# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dimitra Kovala-Demertzi' _publ_contact_author_email DKOVALA@CC.UOI.GR _publ_section_title ; Self-assembly of Dialkyltin(IV) moieties and a thiosemicarbone to a trinuclear macrocycle and the unprecedented formation of two pseudo-polymorfs with different cavities ; loop_ _publ_author_name 'Dimitra Kovala-Demertzi' 'Zbigniew Ciunik' 'John Plakatouras' 'Joanna Wiecek' # Attachment '1.CIF' data_a1abs _database_code_depnum_ccdc_archive 'CCDC 293441' _audit_creation_method SHELXL-97 _chemical_name_common 'Dimethyl(pyruvic-thiosemicarbazonate)tin(IV) THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C18 H33 N9 O6 S3 Sn3, 3(C4 H8 O)' _chemical_formula_sum 'C10 H19 N3 O3 S Sn' _chemical_formula_weight 380.06 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' 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P63/m _symmetry_space_group_name_Hall '-P 6c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 18.2141(5) _cell_length_b 18.2141(5) _cell_length_c 7.6303(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2192.24(12) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11200 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 36.60 _exptl_crystal_description block _exptl_crystal_colour off-white _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 1.895 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.7513 _exptl_absorpt_correction_T_max 0.8045 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37222 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 36.60 _reflns_number_total 3772 _reflns_number_gt 3183 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997); Platon (Spek, 1998)' _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^)+(0.0297P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3772 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0529 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Sn1 Sn -0.172955(7) 0.486406(7) 0.7500 0.01074(4) Uani 1 2 d S . . S1 S -0.04081(3) 0.63327(3) 0.7500 0.01582(9) Uani 1 2 d S . . O1 O -0.22231(8) 0.34169(8) 0.7500 0.0150(2) Uani 1 2 d S . . O2 O -0.18835(8) 0.24018(8) 0.7500 0.0154(2) Uani 1 2 d S . . N1 N -0.06059(9) 0.46100(9) 0.7500 0.0123(3) Uani 1 2 d S . . N2 N 0.02263(9) 0.52357(10) 0.7500 0.0169(3) Uani 1 2 d S . . N3 N 0.11629(11) 0.66406(12) 0.7500 0.0323(5) Uani 1 2 d S . . C1 C -0.16761(11) 0.31742(11) 0.7500 0.0135(3) Uani 1 2 d S . . C2 C -0.07547(10) 0.38352(11) 0.7500 0.0123(3) Uani 1 2 d S . . C3 C -0.00941(12) 0.35851(13) 0.7500 0.0176(3) Uani 1 2 d S . . H3A H 0.0348 0.3931 0.6648 0.026 Uiso 0.50 1 calc PR . . H3B H -0.0351 0.2985 0.7181 0.026 