# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 17 18:36:18 2020
#   Inital geometry file: a 117 line input string
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1(C)[C@H]2C[C@@H](Cl)[C@](C)(C=C)[C@H]([N+]#[C-])[C@H]2c3c[nH]c4cccc1c34
#
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
 8O0  8O0  'None                     '  ligand  47  24  .  2021-08-06  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_8O0
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
 8O0  C10   C   CR16   0  -0.252  -0.1436  -1.4158   0.0171
 8O0  C13   C   CT     0  -0.143   2.2177   0.5084   0.0341
 8O0  C15   C   CH2    0  -0.410   0.4666  -0.8331  -1.2614
 8O0  C21   C   C     -1  -0.148   2.8860  -2.0988   2.2014
 8O0  C01   C   CR16   0  -0.395  -3.7020  -0.4470  -0.9594
 8O0  C02   C   CR16   0  -0.261  -4.4476   0.7467  -0.8635
 8O0  C03   C   CR16   0  -0.331  -4.0375   1.8271  -0.1014
 8O0  C04   C   CR56   0   0.359  -2.8188   1.6968   0.5687
 8O0  C05   C   C      0  -0.036  -2.0714   0.5190   0.4470
 8O0  C06   C   CR66   0   0.164  -2.4999  -0.5814  -0.2903
 8O0  C07   C   CR15   0  -0.102  -0.9514   1.8858   1.7930
 8O0  C08   C   CR56   0   0.038  -0.8839   0.6522   1.2086
 8O0  C09   C   CR16   0  -0.325   0.0894  -0.4817   1.2338
 8O0  C11   C   CR6    0  -0.157  -1.6389  -1.8225  -0.1713
 8O0  C12   C   CH1    0  -0.061   1.5652  -0.0443   1.3411
 8O0  C14   C   CH1    0  -0.270   1.9368  -0.5258  -1.0625
 8O0  C16   C   C1     0  -0.107   3.7113   0.6034   0.2533
 8O0  C18   C   CH3    0  -0.675  -1.7952  -2.7466  -1.3794
 8O0  C19   C   CH3    0  -0.678   1.6258   1.8771  -0.3007
 8O0  N01   N   NR15   0  -0.693  -2.1101   2.5140   1.4027
 8O0  N02   N   N      1  -0.187   2.3085  -1.1650   1.8177
 8O0  CL01  CL  CL     0  -0.146   2.6558   0.0246  -2.6296
 8O0  H1    H   HCR6   0   0.245   0.3884  -2.3513   0.2292
 8O0  H2    H   HCH2   0   0.270   0.3863  -1.5636  -2.0658
 8O0  H3    H   HCH2   0   0.248  -0.0715   0.0581  -1.5911
 8O0  H4    H   HCH3   0   0.237  -3.1272  -2.9470   0.9428
 8O0  H5    H   HCH3   0   0.230  -1.4681  -3.4649   1.2523
 8O0  H6    H   HCH3   0   0.235  -2.0908  -1.9795   1.9764
 8O0  H7    H   H      0   0.246   5.4753   1.6639   0.6351
 8O0  H8    H   H      0   0.242   3.9609   2.6972   0.5033
 8O0  H12   H   HCR6   0   0.239  -4.0985  -1.2591  -1.5562
 8O0  H13   H   HCR6   0   0.245  -5.3855   0.8149  -1.4002
 8O0  H14   H   HCR6   0   0.255  -4.6408   2.7232  -0.0351
 8O0  H15   H   HCR5   0   0.282  -0.2607   2.3948   2.4472
 8O0  H16   H   HCR6   0   0.282  -0.0956  -1.0717   2.1377
 8O0  H17   H   HCH1   0   0.311   1.6585   0.7299   2.1077
 8O0  H18   H   HCH1   0   0.297   2.4690  -1.4515  -0.8319
 8O0  H19   H   H      0   0.252   4.2499  -0.3400   0.2383
 8O0  H20   H   HCH3   0   0.240  -2.7925  -3.1879  -1.3991
 8O0  H21   H   HCH3   0   0.236  -1.6515  -2.2289  -2.3275
