# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Jul 20 23:42:37 2021
#   Inital geometry file: a 107 line input string
#   Ligand name: 2-chloranyl-10-(2-piperidin-4-ylethyl)phenoxazine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccc2Oc3ccccc3N(CCC4CCNCC4)c2c1
#
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
 E2F  E2F  2-chloranyl-10-(2-piperidin-4-ylethyl)phenoxazine  ligand  44  23  .  2022-03-18  2022-07-24
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_E2F
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
 E2F  C4   C   CR16  0  -0.359  17.1059  -34.5400  -1.2242
 E2F  C5   C   CR16  0  -0.256  16.2014  -33.7350  -0.5378
 E2F  C6   C   CR16  0  -0.275  16.1191  -33.7886   0.8412
 E2F  C7   C   CR16  0  -0.366  16.9527  -34.6569   1.5403
 E2F  C8   C   CR66  0   0.326  17.8612  -35.4372   0.8573
 E2F  C10  C   CR66  0   0.334  19.3127  -37.2646   0.9496
 E2F  C13  C   CR6   0  -0.045  20.6683  -39.3270  -0.2483
 E2F  C15  C   CR16  0  -0.376  19.8298  -38.2847   1.7163
 E2F  C17  C   CH2   0  -0.439  18.1587  -36.9386  -3.4334
 E2F  C20  C   CH1   0  -0.238  18.4582  -36.8712  -4.9281
 E2F  C21  C   CH2   0  -0.411  17.6362  -37.9033  -5.7000
 E2F  C22  C   CH2   0  -0.293  17.8906  -37.8072  -7.1972
 E2F  N2   N   NR6   0  -0.623  18.9087  -36.2037  -1.1654
 E2F  C11  C   CR66  0   0.356  19.4467  -37.2597  -0.4461
 E2F  C3   C   CR66  0   0.345  17.9598  -35.3988  -0.5383
 E2F  C12  C   CR16  0  -0.319  20.1327  -38.3163  -1.0384
 E2F  N23  N   NH1   0  -0.595  17.5963  -36.4652  -7.6661
 E2F  CL1  CL  CL    0  -0.131  21.5240  -40.6188  -1.0287
 E2F  C18  C   CH2   0  -0.287  18.4450  -35.4775  -7.0247
 E2F  C14  C   CR16  0  -0.243  20.5279  -39.3329   1.1231
 E2F  C19  C   CH2   0  -0.427  18.2109  -35.4828  -5.5211
 E2F  O9   O   O     0  -0.501  18.6968  -36.2316   1.5917
 E2F  H1   H   HCR6  0   0.267  17.1331  -34.4830  -2.3032
 E2F  H2   H   HCR6  0   0.258  15.5599  -33.0707  -1.1011
 E2F  H3   H   HCR6  0   0.258  15.4150  -33.1694   1.3800
 E2F  H4   H   HCR6  0   0.270  16.9103  -34.7191   2.6205
 E2F  H5   H   HCR6  0   0.280  19.7060  -38.2549   2.7912
 E2F  H6   H   HCH2  0   0.233  17.1294  -36.6140  -3.2512
 E2F  H7   H   HCH2  0   0.241  18.2080  -37.9820  -3.1063
 E2F  H8   H   HCH1  0   0.213  19.5203  -37.1170  -5.0729
 E2F  H9   H   HCH2  0   0.211  16.5705  -37.7421  -5.5035
 E2F  H10  H   HCH2  0   0.226  17.8774  -38.9114  -5.3525
 E2F  H11  H   HCH2  0   0.229  17.2536  -38.5165  -7.7301
 E2F  H12  H   HCH2  0   0.183  18.9339  -38.1044  -7.3976
 E2F  H13  H   HCH2  0   0.271  20.1553  -36.3987  -2.8027
 E2F  H14  H   HCH2  0   0.273  19.0730  -35.0487  -2.8647
