# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_exp_598 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Dilithium D,L-tartrate dihydrate' ; _chemical_name_common 'Lithium tartrate' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C8 H16 Li4 O16' _chemical_formula_sum 'C8 H16 Li4 O16' _chemical_formula_weight 395.97 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1037(4) _cell_length_b 7.3350(7) _cell_length_c 9.0294(8) _cell_angle_alpha 103.450(8) _cell_angle_beta 90.701(7) _cell_angle_gamma 100.790(7) _cell_volume 385.55(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120 _cell_measurement_reflns_used 5451 _cell_measurement_theta_max 29.1609 _cell_measurement_theta_min 2.9056 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_detector_area_resol_mean 16.1183 _diffrn_reflns_number 5451 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 29.23 _reflns_number_total 1842 _reflns_number_gt 1394 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution Superflip _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and Mercury' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1842 _refine_ls_number_parameters 145 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.973 _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 OW2 O 0.15936(17) 1.26454(14) 0.03726(12) 0.0136(2) Uani 1 1 d D . . H6A H 0.062(2) 1.202(2) -0.0334(16) 0.020 Uiso 1 1 d D . . H6B H 0.263(2) 1.325(2) -0.0047(18) 0.020 Uiso 1 1 d D . . O3 O 0.11168(16) 0.93370(14) 0.22100(11) 0.0117(2) Uani 1 1 d . . . H3A H 0.044(3) 1.003(2) 0.291(2) 0.018 Uiso 1 1 d . . . OW1 O 0.51532(17) 0.25860(14) 0.30828(12) 0.0132(2) Uani 1 1 d D . . H5A H 0.621(2) 0.215(2) 0.3424(18) 0.020 Uiso 1 1 d D . . H5B H 0.421(2) 0.272(2) 0.3785(15) 0.020 Uiso 1 1 d D . . O4B O 0.50177(16) 0.62774(14) 0.15991(11) 0.0138(2) Uani 1 1 d . . . O2 O -0.03596(17) 0.53048(14) 0.22005(12) 0.0139(2) Uani 1 1 d . . . H2A H 0.026(3) 0.443(2) 0.171(2) 0.021 Uiso 1 1 d . . . O1B O 0.10824(17) 0.84881(14) 0.58545(11) 0.0144(2) Uani 1 1 d . . . O4A O 0.40667(17) 0.83636(14) 0.03844(11) 0.0147(2) Uani 1 1 d . . . O1A O -0.21932(16) 0.68195(14) 0.46784(11) 0.0147(2) Uani 1 1 d . . . C2 C 0.1170(2) 0.6585(2) 0.33500(16) 0.0113(3) Uani 1 1 d . . . H2 H 0.2227 0.5874 0.3667 0.014 Uiso 1 1 calc R . . C3 C 0.2495(2) 0.82444(19) 0.27735(16) 0.0105(3) Uani 1 1 d . . . H3 H 0.3469 