 8O0  H22   H   HCH3   0   0.237  -1.0789  -3.5697  -1.3306
 8O0  H23   H   HCH3   0   0.251   2.1838   2.3381  -1.1135
 8O0  H24   H   HCH3   0   0.263   0.5822   1.8173  -0.5957
 8O0  H25   H   HCH3   0   0.242   1.6773   2.5427   0.5603
 8O0  H26   H   HNR5   0   0.407  -2.3775   3.4408   1.6879
 8O0  C17   C   CH3    0  -0.640  -2.1036  -2.5938   1.0758
 8O0  C20   C   C2     0  -0.536   4.4062   1.7113   0.4754

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
 8O0  C18  C11   single    1.529  0.020  1.529
 8O0  C17  C11   single    1.538  0.020  1.538
 8O0  C01  C02   aromatic  1.411  0.020  1.411
 8O0  C01  C06   aromatic  1.382  0.020  1.382
 8O0  C02  C03   aromatic  1.384  0.020  1.384
 8O0  C11  C06   single    1.515  0.020  1.515
 8O0  C11  C10   single    1.561  0.020  1.561
 8O0  C06  C05   aromatic  1.392  0.020  1.392
 8O0  C03  C04   aromatic  1.397  0.020  1.397
 8O0  C10  C15   single    1.532  0.020  1.532
 8O0  C10  C09   single    1.552  0.020  1.552
 8O0  C05  C04   aromatic  1.400  0.020  1.400
 8O0  C05  C08   aromatic  1.417  0.020  1.417
 8O0  C04  N01   aromatic  1.366  0.020  1.366
 8O0  C15  C14   single    1.515  0.020  1.515
 8O0  C09  C08   single    1.495  0.020  1.495
 8O0  C09  C12   single    1.543  0.020  1.543
 8O0  C08  C07   aromatic  1.367  0.020  1.367
 8O0  N01  C07   aromatic  1.375  0.020  1.375
 8O0  C21  N02   triple    1.163  0.020  1.163
 8O0  C14  CL01  single    1.810  0.020  1.810
 8O0  C14  C13   single    1.533  0.020  1.533
 8O0  N02  C12   single    1.427  0.020  1.427
 8O0  C12  C13   single    1.562  0.020  1.562
 8O0  C13  C19   single    1.528  0.020  1.528
 8O0  C13  C16   single    1.513  0.020  1.513
 8O0  C16  C20   double    1.327  0.020  1.327
 8O0  C10  H1    single    0.970  0.020  1.090
 8O0  C15  H2    single    0.970  0.020  1.090
 8O0  C15  H3    single    0.970  0.020  1.090
 8O0  C17  H4    single    0.970  0.020  1.090
 8O0  C17  H5    single    0.970  0.020  1.090
 8O0  C17  H6    single    0.970  0.020  1.090
 8O0  C20  H7    single    0.930  0.020  1.080
 8O0  C20  H8    single    0.930  0.020  1.080
 8O0  C01  H12   single    0.930  0.020  1.080
 8O0  C02  H13   single    0.930  0.020  1.080
 8O0  C03  H14   single    0.930  0.020  1.080
 8O0  C07  H15   single    0.930  0.020  1.080
 8O0  C09  H16   single    0.970  0.020  1.090
 8O0  C12  H17   single    0.970  0.020  1.090
 8O0  C14  H18   single    0.970  0.020  1.090
 8O0  C16  H19   single    0.930  0.020  1.080
 8O0  C18  H20   single    0.970  0.020  1.090
 8O0  C18  H21   single    0.970  0.020  1.090
 8O0  C18  H22   single    0.970  0.020  1.090
 8O0  C19  H23   single    0.970  0.020  1.090
 8O0  C19  H24   single    0.970  0.020  1.090
 8O0  C19  H25   single    0.970  0.020  1.090
 8O0  N01  H26   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
 8O0  H1    C10  C11   105.42  3.000
