# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 18:18:51 2020
#   Inital geometry file: a 167 line input string
#   Ligand name: (1R,3S)-1-(3-{[4-(2-fluorophenyl)piperazin-1-yl]methyl}-4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(cc1CN2CCN(CC2)c3ccccc3F)[C@H]4N[C@@H](Cc5c4[nH]c6ccccc56)C(O)=O
#
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
 66R  66R  '(1R,3S)-1-(3-{[4-(2-fluorophenyl)piperazin-1-yl]methyl}-4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid'  ligand  68  38  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_66R
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
 66R  C01  C  CR16   0  -0.328  -7.2956   0.0571   0.2814
 66R  C02  C  CR6    0   0.169  -6.2129  -0.3289  -0.5108
 66R  C03  C  CR6    0   0.502  -6.3652  -1.5169  -1.2328
 66R  C04  C  CR16   0  -0.412  -7.4978  -2.2974  -1.1672
 66R  C05  C  CR16   0  -0.262  -8.5607  -1.8857  -0.3711
 66R  C06  C  CR16   0  -0.260  -8.4570  -0.7039   0.3442
 66R  F07  F  F      0  -0.316  -5.3655  -1.9076  -2.0438
 66R  N08  N  NT     0  -0.499  -5.0391   0.4201  -0.6440
 66R  C09  C  CH2    0  -0.317  -5.1177   1.8250  -0.2927
 66R  C10  C  CH2    0  -0.280  -3.8834   2.5458  -0.8003
 66R  N11  N  NT     0  -0.405  -2.6810   1.9621  -0.2440
 66R  C12  C  CH2    0  -0.282  -2.6034   0.5573  -0.5874
 66R  C13  C  CH2    0  -0.308  -3.8303  -0.1807  -0.0903
 66R  C14  C  CH2    0  -0.334  -1.4994   2.7022  -0.6465
 66R  C15  C  CR6    0   0.024  -0.2683   2.2791   0.1053
 66R  C16  C  CR6    0   0.343  -0.1130   2.5838   1.4663
 66R  C17  C  CR16   0  -0.377   1.0295   2.1631   2.1430
 66R  C18  C  CR16   0  -0.286   2.0117   1.4437   1.4738
 66R  C19  C  CR6    0   0.127   1.8839   1.1362   0.1274
 66R  C20  C  CR16   0  -0.366   0.7358   1.5669  -0.5313
 66R  C21  C  CH1    0  -0.220   2.9682   0.4032  -0.6251
 66R  C22  C  CR5    0   0.304   3.5302  -0.7452   0.1512
 66R  C23  C  CR5    0  -0.019   4.8603  -0.9883   0.3274
 66R  C24  C  CH2    0  -0.504   5.9124  -0.1059  -0.2532
 66R  C25  C  CH1    0  -0.273   5.2901   0.7180  -1.3919
 66R  N26  N  NH1    0  -0.580   4.0259   1.3391  -1.0061
 66R  C27  C  C      0   0.422   5.1759  -0.1060  -2.7003
 66R  O28  O  O      0  -0.595   4.1362   0.0071  -3.3757
 66R  O29  O  OC    -1  -0.610   6.1749  -0.7940  -2.9923
 66R  C30  C  CR5    0   0.038   4.9583  -2.1982   1.0849
 66R  C31  C  CR5    0   0.322   3.6341  -2.6362   1.3286
 66R  N32  N  NR15   0  -0.747   2.7900  -1.7357   0.7424
 66R  C33  C  C1     0  -0.314   3.3605  -3.7983   2.0457
 66R  C34  C  C1     0  -0.289   4.4370  -4.5288   2.5178
 66R  C35  C  C1     0  -0.272   5.7576  -4.1150   2.2829
 66R  C36  C  C1     0  -0.377   6.0256  -2.9585   1.5733
 66R  O37  O  O2     0  -0.457  -1.1037   3.2905   2.0390
 66R  C38  C  CH3    0  -0.437  -0.9829   3.6507   3.3994
 66R  H1   H  HCR6   0   0.274  -7.2335   0.9663   0.8646
