 
data_pf2b
_publ_contact_author_name      'Khanitha Pudhom'
_publ_contact_author_address
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
_publ_contact_author_phone      ?
_publ_contact_author_fax        ?
_publ_contact_author_email      ?
_publ_requested_journal         'Organic Letters'
_publ_requested_coeditor_name   ?

_publ_contact_letter
;
Please send back the ccdc code by mail
;
loop_
_publ_author_name
_publ_author_address
     'Achara Raksat'
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
     'Kedkran Koopklang'
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
     'Siwattra Choodej'
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
     'Thammarat Aree'
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
     'Khanitha Pudhom'
;
     Department of Chemistry
     Faculty of science
     Chulalongkorn University
     Phyathai Rd.,Pathumwan
     Bangkok 10330, Thailand
;
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             'Macropterin A'
_chemical_melting_point           ?
_chemical_formula_moiety          'C40 H56 O5'
_chemical_formula_sum             'C40 H56 O5' 
_chemical_formula_weight          616.84

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'
 
_cell_length_a                    6.9234(2)
_cell_length_b                    12.1772(3)
_cell_length_c                    41.1985(9)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3473.35(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9976
_cell_measurement_theta_min       3.79
_cell_measurement_theta_max       67.88
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.180          
_exptl_crystal_F_000              1344
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.480
_exptl_crystal_size_mid           0.400
_exptl_crystal_size_min           0.180
_exptl_absorpt_coefficient_mu     0.593
_shelx_estimated_absorpt_T_min    0.764
_shelx_estimated_absorpt_T_max    0.901
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.594
_exptl_absorpt_correction_T_max   0.753
_exptl_absorpt_process_details    'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'microfocus I\mS'
_diffrn_measurement_device_type   PROSPECTOR
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             21426
_diffrn_reflns_av_unetI/netI      0.0375
_diffrn_reflns_av_R_equivalents   0.0386
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -48
_diffrn_reflns_limit_l_max        49
_diffrn_reflns_theta_min          2.145
_diffrn_reflns_theta_max          68.351
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.986
_diffrn_measured_fraction_theta_full  0.992
_diffrn_reflns_Laue_measured_fraction_max    0.986
_diffrn_reflns_Laue_measured_fraction_full   0.992
_diffrn_reflns_point_group_measured_fraction_max   0.974
_diffrn_reflns_point_group_measured_fraction_full  0.982
_reflns_number_total              6216
_reflns_number_gt                 5920
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.717
_reflns_Friedel_fraction_max      0.957
_reflns_Friedel_fraction_full     0.968
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.6900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 2314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.02(7)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          6216
_refine_ls_number_parameters      413
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0435
_refine_ls_R_factor_gt            0.0418
_refine_ls_wR_factor_ref          0.1066
_refine_ls_wR_factor_gt           0.1054
_refine_ls_goodness_of_fit_ref    1.045
_refine_ls_restrained_S_all       1.045
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6949(5) 0.2761(3) 0.63485(7) 0.0582(7) Uani 1 1 d . . . . .
H1A H 0.811733 0.258843 0.646800 0.070 Uiso 1 1 calc R U . . .
H1B H 0.617164 0.209903 0.633848 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7496(6) 0.3100(3) 0.60044(8) 0.0718(10) Uani 1 1 d . . . . .
H2A H 0.838429 0.371534 0.601297 0.086 Uiso 1 1 calc R U . . .
H2B H 0.814680 0.249454 0.589723 0.086 Uiso 1 1 calc R U . . .
C3 C 0.5717(6) 0.3423(3) 0.58098(7) 0.0696(9) Uani 1 1 d . . . . .
H3A H 0.488953 0.278486 0.578641 0.084 Uiso 1 1 calc R U . . .
H3B H 0.611778 0.364799 0.559428 0.084 Uiso 1 1 calc R U . . .
C4 C 0.4547(4) 0.4357(3) 0.59654(6) 0.0533(7) Uani 1 1 d . . . . .
C5 C 0.4080(4) 0.4020(2) 0.63230(6) 0.0401(5) Uani 1 1 d . . . . .
H5 H 0.325775 0.336802 0.630407 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2870(4) 0.4849(3) 0.65065(6) 0.0512(7) Uani 1 1 d . . . . .
