# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Nov 21 01:57:44 2022
#   Inital geometry file: a 228 line input string
#   Ligand name: (1R)-4-O-acetyl-1,5-anhydro-3-O-(9-carboxynonanoyl)-2,6-dideoxy-1-[(4aR,6S,6aS,7S,12aS,12bR)-4a,6,7,8,12b-pentahydroxy-3-methyl-1,12-dioxo-1,4,4a,5,6,7,12,12b-octahydro-6a,12a-epoxytetraphen-9-yl]-D-arabino-hexitol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1O[C@H](C[C@@H](OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)[C@@H]1OC(C)=O)c2ccc3C(=O)[C@@]45O[C@@]4([C@@H](O)C[C@]6(O)CC(=CC(=O)[C@]56O)C)[C@@H](O)c3c2O
#
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
 SMQ  SMQ  "SIMOCYCLINONE C4"  ligand  90  52  .  2023-02-16  2023-02-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_SMQ
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
 SMQ  O4    O  OH1   0  -0.601  36.6476  -21.7592  -6.1479
 SMQ  C1A   C  CR6   0  -0.017  44.2271  -35.6847   1.6831
 SMQ  O1A   O  OH1   0  -0.635  45.8472  -33.9249   1.9991
 SMQ  C1B   C  CR6   0   0.319  45.5213  -35.1695   1.5822
 SMQ  O1B   O  OH1   0  -0.657  47.8525  -34.0486   0.1878
 SMQ  C1C   C  CR6   0   0.015  46.5613  -35.9213   1.0234
 SMQ  O1C   O  OH1   0  -0.671  50.8189  -35.8377   1.4768
 SMQ  C1D   C  CH1   0  -0.050  47.9238  -35.2756   0.8793
 SMQ  O1D   O  OH1   0  -0.668  52.1328  -38.4510  -1.2574
 SMQ  C1E   C  CT    0   0.206  48.9037  -36.0940   0.0749
 SMQ  O1E   O  O     0  -0.409  49.8289  -40.7555  -0.2485
 SMQ  C1F   C  CH1   0  -0.016  50.3546  -35.6418   0.1636
 SMQ  O1F   O  OH1   0  -0.681  50.3995  -38.5087   0.8906
 SMQ  C1G   C  CH2   0  -0.508  51.2381  -36.2752  -0.9188
 SMQ  O1G   O  O     0  -0.366  47.2443  -39.3315   0.1295
 SMQ  C1H   C  CT    0   0.270  50.9265  -37.7242  -1.3594
 SMQ  O1H   O  O2    0  -0.446  48.4409  -36.4591  -1.2044
 SMQ  C1I   C  CH2   0  -0.546  50.4207  -37.7454  -2.8132
 SMQ  C1J   C  C     0   0.123  49.6139  -38.9383  -3.2214
 SMQ  C1K   C  CH3   0  -0.714  49.3057  -39.0413  -4.6767
 SMQ  C1L   C  C1    0  -0.375  49.2156  -39.8713  -2.3452
 SMQ  C1M   C  C     0   0.362  49.6103  -39.7873  -0.9492
 SMQ  C1N   C  CT    0   0.040  49.8899  -38.3855  -0.4054
 SMQ  C1O   C  CT    0   0.143  48.6571  -37.4981  -0.2694
 SMQ  C1P   C  C     0   0.397  47.3777  -38.1293   0.1795
 SMQ  C1Q   C  CR6   0  -0.059  46.3003  -37.2383   0.6490
 SMQ  C1R   C  CR16  0  -0.281  45.0193  -37.7726   0.7783
 SMQ  C1S   C  CR16  0  -0.308  43.9942  -36.9930   1.2677
 SMQ  C2A   C  CH1   0  -0.004  43.0860  -34.8184   2.1531
 SMQ  O2A   O  O2    0  -0.491  42.0404  -35.6458   2.5928
 SMQ  C2B   C  CH2   0  -0.481  42.6170  -33.9135   1.0108
 SMQ  O2B   O  O2    0  -0.473  39.2875  -33.2822   2.5468
 SMQ  C2C   C  CH1   0   0.010  41.4099  -33.1149   1.4650
 SMQ  O2C   O  O     0  -0.432  37.8215  -33.8382   0.9415
 SMQ  C2D   C  CH1   0   0.024  40.3427  -34.0595   1.9919
 SMQ  O2D   O  O2    0  -0.485  40.8836  -32.3993   0.3494
 SMQ  C2E   C  CH1   0   0.018  40.9254  -34.9408   3.1036
 SMQ  C2F   C  CH3   0  -0.688  39.9304  -35.9583   3.6194
