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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     Xtal3.7.1
_journal_date_recd_electronic     2003-10-21
_journal_date_accepted     2003-10-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     12
_journal_page_first     o1867
_journal_page_last     o1868
_journal_paper_category     EO
_publ_contact_author_name     'Dr M. R. Taylor'
_publ_contact_author_address
;
School of Chemistry, Physics and Earth Sciences
The Flinders University of South Australia
GPO Box 2100
Adelaide
SA 5001
Australia
;
_publ_contact_author_email     max.taylor@flinders.edu.au
_publ_contact_author_fax     '61 8 8201 2905'
_publ_contact_author_phone     '61 8 201 2467'
_publ_section_title
;
Conformation of (-)-Membrenone-C
;
loop_
    _publ_author_name
    _publ_author_address
    'Sampson, Rebecca A.'
;
School of Chemistry, Physics and Earth Sciences
The Flinders University of South Australia
GPO Box 2100
Adelaide
SA 5001
Australia
;
    'Perkins, Michael V.'
;
School of Chemistry, Physics and Earth Sciences
The Flinders University of South Australia
GPO Box 2100
Adelaide
SA 5001
Australia
;
    'Taylor, Max R.'
;
School of Chemistry, Physics and Earth Sciences
The Flinders University of South Australia
GPO Box 2100
Adelaide
SA 5001
Australia
;
data_I
_chemical_name_systematic
;
(2S,2'R,3S,3'S)-(1S)-2,2'-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro-
4H-pyran-4-one)
;
_chemical_name_common     '(-)-Membrenone C'
_chemical_formula_moiety     'C20 H30 O4'
_chemical_formula_sum     'C20 H30 O4'
_chemical_formula_iupac     'C20 H30 O4'
_chemical_formula_weight     334.46
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     p_2ac_2ab
loop_
    _symmetry_equiv_pos_as_xyz
    +x,+y,+z
    1/2-x,-y,1/2+z
    1/2+x,1/2-y,-z
    -x,1/2+y,1/2-z
_cell_length_a     9.836(3)
_cell_length_b     13.065(4)
_cell_length_c     14.391(4)
_cell_angle_alpha     90.00000
_cell_angle_beta     90.00000
_cell_angle_gamma     90.00000
_cell_volume     1849.3(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3123
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     25.08
_cell_measurement_temperature     123(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.75
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.11
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.201
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     .082
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
A 1 mm diameter collimator was used.
;
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker P4 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12757
_diffrn_reflns_av_R_equivalents     0.07
_diffrn_reflns_theta_max     27.70
_diffrn_reflns_theta_full     26.0
_diffrn_measured_fraction_theta_max     0.934
_diffrn_measured_fraction_theta_full     .995
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against reflections with F²>0. The weighted R-factor
wR and goodness of fit S are based on F², conventional R-factors R are
based on F, with F set to zero for negative F². The threshold expression
of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement
Friedel related data were averaged because an attempt to refine
a Flack parameter was unsuccessful.
;
_reflns_number_total     2294
_reflns_number_gt     1648
_reflns_threshold_expression     F²>2σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     .040
_refine_ls_wR_factor_ref     .079
_refine_ls_goodness_of_fit_ref     1.203
_refine_ls_number_reflns     2177
_refine_ls_number_parameters     217
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                                'w = 1/[σ²(Fₒ²) + (0.02Fₒ²)²]^1/2^'
_refine_ls_shift/su_max     0.0003
_refine_diff_density_max     .260
_refine_diff_density_min     -.326
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O ? .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
    H ? 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
    C ? .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SMART'
_computing_data_reduction
            'SAINT (Bruker, 1999) and Xtal3.7 ADDREF SORTRF (Hall et al., 2000)'
_computing_structure_solution     'SIR97 (Altomare et al., 1994)'
_computing_structure_refinement     'Xtal3.7 CRYLSQ'
_computing_molecular_graphics     'Xtal3.7'
_computing_publication_material     'Xtal3.7 BONDLA CIFIO'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_calc_attached_atom
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C1 .7737(3) .97960(17) .70830(14) .0241(13) Uani ? ? 1.00000 ? ?
