Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_num _database_code_CSD 164964 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Bernard-Rocherulle, Patrica' 'Casar, Zdenko' 'Lorcy, Dominque' 'Marechal, Alenka Majcen-Le' _publ_contact_author_name ' Dr Dominque Lorcy' _publ_contact_author_address ;Synthese et Electrosynthese Organiques Universite de Rennes 1 UMR CNRS 6510 Rennes 35042 FRANCE ; _publ_contact_author_email DOMINIQUE.LORCY@UNIV.RENNES1.FR _audit_creation_method 'SHELXL-97' _chemical_name_systematic ; 4,3'-dimethyl-4H,3'H-spiro[benzo[1,4]selenazine-2,2'-benzoselenazol']-3-one ; _chemical_name_common ; 4,3'-dimethyl-4H,3'H-spiro[benzo[1,4]selenazine-2,2'-benzoselenazol']-3-one ; _chemical_melting_point 193 _chemical_formula_moiety 'C16 H14 N2 O Se2' _chemical_formula_sum 'C16 H14 N2 O Se2' _chemical_formula_weight 408.21 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' 'O' 'O' 0.0106 0.0060 '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_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 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 5.8828(1) _cell_length_b 15.9217(5) _cell_length_c 16.1883(6) _cell_angle_alpha 90.000 _cell_angle_beta 98.955(1) _cell_angle_gamma 90.000 _cell_volume 1497.78(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17183 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.750 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 4.94 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.240 _exptl_absorpt_correction_T_max 0.739 _exptl_absorpt_process_details 'Gaussian integration (Coppens, 1970)' _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 0 -1 0.370000 -2 0 1 0.375000 0 1 0 0.045000 0 -1 0 0.045000 0 0 1 0.040000 0 0 -1 0.040000 0 7 8 0.030000 0 -7 -8 0.040000 0 -3 4 0.040000 0 3 -4 0.040000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 9 # Orientation matrix from 'scale_all.out' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_UB_11 0.0267489 _diffrn_orient_matrix_UB_12 -0.1630425 _diffrn_orient_matrix_UB_13 -0.0481113 _diffrn_orient_matrix_UB_21 0.0043632 _diffrn_orient_matrix_UB_22 -0.0170732 _diffrn_orient_matrix_UB_23 0.0602846 _diffrn_orient_matrix_UB_31 -0.0593581 _diffrn_orient_matrix_UB_32 -0.0196385 _diffrn_orient_matrix_UB_33 -0.0012657 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19344 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 30.034 _reflns_number_total 4370 _reflns_number_gt 2906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; 'HKL Denzo & Scalepack (Otwinowski & Minor, 1997)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0611P)^2^+3.0335P] 