# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 01:18:33 2020
#   Inital geometry file: a 99 line input string
#   Ligand name: (1~{R},2~{S},4~{S})-~{N}-(3-chloranyl-4-cyano-phenyl)sulfonylbicyclo[2.2.1]heptane-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1cc(ccc1C#N)[S](=O)(=O)NC(=O)[C@H]2C[C@H]3CC[C@@H]2C3
#
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
 H4H  H4H  (1~{R},2~{S},4~{S})-~{N}-(3-chloranyl-4-cyano-phenyl)sulfonylbicyclo[2.2.1]heptane-2-carboxamide  ligand  37  22  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_H4H
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
 H4H  C2   C   C     0   0.601   1.5460   0.0416  -0.1169
 H4H  C7   C   CR6   0  -0.199  -1.4626  -1.1500   0.1092
 H4H  C8   C   CR16  0  -0.204  -1.9687  -1.4119  -1.1557
 H4H  C11  C   CSP   0   0.062  -4.8948   0.8568  -1.1540
 H4H  C15  C   CR16  0  -0.157  -2.0579  -0.2503   0.9755
 H4H  C16  C   CH1   0  -0.398   2.7014   0.4399  -0.9919
 H4H  C17  C   CH2   0  -0.426   2.9875   1.9586  -1.0556
 H4H  C18  C   CH1   0  -0.256   4.4640   2.0528  -0.6521
 H4H  C19  C   CH2   0  -0.436   4.5736   1.7726   0.8537
 H4H  C21  C   CH1   0  -0.254   4.0506  -0.1542  -0.5098
 H4H  O1   O   O     0  -0.416   0.9408   0.7619   0.6419
 H4H  N3   N   NC1   0  -0.812   1.2112  -1.2941  -0.2397
 H4H  S4   S   S     0   1.406  -0.0069  -2.0230   0.6337
 H4H  O5   O   OS    0  -0.612   0.1896  -1.7878   2.0462
 H4H  O6   O   OS    0  -0.631  -0.0660  -3.3746   0.1149
 H4H  C9   C   CR16  0  -0.244  -3.1031  -0.7406  -1.5685
 H4H  C10  C   CR6   0   0.105  -3.7233   0.1711  -0.7163
 H4H  N12  N   NS    0  -0.218  -5.8307   1.4105  -1.5311
 H4H  C13  C   CR6   0  -0.042  -3.1994   0.4088   0.5549
 H4H  CL1  CL  CL    0  -0.061  -3.9688   1.5278   1.6026
 H4H  C20  C   CH2   0  -0.453   4.3075   0.2471   0.9491
 H4H  C22  C   CH2   0  -0.438   5.0308   0.7611  -1.2504
 H4H  H1   H   HCR6  0   0.311  -1.4959  -2.1222  -1.8195
 H4H  H2   H   HCR6  0   0.319  -1.6539  -0.0605   1.9592
 H4H  H3   H   HCH1  0   0.301   2.4947   0.0528  -1.9947
 H4H  H4   H   HCH2  0   0.248   2.8311   2.3261  -2.0707
 H4H  H5   H   HCH2  0   0.243   2.3429   2.5401  -0.3968
 H4H  H6   H   HCH1  0   0.231   4.9418   2.9810  -0.9662
 H4H  H7   H   HCH2  0   0.235   5.5706   2.0189   1.2234
 H4H  H8   H   HCH2  0   0.230   3.8595   2.3616   1.4317
 H4H  H9   H   HCH1  0   0.244   4.1514  -1.2227  -0.7026
 H4H  H10  H   HNC1  0   0.449   1.6577  -1.8767  -0.9389
 H4H  H11  H   HCR6  0   0.308  -3.5154  -0.9220  -2.5508
 H4H  H12  H   HCH2  0   0.246   5.1871  -0.2814   1.3205
 H4H  H13  H   HCH2  0   0.236   3.4891  -0.0047   1.6260
 H4H  H14  H   HCH2  0   0.240   4.9383   0.7056  -2.3374
 H4H  H15  H   HCH2  0   0.242   6.0710   0.5721  -0.9761

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
 H4H  C22  C18  single    1.532  0.020  1.532
 H4H  C22  C21  single    1.532  0.020  1.532
 H4H  C17  C18  single    1.534  0.020  1.534
 H4H  C17  C16  single    1.547  0.020  1.547
