# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 03:41:48 2020
#   Inital geometry file: a 97 line input string
#   Ligand name: 3-{[4-amino-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]ethynyl}phenol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)n1nc(C#Cc2cccc(O)c2)c3c(N)ncnc13
#
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
 DLN  DLN  3-{[4-amino-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]ethynyl}phenol  ligand  37  22  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_DLN
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
 DLN  C20   C  CH3   0  -0.630   4.1423   2.7029  -1.0492
 DLN  C19   C  CH1   0  -0.120   4.1439   1.7211   0.1125
 DLN  C21   C  CH3   0  -0.626   4.1889   2.4211   1.4628
 DLN  N7    N  NR5   0  -0.365   2.9895   0.8352   0.0340
 DLN  N8    N  N     0  -0.256   1.7512   1.3268   0.0821
 DLN  C3    C  CR56  0   0.571   2.9897  -0.5110  -0.0609
 DLN  N2    N  N     0  -0.460   4.0470  -1.3244  -0.1307
 DLN  C1    C  CR16  0   0.075   3.6928  -2.5892  -0.2252
 DLN  N6    N  N     0  -0.473   2.4671  -3.1135  -0.2603
 DLN  C5    C  CR6   0   0.459   1.4186  -2.2932  -0.1909
 DLN  N10   N  NH2   0  -0.801   0.1920  -2.8114  -0.2295
 DLN  C4    C  CR56  0  -0.278   1.6556  -0.9073  -0.0781
 DLN  C11   C  CSP   0   0.133  -1.6846   0.5592   0.0368
 DLN  C12   C  CR6   0  -0.082  -3.1002   0.6942   0.0088
 DLN  C13   C  CR16  0  -0.416  -3.9102  -0.3513   0.4598
 DLN  C17   C  CR16  0  -0.295  -3.6789   1.8644  -0.4839
 DLN  C16   C  CR16  0  -0.212  -5.0600   1.9717  -0.5238
 DLN  C15   C  CR16  0  -0.313  -5.8695   0.9386  -0.0834
 DLN  C14   C  CR6   0   0.384  -5.2920  -0.2291   0.4116
 DLN  O18   O  OH1   0  -0.615  -6.1228  -1.2069   0.8251
 DLN  CAI   C  CR5   0   0.130   0.9233   0.3027   0.0174
 DLN  CAM   C  CSP   0   0.094  -0.4812   0.4634   0.0402
 DLN  H201  H  HCH3  0   0.231   5.0440   3.3129  -1.0137
 DLN  H202  H  HCH3  0   0.237   4.1245   2.1845  -2.0072
 DLN  H203  H  HCH3  0   0.230   3.2817   3.3688  -0.9984
 DLN  H19   H  HCH1  0   0.261   5.0075   1.0606   0.0238
 DLN  H211  H  HCH3  0   0.229   3.3415   3.0957   1.5863
 DLN  H212  H  HCH3  0   0.234   4.1827   1.7051   2.2839
 DLN  H213  H  HCH3  0   0.230   5.1015   3.0115   1.5391
 DLN  H1    H  HCR6  0   0.237   4.5028  -3.3077  -0.2849
 DLN  H101  H  HNH2  0   0.385   0.0669  -3.8025  -0.3296
 DLN  H102  H  HNH2  0   0.397  -0.6296  -2.2345  -0.2140
 DLN  H13   H  HCR6  0   0.234  -3.4506  -1.2527   0.8480
 DLN  H17   H  HCR6  0   0.240  -3.0545   2.6739  -0.8338
 DLN  H16   H  HCR6  0   0.248  -5.5146   2.8751  -0.9058
 DLN  H15   H  HCR6  0   0.255  -6.9471   1.0307  -0.1182
 DLN  H18   H  HOH1  0   0.448  -5.6287  -1.9232   1.2330

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
 DLN  C20  C19   single    1.521  0.020  1.521
 DLN  C19  C21   single    1.522  0.020  1.522
 DLN  C19  N7    single    1.457  0.020  1.457
 DLN  N7   N8    aromatic  1.333  0.020  1.333
 DLN  N7   C3    aromatic  1.350  0.020  1.350
 DLN  N8   CAI   aromatic  1.318  0.020  1.318
 DLN  C3   N2    aromatic  1.336  0.020  1.336
 DLN  C3   C4    aromatic  1.392  0.020  1.392
 DLN  N2   C1    aromatic  1.317  0.020  1.317
 DLN  C1   N6    aromatic  1.334  0.020  1.334
 DLN  N6   C5    aromatic  1.333  0.020  1.333
 DLN  C5   N10   single    1.332  0.020  1.332
 DLN  C5   C4    aromatic  1.411  0.020  1.411
 DLN  C4   CAI   aromatic  1.418  0.020  1.418
