# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 11 15:04:10 2020
#   Inital geometry file: a 111 line input string
#   Ligand name: [(3~{R})-3,5-dimethyl-9-oxidanyl-11~{H}-pyrano[3,2-a]carbazol-3-yl]methyl ethanoate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(=O)OC[C@]1(C)Oc2c(C)cc3c([nH]c4cc(O)ccc34)c2C=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
 9ET  9ET  '[(3~{R})-3,5-dimethyl-9-oxidanyl-11~{H}-pyrano[3,2-a]carbazol-3-yl]methyl ethanoate'  ligand  44  25  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9ET
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
 9ET  C10  C  CR66  0  -0.039   0.1041  -1.0903  -0.2791
 9ET  C13  C  CR6   0  -0.025   0.5601   0.9517  -1.5765
 9ET  C15  C  CR16  0  -0.441  -0.7579   1.3527  -1.4051
 9ET  C17  C  CR56  0   0.053  -3.0424   0.6941  -0.3290
 9ET  C20  C  CR6   0   0.352  -5.6115   0.3011   0.6698
 9ET  C22  C  CR16  0  -0.469  -4.6487  -0.6645   0.9306
 9ET  C01  C  CH3   0  -0.770   5.3004   2.4275   0.8330
 9ET  C02  C  C     0   0.569   4.4603   1.3543   1.4571
 9ET  C05  C  CH2   0  -0.154   3.1986  -0.5859   0.9815
 9ET  C06  C  CR6   0   0.093   2.8738  -1.4595  -0.2285
 9ET  C07  C  CH3   0  -0.672   4.1262  -2.0301  -0.8739
 9ET  C08  C  CR16  0  -0.252   1.9471  -2.5543   0.2320
 9ET  C09  C  CR16  0  -0.217   0.6302  -2.3496   0.2192
 9ET  C11  C  CR66  0   0.299   0.9632  -0.2652  -1.0070
 9ET  C14  C  CH3   0  -0.715   1.5413   1.7842  -2.3484
 9ET  C16  C  CR56  0   0.071  -1.6503   0.5657  -0.6825
 9ET  C18  C  CR16  0  -0.360  -4.0292   1.6455  -0.5731
 9ET  C19  C  CR16  0  -0.352  -5.3045   1.4505  -0.0776
 9ET  C23  C  CR56  0   0.353  -3.3723  -0.4498   0.4228
 9ET  C25  C  CR56  0   0.296  -1.2096  -0.6480  -0.1262
 9ET  N24  N  NR15  0  -0.800  -2.2573  -1.2398   0.5331
 9ET  O03  O  O     0  -0.454   4.1690   1.2877   2.6252
 9ET  O04  O  O2    0  -0.448   4.0468   0.4742   0.5513
 9ET  O12  O  O     0  -0.484   2.2357  -0.6676  -1.2342
 9ET  O21  O  OH1   0  -0.637  -6.8805   0.1852   1.1154
 9ET  H1   H  HCR6  0   0.243  -1.0843   2.2942  -1.8320
 9ET  H2   H  HCR6  0   0.274  -4.8844  -1.5531   1.5053
 9ET  H3   H  HCH3  0   0.264   5.8002   3.0137   1.5986
 9ET  H4   H  HCH3  0   0.269   6.0419   2.0048   0.1565
 9ET  H5   H  HCH3  0   0.275   4.6662   3.0937   0.2454
 9ET  H6   H  HCH2  0   0.252   2.2810  -0.1822   1.4193
 9ET  H7   H  HCH2  0   0.256   3.6935  -1.1975   1.7410
 9ET  H8   H  HCH3  0   0.248   3.8625  -2.7082  -1.6855
 9ET  H9   H  HCH3  0   0.252   4.7655  -1.2449  -1.2749
 9ET  H10  H  HCH3  0   0.238   4.7003  -2.5943  -0.1392
 9ET  H11  H  HCR6  0   0.268   2.3774  -3.4823   0.5860
 9ET  H13  H  HCR6  0   0.256  -0.0503  -3.1212   0.5587
 9ET  H15  H  HCH3  0   0.241   1.8603   1.2899  -3.2679
 9ET  H16  H  HCH3  0   0.241   1.0987   2.7395  -2.6261
 9ET  H17  H  HCH3  0   0.238   2.4429   1.9892  -1.7689
