# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 02:57:18 2022
#   Inital geometry file: a 140 line input string
#   Ligand name: 4-(3-cyano-3-methylazetidine-1-carbonyl)-N-[(3R,4S)-7-fluoro-4-hydroxy-6-methyl-3,4-dihydro-2H-1-benzopyran-3-yl]-5-methyl-1H-pyrrole-2-sulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1[nH]c(cc1C(=O)N2CC(C)(C2)C#N)[S](=O)(=O)N[C@@H]3COc4cc(F)c(C)cc4[C@@H]3O
#
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
 C9W  C9W  "4-(3-cyano-3-methylazetidine-1-carbonyl)-N-[(3R,4S)-7-fluoro-4-hydroxy-6-methyl-3,4-dihydro-2H-1-benzopyran-3-yl]-5-methyl-1H-pyrrole-2-sulfonamide"
  ligand  55  32  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C9W
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
 C9W  C5   C  CR5   0   0.382  14.7665   -7.9005   1.7360
 C9W  C8   C  CR5   0   0.072  13.2688   -9.4435   1.1640
 C9W  C1   C  CH3   0  -0.725  15.3428   -6.5339   1.8269
 C9W  C15  C  C     0  -0.238  15.9060  -11.5441   4.0155
 C9W  C11  C  CR5   0  -0.156  15.2358   -9.1370   2.1780
 C9W  C18  C  C     0  -0.253  17.0394  -11.8910   5.0216
 C9W  C23  C  C     0  -0.217  17.8829  -10.7693   4.3509
 C9W  C26  C  CSP   0   0.160  17.5905  -13.2248   4.8420
 C9W  C    C  CR16  0  -0.508   9.5374  -10.8917   6.8272
 C9W  C01  C  CR16  0  -0.337  10.4688   -8.3504   6.2972
 C9W  C02  C  CR6   0  -0.103  10.2616   -8.7019   7.6230
 C9W  C03  C  CR6   0   0.526   9.7967   -9.9940   7.8377
 C9W  N6   N  NR15  0  -0.651  13.5808   -8.1124   1.1388
 C9W  C9   C  CR15  0  -0.335  14.2734  -10.1097   1.8110
 C9W  C12  C  C     0   0.480  16.5264   -9.3139   2.8534
 C9W  O13  O  O     0  -0.484  17.3972   -8.4498   2.8320
 C9W  N14  N  N     0  -0.464  16.7464  -10.4736   3.5018
 C9W  N27  N  NS    0  -0.257  18.0303  -14.2799   4.7108
 C9W  S28  S  S     0   1.355  11.7819  -10.0802   0.5222
 C9W  O29  O  OS    0  -0.651  11.5081   -9.4371  -0.7497
 C9W  O30  O  OS    0  -0.643  11.8971  -11.5232   0.6246
 C9W  N31  N  NC1   0  -0.745  10.5766   -9.6079   1.5230
 C9W  C33  C  CH1   0  -0.147  10.6001   -9.9807   2.9255
 C9W  C35  C  CH2   0  -0.158   9.4819  -10.9732   3.2075
 C9W  O38  O  O2    0  -0.474   9.5094  -11.4161   4.5544
 C9W  C41  C  CR6   0   0.390   9.7507  -10.4951   5.5082
 C9W  C42  C  CR6   0  -0.007  10.2233   -9.2137   5.2329
 C9W  C43  C  CH1   0  -0.041  10.4451   -8.7550   3.8154
 C9W  O45  O  OH1   0  -0.656   9.3503   -8.0144   3.3165
 C9W  F    F  F     0  -0.311   9.5887  -10.3901   9.1047
 C9W  H11  H  HCH3  0   0.263  16.2321   -6.4418   1.2049
 C9W  H12  H  HCH3  0   0.253  14.6198   -5.7887   1.4987
 C9W  H13  H  HCH3  0   0.260  15.6350   -6.2992   2.8484
 C9W  H16  H  H     0   0.274  15.6861  -12.3290   3.2906
 C9W  H17  H  H     0   0.276  14.9784  -11.2176   4.4900
 C9W  H24  H  H     0   0.266  18.1611   -9.9654   5.0348
 C9W  H25  H  H     0   0.265  18.7700  -11.1047   3.8109
 C9W  H    H  HCR6  0   0.282   9.1784  -11.8883   7.0519
 C9W  H04  H  HCR6  0   0.263  10.8486   -7.3575   6.0784
 C9W  H7   H  HNR5  0   0.427  13.0163   -7.3841   0.7243
