Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Chivers, Tristram' ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; 'Laitinen, Risto' ; Department of Chemistry University of Oulu FIN-90401 Oulu, Finland ; 'Maaninen, Tiina' ; Department of Chemistry University of Oulu FIN-90401 Oulu, Finland ; _publ_contact_author_name 'Prof Risto Laitinen' _publ_contact_author_address ; Department of Chemistry University of Oulu PO Box 3000 Oulu FIN-90401 FINLAND ; _publ_contact_author_email RISTO.LAITINEN@OULU.FI _publ_contact_letter ; To: Chemical Communications Please accept the following CIF file which is being submitted in support of an upcoming communication to be published in Chemical Communications. ; _publ_requested_journal 'Chem. Comm.' _publ_section_title ; A monomeric Selenium(IV) Diimide and aDimeric Selenenylamine ; _publ_section_acknowledgements ; NSERC (Canada and Academy of Finland (financial support) ; data_cmpd1b _database_code_CSD 189238 _audit_creation_method 'manual editing of SHELXL template' _chemical_name_systematic ; adamantyl selenium diimide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N2 Se' _chemical_formula_sum 'C20 H30 N2 Se' _chemical_formula_weight 377.42 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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.986(2) _cell_length_b 6.6244(13) _cell_length_c 25.059(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.69(3) _cell_angle_gamma 90.00 _cell_volume 1797.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 2.091 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.6798 _exptl_absorpt_correction_T_max 0.7875 _exptl_absorpt_process_details ? _exptl_special_details ; adamantyl selenium diimide ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappaccd' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14883 _diffrn_reflns_av_R_equivalents 0.1268 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2327 _reflns_number_gt 1741 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0598P)^2^+18.0692P] 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 SHELXL _refine_ls_extinction_coef 0.0017(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2327 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0781 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1804 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Se1 Se 0.06385(9) 0.45759(18) 0.25222(4) 0.0509(5) Uani 1 1 d . . . N1 N 0.0863(7) 0.4593(13) 0.1876(3) 0.049(2) Uani 1 1 d . . . N2 N 0.1996(7) 0.4797(13) 0.2982(3) 0.049(2) Uani 1 1 d . . . C1 C 0.2094(8) 0.4801(15) 0.1699(4) 0.043(2) Uani 1 1 d . . . C2 C 0.2952(9) 0.3046(16) 0.1877(4) 