# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 22 09:58:25 2020
#   Inital geometry file: a 146 line input string
#   Ligand name: 4-azanylidene-2-(3-methoxy-4-propan-2-yloxy-phenyl)-6,7-dihydro-[1,3]benzodioxolo[6,5-a]quinolizine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(ccc1OC(C)C)C2=C(C#N)C(=N)N3CCc4cc5OCOc5cc4C3=C2
#
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
 LQA  LQA  4-azanylidene-2-(3-methoxy-4-propan-2-yloxy-phenyl)-6,7-dihydro-[1,3]benzodioxolo[6,5-a]quinolizine-3-carbonitrile  ligand  55  32  .  2021-08-12  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_LQA
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
 LQA  C1   C  CR6   0  -0.222  -0.2304  -2.3222   0.2692
 LQA  C2   C  CR6   0   0.450   2.0376  -0.7474   0.2183
 LQA  C11  C  CR16  0  -0.415   3.2023   1.4225   0.5954
 LQA  C12  C  CH2   0  -0.304   3.5009  -2.6948   0.3038
 LQA  C13  C  CR56  0   0.320   4.3553   2.1467   0.5008
 LQA  C14  C  CR56  0   0.323   5.5404   1.5858   0.0408
 LQA  C17  C  CR6   0   0.333  -4.1808   0.9636  -0.0764
 LQA  C18  C  CR16  0  -0.403   5.6207   0.2680  -0.3316
 LQA  C19  C  CR16  0  -0.430  -2.6586  -0.7686  -0.8075
 LQA  C20  C  CR6   0   0.315  -3.8954  -0.1579  -0.8881
 LQA  C24  C  CH2   0  -0.540   4.4423  -1.9452  -0.6090
 LQA  C25  C  CH2   0   0.070   5.9559   3.6877   0.6404
 LQA  C26  C  CR16  0  -0.309  -1.9580   0.8156   0.8542
 LQA  C27  C  CR16  0  -0.368  -3.2023   1.4331   0.7868
 LQA  C29  C  CH1   0  -0.006  -5.8351   2.5889   0.5691
 LQA  C30  C  CH3   0  -0.442  -4.6867  -1.7067  -2.4912
 LQA  N3   N  NR6   0  -0.597   2.1643  -2.0977   0.2628
 LQA  C4   C  CR6   0   0.447   1.0700  -2.9670   0.3553
 LQA  C5   C  CR6   0   0.314  -0.3665  -0.9524   0.1649
 LQA  C6   C  CR16  0  -0.510   0.7935  -0.1654   0.1573
 LQA  C7   C  CR6   0   0.033   3.2569   0.0678   0.2018
 LQA  C8   C  CR6   0   0.037  -1.6784  -0.2938   0.0726
 LQA  C9   C  CR6   0   0.108   4.4534  -0.4963  -0.2395
 LQA  C10  C  CSP   0  -0.026  -1.3536  -3.1740   0.3925
 LQA  N15  N  NS    0  -0.255  -2.2397  -3.9069   0.5075
 LQA  N16  N  N     0  -0.670   1.3024  -4.2148   0.5160
 LQA  O21  O  O     0  -0.485   4.5654   3.4471   0.8088
 LQA  O22  O  O     0  -0.476   6.5112   2.5160   0.0484
 LQA  O28  O  O2    0  -0.462  -4.8874  -0.5469  -1.7083
 LQA  C31  C  CH3   0  -0.665  -6.9970   3.2258  -0.1664
 LQA  C32  C  CH3   0  -0.680  -6.2365   2.1133   1.9553
 LQA  H1   H  HCR6  0   0.276   2.2977   1.8727   0.9792
 LQA  H2   H  HCH2  0   0.290   3.4032  -3.7308  -0.0017
 LQA  H3   H  HCH2  0   0.266   3.8640  -2.6853   1.3351
 LQA  H4   H  HCR6  0   0.280   6.5476  -0.1708  -0.6763
