# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 #TrackingRef 'compound 1.cif' # 1. SUBMISSION DETAILS _publ_contact_author ; M.A. Monge Bravo Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; _publ_contact_author_phone '34 1 334-9025' _publ_contact_author_fax '34 1 372-0623' _publ_contact_author_email amonge@icmm.csic.es _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis, Crystal Structure and Characterization of Rare-Earth Sulfate-Succinate 3D Frameworks With Multifunctional Properties ; loop_ _publ_author_name _publ_author_address 'Richard Fernando D`Vries' ; Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; 'Natalia Snejko' ; Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; 'Marta Iglesias' ; Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; 'Enrique Gutierrez-Puebla' ; Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; 'M. Angeles Monge' ; Instituto de Ciencia de Materiales CSIC Campus de Cantoblanco 28049 MADRID Spain ; _publ_contact_author_name 'M.A. Monge Bravo' #============================================================================== data_data2t _database_code_depnum_ccdc_archive 'CCDC 828893' #TrackingRef 'compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 La2 O14 S' _chemical_formula_sum 'C8 H12 La2 O14 S' _chemical_formula_weight 642.07 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' 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' La La -0.2871 2.4523 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.881(2) _cell_length_b 9.6559(16) _cell_length_c 13.088(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.357(3) _cell_angle_gamma 90.00 _cell_volume 1526.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 3510 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.57 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208.0 _exptl_absorpt_coefficient_mu 5.763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5739 _exptl_absorpt_correction_T_max 0.7269 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12024 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3091 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0090P)^2^+16.4269P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3091 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 La1 La 0.45869(3) 0.65956(4) 0.38491(3) 0.01012(11) Uani 1 1 d . . . La2 La 0.55146(3) 0.86532(4) 0.13082(3) 0.00999(11) Uani 1 1 d . . . S1 S 0.74942(14) 0.49710(18) 0.50244(13) 0.0115(3) Uani 1 1 d . . . O2 O 0.5616(4) 0.8622(5) 0.3367(4) 0.0180(11) Uani 1 1 d . . . O14 O 0.6643(4) 0.5986(5) 0.4412(4) 0.0204(11) Uani 1 1 d . . . O6 O 0.4519(4) 0.6687(5) 0.1838(4) 0.0179(11) Uani 1 1 d . . . O12 O 0.2963(4) 0.6002(5) 0.4373(4) 0.0172(11) Uani 1 1 d . . . C7 C 0.3596(6) 0.6029(7) 0.1436(5) 0.0132(14) Uani 1 1 d . . . O4 O 0.4740(4) 0.4050(5) 0.4022(4) 0.0164(11) Uani 1 1 d . . . O11 O 0.3435(4) 0.9273(5) 0.0811(4) 0.0173(11) Uani 1 1 d . . . O1 O 0.6709(5) 1.0064(6) 0.2955(4) 0.0252(13) Uani 1 1 d . . . O7 O 0.5423(5) 0.6827(5) -0.0139(4) 0.0260(13) Uani 1 1 d . . . O8 O 0.5265(4) 1.1156(5) 0.0810(4) 0.0162(10) Uani 1 1 d . . . O5 O 0.3168(4) 0.5500(6) 0.2063(4) 0.0234(12) Uani 1 1 d . . . O3 O 0.4986(5) 0.8128(5) 0.5495(4) 0.0243(12) Uani 1 1 d . . . O9 O 0.7127(4) 0.9215(6) 0.0758(4) 0.0212(12) Uani 1 1 d . . . C2 C 0.6966(6) 0.9834(8) 0.4849(6) 0.0187(16) Uani 1 1 d . . . H2A H 0.6519 0.9537 0.5272 0.022 Uiso 1 1 calc R . . H2B H 0.7087 1.0824 0.4948 0.022 Uiso 1 1 calc R . . O10 O 0.6926(5) 0.6916(6) 0.2406(4) 0.0268(13) Uani 1 1 d . . . H10A H 0.7369 0.6130 0.2239 0.032 Uiso 1 1 d . . . H10B H 0.7410 0.6820 0.3250 0.032 Uiso 1 1 d . . . C8 C 0.5255(6) 0.7231(7) 0.6221(5) 0.0141(15) Uani 1 1 d . . . C1 C 0.6382(6) 0.9508(7) 0.3666(5) 0.0146(15) Uani 1 1 d . . . C6 C 0.3077(6) 0.5932(8) 0.0231(5) 0.0186(16) Uani 1 1 d . . . H6A H 0.3583 0.5458 -0.0053 0.022 Uiso 1 1 calc R . . H6B H 0.2965 0.6860 -0.0071 0.022 Uiso 1 1 calc R . . C3 C 0.5516(6) 0.7657(8) 0.7405(5) 0.0172(15) Uani 1 1 d . . . H3A H 0.5490 0.8659 0.7444 0.021 Uiso 1 1 calc R . . H3B H 0.6264 0.7367 0.7826 0.021 Uiso 1 1 calc R . . C4 C 0.4722(6) 0.7044(8) 0.7921(5) 0.0165(15) Uani 1 1 d . . . H4A H 0.3967 0.7282 0.7481 0.020 Uiso 1 1 calc R . . H4B H 0.4786 0.6042 0.7939 0.020 Uiso 1 1 calc R . . O13 O 0.3232(5) 0.8489(6) 0.2852(4) 0.0263(13) Uani 1 1 d . . . H13A H 0.3012 0.9135 0.3099 0.032 Uiso 1 1 d . . . H13B H 0.3063 0.8572 0.2044 0.032 Uiso 1 1 d . . . C5 C 0.4975(6) 0.7579(7) -0.0950(5) 0.0134(14) 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 La1 0.0105(2) 0.0119(2) 0.00806(18) 0.00103(14) 0.00342(14) -0.00044(16) La2 0.0101(2) 0.0121(2) 0.00800(18) 0.00081(14) 0.00344(14) -0.00020(15) S1 0.0087(8) 0.0150(8) 0.0119(8) 0.0005(6) 0.0048(6) 0.0003(7) O2 0.019(3) 0.019(3) 0.019(3) 0.000(2) 0.011(2) -0.005(2) O14 0.015(3) 0.021(3) 0.024(3) 0.009(2) 0.006(2) 0.005(2) O6 0.017(3) 0.020(3) 0.015(2) -0.002(2) 0.003(2) -0.003(2) O12 0.015(3) 0.021(3) 0.020(3) 0.005(2) 0.012(2) 0.000(2) C7 0.011(3) 0.015(4) 0.010(3) -0.002(3) -0.001(3) 0.005(3) O4 0.021(3) 0.015(3) 0.012(2) -0.0019(19) 0.003(2) 0.004(2) O11 0.016(3) 0.020(3) 0.014(2) 0.002(2) 0.002(2) 0.003(2) O1 0.029(3) 0.030(3) 0.014(3) 0.000(2) 0.005(2) -0.014(3) O7 0.044(4) 0.017(3) 0.016(3) 0.002(2) 0.010(2) 0.007(3) O8 0.022(3) 0.013(3) 0.013(2) -0.0007(19) 0.006(2) 0.002(2) O5 0.022(3) 0.035(3) 0.012(2) 0.005(2) 0.004(2) -0.015(2) O3 0.042(3) 0.015(3) 0.017(3) -0.001(2) 0.010(2) 0.001(2) O9 0.019(3) 0.031(3) 0.017(3) 0.006(2) 0.009(2) -0.002(2) C2 0.018(4) 0.021(4) 0.018(4) -0.004(3) 0.008(3) -0.004(3) O10 0.028(3) 0.027(3) 0.029(3) 0.008(2) 0.014(3) 0.015(3) C8 0.015(4) 0.016(4) 0.013(3) -0.003(3) 0.007(3) 0.002(3) C1 0.020(4) 0.011(3) 0.015(3) 0.004(3) 0.009(3) 