0.049(3) Uani 1 1 d . . . H2A H 0.2543 0.1767 0.1744 0.059 Uiso 1 1 calc R . . H2B H 0.3131 0.2991 0.2277 0.059 Uiso 1 1 calc R . . C3 C 0.4158(8) 0.3260(16) 0.1658(4) 0.047(3) Uani 1 1 d . . . H3 H 0.4713 0.2095 0.1782 0.056 Uiso 1 1 calc R . . C4 C 0.3886(9) 0.3314(17) 0.1040(4) 0.051(3) Uani 1 1 d . . . H4A H 0.3485 0.2037 0.0901 0.062 Uiso 1 1 calc R . . H4B H 0.4667 0.3455 0.0896 0.062 Uiso 1 1 calc R . . C5 C 0.3046(9) 0.5072(15) 0.0856(4) 0.047(3) Uani 1 1 d . . . H5 H 0.2862 0.5096 0.0451 0.057 Uiso 1 1 calc R . . C6 C 0.3656(10) 0.7051(17) 0.1061(4) 0.054(3) Uani 1 1 d . . . H6A H 0.4426 0.7244 0.0911 0.064 Uiso 1 1 calc R . . H6B H 0.3095 0.8194 0.0940 0.064 Uiso 1 1 calc R . . C7 C 0.3947(9) 0.6999(16) 0.1676(4) 0.051(3) Uani 1 1 d . . . H7 H 0.4365 0.8286 0.1811 0.061 Uiso 1 1 calc R . . C8 C 0.2737(9) 0.6785(15) 0.1899(4) 0.045(3) Uani 1 1 d . . . H8A H 0.2188 0.7938 0.1777 0.054 Uiso 1 1 calc R . . H8B H 0.2913 0.6796 0.2300 0.054 Uiso 1 1 calc R . . C9 C 0.4788(8) 0.5233(16) 0.1863(4) 0.050(3) Uani 1 1 d . . . H9A H 0.5574 0.5379 0.1723 0.060 Uiso 1 1 calc R . . H9B H 0.4980 0.5215 0.2263 0.060 Uiso 1 1 calc R . . C10 C 0.1834(9) 0.4841(17) 0.1078(3) 0.051(3) Uani 1 1 d . . . H10A H 0.1277 0.5983 0.0953 0.061 Uiso 1 1 calc R . . H10B H 0.1417 0.3575 0.0940 0.061 Uiso 1 1 calc R . . C11 C 0.1902(8) 0.4908(14) 0.3557(4) 0.039(2) Uani 1 1 d . . . C12 C 0.2711(10) 0.3198(16) 0.3840(4) 0.054(3) Uani 1 1 d . . . H12A H 0.2340 0.1877 0.3721 0.065 Uiso 1 1 calc R . . H12B H 0.3542 0.3264 0.3738 0.065 Uiso 1 1 calc R . . C13 C 0.2823(9) 0.3387(18) 0.4458(4) 0.053(3) Uani 1 1 d . . . H13 H 0.3369 0.2290 0.4638 0.064 Uiso 1 1 calc R . . C14 C 0.1552(10) 0.3192(16) 0.4605(4) 0.053(3) Uani 1 1 d . . . H14A H 0.1608 0.3278 0.5003 0.064 Uiso 1 1 calc R . . H14B H 0.1193 0.1864 0.4485 0.064 Uiso 1 1 calc R . . C15 C 0.0717(9) 0.4896(15) 0.4331(4) 0.047(3) Uani 1 1 d . . . H15 H -0.0125 0.4764 0.4429 0.056 Uiso 1 1 calc R . . C16 C 0.1267(9) 0.6903(16) 0.4529(4) 0.049(3) Uani 1 1 d . . . H16A H 0.1344 0.6981 0.4928 0.059 Uiso 1 1 calc R . . H16B H 0.0721 0.8013 0.4369 0.059 Uiso 1 1 calc R . . C17 C 0.2555(9) 0.7126(16) 0.4364(4) 0.049(3) Uani 1 1 d . . . H17 H 0.2914 0.8467 0.4488 0.058 Uiso 1 1 calc R . . C18 C 0.2472(9) 0.6962(15) 0.3763(4) 0.044(3) Uani 1 1 d . . . H18A H 0.3307 0.7092 0.3667 0.053 Uiso 1 1 calc R . . H18B H 0.1955 0.8074 0.3584 0.053 Uiso 1 1 calc R . . C19 C 0.3372(9) 0.5460(18) 0.4644(4) 0.054(3) Uani 1 1 d . . . H19A H 0.3434 0.5589 0.5041 0.065 Uiso 1 1 calc R . . H19B H 0.4213 0.5583 0.4554 0.065 Uiso 1 1 calc R . . C20 C 0.0623(8) 0.4726(16) 0.3720(4) 0.045(2) Uani 