# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 06:46:38 2020
#   Inital geometry file: a 96 line input string
#   Ligand name: (4R)-4-(5-ethenyl-1H-imidazol-1-yl)-3,3-dimethyl-3,4-dihydro-1H-2-benzopyran-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1(C)OC(=O)c2ccccc2[C@H]1n3cncc3C=C
#
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
 CW4  CW4  (4R)-4-(5-ethenyl-1H-imidazol-1-yl)-3,3-dimethyl-3,4-dihydro-1H-2-benzopyran-1-one  ligand  36  20  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_CW4
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
 CW4  C1   C  CR16  0  -0.231   2.0824   2.9185   0.5215
 CW4  C2   C  CR16  0  -0.247   3.2078   2.3457  -0.0614
 CW4  C3   C  CR16  0  -0.264   3.2005   1.0065  -0.4075
 CW4  C15  C  CR15  0   0.098  -1.0050   0.1703  -1.7098
 CW4  C17  C  CR15  0  -0.242  -3.1048   0.4033  -1.5094
 CW4  C18  C  CR5   0   0.311  -2.6229   0.3064  -0.2270
 CW4  C19  C  C1    0  -0.261  -3.3050   0.3531   1.0528
 CW4  C20  C  C2    0  -0.537  -4.5868   0.6826   1.2152
 CW4  C10  C  CR16  0  -0.232  -0.2754  -0.0451   0.6723
 CW4  C4   C  CR16  0  -0.299   0.9526   2.1516   0.7619
 CW4  C5   C  CR66  0   0.182   0.9415   0.8060   0.4240
 CW4  C6   C  CR66  0  -0.147   2.0667   0.2340  -0.1639
 CW4  C7   C  CR6   0   0.555   2.0523  -1.1860  -0.5777
 CW4  C9   C  CR6   0   0.172   0.1314  -1.5144   0.8671
 CW4  N14  N  NR5   0  -0.474  -1.2584   0.1534  -0.3807
 CW4  N16  N  N     0  -0.436  -2.0951   0.3200  -2.4150
 CW4  O11  O  O     0  -0.416   2.9032  -1.6863  -1.2692
 CW4  O8   O  O     0  -0.452   1.0106  -1.9243  -0.2054
 CW4  H1   H  HCR6  0   0.276   2.0885   3.9654   0.7939
 CW4  H2   H  HCR6  0   0.273   4.0883   2.9464  -0.2445
 CW4  H3   H  HCR6  0   0.274   4.0724   0.5579  -0.8636
 CW4  H4   H  HCH3  0   0.243  -1.7670  -2.2420   1.5799
 CW4  H5   H  HCH3  0   0.257  -1.5591  -2.4247  -0.1660
 CW4  H6   H  HCH3  0   0.263  -0.7029  -3.4897   0.9511
 CW4  H7   H  HCH3  0   0.253   0.1634  -1.4758   3.0193
 CW4  H8   H  HCH3  0   0.261   1.2216  -2.6916   2.3095
 CW4  H9   H  HCH3  0   0.251   1.6981  -0.9883   2.3069
 CW4  H10  H  HCR5  0   0.286  -0.0095   0.0892  -2.1176
 CW4  H11  H  HCR5  0   0.260  -4.1333   0.5292  -1.8128
 CW4  H12  H  H     0   0.265  -2.7334   0.0974   1.9383
 CW4  H13  H  H     0   0.247  -5.2279   0.9628   0.3888
 CW4  H14  H  H     0   0.255  -5.0336   0.6804   2.1990
 CW4  H15  H  HCR6  0   0.314  -0.7327   0.2850   1.6047
 CW4  H16  H  HCR6  0   0.270   0.0798   2.6001   1.2197
 CW4  C12  C  CH3   0  -0.670  -1.0462  -2.4670   0.7944
 CW4  C13  C  CH3   0  -0.658   0.8554  -1.6713   2.2000

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
 CW4  C2   C1   aromatic  1.391  0.020  1.391
 CW4  C2   C3   aromatic  1.383  0.020  1.383
 CW4  C1   C4   aromatic  1.386  0.020  1.386
 CW4  C3   C6   aromatic  1.393  0.020  1.393
 CW4  C4   C5   aromatic  1.387  0.020  1.387
 CW4  C6   C5   aromatic  1.392  0.020  1.392
 CW4  C6   C7   single    1.479  0.020  1.479
 CW4  C13  C9   single    1.525  0.020  1.525
