# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May 10 16:36:42 2020
#   Inital geometry file: a 68 line input string
#   Ligand name: 4-(6-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCn1c2cc(Br)ncc2nc1c3nonc3N
#
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
 Z21  Z21  4-(6-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine  ligand  27  18  .  2021-08-25  2021-08-25  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_Z21
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
 Z21  BR    BR  BR    0  -0.040  -4.3761   0.0735  -0.0467
 Z21  C     C   CR6   0   0.065  -2.5381  -0.3910  -0.0030
 Z21  C1    C   CR16  0  -0.316  -1.6043   0.6179  -0.1382
 Z21  C2    C   CR56  0   0.433  -0.2884   0.1748  -0.0921
 Z21  N2    N   NR5   0  -0.557   0.9084   0.8168  -0.1938
 Z21  C6    C   CH2   0  -0.339   1.0758   2.2584  -0.3329
 Z21  C7    C   CH3   0  -0.661   1.2607   2.9515   1.0040
 Z21  C5    C   CR5   0   0.552   1.8634  -0.1550  -0.0680
 Z21  N1    N   N     0  -0.505   1.3705  -1.3555   0.0905
 Z21  C3    C   CR56  0   0.097   0.0175  -1.1830   0.0796
 Z21  C4    C   CR16  0  -0.112  -1.0279  -2.0911   0.1998
 Z21  N     N   N     0  -0.402  -2.2833  -1.6805   0.1573
 Z21  C8    C   CR5   0   0.090   3.2938   0.0563  -0.0985
 Z21  C9    C   CR5   0   0.355   4.3052  -0.9664  -0.0524
 Z21  N5    N   NH2   0  -0.848   4.1220  -2.2981  -0.0416
 Z21  N4    N   N     0  -0.187   5.4615  -0.3675  -0.0748
 Z21  O     O   O     0  -0.211   5.1905   0.9637  -0.1379
 Z21  N3    N   N     0  -0.119   3.8902   1.2048  -0.1483
 Z21  H1    H   HCR6  0   0.308  -1.8786   1.6550  -0.2691
 Z21  H61C  H   HCH2  0   0.284   1.9170   2.4464  -0.9952
 Z21  H62C  H   HCH2  0   0.282   0.1882   2.6321  -0.8414
 Z21  H71C  H   HCH3  0   0.240   2.1545   2.5985   1.5167
 Z21  H72C  H   HCH3  0   0.249   1.3693   4.0231   0.8413
 Z21  H73C  H   HCH3  0   0.240   0.4017   2.7949   1.6560
 Z21  H4    H   HCR6  0   0.284  -0.8489  -3.1520   0.3295
 Z21  H51N  H   HNH2  0   0.415   3.2048  -2.6240   0.2209
 Z21  H52N  H   HNH2  0   0.405   4.8989  -2.8765   0.2323

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
 Z21  BR  C     single    1.896  0.020  1.896
 Z21  C   C1    aromatic  1.381  0.020  1.381
 Z21  C   N     aromatic  1.324  0.020  1.324
 Z21  C1  C2    aromatic  1.389  0.020  1.389
 Z21  C2  N2    aromatic  1.362  0.020  1.362
 Z21  C2  C3    aromatic  1.402  0.020  1.402
 Z21  N2  C6    single    1.458  0.020  1.458
 Z21  N2  C5    aromatic  1.368  0.020  1.368
 Z21  C6  C7    single    1.517  0.020  1.517
 Z21  C5  N1    aromatic  1.307  0.020  1.307
 Z21  C5  C8    single    1.446  0.020  1.446
 Z21  N1  C3    aromatic  1.364  0.020  1.364
