# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 22:43:11 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 2-({5-[(2-chlorophenoxy)methyl]-1H-tetrazol-1-yl}acetyl)-N-(4-chlorophenyl)hydrazinecarboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccc(NC(=O)NNC(=O)Cn2nnnc2COc3ccccc3Cl)cc1
#
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
 5EG  5EG  2-({5-[(2-chlorophenoxy)methyl]-1H-tetrazol-1-yl}acetyl)-N-(4-chlorophenyl)hydrazinecarboxamide  ligand  44  29  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_5EG
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
 5EG  C2   C   C     0   0.542   0.3992  -0.7017  -0.2549
 5EG  C3   C   CH2   0  -0.444   1.0589  -1.5513  -1.3303
 5EG  O1   O   O     0  -0.417   0.3411  -1.0397   0.9014
 5EG  C11  C   CR6   0   0.476   3.9373   1.2921  -0.4639
 5EG  C12  C   CR16  0  -0.378   4.8858   1.6154  -1.4273
 5EG  C13  C   CR16  0  -0.234   5.2668   2.9386  -1.6135
 5EG  C14  C   CR16  0  -0.282   4.7142   3.9498  -0.8455
 5EG  C15  C   CR16  0  -0.205   3.7750   3.6345   0.1276
 5EG  C16  C   CR6   0  -0.159   3.3962   2.3183   0.3143
 5EG  C20  C   C     0   0.694  -2.1225   1.0801   0.4915
 5EG  C23  C   CR6   0   0.396  -4.1178  -0.2827  -0.0579
 5EG  C24  C   CR16  0  -0.315  -5.0345   0.2851   0.8277
 5EG  C25  C   CR16  0  -0.201  -6.3189  -0.2314   0.9244
 5EG  C26  C   CR6   0  -0.059  -6.7013  -1.3068   0.1424
 5EG  C28  C   CR16  0  -0.201  -5.8049  -1.8780  -0.7469
 5EG  C29  C   CR16  0  -0.355  -4.5242  -1.3661  -0.8410
 5EG  N4   N   NR5   0  -0.309   2.0244  -2.4410  -0.7488
 5EG  N5   N   N     0  -0.063   1.6901  -3.6307  -0.2758
 5EG  N6   N   N     0  -0.135   2.7499  -4.1446   0.2070
 5EG  N7   N   N     0  -0.330   3.7867  -3.3160   0.0805
 5EG  C8   C   CR5   0   0.504   3.3264  -2.2478  -0.5157
 5EG  C9   C   CH2   0  -0.282   4.0837  -1.0344  -0.9040
 5EG  O10  O   O2    0  -0.467   3.4885   0.0464  -0.2134
 5EG  CL1  CL  CL    0  -0.096   2.2563   1.9146   1.5512
 5EG  N18  N   NH1   0  -0.530  -0.1789   0.4239  -0.7495
 5EG  N19  N   NH1   0  -0.502  -0.8289   1.2969   0.0683
 5EG  O21  O   O     0  -0.493  -2.5759   1.7198   1.4218
 5EG  N22  N   NH1   0  -0.770  -2.8072   0.1589  -0.2382
 5EG  CL2  CL  CL    0  -0.136  -8.3102  -1.9413   0.2708
 5EG  H1   H   HCH2  0   0.351   0.2959  -2.1521  -1.8267
 5EG  H2   H   HCH2  0   0.320   1.5406  -0.9491  -2.1000
 5EG  H3   H   HCR6  0   0.298   5.3415   0.8504  -2.0410
 5EG  H4   H   HCR6  0   0.271   6.0052   3.1686  -2.3697
 5EG  H5   H   HCR6  0   0.269   5.0121   4.9788  -0.9911
 5EG  H6   H   HCR6  0   0.284   3.3409   4.4088   0.7455
 5EG  H7   H   HCR6  0   0.290  -4.7688   1.1293   1.4415
 5EG  H8   H   HCR6  0   0.281  -7.0172   0.2203   1.6158
 5EG  H9   H   HCR6  0   0.283  -6.0933  -2.7192  -1.3623
 5EG  H10  H   HCR6  0   0.280  -3.8301  -1.8225  -1.5366
 5EG  H11  H   HCH2  0   0.296   5.1338  -1.1641  -0.6315
 5EG  H12  H   HCH2  0   0.282   4.0261  -0.8980  -1.9896
