Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_Global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _audit_creation_method SHELXL-97 #------------------------------------------------------------------------------ _publ_contact_author ; Masood Parvez Department of Chemistry University of Calgary 2500 University Drive N.W. Calgary, Alberta, Canada T2N 1N4 ; _publ_requested_coeditor_name ' ? ' _publ_contact_author_phone ' (403)220-5348 ' _publ_contact_author_fax ' (403)289-9488 ' _publ_contact_author_email parvez@ucalgary.ca _publ_section_title ;Formation of a Spirodiazaselenurane and its Corresponding Azaselenonium Derivatives from the Oxidation of 2,2'-Selenobis(benzamide). Structure, Properties and Glutathione Peroxidase Activity ; _publ_contact_author_name 'Masood Parvez' loop_ _publ_author_name T.Back D.Kuzma M.Parvez #------------------------------------------------------------------------------ data_Compound_15 _database_code_depnum_ccdc_archive 'CCDC 653872' #----------------------------------------------------------------------------- _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #----------------------------------------------------------------------------- _vrf_PUBL012_GLOBAL ; PROBLEM: _publ_section_abstract is missing. RESPONSE: Will appear in the paper ; # end Validation Reply Form _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl N2 O2.50 Se' _chemical_formula_weight 362.67 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.944(3) _cell_length_b 9.700(4) _cell_length_c 11.001(3) _cell_angle_alpha 81.649(3) _cell_angle_beta 74.131(3) _cell_angle_gamma 67.241(2) _cell_volume 751.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6428 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 27.4 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 2.683 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8556 _exptl_absorpt_correction_T_max 0.9003 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _diffrn_ambient_temperature 173(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 ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6428 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.8 _diffrn_reflns_theta_max 27.4 _reflns_number_total 3416 _reflns_number_gt 2865 _reflns_threshold_expression 'I > 2.0\s(I) ' _refine_special_details ; A difference map showed electron density region consistent with a disordered water molecule lying over two sites across an inversion center with 0.25 site occupancy factor each. H-atoms bonded to N-atoms were allowed to refine. 