# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 22 13:19:26 2020
#   Inital geometry file: a 131 line input string
#   Ligand name: (15S,19S)-1-(hydroxymethyl)-17-pentyl-17-azapentacyclo[6.6.5.0~2,7~.0~9,14~.0~15,19~]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCN1C(=O)[C@H]2C3c4ccccc4C(CO)([C@H]2C1=O)c5ccccc35
#
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
 DAI  DAI  '(15S,19S)-1-(hydroxymethyl)-17-pentyl-17-azapentacyclo[6.6.5.0~2,7~.0~9,14~.0~15,19~]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione (non-preferred name)'  ligand  53  28  .  2021-08-08  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_DAI
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
 DAI  O23   O  O     0  -0.427   1.7417  -1.6762   1.5563
 DAI  C24   C  CR5   0   0.596   1.1889  -0.7190   1.0717
 DAI  C28   C  C     0  -0.371   1.4241  -0.1405  -0.2998
 DAI  C13   C  CR16  0  -0.439   1.0902  -1.1766  -1.4021
 DAI  C15   C  CR6   0   0.144  -0.3642  -1.5179  -1.2406
 DAI  C16   C  CR6   0   0.164  -1.2196  -0.4204  -1.3645
 DAI  C17   C  CR16  0  -0.328  -2.5823  -0.5904  -1.1726
 DAI  C18   C  CR16  0  -0.253  -3.0820  -1.8546  -0.8740
 DAI  C19   C  CR16  0  -0.258  -2.2289  -2.9428  -0.7588
 DAI  C14   C  CR16  0  -0.328  -0.8602  -2.7742  -0.9371
 DAI  C12   C  CR66  0   0.185   1.2595  -0.4348  -2.6951
 DAI  C11   C  CR66  0   0.215   0.4294   0.6803  -2.8139
 DAI  C9    C  CR16  0  -0.340   0.5421   1.4938  -3.9322
 DAI  C8    C  CR16  0  -0.254   1.4618   1.1748  -4.9276
 DAI  C7    C  CR16  0  -0.260   2.2719   0.0547  -4.8096
 DAI  C6    C  CR16  0  -0.348   2.1763  -0.7526  -3.6813
 DAI  C27   C  C     0  -0.376   0.4733   1.0590  -0.3989
 DAI  C10   C  CR6   0  -0.288  -0.4959   0.8910  -1.6208
 DAI  C5    C  CH2   0  -0.182  -1.4037   2.1007  -1.7677
 DAI  O4    O  OH1   0  -0.664  -2.2223   1.9243  -2.8991
 DAI  C26   C  CR5   0   0.602  -0.2363   1.0773   0.9422
 DAI  O22   O  O     0  -0.425  -1.0522   1.8778   1.3313
 DAI  N25   N  NR5   0  -0.525   0.2105   0.0165   1.6962
 DAI  C21   C  CH2   0  -0.313  -0.2622  -0.2671   3.0387
 DAI  C20   C  CH2   0  -0.431   0.5229   0.4785   4.1090
 DAI  C3    C  CH2   0  -0.416   0.0593   0.0945   5.5080
 DAI  C2    C  CH2   0  -0.421   0.8067   0.8396   6.6068
 DAI  C1    C  CH3   0  -0.661   0.3561   0.4322   8.0026
 DAI  H28   H  H     0   0.329   2.4708   0.1566  -0.3839
 DAI  H13   H  HCR6  0   0.283   1.7413  -2.0481  -1.3332
 DAI  H17   H  HCR6  0   0.253  -3.2661   0.2425  -1.2574
 DAI  H18   H  HCR6  0   0.255  -4.1469  -1.9867  -0.7320
 DAI  H19   H  HCR6  0   0.255  -2.6269  -3.9218  -0.5257
 DAI  H14   H  HCR6  0   0.253  -0.1844  -3.6150  -0.8364
