# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 25 16:34:54 2020
#   Inital geometry file: a 127 line input string
#   Ligand name: 1-(2-cyclopropylethyl)-3-(1,1-dioxido-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxyquinolin-2(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC1=C(C(=O)N(CCC2CC2)c3ccc(F)cc13)C4=Nc5ccccc5[S](=O)(=O)N4
#
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
 NN2  NN2  1-(2-cyclopropylethyl)-3-(1,1-dioxido-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxyquinolin-2(1H)-one  ligand  48  30  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_NN2
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
 NN2  C4    C  CR66  0  -0.253   4.3229  -0.3365  -0.1471
 NN2  C5    C  CR66  0   0.317   3.3943  -1.0963   0.5773
 NN2  C6    C  CR16  0  -0.312   3.8702  -2.2357   1.2306
 NN2  C7    C  CR16  0  -0.228   5.2006  -2.5979   1.1363
 NN2  C8    C  CR16  0  -0.258   6.0980  -1.8357   0.3911
 NN2  C9    C  CR16  0  -0.247   5.6607  -0.6936  -0.2540
 NN2  N3    N  N     0  -0.405   2.0435  -0.8110   0.6570
 NN2  C15   C  CR6   0   0.543  -3.7961   2.9591   0.7777
 NN2  C20   C  CR16  0  -0.461  -2.4359   2.8276   0.7163
 NN2  C19   C  CR66  0  -0.047  -1.8867   1.6128   0.2856
 NN2  C22   C  CR6   0   0.499  -0.4619   1.4264   0.2223
 NN2  O23   O  OH1   0  -0.576   0.2585   2.4786   0.5841
 NN2  C16   C  CR16  0  -0.401  -4.6424   1.9151   0.4341
 NN2  C17   C  CR16  0  -0.304  -4.1068   0.7185   0.0120
 NN2  C18   C  CR66  0   0.389  -2.7182   0.5403  -0.0819
 NN2  N14   N  NR6   0  -0.627  -2.1717  -0.6491  -0.5233
 NN2  C24   C  CH2   0  -0.343  -3.0400  -1.7442  -0.9502
 NN2  C25   C  CH2   0  -0.456  -3.4972  -2.6274   0.2051
 NN2  C26   C  CH1   0  -0.241  -4.4171  -3.7134  -0.2871
 NN2  C30   C  CH2   0  -0.491  -5.4503  -4.2989   0.6226
 NN2  C29   C  CH2   0  -0.490  -5.8680  -3.4101  -0.5114
 NN2  C27   C  CR6   0   0.561  -0.8118  -0.8815  -0.5458
 NN2  O28   O  OC    0  -0.475  -0.3569  -1.9587  -0.9042
 NN2  C1    C  CR6   0  -0.360   0.0436   0.2215  -0.1592
 NN2  C2    C  CR6   0   0.385   1.4969  -0.0176  -0.1804
 NN2  N11   N  NR16  0  -0.781   2.1946   0.6808  -1.1463
 NN2  S10   S  S     0   1.397   3.7624   1.1626  -0.8352
 NN2  O13   O  OS    0  -0.629   3.7178   2.1839   0.1995
 NN2  O12   O  OS    0  -0.621   4.4122   1.4722  -2.0904
 NN2  H6    H  HCR6  0   0.278   3.1716  -2.8334   1.8009
 NN2  H7    H  HCR6  0   0.278   5.5466  -3.4885   1.6433
 NN2  H8    H  HCR6  0   0.279   7.1359  -2.1292   0.3193
 NN2  H9    H  HCR6  0   0.292   6.3506  -0.0905  -0.8294
 NN2  H20   H  HCR6  0   0.294  -1.7993   3.6545   0.9987
 NN2  HO23  H  HOH1  0   0.481   1.2132   2.3314   0.5619