 SMQ  C2G   C  C     0   0.561  38.0987  -33.2199   1.9346
 SMQ  C2H   C  CH3   0  -0.774  37.1860  -32.2729   2.6528
 SMQ  C3A   C  C     0   0.595  40.6365  -31.0888   0.4465
 SMQ  O3A   O  O     0  -0.441  40.8346  -30.4325   1.4403
 SMQ  C3B   C  C1    0  -0.431  40.1019  -30.5730  -0.8197
 SMQ  O3B   O  O     0  -0.443  36.6568  -23.7186  -7.2224
 SMQ  C3C   C  C1    0  -0.169  39.7920  -29.2740  -0.9599
 SMQ  C3D   C  C1    0  -0.240  39.2733  -28.7056  -2.1747
 SMQ  C3E   C  C1    0  -0.233  38.9748  -27.3954  -2.2890
 SMQ  C3F   C  C1    0  -0.232  38.4616  -26.8036  -3.4935
 SMQ  C3G   C  C1    0  -0.241  38.1694  -25.4918  -3.6048
 SMQ  C3H   C  C1    0  -0.170  37.6623  -24.9119  -4.8194
 SMQ  C3I   C  C1    0  -0.408  37.3737  -23.6077  -4.9535
 SMQ  C3J   C  C     0   0.524  36.8631  -23.0707  -6.2221
 SMQ  HO4   H  HOH1  0   0.478  36.3149  -21.4329  -6.9974
 SMQ  HO1A  H  HOH1  0   0.486  45.1943  -33.5447   2.5973
 SMQ  HO1C  H  HOH1  0   0.449  50.8509  -36.7925   1.6351
 SMQ  H1D   H  HCH1  0   0.255  48.3498  -35.1449   1.8821
 SMQ  HO1D  H  HOH1  0   0.453  52.1178  -39.2145  -1.8455
 SMQ  H1F   H  HCH1  0   0.263  50.3799  -34.5609   0.0057
 SMQ  HO1F  H  HOH1  0   0.460  50.5296  -39.4545   1.0687
 SMQ  H1G   H  HCH2  0   0.265  51.2098  -35.6334  -1.8010
 SMQ  H1GA  H  HCH2  0   0.269  52.2659  -36.2334  -0.5554
 SMQ  H1I   H  HCH2  0   0.290  49.8299  -36.8575  -3.0381
 SMQ  H1IA  H  HCH2  0   0.280  51.2926  -37.6722  -3.4732
 SMQ  H1K   H  HCH3  0   0.256  48.7878  -38.1420  -5.0174
 SMQ  H1KA  H  HCH3  0   0.258  50.2289  -39.1068  -5.2562
 SMQ  H1KB  H  HCH3  0   0.256  48.6869  -39.9064  -4.9061
 SMQ  H1L   H  H     0   0.273  48.6933  -40.7627  -2.6731
 SMQ  H1R   H  HCR6  0   0.262  44.8266  -38.7941   0.4816
 SMQ  H1S   H  HCR6  0   0.265  42.9981  -37.4057   1.3364
 SMQ  H2A   H  HCH1  0   0.237  43.4032  -34.1849   2.9991
 SMQ  H2B   H  HCH2  0   0.274  43.4209  -33.2381   0.7124
 SMQ  H2BA  H  HCH2  0   0.265  42.3614  -34.5320   0.1458
 SMQ  H2C   H  HCH1  0   0.265  41.7005  -32.4203   2.2582
 SMQ  H2D   H  HCH1  0   0.265  39.9733  -34.6957   1.1823
 SMQ  H2E   H  HCH1  0   0.229  41.2482  -34.2934   3.9340
 SMQ  H2F   H  HCH3  0   0.249  40.3913  -36.5859   4.3818
 SMQ  H2FA  H  HCH3  0   0.242  39.0750  -35.4632   4.0755
 SMQ  H2FB  H  HCH3  0   0.235  39.5683  -36.5992   2.8143
 SMQ  H2H   H  HCH3  0   0.272  37.1100  -32.5316   3.7088
 SMQ  H2HA  H  HCH3  0   0.275  37.5852  -31.2590   2.5967
 SMQ  H2HB  H  HCH3  0   0.263  36.1959  -32.2871   2.2068
 SMQ  H3B   H  H     0   0.278  39.9686  -31.2686  -1.6400
 SMQ  H3C   H  H     0   0.276  39.9357  -28.5982  -0.1221
 SMQ  H3D   H  H     0   0.269  39.1247  -29.3675  -3.0228
 SMQ  H3E   H  H     0   0.271  39.1264  -26.7396  -1.4359
 SMQ  H3F   H  H     0   0.271  38.3095  -27.4576  -4.3478
 SMQ  H3G   H  H     0   0.269  38.3201  -24.8341  -2.7538
 SMQ  H3H   H  H     0   0.276  37.5140  -25.5807  -5.6621
 SMQ  H3I   H  H     0   0.280  37.5142  -22.9211  -4.1266
 SMQ  HO1B  H  HOH1  0   0.465  47.5087  -33.3803   0.7891