 C9W  H10  H  HCR5  0   0.280  14.3092  -11.1752   1.9643
 C9W  H1   H  HNC1  0   0.421  10.1924   -8.6922   1.3152
 C9W  H33  H  HCH1  0   0.298  11.5598  -10.4451   3.1780
 C9W  H51  H  HCH2  0   0.235   8.5108  -10.5227   2.9763
 C9W  H52  H  HCH2  0   0.257   9.6005  -11.8612   2.5883
 C9W  H44  H  HCH1  0   0.254  11.3669   -8.1610   3.7672
 C9W  H45  H  HOH1  0   0.463   9.3322   -7.1562   3.7521
 C9W  H2   H  HCH3  0   0.248   9.6178   -7.5499   9.3288
 C9W  H3   H  HCH3  0   0.247  11.2609   -8.1594   9.4564
 C9W  H4   H  HCH3  0   0.249  10.9045   -6.8106   8.3847
 C9W  CL   C  CH3   0  -0.713  10.5241   -7.7595   8.7588
 C9W  C19  C  CH3   0  -0.643  16.6980  -11.6393   6.4830
 C9W  H20  H  HCH3  0   0.258  17.5863  -11.7179   7.1084
 C9W  H21  H  HCH3  0   0.257  16.2920  -10.6336   6.5907
 C9W  H22  H  HCH3  0   0.258  15.9533  -12.3500   6.8392

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
 C9W  C5   C1   single    1.486  0.020  1.486
 C9W  C5   C11  aromatic  1.394  0.020  1.394
 C9W  C5   N6   aromatic  1.344  0.020  1.344
 C9W  C8   N6   aromatic  1.367  0.020  1.367
 C9W  C8   C9   aromatic  1.368  0.020  1.368
 C9W  C8   S28  single    1.740  0.020  1.740
 C9W  C15  C18  single    1.555  0.020  1.555
 C9W  C15  N14  single    1.455  0.020  1.455
 C9W  C11  C9   aromatic  1.417  0.020  1.417
 C9W  C11  C12  single    1.467  0.020  1.467
 C9W  C19  C18  single    1.522  0.020  1.522
 C9W  C18  C23  single    1.556  0.020  1.556
 C9W  C18  C26  single    1.454  0.020  1.454
 C9W  C23  N14  single    1.449  0.020  1.449
 C9W  C26  N27  triple    1.151  0.020  1.151
 C9W  C    C03  aromatic  1.376  0.020  1.376
 C9W  C    C41  aromatic  1.394  0.020  1.394
 C9W  C01  C02  aromatic  1.387  0.020  1.387
 C9W  C01  C42  aromatic  1.392  0.020  1.392
 C9W  C02  C03  aromatic  1.390  0.020  1.390
 C9W  C03  F    single    1.344  0.020  1.344
 C9W  C12  O13  double    1.227  0.020  1.227
 C9W  C12  N14  single    1.347  0.020  1.347
 C9W  S28  O29  double    1.451  0.020  1.451
 C9W  S28  O30  double    1.451  0.020  1.451
 C9W  S28  N31  single    1.636  0.020  1.636
 C9W  N31  C33  single    1.451  0.020  1.451
 C9W  C33  C35  single    1.522  0.020  1.522
 C9W  C33  C43  single    1.523  0.020  1.523
 C9W  C35  O38  single    1.418  0.020  1.418
 C9W  O38  C41  single    1.348  0.020  1.348
 C9W  C41  C42  aromatic  1.393  0.020  1.393
 C9W  C42  C43  single    1.506  0.020  1.506
 C9W  C43  O45  single    1.413  0.020  1.413
 C9W  C02  CL   single    1.499  0.020  1.499
 C9W  C1   H11  single    0.970  0.020  1.090
 C9W  C1   H12  single    0.970  0.020  1.090
 C9W  C1   H13  single    0.970  0.020  1.090
 C9W  C15  H16  single    0.970  0.020  1.090
 C9W  C15  H17  single    0.970  0.020  1.090
 C9W  C19  H20  single    0.970  0.020  1.090
 C9W  C19  H21  single    0.970  0.020  1.090
 C9W  C19  H22  single    0.970  0.020  1.090
 C9W  C23  H24  single    0.970  0.020  1.090
 C9W  C23  H25  single    0.970  0.020  1.090
 C9W  C    H    single    0.930  0.020  1.080
 C9W  C01  H04  single    0.930  0.020  1.080
