Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'J. Woollins' _publ_contact_author_address ; Department of Chemistry University of St Andrews St Andrews FIFE SCOTLAND KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_section_title ; Structure and Reactivity of Phosphorus-Selenium Heterocycles with Peri-Substituted Naphthalene Backbones ; loop_ _publ_author_name 'J. Woollins' 'Petr Kilian' 'Sahrah Parveen' 'A. Slawin' # Attachment '27.cif' data_spdw19 _database_code_depnum_ccdc_archive 'CCDC 670151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 P2 Se4' _chemical_formula_sum 'C10 H6 P2 Se4' _chemical_formula_weight 503.93 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.0071(5) _cell_length_b 11.2784(8) _cell_length_c 16.6917(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.885(2) _cell_angle_gamma 90.00 _cell_volume 1306.65(16) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 12135 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 11.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.349 _exptl_absorpt_correction_T_max 0.635 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Mercury 2' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13357 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2982 _reflns_number_gt 2468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0285P)^2^+0.7563P] 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 2982 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Se1 Se 0.22127(7) 0.50603(4) 0.17639(3) 0.01864(12) Uani 1 1 d . . . P1 P 0.41452(16) 0.62901(10) 0.13849(7) 0.0139(2) Uani 1 1 d . . . C1 C 0.3490(6) 0.6995(4) 0.0413(3) 0.0129(9) Uani 1 1 d . . . C2 C 0.1679(6) 0.6751(4) -0.0001(3) 0.0171(10) Uani 1 1 d . . . H2A H 0.0860 0.6209 0.0222 0.021 Uiso 1 1 calc R . . C3 C 0.1043(7) 0.7295(4) -0.0744(3) 0.0207(11) Uani 1 1 d . . . H3A H -0.0210 0.7129 -0.1016 0.025 Uiso 1 1 calc R . . C4 C 0.2219(7) 0.8064(4) -0.1081(3) 0.0195(10) Uani 1 1 d . . . H4A H 0.1778 0.8430 -0.1585 0.023 Uiso 1 1 calc R . . C5 C 0.4109(6) 0.8320(4) -0.0677(3) 0.0156(10) Uani 1 1 d . . . C6 C 0.5304(7) 0.9122(4) -0.1033(3) 0.0186(10) Uani 1 1 d . . . H6A H 0.4866 0.9452 -0.1549 0.022 Uiso 1 1 calc R . . C7 C 0.7072(7) 0.9424(4) -0.0643(3) 0.0213(11) Uani 1 1 d . . . H7A H 0.7857 0.9966 -0.0887 0.026 Uiso 1 1 calc R . . C8 C 0.7732(6) 0.8939(4) 0.0114(3) 0.0183(10) Uani 1 1 d . . . H8A H 0.8968 0.9158 0.0380 0.022 Uiso 1 1 calc R . . C9 C 0.6635(6) 0.8150(4) 0.0485(3) 0.0134(9) Uani 1 1 d . . . C10 C 0.4757(6) 0.7806(4) 0.0088(3) 0.0129(9) Uani 1 1 d . . . P9 P 0.75995(16) 0.76447(10) 0.14875(7) 0.0136(2) Uani 1 1 d . . . Se9 Se 1.02403(6) 0.83585(4) 0.19738(3) 0.01904(13) Uani 1 1 d . . . Se19 Se 0.50874(6) 0.78670(4) 0.22077(3) 0.01410(12) Uani 1 1 d . . . Se20 Se 0.72179(6) 0.56379(4) 0.13816(3) 0.01777(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0161(2) 0.0151(2) 0.0239(3) 0.00408(19) -0.00004(19) -0.00462(18) P1 0.0128(6) 0.0130(6) 0.0156(6) 0.0010(5) 0.0009(5) -0.0018(5) C1 0.014(2) 0.011(2) 0.014(2) -0.0018(18) 0.0030(18) -0.0009(17) C2 0.017(2) 0.013(2) 0.021(3) -0.0032(19) 0.002(2) 0.0006(19) C3 0.015(2) 0.026(3) 0.019(3) -0.006(2) -0.005(2) -0.003(2) C4 0.029(3) 0.015(3) 0.013(2) -0.0022(19) -0.003(2) 0.004(2) C5 0.019(2) 0.014(2) 0.014(2) -0.0039(19) 0.0034(19) -0.0005(19) C6 0.031(3) 0.015(2) 0.011(2) -0.0011(18) 0.005(2) -0.001(2) C7 0.024(3) 0.021(3) 0.020(3) 0.004(2) 0.007(2) -0.003(2) C8 0.014(2) 0.021(3) 0.020(3) 0.000(2) 0.0039(19) -0.0021(19) C9 0.021(2) 0.008(2) 0.011(2) -0.0021(17) 0.0028(18) 0.0011(18) C10 0.015(2) 0.011(2) 0.012(2) -0.0030(18) 0.0006(18) 0.0030(18) P9 0.0115(5) 0.0145(6) 0.0148(6) 0.0006(5) 0.0018(5) -0.0005(5) Se9 0.0141(2) 0.0222(3) 0.0203(3) -0.0004(2) 0.00033(19) -0.00145(19) Se19 0.0124(2) 0.0162(2) 0.0139(2) -0.00071(18) 0.00235(18) -0.00213(18) Se20 0.0155(2) 0.0134(2) 0.0240(3) 0.00077(19) 0.00117(19) 0.00184(18) _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 2.0958(12) . ? P1 C1 1.809(5) . ? P1 Se20 2.2760(12) . ? P1 Se19 2.2883(12) . ? C1 C2 1.386(6) . ? C1 C10 1.432(6) . ? C2 C3 1.400(6) . ? C3 C4 1.369(7) . ? C4 C5 1.430(6) . ? C5 C6 1.417(6) . ? C5 C10 1.419(6) . ? C6 C7 1.361(6) . ? C7 C8 1.398(6) . ? C8 C9 1.377(6) . ? C9 C10 1.443(6) . ? C9 P9 1.809(4) . ? P9 Se9 2.0782(12) . ? P9 Se19 2.2776(12) . ? P9 Se20 2.2830(12) . ? 