# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_6c _database_code_depnum_ccdc_archive 'CCDC 911411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(2-Methylphenylimino)-1,3-thiaselenane ; _chemical_name_common ? _chemical_melting_point 62-63 _chemical_formula_moiety 'C11 H13 N S Se' _chemical_formula_sum 'C11 H13 N S Se' _chemical_formula_weight 270.24 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_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.376(2) _cell_length_b 13.152(3) _cell_length_c 11.240(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.024(4) _cell_angle_gamma 90.00 _cell_volume 1201.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3158 _cell_measurement_theta_min 3.0977 _cell_measurement_theta_max 27.4640 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 3.261 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.2841 _exptl_absorpt_correction_T_max 0.4755 _exptl_absorpt_process_details 'NUMABS (Higashi, 1999)' _exptl_special_details ; ???? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type 'Rigaku AFC7R Mercury CCD' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 14.6306 _diffrn_reflns_number 9484 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2749 _reflns_number_gt 1768 _reflns_threshold_expression ' I>2\s(I)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al.,2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0509P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0240(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2749 _refine_ls_number_parameters 158 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.881 _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 N1 N 0.5441(2) 0.02520(16) 0.21670(18) 0.0548(5) Uani 1 1 d . A . C1 C 0.3935(3) 0.01739(17) 0.2142(2) 0.0473(6) Uani 1 1 d . . . Se1A Se 0.23912(4) 0.12449(3) 0.16419(4) 0.0835(2) Uani 0.8299(15) 1 d P A 1 S1B S 0.23912(4) 0.12449(3) 0.16419(4) 0.0835(2) Uani 0.1701(15) 1 d P A 2 C2A C 0.0853(9) 0.0812(5) 0.2538(8) 0.116(3) Uani 0.8299(15) 1 d PDU A 1 H2A H 0.1405 0.0817 0.3403 0.139 Uiso 0.8299(15) 1 calc PR A 1 H2B H -0.0022 0.1312 0.2417 0.139 Uiso 0.8299(15) 1 calc PR A 1 C2B C 0.035(4) 0.083(3) 0.189(3) 0.094(8) Uani 0.1701(15) 1 d PDU A 2 H2C H 0.0264 0.1172 0.2642 0.113 Uiso 0.1701(15) 1 calc PR A 2 H2D H -0.0466 0.1155 0.1239 0.113 Uiso 0.1701(15) 1 calc PR A 2 C3A C 0.0111(8) -0.0174(5) 0.2247(10) 0.120(3) Uani 0.8299(15) 1 d PDU A 1 H3A H -0.0916 -0.0078 0.1636 0.144 Uiso 0.8299(15) 1 calc PR A 1 H3B H -0.0165 -0.0435 0.2979 0.144 Uiso 0.8299(15) 1 calc PR A 1 C3B C -0.027(4) -0.019(2) 0.199(4) 0.088(7) Uani 0.1701(15) 1 d PDU A 2 H3C H -0.0843 -0.0411 0.1172 0.105 Uiso 0.1701(15) 1 calc PR A 2 H3D H -0.1069 -0.0161 0.2483 0.105 Uiso 0.1701(15) 1 calc PR A 2 C4A C 0.1075(5) -0.0989(3) 0.1777(5) 0.0770(12) Uani 0.8299(15) 1 d PDU A 1 H4A H 0.1021 -0.0866 0.0917 0.092 Uiso 0.8299(15) 1 calc PR A 1 H4B H 0.0580 -0.1646 0.1844 0.092 Uiso 0.8299(15) 1 calc PR A 1 C4B C 0.104(3) -0.0964(18) 0.253(2) 0.073(5) Uani 0.1701(15) 1 d PDU A 2 H4C H 0.0618 -0.1596 0.2129 0.088 Uiso 0.1701(15) 1 calc PR A 2 H4D H 0.0950 -0.1037 0.3373 0.088 Uiso 0.1701(15) 1 calc PR A 2 S1A S 0.32303(7) -0.10110(4) 0.26368(6) 0.0670(3) Uani 0.8299(15) 1 d P A 1 Se1B Se 0.32303(7) -0.10110(4) 0.26368(6) 0.0670(3) Uani 0.1701(15) 1 d P A 2 C5 C 0.6081(3) 0.11908(18) 0.1871(2) 0.0489(6) Uani 1 1 d . . . C6 C 0.6902(3) 0.1835(2) 0.2812(2) 0.0561(6) Uani 1 1 d . A . C7 C 0.7567(3) 0.2724(2) 0.2483(3) 0.0660(8) Uani 1 1 d . . . H7 H 0.8106 0.3164 0.3098 0.079 Uiso 1 1 calc R A . C8 C 0.7463(3) 0.2978(2) 0.1296(3) 0.0685(8) Uani 1 1 d . A . H8 H 0.7924 0.3582 0.1105 0.082 Uiso 1 1 calc R . . C9 C 0.6674(4) 0.2336(2) 0.0379(3) 0.0717(8) Uani 1 1 d . . . H9 H 0.6603 0.2504 -0.0436 0.086 Uiso 1 1 calc R A . C10 C 0.5982(4) 0.1442(2) 0.0662(2) 0.0613(7) Uani 1 1 d . A . H10 H 0.5449 0.1008 0.0038 0.074 Uiso 1 1 calc R . . C11 C 0.7045(5) 0.1542(3) 0.4133(3) 0.0945(11) Uani 1 1 d . . . H11C H 0.5969 0.1521 0.4289 0.142 Uiso 1 1 calc R A . H11A H 0.7708 0.2034 0.4662 0.142 Uiso 1 1 calc R . . H11B H 0.7549 0.0884 0.4286 0.142 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 N1 0.0429(12) 0.0449(12) 0.0773(13) 0.0031(10) 0.0158(10) 0.0034(9) C1 0.0473(14) 0.0387(12) 0.0560(13) -0.0020(10) 0.0126(11) 0.0027(10) Se1A 0.0521(3) 0.0494(2) 0.1518(4) 0.02163(19) 0.0301(2) 0.01114(15) S1B 