# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 12 01:49:02 2020
#   Inital geometry file: a 157 line input string
#   Ligand name: 2-[[4-(diethylamino)piperidin-1-yl]methyl]-6-ethynyl-4-(3-phenoxyprop-1-ynyl)phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(CC)C1CCN(CC1)Cc2cc(cc(C#C)c2O)C#CCOc3ccccc3
#
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
 KMN  KMN  2-[[4-(diethylamino)piperidin-1-yl]methyl]-6-ethynyl-4-(3-phenoxyprop-1-ynyl)phenol  ligand  63  31  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_KMN
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
 KMN  C     C  CSP1  0  -0.533  -1.0976  -6.0832   1.5128
 KMN  O     O  O2    0  -0.473   5.2521   0.5865  -0.1358
 KMN  C01   C  CR6   0  -0.110   1.4390  -2.1824  -0.0037
 KMN  C1    C  CR6   0  -0.000  -0.7813  -1.9288  -0.9740
 KMN  N1    N  NT    0  -0.402  -2.7903  -0.5092  -1.0157
 KMN  C02   C  CR16  0  -0.317   1.0400  -3.3672   0.6009
 KMN  C2    C  CH2   0  -0.331  -1.7483  -1.1346  -1.8074
 KMN  N2    N  NT    0  -0.425  -5.4600   2.3685   0.7267
 KMN  C03   C  CH2   0  -0.276  -3.7773   0.1093  -1.8800
 KMN  C3    C  CR16  0  -0.324   0.5137  -1.4828  -0.7871
 KMN  C04   C  CSP   0   0.204   2.7577  -1.6724   0.1728
 KMN  C4    C  CR6   0  -0.159  -0.2569  -3.8446   0.4239
 KMN  C05   C  CSP   0   0.026   3.8620  -1.2140   0.3118
 KMN  C06   C  CH2   0  -0.408   5.2010  -0.6769   0.4987
 KMN  C07   C  CR6   0   0.386   6.4094   1.2839  -0.0730
 KMN  C7    C  CR6   0   0.315  -1.1730  -3.1247  -0.3615
 KMN  C08   C  CR16  0  -0.343   6.4132   2.5178  -0.7259
 KMN  C8    C  CH2   0  -0.479  -4.9256   0.7262  -1.0956
 KMN  C09   C  CR16  0  -0.241   7.5530   3.3025  -0.7148
 KMN  C10   C  CH1   0  -0.029  -4.4144   1.7767  -0.1119
 KMN  C11   C  CH2   0  -0.287  -4.9826   3.5798   1.3818
 KMN  C12   C  CH3   0  -0.680  -5.8933   4.0757   2.4933
 KMN  C13   C  CH2   0  -0.331  -6.7525   2.5615   0.0837
 KMN  C14   C  CH3   0  -0.686  -6.8217   3.6204  -1.0165
 KMN  C15   C  CH2   0  -0.440  -3.3582   1.0905   0.7573
 KMN  C16   C  CH2   0  -0.278  -2.2571   0.4577  -0.0755
 KMN  C17   C  CR16  0  -0.280   8.7022   2.8748  -0.0569
 KMN  C18   C  CR16  0  -0.241   8.6916   1.6494   0.5888
 KMN  C19   C  CR16  0  -0.376   7.5545   0.8470   0.5868
 KMN  C20   C  CSP   0   0.274  -0.6835  -5.0619   1.0266
 KMN  H     H  H     0   0.288  -1.4491  -6.9896   1.9510
 KMN  H061  H  HCH2  0   0.267   5.9414  -1.3639   0.0718
 KMN  H062  H  HCH2  0   0.267   5.4169  -0.5916   1.5703
 KMN  H02   H  HCR6  0   0.275   1.7308  -3.9284   1.2152
 KMN  H3    H  HCR6  0   0.265   0.8155  -0.5553  -1.2580
 KMN  H21C  H  HCH2  0   0.216  -1.1756  -0.3880  -2.3841
 KMN  H22C  H  HCH2  0   0.251  -2.2256  -1.7889  -2.5418
 KMN  H031  H  HCH2  0   0.186  -3.3187   0.8860  -2.5193
 KMN  H032  H  HCH2  0   0.237  -4.1777  -0.6513  -2.5551
 KMN  H161  H  HCH2  0   0.242  -1.5543  -0.0412   0.5944
