# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_yf18131t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H32 O9'
_chemical_formula_weight         452.49
_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 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.4323(13)
_cell_length_b                   9.4544(10)
_cell_length_c                   11.5317(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.545(2)
_cell_angle_gamma                90.00
_cell_volume                     1188.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1993
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      22.67

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6392
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.08
_reflns_number_total             4017
_reflns_number_gt                2577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1920P)²+0.0000P] where P=(Fo²+2Fc²)/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   -1(2)
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     274
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2876
_refine_ls_wR_factor_gt          0.2557
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.003
_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
C1 C 1.1182(5) 0.3080(6) 0.8630(4) 0.0544(13) Uani 1 1 d . . .
H1 H 1.1523 0.2139 0.8580 0.065 Uiso 1 1 calc R . .
O2 O 1.1025(3) 0.3814(4) 0.7500(3) 0.0594(10) Uani 1 1 d . . .
C3 C 1.0317(5) 0.3065(6) 0.6449(5) 0.0577(13) Uani 1 1 d . . .
H3 H 1.0771 0.2263 0.6258 0.069 Uiso 1 1 calc R . .
C4 C 0.9954(6) 0.4108(7) 0.5424(5) 0.0695(16) Uani 1 1 d . . .
H4A H 0.9809 0.3641 0.4644 0.083 Uiso 1 1 calc R . .
H4B H 1.0578 0.4828 0.5509 0.083 Uiso 1 1 calc R . .
C5 C 0.8793(6) 0.4730(7) 0.5553(5) 0.0682(16) Uani 1 1 d . . .
O5 O 0.8280(5) 0.5781(5) 0.5117(4) 0.0929(16) Uani 1 1 d . . .
O6 O 0.8372(3) 0.3903(4) 0.6319(3) 0.0612(10) Uani 1 1 d . . .
C7 C 0.9089(5) 0.2611(6) 0.6581(5) 0.0563(13) Uani 1 1 d . . .
O7 O 0.8594(4) 0.1653(4) 0.5618(3) 0.0685(11) Uani 1 1 d . . .
C70 C 0.7433(8) 0.1128(10) 0.5503(7) 0.103(3) Uani 1 1 d . . .
H7A H 0.7455 0.0577 0.6209 0.154 Uiso 1 1 calc R . .
H7B H 0.7170 0.0542 0.4791 0.154 Uiso 1 1 calc R . .
H7C H 0.6870 0.1900 0.5428 0.154 Uiso 1 1 calc R . .
C8 C 0.9057(5) 0.2055(6) 0.7788(5) 0.0609(14) Uani 1 1 d . . .
H8A H 0.9305 0.1070 0.7869 0.073 Uiso 1 1 calc R . .
H8B H 0.8228 0.2114 0.7843 0.073 Uiso 1 1 calc R . .
C9 C 0.9919(5) 0.2919(5) 0.8802(4) 0.0542(13) Uani 1 1 d . . .
H9 H 0.9564 0.3862 0.8805 0.065 Uiso 1 1 calc R . .
O10 O 1.0046(4) 0.2266(4) 0.9946(3) 0.0607(10) Uani 1 1 d . . .
C11 C 1.0743(5) 0.3101(6) 1.0934(4) 0.0544(13) Uani 1 1 d . . .
H11 H 1.0375 0.4046 1.0860 0.065 Uiso 1 1 calc R . .
C12 C 1.2042(5) 0.3245(7) 1.0863(4) 0.0603(14) Uani 1 1 d . . .
H12 H 1.2422 0.2306 1.0948 0.072 Uiso 1 1 calc R . .
C13 C 1.2042(5) 0.3877(7) 0.9648(5) 0.0648(14) Uani 1 1 d . . .
H13A H 1.1794 0.4862 0.9611 0.078 Uiso 1 1 calc R . .
H13B H 1.2864 0.3837 0.9572 0.078 Uiso 1 1 calc R . .
C110 C 1.0660(6) 0.2434(7) 1.2109(5) 0.0663(16) Uani 1 1 d . . .
H10A H 1.0989 0.1482 1.2173 0.080 Uiso 1 1 calc R . .
H10B H 1.1163 0.2974 1.2794 0.080 Uiso 1 1 calc R . .
C111 C 0.9386(6) 0.2374(6) 1.2183(5) 0.0654(15) Uani 1 1 d . . .
H11A H 0.8854 0.1915 1.1464 0.078 Uiso 1 1 calc R . .
H11B H 0.9365 0.1832 1.2890 0.078 Uiso 1 1 calc R . .
O112 O 0.8970(4) 0.3783(4) 1.2270(3) 0.0690(11) Uani 1 1 d . . .
C113 C 0.7702(3) 0.3811(4) 1.2154(3) 0.0842(19) Uani 1 1 d . . .
H13C H 0.7487 0.4738 1.2387 0.101 Uiso 1 1 calc R . .
H13D H 0.7531 0.3122 1.2705 0.101 Uiso 1 1 calc R . .
C114 C 0.6900(3) 0.3482(4) 1.0842(3) 0.095(2) Uani 1 1 d RU . .
C115 C 0.5904(3) 0.2565(4) 1.0499(3) 0.145(4) Uani 1 1 d RU . .
H115 H 0.5698 0.2026 1.1083 0.174 Uiso 1 1 calc R . .
C116 C 0.5216(3) 0.2454(4) 0.9283(3) 0.128(3) Uani 1 1 d RU . .
H116 H 0.4550 0.1841 0.9053 0.153 Uiso 1 1 calc R . .
C117 C 0.5524(3) 0.3260(4) 0.8409(3) 0.151(4) Uani 1 1 d RU . .
C118 C 0.6520(3) 0.4177(4) 0.8752(3) 0.147(4) Uani 1 1 d RU . .
H118 H 0.6726 0.4716 0.8168 0.176 Uiso 1 1 calc R . .
C119 C 0.7208(3) 0.4287(4) 0.9969(3) 0.141(4) Uani 1 1 d RU . .
H119 H 0.7874 0.4901 1.0198 0.169 Uiso 1 1 calc R . .
O170 O 0.4842(8) 0.3180(11) 0.7110(8) 0.178(4) Uani 1 1 d . . .
C171 C 0.3821(10) 0.2599(17) 0.7034(18) 0.236(10) Uani 1 1 d . . .
H17A H 0.3722 0.1771 0.6532 0.354 Uiso 1 1 calc R . .
H17B H 0.3167 0.3251 0.6681 0.354 Uiso 1 1 calc R . .
H17C H 0.3801 0.2335 0.7832 0.354 Uiso 1 1 calc R . .
O120 O 1.2723(3) 0.4124(5) 1.1869(3) 0.0726(12) Uani 1 1 d . . .
C121 C 1.3977(6) 0.3999(11) 1.2161(7) 0.097(2) Uani 1 1 d . . .
H21A H 1.4359 0.4727 1.2746 0.116 Uiso 1 1 calc R . .
H21B H 1.4223 0.4153 1.1436 0.116 Uiso 1 1 calc R . .
O122 O 1.4406(5) 0.2645(10) 1.2660(6) 0.135(3) Uani 1 1 d . . .
C123 C 1.4231(11) 0.2341(19) 1.3799(10) 0.182(7) Uani 1 1 d . . .
H23A H 1.4231 0.3208 1.4233 0.273 Uiso 1 1 calc R . .
H23B H 1.4883 0.1743 1.4263 0.273 Uiso 1 1 calc R . .
H23C H 1.3460 0.1868 1.3672 0.273 Uiso 1 1 calc R . .