1 1 d . . . H20A H 0.0079 0.5807 0.3541 0.054 Uiso 1 1 calc R . . H20B H 0.0252 0.3409 0.3596 0.054 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 Se1 0.0379(6) 0.0652(8) 0.0486(7) -0.0054(6) 0.0045(4) -0.0053(6) N1 0.040(4) 0.044(5) 0.058(5) 0.003(4) -0.003(4) 0.002(4) N2 0.035(4) 0.065(6) 0.045(5) -0.004(4) 0.001(4) -0.006(4) C1 0.034(5) 0.048(7) 0.048(6) 0.002(5) 0.008(4) 0.003(5) C2 0.054(7) 0.044(7) 0.049(7) -0.003(5) 0.008(5) -0.007(5) C3 0.033(5) 0.050(7) 0.058(7) 0.013(5) 0.010(5) 0.013(5) C4 0.041(6) 0.055(7) 0.060(7) -0.004(5) 0.014(5) -0.001(5) C5 0.042(5) 0.054(8) 0.042(6) -0.005(5) -0.001(4) -0.005(5) C6 0.055(7) 0.056(7) 0.049(7) 0.010(5) 0.006(5) 0.002(6) C7 0.057(7) 0.041(7) 0.052(7) -0.003(5) 0.005(5) -0.016(5) C8 0.044(6) 0.044(7) 0.045(6) 0.001(5) 0.004(5) 0.000(5) C9 0.032(5) 0.070(8) 0.044(6) 0.006(5) 0.001(4) -0.010(5) C10 0.043(5) 0.074(8) 0.031(5) -0.003(5) -0.003(4) -0.002(5) C11 0.034(5) 0.045(7) 0.037(5) 0.001(4) 0.000(4) 0.004(4) C12 0.050(6) 0.046(7) 0.069(8) 0.000(6) 0.018(5) 0.011(6) C13 0.047(6) 0.072(8) 0.040(6) 0.015(5) 0.007(5) 0.023(6) C14 0.063(7) 0.048(7) 0.051(7) 0.013(5) 0.015(5) -0.006(6) C15 0.041(5) 0.051(7) 0.052(6) -0.001(5) 0.016(5) 0.000(5) C16 0.044(6) 0.046(7) 0.057(7) -0.002(5) 0.012(5) 0.008(5) C17 0.044(6) 0.048(7) 0.053(7) -0.008(5) 0.006(5) -0.007(5) C18 0.043(6) 0.041(6) 0.048(6) 0.006(5) 0.007(5) 0.003(5) C19 0.034(5) 0.079(8) 0.049(6) -0.010(6) 0.003(5) -0.006(6) C20 0.038(5) 0.053(7) 0.044(6) 0.003(5) 0.004(4) -0.008(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. ; 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 Se1 N1 1.678(8) . ? Se1 N2 1.731(7) . ? N1 C1 1.499(12) . ? N2 C11 1.464(12) . ? C1 C10 1.535(13) . ? C1 C2 1.515(14) . ? C1 C8 1.536(14) . ? C2 C3 1.523(13) . ? C3 C4 1.526(14) . ? C3 C9 1.527(14) . ? C4 C5 1.510(14) . ? C5 C6 1.522(14) . ? C5 C10 1.535(13) . ? C6 C7 1.521(14) . ? C7 C8 1.533(13) . ? C7 C9 1.516(14) . ? C11 C20 1.532(12) . ? C11 C12 1.537(13) . ? C11 C18 1.550(13) . ? C12 C13 1.536(14) . ? C13 C14 1.509(14) . ? C13 C19 1.540(16) . ? C14 C15 1.542(14) . ? C15 C16 1.509(14) . ? C15 C20 1.522(13) . ? C16 C17 1.548(13) . ? C17 C19 1.517(14) . ? C17 C18 1.496(13) . ? 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 N1 Se1 N2 113.1(4) . . ? C1 N1 Se1 124.9(6) . . ? C11 N2 Se1 117.7(6) . . ? N1 C1 C10 106.1(7) . . ? N1 C1 C2 113.0(8) . . ? C10 C1 C2 108.2(8) . . ? N1 C1 C8 111.8(8) . . ? C10 C1 C8 108.2(8) . . ? C2 C1 C8 109.4(8) . . ? C1 C2 C3 111.0(8) . . ? C4 C3 C9 108.8(8) . . ? C4 C3 C2 109.5(8) . . ? C9 C3 C2 109.3(8) . . ? C3 C4 C5 109.5(8) . . ? C6 C5 C4 110.5(8) . . ? C6 C5 C10 