0.007(3) C6 0.015(4) 0.022(4) 0.012(3) -0.002(3) -0.003(3) -0.009(3) C3 0.022(4) 0.021(4) 0.009(3) -0.008(3) 0.006(3) -0.004(3) C4 0.019(4) 0.020(4) 0.013(3) -0.002(3) 0.009(3) -0.001(3) O13 0.030(3) 0.027(3) 0.027(3) 0.009(2) 0.017(2) 0.015(3) C5 0.009(3) 0.018(4) 0.013(3) -0.005(3) 0.004(3) -0.003(3) _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 La1 O4 2.470(5) . ? La1 O12 2.484(5) . ? La1 O3 2.515(5) . ? La1 O13 2.551(5) . ? La1 O14 2.558(5) . ? La1 O2 2.563(5) . ? La1 O6 2.604(5) . ? La1 O5 2.637(5) . ? La1 O4 2.688(5) 3_666 ? La1 C8 2.982(7) . ? La1 C7 3.016(6) . ? La2 O9 2.483(5) . ? La2 O8 2.494(5) . ? La2 O6 2.519(5) . ? La2 O10 2.523(5) . ? La2 O7 2.560(5) . ? La2 O1 2.562(5) . ? La2 O11 2.597(5) . ? La2 O8 2.607(5) 3_675 ? La2 O2 2.652(5) . ? La2 C5 2.977(7) . ? La2 C1 3.009(7) . ? S1 O9 1.472(5) 2_645 ? S1 O12 1.474(5) 3_666 ? S1 O11 1.480(5) 4_676 ? S1 O14 1.482(5) . ? O2 C1 1.260(9) . ? O6 C7 1.289(8) . ? O12 S1 1.474(5) 3_666 ? C7 O5 1.246(8) . ? C7 C6 1.487(9) . ? O4 C8 1.277(8) 3_666 ? O4 La1 2.688(5) 3_666 ? O11 S1 1.480(5) 4_575 ? O1 C1 1.266(8) . ? O7 C5 1.250(9) . ? O8 C5 1.288(9) 3_675 ? O8 La2 2.607(5) 3_675 ? O3 C8 1.242(8) . ? O9 S1 1.472(5) 2_655 ? C2 C1 1.501(10) . ? C2 C6 1.533(10) 4_676 ? C8 O4 1.277(8) 3_666 ? C8 C3 1.524(9) . ? C6 C2 1.533(10) 4_575 ? C3 C4 1.527(9) . ? C4 C5 1.491(9) 1_556 ? C5 O8 1.288(9) 3_675 ? C5 C4 1.491(9) 1_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 La1 O12 78.07(17) . . ? O4 La1 O3 121.40(16) . . ? O12 La1 O3 80.79(17) . . ? O4 La1 O13 141.14(18) . . ? O12 La1 O13 79.33(17) . . ? O3 La1 O13 85.22(18) . . ? O4 La1 O14 72.72(17) . . ? O12 La1 O14 138.93(16) . . ? O3 La1 O14 90.34(18) . . ? O13 La1 O14 140.15(17) . . ? O4 La1 O2 138.63(16) . . ? O12 La1 O2 143.29(17) . . ? O3 La1 O2 78.05(16) . . ? O13 La1 O2 69.35(18) . . ? O14 La1 O2 70.98(16) . . ? O4 La1 O6 95.72(15) . . ? O12 La1 O6 123.48(16) . . ? O3 La1 O6 140.44(16) . . ? O13 La1 O6 71.47(16) . . ? O14 La1 O6 88.05(16) . . ? O2 La1 O6 64.11(15) . . ? O4 La1 O5 71.97(16) . . ? O12 La1 O5 76.21(16) . . ? O3 La1 O5 150.19(18) . . ? O13 La1 O5 72.17(18) . . ? O14 La1 O5 119.47(18) . . ? O2 La1 O5 110.28(15) . . ? O6 La1 O5 49.35(15) . . ? O4 La1 O4 71.81(17) . 3_666 ? O12 La1 O4 70.05(16) . 3_666 ? O3 La1 O4 49.60(16) . 3_666 ? O13 La1 O4 127.82(16) . 3_666 ? O14 La1 O4 73.74(16) . 3_666 ? O2 La1 O4 115.12(15) . 3_666 ? O6 La1 O4 160.21(16) . 3_666 ? O5 La1 O4 134.44(15) . 3_666 ? O4 La1 C8 97.16(17) . . ? O12 La1 C8 74.08(18) . . ? O3 La1 C8 24.25(18) . . ? O13 La1 C8 106.48(18) . . ? O14 La1 C8 81.53(18) . . ? O2 La1 C8 96.47(18) . . ? O6 La1 C8 160.22(18) . . ? O5 La1 C8 149.92(18) . . ? O4 La1 C8 25.35(17) 3_666 . ? O4 La1 C7 84.63(17) . . ? O12 La1 C7 99.03(18) . . ? O3 La1 C7 152.84(18) . . ? O13 La1 C7 68.23(18) . . ? O14 La1 C7 106.17(17) . . ? O2 La1 C7 86.99(17) . . ? O6 La1 C7 25.17(17) . . ? O5 La1 C7 24.29(17) . . ? O4 La1 C7 155.48(17) 3_666 . ? C8 La1 C7 172.26(19) . . ? O4 La1 La1 37.66(11) . 3_666 ? O12 La1 La1 70.03(11) . 3_666 ? O3 La1 La1 83.75(12) . 3_666 ? O13 La1 La1 148.70(12) . 3_666 ? O14 La1 La1 69.17(11) . 3_666 ? O2 La1 La1 135.77(11) . 3_666 ? O6 La1 La1 131.60(11) . 3_666 ? O5 La1 La1 105.51(12) . 3_666 ? O4 La1 La1 34.16(10) 3_666 3_666 ? C8 La1 La1 59.50(14) . 3_666 ? C7 La1 La1 121.99(13) . 3_666 ? O9 La2 O8 75.98(17) . . ? O9 La2 O6 143.26(17) . . ? O8 La2 O6 140.37(16) . . ? O9 La2 O10 78.51(17) . . ? O8 La2 O10 142.63(18) . . ? O6 La2 O10 71.15(18) . . ? O9 La2 O7 76.34(18) . . ? O8 La2 O7 120.37(16) . . ? O6 La2 O7 77.74(17) . . ? O10 La2 O7 78.60(18) . . ? O9 La2 O1 79.04(17) . . ? O8 La2 O1 71.92(17) . . ? O6 La2 O1 112.53(16) . . ? O10 La2 O1 76.78(19) . . ? O7 La2 O1 148.04(19) . . ? O9 La2 O11 140.42(16) . . ? O8 La2 O11 71.52(16) . . ? O6 La2 O11 70.34(16) . . ? O10 La2 O11 140.53(17) . . ? O7 La2 O11 101.25(17) . . ? O1 La2 O11 110.71(17) . . ? O9 La2 O8 74.18(16) . 3_675 ? O8 La2 O8 71.74(17) . 3_675 ? O6 La2 O8 107.56(15) . 3_675 ? O10 La2 O8 125.99(16) . 3_675 ? O7 La2 O8 50.22(16) . 3_675 ? O1 La2 O8 138.92(16) . 3_675 ? O11 La2 O8 74.64(15) . 3_675 ? O9 La2 O2 123.12(16) . . ? O8 La2 O2 103.45(15) . . ? O6 La2 O2 64.01(15) . . ? O10 La2 O2 69.05(17) . . ? O7 La2 O2 135.82(16) . . ? O1 La2 O2 49.32(16) . . ? O11 La2 O2 86.53(15) . . ? O8 La2 O2 161.15(16) 3_675 . ? O9 La2 C5 73.62(18) . . ? O8 La2 C5 96.53(18) . . ? O6 La2 C5 92.62(17) . . ? O10 La2 C5 101.95(19) . . ? O7 La2 C5 24.63(18) . . ? O1 La2 C5 152.24(18) . . ? O11 La2 C5 88.12(17) . . ? O8 La2 C5 25.59(17) 3_675 . ? O2 La2 C5 156.45(17) . . ? O9 La2 C1 100.82(18) . . ? O8 La2 C1 88.30(17) . . ? O6 La2 C1 88.12(17) . . ? O10 La2 C1 70.18(18) . . ? O7 La2 C1 148.50(17) . . ? O1 La2 C1 24.64(18) . . ? O11 La2 C1 100.18(17) . . ? O8 La2 C1 160.03(17) 3_675 . ? O2 La2 C1 24.71(17) . . ? C5 La2 C1 171.40(19) . . ? O9 La2 La2 71.45(12) . 3_675 ? O8 La2 La2 36.78(11) . 3_675 ? O6 La2 La2 130.92(11) . 3_675 ? O10 La2 La2 148.21(13) . 3_675 ? O7 La2 La2 84.35(12) . 3_675 ? O1 La2 La2 106.74(12) . 3_675 ? O11 La2 La2 69.01(11) . 3_675 ? O8 La2 La2 34.96(10) 3_675 3_675 ? O2 La2 La2 137.48(11) . 3_675 ? C5 La2 La2 60.00(14) . 3_675 ? C1 La2 La2 125.08(13) . 3_675 ? O9 S1 O12 110.3(3) 2_645 3_666 ? O9 S1 O11 109.8(3) 2_645 4_676 ? O12 S1 O11 109.0(3) 3_666 4_676 ? O9 S1 O14 108.3(3) 2_645 . ? O12 S1 O14 110.6(3) 3_666 . ? O11 S1 O14 108.8(3) 4_676 . ? C1 O2 La1 149.0(4) . . ? C1 O2 La2 93.7(4) . . ? La1 O2 La2 114.33(18) . . ? S1 O14 La1 143.6(3) . . ? C7 O6 La2 138.2(4) . . ? C7 O6 La1 95.6(4) . . ? La2 O6 La1 117.55(18) . . ? S1 O12 La1 145.7(3) 3_666 . ? O5 C7 O6 119.4(6) . . ? O5 C7 C6 122.3(6) . . ? O6 C7 C6 118.3(6) . . ? O5 C7 La1 60.6(3) . . ? O6 C7 La1 59.2(3) . . ? C6 C7 La1 173.1(5) . . ? C8 O4 La1 161.4(4) 3_666 . ? C8 O4 La1 90.3(4) 3_666 3_666 ? La1 O4 La1 108.19(17) . 