# Electronic Supplementary Material (ESI) for Chemical Communications # 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_111028_s1_mxf #TrackingRef '16017_web_deposit_cif_file_0_XiaofengMa_1355064798.111028_s1_mxf.cif' _audit_creation_date 2011-11-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.09.07 svn.r1971, GUI svn.r3853) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H22 O5' _chemical_formula_sum 'C12 H22 O5' _chemical_formula_weight 246.30 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula C20H20O5 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' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 6.2466(4) _cell_length_b 6.8285(6) _cell_length_c 16.0444(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.122(8) _cell_angle_gamma 90.00 _cell_volume 682.60(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 771 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1985 _cell_measurement_theta_min 3.2371 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2891 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 3.24 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 13.00 50.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0486 77.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega -47.00 -15.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0486 77.0000 -120.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 56.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 77.0000 60.0000 65 #__ type_ start__ end____ width___ exp.time_ 4 omega -4.00 82.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 77.0000 -60.0000 86 #__ type_ start__ end____ width___ exp.time_ 5 omega -52.00 -27.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 -38.0000 -30.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0643024000 _diffrn_orient_matrix_UB_12 0.0443384000 _diffrn_orient_matrix_UB_13 -0.0330255000 _diffrn_orient_matrix_UB_21 0.0918427000 _diffrn_orient_matrix_UB_22 0.0111806000 _diffrn_orient_matrix_UB_23 -0.0230931000 _diffrn_orient_matrix_UB_31 -0.0195638000 _diffrn_orient_matrix_UB_32 -0.0933096000 _diffrn_orient_matrix_UB_33 -0.0184504000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1356 _reflns_number_total 2004 _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.564 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 2004 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0748 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 11.287 _refine_ls_shift/su_mean 0.057 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1299P)^2^+0.0869P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1934 _refine_ls_wR_factor_ref 0.2271 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.9621(5) -0.9593(6) -0.3437(2) 0.0725(12) Uani 1 1 d . . . O2 O -0.7980(6) -1.0604(8) -0.2172(2) 0.0861(13) Uani 1 1 d . . . O3 O -0.3535(5) -1.0647(7) -0.4156(2) 0.0747(11) Uani 1 1 d . . . H3 H -0.2442 -0.9988 -0.4077 0.112 Uiso 1 1 calc R . . O4 O -0.5302(5) -0.6776(6) -0.4280(3) 0.0763(12) Uani 1 1 d . . . H4 H -0.582(10) -0.624(11) -0.486(5) 0.10(2) Uiso 1 1 d . . . O5 O -1.1339(8) -0.5659(10) -0.3556(4) 0.128(2) Uani 1 1 d . . . H5 H -1.2439 -0.6318 -0.3583 0.192 Uiso 1 1 calc R . . C1 C -0.5139(7) -0.9932(8) -0.3644(3) 0.0563(13) Uani 1 1 d . . . H1 H -0.439(7) -0.925(6) -0.310(3) 0.047(12) Uiso 1 1 d . . . C2 C -0.6560(7) -0.8469(8) -0.4124(4) 0.0592(13) Uani 1 1 d . . . H2 H -0.699(7) -0.902(7) -0.467(3) 0.045(11) Uiso 1 1 d . . . C3 C -0.8395(7) -0.7888(8) -0.3594(4) 0.0650(15) Uani 1 1 d . . . H3A H -0.784(8) -0.733(8) -0.300(3) 0.066(14) Uiso 1 1 d . . . C4 C -0.8481(8) -1.1145(9) -0.3010(4) 0.0713(15) Uani 1 1 d . . . H4A H -1.001(12) -1.228(12) -0.321(5) 0.12(2) Uiso 1 1 d . . . C5 C -0.6390(7) -1.1685(9) -0.3358(4) 0.0623(14) Uani 1 1 d . . . H5A H -0.666(8) -1.253(9) -0.387(3) 0.068(15) Uiso 1 1 d . . . C6 C -0.5262(11) -1.2730(12) -0.2599(4) 0.0882(19) Uani 1 1 d . . . H6A H -0.546(11) -1.432(10) -0.261(4) 0.093(19) Uiso 1 1 d . . . H6B H -0.352(9) -1.246(8) -0.263(3) 0.067(14) Uiso 1 1 d . . . C7 C -0.6219(11) -1.1825(14) -0.1834(4) 0.104(3) Uani 1 1 d . . . C8 C -0.9904(8) -0.6464(9) -0.4047(4) 0.0773(18) Uani 1 1 d . . . H8A H -1.089(4) -0.706(4) -0.4608(16) 0.000(6) Uiso 1 1 d . . . H8B H -0.904(8) -0.521(9) -0.425(3) 0.062(14) Uiso 1 1 d . . . C9 C -0.4672(16) -1.044(3) -0.1346(5) 0.164(5) Uani 1 1 d . . . H9A H -0.4008 -0.9587 -0.1728 0.246 Uiso 1 1 calc R . . H9B H -0.3588 -1.1184 -0.1034 0.246 Uiso 1 1 calc R . . H9C H -0.5450 -0.9665 -0.0969 0.246 Uiso 1 1 calc R . . C10 C -0.695(2) -1.311(3) -0.1167(7) 0.166(5) Uani 1 1 d . . . H10A H -0.5755 -1.3887 -0.0935 0.200 Uiso 1 1 calc R . . H10B H -0.7455 -1.2307 -0.0722 0.200 Uiso 1 1 calc R . . C11 C -0.855(3) -1.431(2) -0.1457(9) 0.207(7) Uani 1 1 d . . . H11A H -0.8042 -1.5075 -0.1914 0.248 Uiso 1 1 calc R . . H11B H -0.9738 -1.3518 -0.1684 0.248 Uiso 1 1 calc R . . C12 C -0.946(2) -1.586(3) -0.0753(7) 0.218(8) Uani 1 1 d . . . H12A H -0.8494 -1.6948 -0.0674 0.327 Uiso 1 1 calc R . . H12B H -1.0857 -1.6332 -0.0950 0.327 Uiso 1 1 calc R . . H12C H -0.9562 -1.5191 -0.0231 0.327 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 0.0301(15) 0.080(3) 0.107(3) 0.008(2) -0.0027(16) -0.0057(18) O2 0.074(2) 0.107(3) 0.078(2) 0.003(3) 0.0113(19) 0.013(3) O3 0.0303(15) 0.100(3) 0.094(2) -0.016(2) 0.0054(15) -0.0001(18) O4 0.0417(17) 0.092(3) 0.094(3) 0.012(2) -0.0051(18) -0.022(2) O5 0.076(3) 0.134(5) 0.170(5) -0.036(5) -0.013(3) 0.006(4) C1 0.031(2) 0.070(3) 0.066(3) -0.010(3) -0.004(2) -0.002(2) C2 0.038(2) 0.068(3) 0.071(3) -0.005(3) -0.002(2) -0.013(3) C3 0.031(2) 0.066(3) 0.097(4) -0.004(3) -0.005(2) -0.006(2) C4 0.045(2) 0.080(4) 0.088(4) 0.007(3) 0.001(2) -0.006(3) C5 0.043(2) 0.071(3) 0.072(3) 0.001(3) -0.002(2) -0.004(3) C6 0.073(4) 0.096(5) 0.096(4) 0.014(4) 0.009(3) 