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 P1 Se1 117.82(15) . . ? C1 P1 Se20 105.30(15) . . ? Se1 P1 Se20 115.94(5) . . ? C1 P1 Se19 102.32(14) . . ? Se1 P1 Se19 118.58(6) . . ? Se20 P1 Se19 93.30(4) . . ? C2 C1 C10 120.7(4) . . ? C2 C1 P1 117.5(3) . . ? C10 C1 P1 121.8(3) . . ? C1 C2 C3 120.9(4) . . ? C4 C3 C2 120.3(4) . . ? C3 C4 C5 120.3(4) . . ? C6 C5 C10 120.2(4) . . ? C6 C5 C4 119.6(4) . . ? C10 C5 C4 120.2(4) . . ? C7 C6 C5 120.7(4) . . ? C6 C7 C8 120.1(4) . . ? C9 C8 C7 121.6(4) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 P9 117.3(3) . . ? C10 C9 P9 122.8(3) . . ? C5 C10 C1 117.6(4) . . ? C5 C10 C9 117.6(4) . . ? C1 C10 C9 124.9(4) . . ? C9 P9 Se9 116.03(15) . . ? C9 P9 Se19 103.64(15) . . ? Se9 P9 Se19 117.54(6) . . ? C9 P9 Se20 102.47(14) . . ? Se9 P9 Se20 120.19(5) . . ? Se19 P9 Se20 93.39(4) . . ? P9 Se19 P1 77.17(4) . . ? P1 Se20 P9 77.30(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 Se1 P1 C1 C2 4.8(4) . . . . ? Se20 P1 C1 C2 135.9(3) . . . . ? Se19 P1 C1 C2 -127.2(3) . . . . ? Se1 P1 C1 C10 -177.1(3) . . . . ? Se20 P1 C1 C10 -46.1(4) . . . . ? Se19 P1 C1 C10 50.9(4) . . . . ? C10 C1 C2 C3 -0.3(7) . . . . ? P1 C1 C2 C3 177.8(3) . . . . ? C1 C2 C3 C4 1.1(7) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C3 C4 C5 C6 -179.7(4) . . . . ? C3 C4 C5 C10 -2.0(7) . . . . ? C10 C5 C6 C7 -0.9(7) . . . . ? C4 C5 C6 C7 176.8(4) . . . . ? C5 C6 C7 C8 0.3(7) . . . . ? C6 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C10 0.2(7) . . . . ? C7 C8 C9 P9 -176.9(4) . . . . ? C6 C5 C10 C1 -179.5(4) . . . . ? C4 C5 C10 C1 2.8(6) . . . . ? C6 C5 C10 C9 1.1(6) . . . . ? C4 C5 C10 C9 -176.6(4) . . . . ? C2 C1 C10 C5 -1.6(6) . . . . ? P1 C1 C10 C5 -179.7(3) . . . . ? C2 C1 C10 C9 177.6(4) . . . . ? P1 C1 C10 C9 -0.4(6) . . . . ? C8 C9 C10 C5 -0.8(6) . . . . ? P9 C9 C10 C5 176.1(3) . . . . ? C8 C9 C10 C1 180.0(4) . . . . ? P9 C9 C10 C1 -3.1(6) . . . . ? C8 C9 P9 Se9 1.6(4) . . . . ? C10 C9 P9 Se9 -175.4(3) . . . . ? C8 C9 P9 Se19 132.0(3) . . . . ? C10 C9 P9 Se19 -45.0(4) . . . . ? C8 C9 P9 Se20 -131.3(3) . . . . ? C10 C9 P9 Se20 51.7(4) . . . . ? C9 P9 Se19 P1 71.65(15) . . . . ? Se9 P9 Se19 P1 -158.86(7) . . . . ? Se20 P9 Se19 P1 -32.06(4) . . . . ? C1 P1 Se19 P9 -74.28(15) . . . . ? Se1 P1 Se19 P9 154.19(7) . . . . ? Se20 P1 Se19 P9 32.17(4) . . . . ? C1 P1 Se20 P9 71.67(15) . . . . ? Se1 P1 Se20 P9 -156.17(7) . . . . ? Se19 P1 Se20 P9 -32.06(4) . . . . ? C9 P9 Se20 P1 -72.54(15) . . . . ? Se9 P9 Se20 P1 157.01(7) . . . . ? Se19 P9 Se20 P1 32.23(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.770 _refine_diff_density_min -0.832 _refine_diff_density_rms 0.149 #============================================================================== data__spdw21_in_P21/c _database_code_depnum_ccdc_archive 'CCDC 670152' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H20 O2 P2 Se2 ' _chemical_formula_moiety 'C16 H20 O2 P2 Se2 ' _chemical_formula_weight 464.20 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.9079(6) _cell_length_b 15.0393(10) _cell_length_c 15.7616(11) _cell_angle_alpha 90.0000 _cell_angle_beta 94.3009(17) _cell_angle_gamma 90.0000 _cell_volume 1869.2(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 15896 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.7 _cell_measurement_temperature 125.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920.00 _exptl_absorpt_coefficient_mu 4.