# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 20 02:16:20 2020
#   Inital geometry file: a 142 line input string
#   Ligand name: (3~{S},14~{E})-19-chloranyl-~{N}-(1-cyanocyclopropyl)-5-oxidanylidene-12,17-dioxa-4-azatricyclo[16.2.2.0^{6,11}]docosa-1(21),6(11),7,9,14,18(22),19-heptaene-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1cc2C[C@H](NC(=O)c3ccccc3OC\C=C\COc1cc2)C(=O)NC4(CC4)C#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
 C3E  C3E  (3~{S},14~{E})-19-chloranyl-~{N}-(1-cyanocyclopropyl)-5-oxidanylidene-12,17-dioxa-4-azatricyclo[16.2.2.0^{6,11}]docosa-1(21),6(11),7,9,14,18(22),19-heptaene-3-carboxamide  ligand  54  32  .  2022-09-16  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_C3E
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
 C3E  CL1  CL  CL    0  -0.111   3.4814   1.6081  -2.3434
 C3E  CAZ  C   C     0  -0.107   2.3632   1.9142  -1.0608
 C3E  CD2  C   C1    0  -0.289   1.0110   1.6879  -1.2648
 C3E  CG   C   C     0   0.147   0.1012   1.9120  -0.2411
 C3E  CB   C   CH2   0  -0.550  -1.3566   1.6017  -0.4319
 C3E  CD1  C   C1    0  -0.286   0.5747   2.3882   0.9787
 C3E  CAM  C   C1    0  -0.315   1.9255   2.6148   1.1787
 C3E  CBB  C   C     0   0.411   2.8419   2.3724   0.1616
 C3E  OAV  O   O2    0  -0.487   4.1716   2.5774   0.3291
 C3E  CAO  C   CH2   0  -0.236   4.8158   1.6670   1.2343
 C3E  CAF  C   C1    0  -0.256   4.5979   0.2540   0.8042
 C3E  CAG  C   C1    0  -0.199   3.8917  -0.6178   1.5122
 C3E  CAP  C   CH2   0  -0.237   3.5757  -1.9958   1.0375
 C3E  OAW  O   O2    0  -0.460   2.1553  -2.0866   1.0186
 C3E  CBC  C   CR6   0   0.398   1.5576  -3.0368   0.2843
 C3E  CAJ  C   CR16  0  -0.382   2.2086  -4.1270  -0.2850
 C3E  CAH  C   CR16  0  -0.241   1.4894  -5.0354  -1.0536
 C3E  CAI  C   CR16  0  -0.275   0.1310  -4.8692  -1.2695
 C3E  CAK  C   CR16  0  -0.244  -0.5162  -3.7790  -0.7001
 C3E  CBD  C   CR6   0  -0.190   0.1825  -2.8716   0.0810
 C3E  CAX  C   C     0   0.525  -0.5377  -1.7442   0.7523
 C3E  OAB  O   O     0  -0.474  -0.7280  -1.7256   1.9570
 C3E  N    N   NH1   0  -0.602  -0.9675  -0.7871  -0.0872
 C3E  CA   C   CH1   0  -0.221  -1.7595   0.3301   0.3359
 C3E  C    C   C     0   0.570  -3.2452   0.0384   0.1256
 C3E  O    O   O     0  -0.448  -3.6452  -0.7992  -0.6567
 C3E  NAU  N   NH1   0  -0.666  -4.0773   0.8115   0.8592
 C3E  CBF  C   CT    0   0.087  -5.4858   0.7258   0.7155
 C3E  CAE  C   CSP   0   0.115  -6.0029   1.3034  -0.5023
 C3E  NAA  N   NS    0  -0.264  -6.4083   1.7650  -1.4759
 C3E  CAQ  C   CH2   0  -0.471  -6.3348   0.8395   1.9555
 C3E  CAR  C   CH2   0  -0.450  -6.2172  -0.4714   1.2713
 C3E  H1   H   H     0   0.273   0.6698   1.3213  -2.2247