0.9098 0.3623 0.013 Uiso 1 1 calc R . . C4 C 0.3969(2) 0.75537(19) 0.14758(16) 0.0113(3) Uani 1 1 d . . . C1 C -0.0108(2) 0.7351(2) 0.47389(16) 0.0117(3) Uani 1 1 d . . . Li1 Li 0.3536(4) 1.1041(4) 0.1045(3) 0.0161(5) Uani 1 1 d . . . Li2 Li 0.6584(4) 0.5081(4) 0.2734(3) 0.0161(5) 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 OW2 0.0114(6) 0.0150(6) 0.0137(6) 0.0029(4) 0.0011(4) 0.0014(4) O3 0.0133(5) 0.0119(5) 0.0117(5) 0.0029(4) 0.0029(4) 0.0064(4) OW1 0.0114(5) 0.0156(5) 0.0133(6) 0.0041(4) 0.0018(4) 0.0034(4) O4B 0.0141(5) 0.0133(5) 0.0162(6) 0.0052(4) 0.0021(4) 0.0060(4) O2 0.0130(5) 0.0122(5) 0.0141(6) -0.0013(4) 0.0025(4) 0.0021(4) O1B 0.0147(5) 0.0163(5) 0.0120(5) 0.0010(4) 0.0012(4) 0.0050(4) O4A 0.0164(6) 0.0165(5) 0.0143(5) 0.0073(4) 0.0057(4) 0.0060(4) O1A 0.0119(5) 0.0174(5) 0.0146(5) 0.0035(4) 0.0039(4) 0.0027(4) C2 0.0109(7) 0.0119(7) 0.0113(7) 0.0026(6) 0.0011(5) 0.0026(6) C3 0.0099(7) 0.0118(7) 0.0106(7) 0.0031(6) 0.0002(5) 0.0035(6) C4 0.0075(7) 0.0116(7) 0.0128(7) 0.0013(6) 0.0012(5) -0.0012(6) C1 0.0151(8) 0.0106(7) 0.0125(7) 0.0062(6) 0.0034(6) 0.0054(6) Li1 0.0170(13) 0.0158(13) 0.0149(13) 0.0026(10) 0.0012(10) 0.0028(10) Li2 0.0142(13) 0.0169(13) 0.0177(13) 0.0059(10) -0.0003(10) 0.0023(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 OW2 Li1 1.999(3) . ? O3 C3 1.4285(16) . ? O3 Li1 2.193(3) . ? OW1 Li2 1.971(3) . ? OW1 Li1 2.052(3) 1_545 ? O4B C4 1.2528(17) . ? O4B Li2 1.856(3) . ? O2 C2 1.4230(17) . ? O2 Li2 1.919(3) 1_455 ? O1B C1 1.2662(17) . ? O4A C4 1.2602(17) . ? O4A Li1 2.004(3) . ? O4A Li1 2.017(3) 2_675 ? O1A C1 1.2557(17) . ? O1A Li2 1.958(3) 1_455 ? C2 C3 1.5308(19) . ? C2 C1 1.535(2) . ? C3 C4 1.536(2) . ? C4 Li1 2.735(3) . ? C1 Li2 2.716(3) 1_455 ? Li1 O4A 2.017(3) 2_675 ? Li1 OW1 2.052(3) 1_565 ? Li1 Li1 2.975(5) 2_675 ? Li1 Li2 3.214(4) 1_565 ? Li2 O2 1.919(3) 1_655 ? Li2 O1A 1.958(3) 1_655 ? Li2 C1 2.716(3) 1_655 ? Li2 Li1 3.214(4) 1_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O3 Li1 101.27(10) . . ? Li2 OW1 Li1 106.03(11) . 1_545 ? C4 O4B Li2 152.23(13) . . ? C2 O2 Li2 113.44(11) . 1_455 ? C4 O4A Li1 111.77(11) . . ? C4 O4A Li1 133.46(12) . 2_675 ? Li1 O4A Li1 95.46(11) . 2_675 ? C1 O1A Li2 113.52(12) . 