# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 17 16:47:47 2020
#   Inital geometry file: a 131 line input string
#   Ligand name: 7-(cyclopropylmethyl)-10-(ethylsulfonyl)-2-methyl-2,4,6,7-tetrahydro-3H-2,4,7-triazadibenzo[cd,f]azulen-3-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[S](=O)(=O)c1ccc2N(CC3CC3)Cc4c[nH]c5C(=O)N(C)C=C(c2c1)c45
#
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
 8NS  8NS  7-(cyclopropylmethyl)-10-(ethylsulfonyl)-2-methyl-2,4,6,7-tetrahydro-3H-2,4,7-triazadibenzo[cd,f]azulen-3-one  ligand  51  28  .  2022-09-16  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8NS
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
 8NS  N1   N  NR15  0  -0.655  -4.4017  -0.8922   1.3547
 8NS  C4   C  CR16  0  -0.253   1.3012   2.1855   0.8613
 8NS  C5   C  CR6   0   0.237   0.0995   1.4964   0.7112
 8NS  C7   C  CH1   0  -0.254  -1.0687   3.6031  -0.9661
 8NS  C8   C  CH2   0  -0.496  -1.5453   3.8175  -2.3707
 8NS  C10  C  CH2   0  -0.421  -1.8504   1.6532   2.1562
 8NS  C13  C  CR56  0   0.131  -3.3903  -1.2825   0.5331
 8NS  C17  C  CR6   0  -0.079  -1.1098  -0.6176  -0.0006
 8NS  C20  C  CR56  0   0.168  -2.3106  -0.4377   0.7489
 8NS  C3   C  CR16  0  -0.263   2.5204   1.6148   0.5525
 8NS  C19  C  CR16  0  -0.352   1.3537  -0.4156  -0.0380
 8NS  C12  C  CR15  0  -0.061  -3.9981   0.1892   2.0672
 8NS  C18  C  CR6   0   0.131   0.1129   0.1718   0.2284
 8NS  C11  C  CR5   0  -0.081  -2.7018   0.5021   1.7299
 8NS  C2   C  CR6   0  -0.160   2.5266   0.3004   0.1091
 8NS  C16  C  CR16  0  -0.040  -1.1483  -1.6056  -0.9368
 8NS  C14  C  CR6   0   0.536  -3.4134  -2.3328  -0.4302
 8NS  C9   C  CH2   0  -0.469  -0.3061   3.0163  -2.1141
 8NS  C    C  CH3   0  -0.672   6.0047  -1.6927   1.2801
 8NS  C1   C  CH2   0  -0.588   4.6385  -1.0378   1.3868
 8NS  N    N  NT    0  -0.523  -1.0746   2.2132   1.0598
 8NS  N2   N  NR6   0  -0.532  -2.2322  -2.4137  -1.1498
 8NS  O2   O  O     0  -0.511  -4.3550  -3.0913  -0.6466
 8NS  O    O  OS    0  -0.671   3.8344  -1.6710  -1.0535
 8NS  O1   O  OS    0  -0.673   5.0124   0.5230  -0.7137
 8NS  S    S  S     0   1.207   4.0770  -0.4901  -0.2244
 8NS  H    H  HNR5  0   0.415  -5.3132  -1.3173   1.4045
 8NS  H7   H  HCR6  0   0.264   1.2587   3.2042   1.2221
 8NS  H8   H  HCH2  0   0.241  -2.6991   3.2720   0.3713
 8NS  H9   H  HCH2  0   0.206  -2.3159   1.9002  -0.6562
 8NS  H10  H  HCH1  0   0.250  -0.6193   4.4594  -0.4736
 8NS  H12  H  HCH2  0   0.242  -2.4365   3.2891  -2.6883
 8NS  H11  H  HCH2  0   0.250  -1.4405   4.8061  -2.7991
 8NS  H16  H  HCH2  0   0.253  -2.4740   2.4453   2.5798
 8NS  H15  H  HCH2  0   0.258  -1.1518   1.3641   2.9458
 8NS  H20  H  HCH3  0   0.258  -2.2694  -4.4274  -1.7638
 8NS  H19  H  HCH3  0   0.258  -2.9636  -3.2829  -2.9208
 8NS  H18  H  HCH3  0   0.257  -1.2135  -3.3633  -2.6977
 8NS  H6   H  HCR6  0   0.281   3.4356   2.1797   0.6681
 8NS  H22  H  HCR6  0   0.275   1.3998  -1.4506  -0.3491
 8NS  H17  H  HCR5  0   0.290  -4.6648   0.6742   2.7626
 8NS  H21  H  HCR6  0   0.296  -0.3114  -1.8047  -1.5906
 8NS  H13  H  HCH2  0   0.247   0.6520   3.4501  -2.3688