H6A H 0.177610 0.506257 0.637360 0.061 Uiso 1 1 calc R U . . .
H6B H 0.363786 0.550002 0.654779 0.061 Uiso 1 1 calc R U . . .
C7 C 0.2136(4) 0.4392(2) 0.68282(6) 0.0473(6) Uani 1 1 d . . . . .
H7A H 0.121408 0.381051 0.678434 0.057 Uiso 1 1 calc R U . . .
H7B H 0.146228 0.496936 0.694418 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3739(3) 0.39387(18) 0.70448(5) 0.0327(5) Uani 1 1 d . . . . .
H8 H 0.457046 0.455616 0.710602 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4976(3) 0.31304(18) 0.68481(5) 0.0340(5) Uani 1 1 d . . . . .
H9 H 0.410896 0.253914 0.677854 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5826(3) 0.36452(19) 0.65331(6) 0.0377(5) Uani 1 1 d . . . . .
C11 C 0.6490(4) 0.2601(3) 0.70691(6) 0.0505(7) Uani 1 1 d . . . . .
H11A H 0.720066 0.205372 0.694639 0.061 Uiso 1 1 calc R U . . .
H11B H 0.740048 0.315827 0.713898 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5620(4) 0.2069(2) 0.73609(6) 0.0417(5) Uani 1 1 d . . . . .
C13 C 0.3868(3) 0.25727(18) 0.74972(5) 0.0347(5) Uani 1 1 d . . . . .
C14 C 0.2982(3) 0.34262(17) 0.73565(5) 0.0318(5) Uani 1 1 d . . . . .
C15 C 0.3095(4) 0.20750(18) 0.78065(6) 0.0375(5) Uani 1 1 d . . . . .
H15 H 0.347255 0.129936 0.780550 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4003(4) 0.2589(2) 0.81073(6) 0.0422(5) Uani 1 1 d . . . . .
C17 C 0.1256(4) 0.39584(19) 0.75139(6) 0.0382(5) Uani 1 1 d . . . . .
H17A H 0.035260 0.416128 0.734423 0.046 Uiso 1 1 calc R U . . .
H17B H 0.168341 0.463194 0.761710 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5627(6) 0.5448(3) 0.59297(8) 0.0707(9) Uani 1 1 d . . . . .
H18A H 0.565036 0.565976 0.570531 0.106 Uiso 1 1 calc R U . . .
H18B H 0.692635 0.536437 0.600728 0.106 Uiso 1 1 calc R U . . .
H18C H 0.498167 0.600436 0.605429 0.106 Uiso 1 1 calc R U . . .
C19 C 0.2633(6) 0.4456(4) 0.57783(8) 0.0866(13) Uani 1 1 d . . . . .
H19A H 0.198542 0.511989 0.584085 0.130 Uiso 1 1 calc R U . . .
H19B H 0.182682 0.383643 0.582772 0.130 Uiso 1 1 calc R U . . .
H19C H 0.289151 0.447215 0.554938 0.130 Uiso 1 1 calc R U . . .
C20 C 0.7180(4) 0.4601(3) 0.66201(7) 0.0536(7) Uani 1 1 d . . . . .
H20A H 0.783573 0.443920 0.681980 0.080 Uiso 1 1 calc R U . . .
H20B H 0.643833 0.526155 0.664497 0.080 Uiso 1 1 calc R U . . .
H20C H 0.811141 0.469833 0.644996 0.080 Uiso 1 1 calc R U . . .
C1' C 0.0673(7) 0.3059(4) 0.93625(7) 0.0842(12) Uani 1 1 d . . . . .
H1'1 H 0.197360 0.326347 0.929943 0.101 Uiso 1 1 calc R U . . .
H1'2 H 0.047776 0.229735 0.930149 0.101 Uiso 1 1 calc R U . . .
C2' C 0.0478(10) 0.3165(5) 0.97314(9) 0.1172(19) Uani 1 1 d . . . . .
H2'1 H -0.079040 0.291445 0.979834 0.141 Uiso 1 1 calc R U . . .
H2'2 H 0.143687 0.270598 0.983670 0.141 Uiso 1 1 calc R U . . .
C3' C 0.0758(10) 0.4347(5) 0.98341(9) 0.127(2) Uani 1 1 d . . . . .
H3'1 H 0.206999 0.456428 0.978206 0.152 Uiso 1 1 calc R U . . .
