# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 02:11:43 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: 1-{1-[2-(hydroxymethyl)phenyl]-7-phenoxyindolizin-3-yl}ethanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(=O)c1cc(c2cc(Oc3ccccc3)ccn12)c4ccccc4CO
#
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
 IR5  IR5  1-{1-[2-(hydroxymethyl)phenyl]-7-phenoxyindolizin-3-yl}ethanone  ligand  46  27  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_IR5
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
 IR5  C01  C  CH3   0  -0.792   2.9747   4.4532   0.1775
 IR5  C02  C  C     0   0.337   1.6210   3.8568  -0.1194
 IR5  O01  O  O     0  -0.443   0.6725   4.5685  -0.4268
 IR5  C03  C  CR5   0   0.228   1.5202   2.4232  -0.0016
 IR5  C04  C  CR15  0  -0.387   2.5176   1.5053   0.3151
 IR5  C05  C  CR5   0  -0.022   1.9927   0.2185   0.3058
 IR5  C06  C  CR6   0   0.040   2.7010  -1.0393   0.5949
 IR5  C07  C  CR16  0  -0.300   3.2035  -1.2550   1.8771
 IR5  C08  C  CR16  0  -0.255   3.8822  -2.4222   2.1939
 IR5  C09  C  CR16  0  -0.251   4.0572  -3.3930   1.2194
 IR5  C10  C  CR16  0  -0.292   3.5697  -3.1861  -0.0640
 IR5  C11  C  CR6   0  -0.006   2.8974  -2.0132  -0.3956
 IR5  C12  C  CH2   0  -0.203   2.4072  -1.7748  -1.8001
 IR5  O02  O  OH1   0  -0.666   3.0337  -2.6658  -2.6879
 IR5  C13  C  CR56  0   0.432   0.6326   0.3483  -0.0061
 IR5  C14  C  CR16  0  -0.507  -0.4047  -0.5943  -0.0974
 IR5  C15  C  CR6   0   0.451  -1.6642  -0.1698  -0.4051
 IR5  O1   O  O2    0  -0.502  -2.6467  -1.0950  -0.5474
 IR5  C16  C  CR6   0   0.331  -3.8927  -0.8397  -0.0339
 IR5  C17  C  CR16  0  -0.315  -4.0642  -0.2400   1.2075
 IR5  C18  C  CR16  0  -0.247  -5.3503  -0.0516   1.6943
 IR5  C19  C  CR16  0  -0.264  -6.4528  -0.4644   0.9579
 IR5  C20  C  CR16  0  -0.249  -6.2639  -1.0703  -0.2774
 IR5  C21  C  CR16  0  -0.325  -4.9844  -1.2562  -0.7819
 IR5  C22  C  CR16  0  -0.430  -1.9143   1.2079  -0.6236
 IR5  C1   C  CR16  0   0.024  -0.9042   2.1056  -0.5101
 IR5  N1   N  N     0  -0.613   0.3560   1.6892  -0.1962
 IR5  H1   H  HCH3  0   0.267   3.2185   4.3327   1.2345
 IR5  H2   H  HCH3  0   0.261   3.7659   3.9685  -0.3938
 IR5  H3   H  HCH3  0   0.265   2.9731   5.5152  -0.0569
 IR5  H4   H  HCR5  0   0.267   3.5468   1.7553   0.5232
 IR5  H5   H  HCR6  0   0.247   3.0511  -0.4961   2.6347
 IR5  H6   H  HCR6  0   0.255   4.2657  -2.5723   3.1948
 IR5  H7   H  HCR6  0   0.254   4.5799  -4.3116   1.4534
 IR5  H8   H  HCR6  0   0.255   3.7294  -3.9458  -0.8164
