# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 21 06:14:33 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: ~{N}-[(2~{R})-3-(2-methylpropoxy)-2-pyrrolidin-1-yl-propyl]-~{N}-(phenylmethyl)aniline
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)COC[C@@H](CN(Cc1ccccc1)c2ccccc2)N3CCCC3
#
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
 CQN  CQN  ~{N}-[(2~{R})-3-(2-methylpropoxy)-2-pyrrolidin-1-yl-propyl]-~{N}-(phenylmethyl)aniline  ligand  61  27  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_CQN
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
 CQN  C1   C  CH2   0  -0.128   2.2423  -0.4665  -1.5504
 CQN  C10  C  CH2   0  -0.493   1.4780  -0.5116   2.8224
 CQN  C11  C  CH2   0  -0.264   1.3467   0.3736   1.5681
 CQN  C12  C  CH2   0  -0.385  -1.7868   1.2528  -1.6752
 CQN  C13  C  CR6   0   0.076  -2.1189   2.1628  -0.5132
 CQN  C14  C  CR16  0  -0.301  -2.6887   3.4096  -0.7592
 CQN  C15  C  CR16  0  -0.245  -2.9691   4.2806   0.2843
 CQN  C16  C  CR16  0  -0.271  -2.6890   3.9112   1.5943
 CQN  C17  C  CR16  0  -0.243  -2.1295   2.6661   1.8466
 CQN  C18  C  CR16  0  -0.292  -1.8473   1.7964   0.8001
 CQN  C19  C  CR6   0   0.395  -2.5361  -0.9015  -0.8169
 CQN  C2   C  CH1   0  -0.136   0.9403  -0.0933  -0.8388
 CQN  C20  C  CR16  0  -0.342  -3.8677  -0.4459  -0.8131
 CQN  C21  C  CR16  0  -0.243  -4.8968  -1.2370  -0.3260
 CQN  C22  C  CR16  0  -0.304  -4.6548  -2.5062   0.1797
 CQN  C23  C  CR16  0  -0.246  -3.3427  -2.9622   0.1948
 CQN  C24  C  CR16  0  -0.341  -2.3036  -2.1813  -0.2825
 CQN  C3   C  CH2   0  -0.308  -0.2239  -0.6328  -1.6828
 CQN  C4   C  CH2   0  -0.103   4.5815  -0.4214  -1.3240
 CQN  C5   C  CH1   0  -0.280   5.6836  -0.0732  -0.3356
 CQN  C6   C  CH3   0  -0.657   5.4557  -0.7415   1.0160
 CQN  C7   C  CH3   0  -0.661   7.0353  -0.4732  -0.9179
 CQN  C8   C  CH2   0  -0.287   1.2513  -1.8665   0.8775
 CQN  C9   C  CH2   0  -0.443   1.0001  -1.8989   2.3760
 CQN  N2   N  NT    0  -0.426   0.8374  -0.5225   0.5353
 CQN  N3   N  NT    0  -0.513  -1.5198  -0.1143  -1.3069
 CQN  O1   O  O2    0  -0.481   3.3420   0.0301  -0.8389
 CQN  H1   H  HCH2  0   0.192   2.3143  -1.5609  -1.6493
 CQN  H2   H  HCH2  0   0.205   2.2189  -0.0659  -2.5752
 CQN  H3   H  HCH2  0   0.228   2.5201  -0.5559   3.1434
 CQN  H4   H  HCH2  0   0.237   0.9029  -0.1277   3.6650
 CQN  H5   H  HCH2  0   0.219   0.6498   1.2018   1.7191
 CQN  H6   H  HCH2  0   0.216   2.3152   0.8135   1.3097
 CQN  H7   H  HCH2  0   0.254  -2.5792   1.3223  -2.4319
 CQN  H8   H  HCH2  0   0.281  -0.8925   1.6404  -2.1684
 CQN  H9   H  HCR6  0   0.246  -2.9177   3.7039  -1.7775
 CQN  H10  H  HCR6  0   0.252  -3.4118   5.2459   0.0738
 CQN  H11  H  HCR6  0   0.251  -2.9105   4.5858   2.4113
 CQN  H12  H  HCR6  0   0.250  -1.9151   2.3654   2.8646