 8O0  H1    C10  C09   106.80  3.000
 8O0  C11   C10  C09   113.29  3.000
 8O0  H1    C10  C15   107.01  3.000
 8O0  C09   C10  C15   111.45  3.000
 8O0  C11   C10  C15   112.33  3.000
 8O0  C19   C13  C16   110.97  3.000
 8O0  C16   C13  C14   109.08  3.000
 8O0  C19   C13  C14   112.11  3.000
 8O0  C16   C13  C12   108.27  3.000
 8O0  C19   C13  C12   109.78  3.000
 8O0  C14   C13  C12   106.45  3.000
 8O0  H3    C15  H2    106.73  3.000
 8O0  H3    C15  C14   110.63  3.000
 8O0  H2    C15  C14   107.72  3.000
 8O0  H3    C15  C10   111.48  3.000
 8O0  H2    C15  C10   109.38  3.000
 8O0  C14   C15  C10   110.74  3.000
 8O0  H12   C01  C06   120.81  3.000
 8O0  H12   C01  C02   118.58  3.000
 8O0  C06   C01  C02   120.60  3.000
 8O0  H13   C02  C03   118.70  3.000
 8O0  H13   C02  C01   118.52  3.000
 8O0  C03   C02  C01   122.77  3.000
 8O0  H14   C03  C04   122.29  3.000
 8O0  H14   C03  C02   120.99  3.000
 8O0  C04   C03  C02   116.72  3.000
 8O0  N01   C04  C05   106.22  3.000
 8O0  N01   C04  C03   133.61  3.000
 8O0  C05   C04  C03   120.17  3.000
 8O0  C08   C05  C06   128.09  3.000
 8O0  C08   C05  C04   108.76  3.000
 8O0  C06   C05  C04   123.13  3.000
 8O0  C11   C06  C05   115.53  3.000
 8O0  C05   C06  C01   116.56  3.000
 8O0  C11   C06  C01   127.72  3.000
 8O0  H15   C07  N01   119.74  3.000
 8O0  H15   C07  C08   130.81  3.000
 8O0  N01   C07  C08   109.43  3.000
 8O0  C09   C08  C07   135.21  3.000
 8O0  C07   C08  C05   105.86  3.000
 8O0  C09   C08  C05   118.92  3.000
 8O0  H16   C09  C12   104.89  3.000
 8O0  H16   C09  C08   108.22  3.000
 8O0  C12   C09  C08   114.14  3.000
 8O0  H16   C09  C10   107.31  3.000
 8O0  C12   C09  C10   111.65  3.000
 8O0  C08   C09  C10   110.22  3.000
 8O0  C18   C11  C06   112.02  3.000
 8O0  C06   C11  C17   107.62  3.000
 8O0  C18   C11  C17   107.86  3.000
 8O0  C06   C11  C10   109.90  3.000
 8O0  C17   C11  C10   108.79  3.000
 8O0  C18   C11  C10   110.53  3.000
 8O0  H17   C12  N02   106.11  3.000
 8O0  H17   C12  C09   109.34  3.000
 8O0  N02   C12  C09   107.39  3.000
 8O0  H17   C12  C13   107.49  3.000
 8O0  N02   C12  C13   109.86  3.000
 8O0  C09   C12  C13   116.21  3.000
 8O0  H18   C14  CL01  104.30  3.000
 8O0  H18   C14  C15   109.19  3.000
 8O0  CL01  C14  C15   109.48  3.000
 8O0  H18   C14  C13   109.35  3.000
 8O0  CL01  C14  C13   109.96  3.000
 8O0  C15   C14  C13   114.11  3.000
 8O0  H19   C16  C20   117.89  3.000
 8O0  H19   C16  C13   115.66  3.000
 8O0  C20   C16  C13   126.44  3.000
 8O0  H22   C18  H21   108.08  3.000
 8O0  H22   C18  H20   107.19  3.000
 8O0  H21   C18  H20   107.28  3.000
 8O0  H22   C18  C11   110.69  3.000
 8O0  H21   C18  C11   112.76  3.000
 8O0  H20   C18  C11   110.62  3.000
 8O0  H25   C19  H24   107.08  3.000
 8O0  H25   C19  H23   107.89  3.000
 8O0  H24   C19  H23   108.25  3.000
