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

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#
#                 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:
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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_tjs1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H38 O7.50'
_chemical_formula_weight         434.53

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           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                   8.6777(2)
_cell_length_b                   15.1269(3)
_cell_length_c                   9.5353(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.722(2)
_cell_angle_gamma                90.00
_cell_volume                     1243.06(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2088
_cell_measurement_theta_min      5.1
_cell_measurement_theta_max      62.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.85495
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Oxford Gemini S ultra'
_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            3870
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         62.65
_reflns_number_total             2869
_reflns_number_gt                2699
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0538P)²+0.1110P] 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     SHELXL
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2869
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8904(2) 0.28795(15) -0.1594(2) 0.0668(6) Uani 1 1 d . . .
H1A H 0.9032 0.2980 -0.2417 0.098(12) Uiso 1 1 calc R . .
O2 O 0.6450(2) 0.2770(2) -0.2522(2) 0.0923(9) Uani 1 1 d . . .
O3 O 0.16915(18) 0.09978(12) 0.25818(18) 0.0545(5) Uani 1 1 d . . .
O4 O -0.07238(19) 0.32276(15) 0.57486(17) 0.0610(5) Uani 1 1 d . . .
H4A H -0.1588 0.3312 0.5322 0.098(13) Uiso 1 1 calc R . .
O5 O 0.34197(15) 0.30127(10) 0.39881(14) 0.0405(4) Uani 1 1 d . . .
O6 O 0.23322(17) 0.43178(11) 0.30504(15) 0.0464(4) Uani 1 1 d . . .
O7 O 0.6613(2) 0.35577(17) 0.40190(19) 0.0668(5) Uani 1 1 d . . .
H7A H 0.6053 0.3122 0.4038 0.121(17) Uiso 1 1 calc R . .
C1 C 0.7422(3) 0.27236(19) -0.1509(3) 0.0538(7) Uani 1 1 d . . .
C2 C 0.7087(3) 0.24855(18) -0.0063(2) 0.0489(6) Uani 1 1 d . . .
C3 C 0.5636(3) 0.22551(18) 0.0093(2) 0.0476(6) Uani 1 1 d . . .
H3A H 0.4919 0.2274 -0.0712 0.057 Uiso 1 1 calc R . .
C4 C 0.5061(3) 0.19778(16) 0.1392(2) 0.0485(6) Uani 1 1 d . . .
H4B H 0.5777 0.1883 0.2183 0.058 Uiso 1 1 calc R . .
C5 C 0.3575(3) 0.18523(17) 0.1514(2) 0.0473(6) Uani 1 1 d . . .
H5A H 0.2888 0.1900 0.0693 0.057 Uiso 1 1 calc R . .
C6 C 0.2889(3) 0.16413(17) 0.2838(2) 0.0440(5) Uani 1 1 d . . .
H6A H 0.3700 0.1421 0.3555 0.053 Uiso 1 1 calc R . .
C7 C 0.2152(2) 0.24666(16) 0.3381(2) 0.0394(5) Uani 1 1 d . . .
H7B H 0.1610 0.2781 0.2569 0.047 Uiso 1 1 calc R . .
C8 C 0.1009(3) 0.23358(19) 0.4480(2) 0.0453(6) Uani 1 1 d . . .
H8A H 0.0129 0.1989 0.4040 0.054 Uiso 1 1 calc R . .
C9 C 0.0426(2) 0.32574(18) 0.4766(2) 0.0460(6) Uani 1 1 d . . .
H9A H -0.0073 0.3498 0.3872 0.055 Uiso 1 1 calc R . .
C10 C 0.1718(3) 0.38833(18) 0.5327(2) 0.0478(6) Uani 1 1 d . . .
H10A H 0.2193 0.3650 0.6235 0.057 Uiso 1 1 calc R . .
C11 C 0.2983(3) 0.38943(16) 0.4306(2) 0.0413(5) Uani 1 1 d . . .
