# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 13:26:59 2022
#   Inital geometry file: a 139 line input string
#   Ligand name: N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=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
 LOC  LOC  N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide  ligand  54  29  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_LOC
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
 LOC  O4    O  O     0  -0.484  -1.3821   2.2460  -2.4250
 LOC  C12   C  C     0   0.520  -1.8072   3.0573  -1.6155
 LOC  C13   C  CH3   0  -0.778  -2.7159   4.1913  -2.0135
 LOC  N1    N  NH1   0  -0.646  -1.5157   2.9831  -0.3009
 LOC  C11   C  CH1   0  -0.129  -0.6855   1.9426   0.2439
 LOC  C14   C  C     0   0.144  -1.3715   0.5814   0.3589
 LOC  C15   C  C1    0  -0.448  -2.7301   0.5709   0.4391
 LOC  C10   C  CH2   0  -0.426  -0.1417   2.3895   1.6068
 LOC  C9    C  CH2   0  -0.560   0.6197   1.2813   2.3417
 LOC  C8    C  CR6   0   0.126   1.5390   0.5473   1.4078
 LOC  C7    C  CR16  0  -0.476   2.9126   0.7487   1.4639
 LOC  C5    C  CR6   0   0.329   3.7578   0.1382   0.5429
 LOC  C3    C  CR6   0   0.201   3.2083  -0.6555  -0.4722
 LOC  C1    C  CR6   0   0.269   1.8345  -0.8652  -0.5157
 LOC  O1    O  O2    0  -0.479   1.3304  -1.6429  -1.5079
 LOC  C2    C  CH3   0  -0.420   0.9182  -0.9108  -2.6549
 LOC  O2    O  O2    0  -0.480   4.0170  -1.1893  -1.4228
 LOC  C4    C  CH3   0  -0.408   4.4771  -2.5022  -1.1305
 LOC  O3    O  O2    0  -0.460   5.0934   0.2672   0.5272
 LOC  C6    C  CH3   0  -0.440   5.7035   1.0712   1.5183
 LOC  C22   C  CR6   0  -0.122   0.9847  -0.2812   0.4302
 LOC  C21   C  C     0   0.069  -0.4793  -0.5395   0.4143
 LOC  C20   C  C1    0  -0.251  -0.8758  -1.8443   0.4842
 LOC  C19   C  C1    0  -0.404  -2.1553  -2.4417   0.5156
 LOC  C17   C  C     0   0.303  -3.4018  -1.8889   0.5507
 LOC  C16   C  C     0   0.345  -3.7385  -0.4532   0.5689
 LOC  O5    O  O     0  -0.466  -4.9201  -0.1313   0.6737
 LOC  O6    O  O2    0  -0.430  -4.5129  -2.6172   0.5941
 LOC  C18   C  CH3   0  -0.448  -4.4402  -4.0320   0.5792
 LOC  H13   H  HCH3  0   0.265  -2.3450   4.6582  -2.9245
 LOC  H13A  H  HCH3  0   0.271  -3.7078   3.7926  -2.2315
 LOC  H13B  H  HCH3  0   0.251  -2.8197   4.9544  -1.2445
 LOC  HN1   H  HNH1  0   0.405  -1.9169   3.6617   0.3266
 LOC  H11   H  HCH1  0   0.280   0.1588   1.8184  -0.4380
 LOC  H15   H  H     0   0.249  -3.2007   1.5471   0.3928
 LOC  H10   H  HCH2  0   0.258   0.5164   3.2460   1.4440
 LOC  H10A  H  HCH2  0   0.249  -0.9689   2.7291   2.2367
 LOC  H9    H  HCH2  0   0.270   1.1843   1.7230   3.1633
 LOC  H9A   H  HCH2  0   0.258  -0.0908   0.5850   2.7944
 LOC  H7    H  HCR6  0   0.277   3.3108   1.3856   2.2430
 LOC  H2    H  HCH3  0   0.227   0.1621  -0.1587  -2.4097
 LOC  H2A   H  HCH3  0   0.225   1.7638  -0.4121  -3.1348
 LOC  H2B   H  HCH3  0   0.240   0.4875  -1.6253  -3.3536
