# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 02:42:41 2022
#   Inital geometry file: a 92 line input string
#   Ligand name: methyl 8-cyclopropyl-2-methyl-9~{H}-pyrido[2,3-b]indole-3-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COC(=O)c1cc2c([nH]c3c(cccc23)C4CC4)nc1C
#
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
 67V  67V  "methyl 8-cyclopropyl-2-methyl-9H-pyrido[2,3-b]indole-3-carboxylate"  ligand  37  21  .  2022-09-16  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_67V
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
 67V  C1   C  CH3   0  -0.418  31.1871  31.4377  65.8113
 67V  C2   C  CR16  0  -0.353  35.4381  38.9673  62.6271
 67V  C3   C  CR16  0  -0.248  35.3753  38.3215  63.8679
 67V  C4   C  CR16  0  -0.389  34.6363  37.1637  64.0314
 67V  C5   C  CR6   0   0.082  34.7674  38.4908  61.5100
 67V  C6   C  CH1   0  -0.314  34.8198  39.1406  60.1753
 67V  C7   C  CH2   0  -0.489  34.8940  40.6275  60.0391
 67V  C8   C  CH2   0  -0.473  33.6298  39.9138  59.6741
 67V  C9   C  CR56  0   0.340  34.0283  37.3222  61.6936
 67V  C10  C  CR56  0   0.042  33.9541  36.6538  62.9296
 67V  C12  C  CR56  0   0.462  32.7177  35.5472  61.3566
 67V  C13  C  CR56  0   0.042  33.1104  35.5078  62.7100
 67V  C14  C  CR16  0  -0.254  32.6381  34.4557  63.4626
 67V  C15  C  CR6   0  -0.198  31.8162  33.5025  62.8516
 67V  C16  C  CR6   0   0.245  31.4855  33.6505  61.4798
 67V  C18  C  C     0   0.578  31.3201  32.3557  63.6454
 67V  C21  C  CH3   0  -0.723  30.6034  32.7022  60.7237
 67V  N11  N  NR15  0  -0.764  33.2736  36.6361  60.7661
 67V  N17  N  N     0  -0.455  31.9373  34.6695  60.7554
 67V  O19  O  O2    0  -0.462  31.5928  32.4894  64.9394
 67V  O20  O  O     0  -0.441  30.7376  31.3950  63.2019
 67V  H1   H  HCH3  0   0.251  31.5188  31.7301  66.8034
 67V  H2   H  HCH3  0   0.237  30.1038  31.3173  65.8144
 67V  H3   H  HCH3  0   0.237  31.6521  30.4900  65.5401
 67V  H4   H  HCR6  0   0.250  36.0313  39.8687  62.5340
 67V  H5   H  HCR6  0   0.251  35.9166  38.7372  64.7075
 67V  H6   H  HCR6  0   0.250  34.5896  36.6661  64.9918
 67V  H7   H  HCH1  0   0.278  35.3514  38.5694  59.4188
 67V  H8   H  HCH2  0   0.254  35.5053  41.0301  59.2422
 67V  H9   H  HCH2  0   0.251  34.8923  41.2255  60.9418
 67V  H10  H  HCH2  0   0.250  32.7841  40.0170  60.3425
 67V  H11  H  HCH2  0   0.254  33.3672  39.8249  58.6280
 67V  H12  H  HCR6  0   0.268  32.9074  34.3690  64.5063
 67V  H13  H  HCH3  0   0.244  30.4591  33.0890  59.7175
 67V  H14  H  HCH3  0   0.251  31.0430  31.7083  60.6520
 67V  H15  H  HCH3  0   0.248  29.6277  32.5854  61.1937
 67V  H16  H  HNR5  0   0.415  33.1443  36.8975  59.8011

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
 67V  C7   C8   single    1.497  0.020  1.497
 67V  C7   C6   single    1.495  0.020  1.495
 67V  C8   C6   single    1.505  0.020  1.505
 67V  C6   C5   single    1.485  0.020  1.485
 67V  N11  C12  aromatic  1.358  0.020  1.358
 67V  N11  C9   aromatic  1.379  0.020  1.379
 67V  N17  C12  aromatic  1.319  0.020  1.319
