# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 00:55:11 2020
#   Inital geometry file: a 124 line input string
#   Ligand name: 5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=O)c1cccc(Cn2c3CCCCCc3c4cccc(C(O)=O)c24)c1
#
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
 I4A  I4A  '5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid'  ligand  48  27  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_I4A
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
 I4A  O27   O  OC    -1  -0.582  -2.1660  -2.9876   1.2709
 I4A  C25   C  C      0   0.364  -1.0533  -2.5687   1.6300
 I4A  O26   O  O      0  -0.597  -0.6957  -2.2994   2.7974
 I4A  C4    C  CR6    0  -0.068   0.0081  -2.4312   0.5498
 I4A  C6    C  CR56   0   0.311   0.8931  -1.3516   0.3746
 I4A  C7    C  CR56   0   0.028   1.9161  -1.3954  -0.6035
 I4A  C9    C  CR5    0  -0.034   2.6158  -0.1499  -0.5663
 I4A  C10   C  CH2    0  -0.524   3.8324   0.1891  -1.3733
 I4A  C12   C  CH2    0  -0.444   4.8461   1.0297  -0.5972
 I4A  C14   C  CH2    0  -0.423   4.4851   2.5124  -0.4930
 I4A  C13   C  CH2    0  -0.448   3.0044   2.8214  -0.2906
 I4A  C11   C  CH2    0  -0.532   2.3050   2.0158   0.8026
 I4A  C8    C  CR5    0   0.328   1.9984   0.6120   0.3852
 I4A  C3    C  CR16   0  -0.390   2.0830  -2.5272  -1.4053
 I4A  C2    C  CR16   0  -0.262   1.2054  -3.5802  -1.2535
 I4A  C1    C  CR16   0  -0.335   0.1808  -3.5144  -0.3029
 I4A  N5    N  NR5    0  -0.580   0.9706  -0.1088   0.9692
 I4A  C15   C  CH2    0  -0.460  -0.0027   0.4988   1.8498
 I4A  C16   C  C      0   0.141  -1.0751   1.2678   1.1152
 I4A  C17   C  C1     0  -0.318  -1.7218   0.7202   0.0129
 I4A  C18   C  C      0  -0.019  -2.7343   1.4138  -0.6426
 I4A  C22   C  C      0   0.489  -3.3798   0.7546  -1.8219
 I4A  N24   N  NH2    0  -0.815  -4.6030   1.1954  -2.1546
 I4A  O23   O  O      0  -0.478  -2.8083  -0.1353  -2.4366
 I4A  C19   C  C1     0  -0.303  -3.0915   2.6870  -0.2020
 I4A  C20   C  C1     0  -0.230  -2.4479   3.2432   0.8917
 I4A  C21   C  C1     0  -0.314  -1.4497   2.5361   1.5479
 I4A  H10   H  HCH2   0   0.238   4.3103  -0.7448  -1.6811
 I4A  H10A  H  HCH2   0   0.230   3.5645   0.6981  -2.3066
 I4A  H12   H  HCH2   0   0.219   4.9597   0.5990   0.4018
 I4A  H12A  H  HCH2   0   0.230   5.8280   0.9474  -1.0697
 I4A  H14   H  HCH2   0   0.221   5.0617   2.9549   0.3244
 I4A  H14A  H  HCH2   0   0.222   4.8102   3.0261  -1.4021
 I4A  H13   H  HCH2   0   0.238   2.9078   3.8828  -0.0502
 I4A  H13A  H  HCH2   0   0.226   2.4581   2.6800  -1.2274
 I4A  H11   H  HCH2   0   0.250   2.9050   2.0218   1.7206
 I4A  H11A  H  HCH2   0   0.255   1.3770   2.5335   1.0547
 I4A  H3    H  HCR6   0   0.235   2.8742  -2.5675  -2.1446
 I4A  H2    H  HCR6   0   0.235   1.3039  -4.4647  -1.8704
 I4A  H1    H  HCR6   0   0.237  -0.4948  -4.3552  -0.2075
 I4A  H15   H  HCH2   0   0.314  -0.4455  -0.2874   2.4572
 I4A  H15A  H  HCH2   0   0.278   0.5155   1.1587   2.5459
 I4A  H17   H  H      0   0.270  -1.4516  -0.2661  -0.3436
 I4A  HN24  H  HNH2   0   0.412  -5.1292   1.8267  -1.5766
 I4A  HN2A  H  HNH2   0   0.404  -5.0951   0.7627  -2.9194
 I4A  H19   H  H      0   0.258  -3.8479   3.2676  -0.7144
 I4A  H20   H  H      0   0.263  -2.7153   4.2369   1.2258
