# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 12 00:18:12 2022
#   Inital geometry file: a 140 line input string
#   Ligand name: 2-[2,6-bis(chloranyl)phenyl]-1-[(1~{S},3~{R})-3-(hydroxymethyl)-1-methyl-5-(3-methyl-3-oxidanyl-butyl)-3,4-dihydro-1~{H}-isoquinolin-2-yl]ethanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H]1N([C@@H](CO)Cc2c(CCC(C)(C)O)cccc12)C(=O)Cc3c(Cl)cccc3Cl
#
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
 G4C  G4C  2-[2,6-bis(chloranyl)phenyl]-1-[(1~{S},3~{R})-3-(hydroxymethyl)-1-methyl-5-(3-methyl-3-oxidanyl-butyl)-3,4-dihydro-1~{H}-isoquinolin-2-yl]ethanone  ligand  59  30  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G4C
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
 G4C  C10  C   CR16  0  -0.184  14.5939  18.9049   -3.1594
 G4C  C12  C   CR16  0  -0.184  14.1844  17.8328   -1.0501
 G4C  C03  C   CH1   0  -0.140  12.5361  12.5837   -5.0271
 G4C  C05  C   C     0   0.588  12.7546  14.8557   -4.2139
 G4C  C06  C   CH2   0  -0.720  12.0540  16.1142   -3.7053
 G4C  C07  C   CR6   0   0.367  13.0255  17.0388   -3.0449
 G4C  C08  C   CR6   0  -0.152  13.7108  18.0208   -3.7580
 G4C  C11  C   CR16  0  -0.293  14.8222  18.8093   -1.7968
 G4C  C13  C   CR6   0  -0.143  13.3087  16.9645   -1.6814
 G4C  C18  C   CR6   0   0.149   9.7933  12.9674   -5.4599
 G4C  O15  O   O     0  -0.472  13.9568  14.7251   -4.0611
 G4C  C16  C   CH1   0  -0.191  10.6178  14.2133   -5.2553
 G4C  C17  C   CH3   0  -0.645  10.6405  15.0098   -6.5670
 G4C  C19  C   CR6   0   0.020  10.3842  11.8396   -6.0343
 G4C  C20  C   CR6   0   0.078   9.6062  10.7154   -6.3335
 G4C  C21  C   CH2   0  -0.527  10.1940   9.4617   -6.9404
 G4C  C22  C   CH2   0  -0.457   9.4030   8.8154   -8.0821
 G4C  C23  C   CT    0   0.226   9.5459   9.4494   -9.4761
 G4C  C24  C   CH3   0  -0.671   9.1226  10.9165   -9.4961
 G4C  C26  C   CH3   0  -0.663  10.9721   9.3154   -9.9964
 G4C  C27  C   CR16  0  -0.317   8.2483  10.7501   -6.0139
 G4C  C28  C   CR16  0  -0.237   7.6673  11.8621   -5.4287
 G4C  C29  C   CR16  0  -0.336   8.4412  12.9799   -5.1553
 G4C  C30  C   CH2   0  -0.546  11.8730  11.9231   -6.2333
 G4C  N04  N   NT    0  -0.474  11.9711  13.9073   -4.7827
 G4C  O25  O   OH1   0  -0.675   8.7386   8.7035  -10.3823
 G4C  CL9  CL  CL    0  -0.119  13.4776  18.1460   -5.4725
 G4C  CL4  CL  CL    0  -0.120  12.5627  15.7286   -0.7195
 G4C  H1   H   HCR6  0   0.284  15.1000  19.6551   -3.7509
 G4C  H2   H   HCR6  0   0.284  14.3704  17.7435    0.0112
 G4C  H5   H   HCH1  0   0.265  13.5981  12.7027   -5.2437
 G4C  H6   H   HCH2  0   0.304  11.5355  16.6356   -4.5095
 G4C  H7   H   HCH2  0   0.304  11.2760  15.8215   -2.9973
 G4C  H8   H   HCR6  0   0.277  15.5066  19.4944   -1.3154
 G4C  H9   H   HCH1  0   0.280  10.1134  14.8144   -4.4966
