# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 05:04:32 2021
#   Inital geometry file: a 122 line input string
#   Ligand name: ({[(6E,9beta,17beta)-3,17-dihydroxyestra-1,3,5(10)-trien-6-ylidene]amino}oxy)acetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12CC[C@H]3[C@@H](CC(=N\OCC(O)=O)/c4cc(O)ccc34)[C@@H]1CC[C@@H]2O
#
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
 ECO  ECO  '({[(6E,9beta,17beta)-3,17-dihydroxyestra-1,3,5(10)-trien-6-ylidene]amino}oxy)acetic acid'  ligand  51  26  .  2022-11-17  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ECO
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
 ECO  C1    C  CR16  0  -0.328  55.8189  76.5464  32.7167
 ECO  C2    C  CR16  0  -0.326  55.0439  75.6284  33.4007
 ECO  C3    C  CR6   0   0.373  54.8973  74.3378  32.8972
 ECO  O3    O  OH1   0  -0.636  54.1400  73.4688  33.5983
 ECO  C4    C  CR16  0  -0.430  55.5290  73.9974  31.7131
 ECO  C5    C  CR6   0   0.045  56.3046  74.9320  31.0214
 ECO  C6    C  C     0   0.207  56.9375  74.5553  29.7421
 ECO  C7    C  CH2   0  -0.509  57.9600  75.4652  29.1301
 ECO  C8    C  CH1   0  -0.262  58.4901  76.5103  30.1003
 ECO  C9    C  CH1   0  -0.269  57.3147  77.2357  30.7732
 ECO  C10   C  CR6   0   0.099  56.4678  76.2304  31.5228
 ECO  C11   C  CH2   0  -0.458  57.7672  78.4220  31.6320
 ECO  C12   C  CH2   0  -0.406  58.7152  79.3708  30.8937
 ECO  C13   C  CT    0  -0.103  59.9022  78.6207  30.3007
 ECO  C14   C  CH1   0  -0.196  59.3568  77.5245  29.3787
 ECO  C15   C  CH2   0  -0.449  60.5793  77.0428  28.5906
 ECO  C16   C  CH2   0  -0.488  61.4758  78.2991  28.4928
 ECO  C17   C  CH1   0   0.103  60.7347  79.4007  29.2799
 ECO  O17   O  OH1   0  -0.674  61.5677  80.3547  29.8901
 ECO  C18   C  CH3   0  -0.675  60.8076  78.0770  31.4108
 ECO  N19   N  N     0  -0.141  56.5429  73.4636  29.2132
 ECO  O19   O  O2    0  -0.395  57.1833  73.1827  28.0380
 ECO  C19   C  CH2   0  -0.228  56.6326  72.0224  27.4690
 ECO  C20   C  C     0   0.496  57.5127  71.5088  26.3573
 ECO  O20   O  OH1   0  -0.576  58.7064  72.0695  26.3212
 ECO  O21   O  O     0  -0.448  57.1416  70.6452  25.6033
 ECO  HC1   H  HCR6  0   0.255  55.9143  77.5379  33.1375
 ECO  HC2   H  HCR6  0   0.264  54.5591  75.9067  34.3280
 ECO  HO3   H  HOH1  0   0.473  54.1128  72.6144  33.1533
 ECO  HC4   H  HCR6  0   0.265  55.4262  72.9944  31.3160
 ECO  HC71  H  HCH2  0   0.258  57.4988  75.9700  28.2711
 ECO  HC72  H  HCH2  0   0.276  58.7836  74.8754  28.7221
 ECO  HC8   H  HCH1  0   0.234  59.0820  75.9985  30.8694
 ECO  HC9   H  HCH1  0   0.237  56.7024  77.6497  29.9572
 ECO  H111  H  HCH2  0   0.224  58.2414  78.0538  32.5465
 ECO  H112  H  HCH2  0   0.241  56.8938  78.9932  31.9545
 ECO  H121  H  HCH2  0   0.229  59.0437  80.1614  31.5740
 ECO  H122  H  HCH2  0   0.215  58.1684  79.8651  30.0819
 ECO  H14   H  HCH1  0   0.219  58.6938  78.0328  28.6614
 ECO  H151  H  HCH2  0   0.236  60.3019  76.6543  27.6100