 I4A  H21   H  H      0   0.260  -0.9506   2.9818   2.4007

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
 I4A  C25  O27   deloc     1.242  0.020  1.242
 I4A  O26  C25   deloc     1.250  0.020  1.250
 I4A  C25  C4    single    1.521  0.020  1.521
 I4A  C6   C4    aromatic  1.407  0.020  1.407
 I4A  C4   C1    aromatic  1.389  0.020  1.389
 I4A  N5   C6    aromatic  1.380  0.020  1.380
 I4A  C6   C7    aromatic  1.416  0.020  1.416
 I4A  C9   C7    aromatic  1.429  0.020  1.429
 I4A  C7   C3    aromatic  1.397  0.020  1.397
 I4A  C8   C9    aromatic  1.366  0.020  1.366
 I4A  C9   C10   single    1.499  0.020  1.499
 I4A  C12  C10   single    1.529  0.020  1.529
 I4A  C10  H10   single    0.970  0.020  1.090
 I4A  C10  H10A  single    0.970  0.020  1.090
 I4A  C14  C12   single    1.530  0.020  1.530
 I4A  C12  H12   single    0.970  0.020  1.090
 I4A  C12  H12A  single    0.970  0.020  1.090
 I4A  C13  C14   single    1.526  0.020  1.526
 I4A  C14  H14   single    0.970  0.020  1.090
 I4A  C14  H14A  single    0.970  0.020  1.090
 I4A  C13  C11   single    1.527  0.020  1.527
 I4A  C13  H13   single    0.970  0.020  1.090
 I4A  C13  H13A  single    0.970  0.020  1.090
 I4A  C11  C8    single    1.496  0.020  1.496
 I4A  C11  H11   single    0.970  0.020  1.090
 I4A  C11  H11A  single    0.970  0.020  1.090
 I4A  N5   C8    aromatic  1.385  0.020  1.385
 I4A  C3   C2    aromatic  1.379  0.020  1.379
 I4A  C3   H3    single    0.930  0.020  1.080
 I4A  C1   C2    aromatic  1.399  0.020  1.399
 I4A  C2   H2    single    0.930  0.020  1.080
 I4A  C1   H1    single    0.930  0.020  1.080
 I4A  C15  N5    single    1.446  0.020  1.446
 I4A  C16  C15   single    1.510  0.020  1.510
 I4A  C15  H15   single    0.970  0.020  1.090
 I4A  C15  H15A  single    0.970  0.020  1.090
 I4A  C17  C16   aromatic  1.390  0.020  1.390
 I4A  C21  C16   aromatic  1.391  0.020  1.391
 I4A  C18  C17   aromatic  1.391  0.020  1.391
 I4A  C17  H17   single    0.930  0.020  1.080
 I4A  C22  C18   single    1.497  0.020  1.497
 I4A  C19  C18   aromatic  1.394  0.020  1.394
 I4A  N24  C22   single    1.342  0.020  1.342
 I4A  C22  O23   double    1.223  0.020  1.223
 I4A  N24  HN24  single    0.860  0.020  1.020
 I4A  N24  HN2A  single    0.860  0.020  1.020
 I4A  C19  C20   aromatic  1.386  0.020  1.386
 I4A  C19  H19   single    0.930  0.020  1.080
 I4A  C20  C21   aromatic  1.388  0.020  1.388
 I4A  C20  H20   single    0.930  0.020  1.080
 I4A  C21  H21   single    0.930  0.020  1.080

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
 I4A  C4    C25  O26   116.37  3.000
 I4A  C4    C25  O27   116.77  3.000
 I4A  O26   C25  O27   126.79  3.000
 I4A  C1    C4   C6    116.34  3.000
 I4A  C1    C4   C25   116.89  3.000
 I4A  C6    C4   C25   126.65  3.000
 I4A  N5    C6   C7    106.55  3.000
 I4A  C7    C6   C4    121.11  3.000
 I4A  N5    C6   C4    132.28  3.000
 I4A  C3    C7   C9    131.49  3.000
 I4A  C3    C7   C6    120.52  3.000
 I4A  C9    C7   C6    107.99  3.000
 I4A  C8    C9   C10   127.99  3.000
 I4A  C10   C9   C7    125.49  3.000
 I4A  C8    C9   C7    106.43  3.000
 I4A  H10A  C10  H10   105.29  3.000
 I4A  H10A  C10  C12   109.82  3.000
 I4A  H10   C10  C12   108.84  3.000
 I4A  H10A  C10  C9    111.40  3.000
 I4A  H10   C10  C9    108.25  3.000