 C9W  N6   H7   single    0.860  0.020  1.020
 C9W  C9   H10  single    0.930  0.020  1.080
 C9W  N31  H1   single    0.890  0.020  1.040
 C9W  C33  H33  single    0.970  0.020  1.090
 C9W  C35  H51  single    0.970  0.020  1.090
 C9W  C35  H52  single    0.970  0.020  1.090
 C9W  C43  H44  single    0.970  0.020  1.090
 C9W  O45  H45  single    0.850  0.020  0.980
 C9W  CL   H2   single    0.970  0.020  1.090
 C9W  CL   H3   single    0.970  0.020  1.090
 C9W  CL   H4   single    0.970  0.020  1.090

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
 C9W  N6   C5   C11  107.33  3.000
 C9W  N6   C5   C1   120.94  3.000
 C9W  C11  C5   C1   131.73  3.000
 C9W  S28  C8   C9   128.59  3.000
 C9W  S28  C8   N6   122.98  3.000
 C9W  C9   C8   N6   108.37  3.000
 C9W  H13  C1   H12  108.28  3.000
 C9W  H13  C1   H11  107.38  3.000
 C9W  H12  C1   H11  108.18  3.000
 C9W  H13  C1   C5   111.10  3.000
 C9W  H12  C1   C5   110.70  3.000
 C9W  H11  C1   C5   111.06  3.000
 C9W  H17  C15  H16  109.43  3.000
 C9W  H17  C15  N14  115.10  3.000
 C9W  H16  C15  N14  114.29  3.000
 C9W  H17  C15  C18  113.87  3.000
 C9W  H16  C15  C18  114.61  3.000
 C9W  N14  C15  C18   88.37  3.000
 C9W  C12  C11  C9   129.35  3.000
 C9W  C12  C11  C5   123.28  3.000
 C9W  C9   C11  C5   107.34  3.000
 C9W  C26  C18  C23  113.74  3.000
 C9W  C26  C18  C19  110.82  3.000
 C9W  C23  C18  C19  114.61  3.000
 C9W  C26  C18  C15  113.64  3.000
 C9W  C23  C18  C15   87.44  3.000
 C9W  C19  C18  C15  114.90  3.000
 C9W  H25  C23  H24  109.22  3.000
 C9W  H25  C23  N14  114.22  3.000
 C9W  H24  C23  N14  114.63  3.000
 C9W  H25  C23  C18  115.62  3.000
 C9W  H24  C23  C18  113.52  3.000
 C9W  N14  C23  C18   88.54  3.000
 C9W  N27  C26  C18  180.00  3.000
 C9W  H    C    C41  120.60  3.000
 C9W  H    C    C03  120.69  3.000
 C9W  C41  C    C03  118.71  3.000
 C9W  H04  C01  C42  118.34  3.000
 C9W  H04  C01  C02  118.48  3.000
 C9W  C42  C01  C02  123.17  3.000
 C9W  CL   C02  C03  121.73  3.000
 C9W  CL   C02  C01  122.60  3.000
 C9W  C03  C02  C01  115.67  3.000
 C9W  F    C03  C02  118.13  3.000
 C9W  F    C03  C    118.10  3.000
 C9W  C02  C03  C    123.77  3.000
 C9W  H7   N6   C8   125.57  3.000
 C9W  H7   N6   C5   124.16  3.000
 C9W  C8   N6   C5   110.27  3.000
 C9W  H10  C9   C11  128.30  3.000
 C9W  H10  C9   C8   124.99  3.000
 C9W  C11  C9   C8   106.68  3.000
 C9W  N14  C12  O13  119.93  3.000
 C9W  N14  C12  C11  117.97  3.000
 C9W  O13  C12  C11  122.10  3.000
 C9W  C12  N14  C23  125.87  3.000
 C9W  C12  N14  C15  135.18  3.000
 C9W  C23  N14  C15   95.51  3.000
 C9W  N31  S28  O30  107.60  3.000
 C9W  N31  S28  O29  105.62  3.000
 C9W  O30  S28  O29  121.15  3.000
 C9W  N31  S28  C8   107.35  3.000
 C9W  O30  S28  C8   105.66  3.000
 C9W  O29  S28  C8   108.80  3.000
 C9W  H1   N31  C33  115.84  3.000
 C9W  H1   N31  S28  114.47  3.000
 C9W  C33  N31  S28  120.33  3.000
 C9W  H33  C33  C43  107.20  3.000
 C9W  H33  C33  C35  108.94  3.000
 C9W  C43  C33  C35  110.00  3.000
 C9W  H33  C33  N31  110.23  3.000
 C9W  C43  C33  N31  110.88  3.000
 C9W  C35  C33  N31  109.56  3.000