 66R  H2   H  HCR6   0   0.276  -7.5557  -3.2064  -1.7527
 66R  H3   H  HCR6   0   0.262  -9.4595  -2.4854  -0.3234
 66R  H4   H  HCR6   0   0.258  -9.2769  -0.3703   0.9666
 66R  H5   H  HCH2   0   0.252  -6.0020   2.2651  -0.7570
 66R  H6   H  HCH2   0   0.210  -5.2006   1.9777   0.7940
 66R  H7   H  HCH2   0   0.193  -3.8838   2.5186  -1.9040
 66R  H8   H  HCH2   0   0.240  -3.9427   3.5959  -0.5039
 66R  H10  H  HCH2   0   0.190  -2.5067   0.4070  -1.6773
 66R  H11  H  HCH2   0   0.245  -1.7209   0.1148  -0.1213
 66R  H12  H  HCH2   0   0.214  -3.8519  -0.1479   1.0092
 66R  H13  H  HCH2   0   0.254  -3.7546  -1.2265  -0.3810
 66R  H14  H  HCH2   0   0.214  -1.3058   2.5982  -1.7277
 66R  H15  H  HCH2   0   0.244  -1.6945   3.7635  -0.4702
 66R  H16  H  HCR6   0   0.276   1.1716   2.3847   3.1920
 66R  H17  H  HCR6   0   0.251   2.8870   1.1192   2.0254
 66R  H18  H  HCR6   0   0.245   0.6122   1.3309  -1.5835
 66R  H19  H  HCH1   0   0.258   2.5257   0.0118  -1.5469
 66R  H20  H  HCH2   0   0.222   6.3238   0.5643   0.5109
 66R  H21  H  HCH2   0   0.231   6.7543  -0.6868  -0.6314
 66R  H22  H  HCH1   0   0.241   5.9739   1.5448  -1.6204
 66R  H23  H  HNH1   0   0.339   4.2035   1.9564  -0.2211
 66R  H26  H  HNR5   0   0.398   1.7849  -1.7675   0.7807
 66R  H27  H  H      0   0.253   2.3432  -4.1227   2.2257
 66R  H28  H  H      0   0.245   4.2562  -5.4377   3.0771
 66R  H29  H  H      0   0.242   6.5757  -4.7138   2.6630
 66R  H30  H  H      0   0.237   7.0482  -2.6466   1.3975
 66R  H31  H  HCH3   0   0.258  -1.8793   4.2124   3.6509
 66R  H32  H  HCH3   0   0.227  -0.9227   2.7750   4.0511
 66R  H33  H  HCH3   0   0.227  -0.1097   4.2835   3.5811

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
 66R  O28  C27  deloc     1.245  0.020  1.245
 66R  C36  C35  aromatic  1.383  0.020  1.383
 66R  C36  C30  aromatic  1.399  0.020  1.399
 66R  C27  O29  deloc     1.248  0.020  1.248
 66R  C27  C25  single    1.550  0.020  1.550
 66R  C35  C34  aromatic  1.404  0.020  1.404
 66R  C24  C25  single    1.537  0.020  1.537
 66R  C24  C23  single    1.491  0.020  1.491
 66R  C25  N26  single    1.460  0.020  1.460
 66R  C30  C23  aromatic  1.431  0.020  1.431
 66R  C30  C31  aromatic  1.416  0.020  1.416
 66R  C23  C22  aromatic  1.364  0.020  1.364
 66R  C34  C33  aromatic  1.384  0.020  1.384
 66R  N26  C21  single    1.463  0.020  1.463
 66R  C31  C33  aromatic  1.393  0.020  1.393
 66R  C31  N32  aromatic  1.366  0.020  1.366
 66R  C22  N32  aromatic  1.371  0.020  1.371
 66R  C22  C21  single    1.496  0.020  1.496
 66R  C21  C19  single    1.510  0.020  1.510
 66R  C18  C19  aromatic  1.387  0.020  1.387
 66R  C18  C17  aromatic  1.389  0.020  1.389
 66R  C19  C20  aromatic  1.392  0.020  1.392
 66R  C17  C16  aromatic  1.393  0.020  1.393
 66R  C20  C15  aromatic  1.386  0.020  1.386
