# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email fabrizia.grepioni@unibo.it _publ_contact_author_name 'Grepioni, Fabrizia' _publ_author_name 'Fabrizia Grepioni' data_PIR.LiBr.2H2O _database_code_depnum_ccdc_archive 'CCDC 884810' #TrackingRef '- PIR_LiBr_2H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'piracetam LiBr 2H2O' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H14 Br Li N2 O4' _chemical_formula_weight 265.04 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7723(5) _cell_length_b 9.8812(7) _cell_length_c 14.8483(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.404(6) _cell_angle_gamma 90.00 _cell_volume 1140.32(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1823 _cell_measurement_theta_min 2.7381 _cell_measurement_theta_max 29.1940 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 3.595 _exptl_absorpt_correction_T_min 0.75967 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6234 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 26.98 _reflns_number_total 2461 _reflns_number_gt 1868 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0332P)^2^+0.7563P] 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 2461 _refine_ls_number_parameters 141 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.088 _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 Li1 Li -0.5605(8) 0.6592(6) 0.7232(4) 0.0393(14) Uani 1 1 d . . . Br1 Br 0.06739(5) 0.13894(4) 0.34945(3) 0.05110(16) Uani 1 1 d . . . C1 C -0.6422(4) 0.1523(3) 0.5989(2) 0.0360(8) Uani 1 1 d . . . O1 O -0.5694(3) 0.1150(2) 0.66867(16) 0.0447(6) Uani 1 1 d . . . N1 N -0.7709(5) 0.0849(4) 0.5624(3) 0.0546(10) Uani 1 1 d . . . H1A H -0.811(6) 0.106(4) 0.508(3) 0.066 Uiso 1 1 d . . . H1B H -0.820(5) 0.018(4) 0.596(3) 0.066 Uiso 1 1 d . . . C2 C -0.5947(5) 0.2815(4) 0.5507(2) 0.0453(10) Uani 1 1 d . . . H2A H -0.6064 0.2672 0.4863 0.054 Uiso 1 1 calc R . . H2B H -0.6753 0.3518 0.5677 0.054 Uiso 1 1 calc R . . N2 N -0.4243(4) 0.3275(3) 0.56971(19) 0.0363(7) Uani 1 1 d . . . C3 C -0.2732(5) 0.2578(4) 0.5372(3) 0.0564(11) Uani 1 1 d . . . H3A H -0.2800 0.2435 0.4726 0.068 Uiso 1 1 calc R . . H3B H -0.2585 0.1712 0.5669 0.068 Uiso 1 1 calc R . . C4 C -0.1280(7) 0.3540(5) 0.5613(4) 0.0918(18) Uani 1 1 d . . . H4A H -0.0363 0.3060 0.5924 0.110 Uiso 1 1 calc R . . H4B H -0.0812 0.3950 0.5074 0.110 Uiso 1 1 calc R . . C5 C -0.2034(5) 0.4600(4) 0.6212(3) 0.0586(12) Uani 1 1 d . . . H5A H -0.1649 0.4474 0.6829 0.070 Uiso 1 1 calc R . . H5B H -0.1700 0.5497 0.6014 0.070 Uiso 1 1 calc R . . C6 C -0.3921(5) 0.4425(3) 0.6139(2) 0.0365(8) Uani 1 1 d . . . O2 O -0.5033(4) 0.5184(3) 0.64182(17) 0.0524(7) Uani 1 1 d . . . O2W O -0.4894(3) 0.8312(2) 0.67647(17) 0.0470(6) Uani 1 1 d . . . H200 H -0.3541 0.8248 0.6628 0.056 Uiso 1 1 d . . . H201 H -0.5553 0.9155 0.6703 0.056 Uiso 1 1 d . . . O1W