 DAI  H9    H  HCR6  0   0.253  -0.0825   2.3672  -4.0514
 DAI  H8    H  HCR6  0   0.254   1.5388   1.8078  -5.8023
 DAI  H7    H  HCR6  0   0.255   2.9805  -0.1881  -5.5908
 DAI  H6    H  HCR6  0   0.252   2.8159  -1.6199  -3.5706
 DAI  H27   H  H     0   0.325   1.0205   1.9996  -0.5061
 DAI  H51   H  HCH2  0   0.239  -2.0037   2.2239  -0.8622
 DAI  H52   H  HCH2  0   0.223  -0.7755   2.9984  -1.8539
 DAI  HO4   H  HOH1  0   0.460  -2.8160   2.6786  -2.9559
 DAI  H211  H  HCH2  0   0.263  -0.1884  -1.3440   3.1915
 DAI  H212  H  HCH2  0   0.265  -1.3200  -0.0081   3.0858
 DAI  H201  H  HCH2  0   0.231   0.4092   1.5563   3.9642
 DAI  H202  H  HCH2  0   0.231   1.5878   0.2549   4.0001
 DAI  H31   H  HCH2  0   0.216   0.1875  -0.9844   5.6471
 DAI  H32   H  HCH2  0   0.217  -1.0143   0.2890   5.6045
 DAI  H21   H  HCH2  0   0.215   0.6647   1.9166   6.4744
 DAI  H22   H  HCH2  0   0.214   1.8807   0.6595   6.5002
 DAI  H11   H  HCH3  0   0.227   0.9018   0.9755   8.7746
 DAI  H12   H  HCH3  0   0.217  -0.7074   0.6311   8.1472
 DAI  H13A  H  HCH3  0   0.217   0.5170  -0.6340   8.1716

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
 DAI  O23  C24   double    1.207  0.020  1.207
 DAI  C24  C28   single    1.507  0.020  1.507
 DAI  C24  N25   single    1.374  0.020  1.374
 DAI  C28  C13   single    1.549  0.020  1.549
 DAI  C28  C27   single    1.534  0.020  1.534
 DAI  C28  H28   single    0.970  0.020  1.090
 DAI  C13  C15   single    1.503  0.020  1.503
 DAI  C13  C12   single    1.500  0.020  1.500
 DAI  C13  H13   single    0.970  0.020  1.090
 DAI  C15  C16   aromatic  1.397  0.020  1.397
 DAI  C15  C14   aromatic  1.384  0.020  1.384
 DAI  C16  C17   aromatic  1.387  0.020  1.387
 DAI  C16  C10   single    1.520  0.020  1.520
 DAI  C17  C18   aromatic  1.392  0.020  1.392
 DAI  C17  H17   single    0.930  0.020  1.080
 DAI  C18  C19   aromatic  1.388  0.020  1.388
 DAI  C18  H18   single    0.930  0.020  1.080
 DAI  C19  C14   aromatic  1.390  0.020  1.390
 DAI  C19  H19   single    0.930  0.020  1.080
 DAI  C14  H14   single    0.930  0.020  1.080
 DAI  C12  C11   aromatic  1.395  0.020  1.395
 DAI  C12  C6    aromatic  1.384  0.020  1.384
 DAI  C11  C9    aromatic  1.387  0.020  1.387
 DAI  C11  C10   single    1.525  0.020  1.525
 DAI  C9   C8    aromatic  1.392  0.020  1.392
 DAI  C9   H9    single    0.930  0.020  1.080
 DAI  C8   C7    aromatic  1.387  0.020  1.387
 DAI  C8   H8    single    0.930  0.020  1.080
 DAI  C7   C6    aromatic  1.391  0.020  1.391
 DAI  C7   H7    single    0.930  0.020  1.080
 DAI  C6   H6    single    0.930  0.020  1.080