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
 SMQ  O4   C3J   single    1.331  0.020  1.331
 SMQ  O4   HO4   single    0.850  0.020  0.980
 SMQ  C1S  C1A   aromatic  1.392  0.020  1.392
 SMQ  C1A  C1B   aromatic  1.397  0.020  1.397
 SMQ  C1A  C2A   single    1.508  0.020  1.508
 SMQ  C1B  O1A   single    1.352  0.020  1.352
 SMQ  O1A  HO1A  single    0.850  0.020  0.980
 SMQ  C1C  C1B   aromatic  1.400  0.020  1.400
 SMQ  C1D  O1B   single    1.410  0.020  1.410
 SMQ  O1B  HO1B  single    0.850  0.020  0.980
 SMQ  C1Q  C1C   aromatic  1.394  0.020  1.394
 SMQ  C1C  C1D   single    1.515  0.020  1.515
 SMQ  C1F  O1C   single    1.407  0.020  1.407
 SMQ  O1C  HO1C  single    0.850  0.020  0.980
 SMQ  C1E  C1D   single    1.509  0.020  1.509
 SMQ  C1D  H1D   single    0.970  0.020  1.090
 SMQ  O1D  C1H   single    1.412  0.020  1.412
 SMQ  O1D  HO1D  single    0.850  0.020  0.980
 SMQ  O1H  C1E   single    1.409  0.020  1.409
 SMQ  C1O  C1E   single    1.467  0.020  1.467
 SMQ  C1E  C1F   single    1.522  0.020  1.522
 SMQ  C1M  O1E   double    1.215  0.020  1.215
 SMQ  C1G  C1F   single    1.534  0.020  1.534
 SMQ  C1F  H1F   single    0.970  0.020  1.090
 SMQ  C1N  O1F   single    1.398  0.020  1.398
 SMQ  O1F  HO1F  single    0.850  0.020  0.980
 SMQ  C1H  C1G   single    1.546  0.020  1.546
 SMQ  C1G  H1G   single    0.970  0.020  1.090
 SMQ  C1G  H1GA  single    0.970  0.020  1.090
 SMQ  O1G  C1P   double    1.211  0.020  1.211
 SMQ  C1I  C1H   single    1.539  0.020  1.539
 SMQ  C1H  C1N   single    1.556  0.020  1.556
 SMQ  O1H  C1O   single    1.414  0.020  1.414
 SMQ  C1J  C1I   single    1.497  0.020  1.497
 SMQ  C1I  H1I   single    0.970  0.020  1.090
 SMQ  C1I  H1IA  single    0.970  0.020  1.090
 SMQ  C1K  C1J   single    1.491  0.020  1.491
 SMQ  C1J  C1L   double    1.341  0.020  1.341
 SMQ  C1K  H1K   single    0.970  0.020  1.090
 SMQ  C1K  H1KA  single    0.970  0.020  1.090
 SMQ  C1K  H1KB  single    0.970  0.020  1.090
 SMQ  C1L  C1M   single    1.453  0.020  1.453
 SMQ  C1L  H1L   single    0.930  0.020  1.080
 SMQ  C1M  C1N   single    1.529  0.020  1.529
 SMQ  C1N  C1O   single    1.525  0.020  1.525
 SMQ  C1O  C1P   single    1.496  0.020  1.496
 SMQ  C1P  C1Q   single    1.475  0.020  1.475
 SMQ  C1R  C1Q   aromatic  1.394  0.020  1.394
 SMQ  C1R  C1S   aromatic  1.378  0.020  1.378
 SMQ  C1R  H1R   single    0.930  0.020  1.080
 SMQ  C1S  H1S   single    0.930  0.020  1.080
 SMQ  C2B  C2A   single    1.531  0.020  1.531
 SMQ  C2A  O2A   single    1.404  0.020  1.404
 SMQ  C2A  H2A   single    0.970  0.020  1.090
 SMQ  O2A  C2E   single    1.415  0.020  1.415
 SMQ  C2B  C2C   single    1.517  0.020  1.517
 SMQ  C2B  H2B   single    0.970  0.020  1.090
 SMQ  C2B  H2BA  single    0.970  0.020  1.090
 SMQ  C2D  O2B   single    1.423  0.020  1.423
 SMQ  C2G  O2B   single    1.339  0.020  1.339
 SMQ  O2D  C2C   single    1.426  0.020  1.426
 SMQ  C2C  C2D   single    1.520  0.020  1.520
 SMQ  C2C  H2C   single    0.970  0.020  1.090