 KMN  H162  H  HCH2  0   0.183  -1.6854   1.2496  -0.5951
 KMN  H1    H  HOH1  0   0.477  -2.5707  -4.3993  -0.1126
 KMN  H10   H  HCH1  0   0.181  -3.9063   2.5573  -0.7092
 KMN  H111  H  HCH2  0   0.233  -4.0067   3.3708   1.8206
 KMN  H112  H  HCH2  0   0.194  -4.8140   4.3941   0.6589
 KMN  H131  H  HCH2  0   0.241  -7.0887   1.6036  -0.3141
 KMN  H132  H  HCH2  0   0.238  -7.4806   2.8089   0.8596
 KMN  H81C  H  HCH2  0   0.241  -5.6230   1.1551  -1.8173
 KMN  H82C  H  HCH2  0   0.224  -5.4604  -0.0594  -0.5529
 KMN  H08   H  HCR6  0   0.264   5.5202   2.8515  -1.2397
 KMN  H19   H  HCR6  0   0.285   7.5859  -0.1042   1.1012
 KMN  H09   H  HCR6  0   0.259   7.5432   4.2564  -1.2265
 KMN  H17   H  HCR6  0   0.255   9.5915   3.4908  -0.0525
 KMN  H151  H  HCH2  0   0.235  -2.8877   1.7886   1.4511
 KMN  H152  H  HCH2  0   0.215  -3.8509   0.3223   1.3610
 KMN  H121  H  HCH3  0   0.223  -6.8531   4.4390   2.1252
 KMN  H122  H  HCH3  0   0.221  -6.0859   3.2857   3.2207
 KMN  H123  H  HCH3  0   0.231  -5.4156   4.9043   3.0170
 KMN  H141  H  HCH3  0   0.225  -6.6495   4.6264  -0.6320
 KMN  H142  H  HCH3  0   0.222  -6.0884   3.4388  -1.8044
 KMN  H143  H  HCH3  0   0.230  -7.8097   3.6147  -1.4790
 KMN  H18   H  HCR6  0   0.260   9.5761   1.3009   1.1063
 KMN  O1    O  OH1   0  -0.586  -2.4205  -3.5549  -0.5601

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
 KMN  C    C20   triple    1.205  0.020  1.205
 KMN  O    C06   single    1.415  0.020  1.415
 KMN  O    C07   single    1.353  0.020  1.353
 KMN  C01  C02   aromatic  1.389  0.020  1.389
 KMN  C01  C3    aromatic  1.400  0.020  1.400
 KMN  C01  C04   single    1.425  0.020  1.425
 KMN  C1   C2    single    1.503  0.020  1.503
 KMN  C1   C3    aromatic  1.382  0.020  1.382
 KMN  C1   C7    aromatic  1.400  0.020  1.400
 KMN  N1   C2    single    1.450  0.020  1.450
 KMN  N1   C03   single    1.450  0.020  1.450
 KMN  N1   C16   single    1.450  0.020  1.450
 KMN  O1   C7    single    1.334  0.020  1.334
 KMN  C02  C4    aromatic  1.393  0.020  1.393
 KMN  N2   C10   single    1.465  0.020  1.465
 KMN  N2   C11   single    1.457  0.020  1.457
 KMN  N2   C13   single    1.456  0.020  1.456
 KMN  C03  C8    single    1.521  0.020  1.521
 KMN  C04  C05   triple    1.204  0.020  1.204
 KMN  C4   C7    aromatic  1.405  0.020  1.405
 KMN  C4   C20   single    1.424  0.020  1.424
 KMN  C05  C06   single    1.455  0.020  1.455
 KMN  C07  C08   aromatic  1.396  0.020  1.396
 KMN  C07  C19   aromatic  1.392  0.020  1.392
 KMN  C08  C09   aromatic  1.384  0.020  1.384
 KMN  C8   C10   single    1.527  0.020  1.527
 KMN  C09  C17   aromatic  1.392  0.020  1.392
 KMN  C10  C15   single    1.530  0.020  1.530
 KMN  C11  C12   single    1.520  0.020  1.520
 KMN  C13  C14   single    1.529  0.020  1.529
 KMN  C15  C16   single    1.519  0.020  1.519
 KMN  C17  C18   aromatic  1.385  0.020  1.385
 KMN  C18  C19   aromatic  1.392  0.020  1.392
