# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Li2 O10' _chemical_formula_weight 280.04 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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.9227(2) _cell_length_b 13.9837(3) _cell_length_c 15.7876(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1086.78(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 26925 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 30.50 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and three \w scans with 1\% steps (683 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26925 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 30.50 _reflns_number_total 1911 _reflns_number_gt 1803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions; all were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. In the absence of a suitable anomalous scatterer, the Friedel pairs have been merged. PLATON/ADDSYM suggests space group Pnma, which does not match the observed systematic extinctions and some fine details of the structure. 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^)+(0.0582P)^2^+0.1623P] 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 -0.6(10) _chemical_absolute_configuration unk _refine_ls_number_reflns 1911 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0881 _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 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.282 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.045 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 Li1 Li 0.6806(6) 0.7076(2) 0.56522(18) 0.0258(5) Uani 1 1 d . . . Li2 Li 0.6576(6) 0.3057(2) 0.56084(17) 0.0249(5) Uani 1 1 d . . . O1 O 0.8616(3) 0.58585(8) 0.57806(6) 0.0231(2) Uani 1 1 d . . . O2 O 0.8415(2) 0.42697(7) 0.56887(6) 0.0220(2) Uani 1 1 d . . . O3 O 0.3728(3) 0.29059(7) 0.64514(6) 0.0215(2) Uani 1 1 d . . . O4 O 0.1334(3) 0.32790(8) 0.76125(7) 0.0231(2) Uani 1 1 d . . . H4 H 0.0464 0.2739 0.7527 0.028 Uiso 1 1 d R . . O5 O 0.7655(3) 0.47825(9) 0.88646(7) 0.0285(3) Uani 1 1 d . . . O6 O 0.3880(2) 0.55102(8) 0.93234(6) 0.0261(2) Uani 1 1 d . . . H6 H 0.4882 0.5506 0.9808 0.031 Uiso 1 1 d R . . O7 O 0.1279(3) 0.68205(8) 0.76006(6) 0.0221(2) Uani 1 1 d . . . O8 O 0.3806(3) 0.72011(8) 0.64705(6) 0.0224(2) Uani 1 1 d . . . O9 O 0.9929(3) 0.79854(8) 0.54952(7) 0.0242(2) Uani 1 1 d . . . H9A H 0.9601 0.8589 0.5617 0.029 Uiso 1 1 d R . . H9B H 1.1029 0.7710 0.5862 0.029 Uiso 1 1 d R . . O10 O 0.9645(2) 0.20990(8) 0.55126(6) 0.0219(2) Uani 1 1 d . . . H10A H 1.0933 0.2217 0.5853 0.026 Uiso 1 1 d R . . H10B H 0.9175 0.1566 0.5670 0.026 Uiso 1 1 d R . . C1 C 0.5148(3) 0.50547(9) 0.65526(8) 0.0176(2) Uani 1 1 d . . . H1 H 0.3461 0.5054 0.6223 0.021 Uiso 1 1 calc R . . C2 C 0.5021(3) 0.42786(9) 0.72555(8) 0.0177(3) Uani 1 1 d . . . H2 H 0.6861 0.4073 0.7407 0.021 Uiso 1 1 calc R . . C3 C 0.4011(3) 0.50394(9) 0.78874(8) 0.0178(2) Uani 1 1 d . . . H3 H 0.2027 0.5035 0.7939 0.021 Uiso 1 1 calc R . . C4 C 0.5004(3) 0.58216(10) 0.72598(8) 0.0178(3) Uani 1 1 d . . . H4A H 0.6842 0.6028 0.7413 0.021 Uiso 1 1 calc R . . C5 C 0.7579(3) 0.50775(11) 0.59653(8) 0.0189(2) Uani 1 1 d . . . C6 C 0.3262(3) 0.34213(10) 0.70831(9) 0.0184(3) Uani 1 1 d . . . C7 C 0.5373(3) 0.50761(10) 0.87377(8) 0.0193(3) Uani 1 1 d . . . C8 C 0.3253(3) 0.66780(10) 0.70939(9) 0.0189(3) 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 Li1 0.0263(13) 0.0256(12) 0.0253(12) 0.0019(10) 0.0008(12) 0.0007(11) Li2 0.0247(13) 0.0250(11) 0.0249(11) -0.0016(10) 0.0023(12) 0.0005(11) O1 0.0238(5) 0.0210(4) 0.0245(5) 0.0008(4) 0.0047(5) -0.0025(4) O2 0.0241(5) 0.0204(4) 0.0216(4) -0.0005(4) 0.0048(5) 0.0011(4) O3 0.0221(5) 0.0215(5) 0.0208(4) -0.0032(4) 0.0020(5) -0.0020(4) O4 0.0232(6) 0.0213(5) 0.0248(5) -0.0018(4) 0.0058(5) -0.0053(4) O5 0.0228(5) 0.0387(7) 0.0241(5) -0.0022(4) -0.0030(4) 0.0072(5) O6 0.0264(5) 0.0341(6) 0.0178(4) -0.0045(4) -0.0031(5) 0.0081(5) O7 0.0219(5) 0.0223(5) 0.0220(5) 0.0006(4) 0.0037(5) 0.0039(4) O8 0.0242(5) 0.0211(5) 0.0220(5) 0.0033(4) 0.0017(5) 0.0007(4) O9 0.0271(6) 0.0225(5) 0.0230(5) 0.0011(4) -0.0016(5) 0.0004(5) O10 0.0228(5) 0.0215(5) 0.0214(5) -0.0001(4) -0.0012(5) -0.0025(4) C1 0.0185(5) 0.0172(5) 0.0171(5) -0.0009(5) 0.0007(4) 0.0005(5) C2 0.0180(6) 0.0168(6) 0.0183(6) -0.0002(4) 0.0000(5) -0.0003(5) C3 0.0181(5) 0.0182(5) 0.0170(5) -0.0002(5) 0.0002(4) 0.0002(6) C4 0.0180(6) 0.0176(6) 0.0177(6) 0.0000(4) 0.0020(5) 0.0000(5) C5 0.0189(5) 0.0214(6) 0.0165(5) 0.0003(5) 0.0003(4) -0.0004(6) C6 0.0189(7) 0.0171(5) 0.0192(6) 0.0014(5) -0.0001(6) 0.0019(5) C7 0.0210(6) 0.0191(6) 0.0177(5) 0.0014(5) 0.0005(5) -0.0003(6) C8 0.0194(7) 0.0181(6) 0.0190(6) -0.0018(5) -0.0013(6) 0.0004(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 Li1 O1 1.932(3) . ? Li1 O8 1.970(3) . ? Li1 O9 2.011(3) . ? Li1 O9 2.035(3) 4_466 ? Li1 Li1 3.422(4) 4_466 ? Li2 O2 1.927(3) . ? Li2 O3 1.945(3) . ? Li2 O10 2.021(3) 4_456 ? Li2 O10 2.024(3) . ? Li2 Li2 3.489(4) 4_556 ? O1 C5 1.2404(18) . ? O2 C5 1.2790(17) . ? O3 C6 1.2517(17) . ? O4 C6 1.2802(19) . ? O4 H4 0.8784 . ? O5 C7 1.2129(19) . ? O6 C7 1.3278(17) . ? O6 H6 0.9101 . ? O7 C8 1.2747(19) . ? O8 C8 1.2562(17) . ? O9 Li1 2.035(3) 4_566 ? O9 H9A 0.8806 . ? O9 H9B 0.8817 . ? O10 Li2 2.021(3) 4_556 ? O10 H10A 0.8476 . ? O10 H10B 0.8196 . ? C1 C5 1.5141(18) . ? C1 C4 1.5498(18) . ? C1 C2 1.5533(18) . ? C1 H1 0.9800 . ? C2 C6 1.504(2) . ? C2 C3 1.5410(18) . ? C2 H2 0.9800 . ? C3 C7 1.5013(18) . ? C3 C4 1.5549(18) . ? C3 H3 0.9800 . ? C4 C8 1.499(2) . ? C4 H4A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Li1 O8 110.82(14) . . ? O1 Li1 O9 102.57(15) . . ? O8 Li1 O9 126.70(15) . . ? O1 Li1 O9 105.41(14) . 