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.377 _exptl_absorpt_correction_T_max 0.719 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku SCXmini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.85 _diffrn_reflns_number 18897 _diffrn_reflns_av_R_equivalents 0.089 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4274 _reflns_number_gt 3051 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1138 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4274 _refine_ls_number_parameters 200 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0434P)^2^+4.3891P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.81 _refine_diff_density_min -0.58 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Se Se -0.093 2.226 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Se(1) Se 0.51113(7) 0.14763(4) 0.75402(4) 0.02936(16) Uani 1.00 1 d . . . Se(9) Se 1.01673(7) 0.28634(4) 0.62469(4) 0.03334(17) Uani 1.00 1 d . . . P(1) P 0.72165(17) 0.11198(9) 0.68966(8) 0.0205(3) Uani 1.00 1 d . . . P(9) P 0.80257(16) 0.20936(9) 0.59237(8) 0.0201(3) Uani 1.00 1 d . . . O(1) O 0.8904(4) 0.0862(2) 0.7460(2) 0.0267(8) Uani 1.00 1 d . . . O(9) O 0.6329(4) 0.2608(2) 0.5616(2) 0.0235(8) Uani 1.00 1 d . . . C(1) C 0.6999(6) 0.0216(3) 0.6147(3) 0.0188(10) Uani 1.00 1 d . . . C(2) C 0.6366(6) -0.0607(3) 0.6334(3) 0.0278(12) Uani 1.00 1 d . . . C(3) C 0.6300(7) -0.1287(3) 0.5718(3) 0.0281(12) Uani 1.00 1 d . . . C(4) C 0.6880(6) -0.1137(3) 0.4933(3) 0.0249(12) Uani 1.00 1 d . . . C(5) C 0.7526(6) -0.0294(3) 0.4717(3) 0.0202(11) Uani 1.00 1 d . . . C(6) C 0.8141(6) -0.0101(3) 0.3918(3) 0.0266(12) Uani 1.00 1 d . . . C(7) C 0.8764(6) 0.0711(3) 0.3729(3) 0.0268(12) Uani 1.00 1 d . . . C(8) C 0.8757(6) 0.1407(3) 0.4335(3) 0.0229(11) Uani 1.00 1 d . . . C(9) C 0.8155(6) 0.1256(3) 0.5120(3) 0.0206(11) Uani 1.00 1 d . . . C(10) C 0.7559(6) 0.0401(3) 0.5329(3) 0.0195(11) Uani 1.00 1 d . . . C(11) C 0.9280(7) 0.1197(3) 0.8334(3) 0.0287(13) Uani 1.00 1 d . . . C(12) C 1.1080(7) 0.1500(5) 0.8407(4) 0.055(2) Uani 1.00 1 d . . . C(13) C 0.8871(10) 0.0463(5) 0.8944(4) 0.060(2) Uani 1.00 1 d . . . C(14) C 0.5990(7) 0.3555(3) 0.5737(3) 0.0284(12) Uani 1.00 1 d . . . C(15) C 0.4494(8) 0.3747(3) 0.5081(3) 0.0367(14) Uani 1.00 1 d . . . C(16) C 0.5569(8) 0.3753(4) 0.6619(3) 0.0421(16) Uani 1.00 1 d . . . H(2A) H 0.5973 -0.0718 0.6880 0.033 Uiso 1.00 1 c R . . H(3A) H 0.5851 -0.1853 0.5847 0.034 Uiso 1.00 1 c R . . H(4A) H 0.6849 -0.1604 0.4527 0.030 Uiso 1.00 1 c R . . H(6A) H 0.8119 -0.0556 0.3499 0.032 Uiso 1.00 1 c R . . H(7A) H 0.9202 0.0812 0.3192 0.032 Uiso 1.00 1 c R . . H(8A) H 0.9169 0.1979 0.4200 0.027 Uiso 1.00 1 c R . . H(11A) H 0.8531 0.1718 0.8426 0.034 Uiso 1.00 1 c R . . H(12B) H 1.1817 0.1004 0.8600 0.066 Uiso 1.00 1 c R . . H(12C) H 1.1211 0.1988 0.8818 0.066 Uiso 1.00 1 c R . . H(12A) H 1.1396 0.1706 0.7851 0.066 Uiso 1.00 1 c R . . H(13A) H 0.7682 0.0511 0.9074 0.072 Uiso 1.00 1 c R . . H(13B) H 0.9605 0.0519 0.9471 0.072 Uiso 1.00 1 c R . . H(13C) H 0.9062 -0.0116 0.8683 0.072 Uiso 1.00 1 c R . . H(14A) H 0.6998 0.3913 0.5597 0.034 Uiso 1.00 1 c R . . H(15B) H 0.4928 0.3927 0.4541 0.044 Uiso 1.00 1 c R . . H(15A) H 0.3798 0.4226 0.5292 0.044 Uiso 1.00 1 c R . . H(15C) H 0.3803 0.3209 0.4994 0.044 Uiso 1.00 1 c R . . H(16A) H 0.4342 0.3703 0.6656 0.050 Uiso 1.00 1 c R . . H(16C) H 0.5935 0.4359 0.6771 0.050 Uiso 1.00 1 c R . . H(16B) H 0.6154 0.3330 0.7012 0.050 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Se(1) 0.0256(3) 0.0378(3) 0.0259(3) 0.0028(2) 0.0099(2) -0.0012(2) Se(9) 0.0237(3) 0.0323(3) 0.0438(3) -0.0067(2) 0.0013(2) -0.0054(2) P(1) 0.0203(6) 0.0252(7) 0.0161(6) 0.0019(5) 0.0027(5) -0.0004(5) P(9) 0.0191(6) 0.0205(7) 0.0208(6) 0.0003(5) 0.0021(5) -0.0015(5) O(1) 0.028(2) 0.037(2) 0.0152(17) 0.0075(17) -0.0006(15) -0.0037(16) O(9) 0.0231(19) 