H3'2 H 0.061406 0.439108 1.006798 0.152 Uiso 1 1 calc R U . . .
C4' C -0.0628(8) 0.5167(4) 0.96782(8) 0.0968(15) Uani 1 1 d . . . . .
C5' C -0.0583(6) 0.4981(3) 0.93006(7) 0.0669(9) Uani 1 1 d . . . . .
H5' H 0.072732 0.519764 0.923738 0.080 Uiso 1 1 calc R U . . .
C6' C -0.1864(7) 0.5746(3) 0.91122(8) 0.0788(11) Uani 1 1 d . . . . .
H6'1 H -0.171307 0.648614 0.919561 0.095 Uiso 1 1 calc R U . . .
H6'2 H -0.320105 0.553140 0.914274 0.095 Uiso 1 1 calc R U . . .
C7' C -0.1393(7) 0.5738(2) 0.87502(7) 0.0697(10) Uani 1 1 d . . . . .
H7'1 H -0.011313 0.604228 0.871682 0.084 Uiso 1 1 calc R U . . .
H7'2 H -0.231082 0.619814 0.863565 0.084 Uiso 1 1 calc R U . . .
C8' C -0.1466(4) 0.4575(2) 0.86116(6) 0.0466(6) Uani 1 1 d . . . . .
H8' H -0.280131 0.431383 0.862839 0.056 Uiso 1 1 calc R U . . .
C9' C -0.0187(4) 0.3798(2) 0.88110(6) 0.0439(6) Uani 1 1 d . . . . .
H9' H 0.113384 0.408556 0.879967 0.053 Uiso 1 1 calc R U . . .
C10' C -0.0768(5) 0.3775(3) 0.91775(6) 0.0546(7) Uani 1 1 d . . . . .
C11' C -0.0166(4) 0.2661(2) 0.86512(6) 0.0445(6) Uani 1 1 d . . . . .
H11C H 0.052690 0.214934 0.878895 0.053 Uiso 1 1 calc R U . . .
H11D H -0.148034 0.239744 0.862743 0.053 Uiso 1 1 calc R U . . .
C12' C 0.0785(3) 0.27091(19) 0.83240(6) 0.0373(5) Uani 1 1 d . . . . .
C13' C 0.0241(3) 0.36999(18) 0.81175(5) 0.0347(5) Uani 1 1 d . . . . .
C14' C -0.0918(4) 0.4589(2) 0.82524(6) 0.0432(6) Uani 1 1 d . . . . .
C15' C 0.0160(3) 0.32733(18) 0.77681(5) 0.0331(5) Uani 1 1 d . . . . .
H15' H -0.119868 0.323306 0.770238 0.040 Uiso 1 1 calc R U . . .
C16' C 0.0906(4) 0.21044(19) 0.78131(6) 0.0383(5) Uani 1 1 d . . . . .
H16' H 0.035866 0.160891 0.764982 0.046 Uiso 1 1 calc R U . . .
C17' C -0.2189(5) 0.5251(3) 0.80307(7) 0.0631(9) Uani 1 1 d . . . . .
H17C H -0.193728 0.601924 0.806249 0.095 Uiso 1 1 calc R U . . .
H17D H -0.351928 0.509980 0.807865 0.095 Uiso 1 1 calc R U . . .
H17E H -0.192167 0.505833 0.780927 0.095 Uiso 1 1 calc R U . . .
C18' C -0.2655(9) 0.5057(5) 0.98244(10) 0.125(2) Uani 1 1 d . . . . .
H18D H -0.261020 0.523490 1.005126 0.187 Uiso 1 1 calc R U . . .
H18E H -0.310308 0.431610 0.979792 0.187 Uiso 1 1 calc R U . . .
H18F H -0.352067 0.555035 0.971557 0.187 Uiso 1 1 calc R U . . .
C19' C 0.0102(13) 0.6332(5) 0.97510(10) 0.158(3) Uani 1 1 d . . . . .
H19D H 0.019245 0.643369 0.998157 0.237 Uiso 1 1 calc R U . . .
H19E H -0.078341 0.685955 0.966211 0.237 Uiso 1 1 calc R U . . .
H19F H 0.135231 0.643260 0.965477 0.237 Uiso 1 1 calc R U . . .
