# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Aug  1 20:29:23 2022
#   Inital geometry file: a 108 line input string
#   Ligand name: 3-(3-cyclopentyloxy-4-methoxy-phenyl)-4,4-dimethyl-1~{H}-pyrazol-5-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(cc1OC2CCCC2)C3=NNC(=O)C3(C)C
#
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
 RLW  RLW  "3-(3-cyclopentyloxy-4-methoxy-phenyl)-4,4-dimethyl-1~{H}-pyrazol-5-one"
  ligand  44  22  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_RLW
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
 RLW  C16   C  CH2   0  -0.453  -23.5732  119.6993  353.9353
 RLW  C17   C  CH2   0  -0.448  -22.5970  119.9755  355.0891
 RLW  C18   C  CH2   0  -0.441  -21.1838  119.7731  354.4928
 RLW  C19   C  CH2   0  -0.481  -21.4022  119.3965  353.0202
 RLW  C20   C  CR16  0  -0.478  -21.8347  116.4524  351.6346
 RLW  C15   C  CH1   0  -0.034  -22.8023  118.7917  352.9902
 RLW  C13   C  CR6   0   0.368  -22.2663  116.4481  352.9495
 RLW  C12   C  CH3   0  -0.438  -22.4867  114.2026  355.7988
 RLW  C10   C  CR6   0   0.290  -22.1508  115.2697  353.7136
 RLW  C02   C  CR5   0   0.613  -20.2011  115.8009  347.4594
 RLW  C03   C  CR5   0  -0.434  -20.8204  116.4754  348.6811
 RLW  C04   C  CH3   0  -0.638  -22.2272  116.9557  348.3096
 RLW  C05   C  CH3   0  -0.640  -19.9137  117.6353  349.1052
 RLW  C06   C  CR5   0   0.352  -20.8151  115.3183  349.6552
 RLW  C07   C  CR6   0   0.068  -21.2834  115.3095  351.0414
 RLW  C08   C  CR16  0  -0.301  -21.1821  114.1528  351.8068
 RLW  C09   C  CR16  0  -0.363  -21.6124  114.1339  353.1253
 RLW  O11   O  O2    0  -0.455  -22.5864  115.3500  354.9804
 RLW  O14   O  O2    0  -0.479  -22.8243  117.4935  353.5831
 RLW  N21   N  N     0  -0.252  -20.3234  114.2554  349.1313
 RLW  N22   N  NR15  0  -0.504  -19.9618  114.5295  347.8460
 RLW  H161  H  HCH2  0   0.238  -23.8086  120.6216  353.4000
 RLW  H162  H  HCH2  0   0.245  -24.5206  119.2639  354.2564
 RLW  H171  H  HCH2  0   0.232  -22.7332  120.9791  355.4916
 RLW  H172  H  HCH2  0   0.231  -22.7694  119.2817  355.9122
 RLW  H181  H  HCH2  0   0.231  -20.6572  118.9749  355.0171
 RLW  H182  H  HCH2  0   0.233  -20.5661  120.6665  354.5838
 RLW  H191  H  HCH2  0   0.254  -20.6243  118.7423  352.6231
 RLW  H192  H  HCH2  0   0.241  -21.4127  120.2894  352.3903
 RLW  H201  H  HCR6  0   0.272  -21.9278  117.3606  351.0601
 RLW  H151  H  HCH1  0   0.249  -23.2435  118.7584  351.9884
 RLW  H121  H  HCH3  0   0.260  -22.8841  114.4831  356.7711
 RLW  H123  H  HCH3  0   0.229  -23.0732  113.3677  355.4065
 RLW  H122  H  HCH3  0   0.229  -21.4503  113.8775  355.9222
 RLW  H042  H  HCH3  0   0.251  -22.7005  117.4861  349.1338
 RLW  H043  H  HCH3  0   0.251  -22.1655  117.6418  347.4647