0.0214(19) 0.0255(19) 0.0053(15) -0.0017(15) -0.0017(15) C(1) 0.013(2) 0.024(2) 0.019(2) 0.002(2) -0.001(2) -0.003(2) C(2) 0.030(3) 0.030(3) 0.023(2) 0.000(2) 0.005(2) 0.005(2) C(3) 0.026(2) 0.022(2) 0.036(3) -0.004(2) -0.000(2) 0.001(2) C(4) 0.023(2) 0.022(2) 0.028(3) 0.004(2) -0.002(2) -0.005(2) C(5) 0.013(2) 0.028(2) 0.019(2) 0.006(2) -0.006(2) -0.006(2) C(6) 0.020(2) 0.038(3) 0.021(2) 0.010(2) -0.004(2) -0.007(2) C(7) 0.028(3) 0.034(3) 0.019(2) 0.007(2) 0.005(2) 0.004(2) C(8) 0.022(2) 0.022(2) 0.024(2) 0.001(2) -0.000(2) 0.008(2) C(9) 0.019(2) 0.021(2) 0.021(2) 0.006(2) 0.002(2) 0.001(2) C(10) 0.015(2) 0.027(2) 0.017(2) 0.002(2) 0.002(2) -0.001(2) C(11) 0.037(3) 0.035(3) 0.014(2) 0.009(2) -0.002(2) -0.003(2) C(12) 0.026(3) 0.094(6) 0.043(4) -0.011(3) -0.007(3) -0.012(4) C(13) 0.070(5) 0.077(5) 0.031(3) -0.007(4) -0.004(3) 0.015(3) C(14) 0.030(3) 0.018(2) 0.038(3) 0.002(2) 0.005(2) -0.001(2) C(15) 0.049(3) 0.026(3) 0.035(3) 0.004(2) -0.000(2) 0.002(2) C(16) 0.057(4) 0.035(3) 0.032(3) 0.006(3) -0.006(3) -0.006(2) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Se(1) P(1) 2.0836(14) yes . . Se(9) P(9) 2.0829(13) yes . . P(1) P(9) 2.2479(18) yes . . P(1) O(1) 1.595(3) yes . . P(1) C(1) 1.801(5) yes . . P(9) O(9) 1.592(3) yes . . P(9) C(9) 1.794(5) yes . . O(1) C(11) 1.476(6) yes . . O(9) C(14) 1.465(6) yes . . C(1) C(2) 1.376(7) yes . . C(1) C(10) 1.423(7) yes . . C(2) C(3) 1.408(7) yes . . C(3) C(4) 1.371(7) yes . . C(4) C(5) 1.418(7) yes . . C(5) C(6) 1.413(7) yes . . C(5) C(10) 1.421(7) yes . . C(6) C(7) 1.358(8) yes . . C(7) C(8) 1.418(7) yes . . C(8) C(9) 1.377(7) yes . . C(9) C(10) 1.416(7) yes . . C(11) C(12) 1.491(8) yes . . C(11) C(13) 1.515(9) yes . . C(14) C(15) 1.538(8) yes . . C(14) C(16) 1.484(8) yes . . C(2) H(2A) 0.950 no . . C(3) H(3A) 0.950 no . . C(4) H(4A) 0.950 no . . C(6) H(6A) 0.950 no . . C(7) H(7A) 0.950 no . . C(8) H(8A) 0.950 no . . C(11) H(11A) 1.000 no . . C(12) H(12B) 0.980 no . . C(12) H(12C) 0.980 no . . C(12) H(12A) 0.980 no . . C(13) H(13A) 0.980 no . . C(13) H(13B) 0.980 no . . C(13) H(13C) 0.980 no . . C(14) H(14A) 1.000 no . . C(15) H(15B) 0.980 no . . C(15) H(15A) 0.980 no . . C(15) H(15C) 0.980 no . . C(16) H(16A) 0.980 no . . C(16) H(16C) 0.980 no . . C(16) H(16B) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Se(1) P(1) P(9) 116.31(7) yes . . . Se(1) P(1) O(1) 117.21(14) yes . . . Se(1) P(1) C(1) 118.23(16) yes . . . P(9) P(1) O(1) 105.62(15) yes . . . P(9) P(1) C(1) 93.59(17) yes . . . O(1) P(1) C(1) 102.5(2) yes . . . Se(9) P(9) P(1) 117.59(6) yes . . . Se(9) P(9) O(9) 117.10(14) yes . . . Se(9) P(9) C(9) 118.31(17) yes . . . P(1) P(9) O(9) 104.36(14) yes . . . P(1) P(9) C(9) 93.34(17) yes . . . O(9) P(9) C(9) 102.5(2) yes . . . P(1) O(1) C(11) 122.6(3) yes . . . P(9) O(9) C(14) 126.2(3) yes . . . P(1) C(1) C(2) 123.9(3) yes . . . P(1) C(1) C(10) 115.2(3) yes . . . C(2) C(1) C(10) 120.9(4) yes . . . C(1) C(2) C(3) 120.0(5) yes . . . C(2) C(3) C(4) 120.4(5) yes . . . C(3) C(4) C(5) 121.0(4) yes . . . C(4) C(5) C(6) 123.5(4) yes . . . C(4) C(5) C(10) 118.9(4) yes . . . C(6) C(5) C(10) 117.7(4) yes . . . C(5) C(6) C(7) 122.3(5) yes . . . C(6) C(7) C(8) 119.7(4) yes . . . C(7) C(8) C(9) 120.2(4) yes . . . P(9) C(9) C(8) 124.1(3) yes . . . P(9) C(9) C(10) 115.8(3) yes . . . C(8) C(9) C(10) 120.1(4) yes . . . C(1) C(10) C(5) 118.7(4) yes . . . C(1) C(10) C(9) 121.3(4) yes . . . C(5) C(10) C(9) 120.0(4) yes . . . O(1) C(11) C(12) 107.5(4) yes . . . O(1) C(11) C(13) 107.9(4) yes . . . C(12) C(11) C(13) 114.9(5) yes . . . O(9) C(14) C(15) 103.5(4) yes . . . O(9) C(14) C(16) 111.9(4) yes . . . C(15) C(14) C(16) 112.1(5) yes . . . C(1) C(2) H(2A) 120.0 no . . . C(3) C(2) H(2A) 120.0 no . . . C(2) C(3) H(3A) 119.8 no . . . C(4) C(3) H(3A) 119.8 no . . . C(3) C(4) H(4A) 119.5 no . . . C(5) C(4) H(4A) 119.5 no . . . C(5) C(6) H(6A) 118.8 