 NN2  H16   H  HCR6  0   0.296  -5.7156   2.0343   0.5002
 NN2  H17   H  HCR6  0   0.292  -4.7922  -0.0764  -0.2378
 NN2  H241  H  HCH2  0   0.271  -3.8921  -1.3305  -1.4877
 NN2  H242  H  HCH2  0   0.281  -2.4904  -2.3405  -1.6742
 NN2  H251  H  HCH2  0   0.249  -2.6215  -3.0654   0.6906
 NN2  H252  H  HCH2  0   0.234  -4.0063  -2.0265   0.9659
 NN2  H26   H  HCH1  0   0.254  -3.9615  -4.4012  -0.9935
 NN2  H301  H  HCH2  0   0.249  -5.6598  -5.3580   0.5452
 NN2  H302  H  HCH2  0   0.244  -5.5216  -3.9060   1.6296
 NN2  H291  H  HCH2  0   0.244  -6.2197  -2.4133  -0.2689
 NN2  H292  H  HCH2  0   0.250  -6.3660  -3.8593  -1.3610
 NN2  HN11  H  HNR6  0   0.460   1.6983   1.1604  -1.8913
 NN2  F21   F  F     0  -0.312  -4.3295   4.1202   1.1846

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
 NN2  C4   C5    aromatic  1.402  0.020  1.402
 NN2  C4   C9    aromatic  1.389  0.020  1.389
 NN2  C4   S10   single    1.742  0.020  1.742
 NN2  C5   C6    aromatic  1.397  0.020  1.397
 NN2  C5   N3    single    1.383  0.020  1.383
 NN2  C6   C7    aromatic  1.382  0.020  1.382
 NN2  C6   H6    single    0.930  0.020  1.080
 NN2  C7   C8    aromatic  1.393  0.020  1.393
 NN2  C7   H7    single    0.930  0.020  1.080
 NN2  C8   C9    aromatic  1.383  0.020  1.383
 NN2  C8   H8    single    0.930  0.020  1.080
 NN2  C9   H9    single    0.930  0.020  1.080
 NN2  N3   C2    double    1.277  0.020  1.277
 NN2  F21  C15   single    1.341  0.020  1.341
 NN2  C15  C20   aromatic  1.368  0.020  1.368
 NN2  C15  C16   aromatic  1.387  0.020  1.387
 NN2  C20  C19   aromatic  1.401  0.020  1.401
 NN2  C20  H20   single    0.930  0.020  1.080
 NN2  C19  C22   aromatic  1.438  0.020  1.438
 NN2  C19  C18   aromatic  1.406  0.020  1.406
 NN2  C22  O23   single    1.326  0.020  1.326
 NN2  C22  C1    aromatic  1.361  0.020  1.361
 NN2  O23  HO23  single    0.850  0.020  0.980
 NN2  C16  C17   aromatic  1.377  0.020  1.377
 NN2  C16  H16   single    0.930  0.020  1.080
 NN2  C17  C18   aromatic  1.403  0.020  1.403
 NN2  C17  H17   single    0.930  0.020  1.080
 NN2  C18  N14   aromatic  1.381  0.020  1.381
 NN2  N14  C24   single    1.461  0.020  1.461
 NN2  N14  C27   aromatic  1.380  0.020  1.380
 NN2  C24  C25   single    1.524  0.020  1.524
 NN2  C24  H241  single    0.970  0.020  1.090
 NN2  C24  H242  single    0.970  0.020  1.090
 NN2  C25  C26   single    1.506  0.020  1.506
 NN2  C25  H251  single    0.970  0.020  1.090
 NN2  C25  H252  single    0.970  0.020  1.090
 NN2  C26  C30   single    1.496  0.020  1.496
 NN2  C26  C29   single    1.499  0.020  1.499
 NN2  C26  H26   single    0.970  0.020  1.090
 NN2  C30  C29   single    1.500  0.020  1.500
