# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 04:18:54 2021
#   Inital geometry file: a 113 line input string
#   Ligand name: 2-chloranyl-10-[3-[(3~{S})-piperidin-3-yl]propyl]phenoxazine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccc2Oc3ccccc3N(CCC[C@@H]4CCCNC4)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
 E2L  E2L  2-chloranyl-10-[3-[(3~{S})-piperidin-3-yl]propyl]phenoxazine  ligand  47  24  .  2022-03-18  2022-07-24
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_E2L
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
 E2L  C4   C   CR16  0  -0.363  32.6142  119.9512  -0.2814
 E2L  C5   C   CR16  0  -0.256  33.2108  118.9754   0.5118
 E2L  C6   C   CR16  0  -0.275  33.1380  119.0485   1.8904
 E2L  C7   C   CR16  0  -0.366  32.4621  120.1123   2.4810
 E2L  C8   C   CR66  0   0.325  31.8894  121.0869   1.6917
 E2L  C10  C   CR66  0   0.337  30.4063  122.8887   1.5977
 E2L  C13  C   CR6   0  -0.049  28.6709  124.5095   0.2218
 E2L  C15  C   CR16  0  -0.376  29.5201  123.6887   2.2842
 E2L  C17  C   CH2   0  -0.462  30.4682  121.1989  -2.6187
 E2L  C20  C   CH2   0  -0.435  29.0065  123.0358  -4.6816
 E2L  C21  C   CH1   0  -0.248  30.4377  122.5215  -4.8438
 E2L  C22  C   CH2   0  -0.262  30.7547  122.3765  -6.3303
 E2L  C24  C   CH2   0  -0.291  29.1608  124.0633  -6.9591
 E2L  C18  C   CH2   0  -0.425  30.6760  121.1910  -4.1306
 E2L  N2   N   NR6   0  -0.624  31.3541  122.0515  -0.4442
 E2L  N23  N   NH1   0  -0.598  30.5454  123.6303  -7.0302
 E2L  C11  C   CR66  0   0.355  30.4369  122.8693   0.1963
 E2L  C3   C   CR66  0   0.346  31.9480  121.0294   0.2943
 E2L  C12  C   CR16  0  -0.315  29.5448  123.6916  -0.4842
 E2L  C19  C   CH2   0  -0.427  28.7736  124.2967  -5.5075
 E2L  CL1  CL  CL    0  -0.131  27.5897  125.5245  -0.6780
 E2L  C14  C   CR16  0  -0.242  28.6399  124.5230   1.5998
 E2L  O9   O   O     0  -0.501  31.2858  122.1399   2.3212
 E2L  H1   H   HCR6  0   0.272  32.6792  119.8551  -1.3560
 E2L  H2   H   HCR6  0   0.259  33.7262  118.1538   0.0330
 E2L  H3   H   HCR6  0   0.258  33.5956  118.2896   2.5101
 E2L  H4   H   HCR6  0   0.270  32.3912  120.1969   3.5582
 E2L  H5   H   HCR6  0   0.280  29.5254  123.6776   3.3667
 E2L  H6   H   HCH2  0   0.238  29.4508  121.5130  -2.3718
 E2L  H7   H   HCH2  0   0.248  30.5584  120.1738  -2.2508
 E2L  H9   H   HCH2  0   0.211  28.3081  122.2530  -5.0027
 E2L  H10  H   HCH1  0   0.218  31.1213  123.2809  -4.4430
 E2L  H11  H   HCH2  0   0.178  30.1359  121.5573  -6.7384
 E2L  H12  H   HCH2  0   0.227  31.7977  122.0740  -6.4561
 E2L  H13  H   HCH2  0   0.228  29.0481  124.9833  -7.5368
 E2L  H14  H   HCH2  0   0.182  28.4672  123.3247  -7.3960
 E2L  H15  H   HCH2  0   0.228  30.0162  120.4346  -4.5672
 E2L  H16  H   HCH2  0   0.225  31.6974  120.8532  -4.3414
