# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sun May 24 13:51:39 2020
#   Inital geometry file: a 243 line input string
#   Ligand name: 1-O-[(3alpha,5beta,12alpha,14beta,16alpha,17alpha)-3-(acetyloxy)-12,16,30-trihydroxy-21,23,28-trioxolanosta-7,24-dien-28-yl]-beta-L-glucopyranose
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)=CC(=O)C[C@@H](C=O)[C@@H]1[C@@H](O)C[C@]2(CO)C3=CC[C@@H]4[C@](C)(CC[C@@H](OC(C)=O)[C@@]4(C)C(=O)O[C@H]5O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]5O)[C@H]3C[C@H](O)[C@@]12C
#
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
 GR4  GR4  1-O-[(3alpha,5beta,12alpha,14beta,16alpha,17alpha)-3-(acetyloxy)-12,16,30-trihydroxy-21,23,28-trioxolanosta-7,24-dien-28-yl]-beta-L-glucopyranose  ligand  108  52  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GR4
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
 GR4  C1    C  CH2   0  -0.428   1.9223   2.1320   -0.4227
 GR4  C2    C  CH2   0  -0.471   2.2499   2.5922   -1.8324
 GR4  C3    C  CH1   0   0.059   1.6907   1.6596   -2.8843
 GR4  C4    C  CT    0  -0.291   0.1685   1.4382   -2.7503
 GR4  C5    C  CH1   0  -0.178  -0.2387   1.1351   -1.2826
 GR4  C6    C  CH2   0  -0.480  -1.7527   1.0992   -1.0837
 GR4  C7    C  C1    0  -0.294  -2.1332   0.8405    0.3389
 GR4  C8    C  C     0   0.240  -1.2857   0.9071    1.3612
 GR4  C9    C  CH1   0  -0.286   0.1871   1.1992    1.1379
 GR4  C10   C  CT    0  -0.057   0.4163   2.0049   -0.1682
 GR4  C11   C  CH2   0  -0.515   0.8235   1.8022    2.3896
 GR4  C12   C  CH1   0   0.106   0.6265   0.9680    3.6796
 GR4  C13   C  CT    0  -0.082  -0.6288   0.0627    3.6396
 GR4  C14   C  CT    0  -0.178  -1.7367   0.7713    2.7939
 GR4  C15   C  CH2   0  -0.478  -2.9600  -0.1102    3.0604
 GR4  C16   C  CH1   0   0.066  -2.8113  -0.5595    4.5284
 GR4  C17   C  CH1   0  -0.256  -1.3863  -0.1662    4.9803
 GR4  C18   C  CH3   0  -0.679  -0.2968  -1.3165    3.0405
 GR4  C19   C  CH3   0  -0.693  -0.1979   3.4015   -0.0217
 GR4  C22   C  CH2   0  -0.617   0.4676  -0.6211    6.6455
 GR4  C23   C  C     0   0.396   1.0031  -1.4361    7.7962
 GR4  C24   C  C1    0  -0.400   2.3233  -1.0020    8.2747
 GR4  C25   C  C     0   0.150   3.0321  -1.4680    9.3193
 GR4  C26   C  CH3   0  -0.709   4.3695  -0.8696    9.6269
 GR4  C27   C  CH3   0  -0.734   2.6220  -2.5571   10.2566
 GR4  C28   C  CH2   0  -0.132  -2.0920   2.1803    3.3472
 GR4  C29   C  C     0   0.669  -0.1428   0.2121   -3.6165
 GR4  C30   C  CH3   0  -0.680  -0.5644   2.6394   -3.3734
 GR4  O31   O  O     0  -0.414  -0.6326  -0.8199   -3.2515
 GR4  O32   O  OH1   0  -0.676  -3.7284   0.0401    5.4219
 GR4  O34   O  O2    0  -0.490   0.2228   0.4310   -4.8887
 GR4  O35   O  O     0  -0.417   0.3563  -2.3582    8.2622
