# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 23:16:30 2022
#   Inital geometry file: a 140 line input string
#   Ligand name: (2S)-2-ethoxy-3-{4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCO[C@@H](Cc1ccc(OCCN2c3ccccc3Oc4ccccc24)cc1)C(O)=O
#
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
 DRF  DRF  '(2S)-2-ethoxy-3-{4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid'  ligand  55  31  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_DRF
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
 DRF  O45   O  OC    -1  -0.621  -2.0946   0.0910  -7.3242
 DRF  C44   C  C      0   0.368  -0.9329   0.4208  -7.0079
 DRF  O55   O  O      0  -0.598  -0.1373   1.1052  -7.6742
 DRF  C41   C  CH1    0  -0.020  -0.4796  -0.0558  -5.6072
 DRF  O46   O  O2     0  -0.480   0.9019   0.0368  -5.3923
 DRF  C48   C  CH2    0  -0.138   1.6566  -0.9492  -6.0497
 DRF  C49   C  CH3    0  -0.688   3.1122  -0.7896  -5.6678
 DRF  C40   C  CH2    0  -0.550  -1.1718   0.7894  -4.5336
 DRF  C33   C  CR6    0   0.126  -0.8731   0.3205  -3.1387
 DRF  C34   C  CR16   0  -0.277   0.2560   0.7600  -2.4460
 DRF  C35   C  CR16   0  -0.338   0.5407   0.3092  -1.1702
 DRF  C30   C  CR6    0   0.375  -0.3006  -0.6134  -0.5464
 DRF  O27   O  O2     0  -0.468   0.0570  -1.0041   0.6959
 DRF  C24   C  CH2    0  -0.180  -0.8075  -1.8516   1.4183
 DRF  C23   C  CH2    0  -0.395  -0.2043  -2.1067   2.7884
 DRF  N22   N  NR6    0  -0.623   0.0168  -0.9228   3.5876
 DRF  C11   C  CR66   0   0.348  -1.0347  -0.3690   4.3129
 DRF  C16   C  CR66   0   0.329  -0.7711   0.6685   5.2168
 DRF  O21   O  O      0  -0.502   0.4980   1.1240   5.4192
 DRF  C4    C  CR6    0   0.324   1.4782   0.7289   4.5549
 DRF  C3    C  CR6    0   0.350   1.2623  -0.2966   3.6258
 DRF  C2    C  C1     0  -0.350   2.3297  -0.6453   2.8010
 DRF  C1    C  C1     0  -0.257   3.5623  -0.0102   2.9115
 DRF  C6    C  C1     0  -0.277   3.7534   1.0007   3.8350
 DRF  C5    C  C1     0  -0.372   2.6942   1.3742   4.6548
 DRF  C15   C  CR16   0  -0.372  -1.7754   1.2495   5.9627
 DRF  C14   C  CR16   0  -0.275  -3.0863   0.7970   5.8456
 DRF  C13   C  CR16   0  -0.256  -3.3670  -0.2322   4.9676
 DRF  C12   C  CR16   0  -0.371  -2.3537  -0.8047   4.2041
 DRF  C31   C  CR16   0  -0.370  -1.4297  -1.0672  -1.2200
 DRF  C32   C  CR16   0  -0.304  -1.6994  -0.5955  -2.5014
 DRF  H41   H  HCH1   0   0.188  -0.8133  -1.0986  -5.4783
 DRF  H481  H  HCH2   0   0.193   1.5462  -0.8742  -7.1380
 DRF  H482  H  HCH2   0   0.183   1.3076  -1.9525  -5.7636
 DRF  H491  H  HCH3   0   0.224   3.7145  -1.5511  -6.1635
 DRF  H492  H  HCH3   0   0.223   3.4975   0.1867  -5.9651
 DRF  H493  H  HCH3   0   0.223   3.2525  -0.8997  -4.5917
 DRF  H401  H  HCH2   0   0.248  -2.2470   0.7510  -4.7154