Uiso 0.50 1 calc PR . . H3C H 0.0157 0.3673 0.8671 0.026 Uiso 0.50 1 calc PR . . C4 C 0.03495(12) 0.60168(12) 0.7500 0.0170(3) Uani 1 2 d S . . C5 C -0.19904(8) 0.47108(9) 0.47839(18) 0.0165(2) Uani 1 1 d . . . H5A H -0.2547 0.4209 0.4587 0.025 Uiso 1 1 calc R . . H5B H -0.1555 0.4640 0.4182 0.025 Uiso 1 1 calc R . . H5C H -0.1990 0.5213 0.4323 0.025 Uiso 1 1 calc R . . O1T O 0.16489(11) 0.83847(10) 0.7500 0.0297(4) Uani 1 2 d S . . C1T1 C 0.1449(10) 0.8709(11) 0.604(3) 0.039(2) Uani 0.50 1 d P . 1 H1T1 H 0.1001 0.8244 0.5333 0.047 Uiso 0.50 1 calc PR . 1 H1T2 H 0.1956 0.9031 0.5288 0.047 Uiso 0.50 1 calc PR . 1 C2T1 C 0.1142(3) 0.9284(3) 0.6726(7) 0.0528(12) Uani 0.50 1 d P . 1 H2T1 H 0.1515 0.9868 0.6292 0.063 Uiso 0.50 1 calc PR . 1 H2T2 H 0.0561 0.9088 0.6292 0.063 Uiso 0.50 1 calc PR . 1 C1T2 C 0.1300(10) 0.8565(11) 0.592(3) 0.040(3) Uani 0.50 1 d P . 2 H1T3 H 0.1758 0.9015 0.5204 0.048 Uiso 0.50 1 calc PR . 2 H1T4 H 0.0989 0.8049 0.5186 0.048 Uiso 0.50 1 calc PR . 2 C2T2 C 0.0721(3) 0.8846(3) 0.6586(7) 0.0544(12) Uani 0.50 1 d P . 2 H2T3 H 0.0903 0.9424 0.6150 0.065 Uiso 0.50 1 calc PR . 2 H2T4 H 0.0139 0.8462 0.6150 0.065 Uiso 0.50 1 calc PR . 2 H3D H 0.1486(18) 0.6461(19) 0.7500 0.030(7) Uiso 1 2 d S . . H3E H 0.130(2) 0.717(2) 0.7500 0.045(9) Uiso 1 2 d S . . 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 Sn1 0.00871(5) 0.01091(5) 0.01235(6) 0.000 0.000 0.00472(4) S1 0.01118(18) 0.01122(18) 0.0243(2) 0.000 0.000 0.00502(15) O1 0.0105(5) 0.0138(6) 0.0206(6) 0.000 0.000 0.0060(5) O2 0.0128(6) 0.0108(5) 0.0218(6) 0.000 0.000 0.0052(5) N1 0.0086(6) 0.0123(6) 0.0152(7) 0.000 0.000 0.0046(5) N2 0.0078(6) 0.0122(6) 0.0281(8) 0.000 0.000 0.0030(5) N3 0.0087(7) 0.0130(8) 0.0721(16) 0.000 0.000 0.0030(6) C1 0.0106(7) 0.0134(7) 0.0139(7) 0.000 0.000 0.0041(6) C2 0.0100(7) 0.0125(7) 0.0133(7) 0.000 0.000 0.0049(6) C3 0.0128(7) 0.0194(8) 0.0233(9) 0.000 0.000 0.0101(7) C4 0.0109(7) 0.0134(7) 0.0252(9) 0.000 0.000 0.0049(6) C5 0.0161(5) 0.0207(6) 0.0129(6) -0.0008(5) -0.0010(4) 0.0093(5) O1T 0.0250(8) 0.0194(7) 0.0431(10) 0.000 0.000 0.0098(6) C1T1 0.027(4) 0.043(7) 0.036(4) 0.000(5) -0.003(3) 0.011(4) C2T1 0.038(2) 0.033(2) 0.088(4) 0.017(2) -0.004(2) 0.0192(18) C1T2 0.043(7) 0.031(4) 0.037(4) 0.003(3) -0.002(5) 0.012(4) C2T2 0.036(2) 0.036(2) 0.090(3) 0.004(2) -0.023(2) 0.0171(18) _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 Sn1 C5 2.1133(14) . ? Sn1 C5 2.1133(14) 10_557 ? Sn1 N1 2.3130(14) . ? Sn1 O1 2.3209(13) . ? Sn1 O2 2.4077(12) 2_565 ? Sn1 S1 2.5516(5) . ? S1 C4 1.7405(19) . ? O1 C1 1.276(2) . ? O2 C1 1.261(2) . ? O2 Sn1 2.4077(12) 3_455 ? N1 C2 1.297(2) . ? N1 N2 1.367(2) . ? N2 