 E2L  H20  H   HNH1  0   0.349  30.8145  123.5197  -7.9990
 E2L  H21  H   HCR6  0   0.284  29.5220  123.7097  -1.5632
 E2L  H22  H   HCH2  0   0.214  29.3739  125.1173  -5.1028
 E2L  H23  H   HCH2  0   0.227  27.7276  124.6048  -5.4459
 E2L  H24  H   HCR6  0   0.280  27.9544  125.1579   2.1425
 E2L  C1   C   CH2   0  -0.360  31.4785  122.0811  -1.8879
 E2L  H8   H   HCH2  0   0.225  28.7762  123.2335  -3.6311
 E2L  H17  H   HCH2  0   0.273  32.4959  121.7826  -2.1480
 E2L  H18  H   HCH2  0   0.271  31.4004  123.1212  -2.2076

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
 E2L  N23  C24  single    1.453  0.020  1.453
 E2L  N23  C22  single    1.451  0.020  1.451
 E2L  C24  C19  single    1.520  0.020  1.520
 E2L  C22  C21  single    1.527  0.020  1.527
 E2L  C19  C20  single    1.525  0.020  1.525
 E2L  C21  C20  single    1.529  0.020  1.529
 E2L  C21  C18  single    1.528  0.020  1.528
 E2L  C18  C17  single    1.526  0.020  1.526
 E2L  C17  C1   single    1.527  0.020  1.527
 E2L  C1   N2   single    1.449  0.020  1.449
 E2L  C4   C5   aromatic  1.392  0.020  1.392
 E2L  C4   C3   aromatic  1.392  0.020  1.392
 E2L  N2   C3   single    1.394  0.020  1.394
 E2L  N2   C11  single    1.386  0.020  1.386
 E2L  C12  C11  aromatic  1.391  0.020  1.391
 E2L  C12  C13  aromatic  1.390  0.020  1.390
 E2L  CL1  C13  single    1.735  0.020  1.735
 E2L  C5   C6   aromatic  1.382  0.020  1.382
 E2L  C3   C8   aromatic  1.400  0.020  1.400
 E2L  C11  C10  aromatic  1.402  0.020  1.402
 E2L  C13  C14  aromatic  1.378  0.020  1.378
 E2L  C8   O9   single    1.367  0.020  1.367
 E2L  C8   C7   aromatic  1.379  0.020  1.379
 E2L  C10  O9   single    1.363  0.020  1.363
 E2L  C10  C15  aromatic  1.377  0.020  1.377
 E2L  C6   C7   aromatic  1.392  0.020  1.392
 E2L  C14  C15  aromatic  1.393  0.020  1.393
 E2L  C4   H1   single    0.930  0.020  1.080
 E2L  C5   H2   single    0.930  0.020  1.080
 E2L  C6   H3   single    0.930  0.020  1.080
 E2L  C7   H4   single    0.930  0.020  1.080
 E2L  C15  H5   single    0.930  0.020  1.080
 E2L  C17  H6   single    0.970  0.020  1.090
 E2L  C17  H7   single    0.970  0.020  1.090
 E2L  C20  H8   single    0.970  0.020  1.090
 E2L  C20  H9   single    0.970  0.020  1.090
 E2L  C21  H10  single    0.970  0.020  1.090
 E2L  C22  H11  single    0.970  0.020  1.090
 E2L  C22  H12  single    0.970  0.020  1.090
 E2L  C24  H13  single    0.970  0.020  1.090
 E2L  C24  H14  single    0.970  0.020  1.090
 E2L  C18  H15  single    0.970  0.020  1.090
 E2L  C18  H16  single    0.970  0.020  1.090
 E2L  C1   H17  single    0.970  0.020  1.090
 E2L  C1   H18  single    0.970  0.020  1.090
 E2L  N23  H20  single    0.890  0.020  1.040
 E2L  C12  H21  single    0.930  0.020  1.080
 E2L  C19  H22  single    0.970  0.020  1.090
 E2L  C19  H23  single    0.970  0.020  1.090