1_455 ? O2 C2 C3 112.06(11) . . ? O2 C2 C1 109.40(11) . . ? C3 C2 C1 110.21(11) . . ? O3 C3 C2 113.47(11) . . ? O3 C3 C4 106.67(11) . . ? C2 C3 C4 111.99(11) . . ? O4B C4 O4A 125.23(13) . . ? O4B C4 C3 118.02(12) . . ? O4A C4 C3 116.73(12) . . ? O4B C4 Li1 155.10(11) . . ? O4A C4 Li1 42.89(8) . . ? C3 C4 Li1 77.87(9) . . ? O1A C1 O1B 126.03(13) . . ? O1A C1 C2 118.57(13) . . ? O1B C1 C2 115.40(12) . . ? O1A C1 Li2 41.39(9) . 1_455 ? O1B C1 Li2 167.40(12) . 1_455 ? C2 C1 Li2 77.18(10) . 1_455 ? OW2 Li1 O4A 137.63(14) . . ? OW2 Li1 O4A 93.63(11) . 2_675 ? O4A Li1 O4A 84.54(11) . 2_675 ? OW2 Li1 OW1 107.45(12) . 1_565 ? O4A Li1 OW1 114.61(13) . 1_565 ? O4A Li1 OW1 99.61(11) 2_675 1_565 ? OW2 Li1 O3 100.13(11) . . ? O4A Li1 O3 74.50(9) . . ? O4A Li1 O3 158.89(14) 2_675 . ? OW1 Li1 O3 91.49(10) 1_565 . ? OW2 Li1 C4 148.19(12) . . ? O4A Li1 C4 25.34(5) . . ? O4A Li1 C4 104.31(11) 2_675 . ? OW1 Li1 C4 95.37(10) 1_565 . ? O3 Li1 C4 56.45(7) . . ? OW2 Li1 Li1 122.72(15) . 2_675 ? O4A Li1 Li1 42.43(7) . 2_675 ? O4A Li1 Li1 42.10(7) 2_675 2_675 ? OW1 Li1 Li1 113.18(14) 1_565 2_675 ? O3 Li1 Li1 116.90(14) . 2_675 ? C4 Li1 Li1 63.82(9) . 2_675 ? OW2 Li1 Li2 84.28(10) . 1_565 ? O4A Li1 Li2 134.41(12) . 1_565 ? O4A Li1 Li2 73.69(9) 2_675 1_565 ? OW1 Li1 Li2 36.12(7) 1_565 1_565 ? O3 Li1 Li2 123.31(11) . 1_565 ? C4 Li1 Li2 125.68(10) . 1_565 ? Li1 Li1 Li2 106.32(12) 2_675 1_565 ? O4B Li2 O2 110.84(13) . 1_655 ? O4B Li2 O1A 111.17(13) . 1_655 ? O2 Li2 O1A 84.99(10) 1_655 1_655 ? O4B Li2 OW1 119.23(13) . . ? O2 Li2 OW1 115.76(13) 1_655 . ? O1A Li2 OW1 109.66(13) 1_655 . ? O4B Li2 C1 116.95(12) . 1_655 ? O2 Li2 C1 59.92(8) 1_655 1_655 ? O1A Li2 C1 25.09(5) 1_655 1_655 ? OW1 Li2 C1 119.25(12) . 1_655 ? O4B Li2 Li1 89.24(10) . 1_545 ? O2 Li2 Li1 112.70(12) 1_655 1_545 ? O1A Li2 Li1 146.85(12) 1_655 1_545 ? OW1 Li2 Li1 37.85(7) . 1_545 ? C1 Li2 Li1 153.81(11) 1_655 1_545 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Li2 O2 C2 C3 -119.86(13) 1_455 . . . ? Li2 O2 C2 C1 2.68(15) 1_455 . . . ? Li1 O3 C3 C2 -167.29(12) . . . . ? Li1 O3 C3 C4 -43.49(13) . . . . ? O2 C2 C3 O3 57.71(15) . . . . ? C1 C2 C3 O3 -64.37(15) . . . . ? O2 C2 C3 C4 -63.13(15) . . . . ? C1 C2 C3 C4 174.79(11) . . . . ? Li2 O4B C4 O4A 142.9(2) . . . . ? Li2 O4B C4 C3 -35.2(3) . . . . ? Li2 O4B C4 Li1 90.4(4) . . . . ? Li1 O4A C4 O4B -150.61(14) . . . . ? Li1 O4A C4 O4B -29.3(2) 2_675 . . . ? Li1 O4A C4 C3 27.43(16) . . . . ? Li1 O4A C4 C3 148.75(14) 2_675 . . . ? Li1 O4A C4 Li1 121.32(17) 2_675 . . . ? O3 C3 C4 O4B -166.90(11) . . . . ? C2 