 E2F  H15  H   HCR6  0   0.289  20.2587  -38.3654  -2.1099
 E2F  H17  H   HNH1  0   0.350  17.7283  -36.4218  -8.6681
 E2F  H18  H   HCH2  0   0.184  19.5171  -35.6554  -7.2143
 E2F  H19  H   HCH2  0   0.229  18.2117  -34.4922  -7.4342
 E2F  H20  H   HCR6  0   0.280  20.9441  -40.1255   1.7280
 E2F  H21  H   HCH2  0   0.231  18.8573  -34.7333  -5.0577
 E2F  H22  H   HCH2  0   0.213  17.1777  -35.1798  -5.3148
 E2F  C1   C   CH2   0  -0.363  19.1247  -36.1040  -2.5945

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
 E2F  N23  C22  single    1.452  0.020  1.452
 E2F  N23  C18  single    1.452  0.020  1.452
 E2F  C22  C21  single    1.522  0.020  1.522
 E2F  C18  C19  single    1.522  0.020  1.522
 E2F  C21  C20  single    1.529  0.020  1.529
 E2F  C19  C20  single    1.530  0.020  1.530
 E2F  C20  C17  single    1.526  0.020  1.526
 E2F  C17  C1   single    1.528  0.020  1.528
 E2F  C1   N2   single    1.449  0.020  1.449
 E2F  N2   C3   single    1.393  0.020  1.393
 E2F  N2   C11  single    1.386  0.020  1.386
 E2F  CL1  C13  single    1.735  0.020  1.735
 E2F  C4   C3   aromatic  1.392  0.020  1.392
 E2F  C4   C5   aromatic  1.392  0.020  1.392
 E2F  C12  C11  aromatic  1.392  0.020  1.392
 E2F  C12  C13  aromatic  1.390  0.020  1.390
 E2F  C3   C8   aromatic  1.400  0.020  1.400
 E2F  C5   C6   aromatic  1.383  0.020  1.383
 E2F  C11  C10  aromatic  1.402  0.020  1.402
 E2F  C13  C14  aromatic  1.379  0.020  1.379
 E2F  C8   O9   single    1.367  0.020  1.367
 E2F  C8   C7   aromatic  1.379  0.020  1.379
 E2F  C10  O9   single    1.363  0.020  1.363
 E2F  C10  C15  aromatic  1.377  0.020  1.377
 E2F  C6   C7   aromatic  1.392  0.020  1.392
 E2F  C14  C15  aromatic  1.392  0.020  1.392
 E2F  C4   H1   single    0.930  0.020  1.080
 E2F  C5   H2   single    0.930  0.020  1.080
 E2F  C6   H3   single    0.930  0.020  1.080
 E2F  C7   H4   single    0.930  0.020  1.080
 E2F  C15  H5   single    0.930  0.020  1.080
 E2F  C17  H6   single    0.970  0.020  1.090
 E2F  C17  H7   single    0.970  0.020  1.090
 E2F  C20  H8   single    0.970  0.020  1.090
 E2F  C21  H9   single    0.970  0.020  1.090
 E2F  C21  H10  single    0.970  0.020  1.090
 E2F  C22  H11  single    0.970  0.020  1.090
 E2F  C22  H12  single    0.970  0.020  1.090
 E2F  C1   H13  single    0.970  0.020  1.090
 E2F  C1   H14  single    0.970  0.020  1.090
 E2F  C12  H15  single    0.930  0.020  1.080
 E2F  N23  H17  single    0.890  0.020  1.040
 E2F  C18  H18  single    0.970  0.020  1.090
 E2F  C18  H19  single    0.970  0.020  1.090
 E2F  C14  H20  single    0.930  0.020  1.080
 E2F  C19  H21  single    0.970  0.020  1.090
 E2F  C19  H22  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