 E2L  C14  H24  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
 E2L  H1   C4   C3   120.58  3.000
 E2L  H1   C4   C5   118.59  3.000
 E2L  C3   C4   C5   120.83  3.000
 E2L  H2   C5   C6   120.44  3.000
 E2L  H2   C5   C4   118.98  3.000
 E2L  C6   C5   C4   120.57  3.000
 E2L  H3   C6   C7   119.92  3.000
 E2L  H3   C6   C5   120.80  3.000
 E2L  C7   C6   C5   119.28  3.000
 E2L  H4   C7   C8   119.15  3.000
 E2L  H4   C7   C6   120.90  3.000
 E2L  C8   C7   C6   119.94  3.000
 E2L  O9   C8   C3   120.64  3.000
 E2L  O9   C8   C7   117.66  3.000
 E2L  C3   C8   C7   121.68  3.000
 E2L  O9   C10  C11  120.60  3.000
 E2L  O9   C10  C15  118.02  3.000
 E2L  C11  C10  C15  121.36  3.000
 E2L  C14  C13  CL1  119.92  3.000
 E2L  C14  C13  C12  121.86  3.000
 E2L  CL1  C13  C12  118.22  3.000
 E2L  H5   C15  C14  120.04  3.000
 E2L  H5   C15  C10  119.30  3.000
 E2L  C14  C15  C10  120.65  3.000
 E2L  H7   C17  H6   105.69  3.000
 E2L  H7   C17  C1   109.03  3.000
 E2L  H6   C17  C1   109.98  3.000
 E2L  H7   C17  C18  108.50  3.000
 E2L  H6   C17  C18  110.61  3.000
 E2L  C1   C17  C18  112.76  3.000
 E2L  H9   C20  H8   106.03  3.000
 E2L  H9   C20  C19  109.52  3.000
 E2L  H8   C20  C19  109.79  3.000
 E2L  H9   C20  C21  108.95  3.000
 E2L  H8   C20  C21  111.09  3.000
 E2L  C19  C20  C21  111.31  3.000
 E2L  H10  C21  C18  109.56  3.000
 E2L  H10  C21  C22  106.97  3.000
 E2L  C18  C21  C22  109.83  3.000
 E2L  H10  C21  C20  108.15  3.000
 E2L  C18  C21  C20  112.90  3.000
 E2L  C22  C21  C20  109.24  3.000
 E2L  H12  C22  H11  106.67  3.000
 E2L  H12  C22  N23  108.73  3.000
 E2L  H11  C22  N23  112.44  3.000
 E2L  H12  C22  C21  109.66  3.000
 E2L  H11  C22  C21  108.29  3.000
 E2L  N23  C22  C21  110.95  3.000
 E2L  H14  C24  H13  106.83  3.000
 E2L  H14  C24  C19  108.71  3.000
 E2L  H13  C24  C19  110.46  3.000
 E2L  H14  C24  N23  112.35  3.000
 E2L  H13  C24  N23  108.88  3.000
 E2L  C19  C24  N23  109.59  3.000
 E2L  H16  C18  H15  105.78  3.000
 E2L  H16  C18  C21  108.90  3.000
 E2L  H15  C18  C21  108.75  3.000
 E2L  H16  C18  C17  108.60  3.000
 E2L  H15  C18  C17  108.46  3.000
 E2L  C21  C18  C17  115.89  3.000
 E2L  C3   N2   C11  118.03  3.000
 E2L  C11  N2   C1   120.34  3.000
 E2L  C3   N2   C1   120.41  3.000
 E2L  H20  N23  C24  109.45  3.000
 E2L  H20  N23  C22  109.22  3.000
 E2L  C24  N23  C22  111.81  3.000
 E2L  C12  C11  N2   123.18  3.000
 E2L  C12  C11  C10  117.83  3.000
 E2L  N2   C11  C10  118.99  3.000
 E2L  N2   C3   C8   118.75  3.000
 E2L  C8   C3   C4   117.69  3.000
 E2L  N2   C3   C4   123.56  3.000
 E2L  H21  C12  C11  120.83  3.000
 E2L  H21  C12  C13  118.99  3.000
 E2L  C11  C12  C13  120.18  3.000
 E2L  H23  C19  H22  107.03  3.000
 E2L  H23  C19  C24  109.94  3.000
 E2L  H22  C19  C24  109.18  3.000
 E2L  H23  C19  C20  110.42  3.000
 E2L  H22  C19  C20  109.63  3.000
