# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 14:52:24 2020
#   Inital geometry file: a 148 line input string
#   Ligand name: (11S)-8-chloro-11-[1-(methylsulfonyl)piperidin-4-yl]-6-piperazin-1-yl-11H-benzo[5,6]cyclohepta[1,2-b]pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[S](=O)(=O)N1CCC(CC1)[C@H]2c3ccc(Cl)cc3C(=Cc4cccnc24)N5CCNCC5
#
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
 736  736  (11S)-8-chloro-11-[1-(methylsulfonyl)piperidin-4-yl]-6-piperazin-1-yl-11H-benzo[5,6]cyclohepta[1,2-b]pyridine  ligand  61  32  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_736
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
 736  C1    C   CR16  0  -0.086   0.0422  -4.8727   0.3240
 736  N2    N   N     0  -0.411  -0.2441  -3.7903  -0.3859
 736  C3    C   CR6   0   0.243   0.1779  -2.6026   0.0361
 736  C4    C   CR6   0   0.060   0.9551  -2.4455   1.1960
 736  C5    C   CR16  0  -0.196   1.2097  -3.5960   1.9472
 736  C6    C   CR16  0  -0.322   0.7561  -4.8261   1.5117
 736  C9    C   CH1   0  -0.439  -0.2316  -1.4168  -0.8007
 736  C10   C   CR6   0   0.146   1.0083  -0.7552  -1.3429
 736  C11   C   CR6   0  -0.014   1.9462  -0.1322  -0.5127
 736  C12   C   C     0   0.332   1.8359  -0.0975   0.9627
 736  C13   C   C1    0  -0.462   1.4262  -1.1599   1.6894
 736  C18   C   CR16  0  -0.325   1.2337  -0.7720  -2.7185
 736  C19   C   CR16  0  -0.203   2.3471  -0.1815  -3.2875
 736  C20   C   CR6   0  -0.045   3.2642   0.4358  -2.4506
 736  C21   C   CR16  0  -0.223   3.0749   0.4654  -1.0846
 736  C24   C   CH1   0  -0.224  -1.2084  -0.4503  -0.1020
 736  C25   C   CH2   0  -0.427  -1.5876   0.6994  -1.0321
 736  C26   C   CH2   0  -0.319  -2.5966   1.6294  -0.3751
 736  N27   N   N     0  -0.568  -3.7730   0.9191   0.1192
 736  C28   C   CH2   0  -0.325  -3.4679  -0.2199   0.9828
 736  C29   C   CH2   0  -0.427  -2.4691  -1.1813   0.3526
 736  CL40  CL  CL    0  -0.132   4.6766   1.1788  -3.1306
 736  S1    S   S     0   1.347  -5.1898   0.9618  -0.7047
 736  N1    N   NT    0  -0.491   2.3188   1.0716   1.5451
 736  C2    C   CH2   0  -0.305   2.6070   1.0659   2.9657
 736  C7    C   CH2   0  -0.304   1.6553   2.3043   1.1250
 736  C8    C   CH2   0  -0.297   3.4204   2.2940   3.3352
 736  C14   C   CH2   0  -0.296   2.4752   3.5143   1.5267
 736  N3    N   NH1   0  -0.599   2.7007   3.4936   2.9578
 736  O1    O   OS    0  -0.670  -5.3004   2.2827  -1.3080
 736  C15   C   CH3   0  -0.804  -5.1013  -0.2289  -2.0263
 736  O2    O   OS    0  -0.672  -6.2341   0.5152   0.2072
 736  H1    H   HCR6  0   0.260  -0.3210  -5.8176  -0.0645
 736  H5    H   HCR6  0   0.265   1.7775  -3.5178   2.8668
 736  H6    H   HCR6  0   0.268   0.9533  -5.7297   2.0719
 736  H9    H   HCH1  0   0.266  -0.7743  -1.8330  -1.6546
 736  H13   H   H     0   0.272   1.4608  -1.0849   2.7698
 736  H18   H   HCR6  0   0.264   0.5099  -1.2547  -3.3635
 736  H19   H   HCR6  0   0.280   2.4946  -0.2002  -4.3586
