# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1728 data_cal9972 # SUBMISSION DETAILS _audit_creation_method 'manual editing of SHELXL template' _publ_contact_author_name 'Dr Tristram Chivers' _publ_contact_author_address ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; _publ_contact_author_email chivers@ucalgary.ca _publ_contact_author_fax '001 403 289 9488' _publ_contact_author_phone '001 403 220 5741' _publ_contact_letter ; To: Chemical Communications (B004137H) Please accept the following CIF data which is being submitted in support of an upcoming communication to be published in your Journal. Please forward any questions concerning this CIF to Dr. Gabriele Schatte (schatte@ucalgary.ca). ; _publ_requested_journal 'Chem. Comm. ' # TITLE AND AUTHOR LIST _publ_section_title ; Cycloaddition Reaction of tBuNCO and Te diimide dimer ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Chivers, Tristram' . ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; 'Schatte, Gabriele' . ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; 'Sandblom, Nicole' . ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; 'Jasksa, Cory' . ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; _publ_section_acknowledgements ; ???? ; # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 N4 O4 Te2, C4 H8 O' _chemical_formula_sum 'C22 H44 N4 O5 Te2' _chemical_formula_weight 699.81 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' 'Te' 'Te' -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'tetragonal' _symmetry_space_group_name_H-M 'P 41 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' _cell_length_a 15.5941(7) _cell_length_b 15.5941(7) _cell_length_c 12.4867(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3036.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.955 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.6304 _exptl_absorpt_correction_T_max 0.7580 _exptl_absorpt_process_details ;SADABS, V 2.01, Software for Area-Detector Absorption Corrections; Bruker AXS Inc., Madison, WI, 2000. ; _exptl_special_details ; ? ; # EXPERIMENTAL DETAILS _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _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_% 'no decay' _diffrn_reflns_number 13101 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2593 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SIR-97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (1.05) in WinGX-1.62' _computing_publication_material 'WinGX-1.62' # REFINEMENT DATA _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^)+(0.0250P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 2593 _refine_ls_number_parameters 178 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0188 