 8NS  H14  H  HCH2  0   0.240  -0.3574   1.9430  -2.2554
 8NS  H1   H  HCH3  0   0.249   5.9818  -2.5708   0.6367
 8NS  H2   H  HCH3  0   0.250   6.7535  -0.9989   0.9024
 8NS  H3   H  HCH3  0   0.266   6.3188  -2.0142   2.2715
 8NS  H4   H  HCH2  0   0.300   3.8832  -1.7268   1.7669
 8NS  H5   H  HCH2  0   0.298   4.6575  -0.1584   2.0320
 8NS  C6   C  CH2   0  -0.280  -1.8662   2.7082  -0.0589
 8NS  C15  C  CH3   0  -0.520  -2.1709  -3.4311  -2.1907

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
 8NS  N1   C13  aromatic  1.360  0.020  1.360
 8NS  N1   C12  aromatic  1.357  0.020  1.357
 8NS  C4   C5   aromatic  1.393  0.020  1.393
 8NS  C4   C3   aromatic  1.381  0.020  1.381
 8NS  C5   C18  aromatic  1.410  0.020  1.410
 8NS  C5   N    single    1.419  0.020  1.419
 8NS  C6   C7   single    1.503  0.020  1.503
 8NS  C6   N    single    1.457  0.020  1.457
 8NS  C7   C8   single    1.499  0.020  1.499
 8NS  C7   C9   single    1.498  0.020  1.498
 8NS  C8   C9   single    1.498  0.020  1.498
 8NS  C10  C11  single    1.494  0.020  1.494
 8NS  C10  N    single    1.455  0.020  1.455
 8NS  C13  C20  aromatic  1.388  0.020  1.388
 8NS  C13  C14  single    1.425  0.020  1.425
 8NS  C15  N2   single    1.457  0.020  1.457
 8NS  C17  C20  single    1.427  0.020  1.427
 8NS  C17  C18  single    1.473  0.020  1.473
 8NS  C17  C16  double    1.362  0.020  1.362
 8NS  C20  C11  aromatic  1.414  0.020  1.414
 8NS  C3   C2   aromatic  1.387  0.020  1.387
 8NS  C19  C18  aromatic  1.398  0.020  1.398
 8NS  C19  C2   aromatic  1.382  0.020  1.382
 8NS  C12  C11  aromatic  1.375  0.020  1.375
 8NS  C2   S    single    1.772  0.020  1.772
 8NS  C16  N2   single    1.369  0.020  1.369
 8NS  C14  N2   single    1.386  0.020  1.386
 8NS  C14  O2   double    1.228  0.020  1.228
 8NS  C    C1   single    1.519  0.020  1.519
 8NS  C1   S    single    1.792  0.020  1.792
 8NS  O    S    double    1.463  0.020  1.463
 8NS  O1   S    double    1.463  0.020  1.463
 8NS  N1   H    single    0.860  0.020  1.020
 8NS  C4   H7   single    0.930  0.020  1.080
 8NS  C6   H8   single    0.970  0.020  1.090
 8NS  C6   H9   single    0.970  0.020  1.090
 8NS  C7   H10  single    0.970  0.020  1.090
 8NS  C8   H12  single    0.970  0.020  1.090
 8NS  C8   H11  single    0.970  0.020  1.090
 8NS  C10  H16  single    0.970  0.020  1.090
 8NS  C10  H15  single    0.970  0.020  1.090
 8NS  C15  H20  single    0.970  0.020  1.090
 8NS  C15  H19  single    0.970  0.020  1.090
 8NS  C15  H18  single    0.970  0.020  1.090
 8NS  C3   H6   single    0.930  0.020  1.080
 8NS  C19  H22  single    0.930  0.020  1.080
 8NS  C12  H17  single    0.930  0.020  1.080
 8NS  C16  H21  single    0.930  0.020  1.080
 8NS  C9   H13  single    0.970  0.020  1.090
 8NS  C9   H14  single    0.970  0.020  1.090
 8NS  C    H1   single    0.970  0.020  1.090
 8NS  C    H2   single    0.970  0.020  1.090
 8NS  C    H3   single    0.970  0.020  1.090
 8NS  C1   H4   single    0.970  0.020  1.090
 8NS  C1   H5   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
 8NS  H    N1   C12  125.44  3.000