 LQA  H5   H  HCR6  0   0.288  -2.4293  -1.6044  -1.4542
 LQA  H6   H  HCH2  0   0.278   5.4396  -2.3756  -0.5174
 LQA  H7   H  HCH2  0   0.271   4.1357  -2.0749  -1.6519
 LQA  H8   H  HCH2  0   0.250   6.1074   4.5401  -0.0224
 LQA  H9   H  HCH2  0   0.243   6.4260   3.8660   1.6116
 LQA  H10  H  HCR6  0   0.262  -1.2231   1.1987   1.5498
 LQA  H11  H  HCR6  0   0.284  -3.3862   2.2836   1.4281
 LQA  H12  H  HCH1  0   0.233  -5.0273   3.3249   0.6453
 LQA  H13  H  HCH3  0   0.263  -5.6116  -1.8740  -3.0371
 LQA  H14  H  HCH3  0   0.231  -3.8719  -1.5801  -3.2087
 LQA  H15  H  HCH3  0   0.227  -4.4772  -2.5839  -1.8724
 LQA  H16  H  HCR6  0   0.277   0.7043   0.9016   0.0319
 LQA  H17  H  H     0   0.341   0.4435  -4.7497   0.5545
 LQA  H19  H  HCH3  0   0.236  -7.3444   4.0965   0.3889
 LQA  H20  H  HCH3  0   0.242  -6.7041   3.5600  -1.1619
 LQA  H21  H  HCH3  0   0.231  -7.8337   2.5319  -0.2622
 LQA  H22  H  HCH3  0   0.243  -5.4101   1.6560   2.4993
 LQA  H23  H  HCH3  0   0.240  -6.5880   2.9600   2.5457
 LQA  H24  H  HCH3  0   0.234  -7.0484   1.3876   1.8913
 LQA  O23  O  O2    0  -0.470  -5.4010   1.4902  -0.2408

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
 LQA  C25  O22  single    1.425  0.020  1.425
 LQA  C25  O21  single    1.421  0.020  1.421
 LQA  O22  C14  single    1.345  0.020  1.345
 LQA  C14  C18  aromatic  1.372  0.020  1.372
 LQA  C14  C13  aromatic  1.389  0.020  1.389
 LQA  O21  C13  single    1.353  0.020  1.353
 LQA  C18  C9   aromatic  1.398  0.020  1.398
 LQA  C12  C24  single    1.510  0.020  1.510
 LQA  C12  N3   single    1.464  0.020  1.464
 LQA  C13  C11  aromatic  1.365  0.020  1.365
 LQA  C9   C24  single    1.495  0.020  1.495
 LQA  C9   C7   aromatic  1.394  0.020  1.394
 LQA  N16  C4   double    1.279  0.020  1.279
 LQA  C11  C7   aromatic  1.412  0.020  1.412
 LQA  N3   C4   single    1.401  0.020  1.401
 LQA  N3   C2   single    1.357  0.020  1.357
 LQA  C7   C2   single    1.467  0.020  1.467
 LQA  C4   C1   single    1.454  0.020  1.454
 LQA  C2   C6   double    1.375  0.020  1.375
 LQA  C1   C10  single    1.415  0.020  1.415
 LQA  C1   C5   double    1.381  0.020  1.381
 LQA  C6   C5   single    1.402  0.020  1.402
 LQA  C10  N15  triple    1.156  0.020  1.156
 LQA  C5   C8   single    1.471  0.020  1.471
 LQA  C26  C8   aromatic  1.386  0.020  1.386
 LQA  C26  C27  aromatic  1.391  0.020  1.391
 LQA  C8   C19  aromatic  1.400  0.020  1.400
 LQA  C27  C17  aromatic  1.387  0.020  1.387
 LQA  C19  C20  aromatic  1.382  0.020  1.382
 LQA  C17  C20  aromatic  1.413  0.020  1.413
 LQA  C17  O23  single    1.339  0.020  1.339
 LQA  C20  O28  single    1.345  0.020  1.345
