# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 11 11:35:38 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: (2S,3E,7E)-9-(3-chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)-3,7-dimethylnona-3,7-dien-2-yl acetate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](OC(C)=O)/C(C)=C/CC\C(C)=C\Cc1c(O)c(Cl)c(C)c(C=O)c1O
#
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
 9BO  9BO  '(2S,3E,7E)-9-(3-chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)-3,7-dimethylnona-3,7-dien-2-yl acetate'  ligand  54  27  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9BO
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
 9BO  CAA  C   CH3   0  -0.769  -7.0781   2.7607   0.0608
 9BO  CAR  C   C     0   0.568  -6.9592   1.2751  -0.1166
 9BO  OAG  O   O     0  -0.460  -7.8165   0.4776   0.1753
 9BO  OAQ  O   O2    0  -0.462  -5.7765   0.9420  -0.6185
 9BO  CBA  C   CH1   0  -0.040  -5.4612  -0.4521  -0.8341
 9BO  CAE  C   CH3   0  -0.682  -6.0105  -0.9042  -2.1776
 9BO  CAT  C   C     0   0.098  -3.9606  -0.5699  -0.7349
 9BO  CAC  C   CH3   0  -0.735  -3.1542   0.2874  -1.6657
 9BO  CAL  C   C1    0  -0.258  -3.4470  -1.4341   0.1435
 9BO  CAN  C   CH2   0  -0.495  -2.0058  -1.7353   0.4032
 9BO  CAO  C   CH2   0  -0.483  -1.5788  -1.2462   1.7961
 9BO  CAS  C   C     0   0.120  -0.1351  -1.5439   2.1088
 9BO  CAB  C   CH3   0  -0.728   0.1958  -2.9952   2.2887
 9BO  CAM  C   C1    0  -0.258   0.7409  -0.5408   2.1998
 9BO  CAP  C   CH2   0  -0.561   2.2169  -0.6162   2.4692
 9BO  CAZ  C   CR6   0  -0.106   3.0019  -0.1530   1.2672
 9BO  CAW  C   CR6   0   0.366   3.2991   1.1939   1.0769
 9BO  OAI  O   OH1   0  -0.617   2.8888   2.0474   2.0073
 9BO  CAY  C   CR6   0  -0.236   4.0096   1.6491  -0.0653
 9BO  CAK  C   C1    0   0.146   4.2982   3.0603  -0.1782
 9BO  OAF  O   O     0  -0.459   3.9547   3.9015   0.6500
 9BO  CAU  C   CR6   0   0.135   4.4196   0.7239  -1.0520
 9BO  CAD  C   CH3   0  -0.739   5.1713   1.1122  -2.2917
 9BO  CAX  C   CR6   0  -0.255   4.1074  -0.6042  -0.8491
 9BO  CLA  CL  CL    0  -0.110   4.5826  -1.8082  -2.0120
 9BO  CAV  C   CR6   0   0.467   3.4024  -1.0514   0.2833
 9BO  OAH  O   OH1   0  -0.585   3.0941  -2.3315   0.4587
 9BO  H1   H   HCH3  0   0.260  -8.0985   3.0320   0.3162
 9BO  H2   H   HCH3  0   0.275  -6.4182   3.0903   0.8652
 9BO  H3   H   HCH3  0   0.268  -6.7770   3.2912  -0.8418
 9BO  H4   H   HCH1  0   0.251  -5.9191  -1.0467  -0.0405
 9BO  H5   H   HCH3  0   0.242  -5.7438  -1.9481  -2.3431
 9BO  H6   H   HCH3  0   0.247  -7.0974  -0.8316  -2.2058
 9BO  H7   H   HCH3  0   0.235  -5.6059  -0.3167  -3.0018
 9BO  H8   H   HCH3  0   0.244  -3.3476   1.3473  -1.4927
 9BO  H9   H   HCH3  0   0.246  -2.0843   0.1293  -1.5544
 9BO  H10  H   HCH3  0   0.242  -3.4041   0.0887  -2.7100
 9BO  H11  H   H     0   0.235  -4.1433  -1.9844   0.7730
 9BO  H12  H   HCH2  0   0.241  -1.8563  -2.8168   0.3349
 9BO  H13  H   HCH2  0   0.241  -1.3553  -1.2835  -0.3472
 9BO  H14  H   HCH2  0   0.238  -1.7575  -0.1699   1.8583