 H4H  C18  C19  single    1.536  0.020  1.536
 H4H  C16  C21  single    1.551  0.020  1.551
 H4H  C16  C2   single    1.503  0.020  1.503
 H4H  C21  C20  single    1.535  0.020  1.535
 H4H  O1   C2   double    1.209  0.020  1.209
 H4H  C19  C20  single    1.551  0.020  1.551
 H4H  C2   N3   single    1.382  0.020  1.382
 H4H  N3   S4   single    1.667  0.020  1.667
 H4H  O5   S4   double    1.445  0.020  1.445
 H4H  S4   C7   single    1.777  0.020  1.777
 H4H  S4   O6   double    1.449  0.020  1.449
 H4H  C15  C7   aromatic  1.384  0.020  1.384
 H4H  C15  C13  aromatic  1.384  0.020  1.384
 H4H  C7   C8   aromatic  1.387  0.020  1.387
 H4H  CL1  C13  single    1.715  0.020  1.715
 H4H  C13  C10  aromatic  1.395  0.020  1.395
 H4H  C8   C9   aromatic  1.381  0.020  1.381
 H4H  C10  C9   aromatic  1.394  0.020  1.394
 H4H  C10  C11  single    1.426  0.020  1.426
 H4H  C11  N12  triple    1.151  0.020  1.151
 H4H  C8   H1   single    0.930  0.020  1.080
 H4H  C15  H2   single    0.930  0.020  1.080
 H4H  C16  H3   single    0.970  0.020  1.090
 H4H  C17  H4   single    0.970  0.020  1.090
 H4H  C17  H5   single    0.970  0.020  1.090
 H4H  C18  H6   single    0.970  0.020  1.090
 H4H  C19  H7   single    0.970  0.020  1.090
 H4H  C19  H8   single    0.970  0.020  1.090
 H4H  C21  H9   single    0.970  0.020  1.090
 H4H  N3   H10  single    0.860  0.020  1.020
 H4H  C9   H11  single    0.930  0.020  1.080
 H4H  C20  H12  single    0.970  0.020  1.090
 H4H  C20  H13  single    0.970  0.020  1.090
 H4H  C22  H14  single    0.970  0.020  1.090
 H4H  C22  H15  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
 H4H  N3   C2   O1   120.68  3.000
 H4H  N3   C2   C16  112.99  3.000
 H4H  O1   C2   C16  126.33  3.000
 H4H  S4   C7   C15  119.16  3.000
 H4H  C15  C7   C8   122.46  3.000
 H4H  S4   C7   C8   118.38  3.000
 H4H  H1   C8   C9   119.67  3.000
 H4H  H1   C8   C7   121.62  3.000
 H4H  C9   C8   C7   118.71  3.000
 H4H  N12  C11  C10  180.00  3.000
 H4H  H2   C15  C13  120.11  3.000
 H4H  H2   C15  C7   121.57  3.000
 H4H  C13  C15  C7   118.32  3.000
 H4H  H3   C16  C21  108.27  3.000
 H4H  H3   C16  C17  110.15  3.000
 H4H  C21  C16  C17  103.18  3.000
 H4H  H3   C16  C2   107.13  3.000
 H4H  C21  C16  C2   112.72  3.000
 H4H  C17  C16  C2   115.24  3.000
 H4H  H5   C17  H4   107.34  3.000
 H4H  H5   C17  C18  112.18  3.000
 H4H  H4   C17  C18  111.24  3.000
 H4H  H5   C17  C16  112.93  3.000
 H4H  H4   C17  C16  110.04  3.000
 H4H  C18  C17  C16  103.16  3.000
 H4H  H6   C18  C22  116.31  3.000
 H4H  H6   C18  C19  113.99  3.000
 H4H  C22  C18  C19  101.69  3.000
 H4H  H6   C18  C17  113.48  3.000
 H4H  C19  C18  C17  108.39  3.000
 H4H  C22  C18  C17  101.63  3.000
 H4H  H8   C19  H7   107.25  3.000
 H4H  H8   C19  C20  112.70  3.000
 H4H  H7   C19  C20  110.96  3.000
 H4H  H8   C19  C18  111.97  3.000
 H4H  H7   C19  C18  110.86  3.000
 H4H  C20  C19  C18  103.15  3.000
 H4H  H9   C21  C22  116.16  3.000
 H4H  H9   C21  C20  114.13  3.000