 C3E  H2   H   HCH2  0   0.281  -1.9677   2.4360  -0.0818
 C3E  H3   H   HCH2  0   0.279  -1.5813   1.4715  -1.4933
 C3E  H4   H   H     0   0.258  -0.1188   2.5787   1.7892
 C3E  H5   H   H     0   0.276   2.2757   2.9840   2.1346
 C3E  H6   H   HCH2  0   0.257   5.8707   1.9410   1.2059
 C3E  H7   H   HCH2  0   0.235   4.4553   1.8198   2.2564
 C3E  H8   H   H     0   0.254   4.9948  -0.0282  -0.1667
 C3E  H9   H   H     0   0.258   3.4824  -0.3307   2.4767
 C3E  H10  H   HCH2  0   0.240   3.9920  -2.1585   0.0385
 C3E  H11  H   HCH2  0   0.241   3.9909  -2.7590   1.7051
 C3E  H12  H   HCR6  0   0.283   3.2691  -4.2834  -0.1388
 C3E  H13  H   HCR6  0   0.265   2.0082  -5.8799  -1.4880
 C3E  H14  H   HCR6  0   0.258  -0.4216  -5.5768  -1.8722
 C3E  H15  H   HCR6  0   0.262  -1.5778  -3.6338  -0.8614
 C3E  H16  H   HNH1  0   0.409  -0.7882  -0.8991  -1.0729
 C3E  H17  H   HCH1  0   0.297  -1.5773   0.4910   1.4007
 C3E  H18  H   HNH1  0   0.418  -3.7045   1.5380   1.4517
 C3E  H19  H   HCH2  0   0.294  -5.7901   0.9927   2.8780
 C3E  H20  H   HCH2  0   0.291  -7.2609   1.3918   1.8747
 C3E  H21  H   HCH2  0   0.287  -7.0625  -0.8406   0.7069
 C3E  H22  H   HCH2  0   0.291  -5.5943  -1.2343   1.7180

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
 C3E  CAR  CAQ  single    1.483  0.020  1.483
 C3E  CAR  CBF  single    1.509  0.020  1.509
 C3E  CAQ  CBF  single    1.507  0.020  1.507
 C3E  NAA  CAE  triple    1.151  0.020  1.151
 C3E  CAE  CBF  single    1.444  0.020  1.444
 C3E  CBF  NAU  single    1.418  0.020  1.418
 C3E  O    C    double    1.214  0.020  1.214
 C3E  NAU  C    single    1.352  0.020  1.352
 C3E  C    CA   single    1.529  0.020  1.529
 C3E  CAK  CAI  aromatic  1.390  0.020  1.390
 C3E  CAK  CBD  single    1.386  0.020  1.386
 C3E  CAI  CAH  aromatic  1.385  0.020  1.385
 C3E  CA   N    single    1.433  0.020  1.433
 C3E  CA   CB   single    1.539  0.020  1.539
 C3E  N    CAX  single    1.344  0.020  1.344
 C3E  CAX  OAB  double    1.220  0.020  1.220
 C3E  CAX  CBD  single    1.497  0.020  1.497
 C3E  CBD  CBC  aromatic  1.400  0.020  1.400
 C3E  CAH  CAJ  aromatic  1.390  0.020  1.390
 C3E  CB   CG   single    1.503  0.020  1.503
 C3E  CBC  CAJ  single    1.392  0.020  1.392
 C3E  CBC  OAW  single    1.341  0.020  1.341
 C3E  CG   CD1  aromatic  1.392  0.020  1.392
 C3E  CG   CD2  aromatic  1.388  0.020  1.388
 C3E  OAW  CAP  single    1.423  0.020  1.423
 C3E  CD1  CAM  aromatic  1.384  0.020  1.384
 C3E  CD2  CAZ  aromatic  1.386  0.020  1.386
 C3E  CAP  CAG  single    1.491  0.020  1.491
 C3E  CAM  CBB  aromatic  1.390  0.020  1.390
 C3E  CAZ  CBB  aromatic  1.390  0.020  1.390
 C3E  CAZ  CL1  single    1.729  0.020  1.729
