# Electronic Supplementary Material (ESI) for RSC Advances # 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_visk201 _database_code_depnum_ccdc_archive 'CCDC 916037' #TrackingRef 'viks201.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 O5' _chemical_formula_sum 'C8 H12 O5' _chemical_formula_weight 188.18 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8622(5) _cell_length_b 5.9939(5) _cell_length_c 14.537(2) _cell_angle_alpha 91.770(6) _cell_angle_beta 99.179(6) _cell_angle_gamma 117.482(5) _cell_volume 444.15(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2608 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 27.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .6 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2608 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1901 _reflns_number_gt 1440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0493P)^2^+0.0000P] 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 1901 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 O1 O 0.73292(18) 0.71893(17) 0.31850(7) 0.0238(3) Uani 1 1 d . . . O2 O 0.83323(18) 0.95622(18) 0.38149(7) 0.0228(3) Uani 1 1 d . . . O3 O 1.02316(18) 1.19533(16) 0.26511(6) 0.0210(3) Uani 1 1 d . . . O4 O 0.23166(19) 0.69026(18) 0.08495(7) 0.0275(3) Uani 1 1 d . . . O5 O 0.1720(2) 0.31019(18) 0.03009(7) 0.0243(3) Uani 1 1 d . . . H1 H 0.040(4) 0.312(3) -0.0071(13) 0.044(5) Uiso 1 1 d . . . C1 C 1.0759(3) 1.1408(3) 0.35872(10) 0.0204(3) Uani 1 1 d . . . C2 C 0.8932(3) 0.9756(2) 0.19751(10) 0.0206(3) Uani 1 1 d . . . H2A H 1.0133 0.9046 0.1911 0.025 Uiso 1 1 calc R . . H2B H 0.8429 1.0222 0.1357 0.025 Uiso 1 1 calc R . . C3 C 0.6500(3) 0.7784(3) 0.22803(9) 0.0193(3) Uani 1 1 d . . . H3 H 0.5267 0.8485 0.2331 0.023 Uiso 1 1 calc R . . C4 C 0.5140(2) 0.5395(3) 0.16076(9) 0.0198(3) Uani 1 1 d . . . C5 C 0.2932(2) 0.5209(2) 0.08907(10) 0.0196(3) Uani 1 1 d . . . C6 C 0.5847(3) 0.3594(3) 0.16246(11) 0.0273(4) Uani 1 1 d . . . H6A H 0.4934 0.2139 0.1171 0.033 Uiso 1 1 calc R . . H6B H 0.7266 0.3754 0.2090 0.033 Uiso 1 1 calc R . . C7 C 1.1483(3) 1.3762(3) 0.42207(11) 0.0265(4) Uani 1 1 d . . . H7A H 1.3103 1.5153 0.4099 0.040 Uiso 1 1 calc R . . H7B H 1.1751 1.3449 0.4877 0.040 Uiso 1 1 calc R . . H7C H 1.0067 1.4218 0.4099 0.040 Uiso 1 1 calc R . . C8 C 1.2825(3) 1.0538(3) 0.37295(11) 0.0263(4) Uani 1 1 d . . . H8A H 1.2204 0.8959 0.3320 0.039 Uiso 1 1 calc R . . H8B H 1.3159 1.0250 0.4386 0.039 Uiso 1 1 calc R . . H8C H 1.4448 1.1842 0.3575 0.039 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 0.0274(5) 0.0212(5) 0.0178(5) -0.0006(4) 0.0017(4) 0.0084(4) O2 0.0215(5) 0.0245(5) 0.0188(5) -0.0040(4) 0.0042(4) 0.0081(4) O3 0.0245(5) 0.0190(5) 0.0191(5) 0.0001(4) 0.0026(4) 0.0105(4) O4 0.0295(5) 0.0248(5) 0.0281(6) -0.0054(5) -0.0038(4) 0.0163(5) O5 0.0262(5) 0.0213(6) 0.0228(6) -0.0040(4) -0.0028(4) 0.0117(5) C1 0.0183(6) 0.0231(7) 0.0207(7) 0.0016(6) 0.0041(5) 0.0105(6) C2 0.0232(7) 0.0203(7) 0.0181(7) -0.0007(6) 0.0052(5) 0.0099(6) C3 0.0201(6) 0.0239(7) 0.0161(7) 0.0012(6) 0.0024(5) 0.0127(6) C4 0.0190(7) 0.0204(7) 0.0194(7) 0.0011(6) 0.0057(5) 0.0083(6) C5 0.0217(7) 0.0173(7) 0.0193(7) 0.0007(6) 0.0061(6) 0.0084(6) C6 0.0270(8) 0.0263(8) 0.0273(8) -0.0016(7) -0.0001(6) 0.0135(7) C7 0.0287(8) 0.0270(8) 0.0248(8) -0.0042(6) 0.0011(6) 0.0157(7) C8 0.0226(7) 0.0284(8) 0.0297(8) 0.0005(7) 0.0020(6) 0.0147(6) _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 1.4416(17) . ? O1 O2 1.4775(13) . ? O2 C1 1.4412(16) . ? O3 C2 1.4268(15) . ? O3 C1 1.4285(17) . ? O4 C5 1.2240(17) . ? O5 C5 1.3214(16) . ? O5 H1 0.87(2) . ? C1 C7 1.504(2) . ? C1 C8 1.513(2) . ? C2 C3 1.5180(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5015(19) . ? C3 H3 1.0000 . ? C4 C6 1.322(2) . ? C4 C5 1.485(2) . ? C6 H6A 0.9500 . ? C6 H6B 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C3 O1 O2 104.09(9) . . ? C1 O2 O1 108.61(9) . . ? C2 O3 C1 113.42(10) . . ? C5 O5 H1 108.3(11) . . ? O3 C1 O2 108.64(10) . . ? O3 C1 C7 106.18(11) . . ? O2 C1 C7 103.71(11) . . ? O3 C1 C8 112.69(11) . . ? O2 C1 C8 111.68(12) . . ? C7 C1 C8 113.38(12) . . ? O3 C2 C3 109.91(11) . . ? O3 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? O3 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C4 108.37(11) . . ? O1 C3 C2 107.57(11) . . ? C4 