# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Aug  1 21:31:16 2022
#   Inital geometry file: a 126 line input string
#   Ligand name: (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(O)cc15)[C@@](O)(CC)C(=O)OC4
#
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
 RS4  RS4  "7-ethyl-10-hydroxycamptothecin"
  ligand  49  29  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_RS4
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
 RS4  C10  C  CR6   0  -0.007  -1.0928  -1.7323  5.2984
 RS4  C11  C  CR6   0   0.021  -0.6496  -1.4399  3.9944
 RS4  C14  C  CH2   0  -0.551  -2.4763  -3.0799  6.8866
 RS4  C15  C  CH3   0  -0.659  -3.8417  -2.4310  7.1206
 RS4  C16  C  CH2   0  -0.312  -0.4860  -0.7583  6.2562
 RS4  C17  C  CR6   0   0.535   0.2443  -0.2929  4.0626
 RS4  C1   C  CR66  0   0.160  -1.8265  -3.1250  3.0885
 RS4  C19  C  CR16  0  -0.463   0.9164   0.3718  3.0875
 RS4  C2   C  CR66  0   0.085  -2.3461  -3.5096  4.3597
 RS4  C20  C  CR6   0   0.258   1.7123   1.4660  3.4920
 RS4  C21  C  CR6   0  -0.244   1.8192   1.8096  4.8082
 RS4  C22  C  CR6   0   0.555   1.0938   1.1145  5.8416
 RS4  C24  C  CH2   0  -0.217   2.7109   2.9319  5.2158
 RS4  C25  C  CT    0  -0.018   2.4377   2.3256  2.4874
 RS4  C28  C  C     0   0.576   3.7858   2.7705  3.0704
 RS4  C3   C  CR16  0  -0.506  -3.2384  -4.6015  4.4282
 RS4  C4   C  CR6   0   0.399  -3.6018  -5.2856  3.2937
 RS4  C5   C  CR16  0  -0.336  -3.0762  -4.9090  2.0348
 RS4  C6   C  CR16  0  -0.288  -2.2141  -3.8588  1.9421
 RS4  C7   C  CH2   0  -0.453   1.6177   3.6032  2.1848
 RS4  C8   C  CH3   0  -0.665   0.2408   3.3235  1.6024
 RS4  C9   C  CR6   0   0.201  -1.9493  -2.7748  5.5168
 RS4  N13  N  N     0  -0.453  -0.9792  -2.0876  2.9157
 RS4  N18  N  NR6   0  -0.636   0.3274   0.0736  5.3713
 RS4  O1   O  OH1   0  -0.647   2.6533   1.5668  1.3399
 RS4  O23  O  O     0  -0.493   1.1215   1.3875  7.0377
 RS4  O29  O  O2    0  -0.423   3.8500   3.0581  4.3607
 RS4  O31  O  O     0  -0.419   4.7660   2.8908  2.3865
 RS4  O7   O  OH1   0  -0.621  -4.4546  -6.3220  3.2942
 RS4  H1   H  HCH2  0   0.258  -2.5450  -4.1582  7.0384
 RS4  H2   H  HCH2  0   0.264  -1.7709  -2.7165  7.6360
 RS4  H3   H  HCH3  0   0.241  -4.2024  -2.6536  8.1245
 RS4  H4   H  HCH3  0   0.235  -3.7806  -1.3476  7.0175
 RS4  H5   H  HCH3  0   0.233  -4.5836  -2.7940  6.4096
 RS4  H6   H  HCH2  0   0.296  -1.2295  -0.1472  6.7730
 RS4  H7   H  HCH2  0   0.295   0.1419  -1.2330  7.0136
 RS4  H8   H  HCR6  0   0.276   0.8235   0.0661  2.0573
 RS4  H9   H  HCH2  0   0.282   3.1098   2.7669  6.2150
 RS4  H10  H  HCH2  0   0.269   2.1776   3.8873  5.2330
 RS4  H11  H  HCR6  0   0.273  -3.6481  -4.9055  5.3842
 RS4  H12  H  HCR6  0   0.275  -3.3690  -5.4631  1.1519
 RS4  H13  H  HCR6  0   0.268  -1.8085  -3.5625  0.9834
 RS4  H14  H  HCH2  0   0.258   2.1990   4.2103  1.4834
 RS4  H15  H  HCH2  0   0.252   1.5140   4.2041  3.0906
 RS4  H16  H  HCH3  0   0.245  -0.2468   4.2644  1.3493
 RS4  H17  H  HCH3  0   0.231   0.2983   2.7281  0.6921
