# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 29 20:57:51 2021
#   Inital geometry file: a 170 line input string
#   Ligand name: (~{E},3~{R},4~{R},6~{R})-8-[(2~{S},3~{S},7~{R},8~{E},10~{R},11~{R})-3,7-dimethyl-10,11-bis(oxidanyl)-12-oxidanylidene-1-oxacyclododec-8-en-2-yl]-3-methoxy-4,6-dimethyl-5-oxidanylidene-non-7-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@H](CC(O)=O)[C@@H](C)C(=O)[C@H](C)\C=C(C)\[C@H]1OC(=O)[C@H](O)[C@H](O)/C=C/[C@H](C)CCC[C@@H]1C
#
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
 C3R  C3R  '(~{E},3~{R},4~{R},6~{R})-8-[(2~{S},3~{S},7~{R},8~{E},10~{R},11~{R})-3,7-dimethyl-10,11-bis(oxidanyl)-12-oxidanylidene-1-oxacyclododec-8-en-2-yl]-3-methoxy-4,6-dimethyl-5-oxidanylidene-non-7-enoic acid'  ligand  73  33  .  2021-08-07  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C3R
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
 C3R  C10  C  CH2   0  -0.449  -57.5006   8.8263  -1.0947
 C3R  C13  C  CH3   0  -0.671  -57.0344   6.6822  -3.3977
 C3R  C15  C  C     0   0.119  -57.1546   4.3289  -1.5092
 C3R  C17  C  C1    0  -0.225  -58.3274   3.7248  -1.7075
 C3R  C20  C  C     0   0.434  -58.9858   2.3347  -3.6021
 C3R  C21  C  CH1   0  -0.374  -57.9089   2.7043  -4.6093
 C3R  C22  C  CH3   0  -0.675  -58.4483   3.6977  -5.6348
 C3R  C01  C  CH3   0  -0.647  -56.3879  11.6711   1.3394
 C3R  C02  C  CH1   0  -0.310  -56.4088  10.2581   0.7574
 C3R  C03  C  C1    0  -0.156  -56.9107   9.2684   1.7650
 C3R  C04  C  C1    0  -0.292  -56.2032   8.2393   2.2169
 C3R  C05  C  CH1   0  -0.024  -56.6792   7.1983   3.1779
 C3R  O06  O  OH1   0  -0.657  -58.0130   7.4374   3.5302
 C3R  C07  C  CH1   0  -0.083  -56.4962   5.7758   2.5907
 C3R  O08  O  OH1   0  -0.662  -56.8982   4.8003   3.5152
 C3R  C09  C  CH2   0  -0.405  -57.2746  10.2197  -0.5125
 C3R  C11  C  CH2   0  -0.416  -56.2074   8.1149  -1.4756
 C3R  C12  C  CH1   0  -0.281  -56.3670   6.6917  -2.0242
 C3R  C14  C  CH1   0  -0.028  -57.1526   5.7767  -1.0814
 C3R  C16  C  CH3   0  -0.761  -55.8124   3.6872  -1.6974
 C3R  C18  C  CH1   0  -0.453  -58.5706   2.3038  -2.1402
 C3R  C19  C  CH3   0  -0.650  -59.6066   1.6341  -1.2473
 C3R  C23  C  CH1   0   0.088  -57.3725   1.4236  -5.2745
 C3R  O24  O  O2    0  -0.499  -56.9264   0.4969  -4.3038
 C3R  C25  C  CH3   0  -0.417  -57.7453  -0.6363  -4.1121
 C3R  O28  O  OH1   0  -0.591  -56.3338  -0.3062  -7.3044
 C3R  O29  O  O     0  -0.441  -54.3199   0.2613  -6.5367
 C3R  O31  O  O2    0  -0.462  -56.5422   5.8751   0.2267
 C3R  C32  C  C     0   0.575  -57.2749   5.6144   1.2943
 C3R  O33  O  O     0  -0.438  -58.4336   5.2838   1.2759
 C3R  H2   H  HCH2  0   0.228  -58.1520   8.9154  -1.9690
 C3R  H1   H  HCH2  0   0.221  -58.0569   8.2321  -0.3644
 C3R  H4   H  HCH3  0   0.241  -57.0404   5.6860  -3.8405
 C3R  H3   H  HCH3  0   0.225  -58.0719   7.0177  -3.3449
 C3R  H5   H  HCH3  0   0.238  -56.5034   7.3433  -4.0830
 C3R  H6   H  H     0   0.248  -59.2339   4.3009  -1.5419