0.0521(3) 0.0494(2) 0.1518(4) 0.02163(19) 0.0301(2) 0.01114(15) C2A 0.078(5) 0.074(3) 0.221(8) -0.033(5) 0.085(5) 0.001(3) C2B 0.033(12) 0.081(10) 0.17(2) 0.019(14) 0.036(13) -0.002(9) C3A 0.054(4) 0.082(4) 0.239(9) 0.020(5) 0.064(5) 0.008(3) C3B 0.039(11) 0.060(10) 0.154(14) -0.046(10) 0.005(10) -0.001(8) C4A 0.051(2) 0.059(2) 0.123(4) -0.001(3) 0.026(3) -0.0097(17) C4B 0.054(10) 0.081(11) 0.091(13) 0.015(12) 0.028(11) -0.003(8) S1A 0.0574(4) 0.0542(4) 0.0919(5) 0.0161(3) 0.0226(3) 0.0012(3) Se1B 0.0574(4) 0.0542(4) 0.0919(5) 0.0161(3) 0.0226(3) 0.0012(3) C5 0.0336(13) 0.0439(13) 0.0699(16) -0.0013(11) 0.0140(11) 0.0031(10) C6 0.0427(15) 0.0580(16) 0.0682(16) -0.0114(13) 0.0144(12) 0.0029(12) C7 0.0463(16) 0.0552(17) 0.093(2) -0.0188(15) 0.0105(13) -0.0035(13) C8 0.0523(18) 0.0497(16) 0.105(2) 0.0040(16) 0.0212(15) -0.0050(13) C9 0.076(2) 0.0602(18) 0.0806(18) 0.0098(15) 0.0232(15) -0.0032(16) C10 0.0630(17) 0.0525(16) 0.0672(17) -0.0053(12) 0.0133(13) -0.0057(13) C11 0.105(3) 0.103(3) 0.072(2) -0.0154(18) 0.0157(18) -0.013(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 N1 C1 1.260(3) . ? N1 C5 1.417(3) . ? C1 S1A 1.801(2) . ? C1 Se1A 1.902(2) . ? Se1A C2A 1.905(8) . ? C2A C3A 1.441(7) . ? C2A H2A 0.9700 . ? C2A H2B 0.9700 . ? C2B C3B 1.450(18) . ? C2B H2C 0.9700 . ? C2B H2D 0.9700 . ? C3A C4A 1.512(8) . ? C3A H3A 0.9700 . ? C3A H3B 0.9700 . ? C3B C4B 1.516(18) . ? C3B H3C 0.9700 . ? C3B H3D 0.9700 . ? C4A S1A 1.830(4) . ? C4A H4A 0.9700 . ? C4A H4B 0.9700 . ? C4B H4C 0.9700 . ? C4B H4D 0.9700 . ? C5 C10 1.381(4) . ? C5 C6 1.399(4) . ? C6 C7 1.382(4) . ? C6 C11 1.511(4) . ? C7 C8 1.358(4) . ? C7 H7 0.9300 . ? C8 C9 1.371(4) . ? C8 H8 0.9300 . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? 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 C1 N1 C5 120.0(2) . . ? N1 C1 S1A 117.70(18) . . ? N1 C1 Se1A 123.47(18) . . ? S1A C1 Se1A 118.81(14) . . ? C1 Se1A C2A 96.9(2) . . ? C3A C2A Se1A 117.3(6) . . ? C3A C2A H2A 108.0 . . ? Se1A C2A H2A 108.0 . . ? C3A C2A H2B 108.0 . . ? Se1A C2A H2B 108.0 . . ? H2A C2A H2B 107.2 . . ? C3B C2B H2C 105.0 . . ? C3B C2B H2D 105.0 . . ? H2C C2B H2D 105.9 . . ? C2A C3A C4A 118.7(6) . . ? C2A C3A H3A 107.6 . . ? C4A C3A H3A 107.6 . . ? C2A C3A H3B 107.6 . . ? C4A C3A H3B 107.6 . . ? H3A C3A H3B 107.1 . . ? C2B C3B C4B 115(3) . . ? C2B C3B H3C 108.6 . . ? C4B C3B H3C 108.6 . . ? C2B C3B H3D 108.6 . . ? C4B C3B H3D 108.6 . . ? H3C C3B H3D 107.6 . . ? C3A C4A S1A 111.7(4) . . ? C3A C4A H4A 109.3 . . ? S1A C4A H4A 109.3 . . ? C3A C4A H4B 109.3 . . ? S1A C4A H4B 109.3 . . ? H4A C4A H4B 108.0 . . ? C3B C4B H4C 104.2 . . ? C3B C4B H4D 104.2 . . ? H4C C4B H4D 105.5 . . ? C1 S1A C4A 100.26(17) . . ? C10 C5 C6 120.0(2) . . ? C10 C5 N1 120.2(2) . . ? C6 C5 N1 119.7(2) . . ? C7 C6 C5 117.8(2) . . ? C7 C6 C11 122.5(3) . . ? C5 C6 C11 119.7(3) . . ? C8 C7 C6 122.4(3) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.1(3) . . ? C5 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C6 C11 H11C 109.5 . . ? C6 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? 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 C5 N1 C1 S1A -175.50(17) . . . . ? C5 N1 C1 Se1A 3.3(3) . . . . ? N1 C1 Se1A C2A -154.7(3) . . . . ? S1A C1 Se1A C2A 24.1(3) . . . . ? C1 Se1A C2A C3A -60.9(6) . . . . ? Se1A C2A C3A C4A 29.3(10) . . . . ? C2A C3A C4A S1A 42.8(9) . . . . ? N1 C1 S1A C4A -153.9(2) . . . . ? Se1A C1 S1A C4A 27.2(2) . . . . ? C3A C4A S1A C1 -68.9(5) . . . . ? C1 N1 C5 C10 -84.3(3) . . . . ? C1 N1 C5 C6 99.6(3) . . . . ? C10 C5 C6 C7 1.2(4) . . . . ? N1 C5 C6 C7 177.3(2) . . . . ? C10 C5 C6 C11 -178.3(3) . . . . ? N1 C5 C6 C11 -2.2(4) . . . . ? C5 C6 C7 C8 -0.8(4) . . . . ? C11 C6 C7 C8 178.8(3) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C6 C5 C10 C9 -0.9(4) . . . . ? N1 C5 C10 C9 -177.0(3) . . . . ? C8 C9 C10 C5 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.475 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.053 data_8b _database_code_depnum_ccdc_archive 'CCDC 911412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Methoxy-5-selena-9-thia-1-(4-tolyl)-1-azaspiro[3.5]nonan-2-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O2 S Se' _chemical_formula_sum 'C14 H17 N O2 S Se' _chemical_formula_weight 342.31 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' 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_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.348(3) _cell_length_b 17.281(4) _cell_length_c 14.350(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.900(4) _cell_angle_gamma 90.00 _cell_volume 3006.