 NN2  C30  H301  single    0.970  0.020  1.090
 NN2  C30  H302  single    0.970  0.020  1.090
 NN2  C29  H291  single    0.970  0.020  1.090
 NN2  C29  H292  single    0.970  0.020  1.090
 NN2  C27  O28   double    1.223  0.020  1.223
 NN2  C27  C1    aromatic  1.448  0.020  1.448
 NN2  C1   C2    single    1.473  0.020  1.473
 NN2  C2   N11   single    1.381  0.020  1.381
 NN2  N11  S10   single    1.669  0.020  1.669
 NN2  N11  HN11  single    0.890  0.020  1.040
 NN2  S10  O13   double    1.455  0.020  1.455
 NN2  S10  O12   double    1.447  0.020  1.447

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
 NN2  S10   C4   C9    120.05  3.000
 NN2  S10   C4   C5    117.22  3.000
 NN2  C9    C4   C5    122.59  3.000
 NN2  N3    C5   C6    118.30  3.000
 NN2  N3    C5   C4    124.41  3.000
 NN2  C6    C5   C4    117.27  3.000
 NN2  H6    C6   C7    120.85  3.000
 NN2  H6    C6   C5    118.50  3.000
 NN2  C7    C6   C5    120.65  3.000
 NN2  H7    C7   C8    119.68  3.000
 NN2  H7    C7   C6    119.45  3.000
 NN2  C8    C7   C6    120.87  3.000
 NN2  H8    C8   C9    119.80  3.000
 NN2  H8    C8   C7    120.35  3.000
 NN2  C9    C8   C7    119.85  3.000
 NN2  H9    C9   C8    120.46  3.000
 NN2  H9    C9   C4    120.79  3.000
 NN2  C8    C9   C4    118.76  3.000
 NN2  C2    N3   C5    120.58  3.000
 NN2  C16   C15  C20   121.55  3.000
 NN2  C16   C15  F21   118.96  3.000
 NN2  C20   C15  F21   119.50  3.000
 NN2  H20   C20  C19   120.85  3.000
 NN2  H20   C20  C15   120.01  3.000
 NN2  C19   C20  C15   119.14  3.000
 NN2  C18   C19  C22   118.39  3.000
 NN2  C18   C19  C20   120.66  3.000
 NN2  C22   C19  C20   120.95  3.000
 NN2  C1    C22  O23   125.26  3.000
 NN2  C1    C22  C19   119.67  3.000
 NN2  O23   C22  C19   115.05  3.000
 NN2  HO23  O23  C22   114.20  3.000
 NN2  H16   C16  C17   120.01  3.000
 NN2  H16   C16  C15   120.48  3.000
 NN2  C17   C16  C15   119.51  3.000
 NN2  H17   C17  C18   121.31  3.000
 NN2  H17   C17  C16   117.65  3.000
 NN2  C18   C17  C16   121.04  3.000
 NN2  N14   C18  C17   121.48  3.000
 NN2  N14   C18  C19   120.42  3.000
 NN2  C17   C18  C19   118.09  3.000
 NN2  C27   N14  C24   117.04  3.000
 NN2  C27   N14  C18   122.69  3.000
 NN2  C24   N14  C18   120.23  3.000
 NN2  H242  C24  H241  105.98  3.000
 NN2  H242  C24  C25   109.79  3.000
 NN2  H241  C24  C25   111.06  3.000
 NN2  H242  C24  N14   107.77  3.000
 NN2  H241  C24  N14   108.93  3.000
 NN2  C25   C24  N14   113.02  3.000
 NN2  H252  C25  H251  106.49  3.000
 NN2  H252  C25  C26   109.81  3.000
 NN2  H251  C25  C26   110.22  3.000
 NN2  H252  C25  C24   110.37  3.000
 NN2  H251  C25  C24   109.18  3.000
 NN2  C26   C25  C24   110.69  3.000
 NN2  H26   C26  C29   115.90  3.000
