# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 05:20:00 2020
#   Inital geometry file: a 79 line input string
#   Ligand name: 3-(5-fluoro-1H-indol-3-yl)propyl dihydrogen phosphate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[P](O)(=O)OCCCc1c[nH]c2ccc(F)cc12
#
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
 FIP  FIP  '3-(5-fluoro-1H-indol-3-yl)propyl dihydrogen phosphate'  ligand  31  18  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_FIP
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
 FIP  C3    C  CR5   0   0.050  -1.3741   0.5453  -1.6551
 FIP  C9    C  CR56  0   0.003  -0.3689   0.1732  -2.6044
 FIP  C8    C  CR56  0   0.310  -1.0356  -0.2967  -3.7559
 FIP  C4    C  CR16  0  -0.533   1.0313   0.2045  -2.5887
 FIP  C2    C  CR15  0  -0.068  -2.5732   0.2883  -2.2607
 FIP  N1    N  NR15  0  -0.628  -2.3760  -0.2167  -3.5134
 FIP  C7    C  CR16  0  -0.249  -0.3445  -0.7363  -4.8822
 FIP  C5    C  CR6   0   0.503   1.6873  -0.2309  -3.7117
 FIP  C6    C  CR16  0  -0.438   1.0341  -0.7030  -4.8553
 FIP  F     F  F     0  -0.316   3.0351  -0.2077  -3.7271
 FIP  C3P   C  CH2   0  -0.567  -1.1600   1.0885  -0.2821
 FIP  C2P   C  CH2   0  -0.457  -0.6314   0.0419   0.7013
 FIP  C1P   C  CH2   0  -0.139  -0.3903   0.6562   2.0629
 FIP  P     P  P     0   1.451   0.4885   0.0003   4.4438
 FIP  OP1   O  O     0  -0.691   1.4478   1.0941   4.6459
 FIP  OP2   O  OH1   0  -0.717   0.9217  -1.4683   4.8946
 FIP  OP3   O  OH1   0  -0.704  -0.8779   0.3342   5.2116
 FIP  OP4   O  O2    0  -0.562   0.0959  -0.3664   2.9423
 FIP  H4    H  HCR6  0   0.252   1.5819   0.5663  -1.7288
 FIP  H2    H  HCR5  0   0.289  -3.5723   0.4350  -1.8814
 FIP  HN1   H  HNR5  0   0.412  -3.1074  -0.4741  -4.1519
 FIP  H7    H  HCR6  0   0.269  -0.8713  -1.0990  -5.7550
 FIP  H6    H  HCR6  0   0.242   1.6159  -1.0356  -5.7031
 FIP  H3P1  H  HCH2  0   0.206  -2.1037   1.4935   0.0947
 FIP  H3P2  H  HCH2  0   0.216  -0.4615   1.9314  -0.3243
 FIP  H2P1  H  HCH2  0   0.253   0.3027  -0.3875   0.3300
 FIP  H2P2  H  HCH2  0   0.212  -1.3505  -0.7766   0.7814
 FIP  H1P1  H  HCH2  0   0.190  -1.3172   1.0826   2.4592
 FIP  H1P2  H  HCH2  0   0.221   0.3456   1.4622   1.9915
 FIP  HO2   H  HOH1  0   0.502   1.4885  -1.4793   5.6753
 FIP  HO3   H  HOH1  0   0.489  -1.5615  -0.3438   5.1956

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
 FIP  C3   C9    aromatic  1.432  0.020  1.432
 FIP  C3   C2    aromatic  1.368  0.020  1.368
 FIP  C3   C3P   single    1.492  0.020  1.492
 FIP  C9   C8    aromatic  1.411  0.020  1.411
 FIP  C9   C4    aromatic  1.401  0.020  1.401
 FIP  C8   N1    aromatic  1.364  0.020  1.364
