# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 18:38:18 2020
#   Inital geometry file: a 83 line input string
#   Ligand name: (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=O)[C@H]1CCCCc2c1[nH]c3ccc(Cl)cc23
#
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
 4I5  4I5  (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide  ligand  33  18  .  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_4I5
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
 4I5  C1    C   CR6   0  -0.047  -3.3901  -0.0708   0.1124
 4I5  N1    N   NH2   0  -0.802   2.7286   1.1426   1.7226
 4I5  O1    O   O     0  -0.494   4.4892   1.6247   0.4040
 4I5  CL1   CL  CL    0  -0.149  -4.9025  -0.9067   0.3291
 4I5  C2    C   CR16  0  -0.248  -3.4031   1.3306   0.0807
 4I5  N2    N   NR15  0  -0.733   0.2379   1.7150  -0.3954
 4I5  C3    C   CR16  0  -0.310  -2.2251   2.0315  -0.0877
 4I5  C4    C   CR56  0   0.343  -1.0467   1.3027  -0.2234
 4I5  C5    C   CR56  0   0.046  -1.0306  -0.1086  -0.1942
 4I5  C6    C   CR16  0  -0.333  -2.2315  -0.8050  -0.0218
 4I5  C7    C   CR5   0  -0.025   0.3293  -0.5255  -0.3579
 4I5  C8    C   CR5   0   0.322   1.0688   0.6240  -0.4782
 4I5  C9    C   CH1   0  -0.487   2.5332   0.8140  -0.6973
 4I5  C10   C   CH2   0  -0.442   3.1802  -0.4142  -1.3536
 4I5  C11   C   CH2   0  -0.443   3.3822  -1.6353  -0.4596
 4I5  C12   C   CH2   0  -0.449   2.1697  -2.1023   0.3517
 4I5  C13   C   CH2   0  -0.525   0.8245  -1.9395  -0.3546
 4I5  C14   C   C     0   0.546   3.3381   1.2343   0.5348
 4I5  HN1   H   HNH2  0   0.403   3.2280   1.3771   2.5654
 4I5  HN1A  H   HNH2  0   0.415   1.7978   0.7754   1.8234
 4I5  H2    H   HCR6  0   0.272  -4.3365   1.8654   0.1912
 4I5  HN2   H   HNR5  0   0.408   0.5346   2.6735  -0.4819
 4I5  H3    H   HCR6  0   0.269  -2.2292   3.1134  -0.1102
 4I5  H6    H   HCR6  0   0.263  -2.2544  -1.8868   0.0051
 4I5  H9    H   HCH1  0   0.298   2.6511   1.6451  -1.4024
 4I5  H10   H   HCH2  0   0.245   2.5716  -0.6832  -2.2200
 4I5  H10A  H   HCH2  0   0.253   4.1503  -0.1164  -1.7544
 4I5  H11   H   HCH2  0   0.235   3.7117  -2.4497  -1.1098
 4I5  H11A  H   HCH2  0   0.229   4.2127  -1.4545   0.2283
 4I5  H12   H   HCH2  0   0.238   2.3169  -3.1535   0.6089
 4I5  H12A  H   HCH2  0   0.218   2.1263  -1.5698   1.3043
 4I5  H13   H   HCH2  0   0.244   0.0831  -2.5623   0.1521
 4I5  H13A  H   HCH2  0   0.239   0.8888  -2.3326  -1.3754

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
 4I5  C1   CL1   single    1.742  0.020  1.742
 4I5  C1   C2    aromatic  1.402  0.020  1.402
 4I5  C1   C6    aromatic  1.378  0.020  1.378
 4I5  N1   C14   single    1.338  0.020  1.338
 4I5  O1   C14   double    1.223  0.020  1.223
 4I5  C2   C3    aromatic  1.381  0.020  1.381
 4I5  N2   C4    aromatic  1.360  0.020  1.360
 4I5  N2   C8    aromatic  1.374  0.020  1.374
 4I5  C3   C4    aromatic  1.392  0.020  1.392