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^)+(0.0339P)^2^+0.6351P] 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 3416 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.081 _refine_ls_wR_factor_gt 0.076 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 0.23981(4) 0.34483(3) 0.85101(2) 0.01987(10) Uani 1 1 d . . . Cl1 Cl 0.19497(9) 0.42361(8) 0.13301(6) 0.02464(16) Uani 1 1 d . . . O1 O 0.2294(3) 0.7494(2) 0.7350(2) 0.0333(5) Uani 1 1 d . . . O2 O 0.2593(3) 0.1087(2) 0.81781(19) 0.0263(4) Uani 1 1 d . . . N1 N 0.2612(3) 0.5285(3) 0.8499(2) 0.0231(5) Uani 1 1 d . . . H1 H 0.233(5) 0.558(4) 0.918(3) 0.028 Uiso 1 1 d . . . N2 N 0.4578(4) -0.1308(3) 0.8212(2) 0.0268(6) Uani 1 1 d . . . H2A H 0.369(5) -0.155(4) 0.810(3) 0.032 Uiso 1 1 d . . . H2B H 0.558(5) -0.195(4) 0.831(3) 0.032 Uiso 1 1 d . . . C1 C 0.2459(4) 0.6176(3) 0.7432(3) 0.0245(6) Uani 1 1 d . . . C2 C 0.2518(4) 0.5331(3) 0.6394(3) 0.0234(6) Uani 1 1 d . . . C3 C 0.2552(4) 0.3890(3) 0.6719(2) 0.0216(6) Uani 1 1 d . . . C4 C 0.2566(4) 0.2972(4) 0.5852(3) 0.0288(7) Uani 1 1 d . . . H4 H 0.2596 0.1976 0.6114 0.035 Uiso 1 1 d R . . C5 C 0.2539(5) 0.3575(4) 0.4627(3) 0.0373(8) Uani 1 1 d . . . H5 H 0.2521 0.2992 0.3999 0.045 Uiso 1 1 d R . . C6 C 0.2510(5) 0.5006(4) 0.4287(3) 0.0355(8) Uani 1 1 d . . . H6 H 0.2497 0.5401 0.3436 0.043 Uiso 1 1 d R . . C7 C 0.2510(4) 0.5898(4) 0.5161(3) 0.0315(7) Uani 1 1 d . . . H7 H 0.2502 0.6893 0.4931 0.038 Uiso 1 1 d R . . C8 C 0.4171(4) 0.0133(3) 0.8264(3) 0.0212(6) Uani 1 1 d . . . C9 C 0.5589(4) 0.0696(3) 0.8424(3) 0.0219(6) Uani 1 1 d . . . C10 C 0.5013(4) 0.2242(3) 0.8513(2) 0.0196(5) Uani 1 1 d . . . C11 C 0.6219(4) 0.2888(3) 0.8659(3) 0.0231(6) Uani 1 1 d . . . H11 H 0.5786 0.3951 0.8728 0.028 Uiso 1 1 d R . . C12 C 0.8051(4) 0.1966(3) 0.8694(3) 0.0282(7) Uani 1 1 d . . . H12 H 0.8917 0.2394 0.8780 0.034 Uiso 1 1 d R . . C13 C 0.8651(4) 0.0433(3) 0.8602(3) 0.0306(7) Uani 1 1 d . . . H13 H 0.9911 -0.0195 0.8645 0.037 Uiso 1 1 d R . . C14 C 0.7421(4) -0.0206(3) 0.8468(3) 0.0261(6) Uani 1 1 d . . . H14 H 0.7826 -0.1267 0.8400 0.031 Uiso 1 1 d R . . O3 O 0.2782(19) 0.9553(11) 0.5072(10) 0.055(3) Uani 0.25 1 d P . . O4 O 0.084(3) 1.0134(18) 0.5072(18) 0.117(8) Uani 0.25 1 d P . . 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 0.01734(15) 0.01928(15) 0.02317(15) -0.00074(10) -0.00679(10) -0.00562(11) Cl1 0.0237(4) 0.0227(4) 0.0257(3) -0.0024(3) -0.0086(3) -0.0042(3) O1 0.0376(13) 0.0227(12) 0.0465(13) 0.0031(9) -0.0211(10) -0.0124(10) O2 0.0197(10) 0.0201(10) 0.0410(12) -0.0002(9) -0.0120(9) -0.0065(8) N1 0.0259(13) 0.0211(13) 0.0244(12) -0.0026(10) -0.0103(10) -0.0074(10) N2 0.0204(13) 0.0217(13) 