 IR5  H9   H  HCH2  0   0.220   1.3161  -1.8951  -1.8310
 IR5  H10  H  HCH2  0   0.216   2.6044  -0.7289  -2.0705
 IR5  H11  H  HOH1  0   0.462   2.6101  -2.5752  -3.5459
 IR5  H12  H  HCR6  0   0.286  -0.1925  -1.6387   0.0905
 IR5  H13  H  HCR6  0   0.282  -3.2104   0.0715   1.7969
 IR5  H14  H  HCR6  0   0.265  -5.4872   0.4171   2.6600
 IR5  H15  H  HCR6  0   0.260  -7.4519  -0.3167   1.3451
 IR5  H16  H  HCR6  0   0.264  -7.1167  -1.3941  -0.8596
 IR5  H17  H  HCR6  0   0.272  -4.8313  -1.7248  -1.7458
 IR5  H18  H  HCR6  0   0.303  -2.8986   1.5676  -0.8872
 IR5  H19  H  HCR6  0   0.326  -1.0468   3.1612  -0.6629

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
 IR5  O02  C12  single    1.405  0.020  1.405
 IR5  C12  C11  single    1.507  0.020  1.507
 IR5  C10  C11  aromatic  1.392  0.020  1.392
 IR5  C10  C09  aromatic  1.388  0.020  1.388
 IR5  C11  C06  aromatic  1.403  0.020  1.403
 IR5  C09  C08  aromatic  1.387  0.020  1.387
 IR5  C06  C05  single    1.472  0.020  1.472
 IR5  C06  C07  aromatic  1.394  0.020  1.394
 IR5  C05  C04  aromatic  1.390  0.020  1.390
 IR5  C05  C13  aromatic  1.401  0.020  1.401
 IR5  C04  C03  aromatic  1.392  0.020  1.392
 IR5  C01  C02  single    1.509  0.020  1.509
 IR5  C17  C18  aromatic  1.388  0.020  1.388
 IR5  C17  C16  aromatic  1.389  0.020  1.389
 IR5  C03  C02  single    1.442  0.020  1.442
 IR5  C03  N1   aromatic  1.390  0.020  1.390
 IR5  C13  N1   aromatic  1.382  0.020  1.382
 IR5  C13  C14  aromatic  1.405  0.020  1.405
 IR5  C02  O01  double    1.225  0.020  1.225
 IR5  C08  C07  aromatic  1.387  0.020  1.387
 IR5  C18  C19  aromatic  1.389  0.020  1.389
 IR5  N1   C1   aromatic  1.364  0.020  1.364
 IR5  C14  C15  aromatic  1.364  0.020  1.364
 IR5  C1   C22  aromatic  1.356  0.020  1.356
 IR5  C15  C22  aromatic  1.417  0.020  1.417
 IR5  C15  O1   single    1.357  0.020  1.357
 IR5  O1   C16  single    1.372  0.020  1.372
 IR5  C16  C21  aromatic  1.387  0.020  1.387
 IR5  C19  C20  aromatic  1.389  0.020  1.389
 IR5  C21  C20  aromatic  1.388  0.020  1.388
 IR5  C01  H1   single    0.970  0.020  1.090
 IR5  C01  H2   single    0.970  0.020  1.090
 IR5  C01  H3   single    0.970  0.020  1.090
 IR5  C04  H4   single    0.930  0.020  1.080
 IR5  C07  H5   single    0.930  0.020  1.080
 IR5  C08  H6   single    0.930  0.020  1.080
 IR5  C09  H7   single    0.930  0.020  1.080
 IR5  C10  H8   single    0.930  0.020  1.080
 IR5  C12  H9   single    0.970  0.020  1.090
 IR5  C12  H10  single    0.970  0.020  1.090
 IR5  O02  H11  single    0.850  0.020  0.980