4_466 ? O8 Li1 O9 104.31(15) . 4_466 ? O9 Li1 O9 105.31(13) . 4_466 ? O2 Li2 O3 112.89(14) . . ? O2 Li2 O10 111.92(14) . 4_456 ? O3 Li2 O10 104.38(15) . 4_456 ? O2 Li2 O10 103.70(15) . . ? O3 Li2 O10 121.17(15) . . ? O10 Li2 O10 102.38(12) 4_456 . ? C5 O1 Li1 127.63(14) . . ? C5 O2 Li2 130.46(14) . . ? C6 O3 Li2 127.95(13) . . ? C6 O4 H4 113.2 . . ? C7 O6 H6 106.4 . . ? C8 O8 Li1 128.64(13) . . ? Li1 O9 Li1 115.48(9) . 4_566 ? Li1 O9 H9A 116.1 . . ? Li1 O9 H9A 108.5 4_566 . ? Li1 O9 H9B 96.5 . . ? Li1 O9 H9B 106.7 4_566 . ? H9A O9 H9B 112.8 . . ? Li2 O10 Li2 119.20(9) 4_556 . ? Li2 O10 H10A 103.0 4_556 . ? Li2 O10 H10A 112.5 . . ? Li2 O10 H10B 107.5 4_556 . ? Li2 O10 H10B 111.7 . . ? H10A O10 H10B 101.2 . . ? C5 C1 C4 117.55(11) . . ? C5 C1 C2 118.95(11) . . ? C4 C1 C2 88.11(9) . . ? C5 C1 H1 110.2 . . ? C4 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C2 C3 118.80(12) . . ? C6 C2 C1 116.81(11) . . ? C3 C2 C1 89.61(10) . . ? C6 C2 H2 110.0 . . ? C3 C2 H2 110.0 . . ? C1 C2 H2 110.0 . . ? C7 C3 C2 117.28(11) . . ? C7 C3 C4 113.90(11) . . ? C2 C3 C4 88.37(9) . . ? C7 C3 H3 111.8 . . ? C2 C3 H3 111.8 . . ? C4 C3 H3 111.8 . . ? C8 C4 C1 116.95(11) . . ? C8 C4 C3 119.51(12) . . ? C1 C4 C3 89.23(9) . . ? C8 C4 H4A 109.8 . . ? C1 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O1 C5 O2 124.39(13) . . ? O1 C5 C1 119.20(13) . . ? O2 C5 C1 116.40(12) . . ? O3 C6 O4 124.50(14) . . ? O3 C6 C2 119.86(13) . . ? O4 C6 C2 115.64(12) . . ? O5 C7 O6 123.52(13) . . ? O5 C7 C3 123.36(13) . . ? O6 C7 C3 113.03(12) . . ? O8 C8 O7 124.47(14) . . ? O8 C8 C4 118.54(14) . . ? O7 C8 C4 117.00(12) . . ? 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 O4 H4 O7 0.88 1.56 2.4345(15) 175.6 3_546 O6 H6 O2 0.91 1.65 2.5523(15) 168.6 2_665 O9 H9A O5 0.88 2.30 2.9583(16) 131.8 3_756 O9 H9B O8 0.88 1.82 2.6864(16) 168.9 1_655 O10 H10A O3 0.85 1.93 2.7403(16) 160.4 1_655 O10 H10B O6 0.82 2.11 2.8310(16) 147.2 3_646 _database_code_depnum_ccdc_archive 'CCDC 948877' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H16 Li4 O13' _chemical_formula_weight 347.97 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.6635(16) _cell_length_b 8.1817(4) _cell_length_c 8.1299(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.514(4) _cell_angle_gamma 90.00 _cell_volume 1425.10(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23295 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and five \w scans with 2\% steps (441 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23295 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1348 _reflns_number_gt 1203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0494P)^2^+1.0728P] 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 1348 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.245 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.058 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 Li1 Li 0.80108(12) 0.6644(3) 0.9447(3) 0.0237(6) Uani 1 1 d . . . Li2 Li 0.91913(13) 0.8181(3) 1.0892(3) 0.0266(6) Uani 1 1 d . . . O1 O 0.86393(5) 0.80760(13) 0.87531(13) 0.0219(3) Uani 1 1 d . . . O2 O 0.90841(5) 1.00731(14) 0.74843(13) 0.0259(3) Uani 1 1 d . . . O3 O 0.72265(5) 0.77289(13) 0.84112(12) 0.0224(3) Uani 1 1 d . . . O4 O 0.68797(5) 0.95141(13) 0.64312(12) 0.0212(3) Uani 1 1 d . . . O5 O 0.91694(5) 0.60635(14) 1.21679(14) 0.0295(3) Uani 1 1 d . . . H5A H 0.8801 0.5739 1.2546 0.035 Uiso 1 1 d R . . H5B H 0.9395 0.5146 1.2142 0.035 Uiso 1 1 d R . . O6 O 1.00764(5) 0.81042(15) 1.05438(14) 0.0277(3) Uani 1 1 d . . . H6A H 1.0296 0.7223 1.1166 0.033 Uiso 1 1 d R . . H6B H 1.0316 0.9004 1.0892 0.033 Uiso 1 1 d R . . O7 O 1.0000 0.3455(2) 1.2500 0.0290(4) Uani 1 2 d S . . H7 H 1.0000 0.2798 1.1539 0.035 Uiso 1 1 d R . . C1 C 0.86821(7) 0.89680(18) 0.75030(18) 0.0201(3) Uani 1 1 d . . . C2 C 0.82374(7) 0.87409(19) 0.58837(17) 0.0216(3) Uani 1 1 d . . . H2A H 0.8478 0.8327 0.5057 0.026 Uiso 1 1 calc R . . H2B H 0.8083 0.9811 0.5511 0.026 Uiso 1 1 calc R . . C3 C 0.76738(7) 0.76169(19) 0.58942(17) 0.0190(3) Uani 1 1 d . . . H3 H 0.7819 0.6550 0.6344 0.023 Uiso 1 1 calc R . . C4 C 0.72280(7) 0.83446(18) 0.69901(18) 0.0186(3) 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 Li1 0.0263(13) 0.0240(13) 0.0212(13) 0.0001(10) 0.0051(10) 0.0002(10) Li2 0.0257(14) 0.0285(15) 0.0248(13) -0.0016(10) 0.0012(10) 0.0010(11) O1 0.0220(6) 0.0235(6) 0.0201(5) 0.0007(4) 0.0030(4) -0.0019(4) O2 0.0249(6) 0.0270(6) 0.0248(6) 0.0031(4) -0.0001(4) -0.0074(5) O3 0.0238(6) 0.0269(6) 0.0169(5) 0.0014(4) 0.0038(4) 0.0023(4) O4 0.0220(5) 0.0200(6) 0.0221(5) 0.0012(4) 0.0044(4) 0.0013(4) O5 0.0257(6) 0.0263(6) 0.0387(7) 0.0017(5) 0.0115(5) 0.0017(5) O6 0.0254(6) 0.0309(7) 0.0261(6) -0.0020(5) 0.0018(5) -0.0031(5) O7 0.0327(9) 0.0281(9) 0.0269(8) 0.000 0.0072(7) 0.000 C1 0.0186(7) 0.0218(8) 0.0199(7) -0.0020(6) 0.0027(6) 0.0008(6) C2 0.0208(7) 0.0253(8) 0.0187(7) -0.0002(6) 0.0035(6) -0.0017(6) C3 0.0192(7) 0.0211(8) 0.0163(7) -0.0010(6) 0.0013(6) 0.0006(6) C4 0.0170(7) 0.0197(7) 0.0185(7) -0.0030(6) 0.0010(5) -0.0033(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Li1 O4 1.911(3) 4_646 ? Li1 O1 1.942(3) . ? Li1 O3 1.956(3) 7_667 ? Li1 O3 1.990(3) . ? Li2 O1 1.961(3) . ? Li2 O2 1.964(3) 6_576 ? Li2 O6 1.980(3) . ? Li2 O5 2.023(3) . ? O1 C1 1.2657(18) . ? O2 C1 1.2570(18) . ? O2 Li2 1.964(3) 6_575 ? O3 C4 1.2609(18) . ? O3 Li1 1.956(3) 7_667 ? O4 C4 1.2609(19) . ? O4 Li1 1.911(3) 4_656 ? O5 H5A 0.9357 . ? O5 H5B 0.8970 . ? O6 H6A 0.9652 . ? O6 H6B 0.9215 . ? O7 H7 0.9485 . ? C1 C2 1.523(2) . ? C2 C3 1.529(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.528(2) . ? C3 C3 1.547(3) 7_666 ? C3 H3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Li1 O1 108.08(13) 4_646 . ? O4 Li1 O3 129.46(14) 4_646 7_667 ? O1 Li1 O3 112.85(14) . 