 RLW  H041  H  HCH3  0   0.248  -22.8739  116.1243  348.0279
 RLW  H052  H  HCH3  0   0.253  -20.3241  118.1783  349.9547
 RLW  H051  H  HCH3  0   0.248  -18.9175  117.2863  349.3778
 RLW  H053  H  HCH3  0   0.250  -19.8137  118.3413  348.2802
 RLW  H081  H  HCR6  0   0.254  -20.7612  113.2527  351.3808
 RLW  H091  H  HCR6  0   0.283  -21.5151  113.2161  353.6895
 RLW  H221  H  HNR5  0   0.413  -19.5554  113.7960  347.2859
 RLW  O01   O  O     0  -0.451  -19.9717  116.2940  346.3745

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
 RLW  O01  C02   double    1.214  0.020  1.214
 RLW  C02  N22   single    1.350  0.020  1.350
 RLW  C02  C03   single    1.527  0.020  1.527
 RLW  N22  N21   single    1.363  0.020  1.363
 RLW  C04  C03   single    1.532  0.020  1.532
 RLW  C03  C05   single    1.532  0.020  1.532
 RLW  C03  C06   single    1.513  0.020  1.513
 RLW  N21  C06   double    1.283  0.020  1.283
 RLW  C06  C07   single    1.463  0.020  1.463
 RLW  C07  C20   aromatic  1.401  0.020  1.401
 RLW  C07  C08   aromatic  1.391  0.020  1.391
 RLW  C20  C13   aromatic  1.384  0.020  1.384
 RLW  C08  C09   aromatic  1.387  0.020  1.387
 RLW  C13  O14   single    1.344  0.020  1.344
 RLW  C13  C10   aromatic  1.409  0.020  1.409
 RLW  C15  C19   single    1.525  0.020  1.525
 RLW  C15  O14   single    1.427  0.020  1.427
 RLW  C15  C16   single    1.520  0.020  1.520
 RLW  C09  C10   aromatic  1.388  0.020  1.388
 RLW  C19  C18   single    1.536  0.020  1.536
 RLW  C16  C17   single    1.536  0.020  1.536
 RLW  C10  O11   single    1.342  0.020  1.342
 RLW  C17  C18   single    1.547  0.020  1.547
 RLW  O11  C12   single    1.413  0.020  1.413
 RLW  C16  H161  single    0.970  0.020  1.090
 RLW  C16  H162  single    0.970  0.020  1.090
 RLW  C17  H171  single    0.970  0.020  1.090
 RLW  C17  H172  single    0.970  0.020  1.090
 RLW  C18  H181  single    0.970  0.020  1.090
 RLW  C18  H182  single    0.970  0.020  1.090
 RLW  C19  H191  single    0.970  0.020  1.090
 RLW  C19  H192  single    0.970  0.020  1.090
 RLW  C20  H201  single    0.930  0.020  1.080
 RLW  C15  H151  single    0.970  0.020  1.090
 RLW  C12  H121  single    0.970  0.020  1.090
 RLW  C12  H123  single    0.970  0.020  1.090
 RLW  C12  H122  single    0.970  0.020  1.090
 RLW  C04  H042  single    0.970  0.020  1.090
 RLW  C04  H043  single    0.970  0.020  1.090
 RLW  C04  H041  single    0.970  0.020  1.090
 RLW  C05  H052  single    0.970  0.020  1.090
 RLW  C05  H051  single    0.970  0.020  1.090
 RLW  C05  H053  single    0.970  0.020  1.090
 RLW  C08  H081  single    0.930  0.020  1.080
 RLW  C09  H091  single    0.930  0.020  1.080
 RLW  N22  H221  single    0.860  0.020  1.020

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