    C2 .7805(3) 1.08753(18) .66693(14) .0229(13) Uani ? ? 1.00000 ? ?
    C2' .7483(3) .89901(17) .63256(14) .0226(13) Uani ? ? 1.00000 ? ?
    C3 .7927(2) 1.17478(18) .73629(14) .0248(14) Uani ? ? 1.00000 ? ?
    C3' .6243(3) .91530(17) .57182(13) .0221(13) Uani ? ? 1.00000 ? ?
    C4 .8026(3) 1.2748(2) .68225(15) .0255(14) Uani ? ? 1.00000 ? ?
    C4' .6040(3) .82316(19) .50883(14) .0260(14) Uani ? ? 1.00000 ? ?
    C5 .8773(3) 1.26960(18) .59387(14) .0239(14) Uani ? ? 1.00000 ? ?
    C5' .6524(3) .72541(19) .54290(14) .0252(14) Uani ? ? 1.00000 ? ?
    C6 .9264(2) 1.17911(19) .56446(13) .0244(14) Uani ? ? 1.00000 ? ?
    C6' .7073(3) .71902(19) .62872(15) .0247(14) Uani ? ? 1.00000 ? ?
    C7 .6755(3) 1.1768(2) .80563(15) .0348(16) Uani ? ? 1.00000 ? ?
    C7' .4931(3) .93527(19) .62545(15) .0306(15) Uani ? ? 1.00000 ? ?
    C8 .9024(3) 1.36845(18) .54250(16) .0349(16) Uani ? ? 1.00000 ? ?
    C8' .6251(3) .63131(19) .48516(16) .0360(16) Uani ? ? 1.00000 ? ?
    C9 1.0178(3) 1.16186(19) .48291(15) .0300(15) Uani ? ? 1.00000 ? ?
    C9' .7450(3) .62110(17) .67683(15) .0305(15) Uani ? ? 1.00000 ? ?
    C10 .9428(3) 1.1174(2) .39987(16) .0407(17) Uani ? ? 1.00000 ? ?
    C10' .7649(3) .62845(18) .78042(17) .0388(16) Uani ? ? 1.00000 ? ?
    C11 .8992(3) .95350(18) .76603(15) .0315(15) Uani ? ? 1.00000 ? ?
    O1 .89603(17) 1.08727(12) .60472(9) .0239(9) Uani ? ? 1.00000 ? ?
    O1' .73589(17) .80256(11) .68176(9) .0246(9) Uani ? ? 1.00000 ? ?
    O4 .7559(2) 1.35533(12) .71207(11) .0355(11) Uani ? ? 1.00000 ? ?
    O4' .54170(18) .83307(14) .43506(10) .0369(11) Uani ? ? 1.00000 ? ?
    H2 .69634 1.10126 .63704 .02900 Uiso ? ? 1.00000 ? ?
    H2' .82189 .90175 .58980 .02900 Uiso ? ? 1.00000 ? ?
    H3 .87252 1.16517 .77258 .03200 Uiso ? ? 1.00000 ? ?
    H3' .64284 .97538 .53690 .02800 Uiso ? ? 1.00000 ? ?
    H7a .68755 1.23257 .84726 .05200 Uiso ? ? 1.00000 ? ?
    H7b .67375 1.11461 .83928 .05200 Uiso ? ? 1.00000 ? ?
    H7c .59224 1.18522 .77289 .05200 Uiso ? ? 1.00000 ? ?
    H7'a .42032 .94509 .58291 .04600 Uiso ? ? 1.00000 ? ?
    H7'b .50349 .99545 .66228 .04600 Uiso ? ? 1.00000 ? ?
