# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Chia-Her LinChia-Her Lin' . ; Department of Chemistry Chung-Yuan Christian University Chung-Li 320 Taiwan ; 'Ting-Guang Chang' '' '' 'Pei-Chi Cheng' '' '' 'Vitezslav Zima' '' '' 'Feng-Shuen Tseng' '' '' 'Chun-Ting Yeh' '' '' 'Ching-Che Kao' '' '' 'Wei-Ren Liu' '' '' 'Jenn-Shing Chen' '' '' _publ_contact_author_address ; Department of Chemistry Chung-Yuan Christian University Chung-Li 320 Taiwan R.O.C. ; _publ_contact_author_email chiaher@cycu.edu.tw _publ_contact_author_fax '886 3 265 3399' _publ_contact_author_phone '886 3 265 3315' #TrackingRef '- all.cif' _publ_contact_author_name 'Chia-Her Lin' data_1 _database_code_depnum_ccdc_archive 'CCDC 805999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Li2 O5' _chemical_formula_sum 'C14 H8 Li2 O5' _chemical_formula_weight 270.08 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' Li Li -0.0003 0.0001 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 8.4363(4) _cell_length_b 5.3754(2) _cell_length_c 25.8792(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1173.58(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3746 _cell_measurement_theta_min 3.1487 _cell_measurement_theta_max 27.9078 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 12075 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 28.32 _reflns_number_total 1466 _reflns_number_gt 986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0391P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1466 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 -0.12791(11) -0.17153(18) -0.02941(4) 0.0249(3) Uani 1 1 d . . . O2 O 0.12258(12) -0.28772(18) -0.04181(4) 0.0268(3) Uani 1 1 d . . . O3 O 0.0000 0.3025(3) -0.2500 0.0362(4) Uani 1 2 d S . . C1 C -0.00212(16) -0.1777(3) -0.05584(5) 0.0211(3) Uani 1 1 d . . . C2 C -0.00015(15) -0.0498(3) -0.10721(5) 0.0215(3) Uani 1 1 d . . . C3 C -0.09182(17) 0.1599(3) -0.11643(5) 0.0267(3) Uani 1 1 d . . . H3A H -0.1546 0.2248 -0.0901 0.032 Uiso 1 1 calc R . . C4 C -0.09057(18) 0.2734(3) -0.16461(6) 0.0292(4) Uani 1 1 d . . . H4A H -0.1498 0.4167 -0.1703 0.035 Uiso 1 1 calc R . . C5 C -0.00128(17) 0.1728(3) -0.20381(5) 0.0260(4) Uani 1 1 d . . . C6 C 0.09070(18) -0.0364(3) -0.19563(6) 0.0308(4) Uani 1 1 d . . . H6A H 0.1505 -0.1040 -0.2224 0.037 Uiso 1 1 calc R . . C7 C 0.09227(17) -0.1435(3) -0.14693(6) 0.0280(4) Uani 1 1 d . . . H7A H 0.1566 -0.2809 -0.1408 0.034 Uiso 1 1 calc R . . Li1 Li -0.2770(3) 0.0564(5) 0.00765(10) 0.0289(6) Uani 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 0.0241(5) 0.0244(5) 0.0262(5) 0.0020(4) 0.0040(4) -0.0025(4) O2 0.0258(5) 0.0235(5) 0.0310(6) 0.0036(4) -0.0049(4) 0.0030(4) O3 0.0662(12) 0.0243(8) 0.0182(8) 0.000 0.0027(7) 0.000 C1 0.0233(8) 0.0160(7) 0.0241(7) -0.0023(6) -0.0021(6) -0.0029(6) C2 0.0216(7) 0.0207(7) 0.0223(8) 0.0004(6) -0.0003(6) -0.0017(6) C3 0.0297(8) 0.0275(8) 0.0230(8) 0.0005(6) 0.0060(6) 0.0054(6) C4 0.0353(9) 0.0232(8) 0.0291(9) 0.0020(6) 0.0009(7) 0.0059(7) C5 0.0338(9) 0.0243(8) 0.0200(7) 0.0015(6) -0.0010(6) -0.0049(7) C6 0.0357(9) 0.0325(9) 0.0241(8) -0.0039(6) 0.0060(7) 0.0048(7) C7 0.0295(8) 0.0258(8) 0.0288(8) -0.0006(6) 0.0019(6) 0.0063(6) Li1 0.0286(14) 0.0241(13) 0.0341(14) 0.0034(11) -0.0020(11) -0.0011(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2630(16) . ? O1 Li1 1.924(3) 7 ? O1 Li1 2.001(3) . ? O2 C1 1.2603(16) . ? O2 Li1 1.894(3) 3_545 ? O2 Li1 2.006(3) 5 ? O3 C5 1.3837(16) 4_554 ? O3 C5 1.3838(16) . ? C1 C2 1.4969(19) . ? C2 C7 1.3852(19) . ? C2 C3 1.3874(19) . ? C3 C4 1.388(2) . ? C3 H3A 0.9300 . ? C4 C5 1.374(2) . ? C4 H4A 0.9300 . ? C5 C6 1.383(2) . ? C6 C7 1.386(2) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? Li1 O2 1.894(3) 3_445 ? Li1 O1 1.924(3) 7_565 ? Li1 O2 2.006(3) 5 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 Li1 126.90(12) . 7 ? C1 O1 Li1 143.49(12) . . ? Li1 O1 Li1 87.96(8) 7 . ? C1 O2 Li1 149.99(12) . 3_545 ? C1 O2 Li1 112.21(11) . 5 ? Li1 O2 Li1 88.65(8) 3_545 5 ? C5 O3 C5 119.50(17) 4_554 . ? O2 C1 O1 123.90(13) . . ? O2 C1 C2 117.52(12) . . ? O1 C1 C2 118.57(12) . . ? C7 C2 C3 118.80(13) . . ? C7 C2 C1 119.88(13) . . ? C3 C2 C1 121.31(12) . . ? C2 C3 C4 120.48(13) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 119.61(14) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.97(13) . . ? C4 C5 O3 116.34(13) . . ? C6 C5 O3 122.52(13) . . ? C5 C6 C7 118.87(13) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C2 C7 C6 121.22(14) . . ? C2 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? O2 Li1 O1 128.75(14) 3_445 7_565 ? O2 Li1 O1 92.17(12) 3_445 . ? O1 Li1 O1 119.26(13) 7_565 . ? O2 Li1 O2 123.88(14) 3_445 5 ? O1 Li1 O2 91.11(12) 7_565 5 ? O1 Li1 O2 100.53(11) . 5 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.227 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.043 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 806000' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Na2 O6' _chemical_formula_sum 'C14 H10 Na2 O6' _chemical_formula_weight 320.20 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' Na Na 0.0362 0.0249 '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 1 c 1' _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' _cell_length_a 29.1055(12) _cell_length_b 5.7959(2) _cell_length_c 7.6970(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.448(2) _cell_angle_gamma 90.00 _cell_volume 1297.24(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4242 _cell_measurement_theta_min 2.8019 _cell_measurement_theta_max 28.1749 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9437 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 6958 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.41 _reflns_number_total 3203 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. The Flack parameter reported cannot be used to determine the absolute structure due to the Mo-Kalpha radiation used with no heavy elements in the structure ; _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^)+(0.0349P)^2^+0.1054P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 3203 _refine_ls_number_parameters 199 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.051 _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 Na1 Na -0.30473(2) 0.34167(13) -0.31840(9) 0.02998(19) Uani 1 1 d . . . Na2 Na -0.24549(3) 0.11340(13) -0.65897(9) 0.02836(17) Uani 1 1 d . . . O1 O -0.31906(4) 0.3135(3) -0.64608(18) 0.0301(3) Uani 1 1 d . . . O1W O -0.27934(5) 0.2160(2) -0.03470(17) 0.0324(3) Uani 1 1 d . . . H1 H -0.2997 0.1620 0.0312 0.049 Uiso 1 1 d R . . H2 H -0.2631 0.2957 0.0154 0.049 Uiso 1 1 d R . . O2 O -0.34170(5) 0.0176(2) -0.81136(18) 0.0330(3) Uani 1 1 d . . . O3 O -0.72581(4) 0.3062(3) -0.86800(17) 0.0300(3) Uani 1 1 d . . . O4 O -0.71945(5) -0.0631(2) -0.79561(18) 0.0345(3) Uani 1 1 d . . . O5 O -0.52934(5) 0.3285(3) -0.4825(2) 0.0455(4) Uani 1 1 d . . . C1 C -0.34974(6) 0.1784(3) -0.7085(2) 0.0224(4) Uani 1 1 d . . . C2 C -0.39839(6) 0.2176(3) -0.6565(2) 0.0215(4) Uani 1 1 d . . . C3 C -0.40908(6) 0.4111(3) -0.5599(2) 0.0270(4) Uani 1 1 d . . . H3A H -0.3861 0.5171 -0.5296 0.032 Uiso 1 1 calc R . . C4 C -0.45354(7) 0.4485(4) -0.5079(3) 0.0308(4) Uani 1 1 d . . . H4A