 GR4  O36   O  O2    0  -0.468   2.2893   0.3552   -2.7556
 GR4  C37   C  C     0   0.570   3.3895   0.0729   -3.4461
 GR4  C38   C  CH3   0  -0.768   3.7726  -1.3690   -3.3100
 GR4  O39   O  O     0  -0.460   3.9772   0.8792   -4.1255
 GR4  O1    O  OH1   0  -0.658  -3.0520   2.7708    2.5004
 GR4  O2    O  OH1   0  -0.666   1.7720   0.1691    3.9147
 GR4  O3    O  O2    0  -0.486  -1.3054  -0.4372   -6.2789
 GR4  C32   C  CH1   0   0.289   0.0112  -0.5712   -5.8496
 GR4  C33   C  CH1   0  -0.043   0.9846  -0.3224   -6.9970
 GR4  C34   C  CH1   0  -0.011   0.6615  -1.3052   -8.1159
 GR4  C35   C  CH1   0   0.034  -0.8117  -1.2135   -8.4993
 GR4  C36   C  CH1   0  -0.020  -1.6795  -1.3950   -7.2522
 GR4  O4    O  OH1   0  -0.670  -1.1637  -2.2085   -9.4260
 GR4  O5    O  OH1   0  -0.670   1.4164  -1.0486   -9.2735
 GR4  O6    O  OH1   0  -0.666   2.3136  -0.5382   -6.5923
 GR4  C31   C  CH2   0  -0.156  -3.1495  -1.1960   -7.5499
 GR4  O7    O  OH1   0  -0.668  -3.8890  -1.4644   -6.3836
 GR4  C20   C  CH1   0  -0.358  -0.8059  -1.1660    6.0080
 GR4  C21   C  C1    0   0.219  -1.8413  -1.4033    7.0827
 GR4  H11   H  HCH2  0   0.239   2.3600   2.8410    0.2834
 GR4  H12A  H  HCH2  0   0.228   2.4102   1.1716   -0.2279
 GR4  H21A  H  HCH2  0   0.244   1.8542   3.5940   -2.0184
 GR4  H22   H  HCH2  0   0.257   3.3307   2.6771   -1.9664
 GR4  H3    H  HCH1  0   0.269   1.9112   2.0546   -3.8775
 GR4  H5    H  HCH1  0   0.237   0.1255   0.1200   -1.0888
 GR4  H61   H  HCH2  0   0.249  -2.2066   0.3427   -1.7259
 GR4  H62   H  HCH2  0   0.234  -2.2081   2.0482   -1.3900
 GR4  H7    H  H     0   0.221  -3.1839   0.6423    0.5223
 GR4  H9    H  HCH1  0   0.238   0.6996   0.2420    0.9758
 GR4  H111  H  HCH2  0   0.251   1.8992   1.9149    2.2324
 GR4  H112  H  HCH2  0   0.237   0.4513   2.8140    2.5535
 GR4  H12   H  HCH1  0   0.212   0.4996   1.6757    4.5109
 GR4  H151  H  HCH2  0   0.240  -2.9670  -0.9758    2.3967
 GR4  H152  H  HCH2  0   0.249  -3.9022   0.4147    2.8968
 GR4  H16   H  HCH1  0   0.219  -2.9189  -1.6500    4.5750
 GR4  H17   H  HCH1  0   0.247  -1.4557   0.7942    5.5037
 GR4  H181  H  HCH3  0   0.247   0.4837  -1.8134    3.6129
 GR4  H182  H  HCH3  0   0.234  -1.1631  -1.9762    3.0579
 GR4  H183  H  HCH3  0   0.249   0.0442  -1.2669    2.0097
 GR4  H191  H  HCH3  0   0.249  -1.2476   3.3578    0.2678
 GR4  H192  H  HCH3  0   0.231   0.3272   3.9609    0.7546
 GR4  H193  H  HCH3  0   0.234  -0.1253   4.0021   -0.9262
 GR4  H221  H  HCH2  0   0.275   0.3071   0.4007    7.0158
 GR4  H222  H  HCH2  0   0.311   1.2491  -0.5250    5.8907
 GR4  H24   H  H     0   0.244   2.7608  -0.1930    7.6984
 GR4  H261  H  HCH3  0   0.250   4.3843  -0.4797   10.6472
 GR4  H262  H  HCH3  0   0.252   5.1462  -1.6362    9.5785
