Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2006-03-16 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence loop_ _publ_contact_author_name _publ_contact_author_address _publ_contact_author_phone _publ_contact_author_fax _publ_contact_author_email 'Roodt, Andreas' ; Department of Chemistry University of the Free State P.O. Box 339 Bloemfontein 9300 South Africa ; ; +27 51 401 2547 ; ; +27 51 444 6384 ; roodta.sci@ufs.ac.za _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in Dalton Transactions. ; _publ_section_title ; Rapid phosphorous(III) ligand evaluation utilising potassium selenocyanate ; loop_ _publ_author_name _publ_author_address _publ_author_footnote A.Muller ; Department of Chemistry University of Johannesburg P.O. Box 524 Johannesburg 2006 South Africa ; ; Current address: Department of Chemistry University of the Free State P.O. Box 339 Bloemfontein 9300 South Africa ; S.Otto ; Department of Chemistry University of the Free State P.O. Box 339 Bloemfontein 9300 South Africa ; ; Currently employed at: Sasol Technology Research & Development P.O. Box 1 Sasolburg 1947 South Africa. ; A.Roodt ; Department of Chemistry University of the Free State P.O. Box 339 Bloemfontein 9300 South Africa ; ; ? ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_seph2cy _database_code_depnum_ccdc_archive 'CCDC 657196' _audit_creation_date 2006-03-16T12:57:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C18 H21 P Se' _chemical_formula_sum 'C18 H21 P Se' _chemical_formula_weight 347.28 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 15.140(2) _cell_length_b 11.6421(19) _cell_length_c 10.1580(17) _cell_angle_alpha 90 _cell_angle_beta 107.741(3) _cell_angle_gamma 90 _cell_volume 1705.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 983 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 24.02 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description cuboid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 2.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3717 _exptl_absorpt_correction_T_max 0.7113 _exptl_absorpt_process_details ; SADABS (Bruker, 2004) ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_detector_area_resol_mean 512 _diffrn_measurement_device_type ; Bruker SMART CCD 1K ; _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11246 _diffrn_reflns_av_R_equivalents 0.0794 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4207 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _exptl_special_details ; See manuscript ; #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker, 1999)' _computing_structure_solution 'SIR97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'WinGX (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4207 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0938 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.598 _refine_diff_density_min -0.568 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' 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 Se 0.23177(2) 0.48820(2) 0.41419(3) 0.06343(13) Uani 1 1 d . . . P P 0.25751(4) 0.40287(5) 0.60628(6) 0.04046(17) Uani 1 1 d . . . C11 C 0.16485(14) 0.30325(19) 0.6117(2) 0.0405(5) Uani 1 1 d . . . H11 H 0.1837 0.2649 0.7019 0.049 Uiso 1 1 calc R . . C12 C 0.07467(15) 0.3692(2) 0.5984(3) 0.0550(7) Uani 1 1 d . . . H12A H 0.0846 0.4229 0.6745 0.066 Uiso 1 1 calc R . . H12B H 0.0572 0.4128 0.5129 0.066 Uiso 1 1 calc