# Electronic Supplementary Material (ESI) for Energy & Environmental Science # 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_x10138 #TrackingRef 'web_deposit_cif_file_1_JoshuaAllen_1333645464.x10138.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H4 F6 Li N O7 S2' _chemical_formula_weight 375.15 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.79510(10) _cell_length_b 12.7103(2) _cell_length_c 16.8547(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1241.47(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used 9829 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 34.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7980 _exptl_absorpt_correction_T_max 0.8521 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Kappa Axis X8 Apex2' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 51077 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 37.88 _reflns_number_total 5986 _reflns_number_gt 5440 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution XS _computing_structure_refinement XL _computing_molecular_graphics NRCVAX _computing_publication_material cif2tables.py _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^)+(0.0411P)^2^+0.2258P] 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 refall _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 0.00(4) _refine_ls_number_reflns 5986 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Li1 Li -0.1275(4) 0.28963(19) 0.72561(13) 0.0189(4) Uani 1 1 d . . . S1 S 0.36985(5) 0.33047(2) 0.806999(16) 0.01245(5) Uani 1 1 d . . . S2 S 0.15777(5) 0.51340(2) 0.754017(17) 0.01324(5) Uani 1 1 d . . . O1 O 0.60366(15) 0.29465(7) 0.79923(6) 0.01790(16) Uani 1 1 d . . . O2 O 0.19497(17) 0.27059(7) 0.76668(6) 0.01897(18) Uani 1 1 d . . . O3 O 0.15156(18) 0.61854(6) 0.78400(6) 0.01927(17) Uani 1 1 d . . . O4 O -0.05592(16) 0.45702(7) 0.74707(6) 0.02026(18) Uani 1 1 d . . . N1 N 0.35914(19) 0.45299(8) 0.79730(7) 0.01792(19) Uani 1 1 d . . . C1 C 0.3050(3) 0.31461(11) 0.91275(8) 0.0225(3) Uani 1 1 d . . . F1 F 0.4592(2) 0.36558(10) 0.95586(6) 0.0465(3) Uani 1 1 d . . . F2 F 0.3082(2) 0.21455(8) 0.93284(6) 0.0347(2) Uani 1 1 d . . . F3 F 0.0975(2) 0.35306(10) 0.92792(7) 0.0438(3) Uani 1 1 d . . . C2 C 0.2699(3) 0.52522(11) 0.65264(8) 0.0252(3) Uani 1 1 d . . . F4 F 0.1347(3) 0.58827(10) 0.61160(6) 0.0515(3) Uani 1 1 d . . . F5 F 0.2735(2) 0.43105(8) 0.61844(6) 0.0366(3) Uani 1 1 d . . . F6 F 0.4808(2) 0.56411(8) 0.65342(7) 0.0372(3) Uani 1 1 d . . . O5 O -0.1532(2) 0.29821(9) 0.61210(6) 0.0299(2) Uani 1 1 d . . . O6 O -0.2765(2) 0.42239(8) 0.52762(6) 0.0236(2) Uani 1 1 d . . . O7 O -0.09974(18) 0.28093(8) 0.48206(6) 0.02125(19) Uani 1 1 d . . . C3 C -0.1757(2) 0.33193(10) 0.54582(7) 0.0176(2) Uani 1 1 d . . . C4 C -0.3059(3) 0.42653(11) 0.44192(9) 0.0243(3) Uani 1 1 d . . . H4A H -0.271(4) 0.4995(15) 0.4253(11) 0.027(5) Uiso 1 1 d . . . H4B H -0.462(4) 0.4064(15) 0.4313(12) 0.023(5) Uiso 1 1 d . . . C5 C -0.1347(3) 0.34680(11) 0.41257(8) 0.0248(3) Uani 1 1 d . . . H5A H -0.192(4) 0.2971(17) 0.3676(13) 0.039(6) Uiso 1 1 d . . . H5B H 0.012(3) 0.3743(13) 0.3978(11) 0.017(4) 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 0.0148(10) 0.0252(10) 0.0167(9) 0.0002(8) -0.0018(8) -0.0012(9) S1 0.01129(10) 0.01191(9) 0.01415(11) 0.00016(8) -0.00012(9) 0.00026(9) S2 0.01296(11) 0.01254(10) 0.01423(11) 0.00074(9) 0.00063(9) 0.00091(8) O1 0.0127(4) 0.0181(4) 0.0229(4) 0.0023(3) 0.0033(3) 0.0021(3) O2 0.0181(4) 0.0142(3) 0.0246(4) -0.0018(3) -0.0055(3) -0.0028(3) O3 0.0236(4) 0.0129(3) 0.0212(4) -0.0012(3) 0.0012(4) 0.0029(3) O4 0.0122(3) 0.0205(4) 0.0281(5) 0.0012(4) -0.0020(4) -0.0009(3) N1 0.0162(4) 0.0126(4) 0.0250(5) 0.0010(3) -0.0060(4) 0.0002(3) C1 0.0269(6) 0.0228(6) 0.0177(5) 0.0017(4) 0.0051(5) 0.0059(5) F1 0.0655(9) 0.0571(7) 0.0170(4) -0.0042(5) -0.0083(5) -0.0132(6) F2 0.0490(6) 0.0275(4) 0.0277(4) 0.0130(4) 0.0137(4) 0.0093(4) F3 0.0421(6) 0.0513(6) 0.0379(6) 0.0120(5) 0.0239(5) 0.0260(5) C2 0.0352(7) 0.0221(6) 0.0182(5) -0.0008(5) 0.0056(5) -0.0036(6) F4 0.0759(9) 0.0570(7) 0.0215(4) 0.0157(5) -0.0050(6) 0.0149(7) F5 0.0494(6) 0.0316(5) 0.0289(5) -0.0152(4) 0.0174(4) -0.0147(5) F6 0.0429(6) 0.0277(5) 0.0411(6) -0.0069(4) 0.0243(5) -0.0152(4) O5 0.0359(6) 0.0376(6) 0.0161(4) 0.0072(4) -0.0075(4) -0.0149(5) O6 0.0297(5) 0.0190(4) 0.0223(5) -0.0033(4) 