# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Lorcy, Dominique' 'Casar, Zdenko' 'Leban, Ivan' 'Majcen-Le Marechal, Alenka' _publ_contact_author_name 'Dr Dominique Lorcy' _publ_contact_author_address ; Synthese et Electrosynthese Organiques, UMRCNRS 6510 University of Rennes 1 Campus de Beaulieu, bat 10A Rennes 35042 FRANCE ; _publ_contact_author_email 'DOMINIQUE.LORCY@UNIV-RENNES1.FR' _publ_section_title ; Synthesis of diselenadiazafulvalenes and influence of steric strain on their anodic behavior ; data_10 _database_code_CSD 183223 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 N2 S2 Se2' _chemical_formula_sum 'C16 H12 N2 S2 Se2' _chemical_formula_weight 454.32 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' 'S' 'S' 0.1246 0.1234 '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 Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8982(3) _cell_length_b 10.0070(3) _cell_length_c 13.9470(3) _cell_angle_alpha 102.747(3) _cell_angle_beta 104.027(3) _cell_angle_gamma 103.336(3) _cell_volume 1246.92(6) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5305 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.815 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 666 _exptl_absorpt_coefficient_mu 4.695 _exptl_absorpt_correction_type 'gaussian' _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.775 _exptl_absorpt_process_details ; contained in maXus (Mackay et al., 1998) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 diffractometer' _diffrn_measurement_method ; 563 frames in 6 sets of \w and \f scans. Rotation/frame=1\%. Crystal-detector distance=32 mm. Measuring time=65 s/\%. ; _diffrn_detector_area_resol_mean 0.055 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9637 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5628 _reflns_number_gt 4728 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection ; KappaCCD Reference Manual (Nonius, 1998) ; _computing_cell_refinement ; DENZO and SCALEPACK (Otwinowski & Minor, 1997) ; _computing_data_reduction ; DENZO and SCALEPACK (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPII (Johnson, 1971), PLATON (Spek, 1998), ORTEP-3 (Farugia, 1999) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0864P)^2^+1.0011P] 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 0.013(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5628 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C11 C 0.4933(4) 0.5063(4) 0.9465(3) 0.0404(8) Uani 1 1 d . . . S1 S 0.30780(11) 0.42622(10) 0.86100(8) 0.0457(2) Uani 1 1 d . . . Se1 Se 0.09961(4) 0.11381(4) 0.77922(3) 0.04344(15) Uani 1 1 d . . . C21 C 0.2905(4) 0.2435(4) 0.8416(2) 0.0358(7) Uani 1 1 d . . . N31 N 0.3943(3) 0.1900(3) 0.8681(2) 0.0379(6) Uani 1 1 d . . . C31A C 0.3443(4) 0.0410(4) 0.8433(3) 0.0362(7) Uani 1 1 d . . . C41 C 0.4359(5) -0.0435(5) 