no . . . C(7) C(6) H(6A) 118.8 no . . . C(6) C(7) H(7A) 120.1 no . . . C(8) C(7) H(7A) 120.1 no . . . C(7) C(8) H(8A) 119.9 no . . . C(9) C(8) H(8A) 119.9 no . . . O(1) C(11) H(11A) 108.8 no . . . C(12) C(11) H(11A) 108.8 no . . . C(13) C(11) H(11A) 108.8 no . . . C(11) C(12) H(12B) 109.5 no . . . C(11) C(12) H(12C) 109.5 no . . . C(11) C(12) H(12A) 109.5 no . . . H(12B) C(12) H(12C) 109.5 no . . . H(12B) C(12) H(12A) 109.5 no . . . H(12C) C(12) H(12A) 109.5 no . . . C(11) C(13) H(13A) 109.5 no . . . C(11) C(13) H(13B) 109.5 no . . . C(11) C(13) H(13C) 109.5 no . . . H(13A) C(13) H(13B) 109.5 no . . . H(13A) C(13) H(13C) 109.5 no . . . H(13B) C(13) H(13C) 109.5 no . . . O(9) C(14) H(14A) 109.7 no . . . C(15) C(14) H(14A) 109.7 no . . . C(16) C(14) H(14A) 109.7 no . . . C(14) C(15) H(15B) 109.5 no . . . C(14) C(15) H(15A) 109.5 no . . . C(14) C(15) H(15C) 109.5 no . . . H(15B) C(15) H(15A) 109.5 no . . . H(15B) C(15) H(15C) 109.5 no . . . H(15A) C(15) H(15C) 109.5 no . . . C(14) C(16) H(16A) 109.5 no . . . C(14) C(16) H(16C) 109.5 no . . . C(14) C(16) H(16B) 109.5 no . . . H(16A) C(16) H(16C) 109.5 no . . . H(16A) C(16) H(16B) 109.5 no . . . H(16C) C(16) H(16B) 109.5 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Se(1) P(1) P(9) Se(9) 104.38(8) ? . . . . Se(1) P(1) P(9) O(9) -27.25(15) ? . . . . Se(1) P(1) P(9) C(9) -131.11(16) ? . . . . Se(1) P(1) O(1) C(11) -25.5(4) ? . . . . Se(1) P(1) C(1) C(2) -51.7(4) ? . . . . Se(1) P(1) C(1) C(10) 129.2(3) ? . . . . P(9) P(1) O(1) C(11) 105.9(3) ? . . . . O(1) P(1) P(9) Se(9) -27.52(16) ? . . . . O(1) P(1) P(9) O(9) -159.15(19) ? . . . . O(1) P(1) P(9) C(9) 97.0(2) ? . . . . P(9) P(1) C(1) C(2) -174.3(4) ? . . . . P(9) P(1) C(1) C(10) 6.7(3) ? . . . . C(1) P(1) P(9) Se(9) -131.59(16) ? . . . . C(1) P(1) P(9) O(9) 96.8(2) ? . . . . C(1) P(1) P(9) C(9) -7.1(2) ? . . . . O(1) P(1) C(1) C(2) 78.9(4) ? . . . . O(1) P(1) C(1) C(10) -100.2(3) ? . . . . C(1) P(1) O(1) C(11) -156.7(3) ? . . . . Se(9) P(9) O(9) C(14) -16.6(4) ? . . . . Se(9) P(9) C(9) C(8) -50.2(4) ? . . . . Se(9) P(9) C(9) C(10) 131.0(3) ? . . . . P(1) P(9) O(9) C(14) 115.3(3) ? . . . . P(1) P(9) C(9) C(8) -174.1(4) ? . . . . P(1) P(9) C(9) C(10) 7.1(3) ? . . . . O(9) P(9) C(9) C(8) 80.3(4) ? . . . . O(9) P(9) C(9) C(10) -98.5(3) ? . . . . C(9) P(9) O(9) C(14) -147.9(4) ? . . . . P(1) O(1) C(11) C(12) -134.3(4) ? . . . . P(1) O(1) C(11) C(13) 101.2(5) ? . . . . P(9) O(9) C(14) C(15) 161.9(3) ? . . . . P(9) O(9) C(14) C(16) -77.2(5) ? . . . . P(1) C(1) C(2) C(3) -177.6(4) ? . . . . P(1) C(1) C(10) C(5) 176.3(3) ? . . . . P(1) C(1) C(10) C(9) -3.2(6) ? . . . . C(2) C(1) C(10) C(5) -2.8(7) ? . . . . C(2) C(1) C(10) C(9) 177.7(4) ? . . . . C(10) C(1) C(2) C(3) 1.4(7) ? . . . . C(1) C(2) C(3) C(4) 0.7(8) ? . . . . C(2) C(3) C(4) C(5) -1.3(7) ? . . . . C(3) C(4) C(5) C(6) 179.9(3) ? . . . . C(3) C(4) C(5) C(10) -0.2(5) ? . . . . C(4) C(5) C(6) C(7) -179.6(4) ? . . . . C(4) C(5) C(10) C(1) 2.2(6) ? . . . . C(4) C(5) C(10) C(9) -178.3(4) ? . . . . C(6) C(5) C(10) C(1) -177.9(4) ? . . . . C(6) C(5) C(10) C(9) 1.6(6) ? . . . . C(10) C(5) C(6) C(7) 0.6(7) ? . . . . C(5) C(6) C(7) C(8) -2.0(7) ? . . . . C(6) C(7) C(8) C(9) 1.4(7) ? . . . . C(7) C(8) C(9) P(9) -178.0(3) ? . . . . C(7) C(8) C(9) C(10) 0.8(7) ? . . . . P(9) C(9) C(10) C(1) -3.9(6) ? . . . . P(9) C(9) C(10) C(5) 176.6(3) ? . . . . C(8) C(9) C(10) C(1) 177.2(4) ? . . . . C(8) C(9) C(10) C(5) -2.2(7) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Se(1) C(12) 3.562(6) ? . 1_455 O(1) C(6) 3.500(6) ? . 3_756 O(9) C(3) 3.469(6) ? . 3_656 O(9) C(4) 3.429(6) ? . 3_656 C(3) O(9) 3.469(6) ? . 3_656 C(4) O(9) 3.429(6) ? . 3_656 C(4) C(8) 3.578(7) ? . 3_756 C(6) O(1) 3.500(6) ? . 3_756 C(6) C(10) 3.545(6) ? . 3_756 C(7) C(10) 3.579(7) ? . 3_756 C(8) C(4) 3.578(7) ? . 3_756 C(10) C(6) 3.545(6) ? . 3_756 C(10) C(7) 3.579(7) ? . 