 GR4  H263  H  HCH3  0   0.249   4.6367  -0.0644    8.9449
 GR4  H271  H  HCH3  0   0.267   1.6565  -2.9922   10.0314
 GR4  H272  H  HCH3  0   0.249   3.3759  -3.3481   10.2504
 GR4  H273  H  HCH3  0   0.249   2.6036  -2.1660   11.2770
 GR4  H281  H  HCH2  0   0.216  -2.4982   2.0850    4.3577
 GR4  H282  H  HCH2  0   0.207  -1.2116   2.8214    3.4257
 GR4  H301  H  HCH3  0   0.254  -0.1425   2.8995   -4.3427
 GR4  H302  H  HCH3  0   0.252  -1.6234   2.4308   -3.5218
 GR4  H303  H  HCH3  0   0.253  -0.4990   3.5193   -2.7404
 GR4  HO3   H  HOH1  0   0.449  -4.5975  -0.3402    5.2623
 GR4  H381  H  HCH3  0   0.266   4.8274  -1.5035   -3.5338
 GR4  H382  H  HCH3  0   0.266   3.5521  -1.7610   -2.3194
 GR4  H383  H  HCH3  0   0.274   3.1976  -1.9501   -4.0341
 GR4  HO1   H  HOH1  0   0.451  -3.4152   3.5297    2.9653
 GR4  HO2   H  HOH1  0   0.451   2.5190   0.7603    4.0506
 GR4  H32   H  HCH1  0   0.219   0.1903  -1.5689   -5.4212
 GR4  H33   H  HCH1  0   0.241   0.8343   0.7007   -7.3688
 GR4  H34   H  HCH1  0   0.219   0.8520  -2.3250   -7.7439
 GR4  H35   H  HCH1  0   0.216  -1.0025  -0.2066   -8.9045
 GR4  H36   H  HCH1  0   0.231  -1.5257  -2.4130   -6.8598
 GR4  HO4   H  HOH1  0   0.456  -0.6177  -2.0937  -10.2109
 GR4  HO5   H  HOH1  0   0.458   2.3383  -1.2581   -9.0925
 GR4  HO6   H  HOH1  0   0.460   2.6861   0.2871   -6.2693
 GR4  H311  H  HCH2  0   0.198  -3.3034  -0.1675   -7.9052
 GR4  H312  H  HCH2  0   0.215  -3.4277  -1.8649   -8.3703
 GR4  HO7   H  HOH1  0   0.457  -4.8224  -1.4086   -6.6061
 GR4  H20   H  HCH1  0   0.258  -0.6072  -2.1258    5.5240
 GR4  H21   H  H     0   0.174  -1.9165  -0.5841    7.8249
 GR4  O33   O  O     0  -0.400  -2.5710  -2.3615    7.1476

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
 GR4  C1   C2    single  1.519  0.020  1.519
 GR4  C1   C10   single  1.533  0.020  1.533
 GR4  C1   H11   single  0.970  0.020  1.090
 GR4  C1   H12A  single  0.970  0.020  1.090
 GR4  C2   C3    single  1.513  0.020  1.513
 GR4  C2   H21A  single  0.970  0.020  1.090
 GR4  C2   H22   single  0.970  0.020  1.090
 GR4  C3   C4    single  1.544  0.020  1.544
 GR4  C3   O36   single  1.441  0.020  1.441
 GR4  C3   H3    single  0.970  0.020  1.090
 GR4  C4   C5    single  1.553  0.020  1.553
 GR4  C4   C29   single  1.533  0.020  1.533
 GR4  C4   C30   single  1.539  0.020  1.539
 GR4  C5   C6    single  1.527  0.020  1.527
 GR4  C5   C10   single  1.558  0.020  1.558
 GR4  C5   H5    single  0.970  0.020  1.090
 GR4  C6   C7    single  1.495  0.020  1.495
 GR4  C6   H61   single  0.970  0.020  1.090
 GR4  C6   H62   single  0.970  0.020  1.090
 GR4  C7   C8    double  1.330  0.020  1.330
 GR4  C7   H7    single  0.930  0.020  1.080
 GR4  C8   C9    single  1.518  0.020  1.518
 GR4  C8   C14   single  1.508  0.020  1.508