H -0.4605 0.5788 -0.4436 0.037 Uiso 1 1 calc R . . C5 C -0.48741(6) 0.2888(3) -0.5530(2) 0.0265(4) Uani 1 1 d . . . C6 C -0.47784(6) 0.0967(4) -0.6528(3) 0.0299(4) Uani 1 1 d . . . H6A H -0.5009 -0.0077 -0.6850 0.036 Uiso 1 1 calc R . . C7 C -0.43311(6) 0.0631(3) -0.7039(2) 0.0268(4) Uani 1 1 d . . . H7A H -0.4263 -0.0650 -0.7709 0.032 Uiso 1 1 calc R . . C8 C -0.57016(6) 0.2695(4) -0.5744(2) 0.0305(4) Uani 1 1 d . . . C9 C -0.59086(7) 0.4340(4) -0.6809(3) 0.0332(5) Uani 1 1 d . . . H9A H -0.5757 0.5715 -0.7034 0.040 Uiso 1 1 calc R . . C10 C -0.63455(7) 0.3925(3) -0.7543(3) 0.0284(4) Uani 1 1 d . . . H10A H -0.6491 0.5038 -0.8242 0.034 Uiso 1 1 calc R . . C11 C -0.65649(6) 0.1846(3) -0.7233(2) 0.0218(4) Uani 1 1 d . . . C12 C -0.63416(6) 0.0194(3) -0.6197(2) 0.0273(4) Uani 1 1 d . . . H12A H -0.6483 -0.1221 -0.6018 0.033 Uiso 1 1 calc R . . C13 C -0.59104(7) 0.0630(4) -0.5427(3) 0.0326(4) Uani 1 1 d . . . H13A H -0.5766 -0.0463 -0.4708 0.039 Uiso 1 1 calc R . . C14 C -0.70388(6) 0.1379(3) -0.8021(2) 0.0223(4) Uani 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 Na1 0.0282(4) 0.0281(4) 0.0336(4) -0.0002(3) -0.0001(3) 0.0018(3) Na2 0.0296(4) 0.0267(4) 0.0288(4) 0.0004(3) 0.0014(3) -0.0023(3) O1 0.0185(6) 0.0338(7) 0.0379(7) -0.0002(6) 0.0014(5) -0.0038(5) O1W 0.0352(8) 0.0331(8) 0.0288(7) 0.0016(6) 0.0003(6) -0.0024(6) O2 0.0274(7) 0.0339(8) 0.0382(8) -0.0086(6) 0.0074(6) 0.0021(6) O3 0.0222(7) 0.0377(8) 0.0298(7) 0.0030(6) -0.0037(5) 0.0043(5) O4 0.0310(8) 0.0337(8) 0.0385(8) 0.0035(6) -0.0026(6) -0.0127(6) O5 0.0156(7) 0.0832(12) 0.0377(8) -0.0253(8) 0.0000(5) -0.0013(7) C1 0.0197(8) 0.0230(9) 0.0243(8) 0.0059(7) 0.0002(7) 0.0026(7) C2 0.0177(8) 0.0237(9) 0.0231(8) 0.0031(7) -0.0003(6) 0.0009(7) C3 0.0192(9) 0.0288(10) 0.0327(10) -0.0051(8) -0.0017(7) -0.0027(7) C4 0.0228(9) 0.0348(11) 0.0346(10) -0.0109(9) -0.0011(7) 0.0007(8) C5 0.0160(8) 0.0381(11) 0.0253(9) -0.0031(8) -0.0011(7) 0.0010(7) C6 0.0182(9) 0.0370(11) 0.0344(10) -0.0064(9) -0.0013(7) -0.0070(7) C7 0.0231(9) 0.0270(10) 0.0301(9) -0.0043(8) 0.0000(7) -0.0024(7) C8 0.0153(8) 0.0496(12) 0.0265(9) -0.0103(9) 0.0006(7) 0.0011(8) C9 0.0264(10) 0.0362(11) 0.0373(11) -0.0041(9) 0.0047(8) -0.0122(8) C10 0.0257(9) 0.0292(10) 0.0301(9) 0.0043(8) 0.0004(7) -0.0013(8) C11 0.0179(8) 0.0267(9) 0.0210(8) -0.0019(7) 0.0016(6) -0.0010(6) C12 0.0245(9) 0.0273(10) 0.0300(10) 0.0039(8) 0.0004(7) 0.0002(7) C13 0.0260(9) 0.0413(12) 0.0303(10) 0.0042(9) -0.0027(7) 0.0076(8) C14 0.0183(8) 0.0299(10) 0.0189(8) -0.0004(7) 0.0043(6) -0.0026(7) _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 Na1 O2 2.3457(15) 2 ? Na1 O1W 2.3889(15) . ? Na1 O1 2.4446(15) 2_565 ? Na1 O3 2.4964(14) 4 ? Na1 O1 2.5441(16) . ? Na1 O4 2.7932(16) 4 ? Na2 O4 2.2944(15) 3 ? Na2 O3 2.3348(15) 4 ? Na2 O1W 2.3689(15) 2_554 ? Na2 O1 2.4408(15) . ? Na2 O3 2.4829(15) 3_545 ? O1 C1 1.267(2) . ? O1 Na1 2.4446(15) 2_564 ? O1W Na2 2.3689(15) 2 ? O1W H1 0.8551 . ? O1W H2 0.7550 . ? O2 C1 1.251(2) . ? O2 Na1 2.3457(15) 2_554 ? O3 C14 1.260(2) . ? O3 Na2 2.3347(15) 4_454 ? O3 Na2 2.4829(15) 3_455 ? O3 Na1 2.4964(14) 4_454 ? O4 C14 1.252(2) . ? O4 Na2 2.2944(15) 3_445 ? O4 Na1 2.7933(16) 4_454 ? O5 C5 1.376(2) . ? O5 C8 1.399(2) . ? C1 C2 1.505(2) . ? C2 C7 1.387(2) . ? C2 C3 1.388(3) . ? C3 C4 1.388(3) . ? C3 H3A 0.9300 . ? C4 C5 1.385(3) . ? C4 H4A 0.9300 . ? C5 C6 1.388(3) . ? C6 C7 1.390(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C13 1.369(3) . ? C8 C9 1.379(3) . ? C9 C10 1.390(3) . ? C9 H9A 0.9300 . ? C10 C11 1.389(3) . ? C10 H10A 0.9300 . ? C11 C12 1.390(3) . ? C11 C14 1.507(2) . ? C12 C13 1.388(3) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 O2 Na1 O1W 80.36(5) 2 . ? O2 Na1 O1 128.63(5) 2 2_565 ? O1W Na1 O1 78.85(5) . 2_565 ? O2 Na1 O3 97.16(5) 2 4 ? O1W Na1 O3 77.55(5) . 4 ? O1 Na1 O3 122.90(5) 2_565 4 ? O2 Na1 O1 84.83(5) 2 . ? O1W Na1 O1 156.61(6) . . ? O1 Na1 O1 124.46(5) 2_565 . ? O3 Na1 O1 86.52(5) 4 . ? O2 Na1 O4 144.47(5) 2 4 ? O1W Na1 O4 80.98(5) . 4 ? O1 Na1 O4 76.23(4) 2_565 4 ? O3 Na1 O4 49.19(4) 4 4 ? O1 Na1 O4 101.50(5) . 4 ? O4 Na2 O3 101.79(6) 3 4 ? O4 Na2 O1W 174.26(6) 3 2_554 ? O3 Na2 O1W 82.11(5) 4 2_554 ? O4 Na2 O1 86.45(5) 3 . ? O3 Na2 O1 92.64(5) 4 . ? O1W Na2 O1 89.19(5) 2_554 . ? O4 Na2 O3 101.48(6) 3 3_545 ? O3 Na2 O3 135.29(5) 4 3_545 ? O1W Na2 O3 78.18(5) 2_554 3_545 ? O1 Na2 O3 126.44(5) . 3_545 ? C1 O1 Na2 107.25(11) . . ? C1 O1 Na1 115.67(11) . 2_564 ? Na2 O1 Na1 101.31(5) . 2_564 ? C1 O1 Na1 119.94(11) . . ? Na2 O1 Na1 87.93(5) . . ? Na1 O1 Na1 117.44(6) 2_564 . ? Na2 O1W Na1 89.68(5) 2 . ? Na2 O1W H1 104.7 2 . ? Na1 O1W H1 117.3 . . ? Na2 O1W H2 115.9 2 . ? Na1 O1W H2 116.3 . . ? H1 O1W H2 110.8 . . ? C1 O2 Na1 140.74(13) . 2_554 ? C14 O3 Na2 129.76(12) . 4_454 ? C14 O3 Na2 114.91(12) . 3_455 ? Na2 O3 Na2 115.13(6) 4_454 3_455 ? C14 O3 Na1 97.25(11) . 4_454 ? Na2 O3 Na1 91.47(5) 4_454 4_454 ? Na2 O3 Na1 84.71(5) 3_455 4_454 ? C14 O4 Na2 154.97(13) . 3_445 ? C14 O4 Na1 83.80(11) . 4_454 ? Na2 O4 Na1 95.40(5) 3_445 4_454 ? C5 O5 C8 120.56(14) . . ? O2 C1 O1 123.54(17) . . ? O2 C1 C2 118.96(16) . . ? O1 C1 C2 117.50(16) . . ? C7 C2 C3 119.00(15) . . ? C7 C2 C1 121.04(16) . . ? C3 C2 C1 119.95(16) . . ? C4 C3 C2 120.91(17) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 119.06(18) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? O5 C5 C4 115.04(17) . . ? O5 C5 C6 123.68(17) . . ? C4 C5 C6 121.14(17) . . ? C5 C6 C7 118.79(17) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C2 C7 C6 121.07(18) . . ? C2 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? C13 C8 C9 121.64(17) . . ? C13 C8 O5 119.81(19) . . ? C9 C8 O5 118.15(19) . . ? C8 C9 C10 119.39(18) . . ? C8 C9 H9A 120.3 . . ? C10 C9 H9A 120.3 . . ? C11 C10 C9 119.97(18) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 119.28(17) . . ? C10 C11 C14 120.40(16) . . ? C12 C11 C14 120.31(16) . . ? C13 C12 C11 120.79(18) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C8 C13 C12 118.88(19) . . ? C8 C13 H13A 120.6 . . ? C12 C13 H13A 120.6 . . ? O4 C14 O3 123.95(17) . . ? O4 C14 C11 118.53(16) . . ? O3 C14 C11 117.51(16) . . ? 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 O1W H1 O2 0.86 1.95 2.7998(18) 174.6 1_556 O1W H2 O4 0.76 2.06 2.7910(19) 163.3 3_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.166 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 806001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 K O5' _chemical_formula_sum 'C14 H9 K O5' _chemical_formula_weight 296.31 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' K K 0.2009 0.2494 '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 orthorhombic _symmetry_space_group_name_H-M 'P n n a' _symmetry_space_group_name_hall '-P 2a 2bc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0308(2) _cell_length_b 28.4845(11) _cell_length_c 7.0345(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1208.42(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5488 _cell_measurement_theta_min 2.8604 _cell_measurement_theta_max 28.2993 _exptl_crystal_description Tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.457 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8456 _exptl_absorpt_correction_T_max 0.9347 