3_756 C(12) Se(1) 3.562(6) ? . 1_655 Se(1) H(4A) 3.5068 ? . 3_656 Se(1) H(6A) 3.2400 ? . 3_656 Se(1) H(12B) 3.277 ? . 1_455 Se(1) H(12A) 3.034 ? . 1_455 Se(1) H(15B) 3.226 ? . 4_555 Se(1) H(16C) 3.484 ? . 2_646 Se(9) H(4A) 3.3274 ? . 3_756 Se(9) H(13C) 3.099 ? . 2_756 Se(9) H(16A) 3.548 ? . 1_655 O(1) H(6A) 2.928 ? . 3_756 O(1) H(7A) 3.142 ? . 3_756 O(9) H(3A) 2.997 ? . 3_656 O(9) H(4A) 2.926 ? . 3_656 C(1) H(7A) 3.469 ? . 3_756 C(2) H(7A) 3.542 ? . 3_756 C(2) H(16A) 3.418 ? . 2_646 C(3) H(12C) 3.305 ? . 2_746 C(3) H(15C) 3.100 ? . 3_656 C(4) H(8A) 3.549 ? . 3_756 C(4) H(15C) 3.167 ? . 3_656 C(7) H(16B) 3.582 ? . 4_554 C(8) H(11A) 3.163 ? . 4_554 C(8) H(12C) 3.240 ? . 4_554 C(9) H(3A) 3.527 ? . 3_656 C(11) H(8A) 3.069 ? . 4_555 C(12) H(6A) 3.424 ? . 3_756 C(12) H(8A) 3.060 ? . 4_555 C(12) H(15B) 3.471 ? . 4_655 C(12) H(15C) 3.205 ? . 4_655 C(13) H(13B) 3.070 ? . 3_757 C(13) H(14A) 3.231 ? . 4_555 C(13) H(15B) 3.448 ? . 4_555 C(13) H(15A) 3.121 ? . 2_646 C(14) H(13A) 3.340 ? . 4_554 C(15) H(3A) 3.205 ? . 3_656 C(15) H(4A) 3.463 ? . 3_656 C(15) H(12B) 3.055 ? . 4_454 C(15) H(12C) 3.339 ? . 4_454 C(15) H(13A) 3.480 ? . 2_656 C(15) H(13A) 3.275 ? . 4_554 C(15) H(15B) 3.572 ? . 3_666 C(15) H(15A) 3.403 ? . 3_666 C(16) H(2A) 2.856 ? . 2_656 H(2A) C(16) 2.856 ? . 2_646 H(2A) H(16A) 2.497 ? . 2_646 H(2A) H(16C) 2.701 ? . 2_646 H(2A) H(16B) 2.894 ? . 2_646 H(3A) O(9) 2.997 ? . 3_656 H(3A) C(9) 3.527 ? . 3_656 H(3A) C(15) 3.205 ? . 3_656 H(3A) H(12C) 2.921 ? . 2_746 H(3A) H(15B) 3.229 ? . 3_656 H(3A) H(15C) 2.459 ? . 3_656 H(4A) Se(1) 3.5068 ? . 3_656 H(4A) Se(9) 3.3274 ? . 3_756 H(4A) O(9) 2.926 ? . 3_656 H(4A) C(15) 3.463 ? . 3_656 H(4A) H(15C) 2.592 ? . 3_656 H(6A) Se(1) 3.2400 ? . 3_656 H(6A) O(1) 2.928 ? . 3_756 H(6A) C(12) 3.424 ? . 3_756 H(6A) H(12B) 3.381 ? . 3_756 H(6A) H(12A) 2.790 ? . 3_756 H(6A) H(16C) 3.596 ? . 4_554 H(7A) O(1) 3.142 ? . 3_756 H(7A) C(1) 3.469 ? . 3_756 H(7A) C(2) 3.542 ? . 3_756 H(7A) H(13C) 3.510 ? . 3_756 H(7A) H(16C) 3.300 ? . 4_554 H(7A) H(16B) 3.204 ? . 4_554 H(8A) C(4) 3.549 ? . 3_756 H(8A) C(11) 3.069 ? . 4_554 H(8A) C(12) 3.060 ? . 4_554 H(8A) H(11A) 2.344 ? . 4_554 H(8A) H(12C) 2.352 ? . 4_554 H(8A) H(12A) 3.479 ? . 4_554 H(11A) C(8) 3.163 ? . 4_555 H(11A) H(8A) 2.344 ? . 4_555 H(11A) H(15B) 3.591 ? . 4_555 H(12B) Se(1) 3.277 ? . 1_655 H(12B) C(15) 3.055 ? . 4_655 H(12B) H(6A) 3.381 ? . 3_756 H(12B) H(14A) 3.492 ? . 2_746 H(12B) H(15B) 2.778 ? . 4_655 H(12B) H(15A) 3.010 ? . 4_655 H(12B) H(15C) 2.858 ? . 4_655 H(12B) H(16C) 3.127 ? . 2_746 H(12C) C(3) 3.305 ? . 2_756 H(12C) C(8) 3.240 ? . 4_555 H(12C) C(15) 3.339 ? . 4_655 H(12C) H(3A) 2.921 ? . 2_756 H(12C) H(8A) 2.352 ? . 4_555 H(12C) H(15B) 3.366 ? . 4_655 H(12C) H(15A) 3.493 ? . 4_655 H(12C) H(15C) 2.674 ? . 4_655 H(12A) Se(1) 3.034 ? . 1_655 H(12A) H(6A) 2.790 ? . 3_756 H(12A) H(8A) 3.479 ? . 4_555 H(13A) C(14) 3.340 ? . 4_555 H(13A) C(15) 3.480 ? . 2_646 H(13A) C(15) 3.275 ? . 4_555 H(13A) H(13B) 3.394 ? . 3_757 H(13A) H(14A) 2.645 ? . 4_555 H(13A) H(15B) 2.498 ? . 4_555 H(13A) H(15A) 2.505 ? . 2_646 H(13A) H(16A) 3.317 ? . 2_646 H(13A) H(16C) 3.520 ? . 2_646 H(13B) C(13) 3.070 ? . 3_757 H(13B) H(13A) 3.394 ? . 3_757 H(13B) H(13B) 2.336 ? . 3_757 H(13B) H(13C) 3.081 ? . 3_757 H(13B) H(14A) 2.946 ? . 4_555 H(13B) H(15A) 3.364 ? . 2_646 H(13B) H(15A) 3.489 ? . 4_655 H(13C) Se(9) 3.099 ? . 2_746 H(13C) H(7A) 3.510 ? . 3_756 H(13C) H(13B) 3.081 ? . 3_757 H(13C) H(14A) 3.549 ? . 2_746 H(13C) H(15A) 3.041 ? . 2_646 H(13C) H(16A) 3.236 ? . 2_646 H(14A) C(13) 3.231 ? . 4_554 H(14A) H(12B) 3.492 ? . 2_756 H(14A) H(13A) 2.645 ? . 4_554 H(14A) H(13B) 2.946 ? . 4_554 H(14A) H(13C) 3.549 ? . 2_756 H(14A) H(15B) 3.588 ? . 3_666 H(14A) H(15A) 3.172 ? . 3_666 H(15B) Se(1) 3.226 ? . 4_554 H(15B) C(12) 3.471 ? . 4_454 H(15B) C(13) 3.448 ? . 4_554 H(15B) C(15) 3.572 ? . 3_666 H(15B) H(3A) 3.229 ? . 