 5EG  H13  H   HNH1  0   0.432   0.0015   0.7350  -1.6934
 5EG  H14  H   HNH1  0   0.400  -0.2496   1.8460   0.6894
 5EG  H15  H   HNH1  0   0.416  -2.3121  -0.2763  -1.0019

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
 5EG  CL2  C26  single    1.734  0.020  1.734
 5EG  C25  C26  aromatic  1.384  0.020  1.384
 5EG  C25  C24  aromatic  1.388  0.020  1.388
 5EG  C26  C28  aromatic  1.386  0.020  1.386
 5EG  C24  C23  aromatic  1.395  0.020  1.395
 5EG  C28  C29  aromatic  1.382  0.020  1.382
 5EG  C23  C29  aromatic  1.397  0.020  1.397
 5EG  C23  N22  single    1.395  0.020  1.395
 5EG  N22  C20  single    1.360  0.020  1.360
 5EG  CL1  C16  single    1.730  0.020  1.730
 5EG  C15  C16  aromatic  1.382  0.020  1.382
 5EG  C15  C14  aromatic  1.389  0.020  1.389
 5EG  C20  O21  double    1.217  0.020  1.217
 5EG  C20  N19  single    1.378  0.020  1.378
 5EG  C16  C11  aromatic  1.397  0.020  1.397
 5EG  N19  N18  single    1.361  0.020  1.361
 5EG  C14  C13  aromatic  1.385  0.020  1.385
 5EG  C11  O10  single    1.348  0.020  1.348
 5EG  C11  C12  aromatic  1.390  0.020  1.390
 5EG  C3   N4   single    1.436  0.020  1.436
 5EG  C3   C2   single    1.521  0.020  1.521
 5EG  O10  C9   single    1.414  0.020  1.414
 5EG  N18  C2   single    1.359  0.020  1.359
 5EG  C13  C12  aromatic  1.389  0.020  1.389
 5EG  N4   N5   aromatic  1.323  0.020  1.323
 5EG  N4   C8   aromatic  1.337  0.020  1.337
 5EG  N5   N6   aromatic  1.273  0.020  1.273
 5EG  C2   O1   double    1.206  0.020  1.206
 5EG  C8   C9   single    1.482  0.020  1.482
 5EG  C8   N7   aromatic  1.307  0.020  1.307
 5EG  N6   N7   aromatic  1.333  0.020  1.333
 5EG  C3   H1   single    0.970  0.020  1.090
 5EG  C3   H2   single    0.970  0.020  1.090
 5EG  C12  H3   single    0.930  0.020  1.080
 5EG  C13  H4   single    0.930  0.020  1.080
 5EG  C14  H5   single    0.930  0.020  1.080
 5EG  C15  H6   single    0.930  0.020  1.080
 5EG  C24  H7   single    0.930  0.020  1.080
 5EG  C25  H8   single    0.930  0.020  1.080
 5EG  C28  H9   single    0.930  0.020  1.080
 5EG  C29  H10  single    0.930  0.020  1.080
 5EG  C9   H11  single    0.970  0.020  1.090
 5EG  C9   H12  single    0.970  0.020  1.090
 5EG  N18  H13  single    0.860  0.020  1.020
 5EG  N19  H14  single    0.890  0.020  1.040
 5EG  N22  H15  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
 5EG  N18  C2   O1   124.10  3.000
 5EG  O1   C2   C3   122.83  3.000
 5EG  N18  C2   C3   112.95  3.000
 5EG  H2   C3   H1   107.00  3.000
 5EG  H2   C3   N4   109.34  3.000
 5EG  H1   C3   N4   108.26  3.000
 5EG  H2   C3   C2   112.49  3.000
 5EG  H1   C3   C2   109.03  3.000
 5EG  N4   C3   C2   110.57  3.000
 5EG  O10  C11  C16  116.52  3.000
 5EG  O10  C11  C12  124.83  3.000
 5EG  C16  C11  C12  118.65  3.000
 5EG  H3   C12  C13  118.82  3.000
 5EG  H3   C12  C11  121.08  3.000
 5EG  C13  C12  C11  120.09  3.000
 5EG  H4   C13  C14  120.32  3.000
