# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 15 15:57:58 2020
#   Inital geometry file: a 85 line input string
#   Ligand name: [3,5-bis(chloranyl)-4-(2-ethylphenyl)phenyl]methanamine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1ccccc1c2c(Cl)cc(CN)cc2Cl
#
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
 AUT  AUT  '[3,5-bis(chloranyl)-4-(2-ethylphenyl)phenyl]methanamine'  ligand  33  18  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_AUT
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
 AUT  C12  C   CH2   0  -0.329   4.4075  -0.2102   0.2848
 AUT  C13  C   CR16  0  -0.236   2.1668  -1.3233   0.4580
 AUT  C9   C   CR6   0  -0.116   0.8695   0.8867  -0.5333
 AUT  C8   C   CR6   0   0.196   0.0917  -0.2106  -0.1716
 AUT  C3   C   CR16  0  -0.306  -3.6205  -0.0496   0.4771
 AUT  C7   C   CR6   0   0.021  -1.3793  -0.2272  -0.3507
 AUT  C11  C   CR6   0   0.048   2.9104  -0.2050   0.0985
 AUT  C14  C   CR6   0  -0.118   0.7901  -1.3119   0.3213
 AUT  CL1  CL  CL    0  -0.114  -0.0921  -2.7348   0.7662
 AUT  C10  C   CR16  0  -0.227   2.2487   0.9062  -0.4055
 AUT  C6   C   CR16  0  -0.259  -1.8869  -0.4637  -1.6258
 AUT  C4   C   CR16  0  -0.246  -4.1248  -0.2815  -0.7936
 AUT  C5   C   CR16  0  -0.264  -3.2535  -0.4917  -1.8534
 AUT  C2   C   CR6   0   0.121  -2.2489  -0.0197   0.7246
 AUT  C1   C   CH2   0  -0.524  -1.7569   0.2725   2.1158
 AUT  N    N   NH2   0  -0.795   5.0761   0.7293  -0.5922
 AUT  C    C   CH3   0  -0.653  -1.4935   1.7591   2.3452
 AUT  H1   H   HCH2  0   0.255   4.6185   0.0826   1.3171
 AUT  H2   H   HCH2  0   0.224   4.7620  -1.2449   0.1893
 AUT  H3   H   HCR6  0   0.275   2.6631  -2.2077   0.8366
 AUT  H4   H   HCR6  0   0.249  -4.3059   0.1053   1.3024
 AUT  H5   H   HCR6  0   0.276   2.8135   1.7779  -0.7051
 AUT  H6   H   HCR6  0   0.252  -1.2002  -0.6291  -2.4469
 AUT  H7   H   HCR6  0   0.255  -5.1952  -0.3024  -0.9538
 AUT  H8   H   HCR6  0   0.256  -3.6335  -0.6803  -2.8488
 AUT  H9   H   HCH2  0   0.245  -2.5074  -0.0701   2.8315
 AUT  H10  H   HCH2  0   0.239  -0.8493  -0.2923   2.3348
 AUT  H11  H   HNH2  0   0.360   6.0426   0.8201  -0.3097
 AUT  H12  H   HNH2  0   0.349   5.0904   0.3668  -1.5371
 AUT  H14  H   HCH3  0   0.222  -0.7138   2.1362   1.6841
 AUT  H15  H   HCH3  0   0.226  -2.3923   2.3505   2.1676
 AUT  H16  H   HCH3  0   0.233  -1.1726   1.9373   3.3719
 AUT  CL   CL  CL    0  -0.114   0.0909   2.2957  -1.1758

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
 AUT  C    C1   single    1.527  0.020  1.527
 AUT  C1   C2   single    1.504  0.020  1.504
 AUT  N    C12  single    1.449  0.020  1.449
 AUT  C12  C11  single    1.509  0.020  1.509
 AUT  C2   C3   aromatic  1.394  0.020  1.394
 AUT  C2   C7   aromatic  1.398  0.020  1.398
 AUT  C13  C11  aromatic  1.390  0.020  1.390
 AUT  C13  C14  aromatic  1.383  0.020  1.383
 AUT  C11  C10  aromatic  1.388  0.020  1.388