3_666 ? S1 O11 La2 144.2(3) 4_575 . ? C1 O1 La2 97.8(4) . . ? C5 O7 La2 96.7(4) . . ? C5 O8 La2 153.8(4) 3_675 . ? C5 O8 La2 93.5(4) 3_675 3_675 ? La2 O8 La2 108.26(17) . 3_675 ? C7 O5 La1 95.2(4) . . ? C8 O3 La1 99.5(4) . . ? S1 O9 La2 145.4(3) 2_655 . ? C1 C2 C6 108.1(6) . 4_676 ? O3 C8 O4 120.6(6) . 3_666 ? O3 C8 C3 119.6(6) . . ? O4 C8 C3 119.7(6) 3_666 . ? O3 C8 La1 56.3(3) . . ? O4 C8 La1 64.3(3) 3_666 . ? C3 C8 La1 174.8(5) . . ? O2 C1 O1 119.0(6) . . ? O2 C1 C2 121.3(6) . . ? O1 C1 C2 119.6(7) . . ? O2 C1 La2 61.6(3) . . ? O1 C1 La2 57.5(4) . . ? C2 C1 La2 171.8(5) . . ? C7 C6 C2 113.6(6) . 4_575 ? C8 C3 C4 113.6(6) . . ? C5 C4 C3 110.8(6) 1_556 . ? O7 C5 O8 119.5(6) . 3_675 ? O7 C5 C4 121.2(6) . 1_554 ? O8 C5 C4 119.3(6) 3_675 1_554 ? O7 C5 La2 58.6(4) . . ? O8 C5 La2 60.9(3) 3_675 . ? C4 C5 La2 179.2(5) 1_554 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.472 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.192 # Attachment 'compound 2.cif' #============================================================================== data_data2t_2 _database_code_depnum_ccdc_archive 'CCDC 828894' #TrackingRef 'compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 O14 Pr2 S' _chemical_formula_sum 'C8 H12 O14 Pr2 S' _chemical_formula_weight 646.07 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' 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' Pr Pr -0.2180 2.8214 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7580(10) _cell_length_b 9.5881(8) _cell_length_c 12.9304(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.2330(10) _cell_angle_gamma 90.00 _cell_volume 1484.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 7211 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 29.23 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224.0 _exptl_absorpt_coefficient_mu 6.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4328 _exptl_absorpt_correction_T_max 0.8502 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11810 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3012 _reflns_number_gt 2705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+23.7203P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3012 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.376 _refine_ls_restrained_S_all 1.376 _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 Pr1 Pr -0.04115(4) 0.15849(5) 0.38439(4) 0.01044(13) Uani 1 1 d . . . Pr2 Pr 0.05132(4) 0.36598(5) 0.13085(3) 0.01038(13) Uani 1 1 d . . . S1 S 0.24912(17) -0.0031(2) 0.50241(17) 0.0123(4) Uani 1 1 d . . . O2 O 0.0598(5) 0.3621(6) 0.3353(5) 0.0164(13) Uani 1 1 d . . . O6 O -0.0469(5) 0.1696(6) 0.1846(5) 0.0176(13) Uani 1 1 d . . . O14 O 0.1635(5) 0.0994(7) 0.4404(5) 0.0207(14) Uani 1 1 d . . . C1 C 0.1374(8) 0.4513(9) 0.3656(7) 0.0170(18) Uani 1 1 d . . . O1 O 0.1699(6) 0.5065(7) 0.2932(5) 0.0242(15) Uani 1 1 d . . . O12 O -0.2034(5) 0.1005(7) 0.4364(5) 0.0182(13) Uani 1 1 d . . . C7 C -0.1392(7) 0.1031(8) 0.1435(7) 0.0117(17) Uani 1 1 d . . . C6 C -0.1919(7) 0.0922(10) 0.0219(7) 0.0176(19) Uani 1 1 d . . . H6A H -0.1411 0.0435 -0.0069 0.021 Uiso 1 1 calc R . . H6B H -0.2028 0.1854 -0.0092 0.021 Uiso 1 1 calc R . . C5 C -0.0025(7) 0.2586(9) -0.0935(7) 0.0152(18) Uani 1 1 d . . . O11 O -0.1552(5) 0.4269(7) 0.0818(5) 0.0172(13) Uani 1 1 d . . . O10 O 0.1926(6) 0.1954(7) 0.2388(5) 0.0259(16) Uani 1 1 d . . . H10A H 0.2374 0.1236 0.2171 0.073 Uiso 1 1 d . . . H10B H 0.1917 0.1723 0.3136 0.050 Uiso 1 1 d . . . O9 O 0.2125(5) 0.4202(7) 0.0767(5) 0.0203(14) Uani 1 1 d . . . O3 O -0.0005(6) 0.3111(7) 0.5464(5) 0.0254(15) Uani 1 1 d . . . O13 O -0.1755(6) 0.3452(7) 0.2866(5) 0.0238(15) Uani 1 1 d . . . H13A H -0.2171 0.4145 0.3151 0.071 Uiso 1 1 d . . . H13B H -0.1854 0.3671 0.2084 0.049 Uiso 1 1 d . . . O8 O 0.0261(5) 0.6140(6) 0.0789(5) 0.0158(13) Uani 1 1 d . . . O5 O -0.1813(5) 0.0486(7) 0.2077(5) 0.0230(15) Uani 1 1 d . . . C2 C 0.1968(8) 0.4833(10) 0.4842(7) 0.0202(19) Uani 1 1 d . . . H2A H 0.1523 0.4528 0.5275 0.024 Uiso 1 1 calc R . . H2B H 0.2087 0.5830 0.4943 0.024 Uiso 1 1 calc R . . C8 C 0.0249(7) 0.2220(9) 0.6214(7) 0.0146(18) Uani 1 1 d . . . O4 O 0.0257(5) 0.0929(6) 0.5963(5) 0.0178(13) Uani 1 1 d . . . C4 C -0.0283(8) 0.2039(10) -0.2085(7) 0.0179(19) Uani 1 1 d . . . H4A H -0.1047 0.2274 -0.2527 0.022 Uiso 1 1 calc R . . H4B H -0.0214 0.1031 -0.2064 0.022 Uiso 1 1 calc R . . O7 O 0.0425(6) 0.1837(7) -0.0110(5) 0.0257(15) Uani 1 1 d . . . C3 C 0.0513(8) 0.2663(10) -0.2610(7) 0.020(2) Uani 1 1 d . . . H3A H 0.0477 0.3672 -0.2580 0.024 Uiso 1 1 calc R . . H3B H 0.1270 0.2382 -0.2185 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pr1 0.0110(2) 0.0120(2) 0.0085(2) 0.00096(17) 0.00373(17) -0.00069(18) Pr2 0.0111(2) 0.0121(2) 0.0082(2) 0.00102(17) 0.00370(17) -0.00013(18) S1 0.0117(10) 0.0138(10) 0.0128(10) 0.0001(8) 0.0062(8) -0.0005(8) O2 0.019(3) 0.015(3) 0.018(3) -0.001(2) 0.010(3) -0.005(3) O6 0.018(3) 0.019(3) 0.016(3) -0.003(3) 0.006(3) -0.005(3) O14 0.020(3) 0.019(3) 0.023(3) 0.008(3) 0.008(3) 0.005(3) C1 0.028(5) 0.007(4) 0.020(4) -0.001(3) 0.012(4) 0.006(4) O1 0.028(4) 0.031(4) 0.013(3) 0.000(3) 0.006(3) -0.016(3) O12 0.013(3) 0.026(3) 0.020(3) 0.006(3) 0.010(3) -0.002(3) C7 0.008(4) 0.010(4) 0.013(4) -0.004(3) -0.002(3) 0.002(3) C6 0.017(4) 0.020(5) 0.011(4) 0.000(3) 0.001(3) -0.005(4) C5 0.015(4) 0.019(4) 0.014(4) -0.003(4) 0.007(3) -0.003(4) O11 0.016(3) 0.020(3) 0.015(3) 0.006(3) 0.004(3) 0.005(3) O10 0.029(4) 0.030(4) 0.024(4) 0.012(3) 0.016(3) 0.012(3) O9 0.021(3) 0.024(3) 0.018(3) 0.006(3) 0.008(3) 0.001(3) O3 0.040(4) 0.019(3) 0.018(3) 0.000(3) 0.011(3) 0.001(3) O13 0.027(4) 0.025(4) 0.024(3) 0.009(3) 0.015(3) 0.010(3) O8 