3_656 H(15B) H(11A) 3.591 ? . 4_554 H(15B) H(12B) 2.778 ? . 4_454 H(15B) H(12C) 3.366 ? . 4_454 H(15B) H(13A) 2.498 ? . 4_554 H(15B) H(14A) 3.588 ? . 3_666 H(15B) H(15B) 3.535 ? . 3_666 H(15B) H(15A) 2.959 ? . 3_666 H(15B) H(16C) 3.343 ? . 3_666 H(15A) C(13) 3.121 ? . 2_656 H(15A) C(15) 3.403 ? . 3_666 H(15A) H(12B) 3.010 ? . 4_454 H(15A) H(12C) 3.493 ? . 4_454 H(15A) H(13A) 2.505 ? . 2_656 H(15A) H(13B) 3.364 ? . 2_656 H(15A) H(13B) 3.489 ? . 4_454 H(15A) H(13C) 3.041 ? . 2_656 H(15A) H(14A) 3.172 ? . 3_666 H(15A) H(15B) 2.959 ? . 3_666 H(15A) H(15A) 3.185 ? . 3_666 H(15C) C(3) 3.100 ? . 3_656 H(15C) C(4) 3.167 ? . 3_656 H(15C) C(12) 3.205 ? . 4_454 H(15C) H(3A) 2.459 ? . 3_656 H(15C) H(4A) 2.592 ? . 3_656 H(15C) H(12B) 2.858 ? . 4_454 H(15C) H(12C) 2.674 ? . 4_454 H(16A) Se(9) 3.548 ? . 1_455 H(16A) C(2) 3.418 ? . 2_656 H(16A) H(2A) 2.497 ? . 2_656 H(16A) H(13A) 3.317 ? . 2_656 H(16A) H(13C) 3.236 ? . 2_656 H(16C) Se(1) 3.484 ? . 2_656 H(16C) H(2A) 2.701 ? . 2_656 H(16C) H(6A) 3.596 ? . 4_555 H(16C) H(7A) 3.300 ? . 4_555 H(16C) H(12B) 3.127 ? . 2_756 H(16C) H(13A) 3.520 ? . 2_656 H(16C) H(15B) 3.343 ? . 3_666 H(16B) C(7) 3.582 ? . 4_555 H(16B) H(2A) 2.894 ? . 2_656 H(16B) H(7A) 3.204 ? . 4_555 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment '35.cif' data_pkadw59 _database_code_depnum_ccdc_archive 'CCDC 670153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 O2 P4 Se2' _chemical_formula_sum 'C22 H18 O2 P4 Se2' _chemical_formula_weight 596.16 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 7.0657(16) _cell_length_b 17.803(4) _cell_length_c 17.866(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.746(7) _cell_angle_gamma 90.00 _cell_volume 2231.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3872 _cell_measurement_theta_min 2.2883 _cell_measurement_theta_max 26.3714 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0500 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 3.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8073 _exptl_absorpt_correction_T_max 0.8381 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7028 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2011 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0219P)^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 2011 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.002 _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 0.06953(6) 0.34014(3) 0.44287(2) 0.03302(17) Uani 1 1 d . . . O1 O 0.4622(4) 0.36943(14) 0.38272(13) 0.0221(6) Uani 1 1 d . . . P1 P 0.23831(14) 0.39209(6) 0.36916(5) 0.0205(3) Uani 1 1 d . . . C1 C 0.2599(5) 0.4921(2) 0.36958(19) 0.0201(9) Uani 1 1 d . . . C2 C 0.2916(6) 0.5375(2) 0.4324(2) 0.0269(10) Uani 1 1 d . . . H2A H 0.2956 0.5165 0.4814 0.032 Uiso 1 1 calc R . . C3 C 0.3180(6) 0.6148(2) 0.4234(2) 0.0325(11) Uani 1 1 d . . . H3A H 0.3418 0.6459 0.4667 0.039 Uiso 1 1 calc R . . C4 C 0.3102(6) 0.6458(2) 0.3540(2) 0.0318(11) Uani 1 1 d . . . H4A H 0.3310 0.6983 0.3497 0.038 Uiso 1 1 calc R . . C5 C 0.2717(5) 0.6021(2) 0.2875(2) 0.0244(9) Uani 1 1 d . . . C6 C 0.2624(5) 0.6317(2) 0.2138(2) 0.0275(10) Uani 1 1 d . . . H6A H 0.2775 0.6842 0.2069 0.033 Uiso 1 1 calc R . . C7 C 0.2321(6) 0.5860(2) 0.1527(2) 0.0279(10) Uani 1 1 d . . . H7A H 0.2288 0.6069 0.1036 0.034 Uiso 1 1 calc R . . C8 C 0.2057(5) 0.5083(2) 0.1609(2) 0.0247(9) Uani 1 1 d . . . H8A H 0.1846 0.4773 0.1175 0.030 Uiso 1 1 calc R . . C9 C 0.2099(5) 0.4767(2) 0.23115(19) 0.0190(8) Uani 1 1 d . . . C10 C 0.2472(5) 0.5240(2) 0.29668(19) 0.0182(8) Uani 1 1 d . . . P9 P 0.15742(15) 0.37747(6) 0.24665(5) 0.0203(3) Uani 1 1 d . . . C11 C 0.5123(6) 0.2932(2) 0.3852(2) 0.0291(10) Uani 1 1 d . . . H11A H 0.4347 0.2664 0.4186 0.044 Uiso 1 1 calc R . . H11B H 0.6474 0.2880 0.4044 0.044 Uiso 1 1 calc R . . H11C H 0.4899 0.2718 0.3344 0.044 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 0.0312(3) 