 9ET  H18  H  HCR6  0   0.248  -3.8076   2.5350  -1.1499
 9ET  H19  H  HCR6  0   0.259  -6.0815   2.1810  -0.2633
 9ET  H20  H  HNR5  0   0.409  -2.2182  -2.1066   1.0423
 9ET  H21  H  HOH1  0   0.474  -6.9876  -0.6332   1.6128

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
 9ET  C14  C13  single    1.501  0.020  1.501
 9ET  C18  C19  aromatic  1.382  0.020  1.382
 9ET  C18  C17  aromatic  1.392  0.020  1.392
 9ET  C15  C13  aromatic  1.388  0.020  1.388
 9ET  C15  C16  aromatic  1.392  0.020  1.392
 9ET  C19  C20  aromatic  1.405  0.020  1.405
 9ET  C13  C11  aromatic  1.403  0.020  1.403
 9ET  C17  C16  aromatic  1.442  0.020  1.442
 9ET  C17  C23  aromatic  1.408  0.020  1.408
 9ET  C16  C25  aromatic  1.406  0.020  1.406
 9ET  C20  O21  single    1.350  0.020  1.350
 9ET  C20  C22  aromatic  1.388  0.020  1.388
 9ET  C11  O12  single    1.354  0.020  1.354
 9ET  C11  C10  aromatic  1.396  0.020  1.396
 9ET  C07  C06  single    1.520  0.020  1.520
 9ET  C23  C22  aromatic  1.390  0.020  1.390
 9ET  C23  N24  aromatic  1.371  0.020  1.371
 9ET  C25  C10  aromatic  1.394  0.020  1.394
 9ET  C25  N24  aromatic  1.372  0.020  1.372
 9ET  O12  C06  single    1.430  0.020  1.430
 9ET  C10  C09  single    1.453  0.020  1.453
 9ET  C06  C08  single    1.506  0.020  1.506
 9ET  C06  C05  single    1.527  0.020  1.527
 9ET  C08  C09  double    1.333  0.020  1.333
 9ET  C05  O04  single    1.424  0.020  1.424
 9ET  O04  C02  single    1.329  0.020  1.329
 9ET  C02  C01  single    1.499  0.020  1.499
 9ET  C02  O03  double    1.206  0.020  1.206
 9ET  C15  H1   single    0.930  0.020  1.080
 9ET  C22  H2   single    0.930  0.020  1.080
 9ET  C01  H3   single    0.970  0.020  1.090
 9ET  C01  H4   single    0.970  0.020  1.090
 9ET  C01  H5   single    0.970  0.020  1.090
 9ET  C05  H6   single    0.970  0.020  1.090
 9ET  C05  H7   single    0.970  0.020  1.090
 9ET  C07  H8   single    0.970  0.020  1.090
 9ET  C07  H9   single    0.970  0.020  1.090
 9ET  C07  H10  single    0.970  0.020  1.090
 9ET  C08  H11  single    0.930  0.020  1.080
 9ET  C09  H13  single    0.930  0.020  1.080
 9ET  C14  H15  single    0.970  0.020  1.090
 9ET  C14  H16  single    0.970  0.020  1.090
 9ET  C14  H17  single    0.970  0.020  1.090
 9ET  C18  H18  single    0.930  0.020  1.080
 9ET  C19  H19  single    0.930  0.020  1.080
 9ET  N24  H20  single    0.860  0.020  1.020
 9ET  O21  H21  single    0.850  0.020  0.980

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
 9ET  C25  C10  C11  116.71  3.000
 9ET  C25  C10  C09  125.34  3.000
 9ET  C11  C10  C09  117.92  3.000
 9ET  C14  C13  C11  120.15  3.000
 9ET  C11  C13  C15  118.25  3.000
 9ET  C14  C13  C15  121.61  3.000
 9ET  H1   C15  C16  120.16  3.000
 9ET  H1   C15  C13  119.21  3.000
 9ET  C16  C15  C13  120.62  3.000
 9ET  C23  C17  C18  118.86  3.000