 736  H21   H   HCR6  0   0.275   3.8012   0.9474  -0.4438
 736  H24   H   HCH1  0   0.241  -0.7340  -0.0215   0.7860
 736  H251  H   HCH2  0   0.228  -1.9945   0.3067  -1.9713
 736  H252  H   HCH2  0   0.252  -0.7065   1.2874  -1.3014
 736  H261  H   HCH2  0   0.277  -2.8990   2.4230  -1.0544
 736  H262  H   HCH2  0   0.250  -2.1357   2.1184   0.4893
 736  H281  H   HCH2  0   0.256  -3.0520   0.1831   1.9113
 736  H282  H   HCH2  0   0.276  -4.3865  -0.7353   1.2562
 736  H291  H   HCH2  0   0.227  -2.9238  -1.7003  -0.4986
 736  H292  H   HCH2  0   0.254  -2.2302  -1.9487   1.0925
 736  H21A  H   HCH2  0   0.212   1.6872   1.0410   3.5695
 736  H22   H   HCH2  0   0.251   3.1853   0.1734   3.2095
 736  H71   H   HCH2  0   0.256   1.5246   2.3064   0.0433
 736  H72   H   HCH2  0   0.221   0.6536   2.3734   1.5752
 736  H81   H   HCH2  0   0.239   3.5855   2.2919   4.4141
 736  H82   H   HCH2  0   0.197   4.4067   2.2175   2.8512
 736  H141  H   HCH2  0   0.239   1.9254   4.4175   1.2558
 736  H142  H   HCH2  0   0.196   3.4108   3.5120   0.9450
 736  HN3   H   HNH1  0   0.357   3.2279   4.3113   3.2337
 736  H151  H   HCH3  0   0.287  -4.2757   0.0175  -2.6900
 736  H152  H   HCH3  0   0.287  -4.9655  -1.2247  -1.6106
 736  H153  H   HCH3  0   0.306  -6.0400  -0.1891  -2.5768

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
 736  C1   N2    aromatic  1.326  0.020  1.326
 736  C1   C6    aromatic  1.387  0.020  1.387
 736  C1   H1    single    0.930  0.020  1.080
 736  N2   C3    aromatic  1.329  0.020  1.329
 736  C3   C4    aromatic  1.405  0.020  1.405
 736  C3   C9    single    1.508  0.020  1.508
 736  C4   C5    aromatic  1.397  0.020  1.397
 736  C4   C13   single    1.455  0.020  1.455
 736  C5   C6    aromatic  1.382  0.020  1.382
 736  C5   H5    single    0.930  0.020  1.080
 736  C6   H6    single    0.930  0.020  1.080
 736  C9   C10   single    1.506  0.020  1.506
 736  C9   C24   single    1.542  0.020  1.542
 736  C9   H9    single    0.970  0.020  1.090
 736  C10  C11   aromatic  1.399  0.020  1.399
 736  C10  C18   aromatic  1.394  0.020  1.394
 736  C11  C12   single    1.480  0.020  1.480
 736  C11  C21   aromatic  1.399  0.020  1.399
 736  C12  C13   double    1.351  0.020  1.351
 736  C12  N1    single    1.392  0.020  1.392
 736  C13  H13   single    0.930  0.020  1.080
 736  C18  C19   aromatic  1.383  0.020  1.383
 736  C18  H18   single    0.930  0.020  1.080
 736  C19  C20   aromatic  1.387  0.020  1.387
 736  C19  H19   single    0.930  0.020  1.080
 736  C20  C21   aromatic  1.379  0.020  1.379
 736  C20  CL40  single    1.735  0.020  1.735
 736  C21  H21   single    0.930  0.020  1.080
 736  C24  C25   single    1.527  0.020  1.527
 736  C24  C29   single    1.527  0.020  1.527
 736  C24  H24   single    0.970  0.020  1.090
 736  C25  C26   single    1.521  0.020  1.521
 736  C25  H251  single    0.970  0.020  1.090
 736  C25  H252  single    0.970  0.020  1.090