C3 C4 O4B -42.20(17) . . . . ? O3 C3 C4 O4A 14.91(16) . . . . ? C2 C3 C4 O4A 139.62(13) . . . . ? O3 C3 C4 Li1 33.61(10) . . . . ? C2 C3 C4 Li1 158.32(12) . . . . ? Li2 O1A C1 O1B 179.02(14) 1_455 . . . ? Li2 O1A C1 C2 -0.73(17) 1_455 . . . ? O2 C2 C1 O1A -1.29(17) . . . . ? C3 C2 C1 O1A 122.36(13) . . . . ? O2 C2 C1 O1B 178.94(11) . . . . ? C3 C2 C1 O1B -57.42(16) . . . . ? O2 C2 C1 Li2 -1.78(10) . . . 1_455 ? C3 C2 C1 Li2 121.86(12) . . . 1_455 ? C4 O4A Li1 OW2 -129.13(19) . . . . ? Li1 O4A Li1 OW2 89.4(2) 2_675 . . . ? C4 O4A Li1 O4A 141.48(12) . . . 2_675 ? Li1 O4A Li1 O4A 0.0 2_675 . . 2_675 ? C4 O4A Li1 OW1 43.39(17) . . . 1_565 ? Li1 O4A Li1 OW1 -98.09(14) 2_675 . . 1_565 ? C4 O4A Li1 O3 -41.03(12) . . . . ? Li1 O4A Li1 O3 177.50(12) 2_675 . . . ? Li1 O4A Li1 C4 -141.48(12) 2_675 . . . ? C4 O4A Li1 Li1 141.48(12) . . . 2_675 ? C4 O4A Li1 Li2 80.72(18) . . . 1_565 ? Li1 O4A Li1 Li2 -60.75(14) 2_675 . . 1_565 ? C3 O3 Li1 OW2 -177.09(10) . . . . ? C3 O3 Li1 O4A 46.08(10) . . . . ? C3 O3 Li1 O4A 53.0(4) . . . 2_675 ? C3 O3 Li1 OW1 -69.07(11) . . . 1_565 ? C3 O3 Li1 C4 26.38(8) . . . . ? C3 O3 Li1 Li1 47.97(17) . . . 2_675 ? C3 O3 Li1 Li2 -87.30(14) . . . 1_565 ? O4B C4 Li1 OW2 154.7(2) . . . . ? O4A C4 Li1 OW2 82.6(2) . . . . ? C3 C4 Li1 OW2 -72.5(2) . . . . ? O4B C4 Li1 O4A 72.2(3) . . . . ? C3 C4 Li1 O4A -155.12(15) . . . . ? O4B C4 Li1 O4A 32.4(3) . . . 2_675 ? O4A C4 Li1 O4A -39.78(13) . . . 2_675 ? C3 C4 Li1 O4A 165.10(12) . . . 2_675 ? O4B C4 Li1 OW1 -69.0(3) . . . 1_565 ? O4A C4 Li1 OW1 -141.15(16) . . . 1_565 ? C3 C4 Li1 OW1 63.73(10) . . . 1_565 ? O4B C4 Li1 O3 -157.2(3) . . . . ? O4A C4 Li1 O3 130.63(14) . . . . ? C3 C4 Li1 O3 -24.49(8) . . . . ? O4B C4 Li1 Li1 44.3(3) . . . 2_675 ? O4A C4 Li1 Li1 -27.92(9) . . . 2_675 ? C3 C4 Li1 Li1 176.96(12) . . . 2_675 ? O4B C4 Li1 Li2 -47.6(3) . . . 1_565 ? O4A C4 Li1 Li2 -119.79(17) . . . 1_565 ? C3 C4 Li1 Li2 85.09(13) . . . 1_565 ? C4 O4B Li2 O2 -114.2(3) . . . 1_655 ? C4 O4B Li2 O1A -21.5(3) . . . 1_655 ? C4 O4B Li2 OW1 107.6(3) . . . . ? C4 O4B Li2 C1 -48.3(3) . . . 1_655 ? C4 O4B Li2 Li1 131.7(2) . . . 1_545 ? Li1 OW1 Li2 O4B 41.85(18) 1_545 . . . ? Li1 OW1 Li2 O2 -94.42(15) 1_545 . . 1_655 ? Li1 OW1 Li2 O1A 171.59(12) 1_545 . . 1_655 ? Li1 OW1 Li2 C1 -162.85(12) 1_545 . . 1_655 ? 