 C9W  H52  C35  H51  108.18  3.000
 C9W  H52  C35  O38  106.46  3.000
 C9W  H51  C35  O38  110.26  3.000
 C9W  H52  C35  C33  110.27  3.000
 C9W  H51  C35  C33  110.13  3.000
 C9W  O38  C35  C33  111.44  3.000
 C9W  C41  O38  C35  117.53  3.000
 C9W  C42  C41  O38  123.33  3.000
 C9W  C42  C41  C    120.04  3.000
 C9W  O38  C41  C    116.61  3.000
 C9W  C43  C42  C41  121.06  3.000
 C9W  C43  C42  C01  120.31  3.000
 C9W  C41  C42  C01  118.62  3.000
 C9W  H44  C43  O45  110.59  3.000
 C9W  H44  C43  C42  109.26  3.000
 C9W  O45  C43  C42  112.20  3.000
 C9W  H44  C43  C33  108.93  3.000
 C9W  O45  C43  C33  107.12  3.000
 C9W  C42  C43  C33  108.65  3.000
 C9W  H45  O45  C43  108.79  3.000
 C9W  H4   CL   H3   107.65  3.000
 C9W  H4   CL   H2   107.60  3.000
 C9W  H3   CL   H2   107.31  3.000
 C9W  H4   CL   C02  110.41  3.000
 C9W  H3   CL   C02  111.87  3.000
 C9W  H2   CL   C02  111.79  3.000
 C9W  H22  C19  H21  108.37  3.000
 C9W  H22  C19  H20  108.82  3.000
 C9W  H21  C19  H20  108.28  3.000
 C9W  H22  C19  C18  111.07  3.000
 C9W  H21  C19  C18  109.34  3.000
 C9W  H20  C19  C18  110.88  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
 C9W  CONST_01  C8   C9   C11  C5      0.00   0.0  0
 C9W  CONST_02  C9   C8   N6   C5      0.00   0.0  0
 C9W  CONST_03  C11  C5   N6   C8      0.00   0.0  0
 C9W  CONST_04  N6   C8   C9   C11     0.00   0.0  0
 C9W  CONST_05  C01  C02  C03  C       0.00   0.0  0
 C9W  CONST_06  C01  C42  C41  C       0.00   0.0  0
 C9W  CONST_07  C41  C42  C01  C02     0.00   0.0  0
 C9W  CONST_08  C41  C    C03  C02     0.00   0.0  0
 C9W  CONST_09  C42  C41  C    C03     0.00   0.0  0
 C9W  CONST_10  C42  C01  C02  C03     0.00   0.0  0
 C9W  CONST_11  C9   C11  C5   N6      0.00   0.0  0
 C9W  CONST_12  S28  C8   N6   C5    180.00   0.0  0
 C9W  CONST_13  C1   C5   N6   C8    180.00   0.0  0
 C9W  CONST_14  C12  C11  C9   C8    180.00   0.0  0
 C9W  CONST_15  C9   C11  C5   C1    180.00   0.0  0
 C9W  CONST_16  S28  C8   C9   C11   180.00   0.0  0
 C9W  CONST_17  CL   C02  C03  C     180.00   0.0  0
 C9W  CONST_18  F    C03  C02  C01   180.00   0.0  0
 C9W  CONST_19  C12  C11  C5   N6    180.00   0.0  0
 C9W  CONST_20  F    C03  C    C41   180.00   0.0  0
 C9W  CONST_21  CL   C02  C01  C42   180.00   0.0  0
 C9W  CONST_23  C23  N14  C12  C11   180.00   0.0  0
 C9W  CONST_24  H10  C9   C11  C5    180.00   0.0  0
 C9W  CONST_25  H7   N6   C5   C11   180.00   0.0  0
 C9W  CONST_26  H    C    C03  C02   180.00   0.0  0
 C9W  CONST_27  H04  C01  C02  C03   180.00   0.0  0
 C9W  CONST_28  H10  C9   C8   N6    180.00   0.0  0
 C9W  CONST_29  H7   N6   C8   C9    180.00   0.0  0
 C9W  CONST_30  H    C    C41  O38     0.00   0.0  0
 C9W  CONST_31  H04  C01  C42  C41   180.00   0.0  0
 C9W  CONST_32  H    C    C41  C42   180.00   0.0  0
 C9W  CONST_33  H04  C01  C42  C43     0.00   0.0  0
 C9W  CONST_35  O13  C12  N14  C23     0.00   0.0  0
 C9W  Var_01    C18  C23  N14  C15    -2.92  30.0  1
 C9W  Var_02    C35  O38  C41  C     168.79  30.0  1
 C9W  Var_03    C41  O38  C35  C33    41.82  30.0  1