R . . C13 C -0.00374(16) 0.2864(3) 0.5991(3) 0.0626(8) Uani 1 1 d . . . H13A H 0.0114 0.2481 0.6881 0.075 Uiso 1 1 calc R . . H13B H -0.0605 0.3295 0.5866 0.075 Uiso 1 1 calc R . . C14 C -0.01900(17) 0.1978(3) 0.4867(3) 0.0685(9) Uani 1 1 d . . . H14A H -0.0391 0.2354 0.3973 0.082 Uiso 1 1 calc R . . H14B H -0.0675 0.1453 0.4921 0.082 Uiso 1 1 calc R . . C15 C 0.06984(19) 0.1309(2) 0.5007(3) 0.0656(8) Uani 1 1 d . . . H15A H 0.0594 0.0768 0.4248 0.079 Uiso 1 1 calc R . . H15B H 0.0865 0.0874 0.5863 0.079 Uiso 1 1 calc R . . C16 C 0.14957(16) 0.2111(2) 0.5002(3) 0.0512(6) Uani 1 1 d . . . H16A H 0.2059 0.1665 0.5155 0.061 Uiso 1 1 calc R . . H16B H 0.1360 0.2476 0.4104 0.061 Uiso 1 1 calc R . . C21 C 0.36451(15) 0.32094(19) 0.6525(2) 0.0432(6) Uani 1 1 d . . . C22 C 0.37684(17) 0.2217(2) 0.7305(3) 0.0580(7) Uani 1 1 d . . . H22 H 0.3286 0.1942 0.7606 0.070 Uiso 1 1 calc R . . C23 C 0.4599(2) 0.1631(3) 0.7642(3) 0.0748(9) Uani 1 1 d . . . H23 H 0.4676 0.0962 0.8165 0.090 Uiso 1 1 calc R . . C24 C 0.5316(2) 0.2045(3) 0.7197(3) 0.0793(10) Uani 1 1 d . . . H24 H 0.5875 0.1648 0.7416 0.095 Uiso 1 1 calc R . . C25 C 0.5209(2) 0.3027(3) 0.6443(4) 0.0816(10) Uani 1 1 d . . . H25 H 0.5700 0.3310 0.6167 0.098 Uiso 1 1 calc R . . C26 C 0.43717(17) 0.3606(2) 0.6085(3) 0.0624(7) Uani 1 1 d . . . H26 H 0.4296 0.4266 0.5546 0.075 Uiso 1 1 calc R . . C31 C 0.26971(16) 0.50107(19) 0.7508(3) 0.0468(6) Uani 1 1 d . . . C32 C 0.22317(16) 0.6053(2) 0.7268(3) 0.0590(7) Uani 1 1 d . . . H32 H 0.1872 0.6244 0.6377 0.071 Uiso 1 1 calc R . . C33 C 0.22965(18) 0.6808(3) 0.8337(4) 0.0748(9) Uani 1 1 d . . . H33 H 0.1981 0.7504 0.8169 0.090 Uiso 1 1 calc R . . C34 C 0.2824(2) 0.6530(3) 0.9636(4) 0.0800(10) Uani 1 1 d . . . H34 H 0.2864 0.7037 1.0359 0.096 Uiso 1 1 calc R . . C35 C 0.3300(2) 0.5509(3) 0.9894(3) 0.0810(10) Uani 1 1 d . . . H35 H 0.3664 0.5329 1.0786 0.097 Uiso 1 1 calc R . . C36 C 0.3234(2) 0.4750(2) 0.8818(3) 0.0632(8) Uani 1 1 d . . . H36 H 0.3557 0.4058 0.8988 0.076 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 Se 0.0820(2) 0.0548(2) 0.0632(2) 0.01835(14) 0.03652(17) 0.01488(14) P 0.0435(3) 0.0348(3) 0.0479(4) 0.0008(3) 0.0213(3) 0.0032(3) C11 0.0400(13) 0.0420(13) 0.0417(14) -0.0009(11) 0.0155(10) -0.0032(11) C12 0.0434(14) 0.0590(16) 0.0662(18) -0.0049(14) 0.0223(13) 0.0011(12) C13 0.0435(15) 0.082(2) 0.0653(19) -0.0023(17) 0.0215(13) -0.0049(14) C14 0.0533(18) 0.085(2) 0.066(2) -0.0053(17) 0.0159(15) -0.0200(15) C15 0.0688(18) 0.0560(17) 0.072(2) -0.0149(15) 0.0221(15) -0.0180(14) C16 0.0514(15) 0.0498(15) 0.0551(16) -0.0082(13) 0.0200(12) -0.0011(12) C21 0.0443(14) 0.0370(13) 0.0509(15) -0.0064(11) 0.0183(11) 0.0012(11) C22 0.0506(16) 0.0544(16) 0.0707(19) 0.0071(15) 0.0212(13) 0.0076(13) C23 0.066(2) 0.067(2) 0.084(2) 0.0056(18) 0.0112(17) 0.0213(16) C24 0.0532(19) 0.097(3) 0.082(2) -0.013(2) 0.0124(17) 0.0311(19) C25 0.0481(18) 0.102(3) 0.103(3) 0.000(2) 0.0350(17) 0.0086(18) C26 0.0512(16) 0.0644(18) 0.079(2) 0.0020(16) 0.0313(15) 0.0012(14) C31 0.0444(14) 0.0401(14) 0.0650(18) -0.0096(13) 0.0302(13) -0.0070(11) C32 0.0467(15) 0.0506(16) 0.078(2) -0.0165(15) 0.0166(13) 0.0055(12) C33 0.0584(19) 0.0594(19) 0.107(3) -0.0324(19) 0.0249(18) 0.0034(14) C34 0.089(2) 0.074(2) 0.088(3) -0.042(2) 0.043(2) -0.0117(18) C35 0.122(3) 0.068(2) 0.053(2) -0.0116(17) 0.0259(19) -0.001(2) C36 0.087(2) 0.0463(16) 0.059(2) -0.0044(14) 0.0259(17) 0.0016(14) _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 Se P 2.1172(7) . ? P C21 1.814(2) . ? P C31 1.825(3) . ? P C11 1.834(2) . ? C11 C16 1.526(3) . ? C11 C12 1.536(3) . ? C11 H11 0.9800 . ? C12 C13 1.531(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.503(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.523(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.527(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C21 C22 1.381(3) . ? C21 C26 1.387(3) . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C23 C24 1.384(4) . ? C23 H23 0.9300 . ? C24 C25 1.358(4) . ? C24 H24 0.9300 . ? C25 C26 1.384(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C36 1.365(4) . ? C31 C32 1.387(3) . ? C32 C33 1.376(3) . ? C32 H32 0.9300 . ? C33 C34 1.357(4) . ? C33 H33 0.9300 . ? C34 C35 1.372(4) . ? C34 H34 0.9300 . ? C35 C36 1.386(4) . ? C35 H35 0.9300 . ? C36 H36 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 C21 P C31 104.93(11) . . ? C21 P C11 106.89(11) . . ? C31 P C11 105.22(10) . . ? C21 P Se 112.60(8) . . ? C31 P Se 113.12(9) . . ? C11 P Se 113.38(8) . . ? C16 C11 C12 110.87(18) . . ? C16 C11 P 111.51(15) . . ? C12 C11 P 110.40(17) . . ? C16 C11 H11 108.0 . . ? C12 C11 H11 108.0 . . ? P C11 H11 108.0 . . ? C13 C12 C11 110.7(2) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 111.6(2) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C15 110.7(2) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.3(2) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C11 C16 C15 111.63(19) . . ? C11 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C11 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C22 C21 C26 118.8(2) . . ? C22 C21 P 122.85(18) . . ? C26 C21 P 118.4(2) . . ? C23 C22 C21 120.7(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.6(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 120.5(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.0(3) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C36 C31 C32 119.1(2) . . ? C36 C31 P 121.91(19) . . ? C32 C31 P 119.0(2) . . ? C33 C32 C31 120.6(3) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 119.6(3) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 120.7(3) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C34 C35 C36 119.6(3) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C31 C36 C35 120.3(3) . . ? C31 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? 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 C21 P C11 C16 -65.96(18) . . . . ? C31 P C11 C16 -177.16(17) . . . . ? Se P C11 C16 58.72(17) . . . . ? C21 P C11 C12 170.32(16) . . . . ? C31 P C11 C12 59.12(18) . . . . ? Se P C11 C12 -65.01(17) . . . . ? C16 C11 C12 C13 54.5(3) . . . . ? P C11 C12 C13 178.57(17) . . . . ? C11 C12 C13 C14 -56.6(3) . . . . ? C12 C13 C14 C15 57.2(3) . . . . ? C13 C14 C15 C16 -56.3(3) . . . . ? C12 C11 C16 C15 -54.3(3) . . . . ? P C11 C16 C15 -177.71(18) . . . . ? C14 C15 C16 C11 55.2(3) . . . . ? C31 P C21 C22 87.2(2) . . . . ? C11 P C21 C22 -24.2(2) . . . . ? Se P C21 C22 -149.39(19) . . . . ? C31 P C21 C26 -92.2(2) . . . . ? C11 P C21 C26 156.40(19) . . . . ? Se P C21 C26 31.3(2) . . . . ? C26 C21 C22 C23 0.1(4) . . . . ? P C21 C22 C23 -179.3(2) . . . . ? C21 C22 C23 C24 0.2(4) . . . . ? C22 C23 C24 C25 0.6(5) . . . . ? C23 C24 C25 C26 -1.6(5) . . . . ? C24 C25 C26 C21 1.9(5) . . . . ? C22 C21 C26 C25 -1.1(4) . . . . ? P C21 C26 C25 178.3(2) . . . . ? C21 P C31 C36 -27.9(2) . . . . ? C11 