# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 16:58:04 2022
#   Inital geometry file: a 148 line input string
#   Ligand name: (2S)-8-benzyl-2-hydroxy-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(2H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(C[C@@]2(O)N=C3N(C=C(N=C3Cc4ccccc4)c5ccc(O)cc5)C2=O)cc1
#
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
 CTZ  CTZ  (2S)-8-benzyl-2-hydroxy-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(2H)-one  ligand  54  33  .  2022-09-15  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_CTZ
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
 CTZ  N1    N  N     0  -0.440   0.3094  -0.7080   1.8363
 CTZ  C2    C  CT    0   0.206   1.6344  -0.6595   2.4210
 CTZ  C3    C  C     0   0.529   2.5961  -0.4889   1.2232
 CTZ  N4    N  NR6   0  -0.594   1.7499  -0.3100   0.1380
 CTZ  C5    C  CR16  0  -0.006   2.0672  -0.1185  -1.1827
 CTZ  C6    C  CR6   0   0.138   1.0534  -0.0396  -2.0725
 CTZ  N7    N  N     0  -0.382  -0.2613  -0.1799  -1.6601
 CTZ  C8    C  CR6   0   0.200  -0.5779  -0.3835  -0.4388
 CTZ  C9    C  CR6   0   0.510   0.4495  -0.4766   0.5894
 CTZ  C10   C  CH2   0  -0.552   1.7797   0.5887   3.3100
 CTZ  C11   C  CR6   0   0.130   0.8143   0.5932   4.4574
 CTZ  C12   C  CR16  0  -0.286   1.1579   0.0391   5.6877
 CTZ  C13   C  CR16  0  -0.328   0.2694   0.0284   6.7514
 CTZ  C14   C  CR6   0   0.340  -1.0014   0.5767   6.5989
 CTZ  C15   C  CR16  0  -0.374  -1.3603   1.1383   5.3761
 CTZ  C16   C  CR16  0  -0.284  -0.4580   1.1395   4.3233
 CTZ  O17   O  OH1   0  -0.634  -1.8369   0.5451   7.6581
 CTZ  O18   O  O     0  -0.389   3.7953  -0.4767   1.1966
 CTZ  C19   C  CR6   0   0.029   1.2458   0.1730  -3.5152
 CTZ  C20   C  CR16  0  -0.276   0.1915  -0.0565  -4.4031
 CTZ  C21   C  CR16  0  -0.321   0.3483   0.1116  -5.7671
 CTZ  C22   C  CR6   0   0.347   1.5739   0.5239  -6.2845
 CTZ  C23   C  CR16  0  -0.364   2.6323   0.7690  -5.4114
 CTZ  C24   C  CR16  0  -0.322   2.4634   0.5975  -4.0489
 CTZ  O25   O  OH1   0  -0.628   1.6792   0.6747  -7.6176
 CTZ  C26   C  CH2   0  -0.608  -2.0041  -0.5492  -0.0105
 CTZ  C27   C  CR6   0   0.157  -2.9805  -0.3628  -1.1336
 CTZ  C28   C  CR16  0  -0.287  -3.2574  -1.4065  -2.0112
 CTZ  C29   C  CR16  0  -0.244  -4.1375  -1.2277  -3.0685
 CTZ  C30   C  CR16  0  -0.269  -4.7540   0.0025  -3.2623
 CTZ  C31   C  CR16  0  -0.242  -4.4864   1.0482  -2.3899
 CTZ  C32   C  CR16  0  -0.307  -3.6029   0.8641  -1.3338
 CTZ  O33   O  OH1   0  -0.632   1.9341  -1.7728   3.1873
 CTZ  H5    H  HCR6  0   0.315   3.1179  -0.0450  -1.4201
 CTZ  H101  H  HCH2  0   0.279   1.6409   1.4770   2.6887
 CTZ  H102  H  HCH2  0   0.273   2.8098   0.6190   3.6744
 CTZ  H12   H  HCR6  0   0.246   2.1444  -0.3856   5.8280
 CTZ  H13   H  HCR6  0   0.260   0.5592  -0.4035   7.7013
 CTZ  H15   H  HCR6  0   0.267  -2.3431   1.5776   5.2435