 4I5  C4   C5    aromatic  1.412  0.020  1.412
 4I5  C5   C6    aromatic  1.399  0.020  1.399
 4I5  C5   C7    aromatic  1.432  0.020  1.432
 4I5  C7   C8    aromatic  1.372  0.020  1.372
 4I5  C7   C13   single    1.498  0.020  1.498
 4I5  C8   C9    single    1.493  0.020  1.493
 4I5  C9   C10   single    1.535  0.020  1.535
 4I5  C9   C14   single    1.531  0.020  1.531
 4I5  C10  C11   single    1.527  0.020  1.527
 4I5  C11  C12   single    1.532  0.020  1.532
 4I5  C12  C13   single    1.528  0.020  1.528
 4I5  N1   HN1   single    0.860  0.020  1.020
 4I5  N1   HN1A  single    0.860  0.020  1.020
 4I5  C2   H2    single    0.930  0.020  1.080
 4I5  N2   HN2   single    0.860  0.020  1.020
 4I5  C3   H3    single    0.930  0.020  1.080
 4I5  C6   H6    single    0.930  0.020  1.080
 4I5  C9   H9    single    0.970  0.020  1.090
 4I5  C10  H10   single    0.970  0.020  1.090
 4I5  C10  H10A  single    0.970  0.020  1.090
 4I5  C11  H11   single    0.970  0.020  1.090
 4I5  C11  H11A  single    0.970  0.020  1.090
 4I5  C12  H12   single    0.970  0.020  1.090
 4I5  C12  H12A  single    0.970  0.020  1.090
 4I5  C13  H13   single    0.970  0.020  1.090
 4I5  C13  H13A  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
 4I5  C6    C1   C2   122.56  3.000
 4I5  C6    C1   CL1  119.11  3.000
 4I5  C2    C1   CL1  118.33  3.000
 4I5  HN1A  N1   HN1  117.39  3.000
 4I5  HN1A  N1   C14  122.38  3.000
 4I5  HN1   N1   C14  120.06  3.000
 4I5  H2    C2   C3   119.85  3.000
 4I5  H2    C2   C1   120.00  3.000
 4I5  C3    C2   C1   120.14  3.000
 4I5  HN2   N2   C8   124.92  3.000
 4I5  HN2   N2   C4   125.28  3.000
 4I5  C8    N2   C4   109.76  3.000
 4I5  H3    C3   C4   121.64  3.000
 4I5  H3    C3   C2   120.44  3.000
 4I5  C4    C3   C2   117.92  3.000
 4I5  C5    C4   C3   122.07  3.000
 4I5  C5    C4   N2   107.15  3.000
 4I5  C3    C4   N2   130.77  3.000
 4I5  C7    C5   C6   133.20  3.000
 4I5  C7    C5   C4   107.43  3.000
 4I5  C6    C5   C4   119.37  3.000
 4I5  H6    C6   C5   121.25  3.000
 4I5  H6    C6   C1   120.81  3.000
 4I5  C5    C6   C1   117.94  3.000
 4I5  C13   C7   C8   127.79  3.000
 4I5  C13   C7   C5   126.05  3.000
 4I5  C8    C7   C5   106.14  3.000
 4I5  C9    C8   C7   130.41  3.000
 4I5  C9    C8   N2   120.07  3.000
 4I5  C7    C8   N2   109.51  3.000
 4I5  H9    C9   C14  104.66  3.000
 4I5  H9    C9   C10  106.63  3.000
 4I5  C14   C9   C10  110.01  3.000
 4I5  H9    C9   C8   107.24  3.000
 4I5  C14   C9   C8   115.63  3.000
 4I5  C10   C9   C8   111.97  3.000
 4I5  H10A  C10  H10  105.73  3.000
 4I5  H10A  C10  C11  108.41  3.000
 4I5  H10   C10  C11  109.94  3.000
 4I5  H10A  C10  C9   108.26  3.000
 4I5  H10   C10  C9   107.53  3.000
 4I5  C11   C10  C9   116.44  3.000
 4I5  H11A  C11  H11  105.57  3.000
 4I5  H11A  C11  C12  108.57  3.000
 4I5  H11   C11  C12  109.06  3.000
 4I5  H11A  C11  C10  109.67  3.000
 4I5  H11   C11  C10  106.71  3.000