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 'constrained' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4370 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.88833(8) 0.15928(3) 0.61329(3) 0.04104(16) Uani 1 1 d . . . Se2 Se 0.44695(8) 0.05475(3) 0.66364(4) 0.04694(17) Uani 1 1 d . . . C1 C 0.6940(7) 0.1380(3) 0.7008(3) 0.0318(9) Uani 1 1 d . . . C2 C 0.7045(7) 0.2557(3) 0.5867(3) 0.0343(9) Uani 1 1 d . . . C3 C 0.6650(7) -0.0283(3) 0.6483(3) 0.0353(9) Uani 1 1 d . . . C4 C 0.8467(7) 0.1030(3) 0.7781(3) 0.0353(9) Uani 1 1 d . . . N1 N 0.5962(6) 0.2182(2) 0.7160(2) 0.0359(8) Uani 1 1 d . . . C5 C 0.7015(9) 0.3063(3) 0.5178(3) 0.0448(11) Uani 1 1 d . . . H5 H 0.7998 0.2956 0.4793 0.054 Uiso 1 1 calc R . . C6 C 0.5629(7) 0.2712(3) 0.6466(3) 0.0344(9) Uani 1 1 d . . . N2 N 0.9235(6) 0.0220(2) 0.7732(2) 0.0360(8) Uani 1 1 d . . . C7 C 0.8718(7) -0.0329(3) 0.7032(3) 0.0334(9) Uani 1 1 d . . . C9 C 0.6177(9) -0.0851(3) 0.5820(3) 0.0446(11) Uani 1 1 d . . . H9 H 0.4808 -0.0807 0.5449 0.054 Uiso 1 1 calc R . . C10 C 0.0276(8) -0.0962(3) 0.6907(3) 0.0421(11) Uani 1 1 d . . . H10 H 0.1668 -0.1003 0.7266 0.051 Uiso 1 1 calc R . . C11 C 0.4426(9) 0.2244(3) 0.7776(3) 0.0472(12) Uani 1 1 d . . . H11A H 0.4540 0.2795 0.8019 0.071 Uiso 1 1 calc R . . H11B H 0.4847 0.1832 0.8205 0.071 Uiso 1 1 calc R . . H11C H 0.2872 0.2146 0.7510 0.071 Uiso 1 1 calc R . . C12 C 0.7707(11) -0.1471(3) 0.5713(4) 0.0523(13) Uani 1 1 d . . . H12 H 0.7371 -0.1855 0.5278 0.063 Uiso 1 1 calc R . . O1 O 0.8998(7) 0.1455(2) 0.8398(2) 0.0503(9) Uani 1 1 d . . . C13 C 0.4097(9) 0.3376(3) 0.6344(4) 0.0497(13) Uani 1 1 d . . . H13 H 0.3120 0.3486 0.6731 0.060 Uiso 1 1 calc R . . C14 C 0.0886(9) -0.0069(4) 0.8451(3) 0.0491(12) Uani 1 1 d . . . H14A H 0.2423 0.0050 0.8355 0.074 Uiso 1 1 calc R . . H14B H 0.0714 -0.0664 0.8520 0.074 Uiso 1 1 calc R . . H14C H 0.0598 0.0216 0.8947 0.074 Uiso 1 1 calc R . . C15 C 0.5507(11) 0.3730(4) 0.5067(4) 0.0555(14) Uani 1 1 d . . . H15 H 0.5476 0.4083 0.4607 0.067 Uiso 1 1 calc R . . C16 C 0.9775(10) -0.1524(3) 0.6260(4) 0.0509(13) Uani 1 1 d . . . H16 H 1.0826 -0.1944 0.6188 0.061 Uiso 1 1 calc R . . C17 C 0.4031(10) 0.3872(3) 0.5645(4) 0.0560(14) Uani 1 1 d . . . H17 H 0.2979 0.4312 0.5557 0.067 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 0.0382(3) 0.0426(3) 0.0444(3) 0.0044(2) 0.01267(19) 0.00635(18) Se2 0.0334(3) 0.0477(3) 0.0575(4) -0.0020(2) 0.0001(2) -0.00062(19) C1 0.0284(19) 0.035(2) 0.031(2) -0.0025(17) 0.0040(15) -0.0004(16) C2 0.038(2) 0.031(2) 0.033(2) -0.0022(18) 0.0010(17) -0.0008(16) C3 0.033(2) 0.032(2) 0.041(3) 0.0040(19) 0.0044(18) -0.0028(16) C4 0.035(2) 0.039(2) 0.030(2) 0.0016(19) 