# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  8 19:16:05 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(Cc2[nH]c(c3sccc3)c4C(=O)c5ccccc5Oc24)cc1
#
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
 24E  24E  3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one  ligand  42  27  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_24E
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
 24E  C18  C  CR16  0  -0.272   3.5356   0.2087  -0.2299
 24E  C19  C  CR16  0  -0.339   4.4736   0.5832  -1.1720
 24E  C22  C  CR6   0   0.391   4.9705   1.8873  -1.1769
 24E  O3   O  OH1   0  -0.720   5.8825   2.2098  -2.1171
 24E  C21  C  CR16  0  -0.330   4.5150   2.7939  -0.2264
 24E  C20  C  CR16  0  -0.264   3.5722   2.3975   0.7148
 24E  C17  C  CR6   0   0.019   3.0676   1.1050   0.7300
 24E  C16  C  CH2   0  -0.663   2.0238   0.6750   1.7342
 24E  C10  C  CR5   0   0.376   0.7021   0.4016   1.1046
 24E  N1   N  NR15  0  -0.745  -0.1531   1.3911   0.6925
 24E  C9   C  CR56  0   0.165   0.0897  -0.7672   0.7523
 24E  O1   O  O     0  -0.459   0.5722  -2.0075   0.9665
 24E  C4   C  CR66  0   0.425  -0.1697  -3.0513   0.5365
 24E  C6   C  CR16  0  -0.356   0.3735  -4.3185   0.7357
 24E  C5   C  CR16  0  -0.273  -0.3238  -5.4294   0.3065
 24E  C3   C  CR16  0  -0.201  -1.5628  -5.2953  -0.3225
 24E  C1   C  CR16  0  -0.263  -2.0973  -4.0385  -0.5067
 24E  C2   C  CR66  0  -0.150  -1.4176  -2.8929  -0.0781
 24E  C7   C  CR6   0   0.345  -2.0077  -1.5553  -0.3013
 24E  O2   O  O     0  -0.494  -3.1118  -1.4077  -0.8057
 24E  C8   C  CR56  0  -0.192  -1.1482  -0.4861   0.1243
 24E  C11  C  CR5   0   0.397  -1.2758   0.9059   0.1105
 24E  C12  C  CR5   0  -0.216  -2.2956   1.8127  -0.3675
 24E  S1   S  S2    0   0.147  -3.7115   1.3141  -1.2284
 24E  C15  C  CR15  0  -0.477  -4.2528   2.9280  -1.3889
 24E  C14  C  CR15  0  -0.111  -3.4031   3.8171  -0.8036
 24E  C13  C  CR15  0  -0.202  -2.2843   3.1804  -0.2206
 24E  H1   H  HCR6  0   0.274   3.1645  -0.8101  -0.2400
 24E  H2   H  HCR6  0   0.278   4.8277  -0.1300  -1.9060
 24E  H3   H  HOH1  0   0.448   6.1599   3.1267  -2.0140
 24E  H4   H  HCR6  0   0.276   4.8904   3.8110  -0.2147
 24E  H5   H  HCR6  0   0.269   3.2262   3.1185   1.4463
 24E  H6   H  HCH2  0   0.314   2.3529  -0.2297   2.2490
 24E  H7   H  HCH2  0   0.294   1.9152   1.4411   2.5062
 24E  H8   H  HNR5  0   0.408   0.0566   2.3715   0.7999
 24E  H9   H  HCR6  0   0.276   1.3356  -4.4192   1.2211
 24E  H10  H  HCR6  0   0.282   0.1008  -6.4125   0.4607
 24E  H11  H  HCR6  0   0.258  -2.0933  -6.1706  -0.6713
 24E  H12  H  HCR6  0   0.278  -3.0546  -3.9202  -0.9973
 24E  H13  H  HCR5  0   0.301  -5.1817   3.1359  -1.8978
 24E  H14  H  HCR5  0   0.267  -3.5661   4.8848  -0.7834
 24E  H15  H  HCR5  0   0.241  -1.5073   3.7292   0.2937

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
 24E  C21  C20  aromatic  1.390  0.020  1.390
 24E  C21  C22  aromatic  1.390  0.020  1.390