C12 C 0.4475(3) 0.43332(19) 0.4914(2) 0.0492(6) Uani 1 1 d . . .
H12A H 0.4893 0.4023 0.5765 0.059 Uiso 1 1 calc R . .
H12B H 0.4258 0.4937 0.5174 0.059 Uiso 1 1 calc R . .
C13 C 0.5675(3) 0.43402(19) 0.3883(3) 0.0510(6) Uani 1 1 d . . .
H13A H 0.6358 0.4849 0.4109 0.061 Uiso 1 1 calc R . .
C14 C 0.4926(3) 0.44447(18) 0.2350(2) 0.0508(6) Uani 1 1 d . . .
H14A H 0.4792 0.3853 0.1936 0.061 Uiso 1 1 calc R . .
C15 C 0.3326(3) 0.48649(18) 0.2314(2) 0.0487(6) Uani 1 1 d . . .
H15A H 0.3446 0.5435 0.2802 0.058 Uiso 1 1 calc R . .
C16 C 0.2448(3) 0.5022(2) 0.0855(3) 0.0645(8) Uani 1 1 d . . .
H16A H 0.3033 0.5461 0.0378 0.077 Uiso 1 1 calc R . .
C17 C 0.0849(4) 0.5417(3) 0.0993(4) 0.0878(11) Uani 1 1 d . . .
H17A H 0.0967 0.5942 0.1560 0.132 Uiso 1 1 calc R . .
H17B H 0.0234 0.4994 0.1433 0.132 Uiso 1 1 calc R . .
H17C H 0.0342 0.5562 0.0072 0.132 Uiso 1 1 calc R . .
C18 C 0.2306(4) 0.4202(3) -0.0062(3) 0.0830(10) Uani 1 1 d . . .
H18A H 0.3321 0.3972 -0.0148 0.125 Uiso 1 1 calc R . .
H18B H 0.1800 0.4351 -0.0982 0.125 Uiso 1 1 calc R . .
H18C H 0.1706 0.3765 0.0361 0.125 Uiso 1 1 calc R . .
C19 C 0.5993(4) 0.4968(3) 0.1484(4) 0.0851(11) Uani 1 1 d . . .
H19A H 0.5512 0.5023 0.0528 0.128 Uiso 1 1 calc R . .
H19B H 0.6965 0.4664 0.1492 0.128 Uiso 1 1 calc R . .
H19C H 0.6171 0.5546 0.1887 0.128 Uiso 1 1 calc R . .
C20 C 0.1132(4) 0.4810(2) 0.5585(4) 0.0748(9) Uani 1 1 d . . .
H20A H 0.0362 0.4781 0.6230 0.112 Uiso 1 1 calc R . .
H20B H 0.0682 0.5061 0.4707 0.112 Uiso 1 1 calc R . .
H20C H 0.1982 0.5172 0.5982 0.112 Uiso 1 1 calc R . .
C21 C 0.1725(3) 0.1841(2) 0.5790(3) 0.0593(7) Uani 1 1 d . . .
H21A H 0.2059 0.1266 0.5522 0.089 Uiso 1 1 calc R . .
H21B H 0.0966 0.1778 0.6440 0.089 Uiso 1 1 calc R . .
H21C H 0.2599 0.2166 0.6232 0.089 Uiso 1 1 calc R . .
C22 C 0.8399(3) 0.2502(3) 0.1098(3) 0.0762(10) Uani 1 1 d . . .
H22A H 0.8028 0.2332 0.1969 0.114 Uiso 1 1 calc R . .
H22B H 0.8823 0.3088 0.1188 0.114 Uiso 1 1 calc R . .
H22C H 0.9189 0.2096 0.0884 0.114 Uiso 1 1 calc R . .
C23 C 0.2261(3) 0.01523(19) 0.2257(3) 0.0643(7) Uani 1 1 d . . .