 IR5  C14  H12  single    0.930  0.020  1.080
 IR5  C17  H13  single    0.930  0.020  1.080
 IR5  C18  H14  single    0.930  0.020  1.080
 IR5  C19  H15  single    0.930  0.020  1.080
 IR5  C20  H16  single    0.930  0.020  1.080
 IR5  C21  H17  single    0.930  0.020  1.080
 IR5  C22  H18  single    0.930  0.020  1.080
 IR5  C1   H19  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
 IR5  H3   C01  H2   108.81  3.000
 IR5  H3   C01  H1   108.48  3.000
 IR5  H2   C01  H1   107.25  3.000
 IR5  H3   C01  C02  110.01  3.000
 IR5  H2   C01  C02  111.87  3.000
 IR5  H1   C01  C02  110.33  3.000
 IR5  C03  C02  O01  122.95  3.000
 IR5  O01  C02  C01  120.96  3.000
 IR5  C03  C02  C01  116.08  3.000
 IR5  N1   C03  C04  106.48  3.000
 IR5  N1   C03  C02  124.90  3.000
 IR5  C04  C03  C02  128.62  3.000
 IR5  H4   C04  C05  125.16  3.000
 IR5  H4   C04  C03  125.05  3.000
 IR5  C05  C04  C03  109.78  3.000
 IR5  C13  C05  C06  126.14  3.000
 IR5  C13  C05  C04  106.39  3.000
 IR5  C06  C05  C04  127.45  3.000
 IR5  C11  C06  C07  119.44  3.000
 IR5  C07  C06  C05  119.10  3.000
 IR5  C11  C06  C05  121.45  3.000
 IR5  H5   C07  C08  119.92  3.000
 IR5  H5   C07  C06  118.96  3.000
 IR5  C08  C07  C06  121.12  3.000
 IR5  H6   C08  C09  120.54  3.000
 IR5  H6   C08  C07  120.09  3.000
 IR5  C09  C08  C07  119.37  3.000
 IR5  H7   C09  C10  119.73  3.000
 IR5  H7   C09  C08  120.20  3.000
 IR5  C10  C09  C08  120.07  3.000
 IR5  H8   C10  C11  119.84  3.000
 IR5  H8   C10  C09  119.13  3.000
 IR5  C11  C10  C09  121.02  3.000
 IR5  C12  C11  C10  120.83  3.000
 IR5  C10  C11  C06  118.97  3.000
 IR5  C12  C11  C06  120.19  3.000
 IR5  H10  C12  H9   106.01  3.000
 IR5  H10  C12  O02  111.61  3.000
 IR5  H9   C12  O02  110.84  3.000
 IR5  H10  C12  C11  108.77  3.000
 IR5  H9   C12  C11  109.40  3.000
 IR5  O02  C12  C11  110.10  3.000
 IR5  H11  O02  C12  107.93  3.000
 IR5  N1   C13  C14  119.63  3.000
 IR5  C14  C13  C05  131.99  3.000
 IR5  N1   C13  C05  108.34  3.000
 IR5  H12  C14  C15  121.37  3.000
 IR5  H12  C14  C13  119.45  3.000
 IR5  C15  C14  C13  119.18  3.000
 IR5  C22  C15  O1   121.26  3.000
 IR5  O1   C15  C14  118.68  3.000
 IR5  C22  C15  C14  120.01  3.000
 IR5  C16  O1   C15  119.44  3.000
 IR5  C21  C16  C17  120.94  3.000
 IR5  C21  C16  O1   117.20  3.000
 IR5  C17  C16  O1   121.80  3.000
 IR5  H13  C17  C18  120.03  3.000
 IR5  H13  C17  C16  120.87  3.000
 IR5  C18  C17  C16  119.10  3.000
 IR5  H14  C18  C19  120.10  3.000
 IR5  H14  C18  C17  119.28  3.000