 C3E  CAG  CAF  double    1.327  0.020  1.327
 C3E  CBB  OAV  single    1.356  0.020  1.356
 C3E  CAF  CAO  single    1.493  0.020  1.493
 C3E  OAV  CAO  single    1.436  0.020  1.436
 C3E  CD2  H1   single    0.930  0.020  1.080
 C3E  CB   H2   single    0.970  0.020  1.090
 C3E  CB   H3   single    0.970  0.020  1.090
 C3E  CD1  H4   single    0.930  0.020  1.080
 C3E  CAM  H5   single    0.930  0.020  1.080
 C3E  CAO  H6   single    0.970  0.020  1.090
 C3E  CAO  H7   single    0.970  0.020  1.090
 C3E  CAF  H8   single    0.930  0.020  1.080
 C3E  CAG  H9   single    0.930  0.020  1.080
 C3E  CAP  H10  single    0.970  0.020  1.090
 C3E  CAP  H11  single    0.970  0.020  1.090
 C3E  CAJ  H12  single    0.930  0.020  1.080
 C3E  CAH  H13  single    0.930  0.020  1.080
 C3E  CAI  H14  single    0.930  0.020  1.080
 C3E  CAK  H15  single    0.930  0.020  1.080
 C3E  N    H16  single    0.860  0.020  1.020
 C3E  CA   H17  single    0.970  0.020  1.090
 C3E  NAU  H18  single    0.860  0.020  1.020
 C3E  CAQ  H19  single    0.970  0.020  1.090
 C3E  CAQ  H20  single    0.970  0.020  1.090
 C3E  CAR  H21  single    0.970  0.020  1.090
 C3E  CAR  H22  single    0.970  0.020  1.090

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
 C3E  CBB  CAZ  CD2  121.27  3.000
 C3E  CBB  CAZ  CL1  119.20  3.000
 C3E  CD2  CAZ  CL1  119.53  3.000
 C3E  H1   CD2  CG   120.14  3.000
 C3E  H1   CD2  CAZ  119.55  3.000
 C3E  CG   CD2  CAZ  120.31  3.000
 C3E  CD1  CG   CB   120.79  3.000
 C3E  CD1  CG   CD2  118.58  3.000
 C3E  CB   CG   CD2  120.60  3.000
 C3E  H3   CB   H2   106.70  3.000
 C3E  H3   CB   CA   109.41  3.000
 C3E  H2   CB   CA   108.96  3.000
 C3E  H3   CB   CG   110.33  3.000
 C3E  H2   CB   CG   110.15  3.000
 C3E  CA   CB   CG   111.18  3.000
 C3E  H4   CD1  CAM  119.19  3.000
 C3E  H4   CD1  CG   119.85  3.000
 C3E  CAM  CD1  CG   120.96  3.000
 C3E  H5   CAM  CBB  119.47  3.000
 C3E  H5   CAM  CD1  119.93  3.000
 C3E  CBB  CAM  CD1  120.59  3.000
 C3E  OAV  CBB  CAM  121.98  3.000
 C3E  OAV  CBB  CAZ  119.74  3.000
 C3E  CAM  CBB  CAZ  118.27  3.000
 C3E  CAO  OAV  CBB  114.95  3.000
 C3E  H7   CAO  H6   107.93  3.000
 C3E  H7   CAO  CAF  110.68  3.000
 C3E  H6   CAO  CAF  111.81  3.000
 C3E  H7   CAO  OAV  110.62  3.000
 C3E  H6   CAO  OAV  104.97  3.000
 C3E  CAF  CAO  OAV  110.66  3.000
 C3E  H8   CAF  CAG  120.05  3.000
 C3E  H8   CAF  CAO  116.75  3.000
 C3E  CAG  CAF  CAO  123.09  3.000
 C3E  H9   CAG  CAP  116.55  3.000
 C3E  H9   CAG  CAF  120.04  3.000
 C3E  CAP  CAG  CAF  123.37  3.000
 C3E  H11  CAP  H10  107.96  3.000
 C3E  H11  CAP  OAW  109.99  3.000
 C3E  H10  CAP  OAW  110.98  3.000
 C3E  H11  CAP  CAG  111.68  3.000
