# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 06:41:08 2022
#   Inital geometry file: a 66 line input string
#   Ligand name: 4-methyl-8-oxidanyl-2,3,7,13-tetrazatricyclo[7.4.0.0^{2,6}]trideca-1(9),3,5,7,10,12-hexaene-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1nn2c3ncccc3c(O)nc2c1C#N
#
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
 HR0  HR0  "5-hydroxy-2-methylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-3-carbonitrile"
  ligand  24  17  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HR0
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
 HR0  C10   C  CR66  0  -0.183   9.2240  -1.9427  20.8622
 HR0  C11   C  CR6   0   0.477  10.0451  -0.8177  20.4812
 HR0  C14   C  CR56  0   0.658   9.9420  -1.4077  18.3096
 HR0  C2    C  CR5   0   0.356   9.3998  -2.5474  16.4708
 HR0  C5    C  CR66  0   0.562   8.7710  -2.8031  19.8511
 HR0  C7    C  CR16  0  -0.034   7.6782  -4.1316  21.3043
 HR0  C8    C  CR16  0  -0.325   8.0627  -3.3540  22.3970
 HR0  C9    C  CR16  0  -0.142   8.8459  -2.2441  22.1729
 HR0  C15   C  CR5   0  -0.314  10.1255  -1.4184  16.9344
 HR0  C16   C  CSP   0  -0.023  10.8844  -0.5123  16.1774
 HR0  N3    N  N     0  -0.290   8.8234  -3.1804  17.4637
 HR0  N4    N  N     0  -0.456   9.1550  -2.4890  18.5693
 HR0  N6    N  N     0  -0.409   8.0201  -3.8690  20.0554
 HR0  N13   N  N     0  -0.479  10.3884  -0.5689  19.2590
 HR0  N17   N  NS    0  -0.254  11.5080   0.2188  15.5377
 HR0  O12   O  OH1   0  -0.569  10.4415  -0.0327  21.4572
 HR0  H11   H  HCH3  0   0.265   8.6640  -3.9043  15.0054
 HR0  H12   H  HCH3  0   0.263   8.7920  -2.2296  14.4547
 HR0  H13   H  HCH3  0   0.263  10.2431  -3.2046  14.6269
 HR0  H71   H  HCR6  0   0.289   7.0625  -5.0105  21.4558
 HR0  H81   H  HCR6  0   0.291   7.7483  -3.6266  23.3939
 HR0  H91   H  HCR6  0   0.297   9.1638  -1.6188  22.9959
 HR0  H121  H  HOH1  0   0.495  10.9836   0.6913  21.1082
 HR0  C1    C  CH3   0  -0.739   9.2654  -3.0002  15.0640

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
 HR0  C1   C2    single    1.484  0.020  1.484
 HR0  N17  C16   triple    1.154  0.020  1.154
 HR0  C16  C15   single    1.404  0.020  1.404
 HR0  C2   C15   aromatic  1.420  0.020  1.420
 HR0  C2   N3    aromatic  1.311  0.020  1.311
 HR0  C15  C14   aromatic  1.387  0.020  1.387
 HR0  N3   N4    aromatic  1.345  0.020  1.345
 HR0  C14  N4    aromatic  1.362  0.020  1.362
 HR0  C14  N13   aromatic  1.343  0.020  1.343
 HR0  N4   C5    aromatic  1.374  0.020  1.374
 HR0  N13  C11   aromatic  1.294  0.020  1.294
 HR0  C5   N6    aromatic  1.320  0.020  1.320
 HR0  C5   C10   aromatic  1.403  0.020  1.403
 HR0  N6   C7    aromatic  1.321  0.020  1.321