 E2F  H1   C4   C3   120.60  3.000
 E2F  H1   C4   C5   118.56  3.000
 E2F  C3   C4   C5   120.83  3.000
 E2F  H2   C5   C6   120.53  3.000
 E2F  H2   C5   C4   118.93  3.000
 E2F  C6   C5   C4   120.54  3.000
 E2F  H3   C6   C7   119.80  3.000
 E2F  H3   C6   C5   120.90  3.000
 E2F  C7   C6   C5   119.30  3.000
 E2F  H4   C7   C8   119.18  3.000
 E2F  H4   C7   C6   120.89  3.000
 E2F  C8   C7   C6   119.93  3.000
 E2F  O9   C8   C3   120.57  3.000
 E2F  O9   C8   C7   117.74  3.000
 E2F  C3   C8   C7   121.67  3.000
 E2F  O9   C10  C11  120.62  3.000
 E2F  O9   C10  C15  117.95  3.000
 E2F  C11  C10  C15  121.40  3.000
 E2F  C14  C13  CL1  119.64  3.000
 E2F  C14  C13  C12  121.95  3.000
 E2F  CL1  C13  C12  118.41  3.000
 E2F  H5   C15  C14  120.08  3.000
 E2F  H5   C15  C10  119.32  3.000
 E2F  C14  C15  C10  120.59  3.000
 E2F  H7   C17  H6   105.98  3.000
 E2F  H7   C17  C1   109.16  3.000
 E2F  H6   C17  C1   109.96  3.000
 E2F  H7   C17  C20  109.03  3.000
 E2F  H6   C17  C20  109.54  3.000
 E2F  C1   C17  C20  112.93  3.000
 E2F  H8   C20  C19  107.93  3.000
 E2F  H8   C20  C21  107.57  3.000
 E2F  C19  C20  C21  109.27  3.000
 E2F  H8   C20  C17  107.98  3.000
 E2F  C19  C20  C17  112.84  3.000
 E2F  C21  C20  C17  111.06  3.000
 E2F  H10  C21  H9   107.05  3.000
 E2F  H10  C21  C22  109.51  3.000
 E2F  H9   C21  C22  109.26  3.000
 E2F  H10  C21  C20  110.08  3.000
 E2F  H9   C21  C20  109.46  3.000
 E2F  C22  C21  C20  111.37  3.000
 E2F  H12  C22  H11  106.74  3.000
 E2F  H12  C22  N23  112.46  3.000
 E2F  H11  C22  N23  108.94  3.000
 E2F  H12  C22  C21  108.66  3.000
 E2F  H11  C22  C21  109.97  3.000
 E2F  N23  C22  C21  110.01  3.000
 E2F  C3   N2   C11  118.08  3.000
 E2F  C11  N2   C1   120.42  3.000
 E2F  C3   N2   C1   120.38  3.000
 E2F  C12  C11  N2   123.28  3.000
 E2F  C12  C11  C10  117.90  3.000
 E2F  N2   C11  C10  118.82  3.000
 E2F  N2   C3   C8   118.75  3.000
 E2F  C8   C3   C4   117.71  3.000
 E2F  N2   C3   C4   123.53  3.000
 E2F  H15  C12  C11  120.94  3.000
 E2F  H15  C12  C13  119.07  3.000
 E2F  C11  C12  C13  119.99  3.000
 E2F  H17  N23  C18  109.40  3.000
 E2F  H17  N23  C22  109.46  3.000
 E2F  C18  N23  C22  111.57  3.000
 E2F  H19  C18  H18  106.77  3.000
 E2F  H19  C18  C19  109.92  3.000
 E2F  H18  C18  C19  108.59  3.000
 E2F  H19  C18  N23  108.86  3.000
 E2F  H18  C18  N23  112.50  3.000
 E2F  C19  C18  N23  110.13  3.000
 E2F  H20  C14  C15  120.46  3.000
 E2F  H20  C14  C13  121.39  3.000
 E2F  C15  C14  C13  118.15  3.000
 E2F  H22  C19  H21  106.74  3.000
 E2F  H22  C19  C18  109.27  3.000
 E2F  H21  C19  C18  109.00  3.000
 E2F  H22  C19  C20  109.28  3.000