7_667 ? O4 Li1 O3 113.21(14) 4_646 . ? O1 Li1 O3 101.49(12) . . ? O3 Li1 O3 86.51(11) 7_667 . ? O1 Li2 O2 120.02(14) . 6_576 ? O1 Li2 O6 110.35(14) . . ? O2 Li2 O6 109.19(14) 6_576 . ? O1 Li2 O5 111.07(14) . . ? O2 Li2 O5 105.72(13) 6_576 . ? O6 Li2 O5 98.21(13) . . ? C1 O1 Li1 135.97(12) . . ? C1 O1 Li2 125.40(13) . . ? Li1 O1 Li2 97.50(12) . . ? C1 O2 Li2 132.90(12) . 6_575 ? C4 O3 Li1 138.39(13) . 7_667 ? C4 O3 Li1 116.62(12) . . ? Li1 O3 Li1 93.49(11) 7_667 . ? C4 O4 Li1 136.53(13) . 4_656 ? Li2 O5 H5A 119.8 . . ? Li2 O5 H5B 130.6 . . ? H5A O5 H5B 105.3 . . ? Li2 O6 H6A 111.2 . . ? Li2 O6 H6B 116.4 . . ? H6A O6 H6B 102.9 . . ? O2 C1 O1 123.90(13) . . ? O2 C1 C2 115.34(13) . . ? O1 C1 C2 120.76(13) . . ? C1 C2 C3 118.15(12) . . ? C1 C2 H2A 107.8 . . ? C3 C2 H2A 107.8 . . ? C1 C2 H2B 107.8 . . ? C3 C2 H2B 107.8 . . ? H2A C2 H2B 107.1 . . ? C4 C3 C2 110.05(12) . . ? C4 C3 C3 109.53(14) . 7_666 ? C2 C3 C3 110.31(14) . 7_666 ? C4 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? C3 C3 H3 109.0 7_666 . ? O3 C4 O4 123.42(13) . . ? O3 C4 C3 117.78(13) . . ? O4 C4 C3 118.80(13) . . ? 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 O5 H5A O4 0.94 1.81 2.7298(15) 167.7 7_667 O5 H5B O7 0.90 1.90 2.7785(17) 166.3 . O6 H6B O2 0.92 1.87 2.6903(15) 147.3 5_777 O6 H6A O5 0.97 1.90 2.8317(17) 161.5 2_757 O7 H7 O6 0.95 1.83 2.7673(13) 168.2 5_767 _database_code_depnum_ccdc_archive 'CCDC 948878' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 Na O8' _chemical_formula_weight 254.13 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' Na Na 0.0362 0.0249 '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' 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 5.3722(2) _cell_length_b 13.4257(11) _cell_length_c 12.4510(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.272(5) _cell_angle_gamma 90.00 _cell_volume 897.81(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 31005 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 30.49 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.880 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and six \w scans with 2\% steps (450 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31005 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 30.49 _reflns_number_total 2734 _reflns_number_gt 2148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions; all were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0549P)^2^+0.1647P] 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 2734 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.340 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.056 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 Na Na 0.25226(10) 0.72590(4) 0.94669(4) 0.02616(15) Uani 1 1 d . . . O1 O 0.35282(18) 0.74555(8) 0.76215(8) 0.0258(2) Uani 1 1 d . . . O2 O 0.49857(18) 0.76641(8) 0.59739(8) 0.0243(2) Uani 1 1 d . . . O3 O 0.65641(19) 0.63096(8) 0.97875(8) 0.0293(2) Uani 1 1 d . . . H3 H 0.7628 0.6491 1.0354 0.035 Uiso 1 1 d R . . O4 O 1.01869(18) 0.58171(8) 0.90945(8) 0.0253(2) Uani 1 1 d . . . O5 O 0.58632(17) 0.35169(7) 0.62007(8) 0.0226(2) Uani 1 1 d . . . O6 O 0.44640(19) 0.38004(7) 0.78424(8) 0.0249(2) Uani 1 1 d . . . H6 H 0.3396 0.3293 0.7674 0.030 Uiso 1 1 d R . . O7 O 1.02527(18) 0.64820(8) 0.50605(8) 0.0254(2) Uani 1 1 d . . . H7 H 1.1903 0.6451 0.4739 0.030 Uiso 1 1 d R . . O8 O 1.20651(18) 0.53486(8) 0.61331(9) 0.0286(2) Uani 1 1 d . . . C1 C 0.7054(2) 0.65155(10) 0.71434(10) 0.0182(2) Uani 1 1 d . . . H1 H 0.8578 0.6871 0.7358 0.022 Uiso 1 1 calc R . . C2 C 0.6479(2) 0.57044(9) 0.80017(10) 0.0192(2) Uani 1 1 d . . . H2 H 0.4693 0.5627 0.8121 0.023 Uiso 1 1 calc R . . C3 C 0.7516(2) 0.49081(10) 0.72355(10) 0.0187(2) Uani 1 1 d . . . H3A H 0.9180 0.4695 0.7478 0.022 Uiso 1 1 calc R . . C4 C 0.7701(2) 0.56834(9) 0.63210(10) 0.0185(2) Uani 1 1 d . . . H4 H 0.6389 0.5596 0.5770 0.022 Uiso 1 1 calc R . . C5 C 0.5033(2) 0.72603(10) 0.68742(10) 0.0193(3) Uani 1 1 d . . . C6 C 0.7940(3) 0.59100(10) 0.90193(10) 0.0216(3) Uani 1 1 d . . . C7 C 0.5849(2) 0.40116(10) 0.70379(10) 0.0197(3) Uani 1 1 d . . . C8 C 1.0231(2) 0.58017(10) 0.58433(10) 0.0199(3) 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 Na 0.0242(3) 0.0314(3) 0.0231(3) -0.0043(2) 0.0039(2) -0.0040(2) O1 0.0279(5) 0.0281(5) 0.0219(5) 0.0024(4) 0.0071(4) 0.0098(4) O2 0.0232(5) 0.0286(5) 0.0211(5) 0.0039(4) 0.0031(4) 0.0055(4) O3 0.0277(5) 0.0399(6) 0.0202(5) -0.0071(4) -0.0001(4) 0.0030(4) O4 0.0217(5) 0.0278(5) 0.0262(5) -0.0018(4) -0.0019(4) -0.0003(4) O5 0.0224(5) 0.0231(5) 0.0224(5) -0.0028(4) 0.0050(4) -0.0029(4) O6 0.0273(5) 0.0246(5) 0.0231(5) -0.0018(4) 0.0076(4) -0.0083(4) O7 0.0195(5) 0.0295(5) 0.0274(5) 0.0078(4) 0.0062(4) 0.0009(4) O8 0.0192(5) 0.0317(6) 0.0350(6) 0.0068(4) 0.0049(4) 0.0038(4) C1 0.0172(6) 0.0190(6) 0.0184(6) -0.0004(4) 0.0015(4) 0.0001(4) C2 0.0188(6) 0.0199(6) 0.0189(6) -0.0005(5) 0.0020(4) 0.0006(5) C3 0.0176(6) 0.0193(6) 0.0194(6) -0.0002(5) 