C20' C -0.2799(6) 0.3295(3) 0.92171(9) 0.0754(10) Uani 1 1 d . . . . .
H20D H -0.284126 0.257495 0.912227 0.113 Uiso 1 1 calc R U . . .
H20E H -0.371805 0.376119 0.911017 0.113 Uiso 1 1 calc R U . . .
H20F H -0.311100 0.324662 0.944372 0.113 Uiso 1 1 calc R U . . .
O1 O 0.6368(3) 0.12735(17) 0.74875(5) 0.0641(6) Uani 1 1 d . . . . .
O2 O 0.5685(3) 0.2811(2) 0.81274(5) 0.0692(6) Uani 1 1 d . . . . .
O3 O 0.2872(2) 0.27240(15) 0.83732(4) 0.0430(4) Uani 1 1 d . . . . .
O4 O 0.1147(3) 0.47157(14) 0.81917(4) 0.0455(4) Uani 1 1 d . . . . .
O5 O 0.0284(3) 0.18045(13) 0.81352(4) 0.0420(4) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.524(4) . ?
C1 C10 1.531(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.522(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.531(5) . ?
C4 C19 1.538(5) . ?
C4 C5 1.563(3) . ?
C5 C6 1.514(4) . ?
C5 C10 1.555(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.524(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.521(3) . ?
C8 C9 1.536(3) . ?
C8 H8 0.9800 . ?
C9 C11 1.531(3) . ?
C9 C10 1.557(3) . ?
C9 H9 0.9800 . ?
C10 C20 1.537(4) . ?
C11 C12 1.493(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.216(3) . ?
C12 C13 1.471(3) . ?
C13 C14 1.339(3) . ?
C13 C15 1.509(3) . ?
C14 C17 1.506(3) . ?
C15 C16' 1.516(3) . ?
C15 C16 1.524(3) . ?
C15 H15 0.9800 . ?
C16 O2 1.198(3) . ?
C16 O3 1.357(3) . ?
C17 C15' 1.539(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C1' C10' 1.529(5) . ?
C1' C2' 1.531(5) . ?
C1' H1'1 0.9700 . ?
C1' H1'2 0.9700 . ?
C2' C3' 1.513(8) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3' C4' 1.526(8) . ?
C3' H3'1 0.9700 . ?
C3' H3'2 0.9700 . ?
C4' C18' 1.533(7) . ?
C4' C19' 1.536(7) . ?
C4' C5' 1.572(4) . ?
C5' C6' 1.502(5) . ?
C5' C10' 1.559(4) . ?
C5' H5' 0.9800 . ?
C6' C7' 1.527(4) . ?
C6' H6'1 0.9700 . ?
C6' H6'2 0.9700 . ?
C7' C8' 1.528(4) . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
C8' C14' 1.528(3) . ?
C8' C9' 1.535(4) . ?
C8' H8' 0.9800 . ?
C9' C11' 1.533(4) . ?
C9' C10' 1.563(3) . ?
C9' H9' 0.9800 . ?
C10' C20' 1.532(5) . ?
C11' C12' 1.501(3) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' O5 1.392(3) . ?
C12' O3 1.459(3) . ?
C12' C13' 1.523(3) . ?
C13' O4 1.420(3) . ?
C13' C14' 1.458(3) . ?
C13' C15' 1.531(3) . ?
C14' O4 1.460(3) . ?
C14' C17' 1.503(4) . ?
C15' C16' 1.526(3) . ?
C15' H15' 0.9800 . ?
C16' O5 1.442(3) . ?
C16' H16' 0.9800 . ?
C17' H17C 0.9600 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C10 113.5(2) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.0(3) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 113.5(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C18 C4 C3 110.2(3) . . ?
C18 C4 C19 107.8(3) . . ?
C3 C4 C19 107.6(3) . . ?
C18 C4 C5 114.8(2) . . ?
C3 C4 C5 107.9(2) . . ?
C19 C4 C5 108.3(2) . . ?
C6 C5 C10 110.3(2) . . ?
C6 C5 C4 114.2(2) . . ?
C10 C5 C4 116.2(2) . . ?
C6 C5 H5 105.0 . . ?
C10 C5 H5 105.0 . . ?
C4 C5 H5 105.0 . . ?
C5 C6 C7 112.0(2) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 113.4(2) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C14 C8 C7 113.01(19) . . ?