C4 1.325(2) . ? N3 C4 1.343(3) . ? N3 H3D 0.80(3) . ? N3 H3E 0.87(3) . ? C1 C2 1.498(2) . ? C2 C3 1.484(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O1T C1T1 1.39(2) . ? O1T C1T1 1.39(2) 10_557 ? O1T C1T2 1.48(2) . ? O1T C1T2 1.48(2) 10_557 ? C1T1 C2T1 1.51(2) . ? C1T1 H1T1 0.9900 . ? C1T1 H1T2 0.9900 . ? C2T1 C2T1 1.181(11) 10_557 ? C2T1 H2T1 0.9900 . ? C2T1 H2T2 0.9900 . ? C1T2 C2T2 1.48(2) . ? C1T2 H1T3 0.9900 . ? C1T2 H1T4 0.9900 . ? C2T2 C2T2 1.395(11) 10_557 ? C2T2 H2T3 0.9900 . ? C2T2 H2T4 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 C5 Sn1 C5 157.43(7) . 10_557 ? C5 Sn1 N1 97.85(4) . . ? C5 Sn1 N1 97.85(4) 10_557 . ? C5 Sn1 O1 85.19(4) . . ? C5 Sn1 O1 85.19(4) 10_557 . ? N1 Sn1 O1 69.62(5) . . ? C5 Sn1 O2 86.10(4) . 2_565 ? C5 Sn1 O2 86.10(4) 10_557 2_565 ? N1 Sn1 O2 156.11(5) . 2_565 ? O1 Sn1 O2 134.27(4) . 2_565 ? C5 Sn1 S1 99.81(4) . . ? C5 Sn1 S1 99.81(4) 10_557 . ? N1 Sn1 S1 75.20(4) . . ? O1 Sn1 S1 144.82(3) . . ? O2 Sn1 S1 80.91(3) 2_565 . ? C4 S1 Sn1 98.14(6) . . ? C1 O1 Sn1 117.86(11) . . ? C1 O2 Sn1 101.17(11) . 3_455 ? C2 N1 N2 116.64(15) . . ? C2 N1 Sn1 119.55(11) . . ? N2 N1 Sn1 123.81(11) . . ? C4 N2 N1 114.65(15) . . ? C4 N3 H3D 112(2) . . ? C4 N3 H3E 122(2) . . ? H3D N3 H3E 126(3) . . ? O2 C1 O1 122.42(16) . . ? O2 C1 C2 119.12(16) . . ? O1 C1 C2 118.46(15) . . ? N1 C2 C3 124.99(16) . . ? N1 C2 C1 114.51(15) . . ? C3 C2 C1 120.50(15) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 N3 115.56(17) . . ? N2 C4 S1 128.20(14) . . ? N3 C4 S1 116.24(15) . . ? Sn1 C5 H5A 109.5 . . ? Sn1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? Sn1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1T1 O1T C1T1 106.5(18) . 10_557 ? C1T1 O1T C1T2 109.2(2) 10_557 . ? C1T1 O1T C1T2 109.2(2) . 10_557 ? C1T2 O1T C1T2 109.9(19) . 10_557 ? O1T C1T1 C2T1 106.3(15) . . ? O1T C1T1 H1T1 110.5 . . ? C2T1 C1T1 H1T1 110.5 . . ? O1T C1T1 H1T2 110.5 . . ? C2T1 C1T1 H1T2 110.5 . . ? H1T1 C1T1 H1T2 108.7 . . ? C2T1 C2T1 C1T1 110.5(10) 10_557 . ? C2T1 C2T1 H2T1 109.6 10_557 . ? C1T1 C2T1 H2T1 109.6 . . ? C2T1 C2T1 H2T2 109.6 10_557 . ? C1T1 C2T1 H2T2 109.6 . . ? H2T1 C2T1 H2T2 108.1 . . ? C2T2 C1T2 O1T 104.8(16) . . ? C2T2 C1T2 H1T3 110.8 . . ? O1T C1T2 H1T3 110.8 . . ? C2T2 C1T2 H1T4 110.8 . . ? O1T C1T2 H1T4 110.8 . . ? H1T3 C1T2 H1T4 108.9 . . ? C2T2 C2T2 C1T2 110.3(10) 10_557 . ? C2T2 C2T2 H2T3 109.6 10_557 . ? C1T2 C2T2 H2T3 109.6 . . ? C2T2 C2T2 H2T4 109.6 10_557 . ? C1T2 C2T2 H2T4 109.6 . . ? H2T3 C2T2 H2T4 108.1 . . ? 