0.0024(4) 0.0001(5) C4 0.0177(6) 0.0193(6) 0.0185(6) -0.0007(4) 0.0027(4) -0.0002(4) C5 0.0184(6) 0.0193(6) 0.0203(6) -0.0009(5) 0.0014(4) -0.0002(5) C6 0.0252(6) 0.0200(6) 0.0196(6) 0.0012(5) 0.0010(5) 0.0001(5) C7 0.0172(6) 0.0194(6) 0.0226(6) 0.0018(5) 0.0020(5) 0.0001(4) C8 0.0194(6) 0.0200(6) 0.0205(6) -0.0016(5) 0.0027(5) -0.0007(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 Na O2 2.3457(11) 4_576 ? Na O7 2.3465(11) 4_576 ? Na O4 2.3477(12) 1_455 ? Na O1 2.3866(11) . ? Na O3 2.5416(12) . ? Na O5 2.6047(11) 2_556 ? O1 C5 1.2734(16) . ? O2 C5 1.2448(16) . ? O2 Na 2.3457(11) 4_675 ? O3 C6 1.3343(17) . ? O3 H3 0.9301 . ? O4 C6 1.2150(17) . ? O4 Na 2.3477(12) 1_655 ? O5 C7 1.2362(16) . ? O5 Na 2.6047(11) 2_546 ? O6 C7 1.2926(16) . ? O6 H6 0.9120 . ? O7 C8 1.3360(16) . ? O7 Na 2.3465(11) 4_675 ? O7 H7 0.9819 . ? O8 C8 1.2066(17) . ? C1 C5 1.5082(18) . ? C1 C4 1.5599(18) . ? C1 C2 1.5612(18) . ? C1 H1 0.9800 . ? C2 C6 1.5011(18) . ? C2 C3 1.5449(18) . ? C2 H2 0.9800 . ? C3 C7 1.5167(18) . ? C3 C4 1.5475(18) . ? C3 H3A 0.9800 . ? C4 C8 1.5039(17) . ? C4 H4 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Na O7 94.97(4) 4_576 4_576 ? O2 Na O4 82.92(4) 4_576 1_455 ? O7 Na O4 169.67(4) 4_576 1_455 ? O2 Na O1 155.95(4) 4_576 . ? O7 Na O1 94.03(4) 4_576 . ? O4 Na O1 91.86(4) 1_455 . ? O2 Na O3 113.95(4) 4_576 . ? O7 Na O3 77.64(4) 4_576 . ? O4 Na O3 93.92(4) 1_455 . ? O1 Na O3 89.76(4) . . ? O2 Na O5 79.21(4) 4_576 2_556 ? O7 Na O5 93.48(4) 4_576 2_556 ? O4 Na O5 96.04(4) 1_455 2_556 ? O1 Na O5 78.02(4) . 2_556 ? O3 Na O5 164.45(4) . 2_556 ? C5 O1 Na 147.32(9) . . ? C5 O2 Na 137.63(9) . 4_675 ? C6 O3 Na 125.03(8) . . ? C6 O3 H3 107.9 . . ? Na O3 H3 119.7 . . ? C6 O4 Na 117.15(9) . 1_655 ? C7 O5 Na 126.89(8) . 2_546 ? C7 O6 H6 110.8 . . ? C8 O7 Na 134.96(8) . 4_675 ? C8 O7 H7 106.9 . . ? Na O7 H7 117.8 4_675 . ? C5 C1 C4 119.92(10) . . ? C5 C1 C2 117.54(10) . . ? C4 C1 C2 90.01(9) . . ? C5 C1 H1 109.3 . . ? C4 C1 H1 109.3 . . ? C2 C1 H1 109.3 . . ? C6 C2 C3 117.37(11) . . ? C6 C2 C1 110.00(10) . . ? C3 C2 C1 88.89(9) . . ? C6 C2 H2 112.8 . . ? C3 C2 H2 112.8 . . ? C1 C2 H2 112.8 . . ? C7 C3 C2 115.46(10) . . ? C7 C3 C4 117.50(11) . . ? C2 C3 C4 91.08(9) . . ? C7 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3A 110.5 . . ? C8 C4 C3 115.82(11) . . ? C8 C4 C1 113.61(11) . . ? C3 C4 C1 88.85(9) . . ? C8 C4 H4 112.2 . . ? C3 C4 H4 112.2 . . ? C1 C4 H4 112.2 . . ? O2 C5 O1 124.59(12) . . ? O2 C5 C1 119.28(11) . . ? O1 C5 C1 116.07(11) . . ? O4 C6 O3 123.45(12) . . ? O4 C6 C2 123.09(12) . . ? O3 C6 C2 113.04(11) . . ? O5 C7 O6 123.36(12) . . ? O5 C7 C3 123.27(11) . . ? O6 C7 C3 113.35(11) . . ? O8 C8 O7 122.85(12) . . ? O8 C8 C4 124.59(12) . . ? O7 C8 C4 112.56(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.93 1.86 2.7090(14) 151.4 4_676 O3 H3 O6 0.93 2.56 3.0179(14) 110.5 3_667 O6 H6 O1 0.91 1.57 2.4773(14) 177.5 2_546 O6 H6 O2 0.91 2.64 3.2203(13) 122.0 2_546 O7 H7 O5 0.98 1.69 2.6392(13) 160.1 3_766 _database_code_depnum_ccdc_archive 'CCDC 948879' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 K2 O12' _chemical_formula_weight 380.39 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' K K 0.2009 0.2494 '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' 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 8.4001(7) _cell_length_b 13.7383(11) _cell_length_c 6.4302(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.284(5) _cell_angle_gamma 90.00 _cell_volume 719.12(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 22296 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps (399 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22296 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1362 _reflns_number_gt 1174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0377P)^2^+0.2230P] 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 1362 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.056 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 K K 0.95222(5) 0.65089(3) 0.11051(6) 0.02402(14) Uani 1 1 d . . . O1 O 0.81027(16) 0.83797(9) -0.0063(2) 0.0259(3) Uani 1 1 d . . . O2 O 0.54484(15) 0.80538(8) -0.0371(2) 0.0236(3) Uani 1 1 d . . . H2 H 0.5798 0.7376 -0.0329 0.028 Uiso 1 1 d R . . O3 O 0.62358(16) 0.87065(9) 0.42833(19) 0.0230(3) Uani 1 1 d . . . O4 O 0.35197(15) 0.88458(9) 0.31143(19) 0.0225(3) Uani 1 1 d . . . O5 O 1.17543(16) 0.76708(10) -0.0414(2) 0.0272(3) Uani 1 1 d . . . H5A H 1.2437 0.8062 0.0570 0.033 Uiso 1 1 d R . . H5B H 1.2525 0.7274 -0.0694 0.033 Uiso 1 1 d R . . O6 O 0.96048(17) 0.46022(9) 0.2277(2) 0.0282(3) Uani 1 1 d . . . H6A H 1.0170 0.4265 0.3335 0.034 Uiso 1 1 d R . . H6B H 0.8594 0.4423 0.2213 0.034 Uiso 1 1 d R . . C1 C 0.6696(2) 0.86447(12) -0.0129(3) 0.0196(4) Uani 1 1 d . . . C2 C 0.6240(2) 0.96985(12) 0.0041(3) 0.0190(4) Uani 1 1 d . . . H2A H 0.7193 1.0128 0.0184 0.023 Uiso 1 1 calc R . . C3 C 0.5247(2) 0.99436(12) 0.1747(3) 0.0187(4) Uani 1 1 d . . . H3 H 0.5756 1.0492 0.2644 0.022 Uiso 1 1 calc R . . C4 C 0.4960(2) 0.91038(12) 0.3144(3) 0.0193(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 K 0.0227(2) 0.0217(2) 0.0274(2) 0.00033(15) 0.00578(17) 0.00019(15) O1 0.0203(7) 0.0218(6) 0.0362(8) -0.0004(5) 0.0080(6) 0.0021(5) O2 0.0223(7) 0.0164(6) 0.0329(7) -0.0020(5) 0.0080(5) 0.0007(5) O3 0.0216(7) 0.0198(6) 0.0258(6) 0.0040(5) 0.0024(5) 0.0009(5) O4 0.0205(7) 0.0223(6) 0.0260(6) 0.0024(5) 0.0082(5) -0.0008(5) O5 0.0230(7) 0.0320(7) 0.0269(7) -0.0057(6) 