 DRF  H402  H  HCH2   0   0.238  -0.8676   1.8338  -4.6542
 DRF  H34   H  HCR6   0   0.239   0.9225   1.4767  -2.9091
 DRF  H35   H  HCR6   0   0.254   1.4177   0.6672  -0.6445
 DRF  H241  H  HCH2   0   0.236  -0.9353  -2.8176   0.9162
 DRF  H242  H  HCH2   0   0.228  -1.7992  -1.3948   1.5078
 DRF  H231  H  HCH2   0   0.285   0.7353  -2.6490   2.6920
 DRF  H232  H  HCH2   0   0.285  -0.8715  -2.7826   3.3276
 DRF  H2    H  H      0   0.266   2.2121  -1.4081   2.0474
 DRF  H1    H  H      0   0.255   4.3676  -0.3144   2.2561
 DRF  H6    H  H      0   0.255   4.7074   1.5025   3.9220
 DRF  H5    H  H      0   0.268   2.8093   2.1621   5.3886
 DRF  H15   H  HCR6   0   0.268  -1.5256   2.0500   6.6479
 DRF  H14   H  HCR6   0   0.257  -3.8675   1.2495   6.4407
 DRF  H13   H  HCR6   0   0.257  -4.3775  -0.6028   4.8599
 DRF  H12   H  HCR6   0   0.271  -2.6151  -1.6024   3.5241
 DRF  H31   H  HCR6   0   0.272  -2.1083  -1.7807  -0.7719
 DRF  H32   H  HCR6   0   0.245  -2.5862  -0.9579  -3.0091

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
 DRF  O45  C44   deloc     1.248  0.020  1.248
 DRF  C44  O55   deloc     1.243  0.020  1.243
 DRF  C44  C41   single    1.547  0.020  1.547
 DRF  C41  O46   single    1.401  0.020  1.401
 DRF  C41  C40   single    1.532  0.020  1.532
 DRF  C41  H41   single    0.970  0.020  1.090
 DRF  O46  C48   single    1.405  0.020  1.405
 DRF  C48  C49   single    1.513  0.020  1.513
 DRF  C48  H481  single    0.970  0.020  1.090
 DRF  C48  H482  single    0.970  0.020  1.090
 DRF  C49  H491  single    0.970  0.020  1.090
 DRF  C49  H492  single    0.970  0.020  1.090
 DRF  C49  H493  single    0.970  0.020  1.090
 DRF  C40  C33   single    1.502  0.020  1.502
 DRF  C40  H401  single    0.970  0.020  1.090
 DRF  C40  H402  single    0.970  0.020  1.090
 DRF  C33  C34   aromatic  1.396  0.020  1.396
 DRF  C33  C32   aromatic  1.389  0.020  1.389
 DRF  C34  C35   aromatic  1.383  0.020  1.383
 DRF  C34  H34   single    0.930  0.020  1.080
 DRF  C35  C30   aromatic  1.396  0.020  1.396
 DRF  C35  H35   single    0.930  0.020  1.080
 DRF  C30  O27   single    1.351  0.020  1.351
 DRF  C30  C31   aromatic  1.391  0.020  1.391
 DRF  O27  C24   single    1.410  0.020  1.410
 DRF  C24  C23   single    1.519  0.020  1.519
 DRF  C24  H241  single    0.970  0.020  1.090
 DRF  C24  H242  single    0.970  0.020  1.090
 DRF  C23  N22   single    1.445  0.020  1.445
 DRF  C23  H231  single    0.970  0.020  1.090
 DRF  C23  H232  single    0.970  0.020  1.090
 DRF  N22  C11   single    1.392  0.020  1.392
 DRF  N22  C3    single    1.395  0.020  1.395
 DRF  C11  C16   aromatic  1.401  0.020  1.401
 DRF  C11  C12   aromatic  1.393  0.020  1.393
 DRF  C16  O21   single    1.363  0.020  1.363