 GR4  C9   C10   single  1.552  0.020  1.552
 GR4  C9   C11   single  1.528  0.020  1.528
 GR4  C9   H9    single  0.970  0.020  1.090
 GR4  C10  C19   single  1.533  0.020  1.533
 GR4  C11  C12   single  1.549  0.020  1.549
 GR4  C11  H111  single  0.970  0.020  1.090
 GR4  C11  H112  single  0.970  0.020  1.090
 GR4  C12  C13   single  1.548  0.020  1.548
 GR4  C12  O2    single  1.416  0.020  1.416
 GR4  C12  H12   single  0.970  0.020  1.090
 GR4  C13  C14   single  1.564  0.020  1.564
 GR4  C13  C17   single  1.557  0.020  1.557
 GR4  C13  C18   single  1.540  0.020  1.540
 GR4  C14  C15   single  1.531  0.020  1.531
 GR4  C14  C28   single  1.555  0.020  1.555
 GR4  C15  C16   single  1.542  0.020  1.542
 GR4  C15  H151  single  0.970  0.020  1.090
 GR4  C15  H152  single  0.970  0.020  1.090
 GR4  C16  C17   single  1.546  0.020  1.546
 GR4  C16  O32   single  1.414  0.020  1.414
 GR4  C16  H16   single  0.970  0.020  1.090
 GR4  C17  C20   single  1.547  0.020  1.547
 GR4  C17  H17   single  0.970  0.020  1.090
 GR4  C18  H181  single  0.970  0.020  1.090
 GR4  C18  H182  single  0.970  0.020  1.090
 GR4  C18  H183  single  0.970  0.020  1.090
 GR4  C19  H191  single  0.970  0.020  1.090
 GR4  C19  H192  single  0.970  0.020  1.090
 GR4  C19  H193  single  0.970  0.020  1.090
 GR4  C22  C23   single  1.508  0.020  1.508
 GR4  C22  C20   single  1.525  0.020  1.525
 GR4  C22  H221  single  0.970  0.020  1.090
 GR4  C22  H222  single  0.970  0.020  1.090
 GR4  C23  C24   single  1.470  0.020  1.470
 GR4  C23  O35   double  1.219  0.020  1.219
 GR4  C24  C25   double  1.346  0.020  1.346
 GR4  C24  H24   single  0.930  0.020  1.080
 GR4  C25  C26   single  1.497  0.020  1.497
 GR4  C25  C27   single  1.494  0.020  1.494
 GR4  C26  H261  single  0.970  0.020  1.090
 GR4  C26  H262  single  0.970  0.020  1.090
 GR4  C26  H263  single  0.970  0.020  1.090
 GR4  C27  H271  single  0.970  0.020  1.090
 GR4  C27  H272  single  0.970  0.020  1.090
 GR4  C27  H273  single  0.970  0.020  1.090
 GR4  C28  O1    single  1.410  0.020  1.410
 GR4  C28  H281  single  0.970  0.020  1.090
 GR4  C28  H282  single  0.970  0.020  1.090
 GR4  C29  O31   double  1.199  0.020  1.199
 GR4  C29  O34   single  1.342  0.020  1.342
 GR4  C30  H301  single  0.970  0.020  1.090
 GR4  C30  H302  single  0.970  0.020  1.090
 GR4  C30  H303  single  0.970  0.020  1.090
 GR4  O32  HO3   single  0.850  0.020  0.980
 GR4  O33  C21   double  1.206  0.020  1.206
 GR4  O34  C32   single  1.404  0.020  1.404
 GR4  O36  C37   single  1.329  0.020  1.329
 GR4  C37  C38   single  1.498  0.020  1.498
 GR4  C37  O39   double  1.207  0.020  1.207
 GR4  C38  H381  single  0.970  0.020  1.090
 GR4  C38  H382  single  0.970  0.020  1.090