 Z21  C3  C4    aromatic  1.390  0.020  1.390
 Z21  C4  N     aromatic  1.321  0.020  1.321
 Z21  C8  C9    aromatic  1.439  0.020  1.439
 Z21  C8  N3    aromatic  1.295  0.020  1.295
 Z21  C9  N5    single    1.344  0.020  1.344
 Z21  C9  N4    aromatic  1.302  0.020  1.302
 Z21  N4  O     aromatic  1.360  0.020  1.360
 Z21  O   N3    aromatic  1.322  0.020  1.322
 Z21  C1  H1    single    0.930  0.020  1.080
 Z21  C6  H61C  single    0.970  0.020  1.090
 Z21  C6  H62C  single    0.970  0.020  1.090
 Z21  C7  H71C  single    0.970  0.020  1.090
 Z21  C7  H72C  single    0.970  0.020  1.090
 Z21  C7  H73C  single    0.970  0.020  1.090
 Z21  C4  H4    single    0.930  0.020  1.080
 Z21  N5  H51N  single    0.890  0.020  1.040
 Z21  N5  H52N  single    0.890  0.020  1.040

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
 Z21  N     C   C1    126.37  3.000
 Z21  N     C   BR    115.33  3.000
 Z21  C1    C   BR    118.30  3.000
 Z21  H1    C1  C2    123.40  3.000
 Z21  H1    C1  C     122.76  3.000
 Z21  C2    C1  C     113.84  3.000
 Z21  C3    C2  N2    105.89  3.000
 Z21  C3    C2  C1    121.30  3.000
 Z21  N2    C2  C1    132.81  3.000
 Z21  C5    N2  C6    129.12  3.000
 Z21  C5    N2  C2    105.76  3.000
 Z21  C6    N2  C2    125.04  3.000
 Z21  H62C  C6  H61C  106.67  3.000
 Z21  H62C  C6  C7    110.73  3.000
 Z21  H61C  C6  C7    111.32  3.000
 Z21  H62C  C6  N2    106.88  3.000
 Z21  H61C  C6  N2    108.54  3.000
 Z21  C7    C6  N2    112.44  3.000
 Z21  H73C  C7  H72C  108.01  3.000
 Z21  H73C  C7  H71C  108.58  3.000
 Z21  H72C  C7  H71C  107.90  3.000
 Z21  H73C  C7  C6    111.44  3.000
 Z21  H72C  C7  C6    109.27  3.000
 Z21  H71C  C7  C6    111.52  3.000
 Z21  C8    C5  N1    120.64  3.000
 Z21  C8    C5  N2    125.77  3.000
 Z21  N1    C5  N2    113.59  3.000
 Z21  C3    N1  C5    104.89  3.000
 Z21  C4    C3  N1    131.51  3.000
 Z21  C4    C3  C2    118.63  3.000
 Z21  N1    C3  C2    109.86  3.000
 Z21  H4    C4  N     117.71  3.000
 Z21  H4    C4  C3    121.72  3.000
 Z21  N     C4  C3    120.57  3.000
 Z21  C4    N   C     119.30  3.000
 Z21  N3    C8  C9    107.93  3.000
 Z21  N3    C8  C5    125.87  3.000
 Z21  C9    C8  C5    126.20  3.000
 Z21  N4    C9  N5    125.23  3.000
 Z21  N4    C9  C8    107.25  3.000
 Z21  N5    C9  C8    127.48  3.000
 Z21  H52N  N5  H51N  116.46  3.000
 Z21  H52N  N5  C9    117.78  3.000
 Z21  H51N  N5  C9    116.51  3.000
 Z21  O     N4  C9    105.91  3.000
 Z21  N3    O   N4    112.01  3.000
 Z21  O     N3  C8    106.91  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
 Z21  CONST_01  N2    C2  C1  C   180.00   0.0  0
 Z21  CONST_02  C3    C2  C1  C     0.00   0.0  0
 Z21  CONST_03  C3    C4  N   C     0.00   0.0  0