108.9(8) . . ? C4 C5 C10 109.6(8) . . ? C7 C6 C5 109.1(8) . . ? C6 C7 C8 109.0(8) . . ? C6 C7 C9 110.1(9) . . ? C8 C7 C9 109.7(8) . . ? C7 C8 C1 109.9(8) . . ? C3 C9 C7 109.8(7) . . ? C1 C10 C5 110.2(7) . . ? N2 C11 C20 118.6(7) . . ? N2 C11 C12 106.6(7) . . ? C20 C11 C12 107.7(8) . . ? N2 C11 C18 106.2(7) . . ? C20 C11 C18 108.5(8) . . ? C12 C11 C18 108.9(7) . . ? C13 C12 C11 110.3(8) . . ? C14 C13 C12 108.6(8) . . ? C14 C13 C19 109.5(9) . . ? C12 C13 C19 109.7(9) . . ? C13 C14 C15 109.5(8) . . ? C16 C15 C20 110.6(8) . . ? C16 C15 C14 108.8(8) . . ? C20 C15 C14 109.2(8) . . ? C15 C16 C17 109.3(8) . . ? C19 C17 C18 110.1(8) . . ? C19 C17 C16 107.6(8) . . ? C18 C17 C16 111.0(8) . . ? C17 C18 C11 110.6(8) . . ? C17 C19 C13 109.7(8) . . ? C15 C20 C11 110.6(7) . . ? 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 Se1 N1 C1 -0.7(9) . . . . ? N1 Se1 N2 C11 176.8(7) . . . . ? Se1 N1 C1 C10 -177.2(7) . . . . ? Se1 N1 C1 C2 64.4(11) . . . . ? Se1 N1 C1 C8 -59.5(10) . . . . ? N1 C1 C2 C3 176.4(8) . . . . ? C10 C1 C2 C3 59.2(10) . . . . ? C8 C1 C2 C3 -58.4(10) . . . . ? C1 C2 C3 C4 -59.9(11) . . . . ? C1 C2 C3 C9 59.1(10) . . . . ? C9 C3 C4 C5 -60.1(10) . . . . ? C2 C3 C4 C5 59.3(11) . . . . ? C3 C4 C5 C6 60.2(10) . . . . ? C3 C4 C5 C10 -59.7(10) . . . . ? C4 C5 C6 C7 -59.0(11) . . . . ? C10 C5 C6 C7 61.3(10) . . . . ? C5 C6 C7 C8 -61.7(11) . . . . ? C5 C6 C7 C9 58.6(10) . . . . ? C6 C7 C8 C1 61.2(11) . . . . ? C9 C7 C8 C1 -59.4(10) . . . . ? N1 C1 C8 C7 -176.0(8) . . . . ? C10 C1 C8 C7 -59.5(10) . . . . ? C2 C1 C8 C7 58.1(10) . . . . ? C4 C3 C9 C7 60.0(10) . . . . ? C2 C3 C9 C7 -59.5(10) . . . . ? C6 C7 C9 C3 -59.8(10) . . . . ? C8 C7 C9 C3 60.1(10) . . . . ? N1 C1 C10 C5 179.5(8) . . . . ? C2 C1 C10 C5 -59.0(11) . . . . ? C8 C1 C10 C5 59.4(10) . . . . ? C6 C5 C10 C1 -60.7(11) . . . . ? C4 C5 C10 C1 60.2(11) . . . . ? Se1 N2 C11 C20 2.7(11) . . . . ? Se1 N2 C11 C12 124.3(7) . . . . ? Se1 N2 C11 C18 -119.7(7) . . . . ? N2 C11 C12 C13 171.6(8) . . . . ? C20 C11 C12 C13 -60.1(10) . . . . ? C18 C11 C12 C13 57.4(10) . . . . ? C11 C12 C13 C14 61.7(11) . . . . ? C11 C12 C13 C19 -58.0(10) . . . . ? C12 C13 C14 C15 -60.7(12) . . . . ? C19 C13 C14 C15 59.1(11) . . . . ? C13 C14 C15 C16 -60.5(11) . . . . ? C13 C14 C15 C20 60.3(11) . . . . ? C20 C15 C16 C17 -58.0(10) . . . . ? C14 C15 C16 C17 62.0(10) . . . . ? C15 C16 C17 C19 -62.5(10) . . . . ? C15 C16 C17 C18 58.1(11) . . . . ? C19 C17 C18 C11 60.6(10) . . . . ? C16 C17 C18 C11 -58.5(11) . . . . ? N2 C11 C18 C17 -173.4(7) . . . . ? C20 C11 C18 C17 58.1(10) . . . . ? C12 C11 C18 C17 -58.9(10) . . . . ? C18 C17 C19 C13 -60.2(10) . . . . ? C16 C17 C19 C13 