 CTZ  H16   H  HCR6  0   0.246  -0.7556   1.5811   3.3803
 CTZ  H17   H  HOH1  0   0.473  -2.6819   0.9466   7.4279
 CTZ  H20   H  HCR6  0   0.266  -0.7677  -0.3756  -4.0178
 CTZ  H21   H  HCR6  0   0.264  -0.4816  -0.0777  -6.4367
 CTZ  H23   H  HCR6  0   0.275   3.5895   1.1055  -5.7927
 CTZ  H24   H  HCR6  0   0.254   3.3039   0.8157  -3.4019
 CTZ  H25   H  HOH1  0   0.476   2.5671   0.9624  -7.8575
 CTZ  H261  H  HCH2  0   0.289  -2.1073  -1.5431   0.4374
 CTZ  H262  H  HCH2  0   0.286  -2.2020   0.1552   0.8030
 CTZ  H28   H  HCR6  0   0.246  -2.7817  -2.3694  -1.8662
 CTZ  H29   H  HCR6  0   0.252  -4.3460  -2.0504  -3.7407
 CTZ  H30   H  HCR6  0   0.253  -5.4429   0.1419  -4.0854
 CTZ  H31   H  HCR6  0   0.253  -4.9660   2.0088  -2.5290
 CTZ  H32   H  HCR6  0   0.248  -3.3985   1.6849  -0.6560
 CTZ  H33   H  HOH1  0   0.462   1.7291  -2.5721   2.6881

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
 CTZ  N1   C2    single    1.449  0.020  1.449
 CTZ  N1   C9    double    1.276  0.020  1.276
 CTZ  C2   C3    single    1.545  0.020  1.545
 CTZ  C2   C10   single    1.539  0.020  1.539
 CTZ  C2   O33   single    1.384  0.020  1.384
 CTZ  C3   N4    single    1.388  0.020  1.388
 CTZ  C3   O18   double    1.200  0.020  1.200
 CTZ  N4   C5    single    1.372  0.020  1.372
 CTZ  N4   C9    single    1.387  0.020  1.387
 CTZ  C5   C6    double    1.351  0.020  1.351
 CTZ  C5   H5    single    0.930  0.020  1.080
 CTZ  C6   N7    single    1.385  0.020  1.385
 CTZ  C6   C19   single    1.471  0.020  1.471
 CTZ  N7   C8    double    1.278  0.020  1.278
 CTZ  C8   C9    single    1.456  0.020  1.456
 CTZ  C8   C26   single    1.498  0.020  1.498
 CTZ  C10  C11   single    1.500  0.020  1.500
 CTZ  C10  H101  single    0.970  0.020  1.090
 CTZ  C10  H102  single    0.970  0.020  1.090
 CTZ  C11  C12   aromatic  1.392  0.020  1.392
 CTZ  C11  C16   aromatic  1.391  0.020  1.391
 CTZ  C12  C13   aromatic  1.386  0.020  1.386
 CTZ  C12  H12   single    0.930  0.020  1.080
 CTZ  C13  C14   aromatic  1.392  0.020  1.392
 CTZ  C13  H13   single    0.930  0.020  1.080
 CTZ  C14  C15   aromatic  1.393  0.020  1.393
 CTZ  C14  O17   single    1.349  0.020  1.349
 CTZ  C15  C16   aromatic  1.387  0.020  1.387
 CTZ  C15  H15   single    0.930  0.020  1.080
 CTZ  C16  H16   single    0.930  0.020  1.080
 CTZ  O17  H17   single    0.850  0.020  0.980
 CTZ  C19  C20   aromatic  1.397  0.020  1.397
 CTZ  C19  C24   aromatic  1.396  0.020  1.396
 CTZ  C20  C21   aromatic  1.383  0.020  1.383
 CTZ  C20  H20   single    0.930  0.020  1.080
 CTZ  C21  C22   aromatic  1.393  0.020  1.393
 CTZ  C21  H21   single    0.930  0.020  1.080
 CTZ  C22  C23   aromatic  1.394  0.020  1.394
 CTZ  C22  O25   single    1.346  0.020  1.346
 CTZ  C23  C24   aromatic  1.384  0.020  1.384
 CTZ  C23  H23   single    0.930  0.020  1.080