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 12535 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1501 _reflns_number_gt 1163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. The carboxylate hydrogen atom required for charge balance is modeled as half occupancy due to only half the OBA anion being present in the asymmetric unit. ; _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^)+(0.0534P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1501 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 K1 K 0.2500 0.0000 0.29700(8) 0.04147(19) Uani 1 2 d S . . O1 O -0.15622(18) -0.03843(3) 0.15291(14) 0.0336(3) Uani 1 1 d . . . H1 H -0.2202 -0.0131 0.1606 0.050 Uiso 0.50 1 d PR . . O2 O -0.40373(19) -0.05820(3) 0.37301(15) 0.0395(3) Uani 1 1 d . . . O3 O 0.1215(3) -0.2500 0.2500 0.0272(3) Uani 1 2 d S . . C1 C -0.2498(2) -0.06836(5) 0.2660(2) 0.0243(3) Uani 1 1 d . . . C2 C -0.1573(2) -0.11704(4) 0.25755(17) 0.0213(3) Uani 1 1 d . . . C3 C -0.2736(2) -0.15387(5) 0.34006(19) 0.0247(3) Uani 1 1 d . . . H3A H -0.4088 -0.1480 0.3992 0.030 Uiso 1 1 calc R . . C4 C -0.1904(3) -0.19927(4) 0.33515(19) 0.0256(3) Uani 1 1 d . . . H4A H -0.2691 -0.2239 0.3896 0.031 Uiso 1 1 calc R . . C5 C 0.0118(3) -0.20727(4) 0.24797(18) 0.0218(3) Uani 1 1 d . . . C6 C 0.1300(2) -0.17105(4) 0.16520(18) 0.0236(3) Uani 1 1 d . . . H6A H 0.2657 -0.1769 0.1069 0.028 Uiso 1 1 calc R . . C7 C 0.0441(2) -0.12593(4) 0.17013(18) 0.0244(3) Uani 1 1 d . . . H7A H 0.1224 -0.1014 0.1143 0.029 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 K1 0.0243(3) 0.0422(3) 0.0578(4) 0.000 0.000 0.0057(2) O1 0.0349(7) 0.0151(5) 0.0507(6) 0.0032(4) 0.0095(5) 0.0051(4) O2 0.0382(7) 0.0294(6) 0.0509(7) 0.0021(5) 0.0145(6) 0.0114(5) O3 0.0246(8) 0.0129(6) 0.0443(8) -0.0003(5) 0.000 0.000 C1 0.0221(9) 0.0208(7) 0.0302(7) -0.0022(5) -0.0005(6) 0.0025(5) C2 0.0235(8) 0.0177(6) 0.0227(6) -0.0007(5) -0.0012(6) 0.0005(6) C3 0.0225(8) 0.0230(7) 0.0285(7) -0.0014(5) 0.0046(6) 0.0008(5) C4 0.0302(9) 0.0184(6) 0.0281(7) 0.0023(5) 0.0052(6) -0.0033(5) C5 0.0282(9) 0.0147(6) 0.0227(6) -0.0022(5) -0.0023(6) 0.0021(5) C6 0.0214(8) 0.0197(6) 0.0296(7) -0.0014(5) 0.0045(6) 0.0010(5) C7 0.0279(9) 0.0163(6) 0.0289(7) 0.0012(5) 0.0048(6) -0.0013(5) _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 K1 O2 2.7193(11) 1_655 ? K1 O2 2.7193(11) 2_455 ? K1 O1 2.8683(11) 2 ? K1 O1 2.8683(11) . ? K1 O2 2.9993(12) 5_556 ? K1 O2 2.9993(12) 6_656 ? K1 O1 3.3962(11) 6_655 ? K1 O1 3.3962(11) 5 ? O1 C1 1.2955(17) . ? O1 H1 0.8202 . ? O2 C1 1.2296(16) . ? O3 C5 1.3855(14) . ? O3 C5 1.3856(14) 3_545 ? C1 C2 1.4957(18) . ? C2 C7 1.3852(19) . ? C2 C3 1.3891(18) . ? C3 C4 1.3875(17) . ? C3 H3A 0.9300 . ? C4 C5 1.384(2) . ? C4 H4A 0.9300 . ? C5 C6 1.3829(18) . ? C6 C7 1.3862(17) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? 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 O2 K1 O2 157.32(5) 1_655 2_455 ? O2 K1 O1 69.28(3) 1_655 2 ? O2 K1 O1 119.52(3) 2_455 2 ? O2 K1 O1 119.52(3) 1_655 . ? O2 K1 O1 69.28(3) 2_455 . ? O1 K1 O1 138.61(4) 2 . ? O2 K1 O2 86.98(3) 1_655 5_556 ? O2 K1 O2 75.42(3) 2_455 5_556 ? O1 K1 O2 78.38(3) 2 5_556 ? O1 K1 O2 138.45(3) . 5_556 ? O2 K1 O2 75.42(3) 1_655 6_656 ? O2 K1 O2 86.98(3) 2_455 6_656 ? O1 K1 O2 138.45(3) 2 6_656 ? O1 K1 O2 78.38(3) . 6_656 ? O2 K1 O2 78.58(4) 5_556 6_656 ? O2 K1 O1 81.89(3) 1_655 6_655 ? O2 K1 O1 120.50(3) 2_455 6_655 ? O1 K1 O1 69.60(3) 2 6_655 ? O1 K1 O1 71.94(2) . 6_655 ? O2 K1 O1 147.98(3) 5_556 6_655 ? O2 K1 O1 126.48(3) 6_656 6_655 ? O2 K1 O1 120.50(3) 1_655 5 ? O2 K1 O1 81.89(3) 2_455 5 ? O1 K1 O1 71.94(2) 2 5 ? O1 K1 O1 69.60(3) . 5 ? O2 K1 O1 126.48(2) 5_556 5 ? O2 K1 O1 147.98(3) 6_656 5 ? O1 K1 O1 42.54(3) 6_655 5 ? C1 O2 K1 127.06(9) . 1_455 ? C1 O2 K1 111.76(9) . 5_556 ? K1 O2 K1 93.02(3) 1_455 5_556 ? C5 O3 C5 122.93(16) . 3_545 ? O2 C1 O1 123.37(13) . . ? O2 C1 C2 121.60(12) . . ? O1 C1 C2 115.03(12) . . ? C7 C2 C3 119.36(12) . . ? C7 C2 C1 120.95(12) . . ? C3 C2 C1 119.69(12) . . ? C4 C3 C2 120.72(13) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C5 C4 C3 118.92(12) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C6 C5 C4 121.20(12) . . ? C6 C5 O3 114.42(13) . . ? C4 C5 O3 124.14(12) . . ? C5 C6 C7 119.25(13) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C2 C7 C6 120.56(12) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? 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 O1 H1 O1 0.82 1.65 2.4643(18) 174.2 2_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.315 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.050 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 806002' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 O5 Rb' _chemical_formula_sum 'C14 H9 O5 Rb' _chemical_formula_weight 342.68 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' Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n n a' _symmetry_space_group_name_hall '-P 2a 2bc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.3248(2) _cell_length_b 28.4469(9) _cell_length_c 7.0194(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1262.94(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5256 _cell_measurement_theta_min 2.8642 _cell_measurement_theta_max 28.2828 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3847 _exptl_absorpt_correction_T_max 0.6087 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 10980 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.33 _reflns_number_total 1574 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. The carboxylate hydrogen atom required for charge balance is modeled as half occupancy due to only half the OBA anion being present in the asymmetric unit. ; _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^)+(0.0409P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1574 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 Rb1 Rb -0.2500 0.0000 0.28562(4) 0.03421(12) Uani 1 2 d S . . O1 O -0.6663(2) -0.03899(4) 0.14818(19) 0.0317(3) Uani 1 1 d . . . H1 H -0.7287 -0.0138 0.1563 0.048 Uiso 0.50 1 d PR . . O2 O -0.8930(2) -0.05883(4) 0.37658(19) 0.0364(3) Uani 1 1 d . . . O3 O -0.3889(3) -0.2500 0.2500 0.0276(4) Uani 1 2 d S . . C1 C -0.7497(3) -0.06882(7) 0.2654(3) 0.0240(4) Uani 1 1 d . . . C2 C -0.6602(3) -0.11729(6) 0.2567(2) 0.0212(4) Uani 1 1 d . . . C3 C -0.4713(3) -0.12646(6) 0.1630(2) 0.0249(4) Uani 1 1 d . . . H3A H -0.4002 -0.1021 0.1023 0.030 Uiso 1 1 calc R . . C4 C -0.3876(3) -0.17119(6) 0.1586(2) 0.0250(4) Uani 1 1 d . . . H4A H -0.2604 -0.1769 0.0962 0.030 Uiso 1 1 calc R . . C5 C -0.4939(3) -0.20737(5) 0.2475(2) 0.0223(4) Uani 1 1 d . . . C6 C -0.6843(3) -0.19947(6) 0.3409(3) 0.0266(4) Uani 1 1 d . . . H6A H -0.7564 -0.2241 0.3993 0.032 Uiso 1 1 calc R . . C7 C -0.7642(3) -0.15422(7) 0.3452(3) 0.0266(4) Uani 1 1 d . . . H7A H -0.8905 -0.1484 0.4089 0.032 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 Rb1 0.02444(17) 0.0405(2) 0.03774(19) 0.000 0.000 0.00372(11) O1 0.0367(7) 0.0145(6) 0.0440(7) 0.0022(6) 0.0062(7) 0.0036(6) O2 0.0375(8) 0.0290(7) 0.0428(8) 0.0002(6) 0.0118(7) 0.0108(6) O3 0.0296(10) 0.0108(8) 0.0425(10) 0.0008(7) 0.000 0.000 C1 0.0265(10) 0.0189(9) 0.0268(9) -0.0032(7) -0.0029(8) 0.0019(7) C2 0.0243(9) 0.0173(9) 0.0220(8) -0.0009(7) -0.0010(7) -0.0002(8) C3 0.0300(10) 0.0158(8) 0.0287(8) 0.0022(7) 0.0065(8) -0.0037(7) C4 0.0262(9) 0.0180(8) 0.0307(9) -0.0009(7) 0.0063(8) 0.0019(7) C5 0.0297(10) 0.0136(8) 0.0237(8) -0.0024(7) -0.0024(7) 0.0022(7) C6 0.0334(10) 0.0171(9) 0.0292(9) 0.0030(8) 0.0063(9) -0.0030(8) C7 0.0288(10) 0.0218(10) 0.0293(9) -0.0001(8) 0.0062(8) 0.0019(7) _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 Rb1 O2 2.8821(12) 1_655 ? Rb1 O2 2.8821(12) 2_355 ? Rb1 O1 3.0158(14) 2_455 ? Rb1 O1 3.0158(14) . ? Rb1 O2 3.0398(13) 5_456 ? Rb1 O2 3.0398(13) 6_656 ? Rb1 O1 3.2836(13) 6_655 ? Rb1 O1 3.2836(13) 5_455 ? O1 C1 1.294(2) . ? O1 H1 0.8200 . ? O2 C1 1.230(2) . ? O3 C5 1.3828(18) . ? O3 C5 1.3829(18) 3_545 ? C1 C2 1.492(3) . ? C2 C7 1.386(3) . ? C2 C3 1.389(2) . ? C3 C4 1.379(2) . ? C3 H3A 0.9300 . ? C4 C5 1.379(2) . ? C4 H4A 0.9300 . ? C5 C6 1.390(2) . ? C6 C7 1.383(2) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? 