 GR4  C38  H383  single  0.970  0.020  1.090
 GR4  O1   HO1   single  0.850  0.020  0.980
 GR4  O2   HO2   single  0.850  0.020  0.980
 GR4  O3   C32   single  1.391  0.020  1.391
 GR4  O3   C36   single  1.416  0.020  1.416
 GR4  C32  C33   single  1.525  0.020  1.525
 GR4  C32  H32   single  0.970  0.020  1.090
 GR4  C33  C34   single  1.524  0.020  1.524
 GR4  C33  O6    single  1.406  0.020  1.406
 GR4  C33  H33   single  0.970  0.020  1.090
 GR4  C34  C35   single  1.525  0.020  1.525
 GR4  C34  O5    single  1.406  0.020  1.406
 GR4  C34  H34   single  0.970  0.020  1.090
 GR4  C35  C36   single  1.530  0.020  1.530
 GR4  C35  O4    single  1.405  0.020  1.405
 GR4  C35  H35   single  0.970  0.020  1.090
 GR4  C36  C31   single  1.513  0.020  1.513
 GR4  C36  H36   single  0.970  0.020  1.090
 GR4  O4   HO4   single  0.850  0.020  0.980
 GR4  O5   HO5   single  0.850  0.020  0.980
 GR4  O6   HO6   single  0.850  0.020  0.980
 GR4  C31  O7    single  1.407  0.020  1.407
 GR4  C31  H311  single  0.970  0.020  1.090
 GR4  C31  H312  single  0.970  0.020  1.090
 GR4  O7   HO7   single  0.850  0.020  0.980
 GR4  C20  C21   single  1.511  0.020  1.511
 GR4  C20  H20   single  0.970  0.020  1.090
 GR4  C21  H21   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
 GR4  H12A  C1   H11   106.01  3.000
 GR4  H12A  C1   C10   109.61  3.000
 GR4  H11   C1   C10   109.90  3.000
 GR4  H12A  C1   C2    109.57  3.000
 GR4  H11   C1   C2    108.48  3.000
 GR4  C10   C1   C2    113.03  3.000
 GR4  H22   C2   H21A  105.43  3.000
 GR4  H22   C2   C3    109.16  3.000
 GR4  H21A  C2   C3    108.23  3.000
 GR4  H22   C2   C1    110.54  3.000
 GR4  H21A  C2   C1    110.95  3.000
 GR4  C3    C2   C1    112.26  3.000
 GR4  H3    C3   O36   108.97  3.000
 GR4  H3    C3   C4    109.27  3.000
 GR4  O36   C3   C4    105.78  3.000
 GR4  H3    C3   C2    109.57  3.000
 GR4  O36   C3   C2    110.02  3.000
 GR4  C4    C3   C2    113.10  3.000
 GR4  C30   C4   C29   107.38  3.000
 GR4  C30   C4   C5    114.21  3.000
 GR4  C29   C4   C5    108.94  3.000
 GR4  C30   C4   C3    108.81  3.000
 GR4  C29   C4   C3    105.42  3.000
 GR4  C5    C4   C3    111.62  3.000
 GR4  H5    C5   C10   104.53  3.000
 GR4  H5    C5   C6    106.54  3.000
 GR4  C10   C5   C6    109.68  3.000
 GR4  H5    C5   C4    105.12  3.000
 GR4  C10   C5   C4    117.18  3.000
 GR4  C6    C5   C4    112.80  3.000
 GR4  H62   C6   H61   105.25  3.000
 GR4  H62   C6   C7    108.05  3.000
 GR4  H61   C6   C7    109.52  3.000
 GR4  H62   C6   C5    110.80  3.000
 GR4  H61   C6   C5    110.61  3.000
 GR4  C7    C6   C5    112.34  3.000
 GR4  H7    C7   C8    119.77  3.000
 GR4  H7    C7   C6    116.03  3.000
 GR4  C8    C7   C6    124.11  3.000
 GR4  C14   C8   C9    116.57  3.000