0.8636(3) 0.0495(9) Uani 1 1 d . . . H21 H 0.5359 -0.0012 0.8949 0.059 Uiso 1 1 calc R . . C51 C 0.3760(6) -0.1908(5) 0.8367(4) 0.0578(11) Uani 1 1 d . . . H28 H 0.4367 -0.2475 0.8496 0.069 Uiso 1 1 calc R . . C61 C 0.2255(5) -0.2565(5) 0.7903(3) 0.0526(10) Uani 1 1 d . . . H19 H 0.1870 -0.3556 0.7740 0.063 Uiso 1 1 calc R . . C71 C 0.1345(4) -0.1746(4) 0.7688(3) 0.0420(8) Uani 1 1 d . . . H12 H 0.0346 -0.2176 0.7375 0.050 Uiso 1 1 calc R . . C71A C 0.1943(4) -0.0265(4) 0.7945(2) 0.0344(7) Uani 1 1 d . . . C12 C 0.0146(5) 0.5766(5) -0.0013(3) 0.0473(9) Uani 1 1 d . . . S2 S 0.20566(11) 0.68018(12) 0.05906(7) 0.0475(2) Uani 1 1 d . . . Se2 Se 0.41065(4) 0.80082(5) 0.28714(3) 0.04855(16) Uani 1 1 d . . . C22 C 0.2210(4) 0.7080(4) 0.1899(3) 0.0396(8) Uani 1 1 d . . . N32 N 0.1159(4) 0.6694(4) 0.2266(2) 0.0443(7) Uani 1 1 d . . . C32A C 0.1637(4) 0.7066(5) 0.3344(3) 0.0445(8) Uani 1 1 d . . . C42 C 0.0696(5) 0.6790(6) 0.3924(3) 0.0610(12) Uani 1 1 d . . . H29 H -0.0294 0.6318 0.3601 0.073 Uiso 1 1 calc R . . C52 C 0.1263(6) 0.7232(7) 0.4988(4) 0.0725(15) Uani 1 1 d . . . H30 H 0.0644 0.7063 0.5383 0.087 Uiso 1 1 calc R . . C62 C 0.2755(6) 0.7933(7) 0.5482(3) 0.0671(14) Uani 1 1 d . . . H32 H 0.3109 0.8226 0.6200 0.081 Uiso 1 1 calc R . . C72 C 0.3702(5) 0.8192(5) 0.4924(3) 0.0545(10) Uani 1 1 d . . . H22 H 0.4695 0.8642 0.5252 0.065 Uiso 1 1 calc R . . C72A C 0.3125(4) 0.7759(4) 0.3842(3) 0.0427(8) Uani 1 1 d . . . C13 C 0.9248(4) 1.0088(4) 0.9820(3) 0.0409(8) Uani 1 1 d . . . S3 S 0.78518(12) 0.83571(13) 0.93248(8) 0.0523(3) Uani 1 1 d . . . Se3 Se 0.69001(7) 0.59691(5) 0.72452(4) 0.06719(19) Uani 1 1 d . . . C23 C 0.7643(4) 0.7934(4) 0.8006(3) 0.0402(8) Uani 1 1 d . . . N33 N 0.7936(3) 0.8831(4) 0.7491(2) 0.0422(7) Uani 1 1 d . . . C33A C 0.7633(4) 0.8132(4) 0.6440(3) 0.0420(8) Uani 1 1 d . . . C43 C 0.7850(5) 0.8873(6) 0.5722(3) 0.0546(10) Uani 1 1 d . . . H25 H 0.8191 0.9870 0.5922 0.066 Uiso 1 1 calc R . . C53 C 0.7541(5) 0.8075(7) 0.4700(4) 0.0676(14) Uani 1 1 d . . . H31 H 0.7696 0.8548 0.4215 0.081 Uiso 1 1 calc R . . C63 C 0.7005(6) 0.6586(7) 0.4391(4) 0.0725(16) Uani 1 1 d . . . H26 H 0.6800 0.6077 0.3703 0.087 Uiso 1 1 calc R . . C73 C 0.6778(6) 0.5868(6) 0.5084(4) 0.0686(14) Uani 1 1 d . . . H33 H 0.6421 0.4871 0.4874 0.082 Uiso 1 1 calc R . . C73A C 0.7086(5) 0.6641(5) 0.6120(3) 0.0507(9) Uani 1 1 d . . . H2A H 0.516(5) 0.594(6) 0.955(4) 0.050(13) Uiso 1 1 d . . . H3A H 0.550(6) 0.462(6) 0.919(4) 0.055(13) Uiso 1 1 d . . . H4A H 0.904(5) 1.070(5) 1.038(3) 0.044(11) Uiso 1 1 d . . . H5A H -0.034(6) 0.626(6) 0.032(4) 0.060(14) Uiso 1 1 d . . . H6A H 0.925(4) 1.062(4) 0.933(3) 0.031(9) Uiso 1 1 d . . . H7A H -0.015(6) 0.591(6) -0.066(5) 0.066(15) 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 C11 0.042(2) 0.0319(19) 0.039(2) 0.0092(14) 0.0062(15) 0.0036(15) S1 