 DLN  C11  C12   single    1.422  0.020  1.422
 DLN  C11  CAM   triple    1.207  0.020  1.207
 DLN  C12  C13   aromatic  1.397  0.020  1.397
 DLN  C12  C17   aromatic  1.395  0.020  1.395
 DLN  C13  C14   aromatic  1.388  0.020  1.388
 DLN  C17  C16   aromatic  1.386  0.020  1.386
 DLN  C16  C15   aromatic  1.384  0.020  1.384
 DLN  C15  C14   aromatic  1.394  0.020  1.394
 DLN  C14  O18   single    1.348  0.020  1.348
 DLN  CAI  CAM   single    1.414  0.020  1.414
 DLN  C20  H201  single    0.970  0.020  1.090
 DLN  C20  H202  single    0.970  0.020  1.090
 DLN  C20  H203  single    0.970  0.020  1.090
 DLN  C19  H19   single    0.970  0.020  1.090
 DLN  C21  H211  single    0.970  0.020  1.090
 DLN  C21  H212  single    0.970  0.020  1.090
 DLN  C21  H213  single    0.970  0.020  1.090
 DLN  C1   H1    single    0.930  0.020  1.080
 DLN  N10  H101  single    0.860  0.020  1.020
 DLN  N10  H102  single    0.860  0.020  1.020
 DLN  C13  H13   single    0.930  0.020  1.080
 DLN  C17  H17   single    0.930  0.020  1.080
 DLN  C16  H16   single    0.930  0.020  1.080
 DLN  C15  H15   single    0.930  0.020  1.080
 DLN  O18  H18   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
 DLN  H203  C20  H202  108.60  3.000
 DLN  H203  C20  H201  108.07  3.000
 DLN  H202  C20  H201  107.98  3.000
 DLN  H203  C20  C19   111.09  3.000
 DLN  H202  C20  C19   111.38  3.000
 DLN  H201  C20  C19   109.62  3.000
 DLN  H19   C19  N7    104.76  3.000
 DLN  H19   C19  C21   109.10  3.000
 DLN  N7    C19  C21   110.54  3.000
 DLN  H19   C19  C20   109.24  3.000
 DLN  N7    C19  C20   110.52  3.000
 DLN  C21   C19  C20   112.39  3.000
 DLN  H213  C21  H212  107.94  3.000
 DLN  H213  C21  H211  107.92  3.000
 DLN  H212  C21  H211  108.47  3.000
 DLN  H213  C21  C19   109.65  3.000
 DLN  H212  C21  C19   111.49  3.000
 DLN  H211  C21  C19   111.24  3.000
 DLN  C3    N7   N8    111.75  3.000
 DLN  C3    N7   C19   127.60  3.000
 DLN  N8    N7   C19   120.64  3.000
 DLN  CAI   N8   N7    107.16  3.000
 DLN  C4    C3   N2    125.78  3.000
 DLN  C4    C3   N7    106.55  3.000
 DLN  N2    C3   N7    127.67  3.000
 DLN  C1    N2   C3    112.07  3.000
 DLN  H1    C1   N6    115.12  3.000
 DLN  H1    C1   N2    116.07  3.000
 DLN  N6    C1   N2    128.81  3.000
 DLN  C5    N6   C1    118.66  3.000
 DLN  C4    C5   N10   122.63  3.000
 DLN  C4    C5   N6    118.46  3.000
 DLN  N10   C5   N6    118.90  3.000
 DLN  H102  N10  H101  117.83  3.000
 DLN  H102  N10  C5    121.97  3.000
 DLN  H101  N10  C5    120.11  3.000
 DLN  CAI   C4   C5    139.22  3.000
 DLN  CAI   C4   C3    104.56  3.000
 DLN  C5    C4   C3    116.22  3.000
 DLN  CAM   C11  C12   180.00  3.000
 DLN  C17   C12  C13   120.07  3.000
 DLN  C17   C12  C11   119.96  3.000
 DLN  C13   C12  C11   119.97  3.000
 DLN  H13   C13  C14   120.53  3.000
 DLN  H13   C13  C12   119.48  3.000
 DLN  C14   C13  C12   119.99  3.000
 DLN  H17   C17  C16   120.57  3.000
 DLN  H17   C17  C12   120.19  3.000
 DLN  C16   C17  C12   119.24  3.000
 DLN  H16   C16  C15   119.35  3.000
 DLN  H16   C16  C17   119.60  3.000
 DLN  C15   C16  C17   121.06  3.000
 DLN  H15   C15  C14   119.70  3.000
 DLN  H15   C15  C16   120.57  3.000
 DLN  C14   C15  C16   119.73  3.000
 DLN  O18   C14  C15   117.48  3.000
 DLN  O18   C14  C13   122.61  3.000
 DLN  C15   C14  C13   119.92  3.000
 DLN  H18   O18  C14   110.74  3.000
 DLN  CAM   CAI  C4    127.69  3.000
 DLN  CAM   CAI  N8    122.32  3.000