C14 C8 C9 112.01(18) . . ?
C7 C8 C9 109.16(18) . . ?
C14 C8 H8 107.5 . . ?
C7 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C11 C9 C8 109.75(19) . . ?
C11 C9 C10 113.97(19) . . ?
C8 C9 C10 113.11(18) . . ?
C11 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C1 C10 C20 109.8(2) . . ?
C1 C10 C5 108.9(2) . . ?
C20 C10 C5 112.4(2) . . ?
C1 C10 C9 108.9(2) . . ?
C20 C10 C9 109.9(2) . . ?
C5 C10 C9 106.76(18) . . ?
C12 C11 C9 112.6(2) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
O1 C12 C13 121.3(2) . . ?
O1 C12 C11 121.2(2) . . ?
C13 C12 C11 117.4(2) . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 C15 121.0(2) . . ?
C12 C13 C15 116.6(2) . . ?
C13 C14 C17 120.7(2) . . ?
C13 C14 C8 121.7(2) . . ?
C17 C14 C8 117.43(19) . . ?
C13 C15 C16' 111.10(19) . . ?
C13 C15 C16 112.1(2) . . ?
C16' C15 C16 112.8(2) . . ?
C13 C15 H15 106.8 . . ?
C16' C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
O2 C16 O3 118.6(2) . . ?
O2 C16 C15 123.3(2) . . ?
O3 C16 C15 117.9(2) . . ?
C14 C17 C15' 116.80(19) . . ?
C14 C17 H17A 108.1 . . ?
C15' C17 H17A 108.1 . . ?
C14 C17 H17B 108.1 . . ?
C15' C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10' C1' C2' 112.9(4) . . ?
C10' C1' H1'1 109.0 . . ?
C2' C1' H1'1 109.0 . . ?
C10' C1' H1'2 109.0 . . ?
C2' C1' H1'2 109.0 . . ?
H1'1 C1' H1'2 107.8 . . ?
C3' C2' C1' 110.3(4) . . ?
C3' C2' H2'1 109.6 . . ?
C1' C2' H2'1 109.6 . . ?
C3' C2' H2'2 109.6 . . ?
C1' C2' H2'2 109.6 . . ?
H2'1 C2' H2'2 108.1 . . ?
C2' C3' C4' 115.1(4) . . ?
C2' C3' H3'1 108.5 . . ?
C4' C3' H3'1 108.5 . . ?
C2' C3' H3'2 108.5 . . ?
C4' C3' H3'2 108.5 . . ?
H3'1 C3' H3'2 107.5 . . ?
C3' C4' C18' 110.7(4) . . ?
C3' C4' C19' 108.4(5) . . ?
C18' C4' C19' 107.8(5) . . ?
C3' C4' C5' 108.1(4) . . ?
C18' C4' C5' 113.2(4) . . ?
C19' C4' C5' 108.6(3) . . ?
C6' C5' C10' 111.6(3) . . ?
C6' C5' C4' 114.2(3) . . ?
C10' C5' C4' 117.1(3) . . ?
C6' C5' H5' 104.0 . . ?
C10' C5' H5' 104.0 . . ?
C4' C5' H5' 104.0 . . ?
C5' C6' C7' 112.0(3) . . ?
C5' C6' H6'1 109.2 . . ?
C7' C6' H6'1 109.2 . . ?
C5' C6' H6'2 109.2 . . ?
C7' C6' H6'2 109.2 . . ?
H6'1 C6' H6'2 107.9 . . ?
C6' C7' C8' 111.4(3) . . ?
C6' C7' H7'1 109.4 . . ?
C8' C7' H7'1 109.4 . . ?
C6' C7' H7'2 109.4 . . ?
C8' C7' H7'2 109.4 . . ?
H7'1 C7' H7'2 108.0 . . ?
C7' C8' C14' 110.1(2) . . ?
C7' C8' C9' 110.6(2) . . ?
C14' C8' C9' 112.5(2) . . ?
C7' C8' H8' 107.8 . . ?
C14' C8' H8' 107.8 . . ?
C9' C8' H8' 107.8 . . ?
C11' C9' C8' 109.4(2) . . ?
C11' C9' C10' 113.7(2) . . ?
C8' C9' C10' 112.3(2) . . ?
C11' C9' H9' 107.0 . . ?