 RS4  H18  H  HCH3  0   0.234  -0.4029   2.8014  2.3100
 RS4  H19  H  HOH1  0   0.461   3.0805   2.1154  0.6717
 RS4  H20  H  HOH1  0   0.477  -4.7638  -6.5096  4.1884

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
 RS4  C8   C7   single    1.521  0.020  1.521
 RS4  C7   C25  single    1.548  0.020  1.548
 RS4  C6   C5   aromatic  1.362  0.020  1.362
 RS4  C6   C1   aromatic  1.415  0.020  1.415
 RS4  C5   C4   aromatic  1.415  0.020  1.415
 RS4  O1   C25  single    1.392  0.020  1.392
 RS4  O31  C28  double    1.201  0.020  1.201
 RS4  C25  C28  single    1.535  0.020  1.535
 RS4  C25  C20  single    1.508  0.020  1.508
 RS4  N13  C1   aromatic  1.350  0.020  1.350
 RS4  N13  C11  aromatic  1.301  0.020  1.301
 RS4  C1   C2   aromatic  1.426  0.020  1.426
 RS4  O7   C4   single    1.342  0.020  1.342
 RS4  C4   C3   aromatic  1.374  0.020  1.374
 RS4  C28  O29  single    1.324  0.020  1.324
 RS4  C19  C20  single    1.412  0.020  1.412
 RS4  C19  C17  double    1.358  0.020  1.358
 RS4  C20  C21  double    1.365  0.020  1.365
 RS4  C11  C17  single    1.456  0.020  1.456
 RS4  C11  C10  aromatic  1.408  0.020  1.408
 RS4  C17  N18  single    1.362  0.020  1.362
 RS4  C3   C2   aromatic  1.412  0.020  1.412
 RS4  C2   C9   aromatic  1.427  0.020  1.427
 RS4  O29  C24  single    1.430  0.020  1.430
 RS4  C21  C24  single    1.490  0.020  1.490
 RS4  C21  C22  single    1.441  0.020  1.441
 RS4  C10  C9   aromatic  1.367  0.020  1.367
 RS4  C10  C16  single    1.495  0.020  1.495
 RS4  C9   C14  single    1.499  0.020  1.499
 RS4  N18  C22  single    1.376  0.020  1.376
 RS4  N18  C16  single    1.462  0.020  1.462
 RS4  C22  O23  double    1.227  0.020  1.227
 RS4  C14  C15  single    1.530  0.020  1.530
 RS4  C14  H1   single    0.970  0.020  1.090
 RS4  C14  H2   single    0.970  0.020  1.090
 RS4  C15  H3   single    0.970  0.020  1.090
 RS4  C15  H4   single    0.970  0.020  1.090
 RS4  C15  H5   single    0.970  0.020  1.090
 RS4  C16  H6   single    0.970  0.020  1.090
 RS4  C16  H7   single    0.970  0.020  1.090
 RS4  C19  H8   single    0.930  0.020  1.080
 RS4  C24  H9   single    0.970  0.020  1.090
 RS4  C24  H10  single    0.970  0.020  1.090
 RS4  C3   H11  single    0.930  0.020  1.080
 RS4  C5   H12  single    0.930  0.020  1.080
 RS4  C6   H13  single    0.930  0.020  1.080
 RS4  C7   H14  single    0.970  0.020  1.090
 RS4  C7   H15  single    0.970  0.020  1.090
 RS4  C8   H16  single    0.970  0.020  1.090
 RS4  C8   H17  single    0.970  0.020  1.090
 RS4  C8   H18  single    0.970  0.020  1.090
 RS4  O1   H19  single    0.850  0.020  0.980
 RS4  O7   H20  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
 RS4  C9   C10  C16  130.47  3.000
 RS4  C16  C10  C11  109.29  3.000
 RS4  C9   C10  C11  120.24  3.000
 RS4  N13  C11  C17  125.93  3.000
 RS4  C17  C11  C10  108.27  3.000
 RS4  N13  C11  C10  125.80  3.000
 RS4  H2   C14  H1   105.91  3.000
 RS4  H2   C14  C9   109.42  3.000
 RS4  H1   C14  C9   110.51  3.000