    H7'c .47368 .87888 .66462 .04600 Uiso ? ? 1.00000 ? ?
    H9a 1.08761 1.11532 .50063 .03700 Uiso ? ? 1.00000 ? ?
    H9b 1.05719 1.22521 .46548 .03700 Uiso ? ? 1.00000 ? ?
    H9'a .82733 .59700 .65037 .03800 Uiso ? ? 1.00000 ? ?
    H9'b .67459 .57270 .66575 .03800 Uiso ? ? 1.00000 ? ?
    H10a 1.00447 1.10793 .34993 .06200 Uiso ? ? 1.00000 ? ?
    H10b .87291 1.16360 .38124 .06200 Uiso ? ? 1.00000 ? ?
    H10c .90333 1.05371 .41639 .06200 Uiso ? ? 1.00000 ? ?
    H10'a .78858 .56316 .80435 .05900 Uiso ? ? 1.00000 ? ?
    H10'b .68328 .65144 .80868 .05900 Uiso ? ? 1.00000 ? ?
    H10'c .83602 .67575 .79330 .05900 Uiso ? ? 1.00000 ? ?
    H1 .69787 .97880 .74954 .03000 Uiso ? ? 1.00000 ? ?
    H11a .89020 .88609 .79014 .04800 Uiso ? ? 1.00000 ? ?
    H11b .90722 1.00071 .81578 .04800 Uiso ? ? 1.00000 ? ?
    H11c .97757 .95717 .72777 .04800 Uiso ? ? 1.00000 ? ?
    H8a .86329 1.36752 .48239 .05300 Uiso ? ? 1.00000 ? ?
    H8b .99815 1.38100 .53693 .05300 Uiso ? ? 1.00000 ? ?
    H8c .86381 1.42533 .57655 .05300 Uiso ? ? 1.00000 ? ?
    H8'a .69304 .57924 .49619 .05200 Uiso ? ? 1.00000 ? ?
    H8'b .62681 .64629 .41960 .05200 Uiso ? ? 1.00000 ? ?
    H8'c .53836 .60220 .49937 .05200 Uiso ? ? 1.00000 ? ?
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C2 C3 . . 1.520(3) ?
    C2 C1 . . 1.532(3) ?
    C2 O1 . . 1.447(3) ?
    C2 H2 . . .950 ?
    C2' C3' . . 1.516(3) ?
    C2' C1 . . 1.536(3) ?
    C2' O1' . . 1.451(3) ?
    C2' H2' . . .950 ?
    C3 C4 . . 1.524(3) ?
    C3 C7 . . 1.525(3) ?
    C3 H3 . . .952 ?
    C3' C4' . . 1.520(3) ?
    C3' C7' . . 1.527(4) ?
    C3' H3' . . .950 ?
    C4 C5 . . 1.470(3) ?
    C4 O4 . . 1.226(3) ?
    C4' C5' . . 1.448(3) ?
    C4' O4' . . 1.233(3) ?
    C5 C6 . . 1.346(3) ?
    C5 C8 . . 1.508(3) ?
    C5' C6' . . 1.351(3) ?
    C5' C8' . . 1.508(3) ?
    C6 C9 . . 1.495(3) ?
    C6 O1 . . 1.366(3) ?
    C6' C9' . . 1.501(3) ?
    C6' O1' . . 1.361(3) ?
    C7 H7a . . .951 ?
    C7 H7b . . .946 ?
    C7 H7c . . .951 ?
    C7' H7'a . . .951 ?
    C7' H7'b . . .954 ?
    C7' H7'c . . .947 ?
    C8 H8a . . .947 ?
    C8 H8b . . .959 ?
    C8 H8c . . .968 ?
    C8' H8'a . . .967 ?
    C8' H8'b . . .964 ?
    C8' H8'c . . .956 ?
    C9 C10 . . 1.520(3) ?
    C9 H9a . . .952 ?
    C9 H9b . . .948 ?
    C9' C10' . . 1.507(3) ?