 I4A  C12   C10  C9    112.91  3.000
 I4A  H12A  C12  H12   105.78  3.000
 I4A  H12A  C12  C14   108.33  3.000
 I4A  H12   C12  C14   110.12  3.000
 I4A  H12A  C12  C10   109.56  3.000
 I4A  H12   C12  C10   108.42  3.000
 I4A  C14   C12  C10   114.28  3.000
 I4A  H14A  C14  H14   105.93  3.000
 I4A  H14A  C14  C13   107.67  3.000
 I4A  H14   C14  C13   109.30  3.000
 I4A  H14A  C14  C12   109.18  3.000
 I4A  H14   C14  C12   108.58  3.000
 I4A  C13   C14  C12   115.74  3.000
 I4A  H13A  C13  H13   105.66  3.000
 I4A  H13A  C13  C11   108.43  3.000
 I4A  H13   C13  C11   108.32  3.000
 I4A  H13A  C13  C14   110.17  3.000
 I4A  H13   C13  C14   108.16  3.000
 I4A  C11   C13  C14   115.62  3.000
 I4A  H11A  C11  H11   105.61  3.000
 I4A  H11A  C11  C8    109.58  3.000
 I4A  H11   C11  C8    110.53  3.000
 I4A  H11A  C11  C13   107.71  3.000
 I4A  H11   C11  C13   110.22  3.000
 I4A  C8    C11  C13   112.89  3.000
 I4A  N5    C8   C11   121.53  3.000
 I4A  N5    C8   C9    109.80  3.000
 I4A  C11   C8   C9    128.67  3.000
 I4A  H3    C3   C2    120.76  3.000
 I4A  H3    C3   C7    120.59  3.000
 I4A  C2    C3   C7    118.64  3.000
 I4A  H2    C2   C1    119.47  3.000
 I4A  H2    C2   C3    120.20  3.000
 I4A  C1    C2   C3    120.33  3.000
 I4A  H1    C1   C2    118.70  3.000
 I4A  H1    C1   C4    118.28  3.000
 I4A  C2    C1   C4    123.00  3.000
 I4A  C15   N5   C8    122.52  3.000
 I4A  C15   N5   C6    127.08  3.000
 I4A  C8    N5   C6    109.20  3.000
 I4A  H15A  C15  H15   105.93  3.000
 I4A  H15A  C15  C16   109.87  3.000
 I4A  H15   C15  C16   110.52  3.000
 I4A  H15A  C15  N5    108.86  3.000
 I4A  H15   C15  N5    108.07  3.000
 I4A  C16   C15  N5    113.31  3.000
 I4A  C21   C16  C17   118.71  3.000
 I4A  C21   C16  C15   120.27  3.000
 I4A  C17   C16  C15   121.02  3.000
 I4A  H17   C17  C18   118.72  3.000
 I4A  H17   C17  C16   120.24  3.000
 I4A  C18   C17  C16   121.04  3.000
 I4A  C19   C18  C22   122.73  3.000
 I4A  C19   C18  C17   119.54  3.000
 I4A  C22   C18  C17   117.72  3.000
 I4A  O23   C22  N24   122.70  3.000
 I4A  O23   C22  C18   120.97  3.000
 I4A  N24   C22  C18   116.33  3.000
 I4A  HN2A  N24  HN24  116.80  3.000
 I4A  HN2A  N24  C22   119.50  3.000
 I4A  HN24  N24  C22   122.76  3.000
 I4A  H19   C19  C20   118.88  3.000
 I4A  H19   C19  C18   121.29  3.000
 I4A  C20   C19  C18   119.81  3.000
 I4A  H20   C20  C21   119.97  3.000
 I4A  H20   C20  C19   119.84  3.000
 I4A  C21   C20  C19   120.18  3.000
 I4A  H21   C21  C20   119.57  3.000
 I4A  H21   C21  C16   119.70  3.000
 I4A  C20   C21  C16   120.72  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
 I4A  CONST_01  C8    N5   C6   C4    180.00   0.0  0
 I4A  CONST_02  C9    C7   C6   C4    180.00   0.0  0
 I4A  CONST_03  C3    C7   C6   C4      0.00   0.0  0
 I4A  CONST_04  C3    C2   C1   C4      0.00   0.0  0
 I4A  CONST_05  C2    C1   C4   C6      0.00   0.0  0
 I4A  CONST_06  C9    C8   N5   C6      0.00   0.0  0
 I4A  CONST_07  C8    C9   C7   C6      0.00   0.0  0
 I4A  CONST_08  C2    C3   C7   C6      0.00   0.0  0
 I4A  CONST_09  C1    C4   C6   C7      0.00   0.0  0
 I4A  CONST_10  C8    N5   C6   C7      0.00   0.0  0
 I4A  CONST_11  N5    C8   C9   C7      0.00   0.0  0
 I4A  CONST_12  C1    C2   C3   C7      0.00   0.0  0