 LQA  O23  C29  single    1.432  0.020  1.432
 LQA  C29  C32  single    1.520  0.020  1.520
 LQA  C29  C31  single    1.515  0.020  1.515
 LQA  O28  C30  single    1.414  0.020  1.414
 LQA  C11  H1   single    0.930  0.020  1.080
 LQA  C12  H2   single    0.970  0.020  1.090
 LQA  C12  H3   single    0.970  0.020  1.090
 LQA  C18  H4   single    0.930  0.020  1.080
 LQA  C19  H5   single    0.930  0.020  1.080
 LQA  C24  H6   single    0.970  0.020  1.090
 LQA  C24  H7   single    0.970  0.020  1.090
 LQA  C25  H8   single    0.970  0.020  1.090
 LQA  C25  H9   single    0.970  0.020  1.090
 LQA  C26  H10  single    0.930  0.020  1.080
 LQA  C27  H11  single    0.930  0.020  1.080
 LQA  C29  H12  single    0.970  0.020  1.090
 LQA  C30  H13  single    0.970  0.020  1.090
 LQA  C30  H14  single    0.970  0.020  1.090
 LQA  C30  H15  single    0.970  0.020  1.090
 LQA  C6   H16  single    0.930  0.020  1.080
 LQA  N16  H17  single    0.890  0.020  1.040
 LQA  C31  H19  single    0.970  0.020  1.090
 LQA  C31  H20  single    0.970  0.020  1.090
 LQA  C31  H21  single    0.970  0.020  1.090
 LQA  C32  H22  single    0.970  0.020  1.090
 LQA  C32  H23  single    0.970  0.020  1.090
 LQA  C32  H24  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
 LQA  C10  C1   C5   121.71  3.000
 LQA  C5   C1   C4   122.18  3.000
 LQA  C10  C1   C4   115.96  3.000
 LQA  C7   C2   C6   121.10  3.000
 LQA  C6   C2   N3   120.48  3.000
 LQA  C7   C2   N3   118.41  3.000
 LQA  H1   C11  C7   122.08  3.000
 LQA  H1   C11  C13  120.70  3.000
 LQA  C7   C11  C13  117.20  3.000
 LQA  H3   C12  H2   107.69  3.000
 LQA  H3   C12  N3   109.02  3.000
 LQA  H2   C12  N3   107.42  3.000
 LQA  H3   C12  C24  111.02  3.000
 LQA  H2   C12  C24  111.10  3.000
 LQA  N3   C12  C24  110.46  3.000
 LQA  O21  C13  C14  109.32  3.000
 LQA  O21  C13  C11  128.72  3.000
 LQA  C14  C13  C11  121.96  3.000
 LQA  O22  C14  C18  128.60  3.000
 LQA  C18  C14  C13  121.84  3.000
 LQA  O22  C14  C13  109.56  3.000
 LQA  O23  C17  C27  125.89  3.000
 LQA  O23  C17  C20  115.19  3.000
 LQA  C27  C17  C20  118.92  3.000
 LQA  H4   C18  C9   120.96  3.000
 LQA  H4   C18  C14  121.76  3.000
 LQA  C9   C18  C14  117.28  3.000
 LQA  H5   C19  C8   119.30  3.000
 LQA  H5   C19  C20  119.78  3.000
 LQA  C8   C19  C20  120.89  3.000
 LQA  O28  C20  C19  124.62  3.000
 LQA  O28  C20  C17  115.52  3.000
 LQA  C19  C20  C17  119.86  3.000
 LQA  H7   C24  H6   106.83  3.000
 LQA  H7   C24  C9   110.62  3.000
 LQA  H6   C24  C9   110.79  3.000
 LQA  H7   C24  C12  110.02  3.000
 LQA  H6   C24  C12  108.88  3.000
 LQA  C9   C24  C12  109.64  3.000