0.0392(15) -0.0010(11) -0.0116(11) -0.0059(11) C1 0.0175(14) 0.0249(16) 0.0329(16) -0.0008(12) -0.0093(11) -0.0077(12) C2 0.0196(14) 0.0246(15) 0.0250(14) 0.0001(11) -0.0055(11) -0.0073(12) C3 0.0182(13) 0.0247(15) 0.0205(13) -0.0021(11) -0.0060(10) -0.0050(11) C4 0.0307(17) 0.0318(17) 0.0269(15) -0.0041(13) -0.0095(12) -0.0118(14) C5 0.041(2) 0.048(2) 0.0253(16) -0.0101(14) -0.0091(14) -0.0140(16) C6 0.0339(18) 0.051(2) 0.0216(15) 0.0040(14) -0.0083(13) -0.0160(16) C7 0.0314(17) 0.0352(18) 0.0296(16) 0.0063(13) -0.0113(13) -0.0140(14) C8 0.0199(14) 0.0212(14) 0.0236(14) -0.0007(11) -0.0058(11) -0.0084(11) C9 0.0191(14) 0.0245(15) 0.0210(13) -0.0012(11) -0.0027(10) -0.0082(11) C10 0.0171(13) 0.0195(14) 0.0216(13) 0.0003(10) -0.0060(10) -0.0055(11) C11 0.0210(14) 0.0212(14) 0.0277(15) 0.0002(11) -0.0065(11) -0.0084(12) C12 0.0206(15) 0.0300(16) 0.0358(16) -0.0032(13) -0.0065(12) -0.0109(13) C13 0.0198(15) 0.0280(16) 0.0424(18) -0.0045(13) -0.0077(13) -0.0059(13) C14 0.0193(14) 0.0212(15) 0.0365(16) -0.0035(12) -0.0071(12) -0.0049(12) O3 0.083(9) 0.018(5) 0.049(6) 0.001(4) -0.013(6) -0.005(5) O4 0.17(2) 0.046(8) 0.101(12) -0.014(8) -0.010(14) -0.019(12) _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 1.852(3) . ? Se1 C3 1.936(3) . ? Se1 C10 1.951(3) . ? Se1 O2 2.311(2) . ? O1 C1 1.225(4) . ? O2 C8 1.256(3) . ? N1 C1 1.357(4) . ? N1 H1 0.78(3) . ? N2 C8 1.314(4) . ? N2 H2A 0.87(4) . ? N2 H2B 0.82(4) . ? C1 C2 1.481(4) . ? C2 C3 1.383(4) . ? C2 C7 1.388(4) . ? C3 C4 1.391(4) . ? C4 C5 1.392(4) . ? C4 H4 0.9599 . ? C5 C6 1.377(5) . ? C5 H5 0.9600 . ? C6 C7 1.383(5) . ? C6 H6 0.9601 . ? C7 H7 0.9600 . ? C8 C9 1.487(4) . ? C9 C14 1.388(4) . ? C9 C10 1.399(4) . ? C10 C11 1.384(4) . ? C11 C12 1.390(4) . ? C11 H11 0.9600 . ? C12 C13 1.385(4) . ? C12 H12 0.9600 . ? C13 C14 1.391(4) . ? C13 H13 0.9602 . ? C14 H14 0.9599 . ? O3 O4 1.43(2) . ? O4 O4 1.50(4) 2_576 ? 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 C3 84.93(11) . . ? N1 Se1 C10 96.03(11) . . ? C3 Se1 C10 101.42(11) . . ? N1 Se1 O2 169.00(9) . . ? C3 Se1 O2 87.28(10) . . ? C10 Se1 O2 77.92(10) . . ? C8 O2 Se1 110.32(17) . . ? C1 N1 Se1 117.17(19) . . ? C1 N1 H1 124(2) . . ? Se1 N1 H1 112(2) . . ? C8 N2 H2A 115(2) . . ? C8 N2 H2B 123(2) . . ? H2A N2 H2B 121(3) . . ? O1 C1 N1 124.4(3) . . ? O1 C1 C2 125.3(3) . . ? N1 C1 C2 110.3(2) . . ? C3 C2 C7 119.7(3) . . ? C3 C2 C1 115.8(2) . . ? C7 C2 C1 124.5(3) . . ? C2 C3 C4 122.4(3) . . ? C2 C3 Se1 110.6(2) . . ? C4 C3 Se1 126.9(2) . . ? C3 C4 C5 116.6(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 123.5 . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5 118.6 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 118.8 . . ? C6 C7 C2 118.8(3) . . ? C6 C7 H7 121.3 . . ? C2 C7 H7 119.9 . . ? O2 C8 N2 122.1(3) . . ? O2 C8 C9 117.4(2) . . ? N2 C8 C9 120.5(3) . . ? C14 C9 C10 119.1(3) . . ? C14 C9 C8 124.3(3) . . ? C10 C9 C8 116.6(2) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 Se1 121.1(2) . . ? C9 C10 Se1 117.4(2) . . ? C10 C11 C12 118.5(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 121.5 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 119.9(3) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 120.7 . . ? 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 N1 Se1 O2 C8 63.2(5) . . . . ? C3 Se1 O2 C8 108.10(19) . . . . ? C10 Se1 O2 C8 5.80(18) . . . . ? C3 Se1 N1 C1 10.5(2) . . . . ? C10 Se1 N1 C1 111.5(2) . . . . ? O2 Se1 N1 C1 55.5(6) . . . . ? Se1 N1 C1 O1 168.8(2) . . . . ? Se1 N1 C1 C2 -11.2(3) . . . . ? O1 C1 C2 C3 -174.8(3) . . . . ? N1 C1 C2 C3 5.2(4) . . . . ? O1 C1 C2 C7 4.2(5) . . . . ? N1 C1 C2 C7 -175.9(3) . . . . ? C7 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C4 178.5(3) . . . . ? C7 C2 C3 Se1 -176.5(2) . . . . ? C1 C2 C3 Se1 2.5(3) . . . . ? N1 Se1 C3 C2 -6.8(2) . . . . ? C10 Se1 C3 C2 -101.9(2) . . . . ? O2 Se1 C3 C2 -179.0(2) . . . . ? N1 Se1 C3 C4 177.5(3) . . . . ? C10 Se1 C3 C4 82.3(3) . . . . ? O2 Se1 C3 C4 5.2(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? Se1 C3 C4 C5 175.2(2) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C2 -0.7(5) . . . . ? C3 C2 C7 C6 0.9(4) . . . . ? C1 C2 C7 C6 -178.0(3) . . . . ? Se1 O2 C8 N2 174.5(2) . . . . ? Se1 O2 C8 C9 -5.7(3) . . . . ? O2 C8 C9 C14 -176.5(3) . . . . ? N2 C8 C9 C14 3.2(4) . . . . ? O2 C8 C9 C10 2.3(4) . . . . ? N2 C8 C9 C10 -177.9(3) . . . . ? C14 C9 C10 C11 -0.9(4) . . . . ? C8 C9 C10 C11 -179.8(2) . . . . ? C14 C9 C10 Se1 -177.8(2) . . . . ? C8 C9 C10 Se1 3.3(3) . . . . ? N1 Se1 C10 C11 7.8(2) . . . . ? C3 Se1 C10 C11 93.8(2) . . . . ? O2 Se1 C10 C11 178.5(2) . . . . ? N1 Se1 C10 C9 -175.3(2) . . . . ? C3 Se1 C10 C9 -89.3(2) . . . . ? O2 Se1 C10 C9 -4.59(19) . . . . ? C9 C10 C11 C12 1.2(4) . . . . ? Se1 C10 C11 C12 178.0(2) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? C8 C9 C14 C13 179.0(3) . . . . ? C12 C13 C14 C9 0.2(5) . . . . ? 