 Z21  CONST_04  C4    N   C   C1    0.00   0.0  0
 Z21  CONST_05  C5    N2  C2  C1  180.00   0.0  0
 Z21  CONST_06  N1    C3  C2  C1  180.00   0.0  0
 Z21  CONST_07  C4    C3  C2  C1    0.00   0.0  0
 Z21  CONST_08  N     C   C1  C2    0.00   0.0  0
 Z21  CONST_09  N1    C5  N2  C2    0.00   0.0  0
 Z21  CONST_10  C8    C5  N2  C2  180.00   0.0  0
 Z21  CONST_11  C5    N1  C3  C2    0.00   0.0  0
 Z21  CONST_12  N     C4  C3  C2    0.00   0.0  0
 Z21  CONST_13  N1    C3  C2  N2    0.00   0.0  0
 Z21  CONST_14  C4    C3  C2  N2  180.00   0.0  0
 Z21  CONST_15  C3    N1  C5  N2    0.00   0.0  0
 Z21  CONST_16  C9    C8  C5  N2  180.00   0.0  0
 Z21  CONST_17  N3    C8  C5  N2    0.00   0.0  0
 Z21  CONST_18  C3    C2  N2  C5    0.00   0.0  0
 Z21  CONST_19  C4    C3  N1  C5  180.00   0.0  0
 Z21  CONST_20  N4    C9  C8  C5  180.00   0.0  0
 Z21  CONST_21  O     N3  C8  C5  180.00   0.0  0
 Z21  CONST_22  C9    C8  C5  N1    0.00   0.0  0
 Z21  CONST_23  N3    C8  C5  N1  180.00   0.0  0
 Z21  CONST_24  N     C4  C3  N1  180.00   0.0  0
 Z21  CONST_25  C8    C5  N1  C3  180.00   0.0  0
 Z21  CONST_26  O     N4  C9  C8    0.00   0.0  0
 Z21  CONST_27  N4    O   N3  C8    0.00   0.0  0
 Z21  CONST_28  O     N3  C8  C9    0.00   0.0  0
 Z21  CONST_29  N3    O   N4  C9    0.00   0.0  0
 Z21  CONST_30  N3    C8  C9  N4    0.00   0.0  0
 Z21  CONST_31  C2    C1  C   BR  180.00   0.0  0
 Z21  CONST_32  C4    N   C   BR  180.00   0.0  0
 Z21  CONST_33  C6    N2  C2  C1    0.00   0.0  0
 Z21  CONST_34  C3    C2  N2  C6  180.00   0.0  0
 Z21  CONST_35  N1    C5  N2  C6  180.00   0.0  0
 Z21  CONST_36  C8    C5  N2  C6    0.00   0.0  0
 Z21  CONST_37  N5    C9  C8  C5    0.00   0.0  0
 Z21  CONST_38  N3    C8  C9  N5  180.00   0.0  0
 Z21  CONST_39  O     N4  C9  N5  180.00   0.0  0
 Z21  CONST_40  H4    C4  N   C   180.00   0.0  0
 Z21  CONST_41  H1    C1  C2  N2    0.00   0.0  0
 Z21  Var_01    C7    C6  N2  C2   92.84  30.0  2
 Z21  Var_02    H71C  C7  C6  N2   61.44  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
 Z21  plan-1  C5    0.020
 Z21  plan-1  C8    0.020
 Z21  plan-1  C9    0.020
 Z21  plan-1  N5    0.020
 Z21  plan-1  N4    0.020
 Z21  plan-1  O     0.020
 Z21  plan-1  N3    0.020
 Z21  plan-2  BR    0.020
 Z21  plan-2  C     0.020
 Z21  plan-2  C1    0.020
 Z21  plan-2  C2    0.020
 Z21  plan-2  N2    0.020
 Z21  plan-2  C6    0.020
 Z21  plan-2  C5    0.020
 Z21  plan-2  N1    0.020
 Z21  plan-2  C3    0.020
 Z21  plan-2  C4    0.020
 Z21  plan-2  N     0.020
 Z21  plan-2  C8    0.020
 Z21  plan-2  H1    0.020
 Z21  plan-2  H4    0.020
 Z21  plan-3  C9    0.020
 Z21  plan-3  N5    0.020
 Z21  plan-3  H51N  0.020
 Z21  plan-3  H52N  0.020