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0413 _refine_ls_wR_factor_gt 0.0405 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 Te1 Te 0.380993(9) 0.248016(11) 0.041491(13) 0.03481(6) Uani 1 1 d . . . O1 O 0.31073(14) 0.03641(13) 0.16748(17) 0.0520(6) Uani 1 1 d . . . O2 O 0.29835(12) 0.32649(12) 0.09620(15) 0.0392(4) Uani 1 1 d . . . N1 N 0.36600(16) 0.17490(15) 0.18026(18) 0.0442(6) Uani 1 1 d . . . N2 N 0.31574(14) 0.13582(13) 0.02493(17) 0.0352(5) Uani 1 1 d . . . C1 C 0.32907(18) 0.10736(19) 0.1316(2) 0.0402(7) Uani 1 1 d . . . C10 C 0.3814(2) 0.1843(2) 0.2970(3) 0.0539(8) Uani 1 1 d . . . C11 C 0.4435(3) 0.1157(2) 0.3347(3) 0.0738(11) Uani 1 1 d . . . H11A H 0.4207 0.0590 0.3166 0.089 Uiso 1 1 calc R . . H11B H 0.4508 0.1201 0.4125 0.089 Uiso 1 1 calc R . . H11C H 0.4990 0.1239 0.2995 0.089 Uiso 1 1 calc R . . C12 C 0.2974(3) 0.1787(4) 0.3572(3) 0.0939(15) Uani 1 1 d . . . H12A H 0.2586 0.2238 0.3320 0.113 Uiso 1 1 calc R . . H12B H 0.3080 0.1861 0.4340 0.113 Uiso 1 1 calc R . . H12C H 0.2712 0.1225 0.3446 0.113 Uiso 1 1 calc R . . C13 C 0.4211(3) 0.2721(2) 0.3140(3) 0.0859(14) Uani 1 1 d . . . H13A H 0.4740 0.2767 0.2719 0.103 Uiso 1 1 calc R . . H13B H 0.4344 0.2799 0.3901 0.103 Uiso 1 1 calc R . . H13C H 0.3806 0.3165 0.2909 0.103 Uiso 1 1 calc R . . C20 C 0.30551(18) 0.07358(17) -0.0662(2) 0.0368(6) Uani 1 1 d . . . C21 C 0.38383(18) 0.01592(18) -0.0733(2) 0.0434(7) Uani 1 1 d . . . H21A H 0.4350 0.0510 -0.0861 0.052 Uiso 1 1 calc R . . H21B H 0.3765 -0.0248 -0.1324 0.052 Uiso 1 1 calc R . . H21C H 0.3905 -0.0157 -0.0060 0.052 Uiso 1 1 calc R . . C22 C 0.22514(17) 0.0208(2) -0.0448(3) 0.0516(8) Uani 1 1 d . . . H22A H 0.2335 -0.0139 0.0198 0.062 Uiso 1 1 calc R . . H22B H 0.2141 -0.0169 -0.1060 0.062 Uiso 1 1 calc R . . H22C H 0.1762 0.0593 -0.0345 0.062 Uiso 1 1 calc R . . C23 C 0.2940(2) 0.12392(19) -0.1701(2) 0.0448(7) Uani 1 1 d . . . H23A H 0.2443 0.1620 -0.1636 0.054 Uiso 1 1 calc R . . H23B H 0.2848 0.0839 -0.2295 0.054 Uiso 1 1 calc R . . H23C H 0.3455 0.1582 -0.1839 0.054 Uiso 1 1 calc R . . O1S O 0.4138(4) 0.4733(5) -0.0528(6) 0.135(3) Uani 0.50 1 d PDU A -1 C1S C 0.4959(8) 0.4486(11) -0.0854(11) 0.101(5) Uani 0.50 1 d PDU A -1 H11S H 0.5193 0.4894 -0.1385 0.122 Uiso 0.50 1 calc PR A -1 H12S H 0.4950 0.3905 -0.1172 0.122 Uiso 0.50 1 calc PR A -1 C2S C 0.5498(9) 0.4499(9) 0.0196(11) 0.125(5) Uani 0.50 1 d PDU A -1 H21S H 0.5615 0.3907 0.0445 0.150 Uiso 0.50 1 calc PR A -1 H22S H 0.6051 0.4796 0.0080 0.150 Uiso 0.50 1 calc PR A -1 C3S C 0.4984(10) 0.4953(12) 0.0965(12) 0.132(5) Uani 0.50 1 d PDU A -1 H31S H 0.5323 0.5412 0.1314 0.158 Uiso 0.50 1 calc PR A -1 H32S H 0.4767 0.4558 0.1523 0.158 Uiso 0.50 1 calc PR