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 N1 H1 Cl1 0.78(3) 2.53(3) 3.100(3) 131(3) 1_556 N2 H2A O1 0.87(4) 2.07(4) 2.904(4) 161(3) 1_545 N2 H2B Cl1 0.82(4) 2.39(4) 3.195(3) 165(3) 2_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.4 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.53 _refine_diff_density_min -0.52 _refine_diff_density_rms 0.091 #--------END------------------------------------------------------------- data_Compound_20 _database_code_depnum_ccdc_archive 'CCDC 653873' #----------------------------------------------------------------------------- _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #----------------------------------------------------------------------------- _vrf_PUBL012_GLOBAL ; PROBLEM: _publ_section_abstract is missing. RESPONSE: Will appear in the paper ; # end Validation Reply Form _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N2 O6 Se' _chemical_formula_weight 389.26 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 Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.554(2) _cell_length_b 18.386(4) _cell_length_c 9.912(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.57(2) _cell_angle_gamma 90.00 _cell_volume 810.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4116 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 2.35 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _diffrn_ambient_temperature 173(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 ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4116 _diffrn_reflns_av_R_equivalents 0.12 _diffrn_reflns_av_sigmaI/netI 0.10 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.9 _diffrn_reflns_theta_max 25.0 _reflns_number_total 1397 _reflns_number_gt 1041 _reflns_threshold_expression >2sigma(I) _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^)+5.32P] 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 0.10(4) _refine_ls_number_reflns 1397 _refine_ls_number_parameters 236 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.120 _refine_ls_R_factor_gt 0.075 _refine_ls_wR_factor_ref 0.159 _refine_ls_wR_factor_gt 0.137 _refine_ls_goodness_of_fit_ref 1.21 _refine_ls_restrained_S_all 1.20 _refine_ls_shift/su_max 0.007 _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 0.6322(8) 0.3934(5) 0.34903(18) 0.0405(8) Uani 0.954(8) 1 d P A 1 Se1' Se 0.469(17) 0.404(2) 0.347(4) 0.0405(8) Uani 0.046(8) 1 d P A 2 O1 O 0.281(3) 0.5842(8) 0.2779(11) 0.048(3) Uani 1 1 d . . . O2 O 0.677(3) 0.2593(9) 0.3235(13) 0.052(3) Uani 1 1 d . . . N1 N 0.579(3) 0.4915(9) 0.3816(15) 0.043(4) Uani 1 1 d D . . H1 H 0.6700 0.5190 0.4510 0.052 Uiso 1 1 d D . . N2 N 0.731(4) 0.1668(9) 0.4765(17) 0.057(4) Uani 1 1 d . . . H2A H 0.8184 0.1392 0.4240 0.069 Uiso 1 1 calc R A . H2B H 0.7034 0.1501 0.5560 0.069 Uiso 1 1 calc R . . C1 C 0.353(4) 0.5192(10) 0.2824(18) 0.046(5) Uani 1 1 d . A . C2 C 0.177(5) 0.4663(12) 0.185(2) 0.044(5) Uani 1 1 d . . . C3 C 0.275(3) 0.3941(15) 0.1997(13) 0.040(4) Uani 1 1 d . A . C4 C 0.148(4) 0.3372(12) 