# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 09:22:33 2020
#   Inital geometry file: a 148 line input string
#   Ligand name: (3S)-N-tert-butyl-3-[(2-chloro-5-ethyl-8-fluoro-5H-dibenzo[b,e][1,4]diazepin-11-yl)amino]pyrrolidine-1-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN1c2ccc(F)cc2N=C(N[C@H]3CCN(C3)C(=O)NC(C)(C)C)c4cc(Cl)ccc14
#
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
 4OR  4OR  (3S)-N-tert-butyl-3-[(2-chloro-5-ethyl-8-fluoro-5H-dibenzo[b,e][1,4]diazepin-11-yl)amino]pyrrolidine-1-carboxamide  ligand  61  32  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_4OR
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
 4OR  C1   C   CH2   0  -0.315   4.2988   0.8536  -2.2635
 4OR  C2   C   CR6   0   0.239   3.2711   1.7114  -0.1598
 4OR  C3   C   CR16  0  -0.280   4.1596   2.6991   0.2558
 4OR  C11  C   CH2   0  -0.297  -3.4652  -0.9022  -1.8092
 4OR  C12  C   CH2   0  -0.226  -2.0793  -0.3042   0.0850
 4OR  C13  C   C     0   0.752  -4.4994  -0.0455   0.3098
 4OR  C14  C   CT    0   0.109  -6.9944   0.2295   0.2826
 4OR  C15  C   CH3   0  -0.642  -7.0432   1.6766   0.7803
 4OR  C16  C   CH3   0  -0.642  -7.3185  -0.7413   1.4186
 4OR  C17  C   CH3   0  -0.681  -8.0304   0.0553  -0.8284
 4OR  C18  C   CR6   0  -0.052   2.3306  -1.1261  -0.0626
 4OR  C19  C   CR16  0  -0.274   2.2028  -2.3714   0.5510
 4OR  C20  C   CR6   0  -0.037   3.3255  -3.1499   0.7595
 4OR  C21  C   CR16  0  -0.214   4.5799  -2.7137   0.3573
 4OR  C22  C   CR16  0  -0.289   4.7068  -1.4610  -0.2150
 4OR  C23  C   CR6   0   0.327   3.5937  -0.6445  -0.4178
 4OR  CL   CL  CL    0  -0.125   3.1618  -4.6948   1.5257
 4OR  N    N   NT    0  -0.610   3.7317   0.6392  -0.9450
 4OR  C    C   CH3   0  -0.648   3.2420   0.8551  -3.3592
 4OR  C8   C   C     0   0.482   1.1134  -0.3377  -0.3882
 4OR  N1   N   N     0  -0.507   0.9411   0.9246  -0.2161
 4OR  C7   C   CR6   0   0.246   1.9182   1.7913   0.2179
 4OR  C6   C   CR16  0  -0.492   1.5065   2.8710   1.0092
 4OR  C5   C   CR6   0   0.527   2.4165   3.8301   1.3919
 4OR  F    F   F     0  -0.322   1.9904   4.8598   2.1462
 4OR  C4   C   CR16  0  -0.435   3.7475   3.7777   1.0230
 4OR  N2   N   NH1   0  -0.661   0.0898  -1.0713  -0.8684
 4OR  C9   C   CH1   0  -0.084  -1.2063  -0.5184  -1.1560
 4OR  N3   N   NT    0  -0.520  -3.4222  -0.3597  -0.4583
 4OR  C10  C   CH2   0  -0.499  -2.0565  -1.4406  -2.0209
 4OR  O    O   O     0  -0.555  -4.3656   0.2448   1.4976
 4OR  N4   N   NH1   0  -0.710  -5.6997  -0.0914  -0.3241
 4OR  H1   H   HCH2  0   0.239   4.8460   1.7981  -2.2668
 4OR  H2   H   HCH2  0   0.240   5.0388   0.0754  -2.4583
 4OR  H3   H   HCR6  0   0.266   5.2009   2.6214  -0.0310
 4OR  H4   H   HCH2  0   0.253  -4.2154  -1.6900  -1.9039
 4OR  H5   H   HCH2  0   0.243  -3.6993  -0.1260  -2.5459