 5EG  H4   C13  C12  118.90  3.000
 5EG  C14  C13  C12  120.77  3.000
 5EG  H5   C14  C15  119.79  3.000
 5EG  H5   C14  C13  120.69  3.000
 5EG  C15  C14  C13  119.52  3.000
 5EG  H6   C15  C16  119.64  3.000
 5EG  H6   C15  C14  120.61  3.000
 5EG  C16  C15  C14  119.74  3.000
 5EG  CL1  C16  C15  119.96  3.000
 5EG  C15  C16  C11  121.21  3.000
 5EG  CL1  C16  C11  118.82  3.000
 5EG  N22  C20  O21  125.37  3.000
 5EG  O21  C20  N19  120.12  3.000
 5EG  N22  C20  N19  114.47  3.000
 5EG  N22  C23  C29  116.51  3.000
 5EG  N22  C23  C24  124.79  3.000
 5EG  C29  C23  C24  118.70  3.000
 5EG  H7   C24  C25  118.71  3.000
 5EG  H7   C24  C23  121.24  3.000
 5EG  C25  C24  C23  120.05  3.000
 5EG  H8   C25  C26  120.50  3.000
 5EG  H8   C25  C24  119.12  3.000
 5EG  C26  C25  C24  120.38  3.000
 5EG  CL2  C26  C28  119.78  3.000
 5EG  C28  C26  C25  120.28  3.000
 5EG  CL2  C26  C25  119.93  3.000
 5EG  H9   C28  C29  119.76  3.000
 5EG  H9   C28  C26  120.88  3.000
 5EG  C29  C28  C26  119.35  3.000
 5EG  H10  C29  C28  118.76  3.000
 5EG  H10  C29  C23  120.01  3.000
 5EG  C28  C29  C23  121.23  3.000
 5EG  C8   N4   N5   108.28  3.000
 5EG  C8   N4   C3   129.49  3.000
 5EG  N5   N4   C3   122.14  3.000
 5EG  N6   N5   N4   106.75  3.000
 5EG  N7   N6   N5   111.13  3.000
 5EG  C8   N7   N6   106.10  3.000
 5EG  C9   C8   N7   127.49  3.000
 5EG  N7   C8   N4   107.72  3.000
 5EG  C9   C8   N4   124.77  3.000
 5EG  H12  C9   H11  108.21  3.000
 5EG  H12  C9   O10  111.50  3.000
 5EG  H11  C9   O10  111.93  3.000
 5EG  H12  C9   C8   109.55  3.000
 5EG  H11  C9   C8   109.18  3.000
 5EG  O10  C9   C8   106.42  3.000
 5EG  C9   O10  C11  118.40  3.000
 5EG  H13  N18  N19  116.68  3.000
 5EG  H13  N18  C2   121.29  3.000
 5EG  N19  N18  C2   121.05  3.000
 5EG  H14  N19  N18  116.34  3.000
 5EG  H14  N19  C20  115.75  3.000
 5EG  N18  N19  C20  122.12  3.000
 5EG  H15  N22  C23  114.98  3.000
 5EG  H15  N22  C20  116.83  3.000
 5EG  C23  N22  C20  128.18  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
 5EG  CONST_01  C14  C15  C16  C11     0.00   0.0  0
 5EG  CONST_02  C14  C13  C12  C11     0.00   0.0  0
 5EG  CONST_03  C15  C16  C11  C12     0.00   0.0  0
 5EG  CONST_04  C15  C14  C13  C12     0.00   0.0  0
 5EG  CONST_05  C16  C15  C14  C13     0.00   0.0  0
 5EG  CONST_06  C16  C11  C12  C13     0.00   0.0  0
 5EG  CONST_07  C26  C25  C24  C23     0.00   0.0  0
 5EG  CONST_08  C26  C28  C29  C23     0.00   0.0  0
 5EG  CONST_09  C28  C26  C25  C24     0.00   0.0  0
 5EG  CONST_10  C28  C29  C23  C24     0.00   0.0  0
 5EG  CONST_11  C29  C28  C26  C25     0.00   0.0  0
 5EG  CONST_12  C29  C23  C24  C25     0.00   0.0  0
 5EG  CONST_13  N7   N6   N5   N4      0.00   0.0  0
 5EG  CONST_14  N6   N7   C8   N4      0.00   0.0  0
 5EG  CONST_15  N7   C8   N4   N5      0.00   0.0  0
 5EG  CONST_16  C8   N7   N6   N5      0.00   0.0  0
 5EG  CONST_17  C8   N4   N5   N6      0.00   0.0  0