P C31 C36 84.7(2) . . . . ? Se P C31 C36 -151.0(2) . . . . ? C21 P C31 C32 152.03(19) . . . . ? C11 P C31 C32 -95.4(2) . . . . ? Se P C31 C32 28.9(2) . . . . ? C36 C31 C32 C33 -1.0(4) . . . . ? P C31 C32 C33 179.0(2) . . . . ? C31 C32 C33 C34 0.3(4) . . . . ? C32 C33 C34 C35 0.5(5) . . . . ? C33 C34 C35 C36 -0.6(5) . . . . ? C32 C31 C36 C35 1.0(4) . . . . ? P C31 C36 C35 -179.1(2) . . . . ? C34 C35 C36 C31 -0.2(5) . . . . ? #===END data_sephcy2 _database_code_depnum_ccdc_archive 'CCDC 657197' _audit_creation_date 2006-03-16T10:41:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C18 H27 P Se' _chemical_formula_moiety 'C18 H27 P Se' _chemical_formula_weight 353.33 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 11.100(2) _cell_length_b 13.668(3) _cell_length_c 11.773(2) _cell_angle_alpha 90 _cell_angle_beta 98.26(3) _cell_angle_gamma 90 _cell_volume 1767.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 847 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.63 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description cuboid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5772 _exptl_absorpt_correction_T_max 0.7477 _exptl_absorpt_process_details ; SADABS (Bruker, 2004) ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_detector_area_resol_mean 512 _diffrn_measurement_device_type ; Bruker SMART CCD 1K ; _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12106 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4364 _reflns_number_gt 2688 _reflns_threshold_expression >2sigma(I) _exptl_special_details ; See manuscript ; #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker, 1999)' _computing_structure_solution 'SIR97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'WinGX (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0322P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4364 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.082 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.258 _refine_diff_density_min -0.28 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Se Se 0.62132(3) 0.40178(2) 0.71374(2) 0.05356(11) Uani 1 d . . . P P 0.66970(6) 0.33799(5) 0.56180(5) 0.03691(16) Uani 1 d . . . C11 C 0.7048(2) 0.43245(16) 0.46078(18) 0.0371(6) Uani 1 d . . . H11 H 0.6327 0.4743 0.4445 0.045 Uiso 1 calc R . . C12 C 0.8095(2) 0.49754(18) 0.5134(2) 0.0470(6) Uani 1 d . . . H12A H 0.7885 0.5276 0.5826 0.056 Uiso 1 calc R . . H12B H 0.8813 0.4575 0.5349 0.056 Uiso 1 calc R . . C13 C 0.8390(3) 0.57731(19) 0.4318(2) 0.0532(7) Uani 1 d . . . H13A H 0.7716 0.623 0.4188 0.064 Uiso 1 calc R . . H13B H 0.9105 0.6129 0.4666 0.064 Uiso 1 calc R . . C14 C 0.8624(2) 0.5352(2) 0.3177(2) 0.0537(7) Uani 1 d . . . H14A H 0.9355 0.4954 0.3294 0.064 Uiso 1 calc R . . H14B H 0.8753 0.5881 0.2659 0.064 Uiso 1 calc R . . C15 C 0.7556(2) 0.47305(19) 0.2642(2) 0.0502(7) Uani 1 d . . . H15A H 0.7736 0.4452 0.1927 0.06 Uiso 1 calc R . . H15B H 0.6838 0.5138 0.247 0.06 Uiso 1 calc R . . C16 C 0.7305(2) 0.39101(17) 0.34539(19) 0.0450(6) Uani 1 d . . . H16A H 0.8004 0.3477 0.3583 0.054 Uiso 1 calc R . . H16B H 0.661 0.3531 0.3106 0.054 Uiso 1 calc R . . C21 C 0.5494(2) 0.25985(17) 0.48658(19) 0.0386(6) Uani 1 d . . . H21 H 0.5813 0.2293 0.4217 0.046 Uiso 1 calc R . . C22 C 0.4376(2) 0.31981(18) 0.4386(2) 0.0507(7) Uani 1 d . . . H22A H 0.409 0.3558 0.5005 0.061 Uiso 1 calc R . . H22B H 0.46 0.3668 0.3835 0.061 Uiso 1 calc R . . C23 C 0.3356(2) 0.2549(2) 0.3804(2) 0.0635(8) Uani 1 d . . . H23A H 0.2644 0.2947 0.3555 0.076 Uiso 1 calc R . . H23B H 0.3609 0.2249 0.313 0.076 Uiso 1 calc R . . C24 C 0.3027(2) 0.1755(2) 0.4608(3) 0.0651(8) Uani 1 d . . . H24A H 0.2703 0.2053 0.5247 0.078 Uiso 1 calc R . . H24B H 0.2401 0.1337 0.4202 0.078 Uiso 1 calc R . . C25 C 0.4122(3) 0.11466(19) 0.5054(3) 0.0581(7) Uani 1 d . . . H25A H 0.4397 0.0798 0.4421 0.07 Uiso 1 calc R . . H25B H 0.3897 0.0666 0.5592 0.07 Uiso 1 calc R . . C26 C 0.5160(2) 0.17794(18) 0.5649(2) 0.0516(7) Uani 1 d . . . H26A H 0.5868 0.1372 0.5878 0.062 Uiso 1 calc R . . H26B H 0.4919 0.2064 0.6337 0.062 Uiso 1 calc R . . C31 C 0.8054(2) 0.26086(17) 0.5881(2) 0.0404(6) Uani 1 d . . . C32 C 0.8315(2) 0.19207(19) 0.5083(2) 0.0505(7) Uani 1 d . . . H32 H 0.7779 0.183 0.4408 0.061 Uiso 1 calc R . . C33 C 0.9369(3) 0.1370(2) 0.5287(3) 0.0663(8) Uani 1 d . . . H33 H 0.9536 0.0907 0.4752 0.08 Uiso 1 calc R . . C34 C 1.0178(3) 0.1504(2) 0.6286(3) 0.0722(9) Uani 1 d . . . H34 H 1.0892 0.114 0.6418 0.087 Uiso 1 calc R . . C35 C 0.9920(2) 0.2174(2) 0.7074(3) 0.0627(8) Uani 1 d . . . H35 H 1.0454 0.2255 0.7752 0.075 Uiso 1 calc R . . C36 C 0.8876(2) 0.27354(19) 0.6879(2) 0.0491(7) Uani 1 d . . . H36 H 0.8723 0.32 0.7417 0.059 Uiso 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 Se 0.0632(2) 0.05849(19) 0.04058(16) -0.00640(13) 0.01284(13) 0.00721(15) P 0.0355(3) 0.0399(4) 0.0349(3) -0.0004(3) 0.0035(3) 0.0037(3) C11 0.0354(14) 0.0363(13) 0.0392(13) -0.0017(10) 0.0041(11) 0.0039(11) C12 0.0466(16) 0.0472(15) 0.0461(14) -0.0092(12) 0.0031(12) -0.0023(13) C13 0.0489(17) 0.0476(16) 0.0643(18) -0.0100(13) 0.0120(14) -0.0112(13) C14 0.0519(17) 0.0522(17) 0.0576(17) 0.0042(13) 0.0105(14) -0.0074(14) C15 0.0546(17) 0.0534(17) 0.0425(14) 0.0035(12) 0.0066(13) -0.0090(14) C16 0.0510(16) 0.0441(15) 0.0391(14) -0.0020(11) 0.0034(12) -0.0076(13) C21 0.0356(14) 0.0416(14) 0.0387(13) 0.0001(10) 0.0052(11) 0.0063(11) C22 0.0347(14) 0.0472(16) 0.0670(18) 0.0030(13) -0.0041(13) 0.0006(12) C23 0.0390(16) 0.065(2) 0.081(2) -0.0067(16) -0.0116(15) 0.0061(15) C24 0.0437(17) 0.063(2) 0.090(2) -0.0223(17) 0.0126(16) -0.0131(15) C25 0.0563(18) 0.0469(17) 0.0717(19) -0.0006(14) 0.0112(15) -0.0069(14) C26 0.0507(16) 0.0474(16) 0.0562(16) 0.0026(12) 0.0065(13) -0.0024(13) C31 0.0352(14) 0.0448(15) 0.0410(14) 0.0087(11) 0.0044(11) 0.0023(12) C32 0.0455(16) 0.0533(16) 0.0520(16) 0.0028(13) 0.0041(13) 0.0156(14) C33 0.062(2) 0.0607(19) 0.079(2) 0.0063(16) 0.0224(18) 0.0204(16) C34 0.0403(17) 0.076(2) 0.101(3) 0.033(2) 0.0134(19) 0.0164(17) C35 0.0350(16) 0.074(2) 0.075(2) 0.0236(17) -0.0060(15) -0.0034(15) C36 0.0403(15) 0.0523(16) 0.0524(16) 0.0093(12) -0.0017(13) -0.0045(13) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Se P 2.1271(8) . ? P C31 1.828(2) . ? P C11 1.835(2) . ? P C21 1.835(2) . ? C11 C12 1.523(3) . ? C11 C16 1.536(3) . ? C11 H11 0.9800 . ? C12 C13 1.520(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.519(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.525(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C21 C22 1.526(3) . ? C21 C26 1.530(3) . ? C21 H21 0.9800 . ? C22 C23 1.521(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.519(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.504(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.527(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C31 C32 1.390(3) . ? C31 