 GR4  C14   C8   C7    122.36  3.000
 GR4  C9    C8   C7    121.00  3.000
 GR4  H9    C9   C11   105.69  3.000
 GR4  H9    C9   C10   105.04  3.000
 GR4  C11   C9   C10   115.03  3.000
 GR4  H9    C9   C8    107.87  3.000
 GR4  C11   C9   C8    111.07  3.000
 GR4  C10   C9   C8    111.54  3.000
 GR4  C19   C10  C9    109.48  3.000
 GR4  C19   C10  C5    114.11  3.000
 GR4  C9    C10  C5    104.48  3.000
 GR4  C19   C10  C1    109.51  3.000
 GR4  C9    C10  C1    109.15  3.000
 GR4  C5    C10  C1    109.92  3.000
 GR4  H112  C11  H111  105.18  3.000
 GR4  H112  C11  C12   109.33  3.000
 GR4  H111  C11  C12   107.49  3.000
 GR4  H112  C11  C9    110.31  3.000
 GR4  H111  C11  C9    109.44  3.000
 GR4  C12   C11  C9    114.63  3.000
 GR4  H12   C12  O2    109.34  3.000
 GR4  H12   C12  C13   107.61  3.000
 GR4  O2    C12  C13   109.29  3.000
 GR4  H12   C12  C11   107.32  3.000
 GR4  O2    C12  C11   109.83  3.000
 GR4  C13   C12  C11   113.36  3.000
 GR4  C18   C13  C17   107.96  3.000
 GR4  C18   C13  C14   110.38  3.000
 GR4  C17   C13  C14   100.82  3.000
 GR4  C18   C13  C12   111.04  3.000
 GR4  C17   C13  C12   117.27  3.000
 GR4  C14   C13  C12   108.88  3.000
 GR4  C28   C14  C15   106.09  3.000
 GR4  C28   C14  C13   112.34  3.000
 GR4  C15   C14  C13   102.18  3.000
 GR4  C28   C14  C8    108.96  3.000
 GR4  C15   C14  C8    117.13  3.000
 GR4  C13   C14  C8    110.04  3.000
 GR4  H152  C15  H151  106.56  3.000
 GR4  H152  C15  C16   111.48  3.000
 GR4  H151  C15  C16   110.40  3.000
 GR4  H152  C15  C14   112.76  3.000
 GR4  H151  C15  C14   110.86  3.000
 GR4  C16   C15  C14   104.85  3.000
 GR4  H16   C16  O32   109.34  3.000
 GR4  H16   C16  C17   109.33  3.000
 GR4  O32   C16  C17   107.77  3.000
 GR4  H16   C16  C15   108.70  3.000
 GR4  O32   C16  C15   114.55  3.000
 GR4  C17   C16  C15   107.04  3.000
 GR4  H17   C17  C20   105.84  3.000
 GR4  H17   C17  C16   107.71  3.000
 GR4  C20   C17  C16   112.07  3.000
 GR4  H17   C17  C13   108.25  3.000
 GR4  C20   C17  C13   118.99  3.000
 GR4  C16   C17  C13   103.54  3.000
 GR4  H183  C18  H182  107.00  3.000
 GR4  H183  C18  H181  107.15  3.000
 GR4  H182  C18  H181  106.59  3.000
 GR4  H183  C18  C13   113.31  3.000
 GR4  H182  C18  C13   111.40  3.000
 GR4  H181  C18  C13   111.04  3.000
 GR4  H193  C19  H192  106.03  3.000
 GR4  H193  C19  H191  107.89  3.000
 GR4  H192  C19  H191  107.15  3.000
 GR4  H193  C19  C10   113.38  3.000
 GR4  H192  C19  C10   110.01  3.000
 GR4  H191  C19  C10   112.02  3.000
 GR4  H222  C22  H221  104.83  3.000
 GR4  H222  C22  C20   109.91  3.000
 GR4  H221  C22  C20   110.57  3.000
 GR4  H222  C22  C23   108.73  3.000
 GR4  H221  C22  C23   107.30  3.000
 GR4  C20   C22  C23   114.99  3.000
 GR4  O35   C23  C24   125.14  3.000