 G4C  H10  H   HCH3  0   0.234  11.2440  15.9150   -6.4885
 G4C  H11  H   HCH3  0   0.240  11.0442  14.4143   -7.3857
 G4C  H12  H   HCH3  0   0.239   9.6275  15.3087   -6.8364
 G4C  H13  H   HCH2  0   0.258  10.2957   8.7194   -6.1425
 G4C  H14  H   HCH2  0   0.246  11.2106   9.6449   -7.2854
 G4C  H15  H   HCH2  0   0.229   8.3391   8.7763   -7.8267
 G4C  H16  H   HCH2  0   0.234   9.7261   7.7739   -8.1646
 G4C  H17  H   HCH3  0   0.224   8.1037  11.0438   -9.1225
 G4C  H18  H   HCH3  0   0.228   9.7753  11.5357   -8.8808
 G4C  H19  H   HCH3  0   0.230   9.1616  11.3034  -10.5161
 G4C  H20  H   HCH3  0   0.227  11.3059   8.2761   -9.9778
 G4C  H21  H   HCH3  0   0.233  11.0427   9.6777  -11.0235
 G4C  H22  H   HCH3  0   0.225  11.6680   9.9018   -9.3969
 G4C  H23  H   HCR6  0   0.246   7.6280   9.8860   -6.2172
 G4C  H24  H   HCR6  0   0.249   6.6128  11.8567   -5.1847
 G4C  H25  H   HCR6  0   0.244   7.9959  13.8586   -4.7031
 G4C  H26  H   HCH2  0   0.268  12.3244  10.9409   -6.3647
 G4C  H27  H   HCH2  0   0.273  12.1184  12.4833   -7.1407
 G4C  H28  H   HOH1  0   0.452  12.6812  11.7597   -1.9027
 G4C  H29  H   HOH1  0   0.437   7.8234   8.7670  -10.0883
 G4C  C02  C   CH2   0  -0.113  12.3773  11.6745   -3.8073
 G4C  O01  O   OH1   0  -0.657  12.9588  12.2639   -2.6725
 G4C  H3   H   HCH2  0   0.200  11.3121  11.4720   -3.6452
 G4C  H4   H   HCH2  0   0.194  12.8507  10.7131   -4.0525

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
 G4C  C26  C23  single    1.524  0.020  1.524
 G4C  C24  C23  single    1.527  0.020  1.527
 G4C  O25  C23  single    1.425  0.020  1.425
 G4C  C23  C22  single    1.538  0.020  1.538
 G4C  C22  C21  single    1.532  0.020  1.532
 G4C  C21  C20  single    1.512  0.020  1.512
 G4C  C20  C27  aromatic  1.395  0.020  1.395
 G4C  C20  C19  aromatic  1.399  0.020  1.399
 G4C  C27  C28  aromatic  1.384  0.020  1.384
 G4C  C30  C19  single    1.504  0.020  1.504
 G4C  C30  C03  single    1.527  0.020  1.527
 G4C  C19  C18  aromatic  1.397  0.020  1.397
 G4C  C17  C16  single    1.535  0.020  1.535
 G4C  C28  C29  aromatic  1.387  0.020  1.387
 G4C  C18  C29  aromatic  1.386  0.020  1.386
 G4C  C18  C16  single    1.508  0.020  1.508
 G4C  C03  N04  single    1.460  0.020  1.460
 G4C  C03  C02  single    1.530  0.020  1.530
 G4C  C16  N04  single    1.466  0.020  1.466
 G4C  N04  C05  single    1.355  0.020  1.355
 G4C  CL9  C08  single    1.735  0.020  1.735
 G4C  C02  O01  single    1.405  0.020  1.405
 G4C  C05  O15  double    1.219  0.020  1.219
 G4C  C05  C06  single    1.528  0.020  1.528
 G4C  C06  C07  single    1.495  0.020  1.495
 G4C  C08  C07  aromatic  1.394  0.020  1.394
 G4C  C08  C10  aromatic  1.386  0.020  1.386
 G4C  C07  C13  aromatic  1.395  0.020  1.395