 E2L  C24  C19  C20  110.56  3.000
 E2L  H24  C14  C15  120.41  3.000
 E2L  H24  C14  C13  121.47  3.000
 E2L  C15  C14  C13  118.12  3.000
 E2L  C10  O9   C8   117.62  3.000
 E2L  H18  C1   H17  104.93  3.000
 E2L  H18  C1   N2   107.77  3.000
 E2L  H17  C1   N2   108.16  3.000
 E2L  H18  C1   C17  111.29  3.000
 E2L  H17  C1   C17  110.16  3.000
 E2L  N2   C1   C17  114.08  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
 E2L  CONST_01  C7   C6   C5   C4      0.00   0.0  0
 E2L  CONST_02  C7   C8   C3   C4      0.00   0.0  0
 E2L  CONST_03  C8   C3   C4   C5      0.00   0.0  0
 E2L  CONST_04  C8   C7   C6   C5      0.00   0.0  0
 E2L  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 E2L  CONST_06  C3   C8   C7   C6      0.00   0.0  0
 E2L  CONST_07  C13  C12  C11  C10     0.00   0.0  0
 E2L  CONST_08  C13  C14  C15  C10     0.00   0.0  0
 E2L  CONST_09  C12  C11  C10  C15     0.00   0.0  0
 E2L  CONST_10  C12  C13  C14  C15     0.00   0.0  0
 E2L  CONST_11  C14  C13  C12  C11     0.00   0.0  0
 E2L  CONST_12  C14  C15  C10  C11     0.00   0.0  0
 E2L  CONST_13  CL1  C13  C14  C15   180.00   0.0  0
 E2L  CONST_14  CL1  C13  C12  C11   180.00   0.0  0
 E2L  CONST_15  H3   C6   C5   C4    180.00   0.0  0
 E2L  CONST_16  H4   C7   C6   C5    180.00   0.0  0
 E2L  CONST_17  H1   C4   C5   C6    180.00   0.0  0
 E2L  CONST_18  H2   C5   C6   C7    180.00   0.0  0
 E2L  CONST_19  H21  C12  C11  C10   180.00   0.0  0
 E2L  CONST_20  H24  C14  C15  C10   180.00   0.0  0
 E2L  CONST_21  H5   C15  C14  C13   180.00   0.0  0
 E2L  Var_01    C11  N2   C3   C4    163.49  30.0  1
 E2L  Var_02    C11  C10  O9   C8    -20.05  30.0  1
 E2L  Var_03    C3   N2   C11  C10    17.11  30.0  1
 E2L  Var_04    C3   C8   O9   C10    19.93  30.0  1
 E2L  Var_05    N23  C24  C19  C20   -56.78  30.0  1
 E2L  Var_06    C24  N23  C22  C21   -62.02  30.0  1
 E2L  Var_07    C24  C19  C20  C21    53.50  30.0  1
 E2L  Var_08    C19  C24  N23  C22    61.62  30.0  1
 E2L  Var_09    C1   C17  C18  C21   -65.41  30.0  3
 E2L  Var_10    N2   C1   C17  C18  -176.76  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
 E2L  chir_01  C21  C22  C20  C18  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
 E2L  plan-1  C4   0.020
 E2L  plan-1  C5   0.020
 E2L  plan-1  C6   0.020
 E2L  plan-1  C7   0.020
 E2L  plan-1  C8   0.020
 E2L  plan-1  N2   0.020
 E2L  plan-1  C3   0.020
 E2L  plan-1  O9   0.020
 E2L  plan-1  H1   0.020
 E2L  plan-1  H2   0.020
 E2L  plan-1  H3   0.020
 E2L  plan-1  H4   0.020
 E2L  plan-2  C10  0.020
 E2L  plan-2  C13  0.020
 E2L  plan-2  C15  0.020
 E2L  plan-2  N2   0.020
 E2L  plan-2  C11  0.020
 E2L  plan-2  C12  0.020
 E2L  plan-2  CL1  0.020
 E2L  plan-2  C14  0.020
 E2L  plan-2  O9   0.020
 E2L  plan-2  H5   0.020
 E2L  plan-2  H21  0.020
 E2L  plan-2  H24  0.020