C8' C9' H9' 107.0 . . ?
C10' C9' H9' 107.0 . . ?
C1' C10' C20' 109.1(3) . . ?
C1' C10' C5' 108.8(3) . . ?
C20' C10' C5' 113.6(3) . . ?
C1' C10' C9' 108.9(3) . . ?
C20' C10' C9' 110.3(2) . . ?
C5' C10' C9' 106.0(2) . . ?
C12' C11' C9' 110.8(2) . . ?
C12' C11' H11C 109.5 . . ?
C9' C11' H11C 109.5 . . ?
C12' C11' H11D 109.5 . . ?
C9' C11' H11D 109.5 . . ?
H11C C11' H11D 108.1 . . ?
O5 C12' O3 109.51(19) . . ?
O5 C12' C11' 111.2(2) . . ?
O3 C12' C11' 108.0(2) . . ?
O5 C12' C13' 104.67(18) . . ?
O3 C12' C13' 108.20(19) . . ?
C11' C12' C13' 115.1(2) . . ?
O4 C13' C14' 60.94(16) . . ?
O4 C13' C12' 117.42(18) . . ?
C14' C13' C12' 120.75(19) . . ?
O4 C13' C15' 120.94(18) . . ?
C14' C13' C15' 126.2(2) . . ?
C12' C13' C15' 105.38(18) . . ?
C13' C14' O4 58.25(16) . . ?
C13' C14' C17' 119.3(2) . . ?
O4 C14' C17' 114.4(2) . . ?
C13' C14' C8' 119.9(2) . . ?
O4 C14' C8' 114.2(2) . . ?
C17' C14' C8' 116.7(2) . . ?
C16' C15' C13' 100.95(17) . . ?
C16' C15' C17 114.92(19) . . ?
C13' C15' C17 115.95(19) . . ?
C16' C15' H15' 108.2 . . ?
C13' C15' H15' 108.2 . . ?
C17 C15' H15' 108.2 . . ?
O5 C16' C15 108.0(2) . . ?
O5 C16' C15' 104.28(18) . . ?
C15 C16' C15' 111.01(19) . . ?
O5 C16' H16' 111.1 . . ?
C15 C16' H16' 111.1 . . ?
C15' C16' H16' 111.1 . . ?
C14' C17' H17C 109.5 . . ?
C14' C17' H17D 109.5 . . ?
H17C C17' H17D 109.5 . . ?
C14' C17' H17E 109.5 . . ?
H17C C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C4' C18' H18D 109.5 . . ?
C4' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C4' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C4' C19' H19D 109.5 . . ?
C4' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C4' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C10' C20' H20D 109.5 . . ?
C10' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C10' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C16 O3 C12' 117.26(18) . . ?
C13' O4 C14' 60.81(16) . . ?
C12' O5 C16' 103.84(17) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C10 C1 C2 C3 -56.4(4) . . . . ?
C1 C2 C3 C4 57.4(4) . . . . ?
C2 C3 C4 C18 72.6(3) . . . . ?
C2 C3 C4 C19 -170.2(3) . . . . ?
C2 C3 C4 C5 -53.5(4) . . . . ?
C18 C4 C5 C6 58.6(3) . . . . ?
C3 C4 C5 C6 -178.2(3) . . . . ?
C19 C4 C5 C6 -61.9(4) . . . . ?
C18 C4 C5 C10 -71.7(3) . . . . ?
C3 C4 C5 C10 51.6(3) . . . . ?
C19 C4 C5 C10 167.9(3) . . . . ?
C10 C5 C6 C7 -57.8(3) . . . . ?
C4 C5 C6 C7 169.1(2) . . . . ?
C5 C6 C7 C8 54.0(3) . . . . ?
C6 C7 C8 C14 -176.7(2) . . . . ?
C6 C7 C8 C9 -51.4(3) . . . . ?
C14 C8 C9 C11 -49.6(3) . . . . ?
C7 C8 C9 C11 -175.6(2) . . . . ?
C14 C8 C9 C10 -178.13(18) . . . . ?
C7 C8 C9 C10 55.9(3) . . . . ?
C2 C1 C10 C20 -71.5(3) . . . . ?
C2 C1 C10 C5 52.1(3) . . . . ?
C2 C1 C10 C9 168.1(3) . . . . ?