 736  C26  N27   single    1.460  0.020  1.460
 736  C26  H261  single    0.970  0.020  1.090
 736  C26  H262  single    0.970  0.020  1.090
 736  N27  C28   single    1.462  0.020  1.462
 736  N27  S1    single    1.639  0.020  1.639
 736  C28  C29   single    1.523  0.020  1.523
 736  C28  H281  single    0.970  0.020  1.090
 736  C28  H282  single    0.970  0.020  1.090
 736  C29  H291  single    0.970  0.020  1.090
 736  C29  H292  single    0.970  0.020  1.090
 736  S1   O1    double    1.456  0.020  1.456
 736  S1   C15   single    1.781  0.020  1.781
 736  S1   O2    double    1.457  0.020  1.457
 736  N1   C2    single    1.450  0.020  1.450
 736  N1   C7    single    1.462  0.020  1.462
 736  C2   C8    single    1.519  0.020  1.519
 736  C2   H21A  single    0.970  0.020  1.090
 736  C2   H22   single    0.970  0.020  1.090
 736  C7   C14   single    1.516  0.020  1.516
 736  C7   H71   single    0.970  0.020  1.090
 736  C7   H72   single    0.970  0.020  1.090
 736  C8   N3    single    1.449  0.020  1.449
 736  C8   H81   single    0.970  0.020  1.090
 736  C8   H82   single    0.970  0.020  1.090
 736  C14  N3    single    1.449  0.020  1.449
 736  C14  H141  single    0.970  0.020  1.090
 736  C14  H142  single    0.970  0.020  1.090
 736  N3   HN3   single    0.890  0.020  1.040
 736  C15  H151  single    0.970  0.020  1.090
 736  C15  H152  single    0.970  0.020  1.090
 736  C15  H153  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
 736  H1    C1   C6    120.58  3.000
 736  H1    C1   N2    116.57  3.000
 736  C6    C1   N2    122.85  3.000
 736  C3    N2   C1    119.41  3.000
 736  C9    C3   C4    121.36  3.000
 736  C9    C3   N2    116.12  3.000
 736  C4    C3   N2    122.52  3.000
 736  C13   C4   C5    119.08  3.000
 736  C13   C4   C3    123.89  3.000
 736  C5    C4   C3    116.91  3.000
 736  H5    C5   C6    120.25  3.000
 736  H5    C5   C4    119.49  3.000
 736  C6    C5   C4    120.25  3.000
 736  H6    C6   C5    121.39  3.000
 736  H6    C6   C1    120.64  3.000
 736  C5    C6   C1    117.97  3.000
 736  H9    C9   C24   106.14  3.000
 736  H9    C9   C10   107.12  3.000
 736  C24   C9   C10   114.16  3.000
 736  H9    C9   C3    105.59  3.000
 736  C24   C9   C3    114.43  3.000
 736  C10   C9   C3    108.76  3.000
 736  C18   C10  C11   118.85  3.000
 736  C18   C10  C9    118.88  3.000
 736  C11   C10  C9    122.26  3.000
 736  C21   C11  C12   117.23  3.000
 736  C21   C11  C10   119.23  3.000
 736  C12   C11  C10   123.51  3.000
 736  N1    C12  C13   122.71  3.000
 736  N1    C12  C11   114.26  3.000
 736  C13   C12  C11   122.72  3.000
 736  H13   C13  C12   118.18  3.000
 736  H13   C13  C4    114.17  3.000
 736  C12   C13  C4    127.63  3.000
 736  H18   C18  C19   118.91  3.000
 736  H18   C18  C10   119.01  3.000
 736  C19   C18  C10   122.07  3.000
 736  H19   C19  C20   121.02  3.000
 736  H19   C19  C18   120.66  3.000