 8NS  H    N1   C13  125.58  3.000
 8NS  C12  N1   C13  108.95  3.000
 8NS  H7   C4   C3   119.90  3.000
 8NS  H7   C4   C5   117.90  3.000
 8NS  C3   C4   C5   122.20  3.000
 8NS  N    C5   C18  124.51  3.000
 8NS  N    C5   C4   115.93  3.000
 8NS  C18  C5   C4   119.56  3.000
 8NS  H10  C7   C9   116.50  3.000
 8NS  H10  C7   C8   116.37  3.000
 8NS  C9   C7   C8    59.98  3.000
 8NS  H10  C7   C6   114.55  3.000
 8NS  C9   C7   C6   119.96  3.000
 8NS  C8   C7   C6   118.82  3.000
 8NS  H11  C8   H12  114.13  3.000
 8NS  H11  C8   C9   118.44  3.000
 8NS  H12  C8   C9   118.02  3.000
 8NS  H11  C8   C7   118.09  3.000
 8NS  H12  C8   C7   117.80  3.000
 8NS  C9   C8   C7    59.98  3.000
 8NS  H15  C10  H16  106.03  3.000
 8NS  H15  C10  N    107.78  3.000
 8NS  H16  C10  N    108.49  3.000
 8NS  H15  C10  C11  111.50  3.000
 8NS  H16  C10  C11  110.10  3.000
 8NS  N    C10  C11  112.67  3.000
 8NS  C14  C13  C20  124.49  3.000
 8NS  C14  C13  N1   127.41  3.000
 8NS  C20  C13  N1   108.06  3.000
 8NS  C16  C17  C18  121.27  3.000
 8NS  C16  C17  C20  115.39  3.000
 8NS  C18  C17  C20  123.32  3.000
 8NS  C11  C20  C17  132.94  3.000
 8NS  C11  C20  C13  107.29  3.000
 8NS  C17  C20  C13  119.76  3.000
 8NS  H6   C3   C2   121.68  3.000
 8NS  H6   C3   C4   120.48  3.000
 8NS  C2   C3   C4   117.84  3.000
 8NS  H22  C19  C2   119.35  3.000
 8NS  H22  C19  C18  119.63  3.000
 8NS  C2   C19  C18  121.01  3.000
 8NS  H17  C12  C11  129.67  3.000
 8NS  H17  C12  N1   120.88  3.000
 8NS  C11  C12  N1   109.45  3.000
 8NS  C19  C18  C17  118.80  3.000
 8NS  C19  C18  C5   117.92  3.000
 8NS  C17  C18  C5   123.28  3.000
 8NS  C12  C11  C20  106.25  3.000
 8NS  C12  C11  C10  129.97  3.000
 8NS  C20  C11  C10  123.54  3.000
 8NS  S    C2   C19  119.43  3.000
 8NS  S    C2   C3   119.13  3.000
 8NS  C19  C2   C3   121.41  3.000
 8NS  H21  C16  N2   114.23  3.000
 8NS  H21  C16  C17  121.86  3.000
 8NS  N2   C16  C17  123.91  3.000
 8NS  O2   C14  N2   121.73  3.000
 8NS  O2   C14  C13  125.91  3.000
 8NS  N2   C14  C13  112.35  3.000
 8NS  H14  C9   H13  114.09  3.000
 8NS  H14  C9   C8   117.93  3.000
 8NS  H13  C9   C8   118.54  3.000
 8NS  H14  C9   C7   117.64  3.000
 8NS  H13  C9   C7   118.30  3.000
 8NS  C8   C9   C7    60.04  3.000
 8NS  H3   C    H2   107.80  3.000
 8NS  H3   C    H1   107.83  3.000
 8NS  H2   C    H1   108.88  3.000
 8NS  H3   C    C1   108.84  3.000
 8NS  H2   C    C1   111.61  3.000
 8NS  H1   C    C1   111.73  3.000
 8NS  H5   C1   H4   108.38  3.000
 8NS  H5   C1   S    106.91  3.000
 8NS  H4   C1   S    106.83  3.000
 8NS  H5   C1   C    111.93  3.000
 8NS  H4   C1   C    112.03  3.000
 8NS  S    C1   C    110.51  3.000
 8NS  C10  N    C6   114.81  3.000
 8NS  C10  N    C5   115.58  3.000
 8NS  C6   N    C5   115.62  3.000
 8NS  C14  N2   C16  124.04  3.000
 8NS  C14  N2   C15  116.60  3.000
 8NS  C16  N2   C15  119.36  3.000
 8NS  O1   S    O    118.38  3.000
 8NS  O1   S    C1   108.18  3.000
 8NS  O    S    C1   108.34  3.000
 8NS  O1   S    C2   108.27  3.000
 8NS  O    S    C2   108.76  3.000
 8NS  C1   S    C2   103.96  3.000