 9BO  H15  H   HCH2  0   0.229  -2.2223  -1.7165   2.5485
 9BO  H16  H   HCH3  0   0.238   0.0006  -3.5596   1.3741
 9BO  H17  H   HCH3  0   0.244   1.2323  -3.1741   2.5619
 9BO  H18  H   HCH3  0   0.232  -0.4383  -3.4337   3.0632
 9BO  H19  H   H     0   0.229   0.3645   0.4679   2.0475
 9BO  H20  H   HCH2  0   0.263   2.4588   0.0246   3.3196
 9BO  H21  H   HCH2  0   0.264   2.5233  -1.6209   2.7545
 9BO  H22  H   HOH1  0   0.477   3.1773   2.9541   1.7390
 9BO  H23  H   H     0   0.229   4.8625   3.3958  -1.0542
 9BO  H24  H   HCH3  0   0.268   6.1757   0.6870  -2.2762
 9BO  H25  H   HCH3  0   0.265   4.6714   0.7249  -3.1791
 9BO  H26  H   HCH3  0   0.261   5.2741   2.1830  -2.4257
 9BO  H27  H   HOH1  0   0.475   3.4213  -2.8783  -0.2685

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
 9BO  CAB  CAS  single    1.499  0.020  1.499
 9BO  OAH  CAV  single    1.328  0.020  1.328
 9BO  CAS  CAO  single    1.507  0.020  1.507
 9BO  CAS  CAM  double    1.335  0.020  1.335
 9BO  CLA  CAX  single    1.740  0.020  1.740
 9BO  CAO  CAN  single    1.537  0.020  1.537
 9BO  CAN  CAL  single    1.495  0.020  1.495
 9BO  CAV  CAX  aromatic  1.407  0.020  1.407
 9BO  CAV  CAZ  aromatic  1.391  0.020  1.391
 9BO  CAP  CAM  single    1.502  0.020  1.502
 9BO  CAP  CAZ  single    1.508  0.020  1.508
 9BO  CAX  CAU  aromatic  1.379  0.020  1.379
 9BO  CAZ  CAW  aromatic  1.392  0.020  1.392
 9BO  CAC  CAT  single    1.501  0.020  1.501
 9BO  CAL  CAT  double    1.335  0.020  1.335
 9BO  CAT  CBA  single    1.509  0.020  1.509
 9BO  CAU  CAD  single    1.501  0.020  1.501
 9BO  CAU  CAY  aromatic  1.413  0.020  1.413
 9BO  CAW  CAY  aromatic  1.420  0.020  1.420
 9BO  CAW  OAI  single    1.328  0.020  1.328
 9BO  CAY  CAK  single    1.445  0.020  1.445
 9BO  CBA  OAQ  single    1.445  0.020  1.445
 9BO  CBA  CAE  single    1.520  0.020  1.520
 9BO  OAQ  CAR  single    1.327  0.020  1.327
 9BO  CAR  OAG  double    1.207  0.020  1.207
 9BO  CAR  CAA  single    1.501  0.020  1.501
 9BO  CAK  OAF  double    1.229  0.020  1.229
 9BO  CAA  H1   single    0.970  0.020  1.090
 9BO  CAA  H2   single    0.970  0.020  1.090
 9BO  CAA  H3   single    0.970  0.020  1.090
 9BO  CBA  H4   single    0.970  0.020  1.090
 9BO  CAE  H5   single    0.970  0.020  1.090
 9BO  CAE  H6   single    0.970  0.020  1.090
 9BO  CAE  H7   single    0.970  0.020  1.090
 9BO  CAC  H8   single    0.970  0.020  1.090
 9BO  CAC  H9   single    0.970  0.020  1.090
 9BO  CAC  H10  single    0.970  0.020  1.090
 9BO  CAL  H11  single    0.930  0.020  1.080
 9BO  CAN  H12  single    0.970  0.020  1.090
 9BO  CAN  H13  single    0.970  0.020  1.090
 9BO  CAO  H14  single    0.970  0.020  1.090
 9BO  CAO  H15  single    0.970  0.020  1.090
 9BO  CAB  H16  single    0.970  0.020  1.090
 9BO  CAB  H17  single    0.970  0.020  1.090
 9BO  CAB  H18  single    0.970  0.020  1.090
 9BO  CAM  H19  single    0.930  0.020  1.080
 9BO  CAP  H20  single    0.970  0.020  1.090
 9BO  CAP  H21  single    0.970  0.020  1.090
 9BO  OAI  H22  single    0.850  0.020  0.980