 66R  C16  C15  aromatic  1.403  0.020  1.403
 66R  C16  O37  single    1.345  0.020  1.345
 66R  C15  C14  single    1.503  0.020  1.503
 66R  O37  C38  single    1.412  0.020  1.412
 66R  C14  N11  single    1.451  0.020  1.451
 66R  N11  C10  single    1.448  0.020  1.448
 66R  N11  C12  single    1.448  0.020  1.448
 66R  C10  C09  single    1.517  0.020  1.517
 66R  C12  C13  single    1.516  0.020  1.516
 66R  C09  N08  single    1.450  0.020  1.450
 66R  C13  N08  single    1.459  0.020  1.459
 66R  N08  C02  single    1.399  0.020  1.399
 66R  C02  C01  aromatic  1.396  0.020  1.396
 66R  C02  C03  aromatic  1.398  0.020  1.398
 66R  C01  C06  aromatic  1.390  0.020  1.390
 66R  F07  C03  single    1.345  0.020  1.345
 66R  C03  C04  aromatic  1.377  0.020  1.377
 66R  C06  C05  aromatic  1.385  0.020  1.385
 66R  C04  C05  aromatic  1.390  0.020  1.390
 66R  C01  H1   single    0.930  0.020  1.080
 66R  C04  H2   single    0.930  0.020  1.080
 66R  C05  H3   single    0.930  0.020  1.080
 66R  C06  H4   single    0.930  0.020  1.080
 66R  C09  H5   single    0.970  0.020  1.090
 66R  C09  H6   single    0.970  0.020  1.090
 66R  C10  H7   single    0.970  0.020  1.090
 66R  C10  H8   single    0.970  0.020  1.090
 66R  C12  H10  single    0.970  0.020  1.090
 66R  C12  H11  single    0.970  0.020  1.090
 66R  C13  H12  single    0.970  0.020  1.090
 66R  C13  H13  single    0.970  0.020  1.090
 66R  C14  H14  single    0.970  0.020  1.090
 66R  C14  H15  single    0.970  0.020  1.090
 66R  C17  H16  single    0.930  0.020  1.080
 66R  C18  H17  single    0.930  0.020  1.080
 66R  C20  H18  single    0.930  0.020  1.080
 66R  C21  H19  single    0.970  0.020  1.090
 66R  C24  H20  single    0.970  0.020  1.090
 66R  C24  H21  single    0.970  0.020  1.090
 66R  C25  H22  single    0.970  0.020  1.090
 66R  N26  H23  single    0.890  0.020  1.040
 66R  N32  H26  single    0.860  0.020  1.020
 66R  C33  H27  single    0.930  0.020  1.080
 66R  C34  H28  single    0.930  0.020  1.080
 66R  C35  H29  single    0.930  0.020  1.080
 66R  C36  H30  single    0.930  0.020  1.080
 66R  C38  H31  single    0.970  0.020  1.090
 66R  C38  H32  single    0.970  0.020  1.090
 66R  C38  H33  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
 66R  H1   C01  C06  118.93  3.000
 66R  H1   C01  C02  119.59  3.000
 66R  C06  C01  C02  121.49  3.000
 66R  N08  C02  C03  119.81  3.000
 66R  C03  C02  C01  116.32  3.000
 66R  N08  C02  C01  123.83  3.000
 66R  F07  C03  C04  118.38  3.000
 66R  C04  C03  C02  123.13  3.000
 66R  F07  C03  C02  118.49  3.000
 66R  H2   C04  C05  121.16  3.000
 66R  H2   C04  C03  119.61  3.000
 66R  C05  C04  C03  119.22  3.000
 66R  H3   C05  C06  120.82  3.000
 66R  H3   C05  C04  119.76  3.000
 66R  C06  C05  C04  119.41  3.000
 66R  H4   C06  C05  120.22  3.000
 66R  H4   C06  C01  119.36  3.000