 KMN  C    H     single    0.913  0.020  1.066
 KMN  C06  H061  single    0.939  0.020  1.096
 KMN  C06  H062  single    0.939  0.020  1.096
 KMN  C02  H02   single    0.929  0.020  1.085
 KMN  C3   H3    single    0.929  0.020  1.085
 KMN  C2   H21C  single    0.939  0.020  1.096
 KMN  C2   H22C  single    0.939  0.020  1.096
 KMN  C03  H031  single    0.939  0.020  1.096
 KMN  C03  H032  single    0.939  0.020  1.096
 KMN  C16  H161  single    0.939  0.020  1.096
 KMN  C16  H162  single    0.939  0.020  1.096
 KMN  O1   H1    single    0.832  0.020  0.971
 KMN  C10  H10   single    0.939  0.020  1.096
 KMN  C11  H111  single    0.939  0.020  1.096
 KMN  C11  H112  single    0.939  0.020  1.096
 KMN  C13  H131  single    0.939  0.020  1.096
 KMN  C13  H132  single    0.939  0.020  1.096
 KMN  C8   H81C  single    0.939  0.020  1.096
 KMN  C8   H82C  single    0.939  0.020  1.096
 KMN  C08  H08   single    0.929  0.020  1.085
 KMN  C19  H19   single    0.929  0.020  1.085
 KMN  C09  H09   single    0.929  0.020  1.085
 KMN  C17  H17   single    0.929  0.020  1.085
 KMN  C15  H151  single    0.939  0.020  1.096
 KMN  C15  H152  single    0.939  0.020  1.096
 KMN  C12  H121  single    0.939  0.020  1.096
 KMN  C12  H122  single    0.939  0.020  1.096
 KMN  C12  H123  single    0.939  0.020  1.096
 KMN  C14  H141  single    0.939  0.020  1.096
 KMN  C14  H142  single    0.939  0.020  1.096
 KMN  C14  H143  single    0.939  0.020  1.096
 KMN  C18  H18   single    0.929  0.020  1.085

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
 KMN  H     C    C20   180.00  3.000
 KMN  C07   O    C06   118.07  3.000
 KMN  C04   C01  C3    120.15  3.000
 KMN  C04   C01  C02   121.16  3.000
 KMN  C3    C01  C02   118.69  3.000
 KMN  C7    C1   C3    118.60  3.000
 KMN  C7    C1   C2    120.93  3.000
 KMN  C3    C1   C2    120.47  3.000
 KMN  C16   N1   C03   110.62  3.000
 KMN  C16   N1   C2    112.16  3.000
 KMN  C03   N1   C2    110.34  3.000
 KMN  H02   C02  C4    119.27  3.000
 KMN  H02   C02  C01   120.43  3.000
 KMN  C4    C02  C01   120.30  3.000
 KMN  H22C  C2   H21C  106.28  3.000
 KMN  H22C  C2   N1    108.12  3.000
 KMN  H21C  C2   N1    111.49  3.000
 KMN  H22C  C2   C1    109.70  3.000
 KMN  H21C  C2   C1    108.26  3.000
 KMN  N1    C2   C1    112.79  3.000
 KMN  C13   N2   C11   112.27  3.000
 KMN  C13   N2   C10   115.73  3.000
 KMN  C11   N2   C10   111.05  3.000
 KMN  H032  C03  H031  106.48  3.000
 KMN  H032  C03  C8    108.91  3.000
 KMN  H031  C03  C8    109.04  3.000
 KMN  H032  C03  N1    108.70  3.000
 KMN  H031  C03  N1    111.22  3.000
 KMN  C8    C03  N1    112.29  3.000
 KMN  H3    C3   C1    118.59  3.000
 KMN  H3    C3   C01   119.15  3.000
 KMN  C1    C3   C01   122.26  3.000
 KMN  C05   C04  C01   180.00  3.000
 KMN  C20   C4   C7    118.64  3.000
 KMN  C20   C4   C02   121.20  3.000
 KMN  C7    C4   C02   120.15  3.000
 KMN  C06   C05  C04   180.00  3.000
 KMN  H062  C06  H061  107.24  3.000
