# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 20 19:17:00 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c5ccc6OCOc6c5)C1=O
#
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
 CIA  CIA  (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione  ligand  48  29  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_CIA
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
 CIA  C3    C  CR16  0  -0.284  -3.6121  -4.4277   0.3463
 CIA  C2    C  CR16  0  -0.269  -4.1890  -3.6226  -0.6491
 CIA  C1    C  CR16  0  -0.380  -3.7173  -2.3473  -0.8954
 CIA  C6    C  CR56  0   0.045  -2.6470  -1.8644  -0.1361
 CIA  C7    C  CR5   0  -0.016  -1.9148  -0.6370  -0.1061
 CIA  C8    C  CR5   0   0.362  -0.9786  -0.7626   0.8676
 CIA  N9    N  NR15  0  -0.753  -1.0671  -1.9912   1.4571
 CIA  C5    C  CR56  0   0.332  -2.0804  -2.6915   0.8625
 CIA  C4    C  CR16  0  -0.314  -2.5550  -3.9761   1.1147
 CIA  C13   C  CH1   0  -0.226   0.0581   0.2466   1.2080
 CIA  N12   N  NT    0  -0.513  -0.3105   1.5549   0.6488
 CIA  C17   C  C     0   0.559   0.3950   2.5936   1.1505
 CIA  O20   O  O     0  -0.473   1.3236   2.4533   1.9262
 CIA  C16   C  CH2   0  -0.395  -0.0310   3.9750   0.7297
 CIA  N15   N  NT    0  -0.475  -0.7336   4.0201  -0.5279
 CIA  C31   C  C     0   0.602  -1.6161   3.0658  -0.8521
 CIA  O32   O  O     0  -0.487  -2.4191   3.1775  -1.7646
 CIA  C11   C  CH1   0  -0.208  -1.6020   1.7905  -0.0113
 CIA  C10   C  CH2   0  -0.540  -2.0278   0.6148  -0.8931
 CIA  C18   C  CH3   0  -0.528  -0.7642   5.2995  -1.2087
 CIA  C22   C  CR6   0   0.150   1.4050  -0.2219   0.6910
 CIA  C27   C  CR16  0  -0.338   2.3211  -0.7764   1.5686
 CIA  C26   C  CR16  0  -0.330   3.5504  -1.2849   1.1288
 CIA  C25   C  CR56  0   0.290   3.8087  -1.1985  -0.2149
 CIA  O30   O  O     0  -0.485   4.8997  -1.6161  -0.9037
 CIA  C29   C  CH2   0   0.068   4.7529  -1.1005  -2.2194
 CIA  O28   O  O     0  -0.486   3.3969  -0.6952  -2.3552
 CIA  C24   C  CR56  0   0.313   2.8956  -0.6393  -1.0972
 CIA  C23   C  CR16  0  -0.374   1.6852  -0.1487  -0.6817
 CIA  H3    H  HCR6  0   0.250  -4.0012  -5.4234   0.5155
 CIA  H2    H  HCR6  0   0.247  -5.0151  -4.0118  -1.2302
 CIA  H1    H  HCR6  0   0.241  -4.1695  -1.7314  -1.6634
 CIA  HN9   H  HNR5  0   0.406  -0.4875  -2.3295   2.2078
 CIA  H4    H  HCR6  0   0.259  -2.1117  -4.5995   1.8808
 CIA  H13   H  HCH1  0   0.298   0.1285   0.3385   2.2975
 CIA  H161  H  HCH2  0   0.292   0.8705   4.5818   0.6531
 CIA  H162  H  HCH2  0   0.288  -0.6328   4.4080   1.5397
 CIA  H11   H  HCH1  0   0.304  -2.3773   1.9189   0.7571
 CIA  H101  H  HCH2  0   0.271  -3.0536   0.7884  -1.2148
 CIA  H102  H  HCH2  0   0.259  -1.4147   0.5795  -1.7993
 CIA  H181  H  HCH3  0   0.251   0.2326   5.7356  -1.1920
 CIA  H182  H  HCH3  0   0.263  -1.0669   5.1692  -2.2430
 CIA  H183  H  HCH3  0   0.247  -1.4550   5.9920  -0.7238
 CIA  H27   H  HCR6  0   0.254   2.0904  -0.8093   2.6262
 CIA  H26   H  HCR6  0   0.273   4.2610  -1.7145   1.8218
 CIA  H291  H  HCH2  0   0.233   5.4134  -0.2372  -2.3570
 CIA  H292  H  HCH2  0   0.247   4.9812  -1.8768  -2.9488
 CIA  H23   H  HCR6  0   0.267   0.9837   0.2848  -1.3830

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
 CIA  C3   C2    aromatic  1.404  0.020  1.404