 CTZ  C24  H24   single    0.930  0.020  1.080
 CTZ  O25  H25   single    0.850  0.020  0.980
 CTZ  C26  C27   single    1.500  0.020  1.500
 CTZ  C26  H261  single    0.970  0.020  1.090
 CTZ  C26  H262  single    0.970  0.020  1.090
 CTZ  C27  C28   aromatic  1.392  0.020  1.392
 CTZ  C27  C32   aromatic  1.390  0.020  1.390
 CTZ  C28  C29   aromatic  1.387  0.020  1.387
 CTZ  C28  H28   single    0.930  0.020  1.080
 CTZ  C29  C30   aromatic  1.390  0.020  1.390
 CTZ  C29  H29   single    0.930  0.020  1.080
 CTZ  C30  C31   aromatic  1.388  0.020  1.388
 CTZ  C30  H30   single    0.930  0.020  1.080
 CTZ  C31  C32   aromatic  1.389  0.020  1.389
 CTZ  C31  H31   single    0.930  0.020  1.080
 CTZ  C32  H32   single    0.930  0.020  1.080
 CTZ  O33  H33   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
 CTZ  C9    N1   C2    106.73  3.000
 CTZ  O33   C2   C10   108.18  3.000
 CTZ  O33   C2   C3    112.52  3.000
 CTZ  C10   C2   C3    107.42  3.000
 CTZ  O33   C2   N1    113.23  3.000
 CTZ  C10   C2   N1    110.27  3.000
 CTZ  C3    C2   N1    105.07  3.000
 CTZ  O18   C3   N4    126.22  3.000
 CTZ  O18   C3   C2    129.82  3.000
 CTZ  N4    C3   C2    103.94  3.000
 CTZ  C9    N4   C5    123.17  3.000
 CTZ  C9    N4   C3    107.57  3.000
 CTZ  C5    N4   C3    129.04  3.000
 CTZ  H5    C5   C6    125.55  3.000
 CTZ  H5    C5   N4    116.50  3.000
 CTZ  C6    C5   N4    117.95  3.000
 CTZ  C19   C6   N7    115.52  3.000
 CTZ  C19   C6   C5    123.79  3.000
 CTZ  N7    C6   C5    120.68  3.000
 CTZ  C8    N7   C6    122.40  3.000
 CTZ  C26   C8   C9    117.56  3.000
 CTZ  C26   C8   N7    121.78  3.000
 CTZ  C9    C8   N7    120.67  3.000
 CTZ  C8    C9   N4    115.10  3.000
 CTZ  C8    C9   N1    128.61  3.000
 CTZ  N4    C9   N1    116.29  3.000
 CTZ  H102  C10  H101  106.66  3.000
 CTZ  H102  C10  C11   110.58  3.000
 CTZ  H101  C10  C11   110.53  3.000
 CTZ  H102  C10  C2    107.70  3.000
 CTZ  H101  C10  C2    108.59  3.000
 CTZ  C11   C10  C2    112.56  3.000
 CTZ  C16   C11  C12   117.85  3.000
 CTZ  C16   C11  C10   121.08  3.000
 CTZ  C12   C11  C10   121.06  3.000
 CTZ  H12   C12  C13   118.78  3.000
 CTZ  H12   C12  C11   119.68  3.000
 CTZ  C13   C12  C11   121.53  3.000
 CTZ  H13   C13  C14   119.82  3.000
 CTZ  H13   C13  C12   120.31  3.000
 CTZ  C14   C13  C12   119.87  3.000
 CTZ  O17   C14  C15   122.62  3.000
 CTZ  O17   C14  C13   118.03  3.000
 CTZ  C15   C14  C13   119.35  3.000
 CTZ  H15   C15  C16   119.76  3.000
 CTZ  H15   C15  C14   120.28  3.000
 CTZ  C16   C15  C14   119.96  3.000
 CTZ  H16   C16  C15   118.86  3.000
 CTZ  H16   C16  C11   119.70  3.000
 CTZ  C15   C16  C11   121.44  3.000
 CTZ  H17   O17  C14   110.23  3.000
 CTZ  C24   C19  C20   117.72  3.000
 CTZ  C24   C19  C6    122.22  3.000
 CTZ  C20   C19  C6    120.06  3.000
 CTZ  H20   C20  C21   119.18  3.000