 8NS  H9   C6   H8   106.29  3.000
 8NS  H9   C6   N    112.90  3.000
 8NS  H8   C6   N    106.66  3.000
 8NS  H9   C6   C7   109.04  3.000
 8NS  H8   C6   C7   109.54  3.000
 8NS  N    C6   C7   112.17  3.000
 8NS  H18  C15  H19  108.71  3.000
 8NS  H18  C15  H20  108.67  3.000
 8NS  H19  C15  H20  108.78  3.000
 8NS  H18  C15  N2   109.10  3.000
 8NS  H19  C15  N2   110.72  3.000
 8NS  H20  C15  N2   110.81  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
 8NS  CONST_01  C11  C20  C13  N1      0.00   0.0  0
 8NS  CONST_02  C20  C11  C12  N1      0.00   0.0  0
 8NS  CONST_03  C19  C18  C5   C4      0.00   0.0  0
 8NS  CONST_04  C19  C2   C3   C4      0.00   0.0  0
 8NS  CONST_05  C2   C3   C4   C5      0.00   0.0  0
 8NS  CONST_06  C2   C19  C18  C5      0.00   0.0  0
 8NS  CONST_07  C11  C12  N1   C13     0.00   0.0  0
 8NS  CONST_08  C12  C11  C20  C13     0.00   0.0  0
 8NS  CONST_09  C12  N1   C13  C20     0.00   0.0  0
 8NS  CONST_10  C18  C5   C4   C3      0.00   0.0  0
 8NS  CONST_11  C18  C19  C2   C3      0.00   0.0  0
 8NS  CONST_12  C16  N2   C14  C13     0.00   0.0  0
 8NS  CONST_13  S    C2   C3   C4    180.00   0.0  0
 8NS  CONST_14  S    C2   C19  C18   180.00   0.0  0
 8NS  CONST_15  C15  N2   C14  C13   180.00   0.0  0
 8NS  CONST_16  O2   C14  N2   C16   180.00   0.0  0
 8NS  CONST_17  H6   C3   C4   C5    180.00   0.0  0
 8NS  CONST_18  H22  C19  C18  C5    180.00   0.0  0
 8NS  CONST_19  H17  C12  C11  C10     0.00   0.0  0
 8NS  CONST_20  H    N1   C13  C20   180.00   0.0  0
 8NS  CONST_21  H7   C4   C5   C18   180.00   0.0  0
 8NS  CONST_22  O2   C14  N2   C15     0.00   0.0  0
 8NS  Var_01    C10  N    C5   C4   -117.94  30.0  1
 8NS  Var_02    C20  C17  C18  C5    -29.56  30.0  1
 8NS  Var_03    C11  C10  N    C5    -79.33  30.0  1
 8NS  Var_04    N    C10  C11  C20    35.33  30.0  1
 8NS  Var_05    C7   C6   N    C5    -57.41  30.0  1
 8NS  Var_06    C9   C8   C7   C6   -109.90  30.0  1
 8NS  Var_07    N    C6   C7   C8    159.31  30.0  2
 8NS  Var_08    H13  C9   C8   C7   -108.02  30.0  1
 8NS  Var_09    C1   S    C2   C3     82.29  30.0  2
 8NS  Var_10    H20  C15  N2   C16   117.56  30.0  3
 8NS  Var_11    C    C1   S    C2   -177.54  30.0  2
 8NS  Var_12    H1   C    C1   S     -61.05  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
 8NS  chir_01  C7  C6  C8  C9  both

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
 8NS  plan-1  N1   0.020
 8NS  plan-1  C10  0.020
 8NS  plan-1  C13  0.020
 8NS  plan-1  C17  0.020
 8NS  plan-1  C20  0.020
 8NS  plan-1  C12  0.020
 8NS  plan-1  C18  0.020
 8NS  plan-1  C11  0.020
 8NS  plan-1  C16  0.020
 8NS  plan-1  C14  0.020
 8NS  plan-1  N2   0.020
 8NS  plan-1  O2   0.020
 8NS  plan-1  H    0.020
 8NS  plan-1  H17  0.020
 8NS  plan-1  H21  0.020
 8NS  plan-1  C15  0.020
 8NS  plan-2  C4   0.020
 8NS  plan-2  C5   0.020
 8NS  plan-2  C17  0.020
 8NS  plan-2  C3   0.020
 8NS  plan-2  C19  0.020
 8NS  plan-2  C18  0.020
 8NS  plan-2  C2   0.020
 8NS  plan-2  N    0.020
 8NS  plan-2  S    0.020
 8NS  plan-2  H7   0.020
 8NS  plan-2  H6   0.020
 8NS  plan-2  H22  0.020