 NN2  H26   C26  C30   115.94  3.000
 NN2  C29   C26  C30    60.11  3.000
 NN2  H26   C26  C25   114.40  3.000
 NN2  C29   C26  C25   119.62  3.000
 NN2  C30   C26  C25   120.35  3.000
 NN2  H302  C30  H301  114.11  3.000
 NN2  H302  C30  C29   118.00  3.000
 NN2  H301  C30  C29   118.16  3.000
 NN2  H302  C30  C26   117.96  3.000
 NN2  H301  C30  C26   118.24  3.000
 NN2  C29   C30  C26    60.05  3.000
 NN2  H292  C29  H291  114.06  3.000
 NN2  H292  C29  C30   118.39  3.000
 NN2  H291  C29  C30   117.76  3.000
 NN2  H292  C29  C26   118.61  3.000
 NN2  H291  C29  C26   117.80  3.000
 NN2  C30   C29  C26    59.84  3.000
 NN2  C1    C27  O28   121.96  3.000
 NN2  C1    C27  N14   116.71  3.000
 NN2  O28   C27  N14   121.31  3.000
 NN2  C2    C1   C27   117.08  3.000
 NN2  C2    C1   C22   120.94  3.000
 NN2  C27   C1   C22   121.98  3.000
 NN2  N11   C2   C1    115.24  3.000
 NN2  N11   C2   N3    123.84  3.000
 NN2  C1    C2   N3    120.92  3.000
 NN2  HN11  N11  S10   117.35  3.000
 NN2  HN11  N11  C2    120.33  3.000
 NN2  S10   N11  C2    119.34  3.000
 NN2  O12   S10  O13   118.72  3.000
 NN2  O12   S10  N11   108.78  3.000
 NN2  O13   S10  N11   107.84  3.000
 NN2  O12   S10  C4    112.47  3.000
 NN2  O13   S10  C4    109.46  3.000
 NN2  N11   S10  C4     97.32  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
 NN2  CONST_01  C7    C6   C5   C4      0.00   0.0  0
 NN2  CONST_02  C7    C8   C9   C4      0.00   0.0  0
 NN2  CONST_03  C8    C9   C4   C5      0.00   0.0  0
 NN2  CONST_04  C8    C7   C6   C5      0.00   0.0  0
 NN2  CONST_05  C9    C4   C5   C6      0.00   0.0  0
 NN2  CONST_06  C9    C8   C7   C6      0.00   0.0  0
 NN2  CONST_07  C22   C19  C20  C15   180.00   0.0  0
 NN2  CONST_08  C18   C19  C20  C15     0.00   0.0  0
 NN2  CONST_09  C18   C17  C16  C15     0.00   0.0  0
 NN2  CONST_10  C17   C16  C15  C20     0.00   0.0  0
 NN2  CONST_11  C1    C22  C19  C20   180.00   0.0  0
 NN2  CONST_12  C17   C18  C19  C20     0.00   0.0  0
 NN2  CONST_13  N14   C18  C19  C20   180.00   0.0  0
 NN2  CONST_14  C16   C15  C20  C19     0.00   0.0  0
 NN2  CONST_15  C27   C1   C22  C19     0.00   0.0  0
 NN2  CONST_16  C16   C17  C18  C19     0.00   0.0  0
 NN2  CONST_17  C27   N14  C18  C19     0.00   0.0  0
 NN2  CONST_18  C17   C18  C19  C22   180.00   0.0  0
 NN2  CONST_19  N14   C18  C19  C22     0.00   0.0  0
 NN2  CONST_20  N14   C27  C1   C22     0.00   0.0  0
 NN2  CONST_21  N14   C18  C17  C16   180.00   0.0  0
 NN2  CONST_22  C27   N14  C18  C17   180.00   0.0  0
 NN2  CONST_23  C1    C22  C19  C18     0.00   0.0  0
 NN2  CONST_24  C1    C27  N14  C18     0.00   0.0  0
 NN2  CONST_25  C2    C1   C22  C19   180.00   0.0  0