C3 C2 111.53(11) . . ? O1 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? C6 C4 C5 121.52(12) . . ? C6 C4 C3 123.81(13) . . ? C5 C4 C3 114.65(12) . . ? O4 C5 O5 123.11(13) . . ? O4 C5 C4 122.06(12) . . ? O5 C5 C4 114.83(12) . . ? C4 C6 H6A 120.0 . . ? C4 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 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 C3 O1 O2 C1 -70.56(12) . . . . ? C2 O3 C1 O2 -55.19(14) . . . . ? C2 O3 C1 C7 -166.19(10) . . . . ? C2 O3 C1 C8 69.12(14) . . . . ? O1 O2 C1 O3 63.67(13) . . . . ? O1 O2 C1 C7 176.31(9) . . . . ? O1 O2 C1 C8 -61.24(13) . . . . ? C1 O3 C2 C3 52.52(15) . . . . ? O2 O1 C3 C4 -173.21(9) . . . . ? O2 O1 C3 C2 66.08(12) . . . . ? O3 C2 C3 O1 -58.78(15) . . . . ? O3 C2 C3 C4 -177.48(10) . . . . ? O1 C3 C4 C6 -35.83(18) . . . . ? C2 C3 C4 C6 82.40(17) . . . . ? O1 C3 C4 C5 145.50(11) . . . . ? C2 C3 C4 C5 -96.28(14) . . . . ? C6 C4 C5 O4 -177.56(13) . . . . ? C3 C4 C5 O4 1.15(19) . . . . ? C6 C4 C5 O5 1.69(19) . . . . ? C3 C4 C5 O5 -179.61(10) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.270 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.050 ####################################################################### # # 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_visk340 _database_code_depnum_ccdc_archive 'CCDC 916038' #TrackingRef 'viks340.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 O5' _chemical_formula_sum 'C11 H16 O5' _chemical_formula_weight 228.24 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.425(3) _cell_length_b 6.0562(8) _cell_length_c 20.621(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.361(6) _cell_angle_gamma 90.00 _cell_volume 2173.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9667 _cell_measurement_theta_min 1.17 _cell_measurement_theta_max 27.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9667 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1669 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4699 _reflns_number_gt 1907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0750P)^2^+0.0000P] 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 4699 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1968 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1840 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _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 O1 O 0.18137(14) 0.3383(4) 0.15457(13) 0.0295(7) Uani 1 1 d . . . O2 O 0.23421(14) 0.1568(4) 0.16084(13) 0.0315(7) Uani 1 1 d . . . O3 O 0.27548(15) 0.5133(4) 0.25638(13) 0.0282(7) Uani 1 1 d . . . O4 O 0.46816(17) 0.0212(4) 0.15602(15) 0.0317(7) Uani 1 1 d . . . H4X H 0.498(3) 0.073(8) 0.138(3) 0.11(2) Uiso 1 1 d . . . O5 O 0.42176(15) 0.3665(4) 0.14007(14) 0.0340(7) Uani 1 1 d . . . C1 C 0.3075(2) 0.2643(5) 0.1821(2) 0.0254(9) Uani 1 1 d . . . H1X H 0.3022 0.3845 0.1469 0.030 Uiso 1 1 calc R . . C2 C 0.3319(2) 0.3612(6) 0.2565(2) 0.0291(10) Uani 1 1 d . . . H2A H 0.3390 0.2409 0.2914 0.035 Uiso 1 1 calc R . . H2B H 0.3816 0.4382 0.2721 0.035 Uiso 1 1 calc R . . C3 C 0.1995(2) 0.4225(5) 0.22555(19) 0.0257(9) Uani 1 1 d . . . C4 C 0.1456(2) 0.6160(5) 0.2123(2) 0.0299(10) Uani 1 1 d . . . H4A H 0.1508 0.7177 0.1771 0.036 Uiso 1 1 calc R . . H4B H 0.1606 0.6977 0.2581 0.036 Uiso 1 1 calc R . . C5 C 0.0617(2) 0.5435(6) 0.1832(2) 0.0327(10) Uani 1 1 d . . . H5A H 0.0292 0.6734 0.1794 0.039 Uiso 1 1 calc R . . H5B H 0.0441 0.4800 0.1342 0.039 Uiso 1 1 calc R . . C6 C 0.0528(2) 0.3715(5) 0.2333(2) 0.0336(10) Uani 1 1 d . . . H6A H 0.0651 0.4402 0.2807 0.040 Uiso 1 1 calc R . . H6B H -0.0012 0.3203 0.2122 0.040 Uiso 1 1 calc R . . C7 C 0.1054(2) 0.1749(6) 0.2443(2) 0.0342(10) Uani 1 1 d . . . H7A H 0.0899 0.0973 0.1976 0.041 Uiso 1 1 calc R . . H7B H 0.1003 0.0703 0.2787 0.041 Uiso 1 1 calc R . . C8 C 0.1893(2) 0.2482(5) 0.2735(2) 0.0263(9) Uani 1 1 d . . . H8A H 0.2067 0.3085 0.3229 0.032 Uiso 1 1 calc R . . H8B H 0.2217 0.1186 0.2766 0.032 Uiso 1 1 calc R . . C9 C 0.3633(2) 0.0945(6) 0.18183(19) 0.0270(10) Uani 1 1 d . . . C10 C 0.4203(2) 0.1727(6) 0.15753(19) 0.0263(9) Uani 1 1 d . . . C11 C 0.3636(2) -0.1123(6) 0.2023(2) 0.0368(11) Uani 1 1 d . . . H11A H 0.4006 -0.2133 0.2016 0.044 Uiso 1 1 calc R . . H11B H 0.3266 -0.1600 0.2178 0.044 Uiso 1 1 calc R . . O6 O 0.19341(14) 0.6949(4) 0.40404(13) 