0.023(3) 0.013(3) 0.012(3) -0.003(2) 0.007(2) 0.001(3) O5 0.023(3) 0.032(4) 0.013(3) 0.004(3) 0.005(3) -0.014(3) C2 0.022(5) 0.020(5) 0.018(5) -0.001(4) 0.007(4) -0.002(4) C8 0.012(4) 0.015(4) 0.016(4) -0.003(3) 0.005(3) 0.002(3) O4 0.025(3) 0.013(3) 0.013(3) -0.002(2) 0.004(3) 0.002(3) C4 0.021(5) 0.018(4) 0.019(4) -0.008(4) 0.013(4) 0.000(4) O7 0.044(4) 0.017(3) 0.017(3) 0.003(3) 0.012(3) 0.008(3) C3 0.026(5) 0.016(4) 0.016(4) -0.004(4) 0.004(4) 0.002(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 Pr1 O4 2.424(6) 3_556 ? Pr1 O12 2.452(6) . ? Pr1 O3 2.459(6) . ? Pr1 O13 2.498(6) . ? Pr1 O14 2.521(6) . ? Pr1 O2 2.537(6) . ? Pr1 O6 2.562(6) . ? Pr1 O5 2.589(6) . ? Pr1 O4 2.648(6) . ? Pr1 C8 2.948(8) . ? Pr1 C7 2.976(8) . ? Pr2 O9 2.446(6) . ? Pr2 O8 2.462(6) . ? Pr2 O10 2.476(7) . ? Pr2 O6 2.490(6) . ? Pr2 O7 2.508(6) . ? Pr2 O1 2.512(6) . ? Pr2 O8 2.552(6) 3_565 ? Pr2 O11 2.555(6) . ? Pr2 O2 2.609(6) . ? Pr2 C5 2.928(8) . ? Pr2 C1 2.963(9) . ? S1 O12 1.468(6) 3_556 ? S1 O9 1.474(6) 2_545 ? S1 O14 1.482(6) . ? S1 O11 1.488(6) 4_666 ? O2 C1 1.264(11) . ? O6 C7 1.281(10) . ? C1 O1 1.262(11) . ? C1 C2 1.489(12) . ? O12 S1 1.468(6) 3_556 ? C7 O5 1.249(10) . ? C7 C6 1.485(11) . ? C6 C2 1.516(12) 4_565 ? C5 O7 1.249(11) . ? C5 O8 1.287(11) 3_565 ? C5 C4 1.501(12) . ? O11 S1 1.488(6) 4_565 ? O9 S1 1.474(6) 2 ? O3 C8 1.249(11) . ? O8 C5 1.287(11) 3_565 ? O8 Pr2 2.552(6) 3_565 ? C2 C6 1.516(12) 4_666 ? C8 O4 1.281(10) . ? C8 C3 1.500(12) 1_556 ? O4 Pr1 2.424(6) 3_556 ? C4 C3 1.525(13) . ? C3 C8 1.500(12) 1_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Pr1 O12 78.0(2) 3_556 . ? O4 Pr1 O3 121.2(2) 3_556 . ? O12 Pr1 O3 81.4(2) . . ? O4 Pr1 O13 141.4(2) 3_556 . ? O12 Pr1 O13 78.7(2) . . ? O3 Pr1 O13 84.9(2) . . ? O4 Pr1 O14 73.0(2) 3_556 . ? O12 Pr1 O14 139.4(2) . . ? O3 Pr1 O14 89.8(2) . . ? O13 Pr1 O14 140.1(2) . . ? O4 Pr1 O2 139.5(2) 3_556 . ? O12 Pr1 O2 142.5(2) . . ? O3 Pr1 O2 77.2(2) . . ? O13 Pr1 O2 69.0(2) . . ? O14 Pr1 O2 71.3(2) . . ? O4 Pr1 O6 96.8(2) 3_556 . ? O12 Pr1 O6 123.6(2) . . ? O3 Pr1 O6 139.3(2) . . ? O13 Pr1 O6 71.6(2) . . ? O14 Pr1 O6 88.0(2) . . ? O2 Pr1 O6 63.62(19) . . ? O4 Pr1 O5 72.1(2) 3_556 . ? O12 Pr1 O5 76.0(2) . . ? O3 Pr1 O5 150.7(2) . . ? O13 Pr1 O5 72.6(2) . . ? O14 Pr1 O5 119.5(2) . . ? O2 Pr1 O5 110.37(19) . . ? O6 Pr1 O5 49.97(19) . . ? O4 Pr1 O4 70.8(2) 3_556 . ? O12 Pr1 O4 70.3(2) . . ? O3 Pr1 O4 50.4(2) . . ? O13 Pr1 O4 127.8(2) . . ? O14 Pr1 O4 73.6(2) . . ? O2 Pr1 O4 115.58(19) . . ? O6 Pr1 O4 160.1(2) . . ? O5 Pr1 O4 133.89(19) . . ? O4 Pr1 C8 96.6(2) 3_556 . ? O12 Pr1 C8 74.1(2) . . ? O3 Pr1 C8 24.7(2) . . ? O13 Pr1 C8 106.1(2) . . ? O14 Pr1 C8 81.5(2) . . ? O2 Pr1 C8 96.5(2) . . ? O6 Pr1 C8 159.8(2) . . ? O5 Pr1 C8 149.7(2) . . ? O4 Pr1 C8 25.7(2) . . ? O4 Pr1 C7 85.4(2) 3_556 . ? O12 Pr1 C7 99.1(2) . . ? O3 Pr1 C7 152.4(2) . . ? O13 Pr1 C7 68.4(2) . . ? O14 Pr1 C7 106.2(2) . . ? O2 Pr1 C7 86.6(2) . . ? O6 Pr1 C7 25.4(2) . . ? O5 Pr1 C7 24.7(2) . . ? O4 Pr1 C7 155.4(2) . . ? C8 Pr1 C7 172.3(2) . . ? O4 Pr1 Pr1 37.21(14) 3_556 3_556 ? O12 Pr1 Pr1 70.27(15) . 3_556 ? O3 Pr1 Pr1 84.01(15) . 3_556 ? O13 Pr1 Pr1 148.26(15) . 3_556 ? O14 Pr1 Pr1 69.41(14) . 3_556 ? O2 Pr1 Pr1 136.25(14) . 3_556 ? O6 Pr1 Pr1 132.16(14) . 3_556 ? O5 Pr1 Pr1 105.30(15) . 3_556 ? O4 Pr1 Pr1 33.62(13) . 3_556 ? C8 Pr1 Pr1 59.35(17) . 3_556 ? C7 Pr1 Pr1 122.36(16) . 3_556 ? O9 Pr2 O8 76.1(2) . . ? O9 Pr2 O10 77.4(2) . . ? O8 Pr2 O10 142.4(2) . . ? O9 Pr2 O6 142.6(2) . . ? O8 Pr2 O6 140.9(2) . . ? O10 Pr2 O6 71.4(2) . . ? O9 Pr2 O7 76.6(2) . . ? O8 Pr2 O7 120.3(2) . . ? O10 Pr2 O7 78.0(2) . . ? O6 Pr2 O7 77.1(2) . . ? O9 Pr2 O1 78.6(2) . . ? O8 Pr2 O1 72.2(2) . . ? O10 Pr2 O1 76.9(2) . . ? O6 Pr2 O1 112.8(2) . . ? O7 Pr2 O1 147.8(2) . . ? O9 Pr2 O8 74.6(2) . 3_565 ? O8 Pr2 O8 70.8(2) . 3_565 ? O10 Pr2 O8 126.0(2) . 3_565 ? O6 Pr2 O8 107.81(19) . 3_565 ? O7 Pr2 O8 51.1(2) . 3_565 ? O1 Pr2 O8 138.4(2) . 3_565 ? O9 Pr2 O11 141.0(2) . . ? O8 Pr2 O11 71.7(2) . . ? O10 Pr2 O11 141.1(2) . . ? O6 Pr2 O11 70.5(2) . . ? O7 Pr2 O11 101.3(2) . . ? O1 Pr2 O11 110.8(2) . . ? O8 Pr2 O11 74.47(19) 3_565 . ? O9 Pr2 O2 123.3(2) . . ? O8 Pr2 O2 104.24(19) . . ? O10 Pr2 O2 69.7(2) . . ? O6 Pr2 O2 63.58(19) . . ? O7 Pr2 O2 135.0(2) . . ? O1 Pr2 O2 50.12(19) . . ? O8 Pr2 O2 160.57(19) 3_565 . ? O11 Pr2 O2 86.12(19) . . ? O9 Pr2 C5 73.9(2) . . ? O8 Pr2 C5 96.1(2) . . ? O10 Pr2 C5 101.7(2) . . ? O6 Pr2 C5 92.4(2) . . ? O7 Pr2 C5 25.1(2) . . ? O1 Pr2 C5 152.1(2) . . ? O8 Pr2 C5 26.0(2) 3_565 . ? O11 Pr2 C5 88.1(2) . . ? O2 Pr2 C5 155.9(2) . . ? O9 Pr2 C1 100.6(2) . . ? O8 Pr2 C1 88.8(2) . . ? O10 Pr2 C1 70.4(2) . . ? O6 Pr2 C1 88.1(2) . . ? O7 Pr2 C1 148.0(2) . . ? O1 Pr2 C1 25.0(2) . . ? O8 Pr2 C1 159.7(2) 3_565 . ? O11 Pr2 C1 100.1(2) . . ? O2 Pr2 C1 25.2(2) . . ? C5 Pr2 C1 171.4(2) . . ? O9 Pr2 Pr2 71.93(15) . 3_565 ? O8 Pr2 Pr2 36.15(13) . 3_565 ? O10 Pr2 Pr2 147.61(15) . 3_565 ? O6 Pr2 Pr2 131.18(14) . 3_565 ? O7 Pr2 Pr2 84.96(15) . 3_565 ? O1 Pr2 Pr2 106.42(15) . 3_565 ? O8 Pr2 Pr2 34.68(13) 3_565 3_565 ? O11 Pr2 Pr2 69.09(13) . 3_565 ? O2 Pr2 Pr2 137.48(14) . 3_565 ? C5 Pr2 Pr2 60.16(18) . 3_565 ? C1 Pr2 Pr2 124.99(16) . 3_565 ? O12 S1 O9 110.3(4) 3_556 2_545 ? O12 S1 O14 110.9(4) 3_556 . ? O9 S1 O14 108.3(4) 2_545 . ? O12 S1 O11 108.9(4) 3_556 4_666 ? O9 S1 O11 109.5(4) 2_545 4_666 ? O14 S1 O11 108.9(4) . 4_666 ? C1 O2 Pr1 148.7(6) . . ? C1 O2 Pr2 93.3(5) . . ? Pr1 O2 Pr2 114.7(2) . . ? C7 O6 Pr2 137.7(5) . . ? C7 O6 Pr1 95.7(5) . . ? Pr2 O6 Pr1 118.1(2) . . ? S1 O14 Pr1 143.2(4) . . ? O1 C1 O2 118.5(8) . . ? O1 C1 C2 119.8(8) . . ? O2 C1 C2 121.5(8) . . ? O1 C1 Pr2 57.1(4) . . ? O2 C1 Pr2 61.5(4) . . ? C2 C1 Pr2 171.2(6) . . ? C1 O1 Pr2 97.9(5) . . ? S1 O12 Pr1 145.3(4) 3_556 . ? O5 C7 O6 118.6(7) . . ? O5 C7 C6 122.2(7) . . ? O6 C7 C6 119.2(8) . . ? O5 C7 Pr1 60.1(4) . . ? O6 C7 Pr1 58.9(4) . . ? C6 C7 Pr1 173.6(6) . . ? C7 C6 C2 113.8(7) . 