 CW4  C5   C10  single    1.506  0.020  1.506
 CW4  C7   O11  double    1.205  0.020  1.205
 CW4  C7   O8   single    1.330  0.020  1.330
 CW4  C10  C9   single    1.537  0.020  1.537
 CW4  C10  N14  single    1.454  0.020  1.454
 CW4  C9   O8   single    1.446  0.020  1.446
 CW4  C9   C12  single    1.516  0.020  1.516
 CW4  N14  C15  aromatic  1.353  0.020  1.353
 CW4  N14  C18  aromatic  1.382  0.020  1.382
 CW4  C20  C19  double    1.333  0.020  1.333
 CW4  C15  N16  aromatic  1.307  0.020  1.307
 CW4  C18  C19  single    1.451  0.020  1.451
 CW4  C18  C17  aromatic  1.373  0.020  1.373
 CW4  N16  C17  aromatic  1.359  0.020  1.359
 CW4  C1   H1   single    0.930  0.020  1.080
 CW4  C2   H2   single    0.930  0.020  1.080
 CW4  C3   H3   single    0.930  0.020  1.080
 CW4  C12  H4   single    0.970  0.020  1.090
 CW4  C12  H5   single    0.970  0.020  1.090
 CW4  C12  H6   single    0.970  0.020  1.090
 CW4  C13  H7   single    0.970  0.020  1.090
 CW4  C13  H8   single    0.970  0.020  1.090
 CW4  C13  H9   single    0.970  0.020  1.090
 CW4  C15  H10  single    0.930  0.020  1.080
 CW4  C17  H11  single    0.930  0.020  1.080
 CW4  C19  H12  single    0.930  0.020  1.080
 CW4  C20  H13  single    0.930  0.020  1.080
 CW4  C20  H14  single    0.930  0.020  1.080
 CW4  C10  H15  single    0.970  0.020  1.090
 CW4  C4   H16  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
 CW4  H1   C1   C4   119.75  3.000
 CW4  H1   C1   C2   119.97  3.000
 CW4  C4   C1   C2   120.28  3.000
 CW4  H2   C2   C3   119.98  3.000
 CW4  H2   C2   C1   120.07  3.000
 CW4  C3   C2   C1   119.95  3.000
 CW4  H3   C3   C6   119.99  3.000
 CW4  H3   C3   C2   120.19  3.000
 CW4  C6   C3   C2   119.82  3.000
 CW4  H10  C15  N16  125.05  3.000
 CW4  H10  C15  N14  122.90  3.000
 CW4  N16  C15  N14  112.04  3.000
 CW4  H11  C17  N16  121.85  3.000
 CW4  H11  C17  C18  127.22  3.000
 CW4  N16  C17  C18  110.93  3.000
 CW4  N14  C18  C19  124.47  3.000
 CW4  C19  C18  C17  131.02  3.000
 CW4  N14  C18  C17  104.51  3.000
 CW4  H12  C19  C20  117.74  3.000
 CW4  H12  C19  C18  117.69  3.000
 CW4  C20  C19  C18  124.56  3.000
 CW4  H14  C20  H13  116.77  3.000
 CW4  H14  C20  C19  120.53  3.000
 CW4  H13  C20  C19  122.69  3.000
 CW4  H15  C10  N14  107.13  3.000
 CW4  H15  C10  C9   106.99  3.000
 CW4  N14  C10  C9   113.65  3.000
 CW4  H15  C10  C5   108.00  3.000
 CW4  N14  C10  C5   110.47  3.000
 CW4  C9   C10  C5   110.33  3.000
 CW4  H16  C4   C5   119.88  3.000
 CW4  H16  C4   C1   120.07  3.000
 CW4  C5   C4   C1   120.05  3.000
 CW4  C6   C5   C4   119.65  3.000
 CW4  C6   C5   C10  119.38  3.000
 CW4  C4   C5   C10  120.97  3.000
 CW4  C7   C6   C5   120.31  3.000
 CW4  C7   C6   C3   119.42  3.000
 CW4  C5   C6   C3   120.24  3.000
 CW4  O8   C7   O11  118.90  3.000
 CW4  O8   C7   C6   117.53  3.000
 CW4  O11  C7   C6   123.52  3.000
 CW4  O8   C9   C10  109.75  3.000
 CW4  O8   C9   C13  109.29  3.000
 CW4  C10  C9   C13  109.56  3.000
 CW4  O8   C9   C12  104.98  3.000