 SMQ  O2C  C2G   double    1.202  0.020  1.202
 SMQ  C2D  C2E   single    1.534  0.020  1.534
 SMQ  C2D  H2D   single    0.970  0.020  1.090
 SMQ  O2D  C3A   single    1.337  0.020  1.337
 SMQ  C2E  C2F   single    1.514  0.020  1.514
 SMQ  C2E  H2E   single    0.970  0.020  1.090
 SMQ  C2F  H2F   single    0.970  0.020  1.090
 SMQ  C2F  H2FA  single    0.970  0.020  1.090
 SMQ  C2F  H2FB  single    0.970  0.020  1.090
 SMQ  C2G  C2H   single    1.499  0.020  1.499
 SMQ  C2H  H2H   single    0.970  0.020  1.090
 SMQ  C2H  H2HA  single    0.970  0.020  1.090
 SMQ  C2H  H2HB  single    0.970  0.020  1.090
 SMQ  C3B  C3A   single    1.468  0.020  1.468
 SMQ  C3A  O3A   double    1.207  0.020  1.207
 SMQ  C3B  C3C   double    1.343  0.020  1.343
 SMQ  C3B  H3B   single    0.930  0.020  1.080
 SMQ  O3B  C3J   double    1.210  0.020  1.210
 SMQ  C3D  C3C   single    1.438  0.020  1.438
 SMQ  C3C  H3C   single    0.930  0.020  1.080
 SMQ  C3E  C3D   double    1.349  0.020  1.349
 SMQ  C3D  H3D   single    0.930  0.020  1.080
 SMQ  C3F  C3E   single    1.437  0.020  1.437
 SMQ  C3E  H3E   single    0.930  0.020  1.080
 SMQ  C3G  C3F   double    1.349  0.020  1.349
 SMQ  C3F  H3F   single    0.930  0.020  1.080
 SMQ  C3H  C3G   single    1.438  0.020  1.438
 SMQ  C3G  H3G   single    0.930  0.020  1.080
 SMQ  C3I  C3H   double    1.342  0.020  1.342
 SMQ  C3H  H3H   single    0.930  0.020  1.080
 SMQ  C3J  C3I   single    1.469  0.020  1.469
 SMQ  C3I  H3I   single    0.930  0.020  1.080

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
 SMQ  HO4   O4   C3J   109.78  3.000
 SMQ  C2A   C1A  C1S   120.42  3.000
 SMQ  C2A   C1A  C1B   120.78  3.000
 SMQ  C1S   C1A  C1B   118.69  3.000
 SMQ  HO1A  O1A  C1B   113.02  3.000
 SMQ  C1C   C1B  O1A   116.00  3.000
 SMQ  C1C   C1B  C1A   121.28  3.000
 SMQ  O1A   C1B  C1A   122.72  3.000
 SMQ  HO1B  O1B  C1D   108.41  3.000
 SMQ  C1Q   C1C  C1D   123.07  3.000
 SMQ  C1D   C1C  C1B   118.51  3.000
 SMQ  C1Q   C1C  C1B   118.40  3.000
 SMQ  HO1C  O1C  C1F   107.51  3.000
 SMQ  H1D   C1D  C1E   107.44  3.000
 SMQ  H1D   C1D  C1C   108.24  3.000
 SMQ  C1E   C1D  C1C   113.81  3.000
 SMQ  H1D   C1D  O1B   111.35  3.000
 SMQ  C1E   C1D  O1B   104.08  3.000
 SMQ  C1C   C1D  O1B   111.84  3.000
 SMQ  HO1D  O1D  C1H   110.51  3.000
 SMQ  C1O   C1E  O1H    58.89  3.000
 SMQ  C1O   C1E  C1F   117.28  3.000
 SMQ  O1H   C1E  C1F   116.30  3.000
 SMQ  C1F   C1E  C1D   115.26  3.000
 SMQ  C1O   C1E  C1D   122.35  3.000
 SMQ  O1H   C1E  C1D   114.29  3.000
 SMQ  H1F   C1F  C1G   107.05  3.000
 SMQ  H1F   C1F  C1E   107.91  3.000
 SMQ  C1G   C1F  C1E   112.66  3.000
 SMQ  H1F   C1F  O1C   105.37  3.000
 SMQ  C1G   C1F  O1C   114.27  3.000
 SMQ  C1E   C1F  O1C   109.12  3.000
 SMQ  HO1F  O1F  C1N   107.74  3.000
 SMQ  H1GA  C1G  H1G   105.74  3.000
 SMQ  H1GA  C1G  C1H   108.70  3.000
 SMQ  H1G   C1G  C1H   108.39  3.000
 SMQ  H1GA  C1G  C1F   106.96  3.000
 SMQ  H1G   C1G  C1F   108.21  3.000
 SMQ  C1H   C1G  C1F   118.16  3.000
 SMQ  C1N   C1H  C1I   110.75  3.000