 I4A  CONST_13  N5    C6   C7   C9      0.00   0.0  0
 I4A  CONST_14  C2    C3   C7   C9    180.00   0.0  0
 I4A  CONST_15  C3    C7   C9   C8    180.00   0.0  0
 I4A  CONST_16  N5    C6   C7   C3    180.00   0.0  0
 I4A  CONST_17  N5    C6   C4   C1    180.00   0.0  0
 I4A  CONST_18  C19   C18  C17  C16     0.00   0.0  0
 I4A  CONST_19  C19   C20  C21  C16     0.00   0.0  0
 I4A  CONST_20  C20   C21  C16  C17     0.00   0.0  0
 I4A  CONST_21  C20   C19  C18  C17     0.00   0.0  0
 I4A  CONST_22  C21   C16  C17  C18     0.00   0.0  0
 I4A  CONST_23  C21   C20  C19  C18     0.00   0.0  0
 I4A  CONST_24  N5    C6   C4   C25     0.00   0.0  0
 I4A  CONST_25  C7    C6   C4   C25   180.00   0.0  0
 I4A  CONST_26  C2    C1   C4   C25   180.00   0.0  0
 I4A  CONST_27  C15   N5   C6   C4      0.00   0.0  0
 I4A  CONST_28  C15   N5   C6   C7    180.00   0.0  0
 I4A  CONST_29  C15   N5   C8   C9    180.00   0.0  0
 I4A  CONST_30  C15   N5   C8   C11     0.00   0.0  0
 I4A  CONST_31  C18   C17  C16  C15   180.00   0.0  0
 I4A  CONST_32  C20   C21  C16  C15   180.00   0.0  0
 I4A  CONST_33  C22   C18  C17  C16   180.00   0.0  0
 I4A  CONST_34  C20   C19  C18  C22   180.00   0.0  0
 I4A  CONST_35  H2    C2   C1   C4    180.00   0.0  0
 I4A  CONST_36  H1    C1   C4   C6    180.00   0.0  0
 I4A  CONST_37  H3    C3   C7   C6    180.00   0.0  0
 I4A  CONST_38  H20   C20  C21  C16   180.00   0.0  0
 I4A  CONST_39  H21   C21  C16  C17   180.00   0.0  0
 I4A  CONST_40  H19   C19  C18  C17   180.00   0.0  0
 I4A  CONST_41  H17   C17  C18  C19   180.00   0.0  0
 I4A  CONST_42  HN24  N24  C22  C18     0.00   0.0  0
 I4A  CONST_43  HN2A  N24  C22  C18   180.00   0.0  0
 I4A  Var_01    C12   C10  C9   C7   -142.02  30.0  1
 I4A  Var_02    C13   C11  C8   C9     24.55  30.0  1
 I4A  Var_03    C14   C12  C10  C9    -78.38  30.0  1
 I4A  Var_04    C13   C14  C12  C10    38.42  30.0  1
 I4A  Var_05    C11   C13  C14  C12    48.12  30.0  1
 I4A  Var_06    C8    C11  C13  C14   -76.32  30.0  1
 I4A  Var_07    C16   C15  N5   C6    -87.70  30.0  2
 I4A  Var_08    C17   C16  C15  N5     46.78  30.0  2
 I4A  Var_09    C6    C4   C25  O27   136.26  30.0  2
 I4A  Var_10    N24   C22  C18  C17   158.35  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
 I4A  plan-1  C15   0.020
 I4A  plan-1  C16   0.020
 I4A  plan-1  C17   0.020
 I4A  plan-1  C18   0.020
 I4A  plan-1  C22   0.020
 I4A  plan-1  C19   0.020
 I4A  plan-1  C20   0.020
 I4A  plan-1  C21   0.020
 I4A  plan-1  H17   0.020
 I4A  plan-1  H19   0.020
 I4A  plan-1  H20   0.020
 I4A  plan-1  H21   0.020
 I4A  plan-2  C25   0.020
 I4A  plan-2  C4    0.020
 I4A  plan-2  C6    0.020
 I4A  plan-2  C7    0.020
 I4A  plan-2  C9    0.020
 I4A  plan-2  C10   0.020
 I4A  plan-2  C11   0.020
 I4A  plan-2  C8    0.020
 I4A  plan-2  C3    0.020
 I4A  plan-2  C2    0.020
 I4A  plan-2  C1    0.020
 I4A  plan-2  N5    0.020
 I4A  plan-2  C15   0.020
 I4A  plan-2  H3    0.020
 I4A  plan-2  H2    0.020
 I4A  plan-2  H1    0.020
 I4A  plan-3  C18   0.020
 I4A  plan-3  C22   0.020
 I4A  plan-3  N24   0.020
 I4A  plan-3  O23   0.020
 I4A  plan-3  HN24  0.020
 I4A  plan-3  HN2A  0.020
 I4A  plan-4  O27   0.020
 I4A  plan-4  C25   0.020
 I4A  plan-4  O26   0.020
 I4A  plan-4  C4    0.020