 DRF  C16  C15   aromatic  1.379  0.020  1.379
 DRF  O21  C4    single    1.365  0.020  1.365
 DRF  C4   C3    aromatic  1.400  0.020  1.400
 DRF  C4   C5    aromatic  1.380  0.020  1.380
 DRF  C3   C2    aromatic  1.393  0.020  1.393
 DRF  C2   C1    aromatic  1.391  0.020  1.391
 DRF  C2   H2    single    0.930  0.020  1.080
 DRF  C1   C6    aromatic  1.383  0.020  1.383
 DRF  C1   H1    single    0.930  0.020  1.080
 DRF  C6   C5    aromatic  1.391  0.020  1.391
 DRF  C6   H6    single    0.930  0.020  1.080
 DRF  C5   H5    single    0.930  0.020  1.080
 DRF  C15  C14   aromatic  1.392  0.020  1.392
 DRF  C15  H15   single    0.930  0.020  1.080
 DRF  C14  C13   aromatic  1.382  0.020  1.382
 DRF  C14  H14   single    0.930  0.020  1.080
 DRF  C13  C12   aromatic  1.392  0.020  1.392
 DRF  C13  H13   single    0.930  0.020  1.080
 DRF  C12  H12   single    0.930  0.020  1.080
 DRF  C31  C32   aromatic  1.392  0.020  1.392
 DRF  C31  H31   single    0.930  0.020  1.080
 DRF  C32  H32   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
 DRF  C41   C44  O55   117.86  3.000
 DRF  C41   C44  O45   114.87  3.000
 DRF  O55   C44  O45   127.24  3.000
 DRF  H41   C41  C40   107.65  3.000
 DRF  H41   C41  O46   110.06  3.000
 DRF  C40   C41  O46   107.56  3.000
 DRF  H41   C41  C44   107.97  3.000
 DRF  C40   C41  C44   109.40  3.000
 DRF  O46   C41  C44   114.03  3.000
 DRF  C48   O46  C41   114.30  3.000
 DRF  H482  C48  H481  106.77  3.000
 DRF  H482  C48  C49   109.62  3.000
 DRF  H481  C48  C49   109.89  3.000
 DRF  H482  C48  O46   110.36  3.000
 DRF  H481  C48  O46   111.24  3.000
 DRF  C49   C48  O46   108.94  3.000
 DRF  H493  C49  H492  108.28  3.000
 DRF  H493  C49  H491  107.89  3.000
 DRF  H492  C49  H491  107.82  3.000
 DRF  H493  C49  C48   111.23  3.000
 DRF  H492  C49  C48   111.43  3.000
 DRF  H491  C49  C48   110.06  3.000
 DRF  H402  C40  H401  106.80  3.000
 DRF  H402  C40  C33   110.18  3.000
 DRF  H401  C40  C33   109.86  3.000
 DRF  H402  C40  C41   108.89  3.000
 DRF  H401  C40  C41   108.01  3.000
 DRF  C33   C40  C41   112.89  3.000
 DRF  C32   C33  C34   117.47  3.000
 DRF  C32   C33  C40   120.94  3.000
 DRF  C34   C33  C40   121.58  3.000
 DRF  H34   C34  C35   118.93  3.000
 DRF  H34   C34  C33   119.61  3.000
 DRF  C35   C34  C33   121.46  3.000
 DRF  H35   C35  C30   119.31  3.000
 DRF  H35   C35  C34   120.44  3.000
 DRF  C30   C35  C34   120.25  3.000
 DRF  C31   C30  O27   124.48  3.000
 DRF  C31   C30  C35   119.24  3.000
 DRF  O27   C30  C35   116.28  3.000
 DRF  C24   O27  C30   118.87  3.000
 DRF  H242  C24  H241  107.42  3.000
 DRF  H242  C24  C23   110.85  3.000
 DRF  H241  C24  C23   108.15  3.000
 DRF  H242  C24  O27   110.26  3.000
 DRF  H241  C24  O27   111.50  3.000
 DRF  C23   C24  O27   108.65  3.000