0.0034(4) 0.0031(4) O7 0.0217(5) 0.0205(4) 0.0216(4) 0.0029(3) 0.0028(4) 0.0054(3) C3 0.0164(5) 0.0205(5) 0.0160(5) 0.0007(4) -0.0022(4) -0.0051(4) C4 0.0255(7) 0.0230(6) 0.0245(6) 0.0062(5) -0.0039(5) 0.0031(5) C5 0.0293(7) 0.0297(6) 0.0155(5) 0.0033(5) 0.0036(5) 0.0025(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 O5 1.922(2) . ? Li1 O1 1.993(3) 1_455 ? Li1 O2 2.007(3) . ? Li1 O3 2.185(3) 3_546 ? Li1 O4 2.198(3) . ? S1 O1 1.4354(9) . ? S1 O2 1.4381(10) . ? S1 N1 1.5671(10) . ? S1 C1 1.8327(14) . ? S2 O3 1.4291(9) . ? S2 O4 1.4356(9) . ? S2 N1 1.5759(11) . ? S2 C2 1.8342(14) . ? O1 Li1 1.993(3) 1_655 ? O3 Li1 2.185(3) 3_556 ? C1 F2 1.3162(16) . ? C1 F1 1.3211(19) . ? C1 F3 1.3231(17) . ? C2 F6 1.3185(19) . ? C2 F4 1.3169(19) . ? C2 F5 1.3288(17) . ? O5 C3 1.2036(15) . ? O6 C3 1.3257(16) . ? O6 C4 1.4554(18) . ? O7 C3 1.3299(16) . ? O7 C5 1.4539(16) . ? C4 C5 1.502(2) . ? C4 H4A 0.99(2) . ? C4 H4B 0.96(2) . ? C5 H5A 1.04(2) . ? C5 H5B 0.950(19) . ? 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 O5 Li1 O1 123.86(14) . 1_455 ? O5 Li1 O2 114.99(13) . . ? O1 Li1 O2 121.13(12) 1_455 . ? O5 Li1 O3 88.72(10) . 3_546 ? O1 Li1 O3 91.61(10) 1_455 3_546 ? O2 Li1 O3 88.00(10) . 3_546 ? O5 Li1 O4 97.10(11) . . ? O1 Li1 O4 90.80(10) 1_455 . ? O2 Li1 O4 83.36(9) . . ? O3 Li1 O4 171.03(13) 3_546 . ? O1 S1 O2 117.02(6) . . ? O1 S1 N1 110.06(6) . . ? O2 S1 N1 116.66(6) . . ? O1 S1 C1 104.32(6) . . ? O2 S1 C1 104.89(7) . . ? N1 S1 C1 101.69(6) . . ? O3 S2 O4 118.29(6) . . ? O3 S2 N1 108.10(6) . . ? O4 S2 N1 115.67(6) . . ? O3 S2 C2 105.17(6) . . ? O4 S2 C2 105.70(7) . . ? N1 S2 C2 102.05(7) . . ? S1 O1 Li1 143.61(9) . 1_655 ? S1 O2 Li1 139.04(9) . . ? S2 O3 Li1 154.96(9) . 3_556 ? S2 O4 Li1 131.26(9) . . ? S1 N1 S2 124.18(7) . . ? F2 C1 F1 108.85(13) . . ? F2 C1 F3 108.66(13) . . ? F1 C1 F3 109.09(13) . . ? F2 C1 S1 110.71(9) . . ? F1 C1 S1 110.02(10) . . ? F3 C1 S1 109.49(10) . . ? F6 C2 F4 109.18(13) . . ? F6 C2 F5 109.13(13) . . ? F4 C2 F5 109.24(13) . . ? F6 C2 S2 110.48(11) . . ? F4 C2 S2 109.17(11) . . ? F5 C2 S2 109.63(10) . . ? C3 O5 Li1 162.27(13) . . ? C3 O6 C4 108.21(10) . . ? C3 O7 C5 108.91(10) . . ? O5 C3 O6 124.83(13) . . ? O5 C3 O7 122.73(13) . . ? O6 C3 O7 112.44(11) . . ? O6 C4 C5 103.02(11) . . ? O6 C4 H4A 106.9(11) . . ? C5 C4 H4A 113.8(12) . . ? O6 C4 H4B 106.6(12) . . ? C5 C4 H4B 112.5(12) . . ? H4A C4 H4B 113.1(16) . . ? O7 C5 C4 102.44(11) . . ? O7 C5 H5A 106.3(12) . . ? C4 C5 H5A 116.0(13) . . ? O7 C5 H5B 107.4(11) . . ? C4 C5 H5B 115.3(10) . . ? H5A C5 H5B 108.5(17) . . ? 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 O2 S1 O1 Li1 76.22(16) . . . 1_655 ? N1 S1 O1 Li1 -60.04(16) . . . 1_655 ? C1 S1 O1 Li1 -168.45(15) . . . 1_655 ? O1 S1 O2 Li1 -158.26(13) . . . . ? N1 S1 O2 Li1 -24.88(16) . . . . ? C1 S1 O2 Li1 86.73(14) . . . . ? O5 Li1 O2 S1 107.24(15) . . . . ? O1 Li1 O2 S1 -74.43(19) 1_455 . . . ? O3 Li1 O2 S1 -165.10(10) 3_546 . . . ? O4 Li1 O2 S1 12.48(16) . . . . ? O4 S2 O3 Li1 -91.0(2) . . . 3_556 ? N1 S2 O3 Li1 135.1(2) . . . 3_556 ? C2 S2 O3 Li1 26.7(2) . . . 3_556 ? O3 S2 O4 Li1 -167.48(10) . . . . ? N1 S2 O4 Li1 -36.93(13) . . . . ? C2 S2 O4 Li1 75.14(12) . . . . ? O5 Li1 O4 S2 -92.95(13) . . . . ? O1 Li1 O4 S2 142.77(10) 1_455 . . . ? O2 Li1 O4 S2 21.51(14) . . . . ? O3 Li1 O4 S2 37.2(9) 3_546 . . . ? O1 S1 N1 S2 142.76(8) . . . . ? O2 S1 N1 S2 6.33(12) . . . . ? C1 S1 N1 S2 -107.10(10) . . . . ? O3 S2 N1 S1 156.09(8) . . . . ? O4 S2 N1 S1 20.83(12) . . . . ? C2 S2 N1 S1 -93.35(10) . . . . ? O1 S1 C1 F2 -64.97(12) . . . . ? O2 S1 C1 F2 58.61(12) . . . . ? N1 S1 C1 F2 -179.44(11) . . . . ? O1 S1 C1 F1 55.39(11) . . . . ? O2 S1 C1 F1 178.96(10) . . . . ? N1 S1 C1 F1 -59.09(11) . . . . ? O1 S1 C1 F3 175.26(10) . . . . ? O2 S1 C1 F3 -61.16(12) . . . . ? N1 S1 C1 F3 60.79(12) . . . . ? O3 S2 C2 F6 62.15(11) . . . . ? O4 S2 C2 F6 -171.95(10) . . . . ? N1 S2 C2 F6 -50.61(11) . . . . ? O3 S2 C2 F4 -57.92(12) . . . . ? O4 S2 C2 F4 67.97(12) . . . . ? N1 S2 C2 F4 -170.68(11) . . . . ? O3 S2 C2 F5 -177.55(11) . . . . ? O4 S2 C2 F5 -51.65(13) . . . . ? N1 S2 C2 F5 69.69(12) . . . . ? O1 Li1 O5 C3 78.9(5) 1_455 . . . ? O2 Li1 O5 C3 -102.8(4) . . . . ? O3 Li1 O5 C3 170.0(4) 3_546 . . . ? O4 Li1 O5 C3 -16.9(5) . . . . ? Li1 O5 C3 O6 -22.9(5) . . . . ? Li1 O5 C3 O7 157.0(4) . . . . ? C4 O6 C3 O5 -170.16(13) . . . . ? C4 O6 C3 O7 9.90(15) . . . . ? C5 O7 C3 O5 -174.85(13) . . . . ? C5 O7 C3 O6 5.10(15) . . . . ? C3 O6 C4 C5 -19.84(15) . . . . ? C3 O7 C5 C4 -17.02(15) . . . . ? O6 C4 C5 O7 21.51(14) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.589 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 875125' ####################################################################### # # 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_x12120 #TrackingRef 'web_deposit_cif_file_0_JoshuaAllen_1334182441.x12120.