# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
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#                                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:
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data_ea29

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Equisetumone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 O6, H2 O'
_chemical_formula_sum            'C15 H26 O7'
_chemical_formula_weight         318.36
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Othorhombic
_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.4125(4)
_cell_length_b                   9.9012(4)
_cell_length_c                   16.0619(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1496.89(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9172
_cell_measurement_theta_min      5.2480
_cell_measurement_theta_max      66.2423

_exptl_crystal_description       prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_T_max  0.9493
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus tube'
_diffrn_radiation_monochromator  'montel mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9756
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         66.45
_reflns_number_total             2582
_reflns_number_gt                2576
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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 > 2σ(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)+(0.0348P)²+0.4565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.02(13)
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
C1 C 0.37090(14) 0.79510(14) 0.32779(8) 0.0131(3) Uani 1 1 d . . .
C2 C 0.42282(14) 0.72268(14) 0.24902(8) 0.0133(3) Uani 1 1 d . . .
H2 H 0.4499 0.6287 0.2655 0.016 Uiso 1 1 calc R . .
C3 C 0.30730(15) 0.71126(14) 0.18165(8) 0.0145(3) Uani 1 1 d . . .
H3A H 0.3523 0.6733 0.1311 0.017 Uiso 1 1 calc R . .
H3B H 0.2365 0.6444 0.2011 0.017 Uiso 1 1 calc R . .
C4 C 0.22681(14) 0.83857(14) 0.15588(8) 0.0136(3) Uani 1 1 d . . .
C5 C 0.00628(15) 0.85715(13) 0.09178(9) 0.0145(3) Uani 1 1 d . . .
C6 C 0.00527(15) 0.95457(14) 0.16423(9) 0.0151(3) Uani 1 1 d . . .
H6A H -0.0887 0.9566 0.1919 0.018 Uiso 1 1 calc R . .
H6B H 0.0308 1.0471 0.1462 0.018 Uiso 1 1 calc R . .
C7 C 0.11864(14) 0.89476(13) 0.22114(8) 0.0129(3) Uani 1 1 d . . .
C8 C 0.18010(14) 0.99234(13) 0.28870(8) 0.0133(3) Uani 1 1 d . . .
C9 C 0.32716(15) 0.94524(14) 0.31883(8) 0.0129(3) Uani 1 1 d . . .
H9 H 0.3983 0.9877 0.2807 0.015 Uiso 1 1 calc R . .
C10 C 0.38074(16) 0.97066(14) 0.40845(9) 0.0161(3) Uani 1 1 d . . .
H10A H 0.3051 0.9660 0.4512 0.019 Uiso 1 1 calc R . .
H10B H 0.4374 1.0543 0.4145 0.019 Uiso 1 1 calc R . .
C11 C 0.47213(15) 0.84002(14) 0.40215(9) 0.0150(3) Uani 1 1 d . . .
C12 C 0.62590(15) 0.87116(15) 0.37935(9) 0.0174(3) Uani 1 1 d . . .
H12A H 0.6712 0.9204 0.4251 0.026 Uiso 1 1 calc R . .
H12B H 0.6282 0.9265 0.3288 0.026 Uiso 1 1 calc R . .
H12C H 0.6771 0.7865 0.3695 0.026 Uiso 1 1 calc R . .
C13 C 0.46994(17) 0.75005(15) 0.47896(9) 0.0193(3) Uani 1 1 d . . .
H13A H 0.5098 0.6615 0.4650 0.029 Uiso 1 1 calc R . .
H13B H 0.3718 0.7390 0.4982 0.029 Uiso 1 1 calc R . .
H13C H 0.5268 0.7917 0.5232 0.029 Uiso 1 1 calc R . .
C14 C 0.32020(15) 0.94364(15) 0.11349(8) 0.0150(3) Uani 1 1 d . . .
H14A H 0.3653 0.9035 0.0644 0.022 Uiso 1 1 calc R . .
H14B H 0.3936 0.9743 0.1524 0.022 Uiso 1 1 calc R . .
H14C H 0.2618 1.0207 0.0964 0.022 Uiso 1 1 calc R . .
C15 C 0.07429(15) 1.00829(15) 0.35978(9) 0.0155(3) Uani 1 1 d . . .
H15A H 0.1067 1.0799 0.3974 0.023 Uiso 1 1 calc R . .
H15B H 0.0672 0.9231 0.3906 0.023 Uiso 1 1 calc R . .
H15C H -0.0191 1.0321 0.3371 0.023 Uiso 1 1 calc R . .
O1 O 0.25429(10) 0.71860(10) 0.36035(6) 0.0140(2) Uani 1 1 d . . .
H1 H 0.2829 0.6416 0.3746 0.021 Uiso 1 1 calc R . .
O2 O 0.54582(10) 0.78448(10) 0.21317(6) 0.0155(2) Uani 1 1 d . . .
H2A H 0.6185 0.7403 0.2266 0.023 Uiso 1 1 calc R . .
O3 O 0.12958(10) 0.79000(10) 0.08926(6) 0.0153(2) Uani 1 1 d . . .
O4 O -0.08579(10) 0.83722(11) 0.04090(6) 0.0182(2) Uani 1 1 d . . .
O5 O 0.04766(10) 0.78340(10) 0.26014(6) 0.0145(2) Uani 1 1 d . . .
H5 H 0.1020 0.7479 0.2954 0.022 Uiso 1 1 calc R . .
O6 O 0.20648(10) 1.12349(10) 0.25190(6) 0.0139(2) Uani 1 1 d . . .
H6C H 0.1311 1.1689 0.2521 0.021 Uiso 1 1 calc R . .
O7 O 0.16913(11) 0.53468(11) 0.90328(7) 0.0218(2) Uani 1 1 d . . .
H7A H 0.1219 0.5979 0.8747 0.080 Uiso 1 1 d . . .
H7B H 0.2407 0.5886 0.9266 0.080 Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.4325(16) . ?
C1 C2 1.5341(18) . ?
C1 C9 1.5492(19) . ?
C1 C11 1.5913(18) . ?
C2 O2 1.4306(16) . ?
C2 C3 1.5383(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.4879(16) . ?
C4 C14 1.5227(19) . ?
C4 C7 1.5637(19) . ?
C5 O4 1.2074(18) . ?
C5 O3 1.3381(17) . ?
C5 C6 1.5115(19) . ?
C6 C7 1.5247(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O5 1.4333(16) . ?
C7 C8 1.5639(18) . ?
C8 O6 1.4481(16) . ?
C8 C15 1.5233(19) . ?
C8 C9 1.5388(19) . ?
C9 C10 1.5458(19) . ?
C9 H9 1.0000 . ?
C10 C11 1.5567(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.5219(19) . ?
C11 C12 1.524(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1 0.8400 . ?
O2 H2A 0.8400 . ?
O5 H5 0.8400 . ?
O6 H6C 0.8400 . ?
O7 H7A 0.8945 . ?
O7 H7B 0.9376 . ?