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 H3A O1B 0.874(18) 1.769(18) 2.6388(14) 173.3(17) 2_576 OW1 H5A O1B 0.858(9) 1.942(10) 2.7922(15) 170.8(16) 2_666 OW1 H5B O1A 0.861(9) 1.881(9) 2.7414(14) 176.3(16) 2_566 OW2 H6A O3 0.849(9) 1.941(10) 2.7779(15) 168.8(17) 2_575 OW2 H6B O4B 0.848(9) 2.057(11) 2.8643(14) 158.9(16) 2_675 OW2 H6B O4A 0.848(9) 2.505(16) 2.9282(15) 111.8(13) 2_675 OW2 H6B O4B 0.848(9) 2.543(16) 3.0295(14) 117.5(14) 1_565 O2 H2A OW2 0.845(18) 1.876(19) 2.7151(15) 172.0(17) 1_545 _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.361 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 944909' ####################################################################### # # 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_exp_617 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Lithium meso-tartrate hemihydrate ; _chemical_name_common 'Lithium tartrate' _chemical_melting_point 'not measured' _chemical_formula_moiety 'C4 H4 Li2 O6 0.5(H2 O)' _chemical_absolute_configuration syn _chemical_formula_sum 'C4 H5 Li2 O6.50' _chemical_formula_weight 170.96 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 'C 2 2 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 5.5637(5) _cell_length_b 9.3007(8) _cell_length_c 24.992(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1293.24(19) _cell_formula_units_Z 8 _cell_measurement_temperature 120.0 _cell_measurement_reflns_used 970 _cell_measurement_theta_min 3.2540 _cell_measurement_theta_max 29.0310 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2222 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 29.10 _reflns_number_total 1462 _reflns_number_gt 1282 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution Superflip _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0307P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary edma _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometry and difmap' _refine_ls_hydrogen_treatment mixed _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 1.9(14) _refine_ls_number_reflns 1462 _refine_ls_number_parameters 123 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O5 O 0.8172(3) 0.03715(15) 0.19596(6) 0.0150(3) Uani 1 1 d . . . O10 O 1.0000 0.3675(2) 0.2500 0.0138(5) Uani 1 2 d SD . . H10 H 1.101(3) 0.4207(18) 0.2343(9) 0.021 Uiso 1 1 d D . . O6 O 1.0383(3) -0.15674(15) 0.17719(6) 0.0147(3) Uani 1 1 d . . . O4 O 1.1206(3) 0.21640(15) 0.15217(7) 0.0169(4) Uani 