 C3R  H7   H  HCH1  0   0.263  -57.0760   3.1625  -4.0691
 C3R  H10  H  HCH3  0   0.248  -58.9273   4.5432  -5.1403
 C3R  H8   H  HCH3  0   0.245  -57.6452   4.0992  -6.2514
 C3R  H9   H  HCH3  0   0.240  -59.1838   3.2349  -6.2928
 C3R  H14  H  HCH3  0   0.229  -55.7184  11.7379   2.1978
 C3R  H13  H  HCH3  0   0.226  -56.0505  12.3933   0.5935
 C3R  H15  H  HCH3  0   0.216  -57.3838  11.9761   1.6682
 C3R  H16  H  HCH1  0   0.230  -55.3810   9.9883   0.4927
 C3R  H17  H  H     0   0.237  -57.9319   9.4182   2.1072
 C3R  H18  H  H     0   0.246  -55.1829   8.1025   1.8672
 C3R  H19  H  HCH1  0   0.245  -56.0267   7.2239   4.0650
 C3R  H20  H  HOH1  0   0.456  -58.2215   6.9238   4.3161
 C3R  H21  H  HCH1  0   0.265  -55.4306   5.6268   2.3982
 C3R  H22  H  HOH1  0   0.449  -57.8541   4.6856   3.4506
 C3R  H23  H  HCH2  0   0.220  -56.8123  10.8645  -1.2673
 C3R  H24  H  HCH2  0   0.217  -58.2482  10.6671  -0.2844
 C3R  H25  H  HCH2  0   0.237  -55.5431   8.0844  -0.6117
 C3R  H26  H  HCH2  0   0.222  -55.6817   8.7087  -2.2309
 C3R  H27  H  HCH1  0   0.244  -55.3563   6.2857  -2.1424
 C3R  H28  H  HCH1  0   0.256  -58.1839   6.1330  -1.0171
 C3R  H30  H  HCH3  0   0.258  -55.1234   3.9584  -0.8964
 C3R  H31  H  HCH3  0   0.255  -55.8683   2.6011  -1.7262
 C3R  H29  H  HCH3  0   0.246  -55.3464   4.0077  -2.6338
 C3R  H32  H  HCH1  0   0.283  -57.6350   1.7388  -2.0988
 C3R  H34  H  HCH3  0   0.240  -59.2356   1.5814  -0.2244
 C3R  H35  H  HCH3  0   0.229  -60.5445   2.1897  -1.2325
 C3R  H33  H  HCH3  0   0.237  -59.8221   0.6175  -1.5781
 C3R  H36  H  HCH1  0   0.236  -58.1750   0.9838  -5.8800
 C3R  H38  H  HCH3  0   0.239  -57.2011  -1.3262  -3.4690
 C3R  H39  H  HCH3  0   0.211  -58.6955  -0.3975  -3.6237
 C3R  H37  H  HCH3  0   0.221  -57.9677  -1.1423  -5.0562
 C3R  H40  H  HOH1  0   0.482  -55.8676  -1.0993  -7.6086
 C3R  O30  O  O     0  -0.392  -60.1157   2.0920  -3.9581
 C3R  C26  C  CH2   0  -0.583  -56.1762   1.7467  -6.1681
 C3R  C27  C  C     0   0.541  -55.4934   0.5027  -6.6683
 C3R  H12  H  HCH2  0   0.267  -55.4458   2.3423  -5.6181
 C3R  H11  H  HCH2  0   0.292  -56.4968   2.3352  -7.0312

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
 C3R  O29  C27  double  1.205  0.020  1.205
 C3R  O28  C27  single  1.329  0.020  1.329
 C3R  C27  C26  single  1.505  0.020  1.505
 C3R  C26  C23  single  1.528  0.020  1.528
 C3R  C22  C21  single  1.526  0.020  1.526
 C3R  C23  C21  single  1.540  0.020  1.540
 C3R  C23  O24  single  1.414  0.020  1.414
 C3R  C21  C20  single  1.520  0.020  1.520
 C3R  O24  C25  single  1.411  0.020  1.411
 C3R  O30  C20  double  1.209  0.020  1.209
 C3R  C20  C18  single  1.520  0.020  1.520
 C3R  C13  C12  single  1.527  0.020  1.527
 C3R  C18  C17  single  1.505  0.020  1.505
 C3R  C18  C19  single  1.523  0.020  1.523
 C3R  C12  C11  single  1.534  0.020  1.534
 C3R  C12  C14  single  1.531  0.020  1.531