 ECO  H152  H  HCH2  0   0.226  61.0930  76.2324  29.1146
 ECO  H161  H  HCH2  0   0.235  61.6568  78.6008  27.4599
 ECO  H162  H  HCH2  0   0.229  62.4532  78.1191  28.9461
 ECO  H17   H  HCH1  0   0.195  60.0297  79.9001  28.5970
 ECO  H17O  H  HOH1  0   0.448  62.0415  80.8273  29.1993
 ECO  H181  H  HCH3  0   0.231  60.2676  77.4496  32.1191
 ECO  H182  H  HCH3  0   0.232  61.6344  77.4788  31.0258
 ECO  H183  H  HCH3  0   0.234  61.2409  78.8979  31.9828
 ECO  H191  H  HCH2  0   0.263  55.6337  72.2034  27.0590
 ECO  H192  H  HCH2  0   0.269  56.5390  71.2209  28.2108
 ECO  H20   H  HOH1  0   0.487  59.2295  71.6802  25.6035

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
 ECO  C1   C2    aromatic  1.382  0.020  1.382
 ECO  C1   C10   aromatic  1.395  0.020  1.395
 ECO  C1   HC1   single    0.930  0.020  1.080
 ECO  C2   C3    aromatic  1.393  0.020  1.393
 ECO  C2   HC2   single    0.930  0.020  1.080
 ECO  C3   O3    single    1.349  0.020  1.349
 ECO  C3   C4    aromatic  1.384  0.020  1.384
 ECO  O3   HO3   single    0.850  0.020  0.980
 ECO  C4   C5    aromatic  1.398  0.020  1.398
 ECO  C4   HC4   single    0.930  0.020  1.080
 ECO  C5   C6    single    1.476  0.020  1.476
 ECO  C5   C10   aromatic  1.401  0.020  1.401
 ECO  C6   C7    single    1.499  0.020  1.499
 ECO  C6   N19   double    1.276  0.020  1.276
 ECO  C7   C8    single    1.521  0.020  1.521
 ECO  C7   HC71  single    0.970  0.020  1.090
 ECO  C7   HC72  single    0.970  0.020  1.090
 ECO  C8   C9    single    1.536  0.020  1.536
 ECO  C8   C14   single    1.517  0.020  1.517
 ECO  C8   HC8   single    0.970  0.020  1.090
 ECO  C9   C10   single    1.513  0.020  1.513
 ECO  C9   C11   single    1.533  0.020  1.533
 ECO  C9   HC9   single    0.970  0.020  1.090
 ECO  C11  C12   single    1.531  0.020  1.531
 ECO  C11  H111  single    0.970  0.020  1.090
 ECO  C11  H112  single    0.970  0.020  1.090
 ECO  C12  C13   single    1.524  0.020  1.524
 ECO  C12  H121  single    0.970  0.020  1.090
 ECO  C12  H122  single    0.970  0.020  1.090
 ECO  C13  C14   single    1.533  0.020  1.533
 ECO  C13  C17   single    1.531  0.020  1.531
 ECO  C13  C18   single    1.532  0.020  1.532
 ECO  C14  C15   single    1.532  0.020  1.532
 ECO  C14  H14   single    0.970  0.020  1.090
 ECO  C15  C16   single    1.546  0.020  1.546
 ECO  C15  H151  single    0.970  0.020  1.090
 ECO  C15  H152  single    0.970  0.020  1.090
 ECO  C16  C17   single    1.544  0.020  1.544
 ECO  C16  H161  single    0.970  0.020  1.090
 ECO  C16  H162  single    0.970  0.020  1.090
 ECO  C17  O17   single    1.406  0.020  1.406
 ECO  C17  H17   single    0.970  0.020  1.090
 ECO  O17  H17O  single    0.850  0.020  0.980
 ECO  C18  H181  single    0.970  0.020  1.090
 ECO  C18  H182  single    0.970  0.020  1.090
 ECO  C18  H183  single    0.970  0.020  1.090
 ECO  N19  O19   single    1.368  0.020  1.368
 ECO  O19  C19   single    1.405  0.020  1.405