 DAI  C27  C10   single    1.569  0.020  1.569
 DAI  C27  C26   single    1.517  0.020  1.517
 DAI  C27  H27   single    0.970  0.020  1.090
 DAI  C10  C5    single    1.520  0.020  1.520
 DAI  C5   O4    single    1.408  0.020  1.408
 DAI  C5   H51   single    0.970  0.020  1.090
 DAI  C5   H52   single    0.970  0.020  1.090
 DAI  O4   HO4   single    0.850  0.020  0.980
 DAI  C26  O22   double    1.208  0.020  1.208
 DAI  C26  N25   single    1.376  0.020  1.376
 DAI  N25  C21   single    1.451  0.020  1.451
 DAI  C21  C20   single    1.522  0.020  1.522
 DAI  C21  H211  single    0.970  0.020  1.090
 DAI  C21  H212  single    0.970  0.020  1.090
 DAI  C20  C3    single    1.523  0.020  1.523
 DAI  C20  H201  single    0.970  0.020  1.090
 DAI  C20  H202  single    0.970  0.020  1.090
 DAI  C3   C2    single    1.524  0.020  1.524
 DAI  C3   H31   single    0.970  0.020  1.090
 DAI  C3   H32   single    0.970  0.020  1.090
 DAI  C2   C1    single    1.522  0.020  1.522
 DAI  C2   H21   single    0.970  0.020  1.090
 DAI  C2   H22   single    0.970  0.020  1.090
 DAI  C1   H11   single    0.970  0.020  1.090
 DAI  C1   H12   single    0.970  0.020  1.090
 DAI  C1   H13A  single    0.970  0.020  1.090

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
 DAI  N25   C24  C28   108.62  3.000
 DAI  N25   C24  O23   124.62  3.000
 DAI  C28   C24  O23   126.76  3.000
 DAI  H28   C28  C27   112.13  3.000
 DAI  H28   C28  C13   109.51  3.000
 DAI  C27   C28  C13   110.09  3.000
 DAI  H28   C28  C24   108.93  3.000
 DAI  C27   C28  C24   105.21  3.000
 DAI  C13   C28  C24   110.92  3.000
 DAI  H13   C13  C12   112.48  3.000
 DAI  H13   C13  C15   112.94  3.000
 DAI  C12   C13  C15   108.31  3.000
 DAI  H13   C13  C28   111.16  3.000
 DAI  C12   C13  C28   104.97  3.000
 DAI  C15   C13  C28   106.50  3.000
 DAI  C14   C15  C16   120.86  3.000
 DAI  C14   C15  C13   125.21  3.000
 DAI  C16   C15  C13   113.87  3.000
 DAI  C10   C16  C17   126.67  3.000
 DAI  C10   C16  C15   113.66  3.000
 DAI  C17   C16  C15   119.55  3.000
 DAI  H17   C17  C18   119.31  3.000
 DAI  H17   C17  C16   121.09  3.000
 DAI  C18   C17  C16   119.60  3.000
 DAI  H18   C18  C19   119.89  3.000
 DAI  H18   C18  C17   119.49  3.000
 DAI  C19   C18  C17   120.62  3.000
 DAI  H19   C19  C14   119.95  3.000
 DAI  H19   C19  C18   120.08  3.000
 DAI  C14   C19  C18   119.97  3.000
 DAI  H14   C14  C19   120.53  3.000
 DAI  H14   C14  C15   120.07  3.000
 DAI  C19   C14  C15   119.39  3.000
 DAI  C6    C12  C11   121.14  3.000
 DAI  C6    C12  C13   125.14  3.000
 DAI  C11   C12  C13   113.67  3.000
 DAI  C10   C11  C9    126.80  3.000
