# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Chen-Wei Liu.' 'Chiang-Shiang Fang.' 'Bijay Sarkar' 'Lee-Yan You.' _publ_contact_author_name 'Chen-Wei Liu' _publ_contact_author_email CHENWEI@MAIL.NDHU.EDU.TW _publ_section_title ; The Chemistry of Phosphorodiselenoates: Structure, Catalysis and Formation of Se-esters ; # Attachment 'Se-C.CIF' data_i _database_code_depnum_ccdc_archive 'CCDC 706306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H19 Cl3 N O2 P Se2' _chemical_formula_weight 444.47 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' P P 0.1023 0.0942 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8693(5) _cell_length_b 14.9715(12) _cell_length_c 17.3393(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.082(3) _cell_angle_gamma 90.00 _cell_volume 1755.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2812 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.78 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7974 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8954 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4033 _reflns_number_gt 3080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0478P)^2^+0.2705P] 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 4033 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.6962(5) 0.5725(2) 0.9360(3) 0.0487(8) Uani 1 1 d . . . Cl1 Cl 0.42672(18) 0.52577(8) 0.39290(7) 0.0716(3) Uani 1 1 d . . . Cl2 Cl 0.1992(2) 0.41093(9) 0.27699(9) 0.0920(4) Uani 1 1 d . . . Cl3 Cl 0.6194(2) 0.41971(9) 0.29112(10) 0.0998(5) Uani 1 1 d . . . Se1 Se 0.82101(4) 0.43433(2) 1.10015(2) 0.04065(11) Uani 1 1 d . . . Se2 Se 1.01872(4) 0.24699(2) 1.00417(2) 0.04260(12) Uani 1 1 d . . . P1 P 0.77027(10) 0.32560(5) 1.01886(5) 0.03018(17) Uani 1 1 d . . . O1 O 0.5942(3) 0.26471(14) 1.03766(13) 0.0371(5) Uani 1 1 d . . . O2 O 0.6620(3) 0.37053(13) 0.93932(12) 0.0354(5) Uani 1 1 d . . . C1 C 0.6233(4) 0.1865(2) 1.0889(2) 0.0408(8) Uani 1 1 d . . . H1A H 0.7659 0.1793 1.1102 0.049 Uiso 1 1 calc R . . C2 C 0.5114(6) 0.2018(3) 1.1551(2) 0.0570(10) Uani 1 1 d . . . H2A H 0.5565 0.2567 1.1821 0.085 Uiso 1 1 calc R . . H2B H 0.5345 0.1522 1.1915 0.085 Uiso 1 1 calc R . . H2C H 0.3711 0.2062 1.1343 0.085 Uiso 1 1 calc R . . C3 C 0.5504(7) 0.1070(3) 1.0387(3) 0.0674(11) Uani 1 1 d . . . H3A H 0.6274 0.1009 0.9971 0.101 Uiso 1 1 calc R . . H3B H 0.4122 0.1155 1.0160 0.101 Uiso 1 1 calc R . . H3C H 0.5646 0.0534 1.0707 0.101 Uiso 1 1 calc R . . C4 C 0.6036(5) 0.3153(2) 0.86871(19) 0.0426(8) Uani 1 1 d . . . H4A H 0.6395 0.2523 0.8818 0.051 Uiso 1 1 calc R . . C5 C 0.3836(6) 0.3219(4) 0.8452(3) 0.0775(14) Uani 1 1 d . . . H5A H 0.3214 0.3075 0.8898 0.116 Uiso 1 1 calc R . . H5B H 0.3389 0.2802 0.8030 0.116 Uiso 1 1 calc R . . H5C H 0.3480 0.3822 0.8277 0.116 Uiso 1 1 calc R . . C6 C 0.7169(9) 0.3469(4) 0.8083(3) 0.0893(16) Uani 1 1 d . . . H6A H 0.8571 0.3379 0.8269 0.134 Uiso 1 1 calc