0.0279(7) Uani 1 1 d . . . O7 O 0.24337(14) 0.8795(4) 0.40600(13) 0.0293(7) Uani 1 1 d . . . O8 O 0.29109(15) 0.5374(3) 0.50633(13) 0.0291(7) Uani 1 1 d . . . O9 O 0.44250(15) 0.6809(4) 0.39918(14) 0.0316(7) Uani 1 1 d . . . O10 O 0.47519(16) 1.0360(4) 0.39783(14) 0.0332(7) Uani 1 1 d . . . H10X H 0.519(3) 0.974(7) 0.381(3) 0.095(18) Uiso 1 1 d . . . C12 C 0.3178(2) 0.7797(5) 0.4277(2) 0.0259(9) Uani 1 1 d . . . H12 H 0.3137 0.6564 0.3939 0.031 Uiso 1 1 calc R . . C13 C 0.3452(2) 0.6912(6) 0.5034(2) 0.0283(10) Uani 1 1 d . . . H13A H 0.3955 0.6178 0.5188 0.034 Uiso 1 1 calc R . . H13B H 0.3519 0.8148 0.5371 0.034 Uiso 1 1 calc R . . C14 C 0.2144(2) 0.6237(5) 0.4766(2) 0.0245(9) Uani 1 1 d . . . C15 C 0.2052(2) 0.8048(5) 0.5223(2) 0.0289(10) Uani 1 1 d . . . H15A H 0.2356 0.9351 0.5214 0.035 Uiso 1 1 calc R . . H15B H 0.2255 0.7537 0.5730 0.035 Uiso 1 1 calc R . . C16 C 0.1206(2) 0.8723(5) 0.4949(2) 0.0270(9) Uani 1 1 d . . . H16A H 0.1161 0.9849 0.5276 0.032 Uiso 1 1 calc R . . H16B H 0.1015 0.9380 0.4460 0.032 Uiso 1 1 calc R . . C17 C 0.0723(2) 0.6732(5) 0.4920(2) 0.0308(10) Uani 1 1 d . . . H17A H 0.0179 0.7188 0.4737 0.037 Uiso 1 1 calc R . . H17B H 0.0894 0.6137 0.5415 0.037 Uiso 1 1 calc R . . C18 C 0.0784(2) 0.4937(6) 0.4434(2) 0.0318(10) Uani 1 1 d . . . H18A H 0.0566 0.5476 0.3928 0.038 Uiso 1 1 calc R . . H18B H 0.0486 0.3628 0.4448 0.038 Uiso 1 1 calc R . . C19 C 0.1626(2) 0.4290(5) 0.4686(2) 0.0306(10) Uani 1 1 d . . . H19A H 0.1813 0.3523 0.5158 0.037 Uiso 1 1 calc R . . H19B H 0.1660 0.3239 0.4334 0.037 Uiso 1 1 calc R . . C20 C 0.3711(2) 0.9558(6) 0.42438(19) 0.0271(10) Uani 1 1 d . . . C21 C 0.4322(2) 0.8782(6) 0.40608(19) 0.0249(9) Uani 1 1 d . . . C22 C 0.3665(2) 1.1669(6) 0.43980(19) 0.0310(10) Uani 1 1 d . . . H22A H 0.4029 1.2704 0.4391 0.037 Uiso 1 1 calc R . . H22B H 0.3267 1.2143 0.4515 0.037 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 0.0270(16) 0.0396(15) 0.0234(16) -0.0014(12) 0.0125(13) 0.0054(13) O2 0.0277(17) 0.0377(15) 0.0325(17) -0.0081(12) 0.0165(14) 0.0001(13) O3 0.0249(16) 0.0275(14) 0.0362(17) -0.0045(11) 0.0170(13) -0.0036(13) O4 0.0302(18) 0.0336(16) 0.0381(18) 0.0042(12) 0.0213(15) 0.0024(14) O5 0.0339(18) 0.0300(15) 0.0467(19) 0.0048(13) 0.0255(15) 0.0021(13) C1 0.023(2) 0.030(2) 0.025(2) 0.0028(16) 0.012(2) -0.0041(19) C2 0.025(2) 0.030(2) 0.033(3) -0.0045(17) 0.013(2) -0.0025(19) C3 0.024(2) 0.031(2) 0.025(2) -0.0001(16) 0.013(2) -0.0011(19) C4 0.035(3) 0.030(2) 0.028(2) 0.0025(17) 0.017(2) 0.0020(19) C5 0.031(3) 0.033(2) 0.037(3) 0.0008(18) 0.018(2) 0.0070(19) C6 0.034(3) 0.035(2) 0.037(3) -0.0033(19) 0.021(2) -0.002(2) C7 0.037(3) 0.032(2) 0.040(3) 0.0027(19) 0.024(2) 0.002(2) C8 0.025(2) 0.030(2) 0.026(2) 0.0018(16) 0.013(2) 0.0013(18) C9 0.031(3) 0.029(2) 0.022(2) 0.0030(16) 0.013(2) 0.0002(19) C10 0.026(3) 0.031(2) 0.020(2) -0.0028(17) 0.0082(19) -0.001(2) C11 0.032(3) 0.044(3) 0.039(3) 0.001(2) 0.020(2) -0.001(2) O6 0.0300(17) 0.0330(14) 0.0234(16) -0.0004(11) 0.0142(13) -0.0103(13) O7 0.0236(16) 0.0322(14) 0.0337(17) 0.0052(11) 0.0141(13) -0.0009(13) O8 0.0308(17) 0.0258(14) 0.0335(17) 0.0021(11) 0.0168(14) 0.0013(13) O9 0.0338(18) 0.0301(15) 0.0357(18) -0.0042(12) 0.0197(14) -0.0005(13) O10 0.0296(18) 0.0323(15) 0.0447(19) -0.0015(12) 0.0229(15) -0.0025(14) C12 0.023(2) 0.028(2) 0.028(3) -0.0016(16) 0.013(2) 0.0023(19) C13 0.022(2) 0.035(2) 0.030(3) 0.0019(17) 0.0130(19) -0.0025(19) C14 0.021(2) 0.030(2) 0.023(2) 0.0033(17) 0.0111(19) 0.0049(18) C15 0.033(3) 0.030(2) 0.026(2) -0.0021(17) 0.015(2) -0.0022(19) C16 0.022(2) 0.033(2) 0.029(2) -0.0035(17) 0.0127(19) 0.0002(19) C17 0.026(2) 0.036(2) 0.034(3) -0.0025(18) 0.016(2) -0.005(2) C18 0.032(3) 0.036(2) 0.032(3) -0.0025(18) 0.018(2) -0.008(2) C19 0.035(3) 0.031(2) 0.030(2) -0.0024(17) 0.019(2) -0.003(2) C20 0.026(2) 0.030(2) 0.025(2) -0.0016(17) 0.0106(19) 0.0008(19) C21 0.025(3) 0.029(2) 0.019(2) 0.0011(17) 0.0083(19) -0.003(2) C22 0.030(3) 0.036(2) 0.033(3) -0.0022(18) 0.019(2) -0.003(2) _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 1.438(4) . ? O1 O2 1.470(3) . ? O2 C1 1.445(4) . ? O3 C2 1.430(4) . ? O3 C3 1.432(4) . ? O4 C10 1.316(4) . ? O4 H4X 0.89(5) . ? O5 C10 1.231(4) . ? C1 C9 1.496(5) . ? C1 C2 1.510(5) . ? C1 H1X 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(5) . ? C3 