 AUT  CL1  C14  single    1.732  0.020  1.732
 AUT  C14  C8   aromatic  1.394  0.020  1.394
 AUT  C3   C4   aromatic  1.387  0.020  1.387
 AUT  C10  C9   aromatic  1.385  0.020  1.385
 AUT  C8   C9   aromatic  1.393  0.020  1.393
 AUT  C8   C7   single    1.482  0.020  1.482
 AUT  C9   CL   single    1.733  0.020  1.733
 AUT  C7   C6   aromatic  1.393  0.020  1.393
 AUT  C4   C5   aromatic  1.388  0.020  1.388
 AUT  C6   C5   aromatic  1.386  0.020  1.386
 AUT  C12  H1   single    0.970  0.020  1.090
 AUT  C12  H2   single    0.970  0.020  1.090
 AUT  C13  H3   single    0.930  0.020  1.080
 AUT  C3   H4   single    0.930  0.020  1.080
 AUT  C10  H5   single    0.930  0.020  1.080
 AUT  C6   H6   single    0.930  0.020  1.080
 AUT  C4   H7   single    0.930  0.020  1.080
 AUT  C5   H8   single    0.930  0.020  1.080
 AUT  C1   H9   single    0.970  0.020  1.090
 AUT  C1   H10  single    0.970  0.020  1.090
 AUT  N    H11  single    0.890  0.020  1.040
 AUT  N    H12  single    0.890  0.020  1.040
 AUT  C    H14  single    0.970  0.020  1.090
 AUT  C    H15  single    0.970  0.020  1.090
 AUT  C    H16  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
 AUT  H2   C12  H1   105.79  3.000
 AUT  H2   C12  N    114.18  3.000
 AUT  H1   C12  N    107.98  3.000
 AUT  H2   C12  C11  108.23  3.000
 AUT  H1   C12  C11  107.88  3.000
 AUT  N    C12  C11  112.39  3.000
 AUT  H3   C13  C14  119.84  3.000
 AUT  H3   C13  C11  120.15  3.000
 AUT  C14  C13  C11  120.01  3.000
 AUT  CL   C9   C10  118.03  3.000
 AUT  CL   C9   C8   119.07  3.000
 AUT  C10  C9   C8   122.90  3.000
 AUT  C14  C8   C7   122.08  3.000
 AUT  C7   C8   C9   122.12  3.000
 AUT  C14  C8   C9   115.75  3.000
 AUT  H4   C3   C2   118.94  3.000
 AUT  H4   C3   C4   119.44  3.000
 AUT  C2   C3   C4   121.61  3.000
 AUT  C2   C7   C6   120.17  3.000
 AUT  C6   C7   C8   118.32  3.000
 AUT  C2   C7   C8   121.51  3.000
 AUT  C10  C11  C13  118.87  3.000
 AUT  C10  C11  C12  121.38  3.000
 AUT  C13  C11  C12  119.74  3.000
 AUT  CL1  C14  C8   118.98  3.000
 AUT  C8   C14  C13  122.68  3.000
 AUT  CL1  C14  C13  118.33  3.000
 AUT  H5   C10  C11  119.81  3.000
 AUT  H5   C10  C9   120.40  3.000
 AUT  C11  C10  C9   119.79  3.000
 AUT  H6   C6   C5   119.84  3.000
 AUT  H6   C6   C7   119.27  3.000
 AUT  C5   C6   C7   120.88  3.000
 AUT  H7   C4   C5   120.32  3.000
 AUT  H7   C4   C3   119.90  3.000
 AUT  C5   C4   C3   119.78  3.000
 AUT  H8   C5   C4   120.55  3.000
 AUT  H8   C5   C6   120.07  3.000
 AUT  C4   C5   C6   119.38  3.000
 AUT  C1   C2   C7   122.45  3.000
 AUT  C7   C2   C3   118.17  3.000
 AUT  C1   C2   C3   119.35  3.000
 AUT  H10  C1   H9   106.13  3.000
 AUT  H10  C1   C    109.28  3.000
 AUT  H9   C1   C    108.99  3.000
 AUT  H10  C1   C2   110.92  3.000
 AUT  H9   C1   C2   108.68  3.000
 AUT  C    C1   C2   112.61  3.000
 AUT  H12  N    H11  106.23  3.000