 CIA  C3   C4    aromatic  1.383  0.020  1.383
 CIA  C3   H3    single    0.930  0.020  1.080
 CIA  C2   C1    aromatic  1.382  0.020  1.382
 CIA  C2   H2    single    0.930  0.020  1.080
 CIA  C1   C6    aromatic  1.398  0.020  1.398
 CIA  C1   H1    single    0.930  0.020  1.080
 CIA  C6   C7    aromatic  1.430  0.020  1.430
 CIA  C6   C5    aromatic  1.415  0.020  1.415
 CIA  C7   C8    aromatic  1.356  0.020  1.356
 CIA  C7   C10   single    1.483  0.020  1.483
 CIA  C8   N9    aromatic  1.366  0.020  1.366
 CIA  C8   C13   single    1.486  0.020  1.486
 CIA  N9   C5    aromatic  1.368  0.020  1.368
 CIA  N9   HN9   single    0.860  0.020  1.020
 CIA  C5   C4    aromatic  1.393  0.020  1.393
 CIA  C4   H4    single    0.930  0.020  1.080
 CIA  C13  N12   single    1.470  0.020  1.470
 CIA  C13  C22   single    1.517  0.020  1.517
 CIA  C13  H13   single    0.970  0.020  1.090
 CIA  N12  C17   single    1.352  0.020  1.352
 CIA  N12  C11   single    1.469  0.020  1.469
 CIA  C17  O20   double    1.218  0.020  1.218
 CIA  C17  C16   single    1.506  0.020  1.506
 CIA  C16  N15   single    1.441  0.020  1.441
 CIA  C16  H161  single    0.970  0.020  1.090
 CIA  C16  H162  single    0.970  0.020  1.090
 CIA  N15  C31   single    1.340  0.020  1.340
 CIA  N15  C18   single    1.450  0.020  1.450
 CIA  C31  O32   double    1.221  0.020  1.221
 CIA  C31  C11   single    1.528  0.020  1.528
 CIA  C11  C10   single    1.530  0.020  1.530
 CIA  C11  H11   single    0.970  0.020  1.090
 CIA  C10  H101  single    0.970  0.020  1.090
 CIA  C10  H102  single    0.970  0.020  1.090
 CIA  C18  H181  single    0.970  0.020  1.090
 CIA  C18  H182  single    0.970  0.020  1.090
 CIA  C18  H183  single    0.970  0.020  1.090
 CIA  C22  C27   aromatic  1.385  0.020  1.385
 CIA  C22  C23   aromatic  1.403  0.020  1.403
 CIA  C27  C26   aromatic  1.401  0.020  1.401
 CIA  C27  H27   single    0.930  0.020  1.080
 CIA  C26  C25   aromatic  1.371  0.020  1.371
 CIA  C26  H26   single    0.930  0.020  1.080
 CIA  C25  O30   single    1.356  0.020  1.356
 CIA  C25  C24   aromatic  1.387  0.020  1.387
 CIA  O30  C29   single    1.421  0.020  1.421
 CIA  C29  O28   single    1.422  0.020  1.422
 CIA  C29  H291  single    0.970  0.020  1.090
 CIA  C29  H292  single    0.970  0.020  1.090
 CIA  O28  C24   single    1.355  0.020  1.355
 CIA  C24  C23   aromatic  1.371  0.020  1.371
 CIA  C23  H23   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
 CIA  H3    C3   C4    119.24  3.000
 CIA  H3    C3   C2    119.38  3.000
 CIA  C4    C3   C2    121.38  3.000
 CIA  H2    C2   C1    119.78  3.000
 CIA  H2    C2   C3    119.21  3.000
 CIA  C1    C2   C3    121.01  3.000
 CIA  H1    C1   C6    120.54  3.000
 CIA  H1    C1   C2    120.56  3.000
 CIA  C6    C1   C2    118.89  3.000
 CIA  C5    C6   C7    106.38  3.000
 CIA  C5    C6   C1    119.20  3.000
 CIA  C7    C6   C1    134.42  3.000
 CIA  C10   C7   C8    120.77  3.000
 CIA  C10   C7   C6    132.42  3.000
 CIA  C8    C7   C6    106.80  3.000
 CIA  C13   C8   N9    123.86  3.000
 CIA  C13   C8   C7    125.66  3.000
 CIA  N9    C8   C7    110.39  3.000
 CIA  HN9   N9   C5    125.35  3.000
 CIA  HN9   N9   C8    125.93  3.000
 CIA  C5    N9   C8    108.72  3.000