C8 1.518(5) . ? C4 C5 1.531(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.530(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.519(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.530(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C11 1.321(4) . ? C9 C10 1.481(5) . ? C11 H11A 0.9500 . ? C11 H11B 0.9500 . ? O6 C14 1.431(4) . ? O6 O7 1.469(3) . ? O7 C12 1.443(4) . ? O8 C13 1.425(4) . ? O8 C14 1.434(4) . ? O9 C21 1.230(4) . ? O10 C21 1.328(4) . ? O10 H10X 1.11(5) . ? C12 C13 1.508(5) . ? C12 C20 1.510(5) . ? C12 H12 1.0000 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.508(5) . ? C14 C19 1.511(5) . ? C15 C16 1.537(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.512(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.531(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C22 1.330(4) . ? C20 C21 1.473(5) . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? 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 C3 O1 O2 109.2(2) . . ? C1 O2 O1 104.2(2) . . ? C2 O3 C3 113.0(2) . . ? C10 O4 H4X 112(3) . . ? O2 C1 C9 107.9(3) . . ? O2 C1 C2 107.7(3) . . ? C9 C1 C2 111.7(3) . . ? O2 C1 H1X 109.8 . . ? C9 C1 H1X 109.8 . . ? C2 C1 H1X 109.8 . . ? O3 C2 C1 110.8(3) . . ? O3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? O3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O3 C3 O1 109.0(3) . . ? O3 C3 C4 106.0(3) . . ? O1 C3 C4 104.7(3) . . ? O3 C3 C8 112.6(3) . . ? O1 C3 C8 111.9(3) . . ? C4 C3 C8 112.1(3) . . ? C3 C4 C5 112.3(3) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 110.5(3) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 111.4(3) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 111.1(3) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C3 C8 C7 111.7(3) . . ? C3 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C3 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C11 C9 C10 121.0(4) . . ? C11 C9 C1 123.4(4) . . ? C10 C9 C1 115.7(3) . . ? O5 C10 O4 123.3(4) . . ? O5 C10 C9 121.4(4) . . ? O4 C10 C9 115.3(3) . . ? C9 C11 H11A 120.0 . . ? C9 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? C14 O6 O7 108.8(2) . . ? C12 O7 O6 104.4(2) . . ? C13 O8 C14 112.9(2) . . ? C21 O10 H10X 114(2) . . ? O7 C12 C13 108.3(3) . . ? O7 C12 C20 107.7(3) . . ? C13 C12 C20 111.4(3) . . ? O7 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C20 C12 H12 109.8 . . ? O8 C13 C12 110.4(3) . . ? O8 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? O8 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? O6 C14 O8 108.5(3) . . ? O6 C14 C15 112.1(3) . . ? O8 C14 C15 112.8(3) . . ? O6 C14 C19 104.7(3) . . ? O8 C14 C19 106.1(3) . . ? C15 C14 C19 112.2(3) . . ? C14 C15 C16 111.6(3) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 110.2(3) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C18 111.6(3) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C17 C18 C19 110.1(3) . . ? C17 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? C17 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.2 . . ? C14 C19 C18 113.4(3) . . ? C14 C19 H19A 108.9 . . ? C18 C19 H19A 108.9 . . ? C14 C19 H19B 108.9 . . ? C18 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C22 C20 C21 121.1(4) . . ? C22 C20 C12 123.2(4) . . ? C21 C20 C12 115.7(3) . . ? O9 C21 O10 122.7(4) . . ? O9 C21 C20 122.0(3) . . ? O10 C21 C20 115.2(3) . . ? C20 C22 H22A 120.0 . . ? C20 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? 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 C3 O1 O2 C1 -70.1(3) . . . . ? O1 O2 C1 C9 -173.8(3) . . . . ? O1 O2 C1 C2 65.4(3) . . . . ? C3 O3 C2 C1 51.5(4) . . . . ? O2 C1 C2 O3 -58.2(4) . . . . ? C9 C1 C2 O3 -176.6(3) . . . . ? C2 O3 C3 O1 -53.9(3) . . . . ? C2 O3 C3 C4 -166.1(3) . . . . ? C2 O3 C3 C8 70.9(4) . . . . ? O2 O1 C3 O3 63.3(3) . . . . ? O2 O1 C3 C4 176.4(2) . . . . ? O2 O1 C3 C8 -61.9(3) . . . . ? O3 C3 C4 C5 -176.6(3) . . . . ? O1 C3 C4 C5 68.2(4) . . . . ? C8 C3 C4 C5 -53.3(4) . . . . ? C3 C4 C5 C6 54.2(4) . . . . ? C4 C5 C6 C7 -55.8(4) . . . . ? C5 C6 C7 C8 56.4(4) . . . . ? O3 C3 C8 C7 172.8(3) . . . . ? O1 C3 C8 C7 -64.0(4) . . . . ? C4 C3 C8 C7 53.3(4) . . . . ? C6 C7 C8 C3 -54.7(4) . . . . ? O2 C1 C9 C11 -36.8(5) . . . . ? C2 C1 C9 C11 81.5(4) . . . . ? O2 C1 C9 C10 143.8(3) . . . . ? C2 C1 C9 C10 -97.9(4) . . . . ? C11 