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 O2 Rb1 O2 154.40(5) 1_655 2_355 ? O2 Rb1 O1 66.44(3) 1_655 2_455 ? O2 Rb1 O1 122.78(3) 2_355 2_455 ? O2 Rb1 O1 122.78(3) 1_655 . ? O2 Rb1 O1 66.44(3) 2_355 . ? O1 Rb1 O1 142.68(5) 2_455 . ? O2 Rb1 O2 85.05(3) 1_655 5_456 ? O2 Rb1 O2 74.97(3) 2_355 5_456 ? O1 Rb1 O2 77.72(3) 2_455 5_456 ? O1 Rb1 O2 135.38(3) . 5_456 ? O2 Rb1 O2 74.97(3) 1_655 6_656 ? O2 Rb1 O2 85.05(3) 2_355 6_656 ? O1 Rb1 O2 135.38(3) 2_455 6_656 ? O1 Rb1 O2 77.72(3) . 6_656 ? O2 Rb1 O2 77.48(5) 5_456 6_656 ? O2 Rb1 O1 83.29(3) 1_655 6_655 ? O2 Rb1 O1 121.86(4) 2_355 6_655 ? O1 Rb1 O1 71.75(4) 2_455 6_655 ? O1 Rb1 O1 73.73(3) . 6_655 ? O2 Rb1 O1 149.47(3) 5_456 6_655 ? O2 Rb1 O1 125.83(3) 6_656 6_655 ? O2 Rb1 O1 121.86(4) 1_655 5_455 ? O2 Rb1 O1 83.29(3) 2_355 5_455 ? O1 Rb1 O1 73.73(3) 2_455 5_455 ? O1 Rb1 O1 71.75(4) . 5_455 ? O2 Rb1 O1 125.83(3) 5_456 5_455 ? O2 Rb1 O1 149.47(3) 6_656 5_455 ? O1 Rb1 O1 43.95(4) 6_655 5_455 ? O2 Rb1 C1 96.81(4) 1_655 5_456 ? O2 Rb1 C1 60.33(3) 2_355 5_456 ? O1 Rb1 C1 94.49(4) 2_455 5_456 ? O1 Rb1 C1 117.73(3) . 5_456 ? O2 Rb1 C1 17.65(3) 5_456 5_456 ? O2 Rb1 C1 68.14(4) 6_656 5_456 ? O1 Rb1 C1 165.03(4) 6_655 5_456 ? O1 Rb1 C1 127.55(4) 5_455 5_456 ? O2 Rb1 C1 60.33(3) 1_655 6_656 ? O2 Rb1 C1 96.81(4) 2_355 6_656 ? O1 Rb1 C1 117.73(3) 2_455 6_656 ? O1 Rb1 C1 94.48(4) . 6_656 ? O2 Rb1 C1 68.14(4) 5_456 6_656 ? O2 Rb1 C1 17.65(3) 6_656 6_656 ? O1 Rb1 C1 127.55(4) 6_655 6_656 ? O1 Rb1 C1 165.03(4) 5_455 6_656 ? C1 Rb1 C1 63.69(6) 5_456 6_656 ? O2 Rb1 C1 69.42(4) 1_655 2_455 ? O2 Rb1 C1 111.62(4) 2_355 2_455 ? O1 Rb1 C1 18.65(4) 2_455 2_455 ? O1 Rb1 C1 157.37(4) . 2_455 ? O2 Rb1 C1 59.16(4) 5_456 2_455 ? O2 Rb1 C1 124.91(4) 6_656 2_455 ? O1 Rb1 C1 90.31(4) 6_655 2_455 ? O1 Rb1 C1 85.63(4) 5_455 2_455 ? C1 Rb1 C1 75.84(5) 5_456 2_455 ? C1 Rb1 C1 108.04(3) 6_656 2_455 ? O2 Rb1 C1 111.62(4) 1_655 . ? O2 Rb1 C1 69.42(4) 2_355 . ? O1 Rb1 C1 157.37(4) 2_455 . ? O1 Rb1 C1 18.65(4) . . ? O2 Rb1 C1 124.91(4) 5_456 . ? O2 Rb1 C1 59.16(4) 6_656 . ? O1 Rb1 C1 85.63(4) 6_655 . ? O1 Rb1 C1 90.31(4) 5_455 . ? C1 Rb1 C1 108.04(3) 5_456 . ? C1 Rb1 C1 75.84(5) 6_656 . ? C1 Rb1 C1 175.62(6) 2_455 . ? O2 Rb1 H1 137.4 1_655 . ? O2 Rb1 H1 52.4 2_355 . ? O1 Rb1 H1 141.6 2_455 . ? O1 Rb1 H1 14.9 . . ? O2 Rb1 H1 125.0 5_456 . ? O2 Rb1 H1 82.6 6_656 . ? O1 Rb1 H1 81.2 6_655 . ? O1 Rb1 H1 67.9 5_455 . ? C1 Rb1 H1 107.9 5_456 . ? C1 Rb1 H1 100.2 6_656 . ? C1 Rb1 H1 149.5 2_455 . ? C1 Rb1 H1 28.0 . . ? C1 O1 Rb1 113.17(11) . . ? C1 O1 Rb1 138.19(11) . 5_455 ? Rb1 O1 Rb1 108.25(4) . 5_455 ? C1 O1 H1 109.5 . . ? Rb1 O1 H1 94.4 . . ? Rb1 O1 H1 72.0 5_455 . ? C1 O2 Rb1 124.83(12) . 1_455 ? C1 O2 Rb1 113.78(11) . 5_456 ? Rb1 O2 Rb1 94.95(3) 1_455 5_456 ? C5 O3 C5 122.6(2) . 3_545 ? O2 C1 O1 123.53(18) . . ? O2 C1 C2 121.28(17) . . ? O1 C1 C2 115.20(15) . . ? O1 C1 Rb1 101.20(11) . 5_456 ? C2 C1 Rb1 121.49(11) . 5_456 ? O2 C1 Rb1 118.71(12) . . ? O1 C1 Rb1 48.18(9) . . ? C2 C1 Rb1 99.53(10) . . ? Rb1 C1 Rb1 71.96(3) 5_456 . ? O1 C1 Rb1 91.47(10) . 1_455 ? C2 C1 Rb1 144.09(12) . 1_455 ? Rb1 C1 Rb1 71.92(3) 5_456 1_455 ? Rb1 C1 Rb1 116.35(5) . 1_455 ? C7 C2 C3 118.56(16) . . ? C7 C2 C1 120.15(16) . . ? C3 C2 C1 121.28(15) . . ? C4 C3 C2 120.95(15) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 119.45(16) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 O3 115.21(16) . . ? C4 C5 C6 121.04(15) . . ? O3 C5 C6 123.52(15) . . ? C7 C6 C5 118.52(16) . . ? C7 C6 H6A 120.7 . . ? C5 C6 H6A 120.7 . . ? C6 C7 C2 121.47(17) . . ? C6 C7 H7A 119.3 . . ? C2 C7 H7A 119.3 . . ? 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 O1 H1 O1 0.82 1.64 2.458(2) 172.3 2_355 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.418 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.062 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 806003' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Cs O5' _chemical_formula_sum 'C14 H9 Cs O5' _chemical_formula_weight 390.12 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n n a' _symmetry_space_group_name_hall '-P 2a 2bc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 6.74770(10) _cell_length_b 28.4272(3) _cell_length_c 7.09860(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1361.64(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7048 _cell_measurement_theta_min 2.8662 _cell_measurement_theta_max 28.3247 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5148 _exptl_absorpt_correction_T_max 0.7176 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 '\w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 11769 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 28.33 _reflns_number_total 1698 _reflns_number_gt 1339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. The carboxylate hydrogen atom required for charge balance is modeled as half occupancy due to only half the OBA anion being present in the asymmetric unit. ; _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^)+(0.0400P)^2^+0.3399P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0159(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1698 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Cs1 Cs 0.2500 0.5000 0.28040(4) 0.03707(13) Uani 1 2 d S . . O3 O 0.5997(3) 0.7500 0.7500 0.0330(5) Uani 1 2 d S . . C6 C 0.5866(3) 0.67182(7) 0.8548(3) 0.0310(5) Uani 1 1 d . . . H6A H 0.7000 0.6777 0.9255 0.037 Uiso 1 1 calc R . . C2 C 0.3368(3) 0.61827(7) 0.7443(3) 0.0239(4) Uani 1 1 d . . . C4 C 0.3288(4) 0.69969(7) 0.6485(4) 0.0319(5) Uani 1 1 d . . . H4A H 0.2692 0.7241 0.5823 0.038 Uiso 1 1 calc R . . O1 O 0.1127(2) 0.56091(5) 0.6250(2) 0.0400(4) Uani 1 1 d . . . C1 C 0.2485(3) 0.56985(10) 0.7343(4) 0.0275(5) Uani 1 1 d . . . C5 C 0.4982(3) 0.70749(7) 0.7535(3) 0.0246(5) Uani 1 1 d . . . C7 C 0.5044(3) 0.62722(7) 0.8500(3) 0.0300(5) Uani 1 1 d . . . H7A H 0.5627 0.6030 0.9186 0.036 Uiso 1 1 calc R . . C3 C 0.2496(3) 0.65470(9) 0.6440(4) 0.0314(5) Uani 1 1 d . . . H3A H 0.1365 0.6489 0.5728 0.038 Uiso 1 1 calc R . . O2 O 0.3262(3) 0.53943(5) 0.8473(3) 0.0355(4) Uani 1 1 d . . . H2 H 0.2781 0.5134 0.8269 0.043 Uiso 0.50 1 calc PR . . 