O -0.8014(4) 0.6442(4) 0.7427(3) 0.0725(9) Uani 1 1 d D . . H100 H -0.883(5) 0.695(4) 0.719(3) 0.082(16) Uiso 1 1 d D . . H101 H -0.848(6) 0.569(3) 0.763(3) 0.11(2) Uiso 1 1 d 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 0.047(3) 0.031(3) 0.039(3) 0.002(3) -0.006(3) 0.004(3) Br1 0.0446(2) 0.0456(2) 0.0630(3) 0.0023(2) -0.01069(18) -0.00022(19) C1 0.0413(19) 0.0284(17) 0.0384(19) -0.0060(15) -0.0041(15) -0.0019(16) O1 0.0552(16) 0.0390(15) 0.0396(14) 0.0048(11) -0.0139(12) -0.0063(12) N1 0.060(2) 0.047(2) 0.057(2) 0.0116(17) -0.0230(18) -0.0195(18) C2 0.057(2) 0.0312(19) 0.048(2) 0.0031(16) -0.0188(19) -0.0041(18) N2 0.0448(17) 0.0269(15) 0.0373(16) -0.0043(12) 0.0030(13) -0.0026(13) C3 0.065(3) 0.047(2) 0.057(3) -0.005(2) 0.018(2) 0.005(2) C4 0.057(3) 0.076(4) 0.143(5) -0.008(4) 0.036(3) -0.016(3) C5 0.060(3) 0.041(2) 0.074(3) 0.008(2) -0.011(2) -0.019(2) C6 0.054(2) 0.0264(18) 0.0286(18) 0.0051(15) -0.0021(16) -0.0045(17) O2 0.0726(19) 0.0336(14) 0.0511(16) -0.0118(12) 0.0001(14) 0.0058(14) O2W 0.0503(16) 0.0317(13) 0.0591(16) 0.0001(12) -0.0001(13) 0.0006(12) O1W 0.0415(17) 0.068(2) 0.108(3) 0.033(2) -0.0024(17) 0.0071(18) _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 Li1 O2 1.898(6) . ? Li1 O1W 1.903(7) . ? Li1 O2W 1.919(6) . ? Li1 O1 1.940(6) 2_456 ? C1 O1 1.233(4) . ? C1 N1 1.315(5) . ? C1 C2 1.511(5) . ? O1 Li1 1.940(6) 2_446 ? N1 H1A 0.88(4) . ? N1 H1B 0.91(4) . ? C2 N2 1.426(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C6 1.335(4) . ? N2 C3 1.447(5) . ? C3 C4 1.516(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.496(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.480(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.219(4) . ? O2W H200 1.0744 . ? O2W H201 0.9817 . ? O1W H100 0.882(19) . ? O1W H101 0.88(2) . ? 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 Li1 O1W 105.9(3) . . ? O2 Li1 O2W 110.5(3) . . ? O1W Li1 O2W 114.2(3) . . ? O2 Li1 O1 103.8(3) . 2_456 ? O1W Li1 O1 111.3(3) . 2_456 ? O2W Li1 O1 110.5(3) . 2_456 ? O1 C1 N1 122.6(3) . . ? O1 C1 C2 122.5(3) . . ? N1 C1 C2 114.9(3) . . ? C1 O1 Li1 149.4(3) . 2_446 ? C1 N1 H1A 121(3) . . ? C1 N1 H1B 117(3) . . ? H1A N1 H1B 121(4) . . ? N2 C2 C1 113.9(3) . . ? N2 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? N2 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C6 N2 C2 122.6(3) . . ? C6 N2 C3 114.8(3) . . ? C2 N2 C3 122.5(3) . . ? N2 C3 C4 103.2(3) . . ? N2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? N2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C5 C4 C3 106.5(4) . . ? C5 C4 H4A 110.4 . . ? C3 C4 H4A 110.4 . . ? C5 C4 H4B 110.4 . . ? C3 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? C6 C5 C4 105.5(3) . . ? C6 C5 H5A 110.6 . . ? C4 C5 H5A 110.6 . . ? C6 C5 H5B 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? O2 C6 N2 124.0(3) . . ? O2 