 C3R  C17  C15  double  1.334  0.020  1.334
 C3R  C11  C10  single  1.524  0.020  1.524
 C3R  C16  C15  single  1.500  0.020  1.500
 C3R  C15  C14  single  1.510  0.020  1.510
 C3R  C10  C09  single  1.527  0.020  1.527
 C3R  C14  O31  single  1.447  0.020  1.447
 C3R  C09  C02  single  1.537  0.020  1.537
 C3R  O31  C32  single  1.321  0.020  1.321
 C3R  C02  C01  single  1.528  0.020  1.528
 C3R  C02  C03  single  1.499  0.020  1.499
 C3R  O33  C32  double  1.205  0.020  1.205
 C3R  C32  C07  single  1.521  0.020  1.521
 C3R  C03  C04  double  1.328  0.020  1.328
 C3R  C04  C05  single  1.495  0.020  1.495
 C3R  C07  C05  single  1.550  0.020  1.550
 C3R  C07  O08  single  1.403  0.020  1.403
 C3R  C05  O06  single  1.400  0.020  1.400
 C3R  C10  H2   single  0.970  0.020  1.090
 C3R  C10  H1   single  0.970  0.020  1.090
 C3R  C13  H4   single  0.970  0.020  1.090
 C3R  C13  H3   single  0.970  0.020  1.090
 C3R  C13  H5   single  0.970  0.020  1.090
 C3R  C17  H6   single  0.930  0.020  1.080
 C3R  C21  H7   single  0.970  0.020  1.090
 C3R  C22  H10  single  0.970  0.020  1.090
 C3R  C22  H8   single  0.970  0.020  1.090
 C3R  C22  H9   single  0.970  0.020  1.090
 C3R  C26  H12  single  0.970  0.020  1.090
 C3R  C26  H11  single  0.970  0.020  1.090
 C3R  C01  H14  single  0.970  0.020  1.090
 C3R  C01  H13  single  0.970  0.020  1.090
 C3R  C01  H15  single  0.970  0.020  1.090
 C3R  C02  H16  single  0.970  0.020  1.090
 C3R  C03  H17  single  0.930  0.020  1.080
 C3R  C04  H18  single  0.930  0.020  1.080
 C3R  C05  H19  single  0.970  0.020  1.090
 C3R  O06  H20  single  0.850  0.020  0.980
 C3R  C07  H21  single  0.970  0.020  1.090
 C3R  O08  H22  single  0.850  0.020  0.980
 C3R  C09  H23  single  0.970  0.020  1.090
 C3R  C09  H24  single  0.970  0.020  1.090
 C3R  C11  H25  single  0.970  0.020  1.090
 C3R  C11  H26  single  0.970  0.020  1.090
 C3R  C12  H27  single  0.970  0.020  1.090
 C3R  C14  H28  single  0.970  0.020  1.090
 C3R  C16  H30  single  0.970  0.020  1.090
 C3R  C16  H31  single  0.970  0.020  1.090
 C3R  C16  H29  single  0.970  0.020  1.090
 C3R  C18  H32  single  0.970  0.020  1.090
 C3R  C19  H34  single  0.970  0.020  1.090
 C3R  C19  H35  single  0.970  0.020  1.090
 C3R  C19  H33  single  0.970  0.020  1.090
 C3R  C23  H36  single  0.970  0.020  1.090
 C3R  C25  H38  single  0.970  0.020  1.090
 C3R  C25  H39  single  0.970  0.020  1.090
 C3R  C25  H37  single  0.970  0.020  1.090
 C3R  O28  H40  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
 C3R  H1   C10  H2   105.97  3.000
 C3R  H1   C10  C11  110.17  3.000
 C3R  H2   C10  C11  110.09  3.000
 C3R  H1   C10  C09  108.46  3.000
 C3R  H2   C10  C09  108.58  3.000
 C3R  C11  C10  C09  113.30  3.000
 C3R  H5   C13  H3   107.88  3.000
 C3R  H5   C13  H4   107.54  3.000
 C3R  H3   C13  H4   107.17  3.000
 C3R  H5   C13  C12  110.41  3.000
 C3R  H3   C13  C12  111.71  3.000
 C3R  H4   C13  C12  111.92  3.000