 RS4  H2   C14  C15  109.30  3.000
 RS4  H1   C14  C15  109.98  3.000
 RS4  C9   C14  C15  111.55  3.000
 RS4  H5   C15  H4   107.90  3.000
 RS4  H5   C15  H3   107.92  3.000
 RS4  H4   C15  H3   107.98  3.000
 RS4  H5   C15  C14  111.50  3.000
 RS4  H4   C15  C14  110.92  3.000
 RS4  H3   C15  C14  110.48  3.000
 RS4  H7   C16  H6   107.83  3.000
 RS4  H7   C16  N18  110.32  3.000
 RS4  H6   C16  N18  110.29  3.000
 RS4  H7   C16  C10  113.23  3.000
 RS4  H6   C16  C10  113.05  3.000
 RS4  N18  C16  C10  102.06  3.000
 RS4  N18  C17  C19  121.88  3.000
 RS4  N18  C17  C11  107.13  3.000
 RS4  C19  C17  C11  130.99  3.000
 RS4  N13  C1   C6   117.80  3.000
 RS4  N13  C1   C2   123.35  3.000
 RS4  C6   C1   C2   118.84  3.000
 RS4  H8   C19  C20  122.80  3.000
 RS4  H8   C19  C17  120.29  3.000
 RS4  C20  C19  C17  116.91  3.000
 RS4  C9   C2   C3   122.32  3.000
 RS4  C9   C2   C1   118.86  3.000
 RS4  C3   C2   C1   118.82  3.000
 RS4  C25  C20  C21  117.47  3.000
 RS4  C21  C20  C19  121.03  3.000
 RS4  C25  C20  C19  121.46  3.000
 RS4  C24  C21  C22  117.92  3.000
 RS4  C22  C21  C20  122.05  3.000
 RS4  C24  C21  C20  120.02  3.000
 RS4  O23  C22  N18  120.94  3.000
 RS4  O23  C22  C21  125.46  3.000
 RS4  N18  C22  C21  113.60  3.000
 RS4  H10  C24  H9   107.25  3.000
 RS4  H10  C24  O29  108.70  3.000
 RS4  H9   C24  O29  105.69  3.000
 RS4  H10  C24  C21  111.73  3.000
 RS4  H9   C24  C21  110.87  3.000
 RS4  O29  C24  C21  112.31  3.000
 RS4  O1   C25  C7   111.76  3.000
 RS4  O1   C25  C28  109.58  3.000
 RS4  C7   C25  C28  107.47  3.000
 RS4  C28  C25  C20  109.55  3.000
 RS4  O1   C25  C20  108.23  3.000
 RS4  C7   C25  C20  110.23  3.000
 RS4  O31  C28  O29  119.58  3.000
 RS4  O29  C28  C25  118.42  3.000
 RS4  O31  C28  C25  121.98  3.000
 RS4  H11  C3   C4   119.27  3.000
 RS4  H11  C3   C2   119.92  3.000
 RS4  C4   C3   C2   120.82  3.000
 RS4  O7   C4   C5   116.22  3.000
 RS4  O7   C4   C3   123.53  3.000
 RS4  C5   C4   C3   120.26  3.000
 RS4  H12  C5   C6   120.69  3.000
 RS4  H12  C5   C4   119.26  3.000
 RS4  C6   C5   C4   120.06  3.000
 RS4  H13  C6   C5   120.57  3.000
 RS4  H13  C6   C1   118.23  3.000
 RS4  C5   C6   C1   121.20  3.000
 RS4  H15  C7   H14  106.07  3.000
 RS4  H15  C7   C8   109.44  3.000
 RS4  H14  C7   C8   109.72  3.000
 RS4  H15  C7   C25  110.02  3.000
 RS4  H14  C7   C25  107.55  3.000
 RS4  C8   C7   C25  113.74  3.000
 RS4  H18  C8   H17  108.18  3.000
 RS4  H18  C8   H16  107.47  3.000
 RS4  H17  C8   H16  107.55  3.000
 RS4  H18  C8   C7   111.97  3.000
 RS4  H17  C8   C7   111.88  3.000
 RS4  H16  C8   C7   109.59  3.000
 RS4  C2   C9   C14  122.58  3.000
 RS4  C14  C9   C10  121.43  3.000
 RS4  C2   C9   C10  115.94  3.000
 RS4  C1   N13  C11  115.81  3.000
 RS4  C22  N18  C17  124.49  3.000
 RS4  C22  N18  C16  122.26  3.000
 RS4  C17  N18  C16  113.25  3.000
 RS4  H19  O1   C25  109.25  3.000
 RS4  C28  O29  C24  121.68  3.000
 RS4  H20  O7   C4   110.75  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