C9 C10 O5 -178.2(3) . . . . ? C1 C9 C10 O5 1.3(5) . . . . ? C11 C9 C10 O4 2.0(5) . . . . ? C1 C9 C10 O4 -178.6(3) . . . . ? C14 O6 O7 C12 70.1(3) . . . . ? O6 O7 C12 C13 -64.6(3) . . . . ? O6 O7 C12 C20 174.9(2) . . . . ? C14 O8 C13 C12 -52.2(4) . . . . ? O7 C12 C13 O8 57.5(4) . . . . ? C20 C12 C13 O8 175.7(3) . . . . ? O7 O6 C14 O8 -64.6(3) . . . . ? O7 O6 C14 C15 60.5(3) . . . . ? O7 O6 C14 C19 -177.6(2) . . . . ? C13 O8 C14 O6 55.8(3) . . . . ? C13 O8 C14 C15 -68.9(4) . . . . ? C13 O8 C14 C19 167.9(3) . . . . ? O6 C14 C15 C16 64.9(4) . . . . ? O8 C14 C15 C16 -172.3(3) . . . . ? C19 C14 C15 C16 -52.5(4) . . . . ? C14 C15 C16 C17 55.9(4) . . . . ? C15 C16 C17 C18 -58.2(4) . . . . ? C16 C17 C18 C19 56.2(4) . . . . ? O6 C14 C19 C18 -70.3(4) . . . . ? O8 C14 C19 C18 175.0(3) . . . . ? C15 C14 C19 C18 51.5(4) . . . . ? C17 C18 C19 C14 -52.6(4) . . . . ? O7 C12 C20 C22 34.1(5) . . . . ? C13 C12 C20 C22 -84.4(4) . . . . ? O7 C12 C20 C21 -148.7(3) . . . . ? C13 C12 C20 C21 92.8(4) . . . . ? C22 C20 C21 O9 172.2(3) . . . . ? C12 C20 C21 O9 -5.1(5) . . . . ? C22 C20 C21 O10 -7.7(5) . . . . ? C12 C20 C21 O10 175.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.307 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.072 ####################################################################### # # 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_visk365 _database_code_depnum_ccdc_archive 'CCDC 916039' #TrackingRef 'viks365.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 O5' _chemical_formula_sum 'C12 H18 O5' _chemical_formula_weight 242.26 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0548(19) _cell_length_b 6.2630(16) _cell_length_c 17.151(5) _cell_angle_alpha 92.206(18) _cell_angle_beta 90.083(15) _cell_angle_gamma 115.426(14) _cell_volume 586.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3140 _cell_measurement_theta_min 1.19 _cell_measurement_theta_max 27.00 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3140 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.1267 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _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 1.19 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2381 _reflns_number_gt 1226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0793P)^2^+0.0000P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2381 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O1 O 0.3933(4) 0.7014(4) 0.30039(12) 0.0263(6) Uani 1 1 d . . . O2 O 0.1671(4) 0.6168(4) 0.25176(12) 0.0271(6) Uani 1 1 d . . . O3 O 0.6297(4) 0.8949(4) 0.19513(12) 0.0236(6) Uani 1 1 d . . . O4 O 0.1780(5) 0.1933(4) 0.06625(14) 0.0314(7) Uani 1 1 d . . . O5 O -0.1959(4) 0.1463(4) 0.02747(13) 0.0250(6) Uani 1 1 d . . . C1 C 0.2380(7) 0.5558(6) 0.17658(18) 0.0234(8) Uani 1 1 d . . . C2 C 0.4227(7) 0.7848(6) 0.1441(2) 0.0237(8) Uani 1 1 d . . . C3 C 0.5663(6) 0.9261(5) 0.27417(18) 0.0237(9) Uani 1 1 d . . . C4 C 0.7956(7) 0.9742(7) 0.32162(19) 0.0254(9) Uani 1 1 d . . . C5 C 0.7729(8) 0.9879(6) 0.4103(2) 0.0278(9) Uani 1 1 d . . . C6 C 0.8215(8) 1.2306(6) 0.4452(2) 0.0302(9) Uani 1 1 d . . . C7 C 0.6879(8) 1.3575(6) 0.4053(2) 0.0316(9) Uani 1 1 d . . . C8 C 0.4464(7) 1.2015(6) 0.36401(19) 0.0278(9) Uani 1 1 d . . . C9 C 0.4698(7) 1.1141(6) 0.2812(2) 0.0255(9) Uani 1 1 d . . . C10 C 0.0121(6) 0.4417(5) 0.12583(18) 0.0212(8) Uani 1 1 d . . . C11 C 0.0064(7) 0.2490(5) 0.07120(18) 0.0228(8) Uani 1 1 d . . . C12 C -0.1672(8) 0.5093(7) 0.1268(2) 0.0293(9) Uani 1 1 d . . . H1 H 0.601(6) 0.871(5) 0.4237(16) 0.015(8) Uiso 1 1 d . . . H2 H 0.341(6) 1.061(5) 0.3952(17) 0.022(9) Uiso 1 1 d . . . H3 H 0.986(7) 1.327(5) 0.4445(17) 0.022(9) Uiso 1 1 d . . . H4 H 0.778(7) 1.214(6) 0.506(2) 0.042(10) Uiso 1 1 d . . . H5 H 0.309(7) 1.046(5) 0.2554(18) 0.025(9) Uiso 1 1 d . . . H6 H 0.491(6) 0.746(5) 0.0968(18) 0.021(9) Uiso 1 1 d . . . H7 H 0.337(6) 1.289(5) 0.3596(16) 0.017(8) Uiso 1 1 d . . . H8 H 0.885(7) 0.928(6) 0.435(2) 0.044(11) Uiso 1 1 d . . . H9 H 0.347(7) 0.894(6) 0.1331(19) 0.033(10) Uiso 1 1 d . . . H10 H 0.917(6) 1.118(6) 0.3064(18) 0.024(9) Uiso 1 1 d . . . H11 H 0.594(7) 1.253(6) 0.2530(19) 0.034(10) Uiso 1 1 d . . . H12 H 0.844(6) 0.846(6) 0.3039(18) 0.028(9) Uiso 1 1 d . . . H13 H 0.798(8) 1.465(7) 0.370(2) 0.055(13) Uiso 1 1 d . . . H14 H -0.308(7) 