4_565 ? O7 C5 O8 118.8(8) . 3_565 ? O7 C5 C4 121.5(8) . . ? O8 C5 C4 119.6(8) 3_565 . ? O7 C5 Pr2 58.3(5) . . ? O8 C5 Pr2 60.5(4) 3_565 . ? C4 C5 Pr2 179.2(6) . . ? S1 O11 Pr2 144.4(4) 4_565 . ? S1 O9 Pr2 144.9(4) 2 . ? C8 O3 Pr1 100.2(5) . . ? C5 O8 Pr2 153.0(5) 3_565 . ? C5 O8 Pr2 93.5(5) 3_565 3_565 ? Pr2 O8 Pr2 109.2(2) . 3_565 ? C7 O5 Pr1 95.2(5) . . ? C1 C2 C6 108.6(7) . 4_666 ? O3 C8 O4 119.1(8) . . ? O3 C8 C3 120.1(8) . 1_556 ? O4 C8 C3 120.8(8) . 1_556 ? O3 C8 Pr1 55.2(4) . . ? O4 C8 Pr1 63.9(4) . . ? C3 C8 Pr1 174.5(6) 1_556 . ? C8 O4 Pr1 160.4(6) . 3_556 ? C8 O4 Pr1 90.3(5) . . ? Pr1 O4 Pr1 109.2(2) 3_556 . ? C5 C4 C3 110.6(7) . . ? C5 O7 Pr2 96.6(5) . . ? C8 C3 C4 112.9(8) 1_554 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.615 _refine_diff_density_min -1.251 _refine_diff_density_rms 0.214 # Attachment 'compound 3.cif' data_data2t_3 _database_code_depnum_ccdc_archive 'CCDC 828895' #TrackingRef 'compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 Nd2 O14 S' _chemical_formula_sum 'C8 H12 Nd2 O14 S' _chemical_formula_weight 652.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7225(19) _cell_length_b 9.5748(14) _cell_length_c 12.897(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.205(2) _cell_angle_gamma 90.00 _cell_volume 1474.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 4737 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 28.86 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 7.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5640 _exptl_absorpt_correction_T_max 0.7381 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11438 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2977 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0001P)^2^+197.6336P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2977 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2002 _refine_ls_wR_factor_gt 0.1961 _refine_ls_goodness_of_fit_ref 1.314 _refine_ls_restrained_S_all 1.314 _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 C3 C 0.0528(19) 0.733(2) 0.7395(17) 0.017(3) Uani 1 1 d . . . H3A H 0.1290 0.7598 0.7821 0.020 Uiso 1 1 calc R . . H3B H 0.0484 0.6316 0.7416 0.020 Uiso 1 1 calc R . . O12 O -0.2025(12) 0.8984(16) 0.4368(12) 0.013(3) Uani 1 1 d . . . Nd1 Nd -0.04081(9) 0.84165(11) 0.38456(8) 0.0091(3) Uani 1 1 d . . . Nd2 Nd 0.05133(9) 0.63321(11) 0.13101(8) 0.0090(3) Uani 1 1 d . . . S1 S 0.2491(4) 1.0032(5) 0.5023(4) 0.0107(10) Uani 1 1 d . . . O14 O 0.1628(13) 0.9001(16) 0.4398(12) 0.018(2) Uani 1 1 d . . . O2 O 0.0599(13) 0.6377(16) 0.3347(13) 0.018(3) Uani 1 1 d . . . C7 C -0.1411(17) 0.897(2) 0.1427(16) 0.013(3) Uani 1 1 d . . . O6 O -0.0454(13) 0.8290(17) 0.1863(12) 0.019(3) Uani 1 1 d . . . C5 C -0.0032(16) 0.741(2) -0.0935(16) 0.012(4) Uani 1 1 d . . . O1 O 0.1697(13) 0.4920(18) 0.2923(12) 0.022(4) Uani 1 1 d . . . O5 O -0.1808(14) 0.9515(18) 0.2084(12) 0.023(4) Uani 1 1 d . . . C1 C 0.1373(17) 0.547(2) 0.3660(16) 0.013(3) Uani 1 1 d . . . O11 O -0.1553(13) 0.5744(16) 0.0822(12) 0.018(2) Uani 1 1 d . . . O7 O 0.0439(15) 0.8170(17) -0.0084(13) 0.024(4) Uani 1 1 d . . . O9 O 0.2125(13) 0.5806(16) 0.0788(12) 0.018(3) Uani 1 1 d . . . C4 C -0.0267(19) 0.796(2) -0.2079(17) 0.017(3) Uani 1 1 d . . . H4A H -0.0188 0.8965 -0.2054 0.020 Uiso 1 1 calc R . . H4B H -0.1033 0.7736 -0.2529 0.020 Uiso 1 1 calc R . . C6 C -0.1903(18) 0.908(2) 0.0224(17) 0.018(5) Uani 1 1 d . . . H6A H -0.2009 0.8144 -0.0092 0.022 Uiso 1 1 calc R . . H6B H -0.1387 0.9567 -0.0052 0.022 Uiso 1 1 calc R . . O4 O 0.0242(13) 0.9076(15) 0.5945(11) 0.014(3) Uani 1 1 d . . . C2 C 0.197(2) 0.515(2) 0.4843(17) 0.019(5) Uani 1 1 d . . . H2A H 0.2087 0.4156 0.4944 0.023 Uiso 1 1 calc R . . H2B H 0.1519 0.5458 0.5277 0.023 Uiso 1 1 calc R . . C8 C 0.0256(18) 0.779(2) 0.6218(17) 0.015(4) Uani 1 1 d . . . O3 O -0.0010(15) 0.6889(17) 0.5450(12) 0.023(4) Uani 1 1 d . . . O13 O -0.1760(15) 0.6553(18) 0.2884(14) 0.026(4) Uani 1 1 d . . . H13A H -0.2021 0.6114 0.3458 0.031 Uiso 1 1 d . . . H13B H -0.1797 0.6415 0.2105 0.031 Uiso 1 1 d . . . O8 O 0.0257(13) 0.3870(15) 0.0777(11) 0.014(3) Uani 1 1 d . . . O10 O 0.1920(14) 0.8029(18) 0.2392(14) 0.025(4) Uani 1 1 d . . . H10A H 0.2455 0.8606 0.2162 0.030 Uiso 1 1 d . . . H10B H 0.2120 0.8177 0.3227 0.030 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 C3 0.022(8) 0.019(8) 0.012(7) 0.009(6) 0.009(6) 0.003(7) O12 0.011(7) 0.017(8) 0.014(7) -0.005(6) 0.007(6) 0.000(6) Nd1 0.0102(5) 0.0102(5) 0.0066(5) -0.0007(4) 0.0027(4) 0.0012(4) Nd2 0.0101(5) 0.0101(5) 0.0065(5) -0.0007(4) 0.0024(4) 0.0002(4) S1 0.011(2) 0.012(2) 0.011(2) -0.0001(18) 0.0048(19) 0.0008(19) O14 0.016(5) 0.020(6) 0.012(5) -0.009(4) -0.001(4) -0.006(4) O2 0.024(8) 0.013(7) 0.027(8) -0.006(6) 0.022(7) -0.001(7) C7 0.016(7) 0.008(7) 0.011(7) 0.000(5) 0.001(6) -0.005(6) O6 0.016(8) 0.019(8) 0.019(8) 0.002(6) 0.004(6) 0.005(6) C5 0.007(9) 0.021(11) 0.010(9) 0.001(8) 0.006(8) 0.004(8) O1 0.021(8) 0.027(9) 0.013(7) 0.004(6) 0.000(6) 0.016(7) O5 0.027(9) 0.034(10) 0.008(7) -0.003(7) 0.007(6) 0.017(8) C1 0.016(7) 0.008(7) 0.011(7) 0.000(5) 0.001(6) -0.005(6) O11 0.016(5) 0.020(6) 0.012(5) -0.009(4) -0.001(4) -0.006(4) O7 0.043(10) 0.015(8) 0.015(8) -0.006(6) 0.012(7) -0.010(8) O9 0.018(8) 0.020(8) 0.013(7) -0.004(6) 0.003(6) 0.000(6) C4 0.022(8) 0.019(8) 0.012(7) 0.009(6) 0.009(6) 0.003(7) C6 0.012(10) 0.019(11) 0.016(10) 0.002(8) -0.005(8) 0.006(9) O4 0.020(8) 0.009(7) 0.009(7) 0.000(5) 0.000(6) -0.006(6) C2 0.027(12) 0.021(12) 0.013(10) 0.000(9) 0.013(9) -0.003(10) C8 0.017(11) 0.016(10) 0.009(10) 0.006(8) 0.000(8) 0.002(8) O3 0.039(10) 0.017(8) 0.011(7) -0.001(6) 