 24E  C20  C17  aromatic  1.388  0.020  1.388
 24E  O3   C22  single    1.349  0.020  1.349
 24E  C22  C19  aromatic  1.396  0.020  1.396
 24E  C17  C16  single    1.511  0.020  1.511
 24E  C17  C18  aromatic  1.394  0.020  1.394
 24E  C16  C10  single    1.489  0.020  1.489
 24E  C19  C18  aromatic  1.381  0.020  1.381
 24E  C10  C9   aromatic  1.366  0.020  1.366
 24E  C10  N1   aromatic  1.371  0.020  1.371
 24E  O1   C9   single    1.348  0.020  1.348
 24E  O1   C4   single    1.351  0.020  1.351
 24E  C6   C4   aromatic  1.393  0.020  1.393
 24E  C6   C5   aromatic  1.380  0.020  1.380
 24E  C9   C8   aromatic  1.416  0.020  1.416
 24E  N1   C11  aromatic  1.355  0.020  1.355
 24E  C4   C2   aromatic  1.400  0.020  1.400
 24E  C5   C3   aromatic  1.396  0.020  1.396
 24E  C8   C11  aromatic  1.398  0.020  1.398
 24E  C8   C7   single    1.436  0.020  1.436
 24E  C11  C12  single    1.446  0.020  1.446
 24E  C2   C7   single    1.479  0.020  1.479
 24E  C2   C1   aromatic  1.399  0.020  1.399
 24E  C3   C1   aromatic  1.378  0.020  1.378
 24E  C7   O2   double    1.223  0.020  1.223
 24E  C12  S1   aromatic  1.730  0.020  1.730
 24E  C12  C13  aromatic  1.376  0.020  1.376
 24E  S1   C15  aromatic  1.710  0.020  1.710
 24E  C13  C14  aromatic  1.413  0.020  1.413
 24E  C15  C14  aromatic  1.362  0.020  1.362
 24E  C18  H1   single    0.930  0.020  1.080
 24E  C19  H2   single    0.930  0.020  1.080
 24E  O3   H3   single    0.850  0.020  0.980
 24E  C21  H4   single    0.930  0.020  1.080
 24E  C20  H5   single    0.930  0.020  1.080
 24E  C16  H6   single    0.970  0.020  1.090
 24E  C16  H7   single    0.970  0.020  1.090
 24E  N1   H8   single    0.860  0.020  1.020
 24E  C6   H9   single    0.930  0.020  1.080
 24E  C5   H10  single    0.930  0.020  1.080
 24E  C3   H11  single    0.930  0.020  1.080
 24E  C1   H12  single    0.930  0.020  1.080
 24E  C15  H13  single    0.930  0.020  1.080
 24E  C14  H14  single    0.930  0.020  1.080
 24E  C13  H15  single    0.930  0.020  1.080

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
 24E  H1   C18  C17  119.71  3.000
 24E  H1   C18  C19  118.74  3.000
 24E  C17  C18  C19  121.55  3.000
 24E  H2   C19  C22  119.78  3.000
 24E  H2   C19  C18  120.38  3.000
 24E  C22  C19  C18  119.84  3.000
 24E  C21  C22  O3   122.83  3.000
 24E  O3   C22  C19  117.81  3.000
 24E  C21  C22  C19  119.36  3.000
 24E  H3   O3   C22  110.34  3.000
 24E  H4   C21  C20  119.68  3.000
 24E  H4   C21  C22  120.38  3.000
 24E  C20  C21  C22  119.95  3.000
 24E  H5   C20  C17  119.75  3.000
 24E  H5   C20  C21  118.94  3.000
 24E  C17  C20  C21  121.31  3.000
 24E  C16  C17  C20  121.57  3.000
 24E  C16  C17  C18  120.44  3.000
 24E  C20  C17  C18  117.98  3.000
 24E  H7   C16  H6   106.13  3.000
 24E  H7   C16  C10  109.82  3.000
 24E  H6   C16  C10  108.35  3.000
 24E  H7   C16  C17  109.79  3.000
 24E  H6   C16  C17  109.94  3.000
 24E  C10  C16  C17  112.60  3.000