H23A H 0.1412 -0.0256 0.2100 0.096 Uiso 1 1 calc R . .
H23B H 0.2982 -0.0051 0.3031 0.096 Uiso 1 1 calc R . .
H23C H 0.2776 0.0192 0.1421 0.096 Uiso 1 1 calc R . .
O1W O 0.6502(6) 0.1739(4) -0.5013(5) 0.0909(14) Uani 0.50 1 d P . .


_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 C1 1.319(3) . ?
O2 C1 1.208(3) . ?
O3 C23 1.418(3) . ?
O3 C6 1.424(3) . ?
O4 C9 1.447(2) . ?
O5 C11 1.429(3) . ?
O5 C7 1.442(3) . ?
O6 C11 1.416(3) . ?
O6 C15 1.437(3) . ?
O7 C13 1.434(3) . ?
C1 C2 1.487(3) . ?
C2 C3 1.332(3) . ?
C2 C22 1.492(4) . ?
C3 C4 1.451(3) . ?
C4 C5 1.322(3) . ?
C5 C6 1.491(3) . ?
C6 C7 1.521(3) . ?
C7 C8 1.538(3) . ?
C8 C9 1.519(4) . ?
C8 C21 1.525(3) . ?
C9 C10 1.517(4) . ?
C10 C20 1.521(4) . ?
C10 C11 1.550(3) . ?
C11 C12 1.509(3) . ?
C12 C13 1.514(3) . ?
C13 C14 1.536(3) . ?
C14 C15 1.524(3) . ?
C14 C19 1.532(4) . ?
C15 C16 1.524(3) . ?
C16 C18 1.514(5) . ?
C16 C17 1.531(5) . ?

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
C23 O3 C6 112.82(18) . . ?
C11 O5 C7 114.30(16) . . ?
C11 O6 C15 118.10(16) . . ?
O2 C1 O1 122.4(2) . . ?
O2 C1 C2 124.2(2) . . ?
O1 C1 C2 113.4(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 C22 124.8(2) . . ?
C1 C2 C22 118.0(2) . . ?
C2 C3 C4 126.5(2) . . ?
C5 C4 C3 123.6(2) . . ?
C4 C5 C6 126.5(2) . . ?
O3 C6 C5 110.89(19) . . ?
O3 C6 C7 106.96(16) . . ?
C5 C6 C7 109.74(19) . . ?
O5 C7 C6 105.98(16) . . ?
O5 C7 C8 108.81(17) . . ?
C6 C7 C8 117.19(19) . . ?
C9 C8 C21 114.6(2) . . ?
C9 C8 C7 105.04(19) . . ?
C21 C8 C7 112.85(19) . . ?
O4 C9 C10 109.20(19) . . ?
O4 C9 C8 110.9(2) . . ?
C10 C9 C8 112.83(19) . . ?
C9 C10 C20 112.6(2) . . ?
C9 C10 C11 109.54(18) . . ?
C20 C10 C11 111.5(2) . . ?
O6 C11 O5 109.40(17) . . ?
O6 C11 C12 111.43(19) . . ?
O5 C11 C12 104.81(18) . . ?
O6 C11 C10 107.09(17) . . ?
O5 C11 C10 110.37(18) . . ?
C12 C11 C10 113.73(18) . . ?
C11 C12 C13 112.21(19) . . ?
O7 C13 C12 111.2(2) . . ?
O7 C13 C14 110.1(2) . . ?
C12 C13 C14 111.85(19) . . ?
C15 C14 C19 112.2(2) . . ?
C15 C14 C13 110.34(19) . . ?
C19 C14 C13 110.6(2) . . ?
O6 C15 C14 110.3(2) . . ?
O6 C15 C16 105.74(19) . . ?
C14 C15 C16 116.3(2) . . ?
C18 C16 C15 113.5(2) . . ?
C18 C16 C17 110.8(3) . . ?