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 Cs1 0.02783(17) 0.0496(2) 0.03380(19) 0.000 0.000 -0.00406(9) O3 0.0312(12) 0.0166(11) 0.0513(14) 0.0003(9) 0.000 0.000 C6 0.0333(11) 0.0250(11) 0.0348(13) 0.0000(9) -0.0125(10) -0.0020(9) C2 0.0253(12) 0.0207(10) 0.0256(11) -0.0011(8) 0.0014(10) -0.0002(10) C4 0.0391(12) 0.0223(10) 0.0343(13) 0.0056(9) -0.0073(13) 0.0022(10) O1 0.0406(9) 0.0353(9) 0.0442(11) -0.0013(8) -0.0117(9) -0.0115(7) C1 0.0292(14) 0.0248(13) 0.0287(13) -0.0038(9) 0.0058(10) -0.0008(9) C5 0.0296(12) 0.0175(10) 0.0266(11) -0.0011(8) 0.0021(10) -0.0001(8) C7 0.0365(12) 0.0207(10) 0.0328(12) 0.0039(9) -0.0091(11) 0.0009(9) C3 0.0325(13) 0.0291(12) 0.0324(14) 0.0013(11) -0.0082(10) -0.0024(9) O2 0.0415(9) 0.0195(8) 0.0455(10) 0.0028(7) -0.0066(9) -0.0053(7) _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 Cs1 O1 3.0723(16) 6_656 ? Cs1 O1 3.0723(16) 5_566 ? Cs1 O1 3.1367(17) 2_565 ? Cs1 O1 3.1367(17) . ? Cs1 O2 3.2026(18) 6_556 ? Cs1 O2 3.2026(18) 5_666 ? Cs1 O2 3.3122(18) 2_564 ? Cs1 O2 3.3122(18) 1_554 ? O3 C5 1.389(2) 4_566 ? O3 C5 1.389(2) . ? C6 C5 1.378(3) . ? C6 C7 1.384(3) . ? C6 H6A 0.9300 . ? C2 C7 1.381(3) . ? C2 C3 1.388(3) . ? C2 C1 1.502(3) . ? C4 C5 1.383(3) . ? C4 C3 1.386(3) . ? C4 H4A 0.9300 . ? O1 C1 1.227(3) . ? O1 Cs1 3.0724(15) 5_566 ? C1 O2 1.291(3) . ? C7 H7A 0.9300 . ? C3 H3A 0.9300 . ? O2 Cs1 3.2026(18) 5_666 ? O2 Cs1 3.3122(18) 1_556 ? O2 H2 0.8200 . ? 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 O1 Cs1 O1 154.74(7) 6_656 5_566 ? O1 Cs1 O1 84.57(4) 6_656 2_565 ? O1 Cs1 O1 75.74(4) 5_566 2_565 ? O1 Cs1 O1 75.74(4) 6_656 . ? O1 Cs1 O1 84.57(4) 5_566 . ? O1 Cs1 O1 77.52(6) 2_565 . ? O1 Cs1 O2 125.17(4) 6_656 6_556 ? O1 Cs1 O2 63.12(4) 5_566 6_556 ? O1 Cs1 O2 132.67(4) 2_565 6_556 ? O1 Cs1 O2 76.34(4) . 6_556 ? O1 Cs1 O2 63.12(4) 6_656 5_666 ? O1 Cs1 O2 125.17(4) 5_566 5_666 ? O1 Cs1 O2 76.34(4) 2_565 5_666 ? O1 Cs1 O2 132.66(4) . 5_666 ? O2 Cs1 O2 147.10(6) 6_556 5_666 ? O1 Cs1 O2 121.15(4) 6_656 2_564 ? O1 Cs1 O2 83.60(4) 5_566 2_564 ? O1 Cs1 O2 125.65(4) 2_565 2_564 ? O1 Cs1 O2 149.85(4) . 2_564 ? O2 Cs1 O2 73.56(5) 6_556 2_564 ? O2 Cs1 O2 75.96(4) 5_666 2_564 ? O1 Cs1 O2 83.60(4) 6_656 1_554 ? O1 Cs1 O2 121.15(4) 5_566 1_554 ? O1 Cs1 O2 149.85(4) 2_565 1_554 ? O1 Cs1 O2 125.65(4) . 1_554 ? O2 Cs1 O2 75.96(4) 6_556 1_554 ? O2 Cs1 O2 73.56(5) 5_666 1_554 ? O2 Cs1 O2 43.71(5) 2_564 1_554 ? O1 Cs1 C1 61.34(4) 6_656 . ? O1 Cs1 C1 96.17(5) 5_566 . ? O1 Cs1 C1 68.08(5) 2_565 . ? O1 Cs1 C1 17.40(4) . . ? O2 Cs1 C1 93.15(5) 6_556 . ? O2 Cs1 C1 115.28(4) 5_666 . ? O2 Cs1 C1 165.29(5) 2_564 . ? O2 Cs1 C1 127.80(5) 1_554 . ? O1 Cs1 C1 96.17(5) 6_656 2_565 ? O1 Cs1 C1 61.34(4) 5_566 2_565 ? O1 Cs1 C1 17.40(4) 2_565 2_565 ? O1 Cs1 C1 68.08(5) . 2_565 ? O2 Cs1 C1 115.28(4) 6_556 2_565 ? O2 Cs1 C1 93.15(5) 5_666 2_565 ? O2 Cs1 C1 127.80(5) 2_564 2_565 ? O2 Cs1 C1 165.29(5) 1_554 2_565 ? C1 Cs1 C1 63.30(9) . 2_565 ? O1 Cs1 C1 167.95(5) 6_656 5_566 ? O1 Cs1 C1 14.91(5) 5_566 5_566 ? O1 Cs1 C1 89.68(5) 2_565 5_566 ? O1 Cs1 C1 92.70(5) . 5_566 ? O2 Cs1 C1 53.25(5) 6_556 5_566 ? O2 Cs1 C1 125.68(5) 5_666 5_566 ? O2 Cs1 C1 70.71(5) 2_564 5_566 ? O2 Cs1 C1 106.31(5) 1_554 5_566 ? C1 Cs1 C1 106.68(4) . 5_566 ? C1 Cs1 C1 76.02(6) 2_565 5_566 ? O1 Cs1 C1 14.91(5) 6_656 6_656 ? O1 Cs1 C1 167.95(5) 5_566 6_656 ? O1 Cs1 C1 92.70(5) 2_565 6_656 ? O1 Cs1 C1 89.68(5) . 6_656 ? O2 Cs1 C1 125.68(5) 6_556 6_656 ? O2 Cs1 C1 53.25(5) 5_666 6_656 ? O2 Cs1 C1 106.31(5) 2_564 6_656 ? O2 Cs1 C1 70.71(5) 1_554 6_656 ? C1 Cs1 C1 76.02(6) . 6_656 ? C1 Cs1 C1 106.68(4) 2_565 6_656 ? C1 Cs1 C1 176.95(8) 5_566 6_656 ? C5 O3 C5 120.9(2) 4_566 . ? C5 C6 C7 119.2(2) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C7 C2 C3 119.2(2) . . ? C7 C2 C1 121.3(2) . . ? C3 C2 C1 119.4(2) . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C1 O1 Cs1 124.97(16) . 5_566 ? C1 O1 Cs1 112.76(14) . . ? Cs1 O1 Cs1 95.43(4) 5_566 . ? O1 C1 O2 123.9(2) . . ? O1 C1 C2 121.1(2) . . ? O2 C1 C2 115.1(2) . . ? O1 C1 Cs1 49.84(12) . . ? O2 C1 Cs1 100.18(15) . . ? C2 C1 Cs1 121.35(15) . . ? O2 C1 Cs1 91.47(14) . 5_566 ? C2 C1 Cs1 143.96(15) . 5_566 ? Cs1 C1 Cs1 73.32(4) . 5_566 ? C6 C5 C4 121.38(19) . . ? C6 C5 O3 115.86(19) . . ? C4 C5 O3 122.50(19) . . ? C2 C7 C6 120.7(2) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C1 O2 Cs1 114.90(14) . 5_666 ? C1 O2 Cs1 137.78(15) . 1_556 ? Cs1 O2 Cs1 106.44(5) 5_666 1_556 ? C1 O2 H2 109.5 . . ? Cs1 O2 H2 89.3 5_666 . ? Cs1 O2 H2 78.3 1_556 . ? 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 O2 H2 O2 0.82 1.67 2.466(3) 164.8 2_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.359 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.096 #END data_6 _database_code_depnum_ccdc_archive 'CCDC 806004' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Mg O7' _chemical_formula_sum 'C14 H12 Mg O7' _chemical_formula_weight 316.55 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' Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' 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 14.0657(8) _cell_length_b 10.0353(6) _cell_length_c 10.2031(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.474(3) _cell_angle_gamma 90.00 _cell_volume 1388.00(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4506 _cell_measurement_theta_min 2.5252 _cell_measurement_theta_max 27.3392 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9684 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 14910 _diffrn_reflns_av_R_equivalents 0.0941 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3376 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.1292P)^2^+0.4412P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3376 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.2446 _refine_ls_wR_factor_gt 0.2269 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 Mg1 Mg 0.52016(9) 0.18579(11) 0.17187(13) 0.0224(3) Uani 1 1 d . . . O1 O 0.38157(19) 0.1515(3) 0.0202(3) 0.0300(6) Uani 1 1 d . . . O1W O 0.5893(2) 0.0108(3) 0.1760(3) 0.0347(7) Uani 1 1 d . . . H1WA H 0.5631 -0.0471 0.2162 0.052 Uiso 1 1 d R . . H1WB H 0.5850 -0.0144 0.0951 0.052 Uiso 1 1 d R . . O2 O 0.41498(19) 0.3408(3) 0.1249(3) 0.0309(7) Uani 1 1 d . . . O2W O 0.4529(2) 0.1028(3) 0.3161(3) 0.0375(7) Uani 1 1 d . . . H2WA H 0.4581 0.0184 0.3157 0.056 Uiso 1 1 d R . . H2WB H 0.4815 0.1329 0.3946 0.056 Uiso 1 1 d R . . O3 O 0.0038(2) 0.5021(3) -0.2671(4) 0.0523(10) Uani 1 1 d . . . O4 O -0.41974(19) 0.2416(3) -0.4776(3) 0.0322(7) Uani 1 1 d . . . O5 O -0.3859(2) 0.2846(3) -0.6746(3) 0.0328(7) Uani 1 1 d . . . C1 C 0.3553(3) 0.2680(4) 0.0400(4) 0.0237(8) Uani 1 1 d . . . C2 C 0.2589(3) 0.3235(4) -0.0382(4) 0.0280(8) Uani 1 1 d . . . C3 C 0.2266(3) 0.4449(4) -0.0023(5) 0.0398(10) Uani 1 1 d . . . H3A H 0.2647 0.4901 0.0731 0.048 Uiso 1 1 calc R . . C4 C 0.1389(3) 0.5001(4) -0.0763(5) 0.0415(11) Uani 1 1 d . . . H4A H 0.1173 0.5810 -0.0503 0.050 Uiso 1 1 calc R . . C5 C 0.0834(3) 0.4333(4) -0.1899(5) 0.0369(10) Uani 1 1 d . . . C6 C 0.1127(3) 0.3107(4) -0.2271(5) 0.0416(11) Uani 1 1 d . . . H6A H 0.0743 0.2655 -0.3024 0.050 Uiso 1 1 calc R . . C7 C 0.2006(3) 0.2566(4) -0.1500(5) 0.0352(10) Uani 1 1 d . . . H7A H 0.2208 0.1739 -0.1737 0.042 Uiso 1 1 calc R . . C8 C -0.0820(3) 0.4370(4) -0.3370(5) 0.0354(10) Uani 1 1 d . . . C9 C -0.1284(3) 0.3479(5) -0.2712(5) 