# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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. # # This CIF is provided on the understanding that it is used for bona # 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 # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nwsb100723 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H20 O3), H2 O' _chemical_formula_sum 'C24 H42 O7' _chemical_formula_weight 442.58 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.6423(13) _cell_length_b 6.0433(3) _cell_length_c 16.8338(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.536(2) _cell_angle_gamma 90.00 _cell_volume 2473.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2620 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 27.36 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9625 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8412 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2835 _reflns_number_gt 2152 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0529P)^2^+0.9210P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2835 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.34102(5) 0.5874(2) -0.01799(7) 0.0233(3) Uani 1 1 d . . . H1 H 0.3240 0.7317 -0.0418 0.028 Uiso 1 1 calc R . . C2 C 0.30735(5) 0.4913(2) 0.03602(8) 0.0269(3) Uani 1 1 d . . . H2A H 0.2705 0.5604 0.0203 0.032 Uiso 1 1 calc R . . H2B H 0.3027 0.3295 0.0274 0.032 Uiso 1 1 calc R . . C3 C 0.33955(5) 0.5423(2) 0.12797(8) 0.0262(3) Uani 1 1 d . . . H3A H 0.3149 0.6044 0.1572 0.031 Uiso 1 1 calc R . . H3B H 0.3570 0.4066 0.1576 0.031 Uiso 1 1 calc R . . C4 C 0.38317(5) 0.7115(2) 0.12493(8) 0.0223(3) Uani 1 1 d . . . C5 C 0.39785(5) 0.6361(2) 0.04637(7) 0.0208(3) Uani 1 1 d . . . C6 C 0.43174(5) 0.8007(2) 0.01636(8) 0.0276(3) Uani 1 1 d . . . H6 H 0.4420 0.9347 0.0468 0.033 Uiso 1 1 calc R . . C7 C 0.44806(5) 0.7692(2) -0.04998(8) 0.0295(3) Uani 1 1 d . . . H7 H 0.4701 0.8815 -0.0628 0.035 Uiso 1 1 calc R . . C8 C 0.43469(5) 0.5712(2) -0.10640(8) 0.0262(3) Uani 1 1 d . . . H8 H 0.4514 0.4368 -0.0734 0.031 Uiso 1 1 calc R . . C9 C 0.37310(5) 0.5330(3) -0.14690(8) 0.0331(3) Uani 1 1 d . . . H9A H 0.3679 0.4320 -0.1951 0.040 Uiso 1 1 calc R . . H9B H 0.3559 0.6762 -0.1695 0.040 Uiso 1 1 calc R . . C10 C 0.34173(5) 0.4372(3) -0.09096(8) 0.0298(3) Uani 1 1 d . . . H10 H 0.3596 0.2945 -0.0670 0.036 Uiso 1 1 calc R . . C11 C 0.36070(6) 0.9459(2) 0.11862(9) 0.0317(3) Uani 1 1 d . . . H11A H 0.3510 0.9805 0.1690 0.048 Uiso 1 1 calc R . . H11B H 0.3279 0.9581 0.0692 0.048 Uiso 1 1 calc R . . H11C H 0.3887 1.0503 0.1136 0.048 Uiso 1 1 calc R . . C12 C 0.28275(6) 0.3861(4) -0.14673(10) 0.0527(5) Uani 1 1 d . . . H12A H 0.2625 0.3152 -0.1131 