0.0457(5) 0.0358(5) 0.0444(5) 0.0092(4) -0.0008(4) 0.0094(4) Se1 0.0343(2) 0.0404(2) 0.0481(2) 0.00843(16) 0.00610(16) 0.00842(15) C21 0.0357(17) 0.0386(18) 0.0274(15) 0.0071(13) 0.0074(13) 0.0058(14) N31 0.0353(15) 0.0375(16) 0.0359(15) 0.0103(12) 0.0065(12) 0.0067(12) C31A 0.0344(17) 0.0415(18) 0.0309(16) 0.0113(13) 0.0083(13) 0.0094(14) C41 0.043(2) 0.051(2) 0.051(2) 0.0192(18) 0.0032(17) 0.0165(18) C51 0.064(3) 0.049(2) 0.061(3) 0.023(2) 0.010(2) 0.023(2) C61 0.062(3) 0.037(2) 0.057(2) 0.0155(17) 0.015(2) 0.0127(18) C71 0.0416(19) 0.0370(18) 0.0410(19) 0.0075(14) 0.0117(15) 0.0049(15) C71A 0.0373(17) 0.0356(17) 0.0310(16) 0.0096(13) 0.0135(13) 0.0095(13) C12 0.048(2) 0.056(2) 0.0318(19) 0.0061(16) 0.0020(16) 0.0206(19) S2 0.0482(5) 0.0576(6) 0.0308(4) 0.0074(4) 0.0077(4) 0.0148(4) Se2 0.0386(2) 0.0595(3) 0.0356(2) 0.00700(17) 0.00697(15) 0.00367(17) C22 0.0405(18) 0.0438(19) 0.0314(17) 0.0059(14) 0.0068(14) 0.0163(15) N32 0.0382(16) 0.0526(19) 0.0316(15) 0.0000(13) 0.0033(12) 0.0137(14) C32A 0.0403(19) 0.052(2) 0.0349(18) 0.0026(15) 0.0099(15) 0.0127(16) C42 0.043(2) 0.084(3) 0.046(2) 0.005(2) 0.0161(18) 0.012(2) C52 0.061(3) 0.110(5) 0.044(2) 0.014(3) 0.025(2) 0.018(3) C62 0.065(3) 0.095(4) 0.031(2) 0.007(2) 0.0127(19) 0.017(3) C72 0.047(2) 0.066(3) 0.035(2) 0.0032(18) 0.0021(16) 0.0092(19) C72A 0.0404(19) 0.050(2) 0.0313(17) 0.0050(15) 0.0078(14) 0.0112(16) C13 0.0412(19) 0.043(2) 0.0344(18) 0.0072(15) 0.0096(15) 0.0113(15) S3 0.0454(5) 0.0619(7) 0.0379(5) 0.0152(4) 0.0093(4) -0.0024(5) Se3 0.0820(4) 0.0428(3) 0.0595(3) 0.0099(2) 0.0119(2) 0.0017(2) C23 0.0325(17) 0.044(2) 0.0352(17) 0.0078(14) 0.0037(13) 0.0053(14) N33 0.0405(16) 0.0425(17) 0.0332(15) 0.0059(12) 0.0052(12) 0.0046(13) C33A 0.0328(17) 0.048(2) 0.0347(18) 0.0066(15) 0.0025(13) 0.0073(15) C43 0.046(2) 0.070(3) 0.039(2) 0.0161(19) 0.0061(17) 0.009(2) C53 0.049(3) 0.107(4) 0.040(2) 0.021(2) 0.0104(19) 0.015(3) C63 0.053(3) 0.103(4) 0.038(2) -0.008(2) 0.0077(19) 0.012(3) C73 0.063(3) 0.063(3) 0.056(3) -0.012(2) 0.009(2) 0.012(2) C73A 0.043(2) 0.050(2) 0.045(2) 0.0019(17) 0.0050(17) 0.0091(17) _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 C11 C11 1.502(7) 2_667 ? C11 S1 1.810(4) . ? C11 H2A 0.83(5) . ? C11 H3A 0.89(5) . ? S1 C21 1.749(4) . ? Se1 C71A 1.881(4) . ? Se1 C21 1.893(3) . ? C21 N31 1.280(5) . ? N31 C31A 1.392(5) . ? C31A C41 1.397(5) . ? C31A C71A 1.403(5) . ? C41 C51 1.382(6) . ? C41 H21 0.9300 . ? C51 C61 1.401(7) . ? C51 H28 0.9300 . ? C61 C71 1.374(6) . ? C61 H19 0.9300 . ? C71 C71A 1.391(5) . ? C71 H12 0.9300 . ? C12 C12 1.503(9) 2_565 ? C12 S2 1.816(4) . ? C12 H5A 0.90(5) . ? C12 H7A 0.94(6) . ? S2 C22 1.746(4) . ? Se2 C72A 1.874(4) . ? Se2 C22 1.906(4) . ? C22 N32 1.286(5) . ? N32 C32A 1.397(5) . ? C32A C42 1.395(6) . ? C32A C72A 1.398(5) . ? C42 C52 1.379(7) . ? C42 H29 0.9300 . ? C52 C62 1.401(8) . ? C52 H30 0.9300 . ? C62 C72 1.372(7) . ? C62 H32 0.9300 . ? C72 C72A 1.404(5) . ? C72 H22 0.9300 . ? C13 C13 1.516(8) 2_777 ? C13 S3 1.814(4) . ? C13 H4A 0.98(4) . ? C13 H6A 0.95(4) . ? S3 C23 1.743(4) . ? Se3 C73A 1.870(5) . ? Se3 C23 1.889(4) . ? C23 N33 1.293(5) . ? N33 C33A 1.403(5) . ? C33A C73A 1.391(6) . ? C33A C43 1.398(6) . ? C43 C53 1.392(7) . ? C43 H25 0.9300 . ? C53 C63 1.389(9) . ? C53 H31 0.9300 . ? C63 C73 1.355(9) . ? C63 H26 0.9300 . ? C73 C73A 1.400(6) . ? C73 H33 0.9300 . ? 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 C11 C11 S1 112.0(4) 2_667 . ? C11 C11 H2A 104(3) 2_667 . ? S1 C11 H2A 108(3) . . ? C11 C11 H3A 110(3) 2_667 . ? S1 C11 H3A 108(3) . . ? H2A C11 H3A 115(5) . . ? C21 S1 C11 100.88(18) . . ? C71A Se1 C21 83.90(16) . . ? N31 C21 S1 126.0(3) . . ? N31 C21 Se1 117.1(3) . . ? S1 C21 Se1 116.9(2) . . ? C21 N31 C31A 111.9(3) . . ? N31 C31A C41 123.3(3) . . ? N31 C31A C71A 117.7(3) . . ? C41 C31A C71A 119.0(4) . . ? C51 C41 C31A 119.2(4) . . ? C51 C41 H21 120.4 . . ? C31A C41 H21 120.4 . . ? C41 C51 C61 121.2(4) . . ? C41 C51 H28 119.4 . . ? C61 C51 H28 119.4 . . ? C71 C61 C51 120.1(4) . . ? C71 C61 H19 119.9 . . ? C51 C61 H19 119.9 . . ? C61 C71 C71A 118.9(4) . . ? C61 C71 H12 120.6 . . ? C71A C71 H12 120.6 . . ? C71 C71A C31A 121.6(3) . . ? C71 C71A Se1 129.1(3) . . ? C31A C71A Se1 109.3(3) . . ? C12 C12 S2 112.6(4) 2_565 . ? C12 C12 H5A 114(3) 2_565 . ? S2 C12 H5A 105(3) . . ? C12 C12 H7A 117(3) 2_565 . ? S2 C12 H7A 107(3) . . ? H5A C12 H7A 100(5) . . ? C22 S2 C12 101.3(2) . . ? C72A Se2 C22 83.55(16) . . ? N32 C22 S2 125.8(3) . . ? N32 C22 Se2 116.9(3) . . ? S2 C22 Se2 117.3(2) . . ? C22 N32 C32A 112.0(3) . . ? N32 C32A C42 122.8(4) . . ? N32 C32A C72A 117.3(3) . . ? C42 C32A C72A 119.9(4) . . ? C52 C42 C32A 118.7(4) . . ? C52 C42 H29 120.7 . . ? C32A C42 H29 120.7 . . ? C42 C52 C62 121.1(4) . . ? C42 C52 H30 119.4 . . ? C62 C52 H30 119.4 . . ? C72 C62 C52 121.1(4) . . ? C72 C62 H32 119.5 . . ? C52 C62 H32 119.5 . . ? C62 C72 C72A 117.9(4) . . ? C62 C72 H22 121.0 . . ? C72A C72 H22 121.0 . . ? C32A C72A C72 121.3(4) . . ? C32A C72A Se2 110.4(3) . . ? C72 C72A Se2 128.3(3) . . ? C13 C13 S3 110.8(4) 2_777 . ? C13 C13 H4A 111(3) 2_777 . ? S3 C13 H4A 109(3) . . ? C13 C13 H6A 108(2) 2_777 . ? S3 C13 H6A 113(2) . . ? H4A C13 H6A 103(3) . . ? C23 S3 C13 101.92(18) . . ? C73A Se3 C23 84.30(17) . . ? N33 C23 S3 126.6(3) . . ? N33 C23 Se3 116.5(3) . . ? S3 C23 Se3 117.0(2) . . ? C23 N33 C33A 111.9(3) . . ? C73A C33A C43 120.1(4) . . ? C73A C33A N33 117.3(4) . . ? C43 C33A N33 122.7(4) . . ? C53 C43 C33A 118.1(5) . . ? C53 C43 H25 120.9 . . ? C33A C43 H25 120.9 . . ? C63 C53 C43 121.3(5) . . ? C63 C53 H31 119.4 . . ? C43 C53 H31 119.4 . . ? C73 C63 C53 120.6(4) . . ? C73 C63 H26 119.7 . . ? C53 C63 H26 119.7 . . ? C63 C73 C73A 