 CQN  H13  H  HCR6  0   0.278  -1.4143   0.8237   1.0024
 CQN  H14  H  HCH1  0   0.240   0.8631   1.0007  -0.8383
 CQN  H15  H  HCR6  0   0.256  -4.1202   0.5342  -1.1916
 CQN  H16  H  HCR6  0   0.246  -5.9068  -0.8465  -0.3498
 CQN  H17  H  HCR6  0   0.241  -5.4626  -3.1190   0.5568
 CQN  H18  H  HCR6  0   0.246  -3.1120  -3.9411   0.5967
 CQN  H19  H  HCR6  0   0.250  -1.3007  -2.5757  -0.2172
 CQN  H20  H  HCH2  0   0.246  -0.0418  -0.3806  -2.7340
 CQN  H21  H  HCH2  0   0.249  -0.2344  -1.7216  -1.6456
 CQN  H22  H  HCH2  0   0.199   4.8004   0.0278  -2.3048
 CQN  H23  H  HCH2  0   0.184   4.5620  -1.5128  -1.4727
 CQN  H24  H  HCH1  0   0.222   5.6813   1.0136  -0.1950
 CQN  H25  H  HCH3  0   0.224   6.2588  -0.4953   1.7127
 CQN  H26  H  HCH3  0   0.240   4.5148  -0.4329   1.4713
 CQN  H27  H  HCH3  0   0.209   5.4331  -1.8292   0.9100
 CQN  H28  H  HCH3  0   0.227   7.2334   0.0261  -1.8680
 CQN  H29  H  HCH3  0   0.232   7.8444  -0.2122  -0.2343
 CQN  H30  H  HCH3  0   0.216   7.0881  -1.5508  -1.0910
 CQN  H31  H  HCH2  0   0.205   2.3148  -2.0641   0.6709
 CQN  H32  H  HCH2  0   0.230   0.6733  -2.6178   0.3344
 CQN  H33  H  HCH2  0   0.227   1.5257  -2.7123   2.8765
 CQN  H34  H  HCH2  0   0.225  -0.0679  -2.0221   2.5659

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
 CQN  C23  C22  aromatic  1.389  0.020  1.389
 CQN  C23  C24  aromatic  1.385  0.020  1.385
 CQN  C22  C21  aromatic  1.387  0.020  1.387
 CQN  C24  C19  aromatic  1.406  0.020  1.406
 CQN  C21  C20  aromatic  1.387  0.020  1.387
 CQN  C17  C18  aromatic  1.390  0.020  1.390
 CQN  C17  C16  aromatic  1.388  0.020  1.388
 CQN  C18  C13  aromatic  1.390  0.020  1.390
 CQN  C16  C15  aromatic  1.390  0.020  1.390
 CQN  C19  C20  aromatic  1.407  0.020  1.407
 CQN  C19  N3   single    1.376  0.020  1.376
 CQN  C13  C12  single    1.513  0.020  1.513
 CQN  C13  C14  aromatic  1.393  0.020  1.393
 CQN  C15  C14  aromatic  1.388  0.020  1.388
 CQN  C12  N3   single    1.441  0.020  1.441
 CQN  N3   C3   single    1.446  0.020  1.446
 CQN  C3   C2   single    1.536  0.020  1.536
 CQN  C10  C11  single    1.541  0.020  1.541
 CQN  C10  C9   single    1.534  0.020  1.534
 CQN  C2   N2   single    1.443  0.020  1.443
 CQN  C2   C1   single    1.530  0.020  1.530
 CQN  C11  N2   single    1.459  0.020  1.459
 CQN  C6   C5   single    1.525  0.020  1.525
 CQN  C9   C8   single    1.520  0.020  1.520
 CQN  N2   C8   single    1.447  0.020  1.447
 CQN  C1   O1   single    1.401  0.020  1.401
 CQN  O1   C4   single    1.406  0.020  1.406
 CQN  C5   C7   single    1.525  0.020  1.525
 CQN  C5   C4   single    1.521  0.020  1.521
 CQN  C1   H1   single    0.970  0.020  1.090
 CQN  C1   H2   single    0.970  0.020  1.090
 CQN  C10  H3   single    0.970  0.020  1.090
 CQN  C10  H4   single    0.970  0.020  1.090