 ECO  C19  C20   single    1.508  0.020  1.508
 ECO  C19  H191  single    0.970  0.020  1.090
 ECO  C19  H192  single    0.970  0.020  1.090
 ECO  C20  O20   single    1.319  0.020  1.319
 ECO  C20  O21   double    1.205  0.020  1.205
 ECO  O20  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
 ECO  HC1   C1   C10   119.98  3.000
 ECO  HC1   C1   C2    117.76  3.000
 ECO  C10   C1   C2    122.26  3.000
 ECO  HC2   C2   C3    120.04  3.000
 ECO  HC2   C2   C1    120.27  3.000
 ECO  C3    C2   C1    119.69  3.000
 ECO  C4    C3   O3    122.83  3.000
 ECO  C4    C3   C2    119.26  3.000
 ECO  O3    C3   C2    117.90  3.000
 ECO  HO3   O3   C3    110.30  3.000
 ECO  HC4   C4   C5    119.35  3.000
 ECO  HC4   C4   C3    119.85  3.000
 ECO  C5    C4   C3    120.80  3.000
 ECO  C10   C5   C6    119.77  3.000
 ECO  C10   C5   C4    120.47  3.000
 ECO  C6    C5   C4    119.75  3.000
 ECO  N19   C6   C7    124.13  3.000
 ECO  N19   C6   C5    116.43  3.000
 ECO  C7    C6   C5    119.42  3.000
 ECO  HC72  C7   HC71  105.83  3.000
 ECO  HC72  C7   C8    110.27  3.000
 ECO  HC71  C7   C8    109.24  3.000
 ECO  HC72  C7   C6    109.82  3.000
 ECO  HC71  C7   C6    108.17  3.000
 ECO  C8    C7   C6    113.22  3.000
 ECO  HC8   C8   C14   109.70  3.000
 ECO  HC8   C8   C9    109.03  3.000
 ECO  C14   C8   C9    109.26  3.000
 ECO  HC8   C8   C7    108.33  3.000
 ECO  C14   C8   C7    110.80  3.000
 ECO  C9    C8   C7    109.70  3.000
 ECO  HC9   C9   C11   106.76  3.000
 ECO  HC9   C9   C10   107.80  3.000
 ECO  C11   C9   C10   113.70  3.000
 ECO  HC9   C9   C8    106.16  3.000
 ECO  C11   C9   C8    112.64  3.000
 ECO  C10   C9   C8    109.35  3.000
 ECO  C9    C10  C5    120.24  3.000
 ECO  C9    C10  C1    122.26  3.000
 ECO  C5    C10  C1    117.50  3.000
 ECO  H112  C11  H111  106.00  3.000
 ECO  H112  C11  C12   108.27  3.000
 ECO  H111  C11  C12   110.08  3.000
 ECO  H112  C11  C9    109.51  3.000
 ECO  H111  C11  C9    109.62  3.000
 ECO  C12   C11  C9    113.10  3.000
 ECO  H122  C12  H121  106.53  3.000
 ECO  H122  C12  C13   108.79  3.000
 ECO  H121  C12  C13   111.33  3.000
 ECO  H122  C12  C11   109.12  3.000
 ECO  H121  C12  C11   109.52  3.000
 ECO  C13   C12  C11   111.40  3.000
 ECO  C18   C13  C17   110.04  3.000
 ECO  C18   C13  C14   113.10  3.000
 ECO  C17   C13  C14    99.02  3.000
 ECO  C18   C13  C12   110.67  3.000
 ECO  C17   C13  C12   115.60  3.000
 ECO  C14   C13  C12   107.99  3.000
 ECO  H14   C14  C15   106.88  3.000
 ECO  H14   C14  C13   106.02  3.000
 ECO  C15   C14  C13   104.50  3.000
 ECO  H14   C14  C8    105.94  3.000
 ECO  C15   C14  C8    119.37  3.000
 ECO  C13   C14  C8    113.29  3.000
 ECO  H152  C15  H151  106.65  3.000
 ECO  H152  C15  C16   111.10  3.000
 ECO  H151  C15  C16   112.33  3.000
 ECO  H152  C15  C14   111.18  3.000
 ECO  H151  C15  C14   111.81  3.000
 ECO  C16   C15  C14   103.87  3.000
 ECO  H162  C16  H161  106.85  3.000
 ECO  H162  C16  C17   109.61  3.000