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 F6 Li N O13 S2' _chemical_formula_weight 551.28 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 ca21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 8.729(3) _cell_length_b 14.045(5) _cell_length_c 16.041(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1966.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used 9791 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 29.84 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8095 _exptl_absorpt_correction_T_max 0.9389 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Kappa Axis X8 Apex2' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 133179 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 37.82 _reflns_number_total 10519 _reflns_number_gt 7953 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2 _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution SIR92 _computing_structure_refinement XL _computing_molecular_graphics NRCVAX _computing_publication_material cif2tables.py _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^)+(0.0674P)^2^+0.5247P] 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), 5097 Friedel pairs' _refine_ls_abs_structure_Flack 0.10(5) _refine_ls_number_reflns 10519 _refine_ls_number_parameters 344 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.025 _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 0.2367(3) 0.2454(2) 0.6412(2) 0.0260(5) Uani 1 1 d . . . S1 S 0.44753(5) 0.30619(3) 0.47116(3) 0.02507(8) Uani 0.9193(14) 1 d PD A 1 O1 O 0.3297(2) 0.30930(12) 0.53216(11) 0.0377(4) Uani 0.9193(14) 1 d P A 1 O2 O 0.60145(19) 0.28307(12) 0.49721(10) 0.0334(3) Uani 0.9193(14) 1 d P A 1 S2 S 0.49311(5) 0.20231(3) 0.32483(3) 0.02164(9) Uani 0.9193(14) 1 d PD A 1 O3 O 0.64837(17) 0.23573(11) 0.32005(11) 0.0341(3) Uani 0.9193(14) 1 d P A 1 O4 O 0.4093(2) 0.19352(11) 0.24897(10) 0.0345(3) Uani 0.9193(14) 1 d P . 1 N1 N 0.38694(18) 0.25149(11) 0.39196(11) 0.0246(3) Uani 0.9193(14) 1 d PD A 1 C1 C 0.4605(3) 0.43008(15) 0.43600(16) 0.0395(4) Uani 0.9193(14) 1 d P A 1 F1 F 0.4995(4) 0.48575(12) 0.49735(13) 0.0827(7) Uani 0.9193(14) 1 d P A 1 F2 F 0.5614(2) 0.43923(11) 0.37638(11) 0.0553(4) Uani 0.9193(14) 1 d P A 1 F3 F 0.3279(2) 0.45842(13) 0.40527(19) 0.0806(7) Uani 0.9193(14) 1 d P A 1 C2 C 0.50969(19) 0.08007(12) 0.36239(12) 0.0259(3) Uani 0.9193(14) 1 d P A 1 F4 F 0.37286(15) 0.04088(10) 0.37076(10) 0.0439(3) Uani 0.9193(14) 1 d P A 1 F5 F 0.58239(17) 0.07414(10) 0.43432(8) 0.0393(3) Uani 0.9193(14) 1 d P A 1 F6 F 0.58731(17) 0.02989(9) 0.30565(9) 0.0402(3) Uani 0.9193(14) 1 d P A 1 S1' S 0.44753(5) 0.30619(3) 0.47116(3) 0.02507(8) Uani 0.0807(14) 1 d PD A 2 O1' O 0.411(3) 0.3080(14) 0.5624(13) 0.0377(4) Uani 0.0807(14) 1 d P A 2 O2' O 0.288(2) 0.3047(13) 0.4270(12) 0.0334(3) Uani 0.0807(14) 1 d P A 2 S2' S 0.5799(5) 0.2122(3) 0.3550(3) 0.0177(10) Uani 0.0807(14) 1 d PD A 2 O3' O 0.739(2) 0.2031(12) 0.3369(12) 0.0341(3) Uani 0.0807(14) 1 d P A 2 O4' O 0.479(2) 0.2460(14) 0.2907(11) 0.0345(3) Uani 0.0807(14) 1 d P A 2 N1' N 0.5794(18) 0.2536(12) 0.4444(10) 0.0246(3) Uani 0.0807(14) 1 d PD A 2 C1' C 0.4605(3) 0.43008(15) 0.43600(16) 0.0395(4) Uani 0.0807(14) 1 d P A 2 F1' F 0.4995(4) 0.48575(12) 0.49735(13) 0.0827(7) Uani 0.0807(14) 1 d P A 2 F2' F 0.5614(2) 0.43923(11) 0.37638(11) 0.0553(4) Uani 0.0807(14) 1 d P A 2 F3' F 0.3279(2) 0.45842(13) 0.40527(19) 0.0806(7) Uani 0.0807(14) 1 d P A 2 C2' C 0.50969(19) 0.08007(12) 0.36239(12) 0.0259(3) Uani 0.0807(14) 1 d P A 2 F4' F 0.37286(15) 0.04088(10) 0.37076(10) 0.0439(3) Uani 0.0807(14) 1 d P A 2 F5' F 0.58239(17) 0.07414(10) 0.43432(8) 0.0393(3) Uani 0.0807(14) 1 d P A 2 F6' F 0.58731(17) 0.02989(9) 0.30565(9) 0.0402(3) Uani 0.0807(14) 1 d P A 2 O5 O 0.2538(2) 0.11932(9) 0.59336(9) 0.0379(3) Uani 1 1 d . A . C3 C 0.2475(2) 