 LQA  H9   C25  H8   110.65  3.000
 LQA  H9   C25  O22  109.60  3.000
 LQA  H8   C25  O22  109.64  3.000
 LQA  H9   C25  O21  110.06  3.000
 LQA  H8   C25  O21  109.90  3.000
 LQA  O22  C25  O21  106.93  3.000
 LQA  H10  C26  C8   120.60  3.000
 LQA  H10  C26  C27  118.79  3.000
 LQA  C8   C26  C27  120.58  3.000
 LQA  H11  C27  C26  118.22  3.000
 LQA  H11  C27  C17  121.04  3.000
 LQA  C26  C27  C17  120.74  3.000
 LQA  H12  C29  C32  109.97  3.000
 LQA  H12  C29  C31  108.47  3.000
 LQA  C32  C29  C31  111.82  3.000
 LQA  H12  C29  O23  109.34  3.000
 LQA  C31  C29  O23  106.28  3.000
 LQA  C32  C29  O23  110.84  3.000
 LQA  H15  C30  H14  108.75  3.000
 LQA  H15  C30  H13  108.89  3.000
 LQA  H14  C30  H13  108.81  3.000
 LQA  H15  C30  O28  111.83  3.000
 LQA  H14  C30  O28  111.99  3.000
 LQA  H13  C30  O28  106.48  3.000
 LQA  C4   N3   C12  117.27  3.000
 LQA  C4   N3   C2   123.15  3.000
 LQA  C12  N3   C2   119.46  3.000
 LQA  N16  C4   N3   118.15  3.000
 LQA  N3   C4   C1   114.81  3.000
 LQA  N16  C4   C1   127.04  3.000
 LQA  C8   C5   C6   119.10  3.000
 LQA  C8   C5   C1   122.48  3.000
 LQA  C6   C5   C1   118.42  3.000
 LQA  H16  C6   C5   119.20  3.000
 LQA  H16  C6   C2   119.93  3.000
 LQA  C5   C6   C2   120.72  3.000
 LQA  C9   C7   C11  120.64  3.000
 LQA  C11  C7   C2   119.87  3.000
 LQA  C9   C7   C2   119.47  3.000
 LQA  C5   C8   C26  120.21  3.000
 LQA  C26  C8   C19  119.00  3.000
 LQA  C5   C8   C19  120.79  3.000
 LQA  C7   C9   C24  117.63  3.000
 LQA  C7   C9   C18  121.07  3.000
 LQA  C24  C9   C18  121.30  3.000
 LQA  N15  C10  C1   180.00  3.000
 LQA  H17  N16  C4   111.46  3.000
 LQA  C25  O21  C13  106.72  3.000
 LQA  C25  O22  C14  106.84  3.000
 LQA  C30  O28  C20  118.06  3.000
 LQA  H21  C31  H20  108.71  3.000
 LQA  H21  C31  H19  107.96  3.000
 LQA  H20  C31  H19  107.82  3.000
 LQA  H21  C31  C29  111.30  3.000
 LQA  H20  C31  C29  111.47  3.000
 LQA  H19  C31  C29  109.45  3.000
 LQA  H24  C32  H23  107.96  3.000
 LQA  H24  C32  H22  108.33  3.000
 LQA  H23  C32  H22  107.46  3.000
 LQA  H24  C32  C29  110.57  3.000
 LQA  H23  C32  C29  109.64  3.000
 LQA  H22  C32  C29  112.73  3.000
 LQA  C29  O23  C17  120.56  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
 LQA  CONST_01  C18  C14  C13  C11     0.00   0.0  0
 LQA  CONST_02  C18  C9   C7   C11     0.00   0.0  0
 LQA  CONST_03  C9   C18  C14  C13     0.00   0.0  0
 LQA  CONST_04  C9   C7   C11  C13     0.00   0.0  0
 LQA  CONST_05  C7   C9   C18  C14     0.00   0.0  0
 LQA  CONST_06  C7   C11  C13  C14     0.00   0.0  0
 LQA  CONST_07  C8   C26  C27  C17     0.00   0.0  0
 LQA  CONST_08  C8   C19  C20  C17     0.00   0.0  0