 24E  C9   C10  N1   105.09  3.000
 24E  N1   C10  C16  123.24  3.000
 24E  C9   C10  C16  131.61  3.000
 24E  H8   N1   C11  124.50  3.000
 24E  H8   N1   C10  122.68  3.000
 24E  C11  N1   C10  112.80  3.000
 24E  C8   C9   O1   124.47  3.000
 24E  C8   C9   C10  109.66  3.000
 24E  O1   C9   C10  125.87  3.000
 24E  C4   O1   C9   117.64  3.000
 24E  C2   C4   C6   120.88  3.000
 24E  C2   C4   O1   122.81  3.000
 24E  C6   C4   O1   116.31  3.000
 24E  H9   C6   C5   120.91  3.000
 24E  H9   C6   C4   119.70  3.000
 24E  C5   C6   C4   119.39  3.000
 24E  H10  C5   C3   120.00  3.000
 24E  H10  C5   C6   119.26  3.000
 24E  C3   C5   C6   120.74  3.000
 24E  H11  C3   C1   120.32  3.000
 24E  H11  C3   C5   120.19  3.000
 24E  C1   C3   C5   119.48  3.000
 24E  H12  C1   C2   118.63  3.000
 24E  H12  C1   C3   120.22  3.000
 24E  C2   C1   C3   121.15  3.000
 24E  C7   C2   C1   120.03  3.000
 24E  C1   C2   C4   118.35  3.000
 24E  C7   C2   C4   121.62  3.000
 24E  C8   C7   O2   124.93  3.000
 24E  O2   C7   C2   122.12  3.000
 24E  C8   C7   C2   112.94  3.000
 24E  C11  C8   C7   133.14  3.000
 24E  C7   C8   C9   120.44  3.000
 24E  C11  C8   C9   106.37  3.000
 24E  C12  C11  C8   133.80  3.000
 24E  C12  C11  N1   120.13  3.000
 24E  C8   C11  N1   106.07  3.000
 24E  C13  C12  S1   110.26  3.000
 24E  C13  C12  C11  125.62  3.000
 24E  S1   C12  C11  124.11  3.000
 24E  C15  S1   C12   91.94  3.000
 24E  H13  C15  C14  127.87  3.000
 24E  H13  C15  S1   119.90  3.000
 24E  C14  C15  S1   112.23  3.000
 24E  H14  C14  C13  123.85  3.000
 24E  H14  C14  C15  123.99  3.000
 24E  C13  C14  C15  112.16  3.000
 24E  H15  C13  C14  122.44  3.000
 24E  H15  C13  C12  124.14  3.000
 24E  C14  C13  C12  113.41  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
 24E  CONST_01  C21  C20  C17  C18    0.00   0.0  0
 24E  CONST_02  C21  C22  C19  C18    0.00   0.0  0
 24E  CONST_03  C20  C21  C22  C19    0.00   0.0  0
 24E  CONST_04  C20  C17  C18  C19    0.00   0.0  0
 24E  CONST_05  C17  C20  C21  C22    0.00   0.0  0
 24E  CONST_06  C17  C18  C19  C22    0.00   0.0  0
 24E  CONST_07  C11  C8   C9   C10    0.00   0.0  0
 24E  CONST_08  C8   C11  N1   C10    0.00   0.0  0
 24E  CONST_09  C12  C11  N1   C10  180.00   0.0  0
 24E  CONST_10  C8   C9   C10  N1     0.00   0.0  0
 24E  CONST_11  C9   C8   C11  N1     0.00   0.0  0
 24E  CONST_12  S1   C12  C11  N1   180.00   0.0  0
 24E  CONST_13  C13  C12  C11  N1     0.00   0.0  0
 24E  CONST_14  C11  N1   C10  C9     0.00   0.0  0
 24E  CONST_15  C12  C11  C8   C9   180.00   0.0  0
 24E  CONST_16  C3   C5   C6   C4     0.00   0.0  0
 24E  CONST_17  C3   C1   C2   C4     0.00   0.0  0
 24E  CONST_18  C1   C2   C4   C6     0.00   0.0  0
 24E  CONST_19  C1   C3   C5   C6     0.00   0.0  0
 24E  CONST_20  C2   C4   C6   C5     0.00   0.0  0
 24E  CONST_21  C2   C1   C3   C5     0.00   0.0  0
 24E  CONST_22  S1   C12  C11  C8     0.00   0.0  0
 24E  CONST_23  C13  C12  C11  C8   180.00   0.0  0