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7586 _cell_measurement_theta_min 3.0569 _cell_measurement_theta_max 27.4676 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 2.633 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.6569 _exptl_absorpt_correction_T_max 0.7724 _exptl_absorpt_process_details 'NUMABS (Higashi, 1999)' _exptl_special_details ; ???? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type 'Rigaku AFC7R Mercury CCD' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 14.6306 _diffrn_reflns_number 24013 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6867 _reflns_number_gt 5286 _reflns_threshold_expression ' I>2\s(I)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ; Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0745P)^2^+2.4092P] 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_number_reflns 6867 _refine_ls_number_parameters 367 _refine_ls_number_restraints 58 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1667 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.073 _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 C1 C 0.1964(3) 0.6367(2) 0.0774(3) 0.0507(8) Uani 1 1 d . . . N1 N 0.2901(2) 0.64286(18) 0.0285(2) 0.0519(7) Uani 1 1 d . A . C2 C 0.2343(4) 0.6810(3) -0.0495(3) 0.0703(12) Uani 1 1 d . . . C3 C 0.1278(3) 0.6837(3) -0.0096(3) 0.0644(11) Uani 1 1 d D A . H3 H 0.1097 0.7362 0.0083 0.077 Uiso 1 1 calc R . . Se1A Se 0.15597(4) 0.53064(3) 0.08904(4) 0.05633(19) Uani 0.627(2) 1 d P A 1 S1B S 0.15597(4) 0.53064(3) 0.08904(4) 0.05633(19) Uani 0.373(2) 1 d P A 2 C4 C 0.0299(4) 0.5480(3) 0.1439(3) 0.0689(11) Uani 1 1 d . . . H4B H -0.0257 0.5736 0.0973 0.083 Uiso 1 1 calc R A 1 H4A H 0.0002 0.4982 0.1577 0.083 Uiso 1 1 calc R A 1 C5 C 0.0488(4) 0.5957(3) 0.2336(3) 0.0765(13) Uani 1 1 d . A . H5B H -0.0184 0.5956 0.2594 0.092 Uiso 1 1 calc R . . H5A H 0.1058 0.5710 0.2798 0.092 Uiso 1 1 calc R . . C6 C 0.0821(4) 0.6785(3) 0.2217(4) 0.0808(15) Uani 1 1 d . . . H6B H 0.0789 0.7064 0.2798 0.097 Uiso 1 1 calc R A 1 H6A H 0.0287 0.7018 0.1713 0.097 Uiso 1 1 calc R A 1 Se1B Se 0.22247(6) 0.69117(4) 0.19367(5) 0.0667(3) Uani 0.373(2) 1 d P A 2 S1A S 0.22247(6) 0.69117(4) 0.19367(5) 0.0667(3) Uani 0.627(2) 1 d P A 1 C7 C 0.4004(3) 0.6162(2) 0.0542(2) 0.0475(7) Uani 1 1 d . . . C8 C 0.4377(3) 0.5854(2) 0.1439(3) 0.0524(8) Uani 1 1 d . A . H8 H 0.3906 0.5822 0.1872 0.063 Uiso 1 1 calc R . . C9 C 0.5451(3) 0.5596(2) 0.1682(3) 0.0563(9) Uani 1 1 d . . . H9 H 0.5696 0.5385 0.2281 0.068 Uiso 1 1 calc R A . C10 C 0.6171(3) 0.5644(2) 0.1053(3) 0.0562(9) Uani 1 1 d . A . C11 C 0.5786(3) 0.5952(3) 0.0170(3) 0.0635(10) Uani 1 1 d . . . H11 H 0.6256 0.5983 -0.0264 0.076 Uiso 1 1 calc R A . C12 C 0.4708(3) 0.6218(3) -0.0091(3) 0.0598(10) Uani 1 1 d . A . H12 H 0.4465 0.6431 -0.0689 0.072 Uiso 1 1 calc R . . C13 C 0.7344(3) 0.5371(3) 0.1337(4) 0.0775(13) Uani 1 1 d . . . H13C H 0.7625 0.5515 0.1983 0.116 Uiso 1 1 calc R A . H13A H 0.7787 0.5604 0.0931 0.116 Uiso 1 1 calc R . . H13B H 0.7368 0.4818 0.1277 0.116 Uiso 1 1 calc R . . O1 O 0.2626(3) 0.7029(3) -0.1208(3) 0.1089(15) Uani 1 1 d . A . O2 O 0.0405(3) 0.6481(2) -0.0666(3) 0.0882(11) Uani 1 1 d D . . C14 C -0.0600(4) 0.6852(3) -0.0783(4) 0.0932(17) Uani 1 1 d . A . H14C H -0.0819 0.6902 -0.0179 0.140 Uiso 1 1 calc R . . H14A H -0.1142 0.6557 -0.1204 0.140 Uiso 1 1 calc R . . H14B H -0.0537 0.7357 -0.1047 0.140 Uiso 1 1 calc R . . C15 C 0.2615(3) 0.3582(3) 0.4205(3) 0.0644(10) Uani 1 1 d . . . N2 N 0.1755(3) 0.3746(2) 0.4772(2) 0.0625(8) Uani 1 1 d . C . C16 C 0.2447(4) 0.3704(3) 0.5640(4) 0.0849(15) Uani 1 1 d . . . C17 C 0.3423(4) 0.3538(4) 0.5181(4) 0.105(2) Uani 1 1 d DU B . H17A H 0.3637 0.2996 0.5305 0.126 Uiso 0.678(11) 1 calc PR B 1 H17B H 0.3755 0.4055 0.5203 0.126 Uiso 0.322(11) 1 calc PR B 2 Se2A Se 0.27525(6) 0.44017(4) 0.33553(7) 0.0924(3) Uani 0.542(3) 1 d P C 1 S2B S 0.27525(6) 0.44017(4) 0.33553(7) 0.0924(3) Uani 0.458(3) 1 d P C 2 C18 C 0.3940(5) 0.4002(4) 0.2871(5) 0.108(2) Uani 1 1 d . . . H18B H 0.4120 0.4365 0.2407 0.129 Uiso 1 1 calc R C 1 H18A H 0.4574 0.3973 0.3385 0.129 Uiso 1 1 calc R C 1 C19 C 0.3772(5) 0.3229(4) 0.2417(4) 0.0937(17) Uani 1 1 d . C . H19B H 0.4394 0.3117 