 SMQ  C1N   C1H  C1G   110.96  3.000
 SMQ  C1I   C1H  C1G   110.37  3.000
 SMQ  C1N   C1H  O1D   107.82  3.000
 SMQ  C1I   C1H  O1D   109.99  3.000
 SMQ  C1G   C1H  O1D   106.83  3.000
 SMQ  C1O   O1H  C1E    62.60  3.000
 SMQ  H1IA  C1I  H1I   104.64  3.000
 SMQ  H1IA  C1I  C1J   108.53  3.000
 SMQ  H1I   C1I  C1J   107.51  3.000
 SMQ  H1IA  C1I  C1H   107.84  3.000
 SMQ  H1I   C1I  C1H   111.21  3.000
 SMQ  C1J   C1I  C1H   116.46  3.000
 SMQ  C1L   C1J  C1K   121.90  3.000
 SMQ  C1L   C1J  C1I   122.45  3.000
 SMQ  C1K   C1J  C1I   115.63  3.000
 SMQ  H1KB  C1K  H1KA  108.73  3.000
 SMQ  H1KB  C1K  H1K   108.62  3.000
 SMQ  H1KA  C1K  H1K   106.54  3.000
 SMQ  H1KB  C1K  C1J   112.22  3.000
 SMQ  H1KA  C1K  C1J   110.33  3.000
 SMQ  H1K   C1K  C1J   110.22  3.000
 SMQ  H1L   C1L  C1M   117.97  3.000
 SMQ  H1L   C1L  C1J   121.19  3.000
 SMQ  C1M   C1L  C1J   120.46  3.000
 SMQ  C1N   C1M  C1L   116.38  3.000
 SMQ  C1N   C1M  O1E   119.50  3.000
 SMQ  C1L   C1M  O1E   123.84  3.000
 SMQ  C1O   C1N  C1M   114.66  3.000
 SMQ  C1O   C1N  C1H   110.24  3.000
 SMQ  C1M   C1N  C1H   107.05  3.000
 SMQ  C1O   C1N  O1F   105.26  3.000
 SMQ  C1M   C1N  O1F   108.39  3.000
 SMQ  C1H   C1N  O1F   111.28  3.000
 SMQ  C1P   C1O  C1N   118.21  3.000
 SMQ  C1P   C1O  O1H   112.19  3.000
 SMQ  C1N   C1O  O1H   119.47  3.000
 SMQ  C1P   C1O  C1E   118.52  3.000
 SMQ  C1N   C1O  C1E   116.24  3.000
 SMQ  O1H   C1O  C1E    58.51  3.000
 SMQ  C1Q   C1P  C1O   117.74  3.000
 SMQ  C1Q   C1P  O1G   122.18  3.000
 SMQ  C1O   C1P  O1G   120.06  3.000
 SMQ  C1R   C1Q  C1P   117.99  3.000
 SMQ  C1R   C1Q  C1C   120.62  3.000
 SMQ  C1P   C1Q  C1C   121.30  3.000
 SMQ  H1R   C1R  C1S   119.97  3.000
 SMQ  H1R   C1R  C1Q   120.04  3.000
 SMQ  C1S   C1R  C1Q   119.99  3.000
 SMQ  H1S   C1S  C1R   119.51  3.000
 SMQ  H1S   C1S  C1A   119.61  3.000
 SMQ  C1R   C1S  C1A   120.88  3.000
 SMQ  H2A   C2A  C2B   108.71  3.000
 SMQ  H2A   C2A  O2A   108.20  3.000
 SMQ  C2B   C2A  O2A   110.72  3.000
 SMQ  H2A   C2A  C1A   110.57  3.000
 SMQ  O2A   C2A  C1A   108.82  3.000
 SMQ  C2B   C2A  C1A   109.81  3.000
 SMQ  C2E   O2A  C2A   113.98  3.000
 SMQ  H2BA  C2B  H2B   107.81  3.000
 SMQ  H2BA  C2B  C2C   110.40  3.000
 SMQ  H2B   C2B  C2C   110.01  3.000
 SMQ  H2BA  C2B  C2A   109.11  3.000
 SMQ  H2B   C2B  C2A   110.13  3.000
 SMQ  C2C   C2B  C2A   109.36  3.000
 SMQ  C2G   O2B  C2D   120.37  3.000
 SMQ  H2C   C2C  O2D   110.29  3.000
 SMQ  H2C   C2C  C2D   109.27  3.000
 SMQ  O2D   C2C  C2D   108.91  3.000
 SMQ  H2C   C2C  C2B   109.88  3.000
 SMQ  C2D   C2C  C2B   109.60  3.000
 SMQ  O2D   C2C  C2B   108.88  3.000
 SMQ  H2D   C2D  C2E   109.31  3.000
 SMQ  H2D   C2D  C2C   110.00  3.000
 SMQ  C2E   C2D  C2C   109.98  3.000
 SMQ  H2D   C2D  O2B   110.84  3.000
 SMQ  C2E   C2D  O2B   108.24  3.000
 SMQ  C2C   C2D  O2B   108.44  3.000
 SMQ  C3A   O2D  C2C   120.21  3.000
 SMQ  H2E   C2E  C2F   109.32  3.000
 SMQ  H2E   C2E  C2D   108.67  3.000
 SMQ  C2F   C2E  C2D   112.55  3.000
 SMQ  H2E   C2E  O2A   109.53  3.000
 SMQ  C2F   C2E  O2A   107.83  3.000