0.019(4) C7 0.086(4) 0.143(7) 0.082(4) 0.022(5) -0.002(4) 0.021(5) C8 0.041(2) 0.067(4) 0.126(5) 0.005(4) 0.016(3) 0.005(3) C9 0.145(8) 0.226(13) 0.114(6) -0.048(8) -0.043(6) 0.031(10) C10 0.167(10) 0.201(12) 0.128(8) -0.008(9) -0.006(7) 0.054(11) C11 0.269(17) 0.166(12) 0.169(11) 0.034(10) -0.086(12) -0.020(13) C12 0.247(15) 0.27(2) 0.140(8) 0.062(12) 0.041(9) -0.054(15) _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 C3 1.426(7) . ? O1 C4 1.424(7) . ? O2 C4 1.407(7) . ? O2 C7 1.454(8) . ? O3 H3 0.8200 . ? O3 C1 1.427(6) . ? O4 H4 1.03(8) . ? O4 C2 1.430(6) . ? O5 H5 0.8200 . ? O5 C8 1.352(8) . ? C1 H1 1.06(4) . ? C1 C2 1.511(7) . ? C1 C5 1.518(8) . ? C2 H2 0.98(4) . ? C2 C3 1.529(7) . ? C3 H3A 1.06(5) . ? C3 C8 1.505(8) . ? C4 H4A 1.26(8) . ? C4 C5 1.503(7) . ? C5 H5A 1.01(6) . ? C5 C6 1.539(9) . ? C6 H6A 1.09(7) . ? C6 H6B 1.11(5) . ? C6 C7 1.533(11) . ? C7 C9 1.529(14) . ? C7 C10 1.482(15) . ? C8 H8A 1.13(3) . ? C8 H8B 1.07(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.347(18) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.68(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C4 O1 C3 115.8(3) . . ? C4 O2 C7 108.4(5) . . ? C1 O3 H3 109.5 . . ? C2 O4 H4 108(4) . . ? C8 O5 H5 109.5 . . ? O3 C1 H1 109(2) . . ? O3 C1 C2 110.1(4) . . ? O3 C1 C5 107.6(5) . . ? C2 C1 H1 110(2) . . ? C2 C1 C5 112.3(3) . . ? C5 C1 H1 108(2) . . ? O4 C2 C1 108.3(4) . . ? O4 C2 H2 106(3) . . ? O4 C2 C3 109.3(4) . . ? C1 C2 H2 109(3) . . ? C1 C2 C3 108.9(4) . . ? C3 C2 H2 116(3) . . ? O1 C3 C2 108.7(4) . . ? O1 C3 H3A 106(3) . . ? O1 C3 C8 106.7(4) . . ? C2 C3 H3A 113(3) . . ? C8 C3 C2 111.6(5) . . ? C8 C3 H3A 111(3) . . ? O1 C4 H4A 89(4) . . ? O1 C4 C5 114.9(5) . . ? O2 C4 O1 109.5(5) . . ? O2 C4 H4A 122(3) . . ? O2 C4 C5 106.3(4) . . ? C5 C4 H4A 115(4) . . ? C1 C5 H5A 105(3) . . ? C1 C5 C6 112.8(5) . . ? C4 C5 C1 113.5(5) . . ? C4 C5 H5A 110(3) . . ? C4 C5 C6 100.4(5) . . ? C6 C5 H5A 115(3) . . ? C5 C6 H6A 114(4) . . ? C5 C6 H6B 106(3) . . ? H6A C6 H6B 106(5) . . ? C7 C6 C5 105.3(5) . . ? C7 C6 H6A 111(4) . . ? C7 C6 H6B 114(3) . . ? O2 C7 C6 105.1(5) . . ? O2 C7 C9 105.6(8) . . ? O2 C7 C10 110.1(7) . . ? C9 C7 C6 113.1(7) . . ? C10 C7 C6 119.9(8) . . ? C10 C7 C9 102.4(9) . . ? O5 C8 C3 113.5(6) . . ? O5 C8 H8A 105.2(14) . . ? O5 C8 H8B 103(3) . . ? C3 C8 H8A 116.2(15) . . ? C3 C8 H8B 110(3) . . ? H8A C8 H8B 108(3) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.3 . . ? C7 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C11 C10 C7 111.7(10) . . ? C11 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C10 C11 H11A 108.4 . . ? C10 C11 H11B 108.4 . . ? C10 C11 C12 115.5(11) . . ? H11A C11 H11B 107.5 . . ? C12 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 H3 O1 0.82 1.99 2.725(4) 148.2 1_655 O4 H4 O3 1.03(8) 1.65(8) 2.676(6) 172(6) 2_454 O5 H5 O4 0.82 2.06 2.765(6) 143.4 1_455 _database_code_depnum_ccdc_archive 'CCDC 851788'