0.428(6) 0.0965(18) 0.028(10) Uiso 1 1 d . . . H15 H 0.660(8) 1.469(7) 0.447(2) 0.054(12) Uiso 1 1 d . . . H16 H 0.326(6) 0.449(5) 0.1821(17) 0.028(9) Uiso 1 1 d . . . H17 H -0.163(7) 0.642(6) 0.162(2) 0.045(11) Uiso 1 1 d . . . H18 H -0.178(7) 0.034(7) -0.004(2) 0.044(12) 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 O1 0.0250(15) 0.0227(12) 0.0262(12) 0.0024(10) -0.0044(11) 0.0055(11) O2 0.0258(15) 0.0277(12) 0.0220(12) -0.0019(10) -0.0001(11) 0.0063(11) O3 0.0195(14) 0.0265(12) 0.0226(12) -0.0024(9) -0.0002(10) 0.0082(11) O4 0.0280(16) 0.0315(13) 0.0371(14) -0.0107(11) -0.0068(12) 0.0159(12) O5 0.0230(15) 0.0250(12) 0.0250(12) -0.0049(10) 0.0001(11) 0.0090(11) C1 0.027(2) 0.0229(18) 0.0224(17) -0.0003(14) 0.0045(16) 0.0124(17) C2 0.022(2) 0.0220(18) 0.0249(18) -0.0011(15) -0.0001(16) 0.0071(16) C3 0.029(2) 0.0187(17) 0.0202(16) 0.0012(13) 0.0011(15) 0.0068(16) C4 0.022(2) 0.0243(19) 0.0292(19) -0.0024(16) -0.0006(16) 0.0090(18) C5 0.028(2) 0.0266(19) 0.0313(19) 0.0009(16) -0.0015(17) 0.0137(18) C6 0.030(3) 0.028(2) 0.030(2) -0.0037(16) -0.0025(18) 0.0107(19) C7 0.035(3) 0.026(2) 0.035(2) -0.0030(18) -0.0028(19) 0.0149(19) C8 0.031(2) 0.0275(19) 0.0283(19) 0.0010(16) 0.0017(17) 0.0158(18) C9 0.023(2) 0.0230(18) 0.0288(19) -0.0006(16) 0.0003(17) 0.0089(17) C10 0.020(2) 0.0197(17) 0.0222(17) 0.0024(14) 0.0027(15) 0.0070(15) C11 0.024(2) 0.0176(17) 0.0228(17) 0.0028(14) 0.0017(16) 0.0055(16) C12 0.026(2) 0.029(2) 0.030(2) -0.0023(17) -0.0008(18) 0.0093(18) _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 1.437(4) . ? O1 O2 1.481(3) . ? O2 C1 1.448(4) . ? O3 C2 1.421(4) . ? O3 C3 1.438(4) . ? O4 C11 1.232(4) . ? O5 C11 1.327(4) . ? O5 H18 0.91(4) . ? C1 C10 1.500(5) . ? C1 C2 1.518(5) . ? C1 H16 1.03(4) . ? C2 H6 0.98(3) . ? C2 H9 1.00(4) . ? C3 C4 1.517(5) . ? C3 C9 1.524(5) . ? C4 C5 1.529(5) . ? C4 H10 0.93(3) . ? C4 H12 1.00(4) . ? C5 C6 1.517(5) . ? C5 H1 1.02(3) . ? C5 H8 1.01(4) . ? C6 C7 1.532(5) . ? C6 H3 0.91(3) . ? C6 H4 1.08(4) . ? C7 C8 1.520(5) . ? C7 H13 0.96(4) . ? C7 H15 1.04(4) . ? C8 C9 1.532(5) . ? C8 H2 1.01(3) . ? C8 H7 1.03(3) . ? C9 H5 0.98(3) . ? C9 H11 1.01(4) . ? C10 C12 1.324(5) . ? C10 C11 1.487(5) . ? C12 H14 0.93(3) . ? C12 H17 1.00(4) . ? 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 C3 O1 O2 109.3(2) . . ? C1 O2 O1 104.1(2) . . ? C2 O3 C3 113.1(3) . . ? C11 O5 H18 107(3) . . ? O2 C1 C10 107.8(3) . . ? O2 C1 C2 106.8(3) . . ? C10 C1 C2 112.0(3) . . ? O2 C1 H16 111.4(17) . . ? C10 C1 H16 112.2(18) . . ? C2 C1 H16 106.6(18) . . ? O3 C2 C1 110.8(3) . . ? O3 C2 H6 103.4(19) . . ? C1 C2 H6 108.4(17) . . ? O3 C2 H9 111.5(19) . . ? C1 C2 H9 111(2) . . ? H6 C2 H9 111(3) . . ? O1 C3 O3 108.8(2) . . ? O1 C3 C4 103.2(2) . . ? O3 C3 C4 104.3(3) . . ? O1 C3 C9 112.2(3) . . ? O3 C3 C9 111.4(3) . . ? C4 C3 C9 116.3(3) . . ? C3 C4 C5 116.0(3) . . ? C3 C4 H10 107(2) . . ? C5 C4 H10 108.3(19) . . ? C3 C4 H12 104.6(19) . . ? C5 C4 H12 112.3(18) . . ? H10 C4 H12 108(3) . . ? C6 C5 C4 115.2(3) . . ? C6 C5 H1 109.1(17) . . ? C4 C5 H1 107.7(16) . . ? C6 C5 H8 111(2) . . ? C4 C5 H8 108(2) . . ? H1 C5 H8 106(3) . . ? C5 C6 C7 115.8(3) . . ? C5 C6 H3 110(2) . . ? C7 C6 H3 108(2) . . ? C5 C6 H4 108.3(19) . . ? C7 C6 H4 110(2) . . ? H3 C6 H4 105(3) . . ? C8 C7 C6 116.6(3) . . ? C8 C7 H13 110(2) . . ? C6 C7 H13 108(3) . . ? C8 C7 H15 109(2) . . ? C6 C7 H15 108(2) . . ? H13 C7 H15 103(3) . . ? C7 C8 C9 114.8(3) . . ? C7 C8 H2 112.5(17) . . ? C9 C8 H2 108.9(17) . . ? C7 C8 H7 111.1(17) . . ? C9 C8 H7 106.5(16) . . ? H2 C8 H7 102(3) . . ? C3 C9 C8 116.5(3) . . ? C3 C9 H5 106.3(19) . . ? C8 C9 H5 109.0(19) . . ? C3 C9 H11 104(2) . . ? C8 C9 H11 108.1(18) . . ? H5 C9 H11 113(3) . . ? C12 C10 C11 121.6(3) . . ? C12 C10 C1 123.5(3) . . ? C11 C10 C1 114.9(3) . . ? O4 C11 O5 123.1(3) . . ? O4 C11 C10 122.4(3) . . ? O5 C11 C10 114.5(3) . . ? C10 C12 H14 121(2) . . ? C10 C12 H17 122(2) . . ? H14 C12 H17 117(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 C3 O1 O2 C1 70.5(3) . . . . ? O1 O2 C1 C10 173.6(2) . . . . ? O1 O2 C1 C2 -65.9(3) . . . . ? C3 O3 C2 C1 -52.6(4) . . . . ? O2 C1 C2 O3 59.4(4) . . . . ? C10 C1 C2 O3 177.2(3) . . . . ? O2 O1 C3 O3 -62.8(3) . . . . ? O2 O1 C3 C4 -173.1(2) . . . . ? O2 O1 C3 C9 60.9(3) . . . . ? C2 O3 C3 O1 54.0(3) . . . . ? C2 O3 C3 C4 