# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_0914-pym-gq-5p46 _database_code_depnum_ccdc_archive 'CCDC 904546' #TrackingRef '2b.cif' _audit_creation_date 2012-09-15 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H12 O5' _chemical_formula_sum 'C11 H12 O5' _chemical_formula_weight 224.07 _chemical_absolute_configuration unk _chemical_melting_point ? 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 orthorhombic _space_group_IT_number 29 _space_group_name_H-M_alt 'P c a 21' _space_group_name_Hall 'P 2c -2ac' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y, z+1/2' 4 'x+1/2, -y, z' _cell_length_a 20.4479(17) _cell_length_b 3.9674(3) _cell_length_c 13.2324(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1073.47(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2238 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.4777 _cell_measurement_theta_min 2.9791 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description acicular _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8509 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.08 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9784 _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 -9.00 18.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.2889 -99.0000 150.0000 54 #__ type_ start__ end____ width___ exp.time_ 2 omega -13.00 14.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.2889 -99.0000 -90.0000 54 #__ type_ start__ end____ width___ exp.time_ 3 omega -49.00 45.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.5389 -57.0000 120.0000 188 #__ type_ start__ end____ width___ exp.time_ 4 omega -1.00 89.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.5389 57.0000 -90.0000 180 #__ type_ start__ end____ width___ exp.time_ 5 omega -11.00 45.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.5389 -57.0000 -60.0000 112 #__ type_ start__ end____ width___ exp.time_ 6 omega -44.00 53.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.5389 -38.0000 0.0000 194 #__ type_ start__ end____ width___ exp.time_ 7 omega -45.00 60.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 21.5389 19.0000 150.0000 210 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0326640000 _diffrn_orient_matrix_UB_12 0.0267958000 _diffrn_orient_matrix_UB_13 -0.0159517000 _diffrn_orient_matrix_UB_21 -0.0093050000 _diffrn_orient_matrix_UB_22 0.0325268000 _diffrn_orient_matrix_UB_23 0.0507017000 _diffrn_orient_matrix_UB_31 0.0067947000 _diffrn_orient_matrix_UB_32 0.1737572000 _diffrn_orient_matrix_UB_33 -0.0070240000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1695 _reflns_number_total 2165 _reflns_odcompleteness_completeness 99.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _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-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.132 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(17) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2165 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0526 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1371 _refine_ls_wR_factor_ref 0.1491 _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 0.53464(11) -0.0081(7) 0.6421(3) 0.0907(9) Uani 1 1 d . . . H1 H 0.5139 0.0738 0.6891 0.136 Uiso 1 1 calc R . . O2 O 0.51795(10) 0.2646(8) 0.8198(2) 0.0801(8) Uani 1 1 d . . . O3 O 0.60494(9) 0.4293(5) 0.90750(17) 0.0600(6) Uani 1 1 d . . . O4 O 0.84839(12) 0.0193(8) 0.6558(3) 0.0957(9) Uani 1 1 d . . . O5 O 0.81831(10) 0.2692(6) 0.7970(2) 0.0739(7) Uani 1 1 d . . . C1 C 0.56175(17) 0.5475(8) 0.9872(3) 0.0679(9) Uani 1 1 d . . . H1A H 0.5342 0.7236 0.9614 0.102 Uiso 1 1 calc R . . H1B H 0.5874 0.6329 1.0423 0.102 Uiso 1 1 calc R . . H1C H 0.5351 0.3640 1.0105 0.102 Uiso 1 1 calc R . . C2 C 0.57721(13) 0.2911(7) 0.8272(2) 0.0519(7) Uani 1 1 d . . . C3 C 0.62339(13) 0.1720(6) 0.7503(2) 0.0483(6) Uani 1 1 d . . . C4 C 0.59956(15) 0.0264(7) 0.6603(3) 0.0601(8) Uani 1 1 d . . . C5 C 0.6434(2) -0.0836(8) 0.5887(3) 0.0663(9) Uani 1 1 d . . . H5 H 0.6272 -0.1772 0.5294 0.080 Uiso 1 1 calc R . . C6 C 0.70990(17) -0.0619(7) 0.6007(3) 0.0562(8) Uani 