C15 C16 C17 110.1(3) . . ?

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
O2 C1 C2 C3 4.6(4) . . . . ?
O1 C1 C2 C3 -175.2(2) . . . . ?
O2 C1 C2 C22 -176.8(3) . . . . ?
O1 C1 C2 C22 3.4(4) . . . . ?
C1 C2 C3 C4 178.3(3) . . . . ?
C22 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 172.1(3) . . . . ?
C3 C4 C5 C6 -174.6(2) . . . . ?
C23 O3 C6 C5 68.6(3) . . . . ?
C23 O3 C6 C7 -171.74(19) . . . . ?
C4 C5 C6 O3 -139.5(3) . . . . ?
C4 C5 C6 C7 102.6(3) . . . . ?
C11 O5 C7 C6 168.22(15) . . . . ?
C11 O5 C7 C8 -64.9(2) . . . . ?
O3 C6 C7 O5 164.81(16) . . . . ?
C5 C6 C7 O5 -74.8(2) . . . . ?
O3 C6 C7 C8 43.2(2) . . . . ?
C5 C6 C7 C8 163.56(19) . . . . ?
O5 C7 C8 C9 62.1(2) . . . . ?
C6 C7 C8 C9 -177.73(19) . . . . ?
O5 C7 C8 C21 -63.3(3) . . . . ?
C6 C7 C8 C21 56.8(3) . . . . ?
C21 C8 C9 O4 -58.1(3) . . . . ?
C7 C8 C9 O4 177.49(17) . . . . ?
C21 C8 C9 C10 64.8(2) . . . . ?
C7 C8 C9 C10 -59.6(2) . . . . ?
O4 C9 C10 C20 -57.2(3) . . . . ?
C8 C9 C10 C20 178.9(2) . . . . ?
O4 C9 C10 C11 178.05(18) . . . . ?
C8 C9 C10 C11 54.2(2) . . . . ?
C15 O6 C11 O5 -96.1(2) . . . . ?
C15 O6 C11 C12 19.3(3) . . . . ?
C15 O6 C11 C10 144.3(2) . . . . ?
C7 O5 C11 O6 -60.2(2) . . . . ?
C7 O5 C11 C12 -179.77(16) . . . . ?
C7 O5 C11 C10 57.4(2) . . . . ?
C9 C10 C11 O6 69.2(2) . . . . ?
C20 C10 C11 O6 -56.1(3) . . . . ?
C9 C10 C11 O5 -49.8(2) . . . . ?
C20 C10 C11 O5 -175.1(2) . . . . ?
C9 C10 C11 C12 -167.2(2) . . . . ?
C20 C10 C11 C12 67.4(3) . . . . ?
O6 C11 C12 C13 -58.2(3) . . . . ?
O5 C11 C12 C13 60.0(3) . . . . ?
C10 C11 C12 C13 -179.4(2) . . . . ?
C11 C12 C13 O7 -89.2(3) . . . . ?
C11 C12 C13 C14 34.4(3) . . . . ?
O7 C13 C14 C15 146.4(2) . . . . ?
C12 C13 C14 C15 22.2(3) . . . . ?
O7 C13 C14 C19 -88.8(3) . . . . ?
C12 C13 C14 C19 147.0(3) . . . . ?
C11 O6 C15 C14 39.0(3) . . . . ?
C11 O6 C15 C16 165.4(2) . . . . ?
C19 C14 C15 O6 175.7(2) . . . . ?
C13 C14 C15 O6 -60.5(3) . . . . ?
C19 C14 C15 C16 55.4(3) . . . . ?
C13 C14 C15 C16 179.2(2) . . . . ?
O6 C15 C16 C18 -69.4(3) . . . . ?
C14 C15 C16 C18 53.3(3) . . . . ?
O6 C15 C16 C17 55.4(3) . . . . ?
C14 C15 C16 C17 178.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        62.65
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 1007092'