0.121(2) 0.044(5) Uani 1 1 d . . . H4 H 0.2198 0.2887 0.1368 0.052 Uiso 1 1 calc R A . C5 C -0.098(5) 0.3560(15) 0.015(3) 0.061(8) Uani 1 1 d . A . H5 H -0.1943 0.3190 -0.0452 0.073 Uiso 1 1 calc R . . C6 C -0.206(5) 0.4276(16) -0.004(2) 0.052(7) Uani 1 1 d . . . H6 H -0.3748 0.4380 -0.0769 0.063 Uiso 1 1 calc R A . C7 C -0.074(5) 0.4810(12) 0.078(2) 0.055(5) Uani 1 1 d . A . H7 H -0.1490 0.5293 0.0635 0.067 Uiso 1 1 calc R . . C8 C 0.642(4) 0.2331(10) 0.436(2) 0.046(5) Uani 1 1 d . A . C9 C 0.491(5) 0.2792(10) 0.523(2) 0.052(5) Uani 1 1 d . . . C10 C 0.459(4) 0.3525(10) 0.4964(19) 0.043(5) Uani 1 1 d . A . C11 C 0.328(3) 0.4033(12) 0.5728(17) 0.040(4) Uani 1 1 d . . . H11 H 0.3143 0.4538 0.5527 0.048 Uiso 1 1 calc R A . C12 C 0.217(4) 0.3709(10) 0.683(2) 0.053(5) Uani 1 1 d . A . H12 H 0.1236 0.4011 0.7398 0.063 Uiso 1 1 calc R . . C13 C 0.241(4) 0.2968(11) 0.7112(19) 0.046(5) Uani 1 1 d . . . H13 H 0.1604 0.2766 0.7837 0.055 Uiso 1 1 calc R A . C14 C 0.382(4) 0.2530(11) 0.6325(17) 0.046(5) Uani 1 1 d . A . H14 H 0.4043 0.2028 0.6545 0.055 Uiso 1 1 calc R . . O3 O 0.0907(18) 0.0561(8) 0.3756(14) 0.064(4) Uani 1 1 d D . . H103 H 0.1300 0.0510 0.2990 0.077 Uiso 1 1 d D . . O4 O 0.5276(9) 0.0468(3) 0.2140(11) 0.082(5) Uani 1 1 d D . . H104 H 0.4271 0.0440 0.2731 0.098 Uiso 1 1 d D . . H204 H 0.6600 0.0160 0.2320 0.098 Uiso 1 1 d D . . O5 O 0.9892(10) 0.1811(2) 0.9220(13) 0.062(4) Uani 1 1 d D . . H105 H 0.8450 0.1880 0.9580 0.075 Uiso 1 1 d D . . H205 H 0.9400 0.1480 0.8660 0.075 Uiso 1 1 d D . . O6 O 0.5706(10) 0.1761(3) 0.0758(13) 0.060(3) Uani 1 1 d D . . H106 H 0.6360 0.1960 0.1500 0.072 Uiso 1 1 d D . . H206 H 0.7100 0.1530 0.0570 0.072 Uiso 1 1 d 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 Se1 0.0426(19) 0.0300(7) 0.0476(9) 0.0024(14) 0.0072(8) -0.0018(15) Se1' 0.0426(19) 0.0300(7) 0.0476(9) 0.0024(14) 0.0072(8) -0.0018(15) O1 0.066(8) 0.026(6) 0.048(7) 0.008(5) 0.007(6) 0.012(6) O2 0.057(9) 0.051(8) 0.050(9) 0.010(7) 0.013(7) 0.015(7) N1 0.051(10) 0.036(8) 0.040(10) -0.005(7) 0.004(8) -0.013(7) N2 0.070(11) 0.034(9) 0.071(11) 0.002(8) 0.021(9) 0.005(8) C1 0.068(13) 0.037(10) 0.040(11) 0.002(8) 0.026(10) 0.003(9) C2 0.055(12) 0.046(12) 0.034(12) 0.006(10) 0.017(10) 0.001(9) C3 0.047(8) 0.036(7) 0.036(8) -0.012(15) 0.002(6) 0.019(14) C4 0.048(12) 0.038(11) 0.045(13) -0.002(11) 0.009(10) -0.010(9) C5 0.038(14) 0.047(14) 0.10(2) -0.007(14) 0.010(14) -0.023(11) C6 0.055(14) 0.087(17) 0.013(10) 0.005(9) 0.003(9) 0.001(12) C7 0.076(15) 0.035(10) 0.050(13) 0.022(10) 0.003(11) -0.009(10) C8 0.058(12) 0.025(9) 0.047(12) -0.010(9) -0.002(10) 0.003(8) C9 0.069(13) 