 CQN  C11  H5   single    0.970  0.020  1.090
 CQN  C11  H6   single    0.970  0.020  1.090
 CQN  C12  H7   single    0.970  0.020  1.090
 CQN  C12  H8   single    0.970  0.020  1.090
 CQN  C14  H9   single    0.930  0.020  1.080
 CQN  C15  H10  single    0.930  0.020  1.080
 CQN  C16  H11  single    0.930  0.020  1.080
 CQN  C17  H12  single    0.930  0.020  1.080
 CQN  C18  H13  single    0.930  0.020  1.080
 CQN  C2   H14  single    0.970  0.020  1.090
 CQN  C20  H15  single    0.930  0.020  1.080
 CQN  C21  H16  single    0.930  0.020  1.080
 CQN  C22  H17  single    0.930  0.020  1.080
 CQN  C23  H18  single    0.930  0.020  1.080
 CQN  C24  H19  single    0.930  0.020  1.080
 CQN  C3   H20  single    0.970  0.020  1.090
 CQN  C3   H21  single    0.970  0.020  1.090
 CQN  C4   H22  single    0.970  0.020  1.090
 CQN  C4   H23  single    0.970  0.020  1.090
 CQN  C5   H24  single    0.970  0.020  1.090
 CQN  C6   H25  single    0.970  0.020  1.090
 CQN  C6   H26  single    0.970  0.020  1.090
 CQN  C6   H27  single    0.970  0.020  1.090
 CQN  C7   H28  single    0.970  0.020  1.090
 CQN  C7   H29  single    0.970  0.020  1.090
 CQN  C7   H30  single    0.970  0.020  1.090
 CQN  C8   H31  single    0.970  0.020  1.090
 CQN  C8   H32  single    0.970  0.020  1.090
 CQN  C9   H33  single    0.970  0.020  1.090
 CQN  C9   H34  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
 CQN  H2   C1   H1   106.23  3.000
 CQN  H2   C1   O1   111.14  3.000
 CQN  H1   C1   O1   110.28  3.000
 CQN  H2   C1   C2   109.04  3.000
 CQN  H1   C1   C2   109.87  3.000
 CQN  O1   C1   C2   110.20  3.000
 CQN  H4   C10  H3   106.90  3.000
 CQN  H4   C10  C9   112.28  3.000
 CQN  H3   C10  C9   110.27  3.000
 CQN  H4   C10  C11  112.46  3.000
 CQN  H3   C10  C11  110.13  3.000
 CQN  C9   C10  C11  104.84  3.000
 CQN  H6   C11  H5   106.99  3.000
 CQN  H6   C11  N2   112.87  3.000
 CQN  H5   C11  N2   109.92  3.000
 CQN  H6   C11  C10  110.34  3.000
 CQN  H5   C11  C10  112.16  3.000
 CQN  N2   C11  C10  104.66  3.000
 CQN  H8   C12  H7   104.91  3.000
 CQN  H8   C12  N3   107.49  3.000
 CQN  H7   C12  N3   111.72  3.000
 CQN  H8   C12  C13  108.24  3.000
 CQN  H7   C12  C13  109.44  3.000
 CQN  N3   C12  C13  114.53  3.000
 CQN  C18  C13  C14  118.86  3.000
 CQN  C14  C13  C12  119.51  3.000
 CQN  C18  C13  C12  121.61  3.000
 CQN  H9   C14  C15  119.54  3.000
 CQN  H9   C14  C13  119.68  3.000
 CQN  C15  C14  C13  120.77  3.000
 CQN  H10  C15  C16  120.18  3.000
 CQN  H10  C15  C14  119.73  3.000
 CQN  C16  C15  C14  120.09  3.000
 CQN  H11  C16  C17  120.28  3.000
 CQN  H11  C16  C15  120.31  3.000
 CQN  C17  C16  C15  119.41  3.000
 CQN  H12  C17  C18  119.60  3.000
 CQN  H12  C17  C16  119.98  3.000
 CQN  C18  C17  C16  120.42  3.000
 CQN  H13  C18  C17  120.15  3.000
 CQN  H13  C18  C13  119.40  3.000