163.7(3) . . . . ? C2 O3 C3 C9 -70.2(3) . . . . ? O1 C3 C4 C5 -59.9(4) . . . . ? O3 C3 C4 C5 -173.5(3) . . . . ? C9 C3 C4 C5 63.5(4) . . . . ? C3 C4 C5 C6 -87.7(4) . . . . ? C4 C5 C6 C7 48.7(5) . . . . ? C5 C6 C7 C8 27.5(5) . . . . ? C6 C7 C8 C9 -83.1(4) . . . . ? O1 C3 C9 C8 70.2(4) . . . . ? O3 C3 C9 C8 -167.6(3) . . . . ? C4 C3 C9 C8 -48.4(4) . . . . ? C7 C8 C9 C3 72.0(4) . . . . ? O2 C1 C10 C12 37.2(4) . . . . ? C2 C1 C10 C12 -79.9(4) . . . . ? O2 C1 C10 C11 -144.8(3) . . . . ? C2 C1 C10 C11 98.0(3) . . . . ? C12 C10 C11 O4 175.6(3) . . . . ? C1 C10 C11 O4 -2.4(4) . . . . ? C12 C10 C11 O5 -3.1(4) . . . . ? C1 C10 C11 O5 178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.285 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.074 ####################################################################### # # 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_VISK374 _database_code_depnum_ccdc_archive 'CCDC 916040' #TrackingRef 'viks374.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N O7' _chemical_formula_sum 'C12 H11 N O7' _chemical_formula_weight 281.22 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' N N 0.0061 0.0033 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8007(3) _cell_length_b 6.1104(4) _cell_length_c 21.5634(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.699(3) _cell_angle_gamma 90.00 _cell_volume 1191.33(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6089 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6089 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2566 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0440P)^2^+0.2686P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2566 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.46704(10) -0.30890(15) -0.07538(5) 0.0208(2) Uani 1 1 d . . . O2 O 0.56225(10) -0.46949(15) -0.08998(5) 0.0203(2) Uani 1 1 d . . . O3 O 0.35692(9) -0.66253(15) -0.16183(5) 0.0202(2) Uani 1 1 d . . . O4 O 0.07363(11) -0.22964(17) -0.00486(5) 0.0267(3) Uani 1 1 d . . . H4 H 0.007(2) -0.300(4) 0.0076(10) 0.056(6) Uiso 1 1 d . . . O5 O 0.12130(10) -0.56755(16) -0.03216(5) 0.0227(2) Uani 1 1 d . . . O6 O 1.02900(10) -0.98782(17) -0.20122(5) 0.0266(2) Uani 1 1 d . . . O7 O 0.94566(10) -1.27260(16) -0.16678(5) 0.0265(3) Uani 1 1 d . . . N1 N 0.94052(12) -1.07793(19) -0.18169(6) 0.0201(3) Uani 1 1 d . . . C1 C 0.48388(15) -0.5466(2) -0.15688(7) 0.0203(3) Uani 1 1 d . . . H1 H 0.4554(15) -0.416(3) -0.1880(7) 0.020(4) Uiso 1 1 d . . . C2 C 0.25895(15) -0.5268(2) -0.14278(7) 0.0192(3) Uani 1 1 d . . . H2A H 0.2214(16) -0.408(3) -0.1756(8) 0.026(4) Uiso 1 1 d . . . H2B H 0.1791(16) -0.616(3) -0.1444(7) 0.020(4) Uiso 1 1 d . . . C3 C 0.34250(14) -0.4306(2) -0.07357(7) 0.0196(3) Uani 1 1 d . . . H3 H 0.3809(15) -0.551(2) -0.0415(7) 0.017(4) Uiso 1 1 d . . . C4 C 0.25466(14) -0.2684(2) -0.05106(7) 0.0203(3) Uani 1 1 d . . . C5 C 0.14394(14) -0.3701(2) -0.02831(6) 0.0197(3) Uani 1 1 d . . . C6 C 0.27464(16) -0.0538(2) -0.04941(8) 0.0271(3) Uani 1 1 d . . . H6A H 0.2181(16) 0.044(3) -0.0333(8) 0.027(4) Uiso 1 1 d . . . H6B H 0.3449(18) 0.014(3) -0.0642(8) 0.035(5) Uiso 1 1 d . . . C7 C 0.59561(14) -0.6959(2) -0.16769(7) 0.0198(3) Uani 1 1 d . . . C8 C 0.68448(14) -0.6112(2) -0.19887(7) 0.0203(3) Uani 1 1 d . . . H8 H 0.6660(15) -0.465(3) -0.2178(8) 0.022(4) Uiso 1 1 d . . . C9 C 0.79933(14) -0.7349(2) -0.20285(7) 0.0200(3) Uani 1 1 d . . . H9 H 0.8633(17) -0.678(3) -0.2236(8) 0.030(4) Uiso 1 1 d . . . C10 C 0.82036(14) -0.9436(2) -0.17615(6) 0.0180(3) Uani 1 1 d . . . C11 C 0.73321(15) -1.0334(2) -0.14508(7) 0.0207(3) Uani 1 1 d . . . H11 H 0.7548(15) -1.171(3) -0.1257(7) 0.018(4) Uiso 1 1 d . . . C12 C 0.61948(15) -0.9060(2) -0.14081(7) 0.0224(3) Uani 1 1 d . . . H12 H 0.5576(17) -0.964(3) -0.1174(8) 0.031(4) 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 O1 0.0185(5) 0.0179(5) 0.0294(5) -0.0049(4) 0.0130(4) 0.0008(4) O2 0.0174(4) 0.0223(5) 0.0233(5) -0.0051(4) 0.0101(4) 0.0021(4) O3 0.0160(4) 0.0220(5) 0.0254(5) -0.0054(4) 0.0112(4) -0.0008(4) O4 0.0295(5) 0.0219(6) 0.0381(6) -0.0049(4) 0.0234(5) 0.0001(4) O5 0.0235(5) 0.0203(5) 0.0292(6) -0.0008(4) 0.0157(4) 0.0014(4) O6 0.0223(5) 0.0316(6) 0.0318(6) -0.0001(5) 0.0169(5) 0.0012(4) O7 0.0240(5) 0.0184(6) 0.0365(6) -0.0027(4) 0.0110(5) 0.0022(4) N1 0.0179(5) 0.0221(6) 