 HR0  C11  C10   aromatic  1.444  0.020  1.444
 HR0  C11  O12   single    1.314  0.020  1.314
 HR0  C10  C9    aromatic  1.397  0.020  1.397
 HR0  C7   C8    aromatic  1.395  0.020  1.395
 HR0  C9   C8    aromatic  1.377  0.020  1.377
 HR0  C1   H11   single    0.970  0.020  1.090
 HR0  C1   H12   single    0.970  0.020  1.090
 HR0  C1   H13   single    0.970  0.020  1.090
 HR0  C7   H71   single    0.930  0.020  1.080
 HR0  C8   H81   single    0.930  0.020  1.080
 HR0  C9   H91   single    0.930  0.020  1.080
 HR0  O12  H121  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
 HR0  C9    C10  C5   117.16  3.000
 HR0  C9    C10  C11  124.72  3.000
 HR0  C5    C10  C11  118.12  3.000
 HR0  O12   C11  N13  120.46  3.000
 HR0  O12   C11  C10  116.17  3.000
 HR0  N13   C11  C10  123.37  3.000
 HR0  N13   C14  N4   123.56  3.000
 HR0  N13   C14  C15  131.41  3.000
 HR0  N4    C14  C15  105.03  3.000
 HR0  N3    C2   C15  111.18  3.000
 HR0  N3    C2   C1   122.06  3.000
 HR0  C15   C2   C1   126.75  3.000
 HR0  N6    C5   N4   119.20  3.000
 HR0  N6    C5   C10  124.58  3.000
 HR0  N4    C5   C10  116.22  3.000
 HR0  H71   C7   N6   116.13  3.000
 HR0  H71   C7   C8   119.94  3.000
 HR0  N6    C7   C8   123.93  3.000
 HR0  H81   C8   C9   121.28  3.000
 HR0  H81   C8   C7   120.13  3.000
 HR0  C9    C8   C7   118.60  3.000
 HR0  H91   C9   C8   120.63  3.000
 HR0  H91   C9   C10  120.65  3.000
 HR0  C8    C9   C10  118.72  3.000
 HR0  C16   C15  C2   127.85  3.000
 HR0  C2    C15  C14  105.20  3.000
 HR0  C16   C15  C14  126.95  3.000
 HR0  N17   C16  C15  180.00  3.000
 HR0  N4    N3   C2   105.42  3.000
 HR0  N3    N4   C5   125.46  3.000
 HR0  C5    N4   C14  121.37  3.000
 HR0  N3    N4   C14  113.18  3.000
 HR0  C7    N6   C5   117.01  3.000
 HR0  C14   N13  C11  117.36  3.000
 HR0  H121  O12  C11  110.33  3.000
 HR0  H13   C1   H12  107.33  3.000
 HR0  H13   C1   H11  108.57  3.000
 HR0  H12   C1   H11  108.50  3.000
 HR0  H13   C1   C2   110.86  3.000
 HR0  H12   C1   C2   110.70  3.000
 HR0  H11   C1   C2   110.78  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
 HR0  CONST_01  N3   N4   C5   C10   180.00   0.0  0
 HR0  CONST_02  C14  N4   C5   C10     0.00   0.0  0
 HR0  CONST_03  C7   N6   C5   C10     0.00   0.0  0
 HR0  CONST_04  C14  N13  C11  C10     0.00   0.0  0
 HR0  CONST_05  C7   C8   C9   C10     0.00   0.0  0
 HR0  CONST_06  C15  C14  N13  C11   180.00   0.0  0
 HR0  CONST_07  N4   C14  N13  C11     0.00   0.0  0
 HR0  CONST_08  N4   C5   C10  C11     0.00   0.0  0
 HR0  CONST_09  N6   C5   C10  C11   180.00   0.0  0
 HR0  CONST_10  C8   C9   C10  C11   180.00   0.0  0
 HR0  CONST_11  N3   C2   C15  C14     0.00   0.0  0