 RLW  H162  C16  H161  107.10  3.000
 RLW  H162  C16  C15   112.65  3.000
 RLW  H161  C16  C15   107.98  3.000
 RLW  H162  C16  C17   113.74  3.000
 RLW  H161  C16  C17   110.69  3.000
 RLW  C15   C16  C17   104.59  3.000
 RLW  H172  C17  H171  106.70  3.000
 RLW  H172  C17  C18   110.62  3.000
 RLW  H171  C17  C18   112.15  3.000
 RLW  H172  C17  C16   110.61  3.000
 RLW  H171  C17  C16   111.32  3.000
 RLW  C18   C17  C16   105.52  3.000
 RLW  H182  C18  H181  106.63  3.000
 RLW  H182  C18  C19   111.21  3.000
 RLW  H181  C18  C19   110.49  3.000
 RLW  H182  C18  C17   112.23  3.000
 RLW  H181  C18  C17   110.58  3.000
 RLW  C19   C18  C17   105.77  3.000
 RLW  H192  C19  H191  106.67  3.000
 RLW  H192  C19  C15   107.69  3.000
 RLW  H191  C19  C15   114.17  3.000
 RLW  H192  C19  C18   110.71  3.000
 RLW  H191  C19  C18   113.24  3.000
 RLW  C15   C19  C18   104.28  3.000
 RLW  H201  C20  C07   119.70  3.000
 RLW  H201  C20  C13   118.80  3.000
 RLW  C07   C20  C13   121.51  3.000
 RLW  H151  C15  O14   110.25  3.000
 RLW  H151  C15  C19   113.57  3.000
 RLW  O14   C15  C19   111.51  3.000
 RLW  H151  C15  C16   112.49  3.000
 RLW  O14   C15  C16   106.08  3.000
 RLW  C19   C15  C16   102.50  3.000
 RLW  O14   C13  C10   115.40  3.000
 RLW  C10   C13  C20   119.49  3.000
 RLW  O14   C13  C20   125.11  3.000
 RLW  H122  C12  H123  108.78  3.000
 RLW  H122  C12  H121  108.80  3.000
 RLW  H123  C12  H121  108.78  3.000
 RLW  H122  C12  O11   111.95  3.000
 RLW  H123  C12  O11   111.99  3.000
 RLW  H121  C12  O11   106.42  3.000
 RLW  O11   C10  C09   125.10  3.000
 RLW  O11   C10  C13   115.80  3.000
 RLW  C09   C10  C13   119.10  3.000
 RLW  N22   C02  C03   105.00  3.000
 RLW  C03   C02  O01   127.77  3.000
 RLW  N22   C02  O01   127.23  3.000
 RLW  C06   C03  C05   113.50  3.000
 RLW  C06   C03  C04   113.53  3.000
 RLW  C05   C03  C04   111.91  3.000
 RLW  C06   C03  C02   100.13  3.000
 RLW  C05   C03  C02   108.42  3.000
 RLW  C04   C03  C02   108.47  3.000
 RLW  H041  C04  H043  108.25  3.000
 RLW  H041  C04  H042  108.01  3.000
 RLW  H043  C04  H042  107.75  3.000
 RLW  H041  C04  C03   111.61  3.000
 RLW  H043  C04  C03   109.47  3.000
 RLW  H042  C04  C03   111.62  3.000
 RLW  H053  C05  H051  108.22  3.000
 RLW  H053  C05  H052  107.58  3.000
 RLW  H051  C05  H052  108.01  3.000
 RLW  H053  C05  C03   109.57  3.000
 RLW  H051  C05  C03   111.56  3.000
 RLW  H052  C05  C03   111.75  3.000
 RLW  N21   C06  C07   120.30  3.000
 RLW  C07   C06  C03   127.85  3.000
 RLW  N21   C06  C03   111.85  3.000
 RLW  C08   C07  C06   120.20  3.000
 RLW  C08   C07  C20   118.31  3.000
 RLW  C06   C07  C20   121.49  3.000
 RLW  H081  C08  C09   118.95  3.000
 RLW  H081  C08  C07   120.26  3.000
 RLW  C09   C08  C07   120.79  3.000