119.5(5) . . ? C63 C73 H33 120.3 . . ? C73A C73 H33 120.3 . . ? C33A C73A C73 120.5(5) . . ? C33A C73A Se3 110.0(3) . . ? C73 C73A Se3 129.5(4) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.984 _refine_diff_density_min -1.600 _refine_diff_density_rms 0.117 data_12 _database_code_CSD 183224 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 N2 S2 Se2' _chemical_formula_sum 'C16 H12 N2 S2 Se2' _chemical_formula_weight 454.32 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' 'S' 'S' 0.1246 0.1234 '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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' 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 16.3534(4) _cell_length_b 5.3820(2) _cell_length_c 19.3559(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.5239(14) _cell_angle_gamma 90.00 _cell_volume 1595.46(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3249 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.4 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 4.893 _exptl_absorpt_correction_type 'gaussian' _exptl_absorpt_correction_T_min 0.520 _exptl_absorpt_correction_T_max 0.854 _exptl_absorpt_process_details ; contained in maXus (Mackay et al., 1998) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 diffractometer' _diffrn_measurement_method ; 346 frames in 4 sets of \w scans. Rotation/frame=1\%. Crystal-detector distance=25 mm. Measuring time=30 s/\%. ; _diffrn_detector_area_resol_mean 0.055 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5500 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2922 _reflns_number_gt 2259 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection ; KappaCCD Reference Manual (Nonius, 1998) ; _computing_cell_refinement ; DENZO and SCALEPACK (Otwinowski & Minor, 1997) ; _computing_data_reduction ; DENZO and SCALEPACK (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPII (Johnson, 1971), PLATON (Spek, 1998), ORTEP-3 (Farugia, 1999) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0377P)^2^+1.0904P] 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 0.0011(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2922 _refine_ls_number_parameters 216 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.005 _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 Se11 Se 0.74461(3) 0.10120(9) 0.02061(3) 0.03767(17) Uani 1 1 d . . . C21 C 0.6596(3) 0.3523(8) -0.0120(2) 0.0309(10) Uani 1 1 d . . . S11 S 0.64548(9) 0.5221(2) -0.08681(7) 0.0426(3) Uani 1 1 d . . . N31 N 0.6131(2) 0.3702(6) 0.03426(19) 0.0278(8) Uani 1 1 d . . . C31 C 0.5436(3) 0.5556(9) 0.0219(3) 0.0307(10) Uani 1 1 d D . . H1 H 0.555(3) 0.677(8) 0.002(2) 0.016(11) Uiso 1 1 d D . . H2 H 0.541(3) 0.604(8) 0.057(2) 0.014(11) Uiso 1 1 d D . . C31A C 0.6325(3) 0.1968(8) 0.0921(2) 0.0284(9) Uani 1 1 d . . . C41 C 0.5887(3) 0.1782(8) 