 AUT  H12  N    C12  109.84  3.000
 AUT  H11  N    C12  109.29  3.000
 AUT  H16  C    H15  107.90  3.000
 AUT  H16  C    H14  107.71  3.000
 AUT  H15  C    H14  107.66  3.000
 AUT  H16  C    C1   110.56  3.000
 AUT  H15  C    C1   111.18  3.000
 AUT  H14  C    C1   111.67  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
 AUT  CONST_01  C9   C10  C11  C13    0.00   0.0  0
 AUT  CONST_02  C9   C8   C14  C13    0.00   0.0  0
 AUT  CONST_03  C7   C8   C14  C13  180.00   0.0  0
 AUT  CONST_06  C11  C13  C14  C8     0.00   0.0  0
 AUT  CONST_07  C11  C10  C9   C8     0.00   0.0  0
 AUT  CONST_08  C3   C2   C7   C8   180.00   0.0  0
 AUT  CONST_09  C5   C6   C7   C8   180.00   0.0  0
 AUT  CONST_10  C6   C7   C2   C3     0.00   0.0  0
 AUT  CONST_11  C6   C5   C4   C3     0.00   0.0  0
 AUT  CONST_12  C4   C3   C2   C7     0.00   0.0  0
 AUT  CONST_13  C10  C9   C8   C7   180.00   0.0  0
 AUT  CONST_14  C4   C5   C6   C7     0.00   0.0  0
 AUT  CONST_15  C10  C11  C13  C14    0.00   0.0  0
 AUT  CONST_16  C10  C9   C8   C14    0.00   0.0  0
 AUT  CONST_19  C2   C3   C4   C5     0.00   0.0  0
 AUT  CONST_20  C2   C7   C6   C5     0.00   0.0  0
 AUT  CONST_21  C14  C13  C11  C12  180.00   0.0  0
 AUT  CONST_22  C9   C10  C11  C12  180.00   0.0  0
 AUT  CONST_23  CL1  C14  C8   C9   180.00   0.0  0
 AUT  CONST_24  C1   C2   C7   C8     0.00   0.0  0
 AUT  CONST_25  CL1  C14  C8   C7     0.00   0.0  0
 AUT  CONST_26  CL   C9   C8   C7     0.00   0.0  0
 AUT  CONST_27  CL1  C14  C13  C11  180.00   0.0  0
 AUT  CONST_28  CL   C9   C10  C11  180.00   0.0  0
 AUT  CONST_29  CL   C9   C8   C14  180.00   0.0  0
 AUT  CONST_30  C1   C2   C7   C6   180.00   0.0  0
 AUT  CONST_31  C1   C2   C3   C4   180.00   0.0  0
 AUT  CONST_32  H5   C10  C11  C13  180.00   0.0  0
 AUT  CONST_33  H3   C13  C14  C8   180.00   0.0  0
 AUT  CONST_34  H6   C6   C7   C8     0.00   0.0  0
 AUT  CONST_35  H8   C5   C4   C3   180.00   0.0  0
 AUT  CONST_36  H4   C3   C2   C7   180.00   0.0  0
 AUT  CONST_37  H7   C4   C5   C6   180.00   0.0  0
 AUT  Var_01    N    C12  C11  C13  156.47  30.0  2
 AUT  Var_02    C    C1   C2   C3   -92.05  30.0  2
 AUT  Var_03    H11  N    C12  C11  169.12  30.0  3
 AUT  Var_04    H14  C    C1   C2   -62.08  30.0  3

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
 AUT  plan-1  C12  0.020
 AUT  plan-1  C13  0.020
 AUT  plan-1  C9   0.020
 AUT  plan-1  C8   0.020
 AUT  plan-1  C7   0.020
 AUT  plan-1  C11  0.020
 AUT  plan-1  C14  0.020
 AUT  plan-1  CL1  0.020
 AUT  plan-1  C10  0.020
 AUT  plan-1  H3   0.020
 AUT  plan-1  H5   0.020
 AUT  plan-1  CL   0.020
 AUT  plan-2  C8   0.020
 AUT  plan-2  C3   0.020
 AUT  plan-2  C7   0.020
 AUT  plan-2  C6   0.020
 AUT  plan-2  C4   0.020
 AUT  plan-2  C5   0.020
 AUT  plan-2  C2   0.020
 AUT  plan-2  C1   0.020
 AUT  plan-2  H4   0.020
 AUT  plan-2  H6   0.020
 AUT  plan-2  H7   0.020
 AUT  plan-2  H8   0.020