 C3E  H10  CAP  CAG  110.33  3.000
 C3E  OAW  CAP  CAG  105.94  3.000
 C3E  CBC  OAW  CAP  119.81  3.000
 C3E  CBD  CBC  CAJ  119.52  3.000
 C3E  CAJ  CBC  OAW  124.78  3.000
 C3E  CBD  CBC  OAW  115.70  3.000
 C3E  H12  CAJ  CAH  119.16  3.000
 C3E  H12  CAJ  CBC  121.10  3.000
 C3E  CAH  CAJ  CBC  119.73  3.000
 C3E  H13  CAH  CAI  120.08  3.000
 C3E  H13  CAH  CAJ  118.93  3.000
 C3E  CAI  CAH  CAJ  120.99  3.000
 C3E  H14  CAI  CAK  120.24  3.000
 C3E  H14  CAI  CAH  120.62  3.000
 C3E  CAK  CAI  CAH  119.14  3.000
 C3E  H15  CAK  CBD  119.34  3.000
 C3E  H15  CAK  CAI  120.02  3.000
 C3E  CBD  CAK  CAI  120.63  3.000
 C3E  CAX  CBD  CAK  120.21  3.000
 C3E  CAX  CBD  CBC  119.77  3.000
 C3E  CAK  CBD  CBC  119.98  3.000
 C3E  N    CAX  OAB  123.80  3.000
 C3E  OAB  CAX  CBD  121.97  3.000
 C3E  N    CAX  CBD  114.22  3.000
 C3E  H16  N    CA   118.26  3.000
 C3E  H16  N    CAX  118.35  3.000
 C3E  CA   N    CAX  123.20  3.000
 C3E  H17  CA   C    108.93  3.000
 C3E  H17  CA   N    108.08  3.000
 C3E  C    CA   N    110.35  3.000
 C3E  H17  CA   CB   108.72  3.000
 C3E  N    CA   CB   110.61  3.000
 C3E  C    CA   CB   110.09  3.000
 C3E  NAU  C    O    122.78  3.000
 C3E  NAU  C    CA   114.48  3.000
 C3E  O    C    CA   122.72  3.000
 C3E  H18  NAU  CBF  118.03  3.000
 C3E  H18  NAU  C    120.20  3.000
 C3E  CBF  NAU  C    121.43  3.000
 C3E  CAR  CBF  CAQ   58.92  3.000
 C3E  CAQ  CBF  CAE  117.52  3.000
 C3E  CAR  CBF  CAE  117.04  3.000
 C3E  CAE  CBF  NAU  114.65  3.000
 C3E  CAQ  CBF  NAU  118.13  3.000
 C3E  CAR  CBF  NAU  119.46  3.000
 C3E  NAA  CAE  CBF  180.00  3.000
 C3E  H20  CAQ  H19  114.99  3.000
 C3E  H20  CAQ  CAR  119.00  3.000
 C3E  H19  CAQ  CAR  118.58  3.000
 C3E  H20  CAQ  CBF  117.35  3.000
 C3E  H19  CAQ  CBF  115.37  3.000
 C3E  CAR  CAQ  CBF   60.60  3.000
 C3E  H22  CAR  H21  115.15  3.000
 C3E  H22  CAR  CAQ  118.59  3.000
 C3E  H21  CAR  CAQ  118.72  3.000
 C3E  H22  CAR  CBF  115.63  3.000
 C3E  H21  CAR  CBF  117.22  3.000
 C3E  CAQ  CAR  CBF   60.48  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
 C3E  CONST_01  CD1  CG   CD2  CAZ     0.00   0.0  0
 C3E  CONST_02  CD1  CAM  CBB  CAZ     0.00   0.0  0
 C3E  CONST_03  CAM  CD1  CG   CD2     0.00   0.0  0
 C3E  CONST_04  CAM  CBB  CAZ  CD2     0.00   0.0  0
 C3E  CONST_05  CBB  CAM  CD1  CG      0.00   0.0  0
 C3E  CONST_06  CBB  CAZ  CD2  CG      0.00   0.0  0
 C3E  CONST_07  CAI  CAK  CBD  CBC     0.00   0.0  0
 C3E  CONST_08  CAI  CAH  CAJ  CBC     0.00   0.0  0
 C3E  CONST_09  CAK  CAI  CAH  CAJ     0.00   0.0  0
 C3E  CONST_10  CAK  CBD  CBC  CAJ     0.00   0.0  0
 C3E  CONST_11  CBD  CAK  CAI  CAH     0.00   0.0  0