 RS4  CONST_01  C1   N13  C11  C10     0.00   0.0  0
 RS4  CONST_02  C1   C2   C9   C10     0.00   0.0  0
 RS4  CONST_03  C3   C2   C9   C10   180.00   0.0  0
 RS4  CONST_04  C6   C1   N13  C11   180.00   0.0  0
 RS4  CONST_05  C2   C1   N13  C11     0.00   0.0  0
 RS4  CONST_06  C2   C9   C10  C11     0.00   0.0  0
 RS4  CONST_07  C4   C5   C6   C1      0.00   0.0  0
 RS4  CONST_08  C4   C3   C2   C1      0.00   0.0  0
 RS4  CONST_09  C5   C6   C1   C2      0.00   0.0  0
 RS4  CONST_10  C5   C4   C3   C2      0.00   0.0  0
 RS4  CONST_11  C6   C5   C4   C3      0.00   0.0  0
 RS4  CONST_12  C6   C1   C2   C3      0.00   0.0  0
 RS4  CONST_13  N13  C1   C2   C3    180.00   0.0  0
 RS4  CONST_14  C9   C2   C3   C4    180.00   0.0  0
 RS4  CONST_15  N13  C1   C6   C5    180.00   0.0  0
 RS4  CONST_16  C9   C2   C1   C6    180.00   0.0  0
 RS4  CONST_17  N13  C1   C2   C9      0.00   0.0  0
 RS4  CONST_18  N13  C11  C10  C9      0.00   0.0  0
 RS4  CONST_19  C21  C22  N18  C16   180.00   0.0  0
 RS4  CONST_20  C21  C22  N18  C17     0.00   0.0  0
 RS4  CONST_21  C14  C9   C10  C11   180.00   0.0  0
 RS4  CONST_22  C1   C2   C9   C14   180.00   0.0  0
 RS4  CONST_23  C3   C2   C9   C14     0.00   0.0  0
 RS4  CONST_24  C16  C10  C9   C14     0.00   0.0  0
 RS4  CONST_25  O7   C4   C3   C2    180.00   0.0  0
 RS4  CONST_26  O7   C4   C5   C6    180.00   0.0  0
 RS4  CONST_27  O23  C22  N18  C16     0.00   0.0  0
 RS4  CONST_28  O23  C22  N18  C17   180.00   0.0  0
 RS4  CONST_29  H12  C5   C6   C1    180.00   0.0  0
 RS4  CONST_30  H11  C3   C2   C1    180.00   0.0  0
 RS4  CONST_31  H13  C6   C1   C2    180.00   0.0  0
 RS4  CONST_32  H12  C5   C4   C3    180.00   0.0  0
 RS4  CONST_33  H13  C6   C5   C4    180.00   0.0  0
 RS4  CONST_34  H11  C3   C4   C5    180.00   0.0  0
 RS4  CONST_35  H11  C3   C2   C9      0.00   0.0  0
 RS4  CONST_36  H13  C6   C1   N13     0.00   0.0  0
 RS4  Var_01    C20  C19  C17  C11   179.82   0.0  0
 RS4  Var_02    N18  C17  C19  C20     0.09   0.0  0
 RS4  Var_03    C19  C17  C11  C10  -179.51  30.0  1
 RS4  Var_04    N18  C17  C11  C10     0.25  30.0  1
 RS4  Var_05    C17  N18  C16  C10     0.68  30.0  1
 RS4  Var_06    C22  N18  C16  C10  -179.15  30.0  1
 RS4  Var_07    C22  N18  C17  C11   179.23  30.0  1
 RS4  Var_08    C16  N18  C17  C11    -0.60  30.0  1
 RS4  Var_09    N18  C16  C10  C11    -0.50  30.0  1
 RS4  Var_10    C19  C17  N18  C16   179.19  30.0  1
 RS4  Var_11    C25  C20  C19  C17  -176.37  30.0  1
 RS4  Var_12    C21  C20  C19  C17     1.55  30.0  1
 RS4  Var_13    C24  C21  C20  C19   177.39  30.0  1
 RS4  Var_14    C22  C21  C20  C19    -2.38  30.0  1
 RS4  Var_15    N13  C11  C17  C19     0.73  30.0  1
 RS4  Var_16    C22  N18  C17  C19    -0.98  30.0  1
 RS4  Var_17    O29  C24  C21  C20   -31.61  30.0  1
 RS4  Var_18    N18  C22  C21  C20     1.44  30.0  1
 RS4  Var_19    C28  O29  C24  C21    33.22  30.0  1
 RS4  Var_20    C25  C20  C21  C22   175.63  30.0  1