 DRF  H232  C23  H231  105.22  3.000
 DRF  H232  C23  N22   109.11  3.000
 DRF  H231  C23  N22   108.96  3.000
 DRF  H232  C23  C24   107.86  3.000
 DRF  H231  C23  C24   110.27  3.000
 DRF  N22   C23  C24   114.96  3.000
 DRF  C3    N22  C11   118.79  3.000
 DRF  C3    N22  C23   121.30  3.000
 DRF  C11   N22  C23   119.89  3.000
 DRF  C12   C11  C16   117.39  3.000
 DRF  C12   C11  N22   123.36  3.000
 DRF  C16   C11  N22   119.25  3.000
 DRF  C15   C16  O21   117.18  3.000
 DRF  C15   C16  C11   121.59  3.000
 DRF  O21   C16  C11   121.21  3.000
 DRF  C4    O21  C16   118.53  3.000
 DRF  C5    C4   C3    121.75  3.000
 DRF  C5    C4   O21   116.83  3.000
 DRF  C3    C4   O21   121.41  3.000
 DRF  C2    C3   C4    117.25  3.000
 DRF  C2    C3   N22   123.75  3.000
 DRF  C4    C3   N22   118.99  3.000
 DRF  H2    C2   C1    118.35  3.000
 DRF  H2    C2   C3    120.47  3.000
 DRF  C1    C2   C3    121.17  3.000
 DRF  H1    C1   C6    120.49  3.000
 DRF  H1    C1   C2    118.89  3.000
 DRF  C6    C1   C2    120.62  3.000
 DRF  H6    C6   C5    119.99  3.000
 DRF  H6    C6   C1    121.00  3.000
 DRF  C5    C6   C1    119.01  3.000
 DRF  H5    C5   C6    120.93  3.000
 DRF  H5    C5   C4    118.88  3.000
 DRF  C6    C5   C4    120.19  3.000
 DRF  H15   C15  C14   120.72  3.000
 DRF  H15   C15  C16   119.05  3.000
 DRF  C14   C15  C16   120.22  3.000
 DRF  H14   C14  C13   120.98  3.000
 DRF  H14   C14  C15   119.88  3.000
 DRF  C13   C14  C15   119.15  3.000
 DRF  H13   C13  C12   118.98  3.000
 DRF  H13   C13  C14   120.55  3.000
 DRF  C12   C13  C14   120.47  3.000
 DRF  H12   C12  C13   118.21  3.000
 DRF  H12   C12  C11   120.61  3.000
 DRF  C13   C12  C11   121.18  3.000
 DRF  H31   C31  C32   118.90  3.000
 DRF  H31   C31  C30   121.59  3.000
 DRF  C32   C31  C30   119.51  3.000
 DRF  H32   C32  C31   118.45  3.000
 DRF  H32   C32  C33   119.49  3.000
 DRF  C31   C32  C33   122.06  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
 DRF  CONST_01  C30   C35  C34  C33     0.00   0.0  0
 DRF  CONST_02  C30   C31  C32  C33     0.00   0.0  0
 DRF  CONST_03  C31   C32  C33  C34     0.00   0.0  0
 DRF  CONST_04  C31   C30  C35  C34     0.00   0.0  0
 DRF  CONST_05  C32   C33  C34  C35     0.00   0.0  0
 DRF  CONST_06  C32   C31  C30  C35     0.00   0.0  0
 DRF  CONST_07  C14   C15  C16  C11     0.00   0.0  0
 DRF  CONST_08  C14   C13  C12  C11     0.00   0.0  0
 DRF  CONST_09  C13   C12  C11  C16     0.00   0.0  0
 DRF  CONST_10  C13   C14  C15  C16     0.00   0.0  0
 DRF  CONST_11  C1    C2   C3   C4      0.00   0.0  0
 DRF  CONST_12  C1    C6   C5   C4      0.00   0.0  0
 DRF  CONST_13  C6    C5   C4   C3      0.00   0.0  0
 DRF  CONST_14  C6    C1   C2   C3      0.00   0.0  0
 DRF  CONST_15  C5    C4   C3   C2      0.00   0.0  0