 LOC  H4    H  HCH3  0   0.237   5.1456  -2.7951  -1.9382
 LOC  H4A   H  HCH3  0   0.221   5.0308  -2.5369  -0.1890
 LOC  H4B   H  HCH3  0   0.222   3.6524  -3.2170  -1.0817
 LOC  H6    H  HCH3  0   0.230   5.5167   0.6897   2.5253
 LOC  H6A   H  HCH3  0   0.262   6.7727   1.0389   1.3250
 LOC  H6B   H  HCH3  0   0.230   5.3663   2.1094   1.4657
 LOC  H20   H  H     0   0.273  -0.0777  -2.5739   0.5332
 LOC  H19   H  H     0   0.300  -2.1033  -3.5224   0.5368
 LOC  H18   H  HCH3  0   0.240  -3.9540  -4.4024  -0.3260
 LOC  H18A  H  HCH3  0   0.240  -3.9104  -4.4179   1.4530
 LOC  H18B  H  HCH3  0   0.270  -5.4664  -4.3876   0.6019

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
 LOC  O4   C12   double    1.222  0.020  1.222
 LOC  C12  C13   single    1.507  0.020  1.507
 LOC  C12  N1    single    1.349  0.020  1.349
 LOC  N1   C11   single    1.438  0.020  1.438
 LOC  C11  C14   single    1.529  0.020  1.529
 LOC  C11  C10   single    1.534  0.020  1.534
 LOC  C14  C15   double    1.361  0.020  1.361
 LOC  C14  C21   single    1.434  0.020  1.434
 LOC  C15  C16   single    1.443  0.020  1.443
 LOC  C10  C9    single    1.532  0.020  1.532
 LOC  C9   C8    single    1.502  0.020  1.502
 LOC  C8   C7    aromatic  1.389  0.020  1.389
 LOC  C8   C22   aromatic  1.396  0.020  1.396
 LOC  C7   C5    aromatic  1.391  0.020  1.391
 LOC  C5   C3    aromatic  1.401  0.020  1.401
 LOC  C5   O3    single    1.342  0.020  1.342
 LOC  C3   C1    aromatic  1.390  0.020  1.390
 LOC  C3   O2    single    1.357  0.020  1.357
 LOC  C1   O1    single    1.358  0.020  1.358
 LOC  C1   C22   aromatic  1.399  0.020  1.399
 LOC  O1   C2    single    1.422  0.020  1.422
 LOC  O2   C4    single    1.422  0.020  1.422
 LOC  O3   C6    single    1.414  0.020  1.414
 LOC  C22  C21   single    1.487  0.020  1.487
 LOC  C21  C20   double    1.366  0.020  1.366
 LOC  C20  C19   single    1.412  0.020  1.412
 LOC  C19  C17   double    1.364  0.020  1.364
 LOC  C17  C16   single    1.475  0.020  1.475
 LOC  C17  O6    single    1.329  0.020  1.329
 LOC  C16  O5    double    1.229  0.020  1.229
 LOC  O6   C18   single    1.417  0.020  1.417
 LOC  C13  H13   single    0.970  0.020  1.090
 LOC  C13  H13A  single    0.970  0.020  1.090
 LOC  C13  H13B  single    0.970  0.020  1.090
 LOC  N1   HN1   single    0.860  0.020  1.020
 LOC  C11  H11   single    0.970  0.020  1.090
 LOC  C15  H15   single    0.930  0.020  1.080
 LOC  C10  H10   single    0.970  0.020  1.090
 LOC  C10  H10A  single    0.970  0.020  1.090
 LOC  C9   H9    single    0.970  0.020  1.090
 LOC  C9   H9A   single    0.970  0.020  1.090
 LOC  C7   H7    single    0.930  0.020  1.080
 LOC  C2   H2    single    0.970  0.020  1.090
 LOC  C2   H2A   single    0.970  0.020  1.090
 LOC  C2   H2B   single    0.970  0.020  1.090
 LOC  C4   H4    single    0.970  0.020  1.090
 LOC  C4   H4A   single    0.970  0.020  1.090
 LOC  C4   H4B   single    0.970  0.020  1.090
 LOC  C6   H6    single    0.970  0.020  1.090