0.079 Uiso 1 1 calc R . . H12B H 0.2838 0.2865 -0.1921 0.079 Uiso 1 1 calc R . . H12C H 0.2643 0.5241 -0.1706 0.079 Uiso 1 1 calc R . . O1 O 0.43035(4) 0.69171(17) 0.19880(5) 0.0275(2) Uani 1 1 d . . . O2 O 0.42541(4) 0.42691(15) 0.06469(6) 0.0262(2) Uani 1 1 d . . . O3 O 0.46037(4) 0.60895(18) -0.17045(6) 0.0316(2) Uani 1 1 d . . . O4 O 0.5000 0.9445(2) -0.2500 0.0321(3) Uani 1 2 d S . . H3O H 0.4478(7) 0.513(3) -0.2094(12) 0.050(5) Uiso 1 1 d . . . H1O H 0.4499(8) 0.811(4) 0.2071(12) 0.059(6) Uiso 1 1 d . . . H2O H 0.4563(7) 0.449(3) 0.1042(12) 0.046(5) Uiso 1 1 d . . . H1W H 0.4853(8) 0.857(3) -0.2222(12) 0.056(6) Uiso 1 1 d . . . 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 C1 0.0182(5) 0.0285(7) 0.0228(6) 0.0029(5) 0.0061(4) -0.0023(5) C2 0.0201(6) 0.0325(7) 0.0288(7) 0.0019(5) 0.0085(5) -0.0037(5) C3 0.0276(6) 0.0278(7) 0.0265(6) 0.0001(5) 0.0134(5) -0.0028(5) C4 0.0224(6) 0.0239(6) 0.0217(6) 0.0001(5) 0.0085(5) -0.0001(5) C5 0.0192(5) 0.0216(6) 0.0222(6) 0.0001(5) 0.0073(4) -0.0010(5) C6 0.0260(6) 0.0302(7) 0.0281(7) -0.0054(6) 0.0106(5) -0.0098(6) C7 0.0264(6) 0.0345(8) 0.0306(7) -0.0035(6) 0.0132(5) -0.0121(6) C8 0.0238(6) 0.0344(7) 0.0235(6) -0.0019(5) 0.0119(5) -0.0053(5) C9 0.0270(6) 0.0500(9) 0.0227(7) -0.0060(6) 0.0085(5) -0.0112(6) C10 0.0232(6) 0.0409(8) 0.0251(6) -0.0064(6) 0.0072(5) -0.0117(6) C11 0.0329(7) 0.0260(7) 0.0391(8) -0.0015(6) 0.0155(6) 0.0037(6) C12 0.0334(8) 0.0913(14) 0.0327(8) -0.0152(9) 0.0097(6) -0.0297(9) O1 0.0290(5) 0.0290(5) 0.0219(4) -0.0001(4) 0.0044(4) -0.0042(4) O2 0.0216(4) 0.0259(5) 0.0287(5) -0.0035(4) 0.0048(4) 0.0029(4) O3 0.0311(5) 0.0415(6) 0.0271(5) -0.0079(5) 0.0164(4) -0.0108(4) O4 0.0378(8) 0.0260(7) 0.0340(8) 0.000 0.0133(6) 0.000 _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 C10 1.5319(18) . ? C1 C5 1.5427(16) . ? C1 C2 1.5522(17) . ? C1 H1 1.0000 . ? C2 C3 1.5364(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5284(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O1 1.4380(14) . ? C4 C11 1.5202(18) . ? C4 C5 1.5542(17) . ? C5 O2 1.4330(15) . ? C5 C6 1.5097(17) . ? C6 C7 1.3249(18) . ? C6 H6 0.9500 . ? C7 C8 1.4983(19) . ? C7 H7 0.9500 . ? C8 O3 1.4491(15) . ? C8 C9 1.5256(17) . ? C8 H8 1.0000 . ? C9 C10 1.5332(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.5367(18) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O1 H1O 0.86(2) . ? O2 H2O 0.868(19) . ? O3 H3O 0.857(19) . ? O4 H1W 0.867(18) . ? 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 C10 C1 C5 115.26(10) . . ? C10 C1 C2 113.48(11) . . ? C5 C1 C2 103.72(9) . . ? C10 C1 H1 108.0 . . ? C5 C1 H1 108.0 . . ? C2 C1 H1 108.0 . . ? C3 C2 C1 107.10(10) . . ? C3 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? C3 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C2 105.39(10) . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? O1 C4 C11 109.52(10) . . ? O1 C4 C3 109.80(10) . . ? C11 C4 C3 111.13(10) . . ? O1 C4 C5 110.28(9) . . ? C11 C4 C5 113.77(11) . . ? C3 C4 C5 102.12(10) . . ? O2 C5 C6 110.88(10) . . ? O2 C5 C1 105.91(10) . . ? C6 C5 C1 113.97(10) . . ? O2 C5 C4 108.17(10) . . ? C6 C5 C4 114.34(10) . . ? C1 C5 C4 102.90(9) . . ? C7 C6 C5 123.86(12) . . ? C7 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C6 C7 C8 125.37(12) . . ? C6 C7 H7 117.3 . . ? C8 C7 H7 117.3 . . ? O3 C8 C7 106.22(10) . . ? O3 C8 C9 110.00(10) . . ? C7 C8 C9 113.56(11) . . ? O3 C8 H8 109.0 . . ? C7 C8 H8 109.0 . . ? C9 C8 H8 109.0 . . ? C8 C9 C10 116.96(11) . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9B 108.1 . . ? C10 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C1 C10 C9 114.27(11) . . ? C1 C10 C12 110.41(11) . . ? C9 C10 C12 107.90(11) . . ? C1 C10 H10 108.0 . . ? C9 C10 H10 108.0 . . ? C12 C10 H10 108.0 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 O1 H1O 110.9(13) . . ? C5 O2 H2O 107.2(12) . . ? C8 O3 H3O 108.4(12) . . ? 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 C10 C1 C2 C3 139.85(11) . . . . ? C5 C1 C2 C3 14.05(13) . . . . ? C1 C2 C3 C4 13.11(14) . . . . ? C2 C3 C4 O1 -151.82(10) . . . . ? C2 C3 C4 C11 86.86(13) . . . . ? C2 C3 C4 C5 -34.80(12) . . . . ? C10 C1 C5 O2 -46.60(13) . . . . ? C2 C1 C5 O2 78.06(11) . . . . ? C10 C1 C5 C6 75.56(14) . . . . ? C2 C1 C5 C6 -159.77(11) . . . . ? C10 C1 C5 C4 -160.06(11) . . . . ? C2 C1 C5 C4 -35.40(13) . . . . ? O1 C4 C5 O2 48.59(13) . . . . ? C11 C4 C5 O2 172.09(10) . . . . ? C3 C4 C5 O2 -68.08(11) . . . . ? O1 C4 C5 C6 -75.49(13) . . . . ? C11 C4 C5 C6 48.01(14) . . . . ? C3 C4 C5 C6 167.85(10) . . . . ? O1 C4 C5 C1 160.37(10) . . . . ? C11 C4 C5 C1 -76.12(12) . . . . ? C3 C4 C5 C1 43.71(12) . . . . ? O2 C5 C6 C7 58.11(16) . . . . ? C1 C5 C6 C7 -61.28(17) . . . . ? C4 C5 C6 C7 -179.27(13) . . . . ? C5 C6 C7 C8 1.5(2) . . . . ? C6 C7 C8 O3 179.35(13) . . . . ? C6 C7 C8 C9 58.32(19) . . . . ? O3 C8 C9 C10 166.00(12) . . . . ? C7 C8 C9 C10 -75.12(17) . . . . ? C5 C1 C10 C9 -62.64(15) . . . . ? C2 C1 C10 C9 177.96(11) . . . . ? C5 C1 C10 C12 175.53(12) . . . . ? C2 C1 C10 C12 56.13(16) . . . . ? C8 C9 C10 C1 63.72(17) . . . . ? C8 C9 C10 C12 -173.07(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O O1 0.857(19) 1.92(2) 2.7678(14) 170.7(17) 6_565 O1 H1O O4 0.86(2) 1.94(2) 2.7906(15) 167.8(18) 5_675 O2 H2O O3 0.868(19) 2.102(18) 2.9119(13) 155.1(16) 5_665 O4 H1W O3 0.867(18) 1.942(19) 2.7933(14) 166.8(18) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 965596'