 4OR  H6   H   HCH2  0   0.222  -1.8970  -1.1008   0.8150
 4OR  H7   H   HCH2  0   0.246  -1.8708   0.6507   0.5660
 4OR  H8   H   HCH3  0   0.237  -6.3329   1.8499   1.5861
 4OR  H9   H   HCH3  0   0.222  -6.8178   2.3714  -0.0312
 4OR  H10  H   HCH3  0   0.220  -8.0422   1.9113   1.1520
 4OR  H11  H   HCH3  0   0.221  -8.3091  -0.5257   1.8222
 4OR  H12  H   HCH3  0   0.222  -7.3207  -1.7707   1.0560
 4OR  H13  H   HCH3  0   0.238  -6.6010  -0.6654   2.2328
 4OR  H14  H   HCH3  0   0.234  -7.8416   0.7418  -1.6571
 4OR  H15  H   HCH3  0   0.236  -8.0271  -0.9637  -1.2205
 4OR  H16  H   HCH3  0   0.240  -9.0294   0.2642  -0.4465
 4OR  H17  H   HCR6  0   0.287   1.2310  -2.7324   0.8623
 4OR  H18  H   HCR6  0   0.285   5.4541  -3.3309   0.5143
 4OR  H19  H   HCR6  0   0.277   5.6882  -1.1022  -0.4973
 4OR  H20  H   HCH3  0   0.225   2.5139   1.6508  -3.1981
 4OR  H21  H   HCH3  0   0.227   3.7000   1.0078  -4.3376
 4OR  H22  H   HCH3  0   0.222   2.7056  -0.0947  -3.3831
 4OR  H23  H   HCR6  0   0.269   0.4652   2.9526   1.2939
 4OR  H24  H   HCR6  0   0.273   4.4449   4.5439   1.3335
 4OR  H25  H   HNH1  0   0.408   0.2461  -2.0437  -1.0752
 4OR  H26  H   HCH1  0   0.261  -1.0758   0.4409  -1.6638
 4OR  H27  H   HCH2  0   0.249  -1.9869  -2.4683  -1.6532
 4OR  H28  H   HCH2  0   0.268  -1.7621  -1.4353  -3.0694
 4OR  H29  H   HNH1  0   0.405  -5.6983  -0.1514  -1.3291

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
 4OR  C16  C14  single    1.529  0.020  1.529
 4OR  C11  C10  single    1.523  0.020  1.523
 4OR  C11  N3   single    1.456  0.020  1.456
 4OR  C10  C9   single    1.524  0.020  1.524
 4OR  N4   C14  single    1.465  0.020  1.465
 4OR  N4   C13  single    1.358  0.020  1.358
 4OR  C17  C14  single    1.529  0.020  1.529
 4OR  C14  C15  single    1.531  0.020  1.531
 4OR  N3   C13  single    1.360  0.020  1.360
 4OR  N3   C12  single    1.450  0.020  1.450
 4OR  C9   C12  single    1.532  0.020  1.532
 4OR  C9   N2   single    1.438  0.020  1.438
 4OR  C13  O    double    1.230  0.020  1.230
 4OR  N2   C8   single    1.348  0.020  1.348
 4OR  CL   C20  single    1.732  0.020  1.732
 4OR  C19  C20  aromatic  1.382  0.020  1.382
 4OR  C19  C18  aromatic  1.394  0.020  1.394
 4OR  C8   N1   double    1.286  0.020  1.286
 4OR  C8   C18  single    1.486  0.020  1.486
 4OR  C20  C21  aromatic  1.388  0.020  1.388
 4OR  N1   C7   single    1.376  0.020  1.376
 4OR  C18  C23  aromatic  1.398  0.020  1.398
 4OR  C21  C22  aromatic  1.383  0.020  1.383
 4OR  C7   C6   aromatic  1.401  0.020  1.401
 4OR  C7   C2   aromatic  1.407  0.020  1.407
 4OR  C23  C22  aromatic  1.395  0.020  1.395
 4OR  C23  N    single    1.395  0.020  1.395
 4OR  C6   C5   aromatic  1.376  0.020  1.376
 4OR  N    C2   single    1.407  0.020  1.407
 4OR  N    C1   single    1.451  0.020  1.451