C6 C5 C10 C1 176.8(2) . . . . ?
C4 C5 C10 C1 -51.2(3) . . . . ?
C6 C5 C10 C20 -61.3(3) . . . . ?
C4 C5 C10 C20 70.7(3) . . . . ?
C6 C5 C10 C9 59.4(3) . . . . ?
C4 C5 C10 C9 -168.6(2) . . . . ?
C11 C9 C10 C1 56.3(3) . . . . ?
C8 C9 C10 C1 -177.4(2) . . . . ?
C11 C9 C10 C20 -64.0(3) . . . . ?
C8 C9 C10 C20 62.3(3) . . . . ?
C11 C9 C10 C5 173.7(2) . . . . ?
C8 C9 C10 C5 -60.0(2) . . . . ?
C8 C9 C11 C12 54.7(3) . . . . ?
C10 C9 C11 C12 -177.3(2) . . . . ?
C9 C11 C12 O1 149.9(3) . . . . ?
C9 C11 C12 C13 -32.6(3) . . . . ?
O1 C12 C13 C14 -177.8(3) . . . . ?
C11 C12 C13 C14 4.7(4) . . . . ?
O1 C12 C13 C15 2.0(4) . . . . ?
C11 C12 C13 C15 -175.5(2) . . . . ?
C12 C13 C14 C17 -176.5(2) . . . . ?
C15 C13 C14 C17 3.8(3) . . . . ?
C12 C13 C14 C8 -0.3(3) . . . . ?
C15 C13 C14 C8 180.0(2) . . . . ?
C7 C8 C14 C13 147.6(2) . . . . ?
C9 C8 C14 C13 23.8(3) . . . . ?
C7 C8 C14 C17 -36.1(3) . . . . ?
C9 C8 C14 C17 -159.88(19) . . . . ?
C14 C13 C15 C16' 35.1(3) . . . . ?
C12 C13 C15 C16' -144.6(2) . . . . ?
C14 C13 C15 C16 -92.1(3) . . . . ?
C12 C13 C15 C16 88.2(2) . . . . ?
C13 C15 C16 O2 -41.1(3) . . . . ?
C16' C15 C16 O2 -167.4(3) . . . . ?
C13 C15 C16 O3 143.9(2) . . . . ?
C16' C15 C16 O3 17.6(3) . . . . ?
C13 C14 C17 C15' -20.2(3) . . . . ?
C8 C14 C17 C15' 163.40(19) . . . . ?
C10' C1' C2' C3' -58.2(6) . . . . ?
C1' C2' C3' C4' 57.7(7) . . . . ?
C2' C3' C4' C18' 73.6(5) . . . . ?
C2' C3' C4' C19' -168.5(5) . . . . ?
C2' C3' C4' C5' -50.9(6) . . . . ?
C3' C4' C5' C6' -179.1(4) . . . . ?
C18' C4' C5' C6' 57.9(5) . . . . ?
C19' C4' C5' C6' -61.8(6) . . . . ?
C3' C4' C5' C10' 47.8(5) . . . . ?
C18' C4' C5' C10' -75.2(5) . . . . ?
C19' C4' C5' C10' 165.2(5) . . . . ?
C10' C5' C6' C7' -59.0(4) . . . . ?
C4' C5' C6' C7' 165.3(3) . . . . ?
C5' C6' C7' C8' 54.8(5) . . . . ?
C6' C7' C8' C14' -178.0(3) . . . . ?
C6' C7' C8' C9' -53.1(4) . . . . ?
C7' C8' C9' C11' -175.7(2) . . . . ?
C14' C8' C9' C11' -52.1(3) . . . . ?
C7' C8' C9' C10' 57.2(3) . . . . ?
C14' C8' C9' C10' -179.3(2) . . . . ?
C2' C1' C10' C20' -71.1(5) . . . . ?
C2' C1' C10' C5' 53.4(5) . . . . ?
C2' C1' C10' C9' 168.5(4) . . . . ?
C6' C5' C10' C1' 176.0(3) . . . . ?
C4' C5' C10' C1' -49.7(5) . . . . ?
C6' C5' C10' C20' -62.2(3) . . . . ?
C4' C5' C10' C20' 72.1(5) . . . . ?
C6' C5' C10' C9' 59.0(4) . . . . ?
C4' C5' C10' C9' -166.7(3) . . . . ?