 HR0  CONST_12  C2   N3   N4   C14     0.00   0.0  0
 HR0  CONST_13  N6   C5   N4   C14   180.00   0.0  0
 HR0  CONST_14  N4   C14  C15  C2      0.00   0.0  0
 HR0  CONST_15  N13  C14  C15  C2    180.00   0.0  0
 HR0  CONST_16  C5   N4   N3   C2    180.00   0.0  0
 HR0  CONST_17  C15  C14  N4   C5    180.00   0.0  0
 HR0  CONST_18  N13  C14  N4   C5      0.00   0.0  0
 HR0  CONST_19  C8   C7   N6   C5      0.00   0.0  0
 HR0  CONST_20  N13  C11  C10  C5      0.00   0.0  0
 HR0  CONST_21  C8   C9   C10  C5      0.00   0.0  0
 HR0  CONST_22  N4   C5   N6   C7    180.00   0.0  0
 HR0  CONST_23  N4   C5   C10  C9    180.00   0.0  0
 HR0  CONST_24  N6   C5   C10  C9      0.00   0.0  0
 HR0  CONST_25  N13  C11  C10  C9    180.00   0.0  0
 HR0  CONST_26  N6   C7   C8   C9      0.00   0.0  0
 HR0  CONST_27  N4   N3   C2   C15     0.00   0.0  0
 HR0  CONST_28  N3   N4   C14  C15     0.00   0.0  0
 HR0  CONST_29  N13  C14  N4   N3    180.00   0.0  0
 HR0  CONST_30  N6   C5   N4   N3      0.00   0.0  0
 HR0  CONST_31  C1   C2   C15  C14   180.00   0.0  0
 HR0  CONST_32  O12  C11  N13  C14   180.00   0.0  0
 HR0  CONST_33  N4   N3   C2   C1    180.00   0.0  0
 HR0  CONST_34  O12  C11  C10  C5    180.00   0.0  0
 HR0  CONST_35  O12  C11  C10  C9      0.00   0.0  0
 HR0  CONST_36  N3   C2   C15  C16   180.00   0.0  0
 HR0  CONST_37  N4   C14  C15  C16   180.00   0.0  0
 HR0  CONST_38  N13  C14  C15  C16     0.00   0.0  0
 HR0  CONST_39  H81  C8   C9   C10   180.00   0.0  0
 HR0  CONST_40  H91  C9   C10  C11     0.00   0.0  0
 HR0  CONST_41  H71  C7   N6   C5    180.00   0.0  0
 HR0  CONST_42  H91  C9   C10  C5    180.00   0.0  0
 HR0  CONST_43  H91  C9   C8   C7    180.00   0.0  0
 HR0  CONST_44  H71  C7   C8   C9    180.00   0.0  0
 HR0  CONST_45  H81  C8   C7   N6    180.00   0.0  0
 HR0  Var_01    H11  C1   C2   C15   179.09  30.0  2
 HR0  Var_02    H12  C1   C2   C15   -60.50  30.0  2
 HR0  Var_03    H13  C1   C2   C15    58.49  30.0  2
 HR0  Var_04    H11  C1   C2   N3     -1.29  30.0  2
 HR0  Var_05    H12  C1   C2   N3    119.12  30.0  2
 HR0  Var_06    H13  C1   C2   N3   -121.89  30.0  2

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
 HR0  plan-1  C14  0.020
 HR0  plan-1  C2   0.020
 HR0  plan-1  C5   0.020
 HR0  plan-1  C15  0.020
 HR0  plan-1  C16  0.020
 HR0  plan-1  N3   0.020
 HR0  plan-1  N4   0.020
 HR0  plan-1  N13  0.020
 HR0  plan-1  N17  0.020
 HR0  plan-1  C1   0.020
 HR0  plan-2  C10  0.020
 HR0  plan-2  C11  0.020
 HR0  plan-2  C5   0.020
 HR0  plan-2  C7   0.020
 HR0  plan-2  C8   0.020
 HR0  plan-2  C9   0.020
 HR0  plan-2  N4   0.020
 HR0  plan-2  N6   0.020
 HR0  plan-2  H71  0.020
 HR0  plan-2  H81  0.020
 HR0  plan-2  H91  0.020