R . . H6B H 0.6912 0.4099 0.7984 0.134 Uiso 1 1 calc R . . H6C H 0.6763 0.3135 0.7603 0.134 Uiso 1 1 calc R . . C7 C 0.4223(6) 0.4240(3) 0.3429(3) 0.0580(10) Uani 1 1 d . . . H7 H 0.447(6) 0.380(3) 0.380(2) 0.062(12) Uiso 1 1 d . . . H8 H 0.727(7) 0.534(4) 0.978(3) 0.085(16) Uiso 1 1 d . . . H9 H 0.746(8) 0.629(4) 0.964(3) 0.12(2) Uiso 1 1 d . . . H10 H 0.569(8) 0.582(3) 0.920(3) 0.092(17) Uiso 1 1 d . . . H11 H 0.770(8) 0.564(3) 0.905(3) 0.092(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0288(16) 0.0368(17) 0.081(3) 0.0037(17) 0.0113(17) 0.0003(12) Cl1 0.0775(7) 0.0786(7) 0.0603(7) -0.0126(5) 0.0162(5) 0.0038(6) Cl2 0.0892(9) 0.0794(8) 0.0938(9) 0.0226(7) -0.0217(7) -0.0318(7) Cl3 0.1021(10) 0.0834(9) 0.1266(12) -0.0210(8) 0.0555(9) 0.0070(7) Se1 0.02883(17) 0.0444(2) 0.0476(2) -0.01354(15) 0.00355(14) -0.00161(13) Se2 0.02595(17) 0.03818(19) 0.0640(2) -0.00721(15) 0.00893(15) 0.00300(13) P1 0.0216(3) 0.0297(4) 0.0391(4) -0.0001(3) 0.0049(3) -0.0007(3) O1 0.0229(10) 0.0394(12) 0.0483(13) 0.0089(10) 0.0041(9) -0.0025(8) O2 0.0371(11) 0.0303(11) 0.0374(12) -0.0008(9) 0.0029(9) -0.0006(9) C1 0.0289(15) 0.0383(17) 0.054(2) 0.0104(15) 0.0047(14) -0.0030(13) C2 0.052(2) 0.075(3) 0.044(2) 0.0116(19) 0.0089(17) -0.005(2) C3 0.070(3) 0.043(2) 0.094(3) -0.009(2) 0.029(2) -0.013(2) C4 0.057(2) 0.0370(17) 0.0331(17) -0.0011(13) 0.0052(15) 0.0013(15) C5 0.066(3) 0.092(4) 0.065(3) -0.020(3) -0.013(2) -0.005(3) C6 0.122(4) 0.105(4) 0.049(3) 0.000(3) 0.037(3) -0.017(3) C7 0.064(3) 0.052(2) 0.057(2) 0.0122(19) 0.007(2) -0.0052(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 H8 0.93(6) . ? N1 H9 1.01(6) . ? N1 H10 0.88(5) . ? N1 H11 0.81(6) . ? Cl1 C7 1.751(4) . ? Cl2 C7 1.756(4) . ? Cl3 C7 1.752(5) . ? Se1 P1 2.1415(8) . ? Se2 P1 2.1248(8) . ? P1 O1 1.593(2) . ? P1 O2 1.597(2) . ? O1 C1 1.462(4) . ? O2 C4 1.474(4) . ? C1 C2 1.507(5) . ? C1 C3 1.508(5) . ? C1 H1A 0.9900 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C6 1.487(6) . ? C4 C5 1.498(5) . ? C4 H4A 0.9900 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 H7 0.92(4) . ? 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 H8 N1 H9 98(4) . . ? H8 N1 H10 115(4) . . ? H9 N1 H10 105(4) . . ? H8 N1 H11 109(5) . . ? H9 N1 H11 105(5) . . ? H10 N1 H11 122(5) . . ? O1 P1 O2 99.33(11) . . ? O1 P1 Se2 111.23(9) . . ? O2 P1 Se2 113.10(9) . . ? O1 P1 Se1 110.01(9) . . ? O2 P1 Se1 104.23(8) . . ? Se2 P1 Se1 117.28(4) . . ? C1 O1 P1 123.66(18) . . ? C4 O2 P1 119.94(19) . . ? O1 C1 C2 107.9(3) . . ? O1 C1 C3 106.6(3) . . ? C2 C1 C3 113.4(3) . . ? O1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? C3 C1 H1A 109.6 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O2 C4 C6 107.9(3) . . ? O2 C4 C5 107.7(3) . . ? C6 C4 C5 114.5(4) . . ? O2 C4 H4A 108.9 . . ? C6 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? Cl1 C7 Cl3 109.7(2) . . ? Cl1 C7 Cl2 110.9(2) . . ? Cl3 C7 Cl2 109.1(3) . . ? Cl1 C7 H7 107(3) . . ? Cl3 C7 H7 106(3) . . ? Cl2 C7 H7 114(3) . . ? 