0.038(10) 0.048(12) 0.003(9) 0.012(10) -0.007(9) C10 0.048(11) 0.033(10) 0.046(12) 0.014(8) 0.005(9) -0.013(8) C11 0.035(8) 0.012(10) 0.070(11) -0.006(10) 0.003(8) 0.002(8) C12 0.045(11) 0.048(13) 0.068(14) -0.001(9) 0.021(10) -0.011(8) C13 0.031(9) 0.052(11) 0.050(12) 0.009(10) -0.003(9) 0.012(8) C14 0.061(12) 0.040(9) 0.028(10) -0.003(8) -0.011(9) 0.004(9) O3 0.060(8) 0.036(7) 0.090(11) -0.002(7) 0.006(8) 0.005(6) O4 0.068(10) 0.072(10) 0.105(13) -0.002(9) 0.019(9) 0.006(8) O5 0.076(9) 0.045(8) 0.070(10) -0.013(7) 0.026(8) -0.003(7) O6 0.073(9) 0.044(7) 0.066(9) -0.003(7) 0.022(7) 0.007(7) 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 1.857(15) . ? Se1 C3 1.945(13) . ? Se1 C10 1.955(17) . ? Se1 O2 2.492(14) . ? Se1' C3 1.54(5) . ? Se1' C10 1.76(4) . ? Se1' C2 2.17(6) . ? Se1' C1 2.24(5) . ? O1 C1 1.24(2) . ? O2 C8 1.26(2) . ? N1 C1 1.36(2) . ? N1 H1 0.88 . ? N2 C8 1.32(2) . ? N2 H2A 0.88 . ? N2 H2B 0.88 . ? C1 C2 1.47(3) . ? C2 C3 1.40(3) . ? C2 C7 1.41(3) . ? C3 C4 1.36(3) . ? C4 C5 1.40(3) . ? C4 H4 0.95 . ? C5 C6 1.41(3) . ? C5 H5 0.95 . ? C6 C7 1.33(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C9 1.48(3) . ? C9 C10 1.37(2) . ? C9 C14 1.38(3) . ? C10 C11 1.41(2) . ? C11 C12 1.43(3) . ? C11 H11 0.95 . ? C12 C13 1.39(2) . ? C12 H12 0.95 . ? C13 C14 1.37(2) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? O3 H103 0.82 . ? O4 H104 0.82 . ? O4 H204 0.82 . ? O5 H105 0.82 . ? O5 H205 0.82 . ? O6 H106 0.82 . ? O6 H206 0.82 . ? 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 C3 90.3(9) . . ? N1 Se1 C10 98.9(7) . . ? C3 Se1 C10 99.5(8) . . ? N1 Se1 O2 174.4(6) . . ? C3 Se1 O2 90.2(8) . . ? C10 Se1 O2 75.5(6) . . ? C8 O2 Se1 105.1(11) . . ? C1 N1 Se1 110.2(11) . . ? C1 N1 H1 120 . . ? Se1 N1 H1 129 . . ? C8 N2 H2A 120.0 . . ? C8 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O1 C1 N1 122.8(17) . . ? O1 C1 C2 120.7(18) . . ? N1 C1 C2 116.3(16) . . ? C3 C2 C7 116.6(18) . . ? C3 C2 C1 116.3(17) . . ? C7 C2 C1 127.1(18) . . ? C4 C3 C2 126.0(16) . . ? C4 C3 Se1 127.8(18) . . ? C2 C3 Se1 106.2(15) . . ? C3 C4 C5 114(2) . . ? C3 C4 H4 122.9 . . ? C5 C4 H4 122.9 . . ? C4 C5 C6 122(2) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C5 120(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 120(2) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O2 C8 N2 122.3(18) . . ? O2 C8 C9 117.4(15) . . ? N2 C8 C9 120.3(18) . . ? C10 C9 C14 116.8(18) . . ? C10 C9 C8 119.7(18) . . ? C14 C9 C8 123.5(17) . . ? C9 C10 C11 125.8(17) . . ? C9 C10 Se1 118.4(15) . . ? C11 C10 Se1 115.6(13) . . ? C10 C11 C12 113.4(18) . . ? C10 C11 H11 123.3 . . ? C12 C11 H11 123.3 . . ? C13 C12 C11 122.2(19) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C14 C13 C12 119(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C9 122.5(18) . . ? C13 C14 H14 118.7 . . ? C9 C14 H14 118.7 . . ? H104 O4 H204 107 . . ? H105 O5 H205 106 . . ? H106 O6 H206 107 . . ? 