# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_PAA-DKR
_database_code_depnum_ccdc_archive 'CCDC 861580'
_chemical_name_systematic        
;
?
;
_chemical_name_common            6A
_chemical_melting_point          354.9
_chemical_formula_moiety         C18H26O9
_chemical_formula_sum            'C18 H26 O9'
_chemical_formula_weight         386.39
_chemical_absolute_configuration syn
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1862(7)
_cell_length_b                   11.0958(13)
_cell_length_c                   11.8947(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.528(10)
_cell_angle_gamma                90.00
_cell_volume                     918.12(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      72.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-58'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3248
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         72.48
_reflns_number_total             2413
_reflns_number_gt                2387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0877P)^2^+0.1831P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.17(17)
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4500(2) 0.61065(16) 0.46419(12) 0.0127(3) Uani 1 1 d . . .
O2 O 0.0337(2) 0.58630(17) 0.47766(13) 0.0159(4) Uani 1 1 d . . .
O3 O 1.0315(2) 0.81942(18) 0.06281(15) 0.0196(4) Uani 1 1 d . . .
O4 O -0.1788(2) 0.39839(18) 0.21538(16) 0.0226(4) Uani 1 1 d . . .
O5 O 0.4656(2) 0.5397(2) 0.02511(14) 0.0232(4) Uani 1 1 d . . .
O6 O 0.2738(2) 0.73849(15) 0.33040(13) 0.0131(3) Uani 1 1 d . . .
O7 O 1.0072(2) 0.99635(17) 0.15071(14) 0.0185(4) Uani 1 1 d . . .
O8 O 0.1678(3) 0.40207(17) 0.49612(14) 0.0203(4) Uani 1 1 d . . .
O9 O 0.1025(3) 0.30142(18) 0.23784(16) 0.0219(4) Uani 1 1 d . . .
C10 C 0.2503(3) 0.5469(2) 0.14767(17) 0.0128(4) Uani 1 1 d . . .
H10A H 0.2040 0.4714 0.1097 0.015 Uiso 1 1 calc R . .
H10B H 0.1484 0.6059 0.1242 0.015 Uiso 1 1 calc R . .
C11 C 0.0984(3) 0.5046(2) 0.30996(17) 0.0103(4) Uani 1 1 d . . .
H11 H 0.0107 0.5713 0.2796 0.012 Uiso 1 1 calc R . .
C12 C 0.7017(3) 0.7282(2) 0.12428(18) 0.0127(4) Uani 1 1 d . . .
H12A H 0.7925 0.6618 0.1384 0.015 Uiso 1 1 calc R . .
H12B H 0.6593 0.7400 0.0410 0.015 Uiso 1 1 calc R . .
C13 C 0.1101(3) 0.4905(2) 0.43862(18) 0.0112(4) Uani 1 1 d . . .
C14 C 0.5287(3) 0.6944(2) 0.17036(18) 0.0118(4) Uani 1 1 d . . .
H14 H 0.4404 0.7632 0.1564 0.014 Uiso 1 1 calc R . .
C15 C 0.2925(3) 0.5291(2) 0.27995(17) 0.0106(4) Uani 1 1 d . . .
H15 H 0.3745 0.4579 0.3011 0.013 Uiso 1 1 calc R . .
C16 C 0.9594(3) 0.8814(2) 0.12432(18) 0.0125(4) Uani 1 1 d . . .
C17 C 0.4218(3) 0.5880(2) 0.10642(18) 0.0133(4) Uani 1 1 d . . .
C18 C 0.3173(4) 0.8037(2) 0.43783(19) 0.0197(5) Uani 1 1 d . . .
H18A H 0.2014 0.8185 0.4634 0.024 Uiso 1 1 calc R . .
H18B H 0.3771 0.8804 0.4293 0.024 Uiso 1 1 calc R . .
C19 C 1.1651(3) 1.0464(2) 0.1095(2) 0.0179(5) Uani 1 1 d . . .
H19A H 1.1352 1.1287 0.0835 0.022 Uiso 1 1 calc R . .
H19B H 1.1831 0.9996 0.0442 0.022 Uiso 1 1 calc R . .
C20 C 0.3983(3) 0.6378(2) 0.34386(17) 0.0096(4) Uani 1 1 d . . .
C21 C 0.4549(3) 0.7236(2) 0.52384(19) 0.0172(5) Uani 1 1 d . . .
H21A H 0.5837 0.7571 0.5433 0.021 Uiso 1 1 calc R . .
H21B H 0.4126 0.7138 0.5946 0.021 Uiso 1 1 calc R . .
C22 C 0.8029(3) 0.8414(2) 0.17970(19) 0.0156(5) Uani 1 1 d . . .
H22A H 0.7094 0.9057 0.1732 0.019 Uiso 1 1 calc R . .
H22B H 0.8582 0.8266 0.2617 0.019 Uiso 1 1 calc R . .