    C9' H9'a . . .948 ?
    C9' H9'b . . .952 ?
    C10 H10a . . .948 ?
    C10 H10b . . .954 ?
    C10 H10c . . .948 ?
    C10' H10'a . . .949 ?
    C10' H10'b . . .949 ?
    C10' H10'c . . .952 ?
    C1 C11 . . 1.527(4) ?
    C1 H1 . . .953 ?
    C11 H11a . . .951 ?
    C11 H11b . . .948 ?
    C11 H11c . . .948 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 C2 C1 . . . 116.01(17) ?
    C3 C2 O1 . . . 110.25(19) ?
    C3 C2 H2 . . . 103.0 ?
    C1 C2 O1 . . . 105.81(18) ?
    C1 C2 H2 . . . 108.2 ?
    O1 C2 H2 . . . 113.87 ?
    C3' C2' C1 . . . 116.3(2) ?
    C3' C2' O1' . . . 109.6(2) ?
    C3' C2' H2' . . . 103.53 ?
    C1 C2' O1' . . . 105.24(16) ?
    C1 C2' H2' . . . 108.1 ?
    O1' C2' H2' . . . 114.4 ?
    C2 C3 C4 . . . 108.24(17) ?
    C2 C3 C7 . . . 112.5(2) ?
    C2 C3 H3 . . . 109.1 ?
    C4 C3 C7 . . . 111.6(2) ?
    C4 C3 H3 . . . 109.9 ?
    C7 C3 H3 . . . 105.49 ?
    C2' C3' C4' . . . 109.8(2) ?
    C2' C3' C7' . . . 114.40(17) ?
    C2' C3' H3' . . . 105.5 ?
    C4' C3' C7' . . . 109.0(2) ?
    C4' C3' H3' . . . 111.36 ?
    C7' C3' H3' . . . 106.8 ?
    C3 C4 C5 . . . 115.7(2) ?
    C3 C4 O4 . . . 122.2(2) ?
    C5 C4 O4 . . . 122.0(2) ?
    C3' C4' C5' . . . 116.95(18) ?
    C3' C4' O4' . . . 119.7(2) ?
    C5' C4' O4' . . . 123.2(2) ?
    C4 C5 C6 . . . 119.5(2) ?
    C4 C5 C8 . . . 117.8(2) ?
    C6 C5 C8 . . . 122.6(2) ?
    C4' C5' C6' . . . 119.7(2) ?
    C4' C5' C8' . . . 118.3(2) ?
    C6' C5' C8' . . . 121.6(2) ?
    C5 C6 C9 . . . 126.5(2) ?
    C5 C6 O1 . . . 124.0(2) ?
    C9 C6 O1 . . . 109.4(2) ?
    C5' C6' C9' . . . 125.0(2) ?
    C5' C6' O1' . . . 123.1(2) ?
    C9' C6' O1' . . . 111.95(18) ?
    C3 C7 H7a . . . 109.3 ?
    C3 C7 H7b . . . 109.5 ?
    C3 C7 H7c . . . 109.2 ?
    H7a C7 H7b . . . 109.8 ?
    H7a C7 H7c . . . 109.3 ?
    H7b C7 H7c . . . 109.7 ?
    C3' C7' H7'a . . . 109.5 ?
    C3' C7' H7'b . . . 109.3 ?
    C3' C7' H7'c . . . 109.8 ?
    H7'a C7' H7'b . . . 109.1 ?
    H7'a C7' H7'c . . . 109.7 ?
    H7'b C7' H7'c . . . 109.4 ?
    C5 C8 H8a . . . 111.7 ?
    C5 C8 H8b . . . 110.4 ?
    C5 C8 H8c . . . 110.2 ?
    H8a C8 H8b . . . 109.0 ?
    H8a C8 H8c . . . 108.2 ?
    H8b C8 H8c . . . 107.2 ?
    C5' C8' H8'a . . . 111.1 ?