 9BO  CAK  H23  single    0.930  0.020  1.080
 9BO  CAD  H24  single    0.970  0.020  1.090
 9BO  CAD  H25  single    0.970  0.020  1.090
 9BO  CAD  H26  single    0.970  0.020  1.090
 9BO  OAH  H27  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
 9BO  H3   CAA  H2   107.24  3.000
 9BO  H3   CAA  H1   109.44  3.000
 9BO  H2   CAA  H1   108.62  3.000
 9BO  H3   CAA  CAR  111.24  3.000
 9BO  H2   CAA  CAR  109.76  3.000
 9BO  H1   CAA  CAR  110.45  3.000
 9BO  OAQ  CAR  OAG  123.96  3.000
 9BO  OAG  CAR  CAA  124.70  3.000
 9BO  OAQ  CAR  CAA  111.33  3.000
 9BO  CBA  OAQ  CAR  119.52  3.000
 9BO  H4   CBA  CAT  109.07  3.000
 9BO  H4   CBA  CAE  109.19  3.000
 9BO  CAT  CBA  CAE  113.22  3.000
 9BO  H4   CBA  OAQ  108.99  3.000
 9BO  CAE  CBA  OAQ  109.87  3.000
 9BO  CAT  CBA  OAQ  106.41  3.000
 9BO  H7   CAE  H6   108.35  3.000
 9BO  H7   CAE  H5   108.09  3.000
 9BO  H6   CAE  H5   107.70  3.000
 9BO  H7   CAE  CBA  111.95  3.000
 9BO  H6   CAE  CBA  111.31  3.000
 9BO  H5   CAE  CBA  109.30  3.000
 9BO  CAL  CAT  CAC  124.84  3.000
 9BO  CAL  CAT  CBA  118.46  3.000
 9BO  CAC  CAT  CBA  116.69  3.000
 9BO  H10  CAC  H9   107.26  3.000
 9BO  H10  CAC  H8   106.73  3.000
 9BO  H9   CAC  H8   107.42  3.000
 9BO  H10  CAC  CAT  111.49  3.000
 9BO  H9   CAC  CAT  112.47  3.000
 9BO  H8   CAC  CAT  111.18  3.000
 9BO  H11  CAL  CAN  114.49  3.000
 9BO  H11  CAL  CAT  117.50  3.000
 9BO  CAN  CAL  CAT  127.99  3.000
 9BO  H13  CAN  H12  106.56  3.000
 9BO  H13  CAN  CAO  109.02  3.000
 9BO  H12  CAN  CAO  109.47  3.000
 9BO  H13  CAN  CAL  111.83  3.000
 9BO  H12  CAN  CAL  108.67  3.000
 9BO  CAO  CAN  CAL  111.17  3.000
 9BO  H15  CAO  H14  106.71  3.000
 9BO  H15  CAO  CAS  109.59  3.000
 9BO  H14  CAO  CAS  109.84  3.000
 9BO  H15  CAO  CAN  108.81  3.000
 9BO  H14  CAO  CAN  108.64  3.000
 9BO  CAS  CAO  CAN  113.04  3.000
 9BO  CAM  CAS  CAB  125.05  3.000
 9BO  CAM  CAS  CAO  119.63  3.000
 9BO  CAB  CAS  CAO  115.31  3.000
 9BO  H18  CAB  H17  108.02  3.000
 9BO  H18  CAB  H16  106.40  3.000
 9BO  H17  CAB  H16  107.21  3.000
 9BO  H18  CAB  CAS  110.20  3.000
 9BO  H17  CAB  CAS  113.58  3.000
 9BO  H16  CAB  CAS  111.12  3.000
 9BO  H19  CAM  CAP  114.32  3.000
 9BO  H19  CAM  CAS  117.41  3.000
 9BO  CAP  CAM  CAS  128.26  3.000
 9BO  H21  CAP  H20  105.98  3.000
 9BO  H21  CAP  CAZ  110.23  3.000
 9BO  H20  CAP  CAZ  108.97  3.000
 9BO  H21  CAP  CAM  111.71  3.000
 9BO  H20  CAP  CAM  109.14  3.000
 9BO  CAZ  CAP  CAM  110.67  3.000
 9BO  CAV  CAZ  CAW  117.81  3.000
 9BO  CAW  CAZ  CAP  121.14  3.000
 9BO  CAV  CAZ  CAP  121.00  3.000
 9BO  CAY  CAW  OAI  120.81  3.000
 9BO  OAI  CAW  CAZ  117.40  3.000
 9BO  CAY  CAW  CAZ  121.79  3.000
 9BO  H22  OAI  CAW  108.01  3.000
 9BO  CAU  CAY  CAK  121.79  3.000
 9BO  CAK  CAY  CAW  118.41  3.000
 9BO  CAU  CAY  CAW  119.79  3.000
 9BO  H23  CAK  OAF  118.26  3.000
 9BO  H23  CAK  CAY  117.69  3.000
 9BO  OAF  CAK  CAY  124.04  3.000
 9BO  CAX  CAU  CAD  118.95  3.000
 9BO  CAD  CAU  CAY  123.54  3.000
 9BO  CAX  CAU  CAY  117.51  3.000