0.0064(5) -0.0003(6) O6 0.0249(7) 0.0273(7) 0.0326(7) 0.0049(6) 0.0072(6) -0.0011(6) C1 0.0212(10) 0.0199(8) 0.0175(8) 0.0013(7) 0.0043(7) -0.0001(7) C2 0.0183(9) 0.0167(8) 0.0223(8) 0.0011(7) 0.0054(7) 0.0001(7) C3 0.0194(9) 0.0161(8) 0.0205(8) -0.0006(7) 0.0047(7) 0.0007(7) C4 0.0241(10) 0.0168(8) 0.0171(8) -0.0029(7) 0.0053(7) 0.0015(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 K O6 2.7219(13) . ? K O3 2.7359(13) 4_575 ? K O5 2.7795(14) 4_576 ? K O5 2.8144(14) . ? K O1 2.8548(13) . ? K O6 2.8957(13) 3_765 ? K O1 2.9941(13) 4_576 ? O1 C1 1.227(2) . ? O1 K 2.9941(13) 4_575 ? O2 C1 1.304(2) . ? O2 H2 0.9749 . ? O3 C4 1.263(2) . ? O3 K 2.7359(13) 4_576 ? O4 C4 1.256(2) . ? O5 K 2.7795(14) 4_575 ? O5 H5A 0.9159 . ? O5 H5B 0.8981 . ? O6 K 2.8957(13) 3_765 ? O6 H6A 0.8621 . ? O6 H6B 0.8754 . ? C1 C2 1.508(2) . ? C2 C3 1.554(2) 3_675 ? C2 C3 1.570(2) . ? C2 H2A 0.9800 . ? C3 C4 1.518(2) . ? C3 C2 1.554(2) 3_675 ? C3 H3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 K O3 88.20(4) . 4_575 ? O6 K O5 101.60(4) . 4_576 ? O3 K O5 142.90(4) 4_575 4_576 ? O6 K O5 131.93(4) . . ? O3 K O5 126.94(4) 4_575 . ? O5 K O5 71.02(3) 4_576 . ? O6 K O1 156.89(4) . . ? O3 K O1 70.91(4) 4_575 . ? O5 K O1 90.11(4) 4_576 . ? O5 K O1 70.66(4) . . ? O6 K O6 72.95(4) . 3_765 ? O3 K O6 92.13(4) 4_575 3_765 ? O5 K O6 124.97(4) 4_576 3_765 ? O5 K O6 74.01(4) . 3_765 ? O1 K O6 116.34(4) . 3_765 ? O6 K O1 79.01(4) . 4_576 ? O3 K O1 78.07(4) 4_575 4_576 ? O5 K O1 69.09(4) 4_576 4_576 ? O5 K O1 133.73(4) . 4_576 ? O1 K O1 86.86(4) . 4_576 ? O6 K O1 150.58(4) 3_765 4_576 ? C1 O1 K 127.75(11) . . ? C1 O1 K 122.16(11) . 4_575 ? K O1 K 92.14(4) . 4_575 ? C1 O2 H2 111.3 . . ? C4 O3 K 156.51(11) . 4_576 ? K O5 K 97.74(4) 4_575 . ? K O5 H5A 120.1 4_575 . ? K O5 H5A 116.8 . . ? K O5 H5B 117.4 4_575 . ? K O5 H5B 107.5 . . ? H5A O5 H5B 97.8 . . ? K O6 K 107.05(4) . 3_765 ? K O6 H6A 135.0 . . ? K O6 H6A 96.7 3_765 . ? K O6 H6B 107.4 . . ? K O6 H6B 103.8 3_765 . ? H6A O6 H6B 103.0 . . ? O1 C1 O2 123.91(16) . . ? O1 C1 C2 122.81(16) . . ? O2 C1 C2 113.28(15) . . ? C1 C2 C3 114.97(14) . 3_675 ? C1 C2 C3 116.40(13) . . ? C3 C2 C3 88.88(13) 3_675 . ? C1 C2 H2A 111.6 . . ? C3 C2 H2A 111.6 3_675 . ? C3 C2 H2A 111.6 . . ? C4 C3 C2 117.53(15) . 3_675 ? C4 C3 C2 116.10(14) . . ? C2 C3 C2 91.12(13) 3_675 . ? C4 C3 H3 110.3 . . ? C2 C3 H3 110.3 3_675 . ? C2 C3 H3 110.3 . . ? O4 C4 O3 124.27(16) . . ? O4 C4 C3 119.91(15) . . ? O3 C4 C3 115.82(15) . . ? 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 O3 0.97 1.57 2.5314(17) 169.5 4_575 O5 H5A O4 0.92 1.98 2.8795(18) 166.0 1_655 O5 H5B O4 0.90 1.99 2.8511(17) 159.6 4_675 O6 H6A O1 0.86 2.01 2.8349(18) 160.9 2_745 O6 H6B O4 0.88 1.91 2.7759(18) 171.0 2_645 _database_code_depnum_ccdc_archive 'CCDC 948880' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 K O8' _chemical_formula_weight 270.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 2/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.6068(2) _cell_length_b 5.5968(2) _cell_length_c 10.7160(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.205(2) _cell_angle_gamma 90.00 _cell_volume 515.81(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15997 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.67 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.819 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and five \w scans with 1\% steps (936 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15997 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.67 _reflns_number_total 1260 _reflns_number_gt 1217 _reflns_threshold_expression >2sigma(I) _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions; the H atom bound to O1 was given an occupancy factor of 0.5 for charge equilibrium and to account for its closeness to its image by symmetry. All H atoms were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0588P)^2^+0.1199P] 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 1260 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 28.67 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.385 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.055 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 K K 0.7500 0.51661(6) 0.2500 0.02508(15) Uani 1 2 d S . . O1 O 1.02036(11) 0.64309(17) 0.08534(8) 0.0320(2) Uani 1 1 d . . . H1 H 1.0286 0.5184 0.0300 0.038 Uiso 0.50 1 d PR . . O2 O 1.17376(10) 0.80715(16) -0.05119(7) 0.0275(2) Uani 1 1 d . . . O3 O 0.88751(9) 0.91982(16) 0.37293(8) 0.0254(2) Uani 1 1 d . . . H3 H 0.8113 1.0258 0.3995 0.030 Uiso 1 1 d R . . O4 O 1.01349(10) 1.26430(16) 0.34035(8) 0.0279(2) Uani 1 1 d . . . C1 C 1.12498(12) 0.7913(2) 0.05606(10) 0.0197(2) Uani 1 1 d . . . C2 C 1.19091(11) 0.94735(19) 0.16023(9) 0.0179(2) Uani 1 1 d . . . H2 H 1.1775 1.1170 0.1399 0.021 Uiso 1 1 calc R . . C3 C 1.13895(11) 0.89391(19) 0.29409(9) 0.0185(2) Uani 1 1 d . . . H3A H 1.1146 0.7240 0.3038 0.022 Uiso 1 1 calc R . . C4 C 1.00907(12) 1.0477(2) 0.33916(9) 0.0199(2) 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 K 0.0258(2) 0.0230(2) 0.0263(2) 0.000 -0.00001(14) 0.000 O1 0.0396(5) 0.0366(5) 0.0205(4) -0.0071(3) 0.0081(3) -0.0205(4) O2 0.0293(4) 0.0345(5) 0.0190(4) -0.0040(3) 0.0053(3) -0.0120(3) O3 0.0203(4) 0.0264(4) 0.0298(4) -0.0028(3) 0.0060(3) 0.0018(3) O4 0.0283(4) 0.0227(4) 0.0328(5) -0.0014(3) 0.0027(3) 0.0047(3) C1 0.0191(5) 0.0216(5) 0.0184(5) -0.0002(4) 0.0006(4) -0.0015(4) C2 0.0177(4) 0.0184(5) 0.0174(5) -0.0002(4) -0.0001(3) -0.0003(4) C3 