 24E  CONST_24  C15  S1   C12  C11  180.00   0.0  0
 24E  CONST_25  C14  C13  C12  C11  180.00   0.0  0
 24E  CONST_26  C14  C15  S1   C12    0.00   0.0  0
 24E  CONST_27  C15  C14  C13  C12    0.00   0.0  0
 24E  CONST_28  C14  C13  C12  S1     0.00   0.0  0
 24E  CONST_29  C13  C14  C15  S1     0.00   0.0  0
 24E  CONST_30  C13  C12  S1   C15    0.00   0.0  0
 24E  CONST_31  C12  C11  C8   C7     0.00   0.0  0
 24E  CONST_32  O3   C22  C19  C18  180.00   0.0  0
 24E  CONST_33  C16  C17  C18  C19  180.00   0.0  0
 24E  CONST_34  C20  C21  C22  O3   180.00   0.0  0
 24E  CONST_35  C16  C17  C20  C21  180.00   0.0  0
 24E  CONST_36  O1   C9   C10  C16    0.00   0.0  0
 24E  CONST_37  C8   C9   C10  C16  180.00   0.0  0
 24E  CONST_38  C11  N1   C10  C16  180.00   0.0  0
 24E  CONST_39  H5   C20  C17  C18  180.00   0.0  0
 24E  CONST_40  H4   C21  C22  C19  180.00   0.0  0
 24E  CONST_41  H1   C18  C19  C22  180.00   0.0  0
 24E  CONST_42  H2   C19  C22  C21  180.00   0.0  0
 24E  CONST_43  H8   N1   C10  C9   180.00   0.0  0
 24E  CONST_44  H9   C6   C4   O1     0.00   0.0  0
 24E  CONST_45  H10  C5   C6   C4   180.00   0.0  0
 24E  CONST_46  H12  C1   C2   C4   180.00   0.0  0
 24E  CONST_47  H11  C3   C5   C6   180.00   0.0  0
 24E  CONST_48  H15  C13  C12  C11    0.00   0.0  0
 24E  CONST_49  H13  C15  S1   C12  180.00   0.0  0
 24E  CONST_50  H14  C14  C13  C12  180.00   0.0  0
 24E  Var_01    C6   C4   O1   C9   178.13  30.0  1
 24E  Var_02    C2   C7   C8   C9    -3.24  30.0  1
 24E  Var_03    C8   C9   O1   C4     0.88  30.0  1
 24E  Var_04    C8   C7   C2   C4     2.35  30.0  1
 24E  Var_05    C10  C16  C17  C18  -67.40  30.0  2
 24E  Var_06    C9   C10  C16  C17  100.57  30.0  2

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
 24E  plan-1  C11  0.020
 24E  plan-1  C12  0.020
 24E  plan-1  S1   0.020
 24E  plan-1  C15  0.020
 24E  plan-1  C14  0.020
 24E  plan-1  C13  0.020
 24E  plan-1  H13  0.020
 24E  plan-1  H14  0.020
 24E  plan-1  H15  0.020
 24E  plan-2  C18  0.020
 24E  plan-2  C19  0.020
 24E  plan-2  C22  0.020
 24E  plan-2  O3   0.020
 24E  plan-2  C21  0.020
 24E  plan-2  C20  0.020
 24E  plan-2  C17  0.020
 24E  plan-2  C16  0.020
 24E  plan-2  H1   0.020
 24E  plan-2  H2   0.020
 24E  plan-2  H4   0.020
 24E  plan-2  H5   0.020
 24E  plan-3  C16  0.020
 24E  plan-3  C10  0.020
 24E  plan-3  N1   0.020
 24E  plan-3  C9   0.020
 24E  plan-3  O1   0.020
 24E  plan-3  C7   0.020
 24E  plan-3  C8   0.020
 24E  plan-3  C11  0.020
 24E  plan-3  C12  0.020
 24E  plan-3  H8   0.020
 24E  plan-4  O1   0.020
 24E  plan-4  C4   0.020
 24E  plan-4  C6   0.020
 24E  plan-4  C5   0.020
 24E  plan-4  C3   0.020
 24E  plan-4  C1   0.020
 24E  plan-4  C2   0.020
 24E  plan-4  C7   0.020
 24E  plan-4  H9   0.020
 24E  plan-4  H10  0.020
 24E  plan-4  H11  0.020
 24E  plan-4  H12  0.020
 24E  plan-5  C2   0.020
 24E  plan-5  C7   0.020
 24E  plan-5  O2   0.020
 24E  plan-5  C8   0.020