 GR4  O35   C23  C22   120.80  3.000
 GR4  C24   C23  C22   114.06  3.000
 GR4  H24   C24  C25   117.26  3.000
 GR4  H24   C24  C23   114.16  3.000
 GR4  C25   C24  C23   128.58  3.000
 GR4  C27   C25  C26   114.06  3.000
 GR4  C27   C25  C24   126.50  3.000
 GR4  C26   C25  C24   119.45  3.000
 GR4  H263  C26  H262  108.47  3.000
 GR4  H263  C26  H261  108.53  3.000
 GR4  H262  C26  H261  106.39  3.000
 GR4  H263  C26  C25   112.72  3.000
 GR4  H262  C26  C25   110.22  3.000
 GR4  H261  C26  C25   110.28  3.000
 GR4  H273  C27  H272  106.01  3.000
 GR4  H273  C27  H271  108.84  3.000
 GR4  H272  C27  H271  108.86  3.000
 GR4  H273  C27  C25   109.23  3.000
 GR4  H272  C27  C25   109.55  3.000
 GR4  H271  C27  C25   114.03  3.000
 GR4  H282  C28  H281  106.52  3.000
 GR4  H282  C28  O1    110.26  3.000
 GR4  H281  C28  O1    109.80  3.000
 GR4  H282  C28  C14   111.92  3.000
 GR4  H281  C28  C14   109.56  3.000
 GR4  O1    C28  C14   108.75  3.000
 GR4  O34   C29  O31   122.70  3.000
 GR4  O34   C29  C4    110.48  3.000
 GR4  O31   C29  C4    126.81  3.000
 GR4  H303  C30  H302  107.04  3.000
 GR4  H303  C30  H301  107.59  3.000
 GR4  H302  C30  H301  107.53  3.000
 GR4  H303  C30  C4    111.58  3.000
 GR4  H302  C30  C4    111.63  3.000
 GR4  H301  C30  C4    111.25  3.000
 GR4  HO3   O32  C16   108.27  3.000
 GR4  C32   O34  C29   119.43  3.000
 GR4  C37   O36  C3    119.32  3.000
 GR4  O39   C37  C38   124.72  3.000
 GR4  O39   C37  O36   123.60  3.000
 GR4  C38   C37  O36   111.65  3.000
 GR4  H383  C38  H382  107.78  3.000
 GR4  H383  C38  H381  107.98  3.000
 GR4  H382  C38  H381  109.86  3.000
 GR4  H383  C38  C37   108.49  3.000
 GR4  H382  C38  C37   112.19  3.000
 GR4  H381  C38  C37   110.40  3.000
 GR4  HO1   O1   C28   107.30  3.000
 GR4  HO2   O2   C12   107.75  3.000
 GR4  C36   O3   C32   113.39  3.000
 GR4  H32   C32  C33   109.69  3.000
 GR4  H32   C32  O3    111.19  3.000
 GR4  C33   C32  O3    110.86  3.000
 GR4  H32   C32  O34   110.86  3.000
 GR4  C33   C32  O34   107.59  3.000
 GR4  O3    C32  O34   106.56  3.000
 GR4  H33   C33  O6    111.69  3.000
 GR4  H33   C33  C34   108.84  3.000
 GR4  O6    C33  C34   108.23  3.000
 GR4  H33   C33  C32   108.61  3.000
 GR4  O6    C33  C32   111.21  3.000
 GR4  C34   C33  C32   108.17  3.000
 GR4  H34   C34  O5    110.73  3.000
 GR4  H34   C34  C35   107.90  3.000
 GR4  O5    C34  C35   107.51  3.000
 GR4  H34   C34  C33   108.20  3.000
 GR4  O5    C34  C33   111.91  3.000
 GR4  C35   C34  C33   110.53  3.000
 GR4  H35   C35  O4    111.18  3.000
 GR4  H35   C35  C36   108.05  3.000
 GR4  O4    C35  C36   108.16  3.000
 GR4  H35   C35  C34   108.34  3.000
 GR4  O4    C35  C34   111.43  3.000
 GR4  C36   C35  C34   109.62  3.000
 GR4  H36   C36  C31   109.10  3.000