 SMQ  C2D   C2E  O2A   108.92  3.000
 SMQ  H2FB  C2F  H2FA  108.39  3.000
 SMQ  H2FB  C2F  H2F   108.55  3.000
 SMQ  H2FA  C2F  H2F   107.53  3.000
 SMQ  H2FB  C2F  C2E   111.20  3.000
 SMQ  H2FA  C2F  C2E   110.71  3.000
 SMQ  H2F   C2F  C2E   110.34  3.000
 SMQ  C2H   C2G  O2C   125.49  3.000
 SMQ  C2H   C2G  O2B   110.55  3.000
 SMQ  O2C   C2G  O2B   123.96  3.000
 SMQ  H2HB  C2H  H2HA  108.94  3.000
 SMQ  H2HB  C2H  H2H   109.34  3.000
 SMQ  H2HA  C2H  H2H   107.20  3.000
 SMQ  H2HB  C2H  C2G   110.50  3.000
 SMQ  H2HA  C2H  C2G   109.86  3.000
 SMQ  H2H   C2H  C2G   110.91  3.000
 SMQ  C3B   C3A  O3A   125.37  3.000
 SMQ  O3A   C3A  O2D   124.21  3.000
 SMQ  C3B   C3A  O2D   110.43  3.000
 SMQ  H3B   C3B  C3C   120.90  3.000
 SMQ  H3B   C3B  C3A   118.17  3.000
 SMQ  C3C   C3B  C3A   120.93  3.000
 SMQ  H3C   C3C  C3D   116.97  3.000
 SMQ  H3C   C3C  C3B   119.40  3.000
 SMQ  C3D   C3C  C3B   123.63  3.000
 SMQ  H3D   C3D  C3E   119.71  3.000
 SMQ  H3D   C3D  C3C   117.91  3.000
 SMQ  C3E   C3D  C3C   122.38  3.000
 SMQ  H3E   C3E  C3F   117.35  3.000
 SMQ  H3E   C3E  C3D   119.27  3.000
 SMQ  C3F   C3E  C3D   123.39  3.000
 SMQ  H3F   C3F  C3G   119.36  3.000
 SMQ  H3F   C3F  C3E   117.46  3.000
 SMQ  C3G   C3F  C3E   123.18  3.000
 SMQ  H3G   C3G  C3H   117.81  3.000
 SMQ  H3G   C3G  C3F   119.62  3.000
 SMQ  C3H   C3G  C3F   122.57  3.000
 SMQ  H3H   C3H  C3I   119.43  3.000
 SMQ  H3H   C3H  C3G   117.07  3.000
 SMQ  C3I   C3H  C3G   123.49  3.000
 SMQ  H3I   C3I  C3J   118.18  3.000
 SMQ  H3I   C3I  C3H   120.75  3.000
 SMQ  C3J   C3I  C3H   121.07  3.000
 SMQ  C3I   C3J  O3B   125.28  3.000
 SMQ  C3I   C3J  O4    111.61  3.000
 SMQ  O3B   C3J  O4    123.11  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
 SMQ  CONST_01  C1Q   C1R  C1S  C1A     0.00   0.0  0
 SMQ  CONST_02  C1Q   C1C  C1B  C1A     0.00   0.0  0
 SMQ  CONST_03  C1R   C1S  C1A  C1B     0.00   0.0  0
 SMQ  CONST_04  C1R   C1Q  C1C  C1B     0.00   0.0  0
 SMQ  CONST_05  C1S   C1A  C1B  C1C     0.00   0.0  0
 SMQ  CONST_06  C1S   C1R  C1Q  C1C     0.00   0.0  0
 SMQ  CONST_07  C2A   C1A  C1B  C1C   180.00   0.0  0
 SMQ  CONST_08  C2A   C1A  C1S  C1R   180.00   0.0  0
 SMQ  CONST_09  C1S   C1A  C1B  O1A   180.00   0.0  0
 SMQ  CONST_10  C2A   C1A  C1B  O1A     0.00   0.0  0
 SMQ  CONST_11  C1Q   C1C  C1B  O1A   180.00   0.0  0
 SMQ  CONST_12  C1D   C1C  C1B  O1A     0.00   0.0  0
 SMQ  CONST_13  H1R   C1R  C1S  C1A   180.00   0.0  0
 SMQ  CONST_14  H1S   C1S  C1A  C1B   180.00   0.0  0
 SMQ  CONST_15  H1R   C1R  C1Q  C1C   180.00   0.0  0
 SMQ  CONST_16  H1R   C1R  C1Q  C1P     0.00   0.0  0
 SMQ  CONST_17  H1S   C1S  C1R  C1Q   180.00   0.0  0
 SMQ  CONST_18  H1S   C1S  C1A  C2A     0.00   0.0  0
 SMQ  CONST_19  HO4   O4   C3J  O3B     0.00   0.0  0
 SMQ  CONST_20  HO4   O4   C3J  C3I   180.00   0.0  0
 SMQ  Var_01    C1O   C1P  C1Q  C1C   -17.76  30.0  1
 SMQ  Var_02    C1O   O1H  C1E  C1D  -114.42  30.0  1
 SMQ  Var_03    C1N   C1O  C1E  C1D  -149.29  30.0  1
 SMQ  Var_04    C1P   C1O  C1E  C1D     0.89  30.0  1