 9ET  C23  C17  C16  106.55  3.000
 9ET  C18  C17  C16  134.59  3.000
 9ET  O21  C20  C19  116.83  3.000
 9ET  O21  C20  C22  122.02  3.000
 9ET  C19  C20  C22  121.16  3.000
 9ET  H2   C22  C23  121.32  3.000
 9ET  H2   C22  C20  121.25  3.000
 9ET  C23  C22  C20  117.43  3.000
 9ET  H5   C01  H4   107.34  3.000
 9ET  H5   C01  H3   108.51  3.000
 9ET  H4   C01  H3   109.52  3.000
 9ET  H5   C01  C02  109.60  3.000
 9ET  H4   C01  C02  111.24  3.000
 9ET  H3   C01  C02  110.53  3.000
 9ET  O04  C02  O03  123.27  3.000
 9ET  O03  C02  C01  125.33  3.000
 9ET  O04  C02  C01  111.39  3.000
 9ET  H7   C05  H6   107.94  3.000
 9ET  H7   C05  O04  110.89  3.000
 9ET  H6   C05  O04  110.23  3.000
 9ET  H7   C05  C06  109.06  3.000
 9ET  H6   C05  C06  110.47  3.000
 9ET  O04  C05  C06  108.24  3.000
 9ET  O12  C06  C08  110.06  3.000
 9ET  C08  C06  C07  111.33  3.000
 9ET  O12  C06  C07  106.07  3.000
 9ET  C08  C06  C05  107.72  3.000
 9ET  O12  C06  C05  109.59  3.000
 9ET  C07  C06  C05  112.07  3.000
 9ET  H10  C07  H9   108.19  3.000
 9ET  H10  C07  H8   107.90  3.000
 9ET  H9   C07  H8   108.44  3.000
 9ET  H10  C07  C06  110.01  3.000
 9ET  H9   C07  C06  111.68  3.000
 9ET  H8   C07  C06  110.51  3.000
 9ET  H11  C08  C09  121.85  3.000
 9ET  H11  C08  C06  118.59  3.000
 9ET  C09  C08  C06  119.55  3.000
 9ET  H13  C09  C08  120.54  3.000
 9ET  H13  C09  C10  119.83  3.000
 9ET  C08  C09  C10  119.62  3.000
 9ET  O12  C11  C13  117.37  3.000
 9ET  O12  C11  C10  119.36  3.000
 9ET  C13  C11  C10  123.20  3.000
 9ET  H17  C14  H16  107.84  3.000
 9ET  H17  C14  H15  106.92  3.000
 9ET  H16  C14  H15  107.53  3.000
 9ET  H17  C14  C13  111.80  3.000
 9ET  H16  C14  C13  110.62  3.000
 9ET  H15  C14  C13  111.91  3.000
 9ET  C25  C16  C17  106.41  3.000
 9ET  C25  C16  C15  119.50  3.000
 9ET  C17  C16  C15  134.09  3.000
 9ET  H18  C18  C19  119.71  3.000
 9ET  H18  C18  C17  120.64  3.000
 9ET  C19  C18  C17  119.65  3.000
 9ET  H19  C19  C18  120.37  3.000
 9ET  H19  C19  C20  119.11  3.000
 9ET  C18  C19  C20  120.52  3.000
 9ET  N24  C23  C22  128.92  3.000
 9ET  N24  C23  C17  108.70  3.000
 9ET  C22  C23  C17  122.38  3.000
 9ET  N24  C25  C16  108.85  3.000
 9ET  N24  C25  C10  129.44  3.000
 9ET  C16  C25  C10  121.71  3.000
 9ET  H20  N24  C25  125.81  3.000
 9ET  H20  N24  C23  124.67  3.000
 9ET  C25  N24  C23  109.50  3.000
 9ET  C05  O04  C02  118.19  3.000
 9ET  C11  O12  C06  117.77  3.000
 9ET  H21  O21  C20  110.35  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
 9ET  CONST_01  C15  C13  C11  C10     0.00   0.0  0
 9ET  CONST_02  C15  C16  C25  C10     0.00   0.0  0
 9ET  CONST_03  C17  C16  C25  C10   180.00   0.0  0
 9ET  CONST_04  C23  N24  C25  C10   180.00   0.0  0
 9ET  CONST_05  C17  C16  C15  C13   180.00   0.0  0
 9ET  CONST_06  C25  C16  C15  C13     0.00   0.0  0
 9ET  CONST_07  C25  C10  C11  C13     0.00   0.0  0