 4OR  C2   C3   aromatic  1.392  0.020  1.392
 4OR  C5   F    single    1.346  0.020  1.346
 4OR  C5   C4   aromatic  1.382  0.020  1.382
 4OR  C1   C    single    1.522  0.020  1.522
 4OR  C3   C4   aromatic  1.386  0.020  1.386
 4OR  C1   H1   single    0.970  0.020  1.090
 4OR  C1   H2   single    0.970  0.020  1.090
 4OR  C3   H3   single    0.930  0.020  1.080
 4OR  C11  H4   single    0.970  0.020  1.090
 4OR  C11  H5   single    0.970  0.020  1.090
 4OR  C12  H6   single    0.970  0.020  1.090
 4OR  C12  H7   single    0.970  0.020  1.090
 4OR  C15  H8   single    0.970  0.020  1.090
 4OR  C15  H9   single    0.970  0.020  1.090
 4OR  C15  H10  single    0.970  0.020  1.090
 4OR  C16  H11  single    0.970  0.020  1.090
 4OR  C16  H12  single    0.970  0.020  1.090
 4OR  C16  H13  single    0.970  0.020  1.090
 4OR  C17  H14  single    0.970  0.020  1.090
 4OR  C17  H15  single    0.970  0.020  1.090
 4OR  C17  H16  single    0.970  0.020  1.090
 4OR  C19  H17  single    0.930  0.020  1.080
 4OR  C21  H18  single    0.930  0.020  1.080
 4OR  C22  H19  single    0.930  0.020  1.080
 4OR  C    H20  single    0.970  0.020  1.090
 4OR  C    H21  single    0.970  0.020  1.090
 4OR  C    H22  single    0.970  0.020  1.090
 4OR  C6   H23  single    0.930  0.020  1.080
 4OR  C4   H24  single    0.930  0.020  1.080
 4OR  N2   H25  single    0.860  0.020  1.020
 4OR  C9   H26  single    0.970  0.020  1.090
 4OR  C10  H27  single    0.970  0.020  1.090
 4OR  C10  H28  single    0.970  0.020  1.090
 4OR  N4   H29  single    0.860  0.020  1.020

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
 4OR  H2   C1   H1   106.06  3.000
 4OR  H2   C1   C    110.06  3.000
 4OR  H1   C1   C    110.18  3.000
 4OR  H2   C1   N    108.77  3.000
 4OR  H1   C1   N    109.05  3.000
 4OR  C    C1   N    112.51  3.000
 4OR  C7   C2   N    120.53  3.000
 4OR  N    C2   C3   119.90  3.000
 4OR  C7   C2   C3   119.56  3.000
 4OR  H3   C3   C4   119.22  3.000
 4OR  H3   C3   C2   118.93  3.000
 4OR  C4   C3   C2   121.84  3.000
 4OR  H5   C11  H4   107.82  3.000
 4OR  H5   C11  C10  110.77  3.000
 4OR  H4   C11  C10  111.62  3.000
 4OR  H5   C11  N3   111.48  3.000
 4OR  H4   C11  N3   111.69  3.000
 4OR  C10  C11  N3   103.49  3.000
 4OR  H7   C12  H6   108.13  3.000
 4OR  H7   C12  N3   112.10  3.000
 4OR  H6   C12  N3   112.08  3.000
 4OR  H7   C12  C9   111.78  3.000
 4OR  H6   C12  C9   110.07  3.000
 4OR  N3   C12  C9   102.64  3.000
 4OR  N4   C13  O    123.70  3.000
 4OR  O    C13  N3   120.91  3.000
 4OR  N4   C13  N3   115.38  3.000
 4OR  N4   C14  C17  105.83  3.000
 4OR  C17  C14  C16  108.89  3.000
 4OR  N4   C14  C16  110.84  3.000
 4OR  C17  C14  C15  108.80  3.000
 4OR  N4   C14  C15  111.70  3.000
 4OR  C16  C14  C15  110.60  3.000
 4OR  H10  C15  H9   107.77  3.000