    C5' C8' H8'b . . . 111.8 ?
    C5' C8' H8'c . . . 111.4 ?
    H8'a C8' H8'b . . . 107.0 ?
    H8'a C8' H8'c . . . 107.6 ?
    H8'b C8' H8'c . . . 107.8 ?
    C6 C9 C10 . . . 112.5(2) ?
    C6 C9 H9a . . . 108.6 ?
    C6 C9 H9b . . . 108.8 ?
    C10 C9 H9a . . . 108.4 ?
    C10 C9 H9b . . . 108.9 ?
    H9a C9 H9b . . . 109.5 ?
    C6' C9' C10' . . . 115.7(2) ?
    C6' C9' H9'a . . . 108.0 ?
    C6' C9' H9'b . . . 108.0 ?
    C10' C9' H9'a . . . 107.9 ?
    C10' C9' H9'b . . . 107.6 ?
    H9'a C9' H9'b . . . 109.5 ?
    C9 C10 H10a . . . 109.6 ?
    C9 C10 H10b . . . 109.2 ?
    C9 C10 H10c . . . 109.7 ?
    H10a C10 H10b . . . 109.3 ?
    H10a C10 H10c . . . 109.8 ?
    H10b C10 H10c . . . 109.3 ?
    C9' C10' H10'a . . . 109.5 ?
    C9' C10' H10'b . . . 109.5 ?
    C9' C10' H10'c . . . 109.2 ?
    H10'a C10' H10'b . . . 109.7 ?
    H10'a C10' H10'c . . . 109.4 ?
    H10'b C10' H10'c . . . 109.4 ?
    C2 C1 C2' . . . 111.24(17) ?
    C2 C1 C11 . . . 112.4(2) ?
    C2 C1 H1 . . . 106.6 ?
    C2' C1 C11 . . . 111.4(2) ?
    C2' C1 H1 . . . 107.9 ?
    C11 C1 H1 . . . 106.95 ?
    C1 C11 H11a . . . 109.3 ?
    C1 C11 H11b . . . 109.4 ?
    C1 C11 H11c . . . 109.3 ?
    H11a C11 H11b . . . 109.6 ?
    H11a C11 H11c . . . 109.6 ?
    H11b C11 H11c . . . 109.8 ?
    C2 O1 C6 . . . 115.63(17) ?
    C2' O1' C6' . . . 116.12(16) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 C2 C3 C4 . . . . 178.2(2) ?
    C1 C2 C3 C7 . . . . -58.0(3) ?
    C1 C2 C3 H3 . . . . 58.6 ?
    O1 C2 C3 C4 . . . . 58.0(2) ?
    O1 C2 C3 C7 . . . . -178.26(18) ?
    O1 C2 C3 H3 . . . . -61.6 ?
    H2 C2 C3 C4 . . . . -63.9 ?
    H2 C2 C3 C7 . . . . 59.9 ?
    H2 C2 C3 H3 . . . . 176.6 y
    C3 C2 C1 C2' . . . . 174.8(2) ?
    C3 C2 C1 C11 . . . . -59.5(3) ?
    C3 C2 C1 H1 . . . . 57.4 ?
    O1 C2 C1 C2' . . . . -62.7(2) ?
    O1 C2 C1 C11 . . . . 63.0(2) ?
    O1 C2 C1 H1 . . . . 179.94 ?
    H2 C2 C1 C2' . . . . 59.7 ?
    H2 C2 C1 C11 . . . . -174.58 ?
    H2 C2 C1 H1 . . . . -57.7 y
    C3 C2 O1 C6 . . . . -49.7(2) ?
    C1 C2 O1 C6 . . . . -175.86(17) ?
    H2 C2 O1 C6 . . . . 65.5 ?
    C1 C2' C3' C4' . . . . -173.15(19) ?
    C1 C2' C3' C7' . . . . -50.2(3) ?