 DRF  CONST_16  C5    C6   C1   C2      0.00   0.0  0
 DRF  CONST_17  C12   C11  C16  C15     0.00   0.0  0
 DRF  CONST_18  C12   C13  C14  C15     0.00   0.0  0
 DRF  CONST_19  C35   C34  C33  C40   180.00   0.0  0
 DRF  CONST_20  C31   C32  C33  C40   180.00   0.0  0
 DRF  CONST_21  O27   C30  C35  C34   180.00   0.0  0
 DRF  CONST_22  C32   C31  C30  O27   180.00   0.0  0
 DRF  CONST_23  H35   C35  C34  C33   180.00   0.0  0
 DRF  CONST_24  H31   C31  C32  C33   180.00   0.0  0
 DRF  CONST_25  H32   C32  C33  C34   180.00   0.0  0
 DRF  CONST_26  H34   C34  C35  C30   180.00   0.0  0
 DRF  CONST_27  H12   C12  C11  N22     0.00   0.0  0
 DRF  CONST_28  H2    C2   C3   N22     0.00   0.0  0
 DRF  CONST_29  H15   C15  C16  C11   180.00   0.0  0
 DRF  CONST_30  H13   C13  C12  C11   180.00   0.0  0
 DRF  CONST_31  H14   C14  C15  C16   180.00   0.0  0
 DRF  CONST_32  H5    C5   C4   O21     0.00   0.0  0
 DRF  CONST_33  H6    C6   C5   C4    180.00   0.0  0
 DRF  CONST_34  H1    C1   C2   C3    180.00   0.0  0
 DRF  Var_01    C4    C3   N22  C11    10.46  30.0  1
 DRF  Var_02    C3    N22  C11  C16    -9.79  30.0  1
 DRF  Var_03    C3    C4   O21  C16   -11.21  30.0  1
 DRF  Var_04    C15   C16  O21  C4   -169.65  30.0  1
 DRF  Var_05    C34   C33  C40  C41    86.52  30.0  2
 DRF  Var_06    C31   C30  O27  C24    -4.99  30.0  2
 DRF  Var_07    C11   N22  C23  C24    82.17  30.0  3
 DRF  Var_08    C23   C24  O27  C30  -178.25  30.0  3
 DRF  Var_09    N22   C23  C24  O27    59.36  30.0  3
 DRF  Var_10    C49   C48  O46  C41  -176.51  30.0  3
 DRF  Var_11    H491  C49  C48  O46   179.63  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
 DRF  chir_01  C41  C44  O46  C40  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
 DRF  plan-1  C40  0.020
 DRF  plan-1  C33  0.020
 DRF  plan-1  C34  0.020
 DRF  plan-1  C35  0.020
 DRF  plan-1  C30  0.020
 DRF  plan-1  O27  0.020
 DRF  plan-1  C31  0.020
 DRF  plan-1  C32  0.020
 DRF  plan-1  H34  0.020
 DRF  plan-1  H35  0.020
 DRF  plan-1  H31  0.020
 DRF  plan-1  H32  0.020
 DRF  plan-2  N22  0.020
 DRF  plan-2  C11  0.020
 DRF  plan-2  C16  0.020
 DRF  plan-2  O21  0.020
 DRF  plan-2  C15  0.020
 DRF  plan-2  C14  0.020
 DRF  plan-2  C13  0.020
 DRF  plan-2  C12  0.020
 DRF  plan-2  H15  0.020
 DRF  plan-2  H14  0.020
 DRF  plan-2  H13  0.020
 DRF  plan-2  H12  0.020
 DRF  plan-3  N22  0.020
 DRF  plan-3  O21  0.020
 DRF  plan-3  C4   0.020
 DRF  plan-3  C3   0.020
 DRF  plan-3  C2   0.020
 DRF  plan-3  C1   0.020
 DRF  plan-3  C6   0.020
 DRF  plan-3  C5   0.020
 DRF  plan-3  H2   0.020
 DRF  plan-3  H1   0.020
 DRF  plan-3  H6   0.020
 DRF  plan-3  H5   0.020
 DRF  plan-4  O45  0.020
 DRF  plan-4  C44  0.020
 DRF  plan-4  O55  0.020
 DRF  plan-4  C41  0.020