C6 C5 127.5(3) . . ? N2 C6 C5 108.5(3) . . ? C6 O2 Li1 146.8(3) . . ? Li1 O2W H200 107.5 . . ? Li1 O2W H201 129.4 . . ? H200 O2W H201 122.9 . . ? Li1 O1W H100 127(3) . . ? Li1 O1W H101 122(4) . . ? H100 O1W H101 108(5) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.440 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.063 # Attachment '- PIR_LiCl.cif' data_PirLiCl _database_code_depnum_ccdc_archive 'CCDC 884811' #TrackingRef '- PIR_LiCl.cif' _chemical_formula_sum 'C6 H10 N2 O2 Li1 Cl1' _chemical_formula_weight 184.549 _chemical_formula_moiety 'C6 H10 N2 O2 Li1 Cl1' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P121/n1 _cell_formula_units_Z 4 _cell_length_a 9.1230(1) _cell_length_b 12.1788(2) _cell_length_c 8.1089(2) _cell_angle_alpha 90 _cell_angle_beta 101.8548(8) _cell_angle_gamma 90 _cell_volume 881.7438 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' _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54060 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ; X'pert in Debye-Scherrer geometry ; _computing_data_collection 'Highscore plus' _computing_cell_refinement 'Topas (Coelho ,2007)' _computing_structure_solution 'DASH (David, Shankland, 2006)' _computing_structure_refinement 'Topas (Coelho ,2007)' _pd_proc_2theta_range_min 5 _pd_proc_2theta_range_max 90 _pd_proc_info_excluded_regions no _pd_proc_ls_background_function Chebyschev _pd_proc_ls_pref_orient_corr ; Spherical Harmonics ; _pd_proc_ls_prof_R_factor 0.022 _pd_proc_ls_prof_wR_factor 0.029 _pd_proc_ls_prof_wR_expected 0.017 _pd_spec_mount_mode transmission _pd_spec_mounting ; 0.5 mm borosilicate glass capillary ; _pd_spec_shape cylinder _refine_ls_hydrogen_treatment constr loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 1 0.55966(18) 0.07474(15) -0.79823(20) 1 2.2237 Li1 Li 1 -0.6207(12) 0.09415(92) -0.0563(14) 1 2.1279 N1z N 1 0.06505 0.85309 0.08331 1 2.317(62) O2z O 1 0.07364812 0.7162321 -0.3025156 1 2.317(62) O1z O 1 -0.1878384 0.8834395 0.02703815 1 2.317(62) N2z N 1 0.0551476 0.6437559 -0.05165169 1 2.317(62) C1z C 1 -0.0671738 0.87457 0.1281128 1 2.317(62) C2z C 1 -0.04188464 0.8858666 0.3119739 1 2.317(62) C3z C 1 0.1286868 0.9004954 0.3726323 1 2.317(62) C4z C 1 0.1929748 0.8563175 0.2254106 1 2.317(62) C5z C 1 0.08067264 0.8450224 -0.09038951 1 2.317(62) C6z C 1 0.07082337 0.7264772 -0.1520119 1 2.317(62) H1z H 1 -0.05940634 0.9637281 0.3425775 1 2.780(75) H2z H 1 -0.1107531 0.8364099 0.3585934 1 2.780(75) H3z H 1 0.1976629 0.9569846 0.4384274 1 2.780(75) H4z H 1 0.1120195 0.8404129 0.4504192 1 2.780(75) H5z H 1 0.2724241 0.9059555 0.1998062 1 2.780(75) H6z H 1 0.2347575 0.7809365 0.250726 1 2.780(75) H7z H 1 -0.0007309067 0.8887586 -0.1624788 1 2.780(75) H8z H 1 0.1802994 0.8756783 -0.1001217 1 2.780(75) H9z H 1 0.05373971 0.6579766 0.07134842 1 2.780(75) H10z H 1 0.0445124 0.565984 -0.09754942 1 2.780(75) # Attachment '- PIR_LiCl_2H2O.CIF' data_[piracetam]LiCl_2H2O _database_code_depnum_ccdc_archive 'CCDC 884812' #TrackingRef '- PIR_LiCl_2H2O.