C23 C 0.0127(3) 0.3892(2) 0.25052(18) 0.0130(4) Uani 1 1 d . . .
C24 C 0.5776(3) 0.6672(2) 0.30112(18) 0.0128(4) Uani 1 1 d . . .
H24A H 0.6656 0.5994 0.3175 0.015 Uiso 1 1 calc R . .
H24B H 0.6421 0.7364 0.3434 0.015 Uiso 1 1 calc R . .
C25 C -0.2760(4) 0.2960(3) 0.1508(2) 0.0268(6) Uani 1 1 d . . .
H25A H -0.2377 0.2882 0.0794 0.040 Uiso 1 1 calc R . .
H25B H -0.4125 0.3079 0.1340 0.040 Uiso 1 1 calc R . .
H25C H -0.2420 0.2240 0.1961 0.040 Uiso 1 1 calc R . .
C26 C 0.0278(4) 0.5819(3) 0.5979(2) 0.0239(5) Uani 1 1 d . . .
H26A H -0.0520 0.5160 0.6093 0.036 Uiso 1 1 calc R . .
H26B H -0.0240 0.6561 0.6185 0.036 Uiso 1 1 calc R . .
H26C H 0.1556 0.5707 0.6460 0.036 Uiso 1 1 calc R . .
C27 C 1.3454(3) 1.0443(3) 0.2054(2) 0.0220(5) Uani 1 1 d . . .
H27A H 1.4495 1.0769 0.1779 0.033 Uiso 1 1 calc R . .
H27B H 1.3748 0.9627 0.2306 0.033 Uiso 1 1 calc R . .
H27C H 1.3277 1.0918 0.2694 0.033 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0180(7) 0.0145(9) 0.0044(6) 0.0011(6) 0.0004(5) -0.0008(6)
O2 0.0219(8) 0.0145(9) 0.0135(7) -0.0030(7) 0.0083(6) 0.0022(6)
O3 0.0243(8) 0.0181(10) 0.0209(8) -0.0025(7) 0.0142(6) -0.0020(7)
O4 0.0173(8) 0.0232(10) 0.0249(8) -0.0071(8) 0.0006(6) -0.0065(7)
O5 0.0285(8) 0.0302(11) 0.0151(8) -0.0100(8) 0.0130(6) -0.0083(8)
O6 0.0167(7) 0.0127(9) 0.0089(7) -0.0017(6) 0.0014(5) 0.0026(6)
O7 0.0234(8) 0.0174(9) 0.0194(8) -0.0051(7) 0.0143(6) -0.0075(7)
O8 0.0316(9) 0.0169(9) 0.0152(7) 0.0048(7) 0.0109(7) 0.0043(7)
O9 0.0282(8) 0.0128(9) 0.0254(8) -0.0035(7) 0.0082(7) -0.0027(7)
C10 0.0156(9) 0.0159(12) 0.0071(9) -0.0022(8) 0.0030(7) -0.0042(9)
C11 0.0127(9) 0.0098(11) 0.0092(9) -0.0012(8) 0.0040(7) -0.0023(8)
C12 0.0147(9) 0.0147(12) 0.0098(9) 0.0018(8) 0.0052(7) -0.0006(9)
C13 0.0131(9) 0.0111(11) 0.0102(9) -0.0010(8) 0.0043(7) -0.0012(8)
C14 0.0150(9) 0.0133(12) 0.0076(9) 0.0006(8) 0.0039(8) -0.0010(8)
C15 0.0136(9) 0.0109(11) 0.0080(9) -0.0005(8) 0.0038(7) 0.0001(8)
C16 0.0171(10) 0.0117(11) 0.0085(8) 0.0022(8) 0.0028(8) -0.0002(9)
C17 0.0159(9) 0.0153(12) 0.0081(9) 0.0004(9) 0.0018(7) -0.0007(9)
C18 0.0353(12) 0.0120(11) 0.0117(9) -0.0033(10) 0.0056(9) -0.0016(10)
C19 0.0233(11) 0.0178(12) 0.0161(10) 0.0005(9) 0.0113(9) -0.0065(9)
C20 0.0137(9) 0.0105(11) 0.0042(9) 0.0013(8) 0.0017(7) 0.0002(8)
C21 0.0218(10) 0.0197(13) 0.0092(9) -0.0052(9) 0.0025(8) -0.0059(10)
C22 0.0180(10) 0.0175(12) 0.0132(9) -0.0020(9) 0.0074(8) -0.0050(9)
C23 0.0187(10) 0.0128(11) 0.0082(8) 0.0003(8) 0.0049(7) -0.0042(9)
C24 0.0120(9) 0.0188(12) 0.0072(9) -0.0006(8) 0.0016(7) -0.0034(9)
C25 0.0274(12) 0.0245(14) 0.0240(12) -0.0055(11) -0.0017(10) -0.0138(11)
C26 0.0348(13) 0.0260(14) 0.0155(11) -0.0075(11) 0.0151(9) -0.0039(11)
C27 0.0225(11) 0.0246(15) 0.0206(11) -0.0012(11) 0.0089(9) -0.0039(10)

_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
O1 C20 1.418(2) . ?