 FIP  C8   C7    aromatic  1.393  0.020  1.393
 FIP  C4   C5    aromatic  1.371  0.020  1.371
 FIP  C4   H4    single    0.930  0.020  1.080
 FIP  C2   N1    aromatic  1.365  0.020  1.365
 FIP  C2   H2    single    0.930  0.020  1.080
 FIP  N1   HN1   single    0.860  0.020  1.020
 FIP  C7   C6    aromatic  1.379  0.020  1.379
 FIP  C7   H7    single    0.930  0.020  1.080
 FIP  C5   C6    aromatic  1.399  0.020  1.399
 FIP  C5   F     single    1.348  0.020  1.348
 FIP  C6   H6    single    0.930  0.020  1.080
 FIP  C3P  C2P   single    1.530  0.020  1.530
 FIP  C3P  H3P1  single    0.970  0.020  1.090
 FIP  C3P  H3P2  single    0.970  0.020  1.090
 FIP  C2P  C1P   single    1.513  0.020  1.513
 FIP  C2P  H2P1  single    0.970  0.020  1.090
 FIP  C2P  H2P2  single    0.970  0.020  1.090
 FIP  C1P  OP4   single    1.434  0.020  1.434
 FIP  C1P  H1P1  single    0.970  0.020  1.090
 FIP  C1P  H1P2  single    0.970  0.020  1.090
 FIP  P    OP1   double    1.469  0.020  1.469
 FIP  P    OP2   single    1.596  0.020  1.596
 FIP  P    OP3   single    1.603  0.020  1.603
 FIP  P    OP4   single    1.595  0.020  1.595
 FIP  OP2  HO2   single    0.850  0.020  0.980
 FIP  OP3  HO3   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
 FIP  C3P   C3   C2    126.99  3.000
 FIP  C3P   C3   C9    127.15  3.000
 FIP  C2    C3   C9    105.85  3.000
 FIP  C4    C9   C8    119.27  3.000
 FIP  C4    C9   C3    133.52  3.000
 FIP  C8    C9   C3    107.21  3.000
 FIP  C7    C8   N1    130.52  3.000
 FIP  C7    C8   C9    122.04  3.000
 FIP  N1    C8   C9    107.43  3.000
 FIP  H4    C4   C5    120.86  3.000
 FIP  H4    C4   C9    121.63  3.000
 FIP  C5    C4   C9    117.51  3.000
 FIP  H2    C2   N1    120.46  3.000
 FIP  H2    C2   C3    129.10  3.000
 FIP  N1    C2   C3    110.44  3.000
 FIP  HN1   N1   C2    124.96  3.000
 FIP  HN1   N1   C8    125.97  3.000
 FIP  C2    N1   C8    109.07  3.000
 FIP  H7    C7   C6    120.69  3.000
 FIP  H7    C7   C8    121.10  3.000
 FIP  C6    C7   C8    118.21  3.000
 FIP  F     C5   C6    117.60  3.000
 FIP  F     C5   C4    118.82  3.000
 FIP  C6    C5   C4    123.58  3.000
 FIP  H6    C6   C5    119.58  3.000
 FIP  H6    C6   C7    121.03  3.000
 FIP  C5    C6   C7    119.39  3.000
 FIP  H3P2  C3P  H3P1  106.17  3.000
 FIP  H3P2  C3P  C2P   109.31  3.000
 FIP  H3P1  C3P  C2P   109.26  3.000
 FIP  H3P2  C3P  C3    109.64  3.000
 FIP  H3P1  C3P  C3    109.14  3.000
 FIP  C2P   C3P  C3    113.08  3.000
 FIP  H2P2  C2P  H2P1  107.04  3.000
 FIP  H2P2  C2P  C1P   110.06  3.000
 FIP  H2P1  C2P  C1P   109.21  3.000
 FIP  H2P2  C2P  C3P   109.40  3.000
 FIP  H2P1  C2P  C3P   110.22  3.000
 FIP  C1P   C2P  C3P   110.84  3.000