 5EG  CONST_18  N6   N5   N4   C3    180.00   0.0  0
 5EG  CONST_19  N7   C8   N4   C3    180.00   0.0  0
 5EG  CONST_20  CL1  C16  C11  C12   180.00   0.0  0
 5EG  CONST_21  O10  C11  C12  C13   180.00   0.0  0
 5EG  CONST_22  CL1  C16  C15  C14   180.00   0.0  0
 5EG  CONST_23  O10  C11  C16  C15   180.00   0.0  0
 5EG  CONST_24  CL2  C26  C25  C24   180.00   0.0  0
 5EG  CONST_25  N22  C23  C24  C25   180.00   0.0  0
 5EG  CONST_26  N22  C23  C29  C28   180.00   0.0  0
 5EG  CONST_27  CL2  C26  C28  C29   180.00   0.0  0
 5EG  CONST_28  C9   C8   N4   N5    180.00   0.0  0
 5EG  CONST_29  C9   C8   N7   N6    180.00   0.0  0
 5EG  CONST_30  H6   C15  C16  C11   180.00   0.0  0
 5EG  CONST_31  H4   C13  C12  C11   180.00   0.0  0
 5EG  CONST_32  H5   C14  C13  C12   180.00   0.0  0
 5EG  CONST_33  H3   C12  C13  C14   180.00   0.0  0
 5EG  CONST_34  H8   C25  C24  C23   180.00   0.0  0
 5EG  CONST_35  H9   C28  C29  C23   180.00   0.0  0
 5EG  CONST_36  H10  C29  C23  C24   180.00   0.0  0
 5EG  CONST_37  H7   C24  C25  C26   180.00   0.0  0
 5EG  CONST_38  C24  C23  N22  C20     0.00   0.0  0
 5EG  CONST_39  C29  C23  N22  C20   180.00   0.0  0
 5EG  CONST_40  H15  N22  C23  C24   180.00   0.0  0
 5EG  CONST_41  O21  C20  N22  C23     0.00   0.0  0
 5EG  CONST_42  N19  C20  N22  C23   180.00   0.0  0
 5EG  CONST_43  N19  N18  C2   C3    180.00   0.0  0
 5EG  CONST_44  N19  N18  C2   O1      0.00   0.0  0
 5EG  CONST_47  H13  N18  C2   C3      0.00   0.0  0
 5EG  CONST_48  H14  N19  C20  O21     0.00   0.0  0
 5EG  Var_01    N5   N4   C3   C2     86.59  30.0  2
 5EG  Var_02    C8   C9   O10  C11  -175.55  30.0  3
 5EG  Var_03    O10  C9   C8   N4     61.53  30.0  2
 5EG  Var_04    N4   C3   C2   O1    -23.75  30.0  1
 5EG  Var_05    C20  N19  N18  C2    -80.72  30.0  2

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
 5EG  plan-1  C3   0.020
 5EG  plan-1  N4   0.020
 5EG  plan-1  N5   0.020
 5EG  plan-1  N6   0.020
 5EG  plan-1  N7   0.020
 5EG  plan-1  C8   0.020
 5EG  plan-1  C9   0.020
 5EG  plan-2  C11  0.020
 5EG  plan-2  C12  0.020
 5EG  plan-2  C13  0.020
 5EG  plan-2  C14  0.020
 5EG  plan-2  C15  0.020
 5EG  plan-2  C16  0.020
 5EG  plan-2  O10  0.020
 5EG  plan-2  CL1  0.020
 5EG  plan-2  H3   0.020
 5EG  plan-2  H4   0.020
 5EG  plan-2  H5   0.020
 5EG  plan-2  H6   0.020
 5EG  plan-3  C23  0.020
 5EG  plan-3  C24  0.020
 5EG  plan-3  C25  0.020
 5EG  plan-3  C26  0.020
 5EG  plan-3  C28  0.020
 5EG  plan-3  C29  0.020
 5EG  plan-3  N22  0.020
 5EG  plan-3  CL2  0.020
 5EG  plan-3  H7   0.020
 5EG  plan-3  H8   0.020
 5EG  plan-3  H9   0.020
 5EG  plan-3  H10  0.020
 5EG  plan-4  C2   0.020
 5EG  plan-4  C3   0.020
 5EG  plan-4  O1   0.020
 5EG  plan-4  N18  0.020
 5EG  plan-4  N19  0.020
 5EG  plan-4  H13  0.020
 5EG  plan-5  C20  0.020
 5EG  plan-5  C23  0.020
 5EG  plan-5  N18  0.020
 5EG  plan-5  N19  0.020
 5EG  plan-5  O21  0.020
 5EG  plan-5  N22  0.020
 5EG  plan-5  H14  0.020
 5EG  plan-5  H15  0.020