0.2115 0.112 Uiso 1 1 calc R . . H19A H 0.3116 0.3247 0.1924 0.112 Uiso 1 1 calc R . . C20 C 0.3652(4) 0.2582(3) 0.3088(4) 0.0808(13) Uani 1 1 d . . . H20B H 0.4283 0.2589 0.3605 0.097 Uiso 1 1 calc R C 1 H20A H 0.3666 0.2094 0.2755 0.097 Uiso 1 1 calc R C 1 Se2B Se 0.23733(6) 0.26174(4) 0.35970(6) 0.0774(3) Uani 0.458(3) 1 d P C 2 S2A S 0.23733(6) 0.26174(4) 0.35970(6) 0.0774(3) Uani 0.542(3) 1 d P C 1 C21 C 0.0606(3) 0.3851(2) 0.4503(3) 0.0539(8) Uani 1 1 d . . . C22 C 0.0101(3) 0.3799(3) 0.3553(3) 0.0616(10) Uani 1 1 d . C . H22 H 0.0516 0.3706 0.3087 0.074 Uiso 1 1 calc R . . C23 C -0.1027(4) 0.3890(3) 0.3316(3) 0.0724(12) Uani 1 1 d . . . H23 H -0.1365 0.3863 0.2680 0.087 Uiso 1 1 calc R C . C24 C -0.1669(3) 0.4017(3) 0.3986(4) 0.0697(11) Uani 1 1 d . C . C25 C -0.1146(4) 0.4080(3) 0.4918(4) 0.0766(13) Uani 1 1 d . . . H25 H -0.1561 0.4179 0.5382 0.092 Uiso 1 1 calc R C . C26 C -0.0012(4) 0.3997(3) 0.5179(3) 0.0703(11) Uani 1 1 d . C . H26 H 0.0327 0.4040 0.5813 0.084 Uiso 1 1 calc R . . C27 C -0.2918(4) 0.4069(4) 0.3702(5) 0.106(2) Uani 1 1 d . . . H27C H -0.3230 0.3560 0.3697 0.158 Uiso 1 1 calc R C . H27A H -0.3110 0.4293 0.3080 0.158 Uiso 1 1 calc R . . H27B H -0.3200 0.4388 0.4149 0.158 Uiso 1 1 calc R . . O3 O 0.2278(4) 0.3772(3) 0.6434(3) 0.1171(15) Uani 1 1 d . C . O4A O 0.4320(5) 0.3962(4) 0.5342(6) 0.139(3) Uani 0.678(11) 1 d PDU B 1 O4B O 0.4232(9) 0.3155(8) 0.5499(11) 0.117(6) Uani 0.322(11) 1 d PDU B 2 C28B C 0.5276(19) 0.340(3) 0.583(4) 0.131(13) Uani 0.322(11) 1 d PDU B 2 H28D H 0.5743 0.2966 0.6030 0.196 Uiso 0.322(11) 1 calc PR B 2 H28E H 0.5281 0.3746 0.6354 0.196 Uiso 0.322(11) 1 calc PR B 2 H28F H 0.5544 0.3671 0.5331 0.196 Uiso 0.322(11) 1 calc PR B 2 C28A C 0.5272(9) 0.3668(14) 0.5842(14) 0.117(6) Uani 0.678(11) 1 d PDU B 1 H28C H 0.5844 0.4051 0.5893 0.175 Uiso 0.678(11) 1 calc PR B 1 H28A H 0.5481 0.3219 0.5522 0.175 Uiso 0.678(11) 1 calc PR B 1 H28B H 0.5167 0.3524 0.6465 0.175 Uiso 0.678(11) 1 calc PR B 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0440(17) 0.055(2) 0.0513(19) -0.0053(15) 0.0031(15) 0.0014(15) N1 0.0477(15) 0.0574(17) 0.0488(16) 0.0091(13) 0.0043(13) -0.0013(13) C2 0.068(3) 0.074(3) 0.062(3) 0.018(2) -0.007(2) -0.005(2) C3 0.059(2) 0.061(2) 0.063(2) -0.0004(18) -0.0140(19) 0.0066(18) Se1A 0.0556(3) 0.0542(3) 0.0628(3) -0.0047(2) 0.0205(2) -0.0023(2) S1B 0.0556(3) 0.0542(3) 0.0628(3) -0.0047(2) 0.0205(2) -0.0023(2) C4 0.054(2) 0.086(3) 0.070(3) -0.002(2) 0.020(2) -0.007(2) C5 0.060(2) 0.117(4) 0.057(2) -0.005(2) 0.020(2) 0.013(3) C6 0.061(2) 0.105(4) 0.073(3) -0.036(3) 0.003(2) 0.023(3) Se1B 0.0558(4) 0.0701(5) 0.0697(5) -0.0243(3) 0.0005(3) 0.0046(3) S1A 0.0558(4) 0.0701(5) 0.0697(5) -0.0243(3) 0.0005(3) 0.0046(3) C7 0.0446(17) 0.0520(18) 0.0442(17) -0.0001(14) 0.0040(14) -0.0063(14) C8 0.0429(17) 0.068(2) 0.0480(19) 0.0077(17) 0.0139(15) 0.0032(16) C9 0.0460(18) 0.069(2) 0.054(2) 0.0025(18) 0.0096(16) 0.0041(17) C10 0.0457(18) 0.063(2) 0.062(2) -0.0163(18) 0.0148(17) -0.0074(16) C11 0.057(2) 0.083(3) 0.057(2) -0.010(2) 0.0276(19) -0.012(2) C12 0.058(2) 0.078(3) 0.0441(19) -0.0011(18) 0.0127(17) -0.0128(19) C13 0.048(2) 0.098(4) 0.090(3) -0.018(3) 0.020(2) 0.009(2) O1 0.097(3) 0.146(4) 0.077(2) 0.058(2) -0.001(2) -0.008(2) O2 0.0636(18) 0.088(2) 0.096(2) -0.0276(19) -0.0279(17) 0.0176(16) C14 0.054(2) 0.101(4) 0.112(4) 0.009(3) -0.014(3) 0.010(3) C15 0.049(2) 0.065(2) 0.077(3) 0.013(2) 0.0062(19) 0.0018(18) N2 0.0532(18) 0.076(2) 0.0545(18) 0.0011(16) -0.0003(15) 0.0019(16) C16 0.077(3) 0.096(4) 0.069(3) 0.000(3) -0.018(3) 0.002(3) C17 0.059(3) 0.139(5) 0.103(4) 0.010(4) -0.021(3) -0.006(3) Se2A 0.0860(5) 0.0585(4) 0.1403(8) 0.0321(4) 0.0406(5) 0.0077(3) S2B 0.0860(5) 0.0585(4) 0.1403(8) 0.0321(4) 0.0406(5) 0.0077(3) C18 0.073(3) 0.104(5) 0.153(6) 0.056(4) 0.037(4) -0.005(3) C19 0.077(3) 0.115(5) 0.097(4) 0.037(3) 0.037(3) 0.022(3) C20 0.074(3) 0.084(3) 0.087(3) 0.011(3) 0.021(3) 0.023(2) Se2B 0.0722(5) 0.0577(4) 0.1080(6) 0.0044(4) 0.0317(4) 0.0017(3) S2A 0.0722(5) 0.0577(4) 0.1080(6) 0.0044(4) 0.0317(4) 0.0017(3) C21 0.054(2) 0.054(2) 0.052(2) 0.0024(16) 0.0063(16) 0.0038(16) C22 0.055(2) 0.078(3) 0.053(2) 0.0035(19) 0.0108(17) 0.0084(19) C23 0.061(2) 0.087(3) 0.065(3) 0.003(2) 0.002(2) 0.012(2) C24 0.054(2) 0.069(3) 0.087(3) 0.007(2) 0.014(2) 0.0106(19) C25 0.073(3) 0.084(3) 0.079(3) 0.001(2) 0.030(2) 0.013(2) C26 0.074(3) 0.082(3) 