    C1 C2' C3' H3' . . . . 66.8 ?
    O1' C2' C3' C4' . . . . -54.0(2) ?
    O1' C2' C3' C7' . . . . 68.9(2) ?
    O1' C2' C3' H3' . . . . -174.05 ?
    H2' C2' C3' C4' . . . . 68.5 ?
    H2' C2' C3' C7' . . . . -168.6 ?
    H2' C2' C3' H3' . . . . -51.6 y
    C3' C2' C1 C2 . . . . -55.0(3) ?
    C3' C2' C1 C11 . . . . 178.7(2) ?
    C3' C2' C1 H1 . . . . 61.6 ?
    O1' C2' C1 C2 . . . . -176.5(2) ?
    O1' C2' C1 C11 . . . . 57.2(2) ?
    O1' C2' C1 H1 . . . . -59.9 ?
    H2' C2' C1 C2 . . . . 60.8 ?
    H2' C2' C1 C11 . . . . -65.4 ?
    H2' C2' C1 H1 . . . . 177.5 y
    C3' C2' O1' C6' . . . . 51.7(2) ?
    C1 C2' O1' C6' . . . . 177.5(2) ?
    H2' C2' O1' C6' . . . . -64.1 ?
    C2 C3 C4 C5 . . . . -35.2(3) ?
    C2 C3 C4 O4 . . . . 147.5(2) ?
    C7 C3 C4 C5 . . . . -159.5(2) ?
    C7 C3 C4 O4 . . . . 23.1(3) ?
    H3 C3 C4 C5 . . . . 83.8 ?
    H3 C3 C4 O4 . . . . -93.5 ?
    C2 C3 C7 H7a . . . . -179.9 ?
    C2 C3 C7 H7b . . . . 59.9 ?
    C2 C3 C7 H7c . . . . -60.3 ?
    C4 C3 C7 H7a . . . . -58.0 ?
    C4 C3 C7 H7b . . . . -178.2 ?
    C4 C3 C7 H7c . . . . 61.6 ?
    H3 C3 C7 H7a . . . . 61.3 ?
    H3 C3 C7 H7b . . . . -58.9 ?
    H3 C3 C7 H7c . . . . -179.1 ?
    C2' C3' C4' C5' . . . . 28.5(3) ?
    C2' C3' C4' O4' . . . . -155.5(2) ?
    C7' C3' C4' C5' . . . . -97.5(2) ?
    C7' C3' C4' O4' . . . . 78.4(3) ?
    H3' C3' C4' C5' . . . . 145.0 ?
    H3' C3' C4' O4' . . . . -39.1 ?
    C2' C3' C7' H7'a . . . . 179.7 ?
    C2' C3' C7' H7'b . . . . 60.1 ?
    C2' C3' C7' H7'c . . . . -59.9 ?
    C4' C3' C7' H7'a . . . . -57.0 ?
    C4' C3' C7' H7'b . . . . -176.5 ?
    C4' C3' C7' H7'c . . . . 63.4 ?
    H3' C3' C7' H7'a . . . . 63.4 ?
    H3' C3' C7' H7'b . . . . -56.1 ?
    H3' C3' C7' H7'c . . . . -176.2 ?
    C3 C4 C5 C6 . . . . 2.6(3) ?
    C3 C4 C5 C8 . . . . -173.9(2) ?
    O4 C4 C5 C6 . . . . 180.0(2) ?
    O4 C4 C5 C8 . . . . 3.5(4) ?
    C3' C4' C5' C6' . . . . 2.6(3) ?
    C3' C4' C5' C8' . . . . 175.8(2) ?
    O4' C4' C5' C6' . . . . -173.1(2) ?
    O4' C4' C5' C8' . . . . .0(4) ?
    C4 C5 C6 C9 . . . . -172.3(2) ?
    C4 C5 C6 O1 . . . . 9.5(4) ?
    C8 C5 C6 C9 . . . . 4.0(4) ?