0.0493(3) 0.0176(3) 0.01284(19) -0.00153(18) -0.0095(2) O1 0.0276(16) 0.0211(14) 0.0171(14) 0.0015(11) 0.0007(11) 0.0018(12) P1 0.0222(6) 0.0265(6) 0.0119(5) 0.0038(4) -0.0014(4) 0.0002(4) C1 0.012(2) 0.031(2) 0.017(2) -0.0027(17) 0.0016(16) 0.0039(17) C2 0.022(2) 0.039(3) 0.020(2) -0.0053(19) 0.0030(17) 0.0018(19) C3 0.021(2) 0.039(3) 0.037(3) -0.022(2) 0.0033(19) 0.0023(19) C4 0.024(3) 0.027(2) 0.044(3) -0.009(2) 0.007(2) 0.0049(19) C5 0.012(2) 0.026(2) 0.035(2) -0.0013(19) 0.0004(17) 0.0010(17) C6 0.017(2) 0.022(2) 0.042(3) 0.013(2) 0.0001(19) -0.0019(18) C7 0.022(2) 0.038(3) 0.023(2) 0.019(2) 0.0006(18) -0.0032(19) C8 0.017(2) 0.043(3) 0.013(2) 0.0027(18) 0.0007(16) -0.0020(19) C9 0.016(2) 0.027(2) 0.0142(19) 0.0029(17) 0.0025(15) 0.0052(17) C10 0.012(2) 0.023(2) 0.021(2) 0.0008(17) 0.0039(16) 0.0025(16) P9 0.0249(6) 0.0221(5) 0.0133(5) -0.0008(4) -0.0005(4) 0.0036(4) C11 0.031(3) 0.033(3) 0.023(2) -0.0001(18) -0.0021(18) -0.0023(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 Se1 P1 2.0930(11) . ? O1 C11 1.402(5) . ? O1 P1 1.623(3) . ? P1 C1 1.788(4) . ? P1 P9 2.2116(13) . ? C1 C2 1.380(5) . ? C1 C10 1.413(5) . ? C2 C3 1.400(6) . ? C2 H2A 0.9500 . ? C3 C4 1.351(6) . ? C3 H3A 0.9500 . ? C4 C5 1.421(6) . ? C4 H4A 0.9500 . ? C5 C6 1.413(6) . ? C5 C10 1.413(5) . ? C6 C7 1.358(6) . ? C6 H6A 0.9500 . ? C7 C8 1.407(6) . ? C7 H7A 0.9500 . ? C8 C9 1.371(5) . ? C8 H8A 0.9500 . ? C9 C10 1.441(5) . ? C9 P9 1.833(4) . ? P9 P9 2.242(2) 2 ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 P1 118.9(2) . . ? O1 P1 C1 99.54(16) . . ? O1 P1 Se1 114.44(10) . . ? C1 P1 Se1 119.49(13) . . ? O1 P1 P9 104.63(10) . . ? C1 P1 P9 97.67(12) . . ? Se1 P1 P9 118.07(5) . . ? C2 C1 C10 120.1(4) . . ? C2 C1 P1 126.4(3) . . ? C10 C1 P1 113.5(3) . . ? C1 C2 C3 119.5(4) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 121.8(4) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C10 118.9(4) . . ? C6 C5 C4 124.0(4) . . ? C10 C5 C4 117.1(4) . . ? C7 C6 C5 120.8(4) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 C8 121.0(4) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 119.1(4) . . ? C8 C9 P9 123.3(3) . . ? C10 C9 P9 117.4(3) . . ? C5 C10 C1 120.4(3) . . ? C5 C10 C9 119.5(3) . . ? C1 C10 C9 120.0(3) . . ? C9 P9 P1 90.16(12) . . ? C9 P9 P9 103.16(12) . 2 ? P1 P9 P9 95.16(6) . 2 ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C11 O1 P1 C1 -179.0(3) . . . . ? C11 O1 P1 Se1 52.3(3) . . . . ? C11 O1 P1 P9 -78.4(2) . . . . ? O1 P1 C1 C2 -80.1(4) . . . . ? Se1 P1 C1 C2 45.1(4) . . . . ? P9 P1 C1 C2 173.6(3) . . . . ? O1 P1 C1 C10 98.0(3) . . . . ? Se1 P1 C1 C10 -136.7(2) . . . . ? P9 P1 C1 C10 -8.3(3) . . . . ? C10 C1 C2 C3 -2.3(6) . . . . ? P1 C1 C2 C3 175.7(3) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? C2 C3 C4 C5 1.2(6) . . . . ? C3 C4 C5 C6 -179.9(4) . . . . ? C3 C4 C5 C10 -1.8(6) . . . . ? C10 C5 C6 C7 -0.6(6) . . . . ? C4 C5 C6 C7 177.5(4) . . . . ? C5 C6 C7 C8 1.2(6) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 C10 -1.7(5) . . . . ? C7 C8 C9 P9 174.8(3) . . . . ? C6 C5 C10 C1 178.6(3) . . . . ? C4 C5 C10 C1 0.3(5) . . . . ? C6 C5 C10 C9 -1.1(5) . . . . ? C4 C5 C10 C9 -179.3(3) . . . . ? C2 C1 C10 C5 1.7(5) . . . . ? P1 C1 C10 C5 -176.6(3) . . . . ? C2 C1 C10 C9 -178.6(3) . . . . ? P1 C1 C10 C9 3.1(4) . . . . ? C8 C9 C10 C5 2.3(5) . . . . ? P9 C9 C10 C5 -174.5(3) . . . . ? C8 C9 C10 C1 -177.4(3) . . . . ? P9 C9 C10 C1 5.9(5) . . . . ? C8 C9 P9 P1 174.1(3) . . . . ? C10 C9 P9 P1 -9.3(3) . . . . ? C8 C9 P9 P9 -90.6(3) . . . 2 ? C10 C9 P9 P9 86.0(3) . . . 2 ? O1 P1 P9 C9 -92.99(15) . . . . ? C1 P1 P9 C9 9.01(17) . . . . ? Se1 P1 P9 C9 138.41(13) . . . . ? O1 P1 P9 P9 163.78(10) . . . 2 ? C1 P1 P9 P9 -94.22(12) . . . 2 ? Se1 P1 P9 P9 35.19(5) . . . 2 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.502 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.103