C36 1.391(3) . ? C32 C33 1.384(4) . ? C32 H32 0.9300 . ? C33 C34 1.385(4) . ? C33 H33 0.9300 . ? C34 C35 1.362(4) . ? C34 H34 0.9300 . ? C35 C36 1.381(4) . ? C35 H35 0.9300 . ? C36 H36 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 C31 P C11 105.61(11) . . ? C31 P C21 105.71(11) . . ? C11 P C21 107.72(10) . . ? C31 P Se 113.28(8) . . ? C11 P Se 111.07(8) . . ? C21 P Se 112.97(8) . . ? C12 C11 C16 110.3(2) . . ? C12 C11 P 111.62(16) . . ? C16 C11 P 113.43(16) . . ? C12 C11 H11 107.0 . . ? C16 C11 H11 107.0 . . ? P C11 H11 107.0 . . ? C13 C12 C11 112.5(2) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 111.5(2) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C15 110.9(2) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C16 110.6(2) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C11 110.94(19) . . ? C15 C16 H16A 109.5 . . ? C11 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? C22 C21 C26 111.2(2) . . ? C22 C21 P 111.26(16) . . ? C26 C21 P 110.97(16) . . ? C22 C21 H21 107.7 . . ? C26 C21 H21 107.7 . . ? P C21 H21 107.7 . . ? C23 C22 C21 111.5(2) . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C22 111.5(2) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C23 111.0(2) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C24 C25 C26 111.4(2) . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C21 111.7(2) . . ? C25 C26 H26A 109.3 . . ? C21 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C21 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C32 C31 C36 118.7(2) . . ? C32 C31 P 121.49(19) . . ? C36 C31 P 119.75(19) . . ? C33 C32 C31 120.3(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 120.3(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 119.6(3) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 120.9(3) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C35 C36 C31 120.3(3) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? 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 C31 P C11 C12 -63.94(19) . . . . ? C21 P C11 C12 -176.56(16) . . . . ? Se P C11 C12 59.24(18) . . . . ? C31 P C11 C16 61.4(2) . . . . ? C21 P C11 C16 -51.2(2) . . . . ? Se P C11 C16 -175.41(15) . . . . ? C16 C11 C12 C13 53.8(3) . . . . ? P C11 C12 C13 -179.16(17) . . . . ? C11 C12 C13 C14 -54.0(3) . . . . ? C12 C13 C14 C15 55.2(3) . . . . ? C13 C14 C15 C16 -57.3(3) . . . . ? C14 C15 C16 C11 57.8(3) . . . . ? C12 C11 C16 C15 -55.5(3) . . . . ? P C11 C16 C15 178.44(17) . . . . ? C31 P C21 C22 -168.95(17) . . . . ? C11 P C21 C22 -56.41(19) . . . . ? Se P C21 C22 66.64(18) . . . . ? C31 P C21 C26 66.69(19) . . . . ? C11 P C21 C26 179.23(17) . . . . ? Se P C21 C26 -57.73(18) . . . . ? C26 C21 C22 C23 -53.4(3) . . . . ? P C21 C22 C23 -177.65(19) . . . . ? C21 C22 C23 C24 55.2(3) . . . . ? C22 C23 C24 C25 -56.6(3) . . . . ? C23 C24 C25 C26 56.3(3) . . . . ? C24 C25 C26 C21 -55.0(3) . . . . ? C22 C21 C26 C25 53.2(3) . . . . ? P C21 C26 C25 177.62(18) . . . . ? C11 P C31 C32 -76.8(2) . . . . ? C21 P C31 C32 37.2(2) . . . . ? Se P C31 C32 161.43(18) . . . . ? C11 P C31 C36 100.4(2) . . . . ? C21 P C31 C36 -145.58(19) . . . . ? Se P C31 C36 -21.4(2) . . . . ? C36 C31 C32 C33 0.6(4) . . . . ? P C31 C32 C33 177.8(2) . . . . ? C31 C32 C33 C34 -0.5(4) . . . . ? C32 C33 C34 C35 0.9(5) . . . . ? C33 C34 C35 C36 -1.4(4) . . . . ? C34 C35 C36 C31 1.5(4) . . . . ? C32 C31 C36 C35 -1.1(4) . . . . ? P C31 C36 C35 -178.4(2) . . . . ? #===END