 4I5  C12   C11  C10  116.69  3.000
 4I5  H12A  C12  H12  105.62  3.000
 4I5  H12A  C12  C13  108.43  3.000
 4I5  H12   C12  C13  109.27  3.000
 4I5  H12A  C12  C11  110.17  3.000
 4I5  H12   C12  C11  108.15  3.000
 4I5  C13   C12  C11  114.81  3.000
 4I5  H13A  C13  H13  105.50  3.000
 4I5  H13A  C13  C12  109.92  3.000
 4I5  H13   C13  C12  108.80  3.000
 4I5  H13A  C13  C7   110.85  3.000
 4I5  H13   C13  C7   108.34  3.000
 4I5  C12   C13  C7   113.11  3.000
 4I5  C9    C14  O1   119.78  3.000
 4I5  C9    C14  N1   117.15  3.000
 4I5  O1    C14  N1   123.07  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
 4I5  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 4I5  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 4I5  CONST_03  C7    C5   C6   C1    180.00   0.0  0
 4I5  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 4I5  CONST_05  N2    C4   C3   C2    180.00   0.0  0
 4I5  CONST_06  C5    C4   C3   C2      0.00   0.0  0
 4I5  CONST_07  C6    C5   C4   N2    180.00   0.0  0
 4I5  CONST_08  C7    C5   C4   N2      0.00   0.0  0
 4I5  CONST_09  C5    C7   C8   N2      0.00   0.0  0
 4I5  CONST_10  C6    C1   C2   C3      0.00   0.0  0
 4I5  CONST_11  C8    N2   C4   C3    180.00   0.0  0
 4I5  CONST_12  C6    C5   C4   C3      0.00   0.0  0
 4I5  CONST_13  C7    C5   C4   C3    180.00   0.0  0
 4I5  CONST_14  C7    C8   N2   C4      0.00   0.0  0
 4I5  CONST_15  C8    C7   C5   C4      0.00   0.0  0
 4I5  CONST_16  C8    N2   C4   C5      0.00   0.0  0
 4I5  CONST_17  C8    C7   C5   C6    180.00   0.0  0
 4I5  CONST_18  C3    C2   C1   CL1   180.00   0.0  0
 4I5  CONST_19  C5    C6   C1   CL1   180.00   0.0  0
 4I5  CONST_20  H3    C3   C2   C1    180.00   0.0  0
 4I5  CONST_21  H6    C6   C1   C2    180.00   0.0  0
 4I5  CONST_22  HN2   N2   C4   C3      0.00   0.0  0
 4I5  CONST_23  H2    C2   C3   C4    180.00   0.0  0
 4I5  CONST_24  HN1   N1   C14  C9    180.00   0.0  0
 4I5  CONST_25  HN1A  N1   C14  C9      0.00   0.0  0
 4I5  Var_01    C12   C13  C7   C5   -141.67  30.0  1
 4I5  Var_02    C11   C12  C13  C7    -76.71  30.0  1
 4I5  Var_03    C12   C11  C10  C9     49.83  30.0  1
 4I5  Var_04    C13   C12  C11  C10    35.43  30.0  1

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
 4I5  chir_01  C9  C8  C10  C14  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
 4I5  plan-1  N1    0.020
 4I5  plan-1  O1    0.020
 4I5  plan-1  C9    0.020
 4I5  plan-1  C14   0.020
 4I5  plan-1  HN1   0.020
 4I5  plan-1  HN1A  0.020
 4I5  plan-2  C1    0.020
 4I5  plan-2  CL1   0.020
 4I5  plan-2  C2    0.020
 4I5  plan-2  N2    0.020
 4I5  plan-2  C3    0.020
 4I5  plan-2  C4    0.020
 4I5  plan-2  C5    0.020
 4I5  plan-2  C6    0.020
 4I5  plan-2  C7    0.020
 4I5  plan-2  C8    0.020
 4I5  plan-2  C9    0.020
 4I5  plan-2  C13   0.020
 4I5  plan-2  H2    0.020
 4I5  plan-2  HN2   0.020
 4I5  plan-2  H3    0.020
 4I5  plan-2  H6    0.020