 GR4  H36   C36  C35   108.70  3.000
 GR4  C31   C36  C35   112.03  3.000
 GR4  H36   C36  O3    110.08  3.000
 GR4  C31   C36  O3    107.64  3.000
 GR4  C35   C36  O3    109.28  3.000
 GR4  HO4   O4   C35   108.14  3.000
 GR4  HO5   O5   C34   108.65  3.000
 GR4  HO6   O6   C33   109.34  3.000
 GR4  H312  C31  H311  107.10  3.000
 GR4  H312  C31  O7    111.79  3.000
 GR4  H311  C31  O7    111.90  3.000
 GR4  H312  C31  C36   108.31  3.000
 GR4  H311  C31  C36   108.83  3.000
 GR4  O7    C31  C36   108.81  3.000
 GR4  HO7   O7   C31   107.91  3.000
 GR4  H20   C20  C21   107.55  3.000
 GR4  H20   C20  C22   110.31  3.000
 GR4  C21   C20  C22   109.33  3.000
 GR4  H20   C20  C17   109.97  3.000
 GR4  C21   C20  C17   108.48  3.000
 GR4  C22   C20  C17   111.11  3.000
 GR4  H21   C21  C20   114.01  3.000
 GR4  H21   C21  O33   120.68  3.000
 GR4  C20   C21  O33   125.28  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
 GR4  Var_01  C10   C1   C2   C3    -58.34  30.0  1
 GR4  Var_02  C8    C7   C6   C5     13.05  30.0  1
 GR4  Var_03  C9    C8   C7   C6     -2.85  30.0  1
 GR4  Var_04  C38   C37  O36  C3   -173.36  30.0  3
 GR4  Var_05  C26   C25  C24  C23  -179.96   0.0  2
 GR4  Var_06  C25   C24  C23  C22   176.02  30.0  2
 GR4  Var_07  C20   C22  C23  C24   172.00  30.0  2
 GR4  Var_08  H261  C26  C25  C24   122.44  30.0  3
 GR4  Var_09  H271  C27  C25  C24     0.56  30.0  3
 GR4  Var_10  H381  C38  C37  O36  -158.07  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
 GR4  chir_01  C3   C2   C4   O36  positiv
 GR4  chir_02  C4   C5   C3   C30  positiv
 GR4  chir_03  C5   C10  C6   C4   negativ
 GR4  chir_04  C9   C8   C10  C11  negativ
 GR4  chir_05  C10  C5   C9   C1   negativ
 GR4  chir_06  C12  O2   C11  C13  negativ
 GR4  chir_07  C13  C14  C17  C12  positiv
 GR4  chir_08  C14  C15  C13  C8   negativ
 GR4  chir_09  C16  O32  C15  C17  negativ
 GR4  chir_10  C17  C13  C16  C20  negativ
 GR4  chir_11  C32  O34  O3   C33  negativ
 GR4  chir_12  C33  O6   C32  C34  positiv
 GR4  chir_13  C34  O5   C33  C35  negativ
 GR4  chir_14  C35  O4   C34  C36  positiv
 GR4  chir_15  C36  O3   C35  C31  positiv
 GR4  chir_16  C20  C17  C22  C21  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
 GR4  plan-1  C22  0.020
 GR4  plan-1  C23  0.020
 GR4  plan-1  C24  0.020
 GR4  plan-1  O35  0.020
 GR4  plan-2  C23  0.020
 GR4  plan-2  C24  0.020
 GR4  plan-2  C25  0.020
 GR4  plan-2  C26  0.020
 GR4  plan-2  C27  0.020
 GR4  plan-2  H24  0.020
 GR4  plan-3  C4   0.020
 GR4  plan-3  C29  0.020
 GR4  plan-3  O31  0.020
 GR4  plan-3  O34  0.020
 GR4  plan-4  C20  0.020
 GR4  plan-4  C21  0.020
 GR4  plan-4  H21  0.020
 GR4  plan-4  O33  0.020
 GR4  plan-5  O36  0.020
 GR4  plan-5  C37  0.020
 GR4  plan-5  C38  0.020
 GR4  plan-5  O39  0.020