 CIA  C4    C5   N9    130.25  3.000
 CIA  C4    C5   C6    122.04  3.000
 CIA  N9    C5   C6    107.71  3.000
 CIA  H4    C4   C5    121.32  3.000
 CIA  H4    C4   C3    121.21  3.000
 CIA  C5    C4   C3    117.46  3.000
 CIA  H13   C13  C22   107.92  3.000
 CIA  H13   C13  N12   108.65  3.000
 CIA  C22   C13  N12   111.59  3.000
 CIA  H13   C13  C8    109.24  3.000
 CIA  C22   C13  C8    109.36  3.000
 CIA  N12   C13  C8    110.02  3.000
 CIA  C11   N12  C17   120.14  3.000
 CIA  C11   N12  C13   122.28  3.000
 CIA  C17   N12  C13   114.31  3.000
 CIA  C16   C17  O20   119.96  3.000
 CIA  C16   C17  N12   116.96  3.000
 CIA  O20   C17  N12   123.07  3.000
 CIA  H162  C16  H161  106.60  3.000
 CIA  H162  C16  N15   111.36  3.000
 CIA  H161  C16  N15   108.95  3.000
 CIA  H162  C16  C17   108.10  3.000
 CIA  H161  C16  C17   107.25  3.000
 CIA  N15   C16  C17   114.23  3.000
 CIA  C18   N15  C31   120.08  3.000
 CIA  C18   N15  C16   116.59  3.000
 CIA  C31   N15  C16   120.67  3.000
 CIA  C11   C31  O32   119.60  3.000
 CIA  C11   C31  N15   117.09  3.000
 CIA  O32   C31  N15   123.30  3.000
 CIA  H11   C11  C10   107.24  3.000
 CIA  H11   C11  C31   106.30  3.000
 CIA  C10   C11  C31   108.77  3.000
 CIA  H11   C11  N12   108.95  3.000
 CIA  C10   C11  N12   112.36  3.000
 CIA  C31   C11  N12   112.91  3.000
 CIA  H102  C10  H101  106.75  3.000
 CIA  H102  C10  C11   110.24  3.000
 CIA  H101  C10  C11   108.05  3.000
 CIA  H102  C10  C7    111.68  3.000
 CIA  H101  C10  C7    111.30  3.000
 CIA  C11   C10  C7    108.75  3.000
 CIA  H183  C18  H182  108.85  3.000
 CIA  H183  C18  H181  108.58  3.000
 CIA  H182  C18  H181  108.55  3.000
 CIA  H183  C18  N15   111.38  3.000
 CIA  H182  C18  N15   110.33  3.000
 CIA  H181  C18  N15   109.09  3.000
 CIA  C23   C22  C27   120.60  3.000
 CIA  C23   C22  C13   119.65  3.000
 CIA  C27   C22  C13   119.68  3.000
 CIA  H27   C27  C26   118.84  3.000
 CIA  H27   C27  C22   119.36  3.000
 CIA  C26   C27  C22   121.80  3.000
 CIA  H26   C26  C25   121.95  3.000
 CIA  H26   C26  C27   121.30  3.000
 CIA  C25   C26  C27   116.75  3.000
 CIA  C24   C25  O30   109.30  3.000
 CIA  C24   C25  C26   121.65  3.000
 CIA  O30   C25  C26   129.05  3.000
 CIA  C29   O30  C25   105.99  3.000
 CIA  H292  C29  H291  110.56  3.000
 CIA  H292  C29  O28   109.82  3.000
 CIA  H291  C29  O28   109.78  3.000
 CIA  H292  C29  O30   109.86  3.000
 CIA  H291  C29  O30   109.88  3.000
 CIA  O28   C29  O30   106.88  3.000
 CIA  C24   O28  C29   106.01  3.000
 CIA  C23   C24  O28   128.52  3.000
 CIA  C23   C24  C25   122.18  3.000
 CIA  O28   C24  C25   109.28  3.000
 CIA  H23   C23  C24   121.28  3.000
 CIA  H23   C23  C22   121.69  3.000
 CIA  C24   C23  C22   117.02  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
 CIA  CONST_01  C6    C1   C2   C3     0.00   0.0  0
 CIA  CONST_02  C6    C5   C4   C3     0.00   0.0  0
 CIA  CONST_03  N9    C5   C4   C3   180.00   0.0  0
 CIA  CONST_04  C5    C4   C3   C2     0.00   0.0  0
 CIA  CONST_05  C7    C6   C1   C2   180.00   0.0  0
 CIA  CONST_06  C5    C6   C1   C2     0.00   0.0  0
 CIA  CONST_07  C4    C3   C2   C1     0.00   0.0  0
 CIA  CONST_08  C8    C7   C6   C1   180.00   0.0  0
 CIA  CONST_09  N9    C5   C6   C1   180.00   0.0  0