 DAI  C10   C11  C12   113.89  3.000
 DAI  C9    C11  C12   119.27  3.000
 DAI  H9    C9   C8    119.22  3.000
 DAI  H9    C9   C11   121.07  3.000
 DAI  C8    C9   C11   119.71  3.000
 DAI  H8    C8   C7    119.96  3.000
 DAI  H8    C8   C9    119.39  3.000
 DAI  C7    C8   C9    120.65  3.000
 DAI  H7    C7   C6    120.03  3.000
 DAI  H7    C7   C8    120.13  3.000
 DAI  C6    C7   C8    119.84  3.000
 DAI  H6    C6   C7    120.47  3.000
 DAI  H6    C6   C12   120.15  3.000
 DAI  C7    C6   C12   119.37  3.000
 DAI  H27   C27  C26   108.08  3.000
 DAI  H27   C27  C10   108.96  3.000
 DAI  C26   C27  C10   113.63  3.000
 DAI  H27   C27  C28   111.64  3.000
 DAI  C26   C27  C28   104.02  3.000
 DAI  C10   C27  C28   110.46  3.000
 DAI  C5    C10  C27   111.05  3.000
 DAI  C5    C10  C11   113.39  3.000
 DAI  C27   C10  C11   104.44  3.000
 DAI  C5    C10  C16   114.76  3.000
 DAI  C27   C10  C16   104.79  3.000
 DAI  C11   C10  C16   107.56  3.000
 DAI  H52   C5   H51   106.66  3.000
 DAI  H52   C5   O4    111.82  3.000
 DAI  H51   C5   O4    111.14  3.000
 DAI  H52   C5   C10   108.44  3.000
 DAI  H51   C5   C10   109.73  3.000
 DAI  O4    C5   C10   108.98  3.000
 DAI  HO4   O4   C5    107.95  3.000
 DAI  N25   C26  O22   123.64  3.000
 DAI  N25   C26  C27   108.85  3.000
 DAI  O22   C26  C27   127.50  3.000
 DAI  C21   N25  C26   123.49  3.000
 DAI  C21   N25  C24   123.22  3.000
 DAI  C26   N25  C24   113.25  3.000
 DAI  H212  C21  H211  107.12  3.000
 DAI  H212  C21  C20   110.72  3.000
 DAI  H211  C21  C20   110.51  3.000
 DAI  H212  C21  N25   108.04  3.000
 DAI  H211  C21  N25   107.49  3.000
 DAI  C20   C21  N25   112.74  3.000
 DAI  H202  C20  H201  106.84  3.000
 DAI  H202  C20  C3    109.65  3.000
 DAI  H201  C20  C3    109.78  3.000
 DAI  H202  C20  C21   109.40  3.000
 DAI  H201  C20  C21   109.64  3.000
 DAI  C3    C20  C21   111.42  3.000
 DAI  H32   C3   H31   106.17  3.000
 DAI  H32   C3   C2    109.30  3.000
 DAI  H31   C3   C2    109.43  3.000
 DAI  H32   C3   C20   109.54  3.000
 DAI  H31   C3   C20   109.23  3.000
 DAI  C2    C3   C20   112.94  3.000
 DAI  H22   C2   H21   106.11  3.000
 DAI  H22   C2   C1    109.62  3.000
 DAI  H21   C2   C1    109.63  3.000
 DAI  H22   C2   C3    109.31  3.000
 DAI  H21   C2   C3    109.30  3.000
 DAI  C1    C2   C3    112.65  3.000
 DAI  H13A  C1   H12   107.53  3.000
 DAI  H13A  C1   H11   107.66  3.000
 DAI  H12   C1   H11   107.64  3.000
 DAI  H13A  C1   C2    111.09  3.000
 DAI  H12   C1   C2    111.16  3.000
 DAI  H11   C1   C2    111.57  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
 DAI  CONST_01  C18  C17  C16  C15     0.00   0.0  0