0.006(7) -0.004(7) O13 0.035(10) 0.019(9) 0.033(9) -0.007(7) 0.024(8) -0.015(8) O8 0.024(8) 0.010(7) 0.007(6) 0.000(5) 0.006(6) -0.001(6) O10 0.029(9) 0.024(9) 0.025(9) -0.010(7) 0.014(7) -0.017(8) _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 C3 C8 1.50(3) . ? C3 C4 1.52(3) 1_556 ? O12 S1 1.475(15) 3_576 ? O12 Nd1 2.437(14) . ? Nd1 O4 2.417(14) 3_576 ? Nd1 O3 2.440(15) . ? Nd1 O13 2.491(16) . ? Nd1 O14 2.502(15) . ? Nd1 O2 2.538(14) . ? Nd1 O6 2.541(15) . ? Nd1 O5 2.577(15) . ? Nd1 O4 2.621(14) . ? Nd1 C8 2.94(2) . ? Nd1 C7 2.98(2) . ? Nd2 O9 2.421(16) . ? Nd2 O8 2.445(14) . ? Nd2 O10 2.462(16) . ? Nd2 O6 2.479(16) . ? Nd2 O7 2.495(16) . ? Nd2 O1 2.502(15) . ? Nd2 O8 2.534(13) 3_565 ? Nd2 O11 2.545(15) . ? Nd2 O2 2.592(15) . ? Nd2 C5 2.92(2) . ? Nd2 C1 2.96(2) . ? S1 O12 1.475(15) 3_576 ? S1 O14 1.489(15) . ? S1 O11 1.493(15) 4_676 ? S1 O9 1.495(16) 2 ? O2 C1 1.27(3) . ? C7 O5 1.24(3) . ? C7 O6 1.32(3) . ? C7 C6 1.46(3) . ? C5 O7 1.28(3) . ? C5 O8 1.29(3) 3_565 ? C5 C4 1.49(3) . ? O1 C1 1.27(3) . ? C1 C2 1.48(3) . ? O11 S1 1.493(15) 4_575 ? O9 S1 1.495(16) 2_545 ? C4 C3 1.52(3) 1_554 ? C6 C2 1.54(3) 4_575 ? O4 C8 1.28(3) . ? O4 Nd1 2.417(14) 3_576 ? C2 C6 1.54(3) 4_676 ? C8 O3 1.27(3) . ? O8 C5 1.29(3) 3_565 ? O8 Nd2 2.534(13) 3_565 ? 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 C8 C3 C4 112.0(18) . 1_556 ? S1 O12 Nd1 145.3(9) 3_576 . ? O4 Nd1 O12 78.3(5) 3_576 . ? O4 Nd1 O3 121.1(5) 3_576 . ? O12 Nd1 O3 81.2(5) . . ? O4 Nd1 O13 141.8(6) 3_576 . ? O12 Nd1 O13 78.1(5) . . ? O3 Nd1 O13 84.2(6) . . ? O4 Nd1 O14 72.8(5) 3_576 . ? O12 Nd1 O14 139.6(5) . . ? O3 Nd1 O14 90.1(6) . . ? O13 Nd1 O14 140.4(5) . . ? O4 Nd1 O2 139.5(5) 3_576 . ? O12 Nd1 O2 142.2(5) . . ? O3 Nd1 O2 77.2(5) . . ? O13 Nd1 O2 69.2(5) . . ? O14 Nd1 O2 71.4(5) . . ? O4 Nd1 O6 97.5(5) 3_576 . ? O12 Nd1 O6 124.1(5) . . ? O3 Nd1 O6 138.7(5) . . ? O13 Nd1 O6 72.1(5) . . ? O14 Nd1 O6 87.7(5) . . ? O2 Nd1 O6 63.0(5) . . ? O4 Nd1 O5 72.5(5) 3_576 . ? O12 Nd1 O5 76.1(5) . . ? O3 Nd1 O5 150.5(6) . . ? O13 Nd1 O5 72.9(6) . . ? O14 Nd1 O5 119.5(5) . . ? O2 Nd1 O5 110.3(5) . . ? O6 Nd1 O5 50.5(5) . . ? O4 Nd1 O4 70.2(5) 3_576 . ? O12 Nd1 O4 69.9(5) . . ? O3 Nd1 O4 50.9(5) . . ? O13 Nd1 O4 127.2(5) . . ? O14 Nd1 O4 74.1(5) . . ? O2 Nd1 O4 116.1(5) . . ? O6 Nd1 O4 160.2(5) . . ? O5 Nd1 O4 133.4(5) . . ? O4 Nd1 C8 95.9(5) 3_576 . ? O12 Nd1 C8 74.0(5) . . ? O3 Nd1 C8 25.2(6) . . ? O13 Nd1 C8 105.9(6) . . ? O14 Nd1 C8 81.5(6) . . ? O2 Nd1 C8 96.8(6) . . ? O6 Nd1 C8 159.4(6) . . ? O5 Nd1 C8 149.6(6) . . ? O4 Nd1 C8 25.7(5) . . ? O4 Nd1 C7 86.0(5) 3_576 . ? O12 Nd1 C7 98.8(5) . . ? O3 Nd1 C7 151.9(5) . . ? O13 Nd1 C7 68.5(5) . . ? O14 Nd1 C7 106.6(5) . . ? O2 Nd1 C7 86.7(5) . . ? O6 Nd1 C7 26.2(5) . . ? O5 Nd1 C7 24.5(5) . . ? O4 Nd1 C7 155.0(5) . . ? C8 Nd1 C7 171.9(6) . . ? O9 Nd2 O8 76.4(5) . . ? O9 Nd2 O10 77.0(5) . . ? O8 Nd2 O10 142.7(6) . . ? O9 Nd2 O6 142.1(5) . . ? O8 Nd2 O6 141.1(5) . . ? O10 Nd2 O6 71.0(6) . . ? O9 Nd2 O7 76.8(6) . . ? O8 Nd2 O7 120.6(5) . . ? O10 Nd2 O7 77.4(5) . . ? O6 Nd2 O7 77.0(5) . . ? O9 Nd2 O1 78.1(5) . . ? O8 Nd2 O1 72.3(5) . . ? O10 Nd2 O1 77.0(6) . . ? O6 Nd2 O1 112.7(5) . . ? O7 Nd2 O1 147.4(6) . . ? O9 Nd2 O8 75.1(5) . 3_565 ? O8 Nd2 O8 70.3(5) . 3_565 ? O10 Nd2 O8 126.2(5) . 3_565 ? O6 Nd2 O8 108.4(5) . 3_565 ? O7 Nd2 O8 52.0(5) . 3_565 ? O1 Nd2 O8 138.0(5) . 3_565 ? O9 Nd2 O11 141.8(5) . . ? O8 Nd2 O11 72.0(5) . . ? O10 Nd2 O11 140.6(5) . . ? O6 Nd2 O11 70.5(5) . . ? O7 Nd2 O11 101.5(6) . . ? O1 Nd2 O11 111.1(5) . . ? O8 Nd2 O11 74.5(5) 3_565 . ? O9 Nd2 O2 122.8(5) . . ? O8 Nd2 O2 104.8(5) . . ? O10 Nd2 O2 69.3(5) . . ? O6 Nd2 O2 63.1(5) . . ? O7 Nd2 O2 134.2(5) . . ? O1 Nd2 O2 50.5(5) . . ? O8 Nd2 O2 160.7(5) 3_565 . ? O11 Nd2 O2 86.1(5) . . ? O9 Nd2 C5 74.5(5) . . ? O8 Nd2 C5 95.7(5) . . ? O10 Nd2 C5 101.8(6) . . ? O6 Nd2 C5 92.6(5) . . ? O7 Nd2 C5 25.8(6) . . ? O1 Nd2 C5 152.1(5) . . ? O8 Nd2 C5 26.2(5) 3_565 . ? O11 Nd2 C5 87.8(5) . . ? O2 Nd2 C5 155.6(5) . . ? O9 Nd2 C1 100.2(5) . . ? O8 Nd2 C1 89.2(5) . . ? O10 Nd2 C1 70.4(6) . . ? O6 Nd2 C1 87.7(5) . . ? O7 Nd2 C1 147.4(5) . . ? O1 Nd2 C1 25.2(6) . . ? O8 Nd2 C1 159.5(5) 3_565 . ? O11 Nd2 C1 100.2(5) . . ? O2 Nd2 C1 25.3(5) . . ? C5 Nd2 C1 171.7(6) . . ? O9 Nd2 Nd2 72.5(3) . 3_565 ? O8 Nd2 Nd2 35.9(3) . 3_565 ? O10 Nd2 Nd2 147.7(4) . 3_565 ? O6 Nd2 Nd2 131.6(3) . 3_565 ? O7 Nd2 Nd2 85.5(3) . 3_565 ? O1 Nd2 Nd2 106.2(4) . 3_565 ? O8 Nd2 Nd2 34.4(3) 3_565 3_565 ? O11 Nd2 Nd2 69.4(3) . 3_565 ? O2 Nd2 Nd2 137.8(3) . 3_565 ? C5 Nd2 Nd2 60.1(4) . 3_565 ? C1 Nd2 Nd2 125.0(4) . 3_565 ? O12 S1 O14 110.8(9) 3_576 . ? O12 S1 O11 109.4(9) 3_576 4_676 ? O14 S1 O11 108.4(9) . 4_676 ? O12 S1 O9 110.2(9) 3_576 2 ? O14 S1 O9 108.0(9) . 2 ? O11 S1 O9 110.1(9) 4_676 2 ? S1 O14 Nd1 143.1(9) . . ? C1 O2 Nd1 148.2(14) . . ? C1 O2 Nd2 93.9(12) . . ? Nd1 O2 Nd2 114.9(6) . . ? O5 C7 O6 116.6(18) . . ? O5 C7 C6 124.7(19) . . ? O6 C7 C6 118.7(19) . . ? O5 C7 Nd1 59.2(11) . . ? O6 C7 Nd1 57.9(10) . . ? C6 C7 Nd1 173.8(15) . . ? C7 O6 Nd2 136.5(13) . . ? C7 O6 Nd1 95.9(12) . . ? Nd2 O6 Nd1 119.0(6) . . ? O7 C5 O8 117.9(18) . 3_565 ? O7 C5 C4 122(2) . . ? O8 C5 C4 120.5(19) 3_565 . ? O7 C5 Nd2 58.0(11) . . ? O8 C5 Nd2 59.8(10) 3_565 . ? C4 C5 Nd2 177.9(14) . . ? C1 O1 Nd2 98.0(12) . . ? C7 O5 Nd1 96.3(12) . . ? O2 C1 O1 117.5(18) . . ? O2 C1 C2 122(2) . . ? O1 C1 C2 120.2(19) . . ? O2 C1 Nd2 60.8(10) . . ? O1 C1 Nd2 56.8(10) . . ? C2 C1 Nd2 171.1(15) . . ? S1 O11 Nd2 143.8(9) 4_575 . ? C5 O7 Nd2 96.2(13) . . ? S1 O9 Nd2 144.1(9) 2_545 . ? C5 C4 C3 111.3(17) . 1_554 ? C7 C6 C2 112.5(19) . 4_575 ? C8 O4 Nd1 158.9(13) . 3_576 ? C8 O4 Nd1 91.3(12) . . ? Nd1 O4 Nd1 109.8(5) 3_576 . ? C1 C2 C6 108.5(18) . 