 G4C  C10  C11  aromatic  1.385  0.020  1.385
 G4C  C13  CL4  single    1.735  0.020  1.735
 G4C  C13  C12  aromatic  1.385  0.020  1.385
 G4C  C11  C12  aromatic  1.385  0.020  1.385
 G4C  C10  H1   single    0.930  0.020  1.080
 G4C  C12  H2   single    0.930  0.020  1.080
 G4C  C02  H3   single    0.970  0.020  1.090
 G4C  C02  H4   single    0.970  0.020  1.090
 G4C  C03  H5   single    0.970  0.020  1.090
 G4C  C06  H6   single    0.970  0.020  1.090
 G4C  C06  H7   single    0.970  0.020  1.090
 G4C  C11  H8   single    0.930  0.020  1.080
 G4C  C16  H9   single    0.970  0.020  1.090
 G4C  C17  H10  single    0.970  0.020  1.090
 G4C  C17  H11  single    0.970  0.020  1.090
 G4C  C17  H12  single    0.970  0.020  1.090
 G4C  C21  H13  single    0.970  0.020  1.090
 G4C  C21  H14  single    0.970  0.020  1.090
 G4C  C22  H15  single    0.970  0.020  1.090
 G4C  C22  H16  single    0.970  0.020  1.090
 G4C  C24  H17  single    0.970  0.020  1.090
 G4C  C24  H18  single    0.970  0.020  1.090
 G4C  C24  H19  single    0.970  0.020  1.090
 G4C  C26  H20  single    0.970  0.020  1.090
 G4C  C26  H21  single    0.970  0.020  1.090
 G4C  C26  H22  single    0.970  0.020  1.090
 G4C  C27  H23  single    0.930  0.020  1.080
 G4C  C28  H24  single    0.930  0.020  1.080
 G4C  C29  H25  single    0.930  0.020  1.080
 G4C  C30  H26  single    0.970  0.020  1.090
 G4C  C30  H27  single    0.970  0.020  1.090
 G4C  O01  H28  single    0.850  0.020  0.980
 G4C  O25  H29  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
 G4C  H1   C10  C11  120.60  3.000
 G4C  H1   C10  C08  120.31  3.000
 G4C  C11  C10  C08  119.09  3.000
 G4C  H2   C12  C13  120.28  3.000
 G4C  H2   C12  C11  120.55  3.000
 G4C  C13  C12  C11  119.16  3.000
 G4C  H5   C03  N04  108.14  3.000
 G4C  H5   C03  C30  108.26  3.000
 G4C  N04  C03  C30  110.88  3.000
 G4C  H5   C03  C02  108.93  3.000
 G4C  N04  C03  C02  111.43  3.000
 G4C  C30  C03  C02  109.13  3.000
 G4C  N04  C05  O15  123.22  3.000
 G4C  O15  C05  C06  119.93  3.000
 G4C  N04  C05  C06  116.82  3.000
 G4C  H7   C06  H6   105.53  3.000
 G4C  H7   C06  C07  110.03  3.000
 G4C  H6   C06  C07  109.83  3.000
 G4C  H7   C06  C05  108.77  3.000
 G4C  H6   C06  C05  111.51  3.000
 G4C  C07  C06  C05  111.01  3.000
 G4C  C13  C07  C08  115.97  3.000
 G4C  C13  C07  C06  122.07  3.000
 G4C  C08  C07  C06  121.96  3.000
 G4C  CL9  C08  C07  119.37  3.000
 G4C  C07  C08  C10  122.81  3.000
 G4C  CL9  C08  C10  117.82  3.000
 G4C  H8   C11  C12  119.88  3.000
 G4C  H8   C11  C10  119.90  3.000
 G4C  C12  C11  C10  120.22  3.000
 G4C  CL4  C13  C07  119.52  3.000
 G4C  CL4  C13  C12  117.75  3.000
 G4C  C07  C13  C12  122.72  3.000
 G4C  C29  C18  C19  120.69  3.000
 G4C  C29  C18  C16  119.74  3.000