_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 O2 1.439(6) . ?
C1 C13 1.489(8) . ?
C1 C9 1.523(8) . ?
O2 C3 1.426(6) . ?
C3 C4 1.499(8) . ?
C3 C7 1.519(8) . ?
C4 C5 1.499(9) . ?
C5 O5 1.186(8) . ?
C5 O6 1.371(7) . ?
O6 C7 1.451(7) . ?
C7 O7 1.412(6) . ?
C7 C8 1.498(7) . ?
O7 C70 1.385(9) . ?
C8 C9 1.520(7) . ?
C9 O10 1.423(6) . ?
O10 C11 1.418(6) . ?
C11 C12 1.518(8) . ?
C11 C110 1.524(7) . ?
C12 O120 1.448(6) . ?
C12 C13 1.523(8) . ?
C110 C111 1.485(8) . ?
C111 O112 1.428(7) . ?
O112 C113 1.415(5) . ?
C113 C114 1.5457 . ?
C114 C115 1.3900 . ?
C114 C119 1.3900 . ?
C115 C116 1.3900 . ?
C116 C117 1.3900 . ?
C117 C118 1.3900 . ?
C117 O170 1.468(9) . ?
C118 C119 1.3900 . ?
O170 C171 1.269(11) . ?
O120 C121 1.376(8) . ?
C121 O122 1.429(12) . ?
O122 C123 1.416(12) . ?

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
O2 C1 C13 110.0(5) . . ?
O2 C1 C9 107.5(4) . . ?
C13 C1 C9 112.0(4) . . ?
C3 O2 C1 114.5(4) . . ?
O2 C3 C4 107.2(5) . . ?
O2 C3 C7 111.1(4) . . ?
C4 C3 C7 102.7(5) . . ?
C3 C4 C5 102.9(4) . . ?
O5 C5 O6 121.7(7) . . ?
O5 C5 C4 128.8(6) . . ?
O6 C5 C4 109.5(5) . . ?
C5 O6 C7 109.2(4) . . ?
O7 C7 O6 108.0(4) . . ?
O7 C7 C8 112.9(5) . . ?
O6 C7 C8 108.6(4) . . ?
O7 C7 C3 105.4(4) . . ?
O6 C7 C3 102.8(4) . . ?
C8 C7 C3 118.3(5) . . ?
C70 O7 C7 116.8(5) . . ?
C7 C8 C9 109.5(5) . . ?
O10 C9 C8 110.0(4) . . ?
O10 C9 C1 109.1(4) . . ?
C8 C9 C1 112.0(4) . . ?
C11 O10 C9 112.3(4) . . ?
O10 C11 C12 109.2(4) . . ?
O10 C11 C110 108.3(4) . . ?
C12 C11 C110 114.2(4) . . ?
O120 C12 C11 107.8(4) . . ?
O120 C12 C13 111.3(5) . . ?
C11 C12 C13 110.9(4) . . ?
C1 C13 C12 110.1(5) . . ?
C111 C110 C11 113.1(4) . . ?
O112 C111 C110 108.7(5) . . ?
C113 O112 C111 111.3(4) . . ?
O112 C113 C114 112.2(2) . . ?
C115 C114 C119 120.0 . . ?
C115 C114 C113 126.7 . . ?
C119 C114 C113 113.2 . . ?
C116 C115 C114 120.0 . . ?
C115 C116 C117 120.0 . . ?
C116 C117 C118 120.0 . . ?
C116 C117 O170 122.6(4) . . ?
C118 C117 O170 117.4(4) . . ?
C119 C118 C117 120.0 . . ?
C118 C119 C114 120.0 . . ?
C171 O170 C117 106.7(11) . . ?
C121 O120 C12 114.6(5) . . ?
O120 C121 O122 112.4(7) . . ?
C123 O122 C121 115.3(9) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 988171'