 CIA  CONST_10  C4    C5   C6   C1     0.00   0.0  0
 CIA  CONST_11  N9    C8   C7   C6     0.00   0.0  0
 CIA  CONST_12  C8    N9   C5   C6     0.00   0.0  0
 CIA  CONST_13  N9    C5   C6   C7     0.00   0.0  0
 CIA  CONST_14  C4    C5   C6   C7   180.00   0.0  0
 CIA  CONST_15  C5    N9   C8   C7     0.00   0.0  0
 CIA  CONST_16  C5    C6   C7   C8     0.00   0.0  0
 CIA  CONST_17  C4    C5   N9   C8   180.00   0.0  0
 CIA  CONST_18  C25   C26  C27  C22    0.00   0.0  0
 CIA  CONST_19  C25   C24  C23  C22    0.00   0.0  0
 CIA  CONST_20  C24   C23  C22  C27    0.00   0.0  0
 CIA  CONST_21  C24   C25  C26  C27    0.00   0.0  0
 CIA  CONST_22  C23   C22  C27  C26    0.00   0.0  0
 CIA  CONST_23  C23   C24  C25  C26    0.00   0.0  0
 CIA  CONST_24  C26   C27  C22  C13  180.00   0.0  0
 CIA  CONST_25  C24   C23  C22  C13  180.00   0.0  0
 CIA  CONST_26  C16   C17  N12  C13  180.00   0.0  0
 CIA  CONST_27  C11   N12  C17  C16    0.00   0.0  0
 CIA  CONST_28  C11   C31  N15  C16    0.00   0.0  0
 CIA  CONST_29  O20   C17  N12  C13    0.00   0.0  0
 CIA  CONST_30  C11   N12  C17  O20  180.00   0.0  0
 CIA  CONST_31  O32   C31  N15  C16  180.00   0.0  0
 CIA  CONST_32  C18   N15  C31  C11  180.00   0.0  0
 CIA  CONST_33  H1    C1   C2   C3   180.00   0.0  0
 CIA  CONST_34  H4    C4   C3   C2   180.00   0.0  0
 CIA  CONST_35  H3    C3   C2   C1   180.00   0.0  0
 CIA  CONST_36  H2    C2   C1   C6   180.00   0.0  0
 CIA  CONST_37  HN9   N9   C5   C6   180.00   0.0  0
 CIA  CONST_38  H27   C27  C22  C13    0.00   0.0  0
 CIA  CONST_39  H23   C23  C22  C13    0.00   0.0  0
 CIA  CONST_40  H26   C26  C27  C22  180.00   0.0  0
 CIA  CONST_41  C18   N15  C31  O32    0.00   0.0  0
 CIA  Var_01    C11   C10  C7   C6   148.74  30.0  1
 CIA  Var_02    N15   C16  C17  N12  -24.38  30.0  1
 CIA  Var_03    C31   N15  C16  C17   39.07  30.0  1
 CIA  Var_04    O28   C29  O30  C25  -15.47  30.0  1
 CIA  Var_05    C24   C25  O30  C29    9.71  30.0  1
 CIA  Var_06    C23   C24  O28  C29  171.40  30.0  1
 CIA  Var_07    H181  C18  N15  C16   45.34  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
 CIA  chir_01  C13  C8   N12  C22  positiv
 CIA  chir_02  C11  N12  C10  C31  positiv

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
 CIA  plan-1  C13  0.020
 CIA  plan-1  C22  0.020
 CIA  plan-1  C27  0.020
 CIA  plan-1  C26  0.020
 CIA  plan-1  C25  0.020
 CIA  plan-1  O30  0.020
 CIA  plan-1  O28  0.020
 CIA  plan-1  C24  0.020
 CIA  plan-1  C23  0.020
 CIA  plan-1  H27  0.020
 CIA  plan-1  H26  0.020
 CIA  plan-1  H23  0.020
 CIA  plan-2  C3   0.020
 CIA  plan-2  C2   0.020
 CIA  plan-2  C1   0.020
 CIA  plan-2  C6   0.020
 CIA  plan-2  C7   0.020
 CIA  plan-2  C8   0.020
 CIA  plan-2  N9   0.020
 CIA  plan-2  C5   0.020
 CIA  plan-2  C4   0.020
 CIA  plan-2  C13  0.020
 CIA  plan-2  C10  0.020
 CIA  plan-2  H3   0.020
 CIA  plan-2  H2   0.020
 CIA  plan-2  H1   0.020
 CIA  plan-2  HN9  0.020
 CIA  plan-2  H4   0.020
 CIA  plan-3  C13  0.020
 CIA  plan-3  N12  0.020
 CIA  plan-3  C17  0.020
 CIA  plan-3  O20  0.020
 CIA  plan-3  C16  0.020
 CIA  plan-3  C11  0.020
 CIA  plan-4  C16  0.020
 CIA  plan-4  N15  0.020
 CIA  plan-4  C31  0.020
 CIA  plan-4  O32  0.020
 CIA  plan-4  C11  0.020
 CIA  plan-4  C18  0.020