 CW4  C10  C9   C12  112.89  3.000
 CW4  C13  C9   C12  110.24  3.000
 CW4  C10  N14  C18  127.03  3.000
 CW4  C18  N14  C15  107.03  3.000
 CW4  C10  N14  C15  125.90  3.000
 CW4  C17  N16  C15  105.50  3.000
 CW4  C9   O8   C7   121.77  3.000
 CW4  H6   C12  H5   108.14  3.000
 CW4  H6   C12  H4   107.37  3.000
 CW4  H5   C12  H4   108.43  3.000
 CW4  H6   C12  C9   109.75  3.000
 CW4  H5   C12  C9   112.54  3.000
 CW4  H4   C12  C9   110.45  3.000
 CW4  H9   C13  H8   108.49  3.000
 CW4  H9   C13  H7   107.74  3.000
 CW4  H8   C13  H7   107.80  3.000
 CW4  H9   C13  C9   112.85  3.000
 CW4  H8   C13  C9   110.11  3.000
 CW4  H7   C13  C9   109.70  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
 CW4  CONST_01  C6   C3   C2   C1     0.00   0.0  0
 CW4  CONST_02  C6   C5   C4   C1     0.00   0.0  0
 CW4  CONST_03  C5   C4   C1   C2     0.00   0.0  0
 CW4  CONST_04  C5   C6   C3   C2     0.00   0.0  0
 CW4  CONST_05  C4   C1   C2   C3     0.00   0.0  0
 CW4  CONST_06  C4   C5   C6   C3     0.00   0.0  0
 CW4  CONST_07  C17  C18  N14  C15    0.00   0.0  0
 CW4  CONST_08  C18  C17  N16  C15    0.00   0.0  0
 CW4  CONST_09  N14  C15  N16  C17    0.00   0.0  0
 CW4  CONST_10  N16  C15  N14  C18    0.00   0.0  0
 CW4  CONST_11  N16  C17  C18  N14    0.00   0.0  0
 CW4  CONST_12  C10  N14  C18  C17  180.00   0.0  0
 CW4  CONST_13  N16  C15  N14  C10  180.00   0.0  0
 CW4  CONST_14  C19  C18  N14  C15  180.00   0.0  0
 CW4  CONST_15  C10  N14  C18  C19    0.00   0.0  0
 CW4  CONST_16  N16  C17  C18  C19  180.00   0.0  0
 CW4  CONST_17  H3   C3   C2   C1   180.00   0.0  0
 CW4  CONST_18  H16  C4   C1   C2   180.00   0.0  0
 CW4  CONST_19  H1   C1   C2   C3   180.00   0.0  0
 CW4  CONST_20  H11  C17  N16  C15  180.00   0.0  0
 CW4  CONST_21  H10  C15  N16  C17  180.00   0.0  0
 CW4  CONST_22  H2   C2   C1   C4   180.00   0.0  0
 CW4  Var_01    O8   C7   C6   C3   173.19  30.0  1
 CW4  Var_02    C20  C19  C18  C17   -9.16  30.0  2
 CW4  Var_03    H7   C13  C9   C10   66.27  30.0  3
 CW4  Var_04    H4   C12  C9   C10  -61.11  30.0  3
 CW4  Var_05    H13  C20  C19  C18   -1.06   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
 CW4  chir_01  C10  C5  C9  N14  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
 CW4  plan-1  C15  0.020
 CW4  plan-1  C17  0.020
 CW4  plan-1  C18  0.020
 CW4  plan-1  C19  0.020
 CW4  plan-1  C10  0.020
 CW4  plan-1  N14  0.020
 CW4  plan-1  N16  0.020
 CW4  plan-1  H10  0.020
 CW4  plan-1  H11  0.020
 CW4  plan-2  C1   0.020
 CW4  plan-2  C2   0.020
 CW4  plan-2  C3   0.020
 CW4  plan-2  C10  0.020
 CW4  plan-2  C4   0.020
 CW4  plan-2  C5   0.020
 CW4  plan-2  C6   0.020
 CW4  plan-2  C7   0.020
 CW4  plan-2  H1   0.020
 CW4  plan-2  H2   0.020
 CW4  plan-2  H3   0.020
 CW4  plan-2  H16  0.020
 CW4  plan-3  C6   0.020
 CW4  plan-3  C7   0.020
 CW4  plan-3  O11  0.020
 CW4  plan-3  O8   0.020
 CW4  plan-4  C18  0.020
 CW4  plan-4  C19  0.020
 CW4  plan-4  C20  0.020
 CW4  plan-4  H12  0.020
 CW4  plan-4  H13  0.020
 CW4  plan-4  H14  0.020