 67V  N17  C16  aromatic  1.329  0.020  1.329
 67V  C21  C16  single    1.500  0.020  1.500
 67V  C12  C13  aromatic  1.410  0.020  1.410
 67V  C5   C9   aromatic  1.395  0.020  1.395
 67V  C5   C2   aromatic  1.387  0.020  1.387
 67V  C16  C15  aromatic  1.419  0.020  1.419
 67V  C9   C10  aromatic  1.407  0.020  1.407
 67V  C13  C10  aromatic  1.440  0.020  1.440
 67V  C13  C14  aromatic  1.377  0.020  1.377
 67V  C2   C3   aromatic  1.400  0.020  1.400
 67V  C10  C4   aromatic  1.393  0.020  1.393
 67V  C15  C14  aromatic  1.399  0.020  1.399
 67V  C15  C18  single    1.480  0.020  1.480
 67V  O20  C18  double    1.208  0.020  1.208
 67V  C18  O19  single    1.329  0.020  1.329
 67V  C3   C4   aromatic  1.383  0.020  1.383
 67V  O19  C1   single    1.425  0.020  1.425
 67V  C1   H1   single    0.970  0.020  1.090
 67V  C1   H2   single    0.970  0.020  1.090
 67V  C1   H3   single    0.970  0.020  1.090
 67V  C2   H4   single    0.930  0.020  1.080
 67V  C3   H5   single    0.930  0.020  1.080
 67V  C4   H6   single    0.930  0.020  1.080
 67V  C6   H7   single    0.970  0.020  1.090
 67V  C7   H8   single    0.970  0.020  1.090
 67V  C7   H9   single    0.970  0.020  1.090
 67V  C8   H10  single    0.970  0.020  1.090
 67V  C8   H11  single    0.970  0.020  1.090
 67V  C14  H12  single    0.930  0.020  1.080
 67V  C21  H13  single    0.970  0.020  1.090
 67V  C21  H14  single    0.970  0.020  1.090
 67V  C21  H15  single    0.970  0.020  1.090
 67V  N11  H16  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
 67V  H3   C1   H2   109.18  3.000
 67V  H3   C1   H1   109.33  3.000
 67V  H2   C1   H1   109.31  3.000
 67V  H3   C1   O19  111.60  3.000
 67V  H2   C1   O19  111.48  3.000
 67V  H1   C1   O19  105.86  3.000
 67V  H4   C2   C5   118.78  3.000
 67V  H4   C2   C3   118.98  3.000
 67V  C5   C2   C3   122.24  3.000
 67V  H5   C3   C4   119.81  3.000
 67V  H5   C3   C2   119.21  3.000
 67V  C4   C3   C2   120.98  3.000
 67V  H6   C4   C10  120.83  3.000
 67V  H6   C4   C3   120.84  3.000
 67V  C10  C4   C3   118.34  3.000
 67V  C9   C5   C6   120.23  3.000
 67V  C9   C5   C2   115.97  3.000
 67V  C6   C5   C2   123.80  3.000
 67V  H7   C6   C8   115.15  3.000
 67V  H7   C6   C7   115.79  3.000
 67V  C8   C6   C7    59.86  3.000
 67V  H7   C6   C5   114.38  3.000
 67V  C8   C6   C5   119.74  3.000
 67V  C7   C6   C5   121.24  3.000
 67V  H9   C7   H8   114.17  3.000
 67V  H9   C7   C8   117.73  3.000
 67V  H8   C7   C8   118.36  3.000
 67V  H9   C7   C6   118.25  3.000
 67V  H8   C7   C6   117.72  3.000
 67V  C8   C7   C6    60.40  3.000
 67V  H11  C8   H10  114.52  3.000
 67V  H11  C8   C7   118.67  3.000
 67V  H10  C8   C7   117.62  3.000
 67V  H11  C8   C6   118.13  3.000
 67V  H10  C8   C6   117.45  3.000
 67V  C7   C8   C6    59.74  3.000
 67V  N11  C9   C10  109.01  3.000
 67V  C10  C9   C5   122.79  3.000
 67V  N11  C9   C5   128.20  3.000
 67V  C13  C10  C9   105.97  3.000
 67V  C13  C10  C4   134.35  3.000
 67V  C9   C10  C4   119.68  3.000
 67V  N17  C12  N11  125.27  3.000
 67V  N17  C12  C13  125.71  3.000