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 C5 Sn1 S1 C4 -95.60(4) . . . . ? C5 Sn1 S1 C4 95.60(4) 10_557 . . . ? N1 Sn1 S1 C4 0.0 . . . . ? O1 Sn1 S1 C4 0.0 . . . . ? O2 Sn1 S1 C4 180.0 2_565 . . . ? C5 Sn1 O1 C1 100.22(4) . . . . ? C5 Sn1 O1 C1 -100.22(4) 10_557 . . . ? N1 Sn1 O1 C1 0.0 . . . . ? O2 Sn1 O1 C1 180.0 2_565 . . . ? S1 Sn1 O1 C1 0.0 . . . . ? C5 Sn1 N1 C2 -81.87(4) . . . . ? C5 Sn1 N1 C2 81.87(4) 10_557 . . . ? O1 Sn1 N1 C2 0.0 . . . . ? O2 Sn1 N1 C2 180.0 2_565 . . . ? S1 Sn1 N1 C2 180.0 . . . . ? C5 Sn1 N1 N2 98.13(4) . . . . ? C5 Sn1 N1 N2 -98.13(4) 10_557 . . . ? O1 Sn1 N1 N2 180.0 . . . . ? O2 Sn1 N1 N2 0.0 2_565 . . . ? S1 Sn1 N1 N2 0.0 . . . . ? C2 N1 N2 C4 180.0 . . . . ? Sn1 N1 N2 C4 0.0 . . . . ? Sn1 O2 C1 O1 0.0 3_455 . . . ? Sn1 O2 C1 C2 180.0 3_455 . . . ? Sn1 O1 C1 O2 180.0 . . . . ? Sn1 O1 C1 C2 0.0 . . . . ? N2 N1 C2 C3 0.0 . . . . ? Sn1 N1 C2 C3 180.0 . . . . ? N2 N1 C2 C1 180.0 . . . . ? Sn1 N1 C2 C1 0.0 . . . . ? O2 C1 C2 N1 180.0 . . . . ? O1 C1 C2 N1 0.0 . . . . ? O2 C1 C2 C3 0.0 . . . . ? O1 C1 C2 C3 180.0 . . . . ? N1 N2 C4 N3 180.0 . . . . ? N1 N2 C4 S1 0.0 . . . . ? Sn1 S1 C4 N2 0.0 . . . . ? Sn1 S1 C4 N3 180.0 . . . . ? C1T1 O1T C1T1 C2T1 2.0(16) 10_557 . . . ? C1T2 O1T C1T1 C2T1 108(10) . . . . ? C1T2 O1T C1T1 C2T1 13.0(6) 10_557 . . . ? O1T C1T1 C2T1 C2T1 -1.3(10) . . . 10_557 ? C1T1 O1T C1T2 C2T2 -89(10) . . . . ? C1T1 O1T C1T2 C2T2 -12.3(7) 10_557 . . . ? C1T2 O1T C1T2 C2T2 -0.8(16) 10_557 . . . ? O1T C1T2 C2T2 C2T2 0.5(10) . . . 10_557 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3E O1T 0.87(3) 1.97(3) 2.840(3) 178(3) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 36.60 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.445 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.104 # Attachment 'A2ABS.CIF' data_a2abs _database_code_depnum_ccdc_archive 'CCDC 293442' _audit_creation_method SHELXL-97 _chemical_name_common 'Dimethyl(pyruvic-thiosemicarbazonate)tin(IV) THF solvate' _chemical_melting_point ? _chemical_formula_moiety 'C18 H33 N9 O6 S3 Sn3, 1.5(C4 H8 O)' _chemical_formula_sum 'C8 H15 N3 O2.50 S Sn' _chemical_formula_weight 343.98 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' 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting cubic _symmetry_space_group_name_H-M I23 _symmetry_space_group_name_Hall 'I 2 2 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'z, x, y' 'z, -x, -y' '-z, -x, y' '-z, x, -y' 'y, z, x' '-y, z, -x' 'y, -z, -x' '-y, -z, x' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'z+1/2, -x+1/2, -y+1/2' '-z+1/2, -x+1/2, y+1/2' '-z+1/2, x+1/2, -y+1/2' 'y+1/2, z+1/2, x+1/2' '-y+1/2, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x+1/2' '-y+1/2, -z+1/2, x+1/2' _cell_length_a 20.1191(5) _cell_length_b 20.1191(5) _cell_length_c 