0.0419(11) Uani 1 1 d . . . H9A H -0.0984 0.3206 -0.1827 0.050 Uiso 1 1 calc R . . C10 C -0.2197(3) 0.3005(4) -0.3392(5) 0.0359(10) Uani 1 1 d . . . H10A H -0.2528 0.2432 -0.2947 0.043 Uiso 1 1 calc R . . C11 C -0.2637(3) 0.3364(4) -0.4729(4) 0.0255(8) Uani 1 1 d . . . C12 C -0.2141(3) 0.4234(4) -0.5379(4) 0.0316(9) Uani 1 1 d . . . H12A H -0.2420 0.4473 -0.6280 0.038 Uiso 1 1 calc R . . C13 C -0.1233(3) 0.4744(4) -0.4683(5) 0.0387(10) Uani 1 1 d . . . H13A H -0.0906 0.5339 -0.5109 0.046 Uiso 1 1 calc R . . C14 C -0.3638(3) 0.2844(4) -0.5467(4) 0.0239(8) Uani 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 Mg1 0.0233(6) 0.0242(6) 0.0185(7) -0.0012(5) 0.0038(5) 0.0016(5) O1 0.0294(14) 0.0298(13) 0.0284(16) -0.0064(11) 0.0035(12) 0.0020(11) O1W 0.0534(18) 0.0273(13) 0.0270(16) 0.0032(11) 0.0170(14) 0.0081(12) O2 0.0282(14) 0.0305(13) 0.0293(16) -0.0104(11) -0.0005(12) 0.0025(11) O2W 0.0428(17) 0.0434(16) 0.0277(17) -0.0024(12) 0.0121(13) -0.0038(13) O3 0.0295(16) 0.0354(16) 0.072(3) 0.0026(15) -0.0221(15) -0.0020(12) O4 0.0270(14) 0.0436(16) 0.0269(16) -0.0073(12) 0.0089(12) -0.0044(11) O5 0.0319(15) 0.0476(16) 0.0175(15) -0.0066(12) 0.0042(12) -0.0058(12) C1 0.0234(18) 0.0278(18) 0.019(2) -0.0020(14) 0.0043(15) -0.0012(14) C2 0.0250(18) 0.0277(18) 0.029(2) 0.0019(15) 0.0034(16) 0.0006(14) C3 0.033(2) 0.040(2) 0.038(3) -0.0103(19) -0.0058(19) 0.0066(18) C4 0.033(2) 0.037(2) 0.047(3) -0.0062(19) -0.003(2) 0.0092(17) C5 0.026(2) 0.032(2) 0.046(3) 0.0065(18) -0.0020(18) -0.0007(16) C6 0.033(2) 0.038(2) 0.043(3) -0.0065(19) -0.009(2) -0.0028(17) C7 0.030(2) 0.0291(19) 0.040(3) -0.0039(17) -0.0028(18) 0.0013(16) C8 0.0223(19) 0.032(2) 0.044(3) -0.0014(18) -0.0036(18) 0.0022(15) C9 0.035(2) 0.052(3) 0.032(3) -0.002(2) -0.0033(19) 0.0022(19) C10 0.027(2) 0.048(2) 0.031(2) 0.0007(18) 0.0053(18) -0.0003(17) C11 0.0206(17) 0.0325(19) 0.023(2) -0.0064(15) 0.0044(15) 0.0021(14) C12 0.0279(19) 0.042(2) 0.023(2) -0.0005(16) 0.0029(16) 0.0025(16) C13 0.029(2) 0.039(2) 0.046(3) -0.0003(19) 0.0070(19) -0.0059(17) C14 0.0210(17) 0.0304(18) 0.019(2) -0.0070(14) 0.0035(14) 0.0031(14) _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 Mg1 O1W 2.002(3) . ? Mg1 O5 2.019(3) 1_656 ? Mg1 O4 2.064(3) 4_666 ? Mg1 O2 2.112(3) . ? Mg1 O2W 2.120(3) . ? Mg1 O1 2.169(3) . ? Mg1 C1 2.491(4) . ? O1 C1 1.259(4) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2 C1 1.265(4) . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? O3 C5 1.371(5) . ? O3 C8 1.390(5) . ? O4 C14 1.263(4) . ? O4 Mg1 2.064(3) 4_465 ? O5 C14 1.259(5) . ? O5 Mg1 2.019(3) 1_454 ? C1 C2 1.486(5) . ? C2 C3 1.384(5) . ? C2 C7 1.388(6) . ? C3 C4 1.379(6) . ? C3 H3A 0.9300 . ? C4 C5 1.385(6) . ? C4 H4A 0.9300 . ? C5 C6 1.383(6) . ? C6 C7 1.386(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C13 1.363(6) . ? C8 C9 1.382(6) . ? C9 C10 1.371(6) . ? C9 H9A 0.9300 . ? C10 C11 1.387(6) . ? C10 H10A 0.9300 . ? C11 C12 1.391(5) . ? C11 C14 1.502(5) . ? C12 C13 1.383(6) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 O1W Mg1 O5 101.58(13) . 1_656 ? O1W Mg1 O4 91.88(12) . 4_666 ? O5 Mg1 O4 95.05(12) 1_656 4_666 ? O1W Mg1 O2 163.26(13) . . ? O5 Mg1 O2 95.06(12) 1_656 . ? O4 Mg1 O2 88.44(12) 4_666 . ? O1W Mg1 O2W 86.84(12) . . ? O5 Mg1 O2W 88.57(12) 1_656 . ? O4 Mg1 O2W 176.34(13) 4_666 . ? O2 Mg1 O2W 91.80(12) . . ? O1W Mg1 O1 102.41(12) . . ? O5 Mg1 O1 155.35(12) 1_656 . ? O4 Mg1 O1 89.78(12) 4_666 . ? O2 Mg1 O1 60.85(10) . . ? O2W Mg1 O1 87.15(12) . . ? O1W Mg1 C1 132.75(13) . . ? O5 Mg1 C1 125.35(13) 1_656 . ? O4 Mg1 C1 89.41(12) 4_666 . ? O2 Mg1 C1 30.52(11) . . ? O2W Mg1 C1 88.94(12) . . ? O1 Mg1 C1 30.34(10) . . ? C1 O1 Mg1 89.2(2) . . ? Mg1 O1W H1WA 109.8 . . ? Mg1 O1W H1WB 109.4 . . ? H1WA O1W H1WB 109.8 . . ? C1 O2 Mg1 91.6(2) . . ? Mg1 O2W H2WA 109.5 . . ? Mg1 O2W H2WB 109.2 . . ? H2WA O2W H2WB 109.8 . . ? C5 O3 C8 121.5(3) . . ? C14 O4 Mg1 137.0(2) . 4_465 ? C14 O5 Mg1 137.2(3) . 1_454 ? O1 C1 O2 118.4(3) . . ? O1 C1 C2 121.8(3) . . ? O2 C1 C2 119.7(3) . . ? O1 C1 Mg1 60.51(19) . . ? O2 C1 Mg1 57.92(18) . . ? C2 C1 Mg1 177.3(3) . . ? C3 C2 C7 118.7(4) . . ? C3 C2 C1 120.3(4) . . ? C7 C2 C1 121.0(3) . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? O3 C5 C6 123.2(4) . . ? O3 C5 C4 115.4(4) . . ? C6 C5 C4 121.2(4) . . ? C5 C6 C7 118.6(4) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C6 C7 C2 121.3(4) . . ? C6 C7 H7A 119.4 . . ? C2 C7 H7A 119.4 . . ? C13 C8 C9 121.5(4) . . ? C13 C8 O3 117.3(4) . . ? C9 C8 O3 120.8(4) . . ? C10 C9 C8 118.6(4) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C9 C10 C11 121.3(4) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C10 C11 C12 118.9(4) . . ? C10 C11 C14 121.0(4) . . ? C12 C11 C14 120.1(4) . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C8 C13 C12 119.7(4) . . ? C8 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? O5 C14 O4 124.1(3) . . ? O5 C14 C11 117.3(3) . . ? O4 C14 C11 118.6(3) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.631 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.098 #END data_7 _database_code_depnum_ccdc_archive 'CCDC 806005' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Ca O6' _chemical_formula_sum 'C14 H10 Ca O6' _chemical_formula_weight 314.30 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' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.63300(10) _cell_length_b 28.9079(5) _cell_length_c 7.85160(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.5170(10) _cell_angle_gamma 90.00 _cell_volume 1272.62(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7447 _cell_measurement_theta_min 2.700 _cell_measurement_theta_max 28.286 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8598 _exptl_absorpt_correction_T_max 0.9123 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 12286 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3173 _reflns_number_gt 2892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0372P)^2^+0.4433P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3173 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Ca1 Ca 0.11757(4) 0.013677(8) 0.29837(3) 0.01927(8) Uani 1 1 d . . . O1 O -0.02142(16) 0.06404(3) 0.07716(11) 0.02764(19) Uani 1 1 d . . . O2 O -0.19273(14) 0.03549(3) 0.45986(11) 0.02222(17) Uani 1 1 d . . . O3 O -0.13088(15) -0.04572(3) 0.16559(12) 0.02664(19) Uani 1 1 d . . . O4 O 0.43675(16) 0.06005(3) 0.38868(15) 0.0359(2) Uani 1 1 d . . . O5 O 0.01488(17) 0.24927(3) 0.43103(16) 0.0384(3) Uani 1 1 d . . . C1 C 0.09625(19) 0.07375(4) -0.04728(15) 0.0216(2) Uani 1 1 d . . . C2 C 0.2002(2) 0.12136(4) -0.05437(15) 0.0222(2) Uani 1 1 d . . . C3 C 0.1030(2) 0.15790(4) 0.03078(16) 0.0262(2) Uani 1 1 d . . . H3A H -0.0260 0.1525 0.0937 0.031 Uiso 1 1 calc R . . C4 C 0.1957(2) 0.20224(4) 0.02331(18) 0.0297(3) Uani 1 1 d . . . H4A H 0.1267 0.2267 0.0773 0.036 Uiso 1 1 calc R . . C5 C 0.3934(2) 0.20935(4) -0.06626(17) 0.0269(3) Uani 1 1 d . . . C6 C 0.4953(2) 0.17332(4) -0.14949(17) 0.0279(3) Uani 1 1 d . . . H6A H 0.6296 0.1784 -0.2071 0.034 Uiso 1 1 calc R . . C7 C 0.3957(2) 0.12969(4) -0.14632(17) 0.0263(2) Uani 1 1 d . . . H7A H 0.4596 0.1057 -0.2060 0.032 Uiso 1 1 calc R . . C8 C -0.0965(2) 0.20672(4) 0.43681(17) 0.0261(2) Uani 1 1 d . . . C9 C 0.0451(2) 0.17225(4) 0.51335(18) 0.0296(3) Uani 1 1 d . . . H9A H 0.1950 0.1794 0.5670 0.035 Uiso 1 1 calc R . . C10 C -0.0358(2) 0.12709(4) 0.51032(17) 0.0264(3) Uani 1 1 d . . . H10A H 0.0611 0.1038 0.5604 0.032 Uiso 1 1 calc R . . C11 C -0.26140(19) 0.11634(4) 0.43279(15) 0.0212(2) Uani 1 1 d . . . C12 C -0.4031(2) 0.15176(4) 0.35859(18) 0.0276(3) Uani 1 1 d . . . H12A H -0.5551 0.1449 0.3078 0.033 Uiso 1 1 calc R . . C13 C -0.3223(2) 0.19708(4) 0.35886(19) 0.0311(3) Uani 1 1 d . . . H13A H -0.4175 0.2205 0.3078 0.037 Uiso 1 1 calc R . . C14 C -0.3484(2) 0.06737(4) 0.42611(15) 0.0207(2) Uani 1 1 d . . . O1W O 0.38535(17) -0.02350(4) 0.14353(15) 0.0397(3) Uani 1 1 d . . . H1 H 0.5204 -0.0273 0.1500 0.060 Uiso 1 1 d R . . H2 H 0.3221 -0.0371 0.0555 0.060 Uiso 1 1 d 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 Ca1 0.01796(11) 0.01683(12) 0.02322(13) 0.00141(8) 0.00293(8) -0.00005(7) O1 0.0322(4) 0.0225(4) 0.0284(4) 0.0054(4) 0.0040(4) -0.0010(3) O2 0.0240(4) 0.0165(4) 0.0266(4) 0.0026(3) 0.0042(3) 0.0033(3) O3 0.0251(4) 0.0193(4) 0.0357(5) -0.0057(4) 0.0039(3) -0.0029(3) O4 0.0218(4) 0.0233(5) 0.0610(7) -0.0004(4) -0.0046(4) -0.0032(3) O5 0.0282(5) 0.0140(4) 0.0727(7) 0.0011(4) 0.0034(5) 0.0006(3) C1 0.0201(5) 0.0176(5) 0.0261(6) 0.0024(4) -0.0019(4) 0.0012(4) C2 0.0260(5) 0.0162(5) 0.0237(5) 0.0011(4) -0.0012(4) -0.0005(4) C3 0.0286(6) 0.0207(6) 0.0295(6) 0.0000(5) 0.0036(5) 0.0006(4) C4 0.0339(6) 0.0185(6) 0.0368(7) -0.0041(5) 0.0036(5) 0.0030(5) C5 0.0285(6) 0.0141(5) 0.0369(7) 0.0021(5) -0.0033(5) -0.0014(4) C6 0.0265(5) 0.0201(6) 0.0375(7) 0.0019(5) 0.0046(5) -0.0010(4) C7 0.0289(6) 0.0178(5) 0.0325(6) -0.0012(5) 0.0047(5) 0.0007(4) C8 0.0278(6) 0.0142(5) 0.0363(7) -0.0017(5) 0.0029(5) 0.0001(4) C9 0.0240(5) 0.0202(6) 0.0428(7) -0.0013(5) -0.0058(5) -0.0008(4) C10 0.0243(5) 0.0178(5) 0.0356(6) 0.0018(5) -0.0052(5) 0.0021(4) C11 0.0212(5) 0.0161(5) 0.0261(6) -0.0012(4) 0.0015(4) 0.0015(4) C12 0.0226(5) 0.0202(6) 0.0383(7) -0.0006(5) -0.0060(5) 0.0027(4) C13 0.0304(6) 0.0179(6) 0.0429(7) 0.0028(5) -0.0071(5) 0.0049(5) C14 0.0212(5) 0.0178(5) 0.0233(5) -0.0005(4) 0.0022(4) 0.0005(4) O1W 0.0222(4) 0.0500(6) 0.0476(6) -0.0154(5) 0.0059(4) 0.0053(4) _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 Ca1 O1W 2.2937(10) . ? Ca1 O4 2.2994(9) . ? Ca1 O2 2.3424(8) . ? Ca1 O1 2.3425(9) . ? Ca1 O2 2.3766(8) 3_556 ? Ca1 O3 2.3902(9) . ? O1 C1 1.2639(15) . ? O2 C14 1.2823(14) . ? O2 Ca1 2.3765(8) 3_556 ? O3 C1 1.2620(15) 3 ? O4 C14 1.2358(14) 1_655 ? O5 C5 1.3791(14) 4_566 ? O5 C8 1.3833(14) . ? C1 O3 1.2619(15) 3 ? C1 C2 1.4988(16) . ? C2 C3 1.3902(17) . ? C2 C7 1.3945(17) . ? C3 C4 1.3875(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3885(18) . ? C4 H4A 0.9300 . ? C5 O5 1.3792(14) 4_665 ? C5 C6 1.3832(18) . ? C6 C7 1.3815(17) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.3777(17) . ? C8 C13 1.3859(18) . ? C9 C10 1.3820(17) . ? C9 H9A 0.9300 . ? C10 C11 1.3904(16) . ? C10 H10A 0.9300 . ? C11 C12 1.3913(16) . ? C11 C14 1.4974(16) . ? C12 C13 1.3868(17) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 O4 1.2357(14) 1_455 ? O1W H1 0.7653 . ? O1W H2 0.8437 . ? 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 O1W Ca1 O4 84.38(4) . . ? O1W Ca1 O2 167.43(4) . . ? O4 Ca1 O2 106.15(3) . . ? O1W Ca1 O1 95.06(4) . . ? O4 Ca1 O1 93.55(4) . . ? O2 Ca1 O1 91.17(3) . . ? O1W Ca1 O2 93.86(4) . 3_556 ? O4 Ca1 O2 91.63(3) . 3_556 ? O2 Ca1 O2 79.25(3) . 3_556 ? O1 Ca1 O2 170.08(3) . 3_556 ? O1W Ca1 O3 79.60(3) . . ? O4 Ca1 O3 163.94(3) . . ? O2 Ca1 O3 89.62(3) . . ? O1 Ca1 O3 89.03(3) . . ? O2 Ca1 O3 88.32(3) 3_556 . ? O1W Ca1 C1 77.22(4) . . ? O4 Ca1 C1 84.84(3) . . ? O2 Ca1 C1 110.02(3) . . ? O1 Ca1 C1 19.19(3) . . ? O2 Ca1 C1 170.67(3) 3_556 . ? O3 Ca1 C1 92.70(3) . . ? O1W Ca1 Ca1 132.30(3) . 3_556 ? O4 Ca1 Ca1 101.41(3) . 3_556 ? O2 Ca1 Ca1 39.97(2) . 3_556 ? O1 Ca1 Ca1 131.09(2) . 3_556 ? O2 Ca1 Ca1 39.282(19) 3_556 3_556 ? O3 Ca1 Ca1 88.66(2) . 3_556 ? C1 Ca1 Ca1 149.98(2) . 3_556 ? O1W Ca1 H2 16.3 . . ? O4 Ca1 H2 99.1 . . ? O2 Ca1 H2 154.8 . . ? O1 Ca1 H2 87.1 . . ? O2 Ca1 H2 100.4 3_556 . ? O3 Ca1 H2 65.2 . . ? C1 Ca1 H2 71.7 . . ? Ca1 Ca1 H2 134.5 3_556 . ? C1 O1 Ca1 123.26(8) . . ? C14 O2 Ca1 127.79(7) . . ? C14 O2 Ca1 131.35(7) . 3_556 ? Ca1 O2 Ca1 100.75(3) . 3_556 ? C1 O3 Ca1 131.07(7) 3 . ? C14 O4 Ca1 153.11(9) 1_655 . ? C5 O5 C8 122.92(10) 4_566 . ? O3 C1 O1 123.79(11) 3 . ? O3 C1 C2 118.27(10) 3 . ? O1 C1 C2 117.94(10) . . ? O3 C1 Ca1 106.18(7) 3 . ? O1 C1 Ca1 37.54(6) . . ? C2 C1 Ca1 122.99(7) . . ? C3 C2 C7 119.01(11) . . ? C3 C2 C1 120.42(11) . . ? C7 C2 C1 120.57(11) . . ? C4 C3 C2 120.95(11) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 118.80(11) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? O5 C5 C6 114.65(11) 4_665 . ? O5 C5 C4 124.03(12) 4_665 . ? C6 C5 C4 121.13(11) . . ? C7 C6 C5 119.44(11) . . ? C7 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C6 C7 C2 120.61(11) . . ? C6 C7 H7A 119.7 . . ? C2 C7 H7A 119.7 . . ? C9 C8 O5 114.35(11) . . ? C9 C8 C13 121.01(11) . . ? O5 C8 C13 124.35(11) . . ? C8 C9 C10 119.99(11) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 120.30(11) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C10 C11 C12 118.85(11) . . ? C10 C11 C14 120.59(10) . . ? C12 C11 C14 120.55(10) . . ? C13 C12 C11 121.29(11) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C8 C13 C12 118.56(11) . . ? C8 C13 H13A 120.7 . . ? C12 C13 H13A 120.7 . . ? O4 C14 O2 124.11(11) 1_455 . ? O4 C14 C11 118.69(10) 1_455 . ? O2 C14 C11 117.21(10) . . ? Ca1 O1W H1 137.1 . . ? Ca1 O1W H2 113.9 . . ? H1 O1W H2 109.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.333 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.044 #END data_8 _database_code_depnum_ccdc_archive 'CCDC 806006' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 O6 Sr' _chemical_formula_sum 'C14 H10 O6 Sr' _chemical_formula_weight 361.84 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' Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_hall 'P 2c -2n' 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' _cell_length_a 29.3128(11) _cell_length_b 6.3013(2) _cell_length_c 7.0793(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1307.61(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7697 _cell_measurement_theta_min 2.7795 _cell_measurement_theta_max 28.2523 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 4.