 ECO  H161  C16  C17   111.41  3.000
 ECO  H162  C16  C15   111.01  3.000
 ECO  H161  C16  C15   112.37  3.000
 ECO  C17   C16  C15   105.62  3.000
 ECO  H17   C17  O17   109.92  3.000
 ECO  H17   C17  C16   108.35  3.000
 ECO  O17   C17  C16   114.91  3.000
 ECO  H17   C17  C13   107.25  3.000
 ECO  O17   C17  C13   112.24  3.000
 ECO  C16   C17  C13   103.74  3.000
 ECO  H17O  O17  C17   108.27  3.000
 ECO  H183  C18  H182  107.26  3.000
 ECO  H183  C18  H181  106.82  3.000
 ECO  H182  C18  H181  106.82  3.000
 ECO  H183  C18  C13   110.35  3.000
 ECO  H182  C18  C13   112.76  3.000
 ECO  H181  C18  C13   112.49  3.000
 ECO  O19   N19  C6    112.79  3.000
 ECO  C19   O19  N19   109.53  3.000
 ECO  H192  C19  H191  107.24  3.000
 ECO  H192  C19  C20   107.44  3.000
 ECO  H191  C19  C20   108.22  3.000
 ECO  H192  C19  O19   111.30  3.000
 ECO  H191  C19  O19   111.89  3.000
 ECO  C20   C19  O19   110.56  3.000
 ECO  O21   C20  O20   124.47  3.000
 ECO  O21   C20  C19   121.71  3.000
 ECO  O20   C20  C19   113.80  3.000
 ECO  H20   O20  C20   109.75  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
 ECO  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 ECO  CONST_02  C4   C5   C10  C1      0.00   0.0  0
 ECO  CONST_03  C5   C10  C1   C2      0.00   0.0  0
 ECO  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 ECO  CONST_05  C10  C1   C2   C3      0.00   0.0  0
 ECO  CONST_06  C10  C5   C4   C3      0.00   0.0  0
 ECO  CONST_07  O3   C3   C2   C1    180.00   0.0  0
 ECO  CONST_08  C5   C4   C3   O3    180.00   0.0  0
 ECO  CONST_09  HC4  C4   C3   C2    180.00   0.0  0
 ECO  CONST_10  HC1  C1   C2   C3    180.00   0.0  0
 ECO  CONST_11  HC2  C2   C3   C4    180.00   0.0  0
 ECO  CONST_12  H20  O20  C20  C19   180.00   0.0  0
 ECO  Var_01    C7   C6   C5   C4   -169.07  30.0  1
 ECO  Var_02    C8   C7   C6   C5     15.26  30.0  1
 ECO  Var_03    C13  C12  C11  C9    -53.28  30.0  1
 ECO  Var_04    C17  C16  C15  C14     2.24  30.0  1
 ECO  Var_05    C20  C19  O19  N19  -166.87  30.0  3
 ECO  Var_06    O20  C20  C19  O19    12.53  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
 ECO  chir_01  C8   C7   C9   C14  positiv
 ECO  chir_02  C9   C8   C10  C11  negativ
 ECO  chir_03  C13  C17  C14  C12  positiv
 ECO  chir_04  C14  C15  C13  C8   positiv
 ECO  chir_05  C17  O17  C13  C16  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
 ECO  plan-1  C19  0.020
 ECO  plan-1  C20  0.020
 ECO  plan-1  O20  0.020
 ECO  plan-1  O21  0.020
 ECO  plan-1  H20  0.020
 ECO  plan-2  C1   0.020
 ECO  plan-2  C2   0.020
 ECO  plan-2  C3   0.020
 ECO  plan-2  O3   0.020
 ECO  plan-2  C4   0.020
 ECO  plan-2  C5   0.020
 ECO  plan-2  C6   0.020
 ECO  plan-2  C9   0.020
 ECO  plan-2  C10  0.020
 ECO  plan-2  HC1  0.020
 ECO  plan-2  HC2  0.020
 ECO  plan-2  HC4  0.020
 ECO  plan-3  C5   0.020
 ECO  plan-3  C6   0.020
 ECO  plan-3  C7   0.020
 ECO  plan-3  N19  0.020
 ECO  plan-3  O19  0.020