    C8 C5 C6 O1 . . . . -174.2(2) ?
    C4 C5 C8 H8a . . . . -120.4 ?
    C4 C5 C8 H8b . . . . 118.2 ?
    C4 C5 C8 H8c . . . .  .0 ?
    C6 C5 C8 H8a . . . . 63.3 ?
    C6 C5 C8 H8b . . . . -58.1 ?
    C6 C5 C8 H8c . . . . -176.4 ?
    C4' C5' C6' C9' . . . . 171.9(2) ?
    C4' C5' C6' O1' . . . . -8.6(4) ?
    C8' C5' C6' C9' . . . . -1.0(4) ?
    C8' C5' C6' O1' . . . . 178.6(2) ?
    C4' C5' C8' H8'a . . . . 153.1 ?
    C4' C5' C8' H8'b . . . . 33.7 ?
    C4' C5' C8' H8'c . . . . -87.0 ?
    C6' C5' C8' H8'a . . . . -33.9 ?
    C6' C5' C8' H8'b . . . . -153.3 ?
    C6' C5' C8' H8'c . . . . 86.0 ?
    C5 C6 C9 C10 . . . . -104.1(3) ?
    C5 C6 C9 H9a . . . . 135.8 ?
    C5 C6 C9 H9b . . . . 16.7 ?
    O1 C6 C9 C10 . . . . 74.3(2) ?
    O1 C6 C9 H9a . . . . -45.8 ?
    O1 C6 C9 H9b . . . . -164.9 ?
    C5 C6 O1 C2 . . . . 15.2(3) ?
    C9 C6 O1 C2 . . . . -163.29(18) ?
    C5' C6' C9' C10' . . . . -162.5(3) ?
    C5' C6' C9' H9'a . . . . 76.5 ?
    C5' C6' C9' H9'b . . . . -41.8 ?
    O1' C6' C9' C10' . . . . 18.0(3) ?
    O1' C6' C9' H9'a . . . . -103.1 ?
    O1' C6' C9' H9'b . . . . 138.6 ?
    C5' C6' O1' C2' . . . . -20.1(3) ?
    C9' C6' O1' C2' . . . . 159.5(2) ?
    C6 C9 C10 H10a . . . . 179.8 ?
    C6 C9 C10 H10b . . . . 60.2 ?
    C6 C9 C10 H10c . . . . -59.6 ?
    H9a C9 C10 H10a . . . . -60.0 ?
    H9a C9 C10 H10b . . . . -179.7 ?
    H9a C9 C10 H10c . . . . 60.6 ?
    H9b C9 C10 H10a . . . . 59.1 ?
    H9b C9 C10 H10b . . . . -60.6 ?
    H9b C9 C10 H10c . . . . 179.7 ?
    C6' C9' C10' H10'a . . . . -179.8 ?
    C6' C9' C10' H10'b . . . . 59.8 ?
    C6' C9' C10' H10'c . . . . -60.0 ?
    H9'a C9' C10' H10'a . . . . -58.8 ?
    H9'a C9' C10' H10'b . . . . -179.1 ?
    H9'a C9' C10' H10'c . . . . 61.0 ?
    H9'b C9' C10' H10'a . . . . 59.3 ?
    H9'b C9' C10' H10'b . . . . -61.0 ?
    H9'b C9' C10' H10'c . . . . 179.1 ?
    C2 C1 C11 H11a . . . . 179.9 ?
    C2 C1 C11 H11b . . . . 60.0 ?
    C2 C1 C11 H11c . . . . -60.2 ?
    C2' C1 C11 H11a . . . . -54.4 ?
    C2' C1 C11 H11b . . . . -174.4 ?
    C2' C1 C11 H11c . . . . 65.4 ?
    H1 C1 C11 H11a . . . . 63.2 ?
    H1 C1 C11 H11b . . . . -56.7 ?
    H1 C1 C11 H11c . . . . -176.9 ?