4_676 ? O3 C8 O4 117.8(18) . . ? O3 C8 C3 119.5(19) . . ? O4 C8 C3 122.7(19) . . ? O3 C8 Nd1 54.8(10) . . ? O4 C8 Nd1 63.0(10) . . ? C3 C8 Nd1 173.8(16) . . ? C8 O3 Nd1 100.1(13) . . ? C5 O8 Nd2 152.4(13) 3_565 . ? C5 O8 Nd2 94.0(12) 3_565 3_565 ? Nd2 O8 Nd2 109.7(5) . 3_565 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 5.802 _refine_diff_density_min -2.565 _refine_diff_density_rms 0.432 # Attachment 'compound 4.cif' data_data2t_4 _database_code_depnum_ccdc_archive 'CCDC 828896' #TrackingRef 'compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 O14 S Sm2' _chemical_formula_sum 'C8 H12 O14 S Sm2' _chemical_formula_weight 664.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6365(6) _cell_length_b 9.5308(4) _cell_length_c 12.8091(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.1280(10) _cell_angle_gamma 90.00 _cell_volume 1448.46(11) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 4513 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.71 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.049 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 8.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5492 _exptl_absorpt_correction_T_max 0.7898 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10285 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2549 _reflns_number_gt 2179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0120P)^2^+26.0064P] 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 2549 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.272 _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 H13B H 0.324(12) 0.370(14) 0.223(12) 0.04(4) Uiso 1 1 d . . . H10A H 0.738(14) 0.141(17) 0.219(12) 0.06(5) Uiso 1 1 d . . . H13A H 0.296(11) 0.382(13) 0.312(10) 0.02(4) Uiso 1 1 d . . . H10B H 0.688(8) 0.167(10) 0.294(9) 0.00(3) Uiso 1 1 d . . . Sm1 Sm 0.45898(4) 0.15763(5) 0.38406(4) 0.00904(14) Uani 1 1 d . . . Sm2 Sm 0.55156(4) 0.36721(5) 0.13110(4) 0.00879(14) Uani 1 1 d . . . S1 S 0.7492(2) -0.0027(3) 0.5026(2) 0.0104(5) Uani 1 1 d . . . O6 O 0.4556(6) 0.1712(7) 0.1864(5) 0.0142(15) Uani 1 1 d . . . O14 O 0.6628(6) 0.1014(7) 0.4405(6) 0.0162(16) Uani 1 1 d . . . C1 C 0.6363(8) 0.4521(10) 0.3644(8) 0.0119(14) Uani 1 1 d . . . C7 C 0.3617(8) 0.1031(10) 0.1436(8) 0.0119(14) Uani 1 1 d . . . C5 C 0.4973(8) 0.2600(10) -0.0923(8) 0.012(2) Uani 1 1 d . . . O2 O 0.5581(6) 0.3622(7) 0.3334(6) 0.0149(15) Uani 1 1 d . . . O1 O 0.6690(6) 0.5072(8) 0.2906(6) 0.0194(17) Uani 1 1 d . . . O11 O 0.3455(6) 0.4256(7) 0.0830(5) 0.0148(15) Uani 1 1 d . . . O7 O 0.5437(7) 0.1847(7) -0.0079(6) 0.0221(18) Uani 1 1 d . . . O12 O 0.2976(6) 0.1016(7) 0.4364(6) 0.0153(15) Uani 1 1 d . . . C6 C 0.3095(9) 0.0921(11) 0.0224(8) 0.016(2) Uani 1 1 d . . . H6A H 0.3607 0.0429 -0.0066 0.019 Uiso 1 1 calc R . . H6B H 0.2986 0.1858 -0.0091 0.019 Uiso 1 1 calc R . . O4 O 0.5250(6) 0.0905(7) 0.5952(6) 0.0160(16) Uani 1 1 d . . . O8 O 0.5252(6) 0.6122(7) 0.0766(5) 0.0141(15) Uani 1 1 d . . . O9 O 0.7119(6) 0.4202(8) 0.0776(5) 0.0176(16) Uani 1 1 d . . . O5 O 0.3197(6) 0.0485(8) 0.2094(6) 0.0217(17) Uani 1 1 d . . . O3 O 0.4989(6) 0.3097(7) 0.5441(6) 0.0185(17) Uani 1 1 d . . . O10 O 0.6922(7) 0.2005(8) 0.2382(7) 0.0195(17) Uani 1 1 d . . . O13 O 0.3251(7) 0.3419(9) 0.2887(7) 0.0217(19) Uani 1 1 d . . . C8 C 0.5249(8) 0.2199(10) 0.6194(8) 0.011(2) Uani 1 1 d . . . C2 C 0.6961(9) 0.4843(11) 0.4841(8) 0.017(2) Uani 1 1 d . . . H2A H 0.6512 0.4535 0.5279 0.021 Uiso 1 1 calc R . . H2B H 0.7080 0.5846 0.4943 0.021 Uiso 1 1 calc R . . C4 C 0.4725(9) 0.2028(11) -0.2077(8) 0.014(2) Uani 1 1 d . . . H4A H 0.3952 0.2243 -0.2528 0.016 Uiso 1 1 calc R . . H4B H 0.4811 0.1016 -0.2044 0.016 Uiso 1 1 calc R . . C3 C 0.5523(9) 0.2668(11) -0.2609(8) 0.015(2) Uani 1 1 d . . . H3A H 0.5477 0.3682 -0.2586 0.018 Uiso 1 1 calc R . . H3B H 0.6291 0.2398 -0.2181 0.018 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.0093(3) 0.0103(3) 0.0076(3) 0.00059(19) 0.0030(2) -0.0007(2) Sm2 0.0089(3) 0.0103(3) 0.0073(3) 0.00087(19) 0.00302(19) 0.0000(2) S1 0.0088(11) 0.0119(12) 0.0115(12) -0.0003(9) 0.0048(10) -0.0012(10) O6 0.012(4) 0.015(4) 0.013(3) -0.001(3) 0.002(3) -0.004(3) O14 0.011(4) 0.018(4) 0.019(4) 0.007(3) 0.003(3) 0.004(3) C1 0.012(3) 0.007(3) 0.015(4) 0.000(3) 0.003(3) 0.005(3) C7 0.012(3) 0.007(3) 0.015(4) 0.000(3) 0.003(3) 0.005(3) C5 0.014(5) 0.014(5) 0.009(5) -0.001(4) 0.006(4) -0.005(4) O2 0.015(4) 0.015(4) 0.017(4) -0.002(3) 0.008(3) -0.005(3) O1 0.022(4) 0.025(4) 0.009(3) 0.000(3) 0.003(3) -0.012(3) O11 0.011(4) 0.022(4) 0.010(3) 0.005(3) 0.003(3) 0.004(3) O7 0.040(5) 0.012(4) 0.015(4) 0.001(3) 0.011(4) 0.008(3) O12 0.013(4) 0.018(4) 0.018(4) 0.008(3) 0.010(3) 0.002(3) C6 0.016(5) 0.015(5) 0.013(5) -0.001(4) 0.001(4) -0.001(4) O4 0.024(4) 0.010(4) 0.015(4) -0.003(3) 0.008(3) 0.002(3) O8 0.017(4) 0.009(4) 0.013(3) -0.001(3) 0.001(3) 0.003(3) O9 0.023(4) 0.021(4) 0.010(4) 0.006(3) 0.007(3) 0.002(3) O5 0.023(4) 0.028(4) 0.016(4) 0.004(3) 0.008(3) -0.012(3) O3 0.029(4) 0.017(4) 0.013(4) 0.002(3) 0.012(3) 0.004(3) O10 0.019(4) 0.024(4) 0.020(4) 0.011(3) 0.013(4) 0.013(3) O13 0.029(5) 0.018(4) 0.024(5) 0.005(4) 0.017(4) 0.013(4) C8 0.009(5) 0.010(5) 0.013(5) -0.004(4) 0.002(4) 0.005(4) C2 0.013(6) 0.022(6) 0.017(5) 0.000(4) 0.005(4) -0.001(5) C4 0.013(5) 0.014(5) 0.015(5) -0.005(4) 0.006(4) -0.003(4) C3 0.016(6) 0.019(6) 0.008(5) -0.006(4) 0.002(4) 0.002(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 Sm1 O4 2.380(7) 3_656 ? Sm1 O12 2.415(7) . ? Sm1 O3 2.417(7) . ? Sm1 O13 2.453(8) . ? Sm1 O14 2.482(7) . ? Sm1 O2 2.520(7) . ? Sm1 O6 2.521(7) . ? Sm1 O5 2.544(7) . ? Sm1 O4 2.621(7) . ? Sm1 C8 2.899(9) . ? Sm1 C7 2.943(10) . ? Sm2 O9 2.406(7) . ? Sm2 O10 2.426(7) . ? Sm2 O8 2.427(7) . ? Sm2 O6 2.460(7) . ? Sm2 O1 2.464(7) . ? Sm2 O7 2.467(7) . ? Sm2 O8 2.507(7) 3_665 ? Sm2 O11 2.523(7) . ? Sm2 O2 2.564(7) . ? Sm2 