20.1191(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8143.8(4) _cell_formula_units_Z 24 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12000 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 36.61 _exptl_crystal_description block _exptl_crystal_colour off-white _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4080 _exptl_absorpt_coefficient_mu 2.029 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7116 _exptl_absorpt_correction_T_max 0.7928 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Kuma KM4CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66056 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 36.61 _reflns_number_total 6610 _reflns_number_gt 5473 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997); Platon (Spek, 1998)' _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^)+(0.0375P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 -0.022(18) _refine_ls_number_reflns 6610 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0630 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _refine_ls_shift/su_max 0.004 _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 Sn1 Sn 0.290695(8) 0.907717(8) 0.221615(8) 0.01204(3) Uani 1 1 d . . . S1 S 0.34676(3) 1.01892(3) 0.24352(3) 0.02079(13) Uani 1 1 d . . . O1 O 0.28497(9) 0.81668(8) 0.15147(8) 0.0156(3) Uani 1 1 d . . . O2 O 0.32094(8) 0.77096(9) 0.05814(8) 0.0154(3) Uani 1 1 d . . . N1 N 0.36909(10) 0.91731(10) 0.13844(10) 0.0123(4) Uani 1 1 d . . . N2 N 0.41286(10) 0.96860(10) 0.13399(11) 0.0149(4) Uani 1 1 d . . . N3 N 0.44825(11) 1.06618(11) 0.17647(11) 0.0187(4) Uani 1 1 d . . . H3D H 0.4833 1.0577 0.1475 0.019 Uiso 1 1 d . . . H3E H 0.4462 1.1040 0.2026 0.018 Uiso 1 1 d . . . C1 C 0.32339(11) 0.81598(12) 0.10135(12) 0.0134(4) Uani 1 1 d . . . C2 C 0.37239(11) 0.87177(11) 0.09289(12) 0.0130(4) Uani 1 1 d . . . C3 C 0.41983(13) 0.87177(13) 0.03630(13) 0.0183(5) Uani 1 1 d . . . H3A H 0.4244 0.9170 0.0189 0.027 Uiso 1 1 calc R . . H3B H 0.4032 0.8425 0.0011 0.027 Uiso 1 1 calc R . . H3C H 0.4633 0.8558 0.0515 0.027 Uiso 1 1 calc R . . C4 C 0.40539(12) 1.01541(12) 0.18037(12) 0.0139(4) Uani 1 1 d . . . C5 C 0.20901(13) 0.94507(13) 0.16790(12) 0.0176(5) Uani 1 1 d . . . H5A H 0.1701 0.9169 0.1758 0.026 Uiso 1 1 calc R . . H5B H 0.2195 0.9452 0.1203 0.026 Uiso 1 1 calc R . . H5C H 0.1994 0.9905 0.1825 0.026 Uiso 1 1 calc R . . C6 C 0.34427(13) 0.84355(14) 0.28472(13) 0.0215(5) Uani 1 1 d . . . H6A H 0.3182 0.8032 0.2928 0.032 Uiso 1 1 calc R . . H6B H 0.3531 0.8660 0.3270 0.032 Uiso 1 1 calc R . . H6C H 0.3865 0.8316 0.2636 0.032 Uiso 1 1 calc R . . O1T O 0.2865(3) 1.0000 0.0000 0.0907(19) Uani 1 2 