 LQA  CONST_09  C27  C26  C8   C19     0.00   0.0  0
 LQA  CONST_10  C27  C17  C20  C19     0.00   0.0  0
 LQA  CONST_11  C26  C8   C19  C20     0.00   0.0  0
 LQA  CONST_12  C26  C27  C17  C20     0.00   0.0  0
 LQA  CONST_13  C5   C8   C19  C20   180.00   0.0  0
 LQA  CONST_14  C5   C8   C26  C27   180.00   0.0  0
 LQA  CONST_15  C12  N3   C4   C1    180.00   0.0  0
 LQA  CONST_16  C2   N3   C4   C1      0.00   0.0  0
 LQA  CONST_17  O23  C17  C20  C19   180.00   0.0  0
 LQA  CONST_18  O23  C17  C27  C26   180.00   0.0  0
 LQA  CONST_19  O28  C20  C17  C27   180.00   0.0  0
 LQA  CONST_20  O28  C20  C19  C8    180.00   0.0  0
 LQA  CONST_21  N16  C4   N3   C2    180.00   0.0  0
 LQA  CONST_22  N16  C4   N3   C12     0.00   0.0  0
 LQA  CONST_23  H1   C11  C7   C2      0.00   0.0  0
 LQA  CONST_24  H4   C18  C14  C13   180.00   0.0  0
 LQA  CONST_25  H10  C26  C27  C17   180.00   0.0  0
 LQA  CONST_26  H5   C19  C20  C17   180.00   0.0  0
 LQA  CONST_27  H11  C27  C17  C20   180.00   0.0  0
 LQA  CONST_28  H17  N16  C4   C1      0.00   0.0  0
 LQA  Var_01    C26  C8   C5   C1    133.47  30.0  2
 LQA  Var_02    C24  C12  N3   C2    -39.72  30.0  1
 LQA  Var_03    N3   C2   C7   C11  -159.07  30.0  1
 LQA  Var_04    C18  C9   C24  C12   144.70  30.0  1
 LQA  Var_05    O22  C25  O21  C13     7.66  30.0  1
 LQA  Var_06    O21  C25  O22  C14    -7.73  30.0  1
 LQA  Var_07    C9   C24  C12  N3     55.57  30.0  1
 LQA  Var_08    C32  C29  O23  C17   -77.42  30.0  3
 LQA  Var_09    H13  C30  O28  C20   177.22  30.0  3
 LQA  Var_10    H22  C32  C29  O23    61.83  30.0  3
 LQA  Var_11    H19  C31  C29  O23  -177.80  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
 LQA  plan-1  C17  0.020
 LQA  plan-1  C19  0.020
 LQA  plan-1  C20  0.020
 LQA  plan-1  C26  0.020
 LQA  plan-1  C27  0.020
 LQA  plan-1  C5   0.020
 LQA  plan-1  C8   0.020
 LQA  plan-1  O28  0.020
 LQA  plan-1  H5   0.020
 LQA  plan-1  H10  0.020
 LQA  plan-1  H11  0.020
 LQA  plan-1  O23  0.020
 LQA  plan-2  C2   0.020
 LQA  plan-2  C11  0.020
 LQA  plan-2  C13  0.020
 LQA  plan-2  C14  0.020
 LQA  plan-2  C18  0.020
 LQA  plan-2  C24  0.020
 LQA  plan-2  C7   0.020
 LQA  plan-2  C9   0.020
 LQA  plan-2  O21  0.020
 LQA  plan-2  O22  0.020
 LQA  plan-2  H1   0.020
 LQA  plan-2  H4   0.020
 LQA  plan-3  C1   0.020
 LQA  plan-3  C2   0.020
 LQA  plan-3  C12  0.020
 LQA  plan-3  N3   0.020
 LQA  plan-3  C4   0.020
 LQA  plan-3  C5   0.020
 LQA  plan-3  C6   0.020
 LQA  plan-3  C7   0.020
 LQA  plan-3  C8   0.020
 LQA  plan-3  C10  0.020
 LQA  plan-3  N15  0.020
 LQA  plan-3  N16  0.020
 LQA  plan-3  H16  0.020
 LQA  plan-3  H17  0.020