 9ET  CONST_08  C18  C17  C16  C15     0.00   0.0  0
 9ET  CONST_09  C23  C17  C16  C15   180.00   0.0  0
 9ET  CONST_10  N24  C25  C16  C15   180.00   0.0  0
 9ET  CONST_11  C20  C19  C18  C17     0.00   0.0  0
 9ET  CONST_12  N24  C25  C16  C17     0.00   0.0  0
 9ET  CONST_13  C20  C22  C23  C17     0.00   0.0  0
 9ET  CONST_14  C25  N24  C23  C17     0.00   0.0  0
 9ET  CONST_15  N24  C23  C22  C20   180.00   0.0  0
 9ET  CONST_16  C18  C19  C20  C22     0.00   0.0  0
 9ET  CONST_17  C18  C17  C23  C22     0.00   0.0  0
 9ET  CONST_18  C16  C17  C23  C22   180.00   0.0  0
 9ET  CONST_19  C25  N24  C23  C22   180.00   0.0  0
 9ET  CONST_20  C16  C15  C13  C11     0.00   0.0  0
 9ET  CONST_21  C16  C25  C10  C11     0.00   0.0  0
 9ET  CONST_22  N24  C25  C10  C11   180.00   0.0  0
 9ET  CONST_23  C19  C18  C17  C16   180.00   0.0  0
 9ET  CONST_24  N24  C23  C17  C16     0.00   0.0  0
 9ET  CONST_25  C23  N24  C25  C16     0.00   0.0  0
 9ET  CONST_26  C25  C16  C17  C18   180.00   0.0  0
 9ET  CONST_27  N24  C23  C17  C18   180.00   0.0  0
 9ET  CONST_28  C23  C17  C18  C19     0.00   0.0  0
 9ET  CONST_29  C23  C22  C20  C19     0.00   0.0  0
 9ET  CONST_30  C25  C16  C17  C23     0.00   0.0  0
 9ET  CONST_31  C14  C13  C11  C10   180.00   0.0  0
 9ET  CONST_32  C16  C15  C13  C14   180.00   0.0  0
 9ET  CONST_33  O12  C11  C13  C14     0.00   0.0  0
 9ET  CONST_34  O21  C20  C19  C18   180.00   0.0  0
 9ET  CONST_35  O21  C20  C22  C23   180.00   0.0  0
 9ET  CONST_36  H20  N24  C25  C10     0.00   0.0  0
 9ET  CONST_37  H19  C19  C18  C17   180.00   0.0  0
 9ET  CONST_38  H1   C15  C16  C17     0.00   0.0  0
 9ET  CONST_39  H2   C22  C23  C17   180.00   0.0  0
 9ET  CONST_40  H18  C18  C19  C20   180.00   0.0  0
 9ET  Var_01    C06  C08  C09  C10     1.99  30.0  1
 9ET  Var_02    C11  C10  C09  C08    14.48  30.0  1
 9ET  Var_03    H15  C14  C13  C15  -113.63  30.0  2
 9ET  Var_04    C06  C05  O04  C02  -179.56  30.0  2
 9ET  Var_05    O03  C02  O04  C05     1.13  30.0  3
 9ET  Var_06    H3   C01  C02  O03    12.85  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
 9ET  chir_01  C06  O12  C08  C05  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
 9ET  plan-1  C01  0.020
 9ET  plan-1  C02  0.020
 9ET  plan-1  O03  0.020
 9ET  plan-1  O04  0.020
 9ET  plan-2  C10  0.020
 9ET  plan-2  C13  0.020
 9ET  plan-2  C15  0.020
 9ET  plan-2  C17  0.020
 9ET  plan-2  C20  0.020
 9ET  plan-2  C22  0.020
 9ET  plan-2  C09  0.020
 9ET  plan-2  C11  0.020
 9ET  plan-2  C14  0.020
 9ET  plan-2  C16  0.020
 9ET  plan-2  C18  0.020
 9ET  plan-2  C19  0.020
 9ET  plan-2  C23  0.020
 9ET  plan-2  C25  0.020
 9ET  plan-2  N24  0.020
 9ET  plan-2  O12  0.020
 9ET  plan-2  O21  0.020
 9ET  plan-2  H1   0.020
 9ET  plan-2  H2   0.020
 9ET  plan-2  H18  0.020
 9ET  plan-2  H19  0.020
 9ET  plan-2  H20  0.020