 CTZ  H20   C20  C19   119.41  3.000
 CTZ  C21   C20  C19   121.41  3.000
 CTZ  H21   C21  C22   119.76  3.000
 CTZ  H21   C21  C20   120.10  3.000
 CTZ  C22   C21  C20   120.14  3.000
 CTZ  O25   C22  C23   122.78  3.000
 CTZ  O25   C22  C21   118.04  3.000
 CTZ  C23   C22  C21   119.18  3.000
 CTZ  H23   C23  C24   119.52  3.000
 CTZ  H23   C23  C22   120.32  3.000
 CTZ  C24   C23  C22   120.16  3.000
 CTZ  H24   C24  C23   117.94  3.000
 CTZ  H24   C24  C19   120.66  3.000
 CTZ  C23   C24  C19   121.39  3.000
 CTZ  H25   O25  C22   110.62  3.000
 CTZ  H262  C26  H261  105.26  3.000
 CTZ  H262  C26  C27   111.03  3.000
 CTZ  H261  C26  C27   110.96  3.000
 CTZ  H262  C26  C8    108.27  3.000
 CTZ  H261  C26  C8    107.88  3.000
 CTZ  C27   C26  C8    113.07  3.000
 CTZ  C32   C27  C28   118.82  3.000
 CTZ  C32   C27  C26   120.59  3.000
 CTZ  C28   C27  C26   120.57  3.000
 CTZ  H28   C28  C29   119.67  3.000
 CTZ  H28   C28  C27   119.65  3.000
 CTZ  C29   C28  C27   120.68  3.000
 CTZ  H29   C29  C30   120.05  3.000
 CTZ  H29   C29  C28   119.82  3.000
 CTZ  C30   C29  C28   120.13  3.000
 CTZ  H30   C30  C31   120.25  3.000
 CTZ  H30   C30  C29   120.16  3.000
 CTZ  C31   C30  C29   119.59  3.000
 CTZ  H31   C31  C32   119.80  3.000
 CTZ  H31   C31  C30   120.15  3.000
 CTZ  C32   C31  C30   120.05  3.000
 CTZ  H32   C32  C31   119.67  3.000
 CTZ  H32   C32  C27   119.59  3.000
 CTZ  C31   C32  C27   120.74  3.000
 CTZ  H33   O33  C2    109.51  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
 CTZ  CONST_01  C14  C13  C12  C11    0.00   0.0  0
 CTZ  CONST_02  C14  C15  C16  C11    0.00   0.0  0
 CTZ  CONST_03  C15  C16  C11  C12    0.00   0.0  0
 CTZ  CONST_04  C15  C14  C13  C12    0.00   0.0  0
 CTZ  CONST_05  C16  C11  C12  C13    0.00   0.0  0
 CTZ  CONST_06  C16  C15  C14  C13    0.00   0.0  0
 CTZ  CONST_07  C22  C21  C20  C19    0.00   0.0  0
 CTZ  CONST_08  C22  C23  C24  C19    0.00   0.0  0
 CTZ  CONST_09  C23  C24  C19  C20    0.00   0.0  0
 CTZ  CONST_10  C23  C22  C21  C20    0.00   0.0  0
 CTZ  CONST_11  C24  C19  C20  C21    0.00   0.0  0
 CTZ  CONST_12  C24  C23  C22  C21    0.00   0.0  0
 CTZ  CONST_13  C30  C29  C28  C27    0.00   0.0  0
 CTZ  CONST_14  C30  C31  C32  C27    0.00   0.0  0
 CTZ  CONST_15  C31  C32  C27  C28    0.00   0.0  0
 CTZ  CONST_16  C31  C30  C29  C28    0.00   0.0  0
 CTZ  CONST_17  C32  C27  C28  C29    0.00   0.0  0
 CTZ  CONST_18  C32  C31  C30  C29    0.00   0.0  0
 CTZ  CONST_19  C21  C20  C19  C6   180.00   0.0  0
 CTZ  CONST_20  C23  C24  C19  C6   180.00   0.0  0
 CTZ  CONST_21  C3   N4   C9   N1     0.00   0.0  0
 CTZ  CONST_22  C5   N4   C9   N1   180.00   0.0  0
 CTZ  CONST_23  N4   C9   N1   C2     0.00   0.0  0
 CTZ  CONST_24  C8   C9   N1   C2   180.00   0.0  0
 CTZ  CONST_25  C5   N4   C3   C2   180.00   0.0  0
 CTZ  CONST_26  C9   N4   C3   C2     0.00   0.0  0