0.0208(6) -0.0038(5) 0.0080(5) 0.0005(5) C1 0.0200(6) 0.0212(7) 0.0213(7) -0.0019(6) 0.0099(6) -0.0009(6) C2 0.0167(6) 0.0210(7) 0.0222(7) -0.0018(6) 0.0100(6) 0.0020(6) C3 0.0186(6) 0.0191(7) 0.0236(7) 0.0014(6) 0.0107(6) 0.0000(5) C4 0.0185(6) 0.0226(7) 0.0205(7) -0.0019(6) 0.0083(6) 0.0007(5) C5 0.0187(6) 0.0226(8) 0.0184(7) -0.0011(5) 0.0077(5) 0.0032(5) C6 0.0272(8) 0.0247(8) 0.0349(9) -0.0008(6) 0.0181(7) 0.0013(6) C7 0.0173(6) 0.0216(7) 0.0202(7) -0.0061(6) 0.0070(5) -0.0010(5) C8 0.0209(7) 0.0184(7) 0.0208(7) -0.0017(6) 0.0072(6) -0.0001(5) C9 0.0203(7) 0.0206(7) 0.0207(7) -0.0034(5) 0.0094(6) -0.0037(5) C10 0.0152(6) 0.0197(7) 0.0184(6) -0.0048(5) 0.0060(5) 0.0006(5) C11 0.0220(7) 0.0192(7) 0.0217(7) -0.0001(6) 0.0093(6) 0.0001(6) C12 0.0219(7) 0.0256(8) 0.0234(7) -0.0028(6) 0.0128(6) -0.0039(6) _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 1.4427(16) . ? O1 O2 1.4696(12) . ? O2 C1 1.4276(16) . ? O3 C1 1.3996(16) . ? O3 C2 1.4433(15) . ? O4 C5 1.3178(16) . ? O4 H4 0.91(2) . ? O5 C5 1.2235(17) . ? O6 N1 1.2306(14) . ? O7 N1 1.2281(15) . ? N1 C10 1.4777(16) . ? C1 C7 1.5109(18) . ? C1 H1 1.008(15) . ? C2 C3 1.5164(19) . ? C2 H2A 0.979(17) . ? C2 H2B 0.945(15) . ? C3 C4 1.5109(18) . ? C3 H3 0.978(15) . ? C4 C6 1.324(2) . ? C4 C5 1.4886(18) . ? C6 H6A 0.966(15) . ? C6 H6B 0.958(17) . ? C7 C8 1.3893(18) . ? C7 C12 1.390(2) . ? C8 C9 1.3856(18) . ? C8 H8 0.969(16) . ? C9 C10 1.3813(19) . ? C9 H9 0.964(16) . ? C10 C11 1.3861(19) . ? C11 C12 1.392(2) . ? C11 H11 0.925(15) . ? C12 H12 0.993(16) . ? 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 C3 O1 O2 105.98(9) . . ? C1 O2 O1 107.36(8) . . ? C1 O3 C2 110.92(10) . . ? C5 O4 H4 110.5(13) . . ? O7 N1 O6 124.04(11) . . ? O7 N1 C10 118.06(11) . . ? O6 N1 C10 117.90(11) . . ? O3 C1 O2 111.09(10) . . ? O3 C1 C7 111.02(11) . . ? O2 C1 C7 102.47(10) . . ? O3 C1 H1 109.8(8) . . ? O2 C1 H1 108.3(8) . . ? C7 C1 H1 113.9(8) . . ? O3 C2 C3 109.68(10) . . ? O3 C2 H2A 109.0(9) . . ? C3 C2 H2A 109.5(9) . . ? O3 C2 H2B 106.8(9) . . ? C3 C2 H2B 112.7(9) . . ? H2A C2 H2B 109.1(12) . . ? O1 C3 C4 105.26(11) . . ? O1 C3 C2 108.32(10) . . ? C4 C3 C2 114.34(11) . . ? O1 C3 H3 107.9(8) . . ? C4 C3 H3 112.1(8) . . ? C2 C3 H3 108.7(8) . . ? C6 C4 C5 121.60(12) . . ? C6 C4 C3 124.18(12) . . ? C5 C4 C3 114.19(12) . . ? O5 C5 O4 124.08(12) . . ? O5 C5 C4 121.72(11) . . ? O4 C5 C4 114.20(12) . . ? C4 C6 H6A 121.5(9) . . ? C4 C6 H6B 122.6(10) . . ? H6A C6 H6B 115.8(14) . . ? C8 C7 C12 120.64(12) . . ? C8 C7 C1 118.47(12) . . ? C12 C7 C1 120.56(11) . . ? C9 C8 C7 120.17(13) . . ? C9 C8 H8 120.0(8) . . ? C7 C8 H8 119.8(8) . . ? C10 C9 C8 118.15(12) . . ? C10 C9 H9 120.4(10) . . ? C8 C9 H9 121.4(10) . . ? C9 C10 C11 123.11(12) . . ? C9 C10 N1 118.34(11) . . ? C11 C10 N1 118.55(12) . . ? C10 C11 C12 117.97(13) . . ? C10 C11 H11 120.2(9) . . ? C12 C11 H11 121.8(9) . . ? C7 C12 C11 119.94(12) . . ? C7 C12 H12 120.4(9) . . ? C11 C12 H12 119.7(9) . . ? 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 C3 O1 O2 C1 67.17(11) . . . . ? C2 O3 C1 O2 59.05(14) . . . . ? C2 O3 C1 C7 172.38(11) . . . . ? O1 O2 C1 O3 -65.27(12) . . . . ? O1 O2 C1 C7 176.12(9) . . . . ? C1 O3 C2 C3 -53.93(14) . . . . ? O2 O1 C3 C4 173.96(9) . . . . ? O2 O1 C3 C2 -63.33(12) . . . . ? O3 C2 C3 O1 57.53(14) . . . . ? O3 C2 C3 C4 174.53(11) . . . . ? O1 C3 C4 C6 13.64(18) . . . . ? C2 C3 C4 C6 -105.11(16) . . . . ? O1 C3 C4 C5 -164.60(11) . . . . ? C2 C3 C4 C5 76.65(15) . . . . ? C6 C4 C5 O5 177.18(14) . . . . ? C3 C4 C5 O5 -4.53(18) . . . . ? C6 C4 C5 O4 -2.2(2) . . . . ? C3 C4 C5 O4 176.09(11) . . . . ? O3 C1 C7 C8 146.67(12) . . . . ? O2 C1 C7 C8 -94.66(13) . . . . ? O3 C1 C7 C12 -39.97(17) . . . . ? O2 C1 C7 C12 78.71(14) . . . . ? C12 C7 C8 C9 -0.7(2) . . . . ? C1 C7 C8 C9 172.65(12) . . . . ? C7 C8 C9 C10 1.1(2) . . . . ? C8 C9 C10 C11 -0.7(2) . . . . ? C8 C9 C10 N1 178.60(11) . . . . ? O7 N1 C10 C9 -169.75(12) . . . . ? O6 N1 C10 C9 9.99(17) . . . . ? O7 N1 C10 C11 9.61(18) . . . . ? O6 N1 C10 C11 -170.66(12) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? N1 C10 C11 C12 -179.36(12) . . . . ? C8 C7 C12 C11 -0.1(2) . . . . ? C1 C7 C12 C11 -173.29(12) . . . . ? C10 C11 C12 C7 0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.299 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.044