 FIP  H1P2  C1P  H1P1  107.84  3.000
 FIP  H1P2  C1P  OP4   109.72  3.000
 FIP  H1P1  C1P  OP4   110.06  3.000
 FIP  H1P2  C1P  C2P   110.34  3.000
 FIP  H1P1  C1P  C2P   110.43  3.000
 FIP  OP4   C1P  C2P   108.45  3.000
 FIP  OP4   P    OP3   106.80  3.000
 FIP  OP4   P    OP2    96.96  3.000
 FIP  OP3   P    OP2   106.73  3.000
 FIP  OP4   P    OP1   117.49  3.000
 FIP  OP3   P    OP1   109.62  3.000
 FIP  OP2   P    OP1   117.97  3.000
 FIP  HO2   OP2  P     113.48  3.000
 FIP  HO3   OP3  P     116.79  3.000
 FIP  P     OP4  C1P   119.80  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
 FIP  CONST_01  N1   C8   C9   C3     0.00   0.0  0
 FIP  CONST_02  C7   C8   C9   C3   180.00   0.0  0
 FIP  CONST_03  C5   C4   C9   C3   180.00   0.0  0
 FIP  CONST_04  C8   N1   C2   C3     0.00   0.0  0
 FIP  CONST_05  N1   C2   C3   C9     0.00   0.0  0
 FIP  CONST_06  C2   N1   C8   C9     0.00   0.0  0
 FIP  CONST_07  C6   C7   C8   C9     0.00   0.0  0
 FIP  CONST_08  C6   C5   C4   C9     0.00   0.0  0
 FIP  CONST_09  C2   C3   C9   C8     0.00   0.0  0
 FIP  CONST_10  C5   C4   C9   C8     0.00   0.0  0
 FIP  CONST_11  C5   C6   C7   C8     0.00   0.0  0
 FIP  CONST_12  C2   C3   C9   C4   180.00   0.0  0
 FIP  CONST_13  N1   C8   C9   C4   180.00   0.0  0
 FIP  CONST_14  C7   C8   C9   C4     0.00   0.0  0
 FIP  CONST_15  C7   C6   C5   C4     0.00   0.0  0
 FIP  CONST_16  C7   C8   N1   C2   180.00   0.0  0
 FIP  CONST_17  C6   C7   C8   N1   180.00   0.0  0
 FIP  CONST_18  F    C5   C4   C9   180.00   0.0  0
 FIP  CONST_19  C3P  C3   C9   C8   180.00   0.0  0
 FIP  CONST_20  C3P  C3   C9   C4     0.00   0.0  0
 FIP  CONST_21  C3P  C3   C2   N1   180.00   0.0  0
 FIP  CONST_22  F    C5   C6   C7   180.00   0.0  0
 FIP  CONST_23  H4   C4   C9   C3     0.00   0.0  0
 FIP  CONST_24  HN1  N1   C2   C3   180.00   0.0  0
 FIP  CONST_25  H2   C2   C3   C9   180.00   0.0  0
 FIP  CONST_26  H7   C7   C8   C9   180.00   0.0  0
 FIP  CONST_27  H6   C6   C7   C8   180.00   0.0  0
 FIP  Var_01    C2P  C3P  C3   C9   -71.64  30.0  2
 FIP  Var_02    C1P  C2P  C3P  C3   178.16  30.0  3
 FIP  Var_03    OP4  C1P  C2P  C3P  179.72  30.0  3
 FIP  Var_04    OP1  P    OP4  C1P  -53.80  30.0  1

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
 FIP  plan-1  C3   0.020
 FIP  plan-1  C9   0.020
 FIP  plan-1  C8   0.020
 FIP  plan-1  C4   0.020
 FIP  plan-1  C2   0.020
 FIP  plan-1  N1   0.020
 FIP  plan-1  C7   0.020
 FIP  plan-1  C5   0.020
 FIP  plan-1  C6   0.020
 FIP  plan-1  F    0.020
 FIP  plan-1  C3P  0.020
 FIP  plan-1  H4   0.020
 FIP  plan-1  H2   0.020
 FIP  plan-1  HN1  0.020
 FIP  plan-1  H7   0.020
 FIP  plan-1  H6   0.020