 4OR  H10  C15  H8   108.12  3.000
 4OR  H9   C15  H8   108.32  3.000
 4OR  H10  C15  C14  110.07  3.000
 4OR  H9   C15  C14  110.69  3.000
 4OR  H8   C15  C14  111.75  3.000
 4OR  H13  C16  H12  108.41  3.000
 4OR  H13  C16  H11  107.95  3.000
 4OR  H12  C16  H11  107.90  3.000
 4OR  H13  C16  C14  111.83  3.000
 4OR  H12  C16  C14  110.64  3.000
 4OR  H11  C16  C14  109.98  3.000
 4OR  H16  C17  H15  107.91  3.000
 4OR  H16  C17  H14  107.68  3.000
 4OR  H15  C17  H14  108.27  3.000
 4OR  H16  C17  C14  110.17  3.000
 4OR  H15  C17  C14  111.42  3.000
 4OR  H14  C17  C14  111.25  3.000
 4OR  C8   C18  C23  120.11  3.000
 4OR  C23  C18  C19  120.16  3.000
 4OR  C8   C18  C19  119.68  3.000
 4OR  H17  C19  C20  119.87  3.000
 4OR  H17  C19  C18  120.45  3.000
 4OR  C20  C19  C18  119.68  3.000
 4OR  CL   C20  C21  119.60  3.000
 4OR  C21  C20  C19  120.90  3.000
 4OR  CL   C20  C19  119.50  3.000
 4OR  H18  C21  C22  120.19  3.000
 4OR  H18  C21  C20  120.61  3.000
 4OR  C22  C21  C20  119.18  3.000
 4OR  H19  C22  C23  119.44  3.000
 4OR  H19  C22  C21  119.43  3.000
 4OR  C23  C22  C21  121.13  3.000
 4OR  N    C23  C22  120.97  3.000
 4OR  N    C23  C18  120.18  3.000
 4OR  C22  C23  C18  118.84  3.000
 4OR  C23  N    C2   117.27  3.000
 4OR  C2   N    C1   121.50  3.000
 4OR  C23  N    C1   121.21  3.000
 4OR  H22  C    H21  107.97  3.000
 4OR  H22  C    H20  108.07  3.000
 4OR  H21  C    H20  108.10  3.000
 4OR  H22  C    C1   110.86  3.000
 4OR  H21  C    C1   110.74  3.000
 4OR  H20  C    C1   110.97  3.000
 4OR  N2   C8   N1   118.71  3.000
 4OR  N1   C8   C18  126.96  3.000
 4OR  N2   C8   C18  114.29  3.000
 4OR  C7   N1   C8   124.43  3.000
 4OR  C6   C7   N1   117.06  3.000
 4OR  C6   C7   C2   118.56  3.000
 4OR  N1   C7   C2   124.22  3.000
 4OR  H23  C6   C5   120.68  3.000
 4OR  H23  C6   C7   119.31  3.000
 4OR  C5   C6   C7   120.00  3.000
 4OR  C4   C5   F    118.92  3.000
 4OR  C4   C5   C6   122.41  3.000
 4OR  F    C5   C6   118.67  3.000
 4OR  H24  C4   C5   121.16  3.000
 4OR  H24  C4   C3   121.23  3.000
 4OR  C5   C4   C3   117.61  3.000
 4OR  H25  N2   C9   118.06  3.000
 4OR  H25  N2   C8   118.76  3.000
 4OR  C9   N2   C8   123.12  3.000
 4OR  H26  C9   C10  109.51  3.000
 4OR  H26  C9   N2   108.83  3.000
 4OR  C10  C9   N2   112.56  3.000
 4OR  H26  C9   C12  108.76  3.000
 4OR  N2   C9   C12  113.90  3.000
 4OR  C10  C9   C12  103.09  3.000
 4OR  C13  N3   C12  120.88  3.000
 4OR  C12  N3   C11  112.91  3.000
 4OR  C13  N3   C11  125.92  3.000
 4OR  H28  C10  H27  108.12  3.000
 4OR  H28  C10  C9   113.13  3.000
 4OR  H27  C10  C9   110.02  3.000
 4OR  H28  C10  C11  112.47  3.000
 4OR  H27  C10  C11  110.14  3.000
 4OR  C9   C10  C11  102.90  3.000
 4OR  H29  N4   C14  115.32  3.000
 4OR  H29  N4   C13  117.82  3.000