 736  C20   C19  C18   118.32  3.000
 736  CL40  C20  C21   119.39  3.000
 736  CL40  C20  C19   119.51  3.000
 736  C21   C20  C19   121.10  3.000
 736  H21   C21  C20   120.27  3.000
 736  H21   C21  C11   119.31  3.000
 736  C20   C21  C11   120.42  3.000
 736  H24   C24  C29   107.70  3.000
 736  H24   C24  C25   107.88  3.000
 736  C29   C24  C25   109.69  3.000
 736  H24   C24  C9    109.80  3.000
 736  C29   C24  C9    110.98  3.000
 736  C25   C24  C9    110.69  3.000
 736  H252  C25  H251  106.31  3.000
 736  H252  C25  C26   108.19  3.000
 736  H251  C25  C26   110.04  3.000
 736  H252  C25  C24   110.80  3.000
 736  H251  C25  C24   110.14  3.000
 736  C26   C25  C24   111.22  3.000
 736  H262  C26  H261  106.51  3.000
 736  H262  C26  N27   106.80  3.000
 736  H261  C26  N27   110.02  3.000
 736  H262  C26  C25   109.56  3.000
 736  H261  C26  C25   111.15  3.000
 736  N27   C26  C25   112.53  3.000
 736  S1    N27  C28   119.85  3.000
 736  S1    N27  C26   120.89  3.000
 736  C28   N27  C26   114.25  3.000
 736  H282  C28  H281  106.38  3.000
 736  H282  C28  C29   111.01  3.000
 736  H281  C28  C29   109.54  3.000
 736  H282  C28  N27   109.96  3.000
 736  H281  C28  N27   107.08  3.000
 736  C29   C28  N27   112.61  3.000
 736  H292  C29  H291  106.51  3.000
 736  H292  C29  C28   107.86  3.000
 736  H291  C29  C28   110.38  3.000
 736  H292  C29  C24   110.94  3.000
 736  H291  C29  C24   109.77  3.000
 736  C28   C29  C24   111.26  3.000
 736  O2    S1   C15   107.17  3.000
 736  O2    S1   O1    118.88  3.000
 736  C15   S1   O1    107.62  3.000
 736  O2    S1   N27   107.28  3.000
 736  C15   S1   N27   108.21  3.000
 736  O1    S1   N27   107.31  3.000
 736  C7    N1   C2    112.04  3.000
 736  C7    N1   C12   115.50  3.000
 736  C2    N1   C12   118.40  3.000
 736  H22   C2   H21A  107.57  3.000
 736  H22   C2   C8    108.86  3.000
 736  H21A  C2   C8    109.42  3.000
 736  H22   C2   N1    109.12  3.000
 736  H21A  C2   N1    111.81  3.000
 736  C8    C2   N1    109.99  3.000
 736  H72   C7   H71   107.27  3.000
 736  H72   C7   C14   109.50  3.000
 736  H71   C7   C14   109.06  3.000
 736  H72   C7   N1    110.40  3.000
 736  H71   C7   N1    109.96  3.000
 736  C14   C7   N1    110.58  3.000
 736  H82   C8   H81   107.38  3.000
 736  H82   C8   N3    112.82  3.000
 736  H81   C8   N3    109.53  3.000
 736  H82   C8   C2    108.46  3.000
 736  H81   C8   C2    108.66  3.000
 736  N3    C8   C2    109.89  3.000
 736  H142  C14  H141  107.36  3.000
 736  H142  C14  N3    112.91  3.000
 736  H141  C14  N3    109.59  3.000
 736  H142  C14  C7    108.53  3.000
 736  H141  C14  C7    108.80  3.000
 736  N3    C14  C7    109.54  3.000
 736  HN3   N3   C14   109.82  3.000
 736  HN3   N3   C8    109.84  3.000
 736  C14   N3   C8    110.26  3.000
 736  H153  C15  H152  109.53  3.000
 736  H153  C15  H151  109.73  3.000
 736  H152  C15  H151  110.24  3.000
 736  H153  C15  S1    107.93  3.000