A -1 C4S C 0.4230(7) 0.5341(9) 0.0307(11) 0.095(4) Uani 0.50 1 d PDU A -1 H41S H 0.3702 0.5384 0.0743 0.114 Uiso 0.50 1 calc PR A -1 H42S H 0.4378 0.5915 0.0023 0.114 Uiso 0.50 1 calc PR A -1 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 Te1 0.02943(9) 0.03445(9) 0.04055(10) 0.00011(9) -0.00072(7) 0.00385(9) O1 0.0654(14) 0.0466(12) 0.0438(12) 0.0119(10) -0.0007(11) -0.0058(11) O2 0.0366(10) 0.0424(10) 0.0386(10) -0.0056(9) -0.0021(9) 0.0100(9) N1 0.0561(15) 0.0431(13) 0.0333(14) 0.0031(11) -0.0109(11) 0.0019(12) N2 0.0380(11) 0.0335(12) 0.0342(13) 0.0030(10) -0.0016(10) 0.0006(10) C1 0.0388(16) 0.0455(16) 0.0364(16) 0.0023(14) -0.0023(13) 0.0056(14) C10 0.0632(19) 0.0602(18) 0.0383(16) -0.0023(16) -0.0136(17) 0.0124(17) C11 0.087(3) 0.088(3) 0.046(2) -0.006(2) -0.0225(19) 0.032(2) C12 0.084(3) 0.152(5) 0.045(2) -0.022(3) 0.000(2) 0.024(3) C13 0.133(4) 0.065(3) 0.060(2) -0.0100(19) -0.044(3) -0.005(2) C20 0.0398(15) 0.0363(14) 0.0342(16) -0.0002(12) -0.0025(12) 0.0002(12) C21 0.0495(16) 0.0410(15) 0.0396(15) 0.0001(13) 0.0035(14) 0.0065(14) C22 0.0435(16) 0.0556(17) 0.056(2) -0.0004(17) -0.0052(15) -0.0101(14) C23 0.0575(17) 0.0418(15) 0.0350(15) -0.0018(13) -0.0063(14) 0.0028(15) O1S 0.064(3) 0.180(7) 0.161(7) -0.120(6) 0.041(4) -0.054(4) C1S 0.078(7) 0.121(12) 0.106(9) -0.053(9) 0.047(6) -0.019(8) C2S 0.105(7) 0.122(10) 0.147(11) -0.066(9) 0.015(7) 0.006(7) C3S 0.163(13) 0.136(11) 0.096(7) -0.042(8) 0.021(8) 0.023(10) C4S 0.068(6) 0.103(9) 0.113(10) -0.070(8) 0.023(6) -0.028(5) _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. ; # MOLECULAR GEOMETRY 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 Te1 O2 1.9040(17) . ? Te1 N2 2.034(2) . ? Te1 O2 2.0723(18) 6 ? Te1 N1 2.087(2) . ? Te1 C1 2.595(3) . ? Te1 Te1 3.1103(3) 6 ? O1 C1 1.227(3) . ? O2 Te1 2.0723(18) 6 ? N1 C1 1.345(4) . ? N1 C10 1.485(4) . ? N2 C1 1.420(3) . ? N2 C20 1.504(3) . ? C10 C12 1.513(5) . ? C10 C13 1.517(5) . ? C10 C11 1.517(4) . ? C20 C21 1.519(4) . ? C20 C22 1.523(4) . ? C20 C23 1.527(4) . ? O1S C1S 1.397(12) . ? O1S C4S 1.417(10) . ? C1S C2S 1.558(14) . ? C2S C3S 1.437(18) . ? C3S C4S 1.557(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Te1 N2 104.52(9) . . ? O2 Te1 O2 77.10(8) . 6 ? N2 Te1 O2 92.08(8) . 6 ? O2 Te1 N1 88.71(9) . . ? N2 Te1 N1 63.81(9) . . ? O2 Te1 N1 148.18(9) 6 . ? O2 Te1 C1 100.16(8) . . ? N2 Te1 C1 32.98(9) . . ? O2 Te1 C1 123.51(8) 6 . ? N1 Te1 C1 31.05(9) . . ? O2 Te1 Te1 40.51(5) . 6 ? N2 Te1 Te1 101.89(6) . 6 ? O2 Te1 Te1 36.65(5) 6 6 ? N1 Te1 Te1 124.48(7) . 6 ? C1 Te1 Te1 120.00(6) . 6 ? Te1 O2 Te1 102.84(8) . 