d S . . C1T C 0.2539(3) 1.0587(4) 0.0360(3) 0.141(4) Uani 1 1 d . . . H1TA H 0.2663 1.1017 0.0157 0.170 Uiso 1 1 calc R . . H1TB H 0.2651 1.0592 0.0839 0.170 Uiso 1 1 calc R . . C2T C 0.1734(4) 1.0404(4) 0.0233(3) 0.162(5) Uani 1 1 d . . . H2TA H 0.1512 1.0743 -0.0024 0.194 Uiso 1 1 d . . . H2TB H 0.1495 1.0355 0.0648 0.194 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 Sn1 0.01096(7) 0.01303(7) 0.01215(7) -0.00129(5) 0.00132(5) -0.00145(5) S1 0.0198(3) 0.0192(3) 0.0234(3) -0.0097(2) 0.0093(2) -0.0072(2) O1 0.0157(8) 0.0145(7) 0.0166(8) -0.0018(6) 0.0029(7) -0.0037(6) O2 0.0151(8) 0.0149(8) 0.0163(8) -0.0039(7) -0.0002(6) -0.0018(6) N1 0.0101(8) 0.0126(9) 0.0141(9) -0.0017(7) -0.0001(7) -0.0023(7) N2 0.0136(9) 0.0118(9) 0.0195(9) -0.0015(7) 0.0017(8) -0.0046(7) N3 0.0182(10) 0.0135(9) 0.0243(11) -0.0049(8) 0.0060(8) -0.0062(8) C1 0.0104(10) 0.0147(10) 0.0151(11) -0.0020(8) -0.0010(8) -0.0009(8) C2 0.0120(9) 0.0139(10) 0.0131(10) -0.0019(8) 0.0023(8) -0.0008(7) C3 0.0165(12) 0.0218(12) 0.0166(11) -0.0014(9) 0.0097(9) -0.0004(9) C4 0.0109(9) 0.0143(10) 0.0164(10) -0.0020(8) 0.0016(8) -0.0002(8) C5 0.0158(11) 0.0228(12) 0.0142(10) 0.0003(8) -0.0002(9) 0.0030(9) C6 0.0227(12) 0.0249(12) 0.0170(12) 0.0008(10) -0.0026(10) 0.0057(10) O1T 0.082(4) 0.111(5) 0.080(4) 0.061(3) 0.000 0.000 C1T 0.092(4) 0.205(7) 0.127(5) 0.149(6) 0.075(4) 0.103(5) C2T 0.140(6) 0.237(9) 0.109(6) 0.155(6) 0.089(5) 0.149(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 Sn1 C5 2.106(2) . ? Sn1 C6 2.107(3) . ? Sn1 N1 2.308(2) . ? Sn1 O1 2.3151(16) . ? Sn1 O2 2.4502(17) 12_665 ? Sn1 S1 2.5441(7) . ? S1 C4 1.735(2) . ? O1 C1 1.271(3) . ? O2 C1 1.257(3) . ? O2 Sn1 2.4502(17) 6_566 ? N1 C2 1.297(3) . ? N1 N2 1.359(3) . ? N2 C4 1.334(3) . ? N3 C4 1.339(3) . ? N3 H3D 0.9307 . ? N3 H3E 0.9258 . ? C1 C2 1.504(3) . ? C2 C3 1.486(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O1T C1T 1.533(8) 4_575 ? O1T C1T 1.533(8) . ? C1T C2T 1.680(12) . ? C1T H1TA 0.9900 . ? C1T H1TB 0.9900 . ? C2T C2T 1.88(2) 4_575 ? C2T H2TA 0.9656 . ? C2T H2TB 0.9686 . ? 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 C5 Sn1 C6 157.99(11) . . ? C5 Sn1 N1 97.55(8) . . ? C6 Sn1 N1 97.97(9) . . ? C5 Sn1 O1 86.03(8) . . ? C6 Sn1 O1 84.72(9) . . ? N1 Sn1 O1 70.01(6) . . ? C5 Sn1 O2 85.61(8) . 12_665 ? C6 Sn1 O2 86.52(8) . 12_665 ? N1 Sn1 O2 156.06(6) . 12_665 ? O1 Sn1 O2 133.93(6) . 12_665 ? C5 Sn1 S1 96.95(8) . . ? C6 Sn1 S1 101.98(8) . . ? N1 Sn1 S1 75.47(5) . . ? O1 Sn1 S1 145.43(5) . . ? O2 Sn1 S1 80.60(4) 12_665 . ? C4 S1 Sn1 97.98(8) . . ? C1 O1 Sn1 117.53(15) . . ? C1 O2 Sn1 101.71(14) . 