 KMN  H062  C06  C05   109.61  3.000
 KMN  H061  C06  C05   109.89  3.000
 KMN  H062  C06  O     111.21  3.000
 KMN  H061  C06  O     111.13  3.000
 KMN  C05   C06  O     107.77  3.000
 KMN  C19   C07  C08   119.79  3.000
 KMN  C19   C07  O     124.34  3.000
 KMN  C08   C07  O     115.87  3.000
 KMN  C4    C7   O1    121.83  3.000
 KMN  C4    C7   C1    120.00  3.000
 KMN  O1    C7   C1    118.16  3.000
 KMN  H08   C08  C09   120.55  3.000
 KMN  H08   C08  C07   119.47  3.000
 KMN  C09   C08  C07   119.98  3.000
 KMN  H82C  C8   H81C  107.32  3.000
 KMN  H82C  C8   C10   109.75  3.000
 KMN  H81C  C8   C10   111.69  3.000
 KMN  H82C  C8   C03   109.48  3.000
 KMN  H81C  C8   C03   107.50  3.000
 KMN  C10   C8   C03   111.00  3.000
 KMN  H09   C09  C17   120.12  3.000
 KMN  H09   C09  C08   119.24  3.000
 KMN  C17   C09  C08   120.65  3.000
 KMN  H10   C10  C15   107.82  3.000
 KMN  H10   C10  C8    106.93  3.000
 KMN  C15   C10  C8    106.77  3.000
 KMN  H10   C10  N2    110.59  3.000
 KMN  C15   C10  N2    110.40  3.000
 KMN  C8    C10  N2    114.06  3.000
 KMN  H112  C11  H111  105.59  3.000
 KMN  H112  C11  C12   109.29  3.000
 KMN  H111  C11  C12   107.72  3.000
 KMN  H112  C11  N2    111.68  3.000
 KMN  H111  C11  N2    108.35  3.000
 KMN  C12   C11  N2    113.80  3.000
 KMN  H123  C12  H122  107.90  3.000
 KMN  H123  C12  H121  107.14  3.000
 KMN  H122  C12  H121  108.12  3.000
 KMN  H123  C12  C11   109.67  3.000
 KMN  H122  C12  C11   110.92  3.000
 KMN  H121  C12  C11   112.90  3.000
 KMN  H132  C13  H131  104.63  3.000
 KMN  H132  C13  C14   108.91  3.000
 KMN  H131  C13  C14   109.39  3.000
 KMN  H132  C13  N2    107.93  3.000
 KMN  H131  C13  N2    108.56  3.000
 KMN  C14   C13  N2    116.72  3.000
 KMN  H143  C14  H142  107.55  3.000
 KMN  H143  C14  H141  107.30  3.000
 KMN  H142  C14  H141  107.57  3.000
 KMN  H143  C14  C13   110.03  3.000
 KMN  H142  C14  C13   111.95  3.000
 KMN  H141  C14  C13   112.21  3.000
 KMN  H152  C15  H151  107.01  3.000
 KMN  H152  C15  C16   109.66  3.000
 KMN  H151  C15  C16   107.62  3.000
 KMN  H152  C15  C10   108.50  3.000
 KMN  H151  C15  C10   111.84  3.000
 KMN  C16   C15  C10   112.07  3.000
 KMN  H162  C16  H161  106.42  3.000
 KMN  H162  C16  C15   109.51  3.000
 KMN  H161  C16  C15   108.70  3.000
 KMN  H162  C16  N1    111.27  3.000
 KMN  H161  C16  N1    109.26  3.000
 KMN  C15   C16  N1    111.52  3.000
 KMN  H17   C17  C18   120.54  3.000
 KMN  H17   C17  C09   120.38  3.000
 KMN  C18   C17  C09   119.07  3.000
 KMN  H18   C18  C19   118.86  3.000
 KMN  H18   C18  C17   120.10  3.000
 KMN  C19   C18  C17   121.04  3.000
 KMN  H19   C19  C18   118.85  3.000
 KMN  H19   C19  C07   121.68  3.000
 KMN  C18   C19  C07   119.47  3.000
 KMN  C4    C20  C     180.00  3.000
 KMN  H1    O1   C7    110.96  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
 KMN  CONST_01  C7    C4   C02  C01     0.00   0.0  0