 IR5  C19  C18  C17  120.62  3.000
 IR5  H15  C19  C20  120.25  3.000
 IR5  H15  C19  C18  120.19  3.000
 IR5  C20  C19  C18  119.56  3.000
 IR5  H16  C20  C21  119.40  3.000
 IR5  H16  C20  C19  120.12  3.000
 IR5  C21  C20  C19  120.48  3.000
 IR5  H17  C21  C20  120.80  3.000
 IR5  H17  C21  C16  119.91  3.000
 IR5  C20  C21  C16  119.29  3.000
 IR5  H18  C22  C1   118.59  3.000
 IR5  H18  C22  C15  121.46  3.000
 IR5  C1   C22  C15  119.95  3.000
 IR5  H19  C1   N1   117.04  3.000
 IR5  H19  C1   C22  122.60  3.000
 IR5  N1   C1   C22  120.36  3.000
 IR5  C1   N1   C13  120.84  3.000
 IR5  C1   N1   C03  130.16  3.000
 IR5  C13  N1   C03  109.00  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
 IR5  CONST_01  C06  C05  C04  C03  180.00   0.0  0
 IR5  CONST_02  C13  C05  C04  C03    0.00   0.0  0
 IR5  CONST_03  C05  C13  N1   C03    0.00   0.0  0
 IR5  CONST_04  C14  C13  N1   C03  180.00   0.0  0
 IR5  CONST_05  C22  C1   N1   C03  180.00   0.0  0
 IR5  CONST_08  N1   C13  C05  C04    0.00   0.0  0
 IR5  CONST_09  C14  C13  C05  C04  180.00   0.0  0
 IR5  CONST_10  C13  N1   C03  C04    0.00   0.0  0
 IR5  CONST_11  C1   N1   C03  C04  180.00   0.0  0
 IR5  CONST_12  C10  C11  C06  C05  180.00   0.0  0
 IR5  CONST_13  C08  C07  C06  C05  180.00   0.0  0
 IR5  CONST_14  N1   C03  C04  C05    0.00   0.0  0
 IR5  CONST_15  C1   N1   C13  C05  180.00   0.0  0
 IR5  CONST_16  C15  C14  C13  C05  180.00   0.0  0
 IR5  CONST_17  C09  C10  C11  C06    0.00   0.0  0
 IR5  CONST_18  N1   C13  C05  C06  180.00   0.0  0
 IR5  CONST_19  C14  C13  C05  C06    0.00   0.0  0
 IR5  CONST_20  C09  C08  C07  C06    0.00   0.0  0
 IR5  CONST_21  C10  C11  C06  C07    0.00   0.0  0
 IR5  CONST_23  C10  C09  C08  C07    0.00   0.0  0
 IR5  CONST_24  C11  C10  C09  C08    0.00   0.0  0
 IR5  CONST_25  C11  C06  C07  C08    0.00   0.0  0
 IR5  CONST_27  C22  C1   N1   C13    0.00   0.0  0
 IR5  CONST_28  C22  C15  C14  C13    0.00   0.0  0
 IR5  CONST_29  C1   N1   C13  C14    0.00   0.0  0
 IR5  CONST_30  C1   C22  C15  C14    0.00   0.0  0
 IR5  CONST_31  N1   C13  C14  C15    0.00   0.0  0
 IR5  CONST_32  N1   C1   C22  C15    0.00   0.0  0
 IR5  CONST_33  C19  C18  C17  C16    0.00   0.0  0
 IR5  CONST_34  C19  C20  C21  C16    0.00   0.0  0
 IR5  CONST_35  C20  C19  C18  C17    0.00   0.0  0
 IR5  CONST_36  C20  C21  C16  C17    0.00   0.0  0
 IR5  CONST_37  C21  C16  C17  C18    0.00   0.0  0
 IR5  CONST_38  C21  C20  C19  C18    0.00   0.0  0
 IR5  CONST_39  C05  C04  C03  C02  180.00   0.0  0