0.1421(2) 0.0325(10) Uani 1 1 d . . . H41 H 0.5423 0.2887 0.1393 0.039 Uiso 1 1 calc R . . C51 C 0.6139(3) -0.0037(8) 0.1956(2) 0.0343(10) Uani 1 1 d . . . H51 H 0.5847 -0.0172 0.2301 0.041 Uiso 1 1 calc R . . C61 C 0.6812(3) -0.1678(8) 0.1999(2) 0.0342(10) Uani 1 1 d . . . H61 H 0.6978 -0.2913 0.2374 0.041 Uiso 1 1 calc R . . C71 C 0.7242(3) -0.1518(8) 0.1499(3) 0.0333(10) Uani 1 1 d . . . H71 H 0.7695 -0.2657 0.1521 0.040 Uiso 1 1 calc R . . C71A C 0.7004(3) 0.0325(8) 0.0965(2) 0.0291(10) Uani 1 1 d . . . Se12 Se 0.97762(3) 1.00200(9) 0.22023(3) 0.03653(16) Uani 1 1 d . . . C22 C 0.9696(3) 0.8717(7) 0.1285(2) 0.0278(9) Uani 1 1 d . . . S22 S 0.90214(7) 0.6407(2) 0.08744(6) 0.0332(3) Uani 1 1 d . . . N32 N 1.0255(2) 0.9916(6) 0.10162(19) 0.0256(7) Uani 1 1 d . . . C32 C 1.0316(4) 0.9251(11) 0.0306(3) 0.0285(10) Uani 1 1 d D . . H3 H 1.076(3) 0.944(7) 0.032(2) 0.012(12) Uiso 1 1 d D . . H4 H 1.023(3) 0.807(7) 0.029(2) 0.006(13) Uiso 1 1 d D . . C32A C 1.0749(3) 1.1872(8) 0.1449(2) 0.0267(9) Uani 1 1 d . . . C42 C 1.1326(3) 1.3403(8) 0.1248(2) 0.0317(10) Uani 1 1 d . . . H42 H 1.1425 1.3160 0.0798 0.038 Uiso 1 1 calc R . . C52 C 1.1743(3) 1.5275(8) 0.1732(3) 0.0379(11) Uani 1 1 d . . . H52 H 1.2131 1.6345 0.1606 0.045 Uiso 1 1 calc R . . C62 C 1.1615(3) 1.5642(9) 0.2394(3) 0.0401(12) Uani 1 1 d . . . H62 H 1.1917 1.6938 0.2715 0.048 Uiso 1 1 calc R . . C72 C 1.1042(3) 1.4116(8) 0.2593(3) 0.0353(11) Uani 1 1 d . . . H72 H 1.0950 1.4362 0.3046 0.042 Uiso 1 1 calc R . . C72A C 1.0612(3) 1.2235(8) 0.2115(2) 0.0294(10) 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 Se11 0.0343(3) 0.0388(3) 0.0448(3) -0.0008(2) 0.0200(2) 0.0038(2) C21 0.029(2) 0.033(2) 0.032(2) -0.0030(19) 0.012(2) -0.0038(19) S11 0.0487(8) 0.0474(7) 0.0375(7) 0.0058(6) 0.0221(6) 0.0027(6) N31 0.0269(19) 0.027(2) 0.0301(19) -0.0003(16) 0.0103(16) 0.0030(15) C31 0.036(3) 0.026(3) 0.031(3) -0.003(2) 0.013(2) 0.004(2) C31A 0.027(2) 0.028(2) 0.030(2) -0.0015(18) 0.0100(19) 0.0008(19) C41 0.032(2) 0.034(2) 0.034(2) -0.002(2) 0.016(2) 0.003(2) C51 0.038(3) 0.036(2) 0.033(2) 0.001(2) 0.017(2) -0.006(2) C61 0.036(3) 0.029(2) 0.034(3) 0.0055(19) 0.008(2) 0.001(2) C71 0.026(2) 0.032(2) 0.042(3) -0.002(2) 0.011(2) 0.0024(19) C71A 0.025(2) 0.030(2) 0.033(2) -0.0072(19) 0.0125(19) -0.0049(18) Se12 0.0466(3) 0.0344(3) 0.0355(3) -0.0015(2) 0.0230(2) -0.0016(2) C22 0.032(2) 0.023(2) 0.031(2) 0.0023(18) 0.0141(19) 0.0033(18) S22 0.0339(6) 0.0297(6) 0.0383(6) -0.0026(5) 0.0154(5) -0.0021(5) N32 0.0262(19) 0.0266(18) 0.0242(17) 0.0007(15) 0.0092(15) 0.0023(15) C32 0.027(3) 0.026(3) 0.035(3) 0.000(2) 0.014(2) 0.002(2) C32A 0.024(2) 0.025(2) 0.028(2) 0.0026(18) 0.0064(18) 0.0082(18) C42 0.024(2) 0.037(3) 0.035(2) 0.006(2) 0.011(2) 0.0029(19) C52 0.024(2) 0.032(3) 0.053(3) 0.009(2) 0.008(2) 0.001(2) C62 0.033(3) 0.031(2) 0.045(3) -0.003(2) 