 66R  C05  C06  C01  120.41  3.000
 66R  C13  N08  C09  110.61  3.000
 66R  C13  N08  C02  116.01  3.000
 66R  C09  N08  C02  116.75  3.000
 66R  H6   C09  H5   107.64  3.000
 66R  H6   C09  C10  109.01  3.000
 66R  H5   C09  C10  108.99  3.000
 66R  H6   C09  N08  112.19  3.000
 66R  H5   C09  N08  109.36  3.000
 66R  C10  C09  N08  109.58  3.000
 66R  H8   C10  H7   107.15  3.000
 66R  H8   C10  N11  109.16  3.000
 66R  H7   C10  N11  111.99  3.000
 66R  H8   C10  C09  108.77  3.000
 66R  H7   C10  C09  108.82  3.000
 66R  N11  C10  C09  110.84  3.000
 66R  C14  N11  C12  112.66  3.000
 66R  C12  N11  C10  110.15  3.000
 66R  C14  N11  C10  111.35  3.000
 66R  H11  C12  H10  107.18  3.000
 66R  H11  C12  C13  108.48  3.000
 66R  H10  C12  C13  109.17  3.000
 66R  H11  C12  N11  109.58  3.000
 66R  H10  C12  N11  111.75  3.000
 66R  C13  C12  N11  110.56  3.000
 66R  H13  C13  H12  107.28  3.000
 66R  H13  C13  C12  108.90  3.000
 66R  H12  C13  C12  109.22  3.000
 66R  H13  C13  N08  110.62  3.000
 66R  H12  C13  N08  110.53  3.000
 66R  C12  C13  N08  110.22  3.000
 66R  H15  C14  H14  106.31  3.000
 66R  H15  C14  C15  109.80  3.000
 66R  H14  C14  C15  108.65  3.000
 66R  H15  C14  N11  107.76  3.000
 66R  H14  C14  N11  111.50  3.000
 66R  C15  C14  N11  112.62  3.000
 66R  C20  C15  C16  118.48  3.000
 66R  C16  C15  C14  120.97  3.000
 66R  C20  C15  C14  120.55  3.000
 66R  O37  C16  C17  123.78  3.000
 66R  O37  C16  C15  116.46  3.000
 66R  C17  C16  C15  119.76  3.000
 66R  H16  C17  C18  118.72  3.000
 66R  H16  C17  C16  121.13  3.000
 66R  C18  C17  C16  120.15  3.000
 66R  H17  C18  C19  120.12  3.000
 66R  H17  C18  C17  118.73  3.000
 66R  C19  C18  C17  121.15  3.000
 66R  C21  C19  C20  120.45  3.000
 66R  C20  C19  C18  117.82  3.000
 66R  C21  C19  C18  121.69  3.000
 66R  H18  C20  C19  119.04  3.000
 66R  H18  C20  C15  118.33  3.000
 66R  C19  C20  C15  122.63  3.000
 66R  H19  C21  N26  107.55  3.000
 66R  H19  C21  C22  108.32  3.000
 66R  N26  C21  C22  110.78  3.000
 66R  H19  C21  C19  107.63  3.000
 66R  C22  C21  C19  112.58  3.000
 66R  N26  C21  C19  109.79  3.000
 66R  N32  C22  C23  110.01  3.000
 66R  N32  C22  C21  125.16  3.000
 66R  C23  C22  C21  124.78  3.000
 66R  C30  C23  C24  131.18  3.000
 66R  C30  C23  C22  106.62  3.000
 66R  C24  C23  C22  122.17  3.000
 66R  H21  C24  H20  106.11  3.000
 66R  H21  C24  C25  109.95  3.000
 66R  H20  C24  C25  109.91  3.000
 66R  H21  C24  C23  111.38  3.000
 66R  H20  C24  C23  110.80  3.000
 66R  C25  C24  C23  108.67  3.000
 66R  H22  C25  C27  105.70  3.000
 66R  H22  C25  N26  105.90  3.000
 66R  C27  C25  N26  112.66  3.000
 66R  H22  C25  C24  107.82  3.000
 66R  N26  C25  C24  112.50  3.000
 66R  C27  C25  C24  111.72  3.000
 66R  H23  N26  C25  108.16  3.000
 66R  H23  N26  C21  108.32  3.000
 66R  C25  N26  C21  115.00  3.000