 736  H152  C15  S1    109.55  3.000
 736  H151  C15  S1    109.83  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
 736  CONST_01  C4    C3   N2   C1      0.00   0.0  0
 736  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 736  CONST_03  C5    C6   C1   N2      0.00   0.0  0
 736  CONST_04  C5    C4   C3   N2      0.00   0.0  0
 736  CONST_05  C6    C1   N2   C3      0.00   0.0  0
 736  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 736  CONST_07  C20   C21  C11  C10     0.00   0.0  0
 736  CONST_08  C20   C19  C18  C10     0.00   0.0  0
 736  CONST_09  C19   C18  C10  C11     0.00   0.0  0
 736  CONST_10  C19   C20  C21  C11     0.00   0.0  0
 736  CONST_11  C21   C11  C10  C18     0.00   0.0  0
 736  CONST_12  C21   C20  C19  C18     0.00   0.0  0
 736  CONST_13  CL40  C20  C21  C11   180.00   0.0  0
 736  CONST_14  CL40  C20  C19  C18   180.00   0.0  0
 736  CONST_15  H5    C5   C6   C1    180.00   0.0  0
 736  CONST_16  H6    C6   C1   N2    180.00   0.0  0
 736  CONST_17  H1    C1   N2   C3    180.00   0.0  0
 736  CONST_18  H18   C18  C10  C9      0.00   0.0  0
 736  CONST_19  H21   C21  C11  C10   180.00   0.0  0
 736  CONST_20  H19   C19  C18  C10   180.00   0.0  0
 736  Var_01    C12   C13  C4   C3    -36.44  30.0  1
 736  Var_02    C11   C12  C13  C4     -4.17  30.0  1
 736  Var_03    C13   C12  C11  C10    40.58  30.0  1
 736  Var_04    C2    N1   C12  C11  -162.95  30.0  2
 736  Var_05    C8    C2   N1   C12   166.50  30.0  1
 736  Var_06    C14   C7   N1   C12  -165.27  30.0  1
 736  Var_07    N27   C26  C25  C24   -53.59  30.0  1
 736  Var_08    N27   C28  C29  C24    53.14  30.0  1
 736  Var_09    C28   N27  C26  C25    52.13  30.0  1
 736  Var_10    C29   C28  N27  C26   -51.91  30.0  1
 736  Var_11    N3    C8   C2   N1     57.60  30.0  1
 736  Var_12    N3    C14  C7   N1    -56.72  30.0  1
 736  Var_13    C14   N3   C8   C2    -60.83  30.0  1
 736  Var_14    C8    N3   C14  C7     60.22  30.0  1
 736  Var_15    O1    S1   N27  C26   -34.80  30.0  3
 736  Var_16    H151  C15  S1   N27   -59.81  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
 736  chir_01  C9   C3   C10  C24  positiv
 736  chir_02  C24  C29  C25  C9   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
 736  plan-1  C12   0.020
 736  plan-1  N1    0.020
 736  plan-1  C2    0.020
 736  plan-1  C7    0.020
 736  plan-2  C1    0.020
 736  plan-2  N2    0.020
 736  plan-2  C3    0.020
 736  plan-2  C4    0.020
 736  plan-2  C5    0.020
 736  plan-2  C6    0.020
 736  plan-2  C9    0.020
 736  plan-2  C13   0.020
 736  plan-2  H1    0.020
 736  plan-2  H5    0.020
 736  plan-2  H6    0.020
 736  plan-3  C9    0.020
 736  plan-3  C10   0.020
 736  plan-3  C11   0.020
 736  plan-3  C12   0.020
 736  plan-3  C18   0.020
 736  plan-3  C19   0.020
 736  plan-3  C20   0.020
 736  plan-3  C21   0.020
 736  plan-3  CL40  0.020
 736  plan-3  H18   0.020
 736  plan-3  H19   0.020
 736  plan-3  H21   0.020