 SMQ  Var_05    C1N   C1O  O1H  C1E  -104.43  30.0  1
 SMQ  Var_06    C1P   C1O  O1H  C1E   110.78  30.0  1
 SMQ  Var_07    C1Q   C1P  C1O  C1E    14.60  30.0  1
 SMQ  Var_08    C1O   O1H  C1E  C1F   107.39  30.0  1
 SMQ  Var_09    C1N   C1O  C1E  C1F     4.23  30.0  1
 SMQ  Var_10    C1P   C1O  C1E  C1F   154.41  30.0  1
 SMQ  Var_11    C1L   C1J  C1I  C1H     7.38  30.0  1
 SMQ  Var_12    C1Q   C1P  C1O  O1H   -50.54  30.0  1
 SMQ  Var_13    C1M   C1L  C1J  C1I    -2.77  30.0  1
 SMQ  Var_14    C1N   C1M  C1L  C1J    27.48  30.0  1
 SMQ  Var_15    C1Q   C1P  C1O  C1N   164.19  30.0  1
 SMQ  Var_16    C1R   C1Q  C1P  C1O   165.68  30.0  1
 SMQ  Var_17    O1G   C1P  C1Q  C1C   163.49  30.0  1
 SMQ  Var_18    O1G   C1P  C1O  C1E  -166.62  30.0  1
 SMQ  Var_19    C1J   C1L  C1M  O1E  -146.33  30.0  1
 SMQ  Var_20    O1H   C1O  C1P  O1G   128.24  30.0  1
 SMQ  Var_21    C1N   C1O  C1P  O1G   -17.02  30.0  1
 SMQ  Var_22    C1R   C1Q  C1P  O1G   -13.08  30.0  1
 SMQ  Var_23    C1K   C1J  C1I  C1H  -171.27  30.0  1
 SMQ  Var_24    C1M   C1L  C1J  C1K   175.79  30.0  1
 SMQ  Var_25    H1L   C1L  C1J  C1I  -175.57  30.0  1
 SMQ  Var_26    H1I   C1I  C1J  C1L  -118.12  30.0  1
 SMQ  Var_27    H1IA  C1I  C1J  C1L   129.22  30.0  1
 SMQ  Var_28    H1L   C1L  C1M  C1N  -159.49  30.0  1
 SMQ  Var_29    H1L   C1L  C1M  O1E    26.70  30.0  1
 SMQ  Var_30    H1K   C1K  C1J  C1I   -56.65  30.0  3
 SMQ  Var_31    H1KA  C1K  C1J  C1I    60.73  30.0  3
 SMQ  Var_32    H1KB  C1K  C1J  C1I  -177.85  30.0  3
 SMQ  Var_33    H1I   C1I  C1J  C1K    63.23  30.0  1
 SMQ  Var_34    H1IA  C1I  C1J  C1K   -49.42  30.0  1
 SMQ  Var_35    H1L   C1L  C1J  C1K     2.99  30.0  1
 SMQ  Var_36    H1K   C1K  C1J  C1L   124.69  30.0  3
 SMQ  Var_37    H1KA  C1K  C1J  C1L  -117.92  30.0  3
 SMQ  Var_38    H1KB  C1K  C1J  C1L     3.50  30.0  3
 SMQ  Var_39    C3B   C3A  O2D  C2C  -179.98  30.0  3
 SMQ  Var_40    O3A   C3A  O2D  C2C     0.28  30.0  3
 SMQ  Var_41    C2D   O2B  C2G  O2C     3.37  30.0  3
 SMQ  Var_42    C2H   C2G  O2B  C2D  -176.17  30.0  1
 SMQ  Var_43    C3D   C3C  C3B  C3A   179.60   0.0  2
 SMQ  Var_44    C3F   C3E  C3D  C3C   179.70   0.0  2
 SMQ  Var_45    C3H   C3G  C3F  C3E   179.69   0.0  2
 SMQ  Var_46    C3J   C3I  C3H  C3G   179.74   0.0  2
 SMQ  Var_47    C3H   C3I  C3J  O4   -179.69  30.0  2
 SMQ  Var_48    C3C   C3B  C3A  O2D  -179.34  30.0  2
 SMQ  Var_49    C3C   C3B  C3A  O3A     0.39  30.0  2
 SMQ  Var_50    C3E   C3D  C3C  C3B  -179.76  30.0  1
 SMQ  Var_51    C3H   C3I  C3J  O3B     0.28  30.0  2
 SMQ  Var_52    C3G   C3F  C3E  C3D  -179.73  30.0  2
 SMQ  Var_53    C3I   C3H  C3G  C3F  -179.54  30.0  2
 SMQ  Var_54    H3C   C3C  C3B  C3A    -0.26   0.0  2
 SMQ  Var_55    H3E   C3E  C3D  C3C    -0.17   0.0  2
 SMQ  Var_56    H3B   C3B  C3C  C3D    -0.11   0.0  2
 SMQ  Var_57    H3G   C3G  C3F  C3E    -0.13   0.0  2
 SMQ  Var_58    H3D   C3D  C3E  C3F    -0.12   0.0  2
 SMQ  Var_59    H3I   C3I  C3H  C3G    -0.11   0.0  2
 SMQ  Var_60    H3F   C3F  C3G  C3H    -0.15   0.0  2