 C3E  CONST_12  CBD  CBC  CAJ  CAH     0.00   0.0  0
 C3E  CONST_13  CA   N    CAX  CBD   180.00   0.0  0
 C3E  CONST_14  CG   CD2  CAZ  CL1   180.00   0.0  0
 C3E  CONST_15  CAM  CBB  CAZ  CL1   180.00   0.0  0
 C3E  CONST_16  OAV  CBB  CAZ  CL1     0.00   0.0  0
 C3E  CONST_17  CA   N    CAX  OAB     0.00   0.0  0
 C3E  CONST_18  H5   CAM  CBB  CAZ   180.00   0.0  0
 C3E  CONST_19  H4   CD1  CG   CD2   180.00   0.0  0
 C3E  CONST_20  H1   CD2  CG   CB      0.00   0.0  0
 C3E  CONST_21  H12  CAJ  CBC  OAW     0.00   0.0  0
 C3E  CONST_22  H15  CAK  CBD  CBC   180.00   0.0  0
 C3E  CONST_23  H13  CAH  CAJ  CBC   180.00   0.0  0
 C3E  CONST_24  H14  CAI  CAH  CAJ   180.00   0.0  0
 C3E  CONST_25  H16  N    CAX  CBD     0.00   0.0  0
 C3E  CONST_26  CBF  NAU  C    CA    180.00   0.0  0
 C3E  CONST_27  CBF  NAU  C    O       0.00   0.0  0
 C3E  CONST_28  H18  NAU  C    CA      0.00   0.0  0
 C3E  Var_01    CAP  CAG  CAF  CAO   174.81   0.0  0
 C3E  Var_02    CA   CB   CG   CD2   106.08  30.0  1
 C3E  Var_03    CAF  CAO  OAV  CBB    56.29  30.0  1
 C3E  Var_04    CAG  CAF  CAO  OAV  -114.20  30.0  1
 C3E  Var_05    OAW  CAP  CAG  CAF  -121.12  30.0  1
 C3E  Var_06    CBD  CBC  OAW  CAP  -166.14  30.0  1
 C3E  Var_07    N    CAX  CBD  CBC   111.12  30.0  1
 C3E  Var_08    CAQ  CAR  CBF  NAU   106.96  30.0  1
 C3E  Var_09    H8   CAF  CAG  CAP    -1.18   0.0  0
 C3E  Var_10    H19  CAQ  CAR  CBF  -104.67  30.0  1
 C3E  Var_11    CAR  CBF  NAU  C      73.42  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
 C3E  chir_01  CA   C    N    CB   negativ
 C3E  chir_02  CBF  CAQ  CAE  NAU  both

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
 C3E  plan-1  CL1  0.020
 C3E  plan-1  CAZ  0.020
 C3E  plan-1  CD2  0.020
 C3E  plan-1  CG   0.020
 C3E  plan-1  CB   0.020
 C3E  plan-1  CD1  0.020
 C3E  plan-1  CAM  0.020
 C3E  plan-1  CBB  0.020
 C3E  plan-1  OAV  0.020
 C3E  plan-1  H1   0.020
 C3E  plan-1  H4   0.020
 C3E  plan-1  H5   0.020
 C3E  plan-2  OAW  0.020
 C3E  plan-2  CBC  0.020
 C3E  plan-2  CAJ  0.020
 C3E  plan-2  CAH  0.020
 C3E  plan-2  CAI  0.020
 C3E  plan-2  CAK  0.020
 C3E  plan-2  CBD  0.020
 C3E  plan-2  CAX  0.020
 C3E  plan-2  H12  0.020
 C3E  plan-2  H13  0.020
 C3E  plan-2  H14  0.020
 C3E  plan-2  H15  0.020
 C3E  plan-3  CBD  0.020
 C3E  plan-3  CAX  0.020
 C3E  plan-3  OAB  0.020
 C3E  plan-3  N    0.020
 C3E  plan-3  CA   0.020
 C3E  plan-3  H16  0.020
 C3E  plan-4  CA   0.020
 C3E  plan-4  C    0.020
 C3E  plan-4  O    0.020
 C3E  plan-4  NAU  0.020
 C3E  plan-4  CBF  0.020
 C3E  plan-4  H18  0.020
 C3E  plan-5  CAO  0.020
 C3E  plan-5  CAF  0.020
 C3E  plan-5  CAG  0.020
 C3E  plan-5  CAP  0.020
 C3E  plan-5  H8   0.020
 C3E  plan-5  H9   0.020