 RS4  Var_21    O29  C24  C21  C22   148.17  30.0  1
 RS4  Var_22    C25  C28  O29  C24     1.55  30.0  1
 RS4  Var_23    C25  C20  C21  C24    -4.60  30.0  1
 RS4  Var_24    N18  C22  C21  C24  -178.33  30.0  1
 RS4  Var_25    N18  C16  C10  C9    179.64  30.0  1
 RS4  Var_26    N18  C17  C11  N13  -179.51  30.0  1
 RS4  Var_27    O23  C22  C21  C20  -178.41  30.0  1
 RS4  Var_28    O31  C28  O29  C24   179.96  30.0  1
 RS4  Var_29    O23  C22  C21  C24     1.82  30.0  1
 RS4  Var_30    H8   C19  C17  C11     0.41   0.0  0
 RS4  Var_31    H8   C19  C17  N18  -179.32   0.0  0
 RS4  Var_32    H6   C16  C10  C11   117.94  30.0  1
 RS4  Var_33    H7   C16  C10  C11  -119.05  30.0  1
 RS4  Var_34    H6   C16  N18  C17  -119.70  30.0  1
 RS4  Var_35    H7   C16  N18  C17   121.29  30.0  1
 RS4  Var_36    H9   C24  C21  C20  -149.60  30.0  1
 RS4  Var_37    H10  C24  C21  C20    90.83  30.0  1
 RS4  Var_38    H8   C19  C20  C21  -179.05  30.0  1
 RS4  Var_39    H9   C24  C21  C22    30.19  30.0  1
 RS4  Var_40    H10  C24  C21  C22   -89.39  30.0  1
 RS4  Var_41    H6   C16  N18  C22    60.47  30.0  1
 RS4  Var_42    H7   C16  N18  C22   -58.54  30.0  1
 RS4  Var_43    H8   C19  C20  C25     3.02  30.0  1
 RS4  Var_44    H9   C24  O29  C28   154.23  30.0  1
 RS4  Var_45    H10  C24  O29  C28   -90.92  30.0  1
 RS4  Var_46    H6   C16  C10  C9    -61.93  30.0  1
 RS4  Var_47    H7   C16  C10  C9     61.08  30.0  1
 RS4  Var_48    C15  C14  C9   C10    94.97  30.0  2
 RS4  Var_49    C2   C9   C14  C15   -82.42  30.0  2
 RS4  Var_50    H1   C14  C9   C10  -142.35  30.0  2
 RS4  Var_51    H2   C14  C9   C10   -26.10  30.0  2
 RS4  Var_52    H1   C14  C9   C2     40.26  30.0  2
 RS4  Var_53    H2   C14  C9   C2    156.52  30.0  2
 RS4  Var_54    H16  C8   C7   C25  -175.94  30.0  3
 RS4  Var_55    H17  C8   C7   C25   -56.74  30.0  3
 RS4  Var_56    H18  C8   C7   C25    64.90  30.0  3
 RS4  Var_57    H3   C15  C14  C9   -179.31  30.0  3
 RS4  Var_58    H4   C15  C14  C9    -59.60  30.0  3
 RS4  Var_59    H5   C15  C14  C9     60.68  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
 RS4  chir_01  C25  O1  C28  C20  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
 RS4  plan-1  C16  0.020
 RS4  plan-1  C17  0.020
 RS4  plan-1  C21  0.020
 RS4  plan-1  C22  0.020
 RS4  plan-1  N18  0.020
 RS4  plan-1  O23  0.020
 RS4  plan-2  C10  0.020
 RS4  plan-2  C11  0.020
 RS4  plan-2  C14  0.020
 RS4  plan-2  C16  0.020
 RS4  plan-2  C17  0.020
 RS4  plan-2  C1   0.020
 RS4  plan-2  C2   0.020
 RS4  plan-2  C3   0.020
 RS4  plan-2  C4   0.020
 RS4  plan-2  C5   0.020
 RS4  plan-2  C6   0.020
 RS4  plan-2  C9   0.020
 RS4  plan-2  N13  0.020
 RS4  plan-2  O7   0.020
 RS4  plan-2  H11  0.020
 RS4  plan-2  H12  0.020
 RS4  plan-2  H13  0.020
 RS4  plan-3  C25  0.020
 RS4  plan-3  C28  0.020
 RS4  plan-3  O29  0.020
 RS4  plan-3  O31  0.020
 RS4  plan-4  C11  0.020
 RS4  plan-4  C17  0.020
 RS4  plan-4  C19  0.020
 RS4  plan-4  C20  0.020
 RS4  plan-4  N18  0.020
 RS4  plan-4  H8   0.020