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_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H8 Se1 0.92(5) 2.58(5) 3.502(5) 177(5) . . . y N1 H9 Se2 1.01(6) 2.46(6) 3.392(4) 154(4) . . 3_767 y N1 H10 Se1 0.88(5) 2.65(6) 3.500(4) 162(4) . . 3_667 y N1 H11 Se1 0.81(5) 2.83(6) 3.483(4) 139(5) . . 3_767 y _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.778 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.100 #===END data_1b _database_code_depnum_ccdc_archive 'CCDC 706307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H28 N O3 P Se2' _chemical_formula_weight 435.25 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' P P 0.1023 0.0942 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9318(13) _cell_length_b 22.409(4) _cell_length_c 11.2624(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.172(3) _cell_angle_gamma 90.00 _cell_volume 1956.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2812 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.78 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 3.866 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7974 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20173 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 24.73 _reflns_number_total 3353 _reflns_number_gt 2363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+4.5856P] 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 3353 _refine_ls_number_parameters 188 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.034 _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 0.63647(10) 0.22383(2) 0.24258(5) 0.1035(3) Uani 1 1 d . . . Se2 Se 0.42538(10) 0.16583(3) -0.05107(5) 0.0996(3) Uani 1 1 d . . . P1 P 0.5750(2) 0.14926(6) 0.12436(12) 0.0785(4) Uani 1 1 d . . . O1 O 0.4921(6) 0.10097(16) 0.1993(3) 0.1007(13) Uani 1 1 d . . . O2 O 0.7439(6) 0.11342(18) 0.1204(4) 0.1019(12) Uani 1 1 d . . . O3 O 0.2428(7) 0.4867(2) 0.0290(5) 0.1150(18) Uani 0.860(4) 1 d PD . . N1 N 0.3838(5) 0.31826(15) 0.0363(3) 0.0630(10) Uani 1 1 d . . . H1A H 0.3354 0.2999 -0.0337 0.076 Uiso 1 1 calc R . . H1D H 0.4471 0.2906 0.0839 0.076 Uiso 1 1 calc R . . C1 C 0.4443(12) 0.0429(3) 0.1508(7) 0.153(3) Uani 1 1 d . . . H1B H 0.3196 0.0418 0.1254 0.183 Uiso 1 1 calc R . . H1C H 0.4911 0.0379 0.0784 0.183 Uiso 1 1 calc R . . C2 C 0.4910(18) -0.0016(3) 0.2195(8) 0.251(7) Uani 1 1 d . . . H2A H 0.4536 -0.0377 0.1761 0.376 Uiso 1 1 calc R . . H2B H 0.4403 0.0011 0.2895 0.376 Uiso 1 1 calc R . . H2C H 0.6144 -0.0018 0.2449 0.376 Uiso 1 1 calc R . . C3 C 0.8711(12) 0.1350(4) 0.0596(7) 0.137(3) Uani 1 1 d . . . H3A H 0.8160 0.1505 -0.0195 0.165 Uiso 1 1 calc R . . H3B H 0.9351 0.1671 0.1061 0.165 Uiso 1 1 calc R . . C4 C 0.9850(13) 0.0883(6) 0.0453(11) 0.229(6) Uani 1 1 d . . . H4A H 1.0713 0.1032 0.0046 0.344 Uiso 1 1 calc R . . H4B H 0.9216 0.0568 -0.0021 0.344 Uiso 1 1 calc R . . H4C H 1.0397 0.0731 0.1237 0.344 Uiso 1 1 calc R . . C5 C 0.5094(6) 0.3647(2) 0.0060(4) 0.0652(12) Uani 1 1 d . . . C6 C 0.4003(7) 0.4152(2) -0.0647(5) 0.0820(16) Uani 1 1 d . . . H6A H 0.4743 0.4488 -0.0722 0.098 Uiso 1 1 calc R . . H6B H 0.3487 0.4013 -0.1459 0.098 Uiso 1 1 calc R . . C7 C 0.2575(9) 0.4354(3) -0.0003(6) 0.0796(18) Uani 0.860(4) 1 d PD . . C8 C 0.1373(7) 0.3868(2) 0.0234(5) 0.0821(15) Uani 1 1 d . . . H8A H 0.0738 0.3711 -0.0533 0.099 Uiso 1 1 calc R . . H8B H 0.0549 0.4033 0.0670 0.099 Uiso 1 1 calc R . . C9 C 0.2375(7) 0.3364(2) 0.0979(4) 0.0729(14) Uani 1 1 d . . . C10 C 0.6204(7) 0.3893(2) 0.1240(5) 0.096(2) Uani 1 1 d D . . H10A H 0.6683 0.4283 0.1138 0.116 Uiso 1 1 calc R . . H10B H 0.7109 0.3620 0.1616 0.116 Uiso 1 1 calc R . . C11 C 0.6150(7) 0.3326(3) -0.0722(5) 0.0923(17) Uani 1 1 d . . . H11A H 0.6752 0.2998 -0.0275 0.138 Uiso 1 1 calc R . . H11B H 0.6968 0.3598 -0.0941 0.138 Uiso 1 1 calc R . . H11C H 0.5398 0.3179 -0.1444 0.138 Uiso 1 1 calc R . . C12 C 0.3163(9) 0.3578(3) 0.2274(5) 0.115(2) Uani 1 1 d D . . H12A H 0.3543 0.3252 0.2832 0.138 Uiso 1 1 calc R . . H12B H 0.2397 0.3840 0.2600 0.138 Uiso 1 1 calc R . . C13 C 0.1277(8) 0.2807(3) 0.0963(6) 0.105(2) Uani 1 1 d . . . H13A H 0.0877 0.2676 0.0140 0.157 Uiso 1 1 calc R . . H13B H 0.0305 0.2896 0.1317 0.157 Uiso 1 1 calc R . . H13C H 0.1954 0.2497 0.1423 0.157 Uiso 1 1 calc R . . O3' O 0.495(4) 0.4458(9) 0.222(3) 0.1150(18) Uani 0.140(4) 1 d PD . . C7' C 0.469(3) 0.3918(8) 0.191(3) 0.0796(18) Uani 0.140(4) 1 d PD . . 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 0.1590(6) 0.0557(3) 0.0699(4) 0.0022(3) -0.0346(4) 0.0089(3) Se2 0.1390(6) 0.0765(4) 0.0643(3) -0.0030(3) -0.0218(3) 0.0086(4) P1 0.1026(11) 0.0546(7) 0.0661(8) 0.0028(6) -0.0096(7) 0.0037(7) O1 0.136(3) 0.068(2) 0.086(3) 0.011(2) -0.004(2) -0.015(2) O2 0.120(3) 0.094(3) 0.087(3) 0.006(2) 0.010(2) 0.015(3) O3 0.135(4) 0.062(3) 0.146(5) 0.000(3) 0.024(3) 0.008(3) N1 0.075(3) 0.051(2) 0.058(2) -0.0018(17) 0.002(2) -0.0070(19) C1 0.204(9) 0.084(5) 0.137(7) 0.012(5) -0.040(6) -0.045(5) C2 0.48(2) 0.077(5) 0.137(7) 0.021(5) -0.062(10) -0.065(9) C3 0.151(8) 0.165(8) 0.099(5) 0.022(5) 0.032(5) -0.027(6) C4 0.163(9) 0.290(15) 0.257(14) 0.068(11) 0.094(9) 0.100(10) C5 0.069(3) 0.059(3) 0.061(3) 0.003(2) 0.000(2) -0.013(2) C6 0.098(4) 0.059(3) 0.076(3) 0.010(3) -0.010(3) -0.015(3) C7 0.094(5) 0.060(4) 0.074(4) 0.006(3) -0.005(3) 0.005(3) C8 0.081(4) 0.076(3) 0.086(4) -0.003(3) 0.009(3) 0.002(3) C9 0.086(4) 0.066(3) 0.068(3) 0.001(2) 0.021(3) -0.002(3) C10 0.099(4) 0.077(4) 0.088(4) 0.015(3) -0.037(3) -0.031(3) C11 0.085(4) 0.101(4) 0.093(4) 0.006(3) 0.025(3) -0.015(3) C12 0.170(7) 0.112(5) 0.060(3) -0.005(3) 0.019(4) 0.038(5) C13 0.115(5) 0.084(4) 0.128(5) 0.016(4) 0.054(4) -0.014(4) O3' 0.135(4) 0.062(3) 0.146(5) 0.000(3) 0.024(3) 0.008(3) C7' 0.094(5) 0.060(4) 0.074(4) 0.006(3) -0.005(3) 0.005(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 Se1 P1 2.1281(15) . ? Se2 P1 2.1123(14) . ? P1 O2 1.570(4) . ? P1 O1 1.597(4) . ? O1 C1 1.431(7) . ? O2 C3 1.418(8) . ? O3 C7 1.209(7) . ? N1 C9 1.527(6) . ? N1 C5 1.528(6) . ? N1 H1A 0.9000 . ? N1 H1D 0.9000 . ? C1 C2 1.269(9) . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.414(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C11 1.518(7) . ? C5 C10 1.534(6) . ? C5 C6 1.540(6) . ? C6 C7 1.537(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.507(8) . ? C8 C9 1.527(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C13 1.519(7) . ? C9 C12 1.538(7) . ? C10 C7' 1.553(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C7' 1.553(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O3' C7' 1.263(18) . ? 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 O2 P1 O1 96.7(2) . . ? O2 P1 Se2 112.20(17) . . ? O1 P1 Se2 113.61(16) . . ? O2 P1 Se1 109.58(17) . . ? O1 P1 Se1 105.49(16) . . ? Se2 P1 Se1 117.17(6) . . ? C1 O1 P1 121.3(5) . . ? C3 O2 P1 122.5(5) . . ? C9 N1 C5 121.0(4) . . ? C9 N1 H1A 107.1 . . ? C5 N1 H1A 107.1 . . ? C9 N1 H1D 107.1 . . ? C5 N1 H1D 107.1 . . ? H1A N1 H1D 106.8 . . ? C2 C1 O1 117.5(7) . . ? C2 C1 H1B 107.9 . . ? O1 C1 H1B 107.9 . . ? C2 C1 H1C 107.9 . . ? O1 C1 H1C 107.9 . . ? H1B C1 H1C 107.2 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 O2 109.9(8) . . ? C4 C3 H3A 109.7 . . ? O2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? O2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C11 C5 N1 105.8(4) . . ? C11 C5 C10 112.8(5) . . ? N1 C5 C10 109.4(4) . . ? C11 C5 C6 111.5(4) . . ? N1 C5 C6 107.1(4) . . ? C10 C5 C6 110.0(4) . . ? C7 C6 C5 111.2(4) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O3 C7 C8 122.5(7) . . ? O3 C7 C6 122.2(6) . . ? C8 C7 C6 115.3(5) . . ? C7 C8 C9 110.9(4) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? C13 C9 C8 111.8(5) . . ? C13 C9 N1 105.4(4) . . ? C8 C9 N1 107.7(4) . . ? C13 C9 C12 112.6(5) . . ? C8 C9 C12 110.5(4) . . ? N1 C9 C12 108.6(4) . . ? C5 C10 C7' 94.2(11) . . ? C5 C10 H10A 112.9 . . ? C7' C10 H10A 112.9 . . ? C5 C10 H10B 112.9 . . ? C7' C10 H10B 112.9 . . ? H10A C10 H10B 110.3 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 C7' 95.0(11) . . ? C9 C12 H12A 112.7 . . ? C7' C12 H12A 112.7 . . ? C9 C12 H12B 112.7 . . ? C7' C12 H12B 112.7 . . ? H12A C12 H12B 110.2 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3' C7' C10 93.9(16) . . ? O3' C7' C12 119.4(17) . . ? C10 C7' C12 146.7(11) . . ? 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_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1D Se1 0.90 2.56 3.454(5) 172 . . . y N1 H1A Se1 0.90 2.73 3.598(6) 163 . . 4_565 y _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.73 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.647 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.061