 RLW  H091  C09  C08   118.65  3.000
 RLW  H091  C09  C10   120.55  3.000
 RLW  C08   C09  C10   120.80  3.000
 RLW  C10   O11  C12   118.38  3.000
 RLW  C13   O14  C15   120.35  3.000
 RLW  N22   N21  C06   108.67  3.000
 RLW  H221  N22  N21   118.97  3.000
 RLW  H221  N22  C02   126.68  3.000
 RLW  N21   N22  C02   114.35  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
 RLW  CONST_01  C09   C08  C07  C20     0.00   0.0  0
 RLW  CONST_02  C09   C10  C13  C20     0.00   0.0  0
 RLW  CONST_03  C08   C07  C20  C13     0.00   0.0  0
 RLW  CONST_04  C08   C09  C10  C13     0.00   0.0  0
 RLW  CONST_05  C07   C20  C13  C10     0.00   0.0  0
 RLW  CONST_06  C07   C08  C09  C10     0.00   0.0  0
 RLW  CONST_07  C06   C07  C20  C13   180.00   0.0  0
 RLW  CONST_08  C09   C08  C07  C06   180.00   0.0  0
 RLW  CONST_09  N21   N22  C02  C03     0.00   0.0  0
 RLW  CONST_10  O11   C10  C13  C20   180.00   0.0  0
 RLW  CONST_11  O14   C13  C20  C07   180.00   0.0  0
 RLW  CONST_12  O11   C10  C09  C08   180.00   0.0  0
 RLW  CONST_13  O14   C13  C10  C09   180.00   0.0  0
 RLW  CONST_14  N21   N22  C02  O01   180.00   0.0  0
 RLW  CONST_15  H081  C08  C07  C20   180.00   0.0  0
 RLW  CONST_16  H091  C09  C10  C13   180.00   0.0  0
 RLW  CONST_17  H201  C20  C13  C10   180.00   0.0  0
 RLW  CONST_18  H081  C08  C09  C10   180.00   0.0  0
 RLW  CONST_19  H201  C20  C07  C06     0.00   0.0  0
 RLW  CONST_20  H081  C08  C07  C06     0.00   0.0  0
 RLW  CONST_21  H091  C09  C08  C07   180.00   0.0  0
 RLW  CONST_22  H201  C20  C07  C08   180.00   0.0  0
 RLW  CONST_23  H221  N22  C02  C03   180.00   0.0  0
 RLW  CONST_24  H221  N22  C02  O01     0.00   0.0  0
 RLW  Var_01    C19   C18  C17  C16     0.29  30.0  1
 RLW  Var_02    C15   C19  C18  C17   -24.90  30.0  1
 RLW  Var_03    C15   C16  C17  C18    24.54  30.0  1
 RLW  Var_04    C03   C06  C07  C20     0.77  30.0  2
 RLW  Var_05    N21   C06  C07  C20  -179.46  30.0  2
 RLW  Var_06    C06   N21  N22  C02     0.02  30.0  1
 RLW  Var_07    N21   C06  C03  C02    -0.07  30.0  1
 RLW  Var_08    C07   C06  C03  C02   179.71  30.0  1
 RLW  Var_09    N22   N21  C06  C03     0.04  30.0  1
 RLW  Var_10    C08   C07  C06  C03  -178.90  30.0  2
 RLW  Var_11    N22   C02  C03  C06     0.08  30.0  1
 RLW  Var_12    N22   N21  C06  C07  -179.76  30.0  1
 RLW  Var_13    N21   C06  C07  C08     0.87  30.0  2
 RLW  Var_14    C15   O14  C13  C20   -11.04  30.0  2
 RLW  Var_15    C10   C13  O14  C15   170.04  30.0  3
 RLW  Var_16    C06   C03  C02  O01  -179.95  30.0  1
 RLW  Var_17    N22   C02  C03  C04  -119.08  30.0  1
 RLW  Var_18    N21   C06  C03  C04   115.32  30.0  1
 RLW  Var_19    C07   C06  C03  C04   -64.89  30.0  1
 RLW  Var_20    N22   C02  C03  C05   119.19  30.0  1