0.0188(5) 0.0192(5) 0.0175(5) -0.0005(3) 0.0005(3) 0.0009(4) C4 0.0202(5) 0.0235(5) 0.0160(5) -0.0008(4) -0.0011(4) 0.0032(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 K O4 2.8117(9) 1_545 ? K O4 2.8117(9) 2_645 ? K O3 2.8476(9) 2_655 ? K O3 2.8476(9) . ? K O2 2.8914(9) 4_566 ? K O2 2.8915(9) 3_765 ? K O1 3.0570(9) . ? K O1 3.0570(9) 2_655 ? O1 C1 1.2724(14) . ? O1 H1 0.9206 . ? O2 C1 1.2418(13) . ? O2 K 2.8914(9) 3_765 ? O3 C4 1.3294(14) . ? O3 H3 0.9369 . ? O4 C4 1.2128(15) . ? O4 K 2.8117(9) 1_565 ? C1 C2 1.5107(14) . ? C2 C3 1.5480(14) . ? C2 C3 1.5551(13) 2_755 ? C2 H2 0.9800 . ? C3 C4 1.5051(14) . ? C3 C2 1.5551(13) 2_755 ? C3 H3A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 K O4 119.71(4) 1_545 2_645 ? O4 K O3 150.77(2) 1_545 2_655 ? O4 K O3 85.60(2) 2_645 2_655 ? O4 K O3 85.60(2) 1_545 . ? O4 K O3 150.77(2) 2_645 . ? O3 K O3 75.16(4) 2_655 . ? O4 K O2 68.56(3) 1_545 4_566 ? O4 K O2 74.70(3) 2_645 4_566 ? O3 K O2 137.34(2) 2_655 4_566 ? O3 K O2 104.94(3) . 4_566 ? O4 K O2 74.70(3) 1_545 3_765 ? O4 K O2 68.56(3) 2_645 3_765 ? O3 K O2 104.94(3) 2_655 3_765 ? O3 K O2 137.34(2) . 3_765 ? O2 K O2 102.39(4) 4_566 3_765 ? O4 K O1 72.14(3) 1_545 . ? O4 K O1 122.64(2) 2_645 . ? O3 K O1 82.04(3) 2_655 . ? O3 K O1 76.79(2) . . ? O2 K O1 140.33(3) 4_566 . ? O2 K O1 61.34(2) 3_765 . ? O4 K O1 122.64(2) 1_545 2_655 ? O4 K O1 72.14(3) 2_645 2_655 ? O3 K O1 76.79(2) 2_655 2_655 ? O3 K O1 82.04(3) . 2_655 ? O2 K O1 61.34(2) 4_566 2_655 ? O2 K O1 140.33(3) 3_765 2_655 ? O1 K O1 153.22(4) . 2_655 ? C1 O1 K 148.75(8) . . ? C1 O1 H1 105.2 . . ? K O1 H1 106.0 . . ? C1 O2 K 137.01(8) . 3_765 ? C4 O3 K 128.19(7) . . ? C4 O3 H3 108.0 . . ? K O3 H3 111.1 . . ? C4 O4 K 118.28(7) . 1_565 ? O2 C1 O1 122.86(10) . . ? O2 C1 C2 120.78(9) . . ? O1 C1 C2 116.35(9) . . ? C1 C2 C3 117.34(9) . . ? C1 C2 C3 116.34(9) . 2_755 ? C3 C2 C3 88.47(8) . 2_755 ? C1 C2 H2 111.0 . . ? C3 C2 H2 111.0 . . ? C3 C2 H2 111.0 2_755 . ? C4 C3 C2 115.56(8) . . ? C4 C3 C2 119.41(9) . 2_755 ? C2 C3 C2 87.27(8) . 2_755 ? C4 C3 H3A 110.9 . . ? C2 C3 H3A 110.9 . . ? C2 C3 H3A 110.9 2_755 . ? O4 C4 O3 124.06(10) . . ? O4 C4 C3 123.48(10) . . ? O3 C4 C3 112.42(10) . . ? 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 0.92 1.57 2.4463(17) 156.4 3_765 O3 H3 O2 0.94 1.61 2.5487(11) 176.1 4_576 _database_code_depnum_ccdc_archive 'CCDC 948881' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 O8 Rb' _chemical_formula_weight 316.61 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 c c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 8.1309(4) _cell_length_b 9.6620(5) _cell_length_c 12.7399(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1000.86(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 56474 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 30.50 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 4.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.304 _exptl_absorpt_correction_T_max 0.408 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and thirteen \w scans with 2\% steps (741 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 56474 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_unetI/netI 0.0142 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 30.50 _reflns_number_total 1527 _reflns_number_gt 1331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions; the H atom bound to O1 was given an occupancy factor of 0.5 for charge equilibrium and to account for its closeness to its image by symmetry. All H atoms were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0430P)^2^+0.1721P] 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 1527 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.291 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.069 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 Rb Rb 0.7500 0.7500 0.445681(16) 0.02820(9) Uani 1 2 d S . . O1 O 1.06921(12) 0.60330(10) 0.46183(7) 0.0241(2) Uani 1 1 d . . . H1 H 1.0517 0.5335 0.4961 0.029 Uiso 0.50 1 d PR . . O2 O 1.20957(13) 0.44061(10) 0.37659(8) 0.0251(2) Uani 1 1 d . . . O3 O 0.96937(12) 0.64409(10) 0.21947(8) 0.0273(2) Uani 1 1 d . . . H3 H 0.8810 0.6068 0.1888 0.033 Uiso 1 1 d R . . O4 O 1.11130(13) 0.50637(11) 0.11118(8) 0.0337(2) Uani 1 1 d . . . C1 C 1.18006(15) 0.56451(13) 0.39633(9) 0.0205(2) Uani 1 1 d . . . C2 C 1.27662(15) 0.67380(13) 0.33856(11) 0.0194(2) Uani 1 1 d . . . H2 H 1.3930 0.6672 0.3579 0.023 Uiso 1 1 calc R . . C3 C 1.25943(14) 0.66948(16) 0.21590(11) 0.0205(3) Uani 1 1 d . . . H3A H 1.3599 0.6381 0.1807 0.025 Uiso 1 1 calc R . . C4 C 1.10703(17) 0.59756(14) 0.17626(10) 0.0228(2) 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 Rb 0.02922(13) 0.02228(12) 0.03309(13) 0.000 0.000 0.00330(6) O1 0.0259(5) 0.0218(5) 0.0245(4) 0.0031(3) 0.0055(3) 0.0022(4) O2 0.0277(5) 0.0198(4) 0.0277(5) 0.0002(4) 0.0061(4) -0.0005(4) O3 0.0245(5) 0.0269(5) 0.0306(5) -0.0062(4) -0.0036(4) -0.0032(4) O4 0.0346(6) 0.0330(6) 0.0337(5) -0.0128(4) 0.0025(4) -0.0077(4) C1 0.0207(6) 0.0214(6) 0.0192(5) 0.0015(4) -0.0007(4) -0.0005(4) C2 0.0197(5) 0.0185(6) 0.0199(6) 0.0002(5) -0.0006(4) -0.0006(4) C3 0.0219(6) 0.0194(6) 0.0201(5) -0.0006(5) 0.0020(4) -0.0021(4) C4 0.0267(6) 0.0214(6) 0.0203(5) 0.0013(5) -0.0012(5) -0.0038(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 Rb O4 2.8164(11) 4_465 ? Rb O4 2.8164(11) 3_755 ? Rb O2 2.9371(10) 5_766 ? Rb O2 2.9371(10) 6_566 ? Rb O1 2.9645(10) . ? Rb O1 2.9645(10) 2_665 ? Rb O3 3.5403(10) 2_665 ? Rb O3 3.5403(10) . ? O1 C1 1.2842(15) . ? O1 H1 0.8159 . ? O2 C1 1.2466(16) . ? O2 Rb 2.9371(10) 5_766 ? O3 C4 1.3259(17) . ? O3 H3 0.8939 . ? O4 C4 1.2103(16) . ? O4 Rb 2.8164(11) 3_745 ? C1 C2 1.5076(17) . ? C2 C2 1.535(3) 2_765 ? C2 C3 1.5695(18) . ? C2 H2 0.9800 . ? C3 C4 1.5078(18) . ? C3 C3 1.564(3) 2_765 ? C3 H3A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Rb O4 150.19(4) 4_465 3_755 ? O4 Rb O2 72.04(3) 4_465 5_766 ? O4 Rb O2 134.83(3) 3_755 5_766 ? O4 Rb O2 134.83(3) 4_465 6_566 ? O4 Rb O2 72.04(3) 3_755 6_566 ? O2 Rb O2 79.13(4) 5_766 6_566 ? O4 Rb O1 87.01(3) 4_465 . ? O4 Rb O1 95.04(3) 3_755 . ? O2 Rb O1 63.17(3) 5_766 . ? O2 Rb O1 110.14(3) 6_566 . ? O4 Rb O1 95.04(3) 4_465 2_665 ? O4 Rb O1 87.01(3) 3_755 2_665 ? O2 Rb O1 110.14(3) 5_766 2_665 ? O2 Rb O1 63.17(3) 6_566 2_665 ? O1 Rb O1 172.04(4) . 2_665 ? O4 Rb O3 80.97(3) 4_465 2_665 ? O4 Rb O3 74.82(3) 3_755 2_665 ? O2 Rb O3 149.90(3) 5_766 2_665 ? O2 Rb O3 112.95(3) 6_566 2_665 ? O1 Rb O3 129.48(3) . 2_665 ? O1 Rb O3 58.48(2) 2_665 2_665 ? O4 Rb O3 74.82(3) 4_465 . ? O4 Rb O3 80.97(3) 3_755 . ? O2 Rb O3 112.95(3) 5_766 . ? O2 Rb O3 149.90(3) 6_566 . ? O1 Rb O3 58.48(2) . . ? O1 Rb O3 129.48(3) 2_665 . ? O3 Rb O3 71.02(3) 2_665 . ? C1 O1 Rb 135.15(8) . . ? C1 O1 H1 103.3 . . ? Rb O1 H1 106.2 . . ? C1 O2 Rb 117.92(8) . 5_766 ? C4 O3 Rb 149.46(8) . . ? C4 O3 H3 111.1 . . ? Rb O3 H3 93.9 . . ? C4 O4 Rb 145.89(10) . 3_745 ? O2 C1 O1 123.12(12) . . ? O2 C1 C2 118.29(11) . . ? O1 C1 C2 118.58(11) . . ? C1 C2 C2 121.67(11) . 2_765 ? C1 C2 C3 114.90(11) . . ? C2 C2 C3 90.02(7) 2_765 . ? C1 C2 H2 109.6 . . ? C2 C2 H2 109.6 2_765 . ? C3 C2 H2 109.6 . . ? C4 C3 C3 112.21(12) . 2_765 ? C4 C3 C2 114.77(10) . . ? C3 C3 C2 88.98(7) 2_765 . ? C4 C3 H3A 112.9 . . ? C3 C3 H3A 112.9 2_765 . ? C2 C3 H3A 112.9 . . ? O4 C4 O3 123.74(12) . . ? O4 C4 C3 122.77(13) . . ? O3 C4 C3 113.48(11) . . ? 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 1.73 2.4894(19) 153.6 5_766 O3 H3 O2 0.89 1.69 2.5748(14) 171.6 4_465 _database_code_depnum_ccdc_archive 'CCDC 948882' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 Cs O8' _chemical_formula_weight 364.05 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 tetragonal _symmetry_space_group_name_H-M 'P 4/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 9.8276(3) _cell_length_b 9.8276(3) _cell_length_c 10.2207(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 987.13(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 34426 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 30.49 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 3.783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.429 _exptl_absorpt_correction_T_max 0.612 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 35 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and eight \w scans with 2\% steps (578 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34426 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 30.49 _reflns_number_total 1497 _reflns_number_gt 1412 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The carboxylic H atoms are probably disordered over the four possible sites and they have not been found. The C-bound H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0344P)^2^+0.5252P] 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 1497 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.116 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.139 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 0.2500 0.79058(2) 0.02263(8) Uani 1 4 d S . . Cs2 Cs 0.2500 0.2500 0.35535(2) 0.01825(8) Uani 1 4 d S . . O1 O 0.13331(17) 0.06122(16) 0.56824(13) 0.0221(3) Uani 1 1 d . . . O2 O 0.05248(16) -0.11429(15) 0.68343(16) 0.0237(3) Uani 1 1 d . . . O3 O 0.42195(17) -0.05108(18) 0.83394(18) 0.0321(4) Uani 1 1 d . . . O4A O 0.5612(3) -0.2158(3) 0.8868(3) 0.0209(8) Uani 0.500(5) 1 d P . . O4B O 0.5727(3) -0.1591(4) 0.9713(4) 0.0285(9) Uani 0.500(5) 1 d P . . C1 C 0.1195(2) -0.0605(2) 0.58349(18) 0.0189(3) Uani 1 1 d . . . C2 C 0.18306(17) -0.16148(17) 0.4906(2) 0.0185(3) Uani 1 1 d . . . H2 H 0.1636 -0.1357 0.3999 0.022 Uiso 1 1 calc R . . C3 C 0.4502(3) -0.1391(3) 0.9150(3) 0.0467(8) Uani 1 1 d . . . C4 C 0.34590(19) -0.19559(18) 1.0088(2) 0.0197(3) Uani 1 1 d . . . H4 H 0.3747 -0.1793 1.0993 0.024 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 Cs1 0.02363(10) 0.02363(10) 0.02064(13) 0.000 0.000 0.000 Cs2 0.01803(9) 0.01803(9) 0.01868(12) 0.000 0.000 0.000 O1 0.0218(7) 0.0167(6) 0.0278(8) -0.0007(5) 0.0036(5) -0.0005(5) O2 0.0292(7) 0.0201(6) 0.0217(6) 0.0012(5) 0.0028(6) -0.0023(5) O3 0.0280(8) 0.0314(8) 0.0370(9) 0.0157(7) 0.0098(7) 0.0051(6) O4A 0.0181(12) 0.0190(13) 0.0255(16) 0.0022(11) 0.0038(11) 0.0020(9) O4B 0.0179(13) 0.0374(18) 0.030(2) 0.0099(14) -0.0001(12) 0.0011(11) C1 0.0159(8) 0.0184(8) 0.0222(8) 0.0002(6) -0.0022(6) 0.0001(6) C2 0.0166(7) 0.0154(7) 0.0234(8) 0.0005(7) 0.0003(6) -0.0002(5) C3 0.0170(10) 0.0512(16) 0.072(2) 0.0422(14) 0.0060(10) 0.0024(10) C4 0.0196(8) 0.0200(8) 0.0194(8) 0.0035(6) -0.0012(7) -0.0028(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cs1 O4B 3.124(3) 7_667 ? Cs1 O4B 3.124(3) 6_567 ? Cs1 O4B 3.124(3) 5_657 ? Cs1 O4B 3.124(3) 8_557 ? Cs1 O1 3.1497(15) 2 ? Cs1 O1 3.1498(15) 4 ? Cs1 O1 3.1498(15) 3 ? Cs1 O1 3.1498(15) . ? Cs1 O3 3.4362(16) 3 ? Cs1 O3 3.4362(16) 2 ? Cs1 O3 3.4362(16) . ? Cs1 O3 3.4362(16) 4 ? Cs2 O1 3.0808(15) . ? Cs2 O1 3.0808(15) 2 ? Cs2 O1 3.0809(15) 4 ? Cs2 O1 