1 1 d . . . H4 H 1.246(5) 0.260(3) 0.1608(11) 0.025 Uiso 1 1 d . . . O3 O 1.3837(3) 0.11836(15) 0.06346(7) 0.0171(4) Uani 1 1 d . . . H1 H 1.536(5) 0.072(3) 0.0653(11) 0.026 Uiso 1 1 d . . . C1 C 0.9651(4) 0.0665(2) 0.05923(9) 0.0135(5) Uani 1 1 d . . . C4 C 0.9976(4) -0.0236(2) 0.17568(9) 0.0141(5) Uani 1 1 d . . . C3 C 1.1816(4) 0.0688(2) 0.14671(9) 0.0128(4) Uani 1 1 d . . . H3 H 1.3387 0.0533 0.1635 0.015 Uiso 1 1 calc R . . C2 C 1.2030(4) 0.0317(2) 0.08685(9) 0.0134(5) Uani 1 1 d . . . H2 H 1.2422 -0.0703 0.0823 0.016 Uiso 1 1 calc R . . Li2 Li 0.8328(7) 0.2474(4) 0.19513(17) 0.0176(8) Uani 1 1 d . . . Li1 Li 1.2575(7) 0.2912(4) 0.03225(16) 0.0163(8) Uani 1 1 d . . . O1 O 0.7949(3) -0.02027(15) 0.06721(6) 0.0146(3) Uani 1 1 d . . . O2 O 0.9532(3) 0.17993(15) 0.03174(6) 0.0156(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 O5 0.0117(7) 0.0144(8) 0.0190(8) 0.0010(7) 0.0035(7) 0.0002(6) O10 0.0110(12) 0.0133(10) 0.0172(12) 0.000 0.0023(10) 0.000 O6 0.0137(8) 0.0108(7) 0.0195(8) 0.0016(7) -0.0002(7) 0.0005(6) O4 0.0170(9) 0.0113(8) 0.0222(9) -0.0025(7) 0.0026(7) -0.0043(7) O3 0.0107(8) 0.0168(8) 0.0238(9) 0.0051(7) 0.0051(7) 0.0003(6) C1 0.0132(11) 0.0147(10) 0.0127(11) -0.0014(9) 0.0013(9) 0.0040(9) C4 0.0136(11) 0.0172(11) 0.0114(11) -0.0008(9) -0.0034(9) 0.0004(9) C3 0.0134(11) 0.0119(10) 0.0132(11) 0.0015(9) -0.0005(9) 0.0013(8) C2 0.0105(11) 0.0117(10) 0.0179(11) 0.0003(9) 0.0026(9) 0.0022(9) Li2 0.0150(19) 0.0197(18) 0.018(2) 0.0017(17) -0.0037(17) -0.0012(17) Li1 0.019(2) 0.0136(18) 0.016(2) 0.0014(16) 0.0027(16) 0.0015(15) O1 0.0120(8) 0.0135(7) 0.0183(8) 0.0013(7) 0.0003(7) -0.0025(6) O2 0.0166(8) 0.0136(8) 0.0167(8) 0.0028(7) -0.0034(7) -0.0007(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 C4 1.258(3) . ? O5 Li2 1.957(4) . ? O10 Li2 1.998(4) . ? O10 Li2 1.998(4) 4_755 ? O6 C4 1.260(2) . ? O6 Li2 1.919(4) 5_545 ? O4 C3 1.421(2) . ? O4 Li2 1.949(4) . ? O3 C2 1.415(3) . ? O3 Li1 1.920(4) . ? C1 O1 1.260(3) . ? C1 O2 1.261(3) . ? C1 C2 1.528(3) . ? C1 Li1 2.733(4) . ? C4 C3 1.520(3) . ? C4 Li2 2.725(4) . ? C3 C2 1.540(3) . ? C2 Li1 2.789(4) . ? Li2 O6 1.919(4) 5_455 ? Li2 Li2 3.314(8) 4_755 ? Li1 O2 1.953(4) 7 ? Li1 O1 1.970(4) 5 ? Li1 O2 1.984(4) . ? Li1 Li1 3.305(4) 7_455 ? Li1 Li1 3.305(4) 7 ? O1 Li1 1.970(4) 5_445 ? O2 Li1 1.953(4) 7_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O5 Li2 114.12(18) . . ? Li2 O10 Li2 112.0(2) . 