 DLN  C4    CAI  N8    109.99  3.000
 DLN  CAI   CAM  C11   180.00  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
 DLN  CONST_01  C4    CAI  N8   N7      0.00   0.0  0
 DLN  CONST_02  C1    N2   C3   N7    180.00   0.0  0
 DLN  CONST_03  C5    C4   C3   N7    180.00   0.0  0
 DLN  CONST_04  CAI   C4   C3   N7      0.00   0.0  0
 DLN  CONST_05  N2    C3   N7   N8    180.00   0.0  0
 DLN  CONST_06  C4    C3   N7   N8      0.00   0.0  0
 DLN  CONST_07  C3    C4   CAI  N8      0.00   0.0  0
 DLN  CONST_08  C5    C4   CAI  N8    180.00   0.0  0
 DLN  CONST_09  CAI   N8   N7   C3      0.00   0.0  0
 DLN  CONST_10  N6    C1   N2   C3      0.00   0.0  0
 DLN  CONST_11  N6    C5   C4   C3      0.00   0.0  0
 DLN  CONST_12  C5    C4   C3   N2      0.00   0.0  0
 DLN  CONST_13  CAI   C4   C3   N2    180.00   0.0  0
 DLN  CONST_14  C5    N6   C1   N2      0.00   0.0  0
 DLN  CONST_15  C4    C3   N2   C1      0.00   0.0  0
 DLN  CONST_16  C4    C5   N6   C1      0.00   0.0  0
 DLN  CONST_17  CAI   C4   C5   N6    180.00   0.0  0
 DLN  CONST_18  C15   C14  C13  C12     0.00   0.0  0
 DLN  CONST_19  C15   C16  C17  C12     0.00   0.0  0
 DLN  CONST_20  C16   C17  C12  C13     0.00   0.0  0
 DLN  CONST_21  C16   C15  C14  C13     0.00   0.0  0
 DLN  CONST_22  C14   C13  C12  C17     0.00   0.0  0
 DLN  CONST_23  C14   C15  C16  C17     0.00   0.0  0
 DLN  CONST_24  CAI   N8   N7   C19   180.00   0.0  0
 DLN  CONST_25  N2    C3   N7   C19     0.00   0.0  0
 DLN  CONST_26  C4    C3   N7   C19   180.00   0.0  0
 DLN  CONST_27  CAM   CAI  N8   N7    180.00   0.0  0
 DLN  CONST_28  N10   C5   C4   C3    180.00   0.0  0
 DLN  CONST_29  CAM   CAI  C4   C3    180.00   0.0  0
 DLN  CONST_30  N10   C5   N6   C1    180.00   0.0  0
 DLN  CONST_31  CAM   CAI  C4   C5      0.00   0.0  0
 DLN  CONST_32  CAI   C4   C5   N10     0.00   0.0  0
 DLN  CONST_33  C14   C13  C12  C11   180.00   0.0  0
 DLN  CONST_34  C16   C17  C12  C11   180.00   0.0  0
 DLN  CONST_35  O18   C14  C13  C12   180.00   0.0  0
 DLN  CONST_36  O18   C14  C15  C16   180.00   0.0  0
 DLN  CONST_37  H1    C1   N2   C3    180.00   0.0  0
 DLN  CONST_38  H16   C16  C17  C12   180.00   0.0  0
 DLN  CONST_39  H17   C17  C12  C13   180.00   0.0  0
 DLN  CONST_40  H15   C15  C14  C13   180.00   0.0  0
 DLN  CONST_41  H13   C13  C12  C17   180.00   0.0  0
 DLN  CONST_42  H101  N10  C5   N6      0.00   0.0  0
 DLN  CONST_43  H102  N10  C5   N6    180.00   0.0  0
 DLN  Var_01    N8    N7   C19  C20   -61.05  30.0  2
 DLN  Var_02    H201  C20  C19  N7   -176.25  30.0  3
 DLN  Var_03    H211  C21  C19  N7    -65.60  30.0  3

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
 DLN  plan-1  C11   0.020
 DLN  plan-1  C12   0.020
 DLN  plan-1  C13   0.020
 DLN  plan-1  C17   0.020
 DLN  plan-1  C16   0.020
 DLN  plan-1  C15   0.020
 DLN  plan-1  C14   0.020
 DLN  plan-1  O18   0.020
 DLN  plan-1  CAM   0.020
 DLN  plan-1  H13   0.020
 DLN  plan-1  H17   0.020
 DLN  plan-1  H16   0.020
 DLN  plan-1  H15   0.020
 DLN  plan-2  C19   0.020
 DLN  plan-2  N7    0.020
 DLN  plan-2  N8    0.020
 DLN  plan-2  C3    0.020
 DLN  plan-2  N2    0.020
 DLN  plan-2  C1    0.020
 DLN  plan-2  N6    0.020
 DLN  plan-2  C5    0.020
 DLN  plan-2  N10   0.020
 DLN  plan-2  C4    0.020
 DLN  plan-2  C11   0.020
 DLN  plan-2  CAI   0.020
 DLN  plan-2  CAM   0.020
 DLN  plan-2  H1    0.020
 DLN  plan-3  C5    0.020
 DLN  plan-3  N10   0.020
 DLN  plan-3  H101  0.020
 DLN  plan-3  H102  0.020