0.0013(17) -0.0013(17) N1 0.041(2) 0.035(2) 0.033(2) -0.0026(16) 0.0076(15) 0.0066(15) C5 0.055(3) 0.042(3) 0.036(3) -0.001(2) 0.001(2) 0.000(2) C6 0.033(2) 0.032(2) 0.036(2) -0.0055(18) 0.0003(17) 0.0019(16) N2 0.0361(19) 0.0354(19) 0.035(2) 0.0021(16) -0.0005(15) 0.0012(15) C7 0.035(2) 0.028(2) 0.038(2) 0.0055(18) 0.0053(17) -0.0004(15) C9 0.049(3) 0.042(3) 0.041(3) 0.000(2) 0.001(2) -0.010(2) C10 0.040(2) 0.035(2) 0.051(3) 0.002(2) 0.005(2) 0.0041(18) C11 0.046(3) 0.054(3) 0.044(3) -0.005(2) 0.013(2) 0.006(2) C12 0.072(4) 0.041(3) 0.046(3) -0.011(2) 0.016(3) -0.012(2) O1 0.062(2) 0.050(2) 0.0342(19) -0.0101(16) -0.0058(16) 0.0041(17) C13 0.050(3) 0.043(3) 0.056(3) -0.002(2) 0.006(2) 0.013(2) C14 0.053(3) 0.050(3) 0.039(3) 0.004(2) -0.008(2) -0.001(2) C15 0.080(4) 0.045(3) 0.037(3) 0.006(2) -0.004(3) 0.002(3) C16 0.056(3) 0.037(3) 0.062(4) -0.006(2) 0.017(3) 0.005(2) C17 0.065(3) 0.042(3) 0.057(4) 0.009(3) -0.001(3) 0.019(2) _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 C2 1.888(4) . ? Se1 C1 1.983(4) . ? Se2 C3 1.885(5) . ? Se2 C1 1.990(4) . ? C1 N1 1.437(5) . ? C1 C4 1.527(6) . ? C2 C5 1.374(7) . ? C2 C6 1.395(6) . ? C3 C7 1.392(6) . ? C3 C9 1.399(7) . ? C4 O1 1.208(6) . ? C4 N2 1.373(6) . ? N1 C6 1.394(6) . ? N1 C11 1.449(6) . ? C5 C15 1.378(8) . ? C5 H5 0.9300 . ? C6 C13 1.383(6) . ? N2 C7 1.426(6) . ? N2 C14 1.469(6) 1_655 ? C7 C10 1.398(6) 1_655 ? C9 C12 1.365(8) . ? C9 H9 0.9300 . ? C10 C16 1.374(8) 1_455 ? C10 C7 1.398(6) 1_455 ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C16 1.391(9) . ? C12 H12 0.9300 . ? C13 C17 1.377(8) . ? C13 H13 0.9300 . ? C14 N2 1.469(6) 1_455 ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C17 1.390(8) . ? C15 H15 0.9300 . ? C16 C10 1.374(8) 1_655 ? C16 H16 0.9300 . ? C17 H17 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 C2 Se1 C1 85.86(19) . . ? C3 Se2 C1 91.54(19) . . ? N1 C1 C4 112.6(4) . . ? N1 C1 Se1 105.1(3) . . ? C4 C1 Se1 108.4(3) . . ? N1 C1 Se2 110.5(3) . . ? C4 C1 Se2 108.3(3) . . ? Se1 C1 Se2 111.9(2) . . ? C5 C2 C6 121.8(4) . . ? C5 C2 Se1 126.6(4) . . ? C6 C2 Se1 111.7(3) . . ? C7 C3 C9 120.3(4) . . ? C7 C3 Se2 119.9(3) . . ? C9 C3 Se2 119.8(4) . . ? O1 C4 N2 122.0(4) . . ? O1 C4 C1 121.1(4) . . ? N2 C4 C1 116.9(4) . . ? C6 N1 C1 114.2(4) . . ? C6 N1 C11 119.2(4) . . ? C1 N1 C11 119.2(4) . . ? C2 C5 C15 119.0(5) . . ? C2 C5 H5 120.5 . . ? C15 C5 H5 120.5 . . ? C13 C6 N1 125.7(4) . . ? C13 C6 C2 118.9(5) . . ? N1 C6 C2 115.3(4) . . ? C4 N2 C7 126.2(4) . . ? C4 N2 C14 115.6(4) . 1_655 ? C7 N2 C14 118.0(4) . 1_655 ? C3 C7 C10 118.3(4) . 