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 C3 Se1 O2 C8 -116.6(12) . . . . ? C10 Se1 O2 C8 -16.8(12) . . . . ? C3 Se1 N1 C1 -7.1(13) . . . . ? C10 Se1 N1 C1 -106.8(13) . . . . ? Se1 N1 C1 O1 -177.2(14) . . . . ? Se1 N1 C1 C2 7.9(19) . . . . ? O1 C1 C2 C3 -179.4(17) . . . . ? N1 C1 C2 C3 -4(2) . . . . ? O1 C1 C2 C7 2(3) . . . . ? N1 C1 C2 C7 177.4(19) . . . . ? C7 C2 C3 C4 -1(3) . . . . ? C1 C2 C3 C4 -179.6(17) . . . . ? C7 C2 C3 Se1 177.1(14) . . . . ? C1 C2 C3 Se1 -1.3(19) . . . . ? N1 Se1 C3 C4 -177.1(17) . . . . ? C10 Se1 C3 C4 -78.1(16) . . . . ? O2 Se1 C3 C4 -2.7(16) . . . . ? N1 Se1 C3 C2 4.6(13) . . . . ? C10 Se1 C3 C2 103.7(13) . . . . ? O2 Se1 C3 C2 179.0(12) . . . . ? C2 C3 C4 C5 2(3) . . . . ? Se1 C3 C4 C5 -176.0(15) . . . . ? C3 C4 C5 C6 -2(3) . . . . ? C4 C5 C6 C7 1(4) . . . . ? C5 C6 C7 C2 0(4) . . . . ? C3 C2 C7 C6 0(3) . . . . ? C1 C2 C7 C6 178.3(19) . . . . ? Se1 O2 C8 N2 -160.9(15) . . . . ? Se1 O2 C8 C9 20.1(19) . . . . ? O2 C8 C9 C10 -15(3) . . . . ? N2 C8 C9 C10 165.7(18) . . . . ? O2 C8 C9 C14 165.8(18) . . . . ? N2 C8 C9 C14 -13(3) . . . . ? C14 C9 C10 C11 1(3) . . . . ? C8 C9 C10 C11 -178.2(17) . . . . ? C14 C9 C10 Se1 176.4(13) . . . . ? C8 C9 C10 Se1 -3(2) . . . . ? N1 Se1 C10 C9 -170.9(15) . . . . ? C3 Se1 C10 C9 97.2(17) . . . . ? O2 Se1 C10 C9 9.5(14) . . . . ? N1 Se1 C10 C11 5.0(14) . . . . ? C3 Se1 C10 C11 -86.8(14) . . . . ? O2 Se1 C10 C11 -174.5(14) . . . . ? C9 C10 C11 C12 -2(3) . . . . ? Se1 C10 C11 C12 -177.3(13) . . . . ? C10 C11 C12 C13 0(3) . . . . ? C11 C12 C13 C14 2(3) . . . . ? C12 C13 C14 C9 -3(3) . . . . ? C10 C9 C14 C13 1(3) . . . . ? C8 C9 C14 C13 -179.6(18) . . . . ? 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 N1 H1 O3 0.88 1.95 2.810(19) 166 2_656 N2 H2A O3 0.88 2.09 2.921(19) 158 1_655 N2 H2A O4 0.88 2.79 3.383(19) 126 . N2 H2B O1 0.88 2.03 2.879(19) 161 2_646 O3 H103 O4 0.82 2.16 2.818(15) 138 . O4 H204 O3 0.82 2.29 2.717(10) 113 1_655 O4 H104 O3 0.82 2.03 2.818(15) 162 . O5 H105 O6 0.82 1.90 2.689(14) 161 1_556 O5 H205 O1 0.82 1.96 2.747(15) 164 2_646 O6 H106 O2 0.82 2.05 2.843(17) 163 . O6 H206 O5 0.82 2.10 2.689(14) 128 1_554 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.67 _refine_diff_density_min -0.85 _refine_diff_density_rms 0.114 #--------END-------------------------------------------------------------