 LOC  C6   H6A   single    0.970  0.020  1.090
 LOC  C6   H6B   single    0.970  0.020  1.090
 LOC  C20  H20   single    0.930  0.020  1.080
 LOC  C19  H19   single    0.930  0.020  1.080
 LOC  C18  H18   single    0.970  0.020  1.090
 LOC  C18  H18A  single    0.970  0.020  1.090
 LOC  C18  H18B  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
 LOC  N1    C12  C13   115.42  3.000
 LOC  N1    C12  O4    122.27  3.000
 LOC  C13   C12  O4    122.30  3.000
 LOC  H13B  C13  H13A  108.10  3.000
 LOC  H13B  C13  H13   108.84  3.000
 LOC  H13A  C13  H13   107.41  3.000
 LOC  H13B  C13  C12   113.49  3.000
 LOC  H13A  C13  C12   109.03  3.000
 LOC  H13   C13  C12   109.78  3.000
 LOC  HN1   N1   C11   118.76  3.000
 LOC  HN1   N1   C12   118.94  3.000
 LOC  C11   N1   C12   122.26  3.000
 LOC  H11   C11  C10   108.28  3.000
 LOC  H11   C11  C14   107.01  3.000
 LOC  C10   C11  C14   110.59  3.000
 LOC  H11   C11  N1    106.97  3.000
 LOC  C10   C11  N1    109.30  3.000
 LOC  C14   C11  N1    114.43  3.000
 LOC  C21   C14  C15   127.80  3.000
 LOC  C21   C14  C11   114.82  3.000
 LOC  C15   C14  C11   117.34  3.000
 LOC  H15   C15  C16   109.84  3.000
 LOC  H15   C15  C14   115.06  3.000
 LOC  C16   C15  C14   135.10  3.000
 LOC  H10A  C10  H10   107.34  3.000
 LOC  H10A  C10  C9    108.91  3.000
 LOC  H10   C10  C9    109.83  3.000
 LOC  H10A  C10  C11   109.51  3.000
 LOC  H10   C10  C11   108.04  3.000
 LOC  C9    C10  C11   113.05  3.000
 LOC  H9A   C9   H9    106.42  3.000
 LOC  H9A   C9   C8    110.12  3.000
 LOC  H9    C9   C8    110.46  3.000
 LOC  H9A   C9   C10   109.66  3.000
 LOC  H9    C9   C10   109.01  3.000
 LOC  C8    C9   C10   111.06  3.000
 LOC  C22   C8   C7    120.45  3.000
 LOC  C22   C8   C9    118.84  3.000
 LOC  C7    C8   C9    120.61  3.000
 LOC  H7    C7   C5    120.75  3.000
 LOC  H7    C7   C8    118.56  3.000
 LOC  C5    C7   C8    120.69  3.000
 LOC  O3    C5   C3    115.88  3.000
 LOC  O3    C5   C7    124.77  3.000
 LOC  C3    C5   C7    119.34  3.000
 LOC  O2    C3   C1    120.49  3.000
 LOC  O2    C3   C5    119.78  3.000
 LOC  C1    C3   C5    119.71  3.000
 LOC  C22   C1   O1    120.50  3.000
 LOC  C22   C1   C3    121.07  3.000
 LOC  O1    C1   C3    118.43  3.000
 LOC  C2    O1   C1    113.72  3.000
 LOC  H2B   C2   H2A   108.90  3.000
 LOC  H2B   C2   H2    108.76  3.000
 LOC  H2A   C2   H2    108.63  3.000
 LOC  H2B   C2   O1    107.13  3.000
 LOC  H2A   C2   O1    111.41  3.000
 LOC  H2    C2   O1    111.93  3.000
 LOC  C4    O2   C3    114.34  3.000
 LOC  H4B   C4   H4A   108.86  3.000
 LOC  H4B   C4   H4    108.71  3.000
 LOC  H4A   C4   H4    108.64  3.000
 LOC  H4B   C4   O2    111.66  3.000
 LOC  H4A   C4   O2    111.74  3.000
 LOC  H4    C4   O2    107.14  3.000
 LOC  C6    O3   C5    118.41  3.000
 LOC  H6B   C6   H6A   108.85  3.000
 LOC  H6B   C6   H6    108.86  3.000
 LOC  H6A   C6   H6    108.76  3.000
 LOC  H6B   C6   O3    111.91  3.000
 LOC  H6A   C6   O3    106.42  3.000