0.055(2) -0.002(2) 0.013(2) 0.007(2) C27 0.061(3) 0.128(5) 0.128(5) 0.012(4) 0.017(3) 0.025(3) O3 0.117(3) 0.156(4) 0.065(2) -0.011(2) -0.017(2) 0.015(3) O4A 0.072(4) 0.102(5) 0.217(8) -0.008(5) -0.040(4) -0.021(3) O4B 0.069(6) 0.101(10) 0.161(12) 0.014(8) -0.032(7) 0.010(6) C28B 0.049(8) 0.13(2) 0.20(3) -0.02(2) -0.011(14) 0.028(10) C28A 0.058(5) 0.183(19) 0.099(8) -0.036(10) -0.009(5) -0.011(7) _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 C1 N1 1.466(5) . ? C1 C3 1.593(5) . ? C1 Se1B 1.890(4) . ? C1 Se1A 1.915(4) . ? N1 C2 1.368(5) . ? N1 C7 1.418(5) . ? C2 O1 1.203(6) . ? C2 C3 1.531(7) . ? C3 O2 1.370(5) . ? C3 H3 0.9800 . ? Se1A C4 1.897(4) . ? C4 C5 1.509(6) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C6 1.506(8) . ? C5 H5B 0.9700 . ? C5 H5A 0.9700 . ? C6 Se1B 1.865(5) . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? C7 C12 1.374(5) . ? C7 C8 1.387(5) . ? C8 C9 1.380(5) . ? C8 H8 0.9300 . ? C9 C10 1.384(6) . ? C9 H9 0.9300 . ? C10 C11 1.374(6) . ? C10 C13 1.505(5) . ? C11 C12 1.391(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? O2 C14 1.379(6) . ? C14 H14C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C15 N2 1.482(6) . ? C15 C17 1.560(7) . ? C15 Se2B 1.879(5) . ? C15 Se2A 1.897(4) . ? N2 C16 1.373(5) . ? N2 C21 1.409(5) . ? C16 O3 1.202(7) . ? C16 C17 1.506(9) . ? C17 O4B 1.214(10) . ? C17 O4A 1.311(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? Se2A C18 1.870(6) . ? C18 C19 1.483(9) . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? C19 C20 1.502(7) . ? C19 H19B 0.9700 . ? C19 H19A 0.9700 . ? C20 Se2B 1.861(5) . ? C20 H20B 0.9700 . ? C20 H20A 0.9700 . ? C21 C26 1.366(6) . ? C21 C22 1.391(5) . ? C22 C23 1.379(6) . ? C22 H22 0.9300 . ? C23 C24 1.375(7) . ? C23 H23 0.9300 . ? C24 C25 1.375(7) . ? C24 C27 1.520(6) . ? C25 C26 1.387(6) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? O4A C28A 1.356(14) . ? O4B C28B 1.36(2) . ? C28B H28D 0.9600 . ? C28B H28E 0.9600 . ? C28B H28F 0.9600 . ? C28A H28C 0.9600 . ? C28A H28A 0.9600 . ? C28A H28B 0.9600 . ? 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 C1 C3 86.5(3) . . ? N1 C1 Se1B 111.6(2) . . ? C3 C1 Se1B 114.5(3) . . ? N1 C1 Se1A 110.8(2) . . ? C3 C1 Se1A 116.6(2) . . ? Se1B C1 Se1A 113.79(19) . . ? C2 N1 C7 132.9(4) . . ? C2 N1 C1 96.0(3) . . ? C7 N1 C1 131.1(3) . . ? O1 C2 N1 131.6(5) . . ? O1 C2 C3 135.8(4) . . ? N1 C2 C3 92.6(3) . . ? O2 C3 C2 113.4(4) . . ? O2 C3 C1 118.8(4) . . ? C2 C3 C1 84.9(3) . . ? O2 C3 H3 112.3 . . ? C2 C3 H3 112.3 . . ? C1 C3 H3 112.3 . . ? C4 Se1A C1 97.64(19) . . ? C5 C4 Se1A 115.7(3) . . ? C5 C4 H4B 108.4 . . ? Se1A C4 H4B 108.4 . . ? C5 C4 H4A 108.4 . . ? Se1A C4 H4A 108.4 . . ? H4B C4 H4A 107.4 . . ? C6 C5 C4 115.1(4) . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? H5B C5 H5A 107.5 . . ? C5 C6 Se1B 114.9(3) . . ? C5 C6 H6B 108.5 . . ? Se1B C6 H6B 108.5 . . ? C5 C6 H6A 108.5 . . ? Se1B C6 H6A 108.5 . . ? H6B C6 H6A 107.5 . . ? C6 Se1B C1 97.02(18) . . ? C12 C7 C8 119.9(3) . . ? C12 C7 N1 120.1(3) . . ? C8 C7 N1 120.0(3) . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 121.3(4) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 118.2(4) . . ? C11 C10 C13 121.2(4) . . ? C9 C10 C13 120.6(4) . . ? C10 C11 C12 121.5(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C7 C12 C11 119.5(4) . . ? C7 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C10 C13 H13C 109.5 . . ? C10 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 O2 C14 116.8(4) . . ? O2 C14 H14C 109.5 . . ? O2 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C15 C17 85.4(4) . . ? N2 C15 Se2B 110.9(3) . . ? C17 C15 Se2B 113.1(4) . . ? N2 C15 Se2A 111.7(3) . . ? C17 C15 Se2A 119.6(3) . . ? Se2B C15 Se2A 112.9(2) . . ? C16 N2 C21 132.6(4) . . ? C16 N2 C15 95.7(4) . . ? C21 N2 C15 131.5(3) . . ? O3 C16 N2 131.7(6) . . ? O3 C16 C17 136.9(5) . . ? N2 C16 C17 91.5(4) . . ? O4B C17 C16 127.6(10) . . ? O4A C17 C16 122.4(7) . . ? O4B C17 C15 134.8(10) . . ? O4A C17 C15 120.4(6) . . ? C16 C17 C15 87.4(4) . . ? O4A C17 H17A 108.2 . . ? C16 C17 H17A 108.2 . . ? C15 C17 H17A 108.2 . . ? O4B C17 H17B 100.2 . . ? C16 C17 H17B 100.2 . . ? C15 C17 H17B 100.2 . . ? C18 Se2A C15 97.7(2) . . ? C19 C18 Se2A 116.2(4) . . ? C19 C18 H18B 108.2 . . ? Se2A C18 H18B 108.2 . . ? C19 C18 H18A 108.2 . . ? Se2A C18 H18A 108.2 . . ? H18B C18 H18A 107.4 . . ? C18 C19 C20 114.3(5) . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? H19B C19 H19A 107.6 . . ? C19 C20 Se2B 114.9(3) . . ? C19 C20 H20B 108.5 . . ? Se2B C20 H20B 108.5 . . ? C19 C20 H20A 108.5 . . ? Se2B C20 H20A 108.5 . . ? H20B C20 H20A 107.5 . . ? C20 Se2B C15 98.0(2) . . ? C26 C21 C22 120.0(4) . . ? C26 C21 N2 119.9(4) . . ? C22 C21 N2 120.1(4) . . ? C23 C22 C21 118.6(4) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C24 C23 C22 122.4(4) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C25 117.7(4) . . ? C23 C24 C27 120.8(5) . . ? C25 C24 C27 121.5(5) . . ? C24 C25 C26 121.3(4) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C21 C26 C25 119.9(4) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C24 C27 H27C 109.5 . . ? C24 C27 H27A 109.5 . . ? H27C C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27C C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C17 O4A C28A 120.2(12) . . ? C17 O4B C28B 128(2) . . ? O4B C28B H28D 109.5 . . ? O4B C28B H28E 109.5 . . ? H28D C28B H28E 109.5 . . ? O4B C28B H28F 109.5 . . ? H28D C28B H28F 109.5 . . ? H28E C28B H28F 109.5 . . ? O4A C28A H28C 109.5 . . ? O4A C28A H28A 109.5 . . ? H28C C28A H28A 109.5 . . ? O4A C28A H28B 109.5 . . ? H28C C28A H28B 109.5 . . ? H28A C28A H28B 109.5 . . ? 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 C1 N1 C2 -1.9(3) . . . . ? Se1B C1 N1 C2 -116.9(3) . . . . ? Se1A C1 N1 C2 115.2(3) . . . . ? C3 C1 N1 C7 179.2(4) . . . . ? Se1B C1 N1 C7 64.2(4) . . . . ? Se1A C1 N1 C7 -63.7(4) . . . . ? C7 N1 C2 O1 0.9(9) . . . . ? C1 N1 C2 O1 -177.9(6) . . . . ? C7 N1 C2 C3 -179.1(4) . . . . ? C1 N1 C2 C3 2.0(3) . . . . ? O1 C2 C3 O2 58.9(8) . . . . ? N1 C2 C3 O2 -121.0(4) . . . . ? O1 C2 C3 C1 178.1(7) . . . . ? N1 C2 C3 C1 -1.9(3) . . . . ? N1 C1 C3 O2 115.7(4) . . . . ? Se1B C1 C3 O2 -132.1(4) . . . . ? Se1A C1 C3 O2 4.2(5) . . . . ? N1 C1 C3 C2 1.7(3) . . . . ? Se1B C1 C3 C2 113.9(3) . . . . ? Se1A C1 C3 C2 -109.8(3) . . . . ? N1 C1 Se1A C4 -175.5(2) . . . . ? C3 C1 Se1A C4 -78.8(3) . . . . ? Se1B C1 Se1A C4 57.8(2) . . . . ? C1 Se1A C4 C5 -55.4(4) . . . . ? Se1A C4 C5 C6 65.1(5) . . . . ? C4 C5 C6 Se1B -68.7(5) . . . . ? C5 C6 Se1B C1 61.5(4) . . . . ? N1 C1 Se1B C6 173.4(3) . . . . ? C3 C1 Se1B C6 77.2(3) . . . . ? Se1A C1 Se1B C6 -60.3(2) . . . . ? C2 N1 C7 C12 -5.7(6) . . . . ? C1 N1 C7 C12 172.8(4) . . . . ? C2 N1 C7 C8 173.5(4) . . . . ? C1 N1 C7 C8 -8.0(6) . . . . ? C12 C7 C8 C9 -0.9(6) . . . . ? N1 C7 C8 C9 180.0(4) . . . . ? C7 C8 C9 C10 0.6(6) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C8 C9 C10 C13 179.1(4) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C13 C10 C11 C12 -178.9(4) . . . . ? C8 C7 C12 C11 1.0(6) . . . . ? N1 C7 C12 C11 -179.8(4) . . . . ? C10 C11 C12 C7 -1.0(6) . . . . ? C2 C3 O2 C14 -137.7(5) . . . . ? C1 C3 O2 C14 125.0(5) . . . . ? C17 C15 N2 C16 -0.5(4) . . . . ? Se2B C15 N2 C16 112.5(3) . . . . ? Se2A C15 N2 C16 -120.5(4) . . . . ? C17 C15 N2 C21 -176.4(5) . . . . ? Se2B C15 N2 C21 -63.4(5) . . . . ? Se2A C15 N2 C21 63.6(5) . . . . ? C21 N2 C16 O3 -3.0(10) . . . . ? C15 N2 C16 O3 -178.8(7) . . . . ? C21 N2 C16 C17 176.3(5) . . . . ? C15 N2 C16 C17 0.5(4) . . . . ? O3 C16 C17 O4B 30.0(15) . . . . ? N2 C16 C17 O4B -149.2(10) . . . . ? O3 C16 C17 O4A -56.4(12) . . . . ? N2 C16 C17 O4A 124.3(7) . . . . ? O3 C16 C17 C15 178.8(8) . . . . ? N2 C16 C17 C15 -0.5(4) . . . . ? N2 C15 C17 O4B 145.0(13) . . . . ? Se2B C15 C17 O4B 34.3(13) . . . . ? Se2A C15 C17 O4B -102.6(13) . . . . ? N2 C15 C17 O4A -126.1(7) . . . . ? Se2B C15 C17 O4A 123.1(7) . . . . ? Se2A C15 C17 O4A -13.7(9) . . . . ? N2 C15 C17 C16 0.4(4) . . . . ? Se2B C15 C17 C16 -110.3(4) . . . . ? Se2A C15 C17 C16 112.9(4) . . . . ? N2 C15 Se2A C18 176.3(4) . . . . ? C17 C15 Se2A C18 79.0(5) . . . . ? Se2B C15 Se2A C18 -57.8(3) . . . . ? C15 Se2A C18 C19 58.0(5) . . . . ? Se2A C18 C19 C20 -66.6(6) . . . . ? C18 C19 C20 Se2B 67.4(6) . . . . ? C19 C20 Se2B C15 -60.1(5) . . . . ? N2 C15 Se2B C20 -174.5(3) . . . . ? C17 C15 Se2B C20 -80.5(4) . . . . ? Se2A C15 Se2B C20 59.2(2) . . . . ? C16 N2 C21 C26 5.4(7) . . . . ? C15 N2 C21 C26 179.8(4) . . . . ? C16 N2 C21 C22 -174.1(5) . . . . ? C15 N2 C21 C22 0.4(7) . . . . ? C26 C21 C22 C23 -0.8(7) . . . . ? N2 C21 C22 C23 178.7(4) . . . . ? C21 C22 C23 C24 -0.9(7) . . . . ? C22 C23 C24 C25 2.1(8) . . . . ? C22 C23 C24 C27 -176.6(5) . . . . ? C23 C24 C25 C26 -1.7(8) . . . . ? C27 C24 C25 C26 