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
O1 C1 C2 107.34(11) . . ?
O1 C1 C9 109.73(11) . . ?
C2 C1 C9 117.17(11) . . ?
O1 C1 C11 109.42(10) . . ?
C2 C1 C11 123.98(11) . . ?
C9 C1 C11 87.74(10) . . ?
O2 C2 C1 112.95(11) . . ?
O2 C2 C3 108.68(11) . . ?
C1 C2 C3 112.91(11) . . ?
O2 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C2 118.71(12) . . ?
C4 C3 H3A 107.6 . . ?
C2 C3 H3A 107.6 . . ?
C4 C3 H3B 107.6 . . ?
C2 C3 H3B 107.6 . . ?
H3A C3 H3B 107.1 . . ?
O3 C4 C14 104.74(11) . . ?
O3 C4 C3 103.48(11) . . ?
C14 C4 C3 113.49(11) . . ?
O3 C4 C7 101.33(10) . . ?
C14 C4 C7 115.63(12) . . ?
C3 C4 C7 115.77(11) . . ?
O4 C5 O3 121.39(12) . . ?
O4 C5 C6 128.39(13) . . ?
O3 C5 C6 110.23(11) . . ?
C5 C6 C7 102.08(11) . . ?
C5 C6 H6A 111.4 . . ?
C7 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C7 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
O5 C7 C6 103.57(10) . . ?
O5 C7 C4 108.84(11) . . ?
C6 C7 C4 101.07(11) . . ?
O5 C7 C8 110.15(11) . . ?
C6 C7 C8 115.78(11) . . ?
C4 C7 C8 116.36(11) . . ?
O6 C8 C15 108.97(11) . . ?
O6 C8 C9 104.24(10) . . ?
C15 C8 C9 112.57(11) . . ?
O6 C8 C7 109.53(10) . . ?
C15 C8 C7 110.01(11) . . ?
C9 C8 C7 111.33(11) . . ?
C8 C9 C10 122.48(11) . . ?
C8 C9 C1 123.99(12) . . ?
C10 C9 C1 89.03(10) . . ?
C8 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C1 C9 H9 106.4 . . ?
C9 C10 C11 89.11(10) . . ?
C9 C10 H10A 113.8 . . ?
C11 C10 H10A 113.8 . . ?
C9 C10 H10B 113.8 . . ?
C11 C10 H10B 113.8 . . ?
H10A C10 H10B 111.0 . . ?
C13 C11 C12 109.03(12) . . ?
C13 C11 C10 115.23(12) . . ?
C12 C11 C10 111.85(11) . . ?
C13 C11 C1 115.90(11) . . ?
C12 C11 C1 116.40(12) . . ?
C10 C11 C1 87.14(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2A 109.5 . . ?
C5 O3 C4 110.56(10) . . ?
C7 O5 H5 109.5 . . ?
C8 O6 H6C 109.5 . . ?
H7A O7 H7B 99.4 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.45
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 1017660'