0.03473(12) 0.60552(10) 0.0242(3) Uani 1 1 d . . . O6 O 0.33359(16) -0.02709(9) 0.56540(9) 0.0283(2) Uani 1 1 d . A . O7 O 0.15432(18) -0.00670(11) 0.66006(10) 0.0362(3) Uani 1 1 d . A . C4 C 0.31035(19) -0.12131(11) 0.59949(11) 0.0253(3) Uani 1 1 d . . . H4A H 0.3993 -0.1415 0.6335 0.030 Uiso 1 1 calc R A . H4B H 0.2930 -0.1686 0.5547 0.030 Uiso 1 1 calc R . . C5 C 0.1688(2) -0.10939(13) 0.65292(12) 0.0289(3) Uani 1 1 d . A . H5A H 0.0777 -0.1375 0.6256 0.035 Uiso 1 1 calc R . . H5B H 0.1827 -0.1393 0.7083 0.035 Uiso 1 1 calc R . . O8 O 0.38999(17) 0.28783(11) 0.71987(10) 0.0347(3) Uani 1 1 d . A . C6 C 0.43084(19) 0.26918(12) 0.79011(12) 0.0265(3) Uani 1 1 d . . . O9 O 0.44176(17) 0.18233(9) 0.81986(9) 0.0300(3) Uani 1 1 d . A . O10 O 0.47313(18) 0.33552(10) 0.84473(12) 0.0390(4) Uani 1 1 d . A . C7 C 0.4894(3) 0.18555(16) 0.90590(14) 0.0388(5) Uani 1 1 d . . . H7A H 0.5833 0.1473 0.9146 0.047 Uiso 1 1 calc R A . H7B H 0.4077 0.1614 0.9431 0.047 Uiso 1 1 calc R . . C8 C 0.5200(3) 0.29016(18) 0.92186(15) 0.0394(5) Uani 1 1 d . A . H8A H 0.4587 0.3137 0.9695 0.047 Uiso 1 1 calc R . . H8B H 0.6299 0.3016 0.9333 0.047 Uiso 1 1 calc R . . O11 O 0.07083(18) 0.33477(14) 0.62474(11) 0.0418(4) Uani 0.472(3) 1 d P A 3 C9 C -0.04605(17) 0.37255(11) 0.64728(10) 0.0249(3) Uani 0.472(3) 1 d PD A 3 O12 O -0.05185(14) 0.45246(13) 0.68969(13) 0.0463(4) Uani 0.472(3) 1 d PD A 3 O13 O -0.1792(4) 0.3490(3) 0.6129(2) 0.0313(6) Uani 0.472(3) 1 d PD A 3 C10' C -0.2091(4) 0.4895(3) 0.6875(3) 0.0292(7) Uani 0.472(3) 1 d PD A 3 H10A H -0.2524 0.4944 0.7444 0.035 Uiso 0.472(3) 1 calc PR A 3 H10B H -0.2127 0.5530 0.6607 0.035 Uiso 0.472(3) 1 calc PR A 3 C11 C -0.2898(4) 0.4208(2) 0.6393(2) 0.0269(4) Uani 0.472(3) 1 d PD A 3 H11A H -0.3373 0.4514 0.5900 0.032 Uiso 0.472(3) 1 calc PR A 3 H11B H -0.3718 0.3910 0.6731 0.032 Uiso 0.472(3) 1 calc PR A 3 O11' O 0.07083(18) 0.33477(14) 0.62474(11) 0.0418(4) Uani 0.528(3) 1 d P A 4 C9' C -0.04605(17) 0.37255(11) 0.64728(10) 0.0249(3) Uani 0.528(3) 1 d PD A 4 O12' O -0.05185(14) 0.45246(13) 0.68969(13) 0.0463(4) Uani 0.528(3) 1 d PD A 4 O13' O -0.1835(3) 0.3326(2) 0.6475(2) 0.0313(6) Uani 0.528(3) 1 d PD A 4 C10 C -0.2125(4) 0.4648(3) 0.7136(2) 0.0292(7) Uani 0.528(3) 1 d PD A 4 H10C H -0.2201 0.4716 0.7749 0.035 Uiso 0.528(3) 1 calc PR A 4 H10D H -0.2535 0.5236 0.6879 0.035 Uiso 0.528(3) 1 calc PR A 4 C11' C -0.2905(3) 0.3944(2) 0.6902(2) 0.0269(4) Uani 0.528(3) 1 d PD A 4 H11C H -0.3735 0.4148 0.6521 0.032 Uiso 0.528(3) 1 calc PR A 4 H11D H -0.3365 0.3614 0.7387 0.032 Uiso 0.528(3) 1 calc PR A 4 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 0.0238(12) 0.0207(12) 0.0333(14) -0.0043(11) -0.0043(11) 0.0032(10) S1 0.03163(19) 0.02197(15) 0.02161(15) 0.00154(14) 0.00708(14) 0.00032(13) O1 0.0453(9) 0.0363(8) 0.0314(8) -0.0009(6) 0.0223(7) 0.0013(7) O2 0.0349(7) 0.0346(7) 0.0307(7) -0.0056(6) -0.0041(6) 0.0084(6) S2 0.02466(19) 0.01922(15) 0.02104(16) 0.00098(15) 0.00463(15) 0.00238(13) O3 0.0319(6) 0.0297(6) 0.0408(8) -0.0097(6) 0.0180(7) -0.0069(5) O4 0.0484(9) 0.0330(7) 0.0221(6) 0.0031(5) -0.0036(6) 0.0140(6) N1 0.0229(6) 0.0241(6) 0.0268(6) -0.0013(5) 0.0042(5) 0.0031(5) C1 0.0482(12) 0.0241(8) 0.0463(11) 0.0056(8) 0.0092(9) 0.0019(8) F1 0.166(2) 0.0303(8) 0.0517(10) -0.0134(7) 0.0131(12) -0.0160(10) F2 0.0807(12) 0.0377(7) 0.0476(8) 0.0063(6) 0.0185(8) -0.0222(7) F3 0.0603(11) 0.0403(8) 0.141(2) 0.0300(11) -0.0119(12) 0.0146(8) C2 0.0255(7) 0.0219(7) 0.0303(8) 0.0014(6) -0.0054(6) 0.0034(5) F4 0.0328(6) 0.0384(6) 0.0606(9) 0.0149(6) -0.0072(6) -0.0103(5) F5 0.0444(7) 0.0394(6) 0.0341(6) 0.0052(5) -0.0159(5) 0.0026(5) F6 0.0473(7) 0.0273(5) 0.0459(7) -0.0084(5) -0.0043(6) 0.0105(5) S1' 0.03163(19) 0.02197(15) 0.02161(15) 0.00154(14) 0.00708(14) 0.00032(13) O1' 0.0453(9) 0.0363(8) 0.0314(8) -0.0009(6) 0.0223(7) 0.0013(7) O2' 0.0349(7) 0.0346(7) 0.0307(7) -0.0056(6) -0.0041(6) 0.0084(6) S2' 0.0132(17) 0.0216(19) 0.0183(18) -0.0032(14) 0.0032(14) -0.0015(13) O3' 0.0319(6) 0.0297(6) 0.0408(8) -0.0097(6) 0.0180(7) -0.0069(5) O4' 0.0484(9) 0.0330(7) 0.0221(6) 0.0031(5) -0.0036(6) 0.0140(6) N1' 0.0229(6) 0.0241(6) 0.0268(6) -0.0013(5) 0.0042(5) 0.0031(5) C1' 0.0482(12) 0.0241(8) 0.0463(11) 0.0056(8) 0.0092(9) 0.0019(8) F1' 0.166(2) 0.0303(8) 0.0517(10) -0.0134(7) 0.0131(12) -0.0160(10) F2' 0.0807(12) 0.0377(7) 0.0476(8) 