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H14 Cl Li N2 O4' _chemical_formula_weight 220.58 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' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5347(11) _cell_length_b 9.7992(12) _cell_length_c 14.732(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.596(13) _cell_angle_gamma 90.00 _cell_volume 1087.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_T_min 0.30075 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4868 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0763 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2353 _reflns_number_gt 1403 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.0533P] 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 2353 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1958 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 Li1 Li -0.5634(8) 0.6605(6) 0.7244(4) 0.0401(14) Uani 1 1 d . . . Cl1 Cl 0.06606(13) 0.13331(9) 0.34859(7) 0.0514(4) Uani 1 1 d . . . C1 C -0.6499(5) 0.1488(3) 0.5959(2) 0.0350(8) Uani 1 1 d . . . O1 O -0.5762(3) 0.1133(2) 0.66765(17) 0.0433(7) Uani 1 1 d . . . N1 N -0.7816(5) 0.0799(4) 0.5581(3) 0.0524(10) Uani 1 1 d . . . H1A H -0.816(7) 0.104(5) 0.514(3) 0.063 Uiso 1 1 d . . . H1B H -0.824(6) 0.011(4) 0.586(3) 0.063 Uiso 1 1 d . . . C2 C -0.6003(5) 0.2776(3) 0.5472(3) 0.0432(9) Uani 1 1 d . . . H2A H -0.6095 0.2612 0.4823 0.052 Uiso 1 1 calc R . . H2B H -0.6854 0.3481 0.5615 0.052 Uiso 1 1 calc R . . N2 N -0.4255(4) 0.3270(3) 0.5692(2) 0.0365(7) Uani 1 1 d . . . C3 C -0.2667(6) 0.2589(4) 0.5396(3) 0.0556(11) Uani 1 1 d . . . H3A H -0.2717 0.2437 0.4746 0.067 Uiso 1 1 calc R . . H3B H -0.2506 0.1720 0.5703 0.067 Uiso 1 1 calc R . . C4 C -0.1200(7) 0.3565(6) 0.5656(5) 0.096(2) Uani 1 1 d . . . H4A H -0.0719 0.3982 0.5119 0.115 Uiso 1 1 calc R . . H4B H -0.0250 0.3090 0.5983 0.115 Uiso 1 1 calc R . . C5 C -0.2010(5) 0.4635(4) 0.6253(3) 0.0585(12) Uani 1 1 d . . . H5A H -0.1627 0.4511 0.6882 0.070 Uiso 1 1 calc R . . H5B H -0.1680 0.5544 0.6060 0.070 Uiso 1 1 calc R . . C6 C -0.3957(5) 0.4423(3) 0.6140(2) 0.0348(8) Uani 1 1 d . . . O2 O -0.5131(4) 0.5177(2) 0.64053(18) 0.0500(7) Uani 1 1 d . . . O3 O -0.4827(3) 0.8315(2) 0.67782(19) 0.0474(7) Uani 1 1 d . . . H300 H -0.3541 0.8248 0.6628 0.057 Uiso 1 1 d . . . H301 H -0.5553 0.9155 0.6703 0.057 Uiso 1 1 d . . . O4 O -0.8141(3) 0.6475(3) 0.7433(2) 0.0621(9) Uani 1 1 d . . . H400 H -0.8459 0.5517 0.7601 0.074 Uiso 1 1 d . . . H401 H -0.8809 0.6710 0.6855 0.074 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Li1 0.047(3) 0.034(3) 0.039(4) -0.001(2) -0.003(3) 0.002(3) Cl1 0.0447(6) 0.0493(6) 