 E2F  H21  C19  C20  111.24  3.000
 E2F  C18  C19  C20  111.18  3.000
 E2F  C10  O9   C8   117.61  3.000
 E2F  H14  C1   H13  104.99  3.000
 E2F  H14  C1   N2   107.70  3.000
 E2F  H13  C1   N2   108.07  3.000
 E2F  H14  C1   C17  111.26  3.000
 E2F  H13  C1   C17  110.16  3.000
 E2F  N2   C1   C17  114.19  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
 E2F  CONST_01  C7   C8   C3   C4      0.00   0.0  0
 E2F  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 E2F  CONST_03  C8   C3   C4   C5      0.00   0.0  0
 E2F  CONST_04  C8   C7   C6   C5      0.00   0.0  0
 E2F  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 E2F  CONST_06  C3   C8   C7   C6      0.00   0.0  0
 E2F  CONST_07  C13  C12  C11  C10     0.00   0.0  0
 E2F  CONST_08  C13  C14  C15  C10     0.00   0.0  0
 E2F  CONST_09  C12  C11  C10  C15     0.00   0.0  0
 E2F  CONST_10  C12  C13  C14  C15     0.00   0.0  0
 E2F  CONST_11  C14  C13  C12  C11     0.00   0.0  0
 E2F  CONST_12  C14  C15  C10  C11     0.00   0.0  0
 E2F  CONST_13  CL1  C13  C14  C15   180.00   0.0  0
 E2F  CONST_14  CL1  C13  C12  C11   180.00   0.0  0
 E2F  CONST_15  H3   C6   C5   C4    180.00   0.0  0
 E2F  CONST_16  H4   C7   C6   C5    180.00   0.0  0
 E2F  CONST_17  H1   C4   C5   C6    180.00   0.0  0
 E2F  CONST_18  H2   C5   C6   C7    180.00   0.0  0
 E2F  CONST_19  H15  C12  C11  C10   180.00   0.0  0
 E2F  CONST_20  H20  C14  C15  C10   180.00   0.0  0
 E2F  CONST_21  H5   C15  C14  C13   180.00   0.0  0
 E2F  Var_01    C11  N2   C3   C4   -163.11  30.0  1
 E2F  Var_02    C11  C10  O9   C8     20.46  30.0  1
 E2F  Var_03    C3   N2   C11  C10   -17.31  30.0  1
 E2F  Var_04    C3   C8   O9   C10   -20.13  30.0  1
 E2F  Var_05    N23  C22  C21  C20   -56.99  30.0  1
 E2F  Var_06    N23  C18  C19  C20    57.06  30.0  1
 E2F  Var_07    C18  N23  C22  C21    61.28  30.0  1
 E2F  Var_08    C19  C18  N23  C22   -61.42  30.0  1
 E2F  Var_09    N2   C1   C17  C20  -176.94  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
 E2F  chir_01  C20  C21  C19  C17  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
 E2F  plan-1  C4   0.020
 E2F  plan-1  C5   0.020
 E2F  plan-1  C6   0.020
 E2F  plan-1  C7   0.020
 E2F  plan-1  C8   0.020
 E2F  plan-1  N2   0.020
 E2F  plan-1  C3   0.020
 E2F  plan-1  O9   0.020
 E2F  plan-1  H1   0.020
 E2F  plan-1  H2   0.020
 E2F  plan-1  H3   0.020
 E2F  plan-1  H4   0.020
 E2F  plan-2  C10  0.020
 E2F  plan-2  C13  0.020
 E2F  plan-2  C15  0.020
 E2F  plan-2  N2   0.020
 E2F  plan-2  C11  0.020
 E2F  plan-2  C12  0.020
 E2F  plan-2  CL1  0.020
 E2F  plan-2  C14  0.020
 E2F  plan-2  O9   0.020
 E2F  plan-2  H5   0.020
 E2F  plan-2  H15  0.020
 E2F  plan-2  H20  0.020