0.0063(6) 0.0185(8) -0.0222(7) F3' 0.0603(11) 0.0403(8) 0.141(2) 0.0300(11) -0.0119(12) 0.0146(8) C2' 0.0255(7) 0.0219(7) 0.0303(8) 0.0014(6) -0.0054(6) 0.0034(5) F4' 0.0328(6) 0.0384(6) 0.0606(9) 0.0149(6) -0.0072(6) -0.0103(5) F5' 0.0444(7) 0.0394(6) 0.0341(6) 0.0052(5) -0.0159(5) 0.0026(5) F6' 0.0473(7) 0.0273(5) 0.0459(7) -0.0084(5) -0.0043(6) 0.0105(5) O5 0.0620(9) 0.0187(5) 0.0329(6) -0.0015(5) -0.0018(7) 0.0032(6) C3 0.0294(7) 0.0221(6) 0.0212(6) -0.0004(5) -0.0034(5) 0.0026(5) O6 0.0339(6) 0.0179(5) 0.0330(6) 0.0047(4) 0.0112(5) 0.0001(4) O7 0.0395(7) 0.0313(7) 0.0376(7) 0.0012(6) 0.0150(6) 0.0076(6) C4 0.0236(6) 0.0182(6) 0.0340(8) 0.0039(6) 0.0014(5) 0.0008(5) C5 0.0265(7) 0.0283(7) 0.0319(8) 0.0056(6) 0.0052(6) -0.0053(6) O8 0.0305(6) 0.0351(7) 0.0383(7) 0.0054(6) -0.0127(6) -0.0076(5) C6 0.0218(6) 0.0228(7) 0.0351(8) -0.0029(6) -0.0072(6) -0.0003(5) O9 0.0400(7) 0.0228(5) 0.0273(6) -0.0046(5) -0.0062(5) 0.0021(4) O10 0.0414(7) 0.0223(6) 0.0533(9) -0.0119(6) -0.0195(6) 0.0027(5) C7 0.0512(12) 0.0340(10) 0.0312(9) -0.0035(8) -0.0143(8) 0.0117(8) C8 0.0413(10) 0.0406(11) 0.0363(10) -0.0125(8) -0.0134(8) 0.0032(8) O11 0.0314(7) 0.0540(9) 0.0401(8) 0.0176(7) 0.0086(6) 0.0222(6) C9 0.0212(6) 0.0280(7) 0.0256(7) 0.0085(6) 0.0001(5) 0.0050(5) O12 0.0167(5) 0.0589(10) 0.0633(11) -0.0271(9) -0.0022(6) -0.0064(6) O13 0.0260(7) 0.0245(11) 0.0433(17) -0.0108(12) -0.0092(12) 0.0046(7) C10' 0.0212(8) 0.037(2) 0.0296(19) -0.0058(13) 0.0004(12) 0.0011(11) C11 0.0153(7) 0.0281(11) 0.0374(11) -0.0018(9) -0.0009(9) 0.0021(7) O11' 0.0314(7) 0.0540(9) 0.0401(8) 0.0176(7) 0.0086(6) 0.0222(6) C9' 0.0212(6) 0.0280(7) 0.0256(7) 0.0085(6) 0.0001(5) 0.0050(5) O12' 0.0167(5) 0.0589(10) 0.0633(11) -0.0271(9) -0.0022(6) -0.0064(6) O13' 0.0260(7) 0.0245(11) 0.0433(17) -0.0108(12) -0.0092(12) 0.0046(7) C10 0.0212(8) 0.037(2) 0.0296(19) -0.0058(13) 0.0004(12) 0.0011(11) C11' 0.0153(7) 0.0281(11) 0.0374(11) -0.0018(9) -0.0009(9) 0.0021(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 Li1 O8 1.933(3) . ? Li1 O11 1.934(3) . ? Li1 O5 1.936(3) . ? Li1 O1 2.127(4) . ? Li1 O1' 2.167(19) . ? Li1 O4 2.267(4) 3 ? S1 O1 1.4203(15) . ? S1 O2 1.4440(17) . ? S1 N1 1.5760(18) . ? S1 C1 1.833(2) . ? S2 O4 1.4254(17) . ? S2 O3 1.4363(16) . ? S2 N1 1.5797(16) . ? S2 C2 1.8252(19) . ? O4 Li1 2.267(4) 3_554 ? C1 F1 1.302(3) . ? C1 F2 1.306(3) . ? C1 F3 1.320(3) . ? C2 F5 1.319(2) . ? C2 F4 1.322(2) . ? C2 F6 1.336(2) . ? S2' O3' 1.425(18) . ? S2' O4' 1.435(18) . ? S2' N1' 1.547(14) . ? O5 C3 1.205(2) . ? C3 O6 1.316(2) . ? C3 O7 1.329(2) . ? O6 C4 1.4462(19) . ? O7 C5 1.452(2) . ? C4 C5 1.513(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? O8 C6 1.210(2) . ? C6 O9 1.313(2) . ? C6 O10 1.331(2) . ? O9 C7 1.442(3) . ? O10 C8 1.450(3) . ? C7 C8 1.515(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O11 C9 1.205(2) . ? C9 O12 1.313(2) . ? C9 O13 1.328(3) . ? O12 C10' 1.469(4) . ? O13 C11 1.458(4) . ? C10' C11 1.424(6) . ? C10' H10A 0.9900 . ? C10' H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? O13' C11' 1.448(3) . ? C10 C11' 1.258(5) . ? C10 H10C 0.9900 . ? C10 H10D 0.9900 . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? 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 O8 Li1 O11 114.06(17) . . ? O8 Li1 O5 119.17(17) . . ? O11 Li1 O5 126.64(18) . . ? O8 Li1 O1 98.21(16) . . ? O11 Li1 O1 84.22(15) . . ? O5 Li1 O1 91.72(15) . . ? O8 Li1 O1' 76.6(7) . . ? O11 Li1 O1' 100.6(6) . . ? O5 Li1 O1' 94.9(5) . . ? O1 Li1 O1' 23.1(7) . . ? O8 Li1 O4 89.47(15) . 3 ? O11 Li1 O4 83.81(14) . 3 ? O5 Li1 O4 92.95(15) . 3 ? O1 Li1 O4 167.65(17) . 3 ? O1' Li1 O4 166.1(7) . 3 ? O1 S1 O2 118.78(12) . . ? O1 S1 N1 109.11(11) . . ? O2 S1 N1 115.85(9) . . ? O1 S1 C1 103.14(10) . . ? O2 S1 C1 104.19(11) . . ? N1 S1 C1 103.62(11) . . ? S1 O1 Li1 146.09(15) . . ? O4 S2 O3 117.85(11) . . ? O4 S2 N1 108.58(10) . . ? O3 S2 N1 116.55(9) . . ? O4 S2 C2 103.95(9) . . ? O3 S2 C2 104.49(9) . . ? N1 S2 C2 103.46(9) . . ? S2 O4 Li1 155.69(13) . 