6_566 ? C2 N1 N2 117.2(2) . . ? C2 N1 Sn1 119.21(15) . . ? N2 N1 Sn1 123.63(15) . . ? C4 N2 N1 114.6(2) . . ? C4 N3 H3D 112.6 . . ? C4 N3 H3E 124.5 . . ? H3D N3 H3E 122.6 . . ? O2 C1 O1 122.2(2) . . ? O2 C1 C2 119.0(2) . . ? O1 C1 C2 118.7(2) . . ? N1 C2 C3 125.0(2) . . ? N1 C2 C1 114.4(2) . . ? C3 C2 C1 120.5(2) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 N3 115.2(2) . . ? N2 C4 S1 128.12(19) . . ? N3 C4 S1 116.72(18) . . ? Sn1 C5 H5A 109.5 . . ? Sn1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? Sn1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? Sn1 C6 H6A 109.5 . . ? Sn1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? Sn1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1T O1T C1T 129.3(8) 4_575 . ? O1T C1T C2T 99.9(7) . . ? O1T C1T H1TA 111.8 . . ? C2T C1T H1TA 111.8 . . ? O1T C1T H1TB 111.8 . . ? C2T C1T H1TB 111.8 . . ? H1TA C1T H1TB 109.5 . . ? C1T C2T C2T 105.4(4) . 4_575 ? C1T C2T H2TA 111.9 . . ? C2T C2T H2TA 110.3 4_575 . ? C1T C2T H2TB 111.7 . . ? C2T C2T H2TB 110.0 4_575 . ? H2TA C2T H2TB 107.6 . . ? 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 C5 Sn1 S1 C4 -98.92(11) . . . . ? C6 Sn1 S1 C4 92.35(11) . . . . ? N1 Sn1 S1 C4 -2.89(10) . . . . ? O1 Sn1 S1 C4 -5.83(13) . . . . ? O2 Sn1 S1 C4 176.73(10) 12_665 . . . ? C5 Sn1 O1 C1 96.71(18) . . . . ? C6 Sn1 O1 C1 -103.28(19) . . . . ? N1 Sn1 O1 C1 -2.81(17) . . . . ? O2 Sn1 O1 C1 176.72(15) 12_665 . . . ? S1 Sn1 O1 C1 0.2(2) . . . . ? C5 Sn1 N1 C2 -81.05(19) . . . . ? C6 Sn1 N1 C2 83.29(19) . . . . ? O1 Sn1 N1 C2 1.91(17) . . . . ? O2 Sn1 N1 C2 -177.25(16) 12_665 . . . ? S1 Sn1 N1 C2 -176.32(18) . . . . ? C5 Sn1 N1 N2 98.93(19) . . . . ? C6 Sn1 N1 N2 -96.73(19) . . . . ? O1 Sn1 N1 N2 -178.11(19) . . . . ? O2 Sn1 N1 N2 2.7(3) 12_665 . . . ? S1 Sn1 N1 N2 3.66(16) . . . . ? C2 N1 N2 C4 177.2(2) . . . . ? Sn1 N1 N2 C4 -2.7(3) . . . . ? Sn1 O2 C1 O1 7.5(3) 6_566 . . . ? Sn1 O2 C1 C2 -171.16(18) 6_566 . . . ? Sn1 O1 C1 O2 -175.26(17) . . . . ? Sn1 O1 C1 C2 3.4(3) . . . . ? N2 N1 C2 C3 -0.5(3) . . . . ? Sn1 N1 C2 C3 179.50(19) . . . . ? N2 N1 C2 C1 179.1(2) . . . . ? Sn1 N1 C2 C1 -1.0(3) . . . . ? O2 C1 C2 N1 177.0(2) . . . . ? O1 C1 C2 N1 -1.7(3) . . . . ? O2 C1 C2 C3 -3.4(3) . . . . ? O1 C1 C2 C3 177.9(2) . . . . ? N1 N2 C4 N3 180.0(2) . . . . ? N1 N2 C4 S1 -1.1(3) . . . . ? Sn1 S1 C4 N2 3.4(2) . . . . ? Sn1 S1 C4 N3 -177.63(19) . . . . ? C1T O1T C1T C2T -0.91(18) 4_575 . . . ? O1T C1T C2T C2T 2.1(4) . . . 4_575 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3D N2 0.93 2.17 3.005(3) 148.5 2_675 N3 H3E O2 0.93 2.04 2.964(3) 172.2 19_564 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.165 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.112