 IR5  CONST_40  C13  N1   C03  C02  180.00   0.0  0
 IR5  CONST_41  C1   N1   C03  C02    0.00   0.0  0
 IR5  CONST_42  C12  C11  C06  C05    0.00   0.0  0
 IR5  CONST_43  C12  C11  C06  C07  180.00   0.0  0
 IR5  CONST_44  C12  C11  C10  C09  180.00   0.0  0
 IR5  CONST_45  O1   C15  C14  C13  180.00   0.0  0
 IR5  CONST_46  C1   C22  C15  O1   180.00   0.0  0
 IR5  CONST_47  C18  C17  C16  O1   180.00   0.0  0
 IR5  CONST_48  C20  C21  C16  O1   180.00   0.0  0
 IR5  CONST_49  H19  C1   N1   C03    0.00   0.0  0
 IR5  CONST_50  H5   C07  C06  C05    0.00   0.0  0
 IR5  CONST_51  H12  C14  C13  C05    0.00   0.0  0
 IR5  CONST_52  H8   C10  C11  C06  180.00   0.0  0
 IR5  CONST_53  H4   C04  C05  C06    0.00   0.0  0
 IR5  CONST_54  H6   C08  C07  C06  180.00   0.0  0
 IR5  CONST_55  H7   C09  C08  C07  180.00   0.0  0
 IR5  CONST_56  H18  C22  C15  C14  180.00   0.0  0
 IR5  CONST_57  H14  C18  C17  C16  180.00   0.0  0
 IR5  CONST_58  H16  C20  C21  C16  180.00   0.0  0
 IR5  CONST_59  H15  C19  C18  C17  180.00   0.0  0
 IR5  CONST_60  H17  C21  C16  C17  180.00   0.0  0
 IR5  CONST_61  H13  C17  C18  C19  180.00   0.0  0
 IR5  Var_01    C17  C16  O1   C15  -41.12  30.0  2
 IR5  Var_02    C22  C15  O1   C16  -43.66  30.0  2
 IR5  Var_03    C04  C03  C02  C01   -1.97  30.0  3
 IR5  Var_04    O02  C12  C11  C06  162.90  30.0  1
 IR5  Var_05    H1   C01  C02  C03  -67.23  30.0  3

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
 IR5  plan-1  C05  0.020
 IR5  plan-1  C06  0.020
 IR5  plan-1  C07  0.020
 IR5  plan-1  C08  0.020
 IR5  plan-1  C09  0.020
 IR5  plan-1  C10  0.020
 IR5  plan-1  C11  0.020
 IR5  plan-1  C12  0.020
 IR5  plan-1  H5   0.020
 IR5  plan-1  H6   0.020
 IR5  plan-1  H7   0.020
 IR5  plan-1  H8   0.020
 IR5  plan-2  O1   0.020
 IR5  plan-2  C16  0.020
 IR5  plan-2  C17  0.020
 IR5  plan-2  C18  0.020
 IR5  plan-2  C19  0.020
 IR5  plan-2  C20  0.020
 IR5  plan-2  C21  0.020
 IR5  plan-2  H13  0.020
 IR5  plan-2  H14  0.020
 IR5  plan-2  H15  0.020
 IR5  plan-2  H16  0.020
 IR5  plan-2  H17  0.020
 IR5  plan-3  C02  0.020
 IR5  plan-3  C03  0.020
 IR5  plan-3  C04  0.020
 IR5  plan-3  C05  0.020
 IR5  plan-3  C06  0.020
 IR5  plan-3  C13  0.020
 IR5  plan-3  C14  0.020
 IR5  plan-3  C15  0.020
 IR5  plan-3  O1   0.020
 IR5  plan-3  C22  0.020
 IR5  plan-3  C1   0.020
 IR5  plan-3  N1   0.020
 IR5  plan-3  H4   0.020
 IR5  plan-3  H12  0.020
 IR5  plan-3  H18  0.020
 IR5  plan-3  H19  0.020
 IR5  plan-4  C01  0.020
 IR5  plan-4  C02  0.020
 IR5  plan-4  O01  0.020
 IR5  plan-4  C03  0.020