 CQN  C17  C18  C13  120.45  3.000
 CQN  N3   C19  C24  122.27  3.000
 CQN  N3   C19  C20  120.97  3.000
 CQN  C24  C19  C20  116.75  3.000
 CQN  H14  C2   N2   106.93  3.000
 CQN  H14  C2   C3   107.30  3.000
 CQN  N2   C2   C3   111.39  3.000
 CQN  H14  C2   C1   107.66  3.000
 CQN  N2   C2   C1   115.53  3.000
 CQN  C3   C2   C1   107.68  3.000
 CQN  H15  C20  C21  117.85  3.000
 CQN  H15  C20  C19  120.92  3.000
 CQN  C21  C20  C19  121.23  3.000
 CQN  H16  C21  C22  120.03  3.000
 CQN  H16  C21  C20  118.60  3.000
 CQN  C22  C21  C20  121.37  3.000
 CQN  H17  C22  C23  121.03  3.000
 CQN  H17  C22  C21  121.00  3.000
 CQN  C23  C22  C21  117.98  3.000
 CQN  H18  C23  C24  118.54  3.000
 CQN  H18  C23  C22  120.13  3.000
 CQN  C24  C23  C22  121.32  3.000
 CQN  H19  C24  C23  118.05  3.000
 CQN  H19  C24  C19  120.60  3.000
 CQN  C23  C24  C19  121.34  3.000
 CQN  H21  C3   H20  105.33  3.000
 CQN  H21  C3   N3   109.93  3.000
 CQN  H20  C3   N3   108.41  3.000
 CQN  H21  C3   C2   109.85  3.000
 CQN  H20  C3   C2   108.68  3.000
 CQN  N3   C3   C2   114.24  3.000
 CQN  H23  C4   H22  106.71  3.000
 CQN  H23  C4   O1   110.44  3.000
 CQN  H22  C4   O1   110.60  3.000
 CQN  H23  C4   C5   109.11  3.000
 CQN  H22  C4   C5   109.97  3.000
 CQN  O1   C4   C5   109.95  3.000
 CQN  H24  C5   C7   108.11  3.000
 CQN  H24  C5   C6   108.70  3.000
 CQN  C7   C5   C6   110.85  3.000
 CQN  H24  C5   C4   107.99  3.000
 CQN  C7   C5   C4   109.52  3.000
 CQN  C6   C5   C4   111.56  3.000
 CQN  H27  C6   H26  107.72  3.000
 CQN  H27  C6   H25  107.55  3.000
 CQN  H26  C6   H25  107.74  3.000
 CQN  H27  C6   C5   110.68  3.000
 CQN  H26  C6   C5   112.04  3.000
 CQN  H25  C6   C5   110.92  3.000
 CQN  H30  C7   H29  107.42  3.000
 CQN  H30  C7   H28  107.73  3.000
 CQN  H29  C7   H28  107.55  3.000
 CQN  H30  C7   C5   111.21  3.000
 CQN  H29  C7   C5   110.82  3.000
 CQN  H28  C7   C5   111.92  3.000
 CQN  H32  C8   H31  107.12  3.000
 CQN  H32  C8   N2   111.70  3.000
 CQN  H31  C8   N2   113.48  3.000
 CQN  H32  C8   C9   112.83  3.000
 CQN  H31  C8   C9   109.93  3.000
 CQN  N2   C8   C9   101.87  3.000
 CQN  H34  C9   H33  107.92  3.000
 CQN  H34  C9   C8   109.61  3.000
 CQN  H33  C9   C8   112.89  3.000
 CQN  H34  C9   C10  110.87  3.000
 CQN  H33  C9   C10  113.02  3.000
 CQN  C8   C9   C10  102.48  3.000
 CQN  C8   N2   C2   118.75  3.000
 CQN  C8   N2   C11  107.65  3.000
 CQN  C2   N2   C11  117.80  3.000
 CQN  C3   N3   C19  123.34  3.000
 CQN  C3   N3   C12  116.10  3.000
 CQN  C19  N3   C12  119.81  3.000
 CQN  C4   O1   C1   113.77  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
 CQN  CONST_01  C16  C17  C18  C13     0.00   0.0  0
 CQN  CONST_02  C16  C15  C14  C13     0.00   0.0  0
 CQN  CONST_03  C17  C18  C13  C14     0.00   0.0  0