0.0597(7) 0.0052(5) -0.0068(5) -0.0019(4) C1 0.0379(19) 0.0248(16) 0.042(2) -0.0046(15) -0.0045(17) 0.0019(15) O1 0.0506(16) 0.0375(13) 0.0409(15) 0.0034(11) -0.0135(13) -0.0038(11) N1 0.058(2) 0.0415(19) 0.057(3) 0.0090(17) -0.0188(19) -0.0152(17) C2 0.052(2) 0.0319(18) 0.045(2) 0.0042(16) -0.0125(18) -0.0093(17) N2 0.0412(17) 0.0278(14) 0.0406(18) -0.0019(12) 0.0048(14) 0.0007(13) C3 0.065(3) 0.046(2) 0.057(3) -0.0007(19) 0.024(2) 0.008(2) C4 0.053(3) 0.084(4) 0.154(6) 0.005(4) 0.037(3) -0.014(3) C5 0.052(3) 0.044(2) 0.078(3) 0.014(2) -0.015(2) -0.015(2) C6 0.049(2) 0.0247(17) 0.0301(19) 0.0066(14) -0.0008(16) -0.0063(16) O2 0.0669(18) 0.0335(13) 0.0496(18) -0.0110(12) 0.0021(14) 0.0109(13) O3 0.0500(16) 0.0344(13) 0.0580(18) -0.0007(12) 0.0031(13) 0.0029(11) O4 0.0426(16) 0.0610(18) 0.082(2) 0.0156(15) -0.0084(15) 0.0018(13) _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 O2 1.912(6) . ? Li1 O3 1.916(6) . ? Li1 O4 1.921(7) . ? Li1 O1 1.938(7) 2_456 ? C1 O1 1.230(4) . ? C1 N1 1.313(5) . ? C1 C2 1.504(5) . ? O1 Li1 1.938(7) 2_446 ? N1 H1A 0.73(5) . ? N1 H1B 0.86(4) . ? C2 N2 1.432(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 C6 1.325(4) . ? N2 C3 1.448(5) . ? C3 C4 1.503(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.508(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.487(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.224(4) . ? O3 H300 1.0016 . ? O3 H301 0.9935 . ? O4 H400 1.0015 . ? O4 H401 1.0047 . ? 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 Li1 O3 109.8(3) . . ? O2 Li1 O4 105.0(3) . . ? O3 Li1 O4 115.7(3) . . ? O2 Li1 O1 104.0(3) . 2_456 ? O3 Li1 O1 109.4(3) . 2_456 ? O4 Li1 O1 112.2(3) . 2_456 ? O1 C1 N1 122.5(3) . . ? O1 C1 C2 122.4(3) . . ? N1 C1 C2 115.1(3) . . ? C1 O1 Li1 149.2(3) . 2_446 ? C1 N1 H1A 117(4) . . ? C1 N1 H1B 120(3) . . ? H1A N1 H1B 123(5) . . ? N2 C2 C1 114.5(3) . . ? N2 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N2 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C6 N2 C2 122.9(3) . . ? C6 N2 C3 114.4(3) . . ? C2 N2 C3 122.6(3) . . ? N2 C3 C4 103.8(3) . . ? N2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? N2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C3 C4 C5 106.5(4) . . ? C3 C4 H4A 110.4 . . ? C5 C4 H4A 110.4 . . ? C3 C4 H4B 110.4 . . ? C5 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? C6 C5 C4 104.6(4) . . ? C6 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? C6 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? O2 C6 N2 124.0(3) . . ? O2 C6 C5 126.9(3) . . ? N2 C6 C5 109.1(3) . . ? C6 O2 Li1 143.7(3) . . ? Li1 O3 H300 109.9 . . ? Li1 O3 H301 125.8 . . ? H300 O3 H301 124.3 . . ? Li1 O4 H400 110.0 . . ? Li1 O4 H401 109.4 . . ? H400 O4 H401 107.9 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.247 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.056