 RLW  Var_21    N21   C06  C03  C05  -115.40  30.0  1
 RLW  Var_22    C07   C06  C03  C05    64.39  30.0  1
 RLW  Var_23    H181  C18  C17  C16  -119.35  30.0  1
 RLW  Var_24    H182  C18  C17  C16   121.72  30.0  1
 RLW  Var_25    H191  C19  C18  C17  -149.59  30.0  1
 RLW  Var_26    H192  C19  C18  C17    90.66  30.0  1
 RLW  Var_27    H161  C16  C17  C18   -91.52  30.0  1
 RLW  Var_28    H162  C16  C17  C18   147.85  30.0  1
 RLW  Var_29    H171  C17  C18  C19  -121.06  30.0  1
 RLW  Var_30    H172  C17  C18  C19   119.95  30.0  1
 RLW  Var_31    H181  C18  C19  C15    94.81  30.0  1
 RLW  Var_32    H182  C18  C19  C15  -146.99  30.0  1
 RLW  Var_33    H171  C17  C16  C15   146.43  30.0  1
 RLW  Var_34    H172  C17  C16  C15   -95.13  30.0  1
 RLW  Var_35    H221  N22  N21  C06  -179.93  30.0  1
 RLW  Var_36    C12   O11  C10  C13  -179.52  30.0  2
 RLW  Var_37    C09   C10  O11  C12     0.60  30.0  2
 RLW  Var_38    C04   C03  C02  O01    60.89  30.0  1
 RLW  Var_39    C05   C03  C02  O01   -60.83  30.0  1
 RLW  Var_40    H042  C04  C03  C02  -177.44  30.0  3
 RLW  Var_41    H043  C04  C03  C02   -58.24  30.0  3
 RLW  Var_42    H041  C04  C03  C02    61.58  30.0  3
 RLW  Var_43    H052  C05  C03  C02   177.99  30.0  3
 RLW  Var_44    H051  C05  C03  C02   -60.97  30.0  3
 RLW  Var_45    H053  C05  C03  C02    58.85  30.0  3
 RLW  Var_46    H042  C04  C03  C06    72.21  30.0  3
 RLW  Var_47    H043  C04  C03  C06  -168.59  30.0  3
 RLW  Var_48    H041  C04  C03  C06   -48.77  30.0  3
 RLW  Var_49    H052  C05  C03  C06   -71.70  30.0  3
 RLW  Var_50    H051  C05  C03  C06    49.33  30.0  3
 RLW  Var_51    H053  C05  C03  C06   169.16  30.0  3
 RLW  Var_52    H121  C12  O11  C10   179.67  30.0  3
 RLW  Var_53    H123  C12  O11  C10   -61.57  30.0  3
 RLW  Var_54    H122  C12  O11  C10    60.92  30.0  3
 RLW  Var_55    H052  C05  C03  C04    58.40  30.0  3
 RLW  Var_56    H051  C05  C03  C04   179.43  30.0  3
 RLW  Var_57    H053  C05  C03  C04   -60.75  30.0  3
 RLW  Var_58    H042  C04  C03  C05   -57.88  30.0  3
 RLW  Var_59    H043  C04  C03  C05    61.32  30.0  3
 RLW  Var_60    H041  C04  C03  C05  -178.86  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
 RLW  chir_01  C15  C19  O14  C16  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
 RLW  plan-1  C02   0.020
 RLW  plan-1  C03   0.020
 RLW  plan-1  N21   0.020
 RLW  plan-1  N22   0.020
 RLW  plan-1  H221  0.020
 RLW  plan-1  O01   0.020
 RLW  plan-2  C20   0.020
 RLW  plan-2  C13   0.020
 RLW  plan-2  C10   0.020
 RLW  plan-2  C06   0.020
 RLW  plan-2  C07   0.020
 RLW  plan-2  C08   0.020
 RLW  plan-2  C09   0.020
 RLW  plan-2  O11   0.020
 RLW  plan-2  O14   0.020
 RLW  plan-2  H201  0.020
 RLW  plan-2  H081  0.020
 RLW  plan-2  H091  0.020