 67V  N11  C12  C13  109.03  3.000
 67V  C14  C13  C12  116.78  3.000
 67V  C14  C13  C10  136.53  3.000
 67V  C12  C13  C10  106.70  3.000
 67V  H12  C14  C15  120.87  3.000
 67V  H12  C14  C13  120.22  3.000
 67V  C15  C14  C13  118.91  3.000
 67V  C18  C15  C16  121.41  3.000
 67V  C18  C15  C14  119.38  3.000
 67V  C16  C15  C14  119.21  3.000
 67V  N17  C16  C21  114.20  3.000
 67V  C21  C16  C15  123.95  3.000
 67V  N17  C16  C15  121.85  3.000
 67V  O20  C18  O19  122.44  3.000
 67V  O19  C18  C15  112.04  3.000
 67V  O20  C18  C15  125.51  3.000
 67V  H15  C21  H14  106.99  3.000
 67V  H15  C21  H13  108.57  3.000
 67V  H14  C21  H13  108.49  3.000
 67V  H15  C21  C16  112.16  3.000
 67V  H14  C21  C16  111.89  3.000
 67V  H13  C21  C16  108.63  3.000
 67V  H16  N11  C12  124.88  3.000
 67V  H16  N11  C9   125.81  3.000
 67V  C12  N11  C9   109.30  3.000
 67V  C16  N17  C12  117.55  3.000
 67V  C18  O19  C1   117.58  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
 67V  CONST_01  N11  C9   C5   C2    180.00   0.0  0
 67V  CONST_02  C10  C9   C5   C2      0.00   0.0  0
 67V  CONST_03  C10  C4   C3   C2      0.00   0.0  0
 67V  CONST_04  C9   C5   C2   C3      0.00   0.0  0
 67V  CONST_05  C9   C10  C4   C3      0.00   0.0  0
 67V  CONST_06  C13  C10  C4   C3    180.00   0.0  0
 67V  CONST_07  N11  C9   C10  C4    180.00   0.0  0
 67V  CONST_08  C5   C9   C10  C4      0.00   0.0  0
 67V  CONST_09  C12  C13  C10  C4    180.00   0.0  0
 67V  CONST_10  C14  C13  C10  C4      0.00   0.0  0
 67V  CONST_11  C5   C2   C3   C4      0.00   0.0  0
 67V  CONST_12  C12  N11  C9   C5    180.00   0.0  0
 67V  CONST_13  C13  C10  C9   C5    180.00   0.0  0
 67V  CONST_14  N17  C12  N11  C9    180.00   0.0  0
 67V  CONST_15  C13  C12  N11  C9      0.00   0.0  0
 67V  CONST_16  C12  C13  C10  C9      0.00   0.0  0
 67V  CONST_17  C14  C13  C10  C9    180.00   0.0  0
 67V  CONST_18  C12  N11  C9   C10     0.00   0.0  0
 67V  CONST_19  N11  C12  C13  C10     0.00   0.0  0
 67V  CONST_20  N17  C12  C13  C10   180.00   0.0  0
 67V  CONST_21  C15  C14  C13  C10   180.00   0.0  0
 67V  CONST_22  C15  C16  N17  C12     0.00   0.0  0
 67V  CONST_23  C15  C14  C13  C12     0.00   0.0  0
 67V  CONST_24  C16  N17  C12  C13     0.00   0.0  0
 67V  CONST_25  N11  C9   C10  C13     0.00   0.0  0
 67V  CONST_26  C16  C15  C14  C13     0.00   0.0  0
 67V  CONST_27  N11  C12  C13  C14   180.00   0.0  0
 67V  CONST_28  N17  C12  C13  C14     0.00   0.0  0
 67V  CONST_29  N17  C16  C15  C14     0.00   0.0  0
 67V  CONST_30  N11  C12  N17  C16   180.00   0.0  0
 67V  CONST_31  C6   C5   C2   C3    180.00   0.0  0
 67V  CONST_32  N11  C9   C5   C6      0.00   0.0  0
 67V  CONST_33  C10  C9   C5   C6    180.00   0.0  0
 67V  CONST_34  C21  C16  N17  C12   180.00   0.0  0
 67V  CONST_35  C18  C15  C14  C13   180.00   0.0  0
 67V  CONST_36  C21  C16  C15  C14   180.00   0.0  0
 67V  CONST_37  N17  C16  C15  C18   180.00   0.0  0
 67V  CONST_38  H6   C4   C3   C2    180.00   0.0  0
 67V  CONST_39  H4   C2   C3   C4    180.00   0.0  0