4_755 ? C4 O6 Li2 128.15(18) . 5_545 ? C3 O4 Li2 113.08(17) . . ? C2 O3 Li1 112.66(17) . . ? O1 C1 O2 125.6(2) . . ? O1 C1 C2 116.35(19) . . ? O2 C1 C2 117.98(19) . . ? O1 C1 Li1 167.46(18) . . ? O2 C1 Li1 42.00(13) . . ? C2 C1 Li1 75.99(14) . . ? O5 C4 O6 125.0(2) . . ? O5 C4 C3 118.39(18) . . ? O6 C4 C3 116.65(19) . . ? O5 C4 Li2 40.96(12) . . ? O6 C4 Li2 164.67(19) . . ? C3 C4 Li2 77.81(14) . . ? O4 C3 C4 109.84(18) . . ? O4 C3 C2 109.17(17) . . ? C4 C3 C2 112.83(18) . . ? O3 C2 C1 107.94(18) . . ? O3 C2 C3 109.18(18) . . ? C1 C2 C3 108.94(18) . . ? O3 C2 Li1 39.43(12) . . ? C1 C2 Li1 71.92(14) . . ? C3 C2 Li1 106.84(15) . . ? O6 Li2 O4 129.9(2) 5_455 . ? O6 Li2 O5 115.4(2) 5_455 . ? O4 Li2 O5 83.95(17) . . ? O6 Li2 O10 107.3(2) 5_455 . ? O4 Li2 O10 94.49(17) . . ? O5 Li2 O10 124.9(2) . . ? O6 Li2 C4 132.48(19) 5_455 . ? O4 Li2 C4 59.26(12) . . ? O5 Li2 C4 24.92(9) . . ? O10 Li2 C4 118.87(18) . . ? O6 Li2 Li2 132.3(2) 5_455 4_755 ? O4 Li2 Li2 89.70(18) . 4_755 ? O5 Li2 Li2 90.92(13) . 4_755 ? O10 Li2 Li2 33.99(12) . 4_755 ? C4 Li2 Li2 87.64(10) . 4_755 ? O3 Li1 O2 104.11(18) . 7 ? O3 Li1 O1 121.8(2) . 5 ? O2 Li1 O1 100.47(18) 7 5 ? O3 Li1 O2 82.99(15) . . ? O2 Li1 O2 122.8(2) 7 . ? O1 Li1 O2 123.9(2) 5 . ? O3 Li1 C1 58.47(11) . . ? O2 Li1 C1 129.72(19) 7 . ? O1 Li1 C1 129.36(19) 5 . ? O2 Li1 C1 25.16(8) . . ? O3 Li1 C2 27.91(8) . . ? O2 Li1 C2 125.45(17) 7 . ? O1 Li1 C2 124.38(18) 5 . ? O2 Li1 C2 57.26(11) . . ? C1 Li1 C2 32.10(8) . . ? O3 Li1 Li1 108.2(2) . 7_455 ? O2 Li1 Li1 95.8(2) 7 7_455 ? O1 Li1 Li1 120.78(17) 5 7_455 ? O2 Li1 Li1 32.63(6) . 7_455 ? C1 Li1 Li1 56.09(11) . 7_455 ? C2 Li1 Li1 86.94(15) . 7_455 ? O3 Li1 Li1 72.31(14) . 7 ? O2 Li1 Li1 33.21(11) 7 7 ? O1 Li1 Li1 109.49(16) 5 7 ? O2 Li1 Li1 126.4(2) . 7 ? C1 Li1 Li1 116.36(18) . 7 ? C2 Li1 Li1 97.43(16) . 7 ? Li1 Li1 Li1 114.6(2) 7_455 7 ? C1 O1 Li1 125.40(19) . 5_445 ? C1 O2 Li1 126.20(18) . 7_455 ? C1 O2 Li1 112.83(17) . . ? Li1 O2 Li1 114.16(11) 7_455 . ? 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 O10 H10 O5 0.847(9) 1.880(9) 2.7256(19) 177(3) 5 O3 H1 O1 0.95(3) 1.68(3) 2.628(2) 176(2) 1_655 O3 H1 O2 0.95(3) 2.66(3) 3.316(2) 126.3(18) 1_655 O4 H4 O6 0.83(3) 1.85(3) 2.680(2) 175(3) 5 _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.216 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 944908'