 CQN  CONST_04  C17  C16  C15  C14     0.00   0.0  0
 CQN  CONST_05  C18  C17  C16  C15     0.00   0.0  0
 CQN  CONST_06  C18  C13  C14  C15     0.00   0.0  0
 CQN  CONST_07  C22  C23  C24  C19     0.00   0.0  0
 CQN  CONST_08  C22  C21  C20  C19     0.00   0.0  0
 CQN  CONST_09  C23  C22  C21  C20     0.00   0.0  0
 CQN  CONST_10  C23  C24  C19  C20     0.00   0.0  0
 CQN  CONST_11  C24  C23  C22  C21     0.00   0.0  0
 CQN  CONST_12  C24  C19  C20  C21     0.00   0.0  0
 CQN  CONST_13  C17  C18  C13  C12   180.00   0.0  0
 CQN  CONST_14  C15  C14  C13  C12   180.00   0.0  0
 CQN  CONST_15  N3   C19  C20  C21   180.00   0.0  0
 CQN  CONST_16  N3   C19  C24  C23   180.00   0.0  0
 CQN  CONST_17  H12  C17  C18  C13   180.00   0.0  0
 CQN  CONST_18  H10  C15  C14  C13   180.00   0.0  0
 CQN  CONST_19  H13  C18  C13  C14   180.00   0.0  0
 CQN  CONST_20  H11  C16  C15  C14   180.00   0.0  0
 CQN  CONST_21  H9   C14  C15  C16   180.00   0.0  0
 CQN  CONST_22  H18  C23  C24  C19   180.00   0.0  0
 CQN  CONST_23  H16  C21  C20  C19   180.00   0.0  0
 CQN  CONST_24  H17  C22  C21  C20   180.00   0.0  0
 CQN  CONST_25  H19  C24  C19  C20   180.00   0.0  0
 CQN  CONST_26  H15  C20  C21  C22   180.00   0.0  0
 CQN  CONST_27  C24  C19  N3   C12   180.00   0.0  0
 CQN  CONST_28  C20  C19  N3   C12     0.00   0.0  0
 CQN  Var_01    C8   N2   C11  C10   -26.22  30.0  1
 CQN  Var_02    N2   C8   C9   C10   -40.51  30.0  1
 CQN  Var_03    C8   C9   C10  C11    24.88  30.0  1
 CQN  Var_04    C9   C8   N2   C11    42.33  30.0  1
 CQN  Var_05    N2   C11  C10  C9     -0.40  30.0  1
 CQN  Var_06    C19  N3   C12  C13    67.83  30.0  3
 CQN  Var_07    N3   C12  C13  C14  -165.33  30.0  2
 CQN  Var_08    C2   C3   N3   C19  -116.47  30.0  3
 CQN  Var_09    C5   C4   O1   C1   -168.40  30.0  3
 CQN  Var_10    O1   C4   C5   C6     61.11  30.0  3
 CQN  Var_11    H1   C1   O1   C4     50.37  30.0  1
 CQN  Var_12    H25  C6   C5   C4    179.26  30.0  3
 CQN  Var_13    H28  C7   C5   C4     58.70  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
 CQN  chir_01  C2  C3  N2  C1  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
 CQN  plan-1  C12  0.020
 CQN  plan-1  C13  0.020
 CQN  plan-1  C14  0.020
 CQN  plan-1  C15  0.020
 CQN  plan-1  C16  0.020
 CQN  plan-1  C17  0.020
 CQN  plan-1  C18  0.020
 CQN  plan-1  H9   0.020
 CQN  plan-1  H10  0.020
 CQN  plan-1  H11  0.020
 CQN  plan-1  H12  0.020
 CQN  plan-1  H13  0.020
 CQN  plan-2  C19  0.020
 CQN  plan-2  C20  0.020
 CQN  plan-2  C21  0.020
 CQN  plan-2  C22  0.020
 CQN  plan-2  C23  0.020
 CQN  plan-2  C24  0.020
 CQN  plan-2  N3   0.020
 CQN  plan-2  H15  0.020
 CQN  plan-2  H16  0.020
 CQN  plan-2  H17  0.020
 CQN  plan-2  H18  0.020
 CQN  plan-2  H19  0.020
 CQN  plan-3  C12  0.020
 CQN  plan-3  C19  0.020
 CQN  plan-3  C3   0.020
 CQN  plan-3  N3   0.020