 NN2  CONST_26  C2    C1   C27  N14   180.00   0.0  0
 NN2  CONST_27  C1    C2   N3   C5    180.00   0.0  0
 NN2  CONST_28  N11   C2   N3   C5      0.00   0.0  0
 NN2  CONST_31  C19   C20  C15  F21   180.00   0.0  0
 NN2  CONST_32  C17   C16  C15  F21   180.00   0.0  0
 NN2  CONST_33  O23   C22  C19  C20     0.00   0.0  0
 NN2  CONST_34  C24   N14  C18  C19   180.00   0.0  0
 NN2  CONST_35  O28   C27  C1   C22   180.00   0.0  0
 NN2  CONST_36  C18   C19  C22  O23   180.00   0.0  0
 NN2  CONST_37  C27   C1   C22  O23   180.00   0.0  0
 NN2  CONST_38  C2    C1   C22  O23     0.00   0.0  0
 NN2  CONST_39  C24   N14  C18  C17     0.00   0.0  0
 NN2  CONST_40  O28   C27  N14  C18   180.00   0.0  0
 NN2  CONST_41  C1    C27  N14  C24   180.00   0.0  0
 NN2  CONST_42  C2    C1   C27  O28     0.00   0.0  0
 NN2  CONST_43  H6    C6   C5   C4    180.00   0.0  0
 NN2  CONST_44  H8    C8   C9   C4    180.00   0.0  0
 NN2  CONST_45  H9    C9   C4   C5    180.00   0.0  0
 NN2  CONST_46  H7    C7   C6   C5    180.00   0.0  0
 NN2  CONST_47  H17   C17  C16  C15   180.00   0.0  0
 NN2  CONST_48  H16   C16  C15  C20   180.00   0.0  0
 NN2  CONST_49  H20   C20  C19  C22     0.00   0.0  0
 NN2  CONST_50  HN11  N11  C2   N3    180.00   0.0  0
 NN2  CONST_51  O28   C27  N14  C24     0.00   0.0  0
 NN2  Var_01    C22   C1   C2   N3    110.79  30.0  3
 NN2  Var_02    O13   S10  C4   C5     79.02  30.0  1
 NN2  Var_03    C29   C30  C26  C25   108.90  30.0  1
 NN2  Var_04    H291  C29  C30  C26  -107.68  30.0  1
 NN2  Var_05    C25   C24  N14  C18   -85.75  30.0  2
 NN2  Var_06    C26   C25  C24  N14   178.45  30.0  3
 NN2  Var_07    C30   C26  C25  C24  -152.53  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
 NN2  chir_01  C26  C25  C30  C29  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
 NN2  plan-1  C15   0.020
 NN2  plan-1  C20   0.020
 NN2  plan-1  C19   0.020
 NN2  plan-1  C22   0.020
 NN2  plan-1  O23   0.020
 NN2  plan-1  C16   0.020
 NN2  plan-1  C17   0.020
 NN2  plan-1  C18   0.020
 NN2  plan-1  N14   0.020
 NN2  plan-1  C24   0.020
 NN2  plan-1  C27   0.020
 NN2  plan-1  O28   0.020
 NN2  plan-1  C1    0.020
 NN2  plan-1  C2    0.020
 NN2  plan-1  H20   0.020
 NN2  plan-1  H16   0.020
 NN2  plan-1  H17   0.020
 NN2  plan-1  F21   0.020
 NN2  plan-2  C4    0.020
 NN2  plan-2  C5    0.020
 NN2  plan-2  C6    0.020
 NN2  plan-2  C7    0.020
 NN2  plan-2  C8    0.020
 NN2  plan-2  C9    0.020
 NN2  plan-2  N3    0.020
 NN2  plan-2  C1    0.020
 NN2  plan-2  C2    0.020
 NN2  plan-2  N11   0.020
 NN2  plan-2  S10   0.020
 NN2  plan-2  H6    0.020
 NN2  plan-2  H7    0.020
 NN2  plan-2  H8    0.020
 NN2  plan-2  H9    0.020
 NN2  plan-2  HN11  0.020