1_655 ? C3 C7 N2 122.1(4) . . ? C10 C7 N2 119.6(4) 1_655 . ? C12 C9 C3 120.6(5) . . ? C12 C9 H9 119.7 . . ? C3 C9 H9 119.7 . . ? C16 C10 C7 120.8(5) 1_455 1_455 ? C16 C10 H10 119.6 1_455 . ? C7 C10 H10 119.6 1_455 . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 C16 119.4(5) . . ? C9 C12 H12 120.3 . . ? C16 C12 H12 120.3 . . ? C17 C13 C6 119.3(5) . . ? C17 C13 H13 120.3 . . ? C6 C13 H13 120.3 . . ? N2 C14 H14A 109.5 1_455 . ? N2 C14 H14B 109.5 1_455 . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 1_455 . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 C15 C17 119.6(5) . . ? C5 C15 H15 120.2 . . ? C17 C15 H15 120.2 . . ? C10 C16 C12 120.6(5) 1_655 . ? C10 C16 H16 119.7 1_655 . ? C12 C16 H16 119.7 . . ? C13 C17 C15 121.3(5) . . ? C13 C17 H17 119.4 . . ? C15 C17 H17 119.4 . . ? 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 C2 Se1 C1 N1 -21.7(3) . . . . ? C2 Se1 C1 C4 -142.3(3) . . . . ? C2 Se1 C1 Se2 98.3(2) . . . . ? C3 Se2 C1 N1 176.8(3) . . . . ? C3 Se2 C1 C4 -59.5(3) . . . . ? C3 Se2 C1 Se1 60.0(2) . . . . ? C1 Se1 C2 C5 -169.4(4) . . . . ? C1 Se1 C2 C6 10.2(3) . . . . ? C1 Se2 C3 C7 36.6(4) . . . . ? C1 Se2 C3 C9 -143.6(4) . . . . ? N1 C1 C4 O1 -9.6(6) . . . . ? Se1 C1 C4 O1 106.4(4) . . . . ? Se2 C1 C4 O1 -132.0(4) . . . . ? N1 C1 C4 N2 171.7(4) . . . . ? Se1 C1 C4 N2 -72.4(4) . . . . ? Se2 C1 C4 N2 49.2(4) . . . . ? C4 C1 N1 C6 148.0(4) . . . . ? Se1 C1 N1 C6 30.1(4) . . . . ? Se2 C1 N1 C6 -90.8(4) . . . . ? C4 C1 N1 C11 -62.3(5) . . . . ? Se1 C1 N1 C11 179.9(3) . . . . ? Se2 C1 N1 C11 58.9(5) . . . . ? C6 C2 C5 C15 -1.6(7) . . . . ? Se1 C2 C5 C15 178.0(4) . . . . ? C1 N1 C6 C13 157.6(5) . . . . ? C11 N1 C6 C13 7.8(7) . . . . ? C1 N1 C6 C2 -24.5(5) . . . . ? C11 N1 C6 C2 -174.2(4) . . . . ? C5 C2 C6 C13 2.5(7) . . . . ? Se1 C2 C6 C13 -177.1(4) . . . . ? C5 C2 C6 N1 -175.7(4) . . . . ? Se1 C2 C6 N1 4.7(5) . . . . ? O1 C4 N2 C7 -179.6(4) . . . . ? C1 C4 N2 C7 -0.9(6) . . . . ? O1 C4 N2 C14 -4.7(7) . . . 1_655 ? C1 C4 N2 C14 174.0(4) . . . 1_655 ? C9 C3 C7 C10 -0.9(7) . . . 1_655 ? Se2 C3 C7 C10 178.9(3) . . . 1_655 ? C9 C3 C7 N2 -177.9(4) . . . . ? Se2 C3 C7 N2 1.9(6) . . . . ? C4 N2 C7 C3 -30.4(7) . . . . ? C14 N2 C7 C3 154.8(4) 1_655 . . . ? C4 N2 C7 C10 152.6(4) . . . 1_655 ? C14 N2 C7 C10 -22.1(6) 1_655 . . 1_655 ? C7 C3 C9 C12 1.6(7) . . . . ? Se2 C3 C9 C12 -178.2(4) . . . . ? C3 C9 C12 C16 -1.3(8) . . . . ? N1 C6 C13 C17 176.9(5) . . . . ? C2 C6 C13 C17 -1.0(8) . . . . ? C2 C5 C15 C17 -0.8(8) . . . . ? C9 C12 C16 C10 0.4(8) . . . 1_655 ? C6 C13 C17 C15 -1.3(9) . . . . ? C5 C15 C17 C13 2.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.034 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.446 _refine_diff_density_min -1.063 _refine_diff_density_rms 0.121