 LOC  H6    C6   O3    111.93  3.000
 LOC  C21   C22  C1    121.22  3.000
 LOC  C21   C22  C8    120.10  3.000
 LOC  C1    C22  C8    118.68  3.000
 LOC  C20   C21  C22   116.83  3.000
 LOC  C20   C21  C14   124.64  3.000
 LOC  C22   C21  C14   118.52  3.000
 LOC  H20   C20  C19   112.45  3.000
 LOC  H20   C20  C21   115.62  3.000
 LOC  C19   C20  C21   131.93  3.000
 LOC  H19   C19  C17   116.63  3.000
 LOC  H19   C19  C20   112.29  3.000
 LOC  C17   C19  C20   131.07  3.000
 LOC  O6    C17  C16   110.01  3.000
 LOC  O6    C17  C19   122.87  3.000
 LOC  C16   C17  C19   127.12  3.000
 LOC  O5    C16  C17   118.39  3.000
 LOC  O5    C16  C15   119.57  3.000
 LOC  C17   C16  C15   122.02  3.000
 LOC  C18   O6   C17   120.26  3.000
 LOC  H18B  C18  H18A  109.02  3.000
 LOC  H18B  C18  H18   109.07  3.000
 LOC  H18A  C18  H18   109.10  3.000
 LOC  H18B  C18  O6    106.15  3.000
 LOC  H18A  C18  O6    111.67  3.000
 LOC  H18   C18  O6    111.73  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
 LOC  CONST_01  C3   C5   C7   C8      0.00   0.0  0
 LOC  CONST_02  C1   C3   C5   C7      0.00   0.0  0
 LOC  CONST_03  C22  C1   C3   C5      0.00   0.0  0
 LOC  CONST_04  O3   C5   C7   C8    180.00   0.0  0
 LOC  CONST_05  O2   C3   C5   C7    180.00   0.0  0
 LOC  CONST_06  O1   C1   C3   C5    180.00   0.0  0
 LOC  CONST_07  O3   C5   C3   C1    180.00   0.0  0
 LOC  CONST_08  C22  C1   C3   O2    180.00   0.0  0
 LOC  CONST_09  H7   C7   C5   C3    180.00   0.0  0
 LOC  CONST_10  C11  N1   C12  O4      0.00   0.0  0
 LOC  CONST_11  C11  N1   C12  C13   180.00   0.0  0
 LOC  CONST_12  HN1  N1   C12  O4    180.00   0.0  0
 LOC  Var_01    C22  C1   O1   C2     86.38  30.0  2
 LOC  Var_02    H6   C6   O3   C5     61.28  30.0  3
 LOC  Var_03    H4   C4   O2   C3   -177.43  30.0  3
 LOC  Var_04    H2   C2   O1   C1    -57.92  30.0  3
 LOC  Var_05    H18  C18  O6   C17   -60.11  30.0  3
 LOC  Var_06    H13  C13  C12  O4    -44.36  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
 LOC  chir_01  C11  N1  C14  C10  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
 LOC  plan-1  O4   0.020
 LOC  plan-1  C12  0.020
 LOC  plan-1  C13  0.020
 LOC  plan-1  N1   0.020
 LOC  plan-1  C11  0.020
 LOC  plan-1  HN1  0.020
 LOC  plan-2  C9   0.020
 LOC  plan-2  C8   0.020
 LOC  plan-2  C7   0.020
 LOC  plan-2  C5   0.020
 LOC  plan-2  C3   0.020
 LOC  plan-2  C1   0.020
 LOC  plan-2  O1   0.020
 LOC  plan-2  O2   0.020
 LOC  plan-2  O3   0.020
 LOC  plan-2  C22  0.020
 LOC  plan-2  C21  0.020
 LOC  plan-2  H7   0.020
 LOC  plan-3  C15  0.020
 LOC  plan-3  C17  0.020
 LOC  plan-3  C16  0.020
 LOC  plan-3  O5   0.020
 LOC  plan-4  C11  0.020
 LOC  plan-4  C14  0.020
 LOC  plan-4  C15  0.020
 LOC  plan-4  C21  0.020
 LOC  plan-4  C16  0.020
 LOC  plan-4  H15  0.020
 LOC  plan-5  C14  0.020
 LOC  plan-5  C22  0.020
 LOC  plan-5  C21  0.020
 LOC  plan-5  C20  0.020
 LOC  plan-5  C19  0.020
 LOC  plan-5  H20  0.020