3.0809(15) 3 ? Cs2 O4A 3.111(3) 7_666 ? Cs2 O4A 3.111(3) 6_566 ? Cs2 O4A 3.111(3) 5_656 ? Cs2 O4A 3.111(3) 8_556 ? Cs2 O2 3.2822(16) 5_556 ? Cs2 O2 3.2822(16) 6_666 ? Cs2 O2 3.2822(16) 7_656 ? Cs2 O2 3.2822(16) 8_566 ? O1 C1 1.214(3) . ? O2 C1 1.325(2) . ? O2 Cs2 3.2822(16) 5_556 ? O3 C3 1.230(3) . ? O4A C3 1.358(4) . ? O4A Cs2 3.111(3) 5_656 ? O4A Cs1 3.798(3) 5_657 ? O4B C3 1.349(4) . ? O4B Cs1 3.124(3) 5_657 ? C1 C2 1.508(3) . ? C2 C2 1.554(2) 7_656 ? C2 C2 1.554(2) 8_556 ? C2 H2 0.9800 . ? C3 C4 1.509(3) . ? C4 C4 1.543(3) 7_657 ? C4 C4 1.543(3) 8_557 ? C4 H4 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4B Cs1 O4B 52.64(8) 7_667 6_567 ? O4B Cs1 O4B 52.64(8) 7_667 5_657 ? O4B Cs1 O4B 77.66(13) 6_567 5_657 ? O4B Cs1 O4B 77.66(13) 7_667 8_557 ? O4B Cs1 O4B 52.64(8) 6_567 8_557 ? O4B Cs1 O4B 52.64(8) 5_657 8_557 ? O4B Cs1 O1 97.43(7) 7_667 2 ? O4B Cs1 O1 126.63(7) 6_567 2 ? O4B Cs1 O1 121.83(6) 5_657 2 ? O4B Cs1 O1 174.16(7) 8_557 2 ? O4B Cs1 O1 121.83(6) 7_667 4 ? O4B Cs1 O1 97.43(7) 6_567 4 ? O4B Cs1 O1 174.16(7) 5_657 4 ? O4B Cs1 O1 126.63(7) 8_557 4 ? O1 Cs1 O1 58.63(3) 2 4 ? O4B Cs1 O1 126.63(7) 7_667 3 ? O4B Cs1 O1 174.16(7) 6_567 3 ? O4B Cs1 O1 97.43(7) 5_657 3 ? O4B Cs1 O1 121.83(6) 8_557 3 ? O1 Cs1 O1 58.63(3) 2 3 ? O1 Cs1 O1 87.65(5) 4 3 ? O4B Cs1 O1 174.16(7) 7_667 . ? O4B Cs1 O1 121.83(6) 6_567 . ? O4B Cs1 O1 126.63(7) 5_657 . ? O4B Cs1 O1 97.43(7) 8_557 . ? O1 Cs1 O1 87.65(5) 2 . ? O1 Cs1 O1 58.63(3) 4 . ? O1 Cs1 O1 58.63(3) 3 . ? O4B Cs1 O3 51.60(8) 7_667 3 ? O4B Cs1 O3 103.84(7) 6_567 3 ? O4B Cs1 O3 63.88(7) 5_657 3 ? O4B Cs1 O3 114.85(8) 8_557 3 ? O1 Cs1 O3 59.33(4) 2 3 ? O1 Cs1 O3 114.91(4) 4 3 ? O1 Cs1 O3 76.40(4) 3 3 ? O1 Cs1 O3 134.13(4) . 3 ? O4B Cs1 O3 63.88(7) 7_667 2 ? O4B Cs1 O3 51.60(8) 6_567 2 ? O4B Cs1 O3 114.85(7) 5_657 2 ? O4B Cs1 O3 103.85(7) 8_557 2 ? O1 Cs1 O3 76.40(4) 2 2 ? O1 Cs1 O3 59.33(4) 4 2 ? O1 Cs1 O3 134.13(4) 3 2 ? O1 Cs1 O3 114.91(4) . 2 ? O3 Cs1 O3 89.045(8) 3 2 ? O4B Cs1 O3 103.84(7) 7_667 . ? O4B Cs1 O3 114.85(7) 6_567 . ? O4B Cs1 O3 51.60(8) 5_657 . ? O4B Cs1 O3 63.88(7) 8_557 . ? O1 Cs1 O3 114.91(4) 2 . ? O1 Cs1 O3 134.13(4) 4 . ? O1 Cs1 O3 59.33(4) 3 . ? O1 Cs1 O3 76.40(4) . . ? O3 Cs1 O3 89.047(8) 3 . ? O3 Cs1 O3 165.18(6) 2 . ? O4B Cs1 O3 114.85(8) 7_667 4 ? O4B Cs1 O3 63.88(7) 6_567 4 ? O4B Cs1 O3 103.85(7) 5_657 4 ? O4B Cs1 O3 51.60(8) 8_557 4 ? O1 Cs1 O3 134.13(4) 2 4 ? O1 Cs1 O3 76.40(4) 4 4 ? O1 Cs1 O3 114.91(4) 3 4 ? O1 Cs1 O3 59.33(4) . 4 ? O3 Cs1 O3 165.18(6) 3 4 ? O3 Cs1 O3 89.047(8) 2 4 ? O3 Cs1 O3 89.047(8) . 4 ? O1 Cs2 O1 90.14(6) . 2 ? O1 Cs2 O1 60.08(3) . 4 ? O1 Cs2 O1 60.08(3) 2 4 ? O1 Cs2 O1 60.08(3) . 3 ? O1 Cs2 O1 60.08(3) 2 3 ? O1 Cs2 O1 90.14(6) 4 3 ? O1 Cs2 O4A 163.97(6) . 7_666 ? O1 Cs2 O4A 99.36(6) 2 7_666 ? O1 Cs2 O4A 113.89(6) 4 7_666 ? O1 Cs2 O4A 135.95(6) 3 7_666 ? O1 Cs2 O4A 113.89(6) . 6_566 ? O1 Cs2 O4A 135.95(6) 2 6_566 ? O1 Cs2 O4A 99.35(6) 4 6_566 ? O1 Cs2 O4A 163.97(6) 3 6_566 ? O4A Cs2 O4A 50.74(7) 7_666 6_566 ? O1 Cs2 O4A 135.95(6) . 5_656 ? O1 Cs2 O4A 113.89(6) 2 5_656 ? O1 Cs2 O4A 163.97(6) 4 5_656 ? O1 Cs2 O4A 99.35(6) 3 5_656 ? O4A Cs2 O4A 50.74(7) 7_666 5_656 ? O4A Cs2 O4A 74.60(11) 6_566 5_656 ? O1 Cs2 O4A 99.35(6) . 8_556 ? O1 Cs2 O4A 163.97(6) 2 8_556 ? O1 Cs2 O4A 135.94(6) 4 8_556 ? O1 Cs2 O4A 113.89(6) 3 8_556 ? O4A Cs2 O4A 74.60(11) 7_666 8_556 ? O4A Cs2 O4A 50.74(7) 6_566 8_556 ? O4A Cs2 O4A 50.74(7) 5_656 8_556 ? O1 Cs2 O2 60.23(4) . 5_556 ? O1 Cs2 O2 131.85(4) 2 5_556 ? O1 Cs2 O2 72.01(4) 4 5_556 ? O1 Cs2 O2 118.65(4) 3 5_556 ? O4A Cs2 O2 104.13(6) 7_666 5_556 ? O4A Cs2 O2 53.69(6) 6_566 5_556 ? O4A Cs2 O2 113.58(6) 5_656 5_556 ? O4A Cs2 O2 64.13(6) 8_556 5_556 ? O1 Cs2 O2 131.85(4) . 6_666 ? O1 Cs2 O2 60.23(4) 2 6_666 ? O1 Cs2 O2 118.65(4) 4 6_666 ? O1 Cs2 O2 72.01(4) 3 6_666 ? O4A Cs2 O2 64.14(6) 7_666 6_666 ? O4A Cs2 O2 113.58(6) 6_566 6_666 ? O4A Cs2 O2 53.69(6) 5_656 6_666 ? O4A Cs2 O2 104.13(6) 8_556 6_666 ? O2 Cs2 O2 166.13(6) 5_556 6_666 ? O1 Cs2 O2 72.01(4) . 7_656 ? O1 Cs2 O2 118.65(4) 2 7_656 ? O1 Cs2 O2 131.85(4) 4 7_656 ? O1 Cs2 O2 60.23(4) 3 7_656 ? O4A Cs2 O2 113.58(6) 7_666 7_656 ? O4A Cs2 O2 104.13(6) 6_566 7_656 ? O4A Cs2 O2 64.13(6) 5_656 7_656 ? O4A Cs2 O2 53.69(6) 8_556 7_656 ? O2 Cs2 O2 89.164(7) 5_556 7_656 ? O2 Cs2 O2 89.164(7) 6_666 7_656 ? O1 Cs2 O2 118.65(4) . 8_566 ? O1 Cs2 O2 72.01(4) 2 8_566 ? O1 Cs2 O2 60.23(4) 4 8_566 ? O1 Cs2 O2 131.85(4) 3 8_566 ? O4A Cs2 O2 53.69(6) 7_666 8_566 ? O4A Cs2 O2 64.13(6) 6_566 8_566 ? O4A Cs2 O2 104.13(6) 5_656 8_566 ? O4A Cs2 O2 113.58(6) 8_556 8_566 ? O2 Cs2 O2 89.166(7) 5_556 8_566 ? O2 Cs2 O2 89.164(7) 6_666 8_566 ? O2 Cs2 O2 166.13(6) 7_656 8_566 ? C1 O1 Cs2 136.52(13) . . ? C1 O1 Cs1 121.90(13) . . ? Cs2 O1 Cs1 91.11(4) . . ? C1 O2 Cs2 121.27(12) . 5_556 ? C3 O3 Cs1 143.5(2) . . ? C3 O4A Cs2 135.1(2) . 5_656 ? C3 O4A Cs1 104.9(2) . 5_657 ? Cs2 O4A Cs1 112.94(8) 5_656 5_657 ? C3 O4B Cs1 150.7(2) . 5_657 ? O1 C1 O2 123.18(19) . . ? O1 C1 C2 121.41(18) . . ? O2 C1 C2 115.38(17) . . ? C1 C2 C2 114.8(2) . 7_656 ? C1 C2 C2 120.8(2) . 8_556 ? C2 C2 C2 89.13(4) 7_656 8_556 ? C1 C2 H2 110.1 . . ? C2 C2 H2 110.1 7_656 . ? C2 C2 H2 110.1 8_556 . ? O3 C3 O4B 126.3(3) . . ? O3 C3 O4A 115.4(3) . . ? O3 C3 C4 122.3(2) . . ? O4B C3 C4 106.3(2) . . ? O4A C3 C4 118.5(2) . . ? C3 C4 C4 117.2(2) . 7_657 ? C3 C4 C4 118.6(2) . 8_557 ? C4 C4 C4 89.22(4) 7_657 8_557 ? C3 C4 H4 110.1 . . ? C4 C4 H4 110.1 7_657 . ? C4 C4 H4 110.1 8_557 . ? _database_code_depnum_ccdc_archive 'CCDC 948883'