 C9W  Var_04    C42  C41  O38  C35   -12.87  30.0  1
 C9W  Var_05    N14  C12  C11  C5    165.18  30.0  2
 C9W  Var_06    C12  N14  C15  C18  -155.86  30.0  1
 C9W  Var_07    C12  N14  C23  C18   158.73  30.0  1
 C9W  Var_08    N14  C12  C11  C9    -17.07  30.0  2
 C9W  Var_09    H24  C23  N14  C15  -118.23  30.0  1
 C9W  Var_10    H25  C23  N14  C15   114.66  30.0  1
 C9W  Var_11    H16  C15  N14  C23  -113.46  30.0  1
 C9W  Var_12    H17  C15  N14  C23   118.63  30.0  1
 C9W  Var_13    H51  C35  O38  C41   -80.80  30.0  1
 C9W  Var_14    H52  C35  O38  C41   162.09  30.0  1
 C9W  Var_15    O13  C12  C11  C5    -15.40  30.0  2
 C9W  Var_16    C33  N31  S28  C8    -58.80  30.0  3
 C9W  Var_17    O29  S28  C8   N6     43.10  30.0  2
 C9W  Var_18    O30  S28  C8   N6    174.63  30.0  2
 C9W  Var_19    N31  S28  C8   N6    -70.75  30.0  2
 C9W  Var_20    O29  S28  C8   C9   -140.11  30.0  2
 C9W  Var_21    O30  S28  C8   C9     -8.58  30.0  2
 C9W  Var_22    N31  S28  C8   C9    106.04  30.0  2
 C9W  Var_23    O13  C12  C11  C9    162.34  30.0  2
 C9W  Var_24    H11  C1   C5   C11    68.26  30.0  2
 C9W  Var_25    H12  C1   C5   C11  -171.54  30.0  2
 C9W  Var_26    H13  C1   C5   C11   -51.19  30.0  2
 C9W  Var_27    H2   CL   C02  C01   118.62  30.0  2
 C9W  Var_28    H3   CL   C02  C01  -121.00  30.0  2
 C9W  Var_29    H4   CL   C02  C01    -1.13  30.0  2
 C9W  Var_30    H2   CL   C02  C03   -61.63  30.0  2
 C9W  Var_31    H3   CL   C02  C03    58.75  30.0  2
 C9W  Var_32    H4   CL   C02  C03   178.61  30.0  2
 C9W  Var_33    H11  C1   C5   N6   -111.62  30.0  2
 C9W  Var_34    H12  C1   C5   N6      8.58  30.0  2
 C9W  Var_35    H13  C1   C5   N6    128.93  30.0  2
 C9W  Var_36    H16  C15  N14  C12    87.76  30.0  1
 C9W  Var_37    H17  C15  N14  C12   -40.15  30.0  1
 C9W  Var_38    H24  C23  N14  C12    43.42  30.0  1
 C9W  Var_39    H25  C23  N14  C12   -83.69  30.0  1
 C9W  Var_40    C33  N31  S28  O29  -174.77  30.0  3
 C9W  Var_41    C33  N31  S28  O30    54.52  30.0  3
 C9W  Var_42    H1   N31  S28  C8     86.40  30.0  3
 C9W  Var_43    H1   N31  S28  O29   -29.58  30.0  3
 C9W  Var_44    H1   N31  S28  O30  -160.29  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
 C9W  chir_01  C18  C15  C23  C26  positiv
 C9W  chir_02  C33  N31  C35  C43  positiv
 C9W  chir_03  C43  O45  C33  C42  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
 C9W  plan-1  C5   0.020
 C9W  plan-1  C8   0.020
 C9W  plan-1  C1   0.020
 C9W  plan-1  C11  0.020
 C9W  plan-1  N6   0.020
 C9W  plan-1  C9   0.020
 C9W  plan-1  C12  0.020
 C9W  plan-1  S28  0.020
 C9W  plan-1  H7   0.020
 C9W  plan-1  H10  0.020
 C9W  plan-2  C    0.020
 C9W  plan-2  C01  0.020
 C9W  plan-2  C02  0.020
 C9W  plan-2  C03  0.020
 C9W  plan-2  O38  0.020
 C9W  plan-2  C41  0.020
 C9W  plan-2  C42  0.020
 C9W  plan-2  C43  0.020
 C9W  plan-2  F    0.020
 C9W  plan-2  H    0.020
 C9W  plan-2  H04  0.020
 C9W  plan-2  CL   0.020
 C9W  plan-3  C15  0.020
 C9W  plan-3  C11  0.020
 C9W  plan-3  C23  0.020
 C9W  plan-3  C12  0.020
 C9W  plan-3  O13  0.020
 C9W  plan-3  N14  0.020