 CTZ  CONST_27  C8   C9   N4   C3   180.00   0.0  0
 CTZ  CONST_28  C8   C9   N4   C5     0.00   0.0  0
 CTZ  CONST_29  C13  C12  C11  C10  180.00   0.0  0
 CTZ  CONST_30  C15  C16  C11  C10  180.00   0.0  0
 CTZ  CONST_31  O17  C14  C13  C12  180.00   0.0  0
 CTZ  CONST_32  O17  C14  C15  C16  180.00   0.0  0
 CTZ  CONST_33  O25  C22  C21  C20  180.00   0.0  0
 CTZ  CONST_34  O25  C22  C23  C24  180.00   0.0  0
 CTZ  CONST_35  C29  C28  C27  C26  180.00   0.0  0
 CTZ  CONST_36  C31  C32  C27  C26  180.00   0.0  0
 CTZ  CONST_37  O18  C3   N4   C5     0.00   0.0  0
 CTZ  CONST_38  O18  C3   N4   C9   180.00   0.0  0
 CTZ  CONST_39  H20  C20  C19  C6     0.00   0.0  0
 CTZ  CONST_40  H24  C24  C19  C6     0.00   0.0  0
 CTZ  CONST_41  H13  C13  C12  C11  180.00   0.0  0
 CTZ  CONST_42  H15  C15  C16  C11  180.00   0.0  0
 CTZ  CONST_43  H16  C16  C11  C12  180.00   0.0  0
 CTZ  CONST_44  H12  C12  C13  C14  180.00   0.0  0
 CTZ  CONST_45  H21  C21  C20  C19  180.00   0.0  0
 CTZ  CONST_46  H23  C23  C24  C19  180.00   0.0  0
 CTZ  CONST_47  H29  C29  C28  C27  180.00   0.0  0
 CTZ  CONST_48  H31  C31  C32  C27  180.00   0.0  0
 CTZ  CONST_49  H32  C32  C27  C28  180.00   0.0  0
 CTZ  CONST_50  H30  C30  C29  C28  180.00   0.0  0
 CTZ  CONST_51  H28  C28  C29  C30  180.00   0.0  0
 CTZ  Var_01    C20  C19  C6   C5   165.49  30.0  2
 CTZ  Var_02    C12  C11  C10  C2    90.94  30.0  2
 CTZ  Var_03    C27  C26  C8   N7    -3.70  30.0  3
 CTZ  Var_04    C28  C27  C26  C8    82.22  30.0  2

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
 CTZ  chir_01  C2  C3  N1  O33  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
 CTZ  plan-1  C10  0.020
 CTZ  plan-1  C11  0.020
 CTZ  plan-1  C12  0.020
 CTZ  plan-1  C13  0.020
 CTZ  plan-1  C14  0.020
 CTZ  plan-1  C15  0.020
 CTZ  plan-1  C16  0.020
 CTZ  plan-1  O17  0.020
 CTZ  plan-1  H12  0.020
 CTZ  plan-1  H13  0.020
 CTZ  plan-1  H15  0.020
 CTZ  plan-1  H16  0.020
 CTZ  plan-2  C6   0.020
 CTZ  plan-2  C19  0.020
 CTZ  plan-2  C20  0.020
 CTZ  plan-2  C21  0.020
 CTZ  plan-2  C22  0.020
 CTZ  plan-2  C23  0.020
 CTZ  plan-2  C24  0.020
 CTZ  plan-2  O25  0.020
 CTZ  plan-2  H20  0.020
 CTZ  plan-2  H21  0.020
 CTZ  plan-2  H23  0.020
 CTZ  plan-2  H24  0.020
 CTZ  plan-3  C26  0.020
 CTZ  plan-3  C27  0.020
 CTZ  plan-3  C28  0.020
 CTZ  plan-3  C29  0.020
 CTZ  plan-3  C30  0.020
 CTZ  plan-3  C31  0.020
 CTZ  plan-3  C32  0.020
 CTZ  plan-3  H28  0.020
 CTZ  plan-3  H29  0.020
 CTZ  plan-3  H30  0.020
 CTZ  plan-3  H31  0.020
 CTZ  plan-3  H32  0.020
 CTZ  plan-4  N1   0.020
 CTZ  plan-4  C2   0.020
 CTZ  plan-4  C3   0.020
 CTZ  plan-4  N4   0.020
 CTZ  plan-4  C5   0.020
 CTZ  plan-4  C6   0.020
 CTZ  plan-4  N7   0.020
 CTZ  plan-4  C8   0.020
 CTZ  plan-4  C9   0.020
 CTZ  plan-4  O18  0.020
 CTZ  plan-4  C19  0.020
 CTZ  plan-4  C26  0.020
 CTZ  plan-4  H5   0.020

