.17  3.000
 Q4M  H251  N25  C26   124.95  3.000
 Q4M  H251  N25  C22   125.61  3.000
 Q4M  C26   N25  C22   109.44  3.000
 Q4M  C15   O14  C13   118.91  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
 Q4M  CONST_01  C07   C08  C09  C10    0.00   0.0  0
 Q4M  CONST_02  C13   C16  C09  C10    0.00   0.0  0
 Q4M  CONST_03  C13   C12  C11  C10    0.00   0.0  0
 Q4M  CONST_04  C08   C07  N17  C10    0.00   0.0  0
 Q4M  CONST_05  C08   C09  C16  C13  180.00   0.0  0
 Q4M  CONST_06  C23   C22  C21  C20    0.00   0.0  0
 Q4M  CONST_07  N25   C22  C21  C20  180.00   0.0  0
 Q4M  CONST_08  C26   C27  C21  C20  180.00   0.0  0
 Q4M  CONST_09  C23   C24  C19  C20    0.00   0.0  0
 Q4M  CONST_10  C24   C19  C20  C21    0.00   0.0  0
 Q4M  CONST_11  C24   C23  C22  C21    0.00   0.0  0
 Q4M  CONST_12  C26   N25  C22  C21    0.00   0.0  0
 Q4M  CONST_13  N25   C26  C27  C21    0.00   0.0  0
 Q4M  CONST_14  C19   C20  C21  C22    0.00   0.0  0
 Q4M  CONST_15  C26   C27  C21  C22    0.00   0.0  0
 Q4M  CONST_16  C19   C24  C23  C22    0.00   0.0  0
 Q4M  CONST_17  C27   C26  N25  C22    0.00   0.0  0
 Q4M  CONST_18  N25   C22  C23  C24  180.00   0.0  0
 Q4M  CONST_19  C23   C22  N25  C26  180.00   0.0  0
 Q4M  CONST_20  C16   C09  C08  C07  180.00   0.0  0
 Q4M  CONST_21  C09   C10  N17  C07    0.00   0.0  0
 Q4M  CONST_22  C11   C10  N17  C07  180.00   0.0  0
 Q4M  CONST_23  C11   C10  C09  C08  180.00   0.0  0
 Q4M  CONST_24  N17   C10  C09  C08    0.00   0.0  0
 Q4M  CONST_25  C12   C11  C10  C09    0.00   0.0  0
 Q4M  CONST_26  N17   C07  C08  C09    0.00   0.0  0
 Q4M  CONST_27  C12   C13  C16  C09    0.00   0.0  0
 Q4M  CONST_28  C16   C09  C10  C11    0.00   0.0  0
 Q4M  CONST_29  C16   C13  C12  C11    0.00   0.0  0
 Q4M  CONST_30  N17   C10  C11  C12  180.00   0.0  0
 Q4M  CONST_31  N17   C10  C09  C16  180.00   0.0  0
 Q4M  CONST_32  C27   C21  C20  C19  180.00   0.0  0
 Q4M  CONST_33  C27   C21  C22  C23  180.00   0.0  0
 Q4M  CONST_34  N25   C22  C21  C27    0.00   0.0  0
 Q4M  CONST_35  C06   C07  N17  C10  180.00   0.0  0
 Q4M  CONST_36  C09   C08  C07  C06  180.00   0.0  0
 Q4M  CONST_37  O14   C13  C16  C09  180.00   0.0  0
 Q4M  CONST_38  O14   C13  C12  C11  180.00   0.0  0
 Q4M  CONST_41  H081  C08  C09  C10  180.00   0.0  0
 Q4M  CONST_42  H161  C16  C09  C10  180.00   0.0  0
 Q4M  CONST_43  H121  C12  C11  C10  180.00   0.0  0
 Q4M  CONST_44  H111  C11  C12  C13  180.00   0.0  0
 Q4M  CONST_45  H271  C27  C21  C20    0.00   0.0  0
 Q4M  CONST_46  H241  C24  C19  C20  180.00   0.0  0
 Q4M  CONST_47  H231  C23  C22  C21  180.00   0.0  0
 Q4M  CONST_48  H251  N25  C22  C21  180.00   0.0  0
 Q4M  CONST_49  H261  C26  C27  C21  180.00   0.0  0
 Q4M  CONST_50  H171  N17  C07  C08  180.00   0.0  0
 Q4M  Var_01    C04   N05  C19  C20   16.31  30.0  1
 Q4M  Var_02    C19   N05  C04  C03  -27.14  30.0  1
 Q4M  Var_03    N05   C06  C07  C08   37.25  30.0  2
 Q4M  Var_04    C12   C13  O14  C15    0.58  30.0  2
 Q4M  Var_05    H151  C15  O14  C13  178.57  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
 Q4M  chir_01  C03  C20  C02  C04  positiv

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
 Q4M  plan-1  C10   0.020
 Q4M  plan-1  C13   0.020
 Q4M  plan-1  C06   0.020
 Q4M  plan-1  C07   0.020
 Q4M  plan-1  C08   0.020
 Q4M  plan-1  C09   0.020
 Q4M  plan-1  C11   0.020
 Q4M  plan-1  C12   0.020
 Q4M  plan-1  C16   0.020
 Q4M  plan-1  N17   0.020
 Q4M  plan-1  O14   0.020
 Q4M  plan-1  H081  0.020
 Q4M  plan-1  H111  0.020
 Q4M  plan-1  H121  0.020
 Q4M  plan-1  H161  0.020
 Q4M  plan-1  H171  0.020
 Q4M  plan-2  C20   0.020
 Q4M  plan-2  C21   0.020
 Q4M  plan-2  C22   0.020
 Q4M  plan-2  C24   0.020
 Q4M  plan-2  C26   0.020
 Q4M  plan-2  C03   0.020
 Q4M  plan-2  C19   0.020
 Q4M  plan-2  C23   0.020
 Q4M  plan-2  C27   0.020
 Q4M  plan-2  N05   0.020
 Q4M  plan-2  N25   0.020
 Q4M  plan-2  H241  0.020
 Q4M  plan-2  H261  0.020
 Q4M  plan-2  H231  0.020
 Q4M  plan-2  H271  0.020
 Q4M  plan-2  H251  0.020
 Q4M  plan-3  C04   0.020
 Q4M  plan-3  C06   0.020
 Q4M  plan-3  C07   0.020
 Q4M  plan-3  C19   0.020
 Q4M  plan-3  N05   0.020
 Q4M  plan-3  O18   0.020