177.0(5) . . . . ? C22 C21 C26 C25 1.2(7) . . . . ? N2 C21 C26 C25 -178.3(4) . . . . ? C24 C25 C26 C21 0.1(8) . . . . ? C16 C17 O4A C28A 110.5(13) . . . . ? C15 C17 O4A C28A -141.4(12) . . . . ? C16 C17 O4B C28B -108(4) . . . . ? C15 C17 O4B C28B 118(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.341 _refine_diff_density_min -1.146 _refine_diff_density_rms 0.065 data_9a _database_code_depnum_ccdc_archive 'CCDC 911413' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Methoxy-N-phenyl-2-(1,3-thiaselenan-2-ylidene)acetamide ; _chemical_name_common ? _chemical_melting_point 115-116 _chemical_formula_moiety 'C13 H15 N O2 S Se' _chemical_formula_sum 'C13 H15 N O2 S Se' _chemical_formula_weight 328.28 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' 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_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.283(5) _cell_length_b 5.835(2) _cell_length_c 19.052(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.933(6) _cell_angle_gamma 90.00 _cell_volume 1364.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4020 _cell_measurement_theta_min 3.2107 _cell_measurement_theta_max 27.4736 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.901 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.3402 _exptl_absorpt_correction_T_max 0.4303 _exptl_absorpt_process_details 'NUMABS (Higashi, 1999)' _exptl_special_details ; ???? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type 'Rigaku AFC7R Mercury CCD' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 14.6306 _diffrn_reflns_number 10404 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.1459 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3084 _reflns_number_gt 1184 _reflns_threshold_expression ' I>2\s(I)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al.,2009)' _computing_publication_material ; Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.1472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3084 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2658 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _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 C1 C 0.7703(6) 0.6398(11) 0.0808(4) 0.0468(17) Uani 1 1 d . . . C2 C 0.6994(5) 0.5072(11) 0.0434(4) 0.0490(17) Uani 1 1 d . A . C3 C 0.7319(6) 0.3508(11) -0.0114(4) 0.0509(19) Uani 1 1 d . . . N1 N 0.6468(5) 0.2648(10) -0.0519(3) 0.0466(14) Uani 1 1 d . A . H1 H 0.5822 0.3100 -0.0425 0.056 Uiso 1 1 calc R . . Se1A Se 0.92027(7) 0.65272(15) 0.06408(5) 0.0592(4) Uani 0.839(4) 1 d P A 1 S1B S 0.92027(7) 0.65272(15) 0.06408(5) 0.0592(4) Uani 0.161(4) 1 d P A 2 C4 C 0.9502(7) 0.9507(17) 0.1010(5) 0.078(3) Uani 1 1 d . . . H4B H 1.0269 0.9818 0.0951 0.094 Uiso 1 1 calc R A 1 H4A H 0.9096 1.0604 0.0722 0.094 Uiso 1 1 calc R A 1 C5 C 0.9256(7) 0.9986(16) 0.1771(6) 0.080(3) Uani 1 1 d . A . H5B H 0.9917 0.9766 0.2056 0.097 Uiso 1 1 calc R . . H5A H 0.9042 1.1579 0.1814 0.097 Uiso 1 1 calc R . . C6 C 0.8367(8) 0.8490(15) 0.2058(5) 0.074(3) Uani 1 1 d . . . H6B H 0.8147 0.9131 0.2501 0.088 Uiso 1 1 calc R A 1 H6A H 0.8668 0.6981 0.2154 0.088 Uiso 1 1 calc R A 1 Se1B Se 0.71638(13) 0.8174(3) 0.14828(9) 0.0580(7) Uani 0.161(4) 1 d P A 2 S1A S 0.71638(13) 0.8174(3) 0.14828(9) 0.0580(7) Uani 0.839(4) 1 d P A 1 O1 O 0.5893(4) 0.5166(8) 0.0586(2) 0.0465(11) Uani 1 1 d . . . C7 C 0.5521(7) 0.3216(13) 0.0981(5) 0.063(2) Uani 1 1 d . A . H7C H 0.5686 0.1829 0.0736 0.094 Uiso 1 1 calc R . . H7A H 0.4749 0.3326 0.1035 0.094 Uiso 1 1 calc R . . H7B H 0.5883 0.3200 0.1436 0.094 Uiso 1 1 calc R . . O2 O 0.8266(4) 0.3110(9) -0.0241(3) 0.0638(16) Uani 1 1 d . A . C8 C 0.6571(6) 0.1049(12) -0.1088(4) 0.0497(18) Uani 1 1 d . . . C9 C 0.5907(6) 0.1279(13) -0.1686(4) 0.0502(18) Uani 1 1 d . A . H9 H 0.5417 0.2490 -0.1726 0.060 Uiso 1 1 calc R . . C10 C 0.5978(6) -0.0308(14) -0.2223(4) 0.0531(19) Uani 1 1 d . . . H10 H 0.5516 -0.0176 -0.2618 0.064 Uiso 1 1 calc R A . C11 C 0.6724(7) -0.2083(14) -0.2184(5) 0.061(2) Uani 1 1 d . A . H11 H 0.6781 -0.3116 -0.2552 0.074 Uiso 1 1 calc R . . C12 C 0.7392(7) -0.2291(14) -0.1578(4) 0.0565(19) Uani 1 1 d . . . H12 H 0.7894 -0.3483 -0.1548 0.068 Uiso 1 1 calc R A . C13 C 0.7328(6) -0.0763(12) -0.1016(4) 0.0500(17) Uani 1 1 d . A . H13 H 0.7765 -0.0934 -0.0612 0.060 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 C1 0.033(4) 0.061(4) 0.047(4) 0.001(3) 0.005(3) 0.003(3) C2 0.030(4) 0.057(4) 