 66R  O29  C27  O28  126.29  3.000
 66R  O29  C27  C25  115.57  3.000
 66R  O28  C27  C25  118.10  3.000
 66R  C36  C30  C31  119.04  3.000
 66R  C31  C30  C23  106.78  3.000
 66R  C36  C30  C23  134.18  3.000
 66R  C33  C31  N32  130.51  3.000
 66R  N32  C31  C30  107.46  3.000
 66R  C33  C31  C30  122.04  3.000
 66R  H26  N32  C31  125.44  3.000
 66R  H26  N32  C22  125.35  3.000
 66R  C31  N32  C22  109.13  3.000
 66R  H27  C33  C34  121.06  3.000
 66R  H27  C33  C31  121.34  3.000
 66R  C34  C33  C31  117.60  3.000
 66R  H28  C34  C35  119.41  3.000
 66R  H28  C34  C33  119.31  3.000
 66R  C35  C34  C33  121.27  3.000
 66R  H29  C35  C36  119.75  3.000
 66R  H29  C35  C34  119.28  3.000
 66R  C36  C35  C34  120.97  3.000
 66R  H30  C36  C35  120.46  3.000
 66R  H30  C36  C30  120.47  3.000
 66R  C35  C36  C30  119.08  3.000
 66R  C38  O37  C16  118.76  3.000
 66R  H33  C38  H32  108.69  3.000
 66R  H33  C38  H31  108.72  3.000
 66R  H32  C38  H31  108.74  3.000
 66R  H33  C38  O37  112.08  3.000
 66R  H32  C38  O37  111.99  3.000
 66R  H31  C38  O37  106.50  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
 66R  CONST_01  C04  C03  C02  C01     0.00   0.0  0
 66R  CONST_02  C04  C05  C06  C01     0.00   0.0  0
 66R  CONST_03  C05  C06  C01  C02     0.00   0.0  0
 66R  CONST_04  C05  C04  C03  C02     0.00   0.0  0
 66R  CONST_05  C06  C01  C02  C03     0.00   0.0  0
 66R  CONST_06  C06  C05  C04  C03     0.00   0.0  0
 66R  CONST_07  C18  C19  C20  C15     0.00   0.0  0
 66R  CONST_08  C18  C17  C16  C15     0.00   0.0  0
 66R  CONST_09  C19  C18  C17  C16     0.00   0.0  0
 66R  CONST_10  C19  C20  C15  C16     0.00   0.0  0
 66R  CONST_11  C20  C19  C18  C17     0.00   0.0  0
 66R  CONST_12  C20  C15  C16  C17     0.00   0.0  0
 66R  CONST_13  C36  C30  C23  C22   180.00   0.0  0
 66R  CONST_14  C31  C30  C23  C22     0.00   0.0  0
 66R  CONST_15  C30  C31  N32  C22     0.00   0.0  0
 66R  CONST_16  C33  C31  N32  C22   180.00   0.0  0
 66R  CONST_17  C35  C36  C30  C23   180.00   0.0  0
 66R  CONST_18  C33  C31  C30  C23   180.00   0.0  0
 66R  CONST_19  N32  C31  C30  C23     0.00   0.0  0
 66R  CONST_20  C31  N32  C22  C23     0.00   0.0  0
 66R  CONST_21  C34  C35  C36  C30     0.00   0.0  0
 66R  CONST_22  N32  C22  C23  C30     0.00   0.0  0
 66R  CONST_23  C34  C33  C31  C30     0.00   0.0  0
 66R  CONST_24  C35  C36  C30  C31     0.00   0.0  0
 66R  CONST_25  C35  C34  C33  C31     0.00   0.0  0
 66R  CONST_26  C36  C30  C31  N32   180.00   0.0  0
 66R  CONST_27  C34  C33  C31  N32   180.00   0.0  0
 66R  CONST_28  C36  C35  C34  C33     0.00   0.0  0
 66R  CONST_29  C36  C30  C31  C33     0.00   0.0  0
 66R  CONST_30  N08  C02  C03  C04   180.00   0.0  0
 66R  CONST_31  N08  C02  C01  C06   180.00   0.0  0
 66R  CONST_32  C21  C19  C20  C15   180.00   0.0  0
 66R  CONST_33  C21  C19  C18  C17   180.00   0.0  0