 G4C  C19  C18  C16  119.45  3.000
 G4C  H9   C16  N04  108.51  3.000
 G4C  H9   C16  C17  108.37  3.000
 G4C  N04  C16  C17  111.73  3.000
 G4C  H9   C16  C18  107.26  3.000
 G4C  N04  C16  C18  112.09  3.000
 G4C  C17  C16  C18  108.72  3.000
 G4C  H12  C17  H11  107.96  3.000
 G4C  H12  C17  H10  107.72  3.000
 G4C  H11  C17  H10  107.62  3.000
 G4C  H12  C17  C16  109.86  3.000
 G4C  H11  C17  C16  111.34  3.000
 G4C  H10  C17  C16  112.17  3.000
 G4C  C30  C19  C20  124.50  3.000
 G4C  C30  C19  C18  115.36  3.000
 G4C  C20  C19  C18  120.09  3.000
 G4C  C27  C20  C21  119.40  3.000
 G4C  C27  C20  C19  118.16  3.000
 G4C  C21  C20  C19  122.40  3.000
 G4C  H14  C21  H13  104.97  3.000
 G4C  H14  C21  C22  108.48  3.000
 G4C  H13  C21  C22  107.76  3.000
 G4C  H14  C21  C20  110.53  3.000
 G4C  H13  C21  C20  107.81  3.000
 G4C  C22  C21  C20  116.63  3.000
 G4C  H16  C22  H15  105.71  3.000
 G4C  H16  C22  C23  107.26  3.000
 G4C  H15  C22  C23  108.45  3.000
 G4C  H16  C22  C21  107.79  3.000
 G4C  H15  C22  C21  110.06  3.000
 G4C  C23  C22  C21  116.97  3.000
 G4C  O25  C23  C26  105.49  3.000
 G4C  O25  C23  C24  109.73  3.000
 G4C  C26  C23  C24  109.84  3.000
 G4C  O25  C23  C22  107.94  3.000
 G4C  C24  C23  C22  112.47  3.000
 G4C  C26  C23  C22  111.11  3.000
 G4C  H19  C24  H18  107.74  3.000
 G4C  H19  C24  H17  108.15  3.000
 G4C  H18  C24  H17  107.41  3.000
 G4C  H19  C24  C23  110.05  3.000
 G4C  H18  C24  C23  111.87  3.000
 G4C  H17  C24  C23  111.47  3.000
 G4C  H22  C26  H21  107.32  3.000
 G4C  H22  C26  H20  107.92  3.000
 G4C  H21  C26  H20  108.20  3.000
 G4C  H22  C26  C23  111.25  3.000
 G4C  H21  C26  C23  110.65  3.000
 G4C  H20  C26  C23  111.35  3.000
 G4C  H23  C27  C28  118.68  3.000
 G4C  H23  C27  C20  119.64  3.000
 G4C  C28  C27  C20  121.68  3.000
 G4C  H24  C28  C29  120.21  3.000
 G4C  H24  C28  C27  120.01  3.000
 G4C  C29  C28  C27  119.78  3.000
 G4C  H25  C29  C28  120.43  3.000
 G4C  H25  C29  C18  119.99  3.000
 G4C  C28  C29  C18  119.58  3.000
 G4C  H27  C30  H26  105.59  3.000
 G4C  H27  C30  C19  111.10  3.000
 G4C  H26  C30  C19  112.09  3.000
 G4C  H27  C30  C03  109.65  3.000
 G4C  H26  C30  C03  107.79  3.000
 G4C  C19  C30  C03  110.45  3.000
 G4C  C16  N04  C05  121.53  3.000
 G4C  C05  N04  C03  118.75  3.000
 G4C  C16  N04  C03  119.52  3.000
 G4C  H29  O25  C23  108.04  3.000
 G4C  H4   C02  H3   106.85  3.000
 G4C  H4   C02  O01  111.65  3.000
 G4C  H3   C02  O01  111.11  3.000
 G4C  H4   C02  C03  107.30  3.000
 G4C  H3   C02  C03  109.18  3.000
 G4C  O01  C02  C03  110.60  3.000
 G4C  H28  O01  C02  107.90  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
 G4C  CONST_01  C13  C07  C08  C10     0.00   0.0  0
 G4C  CONST_02  C13  C12  C11  C10     0.00   0.0  0