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2568 _exptl_absorpt_correction_T_max 0.5750 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 8.3333 _diffrn_reflns_number 14533 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 28.38 _reflns_number_total 3229 _reflns_number_gt 2658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0258P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(9) _refine_ls_number_reflns 3229 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.002 _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 Sr1 Sr 0.473500(9) 0.61000(4) 0.04688(9) 0.01637(8) Uani 1 1 d . . . O1 O 0.54880(12) 0.4641(5) 0.2066(4) 0.0220(7) Uani 1 1 d . . . O2 O 0.54537(13) 0.4097(5) -0.1021(5) 0.0234(8) Uani 1 1 d . . . O3 O 0.74245(7) 0.0373(3) 0.0454(6) 0.0275(5) Uani 1 1 d . . . O4 O 0.45144(8) 0.2302(3) 0.0883(4) 0.0257(8) Uani 1 1 d . . . O5 O 0.42480(9) -0.0744(4) -0.0230(4) 0.0291(7) Uani 1 1 d . . . C1 C 0.56622(10) 0.4002(4) 0.0540(10) 0.0178(7) Uani 1 1 d . . . C2 C 0.61389(10) 0.3113(4) 0.0526(9) 0.0181(6) Uani 1 1 d . . . C3 C 0.64915(12) 0.4137(6) 0.1455(6) 0.0227(8) Uani 1 1 d . . . H3A H 0.6434 0.5385 0.2114 0.027 Uiso 1 1 calc R . . C4 C 0.69316(12) 0.3314(6) 0.1410(6) 0.0231(8) Uani 1 1 d . . . H4A H 0.7169 0.4009 0.2023 0.028 Uiso 1 1 calc R . . C5 C 0.70099(10) 0.1444(4) 0.0440(10) 0.0199(6) Uani 1 1 d . . . C6 C 0.66610(13) 0.0387(6) -0.0464(6) 0.0241(9) Uani 1 1 d . . . H6A H 0.6717 -0.0889 -0.1081 0.029 Uiso 1 1 calc R . . C7 C 0.62230(12) 0.1249(6) -0.0446(6) 0.0238(9) Uani 1 1 d . . . H7A H 0.5987 0.0570 -0.1086 0.029 Uiso 1 1 calc R . . C8 C 0.41934(10) 0.1110(5) 0.0369(10) 0.0190(7) Uani 1 1 d . . . C9 C 0.37182(10) 0.1971(4) 0.0448(9) 0.0173(6) Uani 1 1 d . . . C10 C 0.33611(13) 0.0857(6) -0.0376(6) 0.0256(9) Uani 1 1 d . . . H10A H 0.3417 -0.0447 -0.0946 0.031 Uiso 1 1 calc R . . C11 C 0.29200(13) 0.1678(6) -0.0358(6) 0.0256(9) Uani 1 1 d . . . H11A H 0.2683 0.0935 -0.0925 0.031 Uiso 1 1 calc R . . C12 C 0.28390(10) 0.3575(4) 0.0499(11) 0.0212(6) Uani 1 1 d . . . C13 C 0.31909(12) 0.4702(6) 0.1370(6) 0.0211(8) Uani 1 1 d . . . H13A H 0.3132 0.5988 0.1966 0.025 Uiso 1 1 calc R . . C14 C 0.36257(12) 0.3888(5) 0.1335(6) 0.0209(8) Uani 1 1 d . . . H14A H 0.3861 0.4632 0.1913 0.025 Uiso 1 1 calc R . . O1W O 0.52082(9) 0.9371(4) 0.1234(5) 0.0348(8) Uani 1 1 d . . . H1WA H 0.5300 0.9432 0.2372 0.052 Uiso 1 1 d R . . H1WB H 0.5038 1.0397 0.0904 0.052 Uiso 1 1 d 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 Sr1 0.01677(13) 0.01763(12) 0.01472(14) -0.0001(3) 0.0000(3) 0.00318(12) O1 0.0199(17) 0.0303(16) 0.0158(17) 0.0015(14) 0.0052(14) 0.0081(14) O2 0.0189(16) 0.0344(19) 0.0168(17) 0.0028(12) -0.0004(13) 0.0052(13) O3 0.0105(10) 0.0279(10) 0.0441(16) 0.002(3) -0.004(2) -0.0010(8) O4 0.0152(11) 0.0192(11) 0.043(3) 0.0012(13) 0.0007(13) 0.0008(10) O5 0.0236(14) 0.0241(14) 0.040(2) -0.0073(11) -0.0085(12) 0.0061(11) C1 0.0175(14) 0.0173(12) 0.0187(18) 0.002(2) -0.010(3) -0.0022(12) C2 0.0140(14) 0.0241(13) 0.0162(16) -0.004(3) 0.004(3) 0.0015(11) C3 0.0192(18) 0.0258(19) 0.023(2) -0.0069(16) 0.0011(17) 0.0014(15) C4 0.0164(18) 0.0301(19) 0.023(2) -0.0032(17) -0.0033(17) -0.0050(15) C5 0.0121(13) 0.0266(15) 0.0211(16) 0.005(3) 0.005(3) 0.0005(11) C6 0.022(2) 0.0254(18) 0.024(2) -0.0080(17) 0.0008(18) 0.0017(16) C7 0.0152(18) 0.033(2) 0.024(2) -0.0064(17) -0.0029(16) 0.0005(16) C8 0.0163(14) 0.0218(13) 0.0190(18) 0.003(2) -0.003(3) 0.0034(12) C9 0.0149(14) 0.0183(12) 0.0187(16) 0.000(3) -0.004(3) -0.0002(11) C10 0.025(2) 0.025(2) 0.027(2) -0.0072(16) -0.0014(17) 0.0012(16) C11 0.0162(18) 0.032(2) 0.028(2) -0.0070(17) -0.0067(17) -0.0054(16) C12 0.0141(14) 0.0272(15) 0.0223(17) 0.002(3) 0.000(3) 0.0004(11) C13 0.0163(18) 0.0222(17) 0.025(2) -0.0056(16) 0.0023(17) 0.0015(15) C14 0.0171(17) 0.0251(17) 0.0203(19) -0.0018(16) -0.0005(16) -0.0035(15) O1W 0.0250(15) 0.0272(14) 0.052(2) -0.0014(13) -0.0125(14) 0.0045(11) _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 Sr1 O4 2.496(2) . ? Sr1 O5 2.497(3) 1_565 ? Sr1 O1W 2.543(3) . ? Sr1 O1 2.540(3) 2_664 ? Sr1 O2 2.549(3) 2_665 ? Sr1 O1 2.645(3) . ? Sr1 O2 2.673(4) . ? Sr1 C1 3.023(3) . ? Sr1 H1WB 2.8657 . ? O1 C1 1.261(7) . ? O1 Sr1 2.540(3) 2_665 ? O2 C1 1.265(7) . ? O2 Sr1 2.549(3) 2_664 ? O3 C12 1.384(3) 3 ? O3 C5 1.390(3) . ? O4 C8 1.258(4) . ? O5 C8 1.253(4) . ? O5 Sr1 2.498(3) 1_545 ? C1 C2 1.505(4) . ? C2 C7 1.384(5) . ? C2 C3 1.384(5) . ? C3 C4 1.391(5) . ? C3 H3A 0.9300 . ? C4 C5 1.383(6) . ? C4 H4A 0.9300 . ? C5 C6 1.378(6) . ? C6 C7 1.394(5) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.496(4) . ? C9 C10 1.389(5) . ? C9 C14 1.388(5) . ? C10 C11 1.393(5) . ? C10 H10A 0.9300 . ? C11 C12 1.361(6) . ? C11 H11A 0.9300 . ? C12 O3 1.385(3) 3_455 ? C12 C13 1.396(6) . ? C13 C14 1.374(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8499 . ? 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 O4 Sr1 O5 129.69(8) . 1_565 ? O4 Sr1 O1W 153.30(9) . . ? O5 Sr1 O1W 73.06(8) 1_565 . ? O4 Sr1 O1 82.44(10) . 2_664 ? O5 Sr1 O1 79.12(10) 1_565 2_664 ? O1W Sr1 O1 119.44(11) . 2_664 ? O4 Sr1 O2 77.44(10) . 2_665 ? O5 Sr1 O2 96.20(11) 1_565 2_665 ? O1W Sr1 O2 87.14(11) . 2_665 ? O1 Sr1 O2 149.33(8) 2_664 2_665 ? O4 Sr1 O1 80.37(9) . . ? O5 Sr1 O1 146.98(9) 1_565 . ? O1W Sr1 O1 74.66(9) . . ? O1 Sr1 O1 123.81(9) 2_664 . ? O2 Sr1 O1 75.37(10) 2_665 . ? O4 Sr1 O2 78.34(9) . . ? O5 Sr1 O2 138.44(10) 1_565 . ? O1W Sr1 O2 92.11(10) . . ? O1 Sr1 O2 75.03(10) 2_664 . ? O2 Sr1 O2 122.19(9) 2_665 . ? O1 Sr1 O2 49.21(8) . . ? O4 Sr1 C1 79.14(8) . . ? O5 Sr1 C1 149.93(10) 1_565 . ? O1W Sr1 C1 81.97(8) . . ? O1 Sr1 C1 99.61(15) 2_664 . ? O2 Sr1 C1 99.06(16) 2_665 . ? O1 Sr1 C1 24.56(14) . . ? O2 Sr1 C1 24.68(14) . . ? O4 Sr1 Sr1 70.92(6) . 2_665 ? O5 Sr1 Sr1 130.98(7) 1_565 2_665 ? O1W Sr1 Sr1 83.31(7) . 2_665 ? O1 Sr1 Sr1 148.54(7) 2_664 2_665 ? O2 Sr1 Sr1 39.22(8) 2_665 2_665 ? O1 Sr1 Sr1 36.73(7) . 2_665 ? O2 Sr1 Sr1 83.26(7) . 2_665 ? C1 Sr1 Sr1 59.86(14) . 2_665 ? O4 Sr1 Sr1 82.85(6) . 2_664 ? O5 Sr1 Sr1 108.32(7) 1_565 2_664 ? O1W Sr1 Sr1 104.53(8) . 2_664 ? O1 Sr1 Sr1 38.52(8) 2_664 2_664 ? O2 Sr1 Sr1 154.95(8) 2_665 2_664 ? O1 Sr1 Sr1 86.29(7) . 2_664 ? O2 Sr1 Sr1 37.08(8) . 2_664 ? C1 Sr1 Sr1 61.75(14) . 2_664 ? Sr1 Sr1 Sr1 119.070(12) 2_665 2_664 ? O4 Sr1 H1WB 166.7 . . ? O5 Sr1 H1WB 56.4 1_565 . ? O1W Sr1 H1WB 16.7 . . ? O1 Sr1 H1WB 110.8 2_664 . ? O2 Sr1 H1WB 90.5 2_665 . ? O1 Sr1 H1WB 91.4 . . ? O2 Sr1 H1WB 104.1 . . ? C1 Sr1 H1WB 97.6 . . ? Sr1 Sr1 H1WB 96.3 2_665 . ? Sr1 Sr1 H1WB 107.1 2_664 . ? C1 O1 Sr1 149.1(3) . 2_665 ? C1 O1 Sr1 94.8(3) . . ? Sr1 O1 Sr1 104.74(12) 2_665 . ? C1 O2 Sr1 162.7(3) . 2_664 ? C1 O2 Sr1 93.4(3) . . ? Sr1 O2 Sr1 103.69(13) 2_664 . ? C12 O3 C5 122.3(2) 3 . ? C8 O4 Sr1 137.1(2) . . ? C8 O5 Sr1 138.5(3) . 1_545 ? O2 C1 O1 122.5(3) . . ? O2 C1 C2 117.4(6) . . ? O1 C1 C2 120.0(5) . . ? O2 C1 Sr1 62.0(2) . . ? O1 C1 Sr1 60.7(2) . . ? C2 C1 Sr1 175.7(2) . . ? C7 C2 C3 119.9(3) . . ? C7 C2 C1 119.0(4) . . ? C3 C2 C1 121.1(4) . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C6 C5 C4 121.3(3) . . ? C6 C5 O3 114.7(4) . . ? C4 C5 O3 123.7(4) . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? C2 C7 C6 119.9(4) . . ? C2 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? O5 C8 O4 124.0(3) . . ? O5 C8 C9 118.0(3) . . ? O4 C8 C9 118.0(3) . . ? C10 C9 C14 118.8(3) . . ? C10 C9 C8 120.2(4) . . ? C14 C9 C8 121.0(3) . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? C11 C12 O3 124.3(4) . 3_455 ? C11 C12 C13 121.0(3) . . ? O3 C12 C13 114.5(3) 3_455 . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C9 120.9(3) . . ? C13 C14 H14A 119.5 . . ? C9 C14 H14A 119.5 . . ? Sr1 O1W H1WA 114.3 . . ? Sr1 O1W H1WB 103.7 . . ? H1WA O1W H1WB 114.3 . . ? 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 O1W H1WA O5 0.85 2.31 3.091(4) 153.6 2_665 O1W H1WB O4 0.85 1.95 2.759(3) 159.1 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.485 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.093