 C3R  C16  C15  C14  116.41  3.000
 C3R  C14  C15  C17  118.53  3.000
 C3R  C16  C15  C17  125.05  3.000
 C3R  H6   C17  C18  114.17  3.000
 C3R  H6   C17  C15  118.07  3.000
 C3R  C18  C17  C15  127.76  3.000
 C3R  O30  C20  C18  122.29  3.000
 C3R  C18  C20  C21  116.66  3.000
 C3R  O30  C20  C21  121.04  3.000
 C3R  H7   C21  C23  107.25  3.000
 C3R  H7   C21  C22  109.17  3.000
 C3R  C23  C21  C22  111.98  3.000
 C3R  H7   C21  C20  108.31  3.000
 C3R  C23  C21  C20  109.32  3.000
 C3R  C22  C21  C20  110.68  3.000
 C3R  H9   C22  H8   108.20  3.000
 C3R  H9   C22  H10  107.85  3.000
 C3R  H8   C22  H10  107.14  3.000
 C3R  H9   C22  C21  111.57  3.000
 C3R  H8   C22  C21  111.08  3.000
 C3R  H10  C22  C21  110.81  3.000
 C3R  H15  C01  H13  107.62  3.000
 C3R  H15  C01  H14  107.80  3.000
 C3R  H13  C01  H14  107.91  3.000
 C3R  H15  C01  C02  111.13  3.000
 C3R  H13  C01  C02  110.83  3.000
 C3R  H14  C01  C02  111.39  3.000
 C3R  H16  C02  C09  108.83  3.000
 C3R  H16  C02  C03  108.31  3.000
 C3R  C09  C02  C03  110.50  3.000
 C3R  H16  C02  C01  107.88  3.000
 C3R  C03  C02  C01  111.04  3.000
 C3R  C09  C02  C01  110.20  3.000
 C3R  H17  C03  C04  120.00  3.000
 C3R  H17  C03  C02  115.79  3.000
 C3R  C04  C03  C02  124.19  3.000
 C3R  H18  C04  C05  114.71  3.000
 C3R  H18  C04  C03  119.21  3.000
 C3R  C05  C04  C03  126.07  3.000
 C3R  H19  C05  C07  104.87  3.000
 C3R  H19  C05  O06  110.95  3.000
 C3R  C07  C05  O06  111.38  3.000
 C3R  H19  C05  C04  108.24  3.000
 C3R  O06  C05  C04  110.26  3.000
 C3R  C07  C05  C04  110.98  3.000
 C3R  H20  O06  C05  108.72  3.000
 C3R  H21  C07  C32  109.55  3.000
 C3R  H21  C07  O08  107.50  3.000
 C3R  C32  C07  O08  109.95  3.000
 C3R  H21  C07  C05  107.87  3.000
 C3R  O08  C07  C05  110.77  3.000
 C3R  C32  C07  C05  111.09  3.000
 C3R  H22  O08  C07  108.81  3.000
 C3R  H24  C09  H23  106.15  3.000
 C3R  H24  C09  C02  108.56  3.000
 C3R  H23  C09  C02  108.48  3.000
 C3R  H24  C09  C10  108.69  3.000
 C3R  H23  C09  C10  109.70  3.000
 C3R  C02  C09  C10  114.90  3.000
 C3R  H26  C11  H25  105.62  3.000
 C3R  H26  C11  C12  107.84  3.000
 C3R  H25  C11  C12  108.72  3.000
 C3R  H26  C11  C10  109.06  3.000
 C3R  H25  C11  C10  109.39  3.000
 C3R  C12  C11  C10  115.74  3.000
 C3R  H27  C12  C14  108.57  3.000
 C3R  H27  C12  C11  106.65  3.000
 C3R  C14  C12  C11  112.82  3.000
 C3R  H27  C12  C13  107.69  3.000
 C3R  C14  C12  C13  109.02  3.000
 C3R  C11  C12  C13  111.90  3.000
 C3R  H28  C14  O31  108.83  3.000
 C3R  H28  C14  C12  109.01  3.000
 C3R  O31  C14  C12  107.43  3.000
 C3R  H28  C14  C15  109.15  3.000
 C3R  O31  C14  C15  108.78  3.000
 C3R  C12  C14  C15  113.54  3.000
 C3R  H29  C16  H31  106.96  3.000
 C3R  H29  C16  H30  106.65  3.000
 C3R  H31  C16  H30  107.47  3.000
 C3R  H29  C16  C15  111.31  3.000
 C3R  H31  C16  C15  112.62  3.000
 C3R  H30  C16  C15  111.52  3.000
 C3R  H32  C18  C19  109.43  3.000
 C3R  H32  C18  C20  106.29  3.000