6 ? C1 N1 C10 126.2(3) . . ? C1 N1 Te1 95.79(17) . . ? C10 N1 Te1 138.0(2) . . ? C1 N2 C20 121.6(2) . . ? C1 N2 Te1 95.76(17) . . ? C20 N2 Te1 133.23(17) . . ? O1 C1 N1 129.9(3) . . ? O1 C1 N2 126.2(3) . . ? N1 C1 N2 104.0(2) . . ? O1 C1 Te1 173.2(2) . . ? N1 C1 Te1 53.16(14) . . ? N2 C1 Te1 51.27(13) . . ? N1 C10 C12 110.0(3) . . ? N1 C10 C13 107.0(3) . . ? C12 C10 C13 109.6(3) . . ? N1 C10 C11 109.8(3) . . ? C12 C10 C11 110.9(3) . . ? C13 C10 C11 109.4(3) . . ? N2 C20 C21 109.9(2) . . ? N2 C20 C22 107.7(2) . . ? C21 C20 C22 110.6(2) . . ? N2 C20 C23 108.9(2) . . ? C21 C20 C23 110.4(2) . . ? C22 C20 C23 109.3(2) . . ? C1S O1S C4S 107.8(8) . . ? O1S C1S C2S 104.2(10) . . ? C3S C2S C1S 105.6(8) . . ? C2S C3S C4S 105.0(9) . . ? O1S C4S C3S 101.8(10) . . ? 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 N2 Te1 O2 Te1 -91.41(10) . . . 6 ? O2 Te1 O2 Te1 -2.61(11) 6 . . 6 ? N1 Te1 O2 Te1 -153.90(10) . . . 6 ? C1 Te1 O2 Te1 -124.90(9) . . . 6 ? O2 Te1 N1 C1 112.32(18) . . . . ? N2 Te1 N1 C1 5.43(16) . . . . ? O2 Te1 N1 C1 49.7(3) 6 . . . ? Te1 Te1 N1 C1 92.03(17) 6 . . . ? O2 Te1 N1 C10 -64.4(3) . . . . ? N2 Te1 N1 C10 -171.3(3) . . . . ? O2 Te1 N1 C10 -127.0(3) 6 . . . ? C1 Te1 N1 C10 -176.7(4) . . . . ? Te1 Te1 N1 C10 -84.7(3) 6 . . . ? O2 Te1 N2 C1 -86.32(16) . . . . ? O2 Te1 N2 C1 -163.53(16) 6 . . . ? N1 Te1 N2 C1 -5.14(15) . . . . ? Te1 Te1 N2 C1 -127.90(15) 6 . . . ? O2 Te1 N2 C20 128.9(2) . . . . ? O2 Te1 N2 C20 51.7(2) 6 . . . ? N1 Te1 N2 C20 -149.9(3) . . . . ? C1 Te1 N2 C20 -144.8(3) . . . . ? Te1 Te1 N2 C20 87.3(2) 6 . . . ? C10 N1 C1 O1 -10.5(5) . . . . ? Te1 N1 C1 O1 172.2(3) . . . . ? C10 N1 C1 N2 170.1(3) . . . . ? Te1 N1 C1 N2 -7.2(2) . . . . ? C10 N1 C1 Te1 177.3(3) . . . . ? C20 N2 C1 O1 -21.6(4) . . . . ? Te1 N2 C1 O1 -172.0(3) . . . . ? C20 N2 C1 N1 157.9(2) . . . . ? Te1 N2 C1 N1 7.4(2) . . . . ? C20 N2 C1 Te1 150.5(3) . . . . ? O2 Te1 C1 N1 -69.98(18) . . . . ? N2 Te1 C1 N1 -171.0(3) . . . . ? O2 Te1 C1 N1 -151.16(16) 6 . . . ? Te1 Te1 C1 N1 -107.95(16) 6 . . . ? O2 Te1 C1 N2 101.04(16) . . . . ? O2 Te1 C1 N2 19.87(19) 6 . . . ? N1 Te1 C1 N2 171.0(3) . . . . ? Te1 Te1 C1 N2 63.08(17) 6 . . . ? C1 N1 C10 C12 -58.8(4) . . . . ? Te1 N1 C10 C12 117.2(4) . . . . ? C1 N1 C10 C13 -177.8(3) . . . . ? Te1 N1 C10 C13 -1.9(5) . . . . ? C1 N1 C10 C11 63.5(4) . . . . ? Te1 N1 C10 C11 -120.5(3) . . . . ? C1 N2 C20 C21 -57.8(3) . . . . ? Te1 N2 C20 C21 79.9(3) . . . . ? C1 N2 C20 C22 62.7(3) . . . . ? Te1 N2 C20 C22 -159.6(2) . . . . ? C1 N2 C20 C23 -178.9(2) . . . . ? Te1 N2 C20 C23 -41.2(3) . . . . ? C4S O1S C1S C2S 34.8(13) . . . . ? O1S C1S C2S C3S -13.9(18) . . . . ? C1S C2S C3S C4S -9.9(19) . . . . ? C1S O1S C4S C3S -40.6(12) . . . . ? C2S C3S C4S O1S 30.0(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.143 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.042