3_554 ? S1 N1 S2 124.45(11) . . ? F1 C1 F2 108.5(2) . . ? F1 C1 F3 109.3(2) . . ? F2 C1 F3 106.7(2) . . ? F1 C1 S1 110.71(18) . . ? F2 C1 S1 111.12(16) . . ? F3 C1 S1 110.32(17) . . ? F5 C2 F4 108.63(17) . . ? F5 C2 F6 108.58(15) . . ? F4 C2 F6 107.93(16) . . ? F5 C2 S2 112.71(13) . . ? F4 C2 S2 110.70(12) . . ? F6 C2 S2 108.16(13) . . ? O3' S2' O4' 118.8(12) . . ? O3' S2' N1' 103.0(10) . . ? O4' S2' N1' 122.6(10) . . ? C3 O5 Li1 146.50(17) . . ? O5 C3 O6 123.01(17) . . ? O5 C3 O7 124.50(17) . . ? O6 C3 O7 112.49(15) . . ? C3 O6 C4 109.78(13) . . ? C3 O7 C5 109.25(14) . . ? O6 C4 C5 103.15(13) . . ? O6 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? O6 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? O7 C5 C4 103.04(13) . . ? O7 C5 H5A 111.2 . . ? C4 C5 H5A 111.2 . . ? O7 C5 H5B 111.2 . . ? C4 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C6 O8 Li1 138.13(17) . . ? O8 C6 O9 124.10(17) . . ? O8 C6 O10 122.87(18) . . ? O9 C6 O10 113.01(17) . . ? C6 O9 C7 109.85(15) . . ? C6 O10 C8 109.40(16) . . ? O9 C7 C8 104.06(18) . . ? O9 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? O9 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 109.0 . . ? O10 C8 C7 103.43(16) . . ? O10 C8 H8A 111.1 . . ? C7 C8 H8A 111.1 . . ? O10 C8 H8B 111.1 . . ? C7 C8 H8B 111.1 . . ? H8A C8 H8B 109.0 . . ? C9 O11 Li1 151.40(18) . . ? O11 C9 O12 124.34(18) . . ? O11 C9 O13 120.4(2) . . ? O12 C9 O13 113.21(19) . . ? C9 O12 C10' 109.1(2) . . ? C9 O13 C11 106.7(3) . . ? C11 C10' O12 103.6(3) . . ? C11 C10' H10A 111.0 . . ? O12 C10' H10A 111.0 . . ? C11 C10' H10B 111.0 . . ? O12 C10' H10B 111.0 . . ? H10A C10' H10B 109.0 . . ? C10' C11 O13 107.4(3) . . ? C10' C11 H11A 110.2 . . ? O13 C11 H11A 110.2 . . ? C10' C11 H11B 110.2 . . ? O13 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C11' C10 H10C 109.6 . . ? C11' C10 H10D 109.6 . . ? H10C C10 H10D 108.1 . . ? C10 C11' O13' 105.3(3) . . ? C10 C11' H11C 110.7 . . ? O13' C11' H11C 110.7 . . ? C10 C11' H11D 110.7 . . ? O13' C11' H11D 110.7 . . ? H11C C11' H11D 108.8 . . ? 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 O2 S1 O1 Li1 -39.5(3) . . . . ? N1 S1 O1 Li1 96.3(3) . . . . ? C1 S1 O1 Li1 -154.0(3) . . . . ? O8 Li1 O1 S1 73.1(3) . . . . ? O11 Li1 O1 S1 -173.4(2) . . . . ? O5 Li1 O1 S1 -46.7(3) . . . . ? O1' Li1 O1 S1 51.7(13) . . . . ? O4 Li1 O1 S1 -158.9(7) 3 . . . ? O3 S2 O4 Li1 -83.5(4) . . . 3_554 ? N1 S2 O4 Li1 51.8(4) . . . 3_554 ? C2 S2 O4 Li1 161.5(3) . . . 3_554 ? O1 S1 N1 S2 -158.06(12) . . . . ? O2 S1 N1 S2 -20.85(17) . . . . ? C1 S1 N1 S2 92.58(14) . . . . ? O4 S2 N1 S1 -157.57(12) . . . . ? O3 S2 N1 S1 -21.60(17) . . . . ? C2 S2 N1 S1 92.44(13) . . . . ? O1 S1 C1 F1 61.8(2) . . . . ? O2 S1 C1 F1 -62.9(2) . . . . ? N1 S1 C1 F1 175.5(2) . . . . ? O1 S1 C1 F2 -177.5(2) . . . . ? O2 S1 C1 F2 57.8(2) . . . . ? N1 S1 C1 F2 -63.8(2) . . . . ? O1 S1 C1 F3 -59.3(2) . . . . ? O2 S1 C1 F3 176.0(2) . . . . ? N1 S1 C1 F3 54.4(2) . . . . ? O4 S2 C2 F5 -178.60(14) . . . . ? O3 S2 C2 F5 57.25(16) . . . . ? N1 S2 C2 F5 -65.21(15) . . . . ? O4 S2 C2 F4 -56.69(16) . . . . ? O3 S2 C2 F4 179.15(14) . . . . ? N1 S2 C2 F4 56.70(16) . . . . ? O4 S2 C2 F6 61.36(14) . . . . ? O3 S2 C2 F6 -62.80(14) . . . . ? N1 S2 C2 F6 174.75(12) . . . . ? O8 Li1 O5 C3 68.5(4) . . . . ? O11 Li1 O5 C3 -107.0(3) . . . . ? O1 Li1 O5 C3 168.9(3) . . . . ? O1' Li1 O5 C3 145.9(8) . . . . ? O4 Li1 O5 C3 -22.5(3) 3 . . . ? Li1 O5 C3 O6 -146.7(3) . . . . ? Li1 O5 C3 O7 33.3(4) . . . . ? O5 C3 O6 C4 174.35(17) . . . . ? O7 C3 O6 C4 -5.7(2) . . . . ? O5 C3 O7 C5 175.27(18) . . . . ? O6 C3 O7 C5 -4.7(2) . . . . ? C3 O6 C4 C5 12.89(19) . . . . ? C3 O7 C5 C4 12.3(2) . . . . ? O6 C4 C5 O7 -14.61(18) . . . . ? O11 Li1 O8 C6 107.7(3) . . . . ? O5 Li1 O8 C6 -68.4(3) . . . . ? O1 Li1 O8 C6 -165.0(2) . . . . ? O1' Li1 O8 C6 -156.6(6) . . . . ? O4 Li1 O8 C6 24.7(3) 3 . . . ? Li1 O8 C6 O9 41.1(3) . . . . ? Li1 O8 C6 O10 -140.6(2) . . . . ? O8 C6 O9 C7 -178.4(2) . . . . ? O10 C6 O9 C7 3.1(2) . . . . ? O8 C6 O10 C8 -178.21(19) . . . . ? O9 C6 O10 C8 0.3(2) . . . . ? C6 O9 C7 C8 -4.9(2) . . . . ? C6 O10 C8 C7 -3.3(2) . . . . ? O9 C7 C8 O10 4.8(2) . . . . ? O8 Li1 O11 C9 -76.3(5) . . . . ? O5 Li1 O11 C9 99.4(5) . . . . ? O1 Li1 O11 C9 -172.7(4) . . . . ? O1' Li1 O11 C9 -156.3(7) . . . . ? O4 Li1 O11 C9 10.3(4) 3 . . . ? Li1 O11 C9 O12 92.5(4) . . . . ? Li1 O11 C9 O13 -104.9(5) . . . . ? O11 C9 O12 C10' 165.5(3) . . . . ? O13 C9 O12 C10' 1.8(3) . . . . ? O11 C9 O13 C11 -167.4(3) . . . . ? O12 C9 O13 C11 -2.9(4) . . . . ? C9 O12 C10' C11 0.2(4) . . . . ? O12 C10' C11 O13 -1.9(5) . . . . ? C9 O13 C11 C10' 2.