 66R  CONST_34  F07  C03  C02  C01   180.00   0.0  0
 66R  CONST_35  F07  C03  C04  C05   180.00   0.0  0
 66R  CONST_36  N08  C02  C03  F07     0.00   0.0  0
 66R  CONST_37  C19  C20  C15  C14   180.00   0.0  0
 66R  CONST_38  C17  C16  C15  C14   180.00   0.0  0
 66R  CONST_39  O37  C16  C17  C18   180.00   0.0  0
 66R  CONST_40  O37  C16  C15  C20   180.00   0.0  0
 66R  CONST_41  H3   C05  C06  C01   180.00   0.0  0
 66R  CONST_42  H4   C06  C01  C02   180.00   0.0  0
 66R  CONST_43  H2   C04  C03  C02   180.00   0.0  0
 66R  CONST_44  H1   C01  C02  C03   180.00   0.0  0
 66R  CONST_45  H16  C17  C16  C15   180.00   0.0  0
 66R  CONST_46  H17  C18  C17  C16   180.00   0.0  0
 66R  CONST_47  H18  C20  C15  C16   180.00   0.0  0
 66R  CONST_48  H26  N32  C22  C21     0.00   0.0  0
 66R  CONST_49  H30  C36  C30  C23     0.00   0.0  0
 66R  CONST_50  H29  C35  C36  C30   180.00   0.0  0
 66R  CONST_51  H27  C33  C31  C30   180.00   0.0  0
 66R  CONST_52  H28  C34  C33  C31   180.00   0.0  0
 66R  Var_01    C09  N08  C02  C01   -19.77  30.0  2
 66R  Var_02    C10  C09  N08  C02  -166.58  30.0  1
 66R  Var_03    C12  C13  N08  C02   166.41  30.0  1
 66R  Var_04    N11  C10  C09  N08   -58.37  30.0  1
 66R  Var_05    N11  C12  C13  N08    57.25  30.0  1
 66R  Var_06    C12  N11  C10  C09    58.34  30.0  1
 66R  Var_07    C13  C12  N11  C10   -57.60  30.0  1
 66R  Var_08    C25  C24  C23  C22   -19.34  30.0  1
 66R  Var_09    C15  C14  N11  C10   169.67  30.0  2
 66R  Var_10    C20  C15  C14  N11   109.07  30.0  2
 66R  Var_11    H31  C38  O37  C16   179.74  30.0  3

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
 66R  chir_01  C21  N26  C22  C19  negativ
 66R  chir_02  C25  N26  C24  C27  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
 66R  plan-1  C01  0.020
 66R  plan-1  C02  0.020
 66R  plan-1  C03  0.020
 66R  plan-1  C04  0.020
 66R  plan-1  C05  0.020
 66R  plan-1  C06  0.020
 66R  plan-1  F07  0.020
 66R  plan-1  N08  0.020
 66R  plan-1  H1   0.020
 66R  plan-1  H2   0.020
 66R  plan-1  H3   0.020
 66R  plan-1  H4   0.020
 66R  plan-2  C21  0.020
 66R  plan-2  C22  0.020
 66R  plan-2  C23  0.020
 66R  plan-2  C24  0.020
 66R  plan-2  C30  0.020
 66R  plan-2  C31  0.020
 66R  plan-2  N32  0.020
 66R  plan-2  C33  0.020
 66R  plan-2  C34  0.020
 66R  plan-2  C35  0.020
 66R  plan-2  C36  0.020
 66R  plan-2  H26  0.020
 66R  plan-2  H27  0.020
 66R  plan-2  H28  0.020
 66R  plan-2  H29  0.020
 66R  plan-2  H30  0.020
 66R  plan-3  C14  0.020
 66R  plan-3  C15  0.020
 66R  plan-3  C16  0.020
 66R  plan-3  C17  0.020
 66R  plan-3  C18  0.020
 66R  plan-3  C19  0.020
 66R  plan-3  C20  0.020
 66R  plan-3  C21  0.020
 66R  plan-3  O37  0.020
 66R  plan-3  H16  0.020
 66R  plan-3  H17  0.020
 66R  plan-3  H18  0.020
 66R  plan-4  C25  0.020
 66R  plan-4  C27  0.020
 66R  plan-4  O28  0.020
 66R  plan-4  O29  0.020