C5 2.890(9) . ? Sm2 C1 2.921(10) . ? S1 O12 1.472(7) 3_656 ? S1 O9 1.478(7) 2_645 ? S1 O14 1.487(7) . ? S1 O11 1.490(7) 4_666 ? O6 C7 1.297(12) . ? C1 O2 1.264(12) . ? C1 O1 1.269(12) . ? C1 C2 1.490(14) . ? C7 O5 1.254(12) . ? C7 C6 1.467(13) . ? C5 O7 1.262(12) . ? C5 O8 1.282(12) 3_665 ? C5 C4 1.503(13) . ? O11 S1 1.490(7) 4_565 ? O12 S1 1.472(7) 3_656 ? C6 C2 1.529(14) 4_565 ? O4 C8 1.272(12) . ? O4 Sm1 2.380(7) 3_656 ? O8 C5 1.282(12) 3_665 ? O8 Sm2 2.507(7) 3_665 ? O9 S1 1.478(7) 2_655 ? O3 C8 1.246(12) . ? C8 C3 1.519(13) 1_556 ? C2 C6 1.529(14) 4_666 ? C4 C3 1.526(14) . ? C3 C8 1.519(13) 1_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Sm1 O12 78.3(2) 3_656 . ? O4 Sm1 O3 121.1(2) 3_656 . ? O12 Sm1 O3 81.2(2) . . ? O4 Sm1 O13 141.6(3) 3_656 . ? O12 Sm1 O13 78.1(3) . . ? O3 Sm1 O13 84.3(3) . . ? O4 Sm1 O14 73.3(2) 3_656 . ? O12 Sm1 O14 139.6(2) . . ? O3 Sm1 O14 89.4(2) . . ? O13 Sm1 O14 140.2(3) . . ? O4 Sm1 O2 140.0(2) 3_656 . ? O12 Sm1 O2 141.7(2) . . ? O3 Sm1 O2 77.1(2) . . ? O13 Sm1 O2 68.7(3) . . ? O14 Sm1 O2 71.6(2) . . ? O4 Sm1 O6 97.7(2) 3_656 . ? O12 Sm1 O6 124.5(2) . . ? O3 Sm1 O6 138.3(2) . . ? O13 Sm1 O6 72.1(3) . . ? O14 Sm1 O6 87.8(2) . . ? O2 Sm1 O6 62.6(2) . . ? O4 Sm1 O5 72.4(2) 3_656 . ? O12 Sm1 O5 76.1(2) . . ? O3 Sm1 O5 150.4(3) . . ? O13 Sm1 O5 72.8(3) . . ? O14 Sm1 O5 120.1(2) . . ? O2 Sm1 O5 110.1(2) . . ? O6 Sm1 O5 51.0(2) . . ? O4 Sm1 O4 70.0(3) 3_656 . ? O12 Sm1 O4 70.1(2) . . ? O3 Sm1 O4 51.1(2) . . ? O13 Sm1 O4 127.5(3) . . ? O14 Sm1 O4 73.5(2) . . ? O2 Sm1 O4 116.4(2) . . ? O6 Sm1 O4 159.8(2) . . ? O5 Sm1 O4 133.3(2) . . ? O4 Sm1 C8 96.0(2) 3_656 . ? O12 Sm1 C8 74.0(3) . . ? O3 Sm1 C8 25.1(2) . . ? O13 Sm1 C8 105.9(3) . . ? O14 Sm1 C8 81.0(2) . . ? O2 Sm1 C8 96.8(3) . . ? O6 Sm1 C8 159.0(3) . . ? O5 Sm1 C8 149.6(3) . . ? O4 Sm1 C8 26.0(2) . . ? O4 Sm1 C7 86.0(2) 3_656 . ? O12 Sm1 C7 99.4(3) . . ? O3 Sm1 C7 152.0(2) . . ? O13 Sm1 C7 68.7(3) . . ? O14 Sm1 C7 106.5(3) . . ? O2 Sm1 C7 86.1(2) . . ? O6 Sm1 C7 26.0(2) . . ? O5 Sm1 C7 25.1(2) . . ? O4 Sm1 C7 155.1(2) . . ? C8 Sm1 C7 172.5(3) . . ? O4 Sm1 Sm1 36.92(16) 3_656 3_656 ? O12 Sm1 Sm1 70.36(16) . 3_656 ? O3 Sm1 Sm1 84.16(16) . 3_656 ? O13 Sm1 Sm1 147.6(2) . 3_656 ? O14 Sm1 Sm1 69.66(16) . 3_656 ? O2 Sm1 Sm1 136.85(16) . 3_656 ? O6 Sm1 Sm1 132.69(16) . 3_656 ? O5 Sm1 Sm1 105.27(16) . 3_656 ? O4 Sm1 Sm1 33.07(14) . 3_656 ? C8 Sm1 Sm1 59.08(19) . 3_656 ? C7 Sm1 Sm1 122.62(18) . 3_656 ? O9 Sm2 O10 76.9(3) . . ? O9 Sm2 O8 76.2(2) . . ? O10 Sm2 O8 142.6(3) . . ? O9 Sm2 O6 142.1(2) . . ? O10 Sm2 O6 71.2(3) . . ? O8 Sm2 O6 141.3(2) . . ? O9 Sm2 O1 78.3(2) . . ? O10 Sm2 O1 76.8(3) . . ? O8 Sm2 O1 72.6(2) . . ? O6 Sm2 O1 112.8(2) . . ? O9 Sm2 O7 76.8(3) . . ? O10 Sm2 O7 77.6(3) . . ? O8 Sm2 O7 120.2(2) . . ? O6 Sm2 O7 76.8(2) . . ? O1 Sm2 O7 147.5(3) . . ? O9 Sm2 O8 74.8(2) . 3_665 ? O10 Sm2 O8 126.3(3) . 3_665 ? O8 Sm2 O8 69.8(2) . 3_665 ? O6 Sm2 O8 108.4(2) . 3_665 ? O1 Sm2 O8 137.8(2) . 3_665 ? O7 Sm2 O8 52.0(2) . 3_665 ? O9 Sm2 O11 141.6(2) . . ? O10 Sm2 O11 140.9(3) . . ? O8 Sm2 O11 71.9(2) . . ? O6 Sm2 O11 70.6(2) . . ? O1 Sm2 O11 111.1(2) . . ? O7 Sm2 O11 101.4(2) . . ? O8 Sm2 O11 74.5(2) 3_665 . ? O9 Sm2 O2 123.7(2) . . ? O10 Sm2 O2 69.8(3) . . ? O8 Sm2 O2 105.2(2) . . ? O6 Sm2 O2 62.8(2) . . ? O1 Sm2 O2 51.1(2) . . ? O7 Sm2 O2 134.1(2) . . ? O8 Sm2 O2 160.1(2) 3_665 . ? O11 Sm2 O2 85.6(2) . . ? O9 Sm2 C5 74.2(3) . . ? O10 Sm2 C5 101.9(3) . . ? O8 Sm2 C5 95.3(3) . . ? O6 Sm2 C5 92.5(2) . . ? O1 Sm2 C5 152.0(3) . . ? O7 Sm2 C5 25.7(3) . . ? O8 Sm2 C5 26.3(2) 3_665 . ? O11 Sm2 C5 87.9(3) . . ? O2 Sm2 C5 155.2(2) . . ? O9 Sm2 C1 100.7(3) . . ? O10 Sm2 C1 70.4(3) . . ? O8 Sm2 C1 89.6(2) . . ? O6 Sm2 C1 87.7(2) . . ? O1 Sm2 C1 25.5(3) . . ? O7 Sm2 C1 147.5(2) . . ? O8 Sm2 C1 159.4(2) 3_665 . ? O11 Sm2 C1 100.0(2) . . ? O2 Sm2 C1 25.6(2) . . ? C5 Sm2 C1 171.7(3) . . ? O9 Sm2 Sm2 72.19(16) . 3_665 ? O10 Sm2 Sm2 147.4(2) . 3_665 ? O8 Sm2 Sm2 35.55(15) . 3_665 ? O6 Sm2 Sm2 131.61(16) . 3_665 ? O1 Sm2 Sm2 106.23(17) . 3_665 ? O7 Sm2 Sm2 85.45(16) . 3_665 ? O8 Sm2 Sm2 34.26(15) 3_665 3_665 ? O11 Sm2 Sm2 69.44(15) . 3_665 ? O2 Sm2 Sm2 137.70(16) . 3_665 ? C5 Sm2 Sm2 60.0(2) . 3_665 ? C1 Sm2 Sm2 125.17(18) . 3_665 ? O12 S1 O9 110.0(4) 3_656 2_645 ? O12 S1 O14 110.9(4) 3_656 . ? O9 S1 O14 108.5(4) 2_645 . ? O12 S1 O11 109.4(4) 3_656 4_666 ? O9 S1 O11 109.7(4) 2_645 4_666 ? O14 S1 O11 108.4(4) . 4_666 ? C7 O6 Sm2 136.7(6) . . ? C7 O6 Sm1 95.5(6) . . ? Sm2 O6 Sm1 119.3(3) . . ? S1 O14 Sm1 142.8(4) . . ? O2 C1 O1 117.8(9) . . ? O2 C1 C2 121.9(9) . . ? O1 C1 C2 120.1(9) . . ? O2 C1 Sm2 61.2(5) . . ? O1 C1 Sm2 56.7(5) . . ? C2 C1 Sm2 171.1(7) . . ? O5 C7 O6 117.4(9) . . ? O5 C7 C6 122.8(9) . . ? O6 C7 C6 119.8(9) . . ? O5 C7 Sm1 59.4(5) . . ? O6 C7 Sm1 58.5(5) . . ? C6 C7 Sm1 173.7(7) . . ? O7 C5 O8 118.0(9) . 3_665 ? O7 C5 C4 121.0(9) . . ? O8 C5 C4 121.1(9) 3_665 . ? O7 C5 Sm2 58.0(5) . . ? O8 C5 Sm2 59.9(5) 3_665 . ? C4 C5 Sm2 178.4(7) . . ? C1 O2 Sm1 147.9(6) . . ? C1 O2 Sm2 93.2(6) . . ? Sm1 O2 Sm2 115.4(3) . . ? C1 O1 Sm2 97.8(6) . . ? S1 O11 Sm2 143.8(4) 4_565 . ? C5 O7 Sm2 96.2(6) . . ? S1 O12 Sm1 145.2(4) 3_656 . ? C7 C6 C2 113.8(9) . 4_565 ? C8 O4 Sm1 160.7(6) . 3_656 ? C8 O4 Sm1 89.3(6) . . ? Sm1 O4 Sm1 110.0(2) 3_656 . ? C5 O8 Sm2 152.2(6) 3_665 . ? C5 O8 Sm2 93.8(5) 3_665 3_665 ? Sm2 O8 Sm2 110.2(2) . 3_665 ? S1 O9 Sm2 144.8(4) 2_655 . ? C7 O5 Sm1 95.6(6) . . ? C8 O3 Sm1 99.6(6) . . ? O3 C8 O4 120.0(9) . . ? O3 C8 C3 119.2(8) . 1_556 ? O4 C8 C3 120.8(9) . 1_556 ? O3 C8 Sm1 55.3(5) . . ? O4 C8 Sm1 64.7(5) . . ? C3 C8 Sm1 173.9(7) 1_556 . ? C1 C2 C6 108.6(8) . 4_666 ? C5 C4 C3 110.4(8) . . ? C8 C3 C4 112.2(8) 1_554 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.648 _refine_diff_density_min -1.319 _refine_diff_density_rms 0.218