 9BO  H26  CAD  H25  107.09  3.000
 9BO  H26  CAD  H24  107.43  3.000
 9BO  H25  CAD  H24  107.18  3.000
 9BO  H26  CAD  CAU  113.90  3.000
 9BO  H25  CAD  CAU  110.55  3.000
 9BO  H24  CAD  CAU  110.40  3.000
 9BO  CAV  CAX  CLA  117.06  3.000
 9BO  CAV  CAX  CAU  122.54  3.000
 9BO  CLA  CAX  CAU  120.41  3.000
 9BO  OAH  CAV  CAX  121.93  3.000
 9BO  CAX  CAV  CAZ  120.55  3.000
 9BO  OAH  CAV  CAZ  117.52  3.000
 9BO  H27  OAH  CAV  111.54  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
 9BO  CONST_01  CAU  CAX  CAV  CAZ     0.00   0.0  0
 9BO  CONST_02  CAU  CAY  CAW  CAZ     0.00   0.0  0
 9BO  CONST_03  CAX  CAV  CAZ  CAW     0.00   0.0  0
 9BO  CONST_04  CAX  CAU  CAY  CAW     0.00   0.0  0
 9BO  CONST_05  CAV  CAX  CAU  CAY     0.00   0.0  0
 9BO  CONST_06  CAV  CAZ  CAW  CAY     0.00   0.0  0
 9BO  CONST_07  CAX  CAV  CAZ  CAP   180.00   0.0  0
 9BO  CONST_08  CAY  CAW  CAZ  CAP   180.00   0.0  0
 9BO  CONST_09  CLA  CAX  CAV  CAZ   180.00   0.0  0
 9BO  CONST_10  CAK  CAY  CAW  CAZ   180.00   0.0  0
 9BO  CONST_11  OAH  CAV  CAZ  CAW   180.00   0.0  0
 9BO  CONST_12  CAD  CAU  CAY  CAW   180.00   0.0  0
 9BO  CONST_13  CAV  CAZ  CAW  OAI   180.00   0.0  0
 9BO  CONST_14  CAU  CAY  CAW  OAI   180.00   0.0  0
 9BO  CONST_15  CLA  CAX  CAU  CAY   180.00   0.0  0
 9BO  CONST_16  CAX  CAU  CAY  CAK   180.00   0.0  0
 9BO  CONST_17  OAH  CAV  CAX  CAU   180.00   0.0  0
 9BO  CONST_18  CAV  CAX  CAU  CAD   180.00   0.0  0
 9BO  Var_01    CAV  CAZ  CAP  CAM   -90.48  30.0  2
 9BO  Var_02    OAF  CAK  CAY  CAW    -0.75  30.0  2
 9BO  Var_03    H24  CAD  CAU  CAY   114.17  30.0  2
 9BO  Var_04    CAZ  CAP  CAM  CAS   114.05  30.0  2
 9BO  Var_05    CAN  CAL  CAT  CBA   179.04   0.0  2
 9BO  Var_06    CAP  CAM  CAS  CAO  -178.51   0.0  2
 9BO  Var_07    CAO  CAN  CAL  CAT   111.96  30.0  2
 9BO  Var_08    CAS  CAO  CAN  CAL   179.30  30.0  1
 9BO  Var_09    CAB  CAS  CAO  CAN   -68.46  30.0  1
 9BO  Var_10    H1   CAA  CAR  OAG   -10.23  30.0  3
 9BO  Var_11    H8   CAC  CAT  CBA    60.99  30.0  3
 9BO  Var_12    H16  CAB  CAS  CAO    61.92  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
 9BO  chir_01  CBA  CAT  OAQ  CAE  negativ

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
 9BO  plan-1  CAP  0.020
 9BO  plan-1  CAZ  0.020
 9BO  plan-1  CAW  0.020
 9BO  plan-1  OAI  0.020
 9BO  plan-1  CAY  0.020
 9BO  plan-1  CAK  0.020
 9BO  plan-1  CAU  0.020
 9BO  plan-1  CAD  0.020
 9BO  plan-1  CAX  0.020
 9BO  plan-1  CLA  0.020
 9BO  plan-1  CAV  0.020
 9BO  plan-1  OAH  0.020
 9BO  plan-2  CAO  0.020
 9BO  plan-2  CAS  0.020
 9BO  plan-2  CAB  0.020
 9BO  plan-2  CAM  0.020
 9BO  plan-2  CAP  0.020
 9BO  plan-2  H19  0.020
 9BO  plan-3  CBA  0.020
 9BO  plan-3  CAT  0.020
 9BO  plan-3  CAC  0.020
 9BO  plan-3  CAL  0.020
 9BO  plan-3  CAN  0.020
 9BO  plan-3  H11  0.020
 9BO  plan-4  CAA  0.020
 9BO  plan-4  CAR  0.020
 9BO  plan-4  OAG  0.020
 9BO  plan-4  OAQ  0.020
 9BO  plan-5  CAY  0.020
 9BO  plan-5  CAK  0.020
 9BO  plan-5  OAF  0.020
 9BO  plan-5  H23  0.020