0.061(5) 0.007(4) 0.018(3) 0.002(3) C3 0.031(4) 0.054(4) 0.068(5) -0.003(3) 0.010(4) -0.002(3) N1 0.034(3) 0.062(3) 0.044(3) -0.011(3) 0.006(3) 0.000(3) Se1A 0.0361(6) 0.0707(7) 0.0719(8) -0.0106(4) 0.0168(5) -0.0041(4) S1B 0.0361(6) 0.0707(7) 0.0719(8) -0.0106(4) 0.0168(5) -0.0041(4) C4 0.060(6) 0.107(7) 0.068(6) 0.011(5) -0.003(5) -0.022(5) C5 0.054(6) 0.072(6) 0.115(9) -0.005(6) -0.006(5) -0.008(4) C6 0.083(7) 0.093(7) 0.045(5) -0.006(4) 0.002(5) 0.021(5) Se1B 0.0431(11) 0.0695(12) 0.0624(12) -0.0111(8) 0.0148(8) 0.0070(7) S1A 0.0431(11) 0.0695(12) 0.0624(12) -0.0111(8) 0.0148(8) 0.0070(7) O1 0.031(2) 0.060(3) 0.050(3) 0.009(2) 0.010(2) 0.003(2) C7 0.050(5) 0.076(5) 0.064(6) 0.015(4) 0.023(4) -0.004(4) O2 0.032(3) 0.090(4) 0.070(4) -0.025(3) 0.009(3) -0.002(3) C8 0.037(4) 0.054(4) 0.059(5) 0.001(4) 0.023(3) 0.001(3) C9 0.041(4) 0.069(5) 0.041(4) -0.001(3) 0.010(3) -0.001(3) C10 0.044(4) 0.083(5) 0.032(4) 0.000(4) 0.004(3) -0.014(4) C11 0.055(5) 0.070(5) 0.060(5) -0.013(4) 0.029(4) -0.008(4) C12 0.054(5) 0.067(5) 0.050(5) -0.004(4) 0.020(4) 0.002(4) C13 0.041(4) 0.061(4) 0.048(4) 0.001(4) 0.007(3) -0.001(3) _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 C1 C2 1.350(10) . ? C1 Se1B 1.794(7) . ? C1 Se1A 1.882(7) . ? C2 O1 1.393(8) . ? C2 C3 1.453(10) . ? C3 O2 1.218(8) . ? C3 N1 1.374(9) . ? N1 C8 1.439(9) . ? N1 H1 0.8600 . ? Se1A C4 1.907(10) . ? C4 C5 1.517(14) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C6 1.514(12) . ? C5 H5B 0.9700 . ? C5 H5A 0.9700 . ? C6 Se1B 1.819(10) . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? O1 C7 1.447(8) . ? C7 H7C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C8 C9 1.385(10) . ? C8 C13 1.411(9) . ? C9 C10 1.386(10) . ? C9 H9 0.9300 . ? C10 C11 1.383(11) . ? C10 H10 0.9300 . ? C11 C12 1.398(12) . ? C11 H11 0.9300 . ? C12 C13 1.397(10) . ? C12 H12 0.9300 . ? C13 H13 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 C1 Se1B 117.5(5) . . ? C2 C1 Se1A 123.4(6) . . ? Se1B C1 Se1A 119.0(4) . . ? C1 C2 O1 118.8(6) . . ? C1 C2 C3 123.4(6) . . ? O1 C2 C3 117.8(6) . . ? O2 C3 N1 122.2(7) . . ? O2 C3 C2 123.4(7) . . ? N1 C3 C2 114.2(6) . . ? C3 N1 C8 125.1(6) . . ? C3 N1 H1 117.5 . . ? C8 N1 H1 117.5 . . ? C1 Se1A C4 98.7(3) . . ? C5 C4 Se1A 118.6(7) . . ? C5 C4 H4B 107.7 . . ? Se1A C4 H4B 107.7 . . ? C5 C4 H4A 107.7 . . ? Se1A C4 H4A 107.7 . . ? H4B C4 H4A 107.1 . . ? C6 C5 C4 114.1(8) . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? H5B C5 H5A 107.6 . . ? C5 C6 Se1B 115.0(7) . . ? C5 C6 H6B 108.5 . . ? Se1B C6 H6B 108.5 . . ? C5 C6 H6A 108.5 . . ? Se1B C6 H6A 108.5 . . ? H6B C6 H6A 107.5 . . ? C1 Se1B C6 100.2(4) . . ? C2 O1 C7 113.7(5) . . ? O1 C7 H7C 109.5 . . ? O1 C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C9 C8 C13 121.3(7) . . ? C9 C8 N1 119.5(6) . . ? C13 C8 N1 119.2(7) . . ? C8 C9 C10 119.5(7) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 121.2(7) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 118.6(8) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 122.0(8) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C8 117.3(7) . . ? C12 C13 H13 121.3 . . ? C8 C13 H13 121.3 . . ? 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 Se1B C1 C2 O1 0.5(9) . . . . ? Se1A C1 C2 O1 -177.8(5) . . . . ? Se1B C1 C2 C3 -178.3(6) . . . . ? Se1A C1 C2 C3 3.4(10) . . . . ? C1 C2 C3 O2 6.6(12) . . . . ? O1 C2 C3 O2 -172.2(7) . . . . ? C1 C2 C3 N1 -168.3(7) . . . . ? O1 C2 C3 N1 12.9(9) . . . . ? O2 C3 N1 C8 5.9(12) . . . . ? C2 C3 N1 C8 -179.2(6) . . . . ? C2 C1 Se1A C4 154.9(7) . . . . ? Se1B C1 Se1A C4 -23.4(5) . . . . ? C1 Se1A C4 C5 58.4(8) . . . . ? Se1A C4 C5 C6 -26.0(11) . . . . ? C4 C5 C6 Se1B -45.3(10) . . . . ? C2 C1 Se1B C6 154.9(6) . . . . ? Se1A C1 Se1B C6 -26.7(5) . . . . ? C5 C6 Se1B C1 71.1(7) . . . . ? C1 C2 O1 C7 -103.8(8) . . . . ? C3 C2 O1 C7 75.1(8) . . . . ? C3 N1 C8 C9 -141.8(7) . . . . ? C3 N1 C8 C13 40.0(10) . . . . ? C13 C8 C9 C10 0.5(11) . . . . ? N1 C8 C9 C10 -177.7(6) . . . . ? C8 C9 C10 C11 -1.9(11) . . . . ? C9 C10 C11 C12 1.8(12) . . . . ? C10 C11 C12 C13 -0.1(12) . . . . ? C11 C12 C13 C8 -1.2(11) . . . . ? C9 C8 C13 C12 1.1(11) . . . . ? N1 C8 C13 C12 179.2(6) . . . . ? 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 O1 0.86 2.35 3.166(7) 159.1 3_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.780 _refine_diff_density_min -1.408 _refine_diff_density_rms 0.156