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.691 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.072 _iucr_refine_instructions_details ; TITL x12120: 110K CELL 0.71073 8.72877 14.04451 16.04085 90.0000 90.0000 90.0000 ZERR 4 0.00289 0.00469 0.00577 0.0000 0.0000 0.0000 LATT -1 SYMM -X,-Y, 0.50000+Z SYMM 0.50000-X,Y, 0.50000+Z SYMM 0.50000+X,-Y,Z SFAC C H F LI N O S UNIT 44 48 24 4 4 52 8 TEMP -163 SIZE 0.556 0.216 0.161 ACTA 72.64 EXYZ S1 S1' EXYZ C1 C1' EXYZ F1 F1' EXYZ F2 F2' EXYZ F3 F3' EXYZ C2 C2' EXYZ F4 F4' EXYZ F5 F5' EXYZ F6 F6' EADP S1 S1' EADP C1 C1' EADP F1 F1' EADP F2 F2' EADP F3 F3' EADP C2 C2' EADP F4 F4' EADP F5 F5' EADP F6 F6' EADP O1 O1' EADP O2 O2' EADP N1 N1' EADP O3 O3' EADP O4 O4' DFIX 31 S1 N1 S2 N1 S1' N1' S2' N1' EXYZ O11 O11' EXYZ C9 C9' EXYZ O12 O12' EADP O11 O11' EADP C9 C9' EADP O12 O12' DFIX 1.33 0.005 C9 O12 C9' O12' C9 O13 C9' O13' DFIX 1.45 0.005 O12 C10 O12' C10' O13 C11 O13' C11' DFIX 1.51 0.005 C10 C11 C10' C11' EADP O13 O13' EADP C11 C11' EADP C10 C10' MERG 2 L.S. 12 FMAP 2 PLAN 25 BOND $H CONF TWIN WGHT 0.067400 0.524700 BASF 0.09991 FVAR 0.18353 0.91926 1.53418 0.47234 LI1 4 0.236715 0.245427 0.641246 11.00000 0.02381 0.02072 = 0.03332 -0.00428 -0.00434 0.00320 PART 1 S1 7 0.447525 0.306185 0.471157 21.00000 0.03163 0.02197 = 0.02161 0.00154 0.00708 0.00032 O1 6 0.329686 0.309303 0.532157 21.00000 0.04530 0.03634 = 0.03143 -0.00087 0.02235 0.00126 O2 6 0.601448 0.283075 0.497207 21.00000 0.03493 0.03457 = 0.03067 -0.00560 -0.00410 0.00841 S2 7 0.493108 0.202311 0.324830 21.00000 0.02466 0.01922 = 0.02104 0.00098 0.00463 0.00238 O3 6 0.648375 0.235734 0.320051 21.00000 0.03191 0.02969 = 0.04083 -0.00970 0.01800 -0.00691 O4 6 0.409261 0.193519 0.248966 21.00000 0.04844 0.03300 = 0.02206 0.00311 -0.00360 0.01404 N1 5 0.386938 0.251490 0.391958 21.00000 0.02286 0.02409 = 0.02683 -0.00129 0.00421 0.00307 C1 1 0.460474 0.430078 0.435998 21.00000 0.04823 0.02406 = 0.04627 0.00565 0.00924 0.00185 F1 3 0.499481 0.485749 0.497348 21.00000 0.16602 0.03030 = 0.05173 -0.01338 0.01305 -0.01601 F2 3 0.561366 0.439235 0.376384 21.00000 0.08073 0.03773 = 0.04758 0.00632 0.01846 -0.02220 F3 3 0.327867 0.458422 0.405266 21.00000 0.06032 0.04031 = 0.14107 0.02996 -0.01191 0.01463 C2 1 0.509687 0.080070 0.362391 21.00000 0.02555 0.02185 = 0.03030 0.00135 -0.00535 0.00343 F4 3 0.372862 0.040884 0.370756 21.00000 0.03281 0.03843 = 0.06056 0.01485 -0.00721 -0.01034 F5 3 0.582386 0.074143 0.434315 21.00000 0.04435 0.03937 = 0.03412 0.00524 -0.01591 0.00262 F6 3 0.587314 0.029888 0.305652 21.00000 0.04735 0.02726 = 0.04590 -0.00838 -0.00430 0.01053 PART 2 S1' 7 0.447525 0.306185 0.471157 -21.00000 0.03163 0.02197 = 0.02161 0.00154 0.00708 0.00032 O1' 6 0.411372 0.308041 0.562400 -21.00000 0.04530 0.03634 = 0.03143 -0.00087 0.02235 0.00126 O2' 6 0.287712 0.304707 0.426976 -21.00000 0.03493 0.03457 = 0.03067 -0.00560 -0.00410 0.00841 S2' 7 0.579928 0.212189 0.354965 -21.00000 0.01322 0.02165 = 0.01828 -0.00324 0.00322 -0.00149 O3' 6 0.739170 0.203092 0.336948 -21.00000 0.03191 0.02969 = 0.04083 -0.00970 0.01800 -0.00691 O4' 6 0.479281 0.245995 0.290749 -21.00000 0.04844 0.03300 = 0.02206 0.00311 -0.00360 0.01404 N1' 5 0.579410 0.253584 0.444352 -21.00000 0.02286 0.02409 = 0.02683 -0.00129 0.00421 0.00307 C1' 1 0.460474 0.430078 0.435998 -21.00000 0.04823 0.02406 = 0.04627 0.00565 0.00924 0.00185 F1' 3 0.499481 0.485749 0.497348 -21.00000 0.16602 0.03030 = 0.05173 -0.01338 0.01305 -0.01601 F2' 3 0.561366 0.439235 0.376384 -21.00000 0.08073 0.03773 = 0.04758 0.00632 0.01846 -0.02220 F3' 3 0.327867 0.458422 0.405266 -21.00000 0.06032 0.04031 = 0.14107 0.02996 -0.01191 0.01463 C2' 1 0.509687 0.080070 0.362391 -21.00000 0.02555 0.02185 = 0.03030 0.00135 -0.00535 0.00343 F4' 3 0.372862 0.040884 0.370756 -21.00000 0.03281 0.03843 = 0.06056 0.01485 -0.00721 -0.01034 F5' 3 0.582386 0.074143 0.434315 -21.00000 0.04435 0.03937 = 0.03412 0.00524 -0.01591 0.00262 F6' 3 0.587314 0.029888 0.305652 -21.00000 0.04735 0.02726 = 0.04590 -0.00838 -0.00430 0.01053 PART 0 O5 6 0.253797 0.119316 0.593358 11.00000 0.06196 0.01873 = 0.03286 -0.00151 -0.00178 0.00324 C3 1 0.247466 0.034725 0.605519 11.00000 0.02941 0.02209 = 0.02116 -0.00035 -0.00339 0.00257 O6 6 0.333587 -0.027093 0.565397 11.00000 0.03392 0.01789 = 0.03298 0.00474 0.01124 0.00010 O7 6 0.154321 -0.006700 0.660060 11.00000 0.03955 0.03130 = 0.03761 