0.000(2) 0.002(2) C72 0.035(3) 0.032(2) 0.035(3) 0.000(2) 0.008(2) 0.004(2) C72A 0.031(2) 0.030(2) 0.029(2) 0.0023(19) 0.0125(19) 0.0034(19) _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 Se11 C21 1.882(4) . ? Se11 C71A 1.887(4) . ? C21 N31 1.367(5) . ? C21 S11 1.658(4) . ? N31 C31A 1.406(5) . ? N31 C31 1.467(6) . ? C31 C31 1.505(10) 3_665 ? C31 H1 0.82(4) . ? C31 H2 0.75(4) . ? C31A C41 1.395(6) . ? C31A C71A 1.399(6) . ? C41 C51 1.379(6) . ? C41 H41 0.9500 . ? C51 C61 1.391(6) . ? C51 H51 0.9500 . ? C61 C71 1.385(6) . ? C61 H61 0.9500 . ? C71 C71A 1.386(6) . ? C71 H71 0.9500 . ? Se12 C72A 1.865(4) . ? Se12 C22 1.871(4) . ? C22 N32 1.363(5) . ? C22 S22 1.667(4) . ? N32 C32A 1.410(5) . ? N32 C32 1.457(6) . ? C32 C32 1.506(10) 3_775 ? C32 H3 0.72(4) . ? C32 H4 0.65(4) . ? C32A C72A 1.398(6) . ? C32A C42 1.407(6) . ? C42 C52 1.382(7) . ? C42 H42 0.9500 . ? C52 C62 1.384(7) . ? C52 H52 0.9500 . ? C62 C72 1.397(7) . ? C62 H62 0.9500 . ? C72 C72A 1.385(6) . ? C72 H72 0.9500 . ? 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 C21 Se11 C71A 87.87(19) . . ? N31 C21 S11 126.4(3) . . ? N31 C21 Se11 110.2(3) . . ? S11 C21 Se11 123.3(2) . . ? C21 N31 C31A 116.9(3) . . ? C21 N31 C31 121.2(4) . . ? C31A N31 C31 121.8(4) . . ? N31 C31 C31 110.4(5) . 3_665 ? N31 C31 H1 109(3) . . ? C31 C31 H1 112(3) 3_665 . ? N31 C31 H2 112(3) . . ? C31 C31 H2 108(3) 3_665 . ? H1 C31 H2 105(4) . . ? C41 C31A C71A 120.2(4) . . ? C41 C31A N31 124.9(4) . . ? C71A C31A N31 114.9(4) . . ? C51 C41 C31A 118.7(4) . . ? C51 C41 H41 120.6 . . ? C31A C41 H41 120.6 . . ? C41 C51 C61 121.2(4) . . ? C41 C51 H51 119.4 . . ? C61 C51 H51 119.4 . . ? C71 C61 C51 120.2(4) . . ? C71 C61 H61 119.9 . . ? C51 C61 H61 119.9 . . ? C61 C71 C71A 119.2(4) . . ? C61 C71 H71 120.4 . . ? C71A C71 H71 120.4 . . ? C71 C71A C31A 120.4(4) . . ? C71 C71A Se11 129.5(3) . . ? C31A C71A Se11 110.0(3) . . ? C72A Se12 C22 87.92(18) . . ? N32 C22 S22 126.3(3) . . ? N32 C22 Se12 110.6(3) . . ? S22 C22 Se12 123.1(2) . . ? C22 N32 C32A 116.6(3) . . ? C22 N32 C32 121.4(4) . . ? C32A N32 C32 122.0(4) . . ? N32 C32 C32 110.9(5) . 3_775 ? N32 C32 H3 109(3) . . ? C32 C32 H3 111(3) 3_775 . ? N32 C32 H4 102(4) . . ? C32 C32 H4 113(4) 3_775 . ? H3 C32 H4 110(5) . . ? C72A C32A C42 120.9(4) . . ? C72A C32A N32 114.1(4) . . ? C42 C32A N32 124.9(4) . . ? C52 C42 C32A 117.3(4) . . ? C52 C42 H42 121.3 . . ? C32A C42 H42 121.3 . . ? C42 C52 C62 122.2(4) . . ? C42 C52 H52 118.9 . . ? C62 C52 H52 118.9 . . ? C52 C62 C72 120.4(4) . . ? C52 C62 H62 119.8 . . ? C72 C62 H62 119.8 . . ? C72A C72 C62 118.6(4) . . ? C72A C72 H72 120.7 . . ? C62 C72 H72 120.7 . . ? C72 C72A C32A 120.6(4) . . ? C72 C72A Se12 128.6(3) . . ? C32A C72A Se12 110.7(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.531 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.091