 DAI  CONST_02  C18  C19  C14  C15     0.00   0.0  0
 DAI  CONST_03  C19  C14  C15  C16     0.00   0.0  0
 DAI  CONST_04  C19  C18  C17  C16     0.00   0.0  0
 DAI  CONST_05  C14  C15  C16  C17     0.00   0.0  0
 DAI  CONST_06  C14  C19  C18  C17     0.00   0.0  0
 DAI  CONST_07  C8   C9   C11  C12     0.00   0.0  0
 DAI  CONST_08  C8   C7   C6   C12     0.00   0.0  0
 DAI  CONST_09  C7   C6   C12  C11     0.00   0.0  0
 DAI  CONST_10  C7   C8   C9   C11     0.00   0.0  0
 DAI  CONST_11  C6   C12  C11  C9      0.00   0.0  0
 DAI  CONST_12  C6   C7   C8   C9      0.00   0.0  0
 DAI  CONST_13  C26  N25  C24  C28     0.00   0.0  0
 DAI  CONST_14  C26  N25  C24  O23   180.00   0.0  0
 DAI  CONST_15  C21  N25  C24  C28   180.00   0.0  0
 DAI  CONST_16  H14  C14  C15  C13     0.00   0.0  0
 DAI  CONST_17  H6   C6   C12  C13     0.00   0.0  0
 DAI  CONST_18  H17  C17  C16  C15   180.00   0.0  0
 DAI  CONST_19  H19  C19  C14  C15   180.00   0.0  0
 DAI  CONST_20  H18  C18  C17  C16   180.00   0.0  0
 DAI  CONST_21  H9   C9   C11  C12   180.00   0.0  0
 DAI  CONST_22  H7   C7   C6   C12   180.00   0.0  0
 DAI  CONST_23  H8   C8   C9   C11   180.00   0.0  0
 DAI  CONST_24  C21  N25  C24  O23     0.00   0.0  0
 DAI  Var_01    C27  C26  N25  C24     2.44  30.0  1
 DAI  Var_02    C20  C21  N25  C24    90.20  30.0  3
 DAI  Var_03    C3   C20  C21  N25  -176.51  30.0  3
 DAI  Var_04    C2   C3   C20  C21  -179.00  30.0  3
 DAI  Var_05    C1   C2   C3   C20  -178.94  30.0  3
 DAI  Var_06    H11  C1   C2   C3    180.00  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
 DAI  chir_01  C28  C24  C13  C27  negativ
 DAI  chir_02  C13  C28  C15  C12  negativ
 DAI  chir_03  C27  C28  C10  C26  negativ
 DAI  chir_04  C10  C27  C11  C16  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
 DAI  plan-1  C27  0.020
 DAI  plan-1  C26  0.020
 DAI  plan-1  O22  0.020
 DAI  plan-1  N25  0.020
 DAI  plan-2  C13  0.020
 DAI  plan-2  C15  0.020
 DAI  plan-2  C16  0.020
 DAI  plan-2  C17  0.020
 DAI  plan-2  C18  0.020
 DAI  plan-2  C19  0.020
 DAI  plan-2  C14  0.020
 DAI  plan-2  C10  0.020
 DAI  plan-2  H17  0.020
 DAI  plan-2  H18  0.020
 DAI  plan-2  H19  0.020
 DAI  plan-2  H14  0.020
 DAI  plan-3  C13  0.020
 DAI  plan-3  C12  0.020
 DAI  plan-3  C11  0.020
 DAI  plan-3  C9   0.020
 DAI  plan-3  C8   0.020
 DAI  plan-3  C7   0.020
 DAI  plan-3  C6   0.020
 DAI  plan-3  C10  0.020
 DAI  plan-3  H9   0.020
 DAI  plan-3  H8   0.020
 DAI  plan-3  H7   0.020
 DAI  plan-3  H6   0.020
 DAI  plan-4  O23  0.020
 DAI  plan-4  C24  0.020
 DAI  plan-4  C28  0.020
 DAI  plan-4  C26  0.020
 DAI  plan-4  N25  0.020
 DAI  plan-4  C21  0.020