O1 C21 1.436(3) . ?
O2 C13 1.332(3) . ?
O2 C26 1.443(2) . ?
O3 C16 1.211(3) . ?
O4 C23 1.338(3) . ?
O4 C25 1.449(3) . ?
O5 C17 1.214(3) . ?
O6 C20 1.415(3) . ?
O6 C18 1.433(3) . ?
O7 C16 1.337(3) . ?
O7 C19 1.454(3) . ?
O8 C13 1.208(3) . ?
O9 C23 1.199(3) . ?
C10 C17 1.507(3) . ?
C10 C15 1.539(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C23 1.517(3) . ?
C11 C13 1.520(3) . ?
C11 C15 1.548(3) . ?
C11 H11 0.9800 . ?
C12 C22 1.518(3) . ?
C12 C14 1.526(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C17 1.507(3) . ?
C14 C24 1.536(3) . ?
C14 H14 0.9800 . ?
C15 C20 1.523(3) . ?
C15 H15 0.9800 . ?
C16 C22 1.506(3) . ?
C18 C21 1.519(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C27 1.497(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C24 1.534(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C20 O1 C21 106.34(17) . . ?
C13 O2 C26 115.83(19) . . ?
C23 O4 C25 115.3(2) . . ?
C20 O6 C18 107.91(16) . . ?
C16 O7 C19 117.47(18) . . ?
C17 C10 C15 113.84(17) . . ?
C17 C10 H10A 108.8 . . ?
C15 C10 H10A 108.8 . . ?
C17 C10 H10B 108.8 . . ?
C15 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C23 C11 C13 107.19(18) . . ?
C23 C11 C15 108.95(17) . . ?
C13 C11 C15 115.16(16) . . ?
C23 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C15 C11 H11 108.5 . . ?
C22 C12 C14 113.11(18) . . ?
C22 C12 H12A 109.0 . . ?
C14 C12 H12A 109.0 . . ?
C22 C12 H12B 109.0 . . ?
C14 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O8 C13 O2 124.29(19) . . ?
O8 C13 C11 125.3(2) . . ?
O2 C13 C11 110.19(19) . . ?
C17 C14 C12 111.67(18) . . ?
C17 C14 C24 108.37(18) . . ?
C12 C14 C24 114.33(17) . . ?
C17 C14 H14 107.4 . . ?
C12 C14 H14 107.4 . . ?
C24 C14 H14 107.4 . . ?
C20 C15 C10 110.78(18) . . ?
C20 C15 C11 112.94(17) . . ?
C10 C15 C11 107.48(16) . . ?
C20 C15 H15 108.5 . . ?
C10 C15 H15 108.5 . . ?
C11 C15 H15 108.5 . . ?
O3 C16 O7 124.0(2) . . ?
O3 C16 C22 125.2(2) . . ?
O7 C16 C22 110.76(19) . . ?
O5 C17 C14 123.1(2) . . ?
O5 C17 C10 121.5(2) . . ?
C14 C17 C10 115.32(18) . . ?
O6 C18 C21 105.3(2) . . ?
O6 C18 H18A 110.7 . . ?
C21 C18 H18A 110.7 . . ?
O6 C18 H18B 110.7 . . ?
C21 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
O7 C19 C27 109.65(19) . . ?
O7 C19 H19A 109.7 . . ?
C27 C19 H19A 109.7 . . ?
O7 C19 H19B 109.7 . . ?
C27 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
O6 C20 O1 106.25(16) . . ?
O6 C20 C15 110.25(16) . . ?
O1 C20 C15 107.90(17) . . ?
O6 C20 C24 110.76(18) . . ?
O1 C20 C24 110.52(15) . . ?
C15 C20 C24 111.01(17) . . ?
O1 C21 C18 104.28(17) . . ?
O1 C21 H21A 110.9 . . ?
C18 C21 H21A 110.9 . . ?
O1 C21 H21B 110.9 . . ?
C18 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C16 C22 C12 112.55(18) . . ?
C16 C22 H22A 109.1 . . ?
C12 C22 H22A 109.1 . . ?
C16 C22 H22B 109.1 . . ?
C12 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
O9 C23 O4 124.5(2) . . ?
O9 C23 C11 125.2(2) . . ?
O4 C23 C11 110.3(2) . . ?
C20 C24 C14 112.30(16) . . ?
C20 C24 H24A 109.1 . . ?
C14 C24 H24A 109.1 . . ?
C20 C24 H24B 109.1 . . ?
C14 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C27 H27A 109.5 . . ?
C19 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C19 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        72.48
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.063