60.9(10) . . . . ? C14 C13 C19 C17 -60.5(10) . . . . ? C12 C13 C19 C17 58.6(10) . . . . ? C16 C15 C20 C11 59.8(11) . . . . ? C14 C15 C20 C11 -59.9(11) . . . . ? N2 C11 C20 C15 -179.5(8) . . . . ? C12 C11 C20 C15 59.5(10) . . . . ? C18 C11 C20 C15 -58.3(10) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.695 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.099 data_cmpd2 _database_code_CSD 189239 _chemical_name_systematic ; bis(selenenylamine) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H9 N O Se' _chemical_formula_sum 'C4 H9 N O Se' _chemical_formula_weight 166.08 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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.517(4) _cell_length_b 11.499(2) _cell_length_c 5.6722(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1273.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 5.790 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.2755 _exptl_absorpt_correction_T_max 0.5952 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappaccd' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15441 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1608 _reflns_number_gt 1404 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0395P)^2^+1.8208P] 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 SHELXL _refine_ls_extinction_coef 0.0056(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1608 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 Se1 Se 0.210366(14) 0.12628(2) 0.98339(5) 0.02195(14) Uani 1 1 d . . . O1 O 0.20188(12) 0.0538(2) 0.7400(5) 0.0454(7) Uani 1 1 d . . . N1 N 0.14788(16) 0.2500 0.9546(5) 0.0171(6) Uani 1 2 d S . . N2 N 0.27006(16) 0.2500 0.9081(5) 0.0182(6) Uani 1 2 d S . . C1 C 0.08413(19) 0.2500 1.1011(7) 0.0199(8) Uani 1 2 d S . . C11 C 0.0993(3) 0.2500 1.3663(8) 0.0392(11) Uani 1 2 d S . . H11A H 0.1278 0.3174 1.4056 0.059 Uiso 0.50 1 calc PR . . H11B H 0.1236 0.1784 1.4085 0.059 Uiso 0.50 1 calc PR . . H11C H 0.0561 0.2542 1.4542 0.059 Uiso 1 2 calc SR . . C12 C 0.04460(17) 0.1412(3) 1.0321(6) 0.0316(7) Uani 1 1 d . . . H12A H 0.0365 0.1414 0.8616 0.047 Uiso 1 1 calc R . . H12B H 0.0006 0.1399 1.1153 0.047 Uiso 1 1 calc R . . H12C H 0.0713 0.0721 1.0750 0.047 Uiso 1 1 calc R . . C2 C 0.3413(2) 0.2500 1.0027(6) 0.0176(8) Uani 1 2 d S . . C21 C 0.3425(2) 0.2500 1.2728(6) 0.0252(9) Uani 1 2 d S . . H21A H 0.3153 0.3156 1.3318 0.038 Uiso 0.50 1 calc PR . . H21B H 0.3898 0.2575 1.3280 0.038 Uiso 0.50 1 calc PR . . H21C H 0.3229 0.1770 1.3314 0.038 Uiso 0.50 1 calc PR . . C22 C 0.37622(14) 0.1408(2) 0.9063(5) 0.0233(6) Uani 1 1 d . . . H22A H 0.3538 0.0716 0.9714 0.035 Uiso 1 1 calc R . . H22B