Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Hubert Schmidbaur' 'Frank Wiesbrock' _publ_contact_author_name 'Prof Hubert Schmidbaur ' _publ_contact_author_address ; Anorganisch-chemisches Institut TU Muenchen Lichtenbergstrasse 4 Garching 85747 GERMANY ; _publ_contact_author_email H.SCHMIDBAUR@LRZ.TUM.DE _publ_section_title ; Lithium salicylate monohydrate: A layer structure with carboxylate-bridged delta- and lambda-[(H2O)Li+] helices ; data_wies28 _database_code_depnum_ccdc_archive 'CCDC 221932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 Li O4' _chemical_formula_weight 162.07 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 P2(1)/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 13.1148(8) _cell_length_b 4.6992(2) _cell_length_c 12.8071(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.900(1) _cell_angle_gamma 90.00 _cell_volume 751.08(6) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 27930 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type DELABS _exptl_absorpt_correction_T_min 0.305 _exptl_absorpt_correction_T_max 0.743 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27930 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.27 _reflns_number_total 1601 _reflns_number_gt 1442 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0661P)^2^+0.1353P] 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 1601 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O01 O 0.42711(8) 0.1613(2) 0.70710(8) 0.0369(3) Uani 1 1 d . . . O1 O 0.38455(8) -0.1914(2) 0.88899(8) 0.0410(3) Uani 1 1 d . . . O3 O 0.26515(9) -0.5255(2) 0.74941(8) 0.0419(3) Uani 1 1 d . . . C2 C 0.21752(11) -0.5924(3) 0.82686(10) 0.0360(3) Uani 1 1 d . . . C7 C 0.34849(11) -0.2795(3) 0.96438(10) 0.0348(3) Uani 1 1 d . . . C1 C 0.25210(10) -0.4683(3) 0.93194(10) 0.0346(3) Uani 1 1 d . . . C3 C 0.13347(12) -0.7874(3) 0.80049(12) 0.0426(4) Uani 1 1 d . . . C6 C 0.19574(12) -0.5298(3) 1.00558(12) 0.0421(4) Uani 1 1 d . . . C4 C 0.08047(13) -0.8470(4) 0.87559(13) 0.0497(4) Uani 1 1 d . . . C5 C 0.11005(14) -0.7165(4) 0.97762(12) 0.0504(4) Uani 1 1 d . . . Li Li 0.5012(2) -0.0280(5) 0.85294(18) 0.0391(5) Uani 1 1 d . . . O2 O 0.39092(8) -0.2220(2) 1.06448(7) 0.0392(3) Uani 1 1 d . . . H6 H 0.2179(14) -0.438(4) 1.0796(14) 0.049(5) Uiso 1 1 d . . . H3 H 0.1137(15) -0.880(4) 0.7292(15) 0.050(5) Uiso 1 1 d . . . H5 H 0.0706(17) -0.751(4) 1.0295(16) 0.062(6) Uiso 1 1 d . . . H4 H 0.0215(16) -0.995(4) 0.8550(16) 0.064(6) Uiso 1 1 d . . . H01 H 0.4093(15) 0.017(4) 0.6565(16) 0.056(5) Uiso 1 1 d . . . H02 H 0.3647(19) 0.243(5) 0.7155(17) 0.075(7) Uiso 1 1 d . . . H03 H 0.312(2) -0.373(6) 0.784(2) 0.092(8) 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 O01 0.0450(6) 0.0343(6) 0.0337(5) -0.0008(4) 0.0157(4) 0.0004(4) O1 0.0474(6) 0.0424(6) 0.0382(5) 0.0016(4) 0.0203(4) -0.0048(4) O3 0.0502(6) 0.0467(7) 0.0335(5) -0.0036(4) 0.0199(4) -0.0021(5) C2 0.0419(7) 0.0357(7) 0.0325(6) 0.0016(5) 0.0143(5) 0.0033(5) C7 0.0431(7) 0.0306(7) 0.0337(6) 0.0011(5) 0.0162(5) 0.0029(5) C1 0.0392(7) 0.0335(8) 0.0326(6) 0.0015(5) 0.0133(5) 0.0009(5) C3 0.0495(8) 0.0401(9) 0.0360(7) -0.0005(5) 0.0099(6) -0.0032(6) C6 0.0464(8) 0.0479(9) 0.0342(7) 0.0009(6) 0.0158(6) -0.0046(6) C4 0.0489(9) 0.0539(10) 0.0440(8) 0.0030(7) 0.0107(7) -0.0142(7) C5 0.0506(9) 0.0633(11) 0.0408(8) 0.0039(7) 0.0192(7) -0.0133(7) Li 0.0485(13) 0.0362(13) 