 67V  CONST_40  H16  N11  C9   C5      0.00   0.0  0
 67V  CONST_41  H5   C3   C2   C5    180.00   0.0  0
 67V  CONST_42  H4   C2   C5   C6      0.00   0.0  0
 67V  CONST_43  H4   C2   C5   C9    180.00   0.0  0
 67V  CONST_44  H6   C4   C10  C9    180.00   0.0  0
 67V  CONST_45  H16  N11  C9   C10   180.00   0.0  0
 67V  CONST_46  H12  C14  C13  C10     0.00   0.0  0
 67V  CONST_47  H5   C3   C4   C10   180.00   0.0  0
 67V  CONST_48  H12  C14  C13  C12   180.00   0.0  0
 67V  CONST_49  H16  N11  C12  C13   180.00   0.0  0
 67V  CONST_50  H6   C4   C10  C13     0.00   0.0  0
 67V  CONST_51  H12  C14  C15  C16   180.00   0.0  0
 67V  CONST_52  H16  N11  C12  N17     0.00   0.0  0
 67V  Var_01    C7   C6   C5   C2    -35.18  30.0  2
 67V  Var_02    C8   C6   C5   C2   -105.93  30.0  2
 67V  Var_03    C8   C7   C6   C5   -108.59  30.0  1
 67V  Var_04    C9   C5   C6   C7    145.73  30.0  2
 67V  Var_05    C9   C5   C6   C8     74.98  30.0  2
 67V  Var_06    H7   C6   C5   C2    111.29  30.0  2
 67V  Var_07    H8   C7   C6   C5    142.84  30.0  1
 67V  Var_08    H9   C7   C6   C5     -1.00  30.0  1
 67V  Var_09    H10  C8   C6   C5      3.47  30.0  1
 67V  Var_10    H11  C8   C6   C5   -140.42  30.0  1
 67V  Var_11    H10  C8   C7   C6    107.27  30.0  1
 67V  Var_12    H11  C8   C7   C6   -107.65  30.0  1
 67V  Var_13    H8   C7   C8   C6    107.54  30.0  1
 67V  Var_14    H9   C7   C8   C6   -108.44  30.0  1
 67V  Var_15    H7   C6   C8   C7   -106.45  30.0  1
 67V  Var_16    H7   C6   C5   C9    -67.80  30.0  2
 67V  Var_17    O20  C18  C15  C14  -171.01  30.0  2
 67V  Var_18    O19  C18  C15  C14     8.75  30.0  2
 67V  Var_19    O20  C18  C15  C16     8.44  30.0  2
 67V  Var_20    O19  C18  C15  C16  -171.80  30.0  2
 67V  Var_21    H13  C21  C16  C15   175.95  30.0  2
 67V  Var_22    H14  C21  C16  C15   -64.30  30.0  2
 67V  Var_23    H15  C21  C16  C15    55.94  30.0  2
 67V  Var_24    H13  C21  C16  N17    -3.56  30.0  2
 67V  Var_25    H14  C21  C16  N17   116.19  30.0  2
 67V  Var_26    H15  C21  C16  N17  -123.57  30.0  2
 67V  Var_27    C15  C18  O19  C1   -178.93  30.0  1
 67V  Var_28    O20  C18  O19  C1      0.84  30.0  1
 67V  Var_29    H1   C1   O19  C18   178.81  30.0  3
 67V  Var_30    H2   C1   O19  C18   -62.43  30.0  3
 67V  Var_31    H3   C1   O19  C18    59.95  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
 67V  chir_01  C6  C7  C8  C5  both

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
 67V  plan-1  C2   0.020
 67V  plan-1  C3   0.020
 67V  plan-1  C4   0.020
 67V  plan-1  C5   0.020
 67V  plan-1  C6   0.020
 67V  plan-1  C9   0.020
 67V  plan-1  C10  0.020
 67V  plan-1  C12  0.020
 67V  plan-1  C13  0.020
 67V  plan-1  C14  0.020
 67V  plan-1  C15  0.020
 67V  plan-1  C16  0.020
 67V  plan-1  C18  0.020
 67V  plan-1  C21  0.020
 67V  plan-1  N11  0.020
 67V  plan-1  N17  0.020
 67V  plan-1  H4   0.020
 67V  plan-1  H5   0.020
 67V  plan-1  H6   0.020
 67V  plan-1  H12  0.020
 67V  plan-1  H16  0.020
 67V  plan-2  C15  0.020
 67V  plan-2  C18  0.020
 67V  plan-2  O19  0.020
 67V  plan-2  O20  0.020