 C3R  C19  C18  C20  112.77  3.000
 C3R  H32  C18  C17  109.79  3.000
 C3R  C19  C18  C17  110.89  3.000
 C3R  C20  C18  C17  107.55  3.000
 C3R  H33  C19  H35  108.01  3.000
 C3R  H33  C19  H34  107.88  3.000
 C3R  H35  C19  H34  107.75  3.000
 C3R  H33  C19  C18  111.50  3.000
 C3R  H35  C19  C18  111.66  3.000
 C3R  H34  C19  C18  109.88  3.000
 C3R  H36  C23  O24  110.29  3.000
 C3R  H36  C23  C26  109.55  3.000
 C3R  O24  C23  C26  107.04  3.000
 C3R  H36  C23  C21  108.48  3.000
 C3R  O24  C23  C21  111.01  3.000
 C3R  C26  C23  C21  110.46  3.000
 C3R  C25  O24  C23  115.87  3.000
 C3R  H37  C25  H39  108.02  3.000
 C3R  H37  C25  H38  108.56  3.000
 C3R  H39  C25  H38  107.96  3.000
 C3R  H37  C25  O24  111.85  3.000
 C3R  H39  C25  O24  112.90  3.000
 C3R  H38  C25  O24  107.40  3.000
 C3R  H40  O28  C27  110.14  3.000
 C3R  C32  O31  C14  118.90  3.000
 C3R  O33  C32  O31  125.11  3.000
 C3R  O33  C32  C07  122.31  3.000
 C3R  O31  C32  C07  112.58  3.000
 C3R  H11  C26  H12  107.49  3.000
 C3R  H11  C26  C27  108.41  3.000
 C3R  H12  C26  C27  108.36  3.000
 C3R  H11  C26  C23  110.25  3.000
 C3R  H12  C26  C23  110.17  3.000
 C3R  C27  C26  C23  112.02  3.000
 C3R  O29  C27  O28  123.11  3.000
 C3R  O28  C27  C26  112.05  3.000
 C3R  O29  C27  C26  124.83  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
 C3R  CONST_01  H40  O28  C27  C26   180.00   0.0  0
 C3R  Var_01    C05  C04  C03  C02  -177.42   0.0  0
 C3R  Var_02    C11  C10  C09  C02   -59.22  30.0  1
 C3R  Var_03    C12  C11  C10  C09   178.09  30.0  1
 C3R  Var_04    O33  C32  O31  C14     0.60  30.0  1
 C3R  Var_05    H17  C03  C04  C05     0.93   0.0  0
 C3R  Var_06    C18  C17  C15  C14   179.59   0.0  2
 C3R  Var_07    H30  C16  C15  C14    42.88  30.0  3
 C3R  Var_08    O29  C27  C26  C23  -125.52  30.0  2
 C3R  Var_09    H38  C25  O24  C23   170.87  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
 C3R  chir_01  C21  C22  C23  C20  positiv
 C3R  chir_02  C02  C09  C01  C03  negativ
 C3R  chir_03  C05  O06  C07  C04  negativ
 C3R  chir_04  C07  O08  C05  C32  positiv
 C3R  chir_05  C12  C13  C11  C14  negativ
 C3R  chir_06  C14  O31  C12  C15  negativ
 C3R  chir_07  C18  C20  C17  C19  negativ
 C3R  chir_08  C23  O24  C26  C21  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
 C3R  plan-1  C20  0.020
 C3R  plan-1  C21  0.020
 C3R  plan-1  C18  0.020
 C3R  plan-1  O30  0.020
 C3R  plan-2  O28  0.020
 C3R  plan-2  O29  0.020
 C3R  plan-2  H40  0.020
 C3R  plan-2  C26  0.020
 C3R  plan-2  C27  0.020
 C3R  plan-3  C15  0.020
 C3R  plan-3  C17  0.020
 C3R  plan-3  C14  0.020
 C3R  plan-3  C16  0.020
 C3R  plan-3  C18  0.020
 C3R  plan-3  H6   0.020
 C3R  plan-4  C07  0.020
 C3R  plan-4  O31  0.020
 C3R  plan-4  C32  0.020
 C3R  plan-4  O33  0.020
 C3R  plan-5  C02  0.020
 C3R  plan-5  C03  0.020
 C3R  plan-5  C04  0.020
 C3R  plan-5  C05  0.020
 C3R  plan-5  H17  0.020
 C3R  plan-5  H18  0.020