0.0352(11) -0.0005(9) 0.0169(10) -0.0025(10) O2 0.0472(6) 0.0374(6) 0.0338(5) -0.0008(4) 0.0137(4) -0.0041(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 O01 Li 2.013(3) 2_656 ? O01 Li 2.027(3) . ? O01 H01 0.92(2) . ? O01 H02 0.94(2) . ? O1 C7 1.2681(16) . ? O1 Li 1.891(3) . ? O3 C2 1.3616(16) . ? O3 H03 0.96(3) . ? C2 C3 1.393(2) . ? C2 C1 1.4076(19) . ? C7 O2 1.2600(16) . ? C7 C1 1.4951(19) . ? C1 C6 1.3956(19) . ? C3 C4 1.378(2) . ? C3 H3 0.971(19) . ? C6 C5 1.383(2) . ? C6 H6 1.001(18) . ? C4 C5 1.387(2) . ? C4 H4 1.01(2) . ? C5 H5 0.97(2) . ? Li O2 1.893(3) 3_657 ? Li O01 2.013(3) 2_646 ? Li Li 3.525(3) 2_646 ? Li Li 3.525(3) 2_656 ? O2 Li 1.893(3) 3_657 ? 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 Li O01 Li 121.50(8) 2_656 . ? Li O01 H01 108.2(12) 2_656 . ? Li O01 H01 105.8(12) . . ? Li O01 H02 105.8(14) 2_656 . ? Li O01 H02 105.2(13) . . ? H01 O01 H02 110.0(18) . . ? C7 O1 Li 146.87(12) . . ? C2 O3 H03 102.3(15) . . ? O3 C2 C3 118.77(12) . . ? O3 C2 C1 121.05(13) . . ? C3 C2 C1 120.18(12) . . ? O2 C7 O1 123.59(13) . . ? O2 C7 C1 118.78(12) . . ? O1 C7 C1 117.62(12) . . ? C6 C1 C2 118.58(13) . . ? C6 C1 C7 120.88(12) . . ? C2 C1 C7 120.53(12) . . ? C4 C3 C2 119.73(14) . . ? C4 C3 H3 121.3(11) . . ? C2 C3 H3 119.0(11) . . ? C5 C6 C1 120.88(14) . . ? C5 C6 H6 119.7(10) . . ? C1 C6 H6 119.4(10) . . ? C3 C4 C5 120.87(15) . . ? C3 C4 H4 117.8(11) . . ? C5 C4 H4 121.3(11) . . ? C6 C5 C4 119.61(14) . . ? C6 C5 H5 119.3(12) . . ? C4 C5 H5 121.0(12) . . ? O1 Li O2 129.61(13) . 3_657 ? O1 Li O01 107.87(12) . 2_646 ? O2 Li O01 107.87(13) 3_657 2_646 ? O1 Li O01 102.05(12) . . ? O2 Li O01 107.86(12) 3_657 . ? O01 Li O01 96.56(10) 2_646 . ? O1 Li Li 95.18(9) . 2_646 ? O2 Li Li 131.68(14) 3_657 2_646 ? O01 Li Li 29.36(4) 2_646 2_646 ? O01 Li Li 73.25(10) . 2_646 ? O1 Li Li 129.16(14) . 2_656 ? O2 Li Li 80.64(7) 3_657 2_656 ? O01 Li Li 95.47(11) 2_646 2_656 ? O01 Li Li 29.13(6) . 2_656 ? Li Li Li 83.61(10) 2_646 2_656 ? C7 O2 Li 136.25(11) . 3_657 ? 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 Li O1 C7 O2 15.2(3) . . . . ? Li O1 C7 C1 -163.00(18) . . . . ? O3 C2 C1 C6 175.71(13) . . . . ? C3 C2 C1 C6 -4.4(2) . . . . ? O3 C2 C1 C7 -5.5(2) . . . . ? C3 C2 C1 C7 174.40(13) . . . . ? O2 C7 C1 C6 13.9(2) . . . . ? O1 C7 C1 C6 -167.75(13) . . . . ? O2 C7 C1 C2 -164.85(13) . . . . ? O1 C7 C1 C2 13.5(2) . . . . ? O3 C2 C3 C4 -176.63(14) . . . . ? C1 C2 C3 C4 3.5(2) . . . . ? C2 C1 C6 C5 2.3(2) . . . . ? C7 C1 C6 C5 -176.53(14) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C1 C6 C5 C4 0.8(3) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C7 O1 Li O2 -29.4(3) . . . 3_657 ? C7 O1 Li O01 103.9(2) . . . 2_646 ? C7 O1 Li O01 -155.10(18) . . . . ? C7 O1 Li Li 131.0(2) . . . 2_646 ? C7 O1 Li Li -143.1(2) . . . 2_656 ? Li O01 Li O1 160.63(9) 2_656 . . . ? Li O01 Li O2 21.72(16) 2_656 . . 3_657 ? Li O01 Li O01 -89.47(17) 2_656 . . 2_646 ? Li O01 Li Li -107.53(12) 2_656 . . 2_646 ? O1 C7 O2 Li 10.4(3) . . . 3_657 ? C1 C7 O2 Li -171.33(14) . . . 3_657 ? 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 O01 H01 O2 0.92(2) 1.79(2) 2.7002(14) 173.1(18) 4 O01 H02 O3 0.94(2) 1.85(2) 2.7709(15) 166(2) 1_565 O3 H03 O1 0.96(3) 1.63(3) 2.5282(15) 154(2) . _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.27 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.256 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.049