 SMQ  Var_61    H3H   C3H  C3I  C3J    -0.11   0.0  2
 SMQ  Var_62    H3I   C3I  C3J  O4      0.16  30.0  2
 SMQ  Var_63    H2H   C2H  C2G  O2B   -53.72  30.0  3
 SMQ  Var_64    H2HA  C2H  C2G  O2B    64.62  30.0  3
 SMQ  Var_65    H2HB  C2H  C2G  O2B  -175.15  30.0  3
 SMQ  Var_66    H2H   C2H  C2G  O2C   126.74  30.0  3
 SMQ  Var_67    H2HA  C2H  C2G  O2C  -114.92  30.0  3
 SMQ  Var_68    H2HB  C2H  C2G  O2C     5.32  30.0  3
 SMQ  Var_69    H3B   C3B  C3A  O2D     0.38  30.0  2
 SMQ  Var_70    H3B   C3B  C3A  O3A  -179.89  30.0  2
 SMQ  Var_71    H3D   C3D  C3C  C3B     0.07  30.0  1
 SMQ  Var_72    H3I   C3I  C3J  O3B  -179.87  30.0  2
 SMQ  Var_73    H3F   C3F  C3E  C3D     0.11  30.0  2
 SMQ  Var_74    H3C   C3C  C3D  C3E     0.10  30.0  2
 SMQ  Var_75    H3H   C3H  C3G  C3F     0.31  30.0  2
 SMQ  Var_76    H3E   C3E  C3F  C3G     0.14  30.0  2
 SMQ  Var_77    H3G   C3G  C3H  C3I     0.28  30.0  2
 SMQ  Var_78    H3C   C3C  C3B  H3B  -179.97   0.0  2
 SMQ  Var_79    H3E   C3E  C3D  H3D  -179.99   0.0  2
 SMQ  Var_80    H3G   C3G  C3F  H3F  -179.97   0.0  2
 SMQ  Var_81    H3I   C3I  C3H  H3H  -179.96   0.0  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
 SMQ  chir_01  C1D  O1B  C1C  C1E  negativ
 SMQ  chir_03  C1F  O1C  C1E  C1G  positiv
 SMQ  chir_04  C1H  C1N  C1I  C1G  negativ
 SMQ  chir_05  C1N  C1O  C1M  C1H  negativ
 SMQ  chir_07  C2A  C1A  C2B  O2A  negativ
 SMQ  chir_08  C2C  O2D  C2D  C2B  negativ
 SMQ  chir_09  C2D  O2B  C2E  C2C  positiv
 SMQ  chir_10  C2E  O2A  C2F  C2D  positiv

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
 SMQ  plan-1   O2D  0.020
 SMQ  plan-1   C3A  0.020
 SMQ  plan-1   O3A  0.020
 SMQ  plan-1   C3B  0.020
 SMQ  plan-2   C3A  0.020
 SMQ  plan-2   C3B  0.020
 SMQ  plan-2   C3C  0.020
 SMQ  plan-2   C3D  0.020
 SMQ  plan-2   H3B  0.020
 SMQ  plan-2   H3C  0.020
 SMQ  plan-3   C3C  0.020
 SMQ  plan-3   C3D  0.020
 SMQ  plan-3   C3E  0.020
 SMQ  plan-3   C3F  0.020
 SMQ  plan-3   H3D  0.020
 SMQ  plan-3   H3E  0.020
 SMQ  plan-4   C3E  0.020
 SMQ  plan-4   C3F  0.020
 SMQ  plan-4   C3G  0.020
 SMQ  plan-4   C3H  0.020
 SMQ  plan-4   H3F  0.020
 SMQ  plan-4   H3G  0.020
 SMQ  plan-5   C3G  0.020
 SMQ  plan-5   C3H  0.020
 SMQ  plan-5   C3I  0.020
 SMQ  plan-5   C3J  0.020
 SMQ  plan-5   H3H  0.020
 SMQ  plan-5   H3I  0.020
 SMQ  plan-6   O1E  0.020
 SMQ  plan-6   C1L  0.020
 SMQ  plan-6   C1M  0.020
 SMQ  plan-6   C1N  0.020
 SMQ  plan-7   C1A  0.020
 SMQ  plan-7   O1A  0.020
 SMQ  plan-7   C1B  0.020
 SMQ  plan-7   C1C  0.020
 SMQ  plan-7   C1D  0.020
 SMQ  plan-7   C1P  0.020
 SMQ  plan-7   C1Q  0.020
 SMQ  plan-7   C1R  0.020
 SMQ  plan-7   C1S  0.020
 SMQ  plan-7   C2A  0.020
 SMQ  plan-7   H1R  0.020
 SMQ  plan-7   H1S  0.020
 SMQ  plan-8   O1G  0.020
 SMQ  plan-8   C1O  0.020
 SMQ  plan-8   C1P  0.020
 SMQ  plan-8   C1Q  0.020
 SMQ  plan-9   O4   0.020
 SMQ  plan-9   O3B  0.020
 SMQ  plan-9   C3I  0.020
 SMQ  plan-9   C3J  0.020
 SMQ  plan-9   HO4  0.020
 SMQ  plan-10  O2B  0.020
 SMQ  plan-10  O2C  0.020
 SMQ  plan-10  C2G  0.020
 SMQ  plan-10  C2H  0.020