1 1 d . . . C7 C 0.7532(2) -0.1909(8) 0.5184(3) 0.0746(10) Uani 1 1 d . . . H7A H 0.7783 -0.3781 0.5431 0.112 Uiso 1 1 calc R . . H7B H 0.7823 -0.0148 0.4969 0.112 Uiso 1 1 calc R . . H7C H 0.7269 -0.2627 0.4623 0.112 Uiso 1 1 calc R . . C8 C 0.73433(13) 0.0844(6) 0.6902(2) 0.0490(7) Uani 1 1 d . . . C9 C 0.69040(13) 0.1989(6) 0.7632(3) 0.0488(7) Uani 1 1 d . . . H9 H 0.7066 0.2959 0.8221 0.059 Uiso 1 1 calc R . . C10 C 0.80507(14) 0.1150(7) 0.7098(3) 0.0572(8) Uani 1 1 d . . . C11 C 0.88595(14) 0.3275(11) 0.8191(4) 0.0835(12) Uani 1 1 d . . . H11A H 0.9081 0.3985 0.7588 0.125 Uiso 1 1 calc R . . H11B H 0.9054 0.1232 0.8436 0.125 Uiso 1 1 calc R . . H11C H 0.8896 0.5000 0.8696 0.125 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 0.0691(14) 0.123(2) 0.080(2) -0.0257(18) -0.0204(14) -0.0086(14) O2 0.0497(11) 0.1065(18) 0.084(2) -0.0158(14) -0.0020(12) -0.0019(11) O3 0.0496(10) 0.0774(13) 0.0531(13) -0.0103(11) 0.0040(11) -0.0031(10) O4 0.0716(15) 0.128(2) 0.087(2) -0.0365(19) 0.0184(16) 0.0078(15) O5 0.0493(11) 0.0921(15) 0.0804(19) -0.0221(15) 0.0078(12) -0.0034(10) C1 0.0640(19) 0.0782(19) 0.062(2) -0.0096(18) 0.0088(17) 0.0003(16) C2 0.0480(14) 0.0544(15) 0.0533(19) 0.0038(13) -0.0051(14) -0.0038(13) C3 0.0532(14) 0.0467(13) 0.0451(17) 0.0037(12) 0.0006(13) -0.0057(12) C4 0.0650(18) 0.0617(17) 0.0536(19) -0.0022(15) -0.0120(17) -0.0033(14) C5 0.093(3) 0.0599(18) 0.046(2) -0.0057(15) -0.0108(17) -0.0035(17) C6 0.080(2) 0.0436(13) 0.0446(19) 0.0046(13) 0.0034(16) 0.0000(14) C7 0.105(3) 0.0644(17) 0.054(2) -0.0075(17) 0.011(2) -0.0003(19) C8 0.0599(16) 0.0416(12) 0.0454(19) 0.0034(12) 0.0048(13) -0.0023(12) C9 0.0555(14) 0.0431(13) 0.0477(17) 0.0048(13) -0.0023(14) -0.0021(11) C10 0.0622(18) 0.0534(15) 0.056(2) 0.0003(15) 0.0124(16) 0.0026(13) C11 0.0505(16) 0.089(2) 0.111(4) -0.020(2) 0.003(2) -0.0019(16) _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 H1 0.8200 . ? O1 C4 1.356(4) . ? O2 C2 1.220(3) . ? O3 C1 1.453(4) . ? O3 C2 1.324(4) . ? O4 C10 1.200(4) . ? O5 C10 1.333(4) . ? O5 C11 1.432(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.466(4) . ? C3 C4 1.411(5) . ? C3 C9 1.385(3) . ? C4 C5 1.374(5) . ? C5 H5 0.9300 . ? C5 C6 1.372(5) . ? C6 C7 1.494(5) . ? C6 C8 1.411(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.394(4) . ? C8 C10 1.475(4) . ? C9 H9 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 H1 109.5 . . ? C2 O3 C1 117.1(2) . . ? C10 O5 C11 116.5(3) . . ? O3 C1 H1A 109.5 . . ? O3 C1 H1B 109.5 . . ? O3 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O3 121.7(3) . . ? O2 C2 C3 123.8(3) . . ? O3 C2 C3 114.5(2) . . ? C4 C3 C2 119.7(2) . . ? C9 C3 C2 121.8(3) . . ? C9 C3 C4 118.5(3) . . ? O1 C4 C3 121.9(3) . . ? O1 C4 C5 119.0(3) . . ? C5 C4 C3 119.1(3) . . ? C4 C5 H5 118.4 . . ? C6 C5 C4 123.2(3) . . ? C6 C5 H5 118.4 . . ? C5 C6 C7 118.8(3) . . ? C5 C6 C8 118.2(3) . . ? C8 C6 C7 122.9(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C10 121.9(3) . . ? C9 C8 C6 119.2(3) . . ? C9 C8 C10 118.9(3) . . ? C3 C9 C8 121.8(3) . . ? C3 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? O4 C10 O5 120.7(3) . . ? O4 C10 C8 126.4(3) . . ? O5 C10 C8 112.9(2) . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 O1 C4 C5 C6 -179.5(3) . . . . ? O2 C2 C3 C4 2.1(4) . . . . ? O2 C2 C3 C9 -178.1(3) . . . . ? O3 C2 C3 C4 -178.7(3) . . . . ? O3 C2 C3 C9 1.1(4) . . . . ? C1 O3 C2 O2 0.3(4) . . . . ? C1 O3 C2 C3 -179.0(2) . . . . ? C2 C3 C4 O1 -0.1(4) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C2 C3 C9 C8 179.8(2) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C4 C3 C9 C8 -0.4(4) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? C4 C5 C6 C8 -0.9(5) . . . . ? C5 C6 C8 C9 0.4(4) . . . . ? C5 C6 C8 C10 179.4(3) . . . . ? C6 C8 C9 C3 0.2(4) . . . . ? C6 C8 C10 O4 -1.3(5) . . . . ? C6 C8 C10 O5 178.1(2) . . . . ? C7 C6 C8 C9 179.9(3) . . . . ? C7 C6 C8 C10 -1.1(4) . . . . ? C9 C3 C4 O1 -179.9(3) . . . . ? C9 C3 C4 C5 0.0(4) . . . . ? C9 C8 C10 O4 177.7(3) . . . . ? C9 C8 C10 O5 -3.0(4) . . . . ? C10 C8 C9 C3 -178.8(3) . . . . ? C11 O5 C10 O4 3.0(5) . . . . ? C11 O5 C10 C8 -176.4(3) . . . . ?