 8O0  H25   C19  C13   110.84  3.000
 8O0  H24   C19  C13   112.48  3.000
 8O0  H23   C19  C13   110.14  3.000
 8O0  H26   N01  C07   124.38  3.000
 8O0  H26   N01  C04   125.90  3.000
 8O0  C07   N01  C04   109.71  3.000
 8O0  C12   N02  C21   180.00  3.000
 8O0  H6    C17  H5    107.99  3.000
 8O0  H6    C17  H4    107.10  3.000
 8O0  H5    C17  H4    107.89  3.000
 8O0  H6    C17  C11   112.56  3.000
 8O0  H5    C17  C11   110.80  3.000
 8O0  H4    C17  C11   110.30  3.000
 8O0  H8    C20  H7    116.28  3.000
 8O0  H8    C20  C16   123.34  3.000
 8O0  H7    C20  C16   120.38  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
 8O0  CONST_01  C04  C03  C02  C01     0.00   0.0  0
 8O0  CONST_02  C04  C05  C06  C01     0.00   0.0  0
 8O0  CONST_03  C08  C05  C06  C01   180.00   0.0  0
 8O0  CONST_04  C05  C06  C01  C02     0.00   0.0  0
 8O0  CONST_05  C05  C04  C03  C02     0.00   0.0  0
 8O0  CONST_06  N01  C04  C03  C02   180.00   0.0  0
 8O0  CONST_07  C06  C01  C02  C03     0.00   0.0  0
 8O0  CONST_08  C06  C05  C04  C03     0.00   0.0  0
 8O0  CONST_09  C08  C05  C04  C03   180.00   0.0  0
 8O0  CONST_10  C07  N01  C04  C03   180.00   0.0  0
 8O0  CONST_11  C07  C08  C05  C04     0.00   0.0  0
 8O0  CONST_12  C08  C07  N01  C04     0.00   0.0  0
 8O0  CONST_13  C07  N01  C04  C05     0.00   0.0  0
 8O0  CONST_14  N01  C07  C08  C05     0.00   0.0  0
 8O0  CONST_15  N01  C04  C05  C06   180.00   0.0  0
 8O0  CONST_16  C07  C08  C05  C06   180.00   0.0  0
 8O0  CONST_17  N01  C04  C05  C08     0.00   0.0  0
 8O0  CONST_18  H14  C03  C02  C01   180.00   0.0  0
 8O0  CONST_19  H12  C01  C02  C03   180.00   0.0  0
 8O0  CONST_20  H26  N01  C04  C03     0.00   0.0  0
 8O0  CONST_21  H13  C02  C03  C04   180.00   0.0  0
 8O0  CONST_22  H15  C07  N01  C04   180.00   0.0  0
 8O0  Var_01    C01  C06  C11  C10   152.19  30.0  1
 8O0  Var_02    H20  C18  C11  C10   168.83  30.0  3
 8O0  Var_03    H4   C17  C11  C10  -176.30  30.0  3
 8O0  Var_04    H7   C20  C16  C13   179.05   0.0  2

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
 8O0  chir_01  C10  C11   C15  C09  negativ
 8O0  chir_02  C13  C19   C12  C14  negativ
 8O0  chir_03  C09  C10   C08  C12  positiv
 8O0  chir_04  C12  N02   C13  C09  negativ
 8O0  chir_05  C14  CL01  C15  C13  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
 8O0  plan-1  C13  0.020
 8O0  plan-1  C16  0.020
 8O0  plan-1  H7   0.020
 8O0  plan-1  H8   0.020
 8O0  plan-1  H19  0.020
 8O0  plan-1  C20  0.020
 8O0  plan-2  C01  0.020
 8O0  plan-2  C02  0.020
 8O0  plan-2  C03  0.020
 8O0  plan-2  C04  0.020
 8O0  plan-2  C05  0.020
 8O0  plan-2  C06  0.020
 8O0  plan-2  C07  0.020
 8O0  plan-2  C08  0.020
 8O0  plan-2  C09  0.020
 8O0  plan-2  C11  0.020
 8O0  plan-2  N01  0.020
 8O0  plan-2  H12  0.020
 8O0  plan-2  H13  0.020
 8O0  plan-2  H14  0.020
 8O0  plan-2  H15  0.020
 8O0  plan-2  H26  0.020