C11' C9' C10' C1' 59.7(4) . . . . ?
C8' C9' C10' C1' -175.4(3) . . . . ?
C11' C9' C10' C20' -60.0(3) . . . . ?
C8' C9' C10' C20' 64.9(3) . . . . ?
C11' C9' C10' C5' 176.6(3) . . . . ?
C8' C9' C10' C5' -58.5(3) . . . . ?
C8' C9' C11' C12' 65.2(3) . . . . ?
C10' C9' C11' C12' -168.4(2) . . . . ?
C9' C11' C12' O5 -160.9(2) . . . . ?
C9' C11' C12' O3 78.9(3) . . . . ?
C9' C11' C12' C13' -42.1(3) . . . . ?
O5 C12' C13' O4 -159.18(19) . . . . ?
O3 C12' C13' O4 -42.5(3) . . . . ?
C11' C12' C13' O4 78.4(3) . . . . ?
O5 C12' C13' C14' 130.0(2) . . . . ?
O3 C12' C13' C14' -113.3(2) . . . . ?
C11' C12' C13' C14' 7.6(3) . . . . ?
O5 C12' C13' C15' -21.2(2) . . . . ?
O3 C12' C13' C15' 95.5(2) . . . . ?
C11' C12' C13' C15' -143.5(2) . . . . ?
C12' C13' C14' O4 106.4(2) . . . . ?
C15' C13' C14' O4 -108.8(2) . . . . ?
O4 C13' C14' C17' 102.1(3) . . . . ?
C12' C13' C14' C17' -151.5(3) . . . . ?
C15' C13' C14' C17' -6.7(4) . . . . ?
O4 C13' C14' C8' -101.6(3) . . . . ?
C12' C13' C14' C8' 4.8(4) . . . . ?
C15' C13' C14' C8' 149.6(2) . . . . ?
C7' C8' C14' C13' 142.0(3) . . . . ?
C9' C8' C14' C13' 18.1(4) . . . . ?
C7' C8' C14' O4 76.0(3) . . . . ?
C9' C8' C14' O4 -47.9(3) . . . . ?
C7' C8' C14' C17' -61.2(4) . . . . ?
C9' C8' C14' C17' 175.0(3) . . . . ?
O4 C13' C15' C16' 129.8(2) . . . . ?
C14' C13' C15' C16' -155.5(2) . . . . ?
C12' C13' C15' C16' -6.4(2) . . . . ?
O4 C13' C15' C17 5.0(3) . . . . ?
C14' C13' C15' C17 79.7(3) . . . . ?
C12' C13' C15' C17 -131.2(2) . . . . ?
C14 C17 C15' C16' -3.5(3) . . . . ?
C14 C17 C15' C13' 113.8(2) . . . . ?
C13 C15 C16' O5 -169.82(17) . . . . ?
C16 C15 C16' O5 -43.0(2) . . . . ?
C13 C15 C16' C15' -56.1(3) . . . . ?
C16 C15 C16' C15' 70.7(2) . . . . ?
C13' C15' C16' O5 31.1(2) . . . . ?
C17 C15' C16' O5 156.63(19) . . . . ?
C13' C15' C16' C15 -85.0(2) . . . . ?
C17 C15' C16' C15 40.5(3) . . . . ?
O2 C16 O3 C12' 165.4(2) . . . . ?
C15 C16 O3 C12' -19.4(3) . . . . ?
O5 C12' O3 C16 48.4(3) . . . . ?
C11' C12' O3 C16 169.7(2) . . . . ?
C13' C12' O3 C16 -65.1(3) . . . . ?
C12' C13' O4 C14' -111.8(2) . . . . ?
C15' C13' O4 C14' 117.0(2) . . . . ?
C17' C14' O4 C13' -110.5(2) . . . . ?
C8' C14' O4 C13' 111.3(2) . . . . ?
O3 C12' O5 C16' -74.1(2) . . . . ?
C11' C12' O5 C16' 166.6(2) . . . . ?
C13' C12' O5 C16' 41.7(2) . . . . ?
C15 C16' O5 C12' 71.4(2) . . . . ?
C15' C16' O5 C12' -46.7(2) . . . . ?
 
_refine_diff_density_max    0.143
_refine_diff_density_min   -0.206
_refine_diff_density_rms    0.047