 KMN  CONST_02  C7    C1   C3   C01     0.00   0.0  0
 KMN  CONST_03  C02   C01  C3   C1      0.00   0.0  0
 KMN  CONST_04  C02   C4   C7   C1      0.00   0.0  0
 KMN  CONST_05  C4    C02  C01  C3      0.00   0.0  0
 KMN  CONST_06  C4    C7   C1   C3      0.00   0.0  0
 KMN  CONST_07  C17   C09  C08  C07     0.00   0.0  0
 KMN  CONST_08  C17   C18  C19  C07     0.00   0.0  0
 KMN  CONST_09  C18   C19  C07  C08     0.00   0.0  0
 KMN  CONST_10  C18   C17  C09  C08     0.00   0.0  0
 KMN  CONST_11  C19   C07  C08  C09     0.00   0.0  0
 KMN  CONST_12  C19   C18  C17  C09     0.00   0.0  0
 KMN  CONST_13  C09   C08  C07  O     180.00   0.0  0
 KMN  CONST_14  C18   C19  C07  O     180.00   0.0  0
 KMN  CONST_15  C20   C4   C02  C01   180.00   0.0  0
 KMN  CONST_16  C2    C1   C3   C01   180.00   0.0  0
 KMN  CONST_17  C04   C01  C3   C1    180.00   0.0  0
 KMN  CONST_18  C20   C4   C7   C1    180.00   0.0  0
 KMN  CONST_19  C3    C1   C7   O1    180.00   0.0  0
 KMN  CONST_20  C02   C4   C7   O1    180.00   0.0  0
 KMN  CONST_21  C4    C7   C1   C2    180.00   0.0  0
 KMN  CONST_22  C4    C02  C01  C04   180.00   0.0  0
 KMN  CONST_23  H3    C3   C01  C02   180.00   0.0  0
 KMN  CONST_24  H02   C02  C01  C3    180.00   0.0  0
 KMN  CONST_25  H09   C09  C08  C07   180.00   0.0  0
 KMN  CONST_26  H18   C18  C19  C07   180.00   0.0  0
 KMN  CONST_27  H19   C19  C07  C08   180.00   0.0  0
 KMN  CONST_28  H17   C17  C09  C08   180.00   0.0  0
 KMN  CONST_29  H08   C08  C09  C17   180.00   0.0  0
 KMN  Var_01    C10   C8   C03  N1     58.28  30.0  1
 KMN  Var_02    C10   C15  C16  N1    -57.69  30.0  1
 KMN  Var_03    C15   C16  N1   C03    57.06  30.0  1
 KMN  Var_04    C16   N1   C03  C8    -57.86  30.0  1
 KMN  Var_05    C03   N1   C2   C1   -173.34  30.0  2
 KMN  Var_06    C3    C1   C2   N1   -109.38  30.0  2
 KMN  Var_07    C08   C07  O    C06   179.37  30.0  2
 KMN  Var_08    C12   C11  N2   C10  -167.25  30.0  3
 KMN  Var_09    C14   C13  N2   C10   -68.49  30.0  3
 KMN  Var_10    H061  C06  O    C07   -60.43  30.0  3
 KMN  Var_11    H121  C12  C11  N2    -67.67  30.0  3
 KMN  Var_12    H141  C14  C13  N2    -65.44  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
 KMN  chir_01  C10  N2  C8  C15  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
 KMN  plan-1  C    0.020
 KMN  plan-1  C01  0.020
 KMN  plan-1  C1   0.020
 KMN  plan-1  C02  0.020
 KMN  plan-1  C2   0.020
 KMN  plan-1  C3   0.020
 KMN  plan-1  C04  0.020
 KMN  plan-1  C4   0.020
 KMN  plan-1  C05  0.020
 KMN  plan-1  C7   0.020
 KMN  plan-1  C20  0.020
 KMN  plan-1  H02  0.020
 KMN  plan-1  H3   0.020
 KMN  plan-1  O1   0.020
 KMN  plan-2  O    0.020
 KMN  plan-2  C07  0.020
 KMN  plan-2  C08  0.020
 KMN  plan-2  C09  0.020
 KMN  plan-2  C17  0.020
 KMN  plan-2  C18  0.020
 KMN  plan-2  C19  0.020
 KMN  plan-2  H08  0.020
 KMN  plan-2  H19  0.020
 KMN  plan-2  H09  0.020
 KMN  plan-2  H17  0.020
 KMN  plan-2  H18  0.020