 G4C  CONST_03  C08  C07  C13  C12     0.00   0.0  0
 G4C  CONST_04  C08  C10  C11  C12     0.00   0.0  0
 G4C  CONST_05  C11  C10  C08  C07     0.00   0.0  0
 G4C  CONST_06  C11  C12  C13  C07     0.00   0.0  0
 G4C  CONST_07  C27  C20  C19  C18     0.00   0.0  0
 G4C  CONST_08  C27  C28  C29  C18     0.00   0.0  0
 G4C  CONST_09  C28  C27  C20  C19     0.00   0.0  0
 G4C  CONST_10  C28  C29  C18  C19     0.00   0.0  0
 G4C  CONST_11  C29  C28  C27  C20     0.00   0.0  0
 G4C  CONST_12  C29  C18  C19  C20     0.00   0.0  0
 G4C  CONST_13  C06  C07  C08  C10   180.00   0.0  0
 G4C  CONST_14  C06  C07  C13  C12   180.00   0.0  0
 G4C  CONST_15  CL4  C13  C07  C08   180.00   0.0  0
 G4C  CONST_16  CL9  C08  C10  C11   180.00   0.0  0
 G4C  CONST_17  CL4  C13  C12  C11   180.00   0.0  0
 G4C  CONST_18  CL9  C08  C07  C13   180.00   0.0  0
 G4C  CONST_19  C21  C20  C19  C18   180.00   0.0  0
 G4C  CONST_20  C28  C27  C20  C21   180.00   0.0  0
 G4C  CONST_21  C30  C19  C20  C21     0.00   0.0  0
 G4C  CONST_22  H2   C12  C11  C10   180.00   0.0  0
 G4C  CONST_23  H1   C10  C11  C12   180.00   0.0  0
 G4C  CONST_24  H8   C11  C10  C08   180.00   0.0  0
 G4C  CONST_25  H24  C28  C29  C18   180.00   0.0  0
 G4C  CONST_26  H25  C29  C18  C16     0.00   0.0  0
 G4C  CONST_27  H23  C27  C20  C19   180.00   0.0  0
 G4C  CONST_28  O15  C05  N04  C03     0.00   0.0  0
 G4C  CONST_29  C06  C05  N04  C03   180.00   0.0  0
 G4C  Var_01    C20  C19  C30  C03  -136.49  30.0  1
 G4C  Var_02    C08  C07  C06  C05    89.62  30.0  2
 G4C  Var_03    N04  C05  C06  C07   177.20  30.0  2
 G4C  Var_04    C22  C21  C20  C19  -136.24  30.0  1
 G4C  Var_05    C23  C22  C21  C20    79.50  30.0  2
 G4C  Var_06    C26  C23  C22  C21    64.72  30.0  3
 G4C  Var_07    H20  C26  C23  C22    54.01  30.0  3
 G4C  Var_08    H17  C24  C23  C22   -55.40  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
 G4C  chir_01  C03  C30  N04  C02  negativ
 G4C  chir_02  C16  N04  C18  C17  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
 G4C  plan-1  C10  0.020
 G4C  plan-1  C12  0.020
 G4C  plan-1  C06  0.020
 G4C  plan-1  C07  0.020
 G4C  plan-1  C08  0.020
 G4C  plan-1  C11  0.020
 G4C  plan-1  C13  0.020
 G4C  plan-1  CL9  0.020
 G4C  plan-1  CL4  0.020
 G4C  plan-1  H1   0.020
 G4C  plan-1  H2   0.020
 G4C  plan-1  H8   0.020
 G4C  plan-2  C18  0.020
 G4C  plan-2  C16  0.020
 G4C  plan-2  C19  0.020
 G4C  plan-2  C20  0.020
 G4C  plan-2  C21  0.020
 G4C  plan-2  C27  0.020
 G4C  plan-2  C28  0.020
 G4C  plan-2  C29  0.020
 G4C  plan-2  C30  0.020
 G4C  plan-2  H23  0.020
 G4C  plan-2  H24  0.020
 G4C  plan-2  H25  0.020
 G4C  plan-3  C03  0.020
 G4C  plan-3  C05  0.020
 G4C  plan-3  C06  0.020
 G4C  plan-3  O15  0.020
 G4C  plan-3  C16  0.020
 G4C  plan-3  N04  0.020