0.00119 0.01500 0.00757 C4 1 0.310345 -0.121315 0.599494 11.00000 0.02359 0.01821 = 0.03404 0.00385 0.00140 0.00084 AFIX 23 H4A 2 0.399289 -0.141533 0.633453 11.00000 -1.20000 H4B 2 0.293011 -0.168586 0.554694 11.00000 -1.20000 AFIX 0 C5 1 0.168792 -0.109394 0.652915 11.00000 0.02652 0.02829 = 0.03191 0.00564 0.00523 -0.00533 AFIX 23 H5A 2 0.077705 -0.137489 0.625580 11.00000 -1.20000 H5B 2 0.182735 -0.139279 0.708294 11.00000 -1.20000 AFIX 0 O8 6 0.389988 0.287832 0.719871 11.00000 0.03055 0.03512 = 0.03831 0.00542 -0.01272 -0.00765 C6 1 0.430844 0.269176 0.790109 11.00000 0.02175 0.02275 = 0.03514 -0.00286 -0.00720 -0.00025 O9 6 0.441763 0.182326 0.819861 11.00000 0.03996 0.02275 = 0.02729 -0.00459 -0.00624 0.00211 O10 6 0.473133 0.335518 0.844726 11.00000 0.04136 0.02235 = 0.05325 -0.01185 -0.01954 0.00269 C7 1 0.489443 0.185549 0.905895 11.00000 0.05120 0.03398 = 0.03118 -0.00355 -0.01429 0.01170 AFIX 23 H7A 2 0.583294 0.147252 0.914648 11.00000 -1.20000 H7B 2 0.407673 0.161380 0.943062 11.00000 -1.20000 AFIX 0 C8 1 0.519954 0.290164 0.921858 11.00000 0.04130 0.04065 = 0.03627 -0.01248 -0.01336 0.00322 AFIX 23 H8A 2 0.458653 0.313722 0.969512 11.00000 -1.20000 H8B 2 0.629867 0.301644 0.933293 11.00000 -1.20000 AFIX 0 PART 3 O11 6 0.070834 0.334773 0.624735 41.00000 0.03143 0.05402 = 0.04006 0.01764 0.00859 0.02219 C9 1 -0.046053 0.372545 0.647283 41.00000 0.02117 0.02795 = 0.02560 0.00852 0.00005 0.00500 O12 6 -0.051852 0.452459 0.689686 41.00000 0.01667 0.05886 = 0.06331 -0.02706 -0.00221 -0.00644 O13 6 -0.179197 0.349014 0.612883 41.00000 0.02598 0.02451 = 0.04329 -0.01080 -0.00921 0.00464 C10' 1 -0.209110 0.489544 0.687497 41.00000 0.02116 0.03684 = 0.02960 -0.00579 0.00040 0.00113 AFIX 23 H10A 2 -0.252379 0.494422 0.744387 41.00000 -1.20000 H10B 2 -0.212683 0.553002 0.660696 41.00000 -1.20000 AFIX 0 C11 1 -0.289800 0.420769 0.639261 41.00000 0.01531 0.02809 = 0.03736 -0.00179 -0.00090 0.00212 AFIX 23 H11A 2 -0.337284 0.451382 0.590038 41.00000 -1.20000 H11B 2 -0.371756 0.391041 0.673066 41.00000 -1.20000 AFIX 0 PART 4 O11' 6 0.070834 0.334773 0.624735 -41.00000 0.03143 0.05402 = 0.04006 0.01764 0.00859 0.02219 C9' 1 -0.046053 0.372545 0.647283 -41.00000 0.02117 0.02795 = 0.02560 0.00852 0.00005 0.00500 O12' 6 -0.051852 0.452459 0.689686 -41.00000 0.01667 0.05886 = 0.06331 -0.02706 -0.00221 -0.00644 O13' 6 -0.183481 0.332605 0.647458 -41.00000 0.02598 0.02451 = 0.04329 -0.01080 -0.00921 0.00464 C10 1 -0.212513 0.464841 0.713628 -41.00000 0.02116 0.03684 = 0.02960 -0.00579 0.00040 0.00113 AFIX 23 H10C 2 -0.220057 0.471555 0.774927 -41.00000 -1.20000 H10D 2 -0.253487 0.523614 0.687862 -41.00000 -1.20000 AFIX 0 C11' 1 -0.290456 0.394431 0.690216 -41.00000 0.01531 0.02809 = 0.03736 -0.00179 -0.00090 0.00212 AFIX 23 H11C 2 -0.373493 0.414790 0.652142 -41.00000 -1.20000 H11D 2 -0.336513 0.361450 0.738663 -41.00000 -1.20000 PART 0 HKLF 4 REM x12120: 110K REM R1 = 0.0472 for 7953 Fo > 4sig(Fo) and 0.0730 for all 10519 data REM 344 parameters refined using 15 restraints END WGHT 0.0646 0.5702 REM Highest difference peak 0.691, deepest hole -0.524, 1-sigma level 0.072 Q1 1 0.3655 0.0927 0.3980 11.00000 0.05 0.69 Q2 1 0.6142 0.4543 0.4985 11.00000 0.05 0.64 Q3 1 0.3612 0.4973 0.4854 11.00000 0.05 0.61 Q4 1 0.5034 0.3133 0.4924 11.00000 0.05 0.60 Q5 1 0.3994 0.3329 0.4814 11.00000 0.05 0.53 Q6 1 0.4805 0.4527 0.3798 11.00000 0.05 0.50 Q7 1 0.4999 0.1294 0.3432 11.00000 0.05 0.44 Q8 1 -0.0770 0.4587 0.6599 11.00000 0.05 0.42 Q9 1 0.4545 0.4745 0.4972 11.00000 0.05 0.39 Q10 1 -0.0024 0.3521 0.6184 11.00000 0.05 0.38 Q11 1 0.3154 -0.0008 0.6040 11.00000 0.05 0.37 Q12 1 0.5233 0.0461 0.3098 11.00000 0.05 0.36 Q13 1 0.5991 0.0272 0.4388 11.00000 0.05 0.35 Q14 1 0.5047 0.4956 0.4790 11.00000 0.05 0.34 Q15 1 -0.2183 0.5328 0.7336 11.00000 0.05 0.33 Q16 1 0.0019 0.4511 0.6787 11.00000 0.05 0.33 Q17 1 0.4951 0.4456 0.4665 11.00000 0.05 0.32 Q18 1 0.5320 0.3291 0.8285 11.00000 0.05 0.32 Q19 1 -0.0369 0.4199 0.7018 11.00000 0.05 0.32 Q20 1 0.5615 0.2221 0.3089 11.00000 0.05 0.31 Q21 1 0.4213 0.2757 0.4186 11.00000 0.05 0.30 Q22 1 0.4545 0.3772 0.4533 11.00000 0.05 0.30 Q23 1 0.4491 0.3060 0.8226 11.00000 0.05 0.29 Q24 1 -0.3994 0.3835 0.6462 11.00000 0.05 0.29 Q25 1 0.5502 0.2661 0.4492 11.00000 0.05 0.29 ; _database_code_depnum_ccdc_archive 'CCDC 875816'