H 0.4247 0.1410 0.9518 0.035 Uiso 1 1 calc R . . H22C H 0.3725 0.1398 0.7340 0.035 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 Se1 0.01804(19) 0.0131(2) 0.0347(2) -0.00317(10) -0.00490(10) 0.00111(10) O1 0.0348(13) 0.0338(14) 0.0677(17) -0.0362(13) -0.0126(11) 0.0067(11) N1 0.0147(16) 0.0137(16) 0.0230(15) 0.000 -0.0044(12) 0.000 N2 0.0170(16) 0.0186(17) 0.0190(14) 0.000 -0.0039(12) 0.000 C1 0.0163(18) 0.021(2) 0.0225(18) 0.000 -0.0001(14) 0.000 C11 0.038(3) 0.058(3) 0.022(2) 0.000 0.0032(19) 0.000 C12 0.0214(15) 0.0255(18) 0.0477(18) 0.0022(13) 0.0007(13) -0.0081(12) C2 0.0137(17) 0.023(2) 0.0160(16) 0.000 -0.0014(13) 0.000 C21 0.022(2) 0.036(2) 0.0169(17) 0.000 -0.0037(15) 0.000 C22 0.0185(13) 0.0235(15) 0.0280(13) 0.0006(11) 0.0057(11) 0.0046(11) _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 Se1 O1 1.621(2) . ? Se1 N1 1.881(2) . ? Se1 N2 1.888(2) . ? N1 C1 1.496(5) . ? N1 Se1 1.881(2) 7_565 ? N2 C2 1.490(5) . ? N2 Se1 1.888(2) 7_565 ? C1 C12 1.521(4) . ? C1 C12 1.521(4) 7_565 ? C1 C11 1.533(6) . ? C2 C22 1.530(3) . ? C2 C22 1.530(3) 7_565 ? C2 C21 1.533(5) . ? 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 O1 Se1 N1 104.41(12) . . ? O1 Se1 N2 104.94(14) . . ? N1 Se1 N2 79.08(11) . . ? C1 N1 Se1 119.41(14) . 7_565 ? C1 N1 Se1 119.41(14) . . ? Se1 N1 Se1 98.29(14) 7_565 . ? C2 N2 Se1 119.62(13) . . ? C2 N2 Se1 119.62(13) . 7_565 ? Se1 N2 Se1 97.80(15) . 7_565 ? N1 C1 C12 106.2(2) . . ? N1 C1 C12 106.2(2) . 7_565 ? C12 C1 C12 110.7(4) . 7_565 ? N1 C1 C11 112.6(3) . . ? C12 C1 C11 110.5(2) . . ? C12 C1 C11 110.5(2) 7_565 . ? N2 C2 C22 106.7(2) . . ? N2 C2 C22 106.7(2) . 7_565 ? C22 C2 C22 110.3(3) . 7_565 ? N2 C2 C21 112.0(3) . . ? C22 C2 C21 110.5(2) . . ? C22 C2 C21 110.5(2) 7_565 . ? 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 O1 Se1 N1 C1 108.4(2) . . . . ? N2 Se1 N1 C1 -148.8(2) . . . . ? O1 Se1 N1 Se1 -120.97(14) . . . 7_565 ? N2 Se1 N1 Se1 -18.17(14) . . . 7_565 ? O1 Se1 N2 C2 -109.1(2) . . . . ? N1 Se1 N2 C2 148.8(2) . . . . ? O1 Se1 N2 Se1 120.25(13) . . . 7_565 ? N1 Se1 N2 Se1 18.08(13) . . . 7_565 ? Se1 N1 C1 C12 178.7(2) 7_565 . . . ? Se1 N1 C1 C12 -60.8(3) . . . . ? Se1 N1 C1 C12 60.8(3) 7_565 . . 7_565 ? Se1 N1 C1 C12 -178.7(2) . . . 7_565 ? Se1 N1 C1 C11 -60.25(17) 7_565 . . . ? Se1 N1 C1 C11 60.25(17) . . . . ? Se1 N2 C2 C22 60.9(3) . . . . ? Se1 N2 C2 C22 -178.88(19) 7_565 . . . ? Se1 N2 C2 C22 178.88(19) . . . 7_565 ? Se1 N2 C2 C22 -60.9(3) 7_565 . . 7_565 ? Se1 N2 C2 C21 -60.09(17) . . . . ? Se1 N2 C2 C21 60.09(17) 7_565 . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.666 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.112