 4OR  C14  N4   C13  125.46  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
 4OR  CONST_01  C5   C4   C3   C2     0.00   0.0  0
 4OR  CONST_02  C6   C5   C4   C3     0.00   0.0  0
 4OR  CONST_03  C21  C20  C19  C18    0.00   0.0  0
 4OR  CONST_04  C22  C21  C20  C19    0.00   0.0  0
 4OR  CONST_05  C23  C22  C21  C20    0.00   0.0  0
 4OR  CONST_06  C4   C5   C6   C7     0.00   0.0  0
 4OR  CONST_07  F    C5   C4   C3   180.00   0.0  0
 4OR  CONST_08  CL   C20  C19  C18  180.00   0.0  0
 4OR  CONST_09  CL   C20  C21  C22  180.00   0.0  0
 4OR  CONST_10  F    C5   C6   C7   180.00   0.0  0
 4OR  CONST_11  H24  C4   C3   C2   180.00   0.0  0
 4OR  CONST_12  H18  C21  C20  C19  180.00   0.0  0
 4OR  CONST_13  H19  C22  C21  C20  180.00   0.0  0
 4OR  CONST_14  H17  C19  C20  C21  180.00   0.0  0
 4OR  CONST_15  H3   C3   C4   C5   180.00   0.0  0
 4OR  CONST_16  H23  C6   C5   C4   180.00   0.0  0
 4OR  CONST_17  O    C13  N3   C11  180.00   0.0  0
 4OR  CONST_18  O    C13  N3   C12    0.00   0.0  0
 4OR  CONST_19  N4   C13  N3   C11    0.00   0.0  0
 4OR  CONST_20  N4   C13  N3   C12  180.00   0.0  0
 4OR  CONST_21  N3   C13  N4   C14  180.00   0.0  0
 4OR  CONST_22  H29  N4   C13  N3     0.00   0.0  0
 4OR  CONST_23  O    C13  N4   C14    0.00   0.0  0
 4OR  Var_01    C9   C12  N3   C11   14.12  30.0  1
 4OR  Var_02    C10  C11  N3   C12   10.01  30.0  1
 4OR  Var_03    N3   C11  C10  C9   -30.03  30.0  1
 4OR  Var_04    H20  C    C1   N     60.53  30.0  3
 4OR  Var_05    C16  C14  N4   C13  -63.10  30.0  3
 4OR  Var_06    H11  C16  C14  C15   58.77  30.0  3
 4OR  Var_07    H14  C17  C14  C15   58.68  30.0  3
 4OR  Var_08    H8   C15  C14  C16   59.51  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
 4OR  chir_01  C9  C10  C12  N2  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
 4OR  plan-1  C18  0.020
 4OR  plan-1  C19  0.020
 4OR  plan-1  C20  0.020
 4OR  plan-1  C21  0.020
 4OR  plan-1  C22  0.020
 4OR  plan-1  C23  0.020
 4OR  plan-1  CL   0.020
 4OR  plan-1  N    0.020
 4OR  plan-1  C8   0.020
 4OR  plan-1  H17  0.020
 4OR  plan-1  H18  0.020
 4OR  plan-1  H19  0.020
 4OR  plan-2  C2   0.020
 4OR  plan-2  C3   0.020
 4OR  plan-2  N    0.020
 4OR  plan-2  N1   0.020
 4OR  plan-2  C7   0.020
 4OR  plan-2  C6   0.020
 4OR  plan-2  C5   0.020
 4OR  plan-2  F    0.020
 4OR  plan-2  C4   0.020
 4OR  plan-2  H3   0.020
 4OR  plan-2  H23  0.020
 4OR  plan-2  H24  0.020
 4OR  plan-3  C11  0.020
 4OR  plan-3  C12  0.020
 4OR  plan-3  C13  0.020
 4OR  plan-3  C14  0.020
 4OR  plan-3  N3   0.020
 4OR  plan-3  O    0.020
 4OR  plan-3  N4   0.020
 4OR  plan-3  H29  0.020
 4OR  plan-4  C18  0.020
 4OR  plan-4  C8   0.020
 4OR  plan-4  N1   0.020
 4OR  plan-4  C7   0.020
 4OR  plan-4  N2   0.020
 4OR  plan-4  C9   0.020
 4OR  plan-4  H25  0.020