 H4H  C22  C21  C20  101.31  3.000
 H4H  H9   C21  C16  113.63  3.000
 H4H  C20  C21  C16  109.93  3.000
 H4H  C22  C21  C16  100.22  3.000
 H4H  H10  N3   S4   115.59  3.000
 H4H  H10  N3   C2   120.65  3.000
 H4H  S4   N3   C2   123.58  3.000
 H4H  O6   S4   O5   120.48  3.000
 H4H  O6   S4   N3   104.49  3.000
 H4H  O5   S4   N3   109.97  3.000
 H4H  O6   S4   C7   108.62  3.000
 H4H  O5   S4   C7   108.66  3.000
 H4H  N3   S4   C7   103.25  3.000
 H4H  H11  C9   C10  119.73  3.000
 H4H  H11  C9   C8   120.23  3.000
 H4H  C10  C9   C8   120.04  3.000
 H4H  C13  C10  C9   120.10  3.000
 H4H  C9   C10  C11  119.50  3.000
 H4H  C13  C10  C11  120.40  3.000
 H4H  CL1  C13  C10  119.95  3.000
 H4H  C10  C13  C15  120.37  3.000
 H4H  CL1  C13  C15  119.68  3.000
 H4H  H13  C20  H12  106.35  3.000
 H4H  H13  C20  C21  113.81  3.000
 H4H  H12  C20  C21  109.38  3.000
 H4H  H13  C20  C19  113.18  3.000
 H4H  H12  C20  C19  111.03  3.000
 H4H  C21  C20  C19  103.14  3.000
 H4H  H15  C22  H14  108.77  3.000
 H4H  H15  C22  C21  112.61  3.000
 H4H  H14  C22  C21  113.36  3.000
 H4H  H15  C22  C18  113.59  3.000
 H4H  H14  C22  C18  113.58  3.000
 H4H  C21  C22  C18   94.49  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
 H4H  CONST_01  C10  C13  C15  C7     0.00   0.0  0
 H4H  CONST_02  C10  C9   C8   C7     0.00   0.0  0
 H4H  CONST_03  C13  C15  C7   C8     0.00   0.0  0
 H4H  CONST_04  C13  C10  C9   C8     0.00   0.0  0
 H4H  CONST_05  C9   C8   C7   C15    0.00   0.0  0
 H4H  CONST_06  C9   C10  C13  C15    0.00   0.0  0
 H4H  CONST_07  CL1  C13  C15  C7   180.00   0.0  0
 H4H  CONST_08  C11  C10  C9   C8   180.00   0.0  0
 H4H  CONST_09  C15  C13  C10  C11  180.00   0.0  0
 H4H  CONST_10  C13  C15  C7   S4   180.00   0.0  0
 H4H  CONST_11  C9   C8   C7   S4   180.00   0.0  0
 H4H  CONST_12  CL1  C13  C10  C9   180.00   0.0  0
 H4H  CONST_13  H11  C9   C8   C7   180.00   0.0  0
 H4H  CONST_14  H2   C15  C7   C8   180.00   0.0  0
 H4H  CONST_15  H1   C8   C7   C15  180.00   0.0  0
 H4H  CONST_16  S4   N3   C2   C16  180.00   0.0  0
 H4H  CONST_17  H10  N3   C2   C16    0.00   0.0  0
 H4H  CONST_18  S4   N3   C2   O1     0.00   0.0  0
 H4H  Var_01    C21  C20  C19  C18   -1.08  30.0  1
 H4H  Var_02    N3   S4   C7   C8    73.90  30.0  3
 H4H  Var_03    C7   S4   N3   C2    62.31  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
 H4H  chir_01  C16  C17  C21  C2   negativ
 H4H  chir_02  C18  C22  C17  C19  negativ
 H4H  chir_03  C21  C20  C16  C22  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
 H4H  plan-1  C7   0.020
 H4H  plan-1  C8   0.020
 H4H  plan-1  C11  0.020
 H4H  plan-1  C15  0.020
 H4H  plan-1  S4   0.020
 H4H  plan-1  C9   0.020
 H4H  plan-1  C10  0.020
 H4H  plan-1  N12  0.020
 H4H  plan-1  C13  0.020
 H4H  plan-1  CL1  0.020
 H4H  plan-1  H1   0.020
 H4H  plan-1  H2   0.020
 H4H  plan-1  H11  0.020
 H4H  plan-2  C2   0.020
 H4H  plan-2  C16  0.020
 H4H  plan-2  O1   0.020
 H4H  plan-2  N3   0.020
 H4H  plan-2  